π-Facial selectivities of diastereotopic ketones: p-bromobenzoates of 4-hetero-1-decalinols

Parvez, M.; Yadav, V.K.; Balamurugan, R.

doi:10.1107/S0108270101009544

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π-Facial selectivities of diastereotopic ketones: p-bromobenzoates of 4-hetero-1-decalinols

M. Parvez, V. K. Yadav and R. Balamurugan

The crystal structures of the p-bromobenzoates of cis-4-oxa-1-decalinyl (C₁₆H₁₉BrO₃), trans-4-oxa-1-decalinyl (C₁₆H₁₉BrO₃), N-benzyl-cis-4-aza-1-decalinyl (C₂₃H₂₆BrNO₂), N-benzyl-trans-4-aza-1-decalinyl (C₂₃H₂₆BrNO₂) and trans-4-thia-1-decalinyl (C₁₆H₁₉BrO₂S) (decalin is perhydronaphthalene) have been determined as part of a study directed at predicting and interpreting the π-facial selectivities of diastereotopic ketones in reactions with nucleophiles. All five structures are composed of molecules that are separated by normal van der Waals distances. In all five structures, the heterocyclic and cyclohexyl rings adopt chair conformations, and the p-bromobenzoate groups are planar.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101009544/da1192sup1.cif Contains datablocks global, XVI, XVII, XVIII, XIX, XX
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270101009544/da1192XVIsup2.hkl Contains datablock XVI
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270101009544/da1192XVIIsup3.hkl Contains datablock XVII
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270101009544/da1192XVIIIsup4.hkl Contains datablock XVIII
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270101009544/da1192XIXsup5.hkl Contains datablock XIX
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270101009544/da1192XXsup6.hkl Contains datablock XX

CCDC references: 173376; 173377; 173378; 173379; 173380

Comment top

In studies directed at the evaluation of the cation complexation model (Jeyaraj et al., 1997; Jeyaraj & Yadav, 1997; Yadav & Jeyaraj, 1998; Yadav et al., 1999, 2000) in order to predict and interpret the π-facial selectivities of diastereotopic ketones in reactions with nucleophiles, we have determined the experimental selectivities of cis-4-oxa-1-decalone, (I), trans-4-oxa-1-decalone, (II), cis-N-benzyl-4-aza-1-decalone, (III), trans-N-benzyl-4-aza-1-decalone, (IV), and trans-4-thia-1-decalone, (V), from reductions with LiAlH₄ in Et₂O at 267–273 K, NaBH₄ in MeOH at 267–273 K and NaCNBH₃ in aqueous MeOH at 297 K and pH 3–4. In each case, a mixture of two isomers was produced; the results of the study dealing with the ratios of the products formed will be reported elsewhere (Yadav et al., 2001). The isomers were separated by careful chromatography over silica gel and the relative stereostructure of the major isomer was determined by single-crystal X-ray diffraction. The alcohols cis-4-oxa-1-decalinol, (VI), trans-4-oxa-1-decalinol, (VIII), N-benzyl-cis-4-aza-1-decalinol, (X), and N-benzyl-trans-4-aza-1-decalone, (XII), are liquids at room temperature. Trans-4-thia-1-decalinol, (XIV), produced crystals of very poor quality. All of the alcohols were therefore converted to the p-bromobenzoate esters, cis-4-oxa-1-decalinyl p-bromobenzoate, (XVI), trans-4-oxa-1-decalinyl p-bromobenzoate, (XVII), N-benzyl-cis-4-aza-1-decalinyl p-bromobenzoate, (XVIII), N-benzyl-trans-4-aza-1-decalinyl p-bromobenzoate, (XIX) and trans-4-thia-1-decalinyl p-bromobenzoate, (XX), and the structures of these five compounds are presented in this paper. \sch

The structures of compounds (XVI)-(XX) (Figs. 1–5) are composed of independent molecules which are separated by normal van der Waals distances. The heterocyclic rings in all of the structures exhibit chair conformations, with torsion angles in the range ±53.3 (10)–63.5 (9), ±54.6 (6)–60.5 (6), ±53.1 (6)–64.8 (5), ±50.7 (3)–61.9 (3) and ±56.2 (4)–64.7 (5)°, for (XVI)-(XX), respectively. The heterocyclic ring in (XIX) exhibits the highest degree of flattening amongst the rest of the structures, having three torsion angles of -50.7 (3), 52.5 (4) and 52.7 (3)°. The cyclohexyl rings in all of the structures also exhibit chair conformations, with torsion angles in the range ±52.4 (11)–57.4 (11), ±54.5 (8)–55.4 (8), ±55.6 (7)–58.3 (6), ±53.0 (5)–58.1 (3) and ±54.7 (5)–58.0 (6)°, for (XVI)-(XX), respectively.

The p-bromobenzoate groups in (XVI) and (XX) are essentially planar, with maximum deviations of 0.074 (7) and 0.066 (8) Å, respectively, from the least-squares planes of the phenyl ring C atoms. The O atoms of the corresponding groups in (XVII) and (XVIII) lie 0.179 (9) and 0.205 (9) Å in the former, and 0.229 (9) and 0.203 (9) Å in the latter, on opposite sides from the least-squares planes of the phenyl rings. On the other hand, in (XIX), the carbonyl O atom lies 0.117 (7) Å out of the least-squares plane of the phenyl ring; the rest of the atoms of the p-bromobenzoate group lie in this plane, with a maximum deviation of 0.043 (6) Å. These small but significant differences are also supported by a comparison of the angles between the mean planes of the phenyl rings and the oxalate atoms, e.g. the mean planes between phenyl ring C11—C16 and atoms O2, O3, C10 and C11 in (XVI) are inclined at 3.34 (14)°. The corresponding angles in (XVII)-(XX) are 9.9 (3), 11.2 (4), 2.8 (3) and 2.1 (4)°, respectively.

The conformational differences in the five structures are evident from a comparison of torsion angles. For example, the angle C2—C3—O2—C10 in (XVI) is -154.8 (9)°. The corresponding angles in the structures of (XVII)-(XX) are 113.6 (5), 149.8 (5), 97.8 (3) and -82.3 (5)°, respectively. The bond distances and angles in the five structures are normal and agree well with the expected values (Orpen et al., 1994).

The crystal of (XX) chosen for analysis in this study belongs to a noncentrosymmetric space group, although the starting material was a racemic mixture. An absolute structure was established by the Flack (1983) method; the Flack parameter for the inverted structure was 1.04 (4).

Experimental top

The cis-ketone (I) was synthesized using the method of Kozikowski & Li (1985). However, copper(II) trifluoromethanesulfonate was used instead of zinc(II) trifluoromethanesulfonate for the closure of the heterocyclic ring, as the latter was found ineffective in our hands. The product was isomerized to a mixture of cis-(I) and trans-(II) by reflux in EtOH-Et₃N. The trans-ketone (II) was separated from this mixture by chromatography over silica gel. The trans-ketone (IV) was prepared by following the literature protocol of Traverso (1955) for the formation of trans-(V) and isomerized to a mixture of cis-(III) (minor) and trans-(IV) (major) by treatment with 1,8-diazabicyclo[5.4.0]undec-6-ene (DBU) in CH₂Cl₂ at 297 K. The cis-(III) compound was isolated from this mixture by chromatographic methods. The trans-ketone (V) was fully resistant to isomerization (DBU/CH₂Cl₂/297 K) to its cis-analogue. All the reductions were carried out following standard procedures. The alcohols (VI), (VIII), (X), (XII) and (XIV) were esterified with p-bromobenzoyl chloride (p-Br—C₆H₄COCl) following standard methods, and the resulting benzoates, (XVI)-(XX), were recrystallized from benzene, EtOAc/petroleum ether, EtOAc, petroleum ether and C₆H₅Cl/petroleum ether, respectively.

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988) for (XVI), (XVII), (XVIII); CAD-4 Software (Enraf-Nonius, 1989) for (XIX), (XX). Cell refinement: MSC/AFC Diffractometer Control Software for (XVI), (XVII), (XVIII); CAD-4 Software for (XIX), (XX). For all compounds, data reduction: TEXSAN (Molecular Structure Corporation, 1994); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. The molecular structure of (XVI) with the atom-numbering scheme and 25% probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The molecular structure of (XVII) with the atom-numbering scheme and 30% probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radii.
	Fig. 3. The molecular structure of (XVIII) with the atom-numbering scheme and 30% probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radii.
	Fig. 4. The molecular structure of (XIX) with the atom-numbering scheme and 25% probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radii.
	Fig. 5. The molecular structure of (XX) with the atom-numbering scheme and 30% probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radii.

(XVI) cis-4-oxa-1-decalinyl p-bromobenzoate top

Crystal data top

C₁₆H₁₉BrO₃	F(000) = 696
M_r = 339.22	D_x = 1.500 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71069 Å
a = 10.906 (2) Å	Cell parameters from 12 reflections
b = 8.052 (4) Å	θ = 10–20°
c = 17.195 (3) Å	µ = 2.74 mm⁻¹
β = 95.98 (2)°	T = 170 K
V = 1501.8 (8) Å³	Prismatic, colourless
Z = 4	0.48 × 0.42 × 0.33 mm

Data collection top

Rigaku AFC-6S diffractometer	693 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.08
Graphite monochromator	θ_max = 25.0°, θ_min = 2.5°
ω/2θ scans	h = 0→12
Absorption correction: empirical (using intensity measurements) ψ-scan (3 reflections) (North et al., 1968)	k = 0→9
T_min = 0.28, T_max = 0.41	l = −20→20
2646 measured reflections	3 standard reflections every 200 reflections
2646 independent reflections	intensity decay: < 1.1%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.109	w = 1/[σ²(F_o²)]
S = 0.94	(Δ/σ)_max < 0.001
2646 reflections	Δρ_max = 0.53 e Å⁻³
182 parameters	Δρ_min = −0.77 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00061 (16)

Crystal data top

C₁₆H₁₉BrO₃	V = 1501.8 (8) Å³
M_r = 339.22	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.906 (2) Å	µ = 2.74 mm⁻¹
b = 8.052 (4) Å	T = 170 K
c = 17.195 (3) Å	0.48 × 0.42 × 0.33 mm
β = 95.98 (2)°

Data collection top

Rigaku AFC-6S diffractometer	693 reflections with I > 2σ(I)
Absorption correction: empirical (using intensity measurements) ψ-scan (3 reflections) (North et al., 1968)	R_int = 0.08
T_min = 0.28, T_max = 0.41	3 standard reflections every 200 reflections
2646 measured reflections	intensity decay: < 1.1%
2646 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 0.94	Δρ_max = 0.53 e Å⁻³
2646 reflections	Δρ_min = −0.77 e Å⁻³
182 parameters

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

	x	y	z	U_iso*/U_eq
Br1	1.25240 (10)	0.68612 (17)	0.45505 (6)	0.0543 (4)
O1	0.4194 (6)	0.8678 (8)	0.7348 (4)	0.034 (2)
O2	0.7075 (4)	0.8592 (7)	0.5949 (3)	0.0336 (19)
O3	0.6305 (5)	0.8035 (11)	0.4705 (3)	0.052 (2)
C1	0.4739 (8)	1.0231 (12)	0.7195 (5)	0.035 (3)
H1A	0.4839	1.0896	0.7682	0.042*
H1B	0.4186	1.0849	0.6804	0.042*
C2	0.5994 (8)	1.0001 (12)	0.6891 (5)	0.032 (3)
H2A	0.6325	1.1091	0.6748	0.038*
H2B	0.6581	0.9497	0.7302	0.038*
C3	0.5842 (7)	0.8877 (12)	0.6178 (5)	0.027 (3)
H3	0.5340	0.9471	0.5744	0.032*
C4	0.5209 (7)	0.7262 (10)	0.6336 (5)	0.019 (2)
H4	0.5020	0.6674	0.5826	0.022*
C5	0.6007 (8)	0.6103 (12)	0.6887 (6)	0.037 (3)
H5A	0.6764	0.5807	0.6648	0.044*
H5B	0.6255	0.6685	0.7386	0.044*
C6	0.5303 (9)	0.4530 (12)	0.7048 (5)	0.042 (3)
H6A	0.5826	0.3817	0.7416	0.051*
H6B	0.5114	0.3906	0.6554	0.051*
C7	0.4101 (9)	0.4927 (12)	0.7396 (6)	0.042 (3)
H7A	0.4290	0.5456	0.7915	0.050*
H7B	0.3644	0.3886	0.7469	0.050*
C8	0.3300 (8)	0.6100 (12)	0.6852 (5)	0.035 (3)
H8A	0.3022	0.5503	0.6362	0.042*
H8B	0.2558	0.6409	0.7106	0.042*
C9	0.3976 (7)	0.7690 (11)	0.6650 (6)	0.035 (3)
H9	0.3447	0.8329	0.6244	0.042*
C10	0.7178 (8)	0.8213 (15)	0.5210 (5)	0.036 (3)
C11	0.8490 (7)	0.7872 (13)	0.5057 (5)	0.026 (3)
C12	0.9439 (7)	0.8096 (13)	0.5648 (5)	0.036 (3)
H12	0.9267	0.8426	0.6155	0.043*
C13	1.0652 (8)	0.7831 (12)	0.5487 (5)	0.043 (3)
H13	1.1317	0.8065	0.5874	0.052*
C14	1.0881 (8)	0.7237 (13)	0.4774 (5)	0.034 (3)
C15	0.9931 (8)	0.7037 (13)	0.4177 (5)	0.038 (3)
H15	1.0100	0.6692	0.3671	0.045*
C16	0.8733 (8)	0.7350 (11)	0.4335 (5)	0.041 (3)
H16	0.8074	0.7200	0.3935	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0407 (6)	0.0746 (9)	0.0506 (7)	0.0074 (10)	0.0188 (5)	−0.0010 (11)
O1	0.036 (4)	0.030 (6)	0.035 (5)	0.003 (4)	0.004 (4)	−0.006 (4)
O2	0.016 (3)	0.046 (6)	0.040 (4)	0.003 (3)	0.006 (3)	0.000 (4)
O3	0.033 (4)	0.080 (6)	0.039 (4)	−0.004 (5)	−0.009 (3)	−0.004 (6)
C1	0.033 (6)	0.034 (8)	0.037 (7)	0.003 (6)	0.003 (5)	0.001 (6)
C2	0.035 (7)	0.029 (7)	0.031 (7)	−0.005 (6)	0.002 (6)	0.004 (6)
C3	0.016 (5)	0.031 (7)	0.034 (6)	0.009 (5)	0.003 (5)	0.005 (6)
C4	0.020 (5)	0.013 (7)	0.022 (5)	−0.002 (5)	−0.001 (4)	−0.012 (5)
C5	0.020 (6)	0.032 (8)	0.057 (8)	0.004 (6)	0.001 (6)	0.021 (7)
C6	0.055 (7)	0.031 (8)	0.042 (7)	0.014 (7)	0.008 (6)	0.009 (6)
C7	0.048 (8)	0.035 (8)	0.045 (8)	−0.008 (7)	0.016 (6)	−0.005 (7)
C8	0.031 (6)	0.032 (7)	0.041 (7)	−0.003 (6)	0.000 (5)	−0.005 (6)
C9	0.019 (5)	0.030 (8)	0.056 (7)	0.002 (5)	−0.001 (5)	0.006 (6)
C10	0.043 (7)	0.037 (7)	0.032 (6)	−0.015 (7)	0.019 (5)	−0.013 (7)
C11	0.029 (5)	0.028 (7)	0.021 (5)	0.004 (6)	0.004 (4)	0.011 (6)
C12	0.027 (5)	0.054 (7)	0.028 (5)	0.012 (7)	0.006 (4)	0.006 (7)
C13	0.036 (6)	0.058 (9)	0.034 (6)	−0.002 (6)	0.000 (5)	0.008 (7)
C14	0.035 (6)	0.043 (9)	0.028 (6)	0.006 (6)	0.014 (5)	0.005 (6)
C15	0.039 (6)	0.048 (8)	0.027 (6)	0.009 (7)	0.010 (5)	0.006 (7)
C16	0.037 (6)	0.049 (10)	0.038 (6)	−0.008 (6)	0.001 (5)	−0.025 (6)

Geometric parameters (Å, º) top

Br1—C14	1.895 (8)	C6—H6A	0.9900
O1—C1	1.421 (9)	C6—H6B	0.9900
O1—C9	1.439 (10)	C7—C8	1.537 (12)
O2—C10	1.324 (9)	C7—H7A	0.9900
O2—C3	1.458 (7)	C7—H7B	0.9900
O3—C10	1.228 (9)	C8—C9	1.535 (10)
C1—C2	1.527 (10)	C8—H8A	0.9900
C1—H1A	0.9900	C8—H8B	0.9900
C1—H1B	0.9900	C9—H9	1.0000
C2—C3	1.519 (11)	C10—C11	1.507 (10)
C2—H2A	0.9900	C11—C16	1.363 (10)
C2—H2B	0.9900	C11—C12	1.385 (10)
C3—C4	1.510 (10)	C12—C13	1.396 (9)
C3—H3	1.0000	C12—H12	0.9500
C4—C5	1.534 (10)	C13—C14	1.364 (10)
C4—C9	1.539 (9)	C13—H13	0.9500
C4—H4	1.0000	C14—C15	1.389 (10)
C5—C6	1.521 (11)	C15—C16	1.385 (9)
C5—H5A	0.9900	C15—H15	0.9500
C5—H5B	0.9900	C16—H16	0.9500
C6—C7	1.531 (11)

C1—O1—C9	111.6 (7)	C6—C7—H7A	109.6
C10—O2—C3	117.9 (7)	C8—C7—H7A	109.6
O1—C1—C2	111.3 (8)	C6—C7—H7B	109.6
O1—C1—H1A	109.4	C8—C7—H7B	109.6
C2—C1—H1A	109.4	H7A—C7—H7B	108.1
O1—C1—H1B	109.4	C9—C8—C7	113.3 (8)
C2—C1—H1B	109.4	C9—C8—H8A	108.9
H1A—C1—H1B	108.0	C7—C8—H8A	108.9
C3—C2—C1	108.8 (7)	C9—C8—H8B	108.9
C3—C2—H2A	109.9	C7—C8—H8B	108.9
C1—C2—H2A	109.9	H8A—C8—H8B	107.7
C3—C2—H2B	109.9	O1—C9—C8	108.3 (7)
C1—C2—H2B	109.9	O1—C9—C4	109.9 (7)
H2A—C2—H2B	108.3	C8—C9—C4	110.5 (7)
O2—C3—C4	111.4 (7)	O1—C9—H9	109.4
O2—C3—C2	106.5 (7)	C8—C9—H9	109.4
C4—C3—C2	112.4 (7)	C4—C9—H9	109.4
O2—C3—H3	108.8	O3—C10—O2	124.6 (8)
C4—C3—H3	108.8	O3—C10—C11	122.4 (8)
C2—C3—H3	108.8	O2—C10—C11	112.8 (8)
C3—C4—C5	113.2 (7)	C16—C11—C12	120.5 (8)
C3—C4—C9	107.7 (7)	C16—C11—C10	119.6 (8)
C5—C4—C9	112.3 (7)	C12—C11—C10	119.9 (8)
C3—C4—H4	107.8	C11—C12—C13	119.1 (8)
C5—C4—H4	107.8	C11—C12—H12	120.4
C9—C4—H4	107.8	C13—C12—H12	120.4
C6—C5—C4	110.7 (8)	C14—C13—C12	119.8 (8)
C6—C5—H5A	109.5	C14—C13—H13	120.1
C4—C5—H5A	109.5	C12—C13—H13	120.1
C6—C5—H5B	109.5	C13—C14—C15	120.8 (8)
C4—C5—H5B	109.5	C13—C14—Br1	120.2 (7)
H5A—C5—H5B	108.1	C15—C14—Br1	118.7 (6)
C5—C6—C7	111.5 (8)	C16—C15—C14	118.7 (8)
C5—C6—H6A	109.3	C16—C15—H15	120.6
C7—C6—H6A	109.3	C14—C15—H15	120.6
C5—C6—H6B	109.3	C11—C16—C15	120.8 (9)
C7—C6—H6B	109.3	C11—C16—H16	119.6
H6A—C6—H6B	108.0	C15—C16—H16	119.6
C6—C7—C8	110.2 (8)

C9—O1—C1—C2	−61.7 (10)	C5—C4—C9—O1	66.8 (9)
O1—C1—C2—C3	55.0 (10)	C3—C4—C9—C8	−178.0 (8)
C10—O2—C3—C4	82.3 (10)	C5—C4—C9—C8	−52.7 (11)
C10—O2—C3—C2	−154.8 (9)	C3—O2—C10—O3	−2.2 (17)
C1—C2—C3—O2	−175.6 (7)	C3—O2—C10—C11	−177.3 (8)
C1—C2—C3—C4	−53.3 (10)	O3—C10—C11—C16	0.2 (17)
O2—C3—C4—C5	49.7 (10)	O2—C10—C11—C16	175.4 (9)
C2—C3—C4—C5	−69.8 (9)	O3—C10—C11—C12	179.9 (12)
O2—C3—C4—C9	174.5 (7)	O2—C10—C11—C12	−4.9 (15)
C2—C3—C4—C9	55.0 (10)	C16—C11—C12—C13	2.0 (16)
C3—C4—C5—C6	177.9 (7)	C10—C11—C12—C13	−177.7 (10)
C9—C4—C5—C6	55.7 (10)	C11—C12—C13—C14	−5.0 (16)
C4—C5—C6—C7	−57.4 (11)	C12—C13—C14—C15	6.1 (16)
C5—C6—C7—C8	56.4 (11)	C12—C13—C14—Br1	−179.6 (8)
C6—C7—C8—C9	−54.4 (11)	C13—C14—C15—C16	−4.1 (16)
C1—O1—C9—C8	−175.7 (7)	Br1—C14—C15—C16	−178.5 (7)
C1—O1—C9—C4	63.5 (9)	C12—C11—C16—C15	−0.1 (16)
C7—C8—C9—O1	−68.0 (9)	C10—C11—C16—C15	179.6 (10)
C7—C8—C9—C4	52.4 (11)	C14—C15—C16—C11	1.1 (16)
C3—C4—C9—O1	−58.6 (9)

(XVII) trans-4-oxa-1-decalinyl p-bromobenzoate top

Crystal data top

C₁₆H₁₉BrO₃	Z = 2
M_r = 339.22	F(000) = 348
Triclinic, P1	D_x = 1.485 Mg m⁻³
a = 9.643 (2) Å	Mo Kα radiation, λ = 0.71069 Å
b = 10.679 (2) Å	Cell parameters from 25 reflections
c = 8.772 (2) Å	θ = 10–15°
α = 96.32 (2)°	µ = 2.71 mm⁻¹
β = 111.32 (2)°	T = 293 K
γ = 110.49 (2)°	Plate, colourless
V = 758.5 (3) Å³	0.60 × 0.40 × 0.15 mm

Data collection top

Rigaku AFC-6S diffractometer	1169 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.03
Graphite monochromator	θ_max = 25.0°, θ_min = 2.5°
ω/2θ scans	h = 0→11
Absorption correction: empirical (using intensity measurements) ψ-scan (3 reflections) (North et al., 1968)	k = −12→11
T_min = 0.28, T_max = 0.67	l = −10→9
2702 measured reflections	3 standard reflections every 200 reflections
2702 independent reflections	intensity decay: < 0.8%

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)] = 0.039	Hydrogen site location: difference Fourier map
wR(F²) = 0.130	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0513P)²] where P = (F_o² + 2F_c²)/3
2702 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₆H₁₉BrO₃	γ = 110.49 (2)°
M_r = 339.22	V = 758.5 (3) Å³
Triclinic, P1	Z = 2
a = 9.643 (2) Å	Mo Kα radiation
b = 10.679 (2) Å	µ = 2.71 mm⁻¹
c = 8.772 (2) Å	T = 293 K
α = 96.32 (2)°	0.60 × 0.40 × 0.15 mm
β = 111.32 (2)°

Data collection top

Rigaku AFC-6S diffractometer	1169 reflections with I > 2σ(I)
Absorption correction: empirical (using intensity measurements) ψ-scan (3 reflections) (North et al., 1968)	R_int = 0.03
T_min = 0.28, T_max = 0.67	3 standard reflections every 200 reflections
2702 measured reflections	intensity decay: < 0.8%
2702 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 0.98	Δρ_max = 0.42 e Å⁻³
2702 reflections	Δρ_min = −0.38 e Å⁻³
181 parameters

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

	x	y	z	U_iso*/U_eq
Br1	0.62706 (9)	1.28442 (7)	0.24217 (9)	0.0785 (3)
O1	−0.0142 (4)	0.1901 (4)	0.1044 (5)	0.0590 (10)
O2	0.2942 (4)	0.6079 (4)	0.2383 (5)	0.0635 (11)
O3	0.5457 (5)	0.6687 (4)	0.4412 (5)	0.0817 (14)
C1	0.0561 (7)	0.2611 (6)	0.2776 (7)	0.0618 (16)
H1A	0.1439	0.2365	0.3410	0.074*
H1B	−0.0263	0.2323	0.3206	0.074*
C2	0.1241 (7)	0.4177 (6)	0.3055 (7)	0.0669 (17)
H2A	0.1763	0.4638	0.4262	0.080*
H2B	0.0354	0.4440	0.2505	0.080*
C3	0.2466 (6)	0.4616 (5)	0.2328 (7)	0.0526 (15)
H3	0.3433	0.4465	0.2980	0.063*
C4	0.1697 (7)	0.3806 (5)	0.0479 (7)	0.0545 (15)
H4	0.0761	0.4013	−0.0121	0.065*
C5	0.2765 (8)	0.4151 (7)	−0.0409 (9)	0.083 (2)
H5A	0.3736	0.4004	0.0188	0.099*
H5B	0.3117	0.5127	−0.0380	0.099*
C6	0.1901 (9)	0.3276 (8)	−0.2258 (9)	0.091 (2)
H6A	0.1014	0.3510	−0.2899	0.109*
H6B	0.2672	0.3481	−0.2761	0.109*
C7	0.1229 (9)	0.1762 (8)	−0.2353 (9)	0.088 (2)
H7A	0.2134	0.1511	−0.1837	0.105*
H7B	0.0619	0.1228	−0.3537	0.105*
C8	0.0128 (8)	0.1386 (6)	−0.1477 (8)	0.0769 (18)
H8A	−0.0215	0.0411	−0.1507	0.092*
H8B	−0.0846	0.1531	−0.2070	0.092*
C9	0.1009 (7)	0.2262 (5)	0.0354 (7)	0.0565 (15)
H9	0.1913	0.2026	0.0979	0.068*
C10	0.4493 (7)	0.6999 (6)	0.3404 (7)	0.0511 (14)
C11	0.4874 (6)	0.8392 (5)	0.3144 (6)	0.0418 (13)
C12	0.3821 (6)	0.8653 (5)	0.1799 (6)	0.0486 (14)
H12	0.2823	0.7935	0.1035	0.058*
C13	0.4238 (7)	0.9973 (6)	0.1577 (7)	0.0579 (16)
H13	0.3526	1.0138	0.0659	0.070*
C14	0.5702 (7)	1.1043 (5)	0.2710 (7)	0.0487 (14)
C15	0.6768 (7)	1.0807 (6)	0.4077 (7)	0.0558 (15)
H15	0.7752	1.1533	0.4854	0.067*
C16	0.6356 (6)	0.9484 (6)	0.4274 (7)	0.0528 (15)
H16	0.7081	0.9317	0.5179	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0961 (6)	0.0456 (4)	0.0837 (5)	0.0225 (4)	0.0340 (4)	0.0227 (3)
O1	0.052 (3)	0.048 (2)	0.052 (2)	0.0060 (19)	0.011 (2)	0.0137 (19)
O2	0.047 (3)	0.040 (2)	0.075 (3)	0.009 (2)	0.005 (2)	0.014 (2)
O3	0.059 (3)	0.057 (3)	0.088 (3)	0.011 (2)	−0.002 (2)	0.031 (2)
C1	0.054 (4)	0.059 (4)	0.060 (4)	0.009 (3)	0.025 (3)	0.018 (3)
C2	0.071 (4)	0.063 (4)	0.054 (4)	0.018 (3)	0.024 (3)	0.010 (3)
C3	0.049 (4)	0.032 (3)	0.057 (4)	0.011 (3)	0.007 (3)	0.014 (3)
C4	0.053 (4)	0.047 (3)	0.061 (4)	0.014 (3)	0.028 (3)	0.018 (3)
C5	0.074 (5)	0.078 (5)	0.108 (6)	0.028 (4)	0.049 (5)	0.044 (5)
C6	0.113 (6)	0.100 (6)	0.078 (5)	0.042 (5)	0.059 (5)	0.034 (5)
C7	0.112 (6)	0.083 (5)	0.081 (5)	0.046 (5)	0.051 (5)	0.020 (4)
C8	0.097 (5)	0.059 (4)	0.079 (5)	0.031 (4)	0.044 (4)	0.022 (4)
C9	0.073 (4)	0.045 (3)	0.049 (3)	0.025 (3)	0.023 (3)	0.014 (3)
C10	0.048 (4)	0.049 (4)	0.049 (3)	0.015 (3)	0.018 (3)	0.013 (3)
C11	0.039 (3)	0.043 (3)	0.044 (3)	0.018 (3)	0.018 (3)	0.016 (3)
C12	0.044 (3)	0.041 (3)	0.044 (3)	0.009 (3)	0.014 (3)	0.004 (3)
C13	0.063 (4)	0.053 (4)	0.050 (4)	0.026 (3)	0.013 (3)	0.019 (3)
C14	0.052 (4)	0.039 (3)	0.052 (3)	0.016 (3)	0.023 (3)	0.011 (3)
C15	0.045 (4)	0.044 (3)	0.055 (4)	0.005 (3)	0.013 (3)	0.005 (3)
C16	0.041 (4)	0.052 (4)	0.051 (3)	0.013 (3)	0.011 (3)	0.014 (3)

Geometric parameters (Å, º) top

Br1—C14	1.880 (5)	C6—H6A	0.9700
O1—C9	1.410 (6)	C6—H6B	0.9700
O1—C1	1.407 (6)	C7—C8	1.497 (8)
O2—C10	1.344 (6)	C7—H7A	0.9700
O2—C3	1.456 (6)	C7—H7B	0.9700
O3—C10	1.200 (6)	C8—C9	1.516 (8)
C1—C2	1.520 (7)	C8—H8A	0.9700
C1—H1A	0.9700	C8—H8B	0.9700
C1—H1B	0.9700	C9—H9	0.9800
C2—C3	1.500 (7)	C10—C11	1.468 (7)
C2—H2A	0.9700	C11—C12	1.378 (7)
C2—H2B	0.9700	C11—C16	1.390 (7)
C3—C4	1.516 (7)	C12—C13	1.381 (7)
C3—H3	0.9800	C12—H12	0.9300
C4—C5	1.477 (7)	C13—C14	1.373 (7)
C4—C9	1.521 (7)	C13—H13	0.9300
C4—H4	0.9800	C14—C15	1.382 (7)
C5—C6	1.529 (9)	C15—C16	1.377 (7)
C5—H5A	0.9700	C15—H15	0.9300
C5—H5B	0.9700	C16—H16	0.9300
C6—C7	1.497 (9)

C9—O1—C1	111.9 (4)	C6—C7—H7A	109.1
C10—O2—C3	119.2 (4)	C8—C7—H7A	109.1
O1—C1—C2	111.7 (4)	C6—C7—H7B	109.1
O1—C1—H1A	109.3	C8—C7—H7B	109.1
C2—C1—H1A	109.3	H7A—C7—H7B	107.8
O1—C1—H1B	109.3	C7—C8—C9	110.6 (6)
C2—C1—H1B	109.3	C7—C8—H8A	109.5
H1A—C1—H1B	107.9	C9—C8—H8A	109.5
C1—C2—C3	109.3 (5)	C7—C8—H8B	109.5
C1—C2—H2A	109.8	C9—C8—H8B	109.5
C3—C2—H2A	109.8	H8A—C8—H8B	108.1
C1—C2—H2B	109.8	O1—C9—C8	106.7 (5)
C3—C2—H2B	109.8	O1—C9—C4	111.4 (4)
H2A—C2—H2B	108.3	C8—C9—C4	111.7 (4)
O2—C3—C2	109.1 (5)	O1—C9—H9	109.0
O2—C3—C4	107.3 (4)	C8—C9—H9	109.0
C2—C3—C4	110.1 (4)	C4—C9—H9	109.0
O2—C3—H3	110.1	O3—C10—O2	122.3 (5)
C2—C3—H3	110.1	O3—C10—C11	124.3 (5)
C4—C3—H3	110.1	O2—C10—C11	113.4 (5)
C5—C4—C9	111.1 (5)	C12—C11—C16	118.7 (5)
C5—C4—C3	115.9 (5)	C12—C11—C10	122.2 (5)
C9—C4—C3	108.7 (4)	C16—C11—C10	119.1 (4)
C5—C4—H4	106.9	C11—C12—C13	120.5 (5)
C9—C4—H4	106.9	C11—C12—H12	119.8
C3—C4—H4	106.9	C13—C12—H12	119.8
C4—C5—C6	112.4 (5)	C14—C13—C12	120.1 (5)
C4—C5—H5A	109.1	C14—C13—H13	119.9
C6—C5—H5A	109.1	C12—C13—H13	119.9
C4—C5—H5B	109.1	C13—C14—C15	120.3 (5)
C6—C5—H5B	109.1	C13—C14—Br1	120.3 (4)
H5A—C5—H5B	107.9	C15—C14—Br1	119.3 (4)
C7—C6—C5	110.4 (5)	C16—C15—C14	119.2 (5)
C7—C6—H6A	109.6	C16—C15—H15	120.4
C5—C6—H6A	109.6	C14—C15—H15	120.4
C7—C6—H6B	109.6	C15—C16—C11	121.1 (5)
C5—C6—H6B	109.6	C15—C16—H16	119.4
H6A—C6—H6B	108.1	C11—C16—H16	119.4
C6—C7—C8	112.7 (6)

C9—O1—C1—C2	59.9 (6)	C3—C4—C9—O1	57.4 (6)
O1—C1—C2—C3	−56.7 (6)	C5—C4—C9—C8	−54.7 (7)
C10—O2—C3—C2	113.6 (5)	C3—C4—C9—C8	176.6 (5)
C10—O2—C3—C4	−127.1 (5)	C3—O2—C10—O3	−8.3 (8)
C1—C2—C3—O2	172.1 (4)	C3—O2—C10—C11	171.2 (4)
C1—C2—C3—C4	54.6 (6)	O3—C10—C11—C12	169.5 (5)
O2—C3—C4—C5	60.4 (6)	O2—C10—C11—C12	−9.9 (7)
C2—C3—C4—C5	179.1 (5)	O3—C10—C11—C16	−9.4 (8)
O2—C3—C4—C9	−173.6 (4)	O2—C10—C11—C16	171.1 (5)
C2—C3—C4—C9	−55.0 (6)	C16—C11—C12—C13	0.3 (8)
C9—C4—C5—C6	54.6 (7)	C10—C11—C12—C13	−178.7 (5)
C3—C4—C5—C6	179.3 (5)	C11—C12—C13—C14	−0.7 (8)
C4—C5—C6—C7	−54.5 (8)	C12—C13—C14—C15	0.1 (8)
C5—C6—C7—C8	54.7 (8)	C12—C13—C14—Br1	−179.7 (4)
C6—C7—C8—C9	−55.4 (8)	C13—C14—C15—C16	0.9 (8)
C1—O1—C9—C8	177.4 (5)	Br1—C14—C15—C16	−179.3 (4)
C1—O1—C9—C4	−60.5 (6)	C14—C15—C16—C11	−1.3 (8)
C7—C8—C9—O1	176.4 (5)	C12—C11—C16—C15	0.7 (8)
C7—C8—C9—C4	54.5 (7)	C10—C11—C16—C15	179.7 (5)
C5—C4—C9—O1	−173.9 (5)

(XVIII) N-benzyl-cis-4-aza-1-decalinyl p-bromobenzoate top

Crystal data top

C₂₃H₂₆BrNO₂	Z = 2
M_r = 428.36	F(000) = 444
Triclinic, P1	D_x = 1.409 Mg m⁻³
a = 11.914 (3) Å	Mo Kα radiation, λ = 0.71069 Å
b = 13.144 (3) Å	Cell parameters from 12 reflections
c = 6.922 (2) Å	θ = 10–15°
α = 96.06 (2)°	µ = 2.05 mm⁻¹
β = 106.22 (2)°	T = 170 K
γ = 100.42 (3)°	Prismatic, colourless
V = 1009.6 (5) Å³	0.60 × 0.40 × 0.32 mm

Data collection top

Rigaku AFC-6S diffractometer	1407 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.09
Graphite monochromator	θ_max = 25.0°, θ_min = 2.5°
ω/2θ scans	h = 0→14
Absorption correction: empirical (using intensity measurements) ψ-scan (3 reflections) (North et al., 1968)	k = −15→15
T_min = 0.39, T_max = 0.52	l = −8→7
3574 measured reflections	3 standard reflections every 200 reflections
3574 independent reflections	intensity decay: <1.1%

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: difference Fourier map
wR(F²) = 0.110	H-atom parameters constrained
S = 0.95	w = 1/[σ²(F_o²) + (0.018P)²] where P = (F_o² + 2F_c²)/3
3574 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.76 e Å⁻³

Crystal data top

C₂₃H₂₆BrNO₂	γ = 100.42 (3)°
M_r = 428.36	V = 1009.6 (5) Å³
Triclinic, P1	Z = 2
a = 11.914 (3) Å	Mo Kα radiation
b = 13.144 (3) Å	µ = 2.05 mm⁻¹
c = 6.922 (2) Å	T = 170 K
α = 96.06 (2)°	0.60 × 0.40 × 0.32 mm
β = 106.22 (2)°

Data collection top

Rigaku AFC-6S diffractometer	1407 reflections with I > 2σ(I)
Absorption correction: empirical (using intensity measurements) ψ-scan (3 reflections) (North et al., 1968)	R_int = 0.09
T_min = 0.39, T_max = 0.52	3 standard reflections every 200 reflections
3574 measured reflections	intensity decay: <1.1%
3574 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 0.95	Δρ_max = 0.43 e Å⁻³
3574 reflections	Δρ_min = −0.76 e Å⁻³
244 parameters

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

	x	y	z	U_iso*/U_eq
Br1	0.42113 (7)	0.14473 (6)	0.24555 (11)	0.0465 (2)
O1	0.6728 (3)	0.4668 (3)	−0.2993 (6)	0.0341 (11)
O2	0.7113 (4)	0.3176 (3)	−0.4277 (6)	0.0430 (12)
N1	0.8553 (4)	0.7240 (3)	−0.4752 (6)	0.0246 (12)
C1	0.7295 (5)	0.6837 (4)	−0.5911 (9)	0.0348 (16)
H1A	0.7232	0.6443	−0.7251	0.042*
H1B	0.6894	0.7429	−0.6155	0.042*
C2	0.6676 (5)	0.6120 (4)	−0.4755 (9)	0.0338 (16)
H2A	0.6676	0.6529	−0.3469	0.041*
H2B	0.5832	0.5826	−0.5587	0.041*
C3	0.7303 (5)	0.5240 (4)	−0.4280 (9)	0.0304 (16)
H3	0.7191	0.4763	−0.5576	0.036*
C4	0.8648 (5)	0.5656 (4)	−0.3186 (8)	0.0279 (15)
H4	0.9037	0.5042	−0.3122	0.034*
C5	0.8946 (5)	0.6231 (4)	−0.1002 (8)	0.0323 (16)
H5A	0.8563	0.6840	−0.1017	0.039*
H5B	0.8620	0.5754	−0.0178	0.039*
C6	1.0306 (5)	0.6610 (5)	−0.0026 (9)	0.0441 (18)
H6A	1.0478	0.7014	0.1353	0.053*
H6B	1.0680	0.5997	0.0117	0.053*
C7	1.0843 (5)	0.7299 (5)	−0.1330 (9)	0.0397 (18)
H7A	1.0534	0.7949	−0.1350	0.048*
H7B	1.1726	0.7499	−0.0725	0.048*
C8	1.0528 (5)	0.6724 (4)	−0.3489 (9)	0.0364 (16)
H8A	1.0888	0.6101	−0.3468	0.044*
H8B	1.0877	0.7190	−0.4307	0.044*
C9	0.9177 (5)	0.6375 (4)	−0.4502 (8)	0.0271 (15)
H9	0.9026	0.5957	−0.5879	0.032*
C10	0.9084 (5)	0.8056 (4)	−0.5720 (8)	0.0291 (15)
H10A	0.8963	0.7765	−0.7160	0.035*
H10B	0.9958	0.8267	−0.5023	0.035*
C11	0.8556 (5)	0.9003 (4)	−0.5654 (9)	0.0293 (15)
C12	0.8504 (5)	0.9502 (5)	−0.3834 (10)	0.0433 (18)
H12	0.8808	0.9241	−0.2609	0.052*
C13	0.8017 (6)	1.0370 (5)	−0.3769 (12)	0.057 (2)
H13	0.7965	1.0690	−0.2510	0.068*
C14	0.7601 (6)	1.0783 (5)	−0.5517 (14)	0.061 (2)
H14	0.7287	1.1396	−0.5459	0.074*
C15	0.7647 (6)	1.0300 (6)	−0.7330 (13)	0.055 (2)
H15	0.7348	1.0569	−0.8548	0.066*
C16	0.8130 (5)	0.9419 (5)	−0.7394 (10)	0.0371 (17)
H16	0.8167	0.9094	−0.8661	0.044*
C17	0.6702 (5)	0.3632 (5)	−0.3126 (9)	0.0263 (14)
C18	0.6095 (5)	0.3139 (5)	−0.1750 (8)	0.0252 (15)
C19	0.5804 (5)	0.3723 (5)	−0.0246 (9)	0.0341 (16)
H19	0.5987	0.4467	−0.0075	0.041*
C20	0.5238 (5)	0.3212 (5)	0.1023 (9)	0.0407 (18)
H20	0.5033	0.3604	0.2056	0.049*
C21	0.4985 (5)	0.2126 (5)	0.0742 (9)	0.0337 (16)
C22	0.5246 (5)	0.1556 (5)	−0.0765 (9)	0.0367 (17)
H22	0.5041	0.0812	−0.0959	0.044*
C23	0.5807 (5)	0.2051 (4)	−0.2011 (8)	0.0290 (15)
H23	0.5996	0.1648	−0.3051	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0549 (5)	0.0436 (5)	0.0430 (4)	−0.0009 (3)	0.0237 (3)	0.0128 (3)
O1	0.037 (3)	0.026 (3)	0.050 (3)	0.004 (2)	0.028 (2)	0.014 (2)
O2	0.053 (3)	0.032 (3)	0.055 (3)	0.012 (2)	0.032 (3)	0.009 (2)
N1	0.016 (3)	0.028 (3)	0.032 (3)	0.005 (2)	0.009 (2)	0.010 (2)
C1	0.023 (4)	0.036 (4)	0.047 (4)	0.008 (3)	0.009 (3)	0.020 (3)
C2	0.017 (3)	0.030 (4)	0.052 (4)	0.000 (3)	0.009 (3)	0.011 (3)
C3	0.030 (4)	0.026 (4)	0.040 (4)	0.003 (3)	0.017 (3)	0.012 (3)
C4	0.028 (4)	0.022 (3)	0.041 (4)	0.012 (3)	0.015 (3)	0.011 (3)
C5	0.039 (4)	0.034 (4)	0.031 (4)	0.010 (3)	0.017 (3)	0.010 (3)
C6	0.045 (5)	0.037 (4)	0.047 (4)	0.007 (4)	0.010 (4)	0.004 (3)
C7	0.022 (4)	0.038 (4)	0.055 (5)	0.002 (3)	0.008 (3)	0.013 (4)
C8	0.025 (4)	0.036 (4)	0.055 (4)	0.010 (3)	0.016 (3)	0.018 (4)
C9	0.026 (4)	0.025 (4)	0.031 (4)	0.006 (3)	0.011 (3)	0.002 (3)
C10	0.030 (4)	0.025 (4)	0.038 (4)	0.008 (3)	0.014 (3)	0.014 (3)
C11	0.027 (4)	0.021 (4)	0.043 (4)	0.004 (3)	0.015 (3)	0.010 (3)
C12	0.045 (4)	0.037 (4)	0.059 (5)	0.015 (4)	0.030 (4)	0.007 (4)
C13	0.059 (5)	0.041 (5)	0.091 (6)	0.014 (4)	0.056 (5)	0.007 (5)
C14	0.045 (5)	0.019 (5)	0.137 (8)	0.007 (4)	0.053 (6)	0.022 (5)
C15	0.036 (5)	0.041 (5)	0.095 (7)	0.017 (4)	0.022 (4)	0.029 (5)
C16	0.028 (4)	0.030 (4)	0.053 (5)	0.005 (3)	0.010 (3)	0.012 (4)
C17	0.019 (4)	0.021 (4)	0.038 (4)	0.003 (3)	0.009 (3)	0.008 (3)
C18	0.019 (4)	0.031 (4)	0.026 (4)	0.007 (3)	0.006 (3)	0.010 (3)
C19	0.033 (4)	0.019 (4)	0.042 (4)	−0.001 (3)	0.007 (3)	−0.005 (3)
C20	0.040 (4)	0.040 (5)	0.047 (4)	0.000 (3)	0.026 (4)	0.009 (4)
C21	0.029 (4)	0.041 (4)	0.028 (4)	−0.003 (3)	0.007 (3)	0.015 (3)
C22	0.045 (4)	0.024 (4)	0.042 (4)	0.000 (3)	0.018 (4)	0.010 (3)
C23	0.028 (4)	0.029 (4)	0.030 (4)	0.008 (3)	0.009 (3)	0.002 (3)

Geometric parameters (Å, º) top

Br1—C21	1.894 (5)	C8—H8A	0.9900
O1—C17	1.348 (6)	C8—H8B	0.9900
O1—C3	1.457 (6)	C9—H9	1.0000
O2—C17	1.207 (6)	C10—C11	1.495 (7)
N1—C1	1.457 (6)	C10—H10A	0.9900
N1—C10	1.464 (6)	C10—H10B	0.9900
N1—C9	1.467 (6)	C11—C12	1.380 (7)
C1—C2	1.520 (6)	C11—C16	1.381 (7)
C1—H1A	0.9900	C12—C13	1.373 (8)
C1—H1B	0.9900	C12—H12	0.9500
C2—C3	1.503 (7)	C13—C14	1.379 (9)
C2—H2A	0.9900	C13—H13	0.9500
C2—H2B	0.9900	C14—C15	1.365 (9)
C3—C4	1.536 (7)	C14—H14	0.9500
C3—H3	1.0000	C15—C16	1.385 (8)
C4—C5	1.531 (7)	C15—H15	0.9500
C4—C9	1.551 (7)	C16—H16	0.9500
C4—H4	1.0000	C17—C18	1.482 (7)
C5—C6	1.535 (7)	C18—C19	1.387 (7)
C5—H5A	0.9900	C18—C23	1.389 (7)
C5—H5B	0.9900	C19—C20	1.403 (7)
C6—C7	1.527 (7)	C19—H19	0.9500
C6—H6A	0.9900	C20—C21	1.386 (7)
C6—H6B	0.9900	C20—H20	0.9500
C7—C8	1.513 (7)	C21—C22	1.359 (7)
C7—H7A	0.9900	C22—C23	1.377 (7)
C7—H7B	0.9900	C22—H22	0.9500
C8—C9	1.526 (7)	C23—H23	0.9500

C17—O1—C3	117.3 (4)	N1—C9—C8	114.2 (4)
C1—N1—C10	109.5 (4)	N1—C9—C4	108.7 (4)
C1—N1—C9	110.1 (4)	C8—C9—C4	108.3 (5)
C10—N1—C9	113.9 (4)	N1—C9—H9	108.5
N1—C1—C2	110.4 (4)	C8—C9—H9	108.5
N1—C1—H1A	109.6	C4—C9—H9	108.5
C2—C1—H1A	109.6	N1—C10—C11	112.7 (4)
N1—C1—H1B	109.6	N1—C10—H10A	109.1
C2—C1—H1B	109.6	C11—C10—H10A	109.1
H1A—C1—H1B	108.1	N1—C10—H10B	109.1
C3—C2—C1	110.7 (4)	C11—C10—H10B	109.1
C3—C2—H2A	109.5	H10A—C10—H10B	107.8
C1—C2—H2A	109.5	C12—C11—C16	117.9 (6)
C3—C2—H2B	109.5	C12—C11—C10	120.8 (6)
C1—C2—H2B	109.5	C16—C11—C10	121.3 (6)
H2A—C2—H2B	108.1	C13—C12—C11	120.9 (6)
O1—C3—C2	106.5 (4)	C13—C12—H12	119.6
O1—C3—C4	110.8 (4)	C11—C12—H12	119.6
C2—C3—C4	111.4 (5)	C14—C13—C12	120.6 (7)
O1—C3—H3	109.4	C14—C13—H13	119.7
C2—C3—H3	109.4	C12—C13—H13	119.7
C4—C3—H3	109.4	C15—C14—C13	119.3 (7)
C3—C4—C5	114.4 (5)	C15—C14—H14	120.4
C3—C4—C9	108.4 (4)	C13—C14—H14	120.4
C5—C4—C9	110.7 (4)	C14—C15—C16	120.0 (7)
C3—C4—H4	107.7	C14—C15—H15	120.0
C5—C4—H4	107.7	C16—C15—H15	120.0
C9—C4—H4	107.7	C15—C16—C11	121.3 (6)
C6—C5—C4	110.8 (5)	C15—C16—H16	119.4
C6—C5—H5A	109.5	C11—C16—H16	119.4
C4—C5—H5A	109.5	O2—C17—O1	122.6 (5)
C6—C5—H5B	109.5	O2—C17—C18	125.2 (5)
C4—C5—H5B	109.5	O1—C17—C18	112.2 (5)
H5A—C5—H5B	108.1	C19—C18—C23	119.7 (5)
C7—C6—C5	110.6 (5)	C19—C18—C17	122.4 (5)
C7—C6—H6A	109.5	C23—C18—C17	117.9 (5)
C5—C6—H6A	109.5	C18—C19—C20	119.8 (6)
C7—C6—H6B	109.5	C18—C19—H19	120.1
C5—C6—H6B	109.5	C20—C19—H19	120.1
H6A—C6—H6B	108.1	C21—C20—C19	118.8 (6)
C8—C7—C6	110.7 (5)	C21—C20—H20	120.6
C8—C7—H7A	109.5	C19—C20—H20	120.6
C6—C7—H7A	109.5	C22—C21—C20	121.1 (5)
C8—C7—H7B	109.5	C22—C21—Br1	120.5 (5)
C6—C7—H7B	109.5	C20—C21—Br1	118.3 (5)
H7A—C7—H7B	108.1	C21—C22—C23	120.4 (5)
C7—C8—C9	112.3 (5)	C21—C22—H22	119.8
C7—C8—H8A	109.2	C23—C22—H22	119.8
C9—C8—H8A	109.2	C22—C23—C18	120.0 (5)
C7—C8—H8B	109.2	C22—C23—H23	120.0
C9—C8—H8B	109.2	C18—C23—H23	120.0
H8A—C8—H8B	107.9

C10—N1—C1—C2	−170.8 (4)	C9—N1—C10—C11	−170.8 (5)
C9—N1—C1—C2	63.2 (6)	N1—C10—C11—C12	52.6 (7)
N1—C1—C2—C3	−56.6 (6)	N1—C10—C11—C16	−128.7 (5)
C17—O1—C3—C2	149.8 (5)	C16—C11—C12—C13	1.4 (9)
C17—O1—C3—C4	−88.9 (6)	C10—C11—C12—C13	−179.8 (5)
C1—C2—C3—O1	174.0 (4)	C11—C12—C13—C14	−2.0 (10)
C1—C2—C3—C4	53.1 (6)	C12—C13—C14—C15	1.9 (10)
O1—C3—C4—C5	−48.7 (6)	C13—C14—C15—C16	−1.3 (10)
C2—C3—C4—C5	69.7 (6)	C14—C15—C16—C11	0.8 (9)
O1—C3—C4—C9	−172.8 (4)	C12—C11—C16—C15	−0.9 (8)
C2—C3—C4—C9	−54.4 (6)	C10—C11—C16—C15	−179.6 (5)
C3—C4—C5—C6	179.5 (5)	C3—O1—C17—O2	−1.3 (8)
C9—C4—C5—C6	−57.6 (6)	C3—O1—C17—C18	−179.9 (4)
C4—C5—C6—C7	56.0 (7)	O2—C17—C18—C19	170.0 (6)
C5—C6—C7—C8	−55.6 (7)	O1—C17—C18—C19	−11.4 (8)
C6—C7—C8—C9	58.1 (7)	O2—C17—C18—C23	−10.6 (9)
C1—N1—C9—C8	174.3 (4)	O1—C17—C18—C23	168.1 (5)
C10—N1—C9—C8	50.8 (6)	C23—C18—C19—C20	1.1 (9)
C1—N1—C9—C4	−64.8 (5)	C17—C18—C19—C20	−179.5 (5)
C10—N1—C9—C4	171.8 (4)	C18—C19—C20—C21	0.2 (9)
C7—C8—C9—N1	62.9 (6)	C19—C20—C21—C22	−1.7 (9)
C7—C8—C9—C4	−58.3 (6)	C19—C20—C21—Br1	−179.6 (4)
C3—C4—C9—N1	59.4 (6)	C20—C21—C22—C23	2.0 (9)
C5—C4—C9—N1	−66.8 (6)	Br1—C21—C22—C23	179.9 (4)
C3—C4—C9—C8	−176.0 (5)	C21—C22—C23—C18	−0.8 (9)
C5—C4—C9—C8	57.7 (6)	C19—C18—C23—C22	−0.8 (8)
C1—N1—C10—C11	65.4 (6)	C17—C18—C23—C22	179.7 (5)

(XIX) N-benzyl-trans-4-aza-1-decalinyl p-bromobenzoate top

Crystal data top

C₂₃H₂₆BrNO₂	Z = 2
M_r = 428.36	F(000) = 444
Triclinic, P1	D_x = 1.339 Mg m⁻³
a = 9.561 (2) Å	Cu Kα radiation, λ = 1.54178 Å
b = 9.822 (2) Å	Cell parameters from 25 reflections
c = 13.202 (3) Å	θ = 20–25°
α = 78.34 (2)°	µ = 2.76 mm⁻¹
β = 78.21 (2)°	T = 293 K
γ = 61.92 (3)°	Plate, colourless
V = 1062.7 (4) Å³	0.52 × 0.40 × 0.17 mm

Data collection top

Enraf-Nonius CAD-4 diffractometer	2585 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.02
Graphite monochromator	θ_max = 68.0°, θ_min = 5.0°
ω/2θ scans	h = 0→11
Absorption correction: empirical (using intensity measurements) ψ-scan (3 reflections) (North et al., 1968)	k = −9→11
T_min = 0.31, T_max = 0.63	l = −15→15
3862 measured reflections	3 standard reflections every 200 reflections
3862 independent reflections	intensity decay: <2.0%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.135	w = 1/[σ²(F_o²) + (0.0545P)² + 0.43P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3862 reflections	Δρ_max = 0.33 e Å⁻³
245 parameters	Δρ_min = −0.38 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0052 (5)

Crystal data top

C₂₃H₂₆BrNO₂	γ = 61.92 (3)°
M_r = 428.36	V = 1062.7 (4) Å³
Triclinic, P1	Z = 2
a = 9.561 (2) Å	Cu Kα radiation
b = 9.822 (2) Å	µ = 2.76 mm⁻¹
c = 13.202 (3) Å	T = 293 K
α = 78.34 (2)°	0.52 × 0.40 × 0.17 mm
β = 78.21 (2)°

Data collection top

Enraf-Nonius CAD-4 diffractometer	2585 reflections with I > 2σ(I)
Absorption correction: empirical (using intensity measurements) ψ-scan (3 reflections) (North et al., 1968)	R_int = 0.02
T_min = 0.31, T_max = 0.63	3 standard reflections every 200 reflections
3862 measured reflections	intensity decay: <2.0%
3862 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.03	Δρ_max = 0.33 e Å⁻³
3862 reflections	Δρ_min = −0.38 e Å⁻³
245 parameters

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

	x	y	z	U_iso*/U_eq
Br1	0.25821 (6)	0.62098 (7)	−0.47532 (4)	0.1162 (3)
O1	0.1876 (3)	1.0899 (2)	−0.13734 (18)	0.0700 (6)
O2	−0.0586 (3)	1.2222 (4)	−0.1795 (3)	0.1267 (12)
N1	0.2782 (3)	1.2606 (3)	0.09296 (19)	0.0590 (6)
C1	0.1219 (4)	1.2634 (4)	0.1065 (3)	0.0703 (8)
H1A	0.0421	1.3689	0.0887	0.084*
H1B	0.0945	1.2307	0.1790	0.084*
C2	0.1193 (4)	1.1574 (4)	0.0386 (3)	0.0703 (9)
H2A	0.1944	1.0507	0.0587	0.084*
H2B	0.0135	1.1632	0.0481	0.084*
C3	0.1636 (4)	1.2062 (3)	−0.0735 (2)	0.0621 (8)
H3	0.0778	1.3066	−0.0969	0.075*
C4	0.3180 (4)	1.2184 (3)	−0.0909 (2)	0.0592 (7)
H4	0.4038	1.1131	−0.0774	0.071*
C5	0.3545 (4)	1.2808 (4)	−0.2030 (3)	0.0774 (9)
H5A	0.3554	1.2155	−0.2495	0.093*
H5B	0.2707	1.3848	−0.2186	0.093*
C6	0.5141 (5)	1.2855 (5)	−0.2225 (3)	0.0921 (12)
H6A	0.5286	1.3344	−0.2928	0.110*
H6B	0.5996	1.1803	−0.2164	0.110*
C7	0.5224 (5)	1.3756 (5)	−0.1450 (3)	0.0907 (11)
H7A	0.6290	1.3679	−0.1543	0.109*
H7B	0.4480	1.4845	−0.1588	0.109*
C8	0.4828 (4)	1.3158 (4)	−0.0333 (3)	0.0768 (9)
H8A	0.4841	1.3800	0.0132	0.092*
H8B	0.5639	1.2105	−0.0170	0.092*
C9	0.3192 (4)	1.3172 (3)	−0.0150 (2)	0.0599 (7)
H9	0.2384	1.4245	−0.0307	0.072*
C10	0.2780 (5)	1.3522 (4)	0.1687 (3)	0.0740 (9)
H10A	0.1867	1.4539	0.1629	0.089*
H10B	0.3738	1.3671	0.1513	0.089*
C11	0.2711 (4)	1.2776 (4)	0.2795 (2)	0.0618 (8)
C12	0.3500 (4)	1.1180 (4)	0.3037 (3)	0.0686 (8)
H12	0.4019	1.0554	0.2504	0.082*
C13	0.3526 (4)	1.0509 (5)	0.4060 (3)	0.0807 (10)
H13	0.4058	0.9434	0.4215	0.097*
C14	0.2774 (5)	1.1417 (6)	0.4843 (3)	0.0892 (12)
H14	0.2801	1.0960	0.5533	0.107*
C15	0.1984 (5)	1.2990 (6)	0.4626 (3)	0.0966 (12)
H15	0.1468	1.3604	0.5166	0.116*
C16	0.1947 (5)	1.3676 (5)	0.3602 (3)	0.0844 (10)
H16	0.1403	1.4751	0.3456	0.101*
C17	0.0707 (4)	1.1123 (4)	−0.1872 (3)	0.0677 (8)
C18	0.1175 (4)	0.9899 (4)	−0.2533 (2)	0.0608 (7)
C19	0.2705 (4)	0.8695 (4)	−0.2630 (3)	0.0692 (9)
H19	0.3455	0.8618	−0.2242	0.083*
C20	0.3128 (4)	0.7614 (4)	−0.3290 (3)	0.0772 (9)
H20	0.4168	0.6824	−0.3364	0.093*
C21	0.2012 (4)	0.7699 (4)	−0.3842 (3)	0.0724 (9)
C22	0.0483 (4)	0.8872 (5)	−0.3756 (3)	0.0781 (10)
H22	−0.0269	0.8926	−0.4131	0.094*
C23	0.0076 (4)	0.9969 (4)	−0.3105 (3)	0.0744 (9)
H23	−0.0957	1.0774	−0.3048	0.089*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1135 (4)	0.1417 (5)	0.1110 (4)	−0.0579 (3)	−0.0048 (3)	−0.0603 (3)
O1	0.0696 (13)	0.0622 (13)	0.0825 (15)	−0.0247 (11)	−0.0311 (11)	−0.0085 (11)
O2	0.0685 (17)	0.117 (2)	0.196 (3)	−0.0082 (16)	−0.0480 (19)	−0.076 (2)
N1	0.0674 (16)	0.0518 (14)	0.0609 (15)	−0.0276 (12)	−0.0133 (12)	−0.0053 (11)
C1	0.070 (2)	0.071 (2)	0.067 (2)	−0.0299 (17)	−0.0094 (16)	−0.0077 (16)
C2	0.069 (2)	0.079 (2)	0.073 (2)	−0.0420 (18)	−0.0140 (16)	−0.0031 (17)
C3	0.0628 (18)	0.0528 (17)	0.070 (2)	−0.0210 (14)	−0.0183 (15)	−0.0075 (15)
C4	0.0617 (18)	0.0489 (16)	0.0653 (19)	−0.0228 (14)	−0.0123 (14)	−0.0043 (14)
C5	0.089 (2)	0.075 (2)	0.070 (2)	−0.0379 (19)	−0.0052 (18)	−0.0111 (18)
C6	0.101 (3)	0.096 (3)	0.084 (3)	−0.056 (2)	0.013 (2)	−0.017 (2)
C7	0.097 (3)	0.089 (3)	0.102 (3)	−0.059 (2)	0.008 (2)	−0.022 (2)
C8	0.077 (2)	0.072 (2)	0.093 (3)	−0.0420 (18)	−0.0089 (19)	−0.0141 (19)
C9	0.0639 (18)	0.0447 (15)	0.0667 (19)	−0.0210 (14)	−0.0115 (14)	−0.0031 (14)
C10	0.096 (3)	0.0589 (19)	0.074 (2)	−0.0353 (18)	−0.0190 (18)	−0.0106 (16)
C11	0.0643 (19)	0.0622 (19)	0.0639 (19)	−0.0294 (16)	−0.0139 (15)	−0.0100 (15)
C12	0.0634 (19)	0.070 (2)	0.073 (2)	−0.0279 (16)	−0.0152 (16)	−0.0081 (17)
C13	0.071 (2)	0.088 (3)	0.084 (3)	−0.038 (2)	−0.0257 (19)	0.008 (2)
C14	0.091 (3)	0.130 (4)	0.069 (2)	−0.070 (3)	−0.020 (2)	0.005 (3)
C15	0.107 (3)	0.124 (4)	0.073 (3)	−0.057 (3)	−0.005 (2)	−0.032 (3)
C16	0.091 (3)	0.079 (2)	0.085 (3)	−0.034 (2)	−0.011 (2)	−0.024 (2)
C17	0.061 (2)	0.071 (2)	0.078 (2)	−0.0336 (18)	−0.0159 (16)	−0.0058 (17)
C18	0.0586 (18)	0.071 (2)	0.0618 (18)	−0.0375 (16)	−0.0129 (14)	−0.0007 (15)
C19	0.066 (2)	0.074 (2)	0.075 (2)	−0.0335 (18)	−0.0236 (17)	−0.0052 (17)
C20	0.068 (2)	0.078 (2)	0.083 (2)	−0.0269 (18)	−0.0174 (18)	−0.0130 (19)
C21	0.078 (2)	0.088 (2)	0.065 (2)	−0.048 (2)	−0.0055 (17)	−0.0132 (17)
C22	0.071 (2)	0.111 (3)	0.073 (2)	−0.054 (2)	−0.0118 (17)	−0.018 (2)
C23	0.0559 (19)	0.095 (2)	0.081 (2)	−0.0376 (18)	−0.0134 (16)	−0.016 (2)

Geometric parameters (Å, º) top

Br1—C21	1.891 (3)	C8—H8A	0.9700
O1—C17	1.320 (4)	C8—H8B	0.9700
O1—C3	1.459 (3)	C9—H9	0.9800
O2—C17	1.200 (4)	C10—C11	1.501 (4)
N1—C1	1.456 (4)	C10—H10A	0.9700
N1—C9	1.467 (4)	C10—H10B	0.9700
N1—C10	1.473 (4)	C11—C16	1.380 (5)
C1—C2	1.515 (5)	C11—C12	1.382 (4)
C1—H1A	0.9700	C12—C13	1.377 (5)
C1—H1B	0.9700	C12—H12	0.9300
C2—C3	1.499 (4)	C13—C14	1.359 (6)
C2—H2A	0.9700	C13—H13	0.9300
C2—H2B	0.9700	C14—C15	1.360 (6)
C3—C4	1.504 (4)	C14—H14	0.9300
C3—H3	0.9800	C15—C16	1.382 (6)
C4—C5	1.520 (4)	C15—H15	0.9300
C4—C9	1.535 (4)	C16—H16	0.9300
C4—H4	0.9800	C17—C18	1.472 (5)
C5—C6	1.515 (5)	C18—C23	1.382 (4)
C5—H5A	0.9700	C18—C19	1.383 (4)
C5—H5B	0.9700	C19—C20	1.370 (5)
C6—C7	1.518 (5)	C19—H19	0.9300
C6—H6A	0.9700	C20—C21	1.373 (5)
C6—H6B	0.9700	C20—H20	0.9300
C7—C8	1.514 (5)	C21—C22	1.370 (5)
C7—H7A	0.9700	C22—C23	1.377 (5)
C7—H7B	0.9700	C22—H22	0.9300
C8—C9	1.527 (4)	C23—H23	0.9300

C17—O1—C3	119.5 (2)	N1—C9—C8	112.5 (3)
C1—N1—C9	110.5 (2)	N1—C9—C4	110.6 (2)
C1—N1—C10	108.9 (3)	C8—C9—C4	108.6 (3)
C9—N1—C10	112.5 (2)	N1—C9—H9	108.3
N1—C1—C2	111.6 (3)	C8—C9—H9	108.3
N1—C1—H1A	109.3	C4—C9—H9	108.3
C2—C1—H1A	109.3	N1—C10—C11	113.5 (3)
N1—C1—H1B	109.3	N1—C10—H10A	108.9
C2—C1—H1B	109.3	C11—C10—H10A	108.9
H1A—C1—H1B	108.0	N1—C10—H10B	108.9
C3—C2—C1	109.5 (3)	C11—C10—H10B	108.9
C3—C2—H2A	109.8	H10A—C10—H10B	107.7
C1—C2—H2A	109.8	C16—C11—C12	118.4 (3)
C3—C2—H2B	109.8	C16—C11—C10	120.6 (3)
C1—C2—H2B	109.8	C12—C11—C10	120.9 (3)
H2A—C2—H2B	108.2	C13—C12—C11	120.6 (3)
O1—C3—C2	109.8 (2)	C13—C12—H12	119.7
O1—C3—C4	106.3 (2)	C11—C12—H12	119.7
C2—C3—C4	112.3 (3)	C14—C13—C12	120.0 (4)
O1—C3—H3	109.5	C14—C13—H13	120.0
C2—C3—H3	109.5	C12—C13—H13	120.0
C4—C3—H3	109.5	C13—C14—C15	120.5 (4)
C3—C4—C5	111.8 (3)	C13—C14—H14	119.8
C3—C4—C9	111.9 (2)	C15—C14—H14	119.8
C5—C4—C9	110.5 (2)	C14—C15—C16	120.0 (4)
C3—C4—H4	107.5	C14—C15—H15	120.0
C5—C4—H4	107.5	C16—C15—H15	120.0
C9—C4—H4	107.5	C11—C16—C15	120.5 (4)
C6—C5—C4	112.1 (3)	C11—C16—H16	119.8
C6—C5—H5A	109.2	C15—C16—H16	119.8
C4—C5—H5A	109.2	O2—C17—O1	122.9 (3)
C6—C5—H5B	109.2	O2—C17—C18	124.4 (3)
C4—C5—H5B	109.2	O1—C17—C18	112.7 (3)
H5A—C5—H5B	107.9	C23—C18—C19	118.4 (3)
C5—C6—C7	110.7 (3)	C23—C18—C17	119.6 (3)
C5—C6—H6A	109.5	C19—C18—C17	122.0 (3)
C7—C6—H6A	109.5	C20—C19—C18	120.7 (3)
C5—C6—H6B	109.5	C20—C19—H19	119.7
C7—C6—H6B	109.5	C18—C19—H19	119.7
H6A—C6—H6B	108.1	C19—C20—C21	119.8 (3)
C8—C7—C6	112.2 (3)	C19—C20—H20	120.1
C8—C7—H7A	109.2	C21—C20—H20	120.1
C6—C7—H7A	109.2	C22—C21—C20	120.8 (3)
C8—C7—H7B	109.2	C22—C21—Br1	119.1 (3)
C6—C7—H7B	109.2	C20—C21—Br1	120.2 (3)
H7A—C7—H7B	107.9	C21—C22—C23	119.0 (3)
C7—C8—C9	111.7 (3)	C21—C22—H22	120.5
C7—C8—H8A	109.3	C23—C22—H22	120.5
C9—C8—H8A	109.3	C22—C23—C18	121.3 (3)
C7—C8—H8B	109.3	C22—C23—H23	119.4
C9—C8—H8B	109.3	C18—C23—H23	119.4
H8A—C8—H8B	107.9

C9—N1—C1—C2	61.9 (3)	C9—N1—C10—C11	−167.7 (3)
C10—N1—C1—C2	−174.0 (3)	N1—C10—C11—C16	−148.1 (3)
N1—C1—C2—C3	−58.3 (4)	N1—C10—C11—C12	36.3 (4)
C17—O1—C3—C2	97.8 (3)	C16—C11—C12—C13	−0.2 (5)
C17—O1—C3—C4	−140.5 (3)	C10—C11—C12—C13	175.5 (3)
C1—C2—C3—O1	170.5 (2)	C11—C12—C13—C14	−0.2 (5)
C1—C2—C3—C4	52.5 (4)	C12—C13—C14—C15	0.5 (6)
O1—C3—C4—C5	64.7 (3)	C13—C14—C15—C16	−0.3 (6)
C2—C3—C4—C5	−175.2 (3)	C12—C11—C16—C15	0.4 (5)
O1—C3—C4—C9	−170.7 (2)	C10—C11—C16—C15	−175.3 (3)
C2—C3—C4—C9	−50.7 (3)	C14—C15—C16—C11	−0.1 (6)
C3—C4—C5—C6	−177.0 (3)	C3—O1—C17—O2	−3.0 (5)
C9—C4—C5—C6	57.7 (4)	C3—O1—C17—C18	176.2 (2)
C4—C5—C6—C7	−54.1 (4)	O2—C17—C18—C23	−0.9 (5)
C5—C6—C7—C8	53.0 (5)	O1—C17—C18—C23	179.9 (3)
C6—C7—C8—C9	−56.0 (4)	O2—C17—C18—C19	177.0 (4)
C1—N1—C9—C8	−179.7 (3)	O1—C17—C18—C19	−2.2 (4)
C10—N1—C9—C8	58.3 (3)	C23—C18—C19—C20	1.1 (5)
C1—N1—C9—C4	−58.1 (3)	C17—C18—C19—C20	−176.8 (3)
C10—N1—C9—C4	180.0 (3)	C18—C19—C20—C21	−1.8 (5)
C7—C8—C9—N1	−179.6 (3)	C19—C20—C21—C22	1.2 (6)
C7—C8—C9—C4	57.6 (3)	C19—C20—C21—Br1	−179.8 (3)
C3—C4—C9—N1	52.7 (3)	C20—C21—C22—C23	0.0 (5)
C5—C4—C9—N1	177.9 (3)	Br1—C21—C22—C23	−179.0 (3)
C3—C4—C9—C8	176.6 (3)	C21—C22—C23—C18	−0.6 (5)
C5—C4—C9—C8	−58.1 (3)	C19—C18—C23—C22	0.1 (5)
C1—N1—C10—C11	69.4 (4)	C17—C18—C23—C22	178.1 (3)

(XX) trans-4-thia-1-decalinyl p-bromobenzoate top

Crystal data top

C₁₆H₁₉BrO₂S	F(000) = 364
M_r = 355.28	D_x = 1.491 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54178 Å
a = 8.886 (2) Å	Cell parameters from 25 reflections
b = 5.3714 (9) Å	θ = 15–25°
c = 16.599 (3) Å	µ = 4.76 mm⁻¹
β = 92.70 (2)°	T = 293 K
V = 791.4 (3) Å³	Prismatic, colourless
Z = 2	0.40 × 0.25 × 0.20 mm

Data collection top

Enraf-Nonius CAD-4 diffractometer	2563 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.014
Graphite monochromator	θ_max = 68.0°, θ_min = 5.0°
ω/2θ scans	h = 0→10
Absorption correction: empirical (using intensity measurements) ψ-scan (3 reflections) (North et al., 1968)	k = −6→5
T_min = 0.28, T_max = 0.39	l = −19→19
2984 measured reflections	3 standard reflections every 200 reflections
2797 independent reflections	intensity decay: <0.1%

Refinement top

Refinement on F²	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.048	w = 1/[σ²(F_o²) + (0.08P)² + 0.65P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.133	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.38 e Å⁻³
2797 reflections	Δρ_min = −0.52 e Å⁻³
182 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0237 (16)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.05 (3)

Crystal data top

C₁₆H₁₉BrO₂S	V = 791.4 (3) Å³
M_r = 355.28	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 8.886 (2) Å	µ = 4.76 mm⁻¹
b = 5.3714 (9) Å	T = 293 K
c = 16.599 (3) Å	0.40 × 0.25 × 0.20 mm
β = 92.70 (2)°

Data collection top

Enraf-Nonius CAD-4 diffractometer	2563 reflections with I > 2σ(I)
Absorption correction: empirical (using intensity measurements) ψ-scan (3 reflections) (North et al., 1968)	R_int = 0.014
T_min = 0.28, T_max = 0.39	3 standard reflections every 200 reflections
2984 measured reflections	intensity decay: <0.1%
2797 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.133	Δρ_max = 0.38 e Å⁻³
S = 1.04	Δρ_min = −0.52 e Å⁻³
2797 reflections	Absolute structure: Flack (1983)
182 parameters	Absolute structure parameter: −0.05 (3)
1 restraint

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

	x	y	z	U_iso*/U_eq
Br1	−0.32605 (6)	−0.09427 (17)	0.57524 (4)	0.0915 (3)
S1	0.29850 (18)	−0.3767 (3)	0.02450 (7)	0.0716 (4)
O1	0.0979 (3)	−0.0869 (7)	0.24798 (16)	0.0512 (7)
O2	−0.0165 (5)	0.2766 (8)	0.2242 (3)	0.0870 (13)
C1	0.1403 (6)	−0.1702 (12)	0.0246 (3)	0.0691 (15)
H1A	0.1732	−0.0021	0.0134	0.083*
H1B	0.0670	−0.2188	−0.0176	0.083*
C2	0.0670 (5)	−0.1755 (11)	0.1060 (3)	0.0625 (14)
H2A	−0.0239	−0.0751	0.1030	0.075*
H2B	0.0388	−0.3451	0.1186	0.075*
C3	0.1739 (4)	−0.0765 (10)	0.1719 (2)	0.0488 (9)
H3	0.1999	0.0966	0.1599	0.059*
C4	0.3172 (5)	−0.2278 (8)	0.1853 (2)	0.0447 (9)
H4	0.2886	−0.3983	0.1990	0.054*
C5	0.4182 (5)	−0.1259 (11)	0.2546 (3)	0.0550 (10)
H5A	0.4444	0.0452	0.2429	0.066*
H5B	0.3629	−0.1265	0.3036	0.066*
C6	0.5607 (5)	−0.2754 (13)	0.2683 (3)	0.0667 (14)
H6A	0.5355	−0.4439	0.2837	0.080*
H6B	0.6221	−0.2019	0.3119	0.080*
C7	0.6499 (6)	−0.2815 (14)	0.1917 (4)	0.0760 (16)
H7A	0.6824	−0.1145	0.1787	0.091*
H7B	0.7388	−0.3845	0.2005	0.091*
C8	0.5521 (6)	−0.3860 (12)	0.1218 (3)	0.0698 (14)
H8A	0.5279	−0.5584	0.1329	0.084*
H8B	0.6079	−0.3815	0.0730	0.084*
C9	0.4066 (5)	−0.2382 (9)	0.1086 (3)	0.0521 (10)
H9	0.4329	−0.0676	0.0937	0.062*
C10	0.0045 (5)	0.0959 (10)	0.2649 (3)	0.0526 (11)
C11	−0.0737 (4)	0.0460 (9)	0.3406 (3)	0.0468 (10)
C12	−0.0441 (5)	−0.1642 (9)	0.3862 (3)	0.0504 (11)
H12	0.0265	−0.2794	0.3700	0.060*
C13	−0.1197 (5)	−0.2043 (10)	0.4567 (3)	0.0559 (12)
H13	−0.0989	−0.3445	0.4881	0.067*
C14	−0.2245 (5)	−0.0359 (10)	0.4791 (3)	0.0565 (12)
C15	−0.2567 (6)	0.1731 (12)	0.4354 (3)	0.0677 (14)
H15	−0.3286	0.2854	0.4520	0.081*
C16	−0.1798 (5)	0.2168 (10)	0.3648 (3)	0.0613 (12)
H16	−0.1999	0.3594	0.3344	0.074*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0710 (4)	0.1398 (7)	0.0671 (4)	−0.0211 (4)	0.0381 (3)	−0.0163 (4)
S1	0.0916 (10)	0.0786 (9)	0.0463 (6)	−0.0072 (7)	0.0204 (6)	−0.0129 (6)
O1	0.0470 (14)	0.0640 (17)	0.0443 (14)	0.0101 (16)	0.0201 (11)	0.0065 (15)
O2	0.096 (3)	0.078 (3)	0.091 (3)	0.030 (2)	0.041 (2)	0.032 (2)
C1	0.065 (3)	0.097 (4)	0.045 (2)	−0.015 (3)	0.005 (2)	0.003 (2)
C2	0.049 (2)	0.091 (4)	0.048 (2)	−0.006 (2)	0.0052 (19)	0.010 (2)
C3	0.0449 (19)	0.063 (3)	0.0400 (19)	−0.004 (2)	0.0176 (15)	0.007 (2)
C4	0.043 (2)	0.051 (2)	0.0410 (19)	−0.0018 (17)	0.0144 (17)	0.0011 (17)
C5	0.051 (2)	0.068 (3)	0.047 (2)	−0.005 (2)	0.0095 (17)	−0.004 (2)
C6	0.043 (2)	0.098 (4)	0.059 (3)	0.002 (3)	0.006 (2)	0.009 (3)
C7	0.046 (3)	0.103 (4)	0.081 (4)	0.016 (3)	0.021 (3)	0.023 (3)
C8	0.068 (3)	0.078 (3)	0.066 (3)	0.021 (3)	0.032 (3)	0.009 (3)
C9	0.056 (3)	0.057 (3)	0.045 (2)	0.001 (2)	0.0213 (19)	0.0021 (19)
C10	0.042 (2)	0.064 (3)	0.053 (2)	0.0070 (19)	0.0138 (18)	0.006 (2)
C11	0.035 (2)	0.056 (2)	0.050 (2)	0.0044 (17)	0.0107 (17)	−0.0007 (19)
C12	0.042 (2)	0.061 (3)	0.049 (2)	0.0079 (19)	0.0136 (17)	0.0001 (18)
C13	0.051 (2)	0.071 (3)	0.046 (2)	0.000 (2)	0.011 (2)	0.003 (2)
C14	0.041 (2)	0.077 (4)	0.053 (2)	−0.009 (2)	0.0156 (18)	−0.010 (2)
C15	0.044 (2)	0.086 (4)	0.075 (3)	0.011 (2)	0.020 (2)	−0.016 (3)
C16	0.048 (2)	0.067 (3)	0.070 (3)	0.014 (2)	0.014 (2)	0.000 (2)

Geometric parameters (Å, º) top

Br1—C14	1.897 (4)	C6—H6A	0.9700
S1—C1	1.790 (6)	C6—H6B	0.9700
S1—C9	1.816 (5)	C7—C8	1.524 (9)
O1—C10	1.324 (6)	C7—H7A	0.9700
O1—C3	1.462 (4)	C7—H7B	0.9700
O2—C10	1.193 (6)	C8—C9	1.524 (7)
C1—C2	1.527 (7)	C8—H8A	0.9700
C1—H1A	0.9700	C8—H8B	0.9700
C1—H1B	0.9700	C9—H9	0.9800
C2—C3	1.512 (6)	C10—C11	1.488 (6)
C2—H2A	0.9700	C11—C12	1.378 (6)
C2—H2B	0.9700	C11—C16	1.388 (6)
C3—C4	1.518 (6)	C12—C13	1.393 (6)
C3—H3	0.9800	C12—H12	0.9300
C4—C5	1.527 (6)	C13—C14	1.362 (7)
C4—C9	1.533 (5)	C13—H13	0.9300
C4—H4	0.9800	C14—C15	1.359 (8)
C5—C6	1.507 (7)	C15—C16	1.404 (8)
C5—H5A	0.9700	C15—H15	0.9300
C5—H5B	0.9700	C16—H16	0.9300
C6—C7	1.530 (7)

C1—S1—C9	97.6 (2)	C8—C7—H7A	109.7
C10—O1—C3	118.3 (4)	C6—C7—H7A	109.7
C2—C1—S1	111.0 (4)	C8—C7—H7B	109.7
C2—C1—H1A	109.4	C6—C7—H7B	109.7
S1—C1—H1A	109.4	H7A—C7—H7B	108.2
C2—C1—H1B	109.4	C7—C8—C9	111.5 (5)
S1—C1—H1B	109.4	C7—C8—H8A	109.3
H1A—C1—H1B	108.0	C9—C8—H8A	109.3
C3—C2—C1	110.7 (4)	C7—C8—H8B	109.3
C3—C2—H2A	109.5	C9—C8—H8B	109.3
C1—C2—H2A	109.5	H8A—C8—H8B	108.0
C3—C2—H2B	109.5	C8—C9—C4	111.6 (4)
C1—C2—H2B	109.5	C8—C9—S1	108.2 (4)
H2A—C2—H2B	108.1	C4—C9—S1	112.2 (3)
O1—C3—C2	108.2 (3)	C8—C9—H9	108.3
O1—C3—C4	105.7 (3)	C4—C9—H9	108.3
C2—C3—C4	114.3 (4)	S1—C9—H9	108.3
O1—C3—H3	109.5	O2—C10—O1	124.5 (4)
C2—C3—H3	109.5	O2—C10—C11	123.9 (4)
C4—C3—H3	109.5	O1—C10—C11	111.6 (4)
C3—C4—C5	112.2 (4)	C12—C11—C16	119.8 (4)
C3—C4—C9	111.2 (3)	C12—C11—C10	121.8 (4)
C5—C4—C9	109.2 (3)	C16—C11—C10	118.4 (4)
C3—C4—H4	108.0	C11—C12—C13	120.1 (4)
C5—C4—H4	108.0	C11—C12—H12	120.0
C9—C4—H4	108.0	C13—C12—H12	120.0
C6—C5—C4	112.5 (4)	C14—C13—C12	119.3 (5)
C6—C5—H5A	109.1	C14—C13—H13	120.4
C4—C5—H5A	109.1	C12—C13—H13	120.4
C6—C5—H5B	109.1	C15—C14—C13	122.2 (4)
C4—C5—H5B	109.1	C15—C14—Br1	119.3 (4)
H5A—C5—H5B	107.8	C13—C14—Br1	118.6 (4)
C5—C6—C7	110.5 (4)	C14—C15—C16	119.0 (5)
C5—C6—H6A	109.5	C14—C15—H15	120.5
C7—C6—H6A	109.5	C16—C15—H15	120.5
C5—C6—H6B	109.5	C11—C16—C15	119.7 (5)
C7—C6—H6B	109.5	C11—C16—H16	120.2
H6A—C6—H6B	108.1	C15—C16—H16	120.2
C8—C7—C6	110.0 (4)

C9—S1—C1—C2	−58.3 (4)	C5—C4—C9—S1	176.2 (3)
S1—C1—C2—C3	64.7 (5)	C1—S1—C9—C8	179.7 (3)
C10—O1—C3—C2	−82.3 (5)	C1—S1—C9—C4	56.2 (4)
C10—O1—C3—C4	154.9 (4)	C3—O1—C10—O2	−4.1 (7)
C1—C2—C3—O1	−179.8 (4)	C3—O1—C10—C11	174.8 (4)
C1—C2—C3—C4	−62.3 (6)	O2—C10—C11—C12	−179.1 (5)
O1—C3—C4—C5	−58.9 (5)	O1—C10—C11—C12	2.0 (6)
C2—C3—C4—C5	−177.7 (4)	O2—C10—C11—C16	1.3 (8)
O1—C3—C4—C9	178.5 (4)	O1—C10—C11—C16	−177.6 (4)
C2—C3—C4—C9	59.6 (5)	C16—C11—C12—C13	−0.4 (7)
C3—C4—C5—C6	180.0 (4)	C10—C11—C12—C13	−180.0 (5)
C9—C4—C5—C6	−56.3 (5)	C11—C12—C13—C14	1.0 (7)
C4—C5—C6—C7	58.0 (6)	C12—C13—C14—C15	−0.9 (7)
C5—C6—C7—C8	−56.7 (7)	C12—C13—C14—Br1	−180.0 (4)
C6—C7—C8—C9	56.2 (6)	C13—C14—C15—C16	0.1 (8)
C7—C8—C9—C4	−56.1 (6)	Br1—C14—C15—C16	179.2 (4)
C7—C8—C9—S1	−180.0 (4)	C12—C11—C16—C15	−0.4 (7)
C3—C4—C9—C8	179.0 (4)	C10—C11—C16—C15	179.2 (5)
C5—C4—C9—C8	54.7 (5)	C14—C15—C16—C11	0.5 (8)
C3—C4—C9—S1	−59.4 (4)

Experimental details

	(XVI)	(XVII)	(XVIII)	(XIX)
Crystal data
Chemical formula	C₁₆H₁₉BrO₃	C₁₆H₁₉BrO₃	C₂₃H₂₆BrNO₂	C₂₃H₂₆BrNO₂
M_r	339.22	339.22	428.36	428.36
Crystal system, space group	Monoclinic, P2₁/n	Triclinic, P1	Triclinic, P1	Triclinic, P1
Temperature (K)	170	293	170	293
a, b, c (Å)	10.906 (2), 8.052 (4), 17.195 (3)	9.643 (2), 10.679 (2), 8.772 (2)	11.914 (3), 13.144 (3), 6.922 (2)	9.561 (2), 9.822 (2), 13.202 (3)
α, β, γ (°)	90, 95.98 (2), 90	96.32 (2), 111.32 (2), 110.49 (2)	96.06 (2), 106.22 (2), 100.42 (3)	78.34 (2), 78.21 (2), 61.92 (3)
V (Å³)	1501.8 (8)	758.5 (3)	1009.6 (5)	1062.7 (4)
Z	4	2	2	2
Radiation type	Mo Kα	Mo Kα	Mo Kα	Cu Kα
µ (mm⁻¹)	2.74	2.71	2.05	2.76
Crystal size (mm)	0.48 × 0.42 × 0.33	0.60 × 0.40 × 0.15	0.60 × 0.40 × 0.32	0.52 × 0.40 × 0.17

Data collection
Diffractometer	Rigaku AFC-6S diffractometer	Rigaku AFC-6S diffractometer	Rigaku AFC-6S diffractometer	Enraf-Nonius CAD-4 diffractometer
Absorption correction	Empirical (using intensity measurements) ψ-scan (3 reflections) (North et al., 1968)	Empirical (using intensity measurements) ψ-scan (3 reflections) (North et al., 1968)	Empirical (using intensity measurements) ψ-scan (3 reflections) (North et al., 1968)	Empirical (using intensity measurements) ψ-scan (3 reflections) (North et al., 1968)
T_min, T_max	0.28, 0.41	0.28, 0.67	0.39, 0.52	0.31, 0.63
No. of measured, independent and observed [I > 2σ(I)] reflections	2646, 2646, 693	2702, 2702, 1169	3574, 3574, 1407	3862, 3862, 2585
R_int	0.08	0.03	0.09	0.02
(sin θ/λ)_max (Å⁻¹)	0.595	0.595	0.595	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.109, 0.94	0.039, 0.130, 0.98	0.040, 0.110, 0.95	0.046, 0.135, 1.03
No. of reflections	2646	2702	3574	3862
No. of parameters	182	181	244	245
No. of restraints	0	0	0	0
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.77	0.42, −0.38	0.43, −0.76	0.33, −0.38
Absolute structure	?	?	?	?
Absolute structure parameter	?	?	?	?

	(XX)
Crystal data
Chemical formula	C₁₆H₁₉BrO₂S
M_r	355.28
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	8.886 (2), 5.3714 (9), 16.599 (3)
α, β, γ (°)	90, 92.70 (2), 90
V (Å³)	791.4 (3)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	4.76
Crystal size (mm)	0.40 × 0.25 × 0.20

Data collection
Diffractometer	Enraf-Nonius CAD-4 diffractometer
Absorption correction	Empirical (using intensity measurements) ψ-scan (3 reflections) (North et al., 1968)
T_min, T_max	0.28, 0.39
No. of measured, independent and observed [I > 2σ(I)] reflections	2984, 2797, 2563
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.133, 1.04
No. of reflections	2797
No. of parameters	182
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.52
Absolute structure	Flack (1983)
Absolute structure parameter	−0.05 (3)

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988), CAD-4 Software (Enraf-Nonius, 1989), MSC/AFC Diffractometer Control Software, CAD-4 Software, TEXSAN (Molecular Structure Corporation, 1994), SAPI91 (Fan, 1991), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.

Selected geometric parameters (Å, º) for (XVI) top

Br1—C14	1.895 (8)	O2—C10	1.324 (9)
O1—C1	1.421 (9)	O2—C3	1.458 (7)
O1—C9	1.439 (10)	O3—C10	1.228 (9)

C1—O1—C9	111.6 (7)	C10—O2—C3	117.9 (7)

Selected geometric parameters (Å, º) for (XVII) top

Br1—C14	1.880 (5)	O2—C10	1.344 (6)
O1—C9	1.410 (6)	O2—C3	1.456 (6)
O1—C1	1.407 (6)	O3—C10	1.200 (6)

C9—O1—C1	111.9 (4)	C10—O2—C3	119.2 (4)

Selected geometric parameters (Å, º) for (XVIII) top

Br1—C21	1.894 (5)	N1—C1	1.457 (6)
O1—C17	1.348 (6)	N1—C10	1.464 (6)
O1—C3	1.457 (6)	N1—C9	1.467 (6)
O2—C17	1.207 (6)

C17—O1—C3	117.3 (4)	C1—N1—C9	110.1 (4)
C1—N1—C10	109.5 (4)	C10—N1—C9	113.9 (4)

Selected geometric parameters (Å, º) for (XIX) top

Br1—C21	1.891 (3)	N1—C1	1.456 (4)
O1—C17	1.320 (4)	N1—C9	1.467 (4)
O1—C3	1.459 (3)	N1—C10	1.473 (4)
O2—C17	1.200 (4)

C17—O1—C3	119.5 (2)	C1—N1—C10	108.9 (3)
C1—N1—C9	110.5 (2)	C9—N1—C10	112.5 (2)

Selected geometric parameters (Å, º) for (XX) top

Br1—C14	1.897 (4)	O1—C10	1.324 (6)
S1—C1	1.790 (6)	O1—C3	1.462 (4)
S1—C9	1.816 (5)	O2—C10	1.193 (6)

C1—S1—C9	97.6 (2)	C10—O1—C3	118.3 (4)

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