1-(10,11-Di­hydro­dibenz­[b,f]­azepin-5-yl)­ethano­ne

Nagaraj, B.; Yathirajan, H.S.; Lynch, D.E.

doi:10.1107/S1600536805013115

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 61| Part 6| June 2005| Pages o1609-o1610

https://doi.org/10.1107/S1600536805013115

1-(10,11-Dihydrodibenz[b,f]azepin-5-yl)ethanone

Basavegowda Nagaraj,^a Hemmige S. Yathirajan ^a and Daniel E. Lynch ^b ^*

^aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^bSchool of Science and the Environment, Coventry University, Coventry CV1 5FB, England
^*Correspondence e-mail: apx106@coventry.ac.uk

(Received 20 April 2005; accepted 25 April 2005; online 14 May 2005)

The asymmetric unit of the title compound, C₁₆H₁₅NO, comprises two independent molecules (A and B), both adopting a half-boat conformation, or butterfly shape. The intramolecular dihedral angles between the benzene rings in A and B are 64.40 (4) and 65.24 (5)°, respectively.

Comment

The title compound, (I), is used as an intermediate for the synthesis of carbamazepine and oxcarbazepine (Kricka & Ledwith, 1974 ), two anticonvulsant drugs whose structures have been reported [Grzesiak et al., 2003 (most recent form); Hempel et al., 2005 ]. As part of a series of studies into the structural aspects of iminostilbene analogues, the structure of (I) was determined and is reported here. A search of the Cambridge Structural Database (November 2004 version; Allen, 2002 ) reveals that there are 27 compounds reported that contain a 10,11-dihydrodibenz[b,f]azepine moiety with only two containing an additional N-acetyl group, viz. the N-acetyldibenz[b,f]azepine dimer (Harding, 1983 ) and its hydrate structure (Taga et al., 1986 ). The structure of (I) (Fig. 1) comprises two independent molecules, A and B, in the asymmetric unit, both of which adopt a half-boat conformation (Cremer & Pople, 1975 ) or butterfly shape. The intramolecular dihedral angles between the benzene rings in A and B are 64.40 (4) and 65.24 (5)°, respectively.

Figure 1
The molecular configuration and atom-numbering scheme for both independent molecules of (I

). Displacement ellipsoids are drawn at the 50% probability level and H atoms are drawn as spheres of arbitrary radius. The molecules are shown with similar view directions and not in their true relative orientations.

Experimental

The title compound was prepared by refluxing 10,11-dihydro-5H-dibenz[b,f]azepine (1.95 g, 10 mmol) in acetic anhydride (5 ml) for 6 h. Crystals were grown from methanol.

Crystal data

C₁₆H₁₅NO
M_r = 237.29
Orthorhombic, P2₁2₁2₁
a = 9.5674 (2) Å
b = 11.7020 (3) Å
c = 22.2785 (4) Å
V = 2494.25 (9) Å³
Z = 8
D_x = 1.264 Mg m⁻³
Mo Kα radiation
Cell parameters from 3179 reflections
θ = 2.9–27.5°
μ = 0.08 mm⁻¹
T = 150 (2) K
Prism, colourless
0.60 × 0.40 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer
φ and ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.954, T_max = 0.992
19 122 measured reflections
2778 independent reflections
2540 reflections with I > 2σ(I)
R_int = 0.037
θ_max = 26.0°
h = −11 → 11
k = −14 → 14
l = −27 → 27

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.076
S = 1.02
2778 reflections
328 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.04P)² + 0.3098P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Extinction correction: SHELXL97
Extinction coefficient: 0.0285 (14)

All H atoms were included in the refinement at calculated positions, in the riding-model approximation, with C—H distances of 0.95 (ArH), 0.98 (CH₃) and 0.99 Å (CH₂). The isotropic displacement parameters for all H atoms were set equal to 1.25U_eq of the carrier atom. The absolute configuration could not be accurately determined from the diffraction data, thus 1600 Friedel opposites were merged and the configuration arbitrarily assigned. The number of Friedel pairs is 1660.

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: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536805013115/cv6502sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536805013115/cv6502Isup2.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: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

1-(10,11-Dihydrodibenz[b,f]azepin-5-yl)ethanone top

Crystal data top

C₁₆H₁₅NO	F(000) = 1008
M_r = 237.29	D_x = 1.264 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3179 reflections
a = 9.5674 (2) Å	θ = 2.9–27.5°
b = 11.7020 (3) Å	µ = 0.08 mm⁻¹
c = 22.2785 (4) Å	T = 150 K
V = 2494.25 (9) Å³	Prism, colourless
Z = 8	0.60 × 0.40 × 0.10 mm

Data collection top

Nonius KappaCCD diffractometer	2778 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	2540 reflections with I > 2σ(I)
10 cm confocal mirrors monochromator	R_int = 0.037
Detector resolution: 9.091 pixels mm^-1	θ_max = 26.0°, θ_min = 3.3°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −14→14
T_min = 0.954, T_max = 0.992	l = −27→27
19122 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)] = 0.031	H-atom parameters constrained
wR(F²) = 0.076	w = 1/[σ²(F_o²) + (0.04P)² + 0.3098P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2778 reflections	Δρ_max = 0.26 e Å⁻³
328 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0285 (14)

Special details top

Experimental. The minimum and maximum absorption values stated above are those calculated in SHELXL97 from the given crystal dimensions. The ratio of minimum to maximum apparent transmission was determined experimentally as 0.800837.

Geometry. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

2.9908 (0.0055) x + 5.0064 (0.0065) y + 18.8940 (0.0072) z = 7.7832 (0.0024)

* 0.0017 (0.0011) C1A * 0.0033 (0.0011) C2A * -0.0055 (0.0010) C3A * 0.0026 (0.0010) C4A * 0.0024 (0.0010) C13A * -0.0045 (0.0010) C12A

Rms deviation of fitted atoms = 0.0036

6.8470 (0.0036) x - 2.5291 (0.0063) y - 14.7967 (0.0088) z = 0.8469 (0.0065)

Angle to previous plane (with approximate e.s.d.) = 64.40 (0.04)

* -0.0036 (0.0009) C6A * 0.0049 (0.0010) C7A * -0.0019 (0.0010) C8A * -0.0023 (0.0009) C9A * 0.0035 (0.0009) C15A * -0.0006 (0.0009) C14A

Rms deviation of fitted atoms = 0.0031

7.3973 (0.0036) x - 3.9017 (0.0064) y - 12.0187 (0.0111) z = 5.2566 (0.0031)

Angle to previous plane (with approximate e.s.d.) = 10.36 (0.08)

* -0.0087 (0.0010) C6B * 0.0061 (0.0010) C7B * 0.0017 (0.0011) C8B * -0.0067 (0.0010) C9B * 0.0039 (0.0009) C15B * 0.0038 (0.0009) C14B

Rms deviation of fitted atoms = 0.0056

3.4314 (0.0053) x - 10.3952 (0.0032) y + 6.3889 (0.0124) z = 2.8116 (0.0024)

Angle to previous plane (with approximate e.s.d.) = 65.24 (0.05)

* 0.0055 (0.0010) C1B * -0.0076 (0.0010) C2B * 0.0014 (0.0010) C3B * 0.0069 (0.0010) C4B * -0.0091 (0.0010) C13B * 0.0028 (0.0010) C12B

Rms deviation of fitted atoms = 0.0062

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

	x	y	z	U_iso*/U_eq
O51A	0.82550 (11)	0.28256 (9)	0.15509 (5)	0.0286 (3)
N5A	0.68701 (11)	0.42139 (10)	0.19408 (5)	0.0200 (3)
C1A	0.40748 (16)	0.63632 (14)	0.17892 (7)	0.0303 (4)
H1A	0.3935	0.7098	0.1618	0.038*
C2A	0.29936 (16)	0.58411 (14)	0.20995 (7)	0.0322 (4)
H2A	0.2122	0.6223	0.2140	0.040*
C3A	0.31716 (15)	0.47727 (13)	0.23498 (7)	0.0273 (3)
H3A	0.2424	0.4413	0.2557	0.034*
C4A	0.44473 (14)	0.42304 (12)	0.22959 (6)	0.0218 (3)
H4A	0.4584	0.3499	0.2471	0.027*
C6A	0.85940 (14)	0.39654 (13)	0.27291 (6)	0.0228 (3)
H6A	0.8329	0.3184	0.2745	0.029*
C7A	0.95983 (15)	0.43693 (14)	0.31190 (7)	0.0269 (3)
H7A	1.0031	0.3868	0.3398	0.034*
C8A	0.99707 (15)	0.55152 (14)	0.31001 (7)	0.0277 (4)
H8A	1.0653	0.5807	0.3369	0.035*
C9A	0.93397 (15)	0.62276 (13)	0.26866 (7)	0.0253 (3)
H9A	0.9602	0.7010	0.2677	0.032*
C10A	0.77174 (16)	0.67239 (12)	0.18546 (7)	0.0262 (3)
H10A	0.8500	0.7052	0.1620	0.033*
H11A	0.7324	0.7350	0.2101	0.033*
C11A	0.65919 (16)	0.63516 (13)	0.14111 (7)	0.0270 (3)
H12A	0.6274	0.7023	0.1178	0.034*
H13A	0.6994	0.5791	0.1126	0.034*
C12A	0.53623 (15)	0.58235 (12)	0.17251 (6)	0.0231 (3)
C13A	0.55270 (14)	0.47529 (12)	0.19864 (6)	0.0195 (3)
C14A	0.79621 (13)	0.46853 (12)	0.23116 (6)	0.0191 (3)
C15A	0.83272 (14)	0.58400 (12)	0.22804 (6)	0.0210 (3)
C51A	0.71104 (15)	0.32820 (12)	0.15771 (6)	0.0223 (3)
C52A	0.58861 (16)	0.28645 (14)	0.12150 (7)	0.0307 (4)
H51A	0.6223	0.2388	0.0883	0.038*
H52A	0.5372	0.3520	0.1053	0.038*
H53A	0.5266	0.2413	0.1472	0.038*
O51B	0.84508 (11)	−0.15032 (9)	0.07124 (4)	0.0285 (2)
N5B	0.73882 (12)	−0.00453 (10)	0.02391 (5)	0.0204 (3)
C1B	0.38389 (15)	−0.12928 (13)	0.02440 (6)	0.0252 (3)
H1B	0.3225	−0.1672	−0.0025	0.031*
C2B	0.34099 (16)	−0.10637 (13)	0.08267 (7)	0.0265 (3)
H2B	0.2496	−0.1274	0.0952	0.033*
C3B	0.43030 (16)	−0.05315 (13)	0.12269 (7)	0.0272 (3)
H3B	0.4006	−0.0386	0.1627	0.034*
C4B	0.56308 (16)	−0.02100 (12)	0.10457 (6)	0.0242 (3)
H4B	0.6252	0.0149	0.1319	0.030*
C6B	0.81569 (15)	0.18997 (12)	0.00373 (6)	0.0235 (3)
H6B	0.8693	0.1861	0.0396	0.029*
C7B	0.81555 (16)	0.28942 (13)	−0.02988 (7)	0.0278 (3)
H7B	0.8705	0.3531	−0.0178	0.035*
C8B	0.73456 (16)	0.29516 (14)	−0.08122 (7)	0.0287 (4)
H8B	0.7330	0.3632	−0.1045	0.036*
C9B	0.65584 (16)	0.20186 (13)	−0.09869 (7)	0.0271 (3)
H9B	0.6000	0.2076	−0.1338	0.034*
C10B	0.56362 (16)	0.00460 (13)	−0.09084 (6)	0.0265 (3)
H10B	0.5908	−0.0089	−0.1331	0.033*
H11B	0.4661	0.0328	−0.0911	0.033*
C11B	0.56505 (15)	−0.11070 (12)	−0.05849 (6)	0.0243 (3)
H12B	0.5028	−0.1649	−0.0797	0.030*
H13B	0.6609	−0.1425	−0.0590	0.030*
C12B	0.51687 (14)	−0.09688 (12)	0.00527 (6)	0.0214 (3)
C13B	0.60392 (14)	−0.04200 (12)	0.04596 (6)	0.0204 (3)
C14B	0.73789 (14)	0.09537 (12)	−0.01449 (6)	0.0200 (3)
C15B	0.65551 (14)	0.09932 (12)	−0.06648 (6)	0.0217 (3)
C51B	0.85326 (15)	−0.06939 (13)	0.03633 (6)	0.0224 (3)
C52B	0.98762 (15)	−0.04118 (15)	0.00479 (7)	0.0317 (4)
H51B	1.0385	0.0169	0.0278	0.040*
H52B	0.9671	−0.0117	−0.0354	0.040*
H53B	1.0450	−0.1103	0.0015	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O51A	0.0244 (6)	0.0261 (6)	0.0353 (6)	0.0062 (5)	0.0005 (4)	−0.0072 (5)
N5A	0.0178 (5)	0.0166 (6)	0.0257 (6)	−0.0004 (5)	0.0001 (5)	−0.0018 (5)
C1A	0.0297 (8)	0.0201 (8)	0.0410 (9)	0.0054 (7)	−0.0050 (7)	0.0027 (7)
C2A	0.0228 (7)	0.0267 (9)	0.0471 (9)	0.0059 (7)	−0.0010 (7)	−0.0040 (7)
C3A	0.0211 (7)	0.0259 (9)	0.0348 (8)	−0.0013 (6)	0.0045 (6)	−0.0032 (7)
C4A	0.0229 (7)	0.0176 (8)	0.0247 (7)	0.0001 (6)	−0.0002 (6)	−0.0002 (6)
C6A	0.0192 (7)	0.0220 (8)	0.0273 (7)	0.0028 (6)	0.0039 (6)	−0.0014 (6)
C7A	0.0203 (7)	0.0335 (9)	0.0268 (7)	0.0047 (7)	0.0024 (6)	−0.0009 (6)
C8A	0.0186 (7)	0.0361 (9)	0.0284 (8)	−0.0026 (7)	0.0021 (6)	−0.0104 (7)
C9A	0.0238 (7)	0.0231 (8)	0.0290 (7)	−0.0057 (6)	0.0090 (6)	−0.0087 (6)
C10A	0.0302 (8)	0.0179 (8)	0.0304 (8)	−0.0020 (6)	0.0074 (7)	0.0017 (6)
C11A	0.0323 (8)	0.0215 (8)	0.0274 (8)	0.0003 (7)	0.0027 (6)	0.0060 (6)
C12A	0.0260 (7)	0.0204 (8)	0.0229 (7)	0.0015 (6)	−0.0013 (6)	0.0004 (6)
C13A	0.0184 (7)	0.0182 (8)	0.0220 (7)	0.0015 (6)	−0.0005 (6)	−0.0040 (6)
C14A	0.0156 (6)	0.0198 (7)	0.0219 (6)	−0.0002 (6)	0.0037 (6)	−0.0043 (6)
C15A	0.0200 (7)	0.0206 (7)	0.0224 (7)	−0.0014 (6)	0.0079 (6)	−0.0038 (6)
C51A	0.0237 (8)	0.0187 (8)	0.0245 (7)	−0.0003 (6)	0.0019 (6)	0.0002 (6)
C52A	0.0279 (8)	0.0268 (9)	0.0373 (9)	0.0014 (7)	−0.0027 (7)	−0.0098 (7)
O51B	0.0315 (6)	0.0245 (6)	0.0295 (5)	0.0037 (5)	−0.0040 (5)	0.0058 (4)
N5B	0.0189 (6)	0.0197 (6)	0.0225 (6)	−0.0005 (5)	−0.0011 (5)	0.0039 (5)
C1B	0.0246 (7)	0.0203 (8)	0.0306 (8)	0.0001 (6)	−0.0011 (6)	0.0038 (6)
C2B	0.0237 (7)	0.0249 (8)	0.0310 (8)	0.0025 (7)	0.0040 (6)	0.0079 (6)
C3B	0.0323 (8)	0.0253 (8)	0.0240 (7)	0.0071 (7)	0.0072 (7)	0.0063 (6)
C4B	0.0303 (8)	0.0211 (8)	0.0212 (7)	0.0017 (7)	−0.0017 (6)	0.0039 (6)
C6B	0.0198 (7)	0.0255 (8)	0.0253 (7)	−0.0005 (6)	0.0010 (6)	−0.0015 (6)
C7B	0.0269 (8)	0.0219 (8)	0.0347 (8)	−0.0041 (7)	0.0064 (7)	−0.0012 (6)
C8B	0.0272 (8)	0.0231 (8)	0.0359 (8)	0.0001 (7)	0.0045 (7)	0.0096 (6)
C9B	0.0242 (8)	0.0301 (9)	0.0271 (7)	0.0010 (7)	0.0005 (6)	0.0073 (6)
C10B	0.0291 (8)	0.0292 (8)	0.0214 (7)	−0.0045 (7)	−0.0015 (6)	0.0015 (6)
C11B	0.0245 (7)	0.0235 (8)	0.0250 (7)	−0.0032 (6)	0.0005 (6)	−0.0029 (6)
C12B	0.0236 (7)	0.0155 (7)	0.0251 (7)	0.0012 (6)	0.0002 (6)	0.0029 (6)
C13B	0.0216 (7)	0.0160 (7)	0.0237 (7)	0.0026 (6)	0.0002 (6)	0.0050 (6)
C14B	0.0200 (6)	0.0194 (7)	0.0206 (7)	0.0020 (6)	0.0034 (5)	0.0021 (5)
C15B	0.0204 (7)	0.0232 (8)	0.0215 (7)	0.0013 (6)	0.0033 (6)	0.0016 (6)
C51B	0.0245 (7)	0.0222 (8)	0.0206 (7)	0.0003 (6)	−0.0035 (6)	−0.0029 (6)
C52B	0.0238 (7)	0.0336 (9)	0.0377 (9)	0.0044 (7)	−0.0010 (7)	0.0029 (7)

Geometric parameters (Å, º) top

O51A—C51A	1.2198 (17)	O51B—C51B	1.2279 (17)
N5A—C51A	1.3780 (18)	N5B—C51B	1.3607 (18)
N5A—C13A	1.4350 (17)	N5B—C13B	1.4489 (17)
N5A—C14A	1.4416 (17)	N5B—C14B	1.4486 (17)
C1A—C2A	1.386 (2)	C9B—C8B	1.382 (2)
C1A—C12A	1.392 (2)	C9B—C15B	1.398 (2)
C1A—H1A	0.95	C9B—H9B	0.95
C2A—C3A	1.379 (2)	C8B—C7B	1.383 (2)
C2A—H2A	0.95	C8B—H8B	0.95
C3A—C4A	1.381 (2)	C7B—C6B	1.384 (2)
C3A—H3A	0.95	C7B—H7B	0.95
C4A—C13A	1.3844 (19)	C6B—C14B	1.394 (2)
C4A—H4A	0.95	C6B—H6B	0.95
C6A—C7A	1.379 (2)	C4B—C13B	1.385 (2)
C6A—C14A	1.393 (2)	C4B—C3B	1.385 (2)
C6A—H6A	0.95	C4B—H4B	0.95
C7A—C8A	1.388 (2)	C3B—C2B	1.383 (2)
C7A—H7A	0.95	C3B—H3B	0.95
C8A—C9A	1.381 (2)	C2B—C1B	1.388 (2)
C8A—H8A	0.95	C2B—H2B	0.95
C9A—C15A	1.401 (2)	C1B—C12B	1.394 (2)
C9A—H9A	0.95	C1B—H1B	0.95
C10A—C15A	1.520 (2)	C11B—C12B	1.502 (2)
C10A—C11A	1.525 (2)	C11B—C10B	1.530 (2)
C10A—H10A	0.99	C11B—H12B	0.99
C10A—H11A	0.99	C11B—H13B	0.99
C11A—C12A	1.502 (2)	C10B—C15B	1.515 (2)
C11A—H12A	0.99	C10B—H10B	0.99
C11A—H13A	0.99	C10B—H11B	0.99
C12A—C13A	1.390 (2)	C15B—C14B	1.4017 (19)
C14A—C15A	1.397 (2)	C13B—C12B	1.388 (2)
C51A—C52A	1.504 (2)	C51B—C52B	1.502 (2)
C52A—H51A	0.98	C52B—H51B	0.98
C52A—H52A	0.98	C52B—H52B	0.98
C52A—H53A	0.98	C52B—H53B	0.98

C51A—N5A—C13A	122.60 (11)	C51B—N5B—C13B	118.62 (11)
C51A—N5A—C14A	121.26 (11)	C51B—N5B—C14B	125.12 (11)
C13A—N5A—C14A	116.12 (10)	C13B—N5B—C14B	116.04 (11)
C2A—C1A—C12A	120.78 (14)	C8B—C9B—C15B	122.31 (14)
C2A—C1A—H1A	119.6	C8B—C9B—H9B	118.8
C12A—C1A—H1A	119.6	C15B—C9B—H9B	118.8
C3A—C2A—C1A	120.59 (14)	C9B—C8B—C7B	119.98 (14)
C3A—C2A—H2A	119.7	C9B—C8B—H8B	120.0
C1A—C2A—H2A	119.7	C7B—C8B—H8B	120.0
C4A—C3A—C2A	119.37 (14)	C6B—C7B—C8B	119.26 (14)
C4A—C3A—H3A	120.3	C6B—C7B—H7B	120.4
C2A—C3A—H3A	120.3	C8B—C7B—H7B	120.4
C3A—C4A—C13A	119.99 (13)	C7B—C6B—C14B	120.64 (14)
C3A—C4A—H4A	120.0	C7B—C6B—H6B	119.7
C13A—C4A—H4A	120.0	C14B—C6B—H6B	119.7
C7A—C6A—C14A	121.05 (14)	C13B—C4B—C3B	119.04 (14)
C7A—C6A—H6A	119.5	C13B—C4B—H4B	120.5
C14A—C6A—H6A	119.5	C3B—C4B—H4B	120.5
C6A—C7A—C8A	119.40 (14)	C2B—C3B—C4B	120.07 (13)
C6A—C7A—H7A	120.3	C2B—C3B—H3B	120.0
C8A—C7A—H7A	120.3	C4B—C3B—H3B	120.0
C9A—C8A—C7A	119.41 (14)	C3B—C2B—C1B	120.49 (14)
C9A—C8A—H8A	120.3	C3B—C2B—H2B	119.8
C7A—C8A—H8A	120.3	C1B—C2B—H2B	119.8
C8A—C9A—C15A	122.52 (14)	C2B—C1B—C12B	120.22 (14)
C8A—C9A—H9A	118.7	C2B—C1B—H1B	119.9
C15A—C9A—H9A	118.7	C12B—C1B—H1B	119.9
C15A—C10A—C11A	118.75 (12)	C12B—C11B—C10B	110.36 (12)
C15A—C10A—H10A	107.6	C12B—C11B—H12B	109.6
C11A—C10A—H10A	107.6	C10B—C11B—H13B	109.6
C15A—C10A—H11A	107.6	C12B—C11B—H13B	109.6
C11A—C10A—H11A	107.6	C10B—C11B—H12B	109.6
H10A—C10A—H11A	107.1	H12B—C11B—H13B	108.1
C12A—C11A—C10A	111.64 (12)	C15B—C10B—C11B	118.11 (12)
C12A—C11A—H12A	109.3	C15B—C10B—H10B	107.8
C10A—C11A—H12A	109.3	C11B—C10B—H11B	107.8
C12A—C11A—H13A	109.3	C15B—C10B—H11B	107.8
C10A—C11A—H13A	109.3	C11B—C10B—H10B	107.8
H12A—C11A—H13A	108.0	H10B—C10B—H11B	107.1
C13A—C12A—C1A	117.80 (13)	C9B—C15B—C14B	116.82 (13)
C13A—C12A—C11A	118.49 (13)	C9B—C15B—C10B	116.44 (12)
C1A—C12A—C11A	123.67 (13)	C14B—C15B—C10B	126.73 (13)
C4A—C13A—C12A	121.46 (13)	C6B—C14B—C15B	120.96 (13)
C4A—C13A—N5A	120.62 (12)	C6B—C14B—N5B	117.74 (12)
C12A—C13A—N5A	117.90 (13)	C15B—C14B—N5B	121.20 (12)
C6A—C14A—C15A	120.63 (13)	C4B—C13B—C12B	121.89 (13)
C6A—C14A—N5A	117.76 (12)	C4B—C13B—N5B	121.15 (13)
C15A—C14A—N5A	121.51 (12)	C12B—C13B—N5B	116.94 (12)
C14A—C15A—C9A	116.98 (13)	C13B—C12B—C1B	118.27 (13)
C14A—C15A—C10A	126.38 (13)	C13B—C12B—C11B	118.89 (12)
C9A—C15A—C10A	116.63 (13)	C1B—C12B—C11B	122.67 (13)
O51A—C51A—N5A	121.63 (13)	O51B—C51B—N5B	120.51 (13)
O51A—C51A—C52A	122.10 (13)	O51B—C51B—C52B	121.37 (13)
N5A—C51A—C52A	116.27 (12)	N5B—C51B—C52B	118.10 (12)
C51A—C52A—H51A	109.5	C51B—C52B—H51B	109.5
C51A—C52A—H52A	109.5	C51B—C52B—H52B	109.5
H51A—C52A—H52A	109.5	H51B—C52B—H52B	109.5
C51A—C52A—H53A	109.5	C51B—C52B—H53B	109.5
H51A—C52A—H53A	109.5	H51B—C52B—H53B	109.5
H52A—C52A—H53A	109.5	H52B—C52B—H53B	109.5

C12A—C1A—C2A—C3A	−0.2 (2)	C15B—C9B—C8B—C7B	−0.7 (2)
C1A—C2A—C3A—C4A	0.9 (2)	C9B—C8B—C7B—C6B	−0.5 (2)
C2A—C3A—C4A—C13A	−0.8 (2)	C8B—C7B—C6B—C14B	1.5 (2)
C14A—C6A—C7A—C8A	0.9 (2)	C13B—C4B—C3B—C2B	0.6 (2)
C6A—C7A—C8A—C9A	−0.7 (2)	C4B—C3B—C2B—C1B	0.8 (2)
C7A—C8A—C9A—C15A	0.0 (2)	C3B—C2B—C1B—C12B	−1.2 (2)
C15A—C10A—C11A—C12A	56.69 (17)	C12B—C11B—C10B—C15B	60.81 (17)
C2A—C1A—C12A—C13A	−0.5 (2)	C8B—C9B—C15B—C14B	0.9 (2)
C2A—C1A—C12A—C11A	−178.13 (14)	C8B—C9B—C15B—C10B	179.74 (14)
C10A—C11A—C12A—C13A	−70.72 (17)	C11B—C10B—C15B—C9B	177.41 (13)
C10A—C11A—C12A—C1A	106.87 (16)	C11B—C10B—C15B—C14B	−3.9 (2)
C3A—C4A—C13A—C12A	0.1 (2)	C7B—C6B—C14B—C15B	−1.3 (2)
C3A—C4A—C13A—N5A	178.27 (13)	C7B—C6B—C14B—N5B	−177.85 (12)
C1A—C12A—C13A—C4A	0.6 (2)	C9B—C15B—C14B—C6B	0.12 (19)
C11A—C12A—C13A—C4A	178.33 (13)	C10B—C15B—C14B—C6B	−178.58 (13)
C1A—C12A—C13A—N5A	−177.65 (12)	C9B—C15B—C14B—N5B	176.52 (12)
C11A—C12A—C13A—N5A	0.09 (19)	C10B—C15B—C14B—N5B	−2.2 (2)
C51A—N5A—C13A—C4A	73.45 (18)	C51B—N5B—C14B—C6B	−64.33 (18)
C14A—N5A—C13A—C4A	−105.01 (14)	C13B—N5B—C14B—C6B	121.27 (14)
C51A—N5A—C13A—C12A	−108.30 (15)	C51B—N5B—C14B—C15B	119.16 (15)
C14A—N5A—C13A—C12A	73.24 (16)	C13B—N5B—C14B—C15B	−55.25 (17)
C7A—C6A—C14A—C15A	−0.4 (2)	C3B—C4B—C13B—C12B	−1.6 (2)
C7A—C6A—C14A—N5A	−176.84 (12)	C3B—C4B—C13B—N5B	176.65 (12)
C51A—N5A—C14A—C6A	−58.07 (17)	C51B—N5B—C13B—C4B	81.31 (17)
C13A—N5A—C14A—C6A	120.41 (13)	C14B—N5B—C13B—C4B	−103.90 (15)
C51A—N5A—C14A—C15A	125.49 (14)	C51B—N5B—C13B—C12B	−100.34 (15)
C13A—N5A—C14A—C15A	−56.03 (17)	C14B—N5B—C13B—C12B	74.45 (16)
C6A—C14A—C15A—C9A	−0.31 (19)	C4B—C13B—C12B—C1B	1.2 (2)
N5A—C14A—C15A—C9A	176.03 (11)	N5B—C13B—C12B—C1B	−177.12 (12)
C6A—C14A—C15A—C10A	−179.32 (13)	C4B—C13B—C12B—C11B	176.53 (13)
N5A—C14A—C15A—C10A	−3.0 (2)	N5B—C13B—C12B—C11B	−1.81 (19)
C8A—C9A—C15A—C14A	0.48 (19)	C2B—C1B—C12B—C13B	0.2 (2)
C8A—C9A—C15A—C10A	179.58 (13)	C2B—C1B—C12B—C11B	−174.92 (13)
C11A—C10A—C15A—C14A	0.1 (2)	C10B—C11B—C12B—C13B	−71.31 (16)
C11A—C10A—C15A—C9A	−178.89 (12)	C10B—C11B—C12B—C1B	103.78 (15)
C13A—N5A—C51A—O51A	−178.94 (13)	C13B—N5B—C51B—O51B	−8.42 (19)
C14A—N5A—C51A—O51A	−0.6 (2)	C14B—N5B—C51B—O51B	177.31 (12)
C13A—N5A—C51A—C52A	1.20 (19)	C13B—N5B—C51B—C52B	169.77 (13)
C14A—N5A—C51A—C52A	179.58 (13)	C14B—N5B—C51B—C52B	−4.5 (2)

Acknowledgements

The authors thank the EPSRC National Crystallography Service (Southampton, England) and acknowledge the use of the EPSRC's Chemical Database Service at Daresbury (Fletcher et al., 1996 ).

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