1,4-Phenyl­ene-bis-(3,4-di­chloro-5-phenyl­carbamoyl-1H-pyrrole-2-carbox­amide) bis(tetra­butyl­ammonium chloride) aceto­nitrile disolvate

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

doi:10.1107/S1600536805010688

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 61| Part 5| May 2005| Pages o1300-o1301

https://doi.org/10.1107/S1600536805010688

1,4-Phenylene-bis-(3,4-dichloro-5-phenylcarbamoyl-1H-pyrrole-2-carboxamide) bis(tetrabutylammonium chloride) acetonitrile disolvate

Mark E. Light,^a ^* Philip A. Gale ^a and Korakot Navakhun ^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 title compound, C₃₀H₂₀N₆O₄Cl₄.2C₁₆H₃₆N⁺·2Cl⁻·2C₂H₃N, contains two hydrogen-bonded chloride anions bound to 1,4-phenylene-bis-(3,4-dichloro-5-phenylcarbamoyl-1H-pyrrole-2-carboxamide) as the tetrabutylammonium salt. There is also a short pyrrolic hydrogen bond (N⋯Cl = 3.068 (3) Å), and two longer ones to the amino H atoms [N⋯Cl = 3.269 (3) Å and 3.275 (3) Å]. The neutral molecule lies on an inversion centre situated at the centre of the central benzene ring.

Comment

1,4-Phenylene-bis-(3,4-dichloro-5-phenylcarbamoyl-1H-pyrrole-2-carboxamide) crystallizes from tetrabutylammonium chloride acetonitrile solution as a tetrabutylammonium chloride acetonitrile solvate, (I).

The receptor adopts an S-shaped conformation around a centre of inversion with one chloride bound on each side. The pyrrole and terminal benzene ring pairs are coplanar, and the angle between the central and terminal benzene rings is 32.02 (4)°. Of the three hydrogen bonds to the chloride, the pyrrolic one is the shortest, with an N⋯Cl distance of 3.068 (3) Å, whilst the two either side are longer, with distances of 3.269 (3) Å and 3.275 (3) Å.

Figure 1
Structure of the title compound, with displacement ellipsoids drawn at the 35% probability level and non-acidic H atoms omitted for clarity. Both disorder components are shown.

Experimental

The receptor molecule, 1,4-phenylene-bis-(3,4-dichloro-5-phenylcarbamoyl-1H-pyrrole-2-carboxamide), (1), was synthesized according to literature methods (Gale et al., 2002 ). Crystals of the acetonitrile solvate of the tetrabutylammonium chloride complex were grown by slow evaporation of an acetonitrile solution of (1) in acetonitrile in the presence of excess tetrabutylammonium chloride.

Crystal data

C₃₀H₂₀N₆O₄Cl₄·2C₁₆H₃₆N⁺·2Cl⁻·2C₂H₃N
M_r = 1308.24
Monoclinic, P2₁/c
a = 8.5720 (2) Å
b = 21.1088 (5) Å
c = 19.3520 (6) Å
β = 93.5560 (10)° precision OK?
V = 3494.90 (16) Å³
Z = 2
D_x = 1.243 Mg m⁻³
Mo Kα radiation
Cell parameters from 35384 reflections
θ = 2.9–26.4°
μ = 0.30 mm⁻¹
T = 120 (2) K
Needle, colourless
0.15 × 0.07 × 0.05 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ) T_min = 0.906, T_max = 0.990
13653 measured reflections
7107 independent reflections
4902 reflections with I > 2σ(I)
R_int = 0.046
θ_max = 26.4°
h = −10 → 10
k = −26 → 25
l = −24 → 24

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.144
S = 1.11
7107 reflections
395 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0389P)² + 4.3109P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.001
Δρ_max = 0.70 e Å⁻³
Δρ_min = −1.05 e Å⁻³
Extinction correction: SHELXL97
Extinction coefficient: 0.0023 (4)

Table 1
Hydrogen-bonding geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H91⋯Cl3	0.88	2.40	3.269 (3)	171.6
N2—H92⋯Cl3	0.88	2.20	3.068 (3)	166.8
N3—H93⋯Cl3	0.88	2.40	3.275 (3)	171.2

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(parent atom)]. One arm of the tetrabutylammonium is disordered. It has been modelled as split over two possible orientations with one third and two thirds occupancy. C—C and C—N distances were restrained to standard values and the displacement parameters of split atom pairs were constrained to be equal. The deepest hole is located 1.28 Å from C9.

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, 02sot127. DOI: https://doi.org/10.1107/S1600536805010688/ac6167sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536805010688/ac6167Isup2.hkl

Computing details top

Data collection: DENZO (Otwinowski and 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, 1998).

(I) top

Crystal data top

C₃₀H₂₀N₆O₄Cl₄·2C₁₆H₃₆N⁺·2Cl⁻·2C₂H₃N	F(000) = 1396
M_r = 1308.24	D_x = 1.243 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.5720 (2) Å	Cell parameters from 35384 reflections
b = 21.1088 (5) Å	θ = 2.9–26.4°
c = 19.3520 (6) Å	µ = 0.30 mm⁻¹
β = 93.556 (1)°	T = 120 K
V = 3494.90 (16) Å³	Needle, colourless
Z = 2	0.15 × 0.07 × 0.05 mm

Data collection top

Bruker-Nonius KappaCCD area-detector diffractometer	7107 independent reflections
Radiation source: Rotating Anode, Bruker Nonius FR591	4902 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
Detector resolution: 9.091 pixels mm^-1	θ_max = 26.4°, θ_min = 3.1°
φ and ω scans to fill the asymmetric unit	h = −10→10
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	k = −26→25
T_min = 0.906, T_max = 0.990	l = −24→24
13653 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)] = 0.060	H-atom parameters constrained
wR(F²) = 0.144	w = 1/[σ²(F_o²) + (0.0389P)² + 4.3109P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max = 0.001
7107 reflections	Δρ_max = 0.70 e Å⁻³
395 parameters	Δρ_min = −1.05 e Å⁻³
71 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0023 (4)

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.

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	Occ. (<1)
Cl1	0.16835 (9)	0.70673 (4)	0.60764 (4)	0.0322 (2)
Cl2	0.38459 (10)	0.57889 (4)	0.64814 (4)	0.0336 (2)
Cl3	0.18791 (9)	0.69400 (4)	0.95662 (4)	0.0282 (2)
N1	0.0570 (3)	0.78167 (12)	0.82639 (13)	0.0269 (6)
H91	0.1008	0.7571	0.8588	0.032*
N2	0.2000 (3)	0.66144 (12)	0.80256 (13)	0.0253 (6)
H92	0.1828	0.6667	0.8465	0.030*
N3	0.3598 (3)	0.57156 (13)	0.89035 (13)	0.0299 (6)
H93	0.3070	0.6047	0.9037	0.036*
O1	−0.0100 (3)	0.78668 (13)	0.71095 (13)	0.0488 (7)
O2	0.4268 (3)	0.51780 (11)	0.79409 (12)	0.0354 (6)
C1	−0.1002 (4)	0.87948 (16)	0.80754 (19)	0.0338 (8)
H1	−0.1308	0.8677	0.7613	0.041*
C2	−0.1505 (4)	0.93640 (17)	0.8346 (2)	0.0385 (9)
H2	−0.2162	0.9635	0.8064	0.046*
C3	−0.1069 (4)	0.95440 (17)	0.90160 (19)	0.0386 (9)
H3	−0.1404	0.9938	0.9191	0.046*
C4	−0.0142 (4)	0.91450 (18)	0.94291 (19)	0.0398 (9)
H4	0.0150	0.9263	0.9893	0.048*
C5	0.0367 (4)	0.85722 (16)	0.91719 (18)	0.0326 (8)
H5	0.0999	0.8298	0.9460	0.039*
C6	−0.0048 (3)	0.84006 (15)	0.84902 (17)	0.0268 (7)
C7	0.0562 (4)	0.75944 (16)	0.76053 (17)	0.0291 (7)
C8	0.1449 (3)	0.70049 (15)	0.75015 (16)	0.0259 (7)
C9	0.1974 (3)	0.67619 (15)	0.68946 (16)	0.0251 (7)
C10	0.2860 (3)	0.62214 (15)	0.70655 (16)	0.0248 (7)
C11	0.2856 (3)	0.61305 (15)	0.77710 (16)	0.0249 (7)
C12	0.3633 (4)	0.56283 (15)	0.82090 (16)	0.0268 (7)
C13	0.3841 (4)	0.54326 (15)	1.01052 (17)	0.0287 (7)
H13	0.3042	0.5733	1.0178	0.034*
C14	0.4311 (4)	0.53353 (14)	0.94363 (16)	0.0254 (7)
C15	0.5488 (4)	0.48980 (15)	0.93349 (17)	0.0276 (7)
H15	0.5830	0.4827	0.8884	0.033*
N4	0.6730 (3)	0.78866 (15)	0.53584 (13)	0.0369 (7)
C16	0.6876 (4)	0.71763 (18)	0.53514 (19)	0.0428 (10)
H16A	0.7130	0.7029	0.5831	0.051*
H16B	0.7763	0.7061	0.5073	0.051*
C17	0.5423 (4)	0.68249 (18)	0.5063 (2)	0.0448 (10)
H17A	0.4625	0.6827	0.5411	0.054*
H17B	0.4981	0.7047	0.4645	0.054*
C18	0.5802 (5)	0.6145 (2)	0.4878 (2)	0.0587 (12)
H18A	0.6625	0.6145	0.4541	0.070*
H18B	0.6223	0.5923	0.5300	0.070*
C19	0.4393 (5)	0.5784 (2)	0.4572 (2)	0.0608 (12)
H19A	0.3608	0.5750	0.4918	0.091*
H19B	0.4716	0.5359	0.4437	0.091*
H19C	0.3945	0.6010	0.4164	0.091*
C20A	0.630 (3)	0.8185 (17)	0.4688 (7)	0.0422 (16)	0.33
H20A	0.6117	0.8639	0.4779	0.051*	0.33
H20B	0.5279	0.8003	0.4521	0.051*	0.33
C21A	0.7378 (10)	0.8148 (5)	0.4082 (4)	0.0301 (12)	0.33
H21A	0.8400	0.8342	0.4224	0.036*	0.33
H21B	0.7561	0.7699	0.3966	0.036*	0.33
C22A	0.6656 (11)	0.8494 (5)	0.3439 (3)	0.0382 (13)	0.33
H22A	0.5558	0.8356	0.3349	0.046*	0.33
H22B	0.6654	0.8956	0.3528	0.046*	0.33
C23A	0.7577 (14)	0.8357 (6)	0.2797 (4)	0.0549 (15)	0.33
H23A	0.8626	0.8540	0.2863	0.082*	0.33
H23B	0.7031	0.8546	0.2387	0.082*	0.33
H23C	0.7659	0.7898	0.2733	0.082*	0.33
C20B	0.6322 (15)	0.8116 (7)	0.4628 (3)	0.0422 (16)	0.67
H20C	0.6492	0.8580	0.4613	0.051*	0.67
H20D	0.5196	0.8038	0.4516	0.051*	0.67
C21B	0.7262 (6)	0.7803 (2)	0.4067 (2)	0.0301 (12)	0.67
H21C	0.8386	0.7803	0.4219	0.036*	0.67
H21D	0.6922	0.7357	0.4004	0.036*	0.67
C22B	0.7025 (6)	0.8158 (2)	0.33735 (16)	0.0382 (13)	0.67
H22C	0.7477	0.7906	0.3004	0.046*	0.67
H22D	0.5893	0.8209	0.3253	0.046*	0.67
C23B	0.7807 (7)	0.8815 (2)	0.3413 (3)	0.0549 (15)	0.67
H23D	0.7279	0.9082	0.3741	0.082*	0.67
H23E	0.7729	0.9012	0.2954	0.082*	0.67
H23F	0.8910	0.8768	0.3570	0.082*	0.67
C24	0.8284 (4)	0.81522 (18)	0.56291 (18)	0.0407 (9)
H24A	0.9060	0.8069	0.5282	0.049*
H24B	0.8627	0.7919	0.6055	0.049*
C25	0.8304 (4)	0.8857 (2)	0.5793 (2)	0.0481 (11)
H25A	0.7668	0.8938	0.6194	0.058*
H25B	0.7831	0.9094	0.5391	0.058*
C26	0.9971 (4)	0.9094 (2)	0.5959 (2)	0.0523 (11)
H26A	1.0439	0.8854	0.6360	0.063*
H26B	1.0603	0.9008	0.5559	0.063*
C27	1.0042 (5)	0.9796 (2)	0.6125 (3)	0.0670 (14)
H27A	0.9553	1.0036	0.5736	0.101*
H27B	1.1136	0.9927	0.6203	0.101*
H27C	0.9484	0.9879	0.6542	0.101*
C28	0.5439 (4)	0.80920 (18)	0.58037 (17)	0.0355 (8)
H28A	0.4446	0.7908	0.5607	0.043*
H28B	0.5342	0.8559	0.5771	0.043*
C29	0.5623 (4)	0.79135 (17)	0.65683 (17)	0.0345 (8)
H29A	0.6707	0.8000	0.6751	0.041*
H29B	0.5414	0.7456	0.6624	0.041*
C30	0.4476 (4)	0.83005 (18)	0.69701 (18)	0.0394 (9)
H30A	0.4691	0.8757	0.6906	0.047*
H30B	0.3399	0.8216	0.6778	0.047*
C31	0.4579 (5)	0.8149 (2)	0.77423 (19)	0.0489 (10)
H31A	0.4398	0.7695	0.7809	0.073*
H31B	0.3786	0.8392	0.7971	0.073*
H31C	0.5620	0.8261	0.7943	0.073*
N5	0.1513 (5)	0.4085 (2)	0.3604 (2)	0.0760 (8)
C32	0.1877 (6)	0.4529 (3)	0.3326 (3)	0.0760 (8)
C33	0.2353 (6)	0.5087 (3)	0.2980 (3)	0.0760 (8)
H33A	0.2260	0.5454	0.3285	0.114*
H33B	0.1684	0.5149	0.2556	0.114*
H33C	0.3442	0.5042	0.2861	0.114*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0372 (4)	0.0405 (5)	0.0186 (4)	0.0071 (3)	0.0002 (3)	0.0055 (3)
Cl2	0.0420 (5)	0.0354 (5)	0.0238 (4)	0.0068 (4)	0.0060 (3)	0.0001 (4)
Cl3	0.0298 (4)	0.0346 (5)	0.0200 (4)	0.0070 (3)	−0.0008 (3)	0.0006 (3)
N1	0.0307 (14)	0.0291 (15)	0.0204 (15)	0.0052 (11)	−0.0017 (11)	0.0040 (11)
N2	0.0288 (14)	0.0290 (15)	0.0177 (14)	0.0060 (11)	−0.0010 (10)	0.0017 (11)
N3	0.0402 (16)	0.0271 (15)	0.0225 (15)	0.0138 (12)	0.0019 (11)	0.0038 (12)
O1	0.0698 (18)	0.0513 (17)	0.0244 (14)	0.0326 (14)	−0.0060 (12)	0.0028 (12)
O2	0.0508 (15)	0.0314 (14)	0.0236 (13)	0.0146 (11)	0.0002 (10)	−0.0012 (10)
C1	0.0354 (19)	0.035 (2)	0.031 (2)	0.0050 (15)	0.0032 (14)	0.0037 (16)
C2	0.040 (2)	0.033 (2)	0.043 (2)	0.0071 (15)	0.0041 (16)	0.0038 (17)
C3	0.040 (2)	0.032 (2)	0.044 (2)	0.0012 (16)	0.0071 (16)	−0.0070 (17)
C4	0.041 (2)	0.044 (2)	0.034 (2)	−0.0001 (17)	−0.0039 (16)	−0.0102 (17)
C5	0.0302 (18)	0.035 (2)	0.032 (2)	0.0011 (14)	−0.0031 (14)	−0.0003 (15)
C6	0.0255 (16)	0.0262 (17)	0.0287 (18)	−0.0005 (13)	0.0029 (13)	0.0001 (14)
C7	0.0286 (17)	0.0354 (19)	0.0233 (18)	0.0080 (14)	0.0003 (13)	0.0060 (15)
C8	0.0265 (16)	0.0316 (18)	0.0190 (17)	0.0040 (13)	−0.0029 (12)	0.0038 (13)
C9	0.0278 (16)	0.0277 (18)	0.0193 (17)	0.0001 (13)	−0.0012 (12)	0.0037 (13)
C10	0.0242 (16)	0.0280 (18)	0.0223 (17)	−0.0017 (13)	0.0008 (12)	−0.0010 (13)
C11	0.0266 (16)	0.0265 (17)	0.0211 (17)	0.0016 (13)	−0.0014 (12)	0.0009 (13)
C12	0.0292 (17)	0.0295 (18)	0.0214 (18)	0.0030 (13)	0.0003 (13)	0.0029 (14)
C13	0.0343 (18)	0.0258 (18)	0.0264 (18)	0.0104 (13)	0.0048 (13)	0.0019 (14)
C14	0.0319 (17)	0.0219 (17)	0.0222 (17)	0.0040 (13)	0.0001 (13)	0.0041 (13)
C15	0.0353 (18)	0.0259 (18)	0.0221 (17)	0.0049 (13)	0.0050 (13)	0.0006 (14)
N4	0.0233 (14)	0.065 (2)	0.0223 (15)	0.0097 (13)	0.0012 (11)	0.0114 (14)
C16	0.037 (2)	0.063 (3)	0.029 (2)	0.0218 (18)	0.0035 (15)	0.0039 (18)
C17	0.033 (2)	0.064 (3)	0.037 (2)	0.0110 (18)	0.0034 (16)	0.0024 (19)
C18	0.053 (3)	0.074 (3)	0.050 (3)	0.022 (2)	0.007 (2)	−0.009 (2)
C19	0.064 (3)	0.071 (3)	0.046 (3)	0.008 (2)	−0.007 (2)	−0.005 (2)
C20A	0.0237 (18)	0.084 (4)	0.019 (2)	0.005 (2)	0.0002 (16)	0.016 (3)
C21A	0.026 (2)	0.039 (4)	0.026 (2)	−0.004 (3)	0.0019 (16)	0.007 (3)
C22A	0.043 (3)	0.047 (4)	0.025 (2)	0.007 (3)	0.004 (2)	0.004 (3)
C23A	0.064 (4)	0.048 (3)	0.055 (4)	0.007 (3)	0.028 (3)	0.015 (3)
C20B	0.0237 (18)	0.084 (4)	0.019 (2)	0.005 (2)	0.0002 (16)	0.016 (3)
C21B	0.026 (2)	0.039 (4)	0.026 (2)	−0.004 (3)	0.0019 (16)	0.007 (3)
C22B	0.043 (3)	0.047 (4)	0.025 (2)	0.007 (3)	0.004 (2)	0.004 (3)
C23B	0.064 (4)	0.048 (3)	0.055 (4)	0.007 (3)	0.028 (3)	0.015 (3)
C24	0.0272 (18)	0.069 (3)	0.0257 (19)	0.0113 (17)	0.0005 (14)	0.0096 (18)
C25	0.0283 (19)	0.081 (3)	0.035 (2)	0.0079 (19)	−0.0012 (15)	0.010 (2)
C26	0.034 (2)	0.078 (3)	0.046 (3)	0.005 (2)	0.0065 (17)	0.005 (2)
C27	0.043 (3)	0.095 (4)	0.063 (3)	−0.002 (2)	0.003 (2)	−0.006 (3)
C28	0.0253 (17)	0.050 (2)	0.032 (2)	0.0070 (15)	0.0060 (14)	0.0088 (17)
C29	0.0330 (18)	0.041 (2)	0.030 (2)	0.0041 (15)	0.0050 (14)	0.0069 (16)
C30	0.041 (2)	0.043 (2)	0.036 (2)	−0.0016 (16)	0.0100 (16)	−0.0028 (17)
C31	0.045 (2)	0.066 (3)	0.037 (2)	−0.011 (2)	0.0103 (17)	−0.008 (2)
N5	0.0679 (17)	0.079 (2)	0.079 (2)	0.0018 (16)	−0.0066 (14)	0.0135 (16)
C32	0.0679 (17)	0.079 (2)	0.079 (2)	0.0018 (16)	−0.0066 (14)	0.0135 (16)
C33	0.0679 (17)	0.079 (2)	0.079 (2)	0.0018 (16)	−0.0066 (14)	0.0135 (16)

Geometric parameters (Å, º) top

Cl1—C9	1.713 (3)	C4—H4	0.9500
Cl2—C10	1.716 (3)	C5—H5	0.9500
N1—C7	1.358 (4)	C13—H13	0.9500
N1—C6	1.421 (4)	C15—H15	0.9500
N2—C11	1.367 (4)	C16—H16A	0.9900
N2—C8	1.368 (4)	C16—H16B	0.9900
N3—C12	1.359 (4)	C17—H17A	0.9900
N3—C14	1.416 (4)	C17—H17B	0.9900
O1—C7	1.227 (4)	C18—H18A	0.9900
O2—C12	1.226 (4)	C18—H18B	0.9900
C1—C6	1.387 (4)	C19—H19A	0.9800
C1—C2	1.390 (5)	C19—H19B	0.9800
C2—C3	1.381 (5)	C19—H19C	0.9800
C3—C4	1.379 (5)	C20A—H20A	0.9900
C4—C5	1.388 (5)	C20A—H20B	0.9900
C5—C6	1.393 (5)	C21A—H21A	0.9900
C7—C8	1.478 (4)	C21A—H21B	0.9900
C8—C9	1.382 (4)	C22A—H22A	0.9900
C9—C10	1.399 (4)	C22A—H22B	0.9900
C10—C11	1.379 (4)	C23A—H23A	0.9800
C11—C12	1.489 (4)	C23A—H23B	0.9800
C13—C15ⁱ	1.384 (4)	C23A—H23C	0.9800
C13—C14	1.395 (4)	C20B—H20C	0.9900
C14—C15	1.390 (4)	C20B—H20D	0.9900
C15—C13ⁱ	1.384 (4)	C21B—H21C	0.9900
N4—C20A	1.469 (8)	C21B—H21D	0.9900
N4—C16	1.505 (4)	C22B—H22C	0.9900
N4—C24	1.508 (4)	C22B—H22D	0.9900
N4—C28	1.508 (4)	C23B—H23D	0.9800
N4—C20B	1.514 (5)	C23B—H23E	0.9800
C16—C17	1.525 (5)	C23B—H23F	0.9800
C17—C18	1.519 (5)	C24—H24A	0.9900
C18—C19	1.517 (5)	C24—H24B	0.9900
C20A—C21A	1.5399 (11)	C25—H25A	0.9900
C21A—C22A	1.5398 (11)	C25—H25B	0.9900
C22A—C23A	1.5396 (11)	C26—H26A	0.9900
C20B—C21B	1.5405 (11)	C26—H26B	0.9900
C21B—C22B	1.5403 (10)	C27—H27A	0.9800
C22B—C23B	1.5393 (11)	C27—H27B	0.9800
C24—C25	1.522 (5)	C27—H27C	0.9800
C25—C26	1.529 (5)	C28—H28A	0.9900
C26—C27	1.518 (5)	C28—H28B	0.9900
C28—C29	1.525 (4)	C29—H29A	0.9900
C29—C30	1.528 (5)	C29—H29B	0.9900
C30—C31	1.526 (5)	C30—H30A	0.9900
N5—C32	1.135 (6)	C30—H30B	0.9900
C32—C33	1.427 (7)	C31—H31A	0.9800
N1—H91	0.8800	C31—H31B	0.9800
N2—H92	0.8800	C31—H31C	0.9800
N3—H93	0.8800	C33—H33A	0.9800
C1—H1	0.9500	C33—H33B	0.9800
C2—H2	0.9500	C33—H33C	0.9800
C3—H3	0.9500

C7—N1—C6	127.5 (3)	C17—C18—H18B	109.0
C11—N2—C8	110.6 (3)	H18A—C18—H18B	107.8
C12—N3—C14	127.5 (3)	C18—C19—H19A	109.5
C6—C1—C2	119.1 (3)	C18—C19—H19B	109.5
C3—C2—C1	121.3 (3)	H19A—C19—H19B	109.5
C2—C3—C4	119.3 (3)	C18—C19—H19C	109.5
C3—C4—C5	120.5 (3)	H19A—C19—H19C	109.5
C4—C5—C6	119.9 (3)	H19B—C19—H19C	109.5
C1—C6—C5	119.9 (3)	N4—C20A—H20A	107.0
C1—C6—N1	124.0 (3)	C21A—C20A—H20A	107.0
C5—C6—N1	116.0 (3)	N4—C20A—H20B	107.0
O1—C7—N1	123.2 (3)	C21A—C20A—H20B	107.0
O1—C7—C8	120.3 (3)	H20A—C20A—H20B	106.7
N1—C7—C8	116.5 (3)	C22A—C21A—H21A	109.4
N2—C8—C9	106.9 (3)	C20A—C21A—H21A	109.4
N2—C8—C7	124.3 (3)	C22A—C21A—H21B	109.4
C9—C8—C7	128.7 (3)	C20A—C21A—H21B	109.4
C8—C9—C10	107.6 (3)	H21A—C21A—H21B	108.0
C8—C9—Cl1	127.5 (2)	C23A—C22A—H22A	109.4
C10—C9—Cl1	124.8 (2)	C21A—C22A—H22A	109.4
C11—C10—C9	108.2 (3)	C23A—C22A—H22B	109.4
C11—C10—Cl2	127.6 (2)	C21A—C22A—H22B	109.4
C9—C10—Cl2	124.1 (2)	H22A—C22A—H22B	108.0
N2—C11—C10	106.7 (3)	N4—C20B—H20C	108.6
N2—C11—C12	123.9 (3)	C21B—C20B—H20C	108.6
C10—C11—C12	129.4 (3)	N4—C20B—H20D	108.6
O2—C12—N3	124.2 (3)	C21B—C20B—H20D	108.6
O2—C12—C11	120.4 (3)	H20C—C20B—H20D	107.5
N3—C12—C11	115.4 (3)	C22B—C21B—H21C	109.4
C15ⁱ—C13—C14	121.5 (3)	C20B—C21B—H21C	109.4
C15—C14—C13	118.9 (3)	C22B—C21B—H21D	109.4
C15—C14—N3	123.9 (3)	C20B—C21B—H21D	109.4
C13—C14—N3	117.1 (3)	H21C—C21B—H21D	108.0
C13ⁱ—C15—C14	119.6 (3)	C23B—C22B—H22C	109.4
C20A—N4—C16	115.8 (15)	C21B—C22B—H22C	109.4
C20A—N4—C24	108.5 (15)	C23B—C22B—H22D	109.4
C16—N4—C24	107.6 (3)	C21B—C22B—H22D	109.4
C20A—N4—C28	103.2 (5)	H22C—C22B—H22D	108.0
C16—N4—C28	110.8 (3)	C22B—C23B—H23D	109.5
C24—N4—C28	111.0 (3)	C22B—C23B—H23E	109.5
C16—N4—C20B	109.0 (6)	H23D—C23B—H23E	109.5
C24—N4—C20B	110.7 (7)	C22B—C23B—H23F	109.5
C28—N4—C20B	107.8 (3)	H23D—C23B—H23F	109.5
N4—C16—C17	115.0 (3)	H23E—C23B—H23F	109.5
C18—C17—C16	111.4 (3)	N4—C24—H24A	108.3
C19—C18—C17	112.9 (3)	C25—C24—H24A	108.3
N4—C20A—C21A	121.4 (7)	N4—C24—H24B	108.3
C22A—C21A—C20A	111.18 (11)	C25—C24—H24B	108.3
C23A—C22A—C21A	111.22 (11)	H24A—C24—H24B	107.4
N4—C20B—C21B	114.8 (4)	C24—C25—H25A	109.4
C22B—C21B—C20B	111.06 (10)	C26—C25—H25A	109.4
C23B—C22B—C21B	111.19 (10)	C24—C25—H25B	109.4
N4—C24—C25	115.8 (3)	C26—C25—H25B	109.4
C24—C25—C26	111.2 (3)	H25A—C25—H25B	108.0
C27—C26—C25	112.9 (3)	C27—C26—H26A	109.0
N4—C28—C29	116.6 (3)	C25—C26—H26A	109.0
C28—C29—C30	109.3 (3)	C27—C26—H26B	109.0
C31—C30—C29	112.7 (3)	C25—C26—H26B	109.0
N5—C32—C33	179.3 (6)	H26A—C26—H26B	107.8
C7—N1—H91	116.3	C26—C27—H27A	109.5
C6—N1—H91	116.3	C26—C27—H27B	109.5
C11—N2—H92	124.7	H27A—C27—H27B	109.5
C8—N2—H92	124.7	C26—C27—H27C	109.5
C12—N3—H93	116.3	H27A—C27—H27C	109.5
C14—N3—H93	116.3	H27B—C27—H27C	109.5
C6—C1—H1	120.4	N4—C28—H28A	108.1
C2—C1—H1	120.4	C29—C28—H28A	108.1
C3—C2—H2	119.4	N4—C28—H28B	108.1
C1—C2—H2	119.4	C29—C28—H28B	108.1
C4—C3—H3	120.4	H28A—C28—H28B	107.3
C2—C3—H3	120.4	C28—C29—H29A	109.8
C3—C4—H4	119.8	C30—C29—H29A	109.8
C5—C4—H4	119.8	C28—C29—H29B	109.8
C4—C5—H5	120.0	C30—C29—H29B	109.8
C6—C5—H5	120.0	H29A—C29—H29B	108.3
C15ⁱ—C13—H13	119.2	C31—C30—H30A	109.0
C14—C13—H13	119.2	C29—C30—H30A	109.0
C13ⁱ—C15—H15	120.2	C31—C30—H30B	109.0
C14—C15—H15	120.2	C29—C30—H30B	109.0
N4—C16—H16A	108.5	H30A—C30—H30B	107.8
C17—C16—H16A	108.5	C30—C31—H31A	109.5
N4—C16—H16B	108.5	C30—C31—H31B	109.5
C17—C16—H16B	108.5	H31A—C31—H31B	109.5
H16A—C16—H16B	107.5	C30—C31—H31C	109.5
C18—C17—H17A	109.4	H31A—C31—H31C	109.5
C16—C17—H17A	109.4	H31B—C31—H31C	109.5
C18—C17—H17B	109.4	C32—C33—H33A	109.5
C16—C17—H17B	109.4	C32—C33—H33B	109.5
H17A—C17—H17B	108.0	H33A—C33—H33B	109.5
C19—C18—H18A	109.0	C32—C33—H33C	109.5
C17—C18—H18A	109.0	H33A—C33—H33C	109.5
C19—C18—H18B	109.0	H33B—C33—H33C	109.5

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H91···Cl3	0.88	2.40	3.269 (3)	172
N2—H92···Cl3	0.88	2.20	3.068 (3)	167
N3—H93···Cl3	0.88	2.40	3.275 (3)	171

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
Gale, P. A., Navakhun, K., Camiolo, S., Light, M. E. & Hursthouse, M. B., (2002). J. Am. Chem. Soc. 124, 11228–11229. 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. 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.