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ISSN: 2414-3146

4-Meth­oxy-N,N′-di­phenyl­benzamidinium nitrate

aInstituto de Ciencias Exatas, Departamento de Quimica, Universidade Federal Rural do Rio de Janeiro, Seropedica–RJ, CEP 23070-200, Brazil
*Correspondence e-mail: herbst@ufrrj.br

Edited by J. Simpson, University of Otago, New Zealand (Received 27 August 2016; accepted 31 August 2016; online 5 September 2016)

The asymmetric unit of the title salt N,N′-diphenyl-4-meth­oxy­benzamidinium nitrate, C20H19N2O+·NO3, comprises two independent N,N′-diphenyl-4-meth­oxy­benzamidinium cations and two nitrate anions. The crystal structure features N—H⋯O hydrogen bonds and C—H⋯O contacts responsible for the packing.

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

Structure description

In the asymmetric unit of the title compound there are two independent N,N′-diphenyl-4-meth­oxy-benzamidinium cations (A and B) and two nitrate anions, as shown in Figs. 1[link] and 2[link]. The protonation of the neutral amidine leads to important changes to the NCN moiety of the N,N′-diphenyl-4-meth­oxy-benzamidinium cation, with C—N bond lengths all close to 1.33 Å [C1A—N1A = 1.328 (4) Å, C1A—N2A = C1B—N1B = 1.324 (4) Å and C1B—N2B = 1.331 (3)]. By comparison, in the crystal structure of the neutral N,N′-diphenyl-4-meth­oxy-benzamidine, previously reported (Bortoluzzi et al., 2004[Bortoluzzi, A. J., Echevarria, A. & Rodrigues-Santos, C. E. (2004). Acta Cryst. E60, o1837-o1839.]), two distinct C—N bond lengths, one short, 1.283 (2) Å (signifying C=N double-bond character) and one significantly longer, 1.372 (2) Å (commensurate with a single C—N bond). The maximum difference between the C—N bond lengths (ΔCN) in the amidinium nitrate salt is only 0.011 Å, suggesting greater conjugation than in the neutral amidine, where the corresponding ΔCN = 0.089 Å (Bortoluzzi et al., 2004[Bortoluzzi, A. J., Echevarria, A. & Rodrigues-Santos, C. E. (2004). Acta Cryst. E60, o1837-o1839.]). The N—C—N and N—C—C bond angles in the amidinium moieties range from 117.5 (2) to 123.8 (3)° confirming the sp2 character of the C1A and C1B atoms. This further corroborates the extensive conjugation in the NCN amidinium unit. The 4-meth­oxy-N-phenyl and amidinium moieties are almost coplanar in both the A and B mol­ecules with torsion angles of −22.4 (4)° (N1A—C1A—C2A—C7A), 29.5 (4)° (N1B—C1B—C2B—C7B), 22.0 (4)° (N2A—C1A—C2A—C3A), and 32.9 (4)° (N2B—C1B—C2B—C3B). The 4-meth­oxy-N-phenyl and the two N-benzamidine ring planes are nearly orthogonal in mol­ecule B [86.50 (9) and 88.20 (9)°], while in mol­ecule A they are 74.77 (9) and 75.62 (9)°, respectively.

[Figure 1]
Figure 1
The mol­ecular structure of the first ion pair in the title compound. Displacement ellipsoids are drawn at the 40% probability level.
[Figure 2]
Figure 2
The mol­ecular structure of the second ion pair in the title compound. Displacement ellipsoids are drawn at the 40% probability level.

In the crystal, N—H⋯O and N—H⋯(O,O) hydrogen bonds (Table 1[link]) link the components into [100] chains of alternating cations and anions, as shown in Fig. 3[link]. The packing is consolidated by C—H⋯O contacts.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1A—H1A⋯O5B 0.87 (3) 2.00 (3) 2.838 (4) 160 (3)
N1B—H1B⋯O2Ai 0.87 (3) 2.45 (3) 3.214 (4) 148 (3)
N1B—H1B⋯O3Ai 0.87 (3) 2.01 (3) 2.804 (4) 151 (3)
N1B—H1B⋯N3Ai 0.87 (3) 2.59 (3) 3.431 (4) 165 (3)
N2A—H2A⋯O3Bii 0.84 (3) 2.20 (3) 3.006 (4) 160 (3)
N2A—H2A⋯O4Bii 0.84 (3) 2.41 (3) 3.110 (4) 140 (3)
N2A—H2A⋯N3Bii 0.84 (3) 2.69 (3) 3.506 (4) 163 (3)
N2B—H2B⋯O4A 0.95 (4) 1.88 (4) 2.798 (3) 161 (3)
C20B—H20B⋯O3Aiii 0.93 2.49 3.288 (4) 144
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z; (iii) -x+1, -y+1, -z+1.
[Figure 3]
Figure 3
Details of the crystal packing showing the supra­molecular chain formed by the hydrogen-bonding network. [Symmetry code: (ii) x + 1, y, z.]

Synthesis and crystallization

The preparation of N,N′-diphenyl-4-meth­oxy-benzamidine was performed according to the method described elsewhere (Bortoluzzi et al., 2004[Bortoluzzi, A. J., Echevarria, A. & Rodrigues-Santos, C. E. (2004). Acta Cryst. E60, o1837-o1839.]). The nitrate salt was obtained by mixing equimolar ethano­lic solutions of nitric acid and N,N′-diphenyl-4-meth­oxy-benzamidine at room temperature for 2 h. In a few days, colourless needle single crystals were obtained and filtered off. Additional characterization: m.p. 128–130°C); IR (ATR): 3370, 3190, 2937, 2843, 1626, 1602, 1581, 1554, 1516, 1491, 1373, 1330, 1309, 1257, 1190, 1047, 1022, 868, 754, 688 cm−1. The strong band at 3190 cm−1 is assigned to the N—H stretching in the hydrogen-bonded amidinium-nitrate (N—H⋯O) system. The weak bands at 1373, 1330 and 1047 are tentatively assigned to the ν3 and ν1 nitrate vibrations in a hydrogen-bonded C2v point group.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula C20H19N2O+·NO3
Mr 365.38
Crystal system, space group Monoclinic, P21/n
Temperature (K) 293
a, b, c (Å) 8.9453 (6), 24.8813 (17), 17.3105 (11)
β (°) 103.135 (2)
V3) 3752.0 (4)
Z 8
Radiation type Mo Kα
μ (mm−1) 0.09
Crystal size (mm) 0.36 × 0.24 × 0.21
 
Data collection
Diffractometer Bruker D8 Venture
Absorption correction Multi-scan (SADABS; Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.659, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections 11714, 7113, 4403
Rint 0.033
(sin θ/λ)max−1) 0.610
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.069, 0.209, 1.03
No. of reflections 7036
No. of parameters 503
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.69, −0.29
Computer programs: APEX2 and SAINT (Bruker 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.].), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]), WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Structural data


Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: APEX2 (Bruker, 2012); data reduction: SAINT (Bruker 2012.); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).

4-Methoxy-N,N'-diphenylbenzamidinium nitrate top
Crystal data top
C20H19N2O+·NO3Dx = 1.294 Mg m3
Mr = 365.38Melting point: 402 K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.9453 (6) ÅCell parameters from 7126 reflections
b = 24.8813 (17) Åθ = 2.5–25.8°
c = 17.3105 (11) ŵ = 0.09 mm1
β = 103.135 (2)°T = 293 K
V = 3752.0 (4) Å3Block, colourless
Z = 80.36 × 0.24 × 0.21 mm
F(000) = 1536
Data collection top
Bruker D8 Venture
diffractometer
4403 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.033
φ and ω scansθmax = 25.7°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 1010
Tmin = 0.659, Tmax = 0.745k = 3023
11714 measured reflectionsl = 2021
7113 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.069H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.209 w = 1/[σ2(Fo2) + (0.0824P)2 + 2.7248P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
7036 reflectionsΔρmax = 0.69 e Å3
503 parametersΔρmin = 0.29 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N2A0.7989 (3)0.37589 (10)0.79592 (15)0.0477 (6)
N2B0.3596 (3)0.42303 (10)0.55453 (14)0.0472 (6)
N1A0.5570 (3)0.35693 (10)0.81612 (15)0.0500 (6)
O1B0.2700 (3)0.62172 (10)0.77506 (14)0.0800 (8)
N1B0.1099 (3)0.41057 (10)0.57207 (16)0.0510 (6)
O1A0.6056 (3)0.17070 (9)0.57383 (15)0.0818 (8)
O4A0.6337 (3)0.48135 (11)0.57798 (18)0.0836 (8)
O3A0.8626 (3)0.48148 (11)0.56225 (18)0.0855 (8)
N3B0.1528 (3)0.31588 (11)0.79441 (16)0.0568 (7)
C2A0.6604 (3)0.30014 (11)0.72843 (16)0.0426 (6)
O5B0.2803 (3)0.29768 (11)0.7990 (2)0.1005 (10)
C1A0.6732 (3)0.34595 (11)0.78207 (16)0.0439 (6)
N3A0.7594 (3)0.45868 (11)0.58905 (17)0.0591 (7)
C15B0.3576 (3)0.38825 (12)0.48831 (17)0.0478 (7)
C9B0.0772 (3)0.35765 (11)0.54199 (18)0.0486 (7)
O4B0.0561 (3)0.28941 (14)0.8181 (2)0.1065 (10)
C2B0.2558 (3)0.48531 (11)0.63535 (15)0.0420 (6)
C15A0.8143 (3)0.43056 (11)0.82121 (16)0.0469 (7)
C9A0.5648 (3)0.38266 (11)0.89039 (17)0.0496 (7)
C1B0.2410 (3)0.43739 (11)0.58449 (16)0.0423 (6)
C7A0.5594 (3)0.25777 (12)0.73282 (18)0.0514 (7)
H7A0.50260.25820.77160.062*
O3B0.1133 (4)0.35961 (11)0.76528 (19)0.1012 (10)
C3B0.3441 (3)0.52909 (12)0.62266 (16)0.0477 (7)
H3B0.39770.52750.58260.057*
O2A0.7876 (4)0.41745 (12)0.62410 (19)0.1081 (11)
C4B0.3533 (4)0.57487 (12)0.66859 (17)0.0531 (7)
H4B0.41410.60360.65980.064*
C3A0.7485 (4)0.29716 (12)0.67163 (17)0.0520 (7)
H3A0.81740.32460.66840.062*
C20B0.2472 (4)0.39402 (13)0.41896 (18)0.0572 (8)
H20B0.17430.42120.41350.069*
C10B0.1730 (4)0.31529 (12)0.5716 (2)0.0584 (8)
H10B0.25820.32060.61310.070*
C7B0.1763 (4)0.48893 (13)0.69605 (19)0.0598 (8)
H7B0.11810.46000.70640.072*
C10A0.6878 (4)0.37420 (13)0.95373 (18)0.0584 (8)
H10A0.77100.35380.94690.070*
C6A0.5436 (4)0.21568 (12)0.6804 (2)0.0576 (8)
H6A0.47430.18830.68290.069*
C5A0.6310 (4)0.21391 (12)0.62346 (18)0.0567 (8)
C4A0.7351 (4)0.25428 (12)0.62014 (19)0.0596 (8)
H4A0.79610.25260.58330.072*
C5B0.2723 (4)0.57808 (12)0.72751 (17)0.0554 (8)
C14A0.4422 (4)0.41288 (13)0.9002 (2)0.0638 (9)
H14A0.35910.41880.85780.077*
C20A0.7020 (4)0.46773 (13)0.7925 (2)0.0690 (9)
H20A0.61140.45740.75760.083*
C14B0.0524 (4)0.34912 (14)0.4839 (2)0.0653 (9)
H14B0.11930.37740.46590.078*
C16A0.9499 (4)0.44621 (14)0.87062 (19)0.0643 (9)
H16A1.02750.42130.88830.077*
C16B0.4699 (4)0.34992 (14)0.4945 (2)0.0656 (9)
H16B0.54690.34730.54060.079*
C6B0.1837 (4)0.53497 (14)0.7404 (2)0.0683 (10)
H6B0.12840.53720.77980.082*
C11A0.6876 (5)0.39592 (15)1.0271 (2)0.0752 (11)
H11A0.77050.39001.06960.090*
C11B0.1398 (5)0.26471 (13)0.5383 (2)0.0718 (10)
H11B0.20420.23600.55730.086*
C19B0.2474 (4)0.35803 (16)0.3568 (2)0.0725 (10)
H19B0.17270.36090.30990.087*
C12B0.0139 (5)0.25647 (15)0.4782 (2)0.0730 (10)
H12B0.00530.22260.45520.088*
C13B0.0837 (4)0.29793 (16)0.4518 (2)0.0756 (11)
H13B0.17150.29200.41220.091*
C18B0.3564 (5)0.31886 (15)0.3647 (2)0.0741 (11)
H18B0.35420.29460.32360.089*
C17B0.4679 (5)0.31519 (15)0.4320 (3)0.0786 (11)
H17B0.54380.28910.43620.094*
C13A0.4439 (5)0.43467 (15)0.9749 (3)0.0824 (12)
H13A0.36140.45520.98220.099*
C17A0.9700 (5)0.49970 (17)0.8940 (2)0.0815 (12)
H17A1.06090.51050.92820.098*
C12A0.5663 (6)0.42590 (17)1.0374 (2)0.0844 (12)
H12A0.56650.44051.08690.101*
C18A0.8582 (7)0.53605 (17)0.8672 (3)0.0931 (14)
H18A0.87160.57170.88330.112*
C01G0.3710 (6)0.66524 (16)0.7702 (3)0.0968 (14)
H01A0.35760.69300.80650.145*
H01B0.47520.65270.78370.145*
H01C0.34820.67930.71720.145*
C19A0.7252 (6)0.52031 (16)0.8162 (3)0.0938 (14)
H19A0.64930.54560.79720.113*
C8A0.6977 (7)0.16646 (18)0.5163 (3)0.1156 (18)
H8A10.66940.13460.48500.173*
H8A20.68110.19740.48230.173*
H8A30.80410.16450.54290.173*
H2A0.879 (4)0.3634 (12)0.7843 (17)0.053 (9)*
H1A0.469 (4)0.3412 (12)0.7986 (16)0.047 (8)*
H1B0.031 (4)0.4262 (13)0.5838 (18)0.057 (9)*
H2B0.454 (5)0.4415 (16)0.575 (2)0.090 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N2A0.0402 (14)0.0433 (14)0.0616 (15)0.0014 (11)0.0155 (12)0.0046 (11)
N2B0.0379 (13)0.0495 (14)0.0553 (14)0.0010 (11)0.0130 (11)0.0097 (12)
N1A0.0383 (14)0.0540 (15)0.0580 (15)0.0032 (12)0.0121 (12)0.0098 (12)
O1B0.120 (2)0.0624 (15)0.0703 (15)0.0161 (14)0.0478 (15)0.0238 (12)
N1B0.0408 (14)0.0450 (14)0.0715 (17)0.0002 (11)0.0219 (12)0.0095 (12)
O1A0.116 (2)0.0496 (14)0.0845 (17)0.0149 (13)0.0332 (16)0.0200 (12)
O4A0.0500 (14)0.0763 (17)0.127 (2)0.0007 (13)0.0261 (14)0.0018 (16)
O3A0.0590 (15)0.0775 (17)0.127 (2)0.0092 (13)0.0352 (15)0.0114 (16)
N3B0.0523 (16)0.0511 (16)0.0677 (17)0.0038 (13)0.0148 (13)0.0021 (13)
C2A0.0419 (15)0.0368 (14)0.0474 (15)0.0045 (12)0.0068 (12)0.0020 (12)
O5B0.0414 (14)0.0766 (18)0.185 (3)0.0080 (13)0.0286 (16)0.0061 (19)
C1A0.0408 (15)0.0419 (15)0.0481 (15)0.0046 (12)0.0084 (12)0.0021 (12)
N3A0.0411 (15)0.0553 (17)0.0824 (19)0.0030 (13)0.0171 (14)0.0172 (15)
C15B0.0428 (16)0.0493 (17)0.0550 (17)0.0047 (13)0.0185 (13)0.0084 (14)
C9B0.0460 (16)0.0418 (16)0.0633 (18)0.0031 (13)0.0232 (14)0.0053 (14)
O4B0.0689 (18)0.122 (3)0.139 (3)0.0125 (17)0.0453 (18)0.019 (2)
C2B0.0387 (14)0.0441 (15)0.0429 (14)0.0030 (12)0.0091 (12)0.0019 (12)
C15A0.0525 (17)0.0416 (15)0.0503 (16)0.0056 (13)0.0196 (14)0.0032 (13)
C9A0.0525 (18)0.0438 (16)0.0559 (17)0.0064 (13)0.0194 (14)0.0032 (13)
C1B0.0368 (15)0.0404 (15)0.0488 (15)0.0047 (12)0.0083 (12)0.0044 (12)
C7A0.0455 (17)0.0484 (17)0.0621 (18)0.0007 (13)0.0158 (14)0.0009 (14)
O3B0.125 (3)0.0621 (17)0.112 (2)0.0198 (16)0.0188 (19)0.0215 (16)
C3B0.0469 (16)0.0522 (17)0.0477 (15)0.0011 (13)0.0188 (13)0.0064 (13)
O2A0.150 (3)0.0688 (19)0.117 (2)0.0229 (18)0.055 (2)0.0376 (17)
C4B0.0595 (19)0.0490 (17)0.0543 (17)0.0068 (14)0.0204 (15)0.0057 (14)
C3A0.0634 (19)0.0389 (15)0.0556 (17)0.0019 (14)0.0177 (15)0.0039 (13)
C20B0.0551 (19)0.0554 (19)0.0619 (19)0.0003 (15)0.0148 (16)0.0043 (15)
C10B0.062 (2)0.0495 (18)0.0650 (19)0.0011 (15)0.0175 (16)0.0024 (15)
C7B0.073 (2)0.0535 (19)0.0602 (19)0.0130 (16)0.0296 (17)0.0028 (15)
C10A0.065 (2)0.0535 (18)0.0591 (19)0.0076 (15)0.0191 (16)0.0049 (15)
C6A0.0555 (19)0.0435 (17)0.074 (2)0.0072 (14)0.0149 (16)0.0009 (15)
C5A0.076 (2)0.0370 (16)0.0550 (17)0.0007 (15)0.0095 (16)0.0029 (14)
C4A0.081 (2)0.0431 (17)0.0611 (19)0.0029 (16)0.0300 (17)0.0028 (15)
C5B0.072 (2)0.0507 (18)0.0461 (16)0.0026 (16)0.0182 (15)0.0074 (14)
C14A0.063 (2)0.0553 (19)0.078 (2)0.0001 (16)0.0271 (18)0.0074 (17)
C20A0.069 (2)0.0470 (19)0.092 (2)0.0039 (16)0.0203 (19)0.0046 (18)
C14B0.0459 (18)0.061 (2)0.088 (2)0.0001 (15)0.0140 (17)0.0078 (18)
C16A0.065 (2)0.063 (2)0.065 (2)0.0131 (17)0.0125 (17)0.0012 (16)
C16B0.0525 (19)0.067 (2)0.080 (2)0.0076 (16)0.0208 (17)0.0148 (18)
C6B0.092 (3)0.067 (2)0.0595 (19)0.0111 (19)0.0441 (19)0.0130 (17)
C11A0.100 (3)0.069 (2)0.056 (2)0.021 (2)0.017 (2)0.0027 (18)
C11B0.087 (3)0.0420 (18)0.092 (3)0.0054 (17)0.031 (2)0.0024 (18)
C19B0.076 (2)0.080 (3)0.061 (2)0.017 (2)0.0153 (18)0.0188 (19)
C12B0.076 (2)0.055 (2)0.096 (3)0.0142 (19)0.037 (2)0.021 (2)
C13B0.058 (2)0.080 (3)0.089 (3)0.0154 (19)0.0175 (19)0.026 (2)
C18B0.072 (2)0.070 (2)0.092 (3)0.019 (2)0.040 (2)0.037 (2)
C17B0.065 (2)0.069 (2)0.111 (3)0.0023 (19)0.039 (2)0.026 (2)
C13A0.097 (3)0.063 (2)0.103 (3)0.000 (2)0.056 (3)0.013 (2)
C17A0.103 (3)0.075 (3)0.071 (2)0.041 (2)0.028 (2)0.020 (2)
C12A0.123 (4)0.070 (3)0.071 (3)0.021 (3)0.045 (3)0.016 (2)
C18A0.131 (4)0.051 (2)0.113 (3)0.022 (3)0.061 (3)0.021 (2)
C01G0.151 (4)0.062 (2)0.088 (3)0.025 (3)0.048 (3)0.028 (2)
C19A0.102 (3)0.050 (2)0.139 (4)0.012 (2)0.047 (3)0.003 (2)
C8A0.184 (5)0.077 (3)0.103 (3)0.020 (3)0.068 (4)0.041 (3)
Geometric parameters (Å, º) top
N2A—C1A1.324 (4)C10B—H10B0.9300
N2A—C15A1.426 (4)C7B—C6B1.373 (4)
N2A—H2A0.84 (3)C7B—H7B0.9300
N2B—C1B1.331 (3)C10A—C11A1.380 (5)
N2B—C15B1.433 (4)C10A—H10A0.9300
N2B—H2B0.95 (4)C6A—C5A1.390 (5)
N1A—C1A1.335 (4)C6A—H6A0.9300
N1A—C9A1.424 (4)C5A—C4A1.380 (4)
N1A—H1A0.87 (3)C4A—H4A0.9300
O1B—C5B1.366 (4)C5B—C6B1.382 (4)
O1B—C01G1.425 (5)C14A—C13A1.399 (5)
N1B—C1B1.324 (4)C14A—H14A0.9300
N1B—C9B1.421 (4)C20A—C19A1.372 (5)
N1B—H1B0.87 (3)C20A—H20A0.9300
O1A—C5A1.363 (4)C14B—C13B1.392 (5)
O1A—C8A1.434 (5)C14B—H14B0.9300
O4A—N3A1.233 (3)C16A—C17A1.391 (5)
O3A—N3A1.259 (3)C16A—H16A0.9300
N3B—O5B1.213 (3)C16B—C17B1.382 (5)
N3B—O3B1.217 (3)C16B—H16B0.9300
N3B—O4B1.229 (4)C6B—H6B0.9300
C2A—C3A1.395 (4)C11A—C12A1.362 (6)
C2A—C7A1.401 (4)C11A—H11A0.9300
C2A—C1A1.458 (4)C11B—C12B1.365 (5)
N3A—O2A1.190 (4)C11B—H11B0.9300
C15B—C16B1.372 (4)C19B—C18B1.363 (5)
C15B—C20B1.377 (4)C19B—H19B0.9300
C9B—C14B1.368 (4)C12B—C13B1.361 (5)
C9B—C10B1.381 (4)C12B—H12B0.9300
C2B—C3B1.392 (4)C13B—H13B0.9300
C2B—C7B1.399 (4)C18B—C17B1.354 (6)
C2B—C1B1.470 (4)C18B—H18B0.9300
C15A—C16A1.372 (4)C17B—H17B0.9300
C15A—C20A1.373 (4)C13A—C12A1.371 (6)
C9A—C14A1.372 (4)C13A—H13A0.9300
C9A—C10A1.381 (4)C17A—C18A1.350 (6)
C7A—C6A1.372 (4)C17A—H17A0.9300
C7A—H7A0.9300C12A—H12A0.9300
C3B—C4B1.381 (4)C18A—C19A1.367 (7)
C3B—H3B0.9300C18A—H18A0.9300
C4B—C5B1.381 (4)C01G—H01A0.9600
C4B—H4B0.9300C01G—H01B0.9600
C3A—C4A1.378 (4)C01G—H01C0.9600
C3A—H3A0.9300C19A—H19A0.9300
C20B—C19B1.400 (5)C8A—H8A10.9600
C20B—H20B0.9300C8A—H8A20.9600
C10B—C11B1.388 (5)C8A—H8A30.9600
C1A—N2A—C15A127.7 (3)C4A—C5A—C6A120.0 (3)
C1A—N2A—H2A119 (2)C3A—C4A—C5A119.8 (3)
C15A—N2A—H2A113 (2)C3A—C4A—H4A120.1
C1B—N2B—C15B127.4 (2)C5A—C4A—H4A120.1
C1B—N2B—H2B116 (2)O1B—C5B—C4B125.0 (3)
C15B—N2B—H2B116 (2)O1B—C5B—C6B115.6 (3)
C1A—N1A—C9A127.4 (3)C4B—C5B—C6B119.4 (3)
C1A—N1A—H1A119.4 (19)C9A—C14A—C13A119.0 (4)
C9A—N1A—H1A111.7 (19)C9A—C14A—H14A120.5
C5B—O1B—C01G118.2 (3)C13A—C14A—H14A120.5
C1B—N1B—C9B128.8 (3)C19A—C20A—C15A119.1 (4)
C1B—N1B—H1B118 (2)C19A—C20A—H20A120.5
C9B—N1B—H1B113 (2)C15A—C20A—H20A120.5
C5A—O1A—C8A117.2 (3)C9B—C14B—C13B119.7 (3)
O5B—N3B—O3B122.7 (3)C9B—C14B—H14B120.2
O5B—N3B—O4B120.0 (3)C13B—C14B—H14B120.2
O3B—N3B—O4B117.2 (3)C15A—C16A—C17A119.4 (4)
C3A—C2A—C7A118.2 (3)C15A—C16A—H16A120.3
C3A—C2A—C1A121.0 (3)C17A—C16A—H16A120.3
C7A—C2A—C1A120.8 (3)C15B—C16B—C17B119.6 (3)
N2A—C1A—N1A121.3 (3)C15B—C16B—H16B120.2
N2A—C1A—C2A119.7 (3)C17B—C16B—H16B120.2
N1A—C1A—C2A119.0 (3)C7B—C6B—C5B120.9 (3)
O2A—N3A—O4A123.7 (3)C7B—C6B—H6B119.6
O2A—N3A—O3A119.2 (3)C5B—C6B—H6B119.6
O4A—N3A—O3A117.1 (3)C12A—C11A—C10A120.2 (4)
C16B—C15B—C20B120.5 (3)C12A—C11A—H11A119.9
C16B—C15B—N2B118.7 (3)C10A—C11A—H11A119.9
C20B—C15B—N2B120.7 (3)C12B—C11B—C10B121.0 (3)
C14B—C9B—C10B120.3 (3)C12B—C11B—H11B119.5
C14B—C9B—N1B118.8 (3)C10B—C11B—H11B119.5
C10B—C9B—N1B120.8 (3)C18B—C19B—C20B120.4 (3)
C3B—C2B—C7B118.1 (3)C18B—C19B—H19B119.8
C3B—C2B—C1B121.1 (2)C20B—C19B—H19B119.8
C7B—C2B—C1B120.7 (3)C13B—C12B—C11B119.8 (3)
C16A—C15A—C20A120.3 (3)C13B—C12B—H12B120.1
C16A—C15A—N2A118.2 (3)C11B—C12B—H12B120.1
C20A—C15A—N2A121.3 (3)C12B—C13B—C14B120.3 (3)
C14A—C9A—C10A120.0 (3)C12B—C13B—H13B119.9
C14A—C9A—N1A118.8 (3)C14B—C13B—H13B119.9
C10A—C9A—N1A121.0 (3)C17B—C18B—C19B120.3 (3)
N1B—C1B—N2B123.8 (3)C17B—C18B—H18B119.9
N1B—C1B—C2B117.5 (2)C19B—C18B—H18B119.9
N2B—C1B—C2B118.7 (2)C18B—C17B—C16B120.5 (3)
C6A—C7A—C2A120.6 (3)C18B—C17B—H17B119.7
C6A—C7A—H7A119.7C16B—C17B—H17B119.7
C2A—C7A—H7A119.7C12A—C13A—C14A120.5 (4)
C4B—C3B—C2B121.1 (3)C12A—C13A—H13A119.8
C4B—C3B—H3B119.4C14A—C13A—H13A119.8
C2B—C3B—H3B119.4C18A—C17A—C16A120.2 (4)
C3B—C4B—C5B120.0 (3)C18A—C17A—H17A119.9
C3B—C4B—H4B120.0C16A—C17A—H17A119.9
C5B—C4B—H4B120.0C11A—C12A—C13A120.0 (4)
C4A—C3A—C2A121.2 (3)C11A—C12A—H12A120.0
C4A—C3A—H3A119.4C13A—C12A—H12A120.0
C2A—C3A—H3A119.4C17A—C18A—C19A119.9 (4)
C15B—C20B—C19B118.5 (3)C17A—C18A—H18A120.1
C15B—C20B—H20B120.7C19A—C18A—H18A120.1
C19B—C20B—H20B120.7O1B—C01G—H01A109.5
C9B—C10B—C11B118.8 (3)O1B—C01G—H01B109.5
C9B—C10B—H10B120.6H01A—C01G—H01B109.5
C11B—C10B—H10B120.6O1B—C01G—H01C109.5
C6B—C7B—C2B120.4 (3)H01A—C01G—H01C109.5
C6B—C7B—H7B119.8H01B—C01G—H01C109.5
C2B—C7B—H7B119.8C18A—C19A—C20A121.1 (4)
C11A—C10A—C9A120.2 (3)C18A—C19A—H19A119.5
C11A—C10A—H10A119.9C20A—C19A—H19A119.5
C9A—C10A—H10A119.9O1A—C8A—H8A1109.5
C7A—C6A—C5A120.2 (3)O1A—C8A—H8A2109.5
C7A—C6A—H6A119.9H8A1—C8A—H8A2109.5
C5A—C6A—H6A119.9O1A—C8A—H8A3109.5
O1A—C5A—C4A124.4 (3)H8A1—C8A—H8A3109.5
O1A—C5A—C6A115.6 (3)H8A2—C8A—H8A3109.5
C15A—N2A—C1A—N1A24.1 (4)C8A—O1A—C5A—C4A2.2 (5)
C15A—N2A—C1A—C2A155.7 (3)C8A—O1A—C5A—C6A177.7 (4)
C9A—N1A—C1A—N2A28.3 (4)C7A—C6A—C5A—O1A179.4 (3)
C9A—N1A—C1A—C2A151.9 (3)C7A—C6A—C5A—C4A0.7 (5)
C3A—C2A—C1A—N2A22.0 (4)C2A—C3A—C4A—C5A1.2 (5)
C7A—C2A—C1A—N2A157.8 (3)O1A—C5A—C4A—C3A178.0 (3)
C3A—C2A—C1A—N1A157.8 (3)C6A—C5A—C4A—C3A2.1 (5)
C7A—C2A—C1A—N1A22.4 (4)C01G—O1B—C5B—C4B7.3 (5)
C1B—N2B—C15B—C16B135.7 (3)C01G—O1B—C5B—C6B173.7 (4)
C1B—N2B—C15B—C20B45.9 (4)C3B—C4B—C5B—O1B178.3 (3)
C1B—N1B—C9B—C14B133.1 (3)C3B—C4B—C5B—C6B0.7 (5)
C1B—N1B—C9B—C10B47.8 (5)C10A—C9A—C14A—C13A0.1 (5)
C1A—N2A—C15A—C16A145.9 (3)N1A—C9A—C14A—C13A174.9 (3)
C1A—N2A—C15A—C20A39.0 (4)C16A—C15A—C20A—C19A2.2 (5)
C1A—N1A—C9A—C14A149.4 (3)N2A—C15A—C20A—C19A177.2 (3)
C1A—N1A—C9A—C10A35.7 (4)C10B—C9B—C14B—C13B3.1 (5)
C9B—N1B—C1B—N2B15.2 (5)N1B—C9B—C14B—C13B177.9 (3)
C9B—N1B—C1B—C2B163.9 (3)C20A—C15A—C16A—C17A2.6 (5)
C15B—N2B—C1B—N1B19.6 (5)N2A—C15A—C16A—C17A177.8 (3)
C15B—N2B—C1B—C2B161.3 (3)C20B—C15B—C16B—C17B3.1 (5)
C3B—C2B—C1B—N1B148.0 (3)N2B—C15B—C16B—C17B178.5 (3)
C7B—C2B—C1B—N1B29.5 (4)C2B—C7B—C6B—C5B1.6 (6)
C3B—C2B—C1B—N2B32.9 (4)O1B—C5B—C6B—C7B179.7 (3)
C7B—C2B—C1B—N2B149.6 (3)C4B—C5B—C6B—C7B0.6 (5)
C3A—C2A—C7A—C6A2.6 (4)C9A—C10A—C11A—C12A0.1 (5)
C1A—C2A—C7A—C6A177.6 (3)C9B—C10B—C11B—C12B0.9 (5)
C7B—C2B—C3B—C4B0.0 (4)C15B—C20B—C19B—C18B1.2 (5)
C1B—C2B—C3B—C4B177.6 (3)C10B—C11B—C12B—C13B2.1 (6)
C2B—C3B—C4B—C5B1.0 (5)C11B—C12B—C13B—C14B2.4 (6)
C7A—C2A—C3A—C4A1.1 (4)C9B—C14B—C13B—C12B0.2 (6)
C1A—C2A—C3A—C4A179.1 (3)C20B—C19B—C18B—C17B1.6 (6)
C16B—C15B—C20B—C19B3.5 (5)C19B—C18B—C17B—C16B2.1 (6)
N2B—C15B—C20B—C19B178.1 (3)C15B—C16B—C17B—C18B0.2 (6)
C14B—C9B—C10B—C11B3.5 (5)C9A—C14A—C13A—C12A0.0 (5)
N1B—C9B—C10B—C11B177.5 (3)C15A—C16A—C17A—C18A1.1 (6)
C3B—C2B—C7B—C6B1.2 (5)C10A—C11A—C12A—C13A0.1 (6)
C1B—C2B—C7B—C6B176.3 (3)C14A—C13A—C12A—C11A0.1 (6)
C14A—C9A—C10A—C11A0.2 (5)C16A—C17A—C18A—C19A0.7 (6)
N1A—C9A—C10A—C11A174.7 (3)C17A—C18A—C19A—C20A1.1 (7)
C2A—C7A—C6A—C5A1.7 (5)C15A—C20A—C19A—C18A0.4 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O5B0.87 (3)2.00 (3)2.838 (4)160 (3)
N1B—H1B···O2Ai0.87 (3)2.45 (3)3.214 (4)148 (3)
N1B—H1B···O3Ai0.87 (3)2.01 (3)2.804 (4)151 (3)
N1B—H1B···N3Ai0.87 (3)2.59 (3)3.431 (4)165 (3)
N2A—H2A···O3Bii0.84 (3)2.20 (3)3.006 (4)160 (3)
N2A—H2A···O4Bii0.84 (3)2.41 (3)3.110 (4)140 (3)
N2A—H2A···N3Bii0.84 (3)2.69 (3)3.506 (4)163 (3)
N2B—H2B···O4A0.95 (4)1.88 (4)2.798 (3)161 (3)
C20B—H20B···O3Aiii0.932.493.288 (4)144
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x+1, y+1, z+1.
 

Acknowledgements

The authors thank FAPERJ and CNPq for financial support, as well as LDRX–UFF for use of the crystallographic facilities. RSS is indebted to CAPES for a doctoral fellowship.

References

First citationBortoluzzi, A. J., Echevarria, A. & Rodrigues-Santos, C. E. (2004). Acta Cryst. E60, o1837–o1839.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CSD CrossRef CAS IUCr Journals 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. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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