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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 2| Part 12| December 2017| x171808
https://doi.org/10.1107/S2414314617018089

5,5-Di­phenyl-3-propyl­imidazolidine-2,4-dione

CROSSMARK_Color_square_no_text.svg
Walid Guerrab,a* Joel T. Mague,b Rachida Akrad,a Mhammed Ansar,a Jamal Taoufika and Youssef Ramlia

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: gerrab_walid@yahoo.com

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 15 December 2017; accepted 18 December 2017; online 22 December 2017)

The asymmetric unit of the title compound, C18H18N2O2, consists of two independent mol­ecules differing primarily in the orientation of the propyl substituent. One of the propyl groups is disordered over two positions with an occupancy ratio of 0.859 (2):0.141 (2). The two independent mol­ecules are associated through a C—H⋯π(ring) inter­action and sheets parallel to (011) are formed from further sets of C—H⋯π(ring) inter­actions. The sheets are connected via inversion-related N—H⋯O hydrogen bonds.

CCDC reference: 1812257

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

Structure description

In view of the broad spectrum of applications associated with hydantoïne and as a part of our ongoing work on such mol­ecules (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.],c[Guerrab, W., Akrad, R., Ansar, M., Taoufik, J., Mague, J. T. & Ramli, Y. (2017c). IUCrData, 2, x171693.]), we report herein on the synthesis and crystal structure of the title compound.

The asymmetric unit of the title compound consists of two independent mol­ecules (Fig. 1[link]) which differ in the orientations of the propyl groups, one of which is disordered over two sites [at N3, occupancy ratio 0.859 (2):0.141 (2)], and the phenyl rings. Thus the N1—C4—C5—C6 torsion angle is 58.11 (14)° while the N3—C22—C23—C24 torsion angle is −57.2 (2)°. Each imidazolidine-2,4-dione ring has two phenyl rings attached at the 5-position. The C7–C12 and C13–C18 phenyl rings are inclined to the C1/C2/N1/C3/N2 ring by 67.13 (6) and 66.09 (6)°, respectively, while the C25–C30 and C31–C36 phenyl rings are inclined to the C19/C20/N3/C21/N4 ring by 71.25 (6) and 64.48 (6)°, respectively.

[Figure 1]
Figure 1
The asymmetric unit with labeling scheme and 50% probability ellipsoids. The C—H⋯π(ring) inter­action is shown by a dashed line. Only the major orientation of the disordered propyl group is shown.

In the crystal, C—H⋯π(ring) inter­actions (C5—H5A⋯Cg5, C15—H15⋯Cg2, C23—H23A⋯Cg2, C24—H24C⋯Cg6 and C35—H35⋯Cg5; Table 1[link]) form layers parallel to (011) (Fig. 2[link]; Cg2, Cg5 and Cg6 are the centroids of the C25–C30, C7–C12 and C13–C18 phenyl rings, respectively). These are connected in the direction of the diagonal of the bc face by inversion-related N2—H2⋯O4 and N4—H4⋯O2 hydrogen bonds (Table 1[link] and Figs. 3[link] and 4[link]).

Table 1
Hydrogen-bond geometry (Å, °)

Cg2, Cg5 and Cg6 are the centroids of the C25–C30, C7–C12 and C13–C18 phenyl rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2⋯O4i 0.908 (14) 1.915 (15) 2.8211 (11) 174.8 (12)
N4—H4⋯O2i 0.913 (14) 1.917 (14) 2.8293 (10) 177.3 (12)
C5—H5A⋯Cg5ii 1.033 (15) 2.651 (15) 3.6101 (13) 154.4 (11)
C15—H15⋯Cg2iii 0.971 (15) 2.925 (14) 3.8055 (12) 154.1 (12)
C23—H23A⋯Cg2ii 0.99 2.92 3.8118 (15) 151
C24—H24C⋯Cg6iv 0.98 2.91 3.6320 (13) 131
C35—H35⋯Cg5 0.981 (15) 2.741 (15) 3.6627 (13) 156.9 (13)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x+1, y, z; (iii) x-1, y-1, z+1; (iv) x+1, y+1, z-1.
[Figure 2]
Figure 2
Portion of one layer formed by C—H⋯π(ring) inter­actions (green dashed lines) viewed along the b-axis direction.
[Figure 3]
Figure 3
Edge view of two layers showing the inversion-related N—H⋯O hydrogen bonds (blue dashed lines) holding them together.
[Figure 4]
Figure 4
Packing viewed along the a-axis direction with inter­molecular inter­actions depicted as in Figs. 2[link] and 3[link].

Synthesis and crystallization

To a solution of 5,5-di­phenyl­imidazolidine-2,4-dione (3.96 mol, 1 g) in 20 ml of absolute di­methyl­formamide (DMF) were added equivalent amounts of propyl bromide (3.96 mol), K2CO3 (3.96 mol) and a catalytic amount of tetra­butyl­ammonium bromide. The resulting solution was heated under reflux for 3 h. The progress was monitored by TLC and, when complete, the solid material was removed by filtration and the solvent evaporated under vacuum. The solid product was purified by recrystallization from an ethanol solution to afford colourless block-like crystals of the title compound (yield 69%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The n-propyl group attached to N3 is disordered over two sites in an 0.859 (2):0.141 (2) ratio. The two components of the disorder were refined subject to restraints that their geometries be comparable.

Table 2
Experimental details

Crystal data
Chemical formula C18H18N2O2
Mr 294.34
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 100
a, b, c (Å) 9.0951 (5), 13.9582 (7), 14.1083 (7)
α, β, γ (°) 61.646 (1), 80.859 (1), 83.665 (1)
V (Å3) 1554.92 (14)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.08
Crystal size (mm) 0.38 × 0.26 × 0.13
 
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 0.90, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections 30287, 8294, 6452
Rint 0.025
(sin θ/λ)max (Å−1) 0.687
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.149, 1.06
No. of reflections 8294
No. of parameters 525
No. of restraints 4
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.82, −0.22
Computer programs: APEX3 and 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.]) and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Structural data

CCDC reference: 1812257

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617018089/vm4030sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617018089/vm4030Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617018089/vm4030Isup3.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: SHELXL2016 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

5,5-Diphenyl-3-propylimidazolidine-2,4-dione top
Crystal data top
C18H18N2O2Z = 4
Mr = 294.34F(000) = 624
Triclinic, P1Dx = 1.257 Mg m−3
a = 9.0951 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.9582 (7) ÅCell parameters from 9889 reflections
c = 14.1083 (7) Åθ = 2.6–29.2°
α = 61.646 (1)°µ = 0.08 mm−1
β = 80.859 (1)°T = 100 K
γ = 83.665 (1)°Block, colourless
V = 1554.92 (14) Å30.38 × 0.26 × 0.13 mm
Data collection top
Bruker SMART APEX CCD
diffractometer		8294 independent reflections
Radiation source: fine-focus sealed tube6452 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 8.3333 pixels mm-1θmax = 29.3°, θmin = 1.7°
φ and ω scansh = −12→12
Absorption correction: multi-scan
(SADABS; Bruker, 2016)		k = −19→19
Tmin = 0.90, Tmax = 0.99l = −19→19
30287 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: mixed
wR(F2) = 0.149H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.1024P)2]
where P = (Fo2 + 2Fc2)/3
8294 reflections(Δ/σ)max < 0.001
525 parametersΔρmax = 0.82 e Å−3
4 restraintsΔρmin = −0.22 e Å−3
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 15 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. The n-propyl group attached to N3 is disordered over two sites in an 86/14 ratio. The two components of the disorder were refined subject to restraints that their geometries be comparable. The H-atoms attached to the disordered carbon atoms were included as riding contributions in idealized positions.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.48473 (8)0.18081 (6)0.42407 (6)0.01755 (17)
O20.45883 (8)0.25978 (6)0.70572 (6)0.01828 (17)
N10.51038 (9)0.22639 (7)0.55718 (6)0.01434 (18)
N20.27463 (9)0.24006 (7)0.62162 (7)0.01436 (18)
H20.1962 (15)0.2418 (11)0.6695 (11)0.030 (4)*
C10.26504 (10)0.21140 (8)0.53557 (7)0.01268 (19)
C20.43165 (10)0.20303 (7)0.49574 (7)0.01296 (19)
C30.41530 (10)0.24442 (8)0.63624 (7)0.0136 (2)
C40.67315 (11)0.22770 (9)0.54519 (8)0.0184 (2)
H4A0.6980 (13)0.2227 (9)0.6117 (10)0.022 (3)*
H4B0.7149 (14)0.1610 (11)0.5386 (11)0.035 (4)*
C50.73420 (13)0.32872 (10)0.44664 (10)0.0253 (2)
H5A0.8489 (16)0.3225 (11)0.4434 (11)0.043 (4)*
H5B0.7070 (14)0.3307 (11)0.3781 (11)0.038 (4)*
C60.67328 (17)0.43396 (11)0.44735 (14)0.0404 (4)
H6A0.6946 (18)0.4252 (13)0.5188 (15)0.062 (5)*
H6B0.5670 (18)0.4420 (12)0.4491 (13)0.054 (5)*
H6C0.7232 (16)0.4947 (12)0.3881 (12)0.043 (4)*
C70.19013 (10)0.30287 (8)0.44141 (8)0.0135 (2)
C80.14852 (11)0.40325 (8)0.43836 (8)0.0166 (2)
H80.1644 (14)0.4151 (10)0.4995 (11)0.029 (3)*
C90.08176 (12)0.48500 (9)0.35073 (9)0.0205 (2)
H90.0494 (16)0.5548 (12)0.3491 (12)0.035 (4)*
C100.05632 (12)0.46633 (9)0.26692 (9)0.0215 (2)
H100.0069 (16)0.5229 (12)0.2043 (12)0.039 (4)*
C110.09900 (12)0.36686 (9)0.26855 (9)0.0209 (2)
H110.0797 (14)0.3537 (10)0.2093 (10)0.026 (3)*
C120.16525 (12)0.28500 (8)0.35581 (8)0.0176 (2)
H120.1954 (13)0.2153 (10)0.3587 (10)0.018 (3)*
C130.18734 (11)0.10368 (8)0.58305 (7)0.0139 (2)
C140.03790 (11)0.10227 (9)0.62591 (9)0.0202 (2)
H14−0.0109 (15)0.1712 (11)0.6215 (11)0.034 (4)*
C15−0.03798 (12)0.00581 (9)0.67654 (9)0.0240 (2)
H15−0.1409 (16)0.0034 (11)0.7089 (11)0.031 (4)*
C160.03532 (13)−0.09000 (9)0.68403 (9)0.0221 (2)
H16−0.0178 (15)−0.1563 (12)0.7178 (12)0.034 (4)*
C170.18299 (13)−0.08871 (9)0.64096 (9)0.0219 (2)
H170.2396 (15)−0.1577 (11)0.6466 (11)0.030 (3)*
C180.25930 (12)0.00795 (8)0.59043 (8)0.0182 (2)
H180.3658 (15)0.0081 (10)0.5595 (11)0.027 (3)*
O30.98340 (8)0.69719 (6)−0.07289 (6)0.01940 (17)
O40.95664 (8)0.75840 (6)0.22003 (6)0.01725 (16)
N31.00840 (9)0.73558 (7)0.06558 (7)0.01438 (18)
N40.77230 (9)0.74262 (7)0.13330 (7)0.01473 (18)
H40.6963 (15)0.7401 (11)0.1851 (11)0.027 (3)*
C190.76381 (10)0.71632 (8)0.04547 (8)0.0134 (2)
C200.93049 (10)0.71417 (8)0.00219 (8)0.0136 (2)
C210.91302 (10)0.74716 (8)0.14800 (8)0.0136 (2)
C221.16981 (12)0.74643 (12)0.0510 (2)0.0171 (3)0.859 (2)
H22A1.2165390.722837−0.0032200.021*0.859 (2)
H22B1.2091790.6971800.1205760.021*0.859 (2)
C231.21427 (13)0.86212 (10)0.01399 (10)0.0210 (3)0.859 (2)
H23A1.3243530.8638750.0039230.025*0.859 (2)
H23B1.1758930.8831940.0714710.025*0.859 (2)
C241.15523 (17)0.94499 (11)−0.09161 (12)0.0256 (3)0.859 (2)
H24A1.1923151.016896−0.1140470.038*0.859 (2)
H24B1.0460300.948307−0.0804460.038*0.859 (2)
H24C1.1893970.923007−0.1481750.038*0.859 (2)
C22A1.1716 (3)0.7308 (8)0.0548 (13)0.0171 (3)0.141 (2)
H22C1.2116580.6638100.0507940.021*0.141 (2)
H22D1.2060320.7302860.1182580.021*0.141 (2)
C23A1.2253 (8)0.8313 (6)−0.0489 (6)0.0210 (3)0.141 (2)
H23C1.2005100.826008−0.1120180.025*0.141 (2)
H23D1.3351320.832919−0.0552800.025*0.141 (2)
C24A1.1560 (12)0.9370 (6)−0.0519 (8)0.0256 (3)0.141 (2)
H24D1.1650860.9369140.0164780.038*0.141 (2)
H24E1.0504730.943153−0.0615930.038*0.141 (2)
H24F1.2079350.998951−0.1123860.038*0.141 (2)
C250.68216 (10)0.80642 (8)−0.04580 (8)0.0140 (2)
C260.65579 (11)0.91012 (8)−0.05456 (8)0.0173 (2)
H260.6869 (14)0.9260 (10)0.0004 (11)0.029 (3)*
C270.58340 (12)0.99113 (9)−0.13937 (9)0.0197 (2)
H270.5658 (16)1.0636 (12)−0.1460 (12)0.040 (4)*
C280.53733 (12)0.96829 (9)−0.21508 (9)0.0210 (2)
H280.4791 (16)1.0221 (12)−0.2728 (12)0.042 (4)*
C290.56533 (13)0.86544 (9)−0.20771 (9)0.0249 (2)
H290.5340 (15)0.8493 (11)−0.2617 (12)0.038 (4)*
C300.63728 (13)0.78448 (9)−0.12344 (9)0.0219 (2)
H300.6600 (15)0.7118 (12)−0.1186 (11)0.032 (4)*
C310.69286 (11)0.60606 (8)0.09187 (8)0.0144 (2)
C320.76638 (12)0.51533 (8)0.08758 (9)0.0187 (2)
H320.8703 (15)0.5229 (11)0.0483 (11)0.027 (3)*
C330.69545 (13)0.41643 (9)0.13573 (9)0.0226 (2)
H330.7532 (15)0.3508 (11)0.1336 (11)0.033 (4)*
C340.55150 (13)0.40801 (9)0.18795 (9)0.0228 (2)
H340.5058 (16)0.3381 (12)0.2211 (12)0.037 (4)*
C350.47705 (13)0.49878 (9)0.19224 (10)0.0253 (2)
H350.3752 (16)0.4911 (11)0.2297 (11)0.033 (4)*
C360.54751 (12)0.59709 (9)0.14439 (9)0.0223 (2)
H360.4963 (15)0.6607 (12)0.1505 (11)0.036 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0169 (4)0.0205 (4)0.0159 (3)−0.0007 (3)0.0003 (3)−0.0098 (3)
O20.0158 (4)0.0255 (4)0.0171 (4)−0.0018 (3)−0.0029 (3)−0.0124 (3)
N10.0100 (4)0.0184 (4)0.0143 (4)−0.0007 (3)−0.0003 (3)−0.0077 (3)
N20.0120 (4)0.0197 (4)0.0139 (4)−0.0010 (3)−0.0008 (3)−0.0101 (3)
C10.0111 (4)0.0145 (5)0.0136 (4)−0.0002 (3)−0.0009 (3)−0.0078 (4)
C20.0127 (4)0.0108 (4)0.0122 (4)−0.0001 (3)−0.0017 (3)−0.0028 (4)
C30.0125 (5)0.0134 (5)0.0126 (4)−0.0013 (3)−0.0002 (3)−0.0044 (4)
C40.0098 (5)0.0252 (5)0.0191 (5)−0.0001 (4)−0.0017 (4)−0.0096 (4)
C50.0192 (5)0.0286 (6)0.0268 (6)−0.0057 (4)0.0009 (4)−0.0119 (5)
C60.0348 (8)0.0251 (7)0.0589 (10)−0.0108 (6)0.0067 (7)−0.0194 (7)
C70.0114 (4)0.0136 (5)0.0141 (4)−0.0018 (3)−0.0014 (3)−0.0051 (4)
C80.0154 (5)0.0156 (5)0.0192 (5)−0.0010 (4)−0.0014 (4)−0.0086 (4)
C90.0192 (5)0.0142 (5)0.0243 (5)0.0007 (4)−0.0029 (4)−0.0061 (4)
C100.0200 (5)0.0164 (5)0.0207 (5)−0.0017 (4)−0.0061 (4)−0.0015 (4)
C110.0240 (5)0.0197 (5)0.0172 (5)−0.0022 (4)−0.0071 (4)−0.0057 (4)
C120.0211 (5)0.0154 (5)0.0169 (5)−0.0003 (4)−0.0046 (4)−0.0075 (4)
C130.0145 (5)0.0143 (5)0.0118 (4)−0.0019 (4)−0.0023 (3)−0.0046 (4)
C140.0145 (5)0.0169 (5)0.0251 (5)−0.0003 (4)−0.0017 (4)−0.0067 (4)
C150.0154 (5)0.0231 (6)0.0269 (6)−0.0049 (4)−0.0008 (4)−0.0059 (5)
C160.0261 (6)0.0176 (5)0.0198 (5)−0.0084 (4)−0.0029 (4)−0.0050 (4)
C170.0285 (6)0.0162 (5)0.0214 (5)−0.0013 (4)−0.0015 (4)−0.0096 (4)
C180.0185 (5)0.0174 (5)0.0188 (5)−0.0013 (4)0.0001 (4)−0.0091 (4)
O30.0186 (4)0.0245 (4)0.0165 (4)−0.0013 (3)0.0006 (3)−0.0114 (3)
O40.0155 (4)0.0224 (4)0.0164 (3)−0.0007 (3)−0.0031 (3)−0.0109 (3)
N30.0109 (4)0.0173 (4)0.0151 (4)−0.0003 (3)−0.0006 (3)−0.0080 (3)
N40.0122 (4)0.0201 (4)0.0139 (4)−0.0009 (3)−0.0008 (3)−0.0097 (3)
C190.0126 (4)0.0158 (5)0.0135 (4)−0.0002 (4)−0.0012 (3)−0.0083 (4)
C200.0131 (5)0.0119 (4)0.0135 (4)−0.0006 (3)−0.0016 (3)−0.0039 (4)
C210.0136 (5)0.0119 (4)0.0136 (4)−0.0008 (3)−0.0009 (3)−0.0048 (4)
C220.0098 (5)0.0200 (7)0.0204 (5)−0.0006 (4)−0.0007 (4)−0.0088 (6)
C230.0176 (6)0.0264 (7)0.0203 (6)−0.0082 (5)−0.0008 (4)−0.0109 (5)
C240.0283 (7)0.0226 (6)0.0214 (8)−0.0070 (5)−0.0042 (7)−0.0051 (6)
C22A0.0098 (5)0.0200 (7)0.0204 (5)−0.0006 (4)−0.0007 (4)−0.0088 (6)
C23A0.0176 (6)0.0264 (7)0.0203 (6)−0.0082 (5)−0.0008 (4)−0.0109 (5)
C24A0.0283 (7)0.0226 (6)0.0214 (8)−0.0070 (5)−0.0042 (7)−0.0051 (6)
C250.0121 (4)0.0144 (5)0.0142 (4)−0.0010 (4)−0.0011 (3)−0.0057 (4)
C260.0174 (5)0.0170 (5)0.0190 (5)−0.0015 (4)−0.0023 (4)−0.0093 (4)
C270.0201 (5)0.0137 (5)0.0229 (5)0.0003 (4)−0.0021 (4)−0.0069 (4)
C280.0201 (5)0.0186 (5)0.0192 (5)0.0000 (4)−0.0052 (4)−0.0041 (4)
C290.0338 (6)0.0210 (5)0.0223 (5)0.0021 (5)−0.0128 (5)−0.0097 (5)
C300.0295 (6)0.0180 (5)0.0213 (5)0.0024 (4)−0.0103 (4)−0.0101 (4)
C310.0144 (5)0.0146 (5)0.0135 (4)−0.0012 (4)−0.0033 (3)−0.0054 (4)
C320.0188 (5)0.0190 (5)0.0196 (5)0.0003 (4)−0.0010 (4)−0.0105 (4)
C330.0283 (6)0.0171 (5)0.0237 (5)−0.0001 (4)−0.0031 (4)−0.0107 (4)
C340.0275 (6)0.0175 (5)0.0215 (5)−0.0071 (4)−0.0025 (4)−0.0063 (4)
C350.0188 (5)0.0232 (6)0.0311 (6)−0.0058 (4)0.0022 (4)−0.0109 (5)
C360.0148 (5)0.0208 (5)0.0313 (6)−0.0012 (4)0.0003 (4)−0.0129 (5)
Geometric parameters (Å, º) top
O1—C21.2090 (11)N3—C22A1.466 (3)
O2—C31.2269 (11)N4—C211.3416 (12)
N1—C21.3739 (12)N4—C191.4646 (11)
N1—C31.4026 (12)N4—H40.913 (14)
N1—C41.4642 (12)C19—C311.5302 (13)
N2—C31.3402 (12)C19—C251.5332 (13)
N2—C11.4643 (11)C19—C201.5444 (13)
N2—H20.908 (14)C22—C231.523 (2)
C1—C131.5285 (13)C22—H22A0.9900
C1—C71.5310 (13)C22—H22B0.9900
C1—C21.5421 (13)C23—C241.5251 (18)
C4—C51.5149 (15)C23—H23A0.9900
C4—H4A0.969 (12)C23—H23B0.9900
C4—H4B1.006 (13)C24—H24A0.9800
C5—C61.5156 (18)C24—H24B0.9800
C5—H5A1.033 (14)C24—H24C0.9800
C5—H5B1.022 (14)C22A—C23A1.523 (4)
C6—H6A1.004 (17)C22A—H22C0.9900
C6—H6B0.958 (16)C22A—H22D0.9900
C6—H6C0.957 (15)C23A—C24A1.523 (3)
C7—C81.3925 (13)C23A—H23C0.9900
C7—C121.3991 (13)C23A—H23D0.9900
C8—C91.3946 (14)C24A—H24D0.9800
C8—H80.985 (13)C24A—H24E0.9800
C9—C101.3830 (15)C24A—H24F0.9800
C9—H90.977 (15)C25—C261.3896 (13)
C10—C111.3901 (15)C25—C301.3959 (13)
C10—H100.996 (15)C26—C271.3946 (14)
C11—C121.3899 (14)C26—H260.989 (13)
C11—H110.981 (13)C27—C281.3832 (15)
C12—H120.965 (12)C27—H270.968 (15)
C13—C181.3861 (13)C28—C291.3865 (15)
C13—C141.3952 (14)C28—H280.988 (15)
C14—C151.3908 (14)C29—C301.3880 (15)
C14—H140.992 (14)C29—H290.979 (14)
C15—C161.3913 (16)C30—H300.985 (14)
C15—H150.971 (14)C31—C321.3884 (13)
C16—C171.3816 (16)C31—C361.3963 (14)
C16—H160.961 (15)C32—C331.3963 (14)
C17—C181.3951 (14)C32—H321.006 (13)
C17—H171.014 (14)C33—C341.3842 (16)
C18—H180.997 (13)C33—H331.015 (14)
O3—C201.2087 (11)C34—C351.3921 (15)
O4—C211.2279 (11)C34—H340.968 (15)
N3—C201.3759 (12)C35—C361.3878 (15)
N3—C211.3993 (12)C35—H350.981 (14)
N3—C221.4642 (13)C36—H360.990 (14)
C2—N1—C3111.38 (8)C31—C19—C25111.92 (7)
C2—N1—C4124.52 (8)N4—C19—C20100.77 (7)
C3—N1—C4124.05 (8)C31—C19—C20113.17 (8)
C3—N2—C1113.01 (8)C25—C19—C20108.44 (7)
C3—N2—H2121.6 (8)O3—C20—N3126.18 (9)
C1—N2—H2124.3 (8)O3—C20—C19127.03 (8)
N2—C1—C13109.91 (8)N3—C20—C19106.80 (8)
N2—C1—C7112.14 (8)O4—C21—N4128.22 (9)
C13—C1—C7112.17 (7)O4—C21—N3123.68 (9)
N2—C1—C2100.74 (7)N4—C21—N3108.10 (8)
C13—C1—C2113.12 (7)N3—C22—C23113.35 (11)
C7—C1—C2108.24 (7)N3—C22—H22A108.9
O1—C2—N1125.81 (9)C23—C22—H22A108.9
O1—C2—C1127.32 (8)N3—C22—H22B108.9
N1—C2—C1106.87 (8)C23—C22—H22B108.9
O2—C3—N2128.17 (9)H22A—C22—H22B107.7
O2—C3—N1123.97 (9)C22—C23—C24112.92 (14)
N2—C3—N1107.85 (8)C22—C23—H23A109.0
N1—C4—C5112.45 (9)C24—C23—H23A109.0
N1—C4—H4A106.0 (7)C22—C23—H23B109.0
C5—C4—H4A111.6 (7)C24—C23—H23B109.0
N1—C4—H4B107.8 (7)H23A—C23—H23B107.8
C5—C4—H4B109.5 (8)C23—C24—H24A109.5
H4A—C4—H4B109.3 (10)C23—C24—H24B109.5
C4—C5—C6113.45 (10)H24A—C24—H24B109.5
C4—C5—H5A107.5 (8)C23—C24—H24C109.5
C6—C5—H5A110.9 (7)H24A—C24—H24C109.5
C4—C5—H5B109.3 (7)H24B—C24—H24C109.5
C6—C5—H5B107.4 (7)N3—C22A—C23A107.4 (5)
H5A—C5—H5B108.2 (10)N3—C22A—H22C110.2
C5—C6—H6A104.3 (10)C23A—C22A—H22C110.2
C5—C6—H6B112.3 (9)N3—C22A—H22D110.2
H6A—C6—H6B105.8 (13)C23A—C22A—H22D110.2
C5—C6—H6C110.3 (9)H22C—C22A—H22D108.5
H6A—C6—H6C111.0 (12)C22A—C23A—C24A112.7 (5)
H6B—C6—H6C112.7 (13)C22A—C23A—H23C109.1
C8—C7—C12119.55 (9)C24A—C23A—H23C109.1
C8—C7—C1121.69 (8)C22A—C23A—H23D109.1
C12—C7—C1118.75 (8)C24A—C23A—H23D109.1
C7—C8—C9120.06 (9)H23C—C23A—H23D107.8
C7—C8—H8119.3 (8)C23A—C24A—H24D109.5
C9—C8—H8120.6 (8)C23A—C24A—H24E109.5
C10—C9—C8120.03 (10)H24C—C24A—H24D109.5
C10—C9—H9119.4 (8)C23A—C24A—H24F109.5
C8—C9—H9120.5 (9)H24D—C24A—H24F109.5
C9—C10—C11120.37 (10)H24E—C24A—H24F109.5
C9—C10—H10121.5 (8)C26—C25—C30119.40 (9)
C11—C10—H10118.2 (8)C26—C25—C19121.42 (8)
C12—C11—C10119.84 (10)C30—C25—C19119.16 (8)
C12—C11—H11120.1 (8)C25—C26—C27120.28 (9)
C10—C11—H11120.1 (8)C25—C26—H26119.8 (8)
C11—C12—C7120.14 (9)C27—C26—H26119.9 (8)
C11—C12—H12121.2 (7)C28—C27—C26119.96 (9)
C7—C12—H12118.7 (7)C28—C27—H27119.6 (9)
C18—C13—C14119.27 (9)C26—C27—H27120.4 (9)
C18—C13—C1123.53 (9)C27—C28—C29120.02 (10)
C14—C13—C1117.11 (8)C27—C28—H28121.9 (8)
C15—C14—C13120.54 (10)C29—C28—H28118.0 (8)
C15—C14—H14121.4 (8)C28—C29—C30120.26 (10)
C13—C14—H14118.1 (8)C28—C29—H29120.2 (8)
C14—C15—C16119.80 (10)C30—C29—H29119.5 (8)
C14—C15—H15121.2 (8)C29—C30—C25120.06 (10)
C16—C15—H15119.0 (8)C29—C30—H30120.8 (8)
C17—C16—C15119.80 (10)C25—C30—H30119.1 (8)
C17—C16—H16120.5 (8)C32—C31—C36119.19 (9)
C15—C16—H16119.7 (8)C32—C31—C19123.76 (9)
C16—C17—C18120.43 (10)C36—C31—C19117.01 (9)
C16—C17—H17121.4 (8)C31—C32—C33120.14 (10)
C18—C17—H17118.2 (8)C31—C32—H32118.7 (7)
C13—C18—C17120.15 (10)C33—C32—H32121.2 (7)
C13—C18—H18120.0 (7)C34—C33—C32120.38 (10)
C17—C18—H18119.9 (7)C34—C33—H33121.2 (8)
C20—N3—C21111.29 (8)C32—C33—H33118.4 (8)
C20—N3—C22125.95 (15)C33—C34—C35119.74 (10)
C21—N3—C22122.75 (15)C33—C34—H34118.4 (8)
C20—N3—C22A122.5 (9)C35—C34—H34121.9 (8)
C21—N3—C22A125.6 (9)C36—C35—C34119.89 (10)
C21—N4—C19112.74 (8)C36—C35—H35121.6 (8)
C21—N4—H4119.3 (8)C34—C35—H35118.5 (8)
C19—N4—H4126.3 (8)C35—C36—C31120.65 (10)
N4—C19—C31109.65 (8)C35—C36—H36119.9 (8)
N4—C19—C25112.43 (8)C31—C36—H36119.4 (8)
C3—N2—C1—C13117.44 (9)C22—N3—C20—O32.79 (16)
C3—N2—C1—C7−117.06 (9)C22A—N3—C20—O3−5.6 (3)
C3—N2—C1—C2−2.15 (10)C21—N3—C20—C192.39 (10)
C3—N1—C2—O1−177.65 (9)C22—N3—C20—C19−177.12 (9)
C4—N1—C2—O1−0.14 (15)C22A—N3—C20—C19174.5 (3)
C3—N1—C2—C12.65 (10)N4—C19—C20—O3−178.94 (9)
C4—N1—C2—C1−179.84 (8)C31—C19—C20—O364.08 (12)
N2—C1—C2—O1179.94 (9)C25—C19—C20—O3−60.72 (12)
C13—C1—C2—O162.69 (12)N4—C19—C20—N30.97 (9)
C7—C1—C2—O1−62.26 (12)C31—C19—C20—N3−116.02 (8)
N2—C1—C2—N1−0.37 (9)C25—C19—C20—N3119.18 (8)
C13—C1—C2—N1−117.62 (8)C19—N4—C21—O4−173.52 (9)
C7—C1—C2—N1117.43 (8)C19—N4—C21—N35.89 (11)
C1—N2—C3—O2−175.31 (9)C20—N3—C21—O4174.30 (9)
C1—N2—C3—N13.84 (11)C22—N3—C21—O4−6.17 (15)
C2—N1—C3—O2175.12 (9)C22A—N3—C21—O42.5 (4)
C4—N1—C3—O2−2.40 (15)C20—N3—C21—N4−5.14 (11)
C2—N1—C3—N2−4.07 (11)C22—N3—C21—N4174.39 (9)
C4—N1—C3—N2178.41 (9)C22A—N3—C21—N4−176.9 (4)
C2—N1—C4—C576.00 (12)C20—N3—C22—C23111.2 (2)
C3—N1—C4—C5−106.80 (11)C21—N3—C22—C23−68.2 (2)
N1—C4—C5—C658.11 (14)N3—C22—C23—C24−57.2 (2)
N2—C1—C7—C84.56 (12)C20—N3—C22A—C23A74.1 (12)
C13—C1—C7—C8128.82 (9)C21—N3—C22A—C23A−115.0 (10)
C2—C1—C7—C8−105.67 (10)N3—C22A—C23A—C24A54.6 (15)
N2—C1—C7—C12−176.39 (8)N4—C19—C25—C2615.27 (12)
C13—C1—C7—C12−52.13 (11)C31—C19—C25—C26139.20 (9)
C2—C1—C7—C1273.38 (10)C20—C19—C25—C26−95.26 (10)
C12—C7—C8—C90.36 (15)N4—C19—C25—C30−166.60 (9)
C1—C7—C8—C9179.40 (9)C31—C19—C25—C30−42.67 (12)
C7—C8—C9—C100.23 (15)C20—C19—C25—C3082.87 (11)
C8—C9—C10—C11−0.98 (16)C30—C25—C26—C270.84 (15)
C9—C10—C11—C121.14 (16)C19—C25—C26—C27178.96 (9)
C10—C11—C12—C7−0.54 (16)C25—C26—C27—C280.11 (16)
C8—C7—C12—C11−0.20 (15)C26—C27—C28—C29−1.08 (16)
C1—C7—C12—C11−179.27 (9)C27—C28—C29—C301.12 (17)
N2—C1—C13—C18−111.24 (10)C28—C29—C30—C25−0.17 (17)
C7—C1—C13—C18123.27 (10)C26—C25—C30—C29−0.80 (16)
C2—C1—C13—C180.48 (13)C19—C25—C30—C29−178.97 (10)
N2—C1—C13—C1465.31 (11)N4—C19—C31—C32−116.77 (10)
C7—C1—C13—C14−60.18 (11)C25—C19—C31—C32117.75 (10)
C2—C1—C13—C14177.03 (8)C20—C19—C31—C32−5.14 (13)
C18—C13—C14—C150.66 (15)N4—C19—C31—C3660.99 (11)
C1—C13—C14—C15−176.04 (9)C25—C19—C31—C36−64.49 (11)
C13—C14—C15—C16−0.36 (17)C20—C19—C31—C36172.62 (9)
C14—C15—C16—C17−0.11 (16)C36—C31—C32—C33−0.25 (15)
C15—C16—C17—C180.29 (16)C19—C31—C32—C33177.46 (9)
C14—C13—C18—C17−0.48 (15)C31—C32—C33—C340.06 (16)
C1—C13—C18—C17176.00 (9)C32—C33—C34—C350.13 (16)
C16—C17—C18—C130.01 (16)C33—C34—C35—C36−0.13 (17)
C21—N4—C19—C31115.33 (9)C34—C35—C36—C31−0.07 (17)
C21—N4—C19—C25−119.49 (9)C32—C31—C36—C350.26 (16)
C21—N4—C19—C20−4.22 (10)C19—C31—C36—C35−177.61 (10)
C21—N3—C20—O3−177.70 (9)
Hydrogen-bond geometry (Å, º) top
Cg2, Cg5 and Cg6 are the centroids of the C25–C30, C7–C12 and C13–C18 phenyl rings, respectively.
D—H···AD—HH···AD···AD—H···A
N2—H2···O4i0.908 (14)1.915 (15)2.8211 (11)174.8 (12)
N4—H4···O2i0.913 (14)1.917 (14)2.8293 (10)177.3 (12)
C5—H5A···Cg5ii1.033 (15)2.651 (15)3.6101 (13)154.4 (11)
C15—H15···Cg2iii0.971 (15)2.925 (14)3.8055 (12)154.1 (12)
C23—H23A···Cg2ii0.992.923.8118 (15)151
C24—H24C···Cg6iv0.982.913.6320 (13)131
C35—H35···Cg50.981 (15)2.741 (15)3.6627 (13)156.9 (13)
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) x−1, y−1, z+1; (iv) x+1, y+1, z−1.
 

Acknowledgements

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

References

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 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
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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 2| Part 12| December 2017| x171808
https://doi.org/10.1107/S2414314617018089
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