(4E)-1-Phenyl-4-{[(pyridin-2-yl)amino]­methyl­idene}pyrazolidine-3,5-dione

Mohamed, S.K.; Mague, J.T.; Akkurt, M.; Khodairy, A.; Albayati, M.R.; Ahmed, E.A.

doi:10.1107/S2414314616009093

organic compounds

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ISSN: 2414-3146

Volume 1| Part 6| June 2016| x160909

doi:10.1107/S2414314616009093

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(4E)-1-Phenyl-4-{[(pyridin-2-yl)amino]methylidene}pyrazolidine-3,5-dione

Shaaban K. Mohamed,^a Joel T. Mague,^b Mehmet Akkurt,^c Ahmed Khodairy,^d Mustafa R. Albayati ^e ^* and Eman A. Ahmed ^e

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England, and, Chemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^dChemistry Department, Faculty of Science, Sohagt University, Sohag, Egypt, and ^eKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by E. R. T. Tiekink, Sunway University, Malaysia (Received 27 May 2016; accepted 6 June 2016; online 10 June 2016)

The title compound, C₁₅H₁₂N₄O₂, contains two independent molecules in the asymmetric unit. These differ in terms of dihedral angles that the phenyl and 2-pyridyl rings subtend with the central five-membered ring; 15.2 (2) and 2.9 (2)°, respectively, in one molecule, 8.9 (2) and 5.1 (2)°for the second. In the crystal, the independent molecules each self-associate to form layers through N—H⋯O and C—H⋯O hydrogen bonding. The layers associate through π–π interactions between the phenyl rings and isolated carbon–carbon double bonds [shortest midpoint–centroid distance = 3.347 (4) Å]. The crystal studied was refined as a two-component twin.

Keywords: crystal structure; pyrazoldiones; 1,2,4-triazoles; benzyidene-acetohydrazide.

CCDC reference: 1483676

Structure description

Pyrazolone scaffold compounds have been shown to possess diverse biological properties such as tranquilizing, muscle-relaxant, psycho-analeptic, anti-convulsant, anti-hypertensive, anti-depressant, anti-pyretic and analgesic activities (Turan-Zitouni et al., 2000 ; Rajendra Prasad et al., 2005 ). Some pyrazolone derivatives are used as anti-inflammatory (Bekhit et al., 2009a ,b ), anti-cancer (Nitulescu et al., 2010 ) and enzyme inhibitory (Li et al., 2004 ) agents. In this context, we report here the crystal structure of the title compound.

The asymmetric unit contains two independent molecules which differ modestly in their conformations, Fig. 1. Thus in molecule 1, the the phenyl and 2-pyridyl rings are inclined by 15.2 (2) and 2.9 (2)°, respectively, to the central five-membered ring while in molecule 2, the corresponding angles are 8.9 (2) and 5.1 (2)°. Through N—H⋯O and C—H⋯O hydrogen bonding, each independent molecule forms layers with its symmetry-related counterparts (Table 1 and Fig. 2). These layers are inclined at approximately 81° to one another. Successive layers containing molecule 1 associate via π–π interactions between the C1–C6 phenyl ring and the C8=C10 π-bond in the molecule at 1 − x, 2 − y, 1 − z with a midpoint–centroid distance of 3.347 (4) Å. An analogous interaction occurs between the layers comprising molecule 2 (C16–C21 ring and C23=C25 double bond) with a midpoint–centroid distance of 3.447 (4) Å.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.91 (5)	1.97 (5)	2.869 (3)	168 (4)
N3—H3A⋯O2	0.96 (5)	2.10 (5)	2.812 (4)	130 (4)
C2—H2⋯O1	0.94	2.33	2.920 (4)	121
C6—H6⋯O1ⁱ	0.94	2.57	3.401 (4)	147
C10—H10⋯O2ⁱⁱ	0.94	2.29	3.222 (4)	170
C12—H12⋯O2ⁱⁱ	0.94	2.24	3.175 (4)	170
N5—H5A⋯O3ⁱⁱ	0.86 (4)	2.02 (4)	2.866 (4)	171 (4)
N7—H7A⋯O4	0.94 (4)	2.03 (4)	2.794 (3)	138 (3)
C17—H17⋯O3	0.94	2.27	2.895 (4)	124
C21—H21⋯O3ⁱⁱ	0.94	2.53	3.392 (4)	153
C25—H25⋯O4ⁱ	0.94	2.30	3.230 (4)	172
C27—H27⋯O4ⁱ	0.94	2.29	3.222 (4)	173
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z.

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

Figure 2
Packing showing the intermolecular N—H⋯O and C—H⋯O hydrogen bonds as, respectively, blue and purple dotted lines.

Synthesis and crystallization

The title compound was prepared according to our reported method (Ahmed, 2015 ). Pale-yellow crystals suitable for X-ray analysis were grown from pyridine (m.p. 541–543 K, yield 91%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The crystal studied was refined as a two-component twin. Several reflections, i.e. (0 2 6), ( $[\overline{2}]$ $[\overline{9}]$ 5), ( $[\overline{1}]$ $[\overline{9}]$ 5), (0 $[\overline{9}]$ 5), ( $[\overline{1}]$ 9 $[\overline{5}]$ ) and (1 $[\overline{9}]$ 5) were omitted from the final cycles of refinement owing to poor agreement.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₁₂N₄O₂
M_r	280.29
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	220
a, b, c (Å)	6.2175 (2), 10.2646 (4), 20.7094 (8)
α, β, γ (°)	102.511 (2), 94.343 (2), 95.263 (2)
V (Å³)	1278.63 (8)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.83
Crystal size (mm)	0.21 × 0.07 × 0.02

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (TWINABS; Sheldrick, 2009 )
T_min, T_max	0.81, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	24529, 12138, 10472
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.620

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.171, 1.11
No. of reflections	12138
No. of parameters	396
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.22
Computer programs: APEX3 and SAINT (Bruker, 2016 ), SHELXT (Sheldrick, 2015a ), SHELXL2014/7 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1483676

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2414314616009093/tk4017sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616009093/tk4017Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616009093/tk4017Isup3.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: SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(4E)-1-Phenyl-4-{[(pyridin-2-yl)amino]methylidene}pyrazolidine-3,5-dione top

Crystal data top

C₁₅H₁₂N₄O₂	Z = 4
M_r = 280.29	F(000) = 584
Triclinic, P1	D_x = 1.456 Mg m⁻³
a = 6.2175 (2) Å	Cu Kα radiation, λ = 1.54178 Å
b = 10.2646 (4) Å	Cell parameters from 9905 reflections
c = 20.7094 (8) Å	θ = 4.4–72.9°
α = 102.511 (2)°	µ = 0.83 mm⁻¹
β = 94.343 (2)°	T = 220 K
γ = 95.263 (2)°	Column, yellow
V = 1278.63 (8) Å³	0.21 × 0.07 × 0.02 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	12138 independent reflections
Radiation source: INCOATEC IµS micro–focus source	10472 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.054
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.8°, θ_min = 4.4°
ω scans	h = −7→7
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009)	k = −12→12
T_min = 0.81, T_max = 0.98	l = −25→25
24529 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.066	Hydrogen site location: mixed
wR(F²) = 0.171	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0669P)² + 0.7168P] where P = (F_o² + 2F_c²)/3
12138 reflections	(Δ/σ)_max = 0.001
396 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Special details top

Experimental. Analysis of 1259 reflections having I/σ(I) > 13 and chosen from the full data set with CELL_NOW (Sheldrick, 2008) showed the crystal to belong to the triclinic system and to be twinned by a 180° rotation about the c* axis. The raw data were processed using the multi-component version of SAINT under control of the two-component orientation file generated by CELL_NOW.

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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 Å) and included as riding contributions with isotropic displacement parameters 1.2 times those of the attached atoms. Refined as a 2-component twin.

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

	x	y	z	U_iso*/U_eq
O1	0.2523 (4)	0.9078 (2)	0.56147 (13)	0.0414 (6)
O2	0.7975 (4)	0.6606 (3)	0.46405 (12)	0.0408 (6)
N1	0.7883 (4)	0.8648 (3)	0.53604 (14)	0.0335 (6)
H1A	0.932 (8)	0.888 (4)	0.549 (2)	0.056 (12)*
N2	0.6284 (4)	0.9343 (3)	0.56886 (13)	0.0327 (6)
N3	0.3715 (5)	0.5366 (3)	0.42450 (14)	0.0356 (6)
H3A	0.522 (8)	0.529 (5)	0.419 (2)	0.061 (13)*
N4	0.3472 (5)	0.3343 (3)	0.35087 (14)	0.0378 (6)
C1	0.6862 (5)	1.0608 (3)	0.61282 (15)	0.0315 (7)
C2	0.5388 (6)	1.1181 (4)	0.65468 (17)	0.0400 (8)
H2	0.3995	1.0731	0.6537	0.048*
C3	0.5980 (6)	1.2413 (4)	0.69752 (18)	0.0451 (8)
H3	0.4969	1.2804	0.7251	0.054*
C4	0.8024 (6)	1.3081 (4)	0.70074 (17)	0.0428 (8)
H4	0.8417	1.3914	0.7306	0.051*
C5	0.9486 (6)	1.2506 (4)	0.65940 (18)	0.0411 (8)
H5	1.0884	1.2955	0.6611	0.049*
C6	0.8923 (5)	1.1277 (3)	0.61545 (16)	0.0360 (7)
H6	0.9932	1.0896	0.5875	0.043*
C7	0.4242 (5)	0.8666 (3)	0.54520 (15)	0.0305 (6)
C8	0.4648 (5)	0.7457 (3)	0.49929 (15)	0.0309 (6)
C9	0.6952 (5)	0.7474 (3)	0.49606 (15)	0.0311 (6)
C10	0.3128 (5)	0.6440 (3)	0.46519 (15)	0.0325 (7)
H10	0.1650	0.6502	0.4706	0.039*
C11	0.2378 (5)	0.4245 (3)	0.38691 (15)	0.0328 (7)
C12	0.0137 (5)	0.4102 (3)	0.38836 (16)	0.0356 (7)
H12	−0.0566	0.4775	0.4141	0.043*
C13	−0.1015 (6)	0.2943 (4)	0.35084 (17)	0.0401 (8)
H13	−0.2531	0.2808	0.3508	0.048*
C14	0.0074 (6)	0.1972 (4)	0.31298 (17)	0.0420 (8)
H14	−0.0678	0.1169	0.2872	0.050*
C15	0.2289 (6)	0.2228 (4)	0.31449 (17)	0.0411 (8)
H15	0.3025	0.1579	0.2883	0.049*
O3	0.2981 (4)	0.1607 (3)	0.06003 (12)	0.0408 (6)
O4	−0.3107 (4)	0.3200 (3)	−0.03639 (12)	0.0377 (5)
N5	−0.2559 (4)	0.1755 (3)	0.03312 (14)	0.0332 (6)
H5A	−0.386 (7)	0.164 (4)	0.0435 (18)	0.038 (10)*
N6	−0.0752 (4)	0.1344 (3)	0.06515 (13)	0.0314 (6)
N7	0.0864 (4)	0.4084 (3)	−0.07590 (13)	0.0308 (5)
H7A	−0.065 (7)	0.406 (4)	−0.0776 (17)	0.036 (10)*
N8	0.0571 (4)	0.5406 (3)	−0.15078 (13)	0.0360 (6)
C16	−0.1045 (5)	0.0432 (3)	0.10675 (14)	0.0286 (6)
C17	0.0727 (5)	0.0106 (4)	0.14271 (16)	0.0359 (7)
H17	0.2138	0.0484	0.1394	0.043*
C18	0.0385 (6)	−0.0785 (4)	0.18350 (17)	0.0389 (7)
H18	0.1583	−0.1011	0.2076	0.047*
C19	−0.1664 (6)	−0.1346 (3)	0.18949 (17)	0.0380 (7)
H19	−0.1867	−0.1939	0.2179	0.046*
C20	−0.3419 (6)	−0.1028 (4)	0.15342 (19)	0.0418 (8)
H20	−0.4824	−0.1411	0.1571	0.050*
C21	−0.3126 (5)	−0.0150 (4)	0.11177 (17)	0.0366 (7)
H21	−0.4328	0.0054	0.0869	0.044*
C22	0.1142 (5)	0.1857 (3)	0.04333 (15)	0.0312 (6)
C23	0.0459 (5)	0.2672 (3)	−0.00137 (14)	0.0284 (6)
C24	−0.1876 (5)	0.2606 (3)	−0.00493 (15)	0.0293 (6)
C25	0.1733 (5)	0.3375 (3)	−0.03593 (14)	0.0295 (6)
H25	0.3246	0.3358	−0.0314	0.035*
C26	0.1927 (5)	0.4805 (3)	−0.11675 (14)	0.0298 (6)
C27	0.4153 (5)	0.4882 (4)	−0.12135 (17)	0.0373 (7)
H27	0.5054	0.4444	−0.0965	0.045*
C28	0.4998 (6)	0.5628 (4)	−0.16385 (18)	0.0435 (8)
H28	0.6495	0.5706	−0.1682	0.052*
C29	0.3636 (6)	0.6253 (4)	−0.19946 (19)	0.0483 (9)
H29	0.4173	0.6758	−0.2288	0.058*
C30	0.1447 (6)	0.6116 (4)	−0.19100 (18)	0.0441 (8)
H30	0.0518	0.6552	−0.2151	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0212 (11)	0.0423 (14)	0.0570 (14)	0.0073 (10)	0.0067 (10)	0.0002 (11)
O2	0.0268 (12)	0.0421 (14)	0.0498 (13)	0.0088 (10)	0.0078 (10)	−0.0013 (10)
N1	0.0182 (13)	0.0360 (15)	0.0447 (14)	0.0067 (11)	0.0059 (10)	0.0028 (12)
N2	0.0191 (12)	0.0351 (15)	0.0432 (14)	0.0061 (11)	0.0051 (10)	0.0058 (11)
N3	0.0278 (14)	0.0388 (15)	0.0391 (13)	0.0062 (11)	0.0040 (11)	0.0051 (11)
N4	0.0313 (15)	0.0400 (16)	0.0424 (14)	0.0099 (12)	0.0081 (12)	0.0060 (12)
C1	0.0291 (15)	0.0334 (16)	0.0333 (14)	0.0069 (13)	0.0023 (12)	0.0089 (12)
C2	0.0312 (17)	0.0424 (19)	0.0455 (17)	0.0038 (15)	0.0079 (14)	0.0066 (15)
C3	0.042 (2)	0.044 (2)	0.0460 (18)	0.0065 (16)	0.0089 (15)	0.0023 (15)
C4	0.048 (2)	0.0339 (18)	0.0428 (17)	0.0052 (16)	−0.0029 (15)	0.0029 (14)
C5	0.0360 (19)	0.0374 (19)	0.0488 (18)	−0.0034 (15)	−0.0025 (14)	0.0124 (15)
C6	0.0290 (16)	0.0388 (18)	0.0415 (16)	0.0063 (13)	0.0046 (13)	0.0104 (14)
C7	0.0202 (14)	0.0348 (17)	0.0370 (15)	0.0049 (12)	0.0046 (11)	0.0079 (12)
C8	0.0241 (15)	0.0350 (17)	0.0354 (15)	0.0069 (12)	0.0048 (11)	0.0097 (12)
C9	0.0238 (15)	0.0365 (17)	0.0334 (14)	0.0077 (12)	0.0040 (11)	0.0066 (12)
C10	0.0276 (16)	0.0347 (17)	0.0362 (15)	0.0053 (13)	0.0045 (12)	0.0087 (13)
C11	0.0296 (16)	0.0344 (17)	0.0349 (15)	0.0065 (13)	0.0034 (12)	0.0078 (12)
C12	0.0303 (16)	0.0360 (17)	0.0417 (16)	0.0116 (13)	0.0078 (13)	0.0065 (13)
C13	0.0348 (18)	0.0432 (19)	0.0418 (17)	0.0043 (15)	0.0038 (14)	0.0086 (14)
C14	0.043 (2)	0.0381 (19)	0.0410 (17)	0.0019 (15)	0.0035 (14)	0.0030 (14)
C15	0.044 (2)	0.0365 (18)	0.0418 (17)	0.0107 (15)	0.0070 (15)	0.0029 (14)
O3	0.0229 (11)	0.0524 (15)	0.0549 (14)	0.0105 (10)	0.0052 (10)	0.0261 (12)
O4	0.0228 (11)	0.0484 (14)	0.0474 (12)	0.0089 (10)	0.0013 (9)	0.0218 (11)
N5	0.0172 (13)	0.0410 (16)	0.0466 (14)	0.0076 (11)	0.0040 (11)	0.0190 (12)
N6	0.0211 (13)	0.0354 (14)	0.0417 (13)	0.0080 (11)	0.0025 (10)	0.0158 (11)
N7	0.0222 (13)	0.0358 (14)	0.0374 (13)	0.0072 (10)	0.0041 (10)	0.0125 (11)
N8	0.0287 (14)	0.0420 (16)	0.0406 (14)	0.0074 (12)	0.0017 (11)	0.0158 (12)
C16	0.0278 (15)	0.0265 (15)	0.0320 (13)	0.0056 (12)	0.0052 (11)	0.0057 (11)
C17	0.0277 (16)	0.0405 (18)	0.0428 (16)	0.0045 (14)	0.0047 (13)	0.0158 (14)
C18	0.0344 (17)	0.0436 (19)	0.0416 (17)	0.0100 (15)	0.0010 (13)	0.0145 (14)
C19	0.0393 (18)	0.0355 (18)	0.0427 (17)	0.0065 (14)	0.0071 (14)	0.0143 (14)
C20	0.0290 (17)	0.0409 (19)	0.059 (2)	0.0014 (14)	0.0101 (15)	0.0172 (16)
C21	0.0236 (15)	0.0413 (19)	0.0486 (17)	0.0061 (13)	0.0055 (13)	0.0163 (14)
C22	0.0257 (15)	0.0344 (17)	0.0348 (14)	0.0044 (12)	0.0042 (12)	0.0097 (12)
C23	0.0220 (14)	0.0318 (16)	0.0329 (14)	0.0065 (12)	0.0036 (11)	0.0086 (12)
C24	0.0244 (15)	0.0311 (16)	0.0344 (14)	0.0073 (12)	0.0035 (11)	0.0094 (12)
C25	0.0226 (14)	0.0342 (16)	0.0329 (14)	0.0052 (12)	0.0041 (11)	0.0092 (12)
C26	0.0286 (15)	0.0298 (16)	0.0315 (14)	0.0066 (12)	0.0022 (11)	0.0067 (12)
C27	0.0257 (16)	0.0446 (19)	0.0466 (17)	0.0090 (14)	0.0061 (13)	0.0184 (15)
C28	0.0269 (17)	0.054 (2)	0.054 (2)	0.0039 (15)	0.0116 (14)	0.0197 (17)
C29	0.044 (2)	0.057 (2)	0.0507 (19)	0.0005 (18)	0.0082 (16)	0.0290 (18)
C30	0.0353 (18)	0.057 (2)	0.0472 (18)	0.0104 (16)	0.0016 (14)	0.0258 (17)

Geometric parameters (Å, º) top

O1—C7	1.229 (4)	O3—C22	1.235 (4)
O2—C9	1.245 (4)	O4—C24	1.251 (4)
N1—C9	1.356 (4)	N5—C24	1.358 (4)
N1—N2	1.408 (4)	N5—N6	1.406 (3)
N1—H1A	0.91 (5)	N5—H5A	0.86 (4)
N2—C7	1.390 (4)	N6—C22	1.392 (4)
N2—C1	1.413 (4)	N6—C16	1.412 (4)
N3—C10	1.333 (4)	N7—C25	1.331 (4)
N3—C11	1.400 (4)	N7—C26	1.402 (4)
N3—H3A	0.96 (5)	N7—H7A	0.94 (4)
N4—C11	1.330 (4)	N8—C30	1.334 (4)
N4—C15	1.345 (4)	N8—C26	1.335 (4)
C1—C6	1.389 (5)	C16—C17	1.390 (4)
C1—C2	1.391 (5)	C16—C21	1.395 (4)
C2—C3	1.378 (5)	C17—C18	1.386 (5)
C2—H2	0.9400	C17—H17	0.9400
C3—C4	1.377 (6)	C18—C19	1.375 (5)
C3—H3	0.9400	C18—H18	0.9400
C4—C5	1.380 (5)	C19—C20	1.379 (5)
C4—H4	0.9400	C19—H19	0.9400
C5—C6	1.384 (5)	C20—C21	1.386 (5)
C5—H5	0.9400	C20—H20	0.9400
C6—H6	0.9400	C21—H21	0.9400
C7—C8	1.445 (4)	C22—C23	1.441 (4)
C8—C10	1.371 (4)	C23—C25	1.366 (4)
C8—C9	1.438 (4)	C23—C24	1.442 (4)
C10—H10	0.9400	C25—H25	0.9400
C11—C12	1.391 (5)	C26—C27	1.391 (4)
C12—C13	1.375 (5)	C27—C28	1.388 (5)
C12—H12	0.9400	C27—H27	0.9400
C13—C14	1.390 (5)	C28—C29	1.372 (5)
C13—H13	0.9400	C28—H28	0.9400
C14—C15	1.375 (5)	C29—C30	1.383 (5)
C14—H14	0.9400	C29—H29	0.9400
C15—H15	0.9400	C30—H30	0.9400

C9—N1—N2	109.8 (2)	C24—N5—N6	109.6 (2)
C9—N1—H1A	126 (3)	C24—N5—H5A	125 (3)
N2—N1—H1A	122 (3)	N6—N5—H5A	124 (3)
C7—N2—N1	109.7 (2)	C22—N6—N5	109.5 (2)
C7—N2—C1	129.7 (3)	C22—N6—C16	129.9 (3)
N1—N2—C1	120.2 (2)	N5—N6—C16	120.2 (2)
C10—N3—C11	128.0 (3)	C25—N7—C26	127.9 (3)
C10—N3—H3A	120 (3)	C25—N7—H7A	115 (2)
C11—N3—H3A	112 (3)	C26—N7—H7A	117 (2)
C11—N4—C15	116.3 (3)	C30—N8—C26	116.8 (3)
C6—C1—C2	119.5 (3)	C17—C16—C21	119.7 (3)
C6—C1—N2	120.1 (3)	C17—C16—N6	120.4 (3)
C2—C1—N2	120.4 (3)	C21—C16—N6	119.9 (3)
C3—C2—C1	119.7 (3)	C18—C17—C16	119.1 (3)
C3—C2—H2	120.2	C18—C17—H17	120.4
C1—C2—H2	120.2	C16—C17—H17	120.4
C4—C3—C2	121.3 (3)	C19—C18—C17	121.6 (3)
C4—C3—H3	119.4	C19—C18—H18	119.2
C2—C3—H3	119.4	C17—C18—H18	119.2
C3—C4—C5	118.9 (3)	C18—C19—C20	119.2 (3)
C3—C4—H4	120.6	C18—C19—H19	120.4
C5—C4—H4	120.6	C20—C19—H19	120.4
C4—C5—C6	120.9 (3)	C19—C20—C21	120.5 (3)
C4—C5—H5	119.5	C19—C20—H20	119.7
C6—C5—H5	119.5	C21—C20—H20	119.7
C5—C6—C1	119.8 (3)	C20—C21—C16	119.9 (3)
C5—C6—H6	120.1	C20—C21—H21	120.0
C1—C6—H6	120.1	C16—C21—H21	120.0
O1—C7—N2	124.5 (3)	O3—C22—N6	124.4 (3)
O1—C7—C8	130.4 (3)	O3—C22—C23	129.9 (3)
N2—C7—C8	105.1 (3)	N6—C22—C23	105.8 (3)
C10—C8—C9	124.9 (3)	C25—C23—C22	127.7 (3)
C10—C8—C7	126.7 (3)	C25—C23—C24	124.6 (3)
C9—C8—C7	108.4 (3)	C22—C23—C24	107.7 (3)
O2—C9—N1	124.4 (3)	O4—C24—N5	124.4 (3)
O2—C9—C8	128.8 (3)	O4—C24—C23	128.3 (3)
N1—C9—C8	106.8 (3)	N5—C24—C23	107.3 (3)
N3—C10—C8	121.0 (3)	N7—C25—C23	120.9 (3)
N3—C10—H10	119.5	N7—C25—H25	119.5
C8—C10—H10	119.5	C23—C25—H25	119.5
N4—C11—C12	124.3 (3)	N8—C26—C27	123.7 (3)
N4—C11—N3	113.2 (3)	N8—C26—N7	112.7 (3)
C12—C11—N3	122.5 (3)	C27—C26—N7	123.5 (3)
C13—C12—C11	117.7 (3)	C28—C27—C26	117.7 (3)
C13—C12—H12	121.1	C28—C27—H27	121.1
C11—C12—H12	121.1	C26—C27—H27	121.1
C12—C13—C14	119.7 (3)	C29—C28—C27	119.6 (3)
C12—C13—H13	120.2	C29—C28—H28	120.2
C14—C13—H13	120.2	C27—C28—H28	120.2
C15—C14—C13	117.7 (3)	C28—C29—C30	118.0 (3)
C15—C14—H14	121.2	C28—C29—H29	121.0
C13—C14—H14	121.2	C30—C29—H29	121.0
N4—C15—C14	124.4 (3)	N8—C30—C29	124.2 (3)
N4—C15—H15	117.8	N8—C30—H30	117.9
C14—C15—H15	117.8	C29—C30—H30	117.9

C9—N1—N2—C7	−5.5 (4)	C24—N5—N6—C22	−4.7 (3)
C9—N1—N2—C1	−179.2 (3)	C24—N5—N6—C16	−178.8 (3)
C7—N2—C1—C6	−161.3 (3)	C22—N6—C16—C17	12.5 (5)
N1—N2—C1—C6	11.0 (4)	N5—N6—C16—C17	−174.8 (3)
C7—N2—C1—C2	19.9 (5)	C22—N6—C16—C21	−167.4 (3)
N1—N2—C1—C2	−167.8 (3)	N5—N6—C16—C21	5.3 (4)
C6—C1—C2—C3	0.9 (5)	C21—C16—C17—C18	−0.6 (5)
N2—C1—C2—C3	179.7 (3)	N6—C16—C17—C18	179.5 (3)
C1—C2—C3—C4	−1.2 (6)	C16—C17—C18—C19	−0.4 (5)
C2—C3—C4—C5	0.9 (6)	C17—C18—C19—C20	0.9 (5)
C3—C4—C5—C6	−0.2 (5)	C18—C19—C20—C21	−0.3 (5)
C4—C5—C6—C1	−0.1 (5)	C19—C20—C21—C16	−0.7 (5)
C2—C1—C6—C5	−0.2 (5)	C17—C16—C21—C20	1.2 (5)
N2—C1—C6—C5	−179.0 (3)	N6—C16—C21—C20	−179.0 (3)
N1—N2—C7—O1	−175.1 (3)	N5—N6—C22—O3	−176.0 (3)
C1—N2—C7—O1	−2.2 (5)	C16—N6—C22—O3	−2.6 (5)
N1—N2—C7—C8	4.0 (3)	N5—N6—C22—C23	3.0 (3)
C1—N2—C7—C8	177.0 (3)	C16—N6—C22—C23	176.3 (3)
O1—C7—C8—C10	−3.6 (6)	O3—C22—C23—C25	−0.4 (6)
N2—C7—C8—C10	177.3 (3)	N6—C22—C23—C25	−179.3 (3)
O1—C7—C8—C9	177.7 (3)	O3—C22—C23—C24	178.5 (3)
N2—C7—C8—C9	−1.4 (3)	N6—C22—C23—C24	−0.3 (3)
N2—N1—C9—O2	−175.1 (3)	N6—N5—C24—O4	−175.7 (3)
N2—N1—C9—C8	4.4 (4)	N6—N5—C24—C23	4.3 (3)
C10—C8—C9—O2	−1.1 (6)	C25—C23—C24—O4	−3.5 (5)
C7—C8—C9—O2	177.7 (3)	C22—C23—C24—O4	177.5 (3)
C10—C8—C9—N1	179.4 (3)	C25—C23—C24—N5	176.5 (3)
C7—C8—C9—N1	−1.9 (4)	C22—C23—C24—N5	−2.5 (3)
C11—N3—C10—C8	179.3 (3)	C26—N7—C25—C23	−176.9 (3)
C9—C8—C10—N3	−0.9 (5)	C22—C23—C25—N7	179.7 (3)
C7—C8—C10—N3	−179.4 (3)	C24—C23—C25—N7	0.9 (5)
C15—N4—C11—C12	−0.6 (5)	C30—N8—C26—C27	−0.1 (5)
C15—N4—C11—N3	178.8 (3)	C30—N8—C26—N7	−180.0 (3)
C10—N3—C11—N4	179.6 (3)	C25—N7—C26—N8	179.9 (3)
C10—N3—C11—C12	−1.0 (5)	C25—N7—C26—C27	0.0 (5)
N4—C11—C12—C13	1.1 (5)	N8—C26—C27—C28	0.0 (5)
N3—C11—C12—C13	−178.2 (3)	N7—C26—C27—C28	179.8 (3)
C11—C12—C13—C14	−0.5 (5)	C26—C27—C28—C29	−0.2 (6)
C12—C13—C14—C15	−0.5 (5)	C27—C28—C29—C30	0.4 (6)
C11—N4—C15—C14	−0.5 (5)	C26—N8—C30—C29	0.4 (6)
C13—C14—C15—N4	1.1 (6)	C28—C29—C30—N8	−0.6 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.91 (5)	1.97 (5)	2.869 (3)	168 (4)
N3—H3A···O2	0.96 (5)	2.10 (5)	2.812 (4)	130 (4)
C2—H2···O1	0.94	2.33	2.920 (4)	121
C6—H6···O1ⁱ	0.94	2.57	3.401 (4)	147
C10—H10···O2ⁱⁱ	0.94	2.29	3.222 (4)	170
C12—H12···O2ⁱⁱ	0.94	2.24	3.175 (4)	170
N5—H5A···O3ⁱⁱ	0.86 (4)	2.02 (4)	2.866 (4)	171 (4)
N7—H7A···O4	0.94 (4)	2.03 (4)	2.794 (3)	138 (3)
C17—H17···O3	0.94	2.27	2.895 (4)	124
C21—H21···O3ⁱⁱ	0.94	2.53	3.392 (4)	153
C25—H25···O4ⁱ	0.94	2.30	3.230 (4)	172
C27—H27···O4ⁱ	0.94	2.29	3.222 (4)	173

Symmetry codes: (i) x+1, y, z; (ii) 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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