4-Bromo-2-[({2-[(2-hy­droxy­eth­yl)amino]­eth­yl}imino)­meth­yl]phenol

Samoľová, E.; Dehno Khalaji, A.; Eigner, V.

doi:10.1107/S2414314621003357

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 6| Part 4| April 2021| x210335

https://doi.org/10.1107/S2414314621003357

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4-Bromo-2-[({2-[(2-hydroxyethyl)amino]ethyl}imino)methyl]phenol

Erika Samoľová,^a ^* Aliakbar Dehno Khalaji ^b and Václav Eigner ^a

^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

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 23 March 2021; accepted 29 March 2021; online 9 April 2021)

The new title Schiff base compound, C₁₁H₁₅BrN₂O₂, crystallizes in the monoclinic space group P2₁ with two independent molecules in the asymmetric unit. 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 crystal structure of the title compound.

Keywords: crystal structure; Schiff base; hydrogen bonds.

CCDC reference: 2074082

Structure description

Schiff bases and their derivatives have played a key role in the development of coordination chemistry (Vafazadeh et al., 2019 ; Ghorbani et al., 2017 ) due to their easy preparation, structural diversity, biological properties, catalytic activity 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 crystal structure of the new Schiff base, commonly known as aminoethylethanolamine-5-bromo-2-hydroxybenzaldehyde. The asymmetric unit 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).

Table 1
Hydrogen-bond geometry (Å, °)

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)
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) $[-x+2, y-{\script{1\over 2}}, -z+2]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

Figure 1
The asymmetric unit of the title structure. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
View of the hydrogen-bond system and the Br⋯O interactions in the title compound. Hydrogen atoms not involved in hydrogen bonding are omitted for clarity. Symmetry codes: (i) 2 − x, y − $[{1\over 2}]$ , 2 − z; (ii) 1 − x, $[{1\over 2}]$ + y, 1 − z; (iii) 1 + x, y, z; (iv) 3 − x, $[{1\over 2}]$ + y, 2 − z.

Synthesis 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 refinement details are summarized in Table 2. Marching Cube ELD software (MCS) was used for the electron density map visualization (Rohlíček & Hušák, 2007 ).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₁H₁₅BrN₂O₂
M_r	287.2
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	95
a, b, c (Å)	6.0518 (2), 27.7837 (7), 6.9028 (2)
β (°)	90.497 (2)
V (Å³)	1160.60 (6)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	4.74
Crystal size (mm)	0.38 × 0.25 × 0.04

Data collection
Diffractometer	Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, AtlasS2
Absorption correction	Analytical (CrysAlis PRO; Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.34, 0.816
No. of measured, independent and observed [I > 3σ(I)] reflections	8118, 4637, 4488
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.134, 2.31
No. of reflections	4637
No. of parameters	308
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.81, −0.48
Absolute structure	Flack (1983 ), 2215 Friedel pairs
Absolute structure parameter	−0.03 (3)
Computer programs: CrysAlis PRO (Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SUPERFLIP (Palatinus & Chapuis, (2007 ), JANA2006 (Petříček et al., 2014 ), MCE (Rohlíček & Hušák, 2007) and DIAMOND (Brandenburg, 1999 ).

Structural data

CCDC reference: 2074082

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314621003357/bt4109sup1.cif

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

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: 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).

4-Bromo-2-[({2-[(2-hydroxyethyl)amino]ethyl}imino)methyl]phenol top

Crystal data top

C₁₁H₁₅BrN₂O₂	F(000) = 584
M_r = 287.2	D_x = 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

Data collection top

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	R_int = 0.021
Detector resolution: 5.2027 pixels mm^-1	θ_max = 75.5°, θ_min = 6.4°
ω scans	h = −7→7
Absorption correction: analytical (CrysAlisPro; Rigaku OD, 2015)	k = −34→34
T_min = 0.34, T_max = 0.816	l = −7→8
8118 measured reflections

Refinement top

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	Δρ_max = 0.81 e Å⁻³
4637 reflections	Δρ_min = −0.48 e Å⁻³
308 parameters	Absolute structure: Flack (1983), 2215 Friedel pairs
6 restraints	Absolute structure parameter: −0.03 (3)
103 constraints

Special details top

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 U_iso(H) was set to 1.2U_eq(C,N,O). All non-hydrogen atoms were refined using harmonic refinement.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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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