2-{[(1S,2S)-1-Hy­droxy-1-phenyl­propan-2-yl](methyl)amino}-N-(3-methyl­phen­yl)acetamide

Bobonazarova, S.; Torambetov, B.; Burieva, D.; Abdushukurov, A.; Kadirova, S.; Okmanov, R.Y.; Yusufov, M.

doi:10.1107/S2414314625005784

organic compounds

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ISSN: 2414-3146

Volume 10| Part 7| July 2025| x250578

https://doi.org/10.1107/S2414314625005784

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2-{[(1S,2S)-1-Hydroxy-1-phenylpropan-2-yl](methyl)amino}-N-(3-methylphenyl)acetamide

Sarvinoz Bobonazarova,^a Batirbay Torambetov,^a,^b ^* Dilnoza Burieva,^a Anvar Abdushukurov,^a Shakhnoza Kadirova,^a Rasul Ya Okmanov ^c and Mukhriddin Yusufov ^a

^aNational University of Uzbekistan named after Mirzo Ulugbek, 4 University St., Tashkent, 100174, Uzbekistan, ^bPhysical and Material Chemistry Division, CSIR-National Chemical Laboratory, Pune, 411008, India, and ^cS.Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek St 77, Tashkent 100170, Uzbekistan
^*Correspondence e-mail: [email protected]

Edited by R. J. Butcher, Howard University, USA (Received 24 June 2025; accepted 26 June 2025; online 4 July 2025)

The title compound, C₁₉H₂₄N₂O₂ (m-TAP), was synthesized via the reaction of 2-chloro-N-(m-tolyl)acetamide with pseudoephidrine. It crystallizes in the monoclinic crystal system with a non-centrosymmetric chiral space group P2₁ (No. 4). The asymmetric unit comprises a single molecule. The dihedral angle between the phenyl rings is 89.20 (10)°. m-TAP contains two chiral centers at the C7 and C8 positions, both with an absolute configuration of S.

Keywords: pseudoephedrine; organic synthesis; chiral centers; 2-chloroacetamides; crystal structure.

CCDC reference: 2467626

Structure description

Extensive global research is focused on the efficient synthesis of N-acetamide-bonded compounds via chloroacetylation of amino compounds, especially aromatic and heterocyclic amines containing heteroatoms (Souza et al., 2019 ; Ma et al., 2011 ). These aromatic amides are vital intermediates in pharmaceuticals (e.g., anesthetics such as mepivacaine, articaine, prilocaine), hypnotics, diuretics (e.g., methaqualone), agricultural fungicides (e.g., triazole derivatives), herbicides (e.g., metolachlor), and in the oil and gas industry. In this study, m-toluidine was reacted with chloroacetyl chloride to form 2-chloro-N-m-tolylacetamide, followed by a reactivity study with pseudoephedrine to form m-TAP. The crystal structure of m-TAP (Fig. 1) was determined using single-crystal X-ray diffraction (SCXRD) indicating that it crystallizes in the monoclinic crystal system with a non-centrosymmetric chiral space group P2₁ (No. 4). The dihedral angle between the two phenyl rings is 89.20 (1)°, indicating a nearly perpendicular orientation. The torsion angles for the fragments C18—C13—N2—C12 and C5—C6—C7—C8 are 17.0 (3) and −73.9 (2)°, respectively. The twisted molecular conformation prevents effective π–π stacking interactions between the benzene rings. Additionally, m-TAP possesses two chiral centers at the C7 and C8 positions, with both absolute configurations being S. An intramolecular hydrogen bond [N2—H2⋯O1, H⋯A = 2.23 (3) Å; Table 1] occurs between the hydrogen atom of the amine group and the carbonyl oxygen atom. In addition, two neighbouring molecules are linked through a strong intermolecular hydrogen-bonding interaction [O1—H1⋯O2, H⋯A = 1.88 (3) Å; Table 1] involving the carbonyl oxygen atom and the hydroxyl hydrogen atom of an adjacent molecule. Moreover, the C—H groups of the phenyl ring are involved in H⋯H interactions with hydrogen atoms from the methyl group attached to chiral carbon (C8) and methylene (C11) groups, as well as with the phenyl C—H groups of adjacent molecules (Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯C1ⁱ	0.97	2.83	3.720 (3)	152
C16—H16⋯C12ⁱⁱ	0.93	2.80	3.378 (3)	121
C2—H2A⋯C14ⁱⁱⁱ	0.93	2.86	3.687 (3)	149
C1—H1A⋯C5ⁱⁱⁱ	0.93	2.84	3.762 (3)	171
O1—H1⋯O2^iv	0.90 (3)	1.88 (3)	2.7663 (17)	169 (3)
N2—H2⋯O1	0.87 (4)	2.23 (3)	3.0184 (19)	150 (3)
Symmetry codes: (i) ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+2]$ ; (iii) $[-x+2, y+{\script{1\over 2}}, -z+1]$ ; (iv) .

Figure 1
The molecular structure of m-TAP showing the atom labeling with displacement ellipsoids drawn at the 30% probability level. Hydrogen atoms are represented as small spheres with arbitrary radii. The intramolecular hydrogen bond is indicated by a blue dashed line.

Figure 2
The packing of molecules in m-TAP, connected via O⋯H and H⋯H interactions, viewed along the b-axis direction.

Synthesis and crystallization

Into a 50 ml round-bottom flask, 0.1835 g (1.0 mmol) of 2-chloro-N-o-tolylacetamide and 0.138 g (1.0 mmol) of potassium carbonate (K₂CO₃) were added. To this, 2 ml of N,N-dimethylformamide (DMF) and 0.165 g (1.0 mmol) of pseudoephedrine were added. The reaction mixture was placed in an ultrasonic water bath and stirred at 80°C for 2 h. Reaction progress was monitored every 15 minutes using thin-layer chromatography (TLC), with a mobile phase consisting of hexane:ethyl acetate:methanol in a 1:1:0.25 ratio. After completion, the reaction mixture was poured into 20 ml of ethyl acetate and washed twice with 20 ml of water. The organic layer was dried over anhydrous sodium sulfate (Na₂SO₄), and the solvent was removed under reduced pressure using a rotary evaporator. The crude product was recrystallized from acetone to afford a white crystalline solid. Yield: 91%, m.p. 156–157.3°C. The reaction scheme is shown in Fig. 3.

Figure 3
Reaction scheme.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₉H₂₄N₂O₂
M_r	312.40
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	295
a, b, c (Å)	7.3745 (2), 10.6486 (2), 11.1872 (2)
β (°)	98.727 (1)
V (Å³)	868.34 (3)
Z	2
Radiation type	Cu Kα
μ (mm⁻¹)	0.62
Crystal size (mm)	0.3 × 0.25 × 0.05

Data collection
Diffractometer	Bruker D8 VENTURE dual wavelength Mo/Cu
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.63, 0.97
No. of measured, independent and observed [I > 2σ(I)] reflections	26843, 3310, 3234
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.090, 1.05
No. of reflections	3310
No. of parameters	218
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.14
Absolute structure	Flack x determined using quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.08 (5)
Computer programs: APEX5 and SAINT (Bruker, 2016 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 2467626

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314625005784/bv4055sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314625005784/bv4055Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314625005784/bv4055Isup3.cml

checkCIF report

Computing details top

2-{[(1S,2S)-1-Hydroxy-1-phenylpropan-2-yl](methyl)amino}-N-(3-methylphenyl)acetamide top

Crystal data top

C₁₉H₂₄N₂O₂	F(000) = 336
M_r = 312.40	D_x = 1.195 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54178 Å
a = 7.3745 (2) Å	Cell parameters from 9843 reflections
b = 10.6486 (2) Å	θ = 4.2–72.1°
c = 11.1872 (2) Å	µ = 0.62 mm⁻¹
β = 98.727 (1)°	T = 295 K
V = 868.34 (3) Å³	Prism, colourless
Z = 2	0.3 × 0.25 × 0.05 mm

Data collection top

Bruker D8 VENTURE dual wavelength Mo/Cu diffractometer	3310 independent reflections
Radiation source: microfocus sealed X-ray tube, INCOATEC IµS	3234 reflections with I > 2σ(I)
Detector resolution: 7.3910 pixels mm^-1	R_int = 0.028
φ and ω scans	θ_max = 72.1°, θ_min = 7.4°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −9→9
T_min = 0.63, T_max = 0.97	k = −13→13
26843 measured reflections	l = −13→13

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.033	w = 1/[σ²(F_o²) + (0.062P)² + 0.0428P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.090	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.14 e Å⁻³
3310 reflections	Δρ_min = −0.14 e Å⁻³
218 parameters	Extinction correction: SHELXL-2016/6 (Sheldrick 2015a), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.017 (3)
Primary atom site location: dual	Absolute structure: Flack x determined using ???? quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.08 (5)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Hydrogen atoms attached to both O and N were refined isotropically. All C—H hydrogen atoms were refined with a riding model and thermal parameters at 1.2U_eq(C) [1.5U_eq for CH₃ groups].

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

	x	y	z	U_iso*/U_eq
O2	0.19659 (16)	0.49733 (14)	0.75216 (13)	0.0570 (3)
O1	0.83687 (17)	0.56561 (15)	0.67162 (13)	0.0621 (4)
N2	0.50958 (18)	0.49800 (15)	0.79114 (13)	0.0444 (3)
N1	0.5411 (2)	0.71980 (16)	0.68727 (15)	0.0541 (4)
C12	0.3453 (2)	0.54641 (18)	0.74646 (15)	0.0444 (4)
C11	0.3562 (3)	0.6750 (2)	0.6896 (2)	0.0628 (5)
H11A	0.291810	0.672125	0.607361	0.075*
H11B	0.292958	0.734947	0.733978	0.075*
C8	0.6074 (2)	0.70207 (18)	0.57142 (16)	0.0490 (4)
H8	0.544529	0.627981	0.533165	0.059*
C7	0.8137 (2)	0.67175 (18)	0.59309 (17)	0.0493 (4)
H7	0.880277	0.743225	0.633818	0.059*
C10	0.5830 (4)	0.8383 (3)	0.7480 (2)	0.0760 (7)
H10A	0.710747	0.857139	0.750148	0.114*
H10B	0.555850	0.833006	0.829119	0.114*
H10C	0.510220	0.903462	0.705160	0.114*
C9	0.5630 (3)	0.8113 (3)	0.4835 (2)	0.0727 (7)
H9A	0.590232	0.787704	0.405341	0.109*
H9B	0.635548	0.882956	0.512560	0.109*
H9C	0.435158	0.831937	0.477323	0.109*
C13	0.5518 (2)	0.38461 (16)	0.85436 (14)	0.0422 (4)
C14	0.7304 (2)	0.37236 (18)	0.91462 (16)	0.0473 (4)
H14	0.811827	0.438983	0.914194	0.057*
C15	0.7893 (3)	0.2626 (2)	0.97539 (16)	0.0539 (5)
C16	0.6655 (3)	0.1640 (2)	0.97430 (18)	0.0614 (5)
H16	0.702696	0.089149	1.013278	0.074*
C17	0.4875 (3)	0.1765 (2)	0.9158 (2)	0.0639 (5)
H17	0.405820	0.110039	0.916814	0.077*
C18	0.4286 (3)	0.28598 (19)	0.85571 (17)	0.0539 (4)
H18	0.308415	0.293557	0.816781	0.065*
C19	0.9830 (3)	0.2510 (3)	1.0389 (2)	0.0777 (7)
H19A	0.984099	0.205491	1.113103	0.117*
H19B	1.033580	0.333206	1.056255	0.117*
H19C	1.055267	0.206803	0.987990	0.117*
C6	0.8869 (2)	0.64569 (17)	0.47647 (16)	0.0475 (4)
C5	0.8472 (3)	0.53396 (19)	0.4147 (2)	0.0636 (5)
H5	0.774224	0.474589	0.445596	0.076*
C4	0.9139 (4)	0.5088 (2)	0.3080 (3)	0.0770 (7)
H4	0.883943	0.433812	0.267074	0.092*
C3	1.0244 (3)	0.5950 (3)	0.2629 (2)	0.0734 (6)
H3	1.073542	0.577169	0.193008	0.088*
C2	1.0624 (3)	0.7081 (3)	0.3215 (2)	0.0714 (6)
H2A	1.135170	0.767248	0.290147	0.086*
C1	0.9926 (3)	0.7334 (2)	0.42666 (19)	0.0596 (5)
H1A	1.016741	0.810609	0.464675	0.072*
H1	0.957 (4)	0.551 (3)	0.691 (3)	0.089*
H2	0.604 (4)	0.541 (3)	0.775 (3)	0.089*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0337 (6)	0.0634 (8)	0.0729 (9)	0.0048 (6)	0.0043 (5)	0.0058 (6)
O1	0.0357 (6)	0.0814 (10)	0.0704 (8)	0.0125 (6)	0.0123 (5)	0.0361 (8)
N2	0.0342 (7)	0.0513 (7)	0.0483 (8)	0.0043 (6)	0.0076 (5)	0.0052 (6)
N1	0.0414 (7)	0.0595 (9)	0.0629 (9)	0.0089 (7)	0.0122 (6)	0.0127 (7)
C12	0.0348 (7)	0.0554 (9)	0.0431 (8)	0.0081 (7)	0.0068 (5)	−0.0011 (7)
C11	0.0388 (9)	0.0720 (13)	0.0795 (13)	0.0164 (8)	0.0152 (8)	0.0251 (10)
C8	0.0373 (8)	0.0533 (9)	0.0552 (10)	0.0063 (7)	0.0031 (6)	0.0043 (8)
C7	0.0358 (8)	0.0572 (10)	0.0544 (10)	0.0006 (7)	0.0047 (6)	0.0135 (7)
C10	0.0647 (14)	0.0934 (18)	0.0680 (14)	0.0043 (12)	0.0045 (10)	−0.0130 (12)
C9	0.0660 (13)	0.0922 (17)	0.0605 (13)	0.0334 (12)	0.0115 (9)	0.0251 (11)
C13	0.0402 (8)	0.0496 (9)	0.0377 (8)	0.0061 (6)	0.0092 (6)	0.0001 (6)
C14	0.0420 (8)	0.0559 (10)	0.0438 (8)	0.0051 (7)	0.0061 (6)	−0.0011 (7)
C15	0.0543 (10)	0.0677 (11)	0.0399 (9)	0.0173 (8)	0.0077 (7)	0.0032 (8)
C16	0.0748 (13)	0.0602 (11)	0.0520 (10)	0.0154 (10)	0.0187 (9)	0.0154 (8)
C17	0.0663 (12)	0.0608 (12)	0.0675 (13)	−0.0036 (10)	0.0192 (9)	0.0128 (9)
C18	0.0452 (9)	0.0620 (11)	0.0550 (10)	−0.0012 (8)	0.0091 (7)	0.0065 (8)
C19	0.0674 (14)	0.0945 (18)	0.0653 (13)	0.0278 (13)	−0.0091 (10)	0.0052 (12)
C6	0.0332 (7)	0.0517 (9)	0.0577 (10)	0.0047 (7)	0.0070 (6)	0.0163 (8)
C5	0.0631 (11)	0.0468 (10)	0.0875 (15)	0.0022 (8)	0.0327 (10)	0.0129 (9)
C4	0.0893 (16)	0.0541 (11)	0.0959 (17)	0.0085 (12)	0.0412 (14)	0.0010 (11)
C3	0.0699 (13)	0.0806 (15)	0.0765 (14)	0.0155 (12)	0.0330 (11)	0.0178 (12)
C2	0.0588 (12)	0.0888 (16)	0.0687 (13)	−0.0124 (11)	0.0163 (9)	0.0280 (12)
C1	0.0539 (10)	0.0637 (11)	0.0605 (11)	−0.0135 (9)	0.0059 (8)	0.0151 (9)

Geometric parameters (Å, º) top

O2—C12	1.225 (2)	C13—C18	1.390 (3)
O1—C7	1.426 (2)	C14—H14	0.9300
O1—H1	0.90 (3)	C14—C15	1.389 (3)
N2—C12	1.341 (2)	C15—C16	1.390 (3)
N2—C13	1.410 (2)	C15—C19	1.501 (3)
N2—H2	0.87 (4)	C16—H16	0.9300
N1—C11	1.449 (2)	C16—C17	1.381 (3)
N1—C8	1.465 (2)	C17—H17	0.9300
N1—C10	1.444 (3)	C17—C18	1.383 (3)
C12—C11	1.517 (3)	C18—H18	0.9300
C11—H11A	0.9700	C19—H19A	0.9600
C11—H11B	0.9700	C19—H19B	0.9600
C8—H8	0.9800	C19—H19C	0.9600
C8—C7	1.538 (2)	C6—C5	1.385 (3)
C8—C9	1.526 (3)	C6—C1	1.386 (3)
C7—H7	0.9800	C5—H5	0.9300
C7—C6	1.512 (3)	C5—C4	1.384 (3)
C10—H10A	0.9600	C4—H4	0.9300
C10—H10B	0.9600	C4—C3	1.374 (4)
C10—H10C	0.9600	C3—H3	0.9300
C9—H9A	0.9600	C3—C2	1.379 (4)
C9—H9B	0.9600	C2—H2A	0.9300
C9—H9C	0.9600	C2—C1	1.381 (3)
C13—C14	1.392 (2)	C1—H1A	0.9300

C7—O1—H1	108 (2)	C18—C13—N2	123.90 (15)
C12—N2—C13	129.35 (15)	C18—C13—C14	119.72 (16)
C12—N2—H2	115 (2)	C13—C14—H14	119.4
C13—N2—H2	116 (2)	C15—C14—C13	121.27 (18)
C11—N1—C8	114.52 (17)	C15—C14—H14	119.4
C10—N1—C11	114.43 (18)	C14—C15—C16	118.34 (17)
C10—N1—C8	116.92 (18)	C14—C15—C19	120.4 (2)
O2—C12—N2	125.56 (17)	C16—C15—C19	121.3 (2)
O2—C12—C11	120.75 (15)	C15—C16—H16	119.7
N2—C12—C11	113.64 (15)	C17—C16—C15	120.52 (18)
N1—C11—C12	114.48 (15)	C17—C16—H16	119.7
N1—C11—H11A	108.6	C16—C17—H17	119.4
N1—C11—H11B	108.6	C16—C17—C18	121.1 (2)
C12—C11—H11A	108.6	C18—C17—H17	119.4
C12—C11—H11B	108.6	C13—C18—H18	120.5
H11A—C11—H11B	107.6	C17—C18—C13	119.03 (17)
N1—C8—H8	106.9	C17—C18—H18	120.5
N1—C8—C7	110.02 (14)	C15—C19—H19A	109.5
N1—C8—C9	113.83 (16)	C15—C19—H19B	109.5
C7—C8—H8	106.9	C15—C19—H19C	109.5
C9—C8—H8	106.9	H19A—C19—H19B	109.5
C9—C8—C7	111.84 (16)	H19A—C19—H19C	109.5
O1—C7—C8	106.68 (14)	H19B—C19—H19C	109.5
O1—C7—H7	108.9	C5—C6—C7	120.80 (16)
O1—C7—C6	111.17 (15)	C5—C6—C1	117.90 (18)
C8—C7—H7	108.9	C1—C6—C7	121.29 (19)
C6—C7—C8	112.15 (14)	C6—C5—H5	119.3
C6—C7—H7	108.9	C4—C5—C6	121.38 (19)
N1—C10—H10A	109.5	C4—C5—H5	119.3
N1—C10—H10B	109.5	C5—C4—H4	120.2
N1—C10—H10C	109.5	C3—C4—C5	119.7 (2)
H10A—C10—H10B	109.5	C3—C4—H4	120.2
H10A—C10—H10C	109.5	C4—C3—H3	120.1
H10B—C10—H10C	109.5	C4—C3—C2	119.9 (2)
C8—C9—H9A	109.5	C2—C3—H3	120.1
C8—C9—H9B	109.5	C3—C2—H2A	120.0
C8—C9—H9C	109.5	C3—C2—C1	120.0 (2)
H9A—C9—H9B	109.5	C1—C2—H2A	120.0
H9A—C9—H9C	109.5	C6—C1—H1A	119.5
H9B—C9—H9C	109.5	C2—C1—C6	121.0 (2)
C14—C13—N2	116.35 (15)	C2—C1—H1A	119.5

O2—C12—C11—N1	−178.86 (18)	C10—N1—C8—C9	−48.9 (2)
O1—C7—C6—C5	45.4 (2)	C9—C8—C7—O1	−177.46 (17)
O1—C7—C6—C1	−135.88 (17)	C9—C8—C7—C6	−55.5 (2)
N2—C12—C11—N1	3.4 (3)	C13—N2—C12—O2	−0.8 (3)
N2—C13—C14—C15	−177.17 (15)	C13—N2—C12—C11	176.84 (17)
N2—C13—C18—C17	176.76 (17)	C13—C14—C15—C16	0.3 (3)
N1—C8—C7—O1	55.0 (2)	C13—C14—C15—C19	179.49 (18)
N1—C8—C7—C6	176.94 (16)	C14—C13—C18—C17	−1.0 (3)
C12—N2—C13—C14	−165.19 (17)	C14—C15—C16—C17	−1.1 (3)
C12—N2—C13—C18	17.0 (3)	C15—C16—C17—C18	0.8 (3)
C11—N1—C8—C7	−144.66 (16)	C16—C17—C18—C13	0.2 (3)
C11—N1—C8—C9	88.9 (2)	C18—C13—C14—C15	0.7 (3)
C8—N1—C11—C12	98.9 (2)	C19—C15—C16—C17	179.7 (2)
C8—C7—C6—C5	−73.9 (2)	C6—C5—C4—C3	1.1 (4)
C8—C7—C6—C1	104.8 (2)	C5—C6—C1—C2	−2.7 (3)
C7—C6—C5—C4	−179.8 (2)	C5—C4—C3—C2	−2.5 (4)
C7—C6—C1—C2	178.58 (18)	C4—C3—C2—C1	1.3 (4)
C10—N1—C11—C12	−122.2 (2)	C3—C2—C1—C6	1.3 (3)
C10—N1—C8—C7	77.5 (2)	C1—C6—C5—C4	1.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···C1ⁱ	0.97	2.83	3.720 (3)	152
C16—H16···C12ⁱⁱ	0.93	2.80	3.378 (3)	121
C2—H2A···C14ⁱⁱⁱ	0.93	2.86	3.687 (3)	149
C1—H1A···C5ⁱⁱⁱ	0.93	2.84	3.762 (3)	171
O1—H1···O2^iv	0.90 (3)	1.88 (3)	2.7663 (17)	169 (3)
N2—H2···O1	0.87 (4)	2.23 (3)	3.0184 (19)	150 (3)

Symmetry codes: (i) x−1, y, z; (ii) −x+1, y−1/2, −z+2; (iii) −x+2, y+1/2, −z+1; (iv) x+1, y, z.

Acknowledgements

BT is grateful to the Frank H. Allen International Research and Education (FAIRE) programme, provided by the Cambridge Crystallographic Data Centre (CCDC), for the opportunity to use the Cambridge Structural Database (CSD).

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