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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 11| November 2016| x161849
https://doi.org/10.1107/S2414314616018496

1-Benzyl-3-hy­dr­oxy-4-phenyl-2,3,4,5-tetra­hydro-1H-1,5-benzodiazepin-2-one

CROSSMARK_Color_square_no_text.svg
Mohammed Rida,a* Youness El Bakri,a Mohamadou Lamine Doumbia,b El Mokhtar Essassia and Joel T. Maguec

aLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Mohammed V University, Rabat, Morocco, bUFR–Environnement, UNIV Jean Lorougnon Guédé, BP 150, Daloa, Ivory Coast, and cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: rida.m.b@hotmail.com

Edited by S. Bernès, Benemérita Universidad Autónoma de Puebla, México (Received 7 November 2016; accepted 18 November 2016; online 22 November 2016)

The title compound, C22H20N2O2, forms chains in the [001] direction in the monoclinic crystal, through N—H⋯O hydrogen bonding. The chains are associated via O—H⋯π(ring) and C—H⋯π(ring) inter­actions involving one phenyl ring and the benzene ring of the benzodiazepine as acceptors. For these inter­molecular contacts, the H⋯π separations are close to 2.7 Å.

CCDC reference: 1517939

Similar articles
3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

1,5-Benzodiazepine derivatives have been used as therapeutics for viral infection, cardiovascular disorder (Jacob et al., 2011[Jacob, R. G., Radatz, C. S., Rodrigues, M. B., Alves, D., Perin, G., Lenardão, E. J. & Savegnago, L. (2011). Heteroat. Chem. 22, 180-185.]; Maleki et al., 2014[Maleki, A., Ghamari, N. & Kamalzare, M. (2014). RSC Adv. 4, 9416-9423.]) and as anti­microbial agents against some microorganisms (An et al., 2016[An, Y.-S., Hao, Z.-F., Zhang, X.-J. & Wang, L.-Z. (2016). Chem. Biol. Drug Des. 88, 110-121.]). They are active against peptide hormones and potassium blockers (Claremon et al., 1996[Claremon, D. A., Liverton, N., Selnick, H. G. & Smith, G. R. (1996). PCT Int. Appl. WO 9640653.1074.]). They are also employed as inter­mediates for the synthesis of several heterocyclic compounds (Minnih et al., 2014[Minnih, M. S., Kandri Rodi, Y. & Essassi, E. M. (2014). J. Mar. Chim. Heterocycl. 13, 1-24.]).

As part of our studies in this area, we now describe the synthesis and structure of the title compound. In the mol­ecular structure, the dihedral angle between the C1–C6 and C10–C15 rings is 42.57 (5)°, while the angle between the former and the C17–C22 ring is 81.24 (4)°. A puckering analysis of the seven-membered diazepine ring yielded parameters q2 = 0.992 (1) Å, q3 = 0.183 (1) Å, φ2 = 11.81 (6)° and φ3 = 98.4 (3)°, for a total puckering amplitude of 1.009 (1) Å. There is likely an intra­molecular O1—H1A⋯O2 hydrogen bond forming an S(5) ring (Fig. 1[link] and Table 1[link]), but because of the acute O1—H1A⋯O2 angle of 115 (1)° and the rather long H1A⋯O2 separation of 2.166 (17) Å, it should be considered as a weak interaction.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 phenyl rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1A⋯O2 0.878 (18) 2.166 (17) 2.6601 (12) 115.1 (14)
N1—H1⋯O2i 0.918 (15) 2.045 (16) 2.9531 (12) 169.5 (13)
O1—H1A⋯Cg2ii 0.878 (18) 2.719 (18) 3.4636 (10) 143.4 (16)
C13—H13⋯Cg1iii 0.984 (15) 2.699 (15) 3.3283 (14) 122.1 (10)
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) x+1, y, z.
[Figure 1]
Figure 1
The title mol­ecule, showing the labelling scheme and 50% probability ellipsoids for non-H atoms. The intra­molecular hydrogen bond is shown as a dotted line.

In the crystal, inter­molecular N1—H1⋯O2i hydrogen bonds [symmetry code: (i) x, −y + [{1\over 2}], z − [{1\over 2}]; see Table 1[link] and Fig. 2[link]] form chains parallel to [001]. The cohesion is reinforced by O1—H1A⋯π(ring) inter­actions involving the C10–C15 ring at x, −y + [{1\over 2}], z + [{1\over 2}] (see Table 1[link]). The chains are further associated through contact C13—H13⋯π(ring), involving the C1–C6 benzene ring of the benzodiazepine as acceptor, with symmetry code (1 + x, y, z) (Fig. 3[link] and Table 1[link]).

[Figure 2]
Figure 2
Packing viewed along the a axis, with the N—H⋯O hydrogen bonds shown as dotted lines.
[Figure 3]
Figure 3
A portion of one chain, showing the N—H⋯O (blue dotted line) and O—H⋯π(ring) (orange dotted line) inter­actions on the left and one of the C—H⋯π(ring) inter­actions (black dotted line) between the chains.

Synthesis and crystallization

To a solution of 3-hy­droxy-4-phenyl-4,5-di­hydro-1H-1,5-benzodiazepin-2(3H)-one (1 g, 3.94 mmol) in di­methyl­formamide (20 ml) were added benzyl chloride (0.95 g, 7.88 mmol), potassium carbonate (1 g, 7.4 mmol) and a catalytic amount of tetra-n-butyl­ammonium bromide. The mixture was stirred at room temperature for 48 h. The solution was filtered and the solvent removed under reduced pressure. The residue was recrystallized from ethanol to afford the title compound as colourless crystals.

Refinement

Crystal and refinement details appear in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C22H20N2O2
Mr 344.40
Crystal system, space group Monoclinic, P21/c
Temperature (K) 150
a, b, c (Å) 8.9169 (2), 17.6360 (5), 11.7937 (3)
β (°) 109.199 (1)
V (Å3) 1751.51 (8)
Z 4
Radiation type Cu Kα
μ (mm−1) 0.67
Crystal size (mm) 0.20 × 0.18 × 0.17
 
Data collection
Diffractometer Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction Multi-scan (SADABS; Bruker, 2016[Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.82, 0.89
No. of measured, independent and observed [I > 2σ(I)] reflections 37686, 3413, 3177
Rint 0.037
(sin θ/λ)max (Å−1) 0.617
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.092, 1.04
No. of reflections 3413
No. of parameters 316
H-atom treatment All H-atom parameters refined
Δρmax, Δρmin (e Å−3) 0.26, −0.17
Computer programs: APEX3 and SAINT (Bruker, 2016[Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2014 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]) and DIAMOND (Brandenburg & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]).

Structural data

CCDC reference: 1517939

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314616018496/bh4019sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616018496/bh4019Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314616018496/bh4019Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2414314616018496/bh4019Isup4.cml

checkCIF report


Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).

(3S,4S)-1-Benzyl-3-hydroxy-4-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one top
Crystal data top
C22H20N2O2F(000) = 728
Mr = 344.40Dx = 1.306 Mg m−3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 8.9169 (2) ÅCell parameters from 9851 reflections
b = 17.6360 (5) Åθ = 2.5–71.9°
c = 11.7937 (3) ŵ = 0.67 mm−1
β = 109.199 (1)°T = 150 K
V = 1751.51 (8) Å3Block, colourless
Z = 40.20 × 0.18 × 0.17 mm
Data collection top
Bruker D8 VENTURE PHOTON 100 CMOS
diffractometer		3413 independent reflections
Radiation source: INCOATEC IµS micro-focus source3177 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.037
Detector resolution: 10.4167 pixels mm-1θmax = 72.1°, θmin = 4.7°
ω scansh = −10→10
Absorption correction: multi-scan
(SADABS; Bruker, 2016)		k = −21→19
Tmin = 0.82, Tmax = 0.89l = −11→14
37686 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033All H-atom parameters refined
wR(F2) = 0.092 w = 1/[σ2(Fo2) + (0.0477P)2 + 0.4657P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3413 reflectionsΔρmax = 0.26 e Å−3
316 parametersΔρmin = −0.17 e Å−3
0 restraintsExtinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0054 (4)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.81338 (9)0.35773 (5)0.75652 (7)0.0327 (2)
H1A0.799 (2)0.3328 (10)0.8165 (16)0.056 (5)*
O20.55542 (10)0.32787 (5)0.81467 (7)0.0331 (2)
N10.50274 (11)0.27320 (5)0.49763 (8)0.0276 (2)
H10.5059 (17)0.2401 (9)0.4383 (13)0.041 (4)*
N20.38729 (11)0.37324 (5)0.63890 (8)0.0270 (2)
C10.35548 (12)0.38753 (6)0.51424 (9)0.0269 (2)
C20.25775 (14)0.44790 (7)0.45973 (11)0.0342 (3)
H20.2182 (16)0.4807 (8)0.5110 (12)0.035 (3)*
C30.21116 (15)0.45795 (7)0.33638 (12)0.0409 (3)
H30.1424 (18)0.4987 (9)0.2997 (14)0.048 (4)*
C40.26397 (15)0.40804 (8)0.26721 (11)0.0401 (3)
H40.2317 (17)0.4149 (9)0.1785 (14)0.046 (4)*
C50.36499 (14)0.34917 (7)0.32094 (10)0.0337 (3)
H50.4051 (17)0.3133 (9)0.2716 (13)0.042 (4)*
C60.41277 (12)0.33759 (6)0.44519 (9)0.0266 (2)
C70.66430 (13)0.28233 (6)0.58467 (9)0.0260 (2)
H70.6833 (14)0.2386 (7)0.6399 (11)0.024 (3)*
C80.66829 (12)0.35285 (6)0.66149 (9)0.0254 (2)
H80.6564 (14)0.3996 (7)0.6109 (10)0.022 (3)*
C90.53102 (13)0.34961 (6)0.71094 (9)0.0258 (2)
C100.79289 (13)0.28501 (6)0.52625 (10)0.0273 (2)
C110.78566 (14)0.33802 (7)0.43669 (10)0.0316 (3)
H110.6959 (17)0.3749 (9)0.4111 (12)0.041 (4)*
C120.89886 (14)0.33828 (7)0.37932 (10)0.0353 (3)
H120.8903 (17)0.3761 (9)0.3147 (13)0.043 (4)*
C131.02100 (14)0.28571 (7)0.41097 (11)0.0360 (3)
H131.0997 (18)0.2848 (8)0.3689 (13)0.044 (4)*
C141.03167 (14)0.23378 (7)0.50135 (11)0.0348 (3)
H141.1170 (17)0.1974 (9)0.5247 (12)0.039 (4)*
C150.91782 (13)0.23347 (7)0.55894 (10)0.0305 (3)
H150.9247 (15)0.1973 (8)0.6224 (12)0.031 (3)*
C160.25895 (14)0.37887 (7)0.69117 (11)0.0316 (3)
H16A0.2569 (16)0.3305 (8)0.7363 (12)0.037 (4)*
H16B0.1580 (17)0.3833 (8)0.6241 (12)0.038 (4)*
C170.27738 (12)0.44490 (6)0.77704 (9)0.0279 (2)
C180.38682 (14)0.50269 (6)0.78820 (10)0.0318 (3)
H180.4578 (17)0.5021 (8)0.7375 (13)0.043 (4)*
C190.40120 (15)0.56106 (7)0.87057 (11)0.0365 (3)
H190.4842 (18)0.6010 (9)0.8800 (13)0.048 (4)*
C200.30586 (16)0.56241 (7)0.94175 (11)0.0391 (3)
H200.3194 (18)0.6011 (9)1.0033 (14)0.048 (4)*
C210.19464 (16)0.50561 (8)0.92981 (12)0.0422 (3)
H210.126 (2)0.5057 (9)0.9811 (15)0.058 (5)*
C220.18007 (14)0.44702 (7)0.84832 (11)0.0357 (3)
H220.1029 (17)0.4053 (8)0.8402 (12)0.040 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0286 (4)0.0352 (4)0.0286 (4)−0.0020 (3)0.0017 (3)0.0018 (3)
O20.0426 (5)0.0318 (4)0.0265 (4)0.0005 (3)0.0132 (3)0.0030 (3)
N10.0271 (5)0.0266 (5)0.0297 (5)−0.0033 (4)0.0101 (4)−0.0053 (4)
N20.0281 (5)0.0262 (5)0.0275 (5)−0.0009 (3)0.0103 (4)−0.0034 (4)
C10.0251 (5)0.0259 (5)0.0274 (5)−0.0045 (4)0.0056 (4)−0.0005 (4)
C20.0291 (6)0.0264 (6)0.0416 (6)−0.0026 (4)0.0042 (5)−0.0006 (5)
C30.0327 (6)0.0331 (6)0.0454 (7)−0.0059 (5)−0.0027 (5)0.0110 (5)
C40.0387 (7)0.0455 (7)0.0299 (6)−0.0135 (5)0.0029 (5)0.0078 (5)
C50.0318 (6)0.0412 (7)0.0279 (6)−0.0106 (5)0.0093 (5)−0.0004 (5)
C60.0233 (5)0.0287 (5)0.0271 (5)−0.0069 (4)0.0072 (4)−0.0006 (4)
C70.0273 (5)0.0241 (5)0.0270 (5)−0.0006 (4)0.0097 (4)0.0012 (4)
C80.0259 (5)0.0238 (5)0.0242 (5)−0.0014 (4)0.0052 (4)0.0011 (4)
C90.0327 (6)0.0198 (5)0.0251 (5)−0.0013 (4)0.0096 (4)−0.0021 (4)
C100.0262 (5)0.0284 (5)0.0274 (5)−0.0045 (4)0.0089 (4)−0.0038 (4)
C110.0288 (6)0.0341 (6)0.0321 (6)−0.0040 (5)0.0103 (5)0.0014 (5)
C120.0317 (6)0.0440 (7)0.0304 (6)−0.0114 (5)0.0105 (5)−0.0020 (5)
C130.0269 (6)0.0492 (7)0.0336 (6)−0.0122 (5)0.0124 (5)−0.0131 (5)
C140.0254 (6)0.0397 (7)0.0378 (6)−0.0018 (5)0.0084 (5)−0.0107 (5)
C150.0292 (6)0.0302 (6)0.0308 (6)−0.0024 (4)0.0081 (5)−0.0038 (4)
C160.0292 (6)0.0324 (6)0.0356 (6)−0.0045 (4)0.0143 (5)−0.0058 (5)
C170.0254 (5)0.0304 (6)0.0269 (5)0.0028 (4)0.0074 (4)−0.0006 (4)
C180.0326 (6)0.0301 (6)0.0339 (6)−0.0002 (4)0.0128 (5)−0.0028 (4)
C190.0385 (7)0.0307 (6)0.0367 (6)0.0017 (5)0.0072 (5)−0.0038 (5)
C200.0444 (7)0.0384 (7)0.0298 (6)0.0123 (5)0.0058 (5)−0.0057 (5)
C210.0414 (7)0.0540 (8)0.0355 (6)0.0113 (6)0.0184 (6)−0.0020 (6)
C220.0296 (6)0.0435 (7)0.0361 (6)0.0014 (5)0.0136 (5)−0.0005 (5)
Geometric parameters (Å, º) top
O1—C81.4084 (13)C10—C111.3961 (16)
O1—H1A0.878 (18)C11—C121.3877 (16)
O2—C91.2312 (13)C11—H110.998 (15)
N1—C61.4104 (14)C12—C131.3849 (18)
N1—C71.4774 (14)C12—H120.997 (15)
N1—H10.918 (15)C13—C141.3846 (19)
N2—C91.3498 (14)C13—H130.984 (15)
N2—C11.4253 (14)C14—C151.3947 (16)
N2—C161.4708 (14)C14—H140.963 (15)
C1—C21.3920 (16)C15—H150.971 (14)
C1—C61.4047 (15)C16—C171.5164 (15)
C2—C31.3866 (18)C16—H16A1.009 (15)
C2—H20.983 (14)C16—H16B0.987 (14)
C3—C41.384 (2)C17—C181.3871 (16)
C3—H30.951 (16)C17—C221.3931 (16)
C4—C51.3840 (18)C18—C191.3921 (16)
C4—H40.997 (15)C18—H181.003 (15)
C5—C61.4000 (15)C19—C201.3774 (18)
C5—H51.002 (15)C19—H191.001 (16)
C7—C101.5203 (15)C20—C211.384 (2)
C7—C81.5321 (14)C20—H200.974 (16)
C7—H70.988 (13)C21—C221.3878 (18)
C8—C91.5202 (15)C21—H210.994 (18)
C8—H81.003 (12)C22—H220.990 (15)
C10—C151.3906 (16)
C8—O1—H1A105.7 (11)C15—C10—C7120.59 (10)
C6—N1—C7120.06 (8)C11—C10—C7120.64 (10)
C6—N1—H1109.5 (9)C12—C11—C10120.74 (11)
C7—N1—H1109.4 (9)C12—C11—H11119.3 (8)
C9—N2—C1121.98 (9)C10—C11—H11119.9 (8)
C9—N2—C16117.75 (9)C13—C12—C11120.00 (11)
C1—N2—C16120.13 (9)C13—C12—H12120.6 (8)
C2—C1—C6120.24 (10)C11—C12—H12119.4 (8)
C2—C1—N2119.58 (10)C14—C13—C12119.95 (11)
C6—C1—N2120.01 (9)C14—C13—H13119.8 (9)
C3—C2—C1120.55 (12)C12—C13—H13120.2 (9)
C3—C2—H2121.8 (8)C13—C14—C15120.05 (11)
C1—C2—H2117.6 (8)C13—C14—H14120.5 (8)
C4—C3—C2119.64 (12)C15—C14—H14119.5 (8)
C4—C3—H3120.4 (9)C10—C15—C14120.49 (11)
C2—C3—H3120.0 (9)C10—C15—H15119.0 (8)
C3—C4—C5120.24 (11)C14—C15—H15120.5 (8)
C3—C4—H4120.3 (9)N2—C16—C17113.79 (9)
C5—C4—H4119.4 (9)N2—C16—H16A108.4 (8)
C4—C5—C6121.12 (12)C17—C16—H16A108.3 (8)
C4—C5—H5120.7 (8)N2—C16—H16B107.4 (8)
C6—C5—H5118.2 (8)C17—C16—H16B110.1 (8)
C5—C6—C1118.15 (10)H16A—C16—H16B108.7 (12)
C5—C6—N1120.65 (10)C18—C17—C22118.77 (10)
C1—C6—N1120.89 (9)C18—C17—C16123.09 (10)
N1—C7—C10113.39 (9)C22—C17—C16118.13 (10)
N1—C7—C8109.09 (8)C17—C18—C19120.67 (11)
C10—C7—C8111.62 (9)C17—C18—H18119.9 (8)
N1—C7—H7106.9 (7)C19—C18—H18119.5 (8)
C10—C7—H7109.4 (7)C20—C19—C18120.29 (12)
C8—C7—H7106.2 (7)C20—C19—H19120.1 (9)
O1—C8—C9109.99 (8)C18—C19—H19119.5 (9)
O1—C8—C7110.90 (9)C19—C20—C21119.39 (11)
C9—C8—C7109.35 (8)C19—C20—H20121.1 (9)
O1—C8—H8108.2 (7)C21—C20—H20119.4 (9)
C9—C8—H8108.6 (7)C20—C21—C22120.68 (12)
C7—C8—H8109.8 (7)C20—C21—H21120.2 (10)
O2—C9—N2122.85 (10)C22—C21—H21119.1 (10)
O2—C9—C8119.44 (10)C21—C22—C17120.19 (12)
N2—C9—C8117.68 (9)C21—C22—H22121.6 (8)
C15—C10—C11118.75 (10)C17—C22—H22118.2 (8)
C9—N2—C1—C2−142.60 (10)C7—C8—C9—O299.40 (11)
C16—N2—C1—C241.75 (14)O1—C8—C9—N2155.42 (9)
C9—N2—C1—C642.15 (14)C7—C8—C9—N2−82.57 (11)
C16—N2—C1—C6−133.50 (10)N1—C7—C10—C15−122.85 (11)
C6—C1—C2—C32.31 (16)C8—C7—C10—C15113.45 (11)
N2—C1—C2—C3−172.93 (10)N1—C7—C10—C1155.54 (13)
C1—C2—C3—C4−0.80 (18)C8—C7—C10—C11−68.16 (13)
C2—C3—C4—C5−1.13 (18)C15—C10—C11—C121.45 (16)
C3—C4—C5—C61.57 (18)C7—C10—C11—C12−176.98 (10)
C4—C5—C6—C1−0.08 (16)C10—C11—C12—C13−0.18 (17)
C4—C5—C6—N1173.66 (10)C11—C12—C13—C14−1.16 (17)
C2—C1—C6—C5−1.84 (15)C12—C13—C14—C151.22 (17)
N2—C1—C6—C5173.38 (9)C11—C10—C15—C14−1.38 (16)
C2—C1—C6—N1−175.56 (9)C7—C10—C15—C14177.04 (10)
N2—C1—C6—N1−0.35 (15)C13—C14—C15—C100.07 (17)
C7—N1—C6—C5117.83 (11)C9—N2—C16—C1772.54 (13)
C7—N1—C6—C1−68.60 (13)C1—N2—C16—C17−111.63 (11)
C6—N1—C7—C10−88.73 (11)N2—C16—C17—C1811.59 (16)
C6—N1—C7—C836.34 (13)N2—C16—C17—C22−168.02 (10)
N1—C7—C8—O1171.71 (8)C22—C17—C18—C191.11 (17)
C10—C7—C8—O1−62.20 (11)C16—C17—C18—C19−178.49 (11)
N1—C7—C8—C950.25 (11)C17—C18—C19—C20−0.41 (18)
C10—C7—C8—C9176.34 (8)C18—C19—C20—C21−0.61 (18)
C1—N2—C9—O2−170.58 (10)C19—C20—C21—C220.92 (19)
C16—N2—C9—O25.17 (15)C20—C21—C22—C17−0.21 (19)
C1—N2—C9—C811.46 (14)C18—C17—C22—C21−0.80 (17)
C16—N2—C9—C8−172.79 (9)C16—C17—C22—C21178.82 (11)
O1—C8—C9—O2−22.61 (13)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 phenyl rings, respectively.
D—H···AD—HH···AD···AD—H···A
O1—H1A···O20.878 (18)2.166 (17)2.6601 (12)115.1 (14)
N1—H1···O2i0.918 (15)2.045 (16)2.9531 (12)169.5 (13)
O1—H1A···Cg2ii0.878 (18)2.719 (18)3.4636 (10)143.4 (16)
C13—H13···Cg1iii0.984 (15)2.699 (15)3.3283 (14)122.1 (10)
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2; (iii) x+1, y, z.
 

Acknowledgements

The support of NSF–MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

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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.

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ISSN: 2414-3146
Volume 1| Part 11| November 2016| x161849
https://doi.org/10.1107/S2414314616018496
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