organic compounds
4-Bromo-2-[({2-[(2-hydroxyethyl)amino]ethyl}imino)methyl]phenol
aInstitute of Physics AS CR, v.v.i., Na Slovance 2, 182 21 Prague 8, Czech Republic, and bDepartment of Chemistry, Faculty of Science, Golestan University, Gorgan, Iran
*Correspondence e-mail: samolova@fzu.cz
The new title Schiff base compound, C11H15BrN2O2, crystallizes in the monoclinic P21 with two independent molecules in the It was prepared by the condensation reaction of 5-bromo-2-hydroxybenzaldehyde and aminoethylethanolamine. There is an intramolecular O—H⋯N hydrogen bond with an S(6) ring motif. Moreover, there are intermolecular C—H⋯N, C—H⋯O and Br⋯O interactions in the of the title compound.
Keywords: crystal structure; Schiff base; hydrogen bonds.
CCDC reference: 2074082
Structure description
et al., 2019; Ghorbani et al., 2017) due to their easy preparation, structural diversity, biological properties, and also their ability to act as chelating ligands (Böhme & Fels, 2020; Adrian et al., 2020; Saranya et al., 2020; Yousif et al., 2017; Guo et al., 2019; Bhattacharjee et al., 2017; Shweta et al., 2016; Reimann et al., 2019; Ceylan et al., 2015; Salehi et al., 2016; Zhu et al., 2019; Kumar et al., 2019; Atahan & Durmus, 2015). In the present work, we report the of the new Schiff base, commonly known as aminoethylethanolamine-5-bromo-2-hydroxybenzaldehyde. The of the title compound contains two independent molecules, as shown in Fig. 1. All bond lengths and angles are within their expected ranges according to other published Schiff base structures (Böhme & Fels, 2020; Ceylan et al., 2015; Salehi et al., 2016). The N1a=C7a double bond is 1.273 (6) Å and N1b=C7b 1.276 (7) Å, the N1a—C8a single bond is 1.460 (6) Å and N1b—C8b 1.455 (7) Å, in good agreement with the corresponding values for the similar compounds (Salehi et al., 2016; Ceylan et al., 2015). The bond angles C7a—N1a—C8a [118.0 (4)°], C7b—N1b—C8b [117.9 (4)°], C2a—C7a—N1a [121.5 (4)°] and C2b—C7b—N1b [121.7 (4)°] are also in agreement with those angles in the similar compounds (Salehi et al., 2016; Ceylan et al., 2015). An intramolecular hydrogen bond with an S(6) ring is observed in each independent molecule. Moreover, the O2a and O2b atoms are involved in a second intramolecular hydrogen bond. The molecules are connected through intermolecular O—H⋯N hydrogen bonds and Br⋯O interactions with distances Br1a⋯O2b = 3.206 (2) Å and Br1b⋯O2a = 3.282 (2) Å (Fig. 2, Table 1).
and their derivatives have played a key role in the development of coordination chemistry (VafazadehSynthesis and crystallization
5-Bromo-2-hydroxybenzaldehyde (2 mmol) was dissolved in ethanol (10 ml) and stirred for 10 min. Then, a solution of aminoethylethanolamine (0.2 mmol) dissolved in ethanol (5 ml) was added dropwise. The mixture was stirred and refluxed for 6 h. After that, the solution was concentrated under reduced pressure. Yellow crystals suitable for X-ray analysis were obtained by slow evaporation of solvent at room temperature for several days. These were filtered off and washed several times with cold ethanol.
Refinement
Crystal data, data collection and structure . Marching Cube ELD software (MCS) was used for the visualization (Rohlíček & Hušák, 2007).
details are summarized in Table 2
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Structural data
CCDC reference: 2074082
https://doi.org/10.1107/S2414314621003357/bt4109sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314621003357/bt4109Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314621003357/bt4109Isup3.cml
Data collection: CrysAlis PRO (Rigaku OD, 2015); cell
CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: Superflip (Palatinus & Chapuis, (2007); program(s) used to refine structure: Jana2006 (Petříček et al., 2014), MCE (Rohlíček & Hušák, 2007); molecular graphics: DIAMOND (Brandenburg, 1999).C11H15BrN2O2 | F(000) = 584 |
Mr = 287.2 | Dx = 1.643 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: P 2yb | Cell parameters from 5986 reflections |
a = 6.0518 (2) Å | θ = 6.4–75.4° |
b = 27.7837 (7) Å | µ = 4.74 mm−1 |
c = 6.9028 (2) Å | T = 95 K |
β = 90.497 (2)° | Platelet, colourless |
V = 1160.60 (6) Å3 | 0.38 × 0.25 × 0.04 mm |
Z = 4 |
Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, AtlasS2 diffractometer | 4637 independent reflections |
Radiation source: X-ray tube | 4488 reflections with I > 3σ(I) |
Mirror monochromator | Rint = 0.021 |
Detector resolution: 5.2027 pixels mm-1 | θmax = 75.5°, θmin = 6.4° |
ω scans | h = −7→7 |
Absorption correction: analytical (CrysAlisPro; Rigaku OD, 2015) | k = −34→34 |
Tmin = 0.34, Tmax = 0.816 | l = −7→8 |
8118 measured reflections |
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.055 | Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2) |
wR(F2) = 0.134 | (Δ/σ)max = 0.0004 |
S = 2.31 | Δρmax = 0.81 e Å−3 |
4637 reflections | Δρmin = −0.48 e Å−3 |
308 parameters | Absolute structure: Flack (1983), 2215 Friedel pairs |
6 restraints | Absolute structure parameter: −0.03 (3) |
103 constraints |
Refinement. All hydrogen atoms were discernible in difference Fourier maps and could be refined to reasonable geometry. Marching Cube ELD software (MCS) was used for the electron density map visualization (Rohlicek & Husak, 2007). According to common practice, H atoms bonded to C were kept in ideal positions with C–H = 0.96 Å while positions of H atom bonded to N and O were refined with restrained bond lengths 0.820 (1) Å for O—H bonds and 0.880 (1) Å for N—H bonds. In both cases Uiso(H) was set to 1.2Ueq(C,N,O). All non-hydrogen atoms were refined using harmonic refinement. |
x | y | z | Uiso*/Ueq | ||
Br1a | 0.82327 (7) | 0.119124 (17) | 0.59379 (6) | 0.01689 (14) | |
Br1b | 0.67219 (7) | 0.617268 (17) | 0.82063 (6) | 0.01663 (14) | |
O1a | 0.3912 (6) | 0.31366 (13) | 0.6749 (5) | 0.0160 (10) | |
O2a | 1.4292 (6) | 0.51220 (14) | 0.8603 (5) | 0.0181 (10) | |
O1b | 1.0984 (6) | 0.81041 (13) | 0.9575 (6) | 0.0170 (10) | |
O2b | 0.0585 (6) | 1.01653 (14) | 0.6475 (5) | 0.0173 (10) | |
N1a | 0.7625 (7) | 0.35173 (15) | 0.5676 (6) | 0.0136 (11) | |
N2a | 1.0395 (7) | 0.46689 (15) | 0.7058 (6) | 0.0138 (11) | |
N1b | 0.7210 (7) | 0.84968 (16) | 0.8774 (6) | 0.0147 (11) | |
N2b | 0.4536 (7) | 0.96878 (15) | 0.7831 (6) | 0.0130 (11) | |
C1a | 0.4889 (8) | 0.27034 (18) | 0.6505 (7) | 0.0123 (13) | |
C2a | 0.7071 (8) | 0.26658 (17) | 0.5792 (6) | 0.0113 (12) | |
C3a | 0.8022 (7) | 0.22102 (17) | 0.5563 (7) | 0.0110 (12) | |
C4a | 0.6828 (8) | 0.18042 (17) | 0.6059 (7) | 0.0127 (13) | |
C5a | 0.4692 (8) | 0.18358 (18) | 0.6760 (7) | 0.0135 (13) | |
C6a | 0.3746 (8) | 0.22869 (18) | 0.6977 (7) | 0.0136 (13) | |
C7a | 0.8414 (8) | 0.30963 (18) | 0.5459 (7) | 0.0119 (12) | |
C8a | 0.9119 (8) | 0.39261 (18) | 0.5457 (8) | 0.0153 (14) | |
C9a | 0.9002 (8) | 0.42429 (17) | 0.7262 (7) | 0.0156 (13) | |
C10a | 1.0340 (9) | 0.49712 (19) | 0.8800 (7) | 0.0147 (14) | |
C11a | 1.2178 (9) | 0.53440 (19) | 0.8765 (8) | 0.0169 (14) | |
C1b | 1.0028 (8) | 0.76776 (19) | 0.9183 (7) | 0.0132 (13) | |
C2b | 0.7840 (8) | 0.76505 (17) | 0.8468 (7) | 0.0123 (13) | |
C3b | 0.6901 (7) | 0.71945 (18) | 0.8096 (6) | 0.0111 (12) | |
C4b | 0.8125 (8) | 0.67826 (17) | 0.8475 (7) | 0.0128 (13) | |
C5b | 1.0266 (8) | 0.68081 (17) | 0.9183 (7) | 0.0129 (13) | |
C6b | 1.1215 (8) | 0.72560 (19) | 0.9527 (7) | 0.0138 (13) | |
C7b | 0.6447 (8) | 0.80791 (19) | 0.8387 (7) | 0.0131 (13) | |
C8b | 0.5641 (8) | 0.8890 (2) | 0.8969 (7) | 0.0174 (15) | |
C9b | 0.5974 (8) | 0.92782 (17) | 0.7427 (7) | 0.0132 (12) | |
C10b | 0.4570 (8) | 1.00481 (18) | 0.6268 (7) | 0.0140 (14) | |
C11b | 0.2681 (8) | 1.04018 (18) | 0.6529 (8) | 0.0166 (14) | |
H1o1a | 0.477 (9) | 0.3360 (17) | 0.656 (10) | 0.0192* | |
H1o2a | 1.447 (12) | 0.501 (2) | 0.970 (4) | 0.0217* | |
H1o1b | 1.022 (10) | 0.8341 (15) | 0.933 (10) | 0.0204* | |
H1o2b | 0.047 (12) | 1.006 (2) | 0.537 (4) | 0.0208* | |
H1n2a | 1.177 (3) | 0.460 (2) | 0.679 (9) | 0.0165* | |
H1n2b | 0.316 (4) | 0.958 (2) | 0.786 (9) | 0.0157* | |
H1c3a | 0.949114 | 0.217962 | 0.506473 | 0.0132* | |
H1c5a | 0.388396 | 0.155044 | 0.708997 | 0.0162* | |
H1c6a | 0.226862 | 0.231176 | 0.746291 | 0.0163* | |
H1c7a | 0.992328 | 0.305995 | 0.506916 | 0.0142* | |
H1c8a | 0.868714 | 0.41104 | 0.433975 | 0.0184* | |
H2c8a | 1.06028 | 0.381103 | 0.530093 | 0.0184* | |
H1c9a | 0.750008 | 0.434045 | 0.7466 | 0.0187* | |
H2c9a | 0.947685 | 0.406141 | 0.837289 | 0.0187* | |
H1c10a | 1.050579 | 0.477245 | 0.992939 | 0.0176* | |
H2c10a | 0.893641 | 0.513099 | 0.887122 | 0.0176* | |
H1c11a | 1.194585 | 0.555849 | 0.769179 | 0.0203* | |
H2c11a | 1.213354 | 0.553276 | 0.992845 | 0.0203* | |
H1c3b | 0.542552 | 0.716952 | 0.758373 | 0.0133* | |
H1c5b | 1.108922 | 0.65191 | 0.943463 | 0.0155* | |
H1c6b | 1.270528 | 0.727504 | 1.00081 | 0.0166* | |
H1c7b | 0.491711 | 0.804593 | 0.8034 | 0.0157* | |
H1c8b | 0.579114 | 0.903103 | 1.023326 | 0.0208* | |
H2c8b | 0.41626 | 0.876651 | 0.887421 | 0.0208* | |
H1c9b | 0.748732 | 0.938194 | 0.744645 | 0.0159* | |
H2c9b | 0.561579 | 0.91489 | 0.617336 | 0.0159* | |
H1c10b | 0.441354 | 0.988939 | 0.503918 | 0.0168* | |
H2c10b | 0.59503 | 1.021837 | 0.630526 | 0.0168* | |
H1c11b | 0.285747 | 1.056606 | 0.77445 | 0.0199* | |
H2c11b | 0.273235 | 1.0641 | 0.552719 | 0.0199* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1a | 0.0181 (2) | 0.0121 (2) | 0.0204 (2) | 0.0014 (2) | −0.00076 (17) | −0.0019 (2) |
Br1b | 0.0185 (2) | 0.0122 (2) | 0.0192 (2) | −0.0015 (2) | −0.00028 (17) | −0.0015 (2) |
O1a | 0.0109 (16) | 0.0154 (17) | 0.0216 (18) | 0.0020 (13) | 0.0010 (14) | −0.0024 (15) |
O2a | 0.0133 (17) | 0.0247 (19) | 0.0162 (17) | −0.0031 (14) | 0.0002 (14) | 0.0033 (15) |
O1b | 0.0106 (16) | 0.0154 (17) | 0.0249 (19) | −0.0008 (13) | −0.0014 (14) | −0.0021 (15) |
O2b | 0.0138 (16) | 0.0240 (19) | 0.0143 (16) | 0.0014 (14) | −0.0011 (13) | −0.0026 (14) |
N1a | 0.0119 (18) | 0.015 (2) | 0.0133 (18) | −0.0008 (16) | −0.0012 (14) | 0.0011 (15) |
N2a | 0.0125 (18) | 0.0143 (19) | 0.0146 (19) | −0.0025 (15) | 0.0002 (15) | 0.0001 (16) |
N1b | 0.0149 (19) | 0.014 (2) | 0.015 (2) | 0.0022 (16) | 0.0014 (16) | 0.0023 (16) |
N2b | 0.0105 (18) | 0.0136 (19) | 0.015 (2) | −0.0003 (14) | 0.0009 (15) | −0.0015 (16) |
C1a | 0.011 (2) | 0.017 (2) | 0.009 (2) | 0.0011 (18) | −0.0007 (17) | −0.0011 (18) |
C2a | 0.011 (2) | 0.017 (2) | 0.0064 (19) | −0.0010 (18) | −0.0020 (16) | 0.0004 (17) |
C3a | 0.008 (2) | 0.013 (2) | 0.0116 (19) | −0.0002 (17) | −0.0007 (16) | 0.0009 (17) |
C4a | 0.015 (2) | 0.011 (2) | 0.011 (2) | 0.0018 (17) | −0.0019 (17) | −0.0020 (16) |
C5a | 0.014 (2) | 0.016 (2) | 0.010 (2) | −0.0047 (18) | −0.0037 (18) | 0.0009 (17) |
C6a | 0.008 (2) | 0.022 (3) | 0.011 (2) | −0.0001 (19) | −0.0018 (17) | −0.0017 (18) |
C7a | 0.009 (2) | 0.016 (2) | 0.010 (2) | −0.0003 (17) | −0.0003 (16) | 0.0014 (18) |
C8a | 0.013 (2) | 0.014 (2) | 0.019 (3) | −0.0026 (18) | −0.0001 (18) | 0.0023 (18) |
C9a | 0.016 (2) | 0.015 (2) | 0.016 (2) | −0.0021 (18) | 0.0002 (18) | −0.0004 (18) |
C10a | 0.012 (2) | 0.017 (3) | 0.016 (2) | 0.0000 (19) | −0.0005 (19) | 0.0000 (18) |
C11a | 0.016 (2) | 0.019 (3) | 0.016 (2) | 0.0004 (19) | −0.0018 (19) | −0.0006 (19) |
C1b | 0.012 (2) | 0.017 (2) | 0.010 (2) | −0.0011 (18) | 0.0033 (17) | −0.0001 (18) |
C2b | 0.013 (2) | 0.015 (2) | 0.008 (2) | 0.0004 (18) | 0.0011 (17) | 0.0010 (18) |
C3b | 0.009 (2) | 0.013 (2) | 0.011 (2) | 0.0007 (17) | −0.0004 (16) | 0.0014 (17) |
C4b | 0.016 (2) | 0.013 (2) | 0.010 (2) | −0.0021 (18) | 0.0012 (18) | −0.0023 (17) |
C5b | 0.015 (2) | 0.013 (2) | 0.011 (2) | 0.0054 (18) | 0.0016 (18) | 0.0005 (17) |
C6b | 0.009 (2) | 0.019 (2) | 0.013 (2) | −0.0006 (18) | 0.0011 (19) | 0.0013 (19) |
C7b | 0.009 (2) | 0.018 (2) | 0.013 (2) | 0.0005 (18) | 0.0008 (17) | 0.0010 (18) |
C8b | 0.018 (3) | 0.015 (3) | 0.019 (3) | 0.0007 (17) | 0.004 (2) | −0.0006 (18) |
C9b | 0.012 (2) | 0.013 (2) | 0.014 (2) | 0.0019 (17) | 0.0001 (18) | 0.0003 (18) |
C10b | 0.011 (2) | 0.018 (3) | 0.013 (2) | 0.0013 (18) | 0.0028 (19) | 0.0015 (17) |
C11b | 0.016 (2) | 0.014 (2) | 0.020 (2) | 0.0017 (19) | 0.001 (2) | 0.0009 (19) |
Br1a—C4a | 1.906 (5) | C8a—C9a | 1.528 (7) |
Br1b—C4b | 1.904 (5) | C8a—H1c8a | 0.96 |
O1a—C1a | 1.352 (6) | C8a—H2c8a | 0.96 |
O1a—H1o1a | 0.82 (5) | C9a—H1c9a | 0.96 |
O2a—C11a | 1.425 (6) | C9a—H2c9a | 0.96 |
O2a—H1o2a | 0.82 (3) | C10a—C11a | 1.520 (7) |
O1b—C1b | 1.345 (6) | C10a—H1c10a | 0.96 |
O1b—H1o1b | 0.82 (5) | C10a—H2c10a | 0.96 |
O2b—C11b | 1.429 (6) | C11a—H1c11a | 0.96 |
O2b—H1o2b | 0.82 (3) | C11a—H2c11a | 0.96 |
N1a—C7a | 1.273 (6) | C1b—C2b | 1.411 (7) |
N1a—C8a | 1.460 (6) | C1b—C6b | 1.393 (7) |
N2a—C9a | 1.460 (6) | C2b—C3b | 1.411 (7) |
N2a—C10a | 1.467 (7) | C2b—C7b | 1.460 (7) |
N2a—H1n2a | 0.88 (3) | C3b—C4b | 1.387 (7) |
N1b—C7b | 1.276 (7) | C3b—H1c3b | 0.96 |
N1b—C8b | 1.455 (7) | C4b—C5b | 1.382 (7) |
N2b—C9b | 1.461 (6) | C5b—C6b | 1.390 (7) |
N2b—C10b | 1.472 (7) | C5b—H1c5b | 0.96 |
N2b—H1n2b | 0.88 (3) | C6b—H1c6b | 0.96 |
C1a—C2a | 1.417 (7) | C7b—H1c7b | 0.96 |
C1a—C6a | 1.388 (7) | C8b—C9b | 1.530 (7) |
C2a—C3a | 1.400 (7) | C8b—H1c8b | 0.96 |
C2a—C7a | 1.465 (7) | C8b—H2c8b | 0.96 |
C3a—C4a | 1.384 (7) | C9b—H1c9b | 0.96 |
C3a—H1c3a | 0.96 | C9b—H2c9b | 0.96 |
C4a—C5a | 1.387 (7) | C10b—C11b | 1.519 (7) |
C5a—C6a | 1.387 (7) | C10b—H1c10b | 0.96 |
C5a—H1c5a | 0.96 | C10b—H2c10b | 0.96 |
C6a—H1c6a | 0.96 | C11b—H1c11b | 0.96 |
C7a—H1c7a | 0.96 | C11b—H2c11b | 0.96 |
C1a—O1a—H1o1a | 112 (4) | O2a—C11a—C10a | 111.3 (4) |
C11a—O2a—H1o2a | 101 (5) | O2a—C11a—H1c11a | 109.47 |
C1b—O1b—H1o1b | 115 (4) | O2a—C11a—H2c11a | 109.47 |
C11b—O2b—H1o2b | 105 (5) | C10a—C11a—H1c11a | 109.47 |
C7a—N1a—C8a | 118.0 (4) | C10a—C11a—H2c11a | 109.47 |
C9a—N2a—C10a | 111.6 (4) | H1c11a—C11a—H2c11a | 107.54 |
C9a—N2a—H1n2a | 113 (4) | O1b—C1b—C2b | 121.2 (4) |
C10a—N2a—H1n2a | 109 (4) | O1b—C1b—C6b | 119.1 (4) |
C7b—N1b—C8b | 117.9 (4) | C2b—C1b—C6b | 119.7 (5) |
C9b—N2b—C10b | 112.2 (4) | C1b—C2b—C3b | 119.1 (4) |
C9b—N2b—H1n2b | 108 (4) | C1b—C2b—C7b | 120.6 (4) |
C10b—N2b—H1n2b | 105 (4) | C3b—C2b—C7b | 119.6 (4) |
O1a—C1a—C2a | 121.3 (4) | C2b—C3b—C4b | 119.5 (4) |
O1a—C1a—C6a | 119.5 (4) | C2b—C3b—H1c3b | 120.24 |
C2a—C1a—C6a | 119.2 (4) | C4b—C3b—H1c3b | 120.24 |
C1a—C2a—C3a | 119.4 (4) | Br1b—C4b—C3b | 118.6 (4) |
C1a—C2a—C7a | 120.9 (4) | Br1b—C4b—C5b | 119.7 (4) |
C3a—C2a—C7a | 119.4 (4) | C3b—C4b—C5b | 121.5 (4) |
C2a—C3a—C4a | 119.5 (4) | C4b—C5b—C6b | 119.4 (4) |
C2a—C3a—H1c3a | 120.23 | C4b—C5b—H1c5b | 120.31 |
C4a—C3a—H1c3a | 120.23 | C6b—C5b—H1c5b | 120.31 |
Br1a—C4a—C3a | 118.9 (4) | C1b—C6b—C5b | 120.8 (4) |
Br1a—C4a—C5a | 119.3 (4) | C1b—C6b—H1c6b | 119.6 |
C3a—C4a—C5a | 121.7 (4) | C5b—C6b—H1c6b | 119.6 |
C4a—C5a—C6a | 118.8 (4) | N1b—C7b—C2b | 121.7 (4) |
C4a—C5a—H1c5a | 120.6 | N1b—C7b—H1c7b | 119.13 |
C6a—C5a—H1c5a | 120.6 | C2b—C7b—H1c7b | 119.13 |
C1a—C6a—C5a | 121.4 (5) | N1b—C8b—C9b | 112.0 (4) |
C1a—C6a—H1c6a | 119.31 | N1b—C8b—H1c8b | 109.47 |
C5a—C6a—H1c6a | 119.31 | N1b—C8b—H2c8b | 109.47 |
N1a—C7a—C2a | 121.5 (4) | C9b—C8b—H1c8b | 109.47 |
N1a—C7a—H1c7a | 119.24 | C9b—C8b—H2c8b | 109.47 |
C2a—C7a—H1c7a | 119.24 | H1c8b—C8b—H2c8b | 106.79 |
N1a—C8a—C9a | 109.3 (4) | N2b—C9b—C8b | 109.5 (4) |
N1a—C8a—H1c8a | 109.47 | N2b—C9b—H1c9b | 109.47 |
N1a—C8a—H2c8a | 109.47 | N2b—C9b—H2c9b | 109.47 |
C9a—C8a—H1c8a | 109.47 | C8b—C9b—H1c9b | 109.47 |
C9a—C8a—H2c8a | 109.47 | C8b—C9b—H2c9b | 109.47 |
H1c8a—C8a—H2c8a | 109.64 | H1c9b—C9b—H2c9b | 109.45 |
N2a—C9a—C8a | 111.0 (4) | N2b—C10b—C11b | 109.7 (4) |
N2a—C9a—H1c9a | 109.47 | N2b—C10b—H1c10b | 109.47 |
N2a—C9a—H2c9a | 109.47 | N2b—C10b—H2c10b | 109.47 |
C8a—C9a—H1c9a | 109.47 | C11b—C10b—H1c10b | 109.47 |
C8a—C9a—H2c9a | 109.47 | C11b—C10b—H2c10b | 109.47 |
H1c9a—C9a—H2c9a | 107.95 | H1c10b—C10b—H2c10b | 109.22 |
N2a—C10a—C11a | 110.8 (4) | O2b—C11b—C10b | 111.6 (4) |
N2a—C10a—H1c10a | 109.47 | O2b—C11b—H1c11b | 109.47 |
N2a—C10a—H2c10a | 109.47 | O2b—C11b—H2c11b | 109.47 |
C11a—C10a—H1c10a | 109.47 | C10b—C11b—H1c11b | 109.47 |
C11a—C10a—H2c10a | 109.47 | C10b—C11b—H2c11b | 109.47 |
H1c10a—C10a—H2c10a | 108.1 | H1c11b—C11b—H2c11b | 107.25 |
D—H···A | D—H | H···A | D···A | D—H···A |
O1a—H1o1a···N1a | 0.82 (5) | 1.89 (6) | 2.597 (5) | 144 (5) |
O1a—H1o1a···C7a | 0.82 (5) | 2.45 (6) | 2.876 (6) | 113 (4) |
O2a—H1o2a···N2bi | 0.82 (3) | 2.02 (4) | 2.826 (6) | 168 (6) |
O1b—H1o1b···N1b | 0.82 (5) | 1.91 (6) | 2.587 (6) | 139 (5) |
O2b—H1o2b···N2aii | 0.82 (3) | 2.06 (4) | 2.859 (6) | 165 (6) |
N2a—H1n2a···O2a | 0.88 (3) | 2.45 (5) | 2.871 (6) | 110 (5) |
N2b—H1n2b···O2b | 0.88 (3) | 2.44 (5) | 2.884 (5) | 112 (5) |
Symmetry codes: (i) −x+2, y−1/2, −z+2; (ii) −x+1, y+1/2, −z+1. |
Acknowledgements
The authors are grateful to Golestan University. CzechNanoLab project LM2018110 funded by MEYS CR is gratefully acknowledged for financial support of the measurements at LNSM Research Infrastructure.
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