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

Journal logoIUCrDATA
ISSN: 2414-3146

3-Hexyl-5,5-di­phenyl­imidazolidine-2,4-dione

aLaboratory of Medicinal Chemistry, Faculty of Medicine and Pharmacy, Mohammed V University, Rabat, Morocco, and bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: y.ramli@um5s.net.ma

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 8 January 2018; accepted 9 January 2018; online 12 January 2018)

The asymmetric unit of the title compound, C21H24N2O2, consists of two independent mol­ecules differing primarily in the orientation of the ends of the hexyl substituent, the C—C—C—C torsion angles being 71.7 (3) and170.5 (2)°. In the crystal, each independent mol­ecule forms a chain along the a-axis direction through a C—H⋯O hydrogen bond with one chain also including a C—H⋯π inter­action. Paired N—H⋯O hydrogen bonds between independent mol­ecules form ribbons with additional C—H⋯O hydrogen bonds and C—H⋯π(ring) inter­actions tying them into a three-dimensional structure.

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

Structure description

Hydantoin, a heterocycle containing two nitro­gen atoms, is a nucleus found in numerous natural products and in several clinically important medicines. One of the most significant hydantoin derivatives is 5,5-di­phenyl­imidazolidine-2,4-dione (phenytoin). As part of our ongoing studies of phenytoin derivatives (Ramli, Akrad et al., 2017[Ramli, Y., Akrad, R., Guerrab, W., Taoufik, J., Ansar, M. & Mague, J. T. (2017). IUCrData, 2, x170098.]; Ramli, Guerrab et al., 2017[Ramli, Y., Guerrab, W., Moussaif, A., Taoufik, J., Essassi, E. M. & Mague, J. T. (2017). IUCrData, 2, x171041.]; Akrad et al., 2017[Akrad, R., Mague, J. T., Guerrab, W., Taoufik, J., Ansar, M. & Ramli, Y. (2017). IUCrData, 2, x170033.]; Guerrab et al., 2017a[Guerrab, W., Akrad, R., Ansar, M., Taoufik, J., Mague, J. T. & Ramli, Y. (2017a). IUCrData, 2, x171534.],b[Guerrab, W., Akrad, R., Ansar, M., Taoufik, J., Mague, J. T. & Ramli, Y. (2017b). IUCrData, 2, x171591.]), the title compound was prepared and its crystal structure is reported here.

The asymmetric unit of the title compound consists of two independent mol­ecules differing in the orientations of the substituents on the imidazolidine-2,4-dione ring (Fig. 1[link]). Each imidazolidine-2,4-dione ring has two phenyl groups attached to the 5-position. The C10–C15 and C16–C21 phenyl rings are inclined to the C1/C2/N1/N2/C3 ring by 69.71 (12) and 71.80 (12)°, respectively, while the C31–C36 and C37–C42 phenyl rings make dihedral angles of 71.24 (11) and 67.85 (10)°, respectively, with the C22/C23/N3/C24/N4 ring. More significant are the different orientations of the ends of the n-hexyl chains with the C6—C7—C8—C9 torsion angle being 71.7 (3)° while the C27—C28—C29—C30 torsion angle is 170.5 (2)°.

[Figure 1]
Figure 1
The asymmetric unit with labelling scheme and 50% probability ellipsoids.

In the crystal, the O1-containing mol­ecules form chains along the a-axis direction through a combination of C14—H14⋯O1 hydrogen bonds and C7—H7ACg3 inter­actions (Table 1[link] and Fig. 2[link]; Cg3 is the centroid of phenyl ring C16–C21). O3-containing mol­ecules form chains parallel to these through C35—H35⋯O3 hydrogen bonds. These chains are associated into ribbons by paired N2—H2⋯O4 and N4—H4⋯O2 hydrogen bonds (Table 1[link] and Fig. 2[link]). Finally, C35—H35⋯O3 hydrogen bonds and additional C7—H7ACg3 inter­actions form a three-dimensional network (Table 1[link] and Fig. 3[link]).

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C16–C21 phenyl ring.

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2⋯O4i 0.88 2.04 2.896 (2) 165
N4—H4⋯O2ii 0.88 2.05 2.875 (2) 156
C14—H14⋯O1i 0.95 2.44 3.370 (3) 165
C33—H33⋯O3iii 0.95 2.48 3.413 (3) 169
C35—H35⋯O3ii 0.95 2.45 3.363 (3) 161
C7—H7ACg3iv 0.99 2.85 3.835 (3) 177
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z; (iii) [-x, y+{\script{1\over 2}}, -z+1]; (iv) x-1, y-1, z.
[Figure 2]
Figure 2
Detail of the chain-forming inter­actions. N—H⋯O and C—H⋯O hydrogen bonds are shown, respectively, as blue and black dashed lines. The C—H⋯π(ring) inter­actions are shown by green dashed lines [symmetry codes: (i) x + 1, y, z; (ii) −x + 1, y, z; (iii) −x + 1, −y + 1, z; (iv) −x, −y, −z + 1].
[Figure 3]
Figure 3
Packing viewed along the b-axis direction with inter­molecular inter­actions depicted as in Fig. 2[link].

Synthesis and crystallization

To a solution of 5,5-di­phenyl­imidazolidine-2,4-dione (1 g), one equivalent of hexyl bromide in absolute di­methyl­formamide (DMF) was added and the resulting solution heated under reflux for 2 h in the presence of 1.3 equivalents of K2CO3. The reaction mixture was filtered while hot, and the solvent evaporated under reduced pressure. The residue obtained was dried and crystallized from an ethanol solution to yield colourless block-shaped single crystals of the title compound.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula C21H24N2O2
Mr 336.42
Crystal system, space group Monoclinic, P21
Temperature (K) 100
a, b, c (Å) 8.5395 (13), 8.9377 (13), 23.444 (4)
β (°) 91.066 (2)
V3) 1789.0 (5)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.08
Crystal size (mm) 0.27 × 0.22 × 0.16
 
Data collection
Diffractometer Bruker SMART APEX CCD
Absorption correction Multi-scan (SADABS; Bruker, 2016[Bruker (2016). APEX3, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.87, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections 34684, 9382, 7808
Rint 0.043
(sin θ/λ)max−1) 0.687
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.112, 1.04
No. of reflections 9382
No. of parameters 454
No. of restraints 1
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.35, −0.23
Computer programs: APEX3 (Bruker, 2016[Bruker (2016). APEX3, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SAINT (Bruker, 2016[Bruker (2016). APEX3, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2016 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), DIAMOND (Brandenburg & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND, Crystal Impact GbR, Bonn, Germany.]), SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Structural data


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: SHELXL2016 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

3-Hexyl-5,5-diphenylimidazolidine-2,4-dione top
Crystal data top
C21H24N2O2F(000) = 720
Mr = 336.42Dx = 1.249 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 8.5395 (13) ÅCell parameters from 9959 reflections
b = 8.9377 (13) Åθ = 2.4–29.0°
c = 23.444 (4) ŵ = 0.08 mm1
β = 91.066 (2)°T = 100 K
V = 1789.0 (5) Å3Block, colourless
Z = 40.27 × 0.22 × 0.16 mm
Data collection top
Bruker SMART APEX CCD
diffractometer
9382 independent reflections
Radiation source: fine-focus sealed tube7808 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
Detector resolution: 8.3333 pixels mm-1θmax = 29.2°, θmin = 1.7°
φ and ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
k = 1212
Tmin = 0.87, Tmax = 0.99l = 3132
34684 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.112 w = 1/[σ2(Fo2) + (0.0634P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
9382 reflectionsΔρmax = 0.35 e Å3
454 parametersΔρmin = 0.22 e Å3
1 restraintAbsolute structure: Refined as an inversion twin
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.2 (10)
Special details top

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = –30.00 and 210.00°. The scan time was 20 sec/frame.

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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) 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. Refined as a 2-component inversion twin. H-atoms were placed in calculated positions (C—H = 0.95 - 0.99 Å; N—H = 0.88 Å). All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.36738 (17)0.13246 (19)0.08478 (6)0.0250 (4)
O20.54242 (17)0.05628 (19)0.25579 (6)0.0235 (4)
N10.41641 (19)0.0240 (2)0.17241 (7)0.0192 (4)
N20.6629 (2)0.0916 (2)0.18873 (7)0.0194 (4)
H20.7533100.1050540.2065980.023*
C10.6269 (2)0.1530 (2)0.13210 (8)0.0173 (4)
C20.4539 (2)0.1042 (3)0.12497 (9)0.0194 (4)
C30.5447 (2)0.0128 (3)0.21078 (8)0.0186 (4)
C40.2645 (2)0.0477 (3)0.18156 (9)0.0199 (4)
H4A0.1797940.0221260.1698640.024*
H4B0.2532650.0687870.2227400.024*
C50.2463 (3)0.1920 (3)0.14840 (10)0.0227 (5)
H5A0.3315970.2614810.1598530.027*
H5B0.2566830.1707630.1071960.027*
C60.0888 (2)0.2675 (3)0.15827 (9)0.0235 (5)
H6A0.0035760.1962760.1486030.028*
H6B0.0806820.2932680.1991740.028*
C70.0675 (3)0.4096 (3)0.12246 (10)0.0276 (5)
H7A0.0432760.4414820.1244540.033*
H7B0.0886940.3849820.0821580.033*
C80.1711 (3)0.5404 (3)0.14028 (10)0.0266 (5)
H8A0.1672510.6170740.1098200.032*
H8B0.2806780.5049840.1440250.032*
C90.1242 (4)0.6123 (3)0.19610 (10)0.0419 (7)
H9A0.1963580.6943650.2053750.063*
H9B0.0173250.6514260.1923110.063*
H9C0.1286560.5374120.2266280.063*
C100.7312 (2)0.0792 (2)0.08774 (8)0.0180 (4)
C110.6759 (3)0.0238 (3)0.04790 (8)0.0233 (5)
H110.5669830.0447210.0452920.028*
C120.7783 (3)0.0967 (3)0.01174 (9)0.0281 (5)
H120.7391770.1676930.0151000.034*
C130.9367 (3)0.0659 (3)0.01483 (9)0.0251 (5)
H131.0068160.1169040.0094220.030*
C140.9931 (3)0.0395 (3)0.05343 (9)0.0255 (5)
H141.1016770.0626650.0549820.031*
C150.8914 (2)0.1110 (3)0.08962 (9)0.0218 (5)
H150.9309180.1827100.1161210.026*
C160.6343 (2)0.3240 (3)0.13026 (9)0.0183 (4)
C170.6326 (3)0.3966 (3)0.07764 (9)0.0226 (5)
H170.6309190.3399250.0433660.027*
C180.6334 (3)0.5521 (3)0.07531 (10)0.0272 (5)
H180.6323100.6016650.0394480.033*
C190.6356 (3)0.6347 (3)0.12531 (10)0.0270 (5)
H190.6377030.7408920.1235830.032*
C200.6349 (3)0.5640 (3)0.17756 (10)0.0268 (5)
H200.6354230.6212970.2116950.032*
C210.6335 (3)0.4083 (3)0.18019 (9)0.0225 (5)
H210.6320130.3594410.2161690.027*
O30.12971 (17)0.14512 (18)0.42033 (6)0.0215 (3)
O40.05315 (16)0.08484 (18)0.25818 (6)0.0211 (3)
N30.07408 (19)0.0073 (2)0.33947 (7)0.0174 (4)
N40.1652 (2)0.0900 (2)0.31728 (7)0.0171 (4)
H40.2511790.1084640.2972180.020*
C220.1303 (2)0.1580 (2)0.37302 (8)0.0156 (4)
C230.0409 (2)0.1062 (2)0.38216 (8)0.0165 (4)
C240.0520 (2)0.0039 (2)0.30000 (8)0.0159 (4)
C250.2227 (2)0.0740 (3)0.33453 (9)0.0195 (4)
H25A0.2221940.1289660.2978540.023*
H25B0.3096860.0008760.3338430.023*
C260.2528 (2)0.1844 (2)0.38293 (9)0.0209 (4)
H26A0.2496050.1308120.4198440.025*
H26B0.1689360.2609400.3826580.025*
C270.4117 (3)0.2616 (3)0.37742 (10)0.0245 (5)
H27A0.4396940.3084080.4144940.029*
H27B0.4915790.1842910.3696580.029*
C280.4198 (3)0.3809 (3)0.33106 (10)0.0260 (5)
H28A0.5293210.4162270.3286020.031*
H28B0.3908870.3346280.2939730.031*
C290.3142 (3)0.5154 (3)0.34056 (10)0.0310 (5)
H29A0.2035360.4834990.3363610.037*
H29B0.3304250.5520370.3800790.037*
C300.3441 (3)0.6422 (3)0.29951 (10)0.0360 (6)
H30A0.2688330.7229070.3060120.054*
H30B0.3322320.6058460.2602360.054*
H30C0.4507980.6801610.3056780.054*
C310.2355 (2)0.0896 (2)0.41845 (8)0.0153 (4)
C320.1822 (2)0.0121 (3)0.45902 (8)0.0203 (4)
H320.0746980.0392960.4604490.024*
C330.2851 (3)0.0744 (3)0.49763 (9)0.0234 (5)
H330.2478910.1449430.5249970.028*
C340.4416 (3)0.0341 (3)0.49632 (9)0.0238 (5)
H340.5115590.0763590.5229250.029*
C350.4958 (3)0.0679 (2)0.45615 (9)0.0217 (5)
H350.6032510.0955550.4551810.026*
C360.3939 (2)0.1296 (2)0.41738 (9)0.0190 (4)
H360.4317940.1995760.3899080.023*
C370.1370 (2)0.3279 (2)0.37254 (9)0.0166 (4)
C380.1427 (2)0.4055 (3)0.42411 (9)0.0210 (5)
H380.1429670.3512690.4589630.025*
C390.1481 (3)0.5607 (3)0.42524 (10)0.0238 (5)
H390.1521220.6122560.4606250.029*
C400.1476 (3)0.6403 (3)0.37429 (10)0.0234 (5)
H400.1534880.7463820.3747500.028*
C410.1384 (3)0.5649 (3)0.32287 (10)0.0228 (5)
H410.1354780.6195570.2881570.027*
C420.1333 (2)0.4091 (3)0.32185 (9)0.0199 (5)
H420.1274200.3579780.2864220.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0195 (8)0.0308 (9)0.0243 (8)0.0022 (7)0.0080 (6)0.0069 (7)
O20.0190 (8)0.0316 (9)0.0200 (7)0.0027 (7)0.0016 (6)0.0086 (7)
N10.0137 (8)0.0232 (9)0.0206 (8)0.0034 (8)0.0027 (6)0.0039 (8)
N20.0138 (9)0.0260 (10)0.0181 (8)0.0035 (8)0.0046 (6)0.0070 (7)
C10.0148 (11)0.0199 (11)0.0171 (9)0.0021 (8)0.0050 (8)0.0048 (8)
C20.0148 (10)0.0213 (11)0.0219 (10)0.0003 (9)0.0038 (8)0.0024 (9)
C30.0152 (10)0.0211 (10)0.0196 (9)0.0011 (9)0.0008 (8)0.0009 (9)
C40.0129 (10)0.0241 (11)0.0227 (9)0.0024 (8)0.0003 (8)0.0016 (9)
C50.0190 (11)0.0246 (11)0.0246 (10)0.0001 (9)0.0004 (8)0.0021 (9)
C60.0162 (10)0.0248 (12)0.0295 (11)0.0011 (9)0.0003 (8)0.0028 (9)
C70.0266 (12)0.0268 (12)0.0291 (11)0.0027 (10)0.0052 (9)0.0042 (10)
C80.0273 (12)0.0232 (11)0.0292 (11)0.0032 (10)0.0023 (9)0.0003 (10)
C90.070 (2)0.0289 (14)0.0269 (12)0.0184 (14)0.0046 (12)0.0006 (11)
C100.0187 (10)0.0181 (10)0.0172 (9)0.0009 (9)0.0037 (8)0.0057 (8)
C110.0213 (11)0.0291 (12)0.0194 (9)0.0079 (10)0.0014 (8)0.0021 (9)
C120.0325 (13)0.0312 (13)0.0205 (10)0.0115 (11)0.0006 (9)0.0041 (10)
C130.0278 (12)0.0269 (12)0.0206 (10)0.0013 (10)0.0023 (9)0.0023 (9)
C140.0176 (11)0.0311 (13)0.0276 (11)0.0012 (10)0.0028 (9)0.0021 (10)
C150.0199 (11)0.0221 (11)0.0232 (10)0.0018 (9)0.0059 (8)0.0011 (9)
C160.0129 (11)0.0207 (11)0.0214 (10)0.0000 (8)0.0028 (8)0.0023 (8)
C170.0230 (12)0.0222 (11)0.0224 (11)0.0007 (10)0.0031 (9)0.0032 (9)
C180.0249 (13)0.0257 (13)0.0310 (12)0.0015 (10)0.0024 (10)0.0092 (9)
C190.0200 (12)0.0199 (12)0.0413 (14)0.0019 (10)0.0011 (10)0.0025 (10)
C200.0221 (12)0.0287 (13)0.0295 (12)0.0014 (10)0.0009 (9)0.0070 (10)
C210.0180 (11)0.0279 (12)0.0217 (10)0.0018 (10)0.0007 (8)0.0004 (9)
O30.0167 (8)0.0234 (8)0.0242 (7)0.0007 (6)0.0066 (6)0.0059 (6)
O40.0187 (7)0.0242 (8)0.0202 (7)0.0028 (6)0.0012 (6)0.0065 (6)
N30.0125 (8)0.0210 (9)0.0186 (8)0.0034 (7)0.0021 (6)0.0037 (7)
N40.0147 (9)0.0205 (9)0.0158 (8)0.0044 (7)0.0047 (6)0.0036 (7)
C220.0149 (10)0.0164 (10)0.0155 (9)0.0011 (8)0.0028 (8)0.0029 (8)
C230.0167 (10)0.0154 (10)0.0175 (9)0.0004 (9)0.0002 (8)0.0001 (8)
C240.0156 (10)0.0174 (10)0.0147 (8)0.0005 (8)0.0003 (7)0.0007 (8)
C250.0148 (10)0.0213 (11)0.0225 (10)0.0037 (8)0.0003 (8)0.0034 (9)
C260.0186 (11)0.0190 (10)0.0251 (10)0.0025 (8)0.0003 (8)0.0013 (8)
C270.0196 (11)0.0220 (11)0.0317 (11)0.0031 (9)0.0066 (9)0.0012 (9)
C280.0188 (11)0.0265 (12)0.0327 (12)0.0055 (9)0.0018 (9)0.0036 (10)
C290.0387 (14)0.0269 (12)0.0276 (11)0.0010 (11)0.0031 (10)0.0046 (10)
C300.0512 (17)0.0285 (13)0.0283 (12)0.0048 (12)0.0017 (11)0.0025 (10)
C310.0155 (10)0.0138 (10)0.0167 (9)0.0000 (8)0.0010 (7)0.0039 (8)
C320.0196 (11)0.0205 (11)0.0208 (9)0.0060 (9)0.0018 (8)0.0003 (9)
C330.0273 (12)0.0221 (11)0.0209 (10)0.0046 (9)0.0014 (9)0.0034 (9)
C340.0245 (12)0.0226 (11)0.0243 (10)0.0030 (9)0.0026 (9)0.0004 (9)
C350.0161 (10)0.0220 (11)0.0269 (10)0.0007 (9)0.0008 (8)0.0026 (9)
C360.0178 (10)0.0179 (11)0.0210 (10)0.0015 (9)0.0028 (8)0.0009 (8)
C370.0123 (11)0.0161 (10)0.0215 (10)0.0007 (8)0.0003 (8)0.0026 (8)
C380.0224 (12)0.0215 (11)0.0190 (10)0.0012 (10)0.0003 (8)0.0030 (9)
C390.0236 (12)0.0186 (11)0.0294 (11)0.0023 (9)0.0020 (9)0.0059 (9)
C400.0188 (12)0.0157 (11)0.0355 (12)0.0000 (9)0.0003 (10)0.0009 (9)
C410.0188 (12)0.0218 (12)0.0278 (11)0.0005 (9)0.0009 (9)0.0053 (9)
C420.0187 (11)0.0231 (11)0.0178 (10)0.0014 (9)0.0011 (8)0.0006 (9)
Geometric parameters (Å, º) top
O1—C21.213 (2)O3—C231.213 (2)
O2—C31.223 (2)O4—C241.219 (2)
N1—C21.366 (3)N3—C231.369 (3)
N1—C31.408 (2)N3—C241.410 (2)
N1—C41.466 (3)N3—C251.469 (3)
N2—C31.342 (3)N4—C241.348 (3)
N2—C11.464 (2)N4—C221.467 (2)
N2—H20.8800N4—H40.8800
C1—C101.531 (3)C22—C371.520 (3)
C1—C161.531 (3)C22—C311.533 (3)
C1—C21.547 (3)C22—C231.544 (3)
C4—C51.513 (3)C25—C261.522 (3)
C4—H4A0.9900C25—H25A0.9900
C4—H4B0.9900C25—H25B0.9900
C5—C61.526 (3)C26—C271.530 (3)
C5—H5A0.9900C26—H26A0.9900
C5—H5B0.9900C26—H26B0.9900
C6—C71.531 (3)C27—C281.525 (3)
C6—H6A0.9900C27—H27A0.9900
C6—H6B0.9900C27—H27B0.9900
C7—C81.520 (3)C28—C291.522 (3)
C7—H7A0.9900C28—H28A0.9900
C7—H7B0.9900C28—H28B0.9900
C8—C91.518 (3)C29—C301.512 (3)
C8—H8A0.9900C29—H29A0.9900
C8—H8B0.9900C29—H29B0.9900
C9—H9A0.9800C30—H30A0.9800
C9—H9B0.9800C30—H30B0.9800
C9—H9C0.9800C30—H30C0.9800
C10—C111.388 (3)C31—C321.386 (3)
C10—C151.397 (3)C31—C361.399 (3)
C11—C121.391 (3)C32—C331.390 (3)
C11—H110.9500C32—H320.9500
C12—C131.381 (3)C33—C341.383 (3)
C12—H120.9500C33—H330.9500
C13—C141.387 (3)C34—C351.384 (3)
C13—H130.9500C34—H340.9500
C14—C151.382 (3)C35—C361.385 (3)
C14—H140.9500C35—H350.9500
C15—H150.9500C36—H360.9500
C16—C211.392 (3)C37—C421.393 (3)
C16—C171.394 (3)C37—C381.395 (3)
C17—C181.391 (3)C38—C391.388 (3)
C17—H170.9500C38—H380.9500
C18—C191.385 (3)C39—C401.390 (3)
C18—H180.9500C39—H390.9500
C19—C201.379 (3)C40—C411.385 (3)
C19—H190.9500C40—H400.9500
C20—C211.393 (4)C41—C421.393 (3)
C20—H200.9500C41—H410.9500
C21—H210.9500C42—H420.9500
C2—N1—C3111.46 (16)C23—N3—C24111.06 (16)
C2—N1—C4124.74 (16)C23—N3—C25124.62 (16)
C3—N1—C4123.75 (17)C24—N3—C25124.30 (17)
C3—N2—C1113.56 (16)C24—N4—C22112.97 (16)
C3—N2—H2123.2C24—N4—H4123.5
C1—N2—H2123.2C22—N4—H4123.5
N2—C1—C10109.88 (17)N4—C22—C37113.61 (17)
N2—C1—C16113.07 (17)N4—C22—C31109.97 (16)
C10—C1—C16112.73 (18)C37—C22—C31112.37 (17)
N2—C1—C2100.15 (16)N4—C22—C23100.14 (16)
C10—C1—C2111.81 (17)C37—C22—C23109.62 (17)
C16—C1—C2108.54 (18)C31—C22—C23110.48 (17)
O1—C2—N1126.36 (19)O3—C23—N3126.09 (19)
O1—C2—C1126.3 (2)O3—C23—C22126.43 (19)
N1—C2—C1107.32 (16)N3—C23—C22107.47 (16)
O2—C3—N2128.42 (19)O4—C24—N4128.04 (18)
O2—C3—N1124.22 (19)O4—C24—N3124.38 (19)
N2—C3—N1107.36 (17)N4—C24—N3107.58 (17)
N1—C4—C5112.31 (17)N3—C25—C26113.33 (17)
N1—C4—H4A109.1N3—C25—H25A108.9
C5—C4—H4A109.1C26—C25—H25A108.9
N1—C4—H4B109.1N3—C25—H25B108.9
C5—C4—H4B109.1C26—C25—H25B108.9
H4A—C4—H4B107.9H25A—C25—H25B107.7
C4—C5—C6112.39 (18)C25—C26—C27111.52 (18)
C4—C5—H5A109.1C25—C26—H26A109.3
C6—C5—H5A109.1C27—C26—H26A109.3
C4—C5—H5B109.1C25—C26—H26B109.3
C6—C5—H5B109.1C27—C26—H26B109.3
H5A—C5—H5B107.9H26A—C26—H26B108.0
C5—C6—C7112.30 (18)C28—C27—C26115.30 (18)
C5—C6—H6A109.1C28—C27—H27A108.4
C7—C6—H6A109.1C26—C27—H27A108.5
C5—C6—H6B109.1C28—C27—H27B108.5
C7—C6—H6B109.1C26—C27—H27B108.4
H6A—C6—H6B107.9H27A—C27—H27B107.5
C8—C7—C6115.12 (18)C29—C28—C27114.42 (19)
C8—C7—H7A108.5C29—C28—H28A108.7
C6—C7—H7A108.5C27—C28—H28A108.7
C8—C7—H7B108.5C29—C28—H28B108.7
C6—C7—H7B108.5C27—C28—H28B108.7
H7A—C7—H7B107.5H28A—C28—H28B107.6
C9—C8—C7113.6 (2)C30—C29—C28113.0 (2)
C9—C8—H8A108.8C30—C29—H29A109.0
C7—C8—H8A108.8C28—C29—H29A109.0
C9—C8—H8B108.8C30—C29—H29B109.0
C7—C8—H8B108.8C28—C29—H29B109.0
H8A—C8—H8B107.7H29A—C29—H29B107.8
C8—C9—H9A109.5C29—C30—H30A109.5
C8—C9—H9B109.5C29—C30—H30B109.5
H9A—C9—H9B109.5H30A—C30—H30B109.5
C8—C9—H9C109.5C29—C30—H30C109.5
H9A—C9—H9C109.5H30A—C30—H30C109.5
H9B—C9—H9C109.5H30B—C30—H30C109.5
C11—C10—C15118.4 (2)C32—C31—C36118.98 (19)
C11—C10—C1123.27 (19)C32—C31—C22123.29 (18)
C15—C10—C1118.18 (19)C36—C31—C22117.71 (18)
C10—C11—C12120.8 (2)C31—C32—C33120.4 (2)
C10—C11—H11119.6C31—C32—H32119.8
C12—C11—H11119.6C33—C32—H32119.8
C13—C12—C11120.0 (2)C34—C33—C32120.2 (2)
C13—C12—H12120.0C34—C33—H33119.9
C11—C12—H12120.0C32—C33—H33119.9
C12—C13—C14119.8 (2)C33—C34—C35119.8 (2)
C12—C13—H13120.1C33—C34—H34120.1
C14—C13—H13120.1C35—C34—H34120.1
C15—C14—C13120.0 (2)C34—C35—C36120.2 (2)
C15—C14—H14120.0C34—C35—H35119.9
C13—C14—H14120.0C36—C35—H35119.9
C14—C15—C10120.8 (2)C35—C36—C31120.4 (2)
C14—C15—H15119.6C35—C36—H36119.8
C10—C15—H15119.6C31—C36—H36119.8
C21—C16—C17119.5 (2)C42—C37—C38118.8 (2)
C21—C16—C1121.0 (2)C42—C37—C22121.68 (19)
C17—C16—C1119.4 (2)C38—C37—C22119.48 (19)
C18—C17—C16120.0 (2)C39—C38—C37121.0 (2)
C18—C17—H17120.0C39—C38—H38119.5
C16—C17—H17120.0C37—C38—H38119.5
C19—C18—C17119.9 (2)C38—C39—C40119.6 (2)
C19—C18—H18120.0C38—C39—H39120.2
C17—C18—H18120.0C40—C39—H39120.2
C20—C19—C18120.5 (2)C41—C40—C39120.0 (2)
C20—C19—H19119.8C41—C40—H40120.0
C18—C19—H19119.8C39—C40—H40120.0
C19—C20—C21119.8 (2)C40—C41—C42120.2 (2)
C19—C20—H20120.1C40—C41—H41119.9
C21—C20—H20120.1C42—C41—H41119.9
C16—C21—C20120.2 (2)C41—C42—C37120.3 (2)
C16—C21—H21119.9C41—C42—H42119.8
C20—C21—H21119.9C37—C42—H42119.8
C3—N2—C1—C10114.0 (2)C24—N4—C22—C37125.53 (19)
C3—N2—C1—C16119.1 (2)C24—N4—C22—C31107.5 (2)
C3—N2—C1—C23.8 (2)C24—N4—C22—C238.8 (2)
C3—N1—C2—O1179.8 (2)C24—N3—C23—O3175.7 (2)
C4—N1—C2—O12.7 (4)C25—N3—C23—O33.0 (3)
C3—N1—C2—C10.1 (2)C24—N3—C23—C224.8 (2)
C4—N1—C2—C1177.53 (19)C25—N3—C23—C22176.59 (18)
N2—C1—C2—O1177.7 (2)N4—C22—C23—O3172.6 (2)
C10—C1—C2—O166.0 (3)C37—C22—C23—O352.9 (3)
C16—C1—C2—O159.0 (3)C31—C22—C23—O371.5 (3)
N2—C1—C2—N12.1 (2)N4—C22—C23—N37.8 (2)
C10—C1—C2—N1114.28 (19)C37—C22—C23—N3127.54 (18)
C16—C1—C2—N1120.8 (2)C31—C22—C23—N3108.09 (18)
C1—N2—C3—O2176.6 (2)C22—N4—C24—O4173.8 (2)
C1—N2—C3—N14.0 (3)C22—N4—C24—N36.5 (2)
C2—N1—C3—O2178.2 (2)C23—N3—C24—O4179.5 (2)
C4—N1—C3—O20.7 (3)C25—N3—C24—O41.9 (3)
C2—N1—C3—N22.5 (3)C23—N3—C24—N40.8 (2)
C4—N1—C3—N2179.94 (19)C25—N3—C24—N4177.87 (18)
C2—N1—C4—C577.6 (3)C23—N3—C25—C2665.2 (3)
C3—N1—C4—C599.6 (2)C24—N3—C25—C26116.3 (2)
N1—C4—C5—C6179.51 (17)N3—C25—C26—C27177.58 (17)
C4—C5—C6—C7177.25 (18)C25—C26—C27—C2874.5 (2)
C5—C6—C7—C869.8 (3)C26—C27—C28—C2963.9 (3)
C6—C7—C8—C971.7 (3)C27—C28—C29—C30170.5 (2)
N2—C1—C10—C11107.6 (2)N4—C22—C31—C32105.6 (2)
C16—C1—C10—C11125.3 (2)C37—C22—C31—C32126.8 (2)
C2—C1—C10—C112.6 (3)C23—C22—C31—C324.0 (3)
N2—C1—C10—C1568.7 (2)N4—C22—C31—C3672.5 (2)
C16—C1—C10—C1558.4 (2)C37—C22—C31—C3655.1 (2)
C2—C1—C10—C15178.94 (18)C23—C22—C31—C36177.84 (18)
C15—C10—C11—C121.7 (3)C36—C31—C32—C330.7 (3)
C1—C10—C11—C12174.5 (2)C22—C31—C32—C33177.4 (2)
C10—C11—C12—C130.6 (3)C31—C32—C33—C340.8 (3)
C11—C12—C13—C141.0 (4)C32—C33—C34—C350.4 (3)
C12—C13—C14—C151.5 (3)C33—C34—C35—C360.1 (3)
C13—C14—C15—C100.4 (3)C34—C35—C36—C310.0 (3)
C11—C10—C15—C141.2 (3)C32—C31—C36—C350.3 (3)
C1—C10—C15—C14175.2 (2)C22—C31—C36—C35177.90 (18)
N2—C1—C16—C2116.0 (3)N4—C22—C37—C4216.6 (3)
C10—C1—C16—C21141.4 (2)C31—C22—C37—C42142.31 (19)
C2—C1—C16—C2194.2 (2)C23—C22—C37—C4294.4 (2)
N2—C1—C16—C17167.80 (18)N4—C22—C37—C38165.08 (18)
C10—C1—C16—C1742.4 (3)C31—C22—C37—C3839.4 (3)
C2—C1—C16—C1782.0 (2)C23—C22—C37—C3883.8 (2)
C21—C16—C17—C181.3 (3)C42—C37—C38—C391.3 (3)
C1—C16—C17—C18177.6 (2)C22—C37—C38—C39179.7 (2)
C16—C17—C18—C190.1 (4)C37—C38—C39—C400.1 (4)
C17—C18—C19—C200.9 (4)C38—C39—C40—C411.4 (4)
C18—C19—C20—C210.7 (4)C39—C40—C41—C421.5 (4)
C17—C16—C21—C201.6 (3)C40—C41—C42—C370.2 (4)
C1—C16—C21—C20177.8 (2)C38—C37—C42—C411.2 (3)
C19—C20—C21—C160.6 (4)C22—C37—C42—C41179.5 (2)
Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C16–C21 phenyl ring.
D—H···AD—HH···AD···AD—H···A
N2—H2···O4i0.882.042.896 (2)165
N4—H4···O2ii0.882.052.875 (2)156
C14—H14···O1i0.952.443.370 (3)165
C33—H33···O3iii0.952.483.413 (3)169
C35—H35···O3ii0.952.453.363 (3)161
C7—H7A···Cg3iv0.992.853.835 (3)177
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z; (iii) x, y+1/2, z+1; (iv) x1, y1, z.
 

Acknowledgements

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

References

First citationAkrad, R., Mague, J. T., Guerrab, W., Taoufik, J., Ansar, M. & Ramli, Y. (2017). IUCrData, 2, x170033.  Google Scholar
First citationBrandenburg, K. & Putz, H. (2012). DIAMOND, Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBruker (2016). APEX3, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationGuerrab, W., Akrad, R., Ansar, M., Taoufik, J., Mague, J. T. & Ramli, Y. (2017a). IUCrData, 2, x171534.  Google Scholar
First citationGuerrab, W., Akrad, R., Ansar, M., Taoufik, J., Mague, J. T. & Ramli, Y. (2017b). IUCrData, 2, x171591.  Google Scholar
First citationRamli, Y., Akrad, R., Guerrab, W., Taoufik, J., Ansar, M. & Mague, J. T. (2017). IUCrData, 2, x170098.  Google Scholar
First citationRamli, Y., Guerrab, W., Moussaif, A., Taoufik, J., Essassi, E. M. & Mague, J. T. (2017). IUCrData, 2, x171041.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar

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.

Journal logoIUCrDATA
ISSN: 2414-3146
Follow IUCr Journals
Sign up for e-alerts
Follow IUCr on Twitter
Follow us on facebook
Sign up for RSS feeds

[# https x2 cm 20170801 %]