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The biological potential of compounds of the tricyclic dibenzo[b,e]azepine system has resulted in considerable synthetic efforts to develop efficient methods for the synthesis of new derivatives of this kind. (9RS,15RS)-9-Ethyl-11-methyl-9,13b-di­hydro­dibenzo[c,f]thia­zolo[3,2-a]azepin-3(2H)-one, C19H19NOS, (I), crystallizes as a kryptoracemate with Z′ = 2 in the space group P21, with one mol­ecule each of the (9R,15R) and (9S,15S) configurations in the asymmetric unit, while (9RS,15RS)-9-ethyl-7,12-dimethyl-9,13b-di­hydro­di­benzo[c,f]thia­zolo[3,2-a]aze­pin-3(2H)-one, C20H21NOS, (II), crystallizes with Z′ = 1 in the space group C2/c. Ethyl (13RS)-2-chloro-13-ethyl-4-oxo-8,13-di­hydro-4H-benzo[5,6]azepino[3,2,1-ij]quinoline-5-carboxyl­ate, C22H20ClNO3, (III), exhibits enanti­omeric disorder in the space group P\overline{1} such that the reference site is occupied by the 13R and 13S enanti­omers, with occupancies of 0.900 (6) and 0.100 (6). In each of the two independent mol­ecules in (I), the five-membered ring adopts an envelope conformation, but the corresponding ring in (II) adopts a half-chair conformation, while the six-membered ring in the major form of (III) adopts a twist-boat conformation. The conformation of the seven-membered ring in each of (I), (II) and the major form of (III) approximates to the twist-boat form. The mol­ecules of compound (I) are linked by two C—H...O hydrogen bonds to form two independent anti­parallel C(5) chains, with each type containing only one enanti­omer. These chains are linked into sheets by two C—H...π(arene) hydrogen bonds, in which the two donors are both provided by the (9R,15R) enanti­omer and the two acceptor arene rings form part of a mol­ecule of (9S,15S) configuration, precluding any additional crystallographic symmetry. The mol­ecules of compound (II) are linked by inversion-related C—H...π(arene) hydrogen bonds to form isolated cyclic centrosymmetric dimers. The mol­ecules of compound (III) are linked into cyclic centrosymmetric dimers by C—H...O hydrogen bonds and these dimers are linked into chains by a π–π stacking inter­action. Comparisons are made with some related structures.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616018143/sk3643sup1.cif
Contains datablocks global, I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616018143/sk3643Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616018143/sk3643IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616018143/sk3643IIIsup4.hkl
Contains datablock III

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616018143/sk3643Isup5.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616018143/sk3643IIsup6.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616018143/sk3643IIIsup7.cml
Supplementary material

CCDC references: 1516770; 1516769; 1516768

Computing details top

Data collection: APEX2 (Bruker, 2006) for (I), (II); COLLECT (Nonius, 1998) for (III). Cell refinement: SAINT (Bruker, 2006) for (I), (II); DIRAX/LSQ (Duisenberg et al., 2000) for (III). Data reduction: SAINT (Bruker, 2006) for (I), (II); EVALCCD (Duisenberg et al., 2003) for (III). Program(s) used to solve structure: SIR92 (Altomare et al., 1994) for (I), (II); SIR2014 (Burla et al., 2015) for (III). For all compounds, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

(I) (9RS,15RS)-9-Ethyl-11-methyl-9,13b-dihydrodibenzo[c,f]thiazolo[3,2-a]azepin-3(2H)-one top
Crystal data top
C19H19NOSF(000) = 656
Mr = 309.41Dx = 1.308 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 11.4261 (5) ÅCell parameters from 11002 reflections
b = 8.1847 (3) Åθ = 1.8–32.5°
c = 16.8243 (6) ŵ = 0.21 mm1
β = 93.067 (2)°T = 100 K
V = 1571.14 (11) Å3Block, colourless
Z = 40.40 × 0.35 × 0.22 mm
Data collection top
Bruker Kappa APEXII
diffractometer
10697 reflections with I > 2σ(I)
Radiation source: high brilliance microfocus sealed tubeRint = 0.025
φ and ω scansθmax = 32.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
h = 1716
Tmin = 0.823, Tmax = 0.955k = 1212
61785 measured reflectionsl = 2525
11002 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.029 w = 1/[σ2(Fo2) + (0.0527P)2 + 0.1585P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.079(Δ/σ)max = 0.001
S = 1.05Δρmax = 0.37 e Å3
11002 reflectionsΔρmin = 0.21 e Å3
401 parametersAbsolute structure: Flack x determined using 4787 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute structure parameter: 0.007 (6)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S110.04257 (3)0.64856 (4)0.31677 (2)0.02072 (7)
C120.06240 (11)0.6542 (2)0.39359 (8)0.0221 (2)
H12A0.09750.76430.39730.026*
H12B0.12580.57370.38250.026*
C130.00808 (11)0.61139 (17)0.46981 (8)0.0198 (2)
O130.03273 (10)0.55030 (17)0.52867 (7)0.0298 (2)
N140.12297 (9)0.65093 (16)0.46388 (6)0.01701 (19)
C14A0.20563 (11)0.63483 (17)0.52973 (7)0.0170 (2)
C150.19005 (13)0.72209 (19)0.59932 (8)0.0221 (2)
H150.12460.79270.60320.027*
C160.27158 (15)0.7045 (2)0.66311 (8)0.0256 (3)
H160.26180.76230.71130.031*
C170.36731 (14)0.6021 (2)0.65618 (8)0.0243 (3)
H170.42410.59270.69930.029*
C180.38124 (11)0.51298 (19)0.58668 (7)0.0195 (2)
H180.44660.44220.58320.023*
C18A0.29966 (11)0.52719 (16)0.52223 (7)0.0158 (2)
C190.30872 (10)0.43915 (16)0.44299 (7)0.0151 (2)
H190.22740.40540.42520.018*
C19A0.34743 (11)0.56585 (16)0.38285 (7)0.0148 (2)
C1100.45748 (11)0.55481 (17)0.35032 (7)0.0164 (2)
H1100.50710.46550.36500.020*
C1110.49666 (11)0.67094 (17)0.29695 (7)0.0173 (2)
C1120.42386 (11)0.80170 (18)0.27585 (7)0.0185 (2)
H1120.44820.88080.23880.022*
C1130.31535 (11)0.81690 (17)0.30887 (7)0.0177 (2)
H1130.26720.90830.29510.021*
C1140.27587 (10)0.70040 (16)0.36181 (7)0.0155 (2)
C1150.15382 (11)0.72903 (16)0.38914 (7)0.0160 (2)
H1150.14150.84950.39420.019*
C1160.61535 (12)0.6532 (2)0.26305 (8)0.0246 (3)
H16A0.60570.63250.20570.037*
H16B0.65720.56150.28900.037*
H16C0.66030.75390.27240.037*
C1910.38285 (11)0.28333 (17)0.44701 (7)0.0178 (2)
H19A0.39290.24310.39230.021*
H19B0.46150.30930.47130.021*
C1920.32763 (11)0.14856 (19)0.49539 (8)0.0211 (2)
H19C0.32450.18370.55090.032*
H19D0.37490.04900.49290.032*
H19E0.24800.12650.47340.032*
S210.22593 (3)0.00063 (5)0.08726 (2)0.02161 (7)
C220.06874 (13)0.02911 (19)0.08922 (8)0.0224 (3)
H22A0.04350.11130.12980.027*
H22B0.02760.07500.10160.027*
C230.04285 (12)0.08804 (18)0.00633 (8)0.0205 (2)
O230.04535 (10)0.16254 (18)0.00951 (7)0.0317 (3)
N240.13069 (9)0.04697 (14)0.04793 (6)0.01589 (19)
C24A0.12426 (10)0.08689 (16)0.13011 (7)0.0151 (2)
C250.03501 (11)0.02280 (18)0.17405 (8)0.0196 (2)
H250.02020.05170.15030.024*
C260.02786 (12)0.06939 (18)0.25329 (9)0.0219 (2)
H260.03320.02810.28380.026*
C270.11024 (12)0.17634 (18)0.28750 (8)0.0207 (2)
H270.10570.20750.34160.025*
C280.19976 (11)0.23845 (17)0.24303 (7)0.0175 (2)
H280.25620.31040.26740.021*
C28A0.20726 (10)0.19610 (15)0.16314 (7)0.0141 (2)
C290.30020 (10)0.26061 (15)0.10960 (7)0.0140 (2)
H290.25890.28240.05670.017*
C29A0.38728 (10)0.12397 (15)0.09590 (7)0.0140 (2)
C2100.50569 (10)0.13608 (17)0.12168 (7)0.0157 (2)
H2100.53180.23160.14940.019*
C2110.58688 (10)0.01222 (18)0.10797 (7)0.0170 (2)
C2120.54650 (11)0.12996 (18)0.06995 (7)0.0183 (2)
H2120.59950.21660.06090.022*
C2130.42911 (11)0.14551 (17)0.04519 (7)0.0167 (2)
H2130.40270.24370.02010.020*
C2140.34913 (10)0.01951 (16)0.05650 (7)0.01384 (19)
C2150.22787 (10)0.04930 (15)0.01916 (7)0.0144 (2)
H2150.20880.16780.02480.017*
C2160.71526 (11)0.0308 (2)0.13229 (8)0.0233 (3)
H26A0.73470.14720.13700.035*
H26B0.76250.01950.09200.035*
H26C0.73190.02300.18370.035*
C2910.35367 (11)0.42370 (16)0.13740 (8)0.0172 (2)
H29A0.38870.41170.19220.021*
H29B0.41680.45470.10230.021*
C2920.26090 (13)0.55806 (18)0.13589 (8)0.0222 (2)
H29C0.22270.56520.08240.033*
H29D0.29820.66280.14980.033*
H29E0.20230.53240.17450.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S110.01711 (13)0.02520 (16)0.01967 (13)0.00113 (12)0.00079 (10)0.00009 (12)
C120.0153 (5)0.0253 (7)0.0256 (6)0.0012 (5)0.0011 (4)0.0039 (5)
C130.0151 (5)0.0196 (6)0.0251 (6)0.0016 (4)0.0046 (4)0.0031 (4)
O130.0208 (5)0.0394 (7)0.0298 (5)0.0007 (5)0.0080 (4)0.0110 (5)
N140.0143 (4)0.0211 (5)0.0160 (4)0.0011 (4)0.0037 (3)0.0025 (4)
C14A0.0177 (5)0.0183 (6)0.0153 (4)0.0010 (4)0.0030 (4)0.0013 (4)
C150.0276 (6)0.0210 (6)0.0183 (5)0.0014 (5)0.0063 (5)0.0008 (5)
C160.0371 (8)0.0240 (7)0.0159 (5)0.0034 (6)0.0032 (5)0.0014 (5)
C170.0291 (7)0.0283 (7)0.0151 (5)0.0049 (5)0.0018 (5)0.0008 (5)
C180.0183 (5)0.0243 (6)0.0159 (5)0.0018 (5)0.0004 (4)0.0033 (4)
C18A0.0158 (5)0.0179 (6)0.0139 (4)0.0018 (4)0.0026 (4)0.0019 (4)
C190.0138 (5)0.0174 (5)0.0142 (4)0.0006 (4)0.0015 (4)0.0014 (4)
C19A0.0147 (5)0.0173 (5)0.0126 (4)0.0003 (4)0.0019 (4)0.0004 (4)
C1100.0152 (5)0.0205 (6)0.0137 (4)0.0000 (4)0.0020 (4)0.0001 (4)
C1110.0160 (5)0.0225 (6)0.0136 (4)0.0019 (4)0.0028 (4)0.0001 (4)
C1120.0192 (5)0.0220 (6)0.0145 (5)0.0024 (5)0.0020 (4)0.0028 (4)
C1130.0182 (5)0.0186 (6)0.0162 (5)0.0007 (4)0.0013 (4)0.0028 (4)
C1140.0143 (5)0.0180 (5)0.0143 (4)0.0004 (4)0.0021 (4)0.0003 (4)
C1150.0153 (5)0.0169 (5)0.0159 (5)0.0003 (4)0.0026 (4)0.0014 (4)
C1160.0188 (5)0.0323 (7)0.0234 (6)0.0010 (6)0.0087 (4)0.0042 (5)
C1910.0158 (5)0.0195 (6)0.0181 (5)0.0020 (4)0.0025 (4)0.0030 (4)
C1920.0181 (5)0.0204 (6)0.0250 (5)0.0006 (5)0.0023 (4)0.0051 (5)
S210.02265 (14)0.02804 (18)0.01408 (12)0.00534 (12)0.00057 (10)0.00045 (11)
C220.0241 (6)0.0233 (7)0.0189 (5)0.0003 (5)0.0065 (4)0.0005 (5)
C230.0192 (5)0.0192 (6)0.0223 (5)0.0020 (5)0.0061 (4)0.0026 (5)
O230.0241 (5)0.0360 (6)0.0339 (5)0.0138 (5)0.0088 (4)0.0078 (5)
N240.0131 (4)0.0182 (5)0.0162 (4)0.0020 (4)0.0013 (3)0.0022 (4)
C24A0.0133 (5)0.0158 (5)0.0164 (5)0.0011 (4)0.0010 (4)0.0006 (4)
C250.0141 (5)0.0205 (6)0.0245 (5)0.0009 (4)0.0041 (4)0.0009 (5)
C260.0197 (6)0.0215 (6)0.0253 (6)0.0009 (5)0.0093 (5)0.0024 (5)
C270.0238 (6)0.0210 (6)0.0180 (5)0.0034 (5)0.0062 (4)0.0004 (4)
C280.0199 (5)0.0174 (6)0.0155 (5)0.0009 (4)0.0016 (4)0.0006 (4)
C28A0.0133 (4)0.0142 (5)0.0150 (4)0.0012 (4)0.0014 (4)0.0002 (4)
C290.0149 (5)0.0132 (5)0.0140 (4)0.0013 (4)0.0012 (4)0.0002 (4)
C29A0.0132 (4)0.0152 (5)0.0138 (4)0.0006 (4)0.0021 (3)0.0012 (4)
C2100.0149 (4)0.0183 (5)0.0140 (4)0.0023 (4)0.0016 (3)0.0014 (4)
C2110.0134 (4)0.0232 (6)0.0145 (4)0.0002 (4)0.0023 (4)0.0034 (4)
C2120.0159 (5)0.0226 (6)0.0167 (5)0.0034 (4)0.0037 (4)0.0007 (4)
C2130.0171 (5)0.0175 (6)0.0159 (5)0.0013 (4)0.0032 (4)0.0010 (4)
C2140.0133 (4)0.0148 (5)0.0136 (4)0.0005 (4)0.0019 (3)0.0000 (4)
C2150.0139 (5)0.0149 (5)0.0144 (4)0.0001 (4)0.0008 (4)0.0009 (4)
C2160.0131 (5)0.0336 (8)0.0231 (6)0.0003 (5)0.0002 (4)0.0015 (5)
C2910.0190 (5)0.0149 (5)0.0178 (5)0.0027 (4)0.0001 (4)0.0013 (4)
C2920.0274 (6)0.0155 (6)0.0235 (6)0.0006 (5)0.0005 (5)0.0005 (4)
Geometric parameters (Å, º) top
S11—C121.8102 (14)S21—C221.8096 (15)
S11—C1151.8348 (13)S21—C2151.8354 (12)
C12—C131.5184 (19)C22—C231.520 (2)
C12—H12A0.9900C22—H22A0.9900
C12—H12B0.9900C22—H22B0.9900
C13—O131.2238 (16)C23—O231.2196 (17)
C13—N141.3609 (16)C23—N241.3623 (16)
N14—C14A1.4229 (15)N24—C24A1.4264 (16)
N14—C1151.4702 (16)N24—C2151.4648 (16)
C14A—C151.3911 (18)C24A—C251.3937 (17)
C14A—C18A1.4003 (18)C24A—C28A1.3968 (17)
C15—C161.390 (2)C25—C261.3933 (19)
C15—H150.9500C25—H250.9500
C16—C171.387 (2)C26—C271.388 (2)
C16—H160.9500C26—H260.9500
C17—C181.3947 (19)C27—C281.3951 (18)
C17—H170.9500C27—H270.9500
C18—C18A1.3964 (17)C28—C28A1.3951 (16)
C18—H180.9500C28—H280.9500
C18A—C191.5238 (17)C28A—C291.5232 (17)
C19—C1911.5305 (18)C29—C29A1.5226 (17)
C19—C19A1.5306 (17)C29—C2911.5308 (17)
C19—H191.0000C29—H291.0000
C19A—C1101.4009 (16)C29A—C2101.4020 (16)
C19A—C1141.4056 (18)C29A—C2141.4063 (17)
C110—C1111.3975 (17)C210—C2111.4015 (18)
C110—H1100.9500C210—H2100.9500
C111—C1121.3899 (19)C211—C2121.3946 (19)
C111—C1161.5061 (18)C211—C2161.5094 (17)
C112—C1131.3911 (17)C212—C2131.3890 (18)
C112—H1120.9500C212—H2120.9500
C113—C1141.3960 (17)C213—C2141.3976 (17)
C113—H1130.9500C213—H2130.9500
C114—C1151.5098 (17)C214—C2151.5102 (16)
C115—H1151.0000C215—H2151.0000
C116—H16A0.9800C216—H26A0.9800
C116—H16B0.9800C216—H26B0.9800
C116—H16C0.9800C216—H26C0.9800
C191—C1921.5271 (19)C291—C2921.527 (2)
C191—H19A0.9900C291—H29A0.9900
C191—H19B0.9900C291—H29B0.9900
C192—H19C0.9800C292—H29C0.9800
C192—H19D0.9800C292—H29D0.9800
C192—H19E0.9800C292—H29E0.9800
C12—S11—C11588.80 (6)C22—S21—C21590.38 (6)
C13—C12—S11104.79 (9)C23—C22—S21105.42 (9)
C13—C12—H12A110.8C23—C22—H22A110.7
S11—C12—H12A110.8S21—C22—H22A110.7
C13—C12—H12B110.8C23—C22—H22B110.7
S11—C12—H12B110.8S21—C22—H22B110.7
H12A—C12—H12B108.9H22A—C22—H22B108.8
O13—C13—N14124.56 (13)O23—C23—N24124.38 (13)
O13—C13—C12124.74 (12)O23—C23—C22124.26 (12)
N14—C13—C12110.69 (11)N24—C23—C22111.36 (12)
C13—N14—C14A121.57 (11)C23—N24—C24A121.25 (11)
C13—N14—C115116.26 (10)C23—N24—C215117.10 (10)
C14A—N14—C115121.78 (10)C24A—N24—C215121.52 (10)
C15—C14A—C18A122.15 (12)C25—C24A—C28A122.04 (11)
C15—C14A—N14119.88 (12)C25—C24A—N24120.33 (11)
C18A—C14A—N14117.95 (11)C28A—C24A—N24117.59 (11)
C16—C15—C14A119.06 (14)C26—C25—C24A119.11 (12)
C16—C15—H15120.5C26—C25—H25120.4
C14A—C15—H15120.5C24A—C25—H25120.4
C17—C16—C15119.77 (13)C27—C26—C25119.76 (12)
C17—C16—H16120.1C27—C26—H26120.1
C15—C16—H16120.1C25—C26—H26120.1
C16—C17—C18120.80 (13)C26—C27—C28120.53 (12)
C16—C17—H17119.6C26—C27—H27119.7
C18—C17—H17119.6C28—C27—H27119.7
C17—C18—C18A120.40 (13)C27—C28—C28A120.72 (12)
C17—C18—H18119.8C27—C28—H28119.6
C18A—C18—H18119.8C28A—C28—H28119.6
C18—C18A—C14A117.78 (12)C28—C28A—C24A117.83 (11)
C18—C18A—C19124.48 (12)C28—C28A—C29124.36 (11)
C14A—C18A—C19117.69 (11)C24A—C28A—C29117.81 (10)
C18A—C19—C191114.75 (10)C29A—C29—C28A108.47 (10)
C18A—C19—C19A107.07 (10)C29A—C29—C291115.68 (10)
C191—C19—C19A114.52 (10)C28A—C29—C291113.64 (10)
C18A—C19—H19106.6C29A—C29—H29106.1
C191—C19—H19106.6C28A—C29—H29106.1
C19A—C19—H19106.6C291—C29—H29106.1
C110—C19A—C114118.32 (11)C210—C29A—C214118.33 (11)
C110—C19A—C19120.78 (11)C210—C29A—C29121.93 (11)
C114—C19A—C19120.83 (10)C214—C29A—C29119.74 (10)
C111—C110—C19A122.16 (12)C211—C210—C29A122.29 (12)
C111—C110—H110118.9C211—C210—H210118.9
C19A—C110—H110118.9C29A—C210—H210118.9
C112—C111—C110118.68 (11)C212—C211—C210118.26 (11)
C112—C111—C116121.09 (12)C212—C211—C216120.09 (12)
C110—C111—C116120.23 (12)C210—C211—C216121.64 (12)
C111—C112—C113120.06 (12)C213—C212—C211120.30 (12)
C111—C112—H112120.0C213—C212—H212119.9
C113—C112—H112120.0C211—C212—H212119.9
C112—C113—C114121.27 (12)C212—C213—C214121.30 (12)
C112—C113—H113119.4C212—C213—H213119.3
C114—C113—H113119.4C214—C213—H213119.3
C113—C114—C19A119.49 (11)C213—C214—C29A119.47 (11)
C113—C114—C115115.06 (11)C213—C214—C215114.60 (11)
C19A—C114—C115125.39 (11)C29A—C214—C215125.82 (11)
N14—C115—C114117.43 (10)N24—C215—C214118.07 (10)
N14—C115—S11102.84 (8)N24—C215—S21103.46 (8)
C114—C115—S11111.14 (8)C214—C215—S21109.44 (8)
N14—C115—H115108.4N24—C215—H215108.5
C114—C115—H115108.4C214—C215—H215108.5
S11—C115—H115108.4S21—C215—H215108.5
C111—C116—H16A109.5C211—C216—H26A109.5
C111—C116—H16B109.5C211—C216—H26B109.5
H16A—C116—H16B109.5H26A—C216—H26B109.5
C111—C116—H16C109.5C211—C216—H26C109.5
H16A—C116—H16C109.5H26A—C216—H26C109.5
H16B—C116—H16C109.5H26B—C216—H26C109.5
C192—C191—C19112.46 (10)C292—C291—C29110.95 (10)
C192—C191—H19A109.1C292—C291—H29A109.4
C19—C191—H19A109.1C29—C291—H29A109.4
C192—C191—H19B109.1C292—C291—H29B109.4
C19—C191—H19B109.1C29—C291—H29B109.4
H19A—C191—H19B107.8H29A—C291—H29B108.0
C191—C192—H19C109.5C291—C292—H29C109.5
C191—C192—H19D109.5C291—C292—H29D109.5
H19C—C192—H19D109.5H29C—C292—H29D109.5
C191—C192—H19E109.5C291—C292—H29E109.5
H19C—C192—H19E109.5H29C—C292—H29E109.5
H19D—C192—H19E109.5H29D—C292—H29E109.5
C115—S11—C12—C1335.23 (10)C215—S21—C22—C2330.15 (10)
S11—C12—C13—O13154.57 (14)S21—C22—C23—O23158.58 (14)
S11—C12—C13—N1425.70 (15)S21—C22—C23—N2421.43 (15)
O13—C13—N14—C14A4.8 (2)O23—C23—N24—C24A1.3 (2)
C12—C13—N14—C14A174.94 (13)C22—C23—N24—C24A178.71 (12)
O13—C13—N14—C115177.78 (14)O23—C23—N24—C215177.26 (14)
C12—C13—N14—C1151.96 (18)C22—C23—N24—C2152.73 (17)
C13—N14—C14A—C1560.13 (19)C23—N24—C24A—C2561.92 (18)
C115—N14—C14A—C15112.47 (15)C215—N24—C24A—C25113.89 (13)
C13—N14—C14A—C18A118.52 (14)C23—N24—C24A—C28A115.71 (14)
C115—N14—C14A—C18A68.89 (17)C215—N24—C24A—C28A68.49 (16)
C18A—C14A—C15—C161.2 (2)C28A—C24A—C25—C260.3 (2)
N14—C14A—C15—C16179.83 (13)N24—C24A—C25—C26177.25 (12)
C14A—C15—C16—C170.7 (2)C24A—C25—C26—C271.0 (2)
C15—C16—C17—C181.8 (2)C25—C26—C27—C280.4 (2)
C16—C17—C18—C18A1.0 (2)C26—C27—C28—C28A0.9 (2)
C17—C18—C18A—C14A0.90 (19)C27—C28—C28A—C24A1.56 (19)
C17—C18—C18A—C19178.15 (13)C27—C28—C28A—C29178.65 (12)
C15—C14A—C18A—C182.03 (19)C25—C24A—C28A—C281.00 (19)
N14—C14A—C18A—C18179.36 (12)N24—C24A—C28A—C28178.58 (11)
C15—C14A—C18A—C19179.46 (12)C25—C24A—C28A—C29179.20 (12)
N14—C14A—C18A—C191.92 (17)N24—C24A—C28A—C291.62 (17)
C18—C18A—C19—C19123.65 (17)C28—C28A—C29—C29A106.61 (13)
C14A—C18A—C19—C191159.10 (11)C24A—C28A—C29—C29A73.18 (13)
C18—C18A—C19—C19A104.63 (14)C28—C28A—C29—C29123.55 (17)
C14A—C18A—C19—C19A72.62 (13)C24A—C28A—C29—C291156.66 (11)
C18A—C19—C19A—C110113.42 (12)C28A—C29—C29A—C210117.02 (12)
C191—C19—C19A—C11015.00 (16)C291—C29—C29A—C21012.01 (16)
C18A—C19—C19A—C11463.48 (14)C28A—C29—C29A—C21462.82 (13)
C191—C19—C19A—C114168.09 (11)C291—C29—C29A—C214168.16 (10)
C114—C19A—C110—C1111.25 (18)C214—C29A—C210—C2111.41 (17)
C19—C19A—C110—C111178.23 (11)C29—C29A—C210—C211178.75 (11)
C19A—C110—C111—C1120.21 (19)C29A—C210—C211—C2122.46 (18)
C19A—C110—C111—C116179.52 (12)C29A—C210—C211—C216176.74 (11)
C110—C111—C112—C1131.25 (19)C210—C211—C212—C2131.27 (18)
C116—C111—C112—C113179.02 (13)C216—C211—C212—C213177.94 (12)
C111—C112—C113—C1141.7 (2)C211—C212—C213—C2140.92 (18)
C112—C113—C114—C19A0.62 (19)C212—C213—C214—C29A1.98 (18)
C112—C113—C114—C115176.88 (12)C212—C213—C214—C215174.33 (11)
C110—C19A—C114—C1130.82 (18)C210—C29A—C214—C2130.81 (16)
C19—C19A—C114—C113177.80 (11)C29—C29A—C214—C213179.03 (11)
C110—C19A—C114—C115178.04 (11)C210—C29A—C214—C215175.05 (11)
C19—C19A—C114—C1154.98 (19)C29—C29A—C214—C2155.11 (17)
C13—N14—C115—C114150.37 (12)C23—N24—C215—C214146.00 (12)
C14A—N14—C115—C11436.66 (18)C24A—N24—C215—C21438.03 (17)
C13—N14—C115—S1128.03 (14)C23—N24—C215—S2124.98 (13)
C14A—N14—C115—S11159.00 (11)C24A—N24—C215—S21159.05 (10)
C113—C114—C115—N14158.47 (12)C213—C214—C215—N24161.04 (10)
C19A—C114—C115—N1424.20 (18)C29A—C214—C215—N2422.92 (17)
C113—C114—C115—S1183.55 (12)C213—C214—C215—S2181.06 (12)
C19A—C114—C115—S1193.77 (13)C29A—C214—C215—S2194.98 (12)
C12—S11—C115—N1435.54 (9)C22—S21—C215—N2430.96 (9)
C12—S11—C115—C114162.03 (10)C22—S21—C215—C214157.65 (10)
C18A—C19—C191—C19266.55 (14)C29A—C29—C291—C292170.60 (10)
C19A—C19—C191—C192169.01 (11)C28A—C29—C291—C29262.94 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C115—H115···O13i1.002.473.3084 (18)141
C215—H215···O23ii1.002.373.1681 (18)136
C112—H112···Cg1iii0.952.813.6738 (13)152
C113—H113···Cg2iii0.952.853.7676 (14)163
Symmetry codes: (i) x, y+1/2, z+1; (ii) x, y1/2, z; (iii) x, y+1, z.
(II) (9RS,15RS)-9-Ethyl-7,12-dimethyl-9,13b-dihydrodibenzo[c,f]thiazolo[3,2-a]azepin-3(2H)-one top
Crystal data top
C20H21NOSF(000) = 1376
Mr = 323.44Dx = 1.297 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 18.1021 (12) ÅCell parameters from 3402 reflections
b = 12.4436 (8) Åθ = 2.0–26.4°
c = 14.8429 (9) ŵ = 0.20 mm1
β = 97.645 (3)°T = 298 K
V = 3313.7 (4) Å3Block, colourless
Z = 80.23 × 0.22 × 0.20 mm
Data collection top
Bruker Kappa APEXII
diffractometer
2307 reflections with I > 2σ(I)
Radiation source: high brilliance microfocus sealed tubeRint = 0.048
φ and ω scansθmax = 26.4°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
h = 2222
Tmin = 0.818, Tmax = 0.961k = 1513
30952 measured reflectionsl = 1418
3402 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.168 w = 1/[σ2(Fo2) + (0.070P)2 + 4.8478P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
3402 reflectionsΔρmax = 0.57 e Å3
211 parametersΔρmin = 0.45 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.40943 (5)0.29645 (9)0.65893 (6)0.0801 (4)
C20.32187 (17)0.2270 (3)0.6390 (2)0.0610 (8)
H2A0.31860.17440.68660.073*
H2B0.28110.27760.63910.073*
C30.31728 (16)0.1719 (2)0.5480 (2)0.0524 (7)
O30.26206 (12)0.12615 (19)0.51154 (16)0.0669 (6)
N40.38267 (12)0.18081 (18)0.51161 (15)0.0466 (6)
C4A0.38797 (15)0.1538 (2)0.41955 (18)0.0453 (6)
C50.37768 (18)0.0494 (2)0.3880 (2)0.0589 (8)
H50.36730.00520.42720.071*
C60.38296 (18)0.0273 (2)0.2984 (2)0.0612 (8)
H60.37540.04290.27750.073*
C70.39919 (15)0.1061 (2)0.23845 (19)0.0488 (7)
C80.40901 (14)0.2104 (2)0.27151 (17)0.0421 (6)
H80.41940.26480.23200.051*
C8A0.40380 (13)0.23624 (19)0.36146 (17)0.0392 (6)
C90.41873 (14)0.34878 (19)0.40082 (17)0.0403 (6)
H90.38210.36190.44270.048*
C9A0.49525 (14)0.34356 (19)0.45798 (17)0.0405 (6)
C100.55658 (16)0.4003 (2)0.43479 (19)0.0486 (7)
H1700.54970.44800.38620.058*
C110.62705 (16)0.3875 (3)0.4820 (2)0.0571 (8)
H110.66640.42680.46450.069*
C120.64037 (16)0.3175 (3)0.5547 (2)0.0548 (8)
C130.57916 (15)0.2630 (2)0.57933 (19)0.0494 (7)
H130.58630.21620.62860.059*
C140.50769 (14)0.2758 (2)0.53333 (17)0.0425 (6)
C150.44750 (15)0.2154 (2)0.57304 (18)0.0484 (7)
H150.47030.15120.60340.058*
C710.40746 (18)0.0815 (3)0.1414 (2)0.0613 (8)
H71A0.37210.02720.11870.092*
H71B0.45710.05600.13790.092*
H71C0.39850.14550.10550.092*
C910.40972 (15)0.4383 (2)0.33031 (18)0.0475 (7)
H91A0.42490.50580.35980.057*
H91B0.44260.42430.28510.057*
C920.33049 (18)0.4491 (3)0.2831 (2)0.0630 (8)
H92A0.32760.50850.24150.095*
H92B0.29750.46140.32760.095*
H92C0.31620.38420.25030.095*
C1210.71688 (18)0.3000 (3)0.6059 (3)0.0804 (11)
H12A0.73080.22600.60090.121*
H12B0.71660.31790.66870.121*
H12C0.75210.34490.58070.121*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0711 (6)0.1163 (8)0.0586 (5)0.0213 (5)0.0302 (4)0.0193 (5)
C20.0511 (17)0.081 (2)0.0540 (17)0.0063 (16)0.0195 (14)0.0199 (16)
C30.0453 (16)0.0565 (17)0.0574 (17)0.0010 (14)0.0140 (13)0.0231 (14)
O30.0440 (12)0.0749 (15)0.0830 (15)0.0105 (11)0.0124 (11)0.0168 (12)
N40.0427 (13)0.0499 (13)0.0489 (13)0.0057 (10)0.0120 (10)0.0065 (10)
C4A0.0408 (14)0.0438 (14)0.0523 (15)0.0048 (11)0.0094 (12)0.0030 (12)
C50.067 (2)0.0446 (16)0.0644 (19)0.0152 (14)0.0072 (15)0.0090 (14)
C60.073 (2)0.0397 (15)0.068 (2)0.0096 (14)0.0006 (16)0.0059 (14)
C70.0444 (15)0.0468 (15)0.0538 (16)0.0003 (12)0.0012 (12)0.0047 (13)
C80.0377 (14)0.0407 (14)0.0488 (15)0.0003 (11)0.0090 (11)0.0026 (12)
C8A0.0317 (12)0.0362 (13)0.0509 (15)0.0005 (10)0.0099 (11)0.0021 (11)
C90.0430 (14)0.0376 (13)0.0441 (14)0.0001 (11)0.0192 (11)0.0010 (11)
C9A0.0410 (14)0.0358 (13)0.0474 (15)0.0020 (11)0.0159 (11)0.0077 (11)
C100.0544 (17)0.0455 (15)0.0497 (15)0.0087 (13)0.0211 (13)0.0082 (12)
C110.0441 (17)0.0680 (19)0.0632 (19)0.0156 (14)0.0218 (14)0.0191 (16)
C120.0428 (16)0.0672 (19)0.0559 (17)0.0022 (13)0.0125 (13)0.0187 (15)
C130.0475 (16)0.0523 (16)0.0488 (15)0.0031 (13)0.0084 (13)0.0083 (13)
C140.0425 (15)0.0416 (14)0.0456 (14)0.0004 (11)0.0145 (12)0.0058 (11)
C150.0471 (16)0.0520 (16)0.0470 (15)0.0037 (13)0.0097 (12)0.0064 (13)
C710.064 (2)0.0570 (18)0.0623 (19)0.0020 (15)0.0050 (15)0.0142 (15)
C910.0530 (16)0.0403 (14)0.0530 (16)0.0013 (12)0.0208 (13)0.0024 (12)
C920.063 (2)0.0562 (18)0.071 (2)0.0113 (15)0.0147 (16)0.0179 (15)
C1210.0466 (19)0.111 (3)0.082 (2)0.0024 (19)0.0051 (17)0.022 (2)
Geometric parameters (Å, º) top
S1—C21.795 (3)C9A—C101.397 (4)
S1—C151.831 (3)C10—C111.381 (4)
C2—C31.508 (4)C10—H1700.9300
C2—H2A0.9700C11—C121.382 (4)
C2—H2B0.9700C11—H110.9300
C3—O31.214 (4)C12—C131.389 (4)
C3—N41.369 (3)C12—C1211.504 (4)
N4—C4A1.423 (3)C13—C141.389 (4)
N4—C151.452 (3)C13—H130.9300
C4A—C51.385 (4)C14—C151.507 (4)
C4A—C8A1.394 (3)C15—H150.9800
C5—C61.374 (4)C71—H71A0.9600
C5—H50.9300C71—H71B0.9600
C6—C71.382 (4)C71—H71C0.9600
C6—H60.9300C91—C921.516 (4)
C7—C81.391 (4)C91—H91A0.9700
C7—C711.499 (4)C91—H91B0.9700
C8—C8A1.389 (3)C92—H92A0.9600
C8—H80.9300C92—H92B0.9600
C8A—C91.528 (3)C92—H92C0.9600
C9—C911.522 (3)C121—H12A0.9600
C9—C9A1.527 (4)C121—H12B0.9600
C9—H90.9800C121—H12C0.9600
C9A—C141.395 (4)
C2—S1—C1591.50 (14)C10—C11—C12121.5 (3)
C3—C2—S1107.97 (19)C10—C11—H11119.3
C3—C2—H2A110.1C12—C11—H11119.3
S1—C2—H2A110.1C11—C12—C13116.8 (3)
C3—C2—H2B110.1C11—C12—C121122.6 (3)
S1—C2—H2B110.1C13—C12—C121120.6 (3)
H2A—C2—H2B108.4C12—C13—C14122.6 (3)
O3—C3—N4124.5 (3)C12—C13—H13118.7
O3—C3—C2123.8 (3)C14—C13—H13118.7
N4—C3—C2111.7 (3)C13—C14—C9A120.2 (2)
C3—N4—C4A122.1 (2)C13—C14—C15115.2 (2)
C3—N4—C15116.4 (2)C9A—C14—C15124.6 (2)
C4A—N4—C15121.4 (2)N4—C15—C14117.9 (2)
C5—C4A—C8A120.7 (3)N4—C15—S1104.64 (18)
C5—C4A—N4121.5 (2)C14—C15—S1110.88 (19)
C8A—C4A—N4117.8 (2)N4—C15—H15107.7
C6—C5—C4A119.5 (3)C14—C15—H15107.7
C6—C5—H5120.3S1—C15—H15107.7
C4A—C5—H5120.3C7—C71—H71A109.5
C5—C6—C7121.9 (3)C7—C71—H71B109.5
C5—C6—H6119.0H71A—C71—H71B109.5
C7—C6—H6119.0C7—C71—H71C109.5
C6—C7—C8117.6 (3)H71A—C71—H71C109.5
C6—C7—C71122.0 (3)H71B—C71—H71C109.5
C8—C7—C71120.3 (3)C92—C91—C9113.0 (2)
C8A—C8—C7122.2 (2)C92—C91—H91A109.0
C8A—C8—H8118.9C9—C91—H91A109.0
C7—C8—H8118.9C92—C91—H91B109.0
C8—C8A—C4A118.1 (2)C9—C91—H91B109.0
C8—C8A—C9123.3 (2)H91A—C91—H91B107.8
C4A—C8A—C9118.6 (2)C91—C92—H92A109.5
C91—C9—C9A114.8 (2)C91—C92—H92B109.5
C91—C9—C8A114.2 (2)H92A—C92—H92B109.5
C9A—C9—C8A106.0 (2)C91—C92—H92C109.5
C91—C9—H9107.1H92A—C92—H92C109.5
C9A—C9—H9107.1H92B—C92—H92C109.5
C8A—C9—H9107.1C12—C121—H12A109.5
C14—C9A—C10117.0 (2)C12—C121—H12B109.5
C14—C9A—C9120.6 (2)H12A—C121—H12B109.5
C10—C9A—C9122.3 (2)C12—C121—H12C109.5
C11—C10—C9A121.9 (3)H12A—C121—H12C109.5
C11—C10—H170119.1H12B—C121—H12C109.5
C9A—C10—H170119.1
C15—S1—C2—C318.5 (2)C8A—C9—C9A—C1462.2 (3)
S1—C2—C3—O3173.3 (2)C91—C9—C9A—C1013.3 (3)
S1—C2—C3—N46.3 (3)C8A—C9—C9A—C10113.8 (2)
O3—C3—N4—C4A11.8 (4)C14—C9A—C10—C112.2 (4)
C2—C3—N4—C4A167.8 (2)C9—C9A—C10—C11173.9 (2)
O3—C3—N4—C15165.9 (3)C9A—C10—C11—C120.1 (4)
C2—C3—N4—C1514.6 (3)C10—C11—C12—C131.7 (4)
C3—N4—C4A—C565.0 (4)C10—C11—C12—C121178.5 (3)
C15—N4—C4A—C5112.5 (3)C11—C12—C13—C140.9 (4)
C3—N4—C4A—C8A114.9 (3)C121—C12—C13—C14179.2 (3)
C15—N4—C4A—C8A67.6 (3)C12—C13—C14—C9A1.4 (4)
C8A—C4A—C5—C60.2 (4)C12—C13—C14—C15176.5 (2)
N4—C4A—C5—C6179.7 (3)C10—C9A—C14—C132.9 (3)
C4A—C5—C6—C70.8 (5)C9—C9A—C14—C13173.3 (2)
C5—C6—C7—C81.0 (4)C10—C9A—C14—C15174.8 (2)
C5—C6—C7—C71178.0 (3)C9—C9A—C14—C159.0 (4)
C6—C7—C8—C8A0.7 (4)C3—N4—C15—C14151.3 (2)
C71—C7—C8—C8A178.3 (3)C4A—N4—C15—C1431.0 (4)
C7—C8—C8A—C4A0.2 (4)C3—N4—C15—S127.6 (3)
C7—C8—C8A—C9176.4 (2)C4A—N4—C15—S1154.7 (2)
C5—C4A—C8A—C80.1 (4)C13—C14—C15—N4150.7 (2)
N4—C4A—C8A—C8180.0 (2)C9A—C14—C15—N431.5 (4)
C5—C4A—C8A—C9176.8 (2)C13—C14—C15—S188.7 (3)
N4—C4A—C8A—C93.3 (4)C9A—C14—C15—S189.0 (3)
C8—C8A—C9—C9122.9 (3)C2—S1—C15—N425.27 (19)
C4A—C8A—C9—C91160.6 (2)C2—S1—C15—C14153.4 (2)
C8—C8A—C9—C9A104.5 (3)C9A—C9—C91—C92173.0 (2)
C4A—C8A—C9—C9A72.0 (3)C8A—C9—C91—C9264.3 (3)
C91—C9—C9A—C14170.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2B···O3i0.972.573.120 (4)116
C91—H91A···Cg3ii0.972.823.736 (3)157
Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) x+1, y+1, z+1.
(III) Ethyl 2-chloro-13-ethyl-4-oxo-8,13-dihydro-4H-benzo[5,6]azepino[3,2,1-ij]quinoline-5-carboxylate top
Crystal data top
C22H20ClNO3Z = 2
Mr = 381.84F(000) = 400
Triclinic, P1Dx = 1.394 Mg m3
a = 6.8533 (16) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.612 (5) ÅCell parameters from 4176 reflections
c = 13.561 (3) Åθ = 2.9–27.5°
α = 72.45 (4)°µ = 0.23 mm1
β = 75.840 (19)°T = 120 K
γ = 82.46 (2)°Needle, colourless
V = 910.0 (6) Å30.26 × 0.15 × 0.13 mm
Data collection top
Nonius KappaCCD
diffractometer
3776 independent reflections
Radiation source: fine focus sealed tube2195 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.154
φ and ω scansθmax = 26.6°, θmin = 3.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 88
Tmin = 0.845, Tmax = 0.970k = 1313
20183 measured reflectionsl = 1617
Refinement top
Refinement on F274 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.065H-atom parameters constrained
wR(F2) = 0.118 w = 1/[σ2(Fo2) + (0.0192P)2 + 1.1423P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
3776 reflectionsΔρmax = 0.29 e Å3
322 parametersΔρmin = 0.31 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C110.8032 (8)0.3061 (4)0.6534 (3)0.0131 (8)0.900 (6)
H110.82190.23380.71260.016*0.900 (6)
C120.8306 (11)0.2830 (4)0.5549 (3)0.0131 (8)0.900 (6)
Cl120.9006 (7)0.1222 (2)0.5455 (3)0.0224 (4)0.900 (6)
C130.8071 (8)0.3838 (4)0.4674 (3)0.0134 (10)0.900 (6)
H130.83130.36770.40010.016*0.900 (6)
C13A0.7467 (12)0.5117 (5)0.4780 (3)0.0138 (10)0.900 (6)
C140.7273 (10)0.6182 (5)0.3794 (3)0.0128 (11)0.900 (6)
O140.750 (2)0.5900 (6)0.2952 (3)0.0201 (10)0.900 (6)
C150.675 (2)0.7488 (5)0.3946 (4)0.0154 (9)0.900 (6)
C160.623 (2)0.7619 (4)0.4956 (4)0.0146 (12)0.900 (6)
H160.57860.84760.50360.018*0.900 (6)
N170.6312 (15)0.6629 (4)0.5838 (3)0.0129 (7)0.900 (6)
C180.5458 (9)0.6900 (5)0.6874 (4)0.0151 (8)0.900 (6)
H18A0.45000.62220.73180.018*0.900 (6)
H18B0.47080.77770.67610.018*0.900 (6)
C18A0.7098 (10)0.6883 (4)0.7436 (5)0.0147 (9)0.900 (6)
C190.7676 (9)0.8073 (4)0.7489 (6)0.0198 (14)0.900 (6)
H190.69970.88880.71910.024*0.900 (6)
C1100.9232 (11)0.8066 (5)0.7972 (7)0.0250 (13)0.900 (6)
H1100.96680.88770.79790.030*0.900 (6)
C1111.0156 (8)0.6872 (5)0.8449 (5)0.0244 (12)0.900 (6)
H1111.11710.68620.88190.029*0.900 (6)
C1120.9603 (7)0.5682 (5)0.8387 (4)0.0201 (11)0.900 (6)
H1121.02740.48710.86970.024*0.900 (6)
C12A0.8079 (6)0.5675 (4)0.7876 (3)0.0155 (10)0.900 (6)
C1130.7482 (7)0.4385 (4)0.7797 (3)0.0164 (9)0.900 (6)
H1130.85790.37200.80230.020*0.900 (6)
C13C0.7491 (7)0.4319 (4)0.6683 (3)0.0132 (10)0.900 (6)
C1310.5547 (6)0.3870 (4)0.8619 (3)0.0206 (10)0.900 (6)
H13A0.44680.45900.85710.025*0.900 (6)
H13B0.50950.31340.84390.025*0.900 (6)
C1320.5838 (8)0.3386 (6)0.9751 (3)0.0223 (14)0.900 (6)
H13C0.62970.41060.99350.033*0.900 (6)
H13D0.68490.26380.98160.033*0.900 (6)
H13E0.45560.31011.02340.033*0.900 (6)
C13B0.7097 (12)0.5356 (5)0.5784 (3)0.0137 (11)0.900 (6)
C1510.662 (2)0.8739 (5)0.3103 (4)0.0181 (9)0.900 (6)
O1510.6227 (17)0.9825 (6)0.3249 (5)0.0256 (15)0.900 (6)
O1520.707 (4)0.8574 (8)0.2120 (4)0.0237 (10)0.900 (6)
C1520.6960 (10)0.9782 (7)0.1264 (4)0.0234 (16)0.900 (6)
H15A0.78871.04240.12620.028*0.900 (6)
H15B0.55711.01970.13420.028*0.900 (6)
C1530.757 (3)0.9364 (13)0.0249 (5)0.029 (2)0.900 (6)
H15C0.75251.01430.03590.043*0.900 (6)
H15D0.89480.89530.01860.043*0.900 (6)
H15E0.66450.87270.02650.043*0.900 (6)
C210.822 (8)0.330 (3)0.645 (2)0.0131 (8)0.100 (6)
H210.88660.27060.69700.016*0.100 (6)
C220.844 (11)0.307 (2)0.546 (2)0.0131 (8)0.100 (6)
Cl220.889 (7)0.146 (2)0.536 (3)0.0224 (4)0.100 (6)
C230.830 (9)0.410 (3)0.459 (2)0.0134 (10)0.100 (6)
H230.89250.40390.38960.016*0.100 (6)
C23A0.720 (12)0.527 (3)0.474 (2)0.0138 (10)0.100 (6)
C240.694 (12)0.634 (4)0.377 (2)0.0128 (11)0.100 (6)
O240.73 (2)0.607 (5)0.291 (3)0.0201 (10)0.100 (6)
C250.68 (2)0.766 (3)0.390 (3)0.0154 (9)0.100 (6)
C260.64 (2)0.780 (3)0.490 (3)0.0146 (12)0.100 (6)
H260.61030.86750.49740.018*0.100 (6)
N270.630 (14)0.680 (3)0.579 (2)0.0129 (7)0.100 (6)
C280.536 (7)0.710 (4)0.681 (3)0.0151 (8)0.100 (6)
H28A0.42420.65170.71990.018*0.100 (6)
H28B0.47890.80310.66670.018*0.100 (6)
C28A0.689 (9)0.691 (2)0.748 (5)0.0147 (9)0.100 (6)
C290.800 (10)0.797 (3)0.739 (6)0.0198 (14)0.100 (6)
H290.77620.88160.69220.024*0.100 (6)
C2100.945 (11)0.778 (4)0.798 (7)0.0250 (13)0.100 (6)
H2100.99760.85130.80640.030*0.100 (6)
C2111.013 (8)0.650 (5)0.844 (6)0.0244 (12)0.100 (6)
H2111.13230.63450.87100.029*0.100 (6)
C2120.908 (7)0.543 (4)0.850 (4)0.0201 (11)0.100 (6)
H2120.94270.45630.89100.024*0.100 (6)
C22A0.752 (6)0.561 (2)0.798 (3)0.0155 (10)0.100 (6)
C2130.664 (5)0.446 (2)0.7812 (17)0.0164 (9)0.100 (6)
H2230.51600.46940.79700.020*0.100 (6)
C23C0.704 (8)0.441 (3)0.6666 (17)0.0132 (10)0.100 (6)
C2310.684 (5)0.314 (2)0.8666 (19)0.0206 (10)0.100 (6)
H23A0.59200.25180.86330.025*0.100 (6)
H23B0.82380.27480.85120.025*0.100 (6)
C2320.636 (11)0.330 (5)0.9781 (19)0.0223 (14)0.100 (6)
H23C0.63400.24251.02980.033*0.100 (6)
H23D0.50430.37750.99100.033*0.100 (6)
H23E0.73980.38030.98510.033*0.100 (6)
C23B0.679 (13)0.549 (3)0.576 (2)0.0137 (11)0.100 (6)
C2510.66 (2)0.891 (4)0.305 (3)0.0181 (9)0.100 (6)
O2510.592 (18)0.996 (5)0.320 (5)0.0256 (15)0.100 (6)
O2520.70 (4)0.871 (7)0.208 (4)0.0237 (10)0.100 (6)
C2520.649 (14)0.985 (7)0.124 (4)0.0234 (16)0.100 (6)
H25A0.71561.06370.12250.028*0.100 (6)
H25B0.50161.00680.13540.028*0.100 (6)
C2530.73 (3)0.947 (12)0.022 (4)0.029 (2)0.100 (6)
H25C0.70021.02040.03780.043*0.100 (6)
H25D0.87370.92560.01250.043*0.100 (6)
H25E0.66090.86890.02540.043*0.100 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.0130 (16)0.0069 (15)0.0188 (14)0.0051 (16)0.0023 (12)0.0017 (11)
C120.0130 (16)0.0069 (15)0.0188 (14)0.0051 (16)0.0023 (12)0.0017 (11)
Cl120.0303 (8)0.0107 (10)0.0255 (9)0.0016 (10)0.0043 (6)0.0069 (9)
C130.008 (2)0.017 (2)0.0168 (19)0.0060 (19)0.0014 (15)0.0073 (16)
C13A0.010 (3)0.016 (2)0.0157 (18)0.0007 (16)0.0053 (14)0.0035 (15)
C140.008 (4)0.018 (2)0.0136 (17)0.0013 (16)0.0052 (14)0.0046 (15)
O140.024 (3)0.021 (2)0.0164 (13)0.003 (3)0.0057 (12)0.0078 (13)
C150.0154 (19)0.017 (2)0.0115 (17)0.000 (3)0.0043 (16)0.0001 (15)
C160.015 (3)0.012 (2)0.0172 (18)0.001 (3)0.0053 (17)0.0032 (16)
N170.0182 (16)0.0090 (18)0.0106 (14)0.0009 (19)0.0040 (13)0.0014 (12)
C180.0159 (19)0.017 (2)0.0121 (18)0.0032 (17)0.0020 (14)0.0060 (17)
C18A0.014 (2)0.0192 (18)0.0096 (17)0.0003 (14)0.0009 (17)0.0049 (14)
C190.026 (3)0.0171 (19)0.015 (3)0.0041 (18)0.001 (2)0.0049 (17)
C1100.028 (3)0.026 (3)0.024 (2)0.010 (3)0.006 (2)0.009 (3)
C1110.020 (2)0.036 (3)0.025 (2)0.007 (2)0.0062 (17)0.018 (3)
C1120.013 (3)0.027 (3)0.018 (2)0.0031 (19)0.002 (2)0.0055 (19)
C12A0.015 (3)0.0191 (18)0.0097 (18)0.0027 (16)0.0046 (19)0.0055 (15)
C1130.020 (2)0.0177 (19)0.0114 (18)0.0014 (17)0.0055 (17)0.0029 (14)
C13C0.012 (3)0.0152 (18)0.0138 (17)0.0004 (15)0.0044 (15)0.0042 (14)
C1310.026 (2)0.018 (2)0.017 (2)0.0053 (17)0.0030 (17)0.0037 (17)
C1320.027 (4)0.022 (2)0.0172 (19)0.000 (2)0.0055 (18)0.0029 (16)
C13B0.008 (4)0.0157 (19)0.0180 (17)0.0012 (15)0.0036 (15)0.0046 (15)
C1510.0148 (18)0.021 (2)0.0184 (19)0.004 (3)0.0043 (17)0.0037 (17)
O1510.040 (5)0.0151 (18)0.0198 (15)0.0079 (17)0.0102 (16)0.0028 (14)
O1520.039 (4)0.018 (2)0.0124 (13)0.001 (3)0.0069 (15)0.0001 (13)
C1520.030 (5)0.021 (2)0.0154 (18)0.000 (3)0.008 (2)0.0024 (16)
C1530.039 (7)0.030 (3)0.0157 (19)0.016 (3)0.0037 (18)0.0014 (18)
C210.0130 (16)0.0069 (15)0.0188 (14)0.0051 (16)0.0023 (12)0.0017 (11)
C220.0130 (16)0.0069 (15)0.0188 (14)0.0051 (16)0.0023 (12)0.0017 (11)
Cl220.0303 (8)0.0107 (10)0.0255 (9)0.0016 (10)0.0043 (6)0.0069 (9)
C230.008 (2)0.017 (2)0.0168 (19)0.0060 (19)0.0014 (15)0.0073 (16)
C23A0.010 (3)0.016 (2)0.0157 (18)0.0007 (16)0.0053 (14)0.0035 (15)
C240.008 (4)0.018 (2)0.0136 (17)0.0013 (16)0.0052 (14)0.0046 (15)
O240.024 (3)0.021 (2)0.0164 (13)0.003 (3)0.0057 (12)0.0078 (13)
C250.0154 (19)0.017 (2)0.0115 (17)0.000 (3)0.0043 (16)0.0001 (15)
C260.015 (3)0.012 (2)0.0172 (18)0.001 (3)0.0053 (17)0.0032 (16)
N270.0182 (16)0.0090 (18)0.0106 (14)0.0009 (19)0.0040 (13)0.0014 (12)
C280.0159 (19)0.017 (2)0.0121 (18)0.0032 (17)0.0020 (14)0.0060 (17)
C28A0.014 (2)0.0192 (18)0.0096 (17)0.0003 (14)0.0009 (17)0.0049 (14)
C290.026 (3)0.0171 (19)0.015 (3)0.0041 (18)0.001 (2)0.0049 (17)
C2100.028 (3)0.026 (3)0.024 (2)0.010 (3)0.006 (2)0.009 (3)
C2110.020 (2)0.036 (3)0.025 (2)0.007 (2)0.0062 (17)0.018 (3)
C2120.013 (3)0.027 (3)0.018 (2)0.0031 (19)0.002 (2)0.0055 (19)
C22A0.015 (3)0.0191 (18)0.0097 (18)0.0027 (16)0.0046 (19)0.0055 (15)
C2130.020 (2)0.0177 (19)0.0114 (18)0.0014 (17)0.0055 (17)0.0029 (14)
C23C0.012 (3)0.0152 (18)0.0138 (17)0.0004 (15)0.0044 (15)0.0042 (14)
C2310.026 (2)0.018 (2)0.017 (2)0.0053 (17)0.0030 (17)0.0037 (17)
C2320.027 (4)0.022 (2)0.0172 (19)0.000 (2)0.0055 (18)0.0029 (16)
C23B0.008 (4)0.0157 (19)0.0180 (17)0.0012 (15)0.0036 (15)0.0046 (15)
C2510.0148 (18)0.021 (2)0.0184 (19)0.004 (3)0.0043 (17)0.0037 (17)
O2510.040 (5)0.0151 (18)0.0198 (15)0.0079 (17)0.0102 (16)0.0028 (14)
O2520.039 (4)0.018 (2)0.0124 (13)0.001 (3)0.0069 (15)0.0001 (13)
C2520.030 (5)0.021 (2)0.0154 (18)0.000 (3)0.008 (2)0.0024 (16)
C2530.039 (7)0.030 (3)0.0157 (19)0.016 (3)0.0037 (18)0.0014 (18)
Geometric parameters (Å, º) top
C11—C121.393 (5)C21—C23C1.401 (11)
C11—C13C1.399 (5)C21—C221.402 (10)
C11—H110.9500C21—H210.9500
C12—C131.364 (5)C22—C231.364 (10)
C12—Cl121.746 (4)C22—Cl221.740 (10)
C13—C13A1.405 (5)C23—C23A1.406 (11)
C13—H130.9500C23—H230.9500
C13A—C13B1.416 (5)C23A—C23B1.417 (9)
C13A—C141.489 (5)C23A—C241.490 (10)
C14—O141.236 (4)C24—O241.239 (10)
C14—C151.448 (5)C24—C251.450 (11)
C15—C161.374 (5)C25—C261.374 (10)
C15—C1511.477 (5)C25—C2511.478 (10)
C16—N171.340 (5)C26—N271.341 (9)
C16—H160.9500C26—H260.9500
N17—C13B1.403 (4)N27—C23B1.403 (10)
N17—C181.482 (4)N27—C281.484 (10)
C18—C18A1.500 (5)C28—C28A1.502 (10)
C18—H18A0.9900C28—H28A0.9900
C18—H18B0.9900C28—H28B0.9900
C18A—C191.399 (5)C28A—C291.400 (11)
C18A—C12A1.400 (5)C28A—C22A1.405 (9)
C19—C1101.380 (5)C29—C2101.381 (10)
C19—H190.9500C29—H290.9500
C110—C1111.386 (6)C210—C2111.387 (11)
C110—H1100.9500C210—H2100.9500
C111—C1121.396 (6)C211—C2121.396 (11)
C111—H1110.9500C211—H2110.9500
C112—C12A1.389 (5)C212—C22A1.387 (10)
C112—H1120.9500C212—H2120.9500
C12A—C1131.519 (5)C22A—C2131.521 (10)
C113—C13C1.531 (5)C213—C23C1.527 (9)
C113—C1311.550 (5)C213—C2311.540 (10)
C113—H1131.0000C213—H2231.0000
C13C—C13B1.430 (5)C23C—C23B1.438 (9)
C131—C1321.519 (5)C231—C2321.523 (11)
C131—H13A0.9900C231—H23A0.9900
C131—H13B0.9900C231—H23B0.9900
C132—H13C0.9800C232—H23C0.9800
C132—H13D0.9800C232—H23D0.9800
C132—H13E0.9800C232—H23E0.9800
C151—O1511.213 (5)C251—O2511.214 (11)
C151—O1521.352 (4)C251—O2521.354 (11)
O152—C1521.455 (6)O252—C2521.455 (12)
C152—C1531.517 (5)C252—C2531.518 (11)
C152—H15A0.9900C252—H25A0.9900
C152—H15B0.9900C252—H25B0.9900
C153—H15C0.9800C253—H25C0.9800
C153—H15D0.9800C253—H25D0.9800
C153—H15E0.9800C253—H25E0.9800
C12—C11—C13C122.4 (3)H15D—C153—H15E109.5
C12—C11—H11118.8C23C—C21—C22119.8 (13)
C13C—C11—H11118.8C23C—C21—H21120.1
C13—C12—C11121.0 (3)C22—C21—H21120.1
C13—C12—Cl12120.6 (3)C23—C22—C21120.2 (12)
C11—C12—Cl12118.4 (3)C23—C22—Cl22120.5 (12)
C12—C13—C13A119.3 (3)C21—C22—Cl22119.3 (12)
C12—C13—H13120.4C22—C23—C23A118.0 (14)
C13A—C13—H13120.4C22—C23—H23121.0
C13—C13A—C13B120.4 (3)C23A—C23—H23121.0
C13—C13A—C14116.9 (3)C23—C23A—C23B119.3 (16)
C13B—C13A—C14122.7 (3)C23—C23A—C24116.5 (14)
O14—C14—C15126.0 (3)C23B—C23A—C24122.7 (10)
O14—C14—C13A119.8 (3)O24—C24—C25125 (2)
C15—C14—C13A114.2 (3)O24—C24—C23A118.9 (17)
C16—C15—C14119.3 (3)C25—C24—C23A113.5 (13)
C16—C15—C151114.5 (3)C26—C25—C24118.8 (16)
C14—C15—C151126.0 (3)C26—C25—C251114.7 (14)
N17—C16—C15124.8 (4)C24—C25—C251125.3 (18)
N17—C16—H16117.6N27—C26—C25124.9 (13)
C15—C16—H16117.6N27—C26—H26117.5
C16—N17—C13B121.1 (3)C25—C26—H26117.5
C16—N17—C18118.0 (3)C26—N27—C23B121.3 (11)
C13B—N17—C18120.8 (3)C26—N27—C28117.1 (14)
N17—C18—C18A110.7 (3)C23B—N27—C28120.8 (16)
N17—C18—H18A109.5N27—C28—C28A110.5 (15)
C18A—C18—H18A109.5N27—C28—H28A109.5
N17—C18—H18B109.5C28A—C28—H28A109.5
C18A—C18—H18B109.5N27—C28—H28B109.5
H18A—C18—H18B108.1C28A—C28—H28B109.5
C19—C18A—C12A120.6 (3)H28A—C28—H28B108.1
C19—C18A—C18119.9 (3)C29—C28A—C22A120.2 (14)
C12A—C18A—C18119.5 (3)C29—C28A—C28119.8 (15)
C110—C19—C18A120.1 (4)C22A—C28A—C28118.2 (12)
C110—C19—H19120.0C210—C29—C28A119.7 (15)
C18A—C19—H19120.0C210—C29—H29120.2
C19—C110—C111119.8 (4)C28A—C29—H29120.2
C19—C110—H110120.1C29—C210—C211119.0 (15)
C111—C110—H110120.1C29—C210—H210120.5
C110—C111—C112120.3 (4)C211—C210—H210120.5
C110—C111—H111119.8C210—C211—C212120.0 (14)
C112—C111—H111119.8C210—C211—H211120.0
C12A—C112—C111120.6 (4)C212—C211—H211120.0
C12A—C112—H112119.7C22A—C212—C211120.6 (13)
C111—C112—H112119.7C22A—C212—H212119.7
C112—C12A—C18A118.6 (3)C211—C212—H212119.7
C112—C12A—C113120.8 (3)C212—C22A—C28A118.3 (11)
C18A—C12A—C113120.6 (3)C212—C22A—C213122.4 (13)
C12A—C113—C13C116.4 (3)C28A—C22A—C213118.9 (11)
C12A—C113—C131113.0 (3)C22A—C213—C23C115.5 (14)
C13C—C113—C131112.9 (3)C22A—C213—C231113.8 (13)
C12A—C113—H113104.3C23C—C213—C231117.1 (12)
C13C—C113—H113104.3C22A—C213—H223102.5
C131—C113—H113104.3C23C—C213—H223102.5
C11—C13C—C13B116.6 (3)C231—C213—H223102.5
C11—C13C—C113114.0 (3)C21—C23C—C23B115.6 (14)
C13B—C13C—C113129.4 (3)C21—C23C—C213115.6 (12)
C132—C131—C113113.4 (3)C23B—C23C—C213126.8 (11)
C132—C131—H13A108.9C232—C231—C213112.8 (15)
C113—C131—H13A108.9C232—C231—H23A109.0
C132—C131—H13B108.9C213—C231—H23A109.0
C113—C131—H13B108.9C232—C231—H23B109.0
H13A—C131—H13B107.7C213—C231—H23B109.0
C131—C132—H13C109.5H23A—C231—H23B107.8
C131—C132—H13D109.5C231—C232—H23C109.5
H13C—C132—H13D109.5C231—C232—H23D109.5
C131—C132—H13E109.5H23C—C232—H23D109.5
H13C—C132—H13E109.5C231—C232—H23E109.5
H13D—C132—H13E109.5H23C—C232—H23E109.5
N17—C13B—C13A116.7 (3)H23D—C232—H23E109.5
N17—C13B—C13C123.2 (3)N27—C23B—C23A116.5 (11)
C13A—C13B—C13C120.1 (3)N27—C23B—C23C123.4 (13)
O151—C151—O152121.9 (4)C23A—C23B—C23C119.9 (10)
O151—C151—C15124.7 (4)O251—C251—O252121 (2)
O152—C151—C15113.3 (3)O251—C251—C25125 (2)
C151—O152—C152115.2 (4)O252—C251—C25112.5 (15)
O152—C152—C153105.8 (4)C251—O252—C252115.3 (17)
O152—C152—H15A110.6O252—C252—C253105.7 (14)
C153—C152—H15A110.6O252—C252—H25A110.6
O152—C152—H15B110.6C253—C252—H25A110.6
C153—C152—H15B110.6H25A—C252—H25B108.7
H15A—C152—H15B108.7C252—C253—H25C109.5
C152—C153—H15C109.5C252—C253—H25D109.5
C152—C153—H15D109.5H25C—C253—H25D109.5
H15C—C153—H15D109.5C252—C253—H25E109.5
C152—C153—H15E109.5H25D—C253—H25E109.5
H15C—C153—H15E109.5
C13C—C11—C12—C130.6 (7)C15—C151—O152—C152179.9 (16)
C13C—C11—C12—Cl12179.3 (5)C151—O152—C152—C153178.5 (16)
C11—C12—C13—C13A2.5 (8)C23C—C21—C22—C2328 (6)
Cl12—C12—C13—C13A178.7 (6)C23C—C21—C22—Cl22152 (6)
C12—C13—C13A—C13B0.3 (9)C21—C22—C23—C23A24 (7)
C12—C13—C13A—C14178.9 (6)Cl22—C22—C23—C23A155 (6)
C13—C13A—C14—O145.3 (11)C22—C23—C23A—C23B18 (8)
C13B—C13A—C14—O14175.6 (10)C22—C23—C23A—C24175 (6)
C13—C13A—C14—C15176.8 (9)C23—C23A—C24—O2414 (11)
C13B—C13A—C14—C152.3 (9)C23B—C23A—C24—O24180 (9)
O14—C14—C15—C16169.4 (12)C23—C23A—C24—C25150 (8)
C13A—C14—C15—C168.4 (13)C23B—C23A—C24—C2516 (8)
O14—C14—C15—C1517.4 (16)O24—C24—C25—C26179 (12)
C13A—C14—C15—C151174.8 (10)C23A—C24—C25—C2617 (12)
C14—C15—C16—N175.4 (18)O24—C24—C25—C25114 (15)
C151—C15—C16—N17177.5 (11)C23A—C24—C25—C251176 (9)
C15—C16—N17—C13B4.8 (16)C251—C25—C26—N27176 (11)
C15—C16—N17—C18172.5 (11)C25—C26—N27—C23B4 (16)
C16—N17—C18—C18A110.9 (9)C25—C26—N27—C28166 (10)
C13B—N17—C18—C18A71.9 (8)C26—N27—C28—C28A116 (8)
N17—C18—C18A—C19105.6 (7)C23B—N27—C28—C28A74 (6)
N17—C18—C18A—C12A72.5 (6)N27—C28—C28A—C2990 (7)
C12A—C18A—C19—C1100.4 (10)N27—C28—C28A—C22A74 (4)
C18—C18A—C19—C110177.7 (7)C22A—C28A—C29—C21014 (10)
C18A—C19—C110—C1113.0 (11)C28—C28A—C29—C210178 (7)
C19—C110—C111—C1123.8 (11)C28A—C29—C210—C21116 (12)
C110—C111—C112—C12A2.0 (9)C29—C210—C211—C21214 (12)
C111—C112—C12A—C18A0.7 (7)C210—C211—C212—C22A9 (10)
C111—C112—C12A—C113179.4 (5)C211—C212—C22A—C28A7 (8)
C19—C18A—C12A—C1121.5 (8)C211—C212—C22A—C213166 (5)
C18—C18A—C12A—C112179.6 (5)C29—C28A—C22A—C2129 (8)
C19—C18A—C12A—C113178.6 (5)C28—C28A—C22A—C212174 (5)
C18—C18A—C12A—C1130.5 (8)C29—C28A—C22A—C213164 (5)
C112—C12A—C113—C13C126.3 (4)C28—C28A—C22A—C2131 (7)
C18A—C12A—C113—C13C53.8 (6)C212—C22A—C213—C23C112 (5)
C112—C12A—C113—C131100.6 (4)C28A—C22A—C213—C23C60 (4)
C18A—C12A—C113—C13179.3 (6)C212—C22A—C213—C23127 (5)
C12—C11—C13C—C13B4.0 (7)C28A—C22A—C213—C231160 (4)
C12—C11—C13C—C113173.9 (4)C22—C21—C23C—C23B23 (6)
C12A—C113—C13C—C11146.8 (4)C22—C21—C23C—C213171 (3)
C131—C113—C13C—C1180.1 (5)C22A—C213—C23C—C21116 (4)
C12A—C113—C13C—C13B30.8 (7)C231—C213—C23C—C2122 (5)
C131—C113—C13C—C13B102.3 (6)C22A—C213—C23C—C23B47 (6)
C12A—C113—C131—C13269.4 (5)C231—C213—C23C—C23B175 (5)
C13C—C113—C131—C132155.8 (4)C22A—C213—C231—C23242 (5)
C16—N17—C13B—C13A10.6 (12)C23C—C213—C231—C232179 (4)
C18—N17—C13B—C13A166.5 (7)C26—N27—C23B—C23A5 (11)
C16—N17—C13B—C13C170.4 (10)C28—N27—C23B—C23A165 (6)
C18—N17—C13B—C13C12.4 (11)C26—N27—C23B—C23C170 (10)
C13—C13A—C13B—N17174.0 (8)C28—N27—C23B—C23C20 (11)
C14—C13A—C13B—N176.9 (10)C23—C23A—C23B—N27160 (7)
C13—C13A—C13B—C13C5.0 (10)C24—C23A—C23B—N276 (10)
C14—C13A—C13B—C13C174.1 (7)C23—C23A—C23B—C23C15 (9)
C11—C13C—C13B—N17172.2 (7)C24—C23A—C23B—C23C179 (7)
C113—C13C—C13B—N1710.2 (10)C21—C23C—C23B—N27157 (7)
C11—C13C—C13B—C13A6.7 (9)C213—C23C—C23B—N276 (10)
C113—C13C—C13B—C13A170.9 (6)C21—C23C—C23B—C23A18 (8)
C16—C15—C151—O1514.8 (16)C213—C23C—C23B—C23A179 (5)
C14—C15—C151—O151178.3 (15)C24—C25—C251—O251157 (14)
C16—C15—C151—O152177.8 (16)C26—C25—C251—O252177 (15)
C14—C15—C151—O1520.9 (16)C25—C251—O252—C252170 (16)
O151—C151—O152—C1523 (2)C251—O252—C252—C253171 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18B···O151i0.992.543.483 (9)159
C19—H19···O151i0.952.543.396 (12)149
C28—H28B···O251i0.992.103.13 (7)159
C29—H29···O251i0.952.753.38 (13)124
Symmetry code: (i) x+1, y+2, z+1.
Selected geometric parameters (Å, °) top
Ring-puckering parameters(Å, °)
(a)Five-membered ring
(I), molecule 1(I), molecule 2(II)(III), major(III), minor
Q20.4627 (12)0.3979 (12)0.300)3)
φ2359.12 (17)178.1 (2)339.0 (5)
(b)Six-membered ring
Q0.107 (8)0.16 (7)
θ87 (4)112 (26)
φ39 (4)2(30)
(c)Seven-membered rings
Q0.9540 (13)0.942 (2)0.981 (3)0.843 (6)0.85 (5)
φ238.32 (8)217.47 (8)40.16 (16)271.8 (4)267 (4)
φ3286.0 (3)107.8 (3)281.6 (7)9.6 (10)17 (7)
Dihedral angles
(I), molecule 1(I), molecule 2(II)(III), major(III), minor
70.84 (4)65.44 (4)76.67 (9)52.8 (2)66 (3)
Torsion angles
(I), molecule 1(I), molecule 2(II)(III), major(III), minor
Cx9—Cx9—Cx91—Cx92-169.01 (11)170.60 (10)-173.0 (2)
Cy2A—Cy13—Cy31—Cy32-69.4 (5)42 (5)
Notes: (i) x = 1 or 2 for molecules 1 and 2, respectively, in (I) and x = nul for (II); y = 1 or 2 for the major- and minor-disorder forms, respectively, in (III);

(ii) the ring-puckering angles are calculated for the following atom sequences: five-membered rings Sx1–Cx2–Cx3–Nx4–Cx1, six-membered rings Ny7–Cy3B–Cy3A–Cy4–Cy5–Cy6, and seven-membered rings Nx4–Cx4A–Cx8A–Cx9–Cx9A–Cx14–Cx15 in (I) and (II), and Ny7–Cy3B–Cy3C–Cy13–Cy2A–Cy8A–Cy8 in (III);

(iii) the dihedral angles are those between the mean planes of the two aryl rings in each of (I)–(III).
Parameters (Å, °) for hydrogen bonds and short intermolecular contacts top
CompoundD—H···AD—HH···AD···AD—H···A
(I)C115—H115···O13i1.002.473.3084 (18)141
C215—H215···O23ii1.002.373.1681 (18)136
C112—H112···Cg1iii0.952.813.6738 (13)152
C113—H113···Cg2iii0.952.853.7676 (14)163
(II)C2—H2B···O3iv0.972.573.120 (4)116
C91—H91A···Cg3v0.972.823.736 (3)157
(III)C18—H18B···O151vi0.992.543.483 (9)159
C19—H19···O151vi0.952.543.396 (12)149
C28—H28B···O251vi0.992.183.13 (7)159
C29—H29···O251vi0.952.703.34 (12)125
Cg1–Cg3 represent the centroids of the C29A/C210–C214, C24A/C25–C28/C28A and C9A/C10–C14 rings, respectively.

Symmetry codes: (i) -x, y+1/2, -z+1; (ii) -x, y-1/2, -z; (iii) x, y+1, z; (iv) -x+1/2, -y+1/2, -z+1; (v) -x+1, -y+1, -z+1; (vi) -x+1, -y+2, -z+1.
 

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