(2
RS,4
SR)-7-Bromo-2-(2-methylphenyl)-2,3,4,5-tetrahydro-1
H-naphtho[1,2-
b]azepin-4-ol, C
21H
20BrNO, (I), and (2
RS,4
SR)-2-(3-methylthiophen-2-yl)-2,3,4,5-tetrahydro-1
H-naphtho[1,2-
b]azepin-4-ol, C
19H
19NOS, (II), both crystallize with
Z' = 2 in the space groups
P2
1/
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
(thienyl) interaction to form a three-dimensional array. Comparisons are made with some related compounds.
Supporting information
CCDC references: 934629; 934630
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) (2
RS,4
SR)-7-Bromo-2-(2-methylphenyl)-2,3,4,5-tetrahydro-1
H-naphtho[1,2-
b]azepin-4-ol
top
Crystal data top
C21H20BrNO | F(000) = 1568 |
Mr = 382.28 | Dx = 1.490 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 7810 reflections |
a = 8.438 (2) Å | θ = 2.6–27.5° |
b = 24.957 (5) Å | µ = 2.42 mm−1 |
c = 16.221 (4) Å | T = 120 K |
β = 93.914 (16)° | Needle, colourless |
V = 3408.2 (14) Å3 | 0.41 × 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 anode | 5959 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 2.6° |
φ and ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | k = −32→32 |
Tmin = 0.437, Tmax = 0.830 | l = −21→21 |
57203 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.075 | H-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 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N11 | 0.9199 (2) | 0.31229 (8) | 0.70667 (12) | 0.0166 (4) | |
H11 | 0.9778 | 0.3040 | 0.7546 | 0.020* | |
C12 | 0.8324 (3) | 0.36311 (9) | 0.72063 (14) | 0.0157 (5) | |
H12 | 0.7233 | 0.3532 | 0.7358 | 0.019* | |
C13 | 0.8140 (3) | 0.39754 (10) | 0.64301 (14) | 0.0180 (5) | |
H13A | 0.7721 | 0.4331 | 0.6577 | 0.022* | |
H13B | 0.9199 | 0.4031 | 0.6217 | 0.022* | |
C14 | 0.7040 (3) | 0.37305 (9) | 0.57518 (14) | 0.0164 (5) | |
H14 | 0.5954 | 0.3694 | 0.5957 | 0.020* | |
O141 | 0.6978 (2) | 0.41082 (7) | 0.50792 (10) | 0.0219 (4) | |
H141 | 0.6179 | 0.4025 | 0.4719 | 0.033* | |
C15 | 0.7585 (3) | 0.31843 (9) | 0.54553 (14) | 0.0164 (5) | |
H15A | 0.6985 | 0.3103 | 0.4924 | 0.020* | |
H15B | 0.8720 | 0.3213 | 0.5342 | 0.020* | |
C15a | 0.7403 (3) | 0.27151 (9) | 0.60320 (14) | 0.0155 (5) | |
C16 | 0.6438 (3) | 0.22793 (10) | 0.57567 (15) | 0.0183 (5) | |
H16 | 0.5788 | 0.2311 | 0.5257 | 0.022* | |
C17 | 0.6423 (3) | 0.18132 (10) | 0.61952 (15) | 0.0187 (5) | |
Br17 | 0.51606 (3) | 0.123248 (11) | 0.575089 (18) | 0.03112 (8) | |
C17a | 0.7345 (3) | 0.17451 (10) | 0.69503 (15) | 0.0181 (5) | |
C18 | 0.7355 (3) | 0.12633 (11) | 0.74200 (16) | 0.0236 (6) | |
H18 | 0.6739 | 0.0966 | 0.7220 | 0.028* | |
C19 | 0.8239 (3) | 0.12216 (11) | 0.81539 (16) | 0.0258 (6) | |
H19 | 0.8221 | 0.0899 | 0.8464 | 0.031* | |
C110 | 0.9174 (3) | 0.16548 (11) | 0.84507 (15) | 0.0241 (6) | |
H110 | 0.9796 | 0.1622 | 0.8959 | 0.029* | |
C111 | 0.9195 (3) | 0.21235 (10) | 0.80150 (15) | 0.0212 (5) | |
H111 | 0.9837 | 0.2412 | 0.8226 | 0.025* | |
C11a | 0.8279 (3) | 0.21886 (10) | 0.72534 (14) | 0.0166 (5) | |
C11b | 0.8281 (3) | 0.26779 (9) | 0.67842 (14) | 0.0149 (5) | |
C121 | 0.9136 (3) | 0.39247 (10) | 0.79408 (14) | 0.0174 (5) | |
C122 | 0.8733 (3) | 0.38006 (10) | 0.87446 (15) | 0.0217 (5) | |
C123 | 0.9460 (3) | 0.40867 (11) | 0.94080 (16) | 0.0269 (6) | |
H123 | 0.9172 | 0.4012 | 0.9952 | 0.032* | |
C124 | 1.0586 (3) | 0.44757 (11) | 0.92907 (16) | 0.0288 (6) | |
H124 | 1.1075 | 0.4661 | 0.9752 | 0.035* | |
C125 | 1.1003 (3) | 0.45948 (11) | 0.85000 (17) | 0.0273 (6) | |
H125 | 1.1781 | 0.4861 | 0.8416 | 0.033* | |
C126 | 1.0270 (3) | 0.43215 (10) | 0.78277 (15) | 0.0213 (5) | |
H126 | 1.0545 | 0.4406 | 0.7285 | 0.026* | |
C127 | 0.7535 (3) | 0.33760 (12) | 0.89181 (16) | 0.0303 (6) | |
H17A | 0.6461 | 0.3520 | 0.8808 | 0.045* | |
H17B | 0.7683 | 0.3266 | 0.9498 | 0.045* | |
H17C | 0.7681 | 0.3066 | 0.8561 | 0.045* | |
N21 | 0.5851 (2) | 0.61410 (8) | 0.60357 (12) | 0.0155 (4) | |
H21 | 0.5240 | 0.6254 | 0.6474 | 0.019* | |
C22 | 0.7061 (3) | 0.57388 (9) | 0.63554 (15) | 0.0177 (5) | |
H22 | 0.8028 | 0.5934 | 0.6584 | 0.021* | |
C23 | 0.7535 (3) | 0.53581 (10) | 0.56797 (16) | 0.0218 (5) | |
H23A | 0.8297 | 0.5096 | 0.5938 | 0.026* | |
H23B | 0.6575 | 0.5155 | 0.5482 | 0.026* | |
C24 | 0.8266 (3) | 0.55878 (10) | 0.49301 (15) | 0.0198 (5) | |
H24 | 0.9307 | 0.5758 | 0.5107 | 0.024* | |
O241 | 0.8530 (2) | 0.51623 (7) | 0.43563 (11) | 0.0287 (4) | |
H241 | 0.8257 | 0.4848 | 0.4653 | 0.043* | |
C25 | 0.7207 (3) | 0.60000 (10) | 0.44745 (15) | 0.0198 (5) | |
H25A | 0.7585 | 0.6054 | 0.3916 | 0.024* | |
H25B | 0.6113 | 0.5856 | 0.4406 | 0.024* | |
C25A | 0.7167 (3) | 0.65363 (10) | 0.49059 (14) | 0.0173 (5) | |
C26 | 0.7852 (3) | 0.69819 (10) | 0.45326 (14) | 0.0194 (5) | |
H26 | 0.8294 | 0.6940 | 0.4013 | 0.023* | |
C27 | 0.7891 (3) | 0.74716 (10) | 0.49059 (15) | 0.0199 (5) | |
Br27 | 0.88412 (3) | 0.804103 (11) | 0.433726 (18) | 0.03127 (8) | |
C27A | 0.7276 (3) | 0.75580 (10) | 0.56886 (15) | 0.0173 (5) | |
C28 | 0.7339 (3) | 0.80579 (10) | 0.61050 (16) | 0.0210 (5) | |
H28 | 0.7775 | 0.8360 | 0.5847 | 0.025* | |
C29 | 0.6781 (3) | 0.81117 (10) | 0.68726 (16) | 0.0236 (6) | |
H29 | 0.6831 | 0.8450 | 0.7142 | 0.028* | |
C210 | 0.6132 (3) | 0.76679 (10) | 0.72657 (16) | 0.0230 (6) | |
H210 | 0.5761 | 0.7707 | 0.7802 | 0.028* | |
C211 | 0.6034 (3) | 0.71813 (10) | 0.68783 (15) | 0.0201 (5) | |
H211 | 0.5585 | 0.6886 | 0.7150 | 0.024* | |
C21A | 0.6590 (3) | 0.71080 (10) | 0.60749 (14) | 0.0162 (5) | |
C21B | 0.6530 (3) | 0.65965 (10) | 0.56662 (14) | 0.0163 (5) | |
C221 | 0.6398 (3) | 0.54104 (9) | 0.70425 (15) | 0.0173 (5) | |
C222 | 0.7163 (3) | 0.53879 (10) | 0.78348 (15) | 0.0193 (5) | |
C223 | 0.6570 (3) | 0.50404 (10) | 0.84116 (16) | 0.0243 (6) | |
H223 | 0.7088 | 0.5019 | 0.8949 | 0.029* | |
C224 | 0.5245 (3) | 0.47269 (11) | 0.82211 (17) | 0.0272 (6) | |
H224 | 0.4871 | 0.4489 | 0.8622 | 0.033* | |
C225 | 0.4463 (3) | 0.47605 (11) | 0.74408 (17) | 0.0268 (6) | |
H225 | 0.3540 | 0.4551 | 0.7308 | 0.032* | |
C226 | 0.5038 (3) | 0.50997 (10) | 0.68614 (16) | 0.0223 (6) | |
H226 | 0.4501 | 0.5123 | 0.6328 | 0.027* | |
C227 | 0.8599 (3) | 0.57278 (11) | 0.80795 (17) | 0.0285 (6) | |
H27A | 0.8880 | 0.5685 | 0.8672 | 0.043* | |
H27B | 0.8355 | 0.6105 | 0.7958 | 0.043* | |
H27C | 0.9493 | 0.5614 | 0.7767 | 0.043* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N11 | 0.0156 (10) | 0.0182 (11) | 0.0154 (10) | 0.0045 (8) | −0.0024 (8) | 0.0002 (8) |
C12 | 0.0121 (11) | 0.0189 (13) | 0.0160 (12) | 0.0023 (9) | 0.0006 (9) | −0.0011 (9) |
C13 | 0.0189 (12) | 0.0169 (12) | 0.0179 (12) | −0.0004 (10) | −0.0004 (10) | 0.0015 (10) |
C14 | 0.0173 (12) | 0.0155 (12) | 0.0162 (12) | 0.0009 (10) | −0.0008 (9) | 0.0051 (10) |
O141 | 0.0276 (9) | 0.0187 (9) | 0.0180 (9) | −0.0049 (8) | −0.0077 (7) | 0.0056 (7) |
C15 | 0.0159 (11) | 0.0201 (13) | 0.0129 (11) | 0.0000 (10) | −0.0002 (9) | 0.0003 (9) |
C15a | 0.0151 (11) | 0.0138 (12) | 0.0179 (12) | 0.0033 (10) | 0.0038 (9) | −0.0003 (10) |
C16 | 0.0158 (12) | 0.0218 (13) | 0.0173 (12) | 0.0015 (10) | 0.0001 (10) | −0.0001 (10) |
C17 | 0.0173 (12) | 0.0175 (13) | 0.0219 (13) | −0.0021 (10) | 0.0054 (10) | −0.0024 (10) |
Br17 | 0.03116 (15) | 0.02499 (15) | 0.03679 (16) | −0.01140 (12) | −0.00081 (12) | 0.00232 (12) |
C17a | 0.0188 (12) | 0.0184 (13) | 0.0178 (12) | 0.0045 (10) | 0.0061 (10) | 0.0020 (10) |
C18 | 0.0219 (13) | 0.0213 (14) | 0.0287 (14) | 0.0035 (11) | 0.0105 (11) | 0.0037 (11) |
C19 | 0.0284 (14) | 0.0224 (14) | 0.0280 (14) | 0.0084 (12) | 0.0113 (11) | 0.0100 (12) |
C110 | 0.0258 (13) | 0.0310 (15) | 0.0158 (12) | 0.0125 (12) | 0.0045 (11) | 0.0069 (11) |
C111 | 0.0226 (13) | 0.0232 (14) | 0.0178 (12) | 0.0062 (11) | 0.0026 (10) | −0.0003 (10) |
C11a | 0.0161 (11) | 0.0196 (13) | 0.0145 (11) | 0.0051 (10) | 0.0044 (9) | 0.0003 (10) |
C11b | 0.0133 (11) | 0.0172 (12) | 0.0145 (11) | 0.0031 (10) | 0.0033 (9) | −0.0023 (9) |
C121 | 0.0167 (12) | 0.0191 (13) | 0.0161 (12) | 0.0058 (10) | −0.0015 (10) | −0.0024 (10) |
C122 | 0.0239 (13) | 0.0231 (14) | 0.0180 (12) | 0.0063 (11) | 0.0017 (10) | −0.0020 (11) |
C123 | 0.0301 (14) | 0.0336 (16) | 0.0167 (13) | 0.0101 (13) | 0.0004 (11) | −0.0046 (11) |
C124 | 0.0297 (15) | 0.0325 (16) | 0.0231 (14) | 0.0082 (13) | −0.0069 (12) | −0.0132 (12) |
C125 | 0.0208 (13) | 0.0252 (15) | 0.0353 (16) | 0.0014 (11) | −0.0018 (12) | −0.0103 (12) |
C126 | 0.0195 (12) | 0.0242 (14) | 0.0204 (13) | 0.0028 (11) | 0.0031 (10) | −0.0033 (11) |
C127 | 0.0364 (16) | 0.0358 (17) | 0.0196 (13) | −0.0014 (13) | 0.0087 (12) | 0.0029 (12) |
N21 | 0.0131 (9) | 0.0153 (11) | 0.0181 (10) | 0.0012 (8) | 0.0017 (8) | −0.0015 (8) |
C22 | 0.0157 (12) | 0.0158 (12) | 0.0214 (13) | −0.0006 (10) | 0.0003 (10) | −0.0007 (10) |
C23 | 0.0193 (13) | 0.0177 (13) | 0.0288 (14) | 0.0036 (10) | 0.0054 (11) | −0.0001 (11) |
C24 | 0.0179 (12) | 0.0211 (13) | 0.0205 (13) | 0.0028 (10) | 0.0021 (10) | −0.0067 (10) |
O241 | 0.0292 (10) | 0.0259 (10) | 0.0318 (11) | 0.0043 (8) | 0.0069 (8) | −0.0103 (8) |
C25 | 0.0172 (12) | 0.0257 (14) | 0.0163 (12) | 0.0036 (11) | −0.0006 (10) | −0.0053 (10) |
C25A | 0.0140 (11) | 0.0209 (13) | 0.0164 (12) | 0.0046 (10) | −0.0040 (9) | −0.0010 (10) |
C26 | 0.0178 (12) | 0.0254 (14) | 0.0150 (12) | 0.0052 (11) | 0.0020 (10) | 0.0026 (11) |
C27 | 0.0141 (12) | 0.0244 (14) | 0.0212 (13) | 0.0006 (10) | 0.0008 (10) | 0.0063 (11) |
Br27 | 0.03596 (16) | 0.02612 (15) | 0.03341 (15) | −0.00138 (12) | 0.01467 (12) | 0.00693 (12) |
C27A | 0.0133 (11) | 0.0174 (13) | 0.0209 (13) | 0.0022 (10) | −0.0013 (10) | 0.0026 (10) |
C28 | 0.0174 (12) | 0.0177 (13) | 0.0276 (14) | −0.0013 (10) | −0.0009 (10) | 0.0024 (11) |
C29 | 0.0226 (13) | 0.0175 (13) | 0.0302 (14) | 0.0006 (11) | −0.0018 (11) | −0.0061 (11) |
C210 | 0.0240 (13) | 0.0254 (14) | 0.0198 (13) | −0.0001 (11) | 0.0036 (11) | −0.0056 (11) |
C211 | 0.0222 (13) | 0.0174 (13) | 0.0211 (13) | −0.0026 (10) | 0.0037 (10) | −0.0006 (10) |
C21A | 0.0115 (11) | 0.0190 (13) | 0.0178 (12) | 0.0018 (9) | −0.0022 (9) | 0.0001 (10) |
C21B | 0.0130 (11) | 0.0178 (12) | 0.0176 (12) | 0.0028 (10) | −0.0019 (9) | −0.0012 (10) |
C221 | 0.0159 (12) | 0.0123 (12) | 0.0242 (13) | 0.0027 (10) | 0.0048 (10) | −0.0014 (10) |
C222 | 0.0203 (12) | 0.0160 (13) | 0.0217 (13) | 0.0035 (10) | 0.0026 (10) | −0.0018 (10) |
C223 | 0.0269 (14) | 0.0238 (14) | 0.0223 (13) | 0.0041 (11) | 0.0024 (11) | 0.0009 (11) |
C224 | 0.0290 (14) | 0.0232 (15) | 0.0305 (15) | 0.0003 (12) | 0.0101 (12) | 0.0062 (12) |
C225 | 0.0233 (13) | 0.0225 (14) | 0.0353 (16) | −0.0067 (11) | 0.0069 (12) | −0.0020 (12) |
C226 | 0.0208 (13) | 0.0230 (14) | 0.0233 (13) | 0.0009 (11) | 0.0021 (11) | −0.0024 (11) |
C227 | 0.0308 (15) | 0.0303 (16) | 0.0237 (14) | −0.0069 (12) | −0.0037 (12) | −0.0016 (12) |
Geometric parameters (Å, º) top
N11—C11b | 1.413 (3) | N21—C21B | 1.424 (3) |
N11—C12 | 1.493 (3) | N21—C22 | 1.499 (3) |
N11—H11 | 0.9128 | N21—H21 | 0.9491 |
C12—C121 | 1.521 (3) | C22—C221 | 1.521 (3) |
C12—C13 | 1.523 (3) | C22—C23 | 1.525 (3) |
C12—H12 | 1.0000 | C22—H22 | 1.0000 |
C13—C14 | 1.519 (3) | C23—C24 | 1.513 (3) |
C13—H13A | 0.9900 | C23—H23A | 0.9900 |
C13—H13B | 0.9900 | C23—H23B | 0.9900 |
C14—O141 | 1.440 (3) | C24—O241 | 1.439 (3) |
C14—C15 | 1.527 (3) | C24—C25 | 1.521 (3) |
C14—H14 | 1.0000 | C24—H24 | 1.0000 |
O141—H141 | 0.8865 | O241—H241 | 0.9572 |
C15—C15a | 1.513 (3) | C25—C25A | 1.512 (3) |
C15—H15A | 0.9900 | C25—H25A | 0.9900 |
C15—H15B | 0.9900 | C25—H25B | 0.9900 |
C15a—C11b | 1.387 (3) | C25A—C21B | 1.387 (3) |
C15a—C16 | 1.413 (3) | C25A—C26 | 1.409 (3) |
C16—C17 | 1.364 (3) | C26—C27 | 1.363 (3) |
C16—H16 | 0.9500 | C26—H26 | 0.9500 |
C17—C17a | 1.416 (3) | C27—C27A | 1.420 (3) |
C17—Br17 | 1.910 (2) | C27—Br27 | 1.901 (2) |
C17a—C18 | 1.423 (3) | C27A—C28 | 1.418 (3) |
C17a—C11a | 1.427 (3) | C27A—C21A | 1.428 (3) |
C18—C19 | 1.365 (4) | C28—C29 | 1.367 (4) |
C18—H18 | 0.9500 | C28—H28 | 0.9500 |
C19—C110 | 1.404 (4) | C29—C210 | 1.407 (4) |
C19—H19 | 0.9500 | C29—H29 | 0.9500 |
C110—C111 | 1.367 (4) | C210—C211 | 1.367 (3) |
C110—H110 | 0.9500 | C210—H210 | 0.9500 |
C111—C11a | 1.421 (3) | C211—C21A | 1.427 (3) |
C111—H111 | 0.9500 | C211—H211 | 0.9500 |
C11a—C11b | 1.439 (3) | C21A—C21B | 1.438 (3) |
C121—C126 | 1.398 (3) | C221—C226 | 1.399 (3) |
C121—C122 | 1.404 (3) | C221—C222 | 1.399 (3) |
C122—C123 | 1.398 (4) | C222—C223 | 1.394 (3) |
C122—C127 | 1.505 (4) | C222—C227 | 1.510 (3) |
C123—C124 | 1.381 (4) | C223—C224 | 1.382 (4) |
C123—H123 | 0.9500 | C223—H223 | 0.9500 |
C124—C125 | 1.385 (4) | C224—C225 | 1.389 (4) |
C124—H124 | 0.9500 | C224—H224 | 0.9500 |
C125—C126 | 1.395 (3) | C225—C226 | 1.377 (4) |
C125—H125 | 0.9500 | C225—H225 | 0.9500 |
C126—H126 | 0.9500 | C226—H226 | 0.9500 |
C127—H17A | 0.9800 | C227—H27A | 0.9800 |
C127—H17B | 0.9800 | C227—H27B | 0.9800 |
C127—H17C | 0.9800 | C227—H27C | 0.9800 |
| | | |
C11b—N11—C12 | 116.79 (18) | C21B—N21—C22 | 113.33 (18) |
C11b—N11—H11 | 110.3 | C21B—N21—H21 | 109.5 |
C12—N11—H11 | 107.8 | C22—N21—H21 | 109.3 |
N11—C12—C121 | 109.06 (18) | N21—C22—C221 | 109.77 (18) |
N11—C12—C13 | 112.16 (19) | N21—C22—C23 | 112.01 (19) |
C121—C12—C13 | 113.0 (2) | C221—C22—C23 | 108.6 (2) |
N11—C12—H12 | 107.5 | N21—C22—H22 | 108.8 |
C121—C12—H12 | 107.5 | C221—C22—H22 | 108.8 |
C13—C12—H12 | 107.5 | C23—C22—H22 | 108.8 |
C14—C13—C12 | 113.2 (2) | C24—C23—C22 | 118.9 (2) |
C14—C13—H13A | 108.9 | C24—C23—H23A | 107.6 |
C12—C13—H13A | 108.9 | C22—C23—H23A | 107.6 |
C14—C13—H13B | 108.9 | C24—C23—H23B | 107.6 |
C12—C13—H13B | 108.9 | C22—C23—H23B | 107.6 |
H13A—C13—H13B | 107.7 | H23A—C23—H23B | 107.0 |
O141—C14—C13 | 105.92 (18) | O241—C24—C23 | 109.3 (2) |
O141—C14—C15 | 109.99 (18) | O241—C24—C25 | 107.26 (19) |
C13—C14—C15 | 113.91 (19) | C23—C24—C25 | 112.9 (2) |
O141—C14—H14 | 109.0 | O241—C24—H24 | 109.1 |
C13—C14—H14 | 109.0 | C23—C24—H24 | 109.1 |
C15—C14—H14 | 109.0 | C25—C24—H24 | 109.1 |
C14—O141—H141 | 109.5 | C24—O241—H241 | 103.1 |
C15a—C15—C14 | 116.78 (19) | C25A—C25—C24 | 113.91 (19) |
C15a—C15—H15A | 108.1 | C25A—C25—H25A | 108.8 |
C14—C15—H15A | 108.1 | C24—C25—H25A | 108.8 |
C15a—C15—H15B | 108.1 | C25A—C25—H25B | 108.8 |
C14—C15—H15B | 108.1 | C24—C25—H25B | 108.8 |
H15A—C15—H15B | 107.3 | H25A—C25—H25B | 107.7 |
C11b—C15a—C16 | 119.2 (2) | C21B—C25A—C26 | 119.5 (2) |
C11b—C15a—C15 | 121.7 (2) | C21B—C25A—C25 | 122.0 (2) |
C16—C15a—C15 | 118.8 (2) | C26—C25A—C25 | 118.5 (2) |
C17—C16—C15a | 121.2 (2) | C27—C26—C25A | 121.0 (2) |
C17—C16—H16 | 119.4 | C27—C26—H26 | 119.5 |
C15a—C16—H16 | 119.4 | C25A—C26—H26 | 119.5 |
C16—C17—C17a | 122.0 (2) | C26—C27—C27A | 122.3 (2) |
C16—C17—Br17 | 118.37 (19) | C26—C27—Br27 | 116.93 (18) |
C17a—C17—Br17 | 119.65 (18) | C27A—C27—Br27 | 120.81 (19) |
C17—C17a—C18 | 123.2 (2) | C28—C27A—C27 | 123.7 (2) |
C17—C17a—C11a | 117.6 (2) | C28—C27A—C21A | 119.1 (2) |
C18—C17a—C11a | 119.2 (2) | C27—C27A—C21A | 117.2 (2) |
C19—C18—C17a | 121.0 (3) | C29—C28—C27A | 121.1 (2) |
C19—C18—H18 | 119.5 | C29—C28—H28 | 119.5 |
C17a—C18—H18 | 119.5 | C27A—C28—H28 | 119.5 |
C18—C19—C110 | 120.1 (2) | C28—C29—C210 | 120.3 (2) |
C18—C19—H19 | 120.0 | C28—C29—H29 | 119.9 |
C110—C19—H19 | 120.0 | C210—C29—H29 | 119.9 |
C111—C110—C19 | 120.6 (2) | C211—C210—C29 | 120.3 (2) |
C111—C110—H110 | 119.7 | C211—C210—H210 | 119.9 |
C19—C110—H110 | 119.7 | C29—C210—H210 | 119.9 |
C110—C111—C11a | 121.4 (2) | C210—C211—C21A | 121.3 (2) |
C110—C111—H111 | 119.3 | C210—C211—H211 | 119.3 |
C11a—C111—H111 | 119.3 | C21A—C211—H211 | 119.3 |
C111—C11a—C17a | 117.8 (2) | C211—C21A—C27A | 117.9 (2) |
C111—C11a—C11b | 122.5 (2) | C211—C21A—C21B | 122.1 (2) |
C17a—C11a—C11b | 119.8 (2) | C27A—C21A—C21B | 119.9 (2) |
C15a—C11b—N11 | 118.8 (2) | C25A—C21B—N21 | 118.6 (2) |
C15a—C11b—C11a | 120.2 (2) | C25A—C21B—C21A | 120.2 (2) |
N11—C11b—C11a | 121.1 (2) | N21—C21B—C21A | 121.2 (2) |
C126—C121—C122 | 119.3 (2) | C226—C221—C222 | 119.4 (2) |
C126—C121—C12 | 121.0 (2) | C226—C221—C22 | 118.8 (2) |
C122—C121—C12 | 119.7 (2) | C222—C221—C22 | 121.7 (2) |
C123—C122—C121 | 118.7 (2) | C223—C222—C221 | 118.5 (2) |
C123—C122—C127 | 118.7 (2) | C223—C222—C227 | 119.5 (2) |
C121—C122—C127 | 122.5 (2) | C221—C222—C227 | 122.0 (2) |
C124—C123—C122 | 121.5 (2) | C224—C223—C222 | 121.6 (2) |
C124—C123—H123 | 119.2 | C224—C223—H223 | 119.2 |
C122—C123—H123 | 119.2 | C222—C223—H223 | 119.2 |
C123—C124—C125 | 119.9 (2) | C223—C224—C225 | 119.7 (2) |
C123—C124—H124 | 120.0 | C223—C224—H224 | 120.1 |
C125—C124—H124 | 120.0 | C225—C224—H224 | 120.1 |
C124—C125—C126 | 119.5 (3) | C226—C225—C224 | 119.4 (2) |
C124—C125—H125 | 120.3 | C226—C225—H225 | 120.3 |
C126—C125—H125 | 120.3 | C224—C225—H225 | 120.3 |
C125—C126—C121 | 121.0 (2) | C225—C226—C221 | 121.3 (2) |
C125—C126—H126 | 119.5 | C225—C226—H226 | 119.4 |
C121—C126—H126 | 119.5 | C221—C226—H226 | 119.4 |
C122—C127—H17A | 109.5 | C222—C227—H27A | 109.5 |
C122—C127—H17B | 109.5 | C222—C227—H27B | 109.5 |
H17A—C127—H17B | 109.5 | H27A—C227—H27B | 109.5 |
C122—C127—H17C | 109.5 | C222—C227—H27C | 109.5 |
H17A—C127—H17C | 109.5 | H27A—C227—H27C | 109.5 |
H17B—C127—H17C | 109.5 | H27B—C227—H27C | 109.5 |
| | | |
C11b—N11—C12—C121 | 145.3 (2) | C21B—N21—C22—C221 | 155.11 (19) |
C11b—N11—C12—C13 | −88.8 (2) | C21B—N21—C22—C23 | −84.2 (2) |
N11—C12—C13—C14 | 68.2 (2) | N21—C22—C23—C24 | 59.9 (3) |
C121—C12—C13—C14 | −168.06 (19) | C221—C22—C23—C24 | −178.7 (2) |
C12—C13—C14—O141 | 178.89 (18) | C22—C23—C24—O241 | −176.7 (2) |
C12—C13—C14—C15 | −60.1 (3) | C22—C23—C24—C25 | −57.4 (3) |
O141—C14—C15—C15a | −168.09 (19) | O241—C24—C25—C25A | −164.6 (2) |
C13—C14—C15—C15a | 73.2 (3) | C23—C24—C25—C25A | 75.0 (3) |
C14—C15—C15a—C11b | −66.8 (3) | C24—C25—C25A—C21B | −65.4 (3) |
C14—C15—C15a—C16 | 119.9 (2) | C24—C25—C25A—C26 | 112.3 (2) |
C11b—C15a—C16—C17 | −3.6 (3) | C21B—C25A—C26—C27 | −0.3 (3) |
C15—C15a—C16—C17 | 169.8 (2) | C25—C25A—C26—C27 | −178.0 (2) |
C15a—C16—C17—C17a | 1.1 (4) | C25A—C26—C27—C27A | 1.1 (4) |
C15a—C16—C17—Br17 | −177.04 (17) | C25A—C26—C27—Br27 | −179.76 (17) |
C16—C17—C17a—C18 | −179.8 (2) | C26—C27—C27A—C28 | 178.1 (2) |
Br17—C17—C17a—C18 | −1.7 (3) | Br27—C27—C27A—C28 | −1.0 (3) |
C16—C17—C17a—C11a | 1.3 (3) | C26—C27—C27A—C21A | −0.5 (3) |
Br17—C17—C17a—C11a | 179.42 (16) | Br27—C27—C27A—C21A | −179.67 (17) |
C17—C17a—C18—C19 | −178.6 (2) | C27—C27A—C28—C29 | −177.4 (2) |
C11a—C17a—C18—C19 | 0.3 (3) | C21A—C27A—C28—C29 | 1.2 (4) |
C17a—C18—C19—C110 | −0.9 (4) | C27A—C28—C29—C210 | 0.1 (4) |
C18—C19—C110—C111 | 0.8 (4) | C28—C29—C210—C211 | −0.9 (4) |
C19—C110—C111—C11a | 0.1 (4) | C29—C210—C211—C21A | 0.5 (4) |
C110—C111—C11a—C17a | −0.7 (3) | C210—C211—C21A—C27A | 0.8 (4) |
C110—C111—C11a—C11b | 179.9 (2) | C210—C211—C21A—C21B | 178.6 (2) |
C17—C17a—C11a—C111 | 179.4 (2) | C28—C27A—C21A—C211 | −1.6 (3) |
C18—C17a—C11a—C111 | 0.6 (3) | C27—C27A—C21A—C211 | 177.1 (2) |
C17—C17a—C11a—C11b | −1.2 (3) | C28—C27A—C21A—C21B | −179.4 (2) |
C18—C17a—C11a—C11b | 179.9 (2) | C27—C27A—C21A—C21B | −0.7 (3) |
C16—C15a—C11b—N11 | −177.9 (2) | C26—C25A—C21B—N21 | −179.6 (2) |
C15—C15a—C11b—N11 | 8.9 (3) | C25—C25A—C21B—N21 | −2.0 (3) |
C16—C15a—C11b—C11a | 3.7 (3) | C26—C25A—C21B—C21A | −0.9 (3) |
C15—C15a—C11b—C11a | −169.6 (2) | C25—C25A—C21B—C21A | 176.7 (2) |
C12—N11—C11b—C15a | 60.9 (3) | C22—N21—C21B—C25A | 71.8 (3) |
C12—N11—C11b—C11a | −120.7 (2) | C22—N21—C21B—C21A | −106.9 (2) |
C111—C11a—C11b—C15a | 178.0 (2) | C211—C21A—C21B—C25A | −176.3 (2) |
C17a—C11a—C11b—C15a | −1.3 (3) | C27A—C21A—C21B—C25A | 1.4 (3) |
C111—C11a—C11b—N11 | −0.4 (3) | C211—C21A—C21B—N21 | 2.4 (3) |
C17a—C11a—C11b—N11 | −179.7 (2) | C27A—C21A—C21B—N21 | −179.9 (2) |
N11—C12—C121—C126 | 94.5 (3) | N21—C22—C221—C226 | 61.4 (3) |
C13—C12—C121—C126 | −30.9 (3) | C23—C22—C221—C226 | −61.3 (3) |
N11—C12—C121—C122 | −86.2 (3) | N21—C22—C221—C222 | −122.3 (2) |
C13—C12—C121—C122 | 148.4 (2) | C23—C22—C221—C222 | 115.0 (2) |
C126—C121—C122—C123 | 1.2 (4) | C226—C221—C222—C223 | 2.1 (3) |
C12—C121—C122—C123 | −178.1 (2) | C22—C221—C222—C223 | −174.1 (2) |
C126—C121—C122—C127 | −179.5 (2) | C226—C221—C222—C227 | −177.7 (2) |
C12—C121—C122—C127 | 1.2 (4) | C22—C221—C222—C227 | 6.0 (4) |
C121—C122—C123—C124 | −1.7 (4) | C221—C222—C223—C224 | −0.8 (4) |
C127—C122—C123—C124 | 179.0 (2) | C227—C222—C223—C224 | 179.1 (2) |
C122—C123—C124—C125 | 0.9 (4) | C222—C223—C224—C225 | −0.9 (4) |
C123—C124—C125—C126 | 0.4 (4) | C223—C224—C225—C226 | 1.2 (4) |
C124—C125—C126—C121 | −0.8 (4) | C224—C225—C226—C221 | 0.2 (4) |
C122—C121—C126—C125 | 0.0 (4) | C222—C221—C226—C225 | −1.8 (4) |
C12—C121—C126—C125 | 179.3 (2) | C22—C221—C226—C225 | 174.5 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O141—H141···N21i | 0.89 | 2.08 | 2.961 (3) | 174 |
O241—H241···O141 | 0.96 | 2.27 | 3.197 (3) | 163 |
C28—H28···Cg1ii | 0.95 | 2.98 | 3.709 (3) | 135 |
C110—H110···Cg2iii | 0.95 | 2.91 | 3.673 (3) | 138 |
C111—H111···Cg3iii | 0.95 | 2.98 | 3.718 (3) | 136 |
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. |
(II) (2
RS,4
SR)-2-(3-Methylthiophen-2-yl)-2,3,4,5-tetrahydro-1
H-naphtho[1,2-
b]azepin-4-ol
top
Crystal data top
C19H19NOS | F(000) = 1312 |
Mr = 309.42 | Dx = 1.273 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 7119 reflections |
a = 25.431 (5) Å | θ = 2.8–27.5° |
b = 16.318 (3) Å | µ = 0.20 mm−1 |
c = 8.0193 (6) Å | T = 120 K |
β = 104.021 (10)° | Rod, pale yellow |
V = 3228.8 (9) Å3 | 0.34 × 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 anode | 6110 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.000 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 2.8° |
φ and ω scans | h = −32→32 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | k = −21→21 |
Tmin = 0.935, Tmax = 0.972 | l = −9→10 |
7118 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-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 reflections | Δρmax = 0.39 e Å−3 |
400 parameters | Δρmin = −0.28 e Å−3 |
2 restraints | Absolute structure: Flack (1983), with 3400 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.09 (13) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N11 | 0.48716 (9) | 0.67480 (14) | 0.3141 (3) | 0.0238 (5) | |
H11 | 0.4900 | 0.7120 | 0.2300 | 0.029* | |
C12 | 0.44122 (11) | 0.70530 (16) | 0.3809 (4) | 0.0239 (6) | |
H12 | 0.4564 | 0.7311 | 0.4955 | 0.029* | |
C13 | 0.40359 (11) | 0.63544 (17) | 0.4055 (4) | 0.0261 (6) | |
H13A | 0.3716 | 0.6593 | 0.4375 | 0.031* | |
H13B | 0.3905 | 0.6069 | 0.2942 | 0.031* | |
C14 | 0.42927 (10) | 0.57283 (17) | 0.5405 (4) | 0.0250 (6) | |
H14 | 0.4440 | 0.6024 | 0.6511 | 0.030* | |
O141 | 0.38873 (8) | 0.51583 (12) | 0.5662 (3) | 0.0294 (5) | |
H141 | 0.3711 | 0.4926 | 0.4597 | 0.044* | |
C15 | 0.47569 (11) | 0.52581 (17) | 0.4946 (4) | 0.0252 (6) | |
H15A | 0.4820 | 0.4747 | 0.5631 | 0.030* | |
H15B | 0.4646 | 0.5101 | 0.3718 | 0.030* | |
C15a | 0.52857 (11) | 0.57310 (16) | 0.5253 (3) | 0.0221 (6) | |
C16 | 0.57457 (11) | 0.54204 (17) | 0.6459 (4) | 0.0250 (6) | |
H16 | 0.5709 | 0.4941 | 0.7095 | 0.030* | |
C17 | 0.62394 (11) | 0.57934 (17) | 0.6728 (4) | 0.0262 (6) | |
H17 | 0.6543 | 0.5565 | 0.7523 | 0.031* | |
C17a | 0.63015 (11) | 0.65189 (17) | 0.5827 (4) | 0.0234 (6) | |
C18 | 0.68075 (11) | 0.69296 (18) | 0.6129 (4) | 0.0261 (6) | |
H18 | 0.7119 | 0.6685 | 0.6857 | 0.031* | |
C19 | 0.68547 (11) | 0.76729 (18) | 0.5387 (4) | 0.0283 (6) | |
H19 | 0.7195 | 0.7944 | 0.5617 | 0.034* | |
C110 | 0.63979 (11) | 0.80354 (18) | 0.4282 (4) | 0.0274 (6) | |
H110 | 0.6430 | 0.8557 | 0.3789 | 0.033* | |
C111 | 0.59065 (11) | 0.76401 (17) | 0.3914 (4) | 0.0247 (6) | |
H111 | 0.5605 | 0.7887 | 0.3142 | 0.030* | |
C11a | 0.58396 (10) | 0.68741 (17) | 0.4661 (3) | 0.0211 (5) | |
C11b | 0.53301 (11) | 0.64445 (17) | 0.4362 (3) | 0.0219 (6) | |
S121 | 0.36125 (3) | 0.74292 (5) | 0.07978 (10) | 0.0397 (2) | |
C122 | 0.41056 (11) | 0.77003 (17) | 0.2623 (4) | 0.0264 (6) | |
C123 | 0.41582 (11) | 0.85250 (18) | 0.2770 (4) | 0.0312 (7) | |
C124 | 0.37913 (13) | 0.8946 (2) | 0.1412 (5) | 0.0429 (9) | |
H124 | 0.3769 | 0.9526 | 0.1330 | 0.052* | |
C125 | 0.34776 (14) | 0.8437 (2) | 0.0253 (5) | 0.0477 (9) | |
H125 | 0.3216 | 0.8615 | −0.0737 | 0.057* | |
C126 | 0.45395 (13) | 0.89584 (17) | 0.4187 (4) | 0.0361 (7) | |
H16A | 0.4743 | 0.8557 | 0.5001 | 0.054* | |
H16B | 0.4335 | 0.9317 | 0.4782 | 0.054* | |
H16C | 0.4792 | 0.9288 | 0.3716 | 0.054* | |
N21 | 0.19347 (9) | 0.31908 (14) | −0.0322 (3) | 0.0245 (5) | |
H21 | 0.1792 | 0.2793 | −0.1077 | 0.029* | |
C22 | 0.23738 (11) | 0.28640 (16) | 0.1101 (4) | 0.0256 (6) | |
H22 | 0.2228 | 0.2827 | 0.2151 | 0.031* | |
C23 | 0.28560 (12) | 0.34501 (18) | 0.1497 (4) | 0.0307 (7) | |
H23A | 0.3163 | 0.3181 | 0.2310 | 0.037* | |
H23B | 0.2970 | 0.3561 | 0.0423 | 0.037* | |
C24 | 0.27348 (12) | 0.42620 (18) | 0.2266 (4) | 0.0318 (7) | |
H24 | 0.2620 | 0.4140 | 0.3349 | 0.038* | |
O241 | 0.32154 (9) | 0.47525 (15) | 0.2707 (3) | 0.0451 (6) | |
H241 | 0.3442 | 0.4708 | 0.1915 | 0.068* | |
C25 | 0.22831 (13) | 0.47587 (17) | 0.1090 (4) | 0.0345 (7) | |
H25A | 0.2303 | 0.5327 | 0.1531 | 0.041* | |
H25B | 0.2357 | 0.4780 | −0.0065 | 0.041* | |
C25A | 0.17134 (12) | 0.44569 (17) | 0.0892 (4) | 0.0292 (7) | |
C26 | 0.13307 (14) | 0.49727 (19) | 0.1409 (4) | 0.0350 (7) | |
H26 | 0.1449 | 0.5475 | 0.1975 | 0.042* | |
C27 | 0.07981 (14) | 0.4761 (2) | 0.1110 (4) | 0.0376 (8) | |
H27 | 0.0550 | 0.5120 | 0.1455 | 0.045* | |
C27A | 0.06096 (13) | 0.40160 (19) | 0.0294 (4) | 0.0320 (7) | |
C28 | 0.00564 (13) | 0.3777 (2) | −0.0033 (4) | 0.0382 (8) | |
H28 | −0.0199 | 0.4138 | 0.0270 | 0.046* | |
C29 | −0.01150 (13) | 0.3046 (2) | −0.0768 (4) | 0.0414 (8) | |
H29 | −0.0487 | 0.2900 | −0.0980 | 0.050* | |
C210 | 0.02572 (12) | 0.2503 (2) | −0.1218 (4) | 0.0384 (8) | |
H210 | 0.0136 | 0.1988 | −0.1717 | 0.046* | |
C211 | 0.07938 (12) | 0.27102 (19) | −0.0942 (4) | 0.0305 (7) | |
H211 | 0.1040 | 0.2336 | −0.1255 | 0.037* | |
C21A | 0.09872 (12) | 0.34719 (18) | −0.0200 (4) | 0.0271 (6) | |
C21B | 0.15463 (12) | 0.37093 (17) | 0.0138 (4) | 0.0251 (6) | |
S221 | 0.30602 (3) | 0.18513 (5) | −0.02813 (9) | 0.03378 (18) | |
C222 | 0.25239 (11) | 0.20151 (17) | 0.0668 (4) | 0.0258 (6) | |
C223 | 0.22791 (12) | 0.12960 (17) | 0.0927 (4) | 0.0293 (6) | |
C224 | 0.25286 (13) | 0.06063 (19) | 0.0322 (4) | 0.0371 (8) | |
H224 | 0.2409 | 0.0058 | 0.0384 | 0.045* | |
C225 | 0.29515 (13) | 0.0811 (2) | −0.0349 (5) | 0.0408 (8) | |
H225 | 0.3162 | 0.0427 | −0.0800 | 0.049* | |
C226 | 0.17971 (14) | 0.1228 (2) | 0.1688 (4) | 0.0394 (8) | |
H26A | 0.1666 | 0.1778 | 0.1867 | 0.059* | |
H26B | 0.1902 | 0.0941 | 0.2792 | 0.059* | |
H26C | 0.1509 | 0.0921 | 0.0903 | 0.059* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N11 | 0.0218 (11) | 0.0271 (12) | 0.0226 (12) | 0.0025 (9) | 0.0054 (9) | 0.0055 (10) |
C12 | 0.0248 (14) | 0.0215 (13) | 0.0246 (14) | −0.0009 (11) | 0.0044 (11) | −0.0003 (11) |
C13 | 0.0242 (14) | 0.0244 (14) | 0.0321 (16) | −0.0022 (11) | 0.0117 (12) | 0.0021 (12) |
C14 | 0.0249 (14) | 0.0223 (13) | 0.0295 (15) | −0.0023 (11) | 0.0098 (12) | 0.0012 (12) |
O141 | 0.0300 (10) | 0.0249 (10) | 0.0353 (11) | −0.0054 (8) | 0.0118 (9) | 0.0019 (9) |
C15 | 0.0297 (14) | 0.0200 (13) | 0.0273 (15) | −0.0013 (11) | 0.0099 (12) | 0.0008 (12) |
C15a | 0.0247 (14) | 0.0214 (13) | 0.0225 (14) | 0.0031 (11) | 0.0100 (11) | −0.0009 (11) |
C16 | 0.0301 (15) | 0.0198 (13) | 0.0246 (15) | 0.0055 (11) | 0.0058 (12) | 0.0056 (11) |
C17 | 0.0254 (13) | 0.0245 (14) | 0.0267 (15) | 0.0072 (11) | 0.0020 (11) | 0.0015 (12) |
C17a | 0.0248 (13) | 0.0268 (15) | 0.0197 (14) | 0.0032 (11) | 0.0074 (11) | −0.0019 (11) |
C18 | 0.0224 (13) | 0.0330 (16) | 0.0213 (14) | 0.0010 (11) | 0.0020 (11) | −0.0048 (12) |
C19 | 0.0239 (14) | 0.0379 (17) | 0.0245 (15) | −0.0051 (12) | 0.0089 (11) | −0.0048 (13) |
C110 | 0.0313 (15) | 0.0279 (15) | 0.0251 (15) | −0.0061 (12) | 0.0109 (12) | 0.0005 (12) |
C111 | 0.0236 (13) | 0.0256 (14) | 0.0247 (14) | 0.0009 (11) | 0.0057 (11) | 0.0009 (12) |
C11a | 0.0209 (13) | 0.0252 (13) | 0.0182 (13) | 0.0019 (11) | 0.0067 (10) | −0.0027 (11) |
C11b | 0.0233 (13) | 0.0230 (14) | 0.0200 (14) | 0.0047 (11) | 0.0066 (11) | −0.0016 (11) |
S121 | 0.0305 (4) | 0.0467 (5) | 0.0352 (4) | −0.0051 (4) | −0.0052 (3) | 0.0067 (4) |
C122 | 0.0214 (14) | 0.0289 (15) | 0.0284 (15) | −0.0006 (12) | 0.0052 (11) | 0.0052 (13) |
C123 | 0.0239 (14) | 0.0293 (16) | 0.0409 (18) | 0.0016 (13) | 0.0089 (13) | 0.0067 (14) |
C124 | 0.0331 (17) | 0.0413 (19) | 0.055 (2) | 0.0092 (15) | 0.0122 (16) | 0.0229 (18) |
C125 | 0.0312 (17) | 0.058 (2) | 0.048 (2) | 0.0059 (16) | −0.0020 (15) | 0.0268 (19) |
C126 | 0.0475 (19) | 0.0180 (14) | 0.043 (2) | 0.0016 (13) | 0.0111 (16) | 0.0026 (14) |
N21 | 0.0287 (12) | 0.0253 (12) | 0.0204 (12) | −0.0025 (10) | 0.0080 (10) | −0.0048 (10) |
C22 | 0.0280 (14) | 0.0227 (14) | 0.0254 (14) | −0.0023 (11) | 0.0054 (12) | −0.0005 (12) |
C23 | 0.0292 (15) | 0.0358 (17) | 0.0276 (16) | −0.0102 (13) | 0.0079 (12) | −0.0069 (13) |
C24 | 0.0379 (17) | 0.0327 (16) | 0.0293 (16) | −0.0195 (13) | 0.0169 (13) | −0.0095 (13) |
O241 | 0.0432 (13) | 0.0558 (15) | 0.0417 (14) | −0.0318 (11) | 0.0208 (11) | −0.0257 (12) |
C25 | 0.056 (2) | 0.0205 (14) | 0.0280 (16) | −0.0117 (14) | 0.0129 (14) | −0.0034 (13) |
C25A | 0.0457 (18) | 0.0200 (14) | 0.0230 (15) | 0.0003 (13) | 0.0106 (13) | 0.0038 (12) |
C26 | 0.057 (2) | 0.0218 (14) | 0.0258 (16) | 0.0049 (14) | 0.0100 (15) | −0.0007 (12) |
C27 | 0.054 (2) | 0.0324 (17) | 0.0265 (16) | 0.0163 (15) | 0.0100 (15) | 0.0026 (13) |
C27A | 0.0410 (17) | 0.0352 (17) | 0.0203 (15) | 0.0113 (14) | 0.0085 (13) | 0.0060 (13) |
C28 | 0.0384 (18) | 0.051 (2) | 0.0261 (16) | 0.0155 (16) | 0.0104 (14) | 0.0083 (15) |
C29 | 0.0271 (16) | 0.065 (2) | 0.0323 (18) | 0.0019 (16) | 0.0074 (13) | 0.0075 (17) |
C210 | 0.0327 (17) | 0.049 (2) | 0.0320 (17) | −0.0050 (15) | 0.0058 (14) | −0.0048 (16) |
C211 | 0.0270 (15) | 0.0398 (17) | 0.0257 (15) | −0.0005 (13) | 0.0087 (12) | −0.0041 (13) |
C21A | 0.0337 (15) | 0.0281 (15) | 0.0201 (15) | 0.0051 (12) | 0.0076 (12) | 0.0035 (12) |
C21B | 0.0359 (16) | 0.0244 (14) | 0.0168 (14) | 0.0021 (12) | 0.0097 (11) | 0.0047 (12) |
S221 | 0.0232 (3) | 0.0369 (4) | 0.0410 (5) | 0.0038 (3) | 0.0073 (3) | −0.0025 (4) |
C222 | 0.0223 (13) | 0.0295 (15) | 0.0236 (15) | 0.0006 (11) | 0.0020 (11) | −0.0011 (12) |
C223 | 0.0357 (16) | 0.0272 (15) | 0.0233 (15) | −0.0004 (13) | 0.0037 (12) | −0.0004 (12) |
C224 | 0.0412 (18) | 0.0257 (16) | 0.0385 (18) | 0.0066 (14) | −0.0020 (15) | 0.0019 (14) |
C225 | 0.0348 (18) | 0.0374 (17) | 0.045 (2) | 0.0139 (14) | −0.0004 (16) | −0.0033 (16) |
C226 | 0.052 (2) | 0.0316 (17) | 0.0363 (19) | −0.0110 (15) | 0.0147 (15) | −0.0034 (14) |
Geometric parameters (Å, º) top
N11—C11b | 1.418 (3) | N21—C21B | 1.416 (4) |
N11—C12 | 1.484 (3) | N21—C22 | 1.489 (4) |
N11—H11 | 0.9237 | N21—H21 | 0.9021 |
C12—C122 | 1.506 (4) | C22—C222 | 1.500 (4) |
C12—C13 | 1.532 (4) | C22—C23 | 1.527 (4) |
C12—H12 | 1.0000 | C22—H22 | 1.0000 |
C13—C14 | 1.516 (4) | C23—C24 | 1.524 (4) |
C13—H13A | 0.9900 | C23—H23A | 0.9900 |
C13—H13B | 0.9900 | C23—H23B | 0.9900 |
C14—O141 | 1.440 (3) | C24—O241 | 1.432 (3) |
C14—C15 | 1.526 (4) | C24—C25 | 1.530 (4) |
C14—H14 | 1.0000 | C24—H24 | 1.0000 |
O141—H141 | 0.9424 | O241—H241 | 0.9579 |
C15—C15a | 1.518 (4) | C25—C25A | 1.502 (4) |
C15—H15A | 0.9900 | C25—H25A | 0.9900 |
C15—H15B | 0.9900 | C25—H25B | 0.9900 |
C15a—C11b | 1.385 (4) | C25A—C21B | 1.382 (4) |
C15a—C16 | 1.419 (4) | C25A—C26 | 1.422 (4) |
C16—C17 | 1.365 (4) | C26—C27 | 1.362 (5) |
C16—H16 | 0.9500 | C26—H26 | 0.9500 |
C17—C17a | 1.416 (4) | C27—C27A | 1.408 (4) |
C17—H17 | 0.9500 | C27—H27 | 0.9500 |
C17a—C18 | 1.419 (4) | C27A—C28 | 1.421 (5) |
C17a—C11a | 1.435 (4) | C27A—C21A | 1.432 (4) |
C18—C19 | 1.369 (4) | C28—C29 | 1.356 (5) |
C18—H18 | 0.9500 | C28—H28 | 0.9500 |
C19—C110 | 1.409 (4) | C29—C210 | 1.406 (5) |
C19—H19 | 0.9500 | C29—H29 | 0.9500 |
C110—C111 | 1.373 (4) | C210—C211 | 1.371 (4) |
C110—H110 | 0.9500 | C210—H210 | 0.9500 |
C111—C11a | 1.414 (4) | C211—C21A | 1.414 (4) |
C111—H111 | 0.9500 | C211—H211 | 0.9500 |
C11a—C11b | 1.441 (4) | C21A—C21B | 1.435 (4) |
S121—C125 | 1.714 (4) | S221—C225 | 1.719 (3) |
S121—C122 | 1.738 (3) | S221—C222 | 1.736 (3) |
C122—C123 | 1.355 (4) | C222—C223 | 1.368 (4) |
C123—C124 | 1.426 (4) | C223—C224 | 1.433 (4) |
C123—C126 | 1.483 (4) | C223—C226 | 1.500 (4) |
C124—C125 | 1.353 (5) | C224—C225 | 1.355 (5) |
C124—H124 | 0.9500 | C224—H224 | 0.9500 |
C125—H125 | 0.9500 | C225—H225 | 0.9500 |
C126—H16A | 0.9800 | C226—H26A | 0.9800 |
C126—H16B | 0.9800 | C226—H26B | 0.9800 |
C126—H16C | 0.9800 | C226—H26C | 0.9800 |
| | | |
C11b—N11—C12 | 117.1 (2) | C21B—N21—C22 | 117.1 (2) |
C11b—N11—H11 | 122.5 | C21B—N21—H21 | 114.3 |
C12—N11—H11 | 104.6 | C22—N21—H21 | 111.2 |
N11—C12—C122 | 109.9 (2) | N21—C22—C222 | 109.8 (2) |
N11—C12—C13 | 111.6 (2) | N21—C22—C23 | 110.5 (2) |
C122—C12—C13 | 111.0 (2) | C222—C22—C23 | 113.0 (2) |
N11—C12—H12 | 108.1 | N21—C22—H22 | 107.8 |
C122—C12—H12 | 108.1 | C222—C22—H22 | 107.8 |
C13—C12—H12 | 108.1 | C23—C22—H22 | 107.8 |
C14—C13—C12 | 114.8 (2) | C24—C23—C22 | 113.4 (2) |
C14—C13—H13A | 108.6 | C24—C23—H23A | 108.9 |
C12—C13—H13A | 108.6 | C22—C23—H23A | 108.9 |
C14—C13—H13B | 108.6 | C24—C23—H23B | 108.9 |
C12—C13—H13B | 108.6 | C22—C23—H23B | 108.9 |
H13A—C13—H13B | 107.6 | H23A—C23—H23B | 107.7 |
O141—C14—C13 | 109.8 (2) | O241—C24—C23 | 110.0 (2) |
O141—C14—C15 | 109.4 (2) | O241—C24—C25 | 108.9 (2) |
C13—C14—C15 | 113.0 (2) | C23—C24—C25 | 114.0 (2) |
O141—C14—H14 | 108.2 | O241—C24—H24 | 107.9 |
C13—C14—H14 | 108.2 | C23—C24—H24 | 107.9 |
C15—C14—H14 | 108.2 | C25—C24—H24 | 107.9 |
C14—O141—H141 | 109.3 | C24—O241—H241 | 114.1 |
C15a—C15—C14 | 114.3 (2) | C25A—C25—C24 | 116.9 (2) |
C15a—C15—H15A | 108.7 | C25A—C25—H25A | 108.1 |
C14—C15—H15A | 108.7 | C24—C25—H25A | 108.1 |
C15a—C15—H15B | 108.7 | C25A—C25—H25B | 108.1 |
C14—C15—H15B | 108.7 | C24—C25—H25B | 108.1 |
H15A—C15—H15B | 107.6 | H25A—C25—H25B | 107.3 |
C11b—C15a—C16 | 119.7 (2) | C21B—C25A—C26 | 119.4 (3) |
C11b—C15a—C15 | 121.6 (2) | C21B—C25A—C25 | 121.5 (3) |
C16—C15a—C15 | 118.7 (2) | C26—C25A—C25 | 119.1 (3) |
C17—C16—C15a | 121.6 (3) | C27—C26—C25A | 121.3 (3) |
C17—C16—H16 | 119.2 | C27—C26—H26 | 119.3 |
C15a—C16—H16 | 119.2 | C25A—C26—H26 | 119.3 |
C16—C17—C17a | 120.3 (3) | C26—C27—C27A | 120.9 (3) |
C16—C17—H17 | 119.9 | C26—C27—H27 | 119.6 |
C17a—C17—H17 | 119.9 | C27A—C27—H27 | 119.6 |
C17—C17a—C18 | 121.1 (3) | C27—C27A—C28 | 122.2 (3) |
C17—C17a—C11a | 119.7 (2) | C27—C27A—C21A | 119.2 (3) |
C18—C17a—C11a | 119.1 (3) | C28—C27A—C21A | 118.6 (3) |
C19—C18—C17a | 121.1 (3) | C29—C28—C27A | 121.4 (3) |
C19—C18—H18 | 119.5 | C29—C28—H28 | 119.3 |
C17a—C18—H18 | 119.5 | C27A—C28—H28 | 119.3 |
C18—C19—C110 | 120.0 (3) | C28—C29—C210 | 120.1 (3) |
C18—C19—H19 | 120.0 | C28—C29—H29 | 120.0 |
C110—C19—H19 | 120.0 | C210—C29—H29 | 120.0 |
C111—C110—C19 | 120.4 (3) | C211—C210—C29 | 120.6 (3) |
C111—C110—H110 | 119.8 | C211—C210—H210 | 119.7 |
C19—C110—H110 | 119.8 | C29—C210—H210 | 119.7 |
C110—C111—C11a | 121.4 (3) | C210—C211—C21A | 121.1 (3) |
C110—C111—H111 | 119.3 | C210—C211—H211 | 119.5 |
C11a—C111—H111 | 119.3 | C21A—C211—H211 | 119.5 |
C111—C11a—C17a | 118.0 (2) | C211—C21A—C27A | 118.2 (3) |
C111—C11a—C11b | 123.7 (2) | C211—C21A—C21B | 123.0 (3) |
C17a—C11a—C11b | 118.2 (2) | C27A—C21A—C21B | 118.7 (3) |
C15a—C11b—N11 | 119.6 (2) | C25A—C21B—N21 | 118.8 (3) |
C15a—C11b—C11a | 120.4 (2) | C25A—C21B—C21A | 120.4 (3) |
N11—C11b—C11a | 120.1 (2) | N21—C21B—C21A | 120.8 (2) |
C125—S121—C122 | 91.69 (16) | C225—S221—C222 | 91.63 (16) |
C123—C122—C12 | 128.1 (3) | C223—C222—C22 | 127.3 (3) |
C123—C122—S121 | 111.2 (2) | C223—C222—S221 | 111.7 (2) |
C12—C122—S121 | 120.7 (2) | C22—C222—S221 | 121.0 (2) |
C122—C123—C124 | 112.3 (3) | C222—C223—C224 | 111.5 (3) |
C122—C123—C126 | 124.9 (3) | C222—C223—C226 | 124.9 (3) |
C124—C123—C126 | 122.7 (3) | C224—C223—C226 | 123.5 (3) |
C125—C124—C123 | 113.3 (3) | C225—C224—C223 | 113.6 (3) |
C125—C124—H124 | 123.3 | C225—C224—H224 | 123.2 |
C123—C124—H124 | 123.3 | C223—C224—H224 | 123.2 |
C124—C125—S121 | 111.4 (3) | C224—C225—S221 | 111.6 (2) |
C124—C125—H125 | 124.3 | C224—C225—H225 | 124.2 |
S121—C125—H125 | 124.3 | S221—C225—H225 | 124.2 |
C123—C126—H16A | 109.5 | C223—C226—H26A | 109.5 |
C123—C126—H16B | 109.5 | C223—C226—H26B | 109.5 |
H16A—C126—H16B | 109.5 | H26A—C226—H26B | 109.5 |
C123—C126—H16C | 109.5 | C223—C226—H26C | 109.5 |
H16A—C126—H16C | 109.5 | H26A—C226—H26C | 109.5 |
H16B—C126—H16C | 109.5 | H26B—C226—H26C | 109.5 |
| | | |
C11b—N11—C12—C122 | 152.0 (2) | C21B—N21—C22—C222 | 145.6 (2) |
C11b—N11—C12—C13 | −84.4 (3) | C21B—N21—C22—C23 | −89.1 (3) |
N11—C12—C13—C14 | 64.5 (3) | N21—C22—C23—C24 | 67.5 (3) |
C122—C12—C13—C14 | −172.5 (2) | C222—C22—C23—C24 | −169.0 (3) |
C12—C13—C14—O141 | 173.4 (2) | C22—C23—C24—O241 | 176.1 (2) |
C12—C13—C14—C15 | −64.1 (3) | C22—C23—C24—C25 | −61.2 (3) |
O141—C14—C15—C15a | −159.5 (2) | O241—C24—C25—C25A | −163.0 (2) |
C13—C14—C15—C15a | 77.9 (3) | C23—C24—C25—C25A | 73.8 (3) |
C14—C15—C15a—C11b | −63.3 (3) | C24—C25—C25A—C21B | −64.4 (4) |
C14—C15—C15a—C16 | 118.1 (3) | C24—C25—C25A—C26 | 119.0 (3) |
C11b—C15a—C16—C17 | −2.2 (4) | C21B—C25A—C26—C27 | −2.9 (5) |
C15—C15a—C16—C17 | 176.5 (3) | C25—C25A—C26—C27 | 173.8 (3) |
C15a—C16—C17—C17a | 1.5 (4) | C25A—C26—C27—C27A | 0.8 (5) |
C16—C17—C17a—C18 | 178.0 (3) | C26—C27—C27A—C28 | 179.9 (3) |
C16—C17—C17a—C11a | 1.6 (4) | C26—C27—C27A—C21A | 0.9 (4) |
C17—C17a—C18—C19 | −173.4 (3) | C27—C27A—C28—C29 | −177.8 (3) |
C11a—C17a—C18—C19 | 3.0 (4) | C21A—C27A—C28—C29 | 1.2 (5) |
C17a—C18—C19—C110 | −1.0 (4) | C27A—C28—C29—C210 | 0.3 (5) |
C18—C19—C110—C111 | −1.3 (4) | C28—C29—C210—C211 | −0.9 (5) |
C19—C110—C111—C11a | 1.7 (4) | C29—C210—C211—C21A | 0.1 (5) |
C110—C111—C11a—C17a | 0.2 (4) | C210—C211—C21A—C27A | 1.4 (4) |
C110—C111—C11a—C11b | 178.0 (3) | C210—C211—C21A—C21B | 179.0 (3) |
C17—C17a—C11a—C111 | 173.9 (3) | C27—C27A—C21A—C211 | 177.0 (3) |
C18—C17a—C11a—C111 | −2.5 (4) | C28—C27A—C21A—C211 | −2.0 (4) |
C17—C17a—C11a—C11b | −4.0 (4) | C27—C27A—C21A—C21B | −0.7 (4) |
C18—C17a—C11a—C11b | 179.5 (2) | C28—C27A—C21A—C21B | −179.7 (3) |
C16—C15a—C11b—N11 | 179.2 (2) | C26—C25A—C21B—N21 | −178.0 (3) |
C15—C15a—C11b—N11 | 0.5 (4) | C25—C25A—C21B—N21 | 5.4 (4) |
C16—C15a—C11b—C11a | −0.4 (4) | C26—C25A—C21B—C21A | 3.1 (4) |
C15—C15a—C11b—C11a | −179.0 (2) | C25—C25A—C21B—C21A | −173.5 (3) |
C12—N11—C11b—C15a | 67.3 (3) | C22—N21—C21B—C25A | 64.8 (3) |
C12—N11—C11b—C11a | −113.2 (3) | C22—N21—C21B—C21A | −116.4 (3) |
C111—C11a—C11b—C15a | −174.4 (3) | C211—C21A—C21B—C25A | −179.0 (3) |
C17a—C11a—C11b—C15a | 3.4 (4) | C27A—C21A—C21B—C25A | −1.3 (4) |
C111—C11a—C11b—N11 | 6.0 (4) | C211—C21A—C21B—N21 | 2.2 (4) |
C17a—C11a—C11b—N11 | −176.2 (2) | C27A—C21A—C21B—N21 | 179.8 (3) |
N11—C12—C122—C123 | −96.6 (4) | N21—C22—C222—C223 | −84.9 (3) |
C13—C12—C122—C123 | 139.5 (3) | C23—C22—C222—C223 | 151.2 (3) |
N11—C12—C122—S121 | 83.4 (3) | N21—C22—C222—S221 | 94.8 (3) |
C13—C12—C122—S121 | −40.5 (3) | C23—C22—C222—S221 | −29.1 (3) |
C125—S121—C122—C123 | −0.4 (3) | C225—S221—C222—C223 | 0.5 (2) |
C125—S121—C122—C12 | 179.6 (3) | C225—S221—C222—C22 | −179.3 (2) |
C12—C122—C123—C124 | −179.0 (3) | C22—C222—C223—C224 | 179.0 (3) |
S121—C122—C123—C124 | 1.0 (3) | S221—C222—C223—C224 | −0.8 (3) |
C12—C122—C123—C126 | −0.5 (5) | C22—C222—C223—C226 | 1.1 (5) |
S121—C122—C123—C126 | 179.5 (3) | S221—C222—C223—C226 | −178.7 (2) |
C122—C123—C124—C125 | −1.2 (4) | C222—C223—C224—C225 | 0.8 (4) |
C126—C123—C124—C125 | −179.8 (3) | C226—C223—C224—C225 | 178.7 (3) |
C123—C124—C125—S121 | 0.9 (4) | C223—C224—C225—S221 | −0.4 (4) |
C122—S121—C125—C124 | −0.3 (3) | C222—S221—C225—C224 | −0.1 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O141—H141···O241 | 0.94 | 1.74 | 2.648 (3) | 160 |
O241—H241···O141i | 0.96 | 1.70 | 2.644 (3) | 167 |
C18—H18···Cg4ii | 0.95 | 2.81 | 3.640 (3) | 146 |
C110—H110···Cg2iii | 0.95 | 2.71 | 3.464 (3) | 137 |
C111—H111···Cg3iii | 0.95 | 2.89 | 3.578 (3) | 130 |
Symmetry codes: (i) x, −y+1, z−1/2; (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) topParameter | (I) | | (II) | |
| x = 1 | x = 2 | x = 1 | x = 2 |
(i) Puckering parameters for seven-membered rings | | | | |
Q | 0.746 (2) | 0.785 (2) | 0.756 (3) | 0.748 (3) |
φ2 | 188.6 (4) | 203.7 (3) | 204.1 (4) | 191.5 (5) |
φ3 | 126.9 (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) topCompound | D—H···A | D—H | H···A | D···A | D—H···A |
(I) | O141—H141···N21i | 0.89 | 2.08 | 2.961 (3) | 174 |
| O241—H241···O141 | 0.96 | 2.27 | 3.197 (3) | 163 |
| C28—H28···Cg1ii | 0.95 | 2.98 | 3.709 (3) | 135 |
| C110—H110···Cg2iii | 0.95 | 2.91 | 3.673 (3) | 138 |
| C111—H111···Cg3iii | 0.95 | 2.98 | 3.718 (3) | 136 |
| | | | | |
(II) | O141—H141···O241 | 0.94 | 1.74 | 2.648 (3) | 160 |
| O241—H241···O141iv | 0.96 | 1.70 | 2.644 (3) | 167 |
| C18—H18···Cg4v | 0.95 | 2.81 | 3.640 (3) | 146 |
| C110—H110···Cg2vi | 0.95 | 2.71 | 3.464 (3) | 137 |
| C111—H111···Cg3vi | 0.95 | 2.89 | 3.578 (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. |