(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 (2024)

(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 (27)

V. Kettmann and J. Svetlik

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.

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Supporting information

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100006727/sk1354sup1.cif
Contains datablocks default, II

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100006727/sk1354IIsup2.hkl
Contains datablock II

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 0.5dimethylformamide top

Crystal data

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C19H19N2OS·Br·0.5C3H7NODx = 1.437 Mg m−3
Dm = 1.44 (1) Mg m−3
Dm measured by flotation in bromoform/c-hexane
Mr = 439.89Melting point: 511 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 18.612 (8) ÅCell parameters from 15 reflections
b = 19.807 (9) Åθ = 10–22°
c = 11.087 (5) ŵ = 2.14 mm−1
β = 95.94 (3)°T = 293 K
V = 4065 (3) Å3Plate, colourless
Z = 80.35 × 0.30 × 0.10 mm
F(000) = 1808

Data collection

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Syntex P21
diffractometer		3573 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
Graphite monochromatorθmax = 25.1°, θmin = 1.5°
θ/2θ scansh = −22→0
Absorption correction: ψ scan
(North et al., 1968)		k = 0→23
Tmin = 0.495, Tmax = 0.810l = −12→12
7534 measured reflections2 standard reflections every 100 min
7166 independent reflections intensity decay: none

Refinement

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Refinement on F2H-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) = 0.157Δρmax = 0.39 e Å−3
S = 0.90Δρmin = −0.31 e Å−3
7166 reflectionsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
483 parametersExtinction coefficient: 0.0017 (3)
0 restraints

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

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xyzUiso*/Ueq
C1A0.3670 (5)0.1067 (6)0.7573 (9)0.074 (3)
H1A0.33410.07590.72030.089*
C2A0.4245 (6)0.0846 (6)0.8386 (11)0.088 (4)
H2A0.42890.03890.85690.106*
C3A0.4742 (7)0.1287 (8)0.8915 (11)0.101 (4)
H3A0.51230.11330.94540.122*
C4A0.4675 (5)0.1961 (7)0.8642 (10)0.082 (4)
H4A0.50200.22640.89820.099*
C5A0.4104 (5)0.2193 (6)0.7876 (8)0.059 (3)
O6A0.4056 (3)0.2875 (4)0.7611 (6)0.0685 (18)
C7A0.3422 (5)0.3108 (5)0.6914 (8)0.059 (3)
N8A0.2822 (4)0.3127 (3)0.7667 (6)0.0504 (19)
H8A0.28190.34540.81750.060*
C9A0.2281 (4)0.2685 (4)0.7642 (8)0.045 (2)
S10A0.16091 (12)0.29550 (12)0.8474 (2)0.0560 (7)
C11A0.0991 (4)0.2264 (5)0.8668 (8)0.060 (3)
H11A0.06730.23930.92680.072*
H11B0.06960.21890.79070.072*
C12A0.1363 (4)0.1617 (5)0.9060 (9)0.055 (3)
C13A0.1340 (5)0.1333 (6)1.0171 (9)0.072 (3)
H13A0.11160.15751.07460.086*
C14A0.1619 (7)0.0727 (8)1.0496 (12)0.107 (5)
H14A0.15850.05541.12680.128*
C15A0.1957 (6)0.0369 (6)0.9651 (13)0.096 (4)
H15A0.2150−0.00550.98460.116*
C16A0.2012 (5)0.0640 (5)0.8510 (11)0.072 (3)
H16A0.22480.03960.79530.087*
C17A0.1721 (4)0.1267 (5)0.8184 (9)0.052 (2)
C18A0.1786 (4)0.1577 (5)0.6981 (8)0.056 (3)
H18A0.19150.12290.64270.067*
H18B0.13200.17580.66660.067*
N19A0.2331 (3)0.2123 (4)0.7017 (6)0.0436 (17)
C20A0.2997 (4)0.1997 (5)0.6422 (8)0.053 (2)
H20A0.28950.16590.57810.063*
C21A0.3204 (4)0.2646 (5)0.5871 (8)0.060 (3)
H21A0.28000.28330.53570.072*
H21B0.36030.25770.53860.072*
C22A0.3594 (5)0.1745 (6)0.7325 (8)0.060 (3)
C23A0.3603 (5)0.3822 (5)0.6542 (8)0.076 (3)
H23A0.32190.39930.59790.113*
H23B0.40450.38180.61650.113*
H23C0.36590.41070.72470.113*
C1B−0.1531 (5)0.3465 (5)0.4358 (9)0.063 (3)
H1B−0.10590.33270.45900.076*
C2B−0.1682 (6)0.3859 (5)0.3325 (10)0.081 (3)
H2B−0.13160.39680.28490.098*
C3B−0.2367 (7)0.4085 (5)0.3010 (10)0.081 (3)
H3B−0.24600.43690.23440.097*
C4B−0.2919 (6)0.3900 (5)0.3661 (9)0.070 (3)
H4B−0.33880.40450.34230.084*
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−0.32900.36710.76400.066*
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−0.13160.46421.01550.074*
H11D−0.11030.38900.99430.074*
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−0.06840.54660.91760.069*
C14B−0.0151 (5)0.5356 (5)0.7718 (11)0.075 (3)
H14B0.00460.57880.77340.090*
C15B−0.0013 (5)0.4905 (6)0.6822 (10)0.080 (3)
H15B0.02620.50450.62140.096*
C16B−0.0267 (5)0.4268 (5)0.6804 (9)0.069 (3)
H16B−0.01510.39660.62110.083*
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−0.07090.30570.72520.064*
H18D−0.09280.31850.85590.064*
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−0.15360.25350.60580.058*
C21B−0.2603 (4)0.2459 (4)0.6333 (8)0.052 (2)
H21C−0.25350.21990.70770.063*
H21D−0.27190.21510.56610.063*
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−0.40600.23070.60460.129*
H23E−0.42830.29740.66730.129*
H23F−0.38500.24140.74390.129*
Br10.26794 (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)
H1−0.36270.44060.97620.110*
C2−0.5217 (5)0.3823 (5)1.0024 (10)0.086 (3)
H2C−0.52560.35041.06660.128*
H2D−0.52240.35870.92670.128*
H2E−0.56150.41330.99870.128*
C3−0.4424 (5)0.4544 (6)1.1417 (8)0.087 (4)
H3C−0.43780.42201.20640.131*
H3D−0.48240.48381.15120.131*
H3E−0.39880.48051.14360.131*
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)

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U11U22U33U12U13U23
C1A0.047 (6)0.105 (10)0.074 (8)0.017 (6)0.023 (6)0.001 (7)
C2A0.067 (8)0.100 (10)0.101 (10)0.027 (7)0.028 (8)0.026 (9)
C3A0.085 (10)0.151 (14)0.070 (9)0.036 (10)0.021 (7)0.023 (10)
C4A0.028 (5)0.145 (12)0.072 (8)0.005 (7)−0.004 (5)−0.036 (9)
C5A0.037 (5)0.088 (8)0.054 (6)−0.005 (6)0.016 (5)−0.022 (7)
O6A0.046 (4)0.087 (5)0.071 (5)−0.009 (4)0.004 (4)−0.016 (4)
C7A0.054 (6)0.079 (8)0.045 (6)−0.008 (6)0.011 (5)−0.006 (6)
N8A0.060 (5)0.046 (4)0.045 (4)−0.006 (4)0.010 (4)−0.008 (4)
C9A0.039 (5)0.051 (6)0.043 (6)−0.001 (5)0.000 (4)0.002 (5)
S10A0.0533 (14)0.0569 (15)0.0597 (16)0.0052 (13)0.0155 (13)−0.0110 (14)
C11A0.033 (5)0.088 (7)0.062 (6)−0.007 (5)0.019 (5)−0.009 (6)
C12A0.038 (5)0.070 (7)0.056 (7)−0.010 (5)−0.001 (5)−0.003 (6)
C13A0.083 (8)0.081 (8)0.051 (7)−0.032 (7)0.004 (6)0.012 (7)
C14A0.105 (11)0.116 (13)0.096 (11)−0.033 (9)−0.007 (9)0.049 (10)
C15A0.090 (9)0.069 (9)0.126 (12)−0.013 (7)−0.012 (9)0.046 (9)
C16A0.059 (6)0.054 (7)0.102 (9)−0.003 (5)0.001 (6)0.006 (7)
C17A0.036 (5)0.066 (7)0.054 (6)−0.018 (5)−0.003 (5)0.004 (6)
C18A0.041 (5)0.074 (7)0.049 (6)0.005 (5)−0.015 (5)−0.017 (6)
N19A0.032 (4)0.051 (4)0.047 (4)−0.013 (4)−0.004 (3)−0.014 (4)
C20A0.043 (5)0.074 (7)0.043 (5)−0.001 (5)0.016 (5)−0.016 (6)
C21A0.052 (6)0.089 (8)0.041 (6)0.001 (5)0.010 (5)−0.010 (6)
C22A0.062 (7)0.075 (7)0.044 (6)0.016 (6)0.008 (5)0.001 (6)
C23A0.085 (7)0.085 (8)0.063 (7)−0.016 (6)0.036 (6)−0.005 (6)
C1B0.077 (7)0.068 (7)0.047 (6)−0.006 (6)0.010 (6)−0.009 (6)
C2B0.088 (9)0.081 (8)0.073 (9)−0.023 (7)0.000 (7)0.009 (7)
C3B0.134 (11)0.050 (7)0.056 (7)−0.019 (8)0.000 (8)0.001 (6)
C4B0.092 (8)0.052 (7)0.059 (7)0.007 (6)−0.024 (7)−0.003 (6)
C5B0.057 (6)0.047 (6)0.044 (6)0.003 (5)−0.004 (5)−0.009 (5)
O6B0.044 (4)0.079 (5)0.062 (4)0.007 (3)0.000 (3)0.002 (4)
C7B0.038 (5)0.069 (6)0.059 (6)0.003 (5)0.014 (5)0.001 (6)
N8B0.055 (5)0.061 (5)0.053 (5)0.003 (4)0.018 (4)−0.016 (4)
C9B0.037 (5)0.041 (5)0.061 (6)0.001 (4)0.016 (5)0.010 (5)
S10B0.0558 (15)0.0692 (17)0.0606 (17)0.0006 (13)0.0137 (13)−0.0185 (14)
C11B0.072 (6)0.063 (6)0.046 (6)0.018 (5)−0.006 (5)−0.021 (5)
C12B0.051 (5)0.051 (6)0.049 (6)0.020 (5)−0.009 (5)−0.006 (6)
C13B0.055 (6)0.052 (7)0.062 (7)0.003 (5)−0.010 (5)−0.018 (6)
C14B0.059 (7)0.065 (7)0.097 (9)−0.016 (6)−0.007 (7)−0.005 (7)
C15B0.070 (7)0.088 (9)0.085 (9)−0.022 (7)0.021 (6)−0.006 (8)
C16B0.042 (6)0.076 (8)0.089 (8)−0.005 (5)0.003 (6)−0.015 (7)
C17B0.031 (5)0.061 (6)0.054 (6)0.005 (5)−0.002 (5)−0.001 (6)
C18B0.052 (6)0.056 (6)0.051 (6)0.025 (5)−0.003 (5)−0.001 (5)
N19B0.034 (4)0.050 (4)0.048 (5)0.010 (3)0.001 (4)0.006 (4)
C20B0.052 (5)0.043 (5)0.052 (6)0.008 (5)0.008 (5)−0.002 (5)
C21B0.062 (6)0.051 (6)0.044 (5)−0.009 (5)0.004 (5)−0.007 (5)
C22B0.054 (6)0.039 (5)0.051 (6)0.001 (5)−0.004 (5)−0.008 (5)
C23B0.045 (6)0.112 (9)0.108 (9)−0.021 (6)0.035 (6)−0.018 (8)
Br10.0783 (7)0.0412 (5)0.0662 (7)−0.0008 (5)0.0180 (5)0.0002 (6)
Br20.0467 (5)0.0626 (6)0.0558 (6)−0.0006 (5)0.0017 (4)0.0062 (5)
C10.042 (6)0.109 (10)0.130 (11)−0.002 (6)0.037 (8)−0.028 (9)
C20.054 (6)0.091 (8)0.113 (9)−0.002 (6)0.017 (6)−0.003 (7)
C30.071 (7)0.132 (10)0.058 (7)−0.025 (7)0.004 (6)−0.002 (8)
N0.035 (4)0.062 (5)0.094 (7)0.007 (4)0.010 (5)0.000 (5)
O0.070 (5)0.195 (10)0.151 (8)−0.013 (5)0.041 (6)−0.107 (8)

Geometric parameters (Å, º)

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C1A—C22A1.375 (12)C2B—C3B1.361 (13)
C1A—C2A1.396 (13)C3B—C4B1.366 (12)
C2A—C3A1.360 (15)C4B—C5B1.407 (12)
C3A—C4A1.372 (15)C5B—O6B1.374 (9)
C4A—C5A1.369 (13)C5B—C22B1.377 (11)
C5A—O6A1.384 (11)O6B—C7B1.431 (10)
C5A—C22A1.393 (12)C7B—N8B1.437 (10)
O6A—C7A1.419 (10)C7B—C21B1.506 (10)
C7A—N8A1.462 (10)C7B—C23B1.538 (10)
C7A—C21A1.498 (11)N8B—C9B1.332 (9)
C7A—C23A1.521 (12)C9B—N19B1.289 (9)
N8A—C9A1.332 (9)C9B—S10B1.742 (9)
C9A—N19A1.320 (9)S10B—C11B1.807 (8)
C9A—S10A1.715 (8)C11B—C12B1.484 (11)
S10A—C11A1.814 (8)C12B—C17B1.390 (11)
C11A—C12A1.500 (12)C12B—C13B1.396 (11)
C12A—C13A1.359 (12)C13B—C14B1.366 (12)
C12A—C17A1.414 (11)C14B—C15B1.379 (13)
C13A—C14A1.341 (14)C15B—C16B1.348 (12)
C14A—C15A1.379 (15)C16B—C17B1.399 (11)
C15A—C16A1.387 (14)C17B—C18B1.524 (11)
C16A—C17A1.388 (12)C18B—N19B1.462 (9)
C17A—C18A1.484 (11)N19B—C20B1.513 (9)
C18A—N19A1.481 (10)C20B—C21B1.490 (10)
N19A—C20A1.484 (9)C20B—C22B1.501 (11)
C20A—C21A1.491 (11)C1—O1.224 (12)
C20A—C22A1.502 (11)C1—N1.289 (11)
C1B—C2B1.390 (12)C2—N1.441 (10)
C1B—C22B1.392 (11)C3—N1.466 (11)
C22A—C1A—C2A119.5 (11)C2B—C3B—C4B120.8 (11)
C3A—C2A—C1A121.2 (12)C3B—C4B—C5B119.8 (10)
C2A—C3A—C4A119.2 (13)O6B—C5B—C22B124.2 (8)
C5A—C4A—C3A120.6 (12)O6B—C5B—C4B115.8 (9)
C4A—C5A—O6A119.1 (10)C22B—C5B—C4B119.9 (9)
C4A—C5A—C22A120.6 (11)C5B—O6B—C7B114.5 (6)
O6A—C5A—C22A120.2 (9)O6B—C7B—N8B110.8 (7)
C5A—O6A—C7A117.7 (7)O6B—C7B—C21B111.4 (7)
O6A—C7A—N8A109.7 (7)N8B—C7B—C21B107.0 (7)
O6A—C7A—C21A111.4 (8)O6B—C7B—C23B104.8 (7)
N8A—C7A—C21A107.1 (7)N8B—C7B—C23B110.3 (7)
O6A—C7A—C23A104.8 (8)C21B—C7B—C23B112.6 (8)
N8A—C7A—C23A109.6 (8)C9B—N8B—C7B125.7 (7)
C21A—C7A—C23A114.2 (8)N19B—C9B—N8B120.8 (8)
C9A—N8A—C7A126.3 (7)N19B—C9B—S10B129.0 (7)
N19A—C9A—N8A118.1 (7)N8B—C9B—S10B110.2 (6)
N19A—C9A—S10A129.8 (6)C9B—S10B—C11B110.4 (4)
N8A—C9A—S10A112.1 (7)C12B—C11B—S10B114.5 (6)
C9A—S10A—C11A109.6 (4)C17B—C12B—C13B117.8 (9)
C12A—C11A—S10A113.6 (6)C17B—C12B—C11B120.7 (9)
C13A—C12A—C17A118.7 (9)C13B—C12B—C11B121.5 (9)
C13A—C12A—C11A124.0 (10)C14B—C13B—C12B121.4 (9)
C17A—C12A—C11A117.1 (9)C13B—C14B—C15B119.1 (10)
C14A—C13A—C12A124.5 (12)C16B—C15B—C14B121.7 (10)
C13A—C14A—C15A117.9 (12)C15B—C16B—C17B119.2 (10)
C14A—C15A—C16A120.2 (11)C12B—C17B—C16B120.6 (9)
C17A—C16A—C15A121.4 (11)C12B—C17B—C18B117.9 (8)
C16A—C17A—C12A117.3 (9)C16B—C17B—C18B121.4 (8)
C16A—C17A—C18A122.6 (10)N19B—C18B—C17B113.6 (6)
C12A—C17A—C18A120.2 (9)C9B—N19B—C18B124.5 (7)
N19A—C18A—C17A113.5 (7)C9B—N19B—C20B118.2 (7)
C9A—N19A—C18A123.0 (7)C18B—N19B—C20B117.2 (6)
C9A—N19A—C20A118.9 (6)C21B—C20B—C22B108.4 (7)
C18A—N19A—C20A117.8 (7)C21B—C20B—N19B107.6 (6)
N19A—C20A—C21A107.5 (7)C22B—C20B—N19B110.6 (6)
N19A—C20A—C22A110.7 (7)C20B—C21B—C7B107.2 (7)
C21A—C20A—C22A110.7 (8)C5B—C22B—C1B119.2 (9)
C20A—C21A—C7A105.8 (7)C5B—C22B—C20B119.6 (8)
C1A—C22A—C5A118.8 (10)C1B—C22B—C20B121.2 (8)
C1A—C22A—C20A120.8 (10)O—C1—N125.9 (11)
C5A—C22A—C20A120.3 (10)C1—N—C2122.7 (10)
C2B—C1B—C22B120.2 (9)C1—N—C3120.3 (9)
C3B—C2B—C1B120.0 (11)C2—N—C3116.8 (8)
C22A—C1A—C2A—C3A−1.6 (16)C1B—C2B—C3B—C4B−3.6 (15)
C1A—C2A—C3A—C4A0.0 (18)C2B—C3B—C4B—C5B2.1 (15)
C2A—C3A—C4A—C5A1.9 (18)C3B—C4B—C5B—O6B−177.2 (8)
C3A—C4A—C5A—O6A−179.4 (9)C3B—C4B—C5B—C22B0.3 (13)
C3A—C4A—C5A—C22A−2.2 (15)C22B—C5B—O6B—C7B10.9 (11)
C4A—C5A—O6A—C7A−173.8 (8)C4B—C5B—O6B—C7B−171.7 (7)
C22A—C5A—O6A—C7A9.1 (12)C5B—O6B—C7B—N8B76.8 (8)
C5A—O6A—C7A—N8A74.9 (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—C9B20.4 (11)
C21A—C7A—N8A—C9A17.2 (12)C23B—C7B—N8B—C9B143.2 (8)
C23A—C7A—N8A—C9A141.6 (8)C7B—N8B—C9B—N19B7.7 (13)
C7A—N8A—C9A—N19A10.5 (12)C7B—N8B—C9B—S10B−173.7 (7)
C7A—N8A—C9A—S10A−169.8 (7)N19B—C9B—S10B—C11B1.4 (9)
N19A—C9A—S10A—C11A11.6 (9)N8B—C9B—S10B—C11B−177.0 (6)
N8A—C9A—S10A—C11A−167.9 (6)C9B—S10B—C11B—C12B50.4 (8)
C9A—S10A—C11A—C12A47.4 (8)S10B—C11B—C12B—C17B−66.1 (9)
S10A—C11A—C12A—C13A111.3 (9)S10B—C11B—C12B—C13B114.7 (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—C14B178.6 (8)
C11A—C12A—C13A—C14A174.1 (9)C12B—C13B—C14B—C15B1.6 (14)
C12A—C13A—C14A—C15A0.6 (18)C13B—C14B—C15B—C16B−2.7 (15)
C13A—C14A—C15A—C16A0.9 (18)C14B—C15B—C16B—C17B2.7 (15)
C14A—C15A—C16A—C17A−1.0 (17)C13B—C12B—C17B—C16B0.6 (12)
C15A—C16A—C17A—C12A−0.3 (13)C11B—C12B—C17B—C16B−178.6 (7)
C15A—C16A—C17A—C18A178.5 (9)C13B—C12B—C17B—C18B177.5 (7)
C13A—C12A—C17A—C16A1.7 (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—C18A6.6 (11)C12B—C17B—C18B—N19B79.1 (9)
C16A—C17A—C18A—N19A−103.9 (9)C16B—C17B—C18B—N19B−104.1 (9)
C12A—C17A—C18A—N19A74.9 (9)N8B—C9B—N19B—C18B−176.3 (7)
N8A—C9A—N19A—C18A176.2 (7)S10B—C9B—N19B—C18B5.4 (12)
S10A—C9A—N19A—C18A−3.3 (12)N8B—C9B—N19B—C20B1.4 (11)
N8A—C9A—N19A—C20A2.7 (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—C20B117.3 (8)
C17A—C18A—N19A—C20A111.2 (8)C9B—N19B—C20B—C21B−37.5 (9)
C9A—N19A—C20A—C21A−41.9 (9)C18B—N19B—C20B—C21B140.4 (7)
C18A—N19A—C20A—C21A144.3 (7)C9B—N19B—C20B—C22B80.7 (9)
C9A—N19A—C20A—C22A79.2 (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—C7A67.2 (8)N19B—C20B—C21B—C7B63.7 (8)
C22A—C20A—C21A—C7A−53.9 (9)O6B—C7B—C21B—C20B66.5 (9)
O6A—C7A—C21A—C20A65.8 (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—C1B176.0 (8)
C2A—C1A—C22A—C5A1.3 (14)C4B—C5B—C22B—C1B−1.2 (12)
C2A—C1A—C22A—C20A177.8 (8)O6B—C5B—C22B—C20B−3.5 (12)
C4A—C5A—C22A—C1A0.6 (14)C4B—C5B—C22B—C20B179.2 (7)
O6A—C5A—C22A—C1A177.7 (8)C2B—C1B—C22B—C5B−0.2 (13)
C4A—C5A—C22A—C20A−175.9 (8)C2B—C1B—C22B—C20B179.3 (8)
O6A—C5A—C22A—C20A1.2 (13)C21B—C20B—C22B—C5B27.2 (10)
N19A—C20A—C22A—C1A87.7 (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—C1B89.9 (9)
C21A—C20A—C22A—C5A23.3 (11)O—C1—N—C24.7 (19)
C22B—C1B—C2B—C3B2.6 (14)O—C1—N—C3−179.8 (12)

(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 (2024)

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