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organic compounds
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.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100006727/sk1354sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100006727/sk1354IIsup2.hkl |
CCDC reference: 150840
Computing details top
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 top
Crystal data top
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) Å3 | Plate, colourless |
Z = 8 | 0.35 × 0.30 × 0.10 mm |
F(000) = 1808 |
Data collection top
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 top
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0758P)2] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.063 | (Δ/σ)max = 0.002 |
wR(F2) = 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+0.001xFc2λ3/sin(2θ)]-1/4 |
483 parameters | Extinction coefficient: 0.0017 (3) |
0 restraints |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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 (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
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) top
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) |
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