N,N′-Bis(3-nitro­phen­yl)isophthalamide tetra­butyl­ammonium chloride

Light, M.E.; Gale, P.A.; Navakhun, K.

doi:10.1107/S1600536806005447

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 62| Part 3| March 2006| Pages o1097-o1098

https://doi.org/10.1107/S1600536806005447

N,N′-Bis(3-nitrophenyl)isophthalamide tetrabutylammonium chloride

Mark E. Light,^a ^* Philip A. Gale ^a and Korakot Navakhun ^a

^aSchool of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, England
^*Correspondence e-mail: light@soton.ac.uk

(Received 7 February 2006; accepted 15 February 2006; online 22 February 2006)

The receptor of the title compound, C₁₄H₃₆N⁺·Cl⁻·C₂₀H₁₄N₄O₆, binds a chloride anion via two N—H⋯Cl hydrogen bonds [N⋯Cl = 3.2367 (14) Å and 3.3239 (15)°].

Comment

This work forms part of an ongoing study on the conformational properties of the anion complexes of isophthalamides and their derivatives.

The receptor in the title chloride complex, (I), adopts a similar conformation to that of a bromide–isophthalamide complex reported by Kavallieratos et al. (1997 ). In both cases, the anion lies above the least-squares plane through the central aromatic ring. In the case of the chloride complex, the angle between the plane through the central aromatic ring and a plane defined by the anion and the amide H atoms is 45.54 (4)°, whilst for the larger bromide anion the angle was found to be 63.63 (6)°. The larger size of the bromide anion is also evident in the hydrogen-bond donor–acceptor distances, which were found to be 3.634 (4) and 3.436 (4) Å for the two H⋯Br interactions, and are 3.3239 (15) and 3.2367 (14) Å for the H⋯Cl interactions in the structure reported here (Table 1).

It is interesting to note that the current chloride structure and the previous bromide structure form discrete 1:1 receptor–anion units, whilst the fluoride complex of a similar compound reported by Coles et al. (2003 ) forms a double helix with a 2:2 receptor-to-anion stoichiometry. This double unit is also present in the fluoride complex of a 1,3-diamidoanthraquinone (a `twisted' isophthalamide analogue) reported by Brooks et al. (2005 )

Figure 1
View of the asymmetric unit of (I)

, showing the atom labelling and the hydrogen-bonded chloride anion. Displacement ellipsoids are drawn at the 50% probability level and hydrogen bonds are shown as dashed lines.

Experimental

The title compound was prepared as reported previously by Moore et al. (1997 ) and Coles et al. (2003) Crystals were obtained by slow evaporation of a solution of the receptor in the presence of excess tetrabutylammonium chloride.

Crystal data

C₁₆H₃₆N⁺·Cl⁻·C₂₀H₁₄N₄O₆
M_r = 684.26
Monoclinic, P 2₁ /n
a = 11.6508 (2) Å
b = 26.0390 (4) Å
c = 12.0569 (2) Å
β = 96.753 (1)°
V = 3632.39 (10) Å³
Z = 4
D_x = 1.251 Mg m⁻³
Mo Kα radiation
Cell parameters from 24972 reflections
θ = 2.9–27.5°
μ = 0.16 mm⁻¹
T = 120 (2) K
Slab, colourless
0.60 × 0.60 × 0.10 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
φ and ω scans
Absorption correction: multi-scan(SORTAV; Blessing, 1995 )T_min = 0.902, T_max = 0.985
20923 measured reflections
8136 independent reflections
6851 reflections with I > 2σ(I)
R_int = 0.078
θ_max = 27.5°
h = −15 → 14
k = −31 → 33
l = −14 → 15

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.149
S = 0.99
8136 reflections
438 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0795P)² + 1.9526P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.004
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.31 e Å⁻³
Extinction correction: SHELXL97
Extinction coefficient: 0.0057 (16)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯Cl1	0.88	2.38	3.2367 (14)	163
N3—H3A⋯Cl1	0.88	2.46	3.3239 (15)	166

All H atoms were positioned with ideal geometry and allowed to ride on their parent atoms, with C—H = 0.95 (aromatic), 0.96 (methylene), 0.98 (methyl) and 0.88 Å (N—H), and with U_iso(H) = 1.2U_eq(aromatic, methylene and NH H atoms) or 1.5U_eq(methyl C).

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CAMERON (Watkin et al., 1993 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536806005447/nc2003sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806005447/nc2003Isup2.hkl

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CAMERON (Watkin et al., 1993); software used to prepare material for publication: WinGX (Farrugia, 1999).

N,N'-Bis(3-nitrophenyl)isophthalamide tetrabutylammonium chloride top

Crystal data top

C₁₆H₃₆N⁺·Cl⁻·C₂₀H₁₄N₄O₆	F(000) = 1464
M_r = 684.26	D_x = 1.251 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 24972 reflections
a = 11.6508 (2) Å	θ = 2.9–27.5°
b = 26.0390 (4) Å	µ = 0.16 mm⁻¹
c = 12.0569 (2) Å	T = 120 K
β = 96.753 (1)°	Rod, colourless
V = 3632.39 (10) Å³	0.60 × 0.60 × 0.10 mm
Z = 4

Data collection top

Bruker–Nonius CCD camera on κ-goniostat diffractometer	8136 independent reflections
Radiation source: Bruker Nonius FR591 Rotating Anode	6851 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.078
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 2.9°
φ and ω scans	h = −15→14
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −31→33
T_min = 0.902, T_max = 0.985	l = −14→15
20923 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.149	w = 1/[σ²(F_o²) + (0.0795P)² + 1.9526P] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max = 0.004
8136 reflections	Δρ_max = 0.43 e Å⁻³
438 parameters	Δρ_min = −0.31 e Å⁻³
288 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0057 (16)

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

All H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95 Å (Caromatic), 0.96 (Cmethylene), 0.98 (methyl) and 0.88 (N—H) with U_iso(H) = 1.2Ueq(Caromatic, Cmethylene and N—H) or 1.5Ueq(Cmethyl).

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 > σ(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.

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

	x	y	z	U_iso*/U_eq
Cl1	0.84106 (3)	0.239970 (16)	0.68422 (3)	0.02238 (13)
C1	0.66025 (16)	0.45752 (7)	0.71558 (14)	0.0243 (4)
C2	0.77063 (17)	0.46541 (7)	0.68776 (15)	0.0281 (4)
H2	0.7949	0.4982	0.6649	0.034*
C3	0.84463 (17)	0.42344 (8)	0.69460 (16)	0.0291 (4)
H3	0.9217	0.4276	0.6778	0.035*
C4	0.80711 (15)	0.37543 (7)	0.72582 (14)	0.0240 (4)
H4	0.8584	0.3470	0.7289	0.029*
C5	0.69425 (14)	0.36863 (6)	0.75282 (13)	0.0196 (3)
C6	0.61969 (15)	0.41058 (7)	0.74947 (14)	0.0220 (3)
H6	0.5437	0.4072	0.7697	0.026*
C7	0.57944 (14)	0.30687 (7)	0.84893 (14)	0.0212 (3)
C8	0.57061 (14)	0.25100 (6)	0.87738 (14)	0.0189 (3)
C9	0.60390 (13)	0.21178 (6)	0.80876 (13)	0.0188 (3)
H9	0.6298	0.2199	0.7390	0.023*
C10	0.59913 (13)	0.16064 (6)	0.84253 (14)	0.0192 (3)
C11	0.56073 (14)	0.14881 (7)	0.94520 (14)	0.0217 (3)
H11	0.5588	0.1141	0.9691	0.026*
C12	0.52536 (14)	0.18790 (7)	1.01235 (14)	0.0222 (3)
H12	0.4987	0.1798	1.0817	0.027*
C13	0.52900 (14)	0.23845 (7)	0.97825 (14)	0.0212 (3)
H13	0.5031	0.2649	1.0236	0.025*
C14	0.63103 (15)	0.11653 (7)	0.77184 (14)	0.0217 (3)
C15	0.75027 (15)	0.09243 (6)	0.62296 (14)	0.0211 (3)
C16	0.85457 (15)	0.10464 (7)	0.58215 (15)	0.0240 (4)
H16	0.8934	0.1357	0.6045	0.029*
C17	0.90159 (17)	0.07147 (7)	0.50890 (16)	0.0297 (4)
H17	0.9725	0.0800	0.4818	0.036*
C18	0.84591 (19)	0.02603 (7)	0.47510 (16)	0.0313 (4)
H18	0.8779	0.0031	0.4258	0.038*
C19	0.74235 (18)	0.01530 (7)	0.51560 (15)	0.0281 (4)
C20	0.69181 (16)	0.04725 (7)	0.58902 (15)	0.0245 (4)
H20	0.6204	0.0386	0.6149	0.029*
N1	0.57972 (15)	0.50147 (6)	0.70908 (14)	0.0312 (4)
N2	0.66191 (12)	0.31854 (5)	0.78099 (12)	0.0202 (3)
H2A	0.6976	0.2927	0.7526	0.024*
N3	0.70663 (12)	0.12787 (5)	0.69629 (12)	0.0208 (3)
H3A	0.7300	0.1599	0.6932	0.025*
N4	0.68118 (18)	−0.03238 (6)	0.47957 (15)	0.0387 (4)
O1	0.60268 (15)	0.53933 (6)	0.65573 (15)	0.0474 (4)
O2	0.49396 (14)	0.49842 (6)	0.75905 (15)	0.0458 (4)
O3	0.51966 (12)	0.33909 (5)	0.88865 (12)	0.0320 (3)
O4	0.59087 (13)	0.07377 (5)	0.78344 (12)	0.0328 (3)
O5	0.7175 (2)	−0.05704 (7)	0.40400 (17)	0.0684 (6)
O6	0.59797 (16)	−0.04552 (6)	0.52535 (15)	0.0501 (4)
C21	0.22245 (14)	0.21926 (6)	0.88104 (13)	0.0190 (3)
H21A	0.2108	0.2205	0.9610	0.023*
H21B	0.3066	0.2217	0.8766	0.023*
C22	0.16391 (15)	0.26590 (6)	0.82291 (14)	0.0221 (3)
H22A	0.0791	0.2631	0.8226	0.027*
H22B	0.1810	0.2671	0.7444	0.027*
C23	0.20702 (16)	0.31501 (7)	0.88303 (15)	0.0252 (4)
H23A	0.1891	0.3137	0.9612	0.030*
H23B	0.2920	0.3172	0.8845	0.030*
C24	0.15184 (17)	0.36281 (7)	0.82650 (16)	0.0289 (4)
H24A	0.1696	0.3643	0.7491	0.043*
H24B	0.1826	0.3935	0.8668	0.043*
H24C	0.0679	0.3614	0.8273	0.043*
C25	0.18847 (14)	0.16516 (7)	0.70861 (13)	0.0192 (3)
H25A	0.1375	0.1920	0.6714	0.023*
H25B	0.1589	0.1315	0.6798	0.023*
C26	0.31027 (14)	0.17269 (7)	0.67593 (14)	0.0219 (3)
H26A	0.3472	0.2025	0.7168	0.026*
H26B	0.3576	0.1419	0.6972	0.026*
C27	0.30582 (16)	0.18169 (8)	0.55045 (14)	0.0263 (4)
H27A	0.2627	0.1532	0.5101	0.032*
H27B	0.2634	0.2140	0.5306	0.032*
C28	0.42588 (17)	0.18511 (9)	0.51296 (16)	0.0343 (5)
H28A	0.4707	0.2117	0.5564	0.051*
H28B	0.4191	0.1939	0.4334	0.051*
H28C	0.4651	0.1519	0.5249	0.051*
C29	0.25648 (14)	0.12629 (7)	0.89477 (14)	0.0205 (3)
H29A	0.3365	0.1314	0.8769	0.025*
H29B	0.2571	0.1317	0.9761	0.025*
C30	0.22193 (16)	0.07086 (7)	0.86828 (16)	0.0262 (4)
H30A	0.1911	0.0679	0.7884	0.031*
H30B	0.1601	0.0605	0.9135	0.031*
C31	0.32561 (17)	0.03500 (8)	0.89341 (17)	0.0316 (4)
H31A	0.3840	0.0434	0.8429	0.038*
H31B	0.3612	0.0408	0.9711	0.038*
C32	0.2923 (2)	−0.02112 (9)	0.8791 (2)	0.0516 (6)
H32A	0.2386	−0.0303	0.9327	0.077*
H32B	0.3618	−0.0425	0.8923	0.077*
H32C	0.2549	−0.0269	0.8030	0.077*
C33	0.05375 (13)	0.15878 (7)	0.84952 (13)	0.0186 (3)
H33A	0.0296	0.1248	0.8179	0.022*
H33B	0.0067	0.1852	0.8059	0.022*
C34	0.02629 (15)	0.16085 (8)	0.97008 (15)	0.0266 (4)
H34A	0.0601	0.1923	1.0066	0.032*
H34B	0.0610	0.1308	1.0117	0.032*
C35	−0.10470 (15)	0.16081 (8)	0.97318 (15)	0.0275 (4)
H35A	−0.1392	0.1900	0.9283	0.033*
H35B	−0.1376	0.1287	0.9388	0.033*
C36	−0.13702 (17)	0.16509 (10)	1.09185 (17)	0.0383 (5)
H36A	−0.1110	0.1343	1.1342	0.058*
H36B	−0.2211	0.1683	1.0893	0.058*
H36C	−0.0998	0.1954	1.1282	0.058*
N5	0.17984 (11)	0.16721 (5)	0.83367 (11)	0.0175 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0200 (2)	0.0217 (2)	0.0268 (2)	0.00065 (15)	0.00836 (15)	0.00045 (15)
C1	0.0297 (9)	0.0193 (8)	0.0231 (8)	0.0020 (7)	0.0001 (7)	−0.0013 (6)
C2	0.0354 (10)	0.0213 (8)	0.0280 (9)	−0.0039 (7)	0.0056 (7)	0.0019 (7)
C3	0.0276 (9)	0.0286 (9)	0.0325 (9)	−0.0043 (7)	0.0095 (7)	0.0003 (7)
C4	0.0240 (8)	0.0235 (9)	0.0252 (8)	0.0028 (7)	0.0062 (7)	0.0011 (7)
C5	0.0224 (8)	0.0189 (8)	0.0173 (7)	−0.0004 (6)	0.0017 (6)	−0.0014 (6)
C6	0.0213 (8)	0.0212 (8)	0.0230 (8)	0.0011 (7)	0.0008 (6)	−0.0018 (6)
C7	0.0172 (7)	0.0211 (8)	0.0257 (8)	0.0004 (6)	0.0039 (6)	−0.0031 (6)
C8	0.0123 (7)	0.0211 (8)	0.0232 (8)	−0.0006 (6)	0.0022 (6)	−0.0023 (6)
C9	0.0143 (7)	0.0217 (8)	0.0210 (7)	−0.0003 (6)	0.0045 (6)	−0.0013 (6)
C10	0.0126 (7)	0.0215 (8)	0.0239 (8)	−0.0005 (6)	0.0037 (6)	−0.0004 (6)
C11	0.0162 (7)	0.0238 (8)	0.0251 (8)	0.0003 (6)	0.0029 (6)	0.0037 (6)
C12	0.0166 (7)	0.0302 (9)	0.0202 (7)	−0.0019 (7)	0.0038 (6)	0.0006 (7)
C13	0.0135 (7)	0.0269 (9)	0.0237 (8)	−0.0022 (6)	0.0034 (6)	−0.0058 (6)
C14	0.0201 (8)	0.0200 (8)	0.0257 (8)	0.0024 (6)	0.0052 (6)	0.0004 (6)
C15	0.0244 (8)	0.0183 (8)	0.0211 (7)	0.0039 (6)	0.0046 (6)	0.0024 (6)
C16	0.0249 (8)	0.0207 (8)	0.0272 (8)	0.0028 (7)	0.0058 (7)	0.0034 (7)
C17	0.0320 (9)	0.0271 (9)	0.0324 (9)	0.0074 (8)	0.0144 (8)	0.0049 (7)
C18	0.0437 (11)	0.0244 (9)	0.0280 (9)	0.0099 (8)	0.0143 (8)	0.0018 (7)
C19	0.0412 (10)	0.0184 (8)	0.0253 (8)	0.0016 (7)	0.0054 (7)	0.0003 (7)
C20	0.0291 (9)	0.0198 (8)	0.0254 (8)	−0.0004 (7)	0.0058 (7)	−0.0002 (7)
N1	0.0369 (9)	0.0227 (8)	0.0331 (8)	0.0051 (7)	0.0003 (7)	0.0010 (6)
N2	0.0197 (7)	0.0172 (7)	0.0247 (7)	0.0017 (5)	0.0069 (5)	−0.0016 (5)
N3	0.0211 (7)	0.0174 (7)	0.0251 (7)	−0.0011 (5)	0.0075 (6)	−0.0010 (5)
N4	0.0596 (12)	0.0230 (8)	0.0346 (9)	−0.0039 (8)	0.0098 (8)	−0.0068 (7)
O1	0.0552 (10)	0.0256 (8)	0.0617 (10)	0.0064 (7)	0.0088 (8)	0.0160 (7)
O2	0.0430 (9)	0.0374 (9)	0.0597 (10)	0.0161 (7)	0.0179 (8)	0.0103 (7)
O3	0.0300 (7)	0.0228 (7)	0.0466 (8)	0.0043 (6)	0.0191 (6)	−0.0027 (6)
O4	0.0383 (8)	0.0203 (7)	0.0438 (8)	−0.0041 (6)	0.0213 (6)	−0.0020 (6)
O5	0.1113 (17)	0.0391 (10)	0.0619 (12)	−0.0173 (11)	0.0402 (12)	−0.0280 (9)
O6	0.0586 (11)	0.0344 (9)	0.0589 (10)	−0.0178 (8)	0.0135 (9)	−0.0135 (7)
C21	0.0178 (7)	0.0209 (8)	0.0178 (7)	−0.0026 (6)	−0.0007 (6)	−0.0032 (6)
C22	0.0205 (8)	0.0202 (8)	0.0250 (8)	−0.0010 (6)	0.0002 (6)	−0.0019 (6)
C23	0.0249 (8)	0.0226 (9)	0.0277 (8)	−0.0035 (7)	0.0009 (7)	−0.0048 (7)
C24	0.0327 (10)	0.0228 (9)	0.0315 (9)	−0.0032 (8)	0.0046 (8)	−0.0034 (7)
C25	0.0185 (7)	0.0230 (8)	0.0156 (7)	−0.0006 (6)	0.0007 (6)	−0.0027 (6)
C26	0.0175 (8)	0.0280 (9)	0.0201 (8)	0.0005 (7)	0.0016 (6)	−0.0021 (6)
C27	0.0230 (8)	0.0356 (10)	0.0204 (8)	−0.0018 (7)	0.0031 (7)	−0.0003 (7)
C28	0.0285 (10)	0.0484 (12)	0.0277 (9)	−0.0010 (9)	0.0101 (8)	0.0010 (9)
C29	0.0163 (7)	0.0236 (8)	0.0211 (7)	0.0030 (6)	−0.0004 (6)	0.0019 (6)
C30	0.0232 (8)	0.0241 (9)	0.0310 (9)	0.0027 (7)	0.0018 (7)	0.0001 (7)
C31	0.0309 (10)	0.0312 (10)	0.0330 (10)	0.0114 (8)	0.0050 (8)	0.0034 (8)
C32	0.0627 (16)	0.0269 (11)	0.0639 (15)	0.0154 (11)	0.0012 (13)	0.0013 (10)
C33	0.0126 (7)	0.0233 (8)	0.0195 (7)	−0.0004 (6)	−0.0003 (6)	0.0000 (6)
C34	0.0171 (8)	0.0409 (10)	0.0218 (8)	0.0019 (7)	0.0014 (6)	0.0013 (7)
C35	0.0169 (8)	0.0383 (10)	0.0276 (9)	0.0001 (7)	0.0034 (7)	−0.0006 (7)
C36	0.0220 (9)	0.0644 (15)	0.0298 (10)	0.0037 (9)	0.0076 (8)	0.0037 (9)
N5	0.0146 (6)	0.0204 (7)	0.0172 (6)	0.0002 (5)	0.0004 (5)	−0.0006 (5)

Geometric parameters (Å, º) top

C1—C2	1.382 (3)	C21—H21B	0.9900
C1—C6	1.389 (2)	C22—C23	1.525 (2)
C1—N1	1.476 (2)	C22—H22A	0.9900
C2—C3	1.389 (3)	C22—H22B	0.9900
C2—H2	0.9500	C23—C24	1.524 (3)
C3—C4	1.391 (3)	C23—H23A	0.9900
C3—H3	0.9500	C23—H23B	0.9900
C4—C5	1.402 (2)	C24—H24A	0.9800
C4—H4	0.9500	C24—H24B	0.9800
C5—C6	1.393 (2)	C24—H24C	0.9800
C5—N2	1.410 (2)	C25—N5	1.5239 (19)
C6—H6	0.9500	C25—C26	1.529 (2)
C7—O3	1.223 (2)	C25—H25A	0.9900
C7—N2	1.368 (2)	C25—H25B	0.9900
C7—C8	1.501 (2)	C26—C27	1.526 (2)
C8—C9	1.398 (2)	C26—H26A	0.9900
C8—C13	1.400 (2)	C26—H26B	0.9900
C9—C10	1.395 (2)	C27—C28	1.522 (2)
C9—H9	0.9500	C27—H27A	0.9900
C10—C11	1.399 (2)	C27—H27B	0.9900
C10—C14	1.503 (2)	C28—H28A	0.9800
C11—C12	1.393 (2)	C28—H28B	0.9800
C11—H11	0.9500	C28—H28C	0.9800
C12—C13	1.381 (3)	C29—C30	1.522 (2)
C12—H12	0.9500	C29—N5	1.523 (2)
C13—H13	0.9500	C29—H29A	0.9900
C14—O4	1.222 (2)	C29—H29B	0.9900
C14—N3	1.372 (2)	C30—C31	1.529 (3)
C15—C20	1.396 (2)	C30—H30A	0.9900
C15—C16	1.400 (2)	C30—H30B	0.9900
C15—N3	1.413 (2)	C31—C32	1.517 (3)
C16—C17	1.393 (2)	C31—H31A	0.9900
C16—H16	0.9500	C31—H31B	0.9900
C17—C18	1.387 (3)	C32—H32A	0.9800
C17—H17	0.9500	C32—H32B	0.9800
C18—C19	1.382 (3)	C32—H32C	0.9800
C18—H18	0.9500	C33—N5	1.520 (2)
C19—C20	1.395 (2)	C33—C34	1.526 (2)
C19—N4	1.472 (3)	C33—H33A	0.9900
C20—H20	0.9500	C33—H33B	0.9900
N1—O1	1.224 (2)	C34—C35	1.531 (2)
N1—O2	1.228 (2)	C34—H34A	0.9900
N2—H2A	0.8800	C34—H34B	0.9900
N3—H3A	0.8800	C35—C36	1.526 (3)
N4—O6	1.220 (2)	C35—H35A	0.9900
N4—O5	1.230 (2)	C35—H35B	0.9900
C21—C22	1.523 (2)	C36—H36A	0.9800
C21—N5	1.531 (2)	C36—H36B	0.9800
C21—H21A	0.9900	C36—H36C	0.9800

C2—C1—C6	124.10 (17)	C24—C23—H23B	109.2
C2—C1—N1	118.40 (16)	C22—C23—H23B	109.2
C6—C1—N1	117.50 (16)	H23A—C23—H23B	107.9
C1—C2—C3	117.22 (17)	C23—C24—H24A	109.5
C1—C2—H2	121.4	C23—C24—H24B	109.5
C3—C2—H2	121.4	H24A—C24—H24B	109.5
C2—C3—C4	120.73 (17)	C23—C24—H24C	109.5
C2—C3—H3	119.6	H24A—C24—H24C	109.5
C4—C3—H3	119.6	H24B—C24—H24C	109.5
C3—C4—C5	120.62 (17)	N5—C25—C26	114.93 (13)
C3—C4—H4	119.7	N5—C25—H25A	108.5
C5—C4—H4	119.7	C26—C25—H25A	108.5
C6—C5—C4	119.52 (16)	N5—C25—H25B	108.5
C6—C5—N2	123.28 (15)	C26—C25—H25B	108.5
C4—C5—N2	117.19 (15)	H25A—C25—H25B	107.5
C1—C6—C5	117.76 (16)	C27—C26—C25	110.53 (14)
C1—C6—H6	121.1	C27—C26—H26A	109.5
C5—C6—H6	121.1	C25—C26—H26A	109.5
O3—C7—N2	123.66 (16)	C27—C26—H26B	109.5
O3—C7—C8	121.18 (15)	C25—C26—H26B	109.5
N2—C7—C8	115.08 (14)	H26A—C26—H26B	108.1
C9—C8—C13	119.49 (16)	C28—C27—C26	112.22 (15)
C9—C8—C7	122.80 (15)	C28—C27—H27A	109.2
C13—C8—C7	117.70 (15)	C26—C27—H27A	109.2
C10—C9—C8	120.08 (15)	C28—C27—H27B	109.2
C10—C9—H9	120.0	C26—C27—H27B	109.2
C8—C9—H9	120.0	H27A—C27—H27B	107.9
C9—C10—C11	119.75 (15)	C27—C28—H28A	109.5
C9—C10—C14	122.87 (15)	C27—C28—H28B	109.5
C11—C10—C14	117.37 (15)	H28A—C28—H28B	109.5
C12—C11—C10	120.04 (16)	C27—C28—H28C	109.5
C12—C11—H11	120.0	H28A—C28—H28C	109.5
C10—C11—H11	120.0	H28B—C28—H28C	109.5
C13—C12—C11	120.13 (15)	C30—C29—N5	115.87 (13)
C13—C12—H12	119.9	C30—C29—H29A	108.3
C11—C12—H12	119.9	N5—C29—H29A	108.3
C12—C13—C8	120.46 (16)	C30—C29—H29B	108.3
C12—C13—H13	119.8	N5—C29—H29B	108.3
C8—C13—H13	119.8	H29A—C29—H29B	107.4
O4—C14—N3	123.81 (16)	C29—C30—C31	110.76 (15)
O4—C14—C10	120.52 (15)	C29—C30—H30A	109.5
N3—C14—C10	115.67 (15)	C31—C30—H30A	109.5
C20—C15—C16	120.12 (16)	C29—C30—H30B	109.5
C20—C15—N3	122.31 (15)	C31—C30—H30B	109.5
C16—C15—N3	117.55 (15)	H30A—C30—H30B	108.1
C17—C16—C15	120.29 (17)	C32—C31—C30	112.35 (18)
C17—C16—H16	119.9	C32—C31—H31A	109.1
C15—C16—H16	119.9	C30—C31—H31A	109.1
C18—C17—C16	120.66 (17)	C32—C31—H31B	109.1
C18—C17—H17	119.7	C30—C31—H31B	109.1
C16—C17—H17	119.7	H31A—C31—H31B	107.9
C19—C18—C17	117.77 (17)	C31—C32—H32A	109.5
C19—C18—H18	121.1	C31—C32—H32B	109.5
C17—C18—H18	121.1	H32A—C32—H32B	109.5
C18—C19—C20	123.70 (18)	C31—C32—H32C	109.5
C18—C19—N4	118.60 (17)	H32A—C32—H32C	109.5
C20—C19—N4	117.69 (17)	H32B—C32—H32C	109.5
C19—C20—C15	117.44 (17)	N5—C33—C34	115.40 (13)
C19—C20—H20	121.3	N5—C33—H33A	108.4
C15—C20—H20	121.3	C34—C33—H33A	108.4
O1—N1—O2	123.41 (17)	N5—C33—H33B	108.4
O1—N1—C1	118.40 (17)	C34—C33—H33B	108.4
O2—N1—C1	118.18 (16)	H33A—C33—H33B	107.5
C7—N2—C5	125.17 (14)	C33—C34—C35	110.15 (14)
C7—N2—H2A	117.4	C33—C34—H34A	109.6
C5—N2—H2A	117.4	C35—C34—H34A	109.6
C14—N3—C15	125.54 (14)	C33—C34—H34B	109.6
C14—N3—H3A	117.2	C35—C34—H34B	109.6
C15—N3—H3A	117.2	H34A—C34—H34B	108.1
O6—N4—O5	123.38 (19)	C36—C35—C34	112.30 (15)
O6—N4—C19	119.10 (16)	C36—C35—H35A	109.1
O5—N4—C19	117.52 (19)	C34—C35—H35A	109.1
C22—C21—N5	115.24 (13)	C36—C35—H35B	109.1
C22—C21—H21A	108.5	C34—C35—H35B	109.1
N5—C21—H21A	108.5	H35A—C35—H35B	107.9
C22—C21—H21B	108.5	C35—C36—H36A	109.5
N5—C21—H21B	108.5	C35—C36—H36B	109.5
H21A—C21—H21B	107.5	H36A—C36—H36B	109.5
C21—C22—C23	110.19 (14)	C35—C36—H36C	109.5
C21—C22—H22A	109.6	H36A—C36—H36C	109.5
C23—C22—H22A	109.6	H36B—C36—H36C	109.5
C21—C22—H22B	109.6	C33—N5—C29	111.01 (12)
C23—C22—H22B	109.6	C33—N5—C25	107.26 (12)
H22A—C22—H22B	108.1	C29—N5—C25	110.54 (12)
C24—C23—C22	111.96 (15)	C33—N5—C21	110.91 (12)
C24—C23—H23A	109.2	C29—N5—C21	107.03 (12)
C22—C23—H23A	109.2	C25—N5—C21	110.12 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl1	0.88	2.38	3.2367 (14)	163
N3—H3A···Cl1	0.88	2.46	3.3239 (15)	166

Acknowledgements

The authors thank the EPSRC for funding the crystallographic facilities.

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