N-(4-Chloro­phen­yl)-N′-{4-[(Z)-hy­droxy(1-oxo-1,3-di­hydro-2H-inden-2-yl­idene)meth­yl]phen­yl}urea

Çelik, Í.; Atioğlu, Z.; Ordu, G.; Gezegen, H.; Akkurt, M.

doi:10.1107/S2414314618008179

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 6| June 2018| x180817

https://doi.org/10.1107/S2414314618008179

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N-(4-Chlorophenyl)-N′-{4-[(Z)-hydroxy(1-oxo-1,3-dihydro-2H-inden-2-ylidene)methyl]phenyl}urea

Ísmail Çelik,^a Zeliha Atioğlu,^b Gamze Ordu,^c Hayreddin Gezegen ^d and Mehmet Akkurt ^e ^*

^aDepartment of Physics, Faculty of Sciences, Cumhuriyet University, 58140 Sivas, Turkey, ^bİlke Education and Health Foundation, Cappadocia University, Cappadocia Vocational College, The Medical Imaging Techniques Program, 50420 Mustafapaşa, Ürgüp, Nevşehir, Turkey, ^cCumhuriyet University, Institute of Science, Department of Physics, 58140 Sivas, Turkey, ^dDepartment of Nutrition and Dietetics, Faculty of Health Sciences, Cumhuriyet University, 58140 Sivas, Turkey, and ^eDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 30 May 2018; accepted 3 June 2018; online 8 June 2018)

In the title compound, C₂₃H₁₇ClN₂O₃, the 2,3-dihydro-1H-indene ring system (r.m.s deviation = 0.004 Å) subtends dihedral angles of 81.12 (16) and 7.56 (14)° with the chlorophenyl and benzene rings, respectively. The molecular conformation features an intramolecular O—H⋯O hydrogen bond, forming an S(6) ring motif. In the crystal, molecules are linked by N—H⋯O hydrogen bonds generating [100] chains featuring R₁²(6) loops. Weak aromatic π–π stacking [centroid–centroid distance = 3.656 (2) Å] is also oberved.

Keywords: crystal structure; 2,3-dihydro-1H-indene ring system; N—H⋯O hydrogen bonds; π–π stacking interaction.

CCDC reference: 1846924

Structure description

Organic compounds containing the phenylurea unit are known to be valuable in terms of biological activity (Jiang et al., 2016 ; Sikka et al., 2015 ). As part of our studies in this area, we new report the crystal structure (Fig. 1) of the title compound (Gezegen et al., 2017 ).

Figure 1
The molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.

The 2,3-dihydro-1H-indene ring system (C15–C23) is essentially planar (r.m.s deviation = 0.004 Å), and is inclined at dihedral angles of 81.12 (16) and 7.56 (14)° with the chlorophenyl (C1–C6) and benzene (C8–C13) rings, respectively. The N—(C=O)—N plane involving the urea group is oriented at dihedral angles of 54.36 (17), 40.01 (15) and 56.15 (14)°, respectively, with the chlorophenyl ring, the benzene ring and the 2,3-dihydro-1H-indene ring system, respectively. The bond lengths and the bond angles of the title structure are within their normal ranges and are comparable to related structures (e.g. Yassine et al., 2015 ; Mague et al., 2015 ). The molecular conformation of the title compound is consolidated by an intramolecular O—H⋯O hydrogen bond, forming an S(6) ring motif (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O3	0.89 (5)	1.71 (5)	2.543 (4)	154 (5)
N1—H1N⋯O1ⁱ	0.87 (6)	2.03 (5)	2.853 (4)	158 (4)
N2—H2N⋯O1ⁱ	0.81 (5)	2.18 (5)	2.904 (4)	148 (4)
Symmetry code: (i) x+1, y, z.

In the crystal, adjacent molecules are linked by N—H⋯O hydrogen bonds (Fig. 2), generating infinite [100] chains incorporating $[R_{1}^{2}]$ (6) loops. In addition, weak aromatic π–π stacking interactions are observed [Cg1⋯Cg4ⁱ = 3.656 (2) Å; Cg1 and Cg4 are the centroids of the five- and six-membered rings (C15–C17/C22/C23 and C17–C22) of the 2,3-dihydro-1H-indene ring system, respectively; symmetry code: (i), x + 1, y, z].

Figure 2
A view along the c axis of the crystal packing of the title compound. H bonds are shown as dashed lines and H atoms not involved in these interactions have been omitted for clarity.

Synthesis and crystallization

For the sysnthesis of the title compound, see: Gezegen et al., 2017. The crystals were grown from a DMSO solution by slow evaporation.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₃H₁₇ClN₂O₃
M_r	404.84
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	4.6032 (4), 6.9338 (8), 15.4421 (15)
α, β, γ (°)	89.811 (4), 87.510 (3), 70.866 (3)
V (Å³)	465.18 (8)
Z	1
Radiation type	Mo Kα
μ (mm⁻¹)	0.23
Crystal size (mm)	0.16 × 0.14 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003 )
T_min, T_max	0.680, 0.744
No. of measured, independent and observed [I > 2σ(I)] reflections	16956, 4386, 3678
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.102, 1.11
No. of reflections	4386
No. of parameters	276
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.19
Absolute structure	Flack (1983 )
Absolute structure parameter	0.05 (10)
Computer programs: APEX2 and SAINT (Bruker, 2007 ), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1846924

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314618008179/hb4236sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618008179/hb4236Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

N-(4-Chlorophenyl)-N'-{4-[(Z)-hydroxy(1-oxo-1,3-dihydro-2H-inden-2-ylidene)methyl]phenyl}urea top

Crystal data top

C₂₃H₁₇ClN₂O₃	Z = 1
M_r = 404.84	F(000) = 210
Triclinic, P1	D_x = 1.445 Mg m⁻³
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.6032 (4) Å	Cell parameters from 9876 reflections
b = 6.9338 (8) Å	θ = 3.1–28.3°
c = 15.4421 (15) Å	µ = 0.23 mm⁻¹
α = 89.811 (4)°	T = 296 K
β = 87.510 (3)°	Block, yellow
γ = 70.866 (3)°	0.16 × 0.14 × 0.10 mm
V = 465.18 (8) Å³

Data collection top

Bruker APEXII CCD diffractometer	3678 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.039
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	θ_max = 28.4°, θ_min = 3.1°
T_min = 0.680, T_max = 0.744	h = −6→5
16956 measured reflections	k = −9→9
4386 independent reflections	l = −20→20

Refinement top

Refinement on F²	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0294P)² + 0.143P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.041	(Δ/σ)_max < 0.001
wR(F²) = 0.102	Δρ_max = 0.22 e Å⁻³
S = 1.11	Δρ_min = −0.19 e Å⁻³
4386 reflections	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
276 parameters	Extinction coefficient: 0.128 (16)
3 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.05 (10)
Hydrogen site location: mixed

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. The H-atoms of the OH and NH groups were freely refined [O—H = 0.89 (5) Å, N—H = 0.87 (6) and 0.81 (5) Å]. The C-bound H-atoms were placed at calculated positions, with C—H = 0.93 - 0.97 Å, and refined as riding on their carrier C-atom, with U_iso(H) = 1.2U_eq(C).

Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C1	0.5548 (8)	0.8679 (5)	0.1780 (2)	0.0429 (8)
H1	0.5605	0.7338	0.1700	0.051*
C2	0.3778 (9)	1.0201 (6)	0.1255 (3)	0.0515 (9)
H2	0.2630	0.9891	0.0828	0.062*
C3	0.3741 (9)	1.2159 (5)	0.1371 (2)	0.0515 (10)
C4	0.5390 (10)	1.2646 (5)	0.1997 (3)	0.0576 (11)
H4	0.5330	1.3990	0.2070	0.069*
C5	0.7158 (9)	1.1128 (5)	0.2523 (2)	0.0491 (9)
H5	0.8301	1.1452	0.2948	0.059*
C6	0.7226 (6)	0.9138 (4)	0.2420 (2)	0.0335 (6)
C7	0.8067 (6)	0.6309 (4)	0.3429 (2)	0.0310 (6)
C8	0.9592 (6)	0.3525 (4)	0.4474 (2)	0.0330 (7)
C9	0.7154 (7)	0.4119 (4)	0.5074 (2)	0.0387 (7)
H9	0.5857	0.5468	0.5092	0.046*
C10	0.6618 (7)	0.2726 (4)	0.5648 (2)	0.0389 (7)
H10	0.4958	0.3155	0.6048	0.047*
C11	0.8519 (7)	0.0691 (4)	0.5639 (2)	0.0333 (6)
C12	1.0962 (7)	0.0118 (5)	0.5029 (2)	0.0409 (8)
H12	1.2259	−0.1231	0.5004	0.049*
C13	1.1506 (8)	0.1517 (5)	0.4456 (2)	0.0425 (8)
H13	1.3170	0.1102	0.4057	0.051*
C14	0.8025 (7)	−0.0849 (4)	0.6237 (2)	0.0361 (7)
C15	0.5883 (7)	−0.0554 (5)	0.6905 (2)	0.0374 (7)
C16	0.3507 (7)	0.1363 (5)	0.7274 (2)	0.0384 (7)
H16A	0.4470	0.2324	0.7473	0.046*
H16B	0.2022	0.2020	0.6848	0.046*
C17	0.2012 (8)	0.0579 (5)	0.8020 (2)	0.0403 (7)
C18	−0.0360 (9)	0.1673 (6)	0.8598 (2)	0.0526 (9)
H18	−0.1205	0.3085	0.8565	0.063*
C19	−0.1423 (10)	0.0608 (7)	0.9221 (3)	0.0630 (11)
H19	−0.3000	0.1321	0.9612	0.076*
C20	−0.0203 (10)	−0.1495 (7)	0.9279 (3)	0.0630 (11)
H20	−0.0976	−0.2170	0.9705	0.076*
C21	0.2155 (10)	−0.2602 (6)	0.8710 (3)	0.0560 (10)
H21	0.2989	−0.4015	0.8746	0.067*
C22	0.3231 (8)	−0.1528 (5)	0.8084 (2)	0.0423 (8)
C23	0.5676 (8)	−0.2277 (5)	0.7414 (2)	0.0424 (8)
Cl1	0.1535 (3)	1.40938 (18)	0.07167 (9)	0.0914 (5)
N1	0.9113 (6)	0.7605 (4)	0.29524 (19)	0.0409 (7)
N2	1.0222 (6)	0.4939 (4)	0.38897 (19)	0.0394 (7)
O1	0.5366 (5)	0.6352 (4)	0.34347 (17)	0.0434 (6)
O2	0.9969 (6)	−0.2732 (3)	0.60665 (19)	0.0527 (7)
O3	0.7349 (7)	−0.4103 (3)	0.72891 (19)	0.0589 (7)
H2N	1.202 (10)	0.487 (6)	0.383 (3)	0.052 (11)*
H1N	1.100 (12)	0.752 (7)	0.303 (3)	0.064 (13)*
H2O	0.955 (12)	−0.353 (8)	0.647 (3)	0.083 (16)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1031 (10)	0.0650 (7)	0.0752 (8)	0.0144 (6)	−0.0048 (7)	0.0354 (6)
O1	0.0243 (11)	0.0494 (13)	0.0607 (14)	−0.0172 (10)	−0.0089 (9)	0.0211 (11)
O2	0.0614 (16)	0.0255 (11)	0.0601 (16)	−0.0012 (10)	0.0120 (12)	0.0047 (11)
O3	0.0753 (19)	0.0300 (12)	0.0624 (17)	−0.0063 (12)	0.0066 (14)	0.0116 (11)
N1	0.0239 (13)	0.0464 (15)	0.0561 (18)	−0.0162 (11)	−0.0072 (12)	0.0212 (13)
N2	0.0199 (13)	0.0440 (15)	0.0556 (17)	−0.0122 (11)	−0.0050 (11)	0.0180 (12)
C1	0.0452 (19)	0.0348 (16)	0.049 (2)	−0.0133 (14)	−0.0077 (15)	0.0064 (14)
C2	0.055 (2)	0.050 (2)	0.047 (2)	−0.0142 (17)	−0.0103 (17)	0.0118 (17)
C3	0.053 (2)	0.0430 (18)	0.044 (2)	0.0024 (16)	0.0071 (16)	0.0151 (15)
C4	0.084 (3)	0.0302 (17)	0.056 (2)	−0.0173 (18)	0.005 (2)	0.0048 (15)
C5	0.063 (2)	0.0416 (18)	0.048 (2)	−0.0242 (16)	−0.0075 (17)	0.0037 (15)
C6	0.0261 (14)	0.0352 (15)	0.0399 (16)	−0.0111 (11)	0.0006 (12)	0.0100 (12)
C7	0.0213 (14)	0.0319 (14)	0.0403 (16)	−0.0097 (11)	−0.0011 (11)	0.0053 (12)
C8	0.0268 (15)	0.0333 (15)	0.0403 (17)	−0.0109 (12)	−0.0079 (12)	0.0090 (12)
C9	0.0355 (17)	0.0269 (14)	0.0485 (19)	−0.0035 (12)	0.0002 (14)	0.0059 (13)
C10	0.0357 (17)	0.0318 (16)	0.0437 (19)	−0.0044 (13)	0.0048 (13)	0.0039 (13)
C11	0.0345 (15)	0.0283 (14)	0.0366 (16)	−0.0091 (11)	−0.0065 (12)	0.0034 (12)
C12	0.0406 (18)	0.0268 (15)	0.048 (2)	−0.0009 (13)	−0.0018 (14)	0.0046 (14)
C13	0.0330 (17)	0.0430 (17)	0.0455 (19)	−0.0051 (13)	0.0036 (14)	0.0067 (14)
C14	0.0390 (17)	0.0256 (14)	0.0403 (16)	−0.0056 (12)	−0.0057 (13)	0.0033 (12)
C15	0.0420 (17)	0.0308 (14)	0.0383 (16)	−0.0100 (12)	−0.0059 (13)	0.0090 (12)
C16	0.0404 (17)	0.0332 (15)	0.0377 (17)	−0.0060 (12)	−0.0061 (13)	0.0074 (12)
C17	0.0397 (18)	0.0443 (18)	0.0345 (17)	−0.0100 (14)	−0.0056 (13)	0.0082 (14)
C18	0.052 (2)	0.053 (2)	0.045 (2)	−0.0068 (17)	−0.0007 (16)	0.0094 (17)
C19	0.056 (2)	0.075 (3)	0.047 (2)	−0.009 (2)	0.0057 (18)	0.014 (2)
C20	0.060 (3)	0.073 (3)	0.052 (2)	−0.018 (2)	0.0037 (19)	0.024 (2)
C21	0.059 (2)	0.052 (2)	0.055 (2)	−0.0158 (18)	−0.0078 (18)	0.0229 (18)
C22	0.0459 (19)	0.0421 (17)	0.0383 (18)	−0.0126 (14)	−0.0092 (14)	0.0112 (14)
C23	0.0503 (19)	0.0352 (16)	0.0406 (18)	−0.0120 (14)	−0.0072 (14)	0.0078 (13)

Geometric parameters (Å, º) top

Cl1—C3	1.743 (4)	C15—C16	1.512 (5)
O1—C7	1.234 (4)	C15—C23	1.455 (5)
O2—C14	1.338 (3)	C16—C17	1.506 (5)
O3—C23	1.258 (4)	C17—C18	1.393 (5)
N1—C6	1.418 (4)	C17—C22	1.388 (5)
N1—C7	1.353 (4)	C18—C19	1.379 (6)
N2—C7	1.353 (4)	C19—C20	1.384 (6)
N2—C8	1.420 (4)	C20—C21	1.384 (7)
O2—H2O	0.89 (5)	C21—C22	1.389 (6)
C1—C2	1.387 (5)	C22—C23	1.458 (5)
C1—C6	1.380 (5)	C1—H1	0.9300
N1—H1N	0.87 (6)	C2—H2	0.9300
N2—H2N	0.81 (5)	C4—H4	0.9300
C2—C3	1.365 (5)	C5—H5	0.9300
C3—C4	1.363 (6)	C9—H9	0.9300
C4—C5	1.386 (5)	C10—H10	0.9300
C5—C6	1.380 (4)	C12—H12	0.9300
C8—C9	1.377 (4)	C13—H13	0.9300
C8—C13	1.382 (4)	C16—H16A	0.9700
C9—C10	1.382 (4)	C16—H16B	0.9700
C10—C11	1.395 (4)	C18—H18	0.9300
C11—C14	1.476 (4)	C19—H19	0.9300
C11—C12	1.388 (5)	C20—H20	0.9300
C12—C13	1.386 (5)	C21—H21	0.9300
C14—C15	1.363 (5)

C6—N1—C7	123.5 (3)	C17—C18—C19	118.3 (4)
C7—N2—C8	124.3 (3)	C18—C19—C20	121.7 (4)
C14—O2—H2O	106 (3)	C19—C20—C21	120.7 (4)
C2—C1—C6	120.5 (3)	C20—C21—C22	117.6 (4)
C7—N1—H1N	115 (3)	C17—C22—C21	122.0 (3)
C6—N1—H1N	121 (3)	C17—C22—C23	108.4 (3)
C1—C2—C3	119.2 (4)	C21—C22—C23	129.6 (3)
C8—N2—H2N	116 (3)	O3—C23—C22	126.3 (3)
C7—N2—H2N	120 (3)	C15—C23—C22	108.7 (3)
Cl1—C3—C4	118.8 (3)	O3—C23—C15	125.0 (3)
C2—C3—C4	121.2 (3)	C2—C1—H1	120.00
Cl1—C3—C2	120.0 (3)	C6—C1—H1	120.00
C3—C4—C5	119.6 (3)	C1—C2—H2	120.00
C4—C5—C6	120.2 (3)	C3—C2—H2	120.00
N1—C6—C1	121.7 (3)	C3—C4—H4	120.00
C1—C6—C5	119.1 (3)	C5—C4—H4	120.00
N1—C6—C5	119.1 (3)	C4—C5—H5	120.00
O1—C7—N2	122.5 (3)	C6—C5—H5	120.00
O1—C7—N1	122.6 (3)	C8—C9—H9	120.00
N1—C7—N2	114.9 (3)	C10—C9—H9	120.00
C9—C8—C13	119.1 (3)	C9—C10—H10	119.00
N2—C8—C9	121.5 (2)	C11—C10—H10	119.00
N2—C8—C13	119.4 (3)	C11—C12—H12	119.00
C8—C9—C10	120.5 (3)	C13—C12—H12	119.00
C9—C10—C11	121.3 (3)	C8—C13—H13	120.00
C10—C11—C14	123.1 (3)	C12—C13—H13	120.00
C12—C11—C14	119.5 (3)	C15—C16—H16A	111.00
C10—C11—C12	117.4 (3)	C15—C16—H16B	111.00
C11—C12—C13	121.3 (3)	C17—C16—H16A	111.00
C8—C13—C12	120.4 (3)	C17—C16—H16B	111.00
O2—C14—C11	112.9 (3)	H16A—C16—H16B	109.00
C11—C14—C15	127.9 (3)	C17—C18—H18	121.00
O2—C14—C15	119.3 (3)	C19—C18—H18	121.00
C14—C15—C23	120.2 (3)	C18—C19—H19	119.00
C14—C15—C16	131.5 (3)	C20—C19—H19	119.00
C16—C15—C23	108.2 (3)	C19—C20—H20	120.00
C15—C16—C17	103.0 (3)	C21—C20—H20	120.00
C16—C17—C18	128.7 (3)	C20—C21—H21	121.00
C18—C17—C22	119.7 (3)	C22—C21—H21	121.00
C16—C17—C22	111.6 (3)

C7—N1—C6—C1	−55.6 (4)	C12—C11—C14—C15	175.9 (3)
C7—N1—C6—C5	126.9 (3)	C11—C12—C13—C8	−0.7 (5)
C6—N1—C7—O1	0.4 (5)	O2—C14—C15—C16	177.1 (3)
C6—N1—C7—N2	179.4 (3)	O2—C14—C15—C23	−1.3 (5)
C7—N2—C8—C9	−46.4 (4)	C11—C14—C15—C16	−3.4 (6)
C7—N2—C8—C13	135.2 (3)	C11—C14—C15—C23	178.2 (3)
C8—N2—C7—N1	175.9 (3)	C14—C15—C16—C17	−178.1 (4)
C8—N2—C7—O1	−5.1 (5)	C23—C15—C16—C17	0.5 (4)
C6—C1—C2—C3	0.8 (6)	C14—C15—C23—O3	−0.5 (6)
C2—C1—C6—N1	−178.5 (3)	C14—C15—C23—C22	179.5 (3)
C2—C1—C6—C5	−1.0 (5)	C16—C15—C23—O3	−179.2 (3)
C1—C2—C3—C4	−0.5 (6)	C16—C15—C23—C22	0.8 (4)
C1—C2—C3—Cl1	179.9 (3)	C15—C16—C17—C18	−179.9 (4)
Cl1—C3—C4—C5	−180.0 (3)	C15—C16—C17—C22	−1.6 (4)
C2—C3—C4—C5	0.5 (7)	C16—C17—C18—C19	178.2 (4)
C3—C4—C5—C6	−0.7 (6)	C22—C17—C18—C19	0.0 (6)
C4—C5—C6—N1	178.5 (3)	C16—C17—C22—C21	−178.3 (4)
C4—C5—C6—C1	0.9 (5)	C16—C17—C22—C23	2.2 (4)
N2—C8—C9—C10	−178.7 (3)	C18—C17—C22—C21	0.2 (6)
C13—C8—C9—C10	−0.3 (5)	C18—C17—C22—C23	−179.4 (3)
N2—C8—C13—C12	179.0 (3)	C17—C18—C19—C20	−0.3 (7)
C9—C8—C13—C12	0.6 (5)	C18—C19—C20—C21	0.3 (7)
C8—C9—C10—C11	0.1 (5)	C19—C20—C21—C22	−0.1 (7)
C9—C10—C11—C12	−0.3 (5)	C20—C21—C22—C17	−0.1 (6)
C9—C10—C11—C14	−179.7 (3)	C20—C21—C22—C23	179.4 (4)
C10—C11—C12—C13	0.5 (5)	C17—C22—C23—O3	178.1 (4)
C14—C11—C12—C13	−180.0 (3)	C17—C22—C23—C15	−1.8 (4)
C10—C11—C14—O2	174.9 (3)	C21—C22—C23—O3	−1.4 (7)
C10—C11—C14—C15	−4.7 (5)	C21—C22—C23—C15	178.7 (4)
C12—C11—C14—O2	−4.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O3	0.89 (5)	1.71 (5)	2.543 (4)	154 (5)
N1—H1N···O1ⁱ	0.87 (6)	2.03 (5)	2.853 (4)	158 (4)
N2—H2N···O1ⁱ	0.81 (5)	2.18 (5)	2.904 (4)	148 (4)

Symmetry code: (i) x+1, y, z.

Acknowledgements

The authors are indebted to the X-ray laboratory of Sinop University Scientific and Technological Applied and Research Center, Sinop, Turkey, for use of the X-ray diffractometer.

Funding information

This work was supported by the Scientific Research Project Fund of Cumhuriyet University under the project number F-585. The authors are indebted to the Technical Research Council of Turkey (grant TUBİTAK-114Z634) for the financial support of the synthesis of the compound reported in this work.

References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gezegen, H., Hepokur, C., Tutar, U. & Ceylan, M. (2017). Chem. Biodivers. 14, e1700223. Web of Science CrossRef Google Scholar
Jiang, N., Bu, Y., Wang, Y., Nie, M., Zhang, D. & Zhai, X. (2016). Molecules, 21, 1572–1583. Web of Science CrossRef Google Scholar
Mague, J. T., Mohamed, S. K., Akkurt, M., Omran, O. A. & Albayati, M. R. (2015). Acta Cryst. E71, o88–o89. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sikka, P., Sahu, J. K., Mishra, A. K. & Hashim, S. R. (2015). Med. Chem. 5, 479–483. CrossRef Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yassine, H., Khouili, M., El Ammari, L., Saadi, M. & Ketatni, E. M. (2015). Acta Cryst. E71, o297–o298. Web of Science CrossRef IUCr Journals Google Scholar

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