(6R*,16R*)-9,14-Dihydro-6-methyl-6,16-methano-6H,16H-[2,4]benzothiazepino[3,4-d][1,3,5]benzoxadiazocine hydrobromide dimethylformamide hemisolvate

The title compound, C₁₉H₁₉N₂OS⁺·Br^-·0.5C₃H₇NO, is an oxygen-bridged phenyl­pyrimidine derivative in which the heterocyclic ring is protonated, the positive charge being dispersed over both of the N atoms. Both mol­ecules in the asymmetric unit exist in an identical conformation, which consists of a central planar portion with the two terminal phenyl rings protruding from the same side of the plane. One of the independent mol­ecules forms a strong hydrogen bond with the bromide anion, while the other is hydrogen bonded to the di­methyl­form­amide solvent mol­ecule.

Computing details

Data collection: Syntex P2₁ diffractometer software; cell refinement: Syntex P2₁ diffractometer software; data reduction: XP21 (Pavelčík, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

(6R*,16R*)-9,14-Dihydro-6-methyl-6,16-methano-6H,16H-[2,4]benzo- thiazepino[3,4-d][1,3,5]benzoxadiazocine hydrobromide 0.5 dimethylformamide

Crystal data

C19H19N2OS·Br·0.5C3H7NO	Dx = 1.437 Mg m^−3 Dm = 1.44 (1) Mg m^−3 Dm measured by flotation in bromoform/c-hexane
Mr = 439.89	Melting point: 511 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.612 (8) Å	Cell parameters from 15 reflections
b = 19.807 (9) Å	θ = 10–22°
c = 11.087 (5) Å	µ = 2.14 mm^−1
β = 95.94 (3)°	T = 293 K
V = 4065 (3) Å^3	Plate, colourless
Z = 8	0.35 × 0.30 × 0.10 mm
F(000) = 1808

Data collection

Syntex P21 diffractometer	3573 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 25.1°, θmin = 1.5°
θ/2θ scans	h = −22→0
Absorption correction: ψ scan (North et al., 1968)	k = 0→23
Tmin = 0.495, Tmax = 0.810	l = −12→12
7534 measured reflections	2 standard reflections every 100 min
7166 independent reflections	intensity decay: none

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0758P)^2] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.063	(Δ/σ)max = 0.002
wR(F^2) = 0.157	Δρmax = 0.39 e Å^−3
S = 0.90	Δρmin = −0.31 e Å^−3
7166 reflections	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
483 parameters	Extinction coefficient: 0.0017 (3)
0 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1A	0.3670 (5)	0.1067 (6)	0.7573 (9)	0.074 (3)
H1A	0.3341	0.0759	0.7203	0.089*
C2A	0.4245 (6)	0.0846 (6)	0.8386 (11)	0.088 (4)
H2A	0.4289	0.0389	0.8569	0.106*
C3A	0.4742 (7)	0.1287 (8)	0.8915 (11)	0.101 (4)
H3A	0.5123	0.1133	0.9454	0.122*
C4A	0.4675 (5)	0.1961 (7)	0.8642 (10)	0.082 (4)
H4A	0.5020	0.2264	0.8982	0.099*
C5A	0.4104 (5)	0.2193 (6)	0.7876 (8)	0.059 (3)
O6A	0.4056 (3)	0.2875 (4)	0.7611 (6)	0.0685 (18)
C7A	0.3422 (5)	0.3108 (5)	0.6914 (8)	0.059 (3)
N8A	0.2822 (4)	0.3127 (3)	0.7667 (6)	0.0504 (19)
H8A	0.2819	0.3454	0.8175	0.060*
C9A	0.2281 (4)	0.2685 (4)	0.7642 (8)	0.045 (2)
S10A	0.16091 (12)	0.29550 (12)	0.8474 (2)	0.0560 (7)
C11A	0.0991 (4)	0.2264 (5)	0.8668 (8)	0.060 (3)
H11A	0.0673	0.2393	0.9268	0.072*
H11B	0.0696	0.2189	0.7907	0.072*
C12A	0.1363 (4)	0.1617 (5)	0.9060 (9)	0.055 (3)
C13A	0.1340 (5)	0.1333 (6)	1.0171 (9)	0.072 (3)
H13A	0.1116	0.1575	1.0746	0.086*
C14A	0.1619 (7)	0.0727 (8)	1.0496 (12)	0.107 (5)
H14A	0.1585	0.0554	1.1268	0.128*
C15A	0.1957 (6)	0.0369 (6)	0.9651 (13)	0.096 (4)
H15A	0.2150	−0.0055	0.9846	0.116*
C16A	0.2012 (5)	0.0640 (5)	0.8510 (11)	0.072 (3)
H16A	0.2248	0.0396	0.7953	0.087*
C17A	0.1721 (4)	0.1267 (5)	0.8184 (9)	0.052 (2)
C18A	0.1786 (4)	0.1577 (5)	0.6981 (8)	0.056 (3)
H18A	0.1915	0.1229	0.6427	0.067*
H18B	0.1320	0.1758	0.6666	0.067*
N19A	0.2331 (3)	0.2123 (4)	0.7017 (6)	0.0436 (17)
C20A	0.2997 (4)	0.1997 (5)	0.6422 (8)	0.053 (2)
H20A	0.2895	0.1659	0.5781	0.063*
C21A	0.3204 (4)	0.2646 (5)	0.5871 (8)	0.060 (3)
H21A	0.2800	0.2833	0.5357	0.072*
H21B	0.3603	0.2577	0.5386	0.072*
C22A	0.3594 (5)	0.1745 (6)	0.7325 (8)	0.060 (3)
C23A	0.3603 (5)	0.3822 (5)	0.6542 (8)	0.076 (3)
H23A	0.3219	0.3993	0.5979	0.113*
H23B	0.4045	0.3818	0.6165	0.113*
H23C	0.3659	0.4107	0.7247	0.113*
C1B	−0.1531 (5)	0.3465 (5)	0.4358 (9)	0.063 (3)
H1B	−0.1059	0.3327	0.4590	0.076*
C2B	−0.1682 (6)	0.3859 (5)	0.3325 (10)	0.081 (3)
H2B	−0.1316	0.3968	0.2849	0.098*
C3B	−0.2367 (7)	0.4085 (5)	0.3010 (10)	0.081 (3)
H3B	−0.2460	0.4369	0.2344	0.097*
C4B	−0.2919 (6)	0.3900 (5)	0.3661 (9)	0.070 (3)
H4B	−0.3388	0.4045	0.3423	0.084*
C5B	−0.2778 (5)	0.3489 (4)	0.4693 (8)	0.050 (2)
O6B	−0.3370 (3)	0.3302 (3)	0.5260 (6)	0.0621 (17)
C7B	−0.3202 (4)	0.2965 (5)	0.6396 (9)	0.054 (2)
N8B	−0.2963 (4)	0.3439 (3)	0.7334 (6)	0.055 (2)
H8B	−0.3290	0.3671	0.7640	0.066*
C9B	−0.2280 (4)	0.3551 (4)	0.7770 (8)	0.046 (2)
S10B	−0.22457 (12)	0.40999 (13)	0.9003 (2)	0.0613 (7)
C11B	−0.1319 (4)	0.4289 (4)	0.9549 (8)	0.061 (3)
H11C	−0.1316	0.4642	1.0155	0.074*
H11D	−0.1103	0.3890	0.9943	0.074*
C12B	−0.0866 (4)	0.4508 (5)	0.8594 (8)	0.051 (2)
C13B	−0.0580 (5)	0.5159 (5)	0.8583 (9)	0.057 (3)
H13B	−0.0684	0.5466	0.9176	0.069*
C14B	−0.0151 (5)	0.5356 (5)	0.7718 (11)	0.075 (3)
H14B	0.0046	0.5788	0.7734	0.090*
C15B	−0.0013 (5)	0.4905 (6)	0.6822 (10)	0.080 (3)
H15B	0.0262	0.5045	0.6214	0.096*
C16B	−0.0267 (5)	0.4268 (5)	0.6804 (9)	0.069 (3)
H16B	−0.0151	0.3966	0.6211	0.083*
C17B	−0.0707 (4)	0.4065 (5)	0.7687 (8)	0.049 (2)
C18B	−0.0993 (4)	0.3345 (4)	0.7728 (8)	0.054 (2)
H18C	−0.0709	0.3057	0.7252	0.064*
H18D	−0.0928	0.3185	0.8559	0.064*
N19B	−0.1755 (3)	0.3281 (3)	0.7270 (6)	0.0443 (18)
C20B	−0.1935 (4)	0.2846 (4)	0.6157 (8)	0.049 (2)
H20B	−0.1536	0.2535	0.6058	0.058*
C21B	−0.2603 (4)	0.2459 (4)	0.6333 (8)	0.052 (2)
H21C	−0.2535	0.2199	0.7077	0.063*
H21D	−0.2719	0.2151	0.5661	0.063*
C22B	−0.2083 (5)	0.3278 (4)	0.5046 (8)	0.049 (2)
C23B	−0.3916 (4)	0.2634 (5)	0.6664 (9)	0.086 (3)
H23D	−0.4060	0.2307	0.6046	0.129*
H23E	−0.4283	0.2974	0.6673	0.129*
H23F	−0.3850	0.2414	0.7439	0.129*
Br1	0.26794 (5)	0.44797 (4)	0.93392 (9)	0.0612 (3)
Br2	−0.01535 (4)	0.29124 (5)	1.08177 (9)	0.0553 (3)
C1	−0.4056 (5)	0.4182 (6)	0.9516 (12)	0.092 (4)
H1	−0.3627	0.4406	0.9762	0.110*
C2	−0.5217 (5)	0.3823 (5)	1.0024 (10)	0.086 (3)
H2C	−0.5256	0.3504	1.0666	0.128*
H2D	−0.5224	0.3587	0.9267	0.128*
H2E	−0.5615	0.4133	0.9987	0.128*
C3	−0.4424 (5)	0.4544 (6)	1.1417 (8)	0.087 (4)
H3C	−0.4378	0.4220	1.2064	0.131*
H3D	−0.4824	0.4838	1.1512	0.131*
H3E	−0.3988	0.4805	1.1436	0.131*
N	−0.4549 (4)	0.4191 (4)	1.0251 (8)	0.064 (2)
O	−0.4102 (4)	0.3907 (5)	0.8523 (9)	0.137 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.047 (6)	0.105 (10)	0.074 (8)	0.017 (6)	0.023 (6)	0.001 (7)
C2A	0.067 (8)	0.100 (10)	0.101 (10)	0.027 (7)	0.028 (8)	0.026 (9)
C3A	0.085 (10)	0.151 (14)	0.070 (9)	0.036 (10)	0.021 (7)	0.023 (10)
C4A	0.028 (5)	0.145 (12)	0.072 (8)	0.005 (7)	−0.004 (5)	−0.036 (9)
C5A	0.037 (5)	0.088 (8)	0.054 (6)	−0.005 (6)	0.016 (5)	−0.022 (7)
O6A	0.046 (4)	0.087 (5)	0.071 (5)	−0.009 (4)	0.004 (4)	−0.016 (4)
C7A	0.054 (6)	0.079 (8)	0.045 (6)	−0.008 (6)	0.011 (5)	−0.006 (6)
N8A	0.060 (5)	0.046 (4)	0.045 (4)	−0.006 (4)	0.010 (4)	−0.008 (4)
C9A	0.039 (5)	0.051 (6)	0.043 (6)	−0.001 (5)	0.000 (4)	0.002 (5)
S10A	0.0533 (14)	0.0569 (15)	0.0597 (16)	0.0052 (13)	0.0155 (13)	−0.0110 (14)
C11A	0.033 (5)	0.088 (7)	0.062 (6)	−0.007 (5)	0.019 (5)	−0.009 (6)
C12A	0.038 (5)	0.070 (7)	0.056 (7)	−0.010 (5)	−0.001 (5)	−0.003 (6)
C13A	0.083 (8)	0.081 (8)	0.051 (7)	−0.032 (7)	0.004 (6)	0.012 (7)
C14A	0.105 (11)	0.116 (13)	0.096 (11)	−0.033 (9)	−0.007 (9)	0.049 (10)
C15A	0.090 (9)	0.069 (9)	0.126 (12)	−0.013 (7)	−0.012 (9)	0.046 (9)
C16A	0.059 (6)	0.054 (7)	0.102 (9)	−0.003 (5)	0.001 (6)	0.006 (7)
C17A	0.036 (5)	0.066 (7)	0.054 (6)	−0.018 (5)	−0.003 (5)	0.004 (6)
C18A	0.041 (5)	0.074 (7)	0.049 (6)	0.005 (5)	−0.015 (5)	−0.017 (6)
N19A	0.032 (4)	0.051 (4)	0.047 (4)	−0.013 (4)	−0.004 (3)	−0.014 (4)
C20A	0.043 (5)	0.074 (7)	0.043 (5)	−0.001 (5)	0.016 (5)	−0.016 (6)
C21A	0.052 (6)	0.089 (8)	0.041 (6)	0.001 (5)	0.010 (5)	−0.010 (6)
C22A	0.062 (7)	0.075 (7)	0.044 (6)	0.016 (6)	0.008 (5)	0.001 (6)
C23A	0.085 (7)	0.085 (8)	0.063 (7)	−0.016 (6)	0.036 (6)	−0.005 (6)
C1B	0.077 (7)	0.068 (7)	0.047 (6)	−0.006 (6)	0.010 (6)	−0.009 (6)
C2B	0.088 (9)	0.081 (8)	0.073 (9)	−0.023 (7)	0.000 (7)	0.009 (7)
C3B	0.134 (11)	0.050 (7)	0.056 (7)	−0.019 (8)	0.000 (8)	0.001 (6)
C4B	0.092 (8)	0.052 (7)	0.059 (7)	0.007 (6)	−0.024 (7)	−0.003 (6)
C5B	0.057 (6)	0.047 (6)	0.044 (6)	0.003 (5)	−0.004 (5)	−0.009 (5)
O6B	0.044 (4)	0.079 (5)	0.062 (4)	0.007 (3)	0.000 (3)	0.002 (4)
C7B	0.038 (5)	0.069 (6)	0.059 (6)	0.003 (5)	0.014 (5)	0.001 (6)
N8B	0.055 (5)	0.061 (5)	0.053 (5)	0.003 (4)	0.018 (4)	−0.016 (4)
C9B	0.037 (5)	0.041 (5)	0.061 (6)	0.001 (4)	0.016 (5)	0.010 (5)
S10B	0.0558 (15)	0.0692 (17)	0.0606 (17)	0.0006 (13)	0.0137 (13)	−0.0185 (14)
C11B	0.072 (6)	0.063 (6)	0.046 (6)	0.018 (5)	−0.006 (5)	−0.021 (5)
C12B	0.051 (5)	0.051 (6)	0.049 (6)	0.020 (5)	−0.009 (5)	−0.006 (6)
C13B	0.055 (6)	0.052 (7)	0.062 (7)	0.003 (5)	−0.010 (5)	−0.018 (6)
C14B	0.059 (7)	0.065 (7)	0.097 (9)	−0.016 (6)	−0.007 (7)	−0.005 (7)
C15B	0.070 (7)	0.088 (9)	0.085 (9)	−0.022 (7)	0.021 (6)	−0.006 (8)
C16B	0.042 (6)	0.076 (8)	0.089 (8)	−0.005 (5)	0.003 (6)	−0.015 (7)
C17B	0.031 (5)	0.061 (6)	0.054 (6)	0.005 (5)	−0.002 (5)	−0.001 (6)
C18B	0.052 (6)	0.056 (6)	0.051 (6)	0.025 (5)	−0.003 (5)	−0.001 (5)
N19B	0.034 (4)	0.050 (4)	0.048 (5)	0.010 (3)	0.001 (4)	0.006 (4)
C20B	0.052 (5)	0.043 (5)	0.052 (6)	0.008 (5)	0.008 (5)	−0.002 (5)
C21B	0.062 (6)	0.051 (6)	0.044 (5)	−0.009 (5)	0.004 (5)	−0.007 (5)
C22B	0.054 (6)	0.039 (5)	0.051 (6)	0.001 (5)	−0.004 (5)	−0.008 (5)
C23B	0.045 (6)	0.112 (9)	0.108 (9)	−0.021 (6)	0.035 (6)	−0.018 (8)
Br1	0.0783 (7)	0.0412 (5)	0.0662 (7)	−0.0008 (5)	0.0180 (5)	0.0002 (6)
Br2	0.0467 (5)	0.0626 (6)	0.0558 (6)	−0.0006 (5)	0.0017 (4)	0.0062 (5)
C1	0.042 (6)	0.109 (10)	0.130 (11)	−0.002 (6)	0.037 (8)	−0.028 (9)
C2	0.054 (6)	0.091 (8)	0.113 (9)	−0.002 (6)	0.017 (6)	−0.003 (7)
C3	0.071 (7)	0.132 (10)	0.058 (7)	−0.025 (7)	0.004 (6)	−0.002 (8)
N	0.035 (4)	0.062 (5)	0.094 (7)	0.007 (4)	0.010 (5)	0.000 (5)
O	0.070 (5)	0.195 (10)	0.151 (8)	−0.013 (5)	0.041 (6)	−0.107 (8)

Geometric parameters (Å, º)

C1A—C22A	1.375 (12)	C2B—C3B	1.361 (13)
C1A—C2A	1.396 (13)	C3B—C4B	1.366 (12)
C2A—C3A	1.360 (15)	C4B—C5B	1.407 (12)
C3A—C4A	1.372 (15)	C5B—O6B	1.374 (9)
C4A—C5A	1.369 (13)	C5B—C22B	1.377 (11)
C5A—O6A	1.384 (11)	O6B—C7B	1.431 (10)
C5A—C22A	1.393 (12)	C7B—N8B	1.437 (10)
O6A—C7A	1.419 (10)	C7B—C21B	1.506 (10)
C7A—N8A	1.462 (10)	C7B—C23B	1.538 (10)
C7A—C21A	1.498 (11)	N8B—C9B	1.332 (9)
C7A—C23A	1.521 (12)	C9B—N19B	1.289 (9)
N8A—C9A	1.332 (9)	C9B—S10B	1.742 (9)
C9A—N19A	1.320 (9)	S10B—C11B	1.807 (8)
C9A—S10A	1.715 (8)	C11B—C12B	1.484 (11)
S10A—C11A	1.814 (8)	C12B—C17B	1.390 (11)
C11A—C12A	1.500 (12)	C12B—C13B	1.396 (11)
C12A—C13A	1.359 (12)	C13B—C14B	1.366 (12)
C12A—C17A	1.414 (11)	C14B—C15B	1.379 (13)
C13A—C14A	1.341 (14)	C15B—C16B	1.348 (12)
C14A—C15A	1.379 (15)	C16B—C17B	1.399 (11)
C15A—C16A	1.387 (14)	C17B—C18B	1.524 (11)
C16A—C17A	1.388 (12)	C18B—N19B	1.462 (9)
C17A—C18A	1.484 (11)	N19B—C20B	1.513 (9)
C18A—N19A	1.481 (10)	C20B—C21B	1.490 (10)
N19A—C20A	1.484 (9)	C20B—C22B	1.501 (11)
C20A—C21A	1.491 (11)	C1—O	1.224 (12)
C20A—C22A	1.502 (11)	C1—N	1.289 (11)
C1B—C2B	1.390 (12)	C2—N	1.441 (10)
C1B—C22B	1.392 (11)	C3—N	1.466 (11)
C22A—C1A—C2A	119.5 (11)	C2B—C3B—C4B	120.8 (11)
C3A—C2A—C1A	121.2 (12)	C3B—C4B—C5B	119.8 (10)
C2A—C3A—C4A	119.2 (13)	O6B—C5B—C22B	124.2 (8)
C5A—C4A—C3A	120.6 (12)	O6B—C5B—C4B	115.8 (9)
C4A—C5A—O6A	119.1 (10)	C22B—C5B—C4B	119.9 (9)
C4A—C5A—C22A	120.6 (11)	C5B—O6B—C7B	114.5 (6)
O6A—C5A—C22A	120.2 (9)	O6B—C7B—N8B	110.8 (7)
C5A—O6A—C7A	117.7 (7)	O6B—C7B—C21B	111.4 (7)
O6A—C7A—N8A	109.7 (7)	N8B—C7B—C21B	107.0 (7)
O6A—C7A—C21A	111.4 (8)	O6B—C7B—C23B	104.8 (7)
N8A—C7A—C21A	107.1 (7)	N8B—C7B—C23B	110.3 (7)
O6A—C7A—C23A	104.8 (8)	C21B—C7B—C23B	112.6 (8)
N8A—C7A—C23A	109.6 (8)	C9B—N8B—C7B	125.7 (7)
C21A—C7A—C23A	114.2 (8)	N19B—C9B—N8B	120.8 (8)
C9A—N8A—C7A	126.3 (7)	N19B—C9B—S10B	129.0 (7)
N19A—C9A—N8A	118.1 (7)	N8B—C9B—S10B	110.2 (6)
N19A—C9A—S10A	129.8 (6)	C9B—S10B—C11B	110.4 (4)
N8A—C9A—S10A	112.1 (7)	C12B—C11B—S10B	114.5 (6)
C9A—S10A—C11A	109.6 (4)	C17B—C12B—C13B	117.8 (9)
C12A—C11A—S10A	113.6 (6)	C17B—C12B—C11B	120.7 (9)
C13A—C12A—C17A	118.7 (9)	C13B—C12B—C11B	121.5 (9)
C13A—C12A—C11A	124.0 (10)	C14B—C13B—C12B	121.4 (9)
C17A—C12A—C11A	117.1 (9)	C13B—C14B—C15B	119.1 (10)
C14A—C13A—C12A	124.5 (12)	C16B—C15B—C14B	121.7 (10)
C13A—C14A—C15A	117.9 (12)	C15B—C16B—C17B	119.2 (10)
C14A—C15A—C16A	120.2 (11)	C12B—C17B—C16B	120.6 (9)
C17A—C16A—C15A	121.4 (11)	C12B—C17B—C18B	117.9 (8)
C16A—C17A—C12A	117.3 (9)	C16B—C17B—C18B	121.4 (8)
C16A—C17A—C18A	122.6 (10)	N19B—C18B—C17B	113.6 (6)
C12A—C17A—C18A	120.2 (9)	C9B—N19B—C18B	124.5 (7)
N19A—C18A—C17A	113.5 (7)	C9B—N19B—C20B	118.2 (7)
C9A—N19A—C18A	123.0 (7)	C18B—N19B—C20B	117.2 (6)
C9A—N19A—C20A	118.9 (6)	C21B—C20B—C22B	108.4 (7)
C18A—N19A—C20A	117.8 (7)	C21B—C20B—N19B	107.6 (6)
N19A—C20A—C21A	107.5 (7)	C22B—C20B—N19B	110.6 (6)
N19A—C20A—C22A	110.7 (7)	C20B—C21B—C7B	107.2 (7)
C21A—C20A—C22A	110.7 (8)	C5B—C22B—C1B	119.2 (9)
C20A—C21A—C7A	105.8 (7)	C5B—C22B—C20B	119.6 (8)
C1A—C22A—C5A	118.8 (10)	C1B—C22B—C20B	121.2 (8)
C1A—C22A—C20A	120.8 (10)	O—C1—N	125.9 (11)
C5A—C22A—C20A	120.3 (10)	C1—N—C2	122.7 (10)
C2B—C1B—C22B	120.2 (9)	C1—N—C3	120.3 (9)
C3B—C2B—C1B	120.0 (11)	C2—N—C3	116.8 (8)
C22A—C1A—C2A—C3A	−1.6 (16)	C1B—C2B—C3B—C4B	−3.6 (15)
C1A—C2A—C3A—C4A	0.0 (18)	C2B—C3B—C4B—C5B	2.1 (15)
C2A—C3A—C4A—C5A	1.9 (18)	C3B—C4B—C5B—O6B	−177.2 (8)
C3A—C4A—C5A—O6A	−179.4 (9)	C3B—C4B—C5B—C22B	0.3 (13)
C3A—C4A—C5A—C22A	−2.2 (15)	C22B—C5B—O6B—C7B	10.9 (11)
C4A—C5A—O6A—C7A	−173.8 (8)	C4B—C5B—O6B—C7B	−171.7 (7)
C22A—C5A—O6A—C7A	9.1 (12)	C5B—O6B—C7B—N8B	76.8 (8)
C5A—O6A—C7A—N8A	74.9 (9)	C5B—O6B—C7B—C21B	−42.3 (10)
C5A—O6A—C7A—C21A	−43.6 (10)	C5B—O6B—C7B—C23B	−164.3 (7)
C5A—O6A—C7A—C23A	−167.6 (7)	O6B—C7B—N8B—C9B	−101.2 (9)
O6A—C7A—N8A—C9A	−103.9 (9)	C21B—C7B—N8B—C9B	20.4 (11)
C21A—C7A—N8A—C9A	17.2 (12)	C23B—C7B—N8B—C9B	143.2 (8)
C23A—C7A—N8A—C9A	141.6 (8)	C7B—N8B—C9B—N19B	7.7 (13)
C7A—N8A—C9A—N19A	10.5 (12)	C7B—N8B—C9B—S10B	−173.7 (7)
C7A—N8A—C9A—S10A	−169.8 (7)	N19B—C9B—S10B—C11B	1.4 (9)
N19A—C9A—S10A—C11A	11.6 (9)	N8B—C9B—S10B—C11B	−177.0 (6)
N8A—C9A—S10A—C11A	−167.9 (6)	C9B—S10B—C11B—C12B	50.4 (8)
C9A—S10A—C11A—C12A	47.4 (8)	S10B—C11B—C12B—C17B	−66.1 (9)
S10A—C11A—C12A—C13A	111.3 (9)	S10B—C11B—C12B—C13B	114.7 (8)
S10A—C11A—C12A—C17A	−72.7 (9)	C17B—C12B—C13B—C14B	−0.6 (12)
C17A—C12A—C13A—C14A	−1.9 (15)	C11B—C12B—C13B—C14B	178.6 (8)
C11A—C12A—C13A—C14A	174.1 (9)	C12B—C13B—C14B—C15B	1.6 (14)
C12A—C13A—C14A—C15A	0.6 (18)	C13B—C14B—C15B—C16B	−2.7 (15)
C13A—C14A—C15A—C16A	0.9 (18)	C14B—C15B—C16B—C17B	2.7 (15)
C14A—C15A—C16A—C17A	−1.0 (17)	C13B—C12B—C17B—C16B	0.6 (12)
C15A—C16A—C17A—C12A	−0.3 (13)	C11B—C12B—C17B—C16B	−178.6 (7)
C15A—C16A—C17A—C18A	178.5 (9)	C13B—C12B—C17B—C18B	177.5 (7)
C13A—C12A—C17A—C16A	1.7 (12)	C11B—C12B—C17B—C18B	−1.7 (11)
C11A—C12A—C17A—C16A	−174.6 (7)	C15B—C16B—C17B—C12B	−1.7 (13)
C13A—C12A—C17A—C18A	−177.1 (8)	C15B—C16B—C17B—C18B	−178.5 (8)
C11A—C12A—C17A—C18A	6.6 (11)	C12B—C17B—C18B—N19B	79.1 (9)
C16A—C17A—C18A—N19A	−103.9 (9)	C16B—C17B—C18B—N19B	−104.1 (9)
C12A—C17A—C18A—N19A	74.9 (9)	N8B—C9B—N19B—C18B	−176.3 (7)
N8A—C9A—N19A—C18A	176.2 (7)	S10B—C9B—N19B—C18B	5.4 (12)
S10A—C9A—N19A—C18A	−3.3 (12)	N8B—C9B—N19B—C20B	1.4 (11)
N8A—C9A—N19A—C20A	2.7 (11)	S10B—C9B—N19B—C20B	−176.9 (6)
S10A—C9A—N19A—C20A	−176.8 (6)	C17B—C18B—N19B—C9B	−64.9 (11)
C17A—C18A—N19A—C9A	−62.3 (10)	C17B—C18B—N19B—C20B	117.3 (8)
C17A—C18A—N19A—C20A	111.2 (8)	C9B—N19B—C20B—C21B	−37.5 (9)
C9A—N19A—C20A—C21A	−41.9 (9)	C18B—N19B—C20B—C21B	140.4 (7)
C18A—N19A—C20A—C21A	144.3 (7)	C9B—N19B—C20B—C22B	80.7 (9)
C9A—N19A—C20A—C22A	79.2 (10)	C18B—N19B—C20B—C22B	−101.4 (8)
C18A—N19A—C20A—C22A	−94.7 (9)	C22B—C20B—C21B—C7B	−55.9 (9)
N19A—C20A—C21A—C7A	67.2 (8)	N19B—C20B—C21B—C7B	63.7 (8)
C22A—C20A—C21A—C7A	−53.9 (9)	O6B—C7B—C21B—C20B	66.5 (9)
O6A—C7A—C21A—C20A	65.8 (9)	N8B—C7B—C21B—C20B	−54.7 (9)
N8A—C7A—C21A—C20A	−54.2 (9)	C23B—C7B—C21B—C20B	−176.1 (8)
C23A—C7A—C21A—C20A	−175.7 (7)	O6B—C5B—C22B—C1B	176.0 (8)
C2A—C1A—C22A—C5A	1.3 (14)	C4B—C5B—C22B—C1B	−1.2 (12)
C2A—C1A—C22A—C20A	177.8 (8)	O6B—C5B—C22B—C20B	−3.5 (12)
C4A—C5A—C22A—C1A	0.6 (14)	C4B—C5B—C22B—C20B	179.2 (7)
O6A—C5A—C22A—C1A	177.7 (8)	C2B—C1B—C22B—C5B	−0.2 (13)
C4A—C5A—C22A—C20A	−175.9 (8)	C2B—C1B—C22B—C20B	179.3 (8)
O6A—C5A—C22A—C20A	1.2 (13)	C21B—C20B—C22B—C5B	27.2 (10)
N19A—C20A—C22A—C1A	87.7 (10)	N19B—C20B—C22B—C5B	−90.6 (9)
C21A—C20A—C22A—C1A	−153.2 (8)	C21B—C20B—C22B—C1B	−152.3 (8)
N19A—C20A—C22A—C5A	−95.8 (10)	N19B—C20B—C22B—C1B	89.9 (9)
C21A—C20A—C22A—C5A	23.3 (11)	O—C1—N—C2	4.7 (19)
C22B—C1B—C2B—C3B	2.6 (14)	O—C1—N—C3	−179.8 (12)