4-Amino­methyl-phenyl­amino-bis-(3,4-di­chloro-5-phenyl­carbamoyl-1H-pyrrole-2-carbox­amide) tetra­butyl­ammonium salt

Light, M.E.; Gale, P.A.; Navakhun, K.; Maynard-Smith, M.

doi:10.1107/S160053680501069X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 61| Part 5| May 2005| Pages o1302-o1303

https://doi.org/10.1107/S160053680501069X

4-Aminomethyl-phenylamino-bis-(3,4-dichloro-5-phenylcarbamoyl-1H-pyrrole-2-carboxamide) tetrabutylammonium salt

Mark E. Light,^a ^* Philip A. Gale,^a Korakot Navakhun ^a and Michael Maynard-Smith ^a

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

(Received 22 March 2005; accepted 6 April 2005; online 9 April 2005)

The crystal structure of the tetrabutylammonium salt of doubly deprotonated 4-aminomethyl(phenylamino)bis-(3,4-dichloro-5-phenylcarbamoyl-1H-pyrrole-2-carboxamide), 2C₁₆H₃₆N⁺·C₃₂H₂₂C_l4N₆O₄²⁻, has been elucidated. The anion lies on an inversion centre and adopts a twisted S shape.

Comment

4-Aminomethyl(phenylamino)bis-(3,4-dichloro-5-phenylcarbamoyl-1H-pyrrole-2-carboxamide) crystallizes as the tetrabutylammonium salt, (I), from an acetonitrile solution of the compound in the presence of excess tetrabutylammonium fluoride. The anion adopts a twisted S shape around a centre of inversion. The pyrrole and terminal benzene ring pairs are coplanar and the angle between the central and terminal benzene ring is 73.01 (5)°.

Figure 1
Structure of the title compound, with displacement ellipsoids drawn at the 50% probability level and non-acidic H atoms omitted for clarity.

Experimental

p-Xylenediamine (68 mg, 0.5 mmol, 1 equiv.) was added to a solution of 3,4-dichloro-5-phenylcarbamoyl-1H-pyrrole-2-carboxylic acid (300 mg, 1 mmol, 2 equiv.) in DMF (30 ml) under a nitrogen atmosphere. Triethyamine (104 mg, 1 mmol, 2 equiv.), benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (572 mg, 1.1 mmol, 2.2 equiv.) and 5 mg (0.04 mmol, 0.04 equiv.) of N-hydroxybenzotriazole were added and the reaction was stirred for 72 h. The solvent was then removed and water (50 ml) was added. The product was extracted with dichloromethane (DCM, 3 × 50 ml). The organic phase was collected and the solvent was removed. The product was washed with diethyl ether (75 ml) and a small quantity of 10% MeOH in DCM (v/v). The product was obtained as a white solid (132 mg, 0.19 mmol, 38%).

M.p. 590 K (decomp.). ¹H NMR 300 MHz in DMSO-d₆ δ (p.p.m.): 4.50 (d, J = 5.4, 4H, CH₂), 7.00–7.70 (m, 14H, ArH), 8.50 (t, 2H, J = 5.4, central–CONH), 10.04 (s, 2H, outer–CONH), 12.79 (s, 2H, NH-pyrrole). ¹³C NMR 75 MHz in DMSO-d₆ δ (p.p.m.): 42.3, 112.0, 113.6, 119.8, 122.9, 123.1, 123.9, 127.4, 128.7, 137.6, 138.3, 156.5, 158.1. TOF LD⁺ mass spectrum: m/z (%): 472 (100) [C₂₃H₂₂Cl₂N₄O₃]⁺. Elemental analysis: Calc. for C₃₂H₂₄Cl₄N₆O₄.H₂O: C 53.65, H 3.66, N 11.73%; found: C 53.28, H 3.73, N 12.03%.

Crystals of the title compound were obtained by slow evaporation of an acetonitrile solution in the presence of excess tetrabutylammonium fluoride.

Crystal data

2C₁₆H₃₆N⁺·C₃₂H₂₂Cl₄N₆O₄²⁻
M_r = 1181.27
Triclinic, $[P\overline 1]$
a = 9.524 (2) Å
b = 10.363 (3) Å
c = 17.056 (4) Å
α = 78.293 (11)°
β = 88.733 (14)°
γ = 80.136 (14)°
V = 1623.9 (7) Å³
Z = 1
D_x = 1.208 Mg m⁻³
Mo Kα radiation
Cell parameters from 58835 reflections
θ = 2.9–27.5°
μ = 0.23 mm⁻¹
T = 120 (2) K
Block, colourless
0.20 × 0.10 × 0.07 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ) T_min = 0.732, T_max = 0.984
16494 measured reflections
5757 independent reflections
2777 reflections with I > 2σ(I)
R_int = 0.111
θ_max = 26.1°
h = −11 → 11
k = −12 → 12
l = −20 → 20

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.101
wR(F²) = 0.192
S = 1.04
5757 reflections
361 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0424P)² + 2.4189P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.019
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.24 e Å⁻³

H atoms were identified in a difference map and then placed in calculated positions (N—H 0.88, aromatic C—H 0.95, methylene C—H 0.99, methyl C—H 0.98) and refined using a riding model [U_iso(H) = 1.2 or 1.5 times U_eq(C,N)].

Data collection: DENZO (Otwinowski & Minor, 1997 ) and COLLECT (Hooft, 1998 ); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990 ); 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, s92. DOI: https://doi.org/10.1107/S160053680501069X/ac6168sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680501069X/ac6168Isup2.hkl

Computing details top

Data collection: DENZO (Otwinowski and Minor, 1997), COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski and Minor, 1997), COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski and Minor, 1997), COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); 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, 1998).

(I) top

Crystal data top

C₃₂H₂₂Cl₄N₆O₄·2(C₁₆H₃₆N)	Z = 1
M_r = 1181.27	F(000) = 634
Triclinic, P1	D_x = 1.208 Mg m⁻³
a = 9.524 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.363 (3) Å	Cell parameters from 58835 reflections
c = 17.056 (4) Å	θ = 2.9–27.5°
α = 78.293 (11)°	µ = 0.23 mm⁻¹
β = 88.733 (14)°	T = 120 K
γ = 80.136 (14)°	Block, colourless
V = 1623.9 (7) Å³	0.20 × 0.10 × 0.07 mm

Data collection top

Bruker Nonius Kappa CCD Area detector diffractometer	5757 independent reflections
Radiation source: Rotating Anode, Bruker Nonius FR591	2777 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.111
Detector resolution: 9.091 pixels mm^-1	θ_max = 26.1°, θ_min = 3.1°
φ and ω scans to fill the asymmetric unit	h = −11→11
Absorption correction: multi-scan SORTAV (Blessing, 1997)	k = −12→12
T_min = 0.732, T_max = 0.984	l = −20→20
16494 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)] = 0.101	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.192	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0424P)² + 2.4189P] where P = (F_o² + 2F_c²)/3
5757 reflections	(Δ/σ)_max < 0.001
361 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Special details top

Experimental. The higher angle reflections were very diffuse and weak and data above 26.09 θ theta were omitted from the refinement. As a result the _diffrn_reflns_theta_full is low (26.09) and the data are only 89% complete to this value

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.

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	1.03523 (16)	0.79277 (16)	0.44484 (8)	0.0620 (5)
Cl2	0.75939 (16)	1.05446 (16)	0.41527 (8)	0.0592 (5)
O1	1.1698 (4)	0.6453 (4)	0.3030 (2)	0.0566 (11)
O2	0.5971 (4)	1.1745 (4)	0.2402 (2)	0.0538 (11)
N1	1.0803 (5)	0.7269 (5)	0.1767 (3)	0.0487 (13)
H91	1.0146	0.7881	0.1488	0.058*
N2	0.8929 (5)	0.9176 (5)	0.2225 (3)	0.0428 (12)
N3	0.7274 (5)	1.1256 (5)	0.1331 (3)	0.0509 (13)
H93	0.8143	1.0972	0.1182	0.061*
C1	1.3027 (7)	0.5813 (6)	0.1559 (3)	0.0487 (16)
H1	1.3438	0.5951	0.2031	0.058*
C2	1.3809 (6)	0.5006 (6)	0.1103 (4)	0.0499 (16)
H2	1.4759	0.4599	0.1260	0.060*
C3	1.3233 (7)	0.4776 (6)	0.0415 (4)	0.0517 (16)
H3	1.3772	0.4204	0.0107	0.062*
C4	1.1854 (7)	0.5396 (6)	0.0183 (3)	0.0500 (16)
H4	1.1449	0.5266	−0.0293	0.060*
C5	1.1074 (6)	0.6196 (6)	0.0642 (4)	0.0510 (16)
H5	1.0124	0.6601	0.0483	0.061*
C6	1.1644 (6)	0.6427 (6)	0.1337 (4)	0.0464 (15)
C7	1.0864 (6)	0.7269 (6)	0.2570 (4)	0.0448 (15)
C8	0.9809 (6)	0.8328 (6)	0.2795 (3)	0.0392 (14)
C9	0.9494 (6)	0.8649 (6)	0.3541 (3)	0.0464 (15)
C10	0.8383 (6)	0.9723 (6)	0.3426 (3)	0.0472 (16)
C11	0.8045 (6)	1.0043 (6)	0.2588 (3)	0.0433 (15)
C12	0.6989 (7)	1.1095 (6)	0.2119 (4)	0.0445 (15)
C13	0.6200 (6)	1.1883 (6)	0.0721 (3)	0.0532 (16)
H13A	0.6622	1.2501	0.0298	0.064*
H13B	0.5414	1.2421	0.0964	0.064*
C14	0.5600 (6)	1.0907 (6)	0.0344 (3)	0.0447 (15)
C15	0.5075 (6)	1.1251 (6)	−0.0432 (3)	0.0480 (15)
H15	0.5137	1.2114	−0.0738	0.058*
C16	0.5528 (6)	0.9608 (6)	0.0775 (3)	0.0457 (15)
H16	0.5903	0.9328	0.1305	0.055*
N4	0.1867 (5)	0.2167 (4)	0.3108 (3)	0.0469 (12)
C17	0.2262 (6)	0.0766 (6)	0.3622 (3)	0.0512 (16)
H17A	0.1752	0.0738	0.4135	0.061*
H17B	0.1920	0.0123	0.3346	0.061*
C18	0.3849 (6)	0.0302 (6)	0.3803 (4)	0.0601 (18)
H18A	0.4115	0.0657	0.4266	0.072*
H18B	0.4401	0.0665	0.3336	0.072*
C19	0.4236 (7)	−0.1235 (6)	0.3994 (4)	0.0638 (18)
H19A	0.5150	−0.1498	0.4297	0.077*
H19B	0.3494	−0.1605	0.4341	0.077*
C20	0.4372 (7)	−0.1837 (7)	0.3263 (4)	0.083 (2)
H20A	0.3461	−0.1609	0.2970	0.125*
H20B	0.4630	−0.2811	0.3422	0.125*
H20C	0.5113	−0.1484	0.2919	0.125*
C21	0.2295 (6)	0.2154 (5)	0.2238 (3)	0.0476 (15)
H21A	0.2134	0.3087	0.1932	0.057*
H21B	0.3329	0.1808	0.2229	0.057*
C22	0.1520 (6)	0.1335 (6)	0.1811 (3)	0.0567 (17)
H22A	0.1787	0.0376	0.2060	0.068*
H22B	0.0479	0.1595	0.1869	0.068*
C23	0.1877 (6)	0.1538 (6)	0.0943 (3)	0.0530 (16)
H23A	0.2923	0.1317	0.0891	0.064*
H23B	0.1581	0.2495	0.0696	0.064*
C24	0.1181 (6)	0.0709 (6)	0.0483 (3)	0.0577 (17)
H24A	0.1469	−0.0242	0.0720	0.087*
H24B	0.1481	0.0880	−0.0077	0.087*
H24C	0.0143	0.0952	0.0507	0.087*
C25	0.0263 (5)	0.2587 (6)	0.3169 (3)	0.0482 (16)
H25A	−0.0213	0.1900	0.3010	0.058*
H25B	0.0030	0.2599	0.3737	0.058*
C26	−0.0351 (6)	0.3940 (6)	0.2662 (3)	0.0577 (17)
H26A	0.0094	0.4640	0.2828	0.069*
H26B	−0.0122	0.3943	0.2093	0.069*
C27	−0.1949 (6)	0.4260 (7)	0.2750 (4)	0.0664 (19)
H27A	−0.2386	0.3553	0.2585	0.080*
H27B	−0.2170	0.4243	0.3321	0.080*
C28	−0.2616 (7)	0.5599 (7)	0.2263 (4)	0.082 (2)
H28A	−0.2253	0.6312	0.2454	0.123*
H28B	−0.3653	0.5718	0.2320	0.123*
H28C	−0.2374	0.5638	0.1698	0.123*
C29	0.2666 (6)	0.3149 (5)	0.3386 (3)	0.0478 (16)
H29A	0.3702	0.2818	0.3360	0.057*
H29B	0.2452	0.4019	0.3006	0.057*
C30	0.2328 (6)	0.3380 (6)	0.4224 (3)	0.0522 (16)
H30A	0.2365	0.2508	0.4598	0.063*
H30B	0.1350	0.3889	0.4230	0.063*
C31	0.3377 (7)	0.4151 (6)	0.4504 (3)	0.0605 (18)
H31A	0.3415	0.4980	0.4101	0.073*
H31B	0.4341	0.3600	0.4554	0.073*
C32	0.2938 (7)	0.4511 (7)	0.5310 (4)	0.079 (2)
H32A	0.2018	0.5115	0.5250	0.118*
H32B	0.3661	0.4953	0.5496	0.118*
H32C	0.2854	0.3694	0.5702	0.118*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0602 (10)	0.0784 (12)	0.0446 (9)	−0.0219 (9)	−0.0037 (8)	0.0032 (8)
Cl2	0.0646 (11)	0.0723 (12)	0.0455 (9)	−0.0220 (9)	0.0084 (8)	−0.0148 (8)
O1	0.056 (3)	0.051 (3)	0.055 (3)	−0.001 (2)	−0.010 (2)	0.002 (2)
O2	0.047 (3)	0.059 (3)	0.055 (3)	−0.010 (2)	0.010 (2)	−0.010 (2)
N1	0.047 (3)	0.047 (3)	0.044 (3)	0.006 (3)	−0.005 (2)	−0.003 (3)
N2	0.041 (3)	0.042 (3)	0.044 (3)	−0.012 (3)	0.004 (2)	−0.002 (3)
N3	0.045 (3)	0.063 (4)	0.040 (3)	−0.013 (3)	0.003 (2)	0.002 (3)
C1	0.051 (4)	0.045 (4)	0.046 (4)	−0.011 (4)	0.003 (3)	0.002 (3)
C2	0.042 (4)	0.039 (4)	0.062 (4)	−0.011 (3)	0.005 (3)	0.008 (3)
C3	0.062 (5)	0.035 (4)	0.057 (4)	−0.016 (4)	0.011 (3)	−0.002 (3)
C4	0.051 (4)	0.049 (4)	0.044 (4)	−0.008 (4)	−0.003 (3)	0.005 (3)
C5	0.041 (4)	0.047 (4)	0.059 (4)	0.000 (3)	0.007 (3)	−0.003 (3)
C6	0.046 (4)	0.040 (4)	0.049 (4)	−0.005 (3)	0.003 (3)	0.000 (3)
C7	0.041 (4)	0.045 (4)	0.047 (4)	−0.012 (3)	−0.001 (3)	−0.003 (3)
C8	0.036 (3)	0.037 (4)	0.045 (4)	−0.010 (3)	0.001 (3)	−0.005 (3)
C9	0.049 (4)	0.043 (4)	0.048 (4)	−0.016 (3)	−0.001 (3)	−0.004 (3)
C10	0.060 (4)	0.045 (4)	0.046 (4)	−0.030 (4)	0.006 (3)	−0.012 (3)
C11	0.043 (4)	0.044 (4)	0.046 (4)	−0.018 (3)	0.003 (3)	−0.008 (3)
C12	0.046 (4)	0.044 (4)	0.047 (4)	−0.019 (4)	0.005 (3)	−0.009 (3)
C13	0.057 (4)	0.048 (4)	0.050 (4)	−0.008 (3)	0.001 (3)	0.000 (3)
C14	0.043 (4)	0.043 (4)	0.047 (4)	−0.006 (3)	0.010 (3)	−0.007 (3)
C15	0.059 (4)	0.038 (4)	0.041 (4)	−0.010 (3)	0.007 (3)	0.005 (3)
C16	0.043 (4)	0.048 (4)	0.042 (3)	−0.005 (3)	0.004 (3)	−0.001 (3)
N4	0.049 (3)	0.047 (3)	0.044 (3)	−0.023 (3)	−0.001 (2)	0.004 (2)
C17	0.061 (4)	0.052 (4)	0.043 (3)	−0.028 (3)	0.004 (3)	0.001 (3)
C18	0.056 (4)	0.059 (5)	0.060 (4)	−0.015 (4)	0.002 (3)	0.005 (3)
C19	0.066 (4)	0.065 (5)	0.056 (4)	−0.017 (4)	0.007 (3)	0.004 (4)
C20	0.092 (6)	0.075 (5)	0.083 (5)	−0.016 (5)	−0.003 (4)	−0.012 (4)
C21	0.049 (4)	0.046 (4)	0.047 (4)	−0.015 (3)	−0.001 (3)	−0.001 (3)
C22	0.061 (4)	0.066 (4)	0.046 (4)	−0.030 (4)	0.001 (3)	−0.002 (3)
C23	0.048 (4)	0.059 (4)	0.054 (4)	−0.017 (3)	0.003 (3)	−0.011 (3)
C24	0.062 (4)	0.058 (4)	0.050 (4)	−0.013 (4)	0.008 (3)	−0.002 (3)
C25	0.042 (4)	0.063 (4)	0.045 (4)	−0.025 (3)	0.004 (3)	−0.010 (3)
C26	0.046 (4)	0.070 (5)	0.055 (4)	−0.016 (4)	0.000 (3)	−0.002 (3)
C27	0.053 (4)	0.070 (5)	0.080 (5)	−0.012 (4)	0.004 (4)	−0.023 (4)
C28	0.049 (4)	0.098 (6)	0.096 (6)	−0.001 (4)	−0.011 (4)	−0.022 (5)
C29	0.047 (4)	0.051 (4)	0.046 (4)	−0.023 (3)	−0.007 (3)	0.003 (3)
C30	0.058 (4)	0.053 (4)	0.046 (4)	−0.023 (3)	−0.007 (3)	0.001 (3)
C31	0.071 (4)	0.055 (4)	0.055 (4)	−0.022 (4)	−0.016 (3)	0.003 (3)
C32	0.082 (5)	0.079 (5)	0.078 (5)	−0.017 (4)	−0.015 (4)	−0.019 (4)

Geometric parameters (Å, º) top

Cl1—C9	1.732 (6)	C2—H2	0.9500
Cl2—C10	1.730 (6)	C3—H3	0.9500
O1—C7	1.220 (6)	C4—H4	0.9500
O2—C12	1.231 (6)	C5—H5	0.9500
N1—C7	1.373 (7)	C13—H13A	0.9901
N1—C6	1.391 (7)	C13—H13B	0.9900
N2—C11	1.358 (7)	C15—H15	0.9499
N2—C8	1.362 (6)	C16—H16	0.9499
N3—C12	1.348 (7)	C17—H17A	0.9899
N3—C13	1.447 (6)	C17—H17B	0.9900
C1—C2	1.373 (8)	C18—H18A	0.9901
C1—C6	1.386 (7)	C18—H18B	0.9900
C2—C3	1.385 (8)	C19—H19A	0.9900
C3—C4	1.387 (7)	C19—H19B	0.9900
C4—C5	1.371 (7)	C20—H20A	0.9800
C5—C6	1.394 (8)	C20—H20B	0.9799
C7—C8	1.462 (8)	C20—H20C	0.9800
C8—C9	1.393 (7)	C21—H21A	0.9899
C9—C10	1.384 (7)	C21—H21B	0.9900
C10—C11	1.431 (7)	C22—H22A	0.9900
C11—C12	1.465 (8)	C22—H22B	0.9900
C13—C14	1.498 (7)	C23—H23A	0.9900
C14—C15	1.381 (7)	C23—H23B	0.9899
C14—C16	1.408 (7)	C24—H24A	0.9800
C15—C16ⁱ	1.366 (7)	C24—H24B	0.9799
C16—C15ⁱ	1.366 (7)	C24—H24C	0.9801
N4—C25	1.522 (7)	C25—H25A	0.9900
N4—C29	1.523 (6)	C25—H25B	0.9900
N4—C17	1.526 (6)	C26—H26A	0.9900
N4—C21	1.533 (6)	C26—H26B	0.9901
C17—C18	1.524 (7)	C27—H27A	0.9900
C18—C19	1.540 (8)	C27—H27B	0.9900
C19—C20	1.497 (8)	C28—H28A	0.9800
C21—C22	1.512 (7)	C28—H28B	0.9800
C22—C23	1.492 (7)	C28—H28C	0.9800
C23—C24	1.511 (7)	C29—H29A	0.9900
C25—C26	1.519 (7)	C29—H29B	0.9900
C26—C27	1.512 (7)	C30—H30A	0.9900
C27—C28	1.508 (8)	C30—H30B	0.9900
C29—C30	1.516 (7)	C31—H31A	0.9899
C30—C31	1.521 (7)	C31—H31B	0.9899
C31—C32	1.528 (8)	C32—H32A	0.9800
N1—H91	0.8800	C32—H32B	0.9800
N3—H93	0.8801	C32—H32C	0.9799
C1—H1	0.9500

C7—N1—C6	128.4 (5)	C17—C18—H18A	109.3
C11—N2—C8	108.2 (5)	C19—C18—H18A	109.3
C12—N3—C13	122.2 (5)	C17—C18—H18B	109.3
C2—C1—C6	120.6 (6)	C19—C18—H18B	109.3
C1—C2—C3	121.0 (6)	H18A—C18—H18B	108.0
C2—C3—C4	119.0 (6)	C20—C19—H19A	108.9
C5—C4—C3	119.9 (6)	C18—C19—H19A	108.9
C4—C5—C6	121.5 (6)	C20—C19—H19B	108.9
C1—C6—N1	123.4 (6)	C18—C19—H19B	108.9
C1—C6—C5	118.1 (6)	H19A—C19—H19B	107.7
N1—C6—C5	118.5 (5)	C19—C20—H20A	109.5
O1—C7—N1	122.6 (6)	C19—C20—H20B	109.5
O1—C7—C8	125.4 (6)	H20A—C20—H20B	109.5
N1—C7—C8	112.0 (5)	C19—C20—H20C	109.5
N2—C8—C9	109.8 (5)	H20A—C20—H20C	109.5
N2—C8—C7	119.9 (5)	H20B—C20—H20C	109.5
C9—C8—C7	130.3 (6)	C22—C21—H21A	108.3
C10—C9—C8	107.1 (5)	N4—C21—H21A	108.4
C10—C9—Cl1	124.9 (5)	C22—C21—H21B	108.3
C8—C9—Cl1	128.0 (5)	N4—C21—H21B	108.3
C9—C10—C11	106.6 (5)	H21A—C21—H21B	107.4
C9—C10—Cl2	126.4 (5)	C23—C22—H22A	109.4
C11—C10—Cl2	126.9 (5)	C21—C22—H22A	109.4
N2—C11—C10	108.3 (5)	C23—C22—H22B	109.4
N2—C11—C12	120.5 (5)	C21—C22—H22B	109.4
C10—C11—C12	131.1 (6)	H22A—C22—H22B	108.0
O2—C12—N3	124.2 (6)	C22—C23—H23A	108.7
O2—C12—C11	124.8 (5)	C24—C23—H23A	108.7
N3—C12—C11	111.0 (5)	C22—C23—H23B	108.7
N3—C13—C14	113.6 (5)	C24—C23—H23B	108.7
C15—C14—C16	117.5 (5)	H23A—C23—H23B	107.6
C15—C14—C13	121.4 (5)	C23—C24—H24A	109.5
C16—C14—C13	121.0 (5)	C23—C24—H24B	109.5
C16ⁱ—C15—C14	122.2 (5)	H24A—C24—H24B	109.5
C15ⁱ—C16—C14	120.3 (5)	C23—C24—H24C	109.5
C25—N4—C29	111.0 (4)	H24A—C24—H24C	109.5
C25—N4—C17	107.3 (4)	H24B—C24—H24C	109.5
C29—N4—C17	111.2 (4)	C26—C25—H25A	108.4
C25—N4—C21	110.8 (4)	N4—C25—H25A	108.4
C29—N4—C21	106.6 (4)	C26—C25—H25B	108.6
C17—N4—C21	110.0 (4)	N4—C25—H25B	108.5
C18—C17—N4	115.1 (4)	H25A—C25—H25B	107.5
C17—C18—C19	111.6 (5)	C27—C26—H26A	109.3
C20—C19—C18	113.3 (5)	C25—C26—H26A	109.2
C22—C21—N4	115.8 (4)	C27—C26—H26B	109.4
C23—C22—C21	111.2 (4)	C25—C26—H26B	109.4
C22—C23—C24	114.1 (4)	H26A—C26—H26B	108.0
C26—C25—N4	115.2 (4)	C28—C27—H27A	108.9
C27—C26—C25	111.4 (5)	C26—C27—H27A	108.8
C28—C27—C26	113.7 (5)	C28—C27—H27B	108.8
C30—C29—N4	115.4 (4)	C26—C27—H27B	108.9
C29—C30—C31	111.1 (4)	H27A—C27—H27B	107.7
C30—C31—C32	110.9 (5)	C27—C28—H28A	109.5
C7—N1—H91	115.7	C27—C28—H28B	109.4
C6—N1—H91	115.8	H28A—C28—H28B	109.5
C12—N3—H93	118.9	C27—C28—H28C	109.4
C13—N3—H93	118.8	H28A—C28—H28C	109.5
C2—C1—H1	119.7	H28B—C28—H28C	109.5
C6—C1—H1	119.7	C30—C29—H29A	108.4
C1—C2—H2	119.5	N4—C29—H29A	108.4
C3—C2—H2	119.5	C30—C29—H29B	108.5
C2—C3—H3	120.6	N4—C29—H29B	108.4
C5—C4—H4	120.0	H29A—C29—H29B	107.5
C3—C4—H4	120.1	C29—C30—H30A	109.5
C4—C5—H5	119.2	C31—C30—H30A	109.5
C6—C5—H5	119.3	C29—C30—H30B	109.4
N3—C13—H13A	108.9	C31—C30—H30B	109.3
C14—C13—H13A	108.8	H30A—C30—H30B	108.0
N3—C13—H13B	108.8	C30—C31—H31A	109.6
C14—C13—H13B	108.9	C32—C31—H31A	109.4
H13A—C13—H13B	107.7	C30—C31—H31B	109.4
C16ⁱ—C15—H15	118.9	C32—C31—H31B	109.5
C14—C15—H15	118.9	H31A—C31—H31B	108.1
C15ⁱ—C16—H16	119.9	C31—C32—H32A	109.5
C14—C16—H16	119.9	C31—C32—H32B	109.5
C18—C17—H17A	108.5	H32A—C32—H32B	109.5
N4—C17—H17A	108.5	C31—C32—H32C	109.4
C18—C17—H17B	108.4	H32A—C32—H32C	109.5
N4—C17—H17B	108.5	H32B—C32—H32C	109.5
H17A—C17—H17B	107.5

Symmetry code: (i) −x+1, −y+2, −z.

Acknowledgements

The authors thank the EPSRC for funding the crystallographic facilities. PAG thanks the Royal Society for a University Research Fellowship and Universities UK for an ORS studentship to KN.

References

Blessing, R. H. (1997). J. Appl. Cryst. 30, 421–426. CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Hooft, R. (1998). COLLECT. Nonius BV, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr and R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (1990). Acta Cryst. A46, 467–473. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany. Google Scholar
Watkin, D. M., Pearce, L. & Prout, C. K. (1993). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England. Google Scholar

© International Union of Crystallography. Prior permission is not required to reproduce short quotations, tables and figures from this article, provided the original authors and source are cited. For more information, click here.