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(2RS,4SR)-7-Bromo-2-(2-methyl­phenyl)-2,3,4,5-tetra­hydro-1H-naphtho­[1,2-b]azepin-4-ol, C21H20BrNO, (I), and (2RS,4SR)-2-(3-methyl­thio­phen-2-yl)-2,3,4,5-tetra­hydro-1H-naphtho­[1,2-b]azepin-4-ol, C19H19NOS, (II), both crystallize with Z' = 2 in the space groups P21/c and Cc, respectively; compound (II) crystallizes as a nonmerohedral twin, with twin fractions 0.183 (2) and 0.817 (2). The mol­ecules of (I) are linked by O-H...O and O-H...N hydrogen bonds to form a cyclic centrosymmetric R44(16) tetra­mer. The mol­ecules of (II) are linked by O-H...O hydrogen bonds to form a C22(4) chain and these chains are weakly linked by a single C-H...[pi](thienyl) inter­action to form a three-dimensional array. Comparisons are made with some related compounds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113006458/yf3028sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113006458/yf3028Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113006458/yf3028IIsup3.hkl
Contains datablock II

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113006458/yf3028Isup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113006458/yf3028IIsup5.cml
Supplementary material

CCDC references: 934629; 934630

Computing details top

For both compounds, data collection: COLLECT (Nonius, 1998); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

(I) (2RS,4SR)-7-Bromo-2-(2-methylphenyl)-2,3,4,5-tetrahydro-1H-naphtho[1,2-b]azepin-4-ol top
Crystal data top
C21H20BrNOF(000) = 1568
Mr = 382.28Dx = 1.490 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7810 reflections
a = 8.438 (2) Åθ = 2.6–27.5°
b = 24.957 (5) ŵ = 2.42 mm1
c = 16.221 (4) ÅT = 120 K
β = 93.914 (16)°Needle, colourless
V = 3408.2 (14) Å30.41 × 0.14 × 0.08 mm
Z = 8
Data collection top
Bruker Nonius KappaCCD area-detector
diffractometer
7810 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode5959 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.6°
φ and ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 3232
Tmin = 0.437, Tmax = 0.830l = 2121
57203 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0194P)2 + 3.7917P]
where P = (Fo2 + 2Fc2)/3
7810 reflections(Δ/σ)max = 0.001
435 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.47 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.9199 (2)0.31229 (8)0.70667 (12)0.0166 (4)
H110.97780.30400.75460.020*
C120.8324 (3)0.36311 (9)0.72063 (14)0.0157 (5)
H120.72330.35320.73580.019*
C130.8140 (3)0.39754 (10)0.64301 (14)0.0180 (5)
H13A0.77210.43310.65770.022*
H13B0.91990.40310.62170.022*
C140.7040 (3)0.37305 (9)0.57518 (14)0.0164 (5)
H140.59540.36940.59570.020*
O1410.6978 (2)0.41082 (7)0.50792 (10)0.0219 (4)
H1410.61790.40250.47190.033*
C150.7585 (3)0.31843 (9)0.54553 (14)0.0164 (5)
H15A0.69850.31030.49240.020*
H15B0.87200.32130.53420.020*
C15a0.7403 (3)0.27151 (9)0.60320 (14)0.0155 (5)
C160.6438 (3)0.22793 (10)0.57567 (15)0.0183 (5)
H160.57880.23110.52570.022*
C170.6423 (3)0.18132 (10)0.61952 (15)0.0187 (5)
Br170.51606 (3)0.123248 (11)0.575089 (18)0.03112 (8)
C17a0.7345 (3)0.17451 (10)0.69503 (15)0.0181 (5)
C180.7355 (3)0.12633 (11)0.74200 (16)0.0236 (6)
H180.67390.09660.72200.028*
C190.8239 (3)0.12216 (11)0.81539 (16)0.0258 (6)
H190.82210.08990.84640.031*
C1100.9174 (3)0.16548 (11)0.84507 (15)0.0241 (6)
H1100.97960.16220.89590.029*
C1110.9195 (3)0.21235 (10)0.80150 (15)0.0212 (5)
H1110.98370.24120.82260.025*
C11a0.8279 (3)0.21886 (10)0.72534 (14)0.0166 (5)
C11b0.8281 (3)0.26779 (9)0.67842 (14)0.0149 (5)
C1210.9136 (3)0.39247 (10)0.79408 (14)0.0174 (5)
C1220.8733 (3)0.38006 (10)0.87446 (15)0.0217 (5)
C1230.9460 (3)0.40867 (11)0.94080 (16)0.0269 (6)
H1230.91720.40120.99520.032*
C1241.0586 (3)0.44757 (11)0.92907 (16)0.0288 (6)
H1241.10750.46610.97520.035*
C1251.1003 (3)0.45948 (11)0.85000 (17)0.0273 (6)
H1251.17810.48610.84160.033*
C1261.0270 (3)0.43215 (10)0.78277 (15)0.0213 (5)
H1261.05450.44060.72850.026*
C1270.7535 (3)0.33760 (12)0.89181 (16)0.0303 (6)
H17A0.64610.35200.88080.045*
H17B0.76830.32660.94980.045*
H17C0.76810.30660.85610.045*
N210.5851 (2)0.61410 (8)0.60357 (12)0.0155 (4)
H210.52400.62540.64740.019*
C220.7061 (3)0.57388 (9)0.63554 (15)0.0177 (5)
H220.80280.59340.65840.021*
C230.7535 (3)0.53581 (10)0.56797 (16)0.0218 (5)
H23A0.82970.50960.59380.026*
H23B0.65750.51550.54820.026*
C240.8266 (3)0.55878 (10)0.49301 (15)0.0198 (5)
H240.93070.57580.51070.024*
O2410.8530 (2)0.51623 (7)0.43563 (11)0.0287 (4)
H2410.82570.48480.46530.043*
C250.7207 (3)0.60000 (10)0.44745 (15)0.0198 (5)
H25A0.75850.60540.39160.024*
H25B0.61130.58560.44060.024*
C25A0.7167 (3)0.65363 (10)0.49059 (14)0.0173 (5)
C260.7852 (3)0.69819 (10)0.45326 (14)0.0194 (5)
H260.82940.69400.40130.023*
C270.7891 (3)0.74716 (10)0.49059 (15)0.0199 (5)
Br270.88412 (3)0.804103 (11)0.433726 (18)0.03127 (8)
C27A0.7276 (3)0.75580 (10)0.56886 (15)0.0173 (5)
C280.7339 (3)0.80579 (10)0.61050 (16)0.0210 (5)
H280.77750.83600.58470.025*
C290.6781 (3)0.81117 (10)0.68726 (16)0.0236 (6)
H290.68310.84500.71420.028*
C2100.6132 (3)0.76679 (10)0.72657 (16)0.0230 (6)
H2100.57610.77070.78020.028*
C2110.6034 (3)0.71813 (10)0.68783 (15)0.0201 (5)
H2110.55850.68860.71500.024*
C21A0.6590 (3)0.71080 (10)0.60749 (14)0.0162 (5)
C21B0.6530 (3)0.65965 (10)0.56662 (14)0.0163 (5)
C2210.6398 (3)0.54104 (9)0.70425 (15)0.0173 (5)
C2220.7163 (3)0.53879 (10)0.78348 (15)0.0193 (5)
C2230.6570 (3)0.50404 (10)0.84116 (16)0.0243 (6)
H2230.70880.50190.89490.029*
C2240.5245 (3)0.47269 (11)0.82211 (17)0.0272 (6)
H2240.48710.44890.86220.033*
C2250.4463 (3)0.47605 (11)0.74408 (17)0.0268 (6)
H2250.35400.45510.73080.032*
C2260.5038 (3)0.50997 (10)0.68614 (16)0.0223 (6)
H2260.45010.51230.63280.027*
C2270.8599 (3)0.57278 (11)0.80795 (17)0.0285 (6)
H27A0.88800.56850.86720.043*
H27B0.83550.61050.79580.043*
H27C0.94930.56140.77670.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0156 (10)0.0182 (11)0.0154 (10)0.0045 (8)0.0024 (8)0.0002 (8)
C120.0121 (11)0.0189 (13)0.0160 (12)0.0023 (9)0.0006 (9)0.0011 (9)
C130.0189 (12)0.0169 (12)0.0179 (12)0.0004 (10)0.0004 (10)0.0015 (10)
C140.0173 (12)0.0155 (12)0.0162 (12)0.0009 (10)0.0008 (9)0.0051 (10)
O1410.0276 (9)0.0187 (9)0.0180 (9)0.0049 (8)0.0077 (7)0.0056 (7)
C150.0159 (11)0.0201 (13)0.0129 (11)0.0000 (10)0.0002 (9)0.0003 (9)
C15a0.0151 (11)0.0138 (12)0.0179 (12)0.0033 (10)0.0038 (9)0.0003 (10)
C160.0158 (12)0.0218 (13)0.0173 (12)0.0015 (10)0.0001 (10)0.0001 (10)
C170.0173 (12)0.0175 (13)0.0219 (13)0.0021 (10)0.0054 (10)0.0024 (10)
Br170.03116 (15)0.02499 (15)0.03679 (16)0.01140 (12)0.00081 (12)0.00232 (12)
C17a0.0188 (12)0.0184 (13)0.0178 (12)0.0045 (10)0.0061 (10)0.0020 (10)
C180.0219 (13)0.0213 (14)0.0287 (14)0.0035 (11)0.0105 (11)0.0037 (11)
C190.0284 (14)0.0224 (14)0.0280 (14)0.0084 (12)0.0113 (11)0.0100 (12)
C1100.0258 (13)0.0310 (15)0.0158 (12)0.0125 (12)0.0045 (11)0.0069 (11)
C1110.0226 (13)0.0232 (14)0.0178 (12)0.0062 (11)0.0026 (10)0.0003 (10)
C11a0.0161 (11)0.0196 (13)0.0145 (11)0.0051 (10)0.0044 (9)0.0003 (10)
C11b0.0133 (11)0.0172 (12)0.0145 (11)0.0031 (10)0.0033 (9)0.0023 (9)
C1210.0167 (12)0.0191 (13)0.0161 (12)0.0058 (10)0.0015 (10)0.0024 (10)
C1220.0239 (13)0.0231 (14)0.0180 (12)0.0063 (11)0.0017 (10)0.0020 (11)
C1230.0301 (14)0.0336 (16)0.0167 (13)0.0101 (13)0.0004 (11)0.0046 (11)
C1240.0297 (15)0.0325 (16)0.0231 (14)0.0082 (13)0.0069 (12)0.0132 (12)
C1250.0208 (13)0.0252 (15)0.0353 (16)0.0014 (11)0.0018 (12)0.0103 (12)
C1260.0195 (12)0.0242 (14)0.0204 (13)0.0028 (11)0.0031 (10)0.0033 (11)
C1270.0364 (16)0.0358 (17)0.0196 (13)0.0014 (13)0.0087 (12)0.0029 (12)
N210.0131 (9)0.0153 (11)0.0181 (10)0.0012 (8)0.0017 (8)0.0015 (8)
C220.0157 (12)0.0158 (12)0.0214 (13)0.0006 (10)0.0003 (10)0.0007 (10)
C230.0193 (13)0.0177 (13)0.0288 (14)0.0036 (10)0.0054 (11)0.0001 (11)
C240.0179 (12)0.0211 (13)0.0205 (13)0.0028 (10)0.0021 (10)0.0067 (10)
O2410.0292 (10)0.0259 (10)0.0318 (11)0.0043 (8)0.0069 (8)0.0103 (8)
C250.0172 (12)0.0257 (14)0.0163 (12)0.0036 (11)0.0006 (10)0.0053 (10)
C25A0.0140 (11)0.0209 (13)0.0164 (12)0.0046 (10)0.0040 (9)0.0010 (10)
C260.0178 (12)0.0254 (14)0.0150 (12)0.0052 (11)0.0020 (10)0.0026 (11)
C270.0141 (12)0.0244 (14)0.0212 (13)0.0006 (10)0.0008 (10)0.0063 (11)
Br270.03596 (16)0.02612 (15)0.03341 (15)0.00138 (12)0.01467 (12)0.00693 (12)
C27A0.0133 (11)0.0174 (13)0.0209 (13)0.0022 (10)0.0013 (10)0.0026 (10)
C280.0174 (12)0.0177 (13)0.0276 (14)0.0013 (10)0.0009 (10)0.0024 (11)
C290.0226 (13)0.0175 (13)0.0302 (14)0.0006 (11)0.0018 (11)0.0061 (11)
C2100.0240 (13)0.0254 (14)0.0198 (13)0.0001 (11)0.0036 (11)0.0056 (11)
C2110.0222 (13)0.0174 (13)0.0211 (13)0.0026 (10)0.0037 (10)0.0006 (10)
C21A0.0115 (11)0.0190 (13)0.0178 (12)0.0018 (9)0.0022 (9)0.0001 (10)
C21B0.0130 (11)0.0178 (12)0.0176 (12)0.0028 (10)0.0019 (9)0.0012 (10)
C2210.0159 (12)0.0123 (12)0.0242 (13)0.0027 (10)0.0048 (10)0.0014 (10)
C2220.0203 (12)0.0160 (13)0.0217 (13)0.0035 (10)0.0026 (10)0.0018 (10)
C2230.0269 (14)0.0238 (14)0.0223 (13)0.0041 (11)0.0024 (11)0.0009 (11)
C2240.0290 (14)0.0232 (15)0.0305 (15)0.0003 (12)0.0101 (12)0.0062 (12)
C2250.0233 (13)0.0225 (14)0.0353 (16)0.0067 (11)0.0069 (12)0.0020 (12)
C2260.0208 (13)0.0230 (14)0.0233 (13)0.0009 (11)0.0021 (11)0.0024 (11)
C2270.0308 (15)0.0303 (16)0.0237 (14)0.0069 (12)0.0037 (12)0.0016 (12)
Geometric parameters (Å, º) top
N11—C11b1.413 (3)N21—C21B1.424 (3)
N11—C121.493 (3)N21—C221.499 (3)
N11—H110.9128N21—H210.9491
C12—C1211.521 (3)C22—C2211.521 (3)
C12—C131.523 (3)C22—C231.525 (3)
C12—H121.0000C22—H221.0000
C13—C141.519 (3)C23—C241.513 (3)
C13—H13A0.9900C23—H23A0.9900
C13—H13B0.9900C23—H23B0.9900
C14—O1411.440 (3)C24—O2411.439 (3)
C14—C151.527 (3)C24—C251.521 (3)
C14—H141.0000C24—H241.0000
O141—H1410.8865O241—H2410.9572
C15—C15a1.513 (3)C25—C25A1.512 (3)
C15—H15A0.9900C25—H25A0.9900
C15—H15B0.9900C25—H25B0.9900
C15a—C11b1.387 (3)C25A—C21B1.387 (3)
C15a—C161.413 (3)C25A—C261.409 (3)
C16—C171.364 (3)C26—C271.363 (3)
C16—H160.9500C26—H260.9500
C17—C17a1.416 (3)C27—C27A1.420 (3)
C17—Br171.910 (2)C27—Br271.901 (2)
C17a—C181.423 (3)C27A—C281.418 (3)
C17a—C11a1.427 (3)C27A—C21A1.428 (3)
C18—C191.365 (4)C28—C291.367 (4)
C18—H180.9500C28—H280.9500
C19—C1101.404 (4)C29—C2101.407 (4)
C19—H190.9500C29—H290.9500
C110—C1111.367 (4)C210—C2111.367 (3)
C110—H1100.9500C210—H2100.9500
C111—C11a1.421 (3)C211—C21A1.427 (3)
C111—H1110.9500C211—H2110.9500
C11a—C11b1.439 (3)C21A—C21B1.438 (3)
C121—C1261.398 (3)C221—C2261.399 (3)
C121—C1221.404 (3)C221—C2221.399 (3)
C122—C1231.398 (4)C222—C2231.394 (3)
C122—C1271.505 (4)C222—C2271.510 (3)
C123—C1241.381 (4)C223—C2241.382 (4)
C123—H1230.9500C223—H2230.9500
C124—C1251.385 (4)C224—C2251.389 (4)
C124—H1240.9500C224—H2240.9500
C125—C1261.395 (3)C225—C2261.377 (4)
C125—H1250.9500C225—H2250.9500
C126—H1260.9500C226—H2260.9500
C127—H17A0.9800C227—H27A0.9800
C127—H17B0.9800C227—H27B0.9800
C127—H17C0.9800C227—H27C0.9800
C11b—N11—C12116.79 (18)C21B—N21—C22113.33 (18)
C11b—N11—H11110.3C21B—N21—H21109.5
C12—N11—H11107.8C22—N21—H21109.3
N11—C12—C121109.06 (18)N21—C22—C221109.77 (18)
N11—C12—C13112.16 (19)N21—C22—C23112.01 (19)
C121—C12—C13113.0 (2)C221—C22—C23108.6 (2)
N11—C12—H12107.5N21—C22—H22108.8
C121—C12—H12107.5C221—C22—H22108.8
C13—C12—H12107.5C23—C22—H22108.8
C14—C13—C12113.2 (2)C24—C23—C22118.9 (2)
C14—C13—H13A108.9C24—C23—H23A107.6
C12—C13—H13A108.9C22—C23—H23A107.6
C14—C13—H13B108.9C24—C23—H23B107.6
C12—C13—H13B108.9C22—C23—H23B107.6
H13A—C13—H13B107.7H23A—C23—H23B107.0
O141—C14—C13105.92 (18)O241—C24—C23109.3 (2)
O141—C14—C15109.99 (18)O241—C24—C25107.26 (19)
C13—C14—C15113.91 (19)C23—C24—C25112.9 (2)
O141—C14—H14109.0O241—C24—H24109.1
C13—C14—H14109.0C23—C24—H24109.1
C15—C14—H14109.0C25—C24—H24109.1
C14—O141—H141109.5C24—O241—H241103.1
C15a—C15—C14116.78 (19)C25A—C25—C24113.91 (19)
C15a—C15—H15A108.1C25A—C25—H25A108.8
C14—C15—H15A108.1C24—C25—H25A108.8
C15a—C15—H15B108.1C25A—C25—H25B108.8
C14—C15—H15B108.1C24—C25—H25B108.8
H15A—C15—H15B107.3H25A—C25—H25B107.7
C11b—C15a—C16119.2 (2)C21B—C25A—C26119.5 (2)
C11b—C15a—C15121.7 (2)C21B—C25A—C25122.0 (2)
C16—C15a—C15118.8 (2)C26—C25A—C25118.5 (2)
C17—C16—C15a121.2 (2)C27—C26—C25A121.0 (2)
C17—C16—H16119.4C27—C26—H26119.5
C15a—C16—H16119.4C25A—C26—H26119.5
C16—C17—C17a122.0 (2)C26—C27—C27A122.3 (2)
C16—C17—Br17118.37 (19)C26—C27—Br27116.93 (18)
C17a—C17—Br17119.65 (18)C27A—C27—Br27120.81 (19)
C17—C17a—C18123.2 (2)C28—C27A—C27123.7 (2)
C17—C17a—C11a117.6 (2)C28—C27A—C21A119.1 (2)
C18—C17a—C11a119.2 (2)C27—C27A—C21A117.2 (2)
C19—C18—C17a121.0 (3)C29—C28—C27A121.1 (2)
C19—C18—H18119.5C29—C28—H28119.5
C17a—C18—H18119.5C27A—C28—H28119.5
C18—C19—C110120.1 (2)C28—C29—C210120.3 (2)
C18—C19—H19120.0C28—C29—H29119.9
C110—C19—H19120.0C210—C29—H29119.9
C111—C110—C19120.6 (2)C211—C210—C29120.3 (2)
C111—C110—H110119.7C211—C210—H210119.9
C19—C110—H110119.7C29—C210—H210119.9
C110—C111—C11a121.4 (2)C210—C211—C21A121.3 (2)
C110—C111—H111119.3C210—C211—H211119.3
C11a—C111—H111119.3C21A—C211—H211119.3
C111—C11a—C17a117.8 (2)C211—C21A—C27A117.9 (2)
C111—C11a—C11b122.5 (2)C211—C21A—C21B122.1 (2)
C17a—C11a—C11b119.8 (2)C27A—C21A—C21B119.9 (2)
C15a—C11b—N11118.8 (2)C25A—C21B—N21118.6 (2)
C15a—C11b—C11a120.2 (2)C25A—C21B—C21A120.2 (2)
N11—C11b—C11a121.1 (2)N21—C21B—C21A121.2 (2)
C126—C121—C122119.3 (2)C226—C221—C222119.4 (2)
C126—C121—C12121.0 (2)C226—C221—C22118.8 (2)
C122—C121—C12119.7 (2)C222—C221—C22121.7 (2)
C123—C122—C121118.7 (2)C223—C222—C221118.5 (2)
C123—C122—C127118.7 (2)C223—C222—C227119.5 (2)
C121—C122—C127122.5 (2)C221—C222—C227122.0 (2)
C124—C123—C122121.5 (2)C224—C223—C222121.6 (2)
C124—C123—H123119.2C224—C223—H223119.2
C122—C123—H123119.2C222—C223—H223119.2
C123—C124—C125119.9 (2)C223—C224—C225119.7 (2)
C123—C124—H124120.0C223—C224—H224120.1
C125—C124—H124120.0C225—C224—H224120.1
C124—C125—C126119.5 (3)C226—C225—C224119.4 (2)
C124—C125—H125120.3C226—C225—H225120.3
C126—C125—H125120.3C224—C225—H225120.3
C125—C126—C121121.0 (2)C225—C226—C221121.3 (2)
C125—C126—H126119.5C225—C226—H226119.4
C121—C126—H126119.5C221—C226—H226119.4
C122—C127—H17A109.5C222—C227—H27A109.5
C122—C127—H17B109.5C222—C227—H27B109.5
H17A—C127—H17B109.5H27A—C227—H27B109.5
C122—C127—H17C109.5C222—C227—H27C109.5
H17A—C127—H17C109.5H27A—C227—H27C109.5
H17B—C127—H17C109.5H27B—C227—H27C109.5
C11b—N11—C12—C121145.3 (2)C21B—N21—C22—C221155.11 (19)
C11b—N11—C12—C1388.8 (2)C21B—N21—C22—C2384.2 (2)
N11—C12—C13—C1468.2 (2)N21—C22—C23—C2459.9 (3)
C121—C12—C13—C14168.06 (19)C221—C22—C23—C24178.7 (2)
C12—C13—C14—O141178.89 (18)C22—C23—C24—O241176.7 (2)
C12—C13—C14—C1560.1 (3)C22—C23—C24—C2557.4 (3)
O141—C14—C15—C15a168.09 (19)O241—C24—C25—C25A164.6 (2)
C13—C14—C15—C15a73.2 (3)C23—C24—C25—C25A75.0 (3)
C14—C15—C15a—C11b66.8 (3)C24—C25—C25A—C21B65.4 (3)
C14—C15—C15a—C16119.9 (2)C24—C25—C25A—C26112.3 (2)
C11b—C15a—C16—C173.6 (3)C21B—C25A—C26—C270.3 (3)
C15—C15a—C16—C17169.8 (2)C25—C25A—C26—C27178.0 (2)
C15a—C16—C17—C17a1.1 (4)C25A—C26—C27—C27A1.1 (4)
C15a—C16—C17—Br17177.04 (17)C25A—C26—C27—Br27179.76 (17)
C16—C17—C17a—C18179.8 (2)C26—C27—C27A—C28178.1 (2)
Br17—C17—C17a—C181.7 (3)Br27—C27—C27A—C281.0 (3)
C16—C17—C17a—C11a1.3 (3)C26—C27—C27A—C21A0.5 (3)
Br17—C17—C17a—C11a179.42 (16)Br27—C27—C27A—C21A179.67 (17)
C17—C17a—C18—C19178.6 (2)C27—C27A—C28—C29177.4 (2)
C11a—C17a—C18—C190.3 (3)C21A—C27A—C28—C291.2 (4)
C17a—C18—C19—C1100.9 (4)C27A—C28—C29—C2100.1 (4)
C18—C19—C110—C1110.8 (4)C28—C29—C210—C2110.9 (4)
C19—C110—C111—C11a0.1 (4)C29—C210—C211—C21A0.5 (4)
C110—C111—C11a—C17a0.7 (3)C210—C211—C21A—C27A0.8 (4)
C110—C111—C11a—C11b179.9 (2)C210—C211—C21A—C21B178.6 (2)
C17—C17a—C11a—C111179.4 (2)C28—C27A—C21A—C2111.6 (3)
C18—C17a—C11a—C1110.6 (3)C27—C27A—C21A—C211177.1 (2)
C17—C17a—C11a—C11b1.2 (3)C28—C27A—C21A—C21B179.4 (2)
C18—C17a—C11a—C11b179.9 (2)C27—C27A—C21A—C21B0.7 (3)
C16—C15a—C11b—N11177.9 (2)C26—C25A—C21B—N21179.6 (2)
C15—C15a—C11b—N118.9 (3)C25—C25A—C21B—N212.0 (3)
C16—C15a—C11b—C11a3.7 (3)C26—C25A—C21B—C21A0.9 (3)
C15—C15a—C11b—C11a169.6 (2)C25—C25A—C21B—C21A176.7 (2)
C12—N11—C11b—C15a60.9 (3)C22—N21—C21B—C25A71.8 (3)
C12—N11—C11b—C11a120.7 (2)C22—N21—C21B—C21A106.9 (2)
C111—C11a—C11b—C15a178.0 (2)C211—C21A—C21B—C25A176.3 (2)
C17a—C11a—C11b—C15a1.3 (3)C27A—C21A—C21B—C25A1.4 (3)
C111—C11a—C11b—N110.4 (3)C211—C21A—C21B—N212.4 (3)
C17a—C11a—C11b—N11179.7 (2)C27A—C21A—C21B—N21179.9 (2)
N11—C12—C121—C12694.5 (3)N21—C22—C221—C22661.4 (3)
C13—C12—C121—C12630.9 (3)C23—C22—C221—C22661.3 (3)
N11—C12—C121—C12286.2 (3)N21—C22—C221—C222122.3 (2)
C13—C12—C121—C122148.4 (2)C23—C22—C221—C222115.0 (2)
C126—C121—C122—C1231.2 (4)C226—C221—C222—C2232.1 (3)
C12—C121—C122—C123178.1 (2)C22—C221—C222—C223174.1 (2)
C126—C121—C122—C127179.5 (2)C226—C221—C222—C227177.7 (2)
C12—C121—C122—C1271.2 (4)C22—C221—C222—C2276.0 (4)
C121—C122—C123—C1241.7 (4)C221—C222—C223—C2240.8 (4)
C127—C122—C123—C124179.0 (2)C227—C222—C223—C224179.1 (2)
C122—C123—C124—C1250.9 (4)C222—C223—C224—C2250.9 (4)
C123—C124—C125—C1260.4 (4)C223—C224—C225—C2261.2 (4)
C124—C125—C126—C1210.8 (4)C224—C225—C226—C2210.2 (4)
C122—C121—C126—C1250.0 (4)C222—C221—C226—C2251.8 (4)
C12—C121—C126—C125179.3 (2)C22—C221—C226—C225174.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O141—H141···N21i0.892.082.961 (3)174
O241—H241···O1410.962.273.197 (3)163
C28—H28···Cg1ii0.952.983.709 (3)135
C110—H110···Cg2iii0.952.913.673 (3)138
C111—H111···Cg3iii0.952.983.718 (3)136
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y+1/2, z+3/2; (iii) x+2, y1/2, z+3/2.
(II) (2RS,4SR)-2-(3-Methylthiophen-2-yl)-2,3,4,5-tetrahydro-1H-naphtho[1,2-b]azepin-4-ol top
Crystal data top
C19H19NOSF(000) = 1312
Mr = 309.42Dx = 1.273 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 7119 reflections
a = 25.431 (5) Åθ = 2.8–27.5°
b = 16.318 (3) ŵ = 0.20 mm1
c = 8.0193 (6) ÅT = 120 K
β = 104.021 (10)°Rod, pale yellow
V = 3228.8 (9) Å30.34 × 0.17 × 0.14 mm
Z = 8
Data collection top
Bruker Nonius KappaCCD area-detector
diffractometer
7118 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode6110 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.000
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.8°
φ and ω scansh = 3232
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 2121
Tmin = 0.935, Tmax = 0.972l = 910
7118 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.0216P)2 + 3.8102P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max = 0.001
7118 reflectionsΔρmax = 0.39 e Å3
400 parametersΔρmin = 0.28 e Å3
2 restraintsAbsolute structure: Flack (1983), with 3400 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.09 (13)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.48716 (9)0.67480 (14)0.3141 (3)0.0238 (5)
H110.49000.71200.23000.029*
C120.44122 (11)0.70530 (16)0.3809 (4)0.0239 (6)
H120.45640.73110.49550.029*
C130.40359 (11)0.63544 (17)0.4055 (4)0.0261 (6)
H13A0.37160.65930.43750.031*
H13B0.39050.60690.29420.031*
C140.42927 (10)0.57283 (17)0.5405 (4)0.0250 (6)
H140.44400.60240.65110.030*
O1410.38873 (8)0.51583 (12)0.5662 (3)0.0294 (5)
H1410.37110.49260.45970.044*
C150.47569 (11)0.52581 (17)0.4946 (4)0.0252 (6)
H15A0.48200.47470.56310.030*
H15B0.46460.51010.37180.030*
C15a0.52857 (11)0.57310 (16)0.5253 (3)0.0221 (6)
C160.57457 (11)0.54204 (17)0.6459 (4)0.0250 (6)
H160.57090.49410.70950.030*
C170.62394 (11)0.57934 (17)0.6728 (4)0.0262 (6)
H170.65430.55650.75230.031*
C17a0.63015 (11)0.65189 (17)0.5827 (4)0.0234 (6)
C180.68075 (11)0.69296 (18)0.6129 (4)0.0261 (6)
H180.71190.66850.68570.031*
C190.68547 (11)0.76729 (18)0.5387 (4)0.0283 (6)
H190.71950.79440.56170.034*
C1100.63979 (11)0.80354 (18)0.4282 (4)0.0274 (6)
H1100.64300.85570.37890.033*
C1110.59065 (11)0.76401 (17)0.3914 (4)0.0247 (6)
H1110.56050.78870.31420.030*
C11a0.58396 (10)0.68741 (17)0.4661 (3)0.0211 (5)
C11b0.53301 (11)0.64445 (17)0.4362 (3)0.0219 (6)
S1210.36125 (3)0.74292 (5)0.07978 (10)0.0397 (2)
C1220.41056 (11)0.77003 (17)0.2623 (4)0.0264 (6)
C1230.41582 (11)0.85250 (18)0.2770 (4)0.0312 (7)
C1240.37913 (13)0.8946 (2)0.1412 (5)0.0429 (9)
H1240.37690.95260.13300.052*
C1250.34776 (14)0.8437 (2)0.0253 (5)0.0477 (9)
H1250.32160.86150.07370.057*
C1260.45395 (13)0.89584 (17)0.4187 (4)0.0361 (7)
H16A0.47430.85570.50010.054*
H16B0.43350.93170.47820.054*
H16C0.47920.92880.37160.054*
N210.19347 (9)0.31908 (14)0.0322 (3)0.0245 (5)
H210.17920.27930.10770.029*
C220.23738 (11)0.28640 (16)0.1101 (4)0.0256 (6)
H220.22280.28270.21510.031*
C230.28560 (12)0.34501 (18)0.1497 (4)0.0307 (7)
H23A0.31630.31810.23100.037*
H23B0.29700.35610.04230.037*
C240.27348 (12)0.42620 (18)0.2266 (4)0.0318 (7)
H240.26200.41400.33490.038*
O2410.32154 (9)0.47525 (15)0.2707 (3)0.0451 (6)
H2410.34420.47080.19150.068*
C250.22831 (13)0.47587 (17)0.1090 (4)0.0345 (7)
H25A0.23030.53270.15310.041*
H25B0.23570.47800.00650.041*
C25A0.17134 (12)0.44569 (17)0.0892 (4)0.0292 (7)
C260.13307 (14)0.49727 (19)0.1409 (4)0.0350 (7)
H260.14490.54750.19750.042*
C270.07981 (14)0.4761 (2)0.1110 (4)0.0376 (8)
H270.05500.51200.14550.045*
C27A0.06096 (13)0.40160 (19)0.0294 (4)0.0320 (7)
C280.00564 (13)0.3777 (2)0.0033 (4)0.0382 (8)
H280.01990.41380.02700.046*
C290.01150 (13)0.3046 (2)0.0768 (4)0.0414 (8)
H290.04870.29000.09800.050*
C2100.02572 (12)0.2503 (2)0.1218 (4)0.0384 (8)
H2100.01360.19880.17170.046*
C2110.07938 (12)0.27102 (19)0.0942 (4)0.0305 (7)
H2110.10400.23360.12550.037*
C21A0.09872 (12)0.34719 (18)0.0200 (4)0.0271 (6)
C21B0.15463 (12)0.37093 (17)0.0138 (4)0.0251 (6)
S2210.30602 (3)0.18513 (5)0.02813 (9)0.03378 (18)
C2220.25239 (11)0.20151 (17)0.0668 (4)0.0258 (6)
C2230.22791 (12)0.12960 (17)0.0927 (4)0.0293 (6)
C2240.25286 (13)0.06063 (19)0.0322 (4)0.0371 (8)
H2240.24090.00580.03840.045*
C2250.29515 (13)0.0811 (2)0.0349 (5)0.0408 (8)
H2250.31620.04270.08000.049*
C2260.17971 (14)0.1228 (2)0.1688 (4)0.0394 (8)
H26A0.16660.17780.18670.059*
H26B0.19020.09410.27920.059*
H26C0.15090.09210.09030.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0218 (11)0.0271 (12)0.0226 (12)0.0025 (9)0.0054 (9)0.0055 (10)
C120.0248 (14)0.0215 (13)0.0246 (14)0.0009 (11)0.0044 (11)0.0003 (11)
C130.0242 (14)0.0244 (14)0.0321 (16)0.0022 (11)0.0117 (12)0.0021 (12)
C140.0249 (14)0.0223 (13)0.0295 (15)0.0023 (11)0.0098 (12)0.0012 (12)
O1410.0300 (10)0.0249 (10)0.0353 (11)0.0054 (8)0.0118 (9)0.0019 (9)
C150.0297 (14)0.0200 (13)0.0273 (15)0.0013 (11)0.0099 (12)0.0008 (12)
C15a0.0247 (14)0.0214 (13)0.0225 (14)0.0031 (11)0.0100 (11)0.0009 (11)
C160.0301 (15)0.0198 (13)0.0246 (15)0.0055 (11)0.0058 (12)0.0056 (11)
C170.0254 (13)0.0245 (14)0.0267 (15)0.0072 (11)0.0020 (11)0.0015 (12)
C17a0.0248 (13)0.0268 (15)0.0197 (14)0.0032 (11)0.0074 (11)0.0019 (11)
C180.0224 (13)0.0330 (16)0.0213 (14)0.0010 (11)0.0020 (11)0.0048 (12)
C190.0239 (14)0.0379 (17)0.0245 (15)0.0051 (12)0.0089 (11)0.0048 (13)
C1100.0313 (15)0.0279 (15)0.0251 (15)0.0061 (12)0.0109 (12)0.0005 (12)
C1110.0236 (13)0.0256 (14)0.0247 (14)0.0009 (11)0.0057 (11)0.0009 (12)
C11a0.0209 (13)0.0252 (13)0.0182 (13)0.0019 (11)0.0067 (10)0.0027 (11)
C11b0.0233 (13)0.0230 (14)0.0200 (14)0.0047 (11)0.0066 (11)0.0016 (11)
S1210.0305 (4)0.0467 (5)0.0352 (4)0.0051 (4)0.0052 (3)0.0067 (4)
C1220.0214 (14)0.0289 (15)0.0284 (15)0.0006 (12)0.0052 (11)0.0052 (13)
C1230.0239 (14)0.0293 (16)0.0409 (18)0.0016 (13)0.0089 (13)0.0067 (14)
C1240.0331 (17)0.0413 (19)0.055 (2)0.0092 (15)0.0122 (16)0.0229 (18)
C1250.0312 (17)0.058 (2)0.048 (2)0.0059 (16)0.0020 (15)0.0268 (19)
C1260.0475 (19)0.0180 (14)0.043 (2)0.0016 (13)0.0111 (16)0.0026 (14)
N210.0287 (12)0.0253 (12)0.0204 (12)0.0025 (10)0.0080 (10)0.0048 (10)
C220.0280 (14)0.0227 (14)0.0254 (14)0.0023 (11)0.0054 (12)0.0005 (12)
C230.0292 (15)0.0358 (17)0.0276 (16)0.0102 (13)0.0079 (12)0.0069 (13)
C240.0379 (17)0.0327 (16)0.0293 (16)0.0195 (13)0.0169 (13)0.0095 (13)
O2410.0432 (13)0.0558 (15)0.0417 (14)0.0318 (11)0.0208 (11)0.0257 (12)
C250.056 (2)0.0205 (14)0.0280 (16)0.0117 (14)0.0129 (14)0.0034 (13)
C25A0.0457 (18)0.0200 (14)0.0230 (15)0.0003 (13)0.0106 (13)0.0038 (12)
C260.057 (2)0.0218 (14)0.0258 (16)0.0049 (14)0.0100 (15)0.0007 (12)
C270.054 (2)0.0324 (17)0.0265 (16)0.0163 (15)0.0100 (15)0.0026 (13)
C27A0.0410 (17)0.0352 (17)0.0203 (15)0.0113 (14)0.0085 (13)0.0060 (13)
C280.0384 (18)0.051 (2)0.0261 (16)0.0155 (16)0.0104 (14)0.0083 (15)
C290.0271 (16)0.065 (2)0.0323 (18)0.0019 (16)0.0074 (13)0.0075 (17)
C2100.0327 (17)0.049 (2)0.0320 (17)0.0050 (15)0.0058 (14)0.0048 (16)
C2110.0270 (15)0.0398 (17)0.0257 (15)0.0005 (13)0.0087 (12)0.0041 (13)
C21A0.0337 (15)0.0281 (15)0.0201 (15)0.0051 (12)0.0076 (12)0.0035 (12)
C21B0.0359 (16)0.0244 (14)0.0168 (14)0.0021 (12)0.0097 (11)0.0047 (12)
S2210.0232 (3)0.0369 (4)0.0410 (5)0.0038 (3)0.0073 (3)0.0025 (4)
C2220.0223 (13)0.0295 (15)0.0236 (15)0.0006 (11)0.0020 (11)0.0011 (12)
C2230.0357 (16)0.0272 (15)0.0233 (15)0.0004 (13)0.0037 (12)0.0004 (12)
C2240.0412 (18)0.0257 (16)0.0385 (18)0.0066 (14)0.0020 (15)0.0019 (14)
C2250.0348 (18)0.0374 (17)0.045 (2)0.0139 (14)0.0004 (16)0.0033 (16)
C2260.052 (2)0.0316 (17)0.0363 (19)0.0110 (15)0.0147 (15)0.0034 (14)
Geometric parameters (Å, º) top
N11—C11b1.418 (3)N21—C21B1.416 (4)
N11—C121.484 (3)N21—C221.489 (4)
N11—H110.9237N21—H210.9021
C12—C1221.506 (4)C22—C2221.500 (4)
C12—C131.532 (4)C22—C231.527 (4)
C12—H121.0000C22—H221.0000
C13—C141.516 (4)C23—C241.524 (4)
C13—H13A0.9900C23—H23A0.9900
C13—H13B0.9900C23—H23B0.9900
C14—O1411.440 (3)C24—O2411.432 (3)
C14—C151.526 (4)C24—C251.530 (4)
C14—H141.0000C24—H241.0000
O141—H1410.9424O241—H2410.9579
C15—C15a1.518 (4)C25—C25A1.502 (4)
C15—H15A0.9900C25—H25A0.9900
C15—H15B0.9900C25—H25B0.9900
C15a—C11b1.385 (4)C25A—C21B1.382 (4)
C15a—C161.419 (4)C25A—C261.422 (4)
C16—C171.365 (4)C26—C271.362 (5)
C16—H160.9500C26—H260.9500
C17—C17a1.416 (4)C27—C27A1.408 (4)
C17—H170.9500C27—H270.9500
C17a—C181.419 (4)C27A—C281.421 (5)
C17a—C11a1.435 (4)C27A—C21A1.432 (4)
C18—C191.369 (4)C28—C291.356 (5)
C18—H180.9500C28—H280.9500
C19—C1101.409 (4)C29—C2101.406 (5)
C19—H190.9500C29—H290.9500
C110—C1111.373 (4)C210—C2111.371 (4)
C110—H1100.9500C210—H2100.9500
C111—C11a1.414 (4)C211—C21A1.414 (4)
C111—H1110.9500C211—H2110.9500
C11a—C11b1.441 (4)C21A—C21B1.435 (4)
S121—C1251.714 (4)S221—C2251.719 (3)
S121—C1221.738 (3)S221—C2221.736 (3)
C122—C1231.355 (4)C222—C2231.368 (4)
C123—C1241.426 (4)C223—C2241.433 (4)
C123—C1261.483 (4)C223—C2261.500 (4)
C124—C1251.353 (5)C224—C2251.355 (5)
C124—H1240.9500C224—H2240.9500
C125—H1250.9500C225—H2250.9500
C126—H16A0.9800C226—H26A0.9800
C126—H16B0.9800C226—H26B0.9800
C126—H16C0.9800C226—H26C0.9800
C11b—N11—C12117.1 (2)C21B—N21—C22117.1 (2)
C11b—N11—H11122.5C21B—N21—H21114.3
C12—N11—H11104.6C22—N21—H21111.2
N11—C12—C122109.9 (2)N21—C22—C222109.8 (2)
N11—C12—C13111.6 (2)N21—C22—C23110.5 (2)
C122—C12—C13111.0 (2)C222—C22—C23113.0 (2)
N11—C12—H12108.1N21—C22—H22107.8
C122—C12—H12108.1C222—C22—H22107.8
C13—C12—H12108.1C23—C22—H22107.8
C14—C13—C12114.8 (2)C24—C23—C22113.4 (2)
C14—C13—H13A108.6C24—C23—H23A108.9
C12—C13—H13A108.6C22—C23—H23A108.9
C14—C13—H13B108.6C24—C23—H23B108.9
C12—C13—H13B108.6C22—C23—H23B108.9
H13A—C13—H13B107.6H23A—C23—H23B107.7
O141—C14—C13109.8 (2)O241—C24—C23110.0 (2)
O141—C14—C15109.4 (2)O241—C24—C25108.9 (2)
C13—C14—C15113.0 (2)C23—C24—C25114.0 (2)
O141—C14—H14108.2O241—C24—H24107.9
C13—C14—H14108.2C23—C24—H24107.9
C15—C14—H14108.2C25—C24—H24107.9
C14—O141—H141109.3C24—O241—H241114.1
C15a—C15—C14114.3 (2)C25A—C25—C24116.9 (2)
C15a—C15—H15A108.7C25A—C25—H25A108.1
C14—C15—H15A108.7C24—C25—H25A108.1
C15a—C15—H15B108.7C25A—C25—H25B108.1
C14—C15—H15B108.7C24—C25—H25B108.1
H15A—C15—H15B107.6H25A—C25—H25B107.3
C11b—C15a—C16119.7 (2)C21B—C25A—C26119.4 (3)
C11b—C15a—C15121.6 (2)C21B—C25A—C25121.5 (3)
C16—C15a—C15118.7 (2)C26—C25A—C25119.1 (3)
C17—C16—C15a121.6 (3)C27—C26—C25A121.3 (3)
C17—C16—H16119.2C27—C26—H26119.3
C15a—C16—H16119.2C25A—C26—H26119.3
C16—C17—C17a120.3 (3)C26—C27—C27A120.9 (3)
C16—C17—H17119.9C26—C27—H27119.6
C17a—C17—H17119.9C27A—C27—H27119.6
C17—C17a—C18121.1 (3)C27—C27A—C28122.2 (3)
C17—C17a—C11a119.7 (2)C27—C27A—C21A119.2 (3)
C18—C17a—C11a119.1 (3)C28—C27A—C21A118.6 (3)
C19—C18—C17a121.1 (3)C29—C28—C27A121.4 (3)
C19—C18—H18119.5C29—C28—H28119.3
C17a—C18—H18119.5C27A—C28—H28119.3
C18—C19—C110120.0 (3)C28—C29—C210120.1 (3)
C18—C19—H19120.0C28—C29—H29120.0
C110—C19—H19120.0C210—C29—H29120.0
C111—C110—C19120.4 (3)C211—C210—C29120.6 (3)
C111—C110—H110119.8C211—C210—H210119.7
C19—C110—H110119.8C29—C210—H210119.7
C110—C111—C11a121.4 (3)C210—C211—C21A121.1 (3)
C110—C111—H111119.3C210—C211—H211119.5
C11a—C111—H111119.3C21A—C211—H211119.5
C111—C11a—C17a118.0 (2)C211—C21A—C27A118.2 (3)
C111—C11a—C11b123.7 (2)C211—C21A—C21B123.0 (3)
C17a—C11a—C11b118.2 (2)C27A—C21A—C21B118.7 (3)
C15a—C11b—N11119.6 (2)C25A—C21B—N21118.8 (3)
C15a—C11b—C11a120.4 (2)C25A—C21B—C21A120.4 (3)
N11—C11b—C11a120.1 (2)N21—C21B—C21A120.8 (2)
C125—S121—C12291.69 (16)C225—S221—C22291.63 (16)
C123—C122—C12128.1 (3)C223—C222—C22127.3 (3)
C123—C122—S121111.2 (2)C223—C222—S221111.7 (2)
C12—C122—S121120.7 (2)C22—C222—S221121.0 (2)
C122—C123—C124112.3 (3)C222—C223—C224111.5 (3)
C122—C123—C126124.9 (3)C222—C223—C226124.9 (3)
C124—C123—C126122.7 (3)C224—C223—C226123.5 (3)
C125—C124—C123113.3 (3)C225—C224—C223113.6 (3)
C125—C124—H124123.3C225—C224—H224123.2
C123—C124—H124123.3C223—C224—H224123.2
C124—C125—S121111.4 (3)C224—C225—S221111.6 (2)
C124—C125—H125124.3C224—C225—H225124.2
S121—C125—H125124.3S221—C225—H225124.2
C123—C126—H16A109.5C223—C226—H26A109.5
C123—C126—H16B109.5C223—C226—H26B109.5
H16A—C126—H16B109.5H26A—C226—H26B109.5
C123—C126—H16C109.5C223—C226—H26C109.5
H16A—C126—H16C109.5H26A—C226—H26C109.5
H16B—C126—H16C109.5H26B—C226—H26C109.5
C11b—N11—C12—C122152.0 (2)C21B—N21—C22—C222145.6 (2)
C11b—N11—C12—C1384.4 (3)C21B—N21—C22—C2389.1 (3)
N11—C12—C13—C1464.5 (3)N21—C22—C23—C2467.5 (3)
C122—C12—C13—C14172.5 (2)C222—C22—C23—C24169.0 (3)
C12—C13—C14—O141173.4 (2)C22—C23—C24—O241176.1 (2)
C12—C13—C14—C1564.1 (3)C22—C23—C24—C2561.2 (3)
O141—C14—C15—C15a159.5 (2)O241—C24—C25—C25A163.0 (2)
C13—C14—C15—C15a77.9 (3)C23—C24—C25—C25A73.8 (3)
C14—C15—C15a—C11b63.3 (3)C24—C25—C25A—C21B64.4 (4)
C14—C15—C15a—C16118.1 (3)C24—C25—C25A—C26119.0 (3)
C11b—C15a—C16—C172.2 (4)C21B—C25A—C26—C272.9 (5)
C15—C15a—C16—C17176.5 (3)C25—C25A—C26—C27173.8 (3)
C15a—C16—C17—C17a1.5 (4)C25A—C26—C27—C27A0.8 (5)
C16—C17—C17a—C18178.0 (3)C26—C27—C27A—C28179.9 (3)
C16—C17—C17a—C11a1.6 (4)C26—C27—C27A—C21A0.9 (4)
C17—C17a—C18—C19173.4 (3)C27—C27A—C28—C29177.8 (3)
C11a—C17a—C18—C193.0 (4)C21A—C27A—C28—C291.2 (5)
C17a—C18—C19—C1101.0 (4)C27A—C28—C29—C2100.3 (5)
C18—C19—C110—C1111.3 (4)C28—C29—C210—C2110.9 (5)
C19—C110—C111—C11a1.7 (4)C29—C210—C211—C21A0.1 (5)
C110—C111—C11a—C17a0.2 (4)C210—C211—C21A—C27A1.4 (4)
C110—C111—C11a—C11b178.0 (3)C210—C211—C21A—C21B179.0 (3)
C17—C17a—C11a—C111173.9 (3)C27—C27A—C21A—C211177.0 (3)
C18—C17a—C11a—C1112.5 (4)C28—C27A—C21A—C2112.0 (4)
C17—C17a—C11a—C11b4.0 (4)C27—C27A—C21A—C21B0.7 (4)
C18—C17a—C11a—C11b179.5 (2)C28—C27A—C21A—C21B179.7 (3)
C16—C15a—C11b—N11179.2 (2)C26—C25A—C21B—N21178.0 (3)
C15—C15a—C11b—N110.5 (4)C25—C25A—C21B—N215.4 (4)
C16—C15a—C11b—C11a0.4 (4)C26—C25A—C21B—C21A3.1 (4)
C15—C15a—C11b—C11a179.0 (2)C25—C25A—C21B—C21A173.5 (3)
C12—N11—C11b—C15a67.3 (3)C22—N21—C21B—C25A64.8 (3)
C12—N11—C11b—C11a113.2 (3)C22—N21—C21B—C21A116.4 (3)
C111—C11a—C11b—C15a174.4 (3)C211—C21A—C21B—C25A179.0 (3)
C17a—C11a—C11b—C15a3.4 (4)C27A—C21A—C21B—C25A1.3 (4)
C111—C11a—C11b—N116.0 (4)C211—C21A—C21B—N212.2 (4)
C17a—C11a—C11b—N11176.2 (2)C27A—C21A—C21B—N21179.8 (3)
N11—C12—C122—C12396.6 (4)N21—C22—C222—C22384.9 (3)
C13—C12—C122—C123139.5 (3)C23—C22—C222—C223151.2 (3)
N11—C12—C122—S12183.4 (3)N21—C22—C222—S22194.8 (3)
C13—C12—C122—S12140.5 (3)C23—C22—C222—S22129.1 (3)
C125—S121—C122—C1230.4 (3)C225—S221—C222—C2230.5 (2)
C125—S121—C122—C12179.6 (3)C225—S221—C222—C22179.3 (2)
C12—C122—C123—C124179.0 (3)C22—C222—C223—C224179.0 (3)
S121—C122—C123—C1241.0 (3)S221—C222—C223—C2240.8 (3)
C12—C122—C123—C1260.5 (5)C22—C222—C223—C2261.1 (5)
S121—C122—C123—C126179.5 (3)S221—C222—C223—C226178.7 (2)
C122—C123—C124—C1251.2 (4)C222—C223—C224—C2250.8 (4)
C126—C123—C124—C125179.8 (3)C226—C223—C224—C225178.7 (3)
C123—C124—C125—S1210.9 (4)C223—C224—C225—S2210.4 (4)
C122—S121—C125—C1240.3 (3)C222—S221—C225—C2240.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O141—H141···O2410.941.742.648 (3)160
O241—H241···O141i0.961.702.644 (3)167
C18—H18···Cg4ii0.952.813.640 (3)146
C110—H110···Cg2iii0.952.713.464 (3)137
C111—H111···Cg3iii0.952.893.578 (3)130
Symmetry codes: (i) x, y+1, z1/2; (ii) x+1/2, y+1/2, z+1; (iii) x+1/2, y+1/2, z.
Selected geometric parameters (Å, °) for compounds (I) and (II) top
Parameter(I)(II)
x = 1x = 2x = 1x = 2
(i) Puckering parameters for seven-membered rings
Q0.746 (2)0.785 (2)0.756 (3)0.748 (3)
φ2188.6 (4)203.7 (3)204.1 (4)191.5 (5)
φ3126.9 (2)129.9 (2)127.9 (3)128.3 (3)
(ii) Torsion angles
Mx1—Cx2—Cx21—Cx22-86.2 (3)-122.3 (2)
Mx1—Cx2—Cx22—Cx23-96.6 (4)-84.9 (3)
Puckering parameters for seven-membered rings are defined for the atom sequence Nx1–Cx1B–Cx5A–Cx5–Cx4–Cx3–Cx2.
Parameters (Å, °) for hydrogen bonds and short intermolecular contacts in compounds (I) and (II) top
CompoundD—H···AD—HH···AD···AD—H···A
(I)O141—H141···N21i0.892.082.961 (3)174
O241—H241···O1410.962.273.197 (3)163
C28—H28···Cg1ii0.952.983.709 (3)135
C110—H110···Cg2iii0.952.913.673 (3)138
C111—H111···Cg3iii0.952.983.718 (3)136
(II)O141—H141···O2410.941.742.648 (3)160
O241—H241···O141iv0.961.702.644 (3)167
C18—H18···Cg4v0.952.813.640 (3)146
C110—H110···Cg2vi0.952.713.464 (3)137
C111—H111···Cg3vi0.952.893.578 (3)130
Cg1 represents the centroid of the C121–C126 ring, Cg2 the centroid of the C21A/C21B/C25A/C26/C27/C27A ring, Cg3 the centroid of the C21A/C27A/C28/C29/C210/C211 ring and Cg4 the centroid of the S221/C222–C225 ring.

Symmetry codes: (i) -x + 1, -y + 1, -z + 1; (ii) -x + 2, y + 1/2, -z + 3/2; (iii) -x + 2, y - 1/2, -z + 3/2; (iv) x, -y + 1, z - 1/2; (v) x + 1/2, y + 1/2, z + 1; (vi) x + 1/2, y + 1/2, z.
 

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