Design, synthesis and crystallographic study of novel indole-based cyano derivatives as key building blocks for heteropolycyclic compounds of major complexity

A four-stage reaction sequence has been designed and developed for the synthesis of highly functionalized enolate esters as key building blocks for the synthesis of novel heteropolycyclic compounds of potential pharmaceutical value. The sequence starts with simple commercially available indoles and proceeds via 3-(indol-3-yl)-3-oxo­propane­nitriles, which react with 2-bromo­benzaldehyde to form the corresponding chalcones; these are readily reduced to di­hydro­chalcones, which are in turn acyl­ated to form the enolate esters. The com­pounds in this sequence have been characterized by IR and ¹H and ¹³C NMR spectroscopy, by mass spectrometry and by elemental analysis. The mol­ecular and supra­molecular structures are reported for representative examples, namely (E)-3-(2-bromo­phen­yl)-2-(1-methyl-1H-indole-3-carbon­yl)acrylo­nitrile, C₁₉H₁₃BrN₂O, (Ib), (2RS)-2-(2-bromo­benz­yl)-3-(1-methyl-1H-in­dol-3-yl)-3-oxo­propane­nitrile, C₁₉H₁₅BrN₂O, (IIb), and (2RS)-3-(1-benzyl-1H-indol-3-yl)-2-(2-bromo­benz­yl)-3-oxo­propane­nitrile, C₂₅H₁₉BrN₂O, (IIc), the latter two of which crystallize with Z′ = 2, and (E)-1-(1-acetyl-1H-indol-3-yl)-3-(2-bromo­phen­yl)-2-cyano­prop-1-en-1-yl acetate, C₂₂H₁₇BrN₂O, (III), and (E)-1-(1-benzyl-1H-indol-3-yl)-3-(2-bromo­phen­yl)-2-cyano­prop-1-en-1-yl ben­zoate, C₃₂H₂₃BrN₂O, (IV). The structure of the related chalcone (E)-2-benzoyl-3-(2-bromo­phen­yl)prop-2-ene­nitrile, (V), has been redetermined at 100 K, where it is monoclinic, as opposed to the triclinic form reported at ambient temperature.

Computing details

For all structures, data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

(E)-3-(2-Bromophenyl)-2-(1-methyl-1H-indole-3-carbonyl)acrylonitrile (Ib)

Crystal data

C19H13BrN2O	Z = 2
Mr = 365.22	F(000) = 368
Triclinic, P1	Dx = 1.628 Mg m^−3
a = 9.188 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.308 (5) Å	Cell parameters from 3467 reflections
c = 10.887 (5) Å	θ = 2.5–27.7°
α = 113.56 (2)°	µ = 2.76 mm^−1
β = 90.782 (18)°	T = 100 K
γ = 116.173 (16)°	Block, yellow
V = 745.3 (7) Å^3	0.33 × 0.21 × 0.19 mm

Data collection

Bruker D8 Venture diffractometer	3467 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube	3296 reflections with I > 2σ(I)
Multilayer mirror monochromator	Rint = 0.040
φ and ω scans	θmax = 27.7°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −11→11
Tmin = 0.446, Tmax = 0.591	k = −12→12
46632 measured reflections	l = −14→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.020	H-atom parameters constrained
wR(F^2) = 0.049	w = 1/[σ^2(Fo^2) + (0.0202P)^2 + 0.6373P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
3467 reflections	Δρmax = 0.40 e Å^−3
209 parameters	Δρmin = −0.39 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
N1	0.29057 (17)	0.14946 (19)	0.81720 (15)	0.0189 (3)
C1	0.41876 (18)	0.2564 (2)	0.82078 (15)	0.0119 (3)
C2	0.57679 (18)	0.39150 (19)	0.82260 (14)	0.0100 (3)
C3	0.72260 (18)	0.40212 (19)	0.86046 (14)	0.0098 (3)
H3	0.8179	0.4924	0.8513	0.012*
C28	0.58375 (18)	0.52896 (19)	0.77826 (14)	0.0098 (3)
O28	0.71080 (13)	0.67527 (14)	0.82765 (11)	0.0150 (2)
N21	0.21687 (15)	0.33281 (16)	0.50736 (12)	0.0101 (2)
C22	0.31281 (17)	0.31821 (19)	0.59208 (14)	0.0100 (3)
H22	0.2916	0.2088	0.5923	0.012*
C23	0.44624 (17)	0.48493 (18)	0.67852 (14)	0.0087 (3)
C23A	0.43162 (17)	0.61089 (19)	0.64119 (14)	0.0090 (3)
C24	0.52727 (18)	0.79570 (19)	0.68562 (14)	0.0105 (3)
H24	0.6262	0.8660	0.7565	0.013*
C25	0.47404 (19)	0.87307 (19)	0.62369 (15)	0.0126 (3)
H25	0.5386	0.9982	0.6519	0.015*
C26	0.32693 (19)	0.7718 (2)	0.51994 (15)	0.0131 (3)
H26	0.2934	0.8302	0.4807	0.016*
C27	0.22994 (18)	0.5887 (2)	0.47382 (15)	0.0120 (3)
H27	0.1303	0.5194	0.4037	0.014*
C27A	0.28581 (17)	0.51137 (19)	0.53536 (14)	0.0094 (3)
C211	0.07277 (18)	0.1855 (2)	0.39592 (16)	0.0150 (3)
H21A	0.0497	0.0716	0.3949	0.022*
H21B	0.0963	0.1829	0.3077	0.022*
H21C	−0.0244	0.2029	0.4103	0.022*
C31	0.75642 (17)	0.29564 (18)	0.91350 (14)	0.0091 (3)
C32	0.88829 (17)	0.25981 (18)	0.88333 (14)	0.0092 (3)
Br32	1.00583 (2)	0.32293 (2)	0.75519 (2)	0.01222 (5)
C33	0.93663 (18)	0.17583 (19)	0.94167 (15)	0.0114 (3)
H33	1.0270	0.1542	0.9195	0.014*
C34	0.85086 (18)	0.1236 (2)	1.03316 (15)	0.0127 (3)
H34	0.8831	0.0669	1.0751	0.015*
C35	0.71789 (19)	0.1542 (2)	1.06365 (15)	0.0130 (3)
H35	0.6585	0.1167	1.1255	0.016*
C36	0.67111 (18)	0.2388 (2)	1.00457 (15)	0.0116 (3)
H36	0.5797	0.2586	1.0263	0.014*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0142 (6)	0.0248 (7)	0.0258 (7)	0.0094 (6)	0.0057 (5)	0.0187 (6)
C1	0.0131 (7)	0.0160 (7)	0.0128 (7)	0.0096 (6)	0.0042 (5)	0.0092 (6)
C2	0.0114 (7)	0.0103 (6)	0.0092 (6)	0.0055 (6)	0.0033 (5)	0.0050 (5)
C3	0.0109 (6)	0.0092 (6)	0.0086 (6)	0.0044 (5)	0.0021 (5)	0.0039 (5)
C28	0.0111 (6)	0.0108 (6)	0.0096 (6)	0.0068 (5)	0.0041 (5)	0.0048 (5)
O28	0.0135 (5)	0.0108 (5)	0.0181 (5)	0.0036 (4)	−0.0017 (4)	0.0067 (4)
N21	0.0087 (5)	0.0106 (6)	0.0105 (6)	0.0039 (5)	0.0019 (5)	0.0053 (5)
C22	0.0115 (6)	0.0121 (7)	0.0105 (6)	0.0073 (6)	0.0051 (5)	0.0070 (6)
C23	0.0092 (6)	0.0099 (6)	0.0097 (6)	0.0059 (5)	0.0045 (5)	0.0055 (5)
C23A	0.0097 (6)	0.0120 (7)	0.0086 (6)	0.0068 (5)	0.0046 (5)	0.0058 (5)
C24	0.0107 (6)	0.0105 (7)	0.0088 (6)	0.0050 (6)	0.0026 (5)	0.0031 (5)
C25	0.0154 (7)	0.0097 (6)	0.0125 (7)	0.0066 (6)	0.0050 (6)	0.0043 (6)
C26	0.0175 (7)	0.0170 (7)	0.0133 (7)	0.0125 (6)	0.0061 (6)	0.0098 (6)
C27	0.0116 (7)	0.0153 (7)	0.0108 (7)	0.0075 (6)	0.0025 (5)	0.0064 (6)
C27A	0.0105 (6)	0.0110 (6)	0.0093 (6)	0.0063 (5)	0.0051 (5)	0.0056 (5)
C211	0.0111 (7)	0.0123 (7)	0.0134 (7)	0.0015 (6)	−0.0020 (6)	0.0035 (6)
C31	0.0082 (6)	0.0079 (6)	0.0086 (6)	0.0027 (5)	−0.0002 (5)	0.0030 (5)
C32	0.0078 (6)	0.0090 (6)	0.0082 (6)	0.0019 (5)	0.0010 (5)	0.0039 (5)
Br32	0.01107 (7)	0.01656 (8)	0.01307 (8)	0.00725 (6)	0.00570 (5)	0.00963 (6)
C33	0.0092 (6)	0.0110 (7)	0.0129 (7)	0.0048 (5)	0.0012 (5)	0.0047 (6)
C34	0.0134 (7)	0.0117 (7)	0.0134 (7)	0.0050 (6)	0.0003 (5)	0.0074 (6)
C35	0.0137 (7)	0.0140 (7)	0.0123 (7)	0.0055 (6)	0.0038 (5)	0.0082 (6)
C36	0.0099 (6)	0.0140 (7)	0.0115 (7)	0.0062 (6)	0.0027 (5)	0.0059 (6)

Geometric parameters (Å, º)

N1—C1	1.146 (2)	C25—H25	0.9500
C1—C2	1.435 (2)	C26—C27	1.384 (2)
C2—C3	1.345 (2)	C26—H26	0.9500
C2—C28	1.516 (2)	C27—C27A	1.390 (2)
C3—C31	1.462 (2)	C27—H27	0.9500
C3—H3	0.9500	C211—H21A	0.9800
C28—O28	1.2253 (19)	C211—H21B	0.9800
C28—C23	1.447 (2)	C211—H21C	0.9800
N21—C22	1.3528 (19)	C31—C36	1.397 (2)
N21—C27A	1.385 (2)	C31—C32	1.402 (2)
N21—C211	1.459 (2)	C32—C33	1.381 (2)
C22—C23	1.385 (2)	C32—Br32	1.8959 (15)
C22—H22	0.9500	C33—C34	1.385 (2)
C23—C23A	1.441 (2)	C33—H33	0.9500
C23A—C24	1.398 (2)	C34—C35	1.388 (2)
C23A—C27A	1.411 (2)	C34—H34	0.9500
C24—C25	1.379 (2)	C35—C36	1.384 (2)
C24—H24	0.9500	C35—H35	0.9500
C25—C26	1.405 (2)	C36—H36	0.9500
N1—C1—C2	178.21 (16)	C26—C27—C27A	116.53 (14)
C3—C2—C1	123.11 (14)	C26—C27—H27	121.7
C3—C2—C28	117.10 (13)	C27A—C27—H27	121.7
C1—C2—C28	119.78 (13)	N21—C27A—C27	128.84 (14)
C2—C3—C31	129.71 (13)	N21—C27A—C23A	108.03 (12)
C2—C3—H3	115.1	C27—C27A—C23A	123.12 (14)
C31—C3—H3	115.1	N21—C211—H21A	109.5
O28—C28—C23	122.07 (13)	N21—C211—H21B	109.5
O28—C28—C2	117.42 (13)	H21A—C211—H21B	109.5
C23—C28—C2	120.49 (13)	N21—C211—H21C	109.5
C22—N21—C27A	108.76 (12)	H21A—C211—H21C	109.5
C22—N21—C211	126.51 (13)	H21B—C211—H21C	109.5
C27A—N21—C211	124.52 (12)	C36—C31—C32	116.99 (13)
N21—C22—C23	110.62 (13)	C36—C31—C3	122.58 (13)
N21—C22—H22	124.7	C32—C31—C3	120.20 (13)
C23—C22—H22	124.7	C33—C32—C31	122.72 (13)
C22—C23—C23A	105.98 (13)	C33—C32—Br32	117.14 (11)
C22—C23—C28	128.88 (13)	C31—C32—Br32	120.13 (11)
C23A—C23—C28	124.91 (13)	C32—C33—C34	118.77 (14)
C24—C23A—C27A	119.08 (13)	C32—C33—H33	120.6
C24—C23A—C23	134.34 (14)	C34—C33—H33	120.6
C27A—C23A—C23	106.58 (13)	C33—C34—C35	120.09 (13)
C25—C24—C23A	118.17 (14)	C33—C34—H34	120.0
C25—C24—H24	120.9	C35—C34—H34	120.0
C23A—C24—H24	120.9	C36—C35—C34	120.46 (14)
C24—C25—C26	121.77 (14)	C36—C35—H35	119.8
C24—C25—H25	119.1	C34—C35—H35	119.8
C26—C25—H25	119.1	C35—C36—C31	120.95 (14)
C27—C26—C25	121.31 (14)	C35—C36—H36	119.5
C27—C26—H26	119.3	C31—C36—H36	119.5
C25—C26—H26	119.3
C1—C2—C3—C31	−4.1 (2)	C22—N21—C27A—C27	179.90 (14)
C28—C2—C3—C31	176.84 (13)	C211—N21—C27A—C27	4.9 (2)
C3—C2—C28—O28	−28.16 (19)	C22—N21—C27A—C23A	0.57 (15)
C1—C2—C28—O28	152.77 (14)	C211—N21—C27A—C23A	−174.47 (13)
C3—C2—C28—C23	150.23 (14)	C26—C27—C27A—N21	−178.17 (14)
C1—C2—C28—C23	−28.8 (2)	C26—C27—C27A—C23A	1.1 (2)
C27A—N21—C22—C23	0.38 (16)	C24—C23A—C27A—N21	178.21 (12)
C211—N21—C22—C23	175.30 (13)	C23—C23A—C27A—N21	−1.26 (15)
N21—C22—C23—C23A	−1.15 (16)	C24—C23A—C27A—C27	−1.2 (2)
N21—C22—C23—C28	−175.81 (13)	C23—C23A—C27A—C27	179.37 (13)
O28—C28—C23—C22	164.56 (14)	C2—C3—C31—C36	−38.0 (2)
C2—C28—C23—C22	−13.7 (2)	C2—C3—C31—C32	147.66 (16)
O28—C28—C23—C23A	−9.2 (2)	C36—C31—C32—C33	−1.3 (2)
C2—C28—C23—C23A	172.51 (13)	C3—C31—C32—C33	173.30 (13)
C22—C23—C23A—C24	−177.89 (15)	C36—C31—C32—Br32	177.45 (10)
C28—C23—C23A—C24	−3.0 (2)	C3—C31—C32—Br32	−7.92 (18)
C22—C23—C23A—C27A	1.45 (15)	C31—C32—C33—C34	0.4 (2)
C28—C23—C23A—C27A	176.39 (13)	Br32—C32—C33—C34	−178.40 (11)
C27A—C23A—C24—C25	0.2 (2)	C32—C33—C34—C35	0.7 (2)
C23—C23A—C24—C25	179.45 (15)	C33—C34—C35—C36	−0.8 (2)
C23A—C24—C25—C26	0.9 (2)	C34—C35—C36—C31	−0.1 (2)
C24—C25—C26—C27	−1.0 (2)	C32—C31—C36—C35	1.2 (2)
C25—C26—C27—C27A	0.0 (2)	C3—C31—C36—C35	−173.32 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24···Cg1^i	0.95	2.77	3.544 (3)	139

Symmetry code: (i) x, y+1, z.

(2RS)-2-(2-Bromobenzyl)-3-(1-methyl-1H-indol-3-yl)-\ 3-oxopropanenitrile (IIb)

Crystal data

C19H15BrN2O	F(000) = 1488
Mr = 367.24	Dx = 1.539 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.728 (6) Å	Cell parameters from 7297 reflections
b = 14.901 (6) Å	θ = 2.4–27.6°
c = 15.507 (6) Å	µ = 2.60 mm^−1
β = 92.165 (19)°	T = 100 K
V = 3170 (2) Å^3	Plate, yellow-brown
Z = 8	0.40 × 0.30 × 0.10 mm

Data collection

Bruker D8 Venture diffractometer	7297 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube	5456 reflections with I > 2σ(I)
Multilayer mirror monochromator	Rint = 0.090
φ and ω scans	θmax = 27.6°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −17→17
Tmin = 0.489, Tmax = 0.771	k = −18→19
79963 measured reflections	l = −20→20

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.072	w = 1/[σ^2(Fo^2) + (0.0217P)^2 + 3.7392P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.002
7297 reflections	Δρmax = 0.54 e Å^−3
417 parameters	Δρmin = −0.76 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
N11	0.18232 (18)	0.42519 (15)	0.29826 (14)	0.0248 (5)
C11	0.2371 (2)	0.47754 (16)	0.27615 (16)	0.0168 (5)
C12	0.30553 (18)	0.54607 (16)	0.24554 (15)	0.0133 (5)
H12	0.2725	0.6059	0.2438	0.016*
C13	0.33425 (18)	0.51972 (15)	0.15332 (15)	0.0133 (5)
O13	0.34791 (14)	0.44049 (11)	0.13777 (11)	0.0198 (4)
C127	0.39870 (19)	0.55156 (16)	0.30549 (15)	0.0146 (5)
H12A	0.4337	0.4936	0.3035	0.018*
H12B	0.4423	0.5985	0.2834	0.018*
C121	0.37709 (18)	0.57268 (16)	0.39815 (16)	0.0134 (5)
C122	0.35456 (18)	0.65859 (16)	0.42667 (16)	0.0131 (5)
Br12	0.34405 (2)	0.75572 (2)	0.34672 (2)	0.01692 (7)
C123	0.33681 (19)	0.67677 (17)	0.51225 (16)	0.0153 (5)
H123	0.3223	0.7361	0.5300	0.018*
C124	0.34047 (19)	0.60709 (17)	0.57167 (16)	0.0186 (6)
H124	0.3284	0.6188	0.6305	0.022*
C125	0.3616 (2)	0.52069 (17)	0.54579 (17)	0.0194 (6)
H125	0.3636	0.4730	0.5865	0.023*
C126	0.37979 (19)	0.50432 (17)	0.45965 (16)	0.0181 (5)
H126	0.3945	0.4449	0.4422	0.022*
N131	0.33943 (15)	0.72482 (13)	0.02457 (13)	0.0130 (4)
C132	0.32742 (18)	0.68181 (16)	0.10035 (15)	0.0129 (5)
H132	0.3100	0.7100	0.1525	0.016*
C133	0.34426 (18)	0.59041 (16)	0.09058 (15)	0.0132 (5)
C13A	0.36750 (18)	0.57742 (16)	0.00110 (15)	0.0126 (5)
C134	0.38778 (18)	0.50255 (17)	−0.04959 (15)	0.0156 (5)
H134	0.3906	0.4442	−0.0250	0.019*
C135	0.40367 (19)	0.51530 (18)	−0.13629 (17)	0.0196 (6)
H135	0.4165	0.4649	−0.1716	0.024*
C136	0.40119 (19)	0.60133 (18)	−0.17306 (16)	0.0196 (6)
H136	0.4134	0.6081	−0.2326	0.023*
C137	0.38127 (19)	0.67663 (17)	−0.12446 (16)	0.0163 (5)
H137	0.3798	0.7350	−0.1492	0.020*
C17A	0.36354 (18)	0.66288 (16)	−0.03762 (15)	0.0132 (5)
C131	0.3262 (2)	0.82032 (16)	0.00842 (17)	0.0190 (6)
H13A	0.3095	0.8504	0.0621	0.029*
H13B	0.2734	0.8291	−0.0351	0.029*
H13C	0.3867	0.8457	−0.0126	0.029*
N21	0.22989 (19)	0.33176 (16)	0.79585 (15)	0.0273 (6)
C21	0.2823 (2)	0.27789 (16)	0.77344 (16)	0.0164 (5)
C22	0.34802 (18)	0.20737 (16)	0.74254 (15)	0.0126 (5)
H22	0.3133	0.1484	0.7423	0.015*
C23	0.37571 (18)	0.23082 (15)	0.64954 (15)	0.0137 (5)
O23	0.39429 (14)	0.30937 (11)	0.63232 (11)	0.0198 (4)
C227	0.44284 (18)	0.20000 (16)	0.79972 (15)	0.0140 (5)
H22A	0.4848	0.1527	0.7760	0.017*
H22B	0.4787	0.2575	0.7973	0.017*
C221	0.42413 (18)	0.17826 (16)	0.89260 (15)	0.0130 (5)
C222	0.40507 (18)	0.09155 (16)	0.92183 (15)	0.0138 (5)
Br22	0.39344 (2)	−0.00513 (2)	0.84159 (2)	0.01913 (7)
C223	0.39041 (19)	0.07332 (17)	1.00809 (16)	0.0166 (5)
H223	0.3797	0.0135	1.0266	0.020*
C224	0.39156 (19)	0.14326 (17)	1.06685 (16)	0.0177 (5)
H224	0.3811	0.1313	1.1260	0.021*
C225	0.40795 (19)	0.23065 (17)	1.04010 (16)	0.0177 (5)
H225	0.4074	0.2787	1.0804	0.021*
C226	0.42517 (18)	0.24722 (16)	0.95389 (16)	0.0159 (5)
H226	0.4380	0.3069	0.9360	0.019*
N231	0.36915 (16)	0.02132 (13)	0.52880 (13)	0.0140 (4)
C232	0.35817 (18)	0.06868 (16)	0.60173 (15)	0.0136 (5)
H232	0.3381	0.0442	0.6548	0.016*
C233	0.38029 (18)	0.15829 (15)	0.58849 (15)	0.0126 (5)
C23A	0.40570 (18)	0.16573 (16)	0.49902 (15)	0.0133 (5)
C234	0.43411 (19)	0.23648 (17)	0.44611 (16)	0.0180 (5)
H234	0.4402	0.2958	0.4682	0.022*
C235	0.4530 (2)	0.21792 (19)	0.36101 (17)	0.0231 (6)
H235	0.4708	0.2655	0.3240	0.028*
C236	0.4466 (2)	0.13043 (19)	0.32817 (17)	0.0237 (6)
H236	0.4615	0.1198	0.2697	0.028*
C237	0.41896 (19)	0.05918 (18)	0.37893 (16)	0.0190 (6)
H237	0.4144	−0.0002	0.3568	0.023*
C27A	0.39814 (18)	0.07874 (16)	0.46411 (15)	0.0143 (5)
C231	0.3488 (2)	−0.07415 (16)	0.51695 (17)	0.0177 (5)
H23A	0.3322	−0.1007	0.5723	0.027*
H23B	0.4065	−0.1041	0.4953	0.027*
H23C	0.2939	−0.0817	0.4753	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0269 (14)	0.0297 (12)	0.0177 (12)	−0.0120 (11)	−0.0031 (10)	0.0050 (10)
C11	0.0179 (15)	0.0211 (13)	0.0111 (12)	−0.0018 (11)	−0.0050 (10)	0.0003 (10)
C12	0.0141 (14)	0.0124 (11)	0.0133 (12)	−0.0004 (9)	−0.0005 (10)	0.0006 (9)
C13	0.0116 (13)	0.0140 (12)	0.0142 (12)	−0.0020 (9)	−0.0007 (10)	−0.0007 (9)
O13	0.0268 (11)	0.0137 (9)	0.0189 (9)	−0.0008 (8)	0.0017 (8)	−0.0017 (7)
C127	0.0138 (14)	0.0134 (11)	0.0166 (12)	0.0003 (10)	−0.0009 (10)	−0.0030 (9)
C121	0.0084 (13)	0.0160 (12)	0.0157 (12)	−0.0027 (10)	−0.0020 (10)	−0.0021 (9)
C122	0.0092 (13)	0.0160 (12)	0.0139 (12)	−0.0031 (9)	−0.0021 (10)	0.0011 (9)
Br12	0.02524 (15)	0.01184 (11)	0.01379 (12)	−0.00209 (10)	0.00211 (10)	−0.00004 (9)
C123	0.0123 (14)	0.0182 (12)	0.0152 (13)	−0.0036 (10)	−0.0026 (10)	−0.0023 (10)
C124	0.0149 (14)	0.0287 (14)	0.0119 (12)	−0.0048 (11)	−0.0021 (10)	0.0005 (10)
C125	0.0158 (14)	0.0234 (13)	0.0186 (13)	−0.0012 (11)	−0.0044 (11)	0.0083 (10)
C126	0.0164 (14)	0.0149 (12)	0.0225 (13)	0.0012 (10)	−0.0049 (10)	0.0013 (10)
N131	0.0130 (11)	0.0134 (10)	0.0125 (10)	−0.0015 (8)	−0.0028 (8)	−0.0008 (8)
C132	0.0106 (13)	0.0164 (12)	0.0116 (12)	−0.0013 (9)	−0.0032 (10)	−0.0013 (9)
C133	0.0116 (13)	0.0150 (12)	0.0127 (12)	−0.0009 (9)	−0.0010 (10)	−0.0001 (9)
C13A	0.0085 (13)	0.0163 (12)	0.0128 (12)	−0.0021 (9)	−0.0022 (10)	−0.0002 (9)
C134	0.0123 (13)	0.0176 (12)	0.0170 (12)	0.0009 (10)	0.0004 (10)	−0.0021 (10)
C135	0.0133 (14)	0.0265 (14)	0.0191 (13)	0.0007 (11)	0.0019 (11)	−0.0081 (11)
C136	0.0143 (14)	0.0343 (15)	0.0099 (12)	−0.0018 (11)	−0.0011 (10)	−0.0010 (10)
C137	0.0116 (14)	0.0231 (13)	0.0138 (12)	−0.0025 (10)	−0.0032 (10)	0.0032 (10)
C17A	0.0074 (13)	0.0164 (12)	0.0155 (12)	−0.0020 (9)	−0.0042 (10)	−0.0014 (9)
C131	0.0241 (16)	0.0135 (12)	0.0191 (13)	0.0009 (11)	−0.0026 (11)	0.0026 (10)
N21	0.0259 (15)	0.0317 (13)	0.0243 (13)	0.0088 (11)	0.0008 (11)	−0.0055 (10)
C21	0.0172 (14)	0.0205 (12)	0.0111 (12)	0.0001 (11)	−0.0023 (10)	−0.0016 (10)
C22	0.0133 (13)	0.0122 (11)	0.0122 (12)	0.0009 (9)	0.0000 (10)	−0.0005 (9)
C23	0.0118 (13)	0.0157 (12)	0.0133 (12)	0.0026 (10)	−0.0029 (10)	0.0006 (9)
O23	0.0284 (12)	0.0114 (8)	0.0197 (10)	0.0007 (7)	0.0013 (8)	0.0009 (7)
C227	0.0127 (14)	0.0147 (11)	0.0145 (12)	0.0006 (10)	−0.0017 (10)	0.0005 (9)
C221	0.0081 (13)	0.0168 (12)	0.0140 (12)	0.0021 (9)	−0.0009 (10)	0.0008 (9)
C222	0.0126 (13)	0.0155 (12)	0.0130 (12)	0.0032 (10)	−0.0037 (10)	−0.0019 (9)
Br22	0.03058 (16)	0.01197 (12)	0.01466 (12)	0.00296 (11)	−0.00141 (10)	−0.00100 (9)
C223	0.0155 (14)	0.0176 (12)	0.0165 (13)	0.0019 (10)	−0.0025 (10)	0.0039 (10)
C224	0.0140 (14)	0.0280 (13)	0.0110 (12)	0.0004 (11)	−0.0033 (10)	0.0019 (10)
C225	0.0135 (14)	0.0226 (13)	0.0168 (13)	0.0003 (10)	−0.0040 (10)	−0.0066 (10)
C226	0.0130 (13)	0.0155 (11)	0.0189 (12)	−0.0002 (10)	−0.0028 (10)	0.0002 (10)
N231	0.0160 (12)	0.0124 (10)	0.0135 (10)	0.0012 (8)	−0.0028 (9)	−0.0027 (8)
C232	0.0138 (14)	0.0157 (11)	0.0111 (12)	0.0050 (10)	−0.0028 (10)	0.0005 (9)
C233	0.0094 (13)	0.0158 (11)	0.0124 (12)	0.0033 (9)	−0.0028 (10)	0.0009 (9)
C23A	0.0091 (13)	0.0183 (12)	0.0123 (12)	0.0039 (10)	−0.0022 (10)	−0.0002 (9)
C234	0.0157 (14)	0.0196 (13)	0.0188 (13)	0.0020 (10)	0.0009 (10)	0.0042 (10)
C235	0.0196 (15)	0.0330 (15)	0.0169 (13)	0.0001 (12)	0.0021 (11)	0.0058 (11)
C236	0.0188 (16)	0.0404 (16)	0.0117 (13)	0.0026 (12)	−0.0005 (11)	−0.0025 (11)
C237	0.0122 (14)	0.0295 (14)	0.0149 (13)	0.0022 (11)	−0.0044 (11)	−0.0086 (11)
C27A	0.0094 (13)	0.0200 (12)	0.0132 (12)	0.0025 (10)	−0.0044 (10)	−0.0007 (9)
C231	0.0190 (15)	0.0135 (12)	0.0205 (13)	−0.0011 (10)	−0.0032 (11)	−0.0034 (10)

Geometric parameters (Å, º)

N11—C11	1.145 (3)	N21—C21	1.141 (3)
C11—C12	1.478 (3)	C21—C22	1.476 (3)
C12—C13	1.548 (3)	C22—C23	1.545 (3)
C12—C127	1.555 (3)	C22—C227	1.551 (3)
C12—H12	1.0000	C22—H22	1.0000
C13—O13	1.221 (3)	C23—O23	1.229 (3)
C13—C133	1.444 (3)	C23—C233	1.440 (3)
C127—C121	1.511 (3)	C227—C221	1.508 (3)
C127—H12A	0.9900	C227—H22A	0.9900
C127—H12B	0.9900	C227—H22B	0.9900
C121—C122	1.393 (3)	C221—C222	1.397 (3)
C121—C126	1.395 (3)	C221—C226	1.399 (3)
C122—C123	1.385 (3)	C222—C223	1.387 (3)
C122—Br12	1.908 (2)	C222—Br22	1.906 (2)
C123—C124	1.388 (3)	C223—C224	1.384 (4)
C123—H123	0.9500	C223—H223	0.9500
C124—C125	1.383 (4)	C224—C225	1.388 (4)
C124—H124	0.9500	C224—H224	0.9500
C125—C126	1.390 (4)	C225—C226	1.389 (3)
C125—H125	0.9500	C225—H225	0.9500
C126—H126	0.9500	C226—H226	0.9500
N131—C132	1.354 (3)	N231—C232	1.346 (3)
N131—C17A	1.384 (3)	N231—C27A	1.388 (3)
N131—C131	1.455 (3)	N231—C231	1.460 (3)
C132—C133	1.391 (3)	C232—C233	1.386 (3)
C132—H132	0.9500	C232—H232	0.9500
C133—C13A	1.449 (3)	C233—C23A	1.448 (3)
C13A—C134	1.399 (3)	C23A—C234	1.400 (3)
C13A—C17A	1.408 (3)	C23A—C27A	1.407 (3)
C134—C135	1.383 (4)	C234—C235	1.382 (4)
C134—H134	0.9500	C234—H234	0.9500
C135—C136	1.403 (4)	C235—C236	1.401 (4)
C135—H135	0.9500	C235—H235	0.9500
C136—C137	1.385 (4)	C236—C237	1.383 (4)
C136—H136	0.9500	C236—H236	0.9500
C137—C17A	1.393 (3)	C237—C27A	1.393 (3)
C137—H137	0.9500	C237—H237	0.9500
C131—H13A	0.9800	C231—H23A	0.9800
C131—H13B	0.9800	C231—H23B	0.9800
C131—H13C	0.9800	C231—H23C	0.9800
N11—C11—C12	178.2 (3)	N21—C21—C22	178.4 (3)
C11—C12—C13	107.97 (19)	C21—C22—C23	108.47 (19)
C11—C12—C127	111.3 (2)	C21—C22—C227	112.0 (2)
C13—C12—C127	109.5 (2)	C23—C22—C227	108.6 (2)
C11—C12—H12	109.4	C21—C22—H22	109.2
C13—C12—H12	109.4	C23—C22—H22	109.2
C127—C12—H12	109.4	C227—C22—H22	109.2
O13—C13—C133	123.6 (2)	O23—C23—C233	123.9 (2)
O13—C13—C12	118.3 (2)	O23—C23—C22	118.6 (2)
C133—C13—C12	118.1 (2)	C233—C23—C22	117.5 (2)
C121—C127—C12	113.1 (2)	C221—C227—C22	113.1 (2)
C121—C127—H12A	109.0	C221—C227—H22A	109.0
C12—C127—H12A	109.0	C22—C227—H22A	109.0
C121—C127—H12B	109.0	C221—C227—H22B	109.0
C12—C127—H12B	109.0	C22—C227—H22B	109.0
H12A—C127—H12B	107.8	H22A—C227—H22B	107.8
C122—C121—C126	117.0 (2)	C222—C221—C226	117.1 (2)
C122—C121—C127	123.2 (2)	C222—C221—C227	123.3 (2)
C126—C121—C127	119.8 (2)	C226—C221—C227	119.6 (2)
C123—C122—C121	122.2 (2)	C223—C222—C221	122.0 (2)
C123—C122—Br12	117.56 (18)	C223—C222—Br22	118.02 (18)
C121—C122—Br12	120.21 (18)	C221—C222—Br22	119.95 (18)
C122—C123—C124	119.1 (2)	C224—C223—C222	119.3 (2)
C122—C123—H123	120.4	C224—C223—H223	120.4
C124—C123—H123	120.4	C222—C223—H223	120.4
C125—C124—C123	120.4 (2)	C223—C224—C225	120.5 (2)
C125—C124—H124	119.8	C223—C224—H224	119.7
C123—C124—H124	119.8	C225—C224—H224	119.7
C124—C125—C126	119.3 (2)	C224—C225—C226	119.4 (2)
C124—C125—H125	120.3	C224—C225—H225	120.3
C126—C125—H125	120.3	C226—C225—H225	120.3
C125—C126—C121	121.9 (2)	C225—C226—C221	121.7 (2)
C125—C126—H126	119.1	C225—C226—H226	119.1
C121—C126—H126	119.1	C221—C226—H226	119.1
C132—N131—C17A	109.22 (19)	C232—N231—C27A	109.2 (2)
C132—N131—C131	126.4 (2)	C232—N231—C231	126.1 (2)
C17A—N131—C131	124.3 (2)	C27A—N231—C231	124.6 (2)
N131—C132—C133	110.0 (2)	N231—C232—C233	110.4 (2)
N131—C132—H132	125.0	N231—C232—H232	124.8
C133—C132—H132	125.0	C233—C232—H232	124.8
C132—C133—C13	128.4 (2)	C232—C233—C23	127.6 (2)
C132—C133—C13A	106.2 (2)	C232—C233—C23A	106.1 (2)
C13—C133—C13A	125.3 (2)	C23—C233—C23A	126.2 (2)
C134—C13A—C17A	119.1 (2)	C234—C23A—C27A	119.1 (2)
C134—C13A—C133	134.5 (2)	C234—C23A—C233	134.6 (2)
C17A—C13A—C133	106.3 (2)	C27A—C23A—C233	106.3 (2)
C135—C134—C13A	118.6 (2)	C235—C234—C23A	118.4 (2)
C135—C134—H134	120.7	C235—C234—H234	120.8
C13A—C134—H134	120.7	C23A—C234—H234	120.8
C134—C135—C136	121.2 (2)	C234—C235—C236	121.4 (3)
C134—C135—H135	119.4	C234—C235—H235	119.3
C136—C135—H135	119.4	C236—C235—H235	119.3
C137—C136—C135	121.4 (2)	C237—C236—C235	121.5 (2)
C137—C136—H136	119.3	C237—C236—H236	119.3
C135—C136—H136	119.3	C235—C236—H236	119.3
C136—C137—C17A	116.9 (2)	C236—C237—C27A	116.7 (2)
C136—C137—H137	121.5	C236—C237—H237	121.6
C17A—C137—H137	121.5	C27A—C237—H237	121.6
N131—C17A—C137	129.1 (2)	N231—C27A—C237	129.1 (2)
N131—C17A—C13A	108.2 (2)	N231—C27A—C23A	108.0 (2)
C137—C17A—C13A	122.7 (2)	C237—C27A—C23A	122.9 (2)
N131—C131—H13A	109.5	N231—C231—H23A	109.5
N131—C131—H13B	109.5	N231—C231—H23B	109.5
H13A—C131—H13B	109.5	H23A—C231—H23B	109.5
N131—C131—H13C	109.5	N231—C231—H23C	109.5
H13A—C131—H13C	109.5	H23A—C231—H23C	109.5
H13B—C131—H13C	109.5	H23B—C231—H23C	109.5
C11—C12—C13—O13	−39.4 (3)	C21—C22—C23—O23	41.5 (3)
C127—C12—C13—O13	81.8 (3)	C227—C22—C23—O23	−80.5 (3)
C11—C12—C13—C133	141.1 (2)	C21—C22—C23—C233	−139.9 (2)
C127—C12—C13—C133	−97.6 (3)	C227—C22—C23—C233	98.1 (3)
C11—C12—C127—C121	−58.0 (3)	C21—C22—C227—C221	59.6 (3)
C13—C12—C127—C121	−177.27 (19)	C23—C22—C227—C221	179.33 (19)
C12—C127—C121—C122	−77.7 (3)	C22—C227—C221—C222	80.5 (3)
C12—C127—C121—C126	102.7 (3)	C22—C227—C221—C226	−99.3 (3)
C126—C121—C122—C123	0.9 (4)	C226—C221—C222—C223	−1.8 (4)
C127—C121—C122—C123	−178.7 (2)	C227—C221—C222—C223	178.4 (2)
C126—C121—C122—Br12	−177.55 (19)	C226—C221—C222—Br22	175.73 (18)
C127—C121—C122—Br12	2.8 (3)	C227—C221—C222—Br22	−4.1 (3)
C121—C122—C123—C124	−0.7 (4)	C221—C222—C223—C224	2.1 (4)
Br12—C122—C123—C124	177.78 (19)	Br22—C222—C223—C224	−175.5 (2)
C122—C123—C124—C125	0.0 (4)	C222—C223—C224—C225	−0.5 (4)
C123—C124—C125—C126	0.4 (4)	C223—C224—C225—C226	−1.3 (4)
C124—C125—C126—C121	−0.2 (4)	C224—C225—C226—C221	1.6 (4)
C122—C121—C126—C125	−0.4 (4)	C222—C221—C226—C225	−0.1 (4)
C127—C121—C126—C125	179.2 (2)	C227—C221—C226—C225	179.7 (2)
C17A—N131—C132—C133	0.6 (3)	C27A—N231—C232—C233	−0.6 (3)
C131—N131—C132—C133	178.6 (2)	C231—N231—C232—C233	−177.4 (2)
N131—C132—C133—C13	−176.3 (2)	N231—C232—C233—C23	178.6 (2)
N131—C132—C133—C13A	−0.5 (3)	N231—C232—C233—C23A	0.8 (3)
O13—C13—C133—C132	177.6 (3)	O23—C23—C233—C232	−178.1 (3)
C12—C13—C133—C132	−2.9 (4)	C22—C23—C233—C232	3.3 (4)
O13—C13—C133—C13A	2.6 (4)	O23—C23—C233—C23A	−0.7 (4)
C12—C13—C133—C13A	−177.9 (2)	C22—C23—C233—C23A	−179.3 (2)
C132—C133—C13A—C134	−177.3 (3)	C232—C233—C23A—C234	179.7 (3)
C13—C133—C13A—C134	−1.4 (5)	C23—C233—C23A—C234	1.9 (5)
C132—C133—C13A—C17A	0.3 (3)	C232—C233—C23A—C27A	−0.6 (3)
C13—C133—C13A—C17A	176.2 (2)	C23—C233—C23A—C27A	−178.5 (2)
C17A—C13A—C134—C135	0.3 (4)	C27A—C23A—C234—C235	0.5 (4)
C133—C13A—C134—C135	177.5 (3)	C233—C23A—C234—C235	−180.0 (3)
C13A—C134—C135—C136	1.0 (4)	C23A—C234—C235—C236	−1.6 (4)
C134—C135—C136—C137	−1.0 (4)	C234—C235—C236—C237	1.4 (4)
C135—C136—C137—C17A	−0.2 (4)	C235—C236—C237—C27A	−0.1 (4)
C132—N131—C17A—C137	179.1 (3)	C232—N231—C27A—C237	179.3 (3)
C131—N131—C17A—C137	1.1 (4)	C231—N231—C27A—C237	−4.0 (4)
C132—N131—C17A—C13A	−0.4 (3)	C232—N231—C27A—C23A	0.2 (3)
C131—N131—C17A—C13A	−178.5 (2)	C231—N231—C27A—C23A	177.0 (2)
C136—C137—C17A—N131	−178.0 (2)	C236—C237—C27A—N231	−180.0 (3)
C136—C137—C17A—C13A	1.5 (4)	C236—C237—C27A—C23A	−1.0 (4)
C134—C13A—C17A—N131	178.1 (2)	C234—C23A—C27A—N231	180.0 (2)
C133—C13A—C17A—N131	0.1 (3)	C233—C23A—C27A—N231	0.3 (3)
C134—C13A—C17A—C137	−1.5 (4)	C234—C23A—C27A—C237	0.9 (4)
C133—C13A—C17A—C137	−179.5 (2)	C233—C23A—C27A—C237	−178.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C125—H125···O23	0.95	2.57	3.446 (3)	153

(2RS)-3-(1-benzyl-1H-indol-3-yl)-\ 2-(2-bromobenzyl)-3-oxopropanenitrile (IIc)

Crystal data

C25H19BrN2O	Z = 4
Mr = 443.32	F(000) = 904
Triclinic, P1	Dx = 1.468 Mg m^−3
a = 10.912 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.544 (8) Å	Cell parameters from 9244 reflections
c = 15.583 (7) Å	θ = 2.2–27.6°
α = 89.23 (4)°	µ = 2.07 mm^−1
β = 79.49 (3)°	T = 100 K
γ = 73.20 (3)°	Plate, colourless
V = 2006.0 (18) Å^3	0.22 × 0.21 × 0.10 mm

Data collection

Bruker D8 Venture diffractometer	9244 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube	6872 reflections with I > 2σ(I)
Multilayer mirror monochromator	Rint = 0.112
φ and ω scans	θmax = 27.6°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −14→14
Tmin = 0.737, Tmax = 0.813	k = −16→16
96931 measured reflections	l = −20→20

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.084	w = 1/[σ^2(Fo^2) + (0.025P)^2 + 2.2423P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.002
9244 reflections	Δρmax = 0.40 e Å^−3
523 parameters	Δρmin = −0.57 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
N11	0.5097 (2)	0.73044 (17)	0.58025 (14)	0.0195 (5)
C11	0.5794 (2)	0.64664 (19)	0.59130 (15)	0.0131 (5)
C12	0.6656 (2)	0.53736 (18)	0.60712 (15)	0.0120 (5)
H12	0.7183	0.5464	0.6512	0.014*
C13	0.7577 (2)	0.48592 (19)	0.52103 (15)	0.0135 (5)
O13	0.71866 (16)	0.50668 (14)	0.45193 (11)	0.0195 (4)
C127	0.5832 (2)	0.45808 (19)	0.64171 (15)	0.0143 (5)
H12A	0.5311	0.4499	0.5978	0.017*
H12B	0.6427	0.3836	0.6488	0.017*
C121	0.4926 (2)	0.49869 (19)	0.72782 (15)	0.0142 (5)
C122	0.5251 (2)	0.4672 (2)	0.80876 (16)	0.0183 (5)
Br12	0.69435 (3)	0.37370 (2)	0.81581 (2)	0.02901 (8)
C123	0.4382 (3)	0.5025 (2)	0.88675 (17)	0.0260 (6)
H123	0.4620	0.4766	0.9407	0.031*
C124	0.3165 (3)	0.5757 (2)	0.88513 (18)	0.0265 (6)
H124	0.2569	0.6020	0.9382	0.032*
C125	0.2820 (2)	0.6105 (2)	0.80614 (17)	0.0222 (6)
H125	0.1989	0.6614	0.8049	0.027*
C126	0.3682 (2)	0.5712 (2)	0.72888 (16)	0.0157 (5)
H126	0.3421	0.5943	0.6750	0.019*
N131	1.05957 (19)	0.31755 (16)	0.58068 (13)	0.0148 (4)
C132	0.9391 (2)	0.39054 (19)	0.60079 (15)	0.0154 (5)
H132	0.8986	0.4230	0.6574	0.019*
C133	0.8832 (2)	0.41133 (19)	0.52668 (15)	0.0133 (5)
C13A	0.9782 (2)	0.34516 (19)	0.45581 (15)	0.0133 (5)
C134	0.9828 (2)	0.3297 (2)	0.36647 (16)	0.0170 (5)
H134	0.9101	0.3658	0.3405	0.020*
C135	1.0950 (2)	0.2608 (2)	0.31686 (17)	0.0217 (6)
H135	1.0997	0.2509	0.2559	0.026*
C136	1.2021 (2)	0.2051 (2)	0.35422 (17)	0.0224 (6)
H136	1.2780	0.1586	0.3181	0.027*
C137	1.1995 (2)	0.2166 (2)	0.44269 (16)	0.0174 (5)
H137	1.2712	0.1775	0.4686	0.021*
C17A	1.0870 (2)	0.28790 (19)	0.49215 (15)	0.0129 (5)
C131	1.1538 (2)	0.2766 (2)	0.63886 (16)	0.0218 (6)
H13A	1.2325	0.3007	0.6178	0.026*
H13B	1.1805	0.1941	0.6367	0.026*
C141	1.0984 (2)	0.3190 (2)	0.73197 (16)	0.0149 (5)
C142	1.1034 (2)	0.4222 (2)	0.75954 (17)	0.0202 (5)
H142	1.1446	0.4651	0.7199	0.024*
C143	1.0485 (2)	0.4633 (2)	0.84465 (17)	0.0214 (6)
H143	1.0501	0.5349	0.8626	0.026*
C144	0.9916 (2)	0.3996 (2)	0.90330 (16)	0.0179 (5)
H144	0.9546	0.4273	0.9616	0.022*
C145	0.9885 (2)	0.2956 (2)	0.87698 (16)	0.0184 (5)
H145	0.9507	0.2514	0.9174	0.022*
C146	1.0409 (2)	0.2560 (2)	0.79148 (17)	0.0182 (5)
H146	1.0373	0.1851	0.7734	0.022*
N21	−0.0140 (2)	0.75831 (17)	0.92059 (14)	0.0192 (5)
C21	−0.0827 (2)	0.84265 (19)	0.90939 (15)	0.0127 (5)
C22	−0.1675 (2)	0.95153 (18)	0.89134 (15)	0.0119 (5)
H22	−0.2217	0.9411	0.8486	0.014*
C23	−0.2577 (2)	1.00946 (18)	0.97633 (15)	0.0121 (5)
O23	−0.21598 (16)	0.99589 (14)	1.04483 (11)	0.0193 (4)
C227	−0.0836 (2)	1.02767 (19)	0.85264 (15)	0.0140 (5)
H22A	−0.1419	1.1008	0.8409	0.017*
H22B	−0.0334	1.0405	0.8964	0.017*
C221	0.0100 (2)	0.97895 (19)	0.76913 (15)	0.0134 (5)
C222	−0.0218 (2)	0.9938 (2)	0.68648 (16)	0.0192 (5)
Br22	−0.19115 (3)	1.08181 (2)	0.67357 (2)	0.03007 (8)
C223	0.0658 (3)	0.9457 (2)	0.61163 (17)	0.0278 (6)
H223	0.0407	0.9565	0.5562	0.033*
C224	0.1898 (3)	0.8817 (2)	0.61815 (17)	0.0234 (6)
H224	0.2508	0.8489	0.5671	0.028*
C225	0.2247 (2)	0.8658 (2)	0.69909 (16)	0.0180 (5)
H225	0.3099	0.8217	0.7038	0.022*
C226	0.1361 (2)	0.9140 (2)	0.77368 (16)	0.0151 (5)
H226	0.1617	0.9025	0.8290	0.018*
N231	−0.55993 (18)	1.17202 (16)	0.91369 (13)	0.0137 (4)
C232	−0.4425 (2)	1.09431 (19)	0.89647 (15)	0.0137 (5)
H232	−0.4059	1.0531	0.8426	0.016*
C233	−0.3829 (2)	1.08334 (19)	0.96888 (15)	0.0124 (5)
C23A	−0.4724 (2)	1.16068 (18)	1.03560 (15)	0.0111 (4)
C234	−0.4707 (2)	1.1906 (2)	1.12156 (15)	0.0159 (5)
H234	−0.3978	1.1566	1.1479	0.019*
C235	−0.5773 (2)	1.2708 (2)	1.16723 (16)	0.0191 (5)
H235	−0.5775	1.2910	1.2258	0.023*
C236	−0.6849 (2)	1.3230 (2)	1.12889 (16)	0.0198 (5)
H236	−0.7565	1.3779	1.1619	0.024*
C237	−0.6888 (2)	1.2960 (2)	1.04415 (16)	0.0166 (5)
H237	−0.7613	1.3316	1.0178	0.020*
C27A	−0.5817 (2)	1.21439 (19)	0.99891 (15)	0.0123 (5)
C231	−0.6569 (2)	1.2033 (2)	0.85626 (16)	0.0191 (5)
H23B	−0.6932	1.2854	0.8583	0.023*
H23A	−0.7294	1.1714	0.8779	0.023*
C241	−0.5981 (2)	1.16213 (19)	0.76315 (15)	0.0145 (5)
C242	−0.5973 (2)	1.0580 (2)	0.73402 (17)	0.0194 (5)
H242	−0.6364	1.0129	0.7727	0.023*
C243	−0.5399 (2)	1.0189 (2)	0.64900 (17)	0.0204 (5)
H243	−0.5384	0.9468	0.6300	0.025*
C244	−0.4846 (2)	1.0852 (2)	0.59180 (16)	0.0178 (5)
H244	−0.4451	1.0586	0.5336	0.021*
C245	−0.4871 (2)	1.1902 (2)	0.61982 (16)	0.0187 (5)
H245	−0.4506	1.2363	0.5805	0.022*
C246	−0.5431 (2)	1.22815 (19)	0.70545 (16)	0.0156 (5)
H246	−0.5437	1.2999	0.7246	0.019*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0183 (11)	0.0179 (11)	0.0181 (11)	−0.0017 (9)	0.0017 (9)	0.0006 (9)
C11	0.0118 (11)	0.0158 (12)	0.0105 (11)	−0.0041 (9)	0.0015 (9)	−0.0027 (9)
C12	0.0126 (11)	0.0112 (11)	0.0105 (11)	−0.0006 (9)	−0.0023 (9)	−0.0011 (9)
C13	0.0137 (11)	0.0124 (12)	0.0145 (12)	−0.0041 (9)	−0.0025 (9)	−0.0017 (9)
O13	0.0193 (9)	0.0243 (10)	0.0112 (9)	0.0016 (7)	−0.0062 (7)	−0.0024 (7)
C127	0.0161 (12)	0.0106 (11)	0.0156 (12)	−0.0036 (9)	−0.0021 (9)	−0.0017 (9)
C121	0.0170 (12)	0.0143 (12)	0.0141 (12)	−0.0093 (9)	−0.0020 (9)	−0.0003 (9)
C122	0.0203 (13)	0.0197 (13)	0.0178 (13)	−0.0092 (10)	−0.0053 (10)	0.0017 (10)
Br12	0.02806 (16)	0.03083 (16)	0.02740 (16)	−0.00258 (12)	−0.01353 (12)	0.00779 (12)
C123	0.0300 (15)	0.0390 (17)	0.0155 (13)	−0.0199 (13)	−0.0049 (11)	0.0026 (12)
C124	0.0236 (14)	0.0372 (16)	0.0196 (14)	−0.0165 (12)	0.0068 (11)	−0.0091 (12)
C125	0.0154 (12)	0.0234 (14)	0.0268 (15)	−0.0077 (10)	0.0024 (11)	−0.0029 (11)
C126	0.0152 (12)	0.0183 (13)	0.0167 (12)	−0.0096 (10)	−0.0030 (10)	0.0013 (10)
N131	0.0139 (10)	0.0157 (10)	0.0128 (10)	0.0001 (8)	−0.0045 (8)	−0.0008 (8)
C132	0.0157 (12)	0.0165 (12)	0.0116 (12)	−0.0011 (9)	−0.0015 (9)	−0.0021 (9)
C133	0.0139 (11)	0.0140 (12)	0.0121 (12)	−0.0034 (9)	−0.0035 (9)	−0.0011 (9)
C13A	0.0141 (11)	0.0120 (11)	0.0136 (12)	−0.0040 (9)	−0.0014 (9)	−0.0009 (9)
C134	0.0183 (12)	0.0171 (12)	0.0157 (12)	−0.0046 (10)	−0.0046 (10)	0.0000 (10)
C135	0.0236 (13)	0.0268 (14)	0.0124 (12)	−0.0052 (11)	−0.0007 (10)	−0.0071 (10)
C136	0.0175 (13)	0.0242 (14)	0.0207 (14)	−0.0023 (10)	0.0035 (10)	−0.0080 (11)
C137	0.0125 (12)	0.0172 (13)	0.0197 (13)	−0.0015 (9)	−0.0004 (10)	−0.0019 (10)
C17A	0.0144 (11)	0.0107 (11)	0.0136 (12)	−0.0043 (9)	−0.0016 (9)	−0.0011 (9)
C131	0.0140 (12)	0.0283 (15)	0.0174 (13)	0.0042 (10)	−0.0056 (10)	0.0003 (11)
C141	0.0114 (11)	0.0170 (12)	0.0147 (12)	0.0007 (9)	−0.0063 (9)	0.0015 (9)
C142	0.0191 (13)	0.0200 (13)	0.0237 (14)	−0.0076 (10)	−0.0075 (11)	0.0099 (11)
C143	0.0244 (14)	0.0154 (13)	0.0259 (15)	−0.0064 (10)	−0.0074 (11)	−0.0007 (10)
C144	0.0182 (12)	0.0206 (13)	0.0152 (13)	−0.0043 (10)	−0.0056 (10)	−0.0014 (10)
C145	0.0215 (13)	0.0219 (13)	0.0154 (13)	−0.0104 (10)	−0.0067 (10)	0.0060 (10)
C146	0.0212 (13)	0.0141 (12)	0.0223 (14)	−0.0059 (10)	−0.0106 (10)	0.0011 (10)
N21	0.0190 (11)	0.0189 (11)	0.0163 (11)	−0.0018 (9)	−0.0010 (9)	0.0026 (9)
C21	0.0127 (11)	0.0154 (12)	0.0094 (11)	−0.0040 (9)	−0.0001 (9)	−0.0024 (9)
C22	0.0125 (11)	0.0125 (11)	0.0094 (11)	−0.0007 (9)	−0.0033 (9)	−0.0003 (9)
C23	0.0152 (11)	0.0117 (11)	0.0096 (11)	−0.0040 (9)	−0.0028 (9)	−0.0002 (9)
O23	0.0185 (9)	0.0236 (10)	0.0123 (9)	0.0013 (7)	−0.0062 (7)	−0.0025 (7)
C227	0.0144 (11)	0.0115 (11)	0.0148 (12)	−0.0017 (9)	−0.0029 (9)	−0.0005 (9)
C221	0.0145 (11)	0.0119 (11)	0.0146 (12)	−0.0064 (9)	−0.0010 (9)	0.0010 (9)
C222	0.0164 (12)	0.0184 (13)	0.0192 (13)	0.0010 (10)	−0.0044 (10)	0.0031 (10)
Br22	0.02352 (15)	0.03471 (17)	0.02276 (16)	0.00809 (11)	−0.00826 (11)	0.00540 (12)
C223	0.0295 (15)	0.0362 (16)	0.0118 (13)	−0.0010 (12)	−0.0029 (11)	0.0038 (11)
C224	0.0208 (13)	0.0263 (14)	0.0171 (13)	−0.0025 (11)	0.0048 (10)	−0.0002 (11)
C225	0.0122 (11)	0.0198 (13)	0.0209 (13)	−0.0043 (9)	−0.0008 (10)	0.0015 (10)
C226	0.0147 (12)	0.0179 (12)	0.0149 (12)	−0.0078 (9)	−0.0034 (9)	0.0019 (9)
N231	0.0111 (9)	0.0161 (10)	0.0120 (10)	−0.0002 (8)	−0.0030 (8)	−0.0018 (8)
C232	0.0132 (11)	0.0141 (12)	0.0117 (12)	−0.0006 (9)	−0.0026 (9)	−0.0015 (9)
C233	0.0146 (11)	0.0112 (11)	0.0107 (11)	−0.0027 (9)	−0.0023 (9)	−0.0008 (9)
C23A	0.0128 (11)	0.0100 (11)	0.0101 (11)	−0.0037 (9)	−0.0007 (9)	0.0000 (9)
C234	0.0155 (12)	0.0175 (12)	0.0147 (12)	−0.0042 (9)	−0.0038 (9)	0.0001 (10)
C235	0.0233 (13)	0.0222 (13)	0.0115 (12)	−0.0079 (10)	−0.0002 (10)	−0.0059 (10)
C236	0.0178 (12)	0.0191 (13)	0.0187 (13)	−0.0027 (10)	0.0023 (10)	−0.0043 (10)
C237	0.0123 (11)	0.0162 (12)	0.0200 (13)	−0.0032 (9)	−0.0015 (10)	0.0007 (10)
C27A	0.0136 (11)	0.0124 (11)	0.0108 (11)	−0.0050 (9)	0.0000 (9)	0.0008 (9)
C231	0.0156 (12)	0.0252 (14)	0.0145 (13)	0.0000 (10)	−0.0073 (10)	0.0006 (10)
C241	0.0135 (12)	0.0164 (12)	0.0133 (12)	−0.0011 (9)	−0.0070 (9)	0.0022 (9)
C242	0.0223 (13)	0.0186 (13)	0.0195 (13)	−0.0067 (10)	−0.0085 (11)	0.0076 (10)
C243	0.0253 (14)	0.0148 (12)	0.0247 (14)	−0.0073 (10)	−0.0107 (11)	−0.0007 (10)
C244	0.0188 (12)	0.0197 (13)	0.0150 (12)	−0.0042 (10)	−0.0058 (10)	−0.0023 (10)
C245	0.0225 (13)	0.0194 (13)	0.0174 (13)	−0.0096 (10)	−0.0066 (10)	0.0028 (10)
C246	0.0213 (12)	0.0109 (11)	0.0166 (13)	−0.0043 (9)	−0.0091 (10)	−0.0008 (9)

Geometric parameters (Å, º)

N11—C11	1.137 (3)	N21—C21	1.139 (3)
C11—C12	1.468 (3)	C21—C22	1.468 (3)
C12—C13	1.544 (3)	C22—C23	1.545 (3)
C12—C127	1.554 (3)	C22—C227	1.551 (3)
C12—H12	1.0000	C22—H22	1.0000
C13—O13	1.227 (3)	C23—O23	1.226 (3)
C13—C133	1.435 (3)	C23—C233	1.436 (3)
C127—C121	1.510 (3)	C227—C221	1.511 (3)
C127—H12A	0.9900	C227—H22A	0.9900
C127—H12B	0.9900	C227—H22B	0.9900
C121—C122	1.393 (3)	C221—C222	1.391 (3)
C121—C126	1.396 (3)	C221—C226	1.396 (3)
C122—C123	1.387 (4)	C222—C223	1.385 (4)
C122—Br12	1.902 (3)	C222—Br22	1.903 (2)
C123—C124	1.384 (4)	C223—C224	1.381 (4)
C123—H123	0.9500	C223—H223	0.9500
C124—C125	1.381 (4)	C224—C225	1.378 (4)
C124—H124	0.9500	C224—H224	0.9500
C125—C126	1.383 (3)	C225—C226	1.387 (3)
C125—H125	0.9500	C225—H225	0.9500
C126—H126	0.9500	C226—H226	0.9500
N131—C132	1.351 (3)	N231—C232	1.351 (3)
N131—C17A	1.389 (3)	N231—C27A	1.390 (3)
N131—C131	1.472 (3)	N231—C231	1.473 (3)
C132—C133	1.390 (3)	C232—C233	1.388 (3)
C132—H132	0.9500	C232—H232	0.9500
C133—C13A	1.447 (3)	C233—C23A	1.444 (3)
C13A—C134	1.398 (3)	C23A—C234	1.401 (3)
C13A—C17A	1.409 (3)	C23A—C27A	1.406 (3)
C134—C135	1.381 (3)	C234—C235	1.382 (3)
C134—H134	0.9500	C234—H234	0.9500
C135—C136	1.398 (4)	C235—C236	1.402 (4)
C135—H135	0.9500	C235—H235	0.9500
C136—C137	1.382 (4)	C236—C237	1.379 (3)
C136—H136	0.9500	C236—H236	0.9500
C137—C17A	1.393 (3)	C237—C27A	1.392 (3)
C137—H137	0.9500	C237—H237	0.9500
C131—C141	1.506 (3)	C231—C241	1.507 (3)
C131—H13A	0.9900	C231—H23B	0.9900
C131—H13B	0.9900	C231—H23A	0.9900
C141—C142	1.389 (4)	C241—C242	1.385 (3)
C141—C146	1.390 (4)	C241—C246	1.388 (3)
C142—C143	1.391 (4)	C242—C243	1.388 (4)
C142—H142	0.9500	C242—H242	0.9500
C143—C144	1.385 (4)	C243—C244	1.387 (4)
C143—H143	0.9500	C243—H243	0.9500
C144—C145	1.384 (4)	C244—C245	1.384 (3)
C144—H144	0.9500	C244—H244	0.9500
C145—C146	1.387 (4)	C245—C246	1.390 (3)
C145—H145	0.9500	C245—H245	0.9500
C146—H146	0.9500	C246—H246	0.9500
N11—C11—C12	178.1 (3)	N21—C21—C22	177.5 (3)
C11—C12—C13	109.69 (19)	C21—C22—C23	110.56 (19)
C11—C12—C127	109.87 (19)	C21—C22—C227	109.81 (19)
C13—C12—C127	108.84 (18)	C23—C22—C227	108.10 (19)
C11—C12—H12	109.5	C21—C22—H22	109.4
C13—C12—H12	109.5	C23—C22—H22	109.4
C127—C12—H12	109.5	C227—C22—H22	109.4
O13—C13—C133	123.3 (2)	O23—C23—C233	123.7 (2)
O13—C13—C12	118.9 (2)	O23—C23—C22	118.8 (2)
C133—C13—C12	117.8 (2)	C233—C23—C22	117.35 (19)
C121—C127—C12	113.25 (19)	C221—C227—C22	112.96 (19)
C121—C127—H12A	108.9	C221—C227—H22A	109.0
C12—C127—H12A	108.9	C22—C227—H22A	109.0
C121—C127—H12B	108.9	C221—C227—H22B	109.0
C12—C127—H12B	108.9	C22—C227—H22B	109.0
H12A—C127—H12B	107.7	H22A—C227—H22B	107.8
C122—C121—C126	116.5 (2)	C222—C221—C226	116.9 (2)
C122—C121—C127	123.7 (2)	C222—C221—C227	124.0 (2)
C126—C121—C127	119.8 (2)	C226—C221—C227	119.1 (2)
C123—C122—C121	122.5 (2)	C223—C222—C221	122.2 (2)
C123—C122—Br12	117.2 (2)	C223—C222—Br22	117.78 (19)
C121—C122—Br12	120.30 (19)	C221—C222—Br22	120.00 (18)
C124—C123—C122	119.3 (3)	C224—C223—C222	119.6 (2)
C124—C123—H123	120.4	C224—C223—H223	120.2
C122—C123—H123	120.4	C222—C223—H223	120.2
C125—C124—C123	119.8 (2)	C225—C224—C223	119.7 (2)
C125—C124—H124	120.1	C225—C224—H224	120.2
C123—C124—H124	120.1	C223—C224—H224	120.2
C124—C125—C126	120.1 (2)	C224—C225—C226	120.3 (2)
C124—C125—H125	119.9	C224—C225—H225	119.8
C126—C125—H125	119.9	C226—C225—H225	119.8
C125—C126—C121	121.8 (2)	C225—C226—C221	121.3 (2)
C125—C126—H126	119.1	C225—C226—H226	119.3
C121—C126—H126	119.1	C221—C226—H226	119.3
C132—N131—C17A	109.16 (19)	C232—N231—C27A	109.04 (19)
C132—N131—C131	127.8 (2)	C232—N231—C231	127.2 (2)
C17A—N131—C131	122.94 (19)	C27A—N231—C231	123.64 (19)
N131—C132—C133	110.2 (2)	N231—C232—C233	110.2 (2)
N131—C132—H132	124.9	N231—C232—H232	124.9
C133—C132—H132	124.9	C233—C232—H232	124.9
C132—C133—C13	126.9 (2)	C232—C233—C23	127.0 (2)
C132—C133—C13A	106.3 (2)	C232—C233—C23A	106.3 (2)
C13—C133—C13A	126.8 (2)	C23—C233—C23A	126.8 (2)
C134—C13A—C17A	118.9 (2)	C234—C23A—C27A	118.7 (2)
C134—C13A—C133	134.8 (2)	C234—C23A—C233	134.8 (2)
C17A—C13A—C133	106.4 (2)	C27A—C23A—C233	106.5 (2)
C135—C134—C13A	118.6 (2)	C235—C234—C23A	118.7 (2)
C135—C134—H134	120.7	C235—C234—H234	120.7
C13A—C134—H134	120.7	C23A—C234—H234	120.7
C134—C135—C136	121.6 (2)	C234—C235—C236	121.4 (2)
C134—C135—H135	119.2	C234—C235—H235	119.3
C136—C135—H135	119.2	C236—C235—H235	119.3
C137—C136—C135	121.2 (2)	C237—C236—C235	121.3 (2)
C137—C136—H136	119.4	C237—C236—H236	119.4
C135—C136—H136	119.4	C235—C236—H236	119.4
C136—C137—C17A	116.9 (2)	C236—C237—C27A	117.0 (2)
C136—C137—H137	121.5	C236—C237—H237	121.5
C17A—C137—H137	121.5	C27A—C237—H237	121.5
N131—C17A—C137	129.2 (2)	N231—C27A—C237	129.0 (2)
N131—C17A—C13A	108.0 (2)	N231—C27A—C23A	107.97 (19)
C137—C17A—C13A	122.8 (2)	C237—C27A—C23A	123.0 (2)
N131—C131—C141	112.18 (19)	N231—C231—C241	111.72 (19)
N131—C131—H13A	109.2	N231—C231—H23B	109.3
C141—C131—H13A	109.2	C241—C231—H23B	109.3
N131—C131—H13B	109.2	N231—C231—H23A	109.3
C141—C131—H13B	109.2	C241—C231—H23A	109.3
H13A—C131—H13B	107.9	H23B—C231—H23A	107.9
C142—C141—C146	118.9 (2)	C242—C241—C246	119.0 (2)
C142—C141—C131	120.3 (2)	C242—C241—C231	120.8 (2)
C146—C141—C131	120.7 (2)	C246—C241—C231	120.2 (2)
C141—C142—C143	120.5 (2)	C241—C242—C243	120.7 (2)
C141—C142—H142	119.7	C241—C242—H242	119.6
C143—C142—H142	119.7	C243—C242—H242	119.6
C144—C143—C142	119.9 (2)	C244—C243—C242	119.9 (2)
C144—C143—H143	120.1	C244—C243—H243	120.1
C142—C143—H143	120.1	C242—C243—H243	120.1
C145—C144—C143	120.0 (2)	C245—C244—C243	119.8 (2)
C145—C144—H144	120.0	C245—C244—H244	120.1
C143—C144—H144	120.0	C243—C244—H244	120.1
C144—C145—C146	119.9 (2)	C244—C245—C246	120.0 (2)
C144—C145—H145	120.1	C244—C245—H245	120.0
C146—C145—H145	120.1	C246—C245—H245	120.0
C145—C146—C141	120.7 (2)	C241—C246—C245	120.5 (2)
C145—C146—H146	119.6	C241—C246—H246	119.7
C141—C146—H146	119.6	C245—C246—H246	119.7
C11—C12—C13—O13	−31.9 (3)	C21—C22—C23—O23	34.5 (3)
C127—C12—C13—O13	88.3 (3)	C227—C22—C23—O23	−85.7 (3)
C11—C12—C13—C133	151.1 (2)	C21—C22—C23—C233	−150.1 (2)
C127—C12—C13—C133	−88.6 (2)	C227—C22—C23—C233	89.7 (2)
C11—C12—C127—C121	−61.9 (3)	C21—C22—C227—C221	58.8 (3)
C13—C12—C127—C121	177.96 (19)	C23—C22—C227—C221	179.53 (18)
C12—C127—C121—C122	−93.1 (3)	C22—C227—C221—C222	87.4 (3)
C12—C127—C121—C126	87.4 (3)	C22—C227—C221—C226	−92.0 (3)
C126—C121—C122—C123	2.0 (4)	C226—C221—C222—C223	0.9 (4)
C127—C121—C122—C123	−177.5 (2)	C227—C221—C222—C223	−178.5 (2)
C126—C121—C122—Br12	−177.34 (17)	C226—C221—C222—Br22	−179.65 (18)
C127—C121—C122—Br12	3.1 (3)	C227—C221—C222—Br22	0.9 (3)
C121—C122—C123—C124	−3.0 (4)	C221—C222—C223—C224	−0.9 (4)
Br12—C122—C123—C124	176.3 (2)	Br22—C222—C223—C224	179.7 (2)
C122—C123—C124—C125	1.6 (4)	C222—C223—C224—C225	0.5 (4)
C123—C124—C125—C126	0.7 (4)	C223—C224—C225—C226	−0.2 (4)
C124—C125—C126—C121	−1.8 (4)	C224—C225—C226—C221	0.2 (4)
C122—C121—C126—C125	0.4 (3)	C222—C221—C226—C225	−0.6 (3)
C127—C121—C126—C125	179.9 (2)	C227—C221—C226—C225	178.9 (2)
C17A—N131—C132—C133	0.1 (3)	C27A—N231—C232—C233	−0.4 (3)
C131—N131—C132—C133	177.4 (2)	C231—N231—C232—C233	−175.8 (2)
N131—C132—C133—C13	−178.4 (2)	N231—C232—C233—C23	180.0 (2)
N131—C132—C133—C13A	−0.1 (3)	N231—C232—C233—C23A	0.3 (3)
O13—C13—C133—C132	174.1 (2)	O23—C23—C233—C232	−172.6 (2)
C12—C13—C133—C132	−9.1 (4)	C22—C23—C233—C232	12.3 (4)
O13—C13—C133—C13A	−3.9 (4)	O23—C23—C233—C23A	7.0 (4)
C12—C13—C133—C13A	172.9 (2)	C22—C23—C233—C23A	−168.1 (2)
C132—C133—C13A—C134	−179.2 (3)	C232—C233—C23A—C234	−179.3 (3)
C13—C133—C13A—C134	−0.9 (4)	C23—C233—C23A—C234	1.1 (4)
C132—C133—C13A—C17A	0.0 (3)	C232—C233—C23A—C27A	−0.1 (3)
C13—C133—C13A—C17A	178.4 (2)	C23—C233—C23A—C27A	−179.8 (2)
C17A—C13A—C134—C135	−1.5 (4)	C27A—C23A—C234—C235	0.8 (3)
C133—C13A—C134—C135	177.7 (3)	C233—C23A—C234—C235	179.9 (3)
C13A—C134—C135—C136	1.3 (4)	C23A—C234—C235—C236	−0.8 (4)
C134—C135—C136—C137	0.3 (4)	C234—C235—C236—C237	0.2 (4)
C135—C136—C137—C17A	−1.5 (4)	C235—C236—C237—C27A	0.5 (4)
C132—N131—C17A—C137	179.0 (2)	C232—N231—C27A—C237	179.6 (2)
C131—N131—C17A—C137	1.5 (4)	C231—N231—C27A—C237	−4.8 (4)
C132—N131—C17A—C13A	−0.1 (3)	C232—N231—C27A—C23A	0.3 (3)
C131—N131—C17A—C13A	−177.6 (2)	C231—N231—C27A—C23A	176.0 (2)
C136—C137—C17A—N131	−177.7 (2)	C236—C237—C27A—N231	−179.7 (2)
C136—C137—C17A—C13A	1.2 (4)	C236—C237—C27A—C23A	−0.5 (4)
C134—C13A—C17A—N131	179.4 (2)	C234—C23A—C27A—N231	179.2 (2)
C133—C13A—C17A—N131	0.1 (3)	C233—C23A—C27A—N231	−0.1 (3)
C134—C13A—C17A—C137	0.3 (4)	C234—C23A—C27A—C237	−0.1 (4)
C133—C13A—C17A—C137	−179.1 (2)	C233—C23A—C27A—C237	−179.4 (2)
C132—N131—C131—C141	4.5 (4)	C232—N231—C231—C241	−16.2 (3)
C17A—N131—C131—C141	−178.5 (2)	C27A—N231—C231—C241	169.0 (2)
N131—C131—C141—C142	−85.5 (3)	N231—C231—C241—C242	89.9 (3)
N131—C131—C141—C146	94.2 (3)	N231—C231—C241—C246	−89.6 (3)
C146—C141—C142—C143	−1.8 (3)	C246—C241—C242—C243	1.4 (3)
C131—C141—C142—C143	177.9 (2)	C231—C241—C242—C243	−178.2 (2)
C141—C142—C143—C144	1.8 (4)	C241—C242—C243—C244	−1.1 (4)
C142—C143—C144—C145	−0.4 (4)	C242—C243—C244—C245	−0.1 (4)
C143—C144—C145—C146	−1.0 (4)	C243—C244—C245—C246	1.0 (4)
C144—C145—C146—C141	1.0 (4)	C242—C241—C246—C245	−0.4 (3)
C142—C141—C146—C145	0.4 (3)	C231—C241—C246—C245	179.1 (2)
C131—C141—C146—C145	−179.3 (2)	C244—C245—C246—C241	−0.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C225—H225···N11	0.95	2.62	3.304 (4)	129
C231—H23A···O23^i	0.99	2.57	3.415 (4)	143

Symmetry code: (i) −x−1, −y+2, −z+2.

(E)-1-(1-Acetyl-1H-indol-3-yl)-3-(2-bromophenyl)-2-cyanoprop-1-en-1-yl acetate (III)

Crystal data

C22H17BrN2O3	F(000) = 1776
Mr = 437.28	Dx = 1.523 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.406 (9) Å	Cell parameters from 4412 reflections
b = 8.773 (4) Å	θ = 2.5–27.6°
c = 23.028 (9) Å	µ = 2.18 mm^−1
β = 103.318 (15)°	T = 173 K
V = 3815 (3) Å^3	Block, colourless
Z = 8	0.42 × 0.32 × 0.24 mm

Data collection

Bruker D8 Venture diffractometer	4379 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube	3435 reflections with I > 2σ(I)
Multilayer mirror monochromator	Rint = 0.057
φ and ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −25→25
Tmin = 0.420, Tmax = 0.594	k = −11→11
49228 measured reflections	l = −29→29

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.136	w = 1/[σ^2(Fo^2) + (0.0427P)^2 + 18.903P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
4379 reflections	Δρmax = 0.80 e Å^−3
255 parameters	Δρmin = −1.89 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
C1	0.62414 (17)	0.3935 (4)	0.29701 (16)	0.0337 (8)
C2	0.62775 (17)	0.4887 (4)	0.34346 (16)	0.0379 (8)
C3	0.65936 (19)	0.4495 (5)	0.40750 (16)	0.0428 (10)
H3A	0.6666	0.3378	0.4107	0.051*
H3B	0.6250	0.4771	0.4316	0.051*
O11	0.64160 (14)	0.2417 (3)	0.31041 (10)	0.0376 (6)
C11	0.6943 (2)	0.1770 (4)	0.28804 (15)	0.0372 (8)
O12	0.73268 (15)	0.2507 (3)	0.26607 (14)	0.0533 (8)
C111	0.6960 (3)	0.0090 (4)	0.29636 (17)	0.0619 (14)
H11A	0.7145	−0.0392	0.2647	0.093*
H11B	0.6480	−0.0284	0.2946	0.093*
H11C	0.7266	−0.0163	0.3353	0.093*
N11	0.57308 (15)	0.5602 (3)	0.14756 (14)	0.0386 (7)
C12	0.60600 (18)	0.5633 (4)	0.20784 (16)	0.0374 (8)
H12	0.6310	0.6483	0.2280	0.045*
C13	0.59756 (16)	0.4290 (4)	0.23388 (16)	0.0325 (7)
C13A	0.55771 (16)	0.3298 (4)	0.18758 (16)	0.0359 (8)
C14	0.53385 (19)	0.1801 (5)	0.18688 (18)	0.0452 (10)
H14	0.5439	0.1197	0.2221	0.054*
C15	0.4948 (2)	0.1214 (5)	0.1331 (2)	0.0531 (12)
H15	0.4766	0.0206	0.1321	0.064*
C16	0.48178 (18)	0.2070 (5)	0.08106 (19)	0.0474 (11)
H16	0.4562	0.1621	0.0449	0.057*
C17	0.50493 (16)	0.3554 (5)	0.08029 (18)	0.0408 (9)
H17	0.4958	0.4140	0.0446	0.049*
C17A	0.54247 (16)	0.4151 (4)	0.13455 (17)	0.0373 (8)
C18	0.5663 (2)	0.6840 (4)	0.10827 (19)	0.0518 (11)
O18	0.52769 (17)	0.6757 (3)	0.05891 (13)	0.0612 (9)
C19	0.6093 (3)	0.8218 (5)	0.1310 (2)	0.083 (2)
H19A	0.6047	0.8970	0.0988	0.125*
H19B	0.6592	0.7927	0.1449	0.125*
H19C	0.5923	0.8662	0.1642	0.125*
C21	0.59703 (18)	0.6371 (5)	0.33325 (19)	0.0472 (10)
N21	0.57241 (18)	0.7561 (5)	0.32946 (19)	0.0635 (12)
C31	0.72899 (17)	0.5274 (4)	0.43386 (15)	0.0318 (7)
C32	0.75899 (19)	0.5183 (4)	0.49450 (16)	0.0363 (8)
Br32	0.71124 (3)	0.40569 (5)	0.54420 (2)	0.06003 (18)
C33	0.82242 (19)	0.5875 (4)	0.52081 (19)	0.0450 (9)
H33	0.8413	0.5791	0.5626	0.054*
C34	0.85800 (19)	0.6691 (5)	0.4856 (2)	0.0520 (12)
H34	0.9016	0.7177	0.5030	0.062*
C35	0.82997 (19)	0.6798 (5)	0.4250 (2)	0.0478 (11)
H35	0.8547	0.7353	0.4007	0.057*
C36	0.76622 (17)	0.6105 (4)	0.39925 (17)	0.0357 (8)
H36	0.7475	0.6194	0.3575	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0289 (16)	0.0368 (18)	0.0431 (18)	−0.0134 (14)	0.0244 (14)	−0.0193 (15)
C2	0.0262 (16)	0.046 (2)	0.049 (2)	−0.0179 (15)	0.0247 (15)	−0.0261 (17)
C3	0.042 (2)	0.054 (2)	0.0413 (19)	−0.0323 (17)	0.0287 (16)	−0.0278 (17)
O11	0.0553 (15)	0.0328 (12)	0.0344 (12)	−0.0188 (11)	0.0304 (11)	−0.0129 (10)
C11	0.063 (2)	0.0254 (16)	0.0305 (16)	−0.0017 (15)	0.0254 (16)	0.0015 (13)
O12	0.0598 (17)	0.0359 (14)	0.080 (2)	0.0198 (13)	0.0487 (16)	0.0268 (14)
C111	0.135 (5)	0.0218 (17)	0.0329 (19)	−0.010 (2)	0.028 (2)	−0.0060 (14)
N11	0.0341 (15)	0.0296 (14)	0.0467 (17)	0.0119 (12)	−0.0017 (13)	−0.0189 (13)
C12	0.0333 (17)	0.0328 (17)	0.0437 (19)	0.0079 (14)	0.0034 (15)	−0.0211 (15)
C13	0.0243 (15)	0.0335 (17)	0.0435 (18)	−0.0025 (13)	0.0158 (14)	−0.0209 (14)
C13A	0.0199 (15)	0.0441 (19)	0.049 (2)	−0.0058 (13)	0.0203 (14)	−0.0261 (16)
C14	0.0328 (18)	0.056 (2)	0.056 (2)	−0.0243 (17)	0.0307 (17)	−0.0271 (19)
C15	0.038 (2)	0.064 (3)	0.067 (3)	−0.0304 (19)	0.033 (2)	−0.036 (2)
C16	0.0216 (16)	0.065 (3)	0.060 (2)	−0.0111 (16)	0.0176 (16)	−0.036 (2)
C17	0.0166 (14)	0.050 (2)	0.055 (2)	0.0042 (14)	0.0073 (14)	−0.0285 (18)
C17A	0.0171 (14)	0.0426 (19)	0.053 (2)	0.0052 (13)	0.0102 (14)	−0.0257 (17)
C18	0.061 (3)	0.0333 (19)	0.050 (2)	0.0215 (18)	−0.010 (2)	−0.0204 (17)
O18	0.070 (2)	0.0474 (17)	0.0525 (17)	0.0266 (15)	−0.0145 (15)	−0.0224 (14)
C19	0.134 (5)	0.0234 (19)	0.064 (3)	0.011 (2)	−0.035 (3)	−0.0124 (19)
C21	0.0237 (16)	0.061 (2)	0.061 (2)	−0.0117 (17)	0.0190 (16)	−0.042 (2)
N21	0.0372 (18)	0.066 (2)	0.090 (3)	0.0017 (17)	0.0200 (18)	−0.051 (2)
C31	0.0292 (16)	0.0276 (15)	0.0457 (19)	−0.0128 (13)	0.0235 (14)	−0.0206 (14)
C32	0.0383 (18)	0.0296 (17)	0.047 (2)	−0.0078 (14)	0.0212 (16)	−0.0194 (15)
Br32	0.0965 (4)	0.0472 (3)	0.0470 (2)	−0.0271 (2)	0.0384 (2)	−0.01872 (18)
C33	0.0353 (19)	0.046 (2)	0.055 (2)	0.0015 (16)	0.0134 (17)	−0.0282 (18)
C34	0.0247 (17)	0.060 (3)	0.076 (3)	−0.0150 (17)	0.0211 (18)	−0.042 (2)
C35	0.0351 (19)	0.048 (2)	0.072 (3)	−0.0234 (16)	0.0369 (19)	−0.031 (2)
C36	0.0312 (17)	0.0341 (17)	0.050 (2)	−0.0160 (14)	0.0267 (15)	−0.0218 (15)

Geometric parameters (Å, º)

C1—C2	1.346 (4)	C15—C16	1.388 (7)
C1—O11	1.391 (4)	C15—H15	0.9500
C1—C13	1.460 (5)	C16—C17	1.378 (6)
C2—C21	1.429 (6)	C16—H16	0.9500
C2—C3	1.501 (6)	C17—C17A	1.395 (5)
C3—C31	1.511 (4)	C17—H17	0.9500
C3—H3A	0.9900	C18—O18	1.211 (5)
C3—H3B	0.9900	C18—C19	1.494 (6)
O11—C11	1.369 (4)	C19—H19A	0.9800
C11—O12	1.185 (4)	C19—H19B	0.9800
C11—C111	1.486 (5)	C19—H19C	0.9800
C111—H11A	0.9800	C21—N21	1.143 (6)
C111—H11B	0.9800	C31—C32	1.386 (5)
C111—H11C	0.9800	C31—C36	1.398 (4)
N11—C12	1.388 (5)	C32—C33	1.381 (5)
N11—C18	1.400 (5)	C32—Br32	1.906 (4)
N11—C17A	1.407 (4)	C33—C34	1.381 (6)
C12—C13	1.349 (5)	C33—H33	0.9500
C12—H12	0.9500	C34—C35	1.378 (6)
C13—C13A	1.453 (4)	C34—H34	0.9500
C13A—C14	1.392 (5)	C35—C36	1.383 (5)
C13A—C17A	1.404 (6)	C35—H35	0.9500
C14—C15	1.393 (5)	C36—H36	0.9500
C14—H14	0.9500
C2—C1—O11	116.9 (3)	C14—C15—H15	119.3
C2—C1—C13	126.9 (3)	C17—C16—C15	121.8 (4)
O11—C1—C13	115.9 (3)	C17—C16—H16	119.1
C1—C2—C21	119.4 (4)	C15—C16—H16	119.1
C1—C2—C3	125.0 (4)	C16—C17—C17A	116.6 (4)
C21—C2—C3	115.5 (3)	C16—C17—H17	121.7
C2—C3—C31	114.6 (3)	C17A—C17—H17	121.7
C2—C3—H3A	108.6	C17—C17A—C13A	122.7 (4)
C31—C3—H3A	108.6	C17—C17A—N11	129.6 (4)
C2—C3—H3B	108.6	C13A—C17A—N11	107.6 (3)
C31—C3—H3B	108.6	O18—C18—N11	120.4 (4)
H3A—C3—H3B	107.6	O18—C18—C19	123.5 (4)
C11—O11—C1	118.6 (2)	N11—C18—C19	116.1 (3)
O12—C11—O11	122.1 (3)	C18—C19—H19A	109.5
O12—C11—C111	126.8 (4)	C18—C19—H19B	109.5
O11—C11—C111	111.1 (3)	H19A—C19—H19B	109.5
C11—C111—H11A	109.5	C18—C19—H19C	109.5
C11—C111—H11B	109.5	H19A—C19—H19C	109.5
H11A—C111—H11B	109.5	H19B—C19—H19C	109.5
C11—C111—H11C	109.5	N21—C21—C2	174.9 (5)
H11A—C111—H11C	109.5	C32—C31—C36	116.9 (3)
H11B—C111—H11C	109.5	C32—C31—C3	120.5 (3)
C12—N11—C18	125.7 (3)	C36—C31—C3	122.6 (3)
C12—N11—C17A	107.8 (3)	C33—C32—C31	122.8 (3)
C18—N11—C17A	126.3 (3)	C33—C32—Br32	118.1 (3)
C13—C12—N11	110.6 (3)	C31—C32—Br32	119.0 (2)
C13—C12—H12	124.7	C32—C33—C34	119.1 (4)
N11—C12—H12	124.7	C32—C33—H33	120.5
C12—C13—C13A	107.2 (3)	C34—C33—H33	120.5
C12—C13—C1	125.3 (3)	C35—C34—C33	119.7 (3)
C13A—C13—C1	127.5 (3)	C35—C34—H34	120.1
C14—C13A—C17A	119.3 (3)	C33—C34—H34	120.1
C14—C13A—C13	133.9 (4)	C34—C35—C36	120.6 (4)
C17A—C13A—C13	106.8 (3)	C34—C35—H35	119.7
C13A—C14—C15	118.1 (4)	C36—C35—H35	119.7
C13A—C14—H14	121.0	C35—C36—C31	120.9 (4)
C15—C14—H14	121.0	C35—C36—H36	119.6
C16—C15—C14	121.4 (4)	C31—C36—H36	119.6
C16—C15—H15	119.3
O11—C1—C2—C21	−167.3 (3)	C16—C17—C17A—C13A	1.2 (4)
C13—C1—C2—C21	6.6 (5)	C16—C17—C17A—N11	179.2 (3)
O11—C1—C2—C3	9.8 (5)	C14—C13A—C17A—C17	−1.0 (5)
C13—C1—C2—C3	−176.3 (3)	C13—C13A—C17A—C17	179.5 (3)
C1—C2—C3—C31	108.7 (4)	C14—C13A—C17A—N11	−179.4 (3)
C21—C2—C3—C31	−74.1 (4)	C13—C13A—C17A—N11	1.2 (3)
C2—C1—O11—C11	−123.6 (3)	C12—N11—C17A—C17	−178.7 (3)
C13—C1—O11—C11	61.9 (4)	C18—N11—C17A—C17	6.6 (6)
C1—O11—C11—O12	12.3 (5)	C12—N11—C17A—C13A	−0.5 (3)
C1—O11—C11—C111	−168.6 (3)	C18—N11—C17A—C13A	−175.2 (3)
C18—N11—C12—C13	174.3 (3)	C12—N11—C18—O18	−168.9 (4)
C17A—N11—C12—C13	−0.5 (4)	C17A—N11—C18—O18	4.9 (6)
N11—C12—C13—C13A	1.2 (4)	C12—N11—C18—C19	11.6 (6)
N11—C12—C13—C1	−178.8 (3)	C17A—N11—C18—C19	−174.6 (4)
C2—C1—C13—C12	36.4 (5)	C2—C3—C31—C32	171.0 (3)
O11—C1—C13—C12	−149.7 (3)	C2—C3—C31—C36	−9.3 (5)
C2—C1—C13—C13A	−143.5 (3)	C36—C31—C32—C33	0.3 (5)
O11—C1—C13—C13A	30.3 (4)	C3—C31—C32—C33	−179.9 (3)
C12—C13—C13A—C14	179.2 (3)	C36—C31—C32—Br32	−179.6 (2)
C1—C13—C13A—C14	−0.8 (6)	C3—C31—C32—Br32	0.2 (4)
C12—C13—C13A—C17A	−1.4 (3)	C31—C32—C33—C34	−0.2 (5)
C1—C13—C13A—C17A	178.5 (3)	Br32—C32—C33—C34	179.7 (3)
C17A—C13A—C14—C15	−0.7 (5)	C32—C33—C34—C35	−0.2 (6)
C13—C13A—C14—C15	178.6 (3)	C33—C34—C35—C36	0.5 (6)
C13A—C14—C15—C16	2.2 (5)	C34—C35—C36—C31	−0.4 (6)
C14—C15—C16—C17	−2.0 (6)	C32—C31—C36—C35	0.0 (5)
C15—C16—C17—C17A	0.3 (5)	C3—C31—C36—C35	−179.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O18	0.95	2.38	2.904 (5)	114
C17—H17···O18^i	0.95	2.45	3.133 (5)	129
C35—H35···Cg2^ii	0.95	2.76	3.582 (5)	146

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+3/2, y+1/2, −z+1/2.

(E)-1-(1-Benzyl-1H-indol-3-yl)-3-(2-bromophenyl)-2-cyanoprop-1-en-1-yl benzoate (IV)

Crystal data

C32H23BrN2O2	F(000) = 1120
Mr = 547.42	Dx = 1.449 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.886 (4) Å	Cell parameters from 7902 reflections
b = 8.129 (3) Å	θ = 2.7–31.7°
c = 21.432 (6) Å	µ = 1.67 mm^−1
β = 104.638 (12)°	T = 100 K
V = 2509.3 (14) Å^3	Block, colourless
Z = 4	0.21 × 0.12 × 0.12 mm

Data collection

Bruker D8 Venture diffractometer	6999 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube	5828 reflections with I > 2σ(I)
Multilayer mirror monochromator	Rint = 0.074
φ and ω scans	θmax = 29.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −20→20
Tmin = 0.676, Tmax = 0.818	k = −10→11
87392 measured reflections	l = −29→29

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.086	w = 1/[σ^2(Fo^2) + (0.0363P)^2 + 2.1078P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.002
6999 reflections	Δρmax = 0.46 e Å^−3
334 parameters	Δρmin = −0.94 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
C1	0.25289 (10)	0.82801 (18)	0.47696 (7)	0.0105 (3)
C2	0.27542 (10)	0.93568 (19)	0.52616 (7)	0.0106 (3)
C3	0.20854 (11)	1.04297 (19)	0.55102 (7)	0.0124 (3)
H3A	0.2265	1.1599	0.5494	0.015*
H3B	0.1450	1.0294	0.5229	0.015*
O11	0.15866 (7)	0.80355 (14)	0.44880 (5)	0.0130 (2)
C11	0.13009 (11)	0.83794 (18)	0.38406 (7)	0.0127 (3)
O12	0.17813 (8)	0.91169 (15)	0.35614 (6)	0.0191 (2)
C111	0.03599 (11)	0.7745 (2)	0.35434 (8)	0.0142 (3)
C112	−0.00318 (12)	0.8198 (2)	0.29061 (8)	0.0183 (3)
H112	0.0285	0.8939	0.2693	0.022*
C113	−0.08877 (12)	0.7562 (2)	0.25838 (9)	0.0239 (4)
H113	−0.1155	0.7856	0.2147	0.029*
C114	−0.13509 (12)	0.6503 (2)	0.28971 (10)	0.0272 (4)
H114	−0.1934	0.6061	0.2673	0.033*
C115	−0.09723 (12)	0.6078 (2)	0.35362 (10)	0.0258 (4)
H115	−0.1300	0.5360	0.3750	0.031*
C116	−0.01135 (11)	0.6703 (2)	0.38637 (9)	0.0190 (3)
H116	0.0147	0.6420	0.4302	0.023*
N11	0.44244 (9)	0.61866 (17)	0.42862 (6)	0.0104 (2)
C12	0.40480 (10)	0.75381 (19)	0.45008 (7)	0.0114 (3)
H12	0.4357	0.8560	0.4610	0.014*
C13	0.31527 (10)	0.72040 (19)	0.45362 (7)	0.0105 (3)
C13A	0.29651 (10)	0.55208 (19)	0.43271 (7)	0.0098 (3)
C14	0.22226 (10)	0.4437 (2)	0.42943 (7)	0.0127 (3)
H14	0.1665	0.4805	0.4388	0.015*
C15	0.23190 (11)	0.2821 (2)	0.41223 (8)	0.0147 (3)
H15	0.1820	0.2076	0.4099	0.018*
C16	0.31388 (11)	0.2253 (2)	0.39810 (7)	0.0147 (3)
H16	0.3183	0.1134	0.3865	0.018*
C17	0.38813 (11)	0.32977 (19)	0.40090 (7)	0.0128 (3)
H17	0.4437	0.2921	0.3916	0.015*
C17A	0.37781 (10)	0.49289 (19)	0.41803 (7)	0.0100 (3)
C21	0.37140 (11)	0.95045 (19)	0.55964 (7)	0.0116 (3)
N21	0.44759 (9)	0.96982 (18)	0.58749 (7)	0.0165 (3)
C31	0.20907 (11)	0.99745 (19)	0.61958 (7)	0.0127 (3)
C32	0.14347 (11)	0.8950 (2)	0.63576 (8)	0.0159 (3)
Br32	0.03898 (2)	0.81786 (2)	0.57128 (2)	0.02400 (6)
C33	0.14907 (13)	0.8471 (2)	0.69864 (9)	0.0223 (4)
H33	0.1034	0.7763	0.7080	0.027*
C34	0.22217 (14)	0.9037 (2)	0.74773 (8)	0.0253 (4)
H34	0.2275	0.8703	0.7910	0.030*
C35	0.28693 (13)	1.0083 (2)	0.73362 (8)	0.0225 (4)
H35	0.3364	1.0485	0.7673	0.027*
C36	0.28043 (11)	1.0552 (2)	0.67051 (8)	0.0179 (3)
H36	0.3254	1.1283	0.6616	0.022*
C18	0.54006 (10)	0.5994 (2)	0.42926 (7)	0.0119 (3)
H18A	0.5652	0.5035	0.4565	0.014*
H18B	0.5743	0.6980	0.4496	0.014*
C181	0.55868 (10)	0.57590 (19)	0.36390 (7)	0.0105 (3)
C182	0.63057 (11)	0.4722 (2)	0.35846 (8)	0.0160 (3)
H182	0.6651	0.4142	0.3952	0.019*
C183	0.65196 (12)	0.4533 (2)	0.29938 (9)	0.0217 (4)
H183	0.7011	0.3822	0.2958	0.026*
C184	0.60197 (13)	0.5376 (2)	0.24594 (8)	0.0216 (4)
H184	0.6169	0.5249	0.2056	0.026*
C185	0.53023 (12)	0.6405 (2)	0.25104 (8)	0.0207 (3)
H185	0.4957	0.6980	0.2142	0.025*
C186	0.50856 (11)	0.6599 (2)	0.30995 (8)	0.0154 (3)
H186	0.4593	0.7309	0.3133	0.018*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0080 (6)	0.0117 (7)	0.0113 (6)	−0.0008 (5)	0.0017 (5)	0.0019 (5)
C2	0.0106 (6)	0.0112 (7)	0.0101 (6)	0.0008 (5)	0.0028 (5)	0.0012 (5)
C3	0.0134 (7)	0.0125 (7)	0.0116 (7)	0.0021 (6)	0.0036 (5)	0.0000 (5)
O11	0.0076 (5)	0.0175 (6)	0.0133 (5)	−0.0005 (4)	0.0012 (4)	−0.0021 (4)
C11	0.0131 (7)	0.0091 (7)	0.0139 (7)	0.0009 (5)	−0.0005 (5)	−0.0016 (5)
O12	0.0185 (6)	0.0183 (6)	0.0176 (6)	−0.0046 (5)	−0.0007 (5)	0.0040 (5)
C111	0.0104 (7)	0.0122 (7)	0.0180 (7)	0.0022 (5)	−0.0004 (6)	−0.0049 (6)
C112	0.0153 (7)	0.0199 (8)	0.0175 (8)	0.0036 (6)	−0.0002 (6)	−0.0054 (6)
C113	0.0159 (8)	0.0299 (10)	0.0214 (8)	0.0049 (7)	−0.0037 (6)	−0.0098 (7)
C114	0.0110 (8)	0.0288 (10)	0.0365 (11)	0.0003 (7)	−0.0034 (7)	−0.0127 (8)
C115	0.0132 (8)	0.0226 (9)	0.0398 (11)	−0.0030 (7)	0.0032 (7)	−0.0025 (8)
C116	0.0119 (7)	0.0182 (8)	0.0253 (8)	0.0008 (6)	0.0019 (6)	−0.0012 (7)
N11	0.0086 (6)	0.0133 (6)	0.0100 (6)	−0.0008 (5)	0.0034 (4)	−0.0013 (5)
C12	0.0125 (7)	0.0117 (7)	0.0108 (6)	−0.0008 (5)	0.0043 (5)	−0.0004 (5)
C13	0.0095 (6)	0.0124 (7)	0.0095 (6)	−0.0010 (5)	0.0020 (5)	−0.0003 (5)
C13A	0.0111 (6)	0.0116 (7)	0.0061 (6)	0.0005 (5)	0.0009 (5)	0.0003 (5)
C14	0.0109 (7)	0.0157 (7)	0.0113 (6)	−0.0009 (6)	0.0027 (5)	0.0000 (6)
C15	0.0160 (7)	0.0139 (7)	0.0142 (7)	−0.0038 (6)	0.0037 (6)	−0.0003 (6)
C16	0.0200 (8)	0.0114 (7)	0.0129 (7)	−0.0010 (6)	0.0043 (6)	−0.0012 (6)
C17	0.0151 (7)	0.0135 (7)	0.0103 (6)	0.0024 (6)	0.0040 (5)	−0.0005 (5)
C17A	0.0116 (6)	0.0126 (7)	0.0056 (6)	−0.0003 (5)	0.0019 (5)	0.0007 (5)
C21	0.0144 (7)	0.0098 (7)	0.0116 (7)	−0.0004 (5)	0.0053 (5)	−0.0012 (5)
N21	0.0135 (6)	0.0194 (7)	0.0164 (6)	−0.0005 (5)	0.0031 (5)	−0.0039 (5)
C31	0.0124 (7)	0.0136 (7)	0.0126 (7)	0.0041 (6)	0.0041 (5)	−0.0010 (6)
C32	0.0151 (7)	0.0165 (8)	0.0172 (7)	0.0029 (6)	0.0059 (6)	−0.0003 (6)
Br32	0.01663 (9)	0.02752 (10)	0.02782 (10)	−0.00654 (7)	0.00557 (7)	−0.00047 (7)
C33	0.0272 (9)	0.0222 (9)	0.0222 (8)	0.0060 (7)	0.0152 (7)	0.0040 (7)
C34	0.0354 (10)	0.0293 (10)	0.0134 (8)	0.0150 (8)	0.0105 (7)	0.0036 (7)
C35	0.0233 (9)	0.0296 (10)	0.0132 (7)	0.0114 (7)	0.0019 (6)	−0.0042 (7)
C36	0.0145 (7)	0.0227 (8)	0.0165 (7)	0.0037 (6)	0.0035 (6)	−0.0051 (6)
C18	0.0083 (6)	0.0179 (8)	0.0094 (6)	0.0009 (5)	0.0020 (5)	−0.0005 (5)
C181	0.0090 (6)	0.0123 (7)	0.0104 (6)	−0.0024 (5)	0.0029 (5)	−0.0014 (5)
C182	0.0136 (7)	0.0167 (8)	0.0187 (7)	0.0022 (6)	0.0061 (6)	0.0018 (6)
C183	0.0200 (8)	0.0218 (9)	0.0283 (9)	0.0004 (7)	0.0154 (7)	−0.0041 (7)
C184	0.0249 (9)	0.0283 (9)	0.0158 (7)	−0.0097 (7)	0.0129 (7)	−0.0066 (7)
C185	0.0201 (8)	0.0305 (9)	0.0116 (7)	−0.0042 (7)	0.0041 (6)	0.0027 (7)
C186	0.0122 (7)	0.0212 (8)	0.0128 (7)	0.0016 (6)	0.0032 (6)	0.0018 (6)

Geometric parameters (Å, º)

C1—C2	1.346 (2)	C15—C16	1.408 (2)
C1—O11	1.3942 (18)	C15—H15	0.9500
C1—C13	1.453 (2)	C16—C17	1.383 (2)
C2—C21	1.433 (2)	C16—H16	0.9500
C2—C3	1.518 (2)	C17—C17A	1.395 (2)
C3—C31	1.513 (2)	C17—H17	0.9500
C3—H3A	0.9900	C21—N21	1.151 (2)
C3—H3B	0.9900	C31—C32	1.392 (2)
O11—C11	1.3734 (19)	C31—C36	1.398 (2)
C11—O12	1.202 (2)	C32—C33	1.385 (2)
C11—C111	1.477 (2)	C32—Br32	1.9068 (17)
C111—C116	1.389 (2)	C33—C34	1.387 (3)
C111—C112	1.393 (2)	C33—H33	0.9500
C112—C113	1.387 (2)	C34—C35	1.375 (3)
C112—H112	0.9500	C34—H34	0.9500
C113—C114	1.379 (3)	C35—C36	1.385 (2)
C113—H113	0.9500	C35—H35	0.9500
C114—C115	1.387 (3)	C36—H36	0.9500
C114—H114	0.9500	C18—C181	1.507 (2)
C115—C116	1.390 (2)	C18—H18A	0.9900
C115—H115	0.9500	C18—H18B	0.9900
C116—H116	0.9500	C181—C186	1.387 (2)
N11—C12	1.365 (2)	C181—C182	1.390 (2)
N11—C17A	1.383 (2)	C182—C183	1.390 (2)
N11—C18	1.4581 (19)	C182—H182	0.9500
C12—C13	1.381 (2)	C183—C184	1.380 (3)
C12—H12	0.9500	C183—H183	0.9500
C13—C13A	1.445 (2)	C184—C185	1.382 (3)
C13A—C14	1.401 (2)	C184—H184	0.9500
C13A—C17A	1.410 (2)	C185—C186	1.389 (2)
C14—C15	1.381 (2)	C185—H185	0.9500
C14—H14	0.9500	C186—H186	0.9500
C2—C1—O11	117.13 (13)	C17—C16—C15	121.04 (15)
C2—C1—C13	127.35 (14)	C17—C16—H16	119.5
O11—C1—C13	115.19 (13)	C15—C16—H16	119.5
C1—C2—C21	117.79 (14)	C16—C17—C17A	117.09 (14)
C1—C2—C3	126.37 (14)	C16—C17—H17	121.5
C21—C2—C3	115.83 (13)	C17A—C17—H17	121.5
C31—C3—C2	110.94 (12)	N11—C17A—C17	128.89 (14)
C31—C3—H3A	109.5	N11—C17A—C13A	108.18 (13)
C2—C3—H3A	109.5	C17—C17A—C13A	122.75 (14)
C31—C3—H3B	109.5	N21—C21—C2	176.67 (17)
C2—C3—H3B	109.5	C32—C31—C36	116.67 (15)
H3A—C3—H3B	108.0	C32—C31—C3	123.79 (14)
C11—O11—C1	115.40 (12)	C36—C31—C3	119.50 (15)
O12—C11—O11	122.22 (14)	C33—C32—C31	122.49 (16)
O12—C11—C111	125.31 (15)	C33—C32—Br32	116.75 (13)
O11—C11—C111	112.47 (14)	C31—C32—Br32	120.75 (12)
C116—C111—C112	120.47 (15)	C32—C33—C34	119.17 (17)
C116—C111—C11	122.96 (15)	C32—C33—H33	120.4
C112—C111—C11	116.54 (15)	C34—C33—H33	120.4
C113—C112—C111	119.61 (18)	C35—C34—C33	119.83 (16)
C113—C112—H112	120.2	C35—C34—H34	120.1
C111—C112—H112	120.2	C33—C34—H34	120.1
C114—C113—C112	119.99 (18)	C34—C35—C36	120.35 (17)
C114—C113—H113	120.0	C34—C35—H35	119.8
C112—C113—H113	120.0	C36—C35—H35	119.8
C113—C114—C115	120.54 (17)	C35—C36—C31	121.45 (17)
C113—C114—H114	119.7	C35—C36—H36	119.3
C115—C114—H114	119.7	C31—C36—H36	119.3
C114—C115—C116	120.01 (18)	N11—C18—C181	114.95 (12)
C114—C115—H115	120.0	N11—C18—H18A	108.5
C116—C115—H115	120.0	C181—C18—H18A	108.5
C111—C116—C115	119.35 (17)	N11—C18—H18B	108.5
C111—C116—H116	120.3	C181—C18—H18B	108.5
C115—C116—H116	120.3	H18A—C18—H18B	107.5
C12—N11—C17A	108.82 (12)	C186—C181—C182	119.47 (14)
C12—N11—C18	125.19 (13)	C186—C181—C18	121.72 (14)
C17A—N11—C18	124.93 (13)	C182—C181—C18	118.76 (14)
N11—C12—C13	110.14 (14)	C181—C182—C183	120.12 (15)
N11—C12—H12	124.9	C181—C182—H182	119.9
C13—C12—H12	124.9	C183—C182—H182	119.9
C12—C13—C13A	106.43 (13)	C184—C183—C182	120.09 (16)
C12—C13—C1	127.59 (14)	C184—C183—H183	120.0
C13A—C13—C1	125.90 (13)	C182—C183—H183	120.0
C14—C13A—C17A	119.00 (14)	C183—C184—C185	120.01 (15)
C14—C13A—C13	134.36 (14)	C183—C184—H184	120.0
C17A—C13A—C13	106.43 (13)	C185—C184—H184	120.0
C15—C14—C13A	118.52 (14)	C184—C185—C186	120.15 (16)
C15—C14—H14	120.7	C184—C185—H185	119.9
C13A—C14—H14	120.7	C186—C185—H185	119.9
C14—C15—C16	121.59 (15)	C181—C186—C185	120.15 (15)
C14—C15—H15	119.2	C181—C186—H186	119.9
C16—C15—H15	119.2	C185—C186—H186	119.9
O11—C1—C2—C21	174.10 (13)	C14—C15—C16—C17	−0.1 (2)
C13—C1—C2—C21	1.0 (2)	C15—C16—C17—C17A	−0.2 (2)
O11—C1—C2—C3	−4.8 (2)	C12—N11—C17A—C17	−174.54 (14)
C13—C1—C2—C3	−177.92 (14)	C18—N11—C17A—C17	−5.8 (2)
C1—C2—C3—C31	115.94 (17)	C12—N11—C17A—C13A	0.67 (16)
C21—C2—C3—C31	−63.03 (17)	C18—N11—C17A—C13A	169.37 (13)
C2—C1—O11—C11	121.15 (15)	C16—C17—C17A—N11	175.16 (15)
C13—C1—O11—C11	−64.94 (17)	C16—C17—C17A—C13A	0.6 (2)
C1—O11—C11—O12	−13.0 (2)	C14—C13A—C17A—N11	−176.22 (13)
C1—O11—C11—C111	166.92 (12)	C13—C13A—C17A—N11	−0.69 (16)
O12—C11—C111—C116	170.58 (16)	C14—C13A—C17A—C17	−0.7 (2)
O11—C11—C111—C116	−9.4 (2)	C13—C13A—C17A—C17	174.88 (14)
O12—C11—C111—C112	−7.3 (2)	C2—C3—C31—C32	−98.04 (18)
O11—C11—C111—C112	172.79 (14)	C2—C3—C31—C36	79.71 (18)
C116—C111—C112—C113	−2.0 (2)	C36—C31—C32—C33	−2.0 (2)
C11—C111—C112—C113	175.86 (15)	C3—C31—C32—C33	175.78 (15)
C111—C112—C113—C114	0.8 (3)	C36—C31—C32—Br32	176.51 (12)
C112—C113—C114—C115	0.6 (3)	C3—C31—C32—Br32	−5.7 (2)
C113—C114—C115—C116	−0.9 (3)	C31—C32—C33—C34	0.5 (3)
C112—C111—C116—C115	1.8 (2)	Br32—C32—C33—C34	−178.09 (13)
C11—C111—C116—C115	−175.96 (16)	C32—C33—C34—C35	1.1 (3)
C114—C115—C116—C111	−0.4 (3)	C33—C34—C35—C36	−1.1 (3)
C17A—N11—C12—C13	−0.38 (17)	C34—C35—C36—C31	−0.5 (3)
C18—N11—C12—C13	−169.05 (13)	C32—C31—C36—C35	2.0 (2)
N11—C12—C13—C13A	−0.05 (17)	C3—C31—C36—C35	−175.87 (15)
N11—C12—C13—C1	176.84 (14)	C12—N11—C18—C181	−119.05 (16)
C2—C1—C13—C12	−36.3 (3)	C17A—N11—C18—C181	74.06 (19)
O11—C1—C13—C12	150.51 (15)	N11—C18—C181—C186	38.1 (2)
C2—C1—C13—C13A	140.01 (16)	N11—C18—C181—C182	−144.58 (15)
O11—C1—C13—C13A	−33.2 (2)	C186—C181—C182—C183	0.1 (2)
C12—C13—C13A—C14	174.99 (16)	C18—C181—C182—C183	−177.33 (15)
C1—C13—C13A—C14	−2.0 (3)	C181—C182—C183—C184	0.1 (3)
C12—C13—C13A—C17A	0.45 (16)	C182—C183—C184—C185	−0.3 (3)
C1—C13—C13A—C17A	−176.50 (14)	C183—C184—C185—C186	0.3 (3)
C17A—C13A—C14—C15	0.4 (2)	C182—C181—C186—C185	−0.1 (2)
C13—C13A—C14—C15	−173.65 (16)	C18—C181—C186—C185	177.27 (15)
C13A—C14—C15—C16	0.0 (2)	C184—C185—C186—C181	−0.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C36—H36···Cg3^i	0.95	2.92	3.739 (2)	145
C183—H183···Cg1^ii	0.95	2.97	3.807 (2)	148

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+1, −z+1.

2-Benzoyl-3-(2-bromophenyl)acrylonitrile (V)

Crystal data

C16H10BrNO	F(000) = 624
Mr = 312.15	Dx = 1.604 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.986 (4) Å	Cell parameters from 2986 reflections
b = 8.977 (4) Å	θ = 2.3–27.6°
c = 13.209 (5) Å	µ = 3.17 mm^−1
β = 97.140 (17)°	T = 100 K
V = 1292.6 (9) Å^3	Block, orange
Z = 4	0.27 × 0.26 × 0.23 mm

Data collection

Bruker D8 Venture diffractometer	2985 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube	2754 reflections with I > 2σ(I)
Multilayer mirror monochromator	Rint = 0.036
φ and ω scans	θmax = 27.6°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −14→14
Tmin = 0.366, Tmax = 0.482	k = −11→11
30048 measured reflections	l = −17→17

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.022	H-atom parameters constrained
wR(F^2) = 0.053	w = 1/[σ^2(Fo^2) + (0.023P)^2 + 0.9733P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max = 0.002
2985 reflections	Δρmax = 0.34 e Å^−3
172 parameters	Δρmin = −0.52 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
C1	0.52114 (14)	0.09372 (17)	0.66805 (12)	0.0114 (3)
N1	0.46836 (14)	0.03411 (16)	0.72541 (11)	0.0179 (3)
C2	0.59444 (13)	0.16873 (17)	0.60003 (11)	0.0092 (3)
C3	0.58208 (13)	0.31481 (17)	0.57997 (11)	0.0087 (3)
H3	0.6362	0.3569	0.5369	0.010*
C27	0.67937 (14)	0.06881 (17)	0.55029 (11)	0.0096 (3)
O27	0.65240 (11)	−0.06180 (13)	0.53670 (9)	0.0158 (2)
C21	0.79280 (14)	0.13384 (16)	0.51742 (11)	0.0098 (3)
C22	0.83791 (15)	0.07181 (18)	0.43254 (12)	0.0132 (3)
H22	0.7956	−0.0083	0.3967	0.016*
C23	0.94443 (16)	0.1274 (2)	0.40076 (13)	0.0176 (3)
H23	0.9746	0.0862	0.3425	0.021*
C24	1.00734 (15)	0.2433 (2)	0.45368 (13)	0.0190 (3)
H24	1.0804	0.2811	0.4316	0.023*
C25	0.96375 (15)	0.30402 (19)	0.53877 (13)	0.0158 (3)
H25	1.0072	0.3828	0.5751	0.019*
C26	0.85669 (14)	0.24971 (17)	0.57080 (11)	0.0115 (3)
H26	0.8268	0.2914	0.6291	0.014*
C31	0.49311 (14)	0.41605 (16)	0.61805 (11)	0.0091 (3)
C32	0.53014 (14)	0.55567 (17)	0.65733 (11)	0.0102 (3)
Br32	0.69900 (2)	0.60654 (2)	0.67042 (2)	0.01496 (6)
C33	0.44831 (15)	0.65635 (18)	0.69096 (12)	0.0140 (3)
H33	0.4756	0.7510	0.7168	0.017*
C34	0.32568 (15)	0.61617 (19)	0.68605 (12)	0.0155 (3)
H34	0.2684	0.6836	0.7091	0.019*
C35	0.28618 (14)	0.47790 (19)	0.64766 (12)	0.0152 (3)
H35	0.2022	0.4510	0.6450	0.018*
C36	0.36892 (14)	0.37893 (17)	0.61324 (12)	0.0122 (3)
H36	0.3410	0.2852	0.5862	0.015*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0104 (7)	0.0090 (7)	0.0152 (7)	0.0003 (5)	0.0025 (6)	−0.0013 (6)
N1	0.0202 (7)	0.0143 (7)	0.0210 (7)	−0.0010 (6)	0.0093 (6)	0.0022 (6)
C2	0.0079 (6)	0.0104 (7)	0.0095 (6)	−0.0018 (5)	0.0017 (5)	−0.0012 (5)
C3	0.0077 (6)	0.0113 (7)	0.0071 (6)	−0.0017 (5)	0.0014 (5)	−0.0019 (5)
C27	0.0108 (7)	0.0103 (7)	0.0076 (6)	0.0010 (5)	−0.0001 (5)	0.0002 (5)
O27	0.0186 (6)	0.0097 (5)	0.0197 (6)	−0.0017 (4)	0.0047 (5)	−0.0031 (4)
C21	0.0091 (7)	0.0105 (7)	0.0097 (7)	0.0024 (5)	0.0015 (5)	0.0017 (5)
C22	0.0152 (7)	0.0135 (7)	0.0111 (7)	0.0037 (6)	0.0024 (6)	−0.0001 (6)
C23	0.0183 (8)	0.0240 (9)	0.0121 (7)	0.0060 (7)	0.0073 (6)	0.0017 (6)
C24	0.0121 (7)	0.0270 (9)	0.0192 (8)	−0.0003 (7)	0.0068 (6)	0.0063 (7)
C25	0.0118 (7)	0.0181 (8)	0.0174 (8)	−0.0028 (6)	0.0012 (6)	0.0005 (6)
C26	0.0115 (7)	0.0128 (7)	0.0103 (7)	0.0011 (6)	0.0019 (5)	0.0005 (6)
C31	0.0106 (7)	0.0099 (7)	0.0069 (6)	0.0013 (5)	0.0019 (5)	0.0013 (5)
C32	0.0111 (7)	0.0115 (7)	0.0081 (6)	−0.0004 (5)	0.0010 (5)	0.0014 (5)
Br32	0.01375 (9)	0.01610 (9)	0.01532 (9)	−0.00647 (6)	0.00294 (6)	−0.00398 (6)
C33	0.0215 (8)	0.0103 (7)	0.0105 (7)	0.0024 (6)	0.0028 (6)	−0.0003 (6)
C34	0.0172 (8)	0.0185 (8)	0.0113 (7)	0.0102 (6)	0.0038 (6)	0.0021 (6)
C35	0.0097 (7)	0.0224 (8)	0.0139 (7)	0.0025 (6)	0.0023 (6)	0.0018 (6)
C36	0.0113 (7)	0.0141 (7)	0.0113 (7)	−0.0007 (6)	0.0016 (6)	0.0004 (6)

Geometric parameters (Å, º)

C1—N1	1.143 (2)	C24—H24	0.9500
C1—C2	1.445 (2)	C25—C26	1.387 (2)
C2—C3	1.341 (2)	C25—H25	0.9500
C2—C27	1.503 (2)	C26—H26	0.9500
C3—C31	1.469 (2)	C31—C32	1.398 (2)
C3—H3	0.9500	C31—C36	1.398 (2)
C27—O27	1.217 (2)	C32—C33	1.386 (2)
C27—C21	1.489 (2)	C32—Br32	1.8973 (17)
C21—C26	1.396 (2)	C33—C34	1.388 (2)
C21—C22	1.397 (2)	C33—H33	0.9500
C22—C23	1.385 (2)	C34—C35	1.390 (2)
C22—H22	0.9500	C34—H34	0.9500
C23—C24	1.389 (3)	C35—C36	1.387 (2)
C23—H23	0.9500	C35—H35	0.9500
C24—C25	1.387 (2)	C36—H36	0.9500
N1—C1—C2	176.52 (17)	C24—C25—H25	120.0
C3—C2—C1	121.85 (14)	C26—C25—H25	120.0
C3—C2—C27	123.38 (13)	C25—C26—C21	120.01 (15)
C1—C2—C27	114.70 (13)	C25—C26—H26	120.0
C2—C3—C31	126.35 (14)	C21—C26—H26	120.0
C2—C3—H3	116.8	C32—C31—C36	117.91 (14)
C31—C3—H3	116.8	C32—C31—C3	120.45 (14)
O27—C27—C21	122.14 (14)	C36—C31—C3	121.61 (14)
O27—C27—C2	119.10 (14)	C33—C32—C31	122.22 (15)
C21—C27—C2	118.75 (13)	C33—C32—Br32	118.65 (12)
C26—C21—C22	119.75 (14)	C31—C32—Br32	119.07 (11)
C26—C21—C27	122.10 (14)	C32—C33—C34	118.67 (15)
C22—C21—C27	118.10 (14)	C32—C33—H33	120.7
C23—C22—C21	119.81 (15)	C34—C33—H33	120.7
C23—C22—H22	120.1	C33—C34—C35	120.42 (15)
C21—C22—H22	120.1	C33—C34—H34	119.8
C22—C23—C24	120.27 (15)	C35—C34—H34	119.8
C22—C23—H23	119.9	C36—C35—C34	120.26 (15)
C24—C23—H23	119.9	C36—C35—H35	119.9
C25—C24—C23	120.14 (15)	C34—C35—H35	119.9
C25—C24—H24	119.9	C35—C36—C31	120.52 (15)
C23—C24—H24	119.9	C35—C36—H36	119.7
C24—C25—C26	120.02 (16)	C31—C36—H36	119.7
C1—C2—C3—C31	−2.8 (2)	C22—C21—C26—C25	0.8 (2)
C27—C2—C3—C31	173.86 (14)	C27—C21—C26—C25	178.30 (14)
C3—C2—C27—O27	−149.43 (15)	C2—C3—C31—C32	134.36 (16)
C1—C2—C27—O27	27.4 (2)	C2—C3—C31—C36	−47.8 (2)
C3—C2—C27—C21	29.4 (2)	C36—C31—C32—C33	0.0 (2)
C1—C2—C27—C21	−153.71 (14)	C3—C31—C32—C33	177.87 (14)
O27—C27—C21—C26	−147.87 (15)	C36—C31—C32—Br32	177.34 (11)
C2—C27—C21—C26	33.3 (2)	C3—C31—C32—Br32	−4.77 (19)
O27—C27—C21—C22	29.7 (2)	C31—C32—C33—C34	0.5 (2)
C2—C27—C21—C22	−149.12 (14)	Br32—C32—C33—C34	−176.85 (11)
C26—C21—C22—C23	−1.2 (2)	C32—C33—C34—C35	−0.3 (2)
C27—C21—C22—C23	−178.82 (14)	C33—C34—C35—C36	−0.4 (2)
C21—C22—C23—C24	0.8 (2)	C34—C35—C36—C31	0.9 (2)
C22—C23—C24—C25	0.0 (3)	C32—C31—C36—C35	−0.7 (2)
C23—C24—C25—C26	−0.4 (3)	C3—C31—C36—C35	−178.56 (14)
C24—C25—C26—C21	0.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C33—H33···N1^i	0.95	2.55	3.425 (3)	154
C36—H36···O27^ii	0.95	2.59	3.459 (2)	153
C3—H3···Cg1^iii	0.95	2.73	3.431 (2)	131
C23—H23···Cg1^iv	0.95	2.69	3.506 (2)	144

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