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Cooperative action of hydrogen and halogen bonding in the reaction of 3-(3,5-di-tert-butyl-4-hy­droxy­phen­yl)-1-phenyl­prop-2-en-1-one with HCl or HBr in alcohol medium under microwave irradiation (20 W, 80 °C, 10 min) allows the isolation of the haloetherification products (2S,3S)-3-(3-tert-butyl-5-chloro-4-hy­droxy­phen­yl)-2-chloro-3-eth­oxy-1-phenyl­propan-1-one, C21H24Cl2O3, (2S,3S)-2-bromo-3-(3-tert-butyl-5-bromo-4-hy­droxy­phen­yl)-3-meth­oxy-1-phenyl­propan-1-one, C20H22Br2O3, and (2S,3S)-2-bromo-3-(3-tert-butyl-5-bromo-4-hy­droxy­phen­yl)-3-eth­oxy-1-phenyl­propan-1-one, C21H24Br2O3, in good yields. Both types of noncovalent interactions, e.g. hydrogen and halogen bonds, are formed to stabilize the obtained products in the solid state.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619001025/lf3083sup1.cif
Contains datablocks 2, 3, 4, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619001025/lf30832sup2.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619001025/lf30833sup3.hkl
Contains datablock 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619001025/lf30834sup4.hkl
Contains datablock 4

CCDC references: 1523181; 1523183; 1523182

Computing details top

For all structures, data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

3-(3-tert-Butyl-5-chloro-4-hydroxyphenyl)-2-chloro-3-ethoxy-1-phenylpropan-1-one (2) top
Crystal data top
C21H24Cl2O3F(000) = 832
Mr = 395.30Dx = 1.271 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 9.4460 (13) ÅCell parameters from 4304 reflections
b = 19.783 (3) Åθ = 2.4–25.9°
c = 11.0766 (15) ŵ = 0.33 mm1
β = 93.821 (3)°T = 296 K
V = 2065.2 (5) Å3Prism, colorless
Z = 40.22 × 0.18 × 0.16 mm
Data collection top
Bruker APEXII CCD
diffractometer
2932 reflections with I > 2σ(I)
φ and ω scansRint = 0.025
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
θmax = 26.0°, θmin = 2.1°
Tmin = 0.926, Tmax = 0.940h = 911
15808 measured reflectionsk = 2424
4061 independent reflectionsl = 1313
Refinement top
Refinement on F287 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.053H-atom parameters constrained
wR(F2) = 0.159 w = 1/[σ2(Fo2) + (0.0767P)2 + 0.9719P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
4061 reflectionsΔρmax = 0.59 e Å3
257 parametersΔρmin = 0.52 e Å3
Special details top

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

Refinement. The C16 and C17 atoms of the ethyl fragment are disordered over two position. The disorder was modeled and refined including alternative positions with relative occupancies of 0.53 (4):0.47 (4).

Moreover, in compound 2, the RIGU routine (Sheldrick, 2015) in SHELXTL-97 program (Sheldrick, 2015) was applied to remove diffuse electron density caused by badly disordered tetrasbusbtituted phenyl ring.

The X-ray diffraction patterns of 24 were collected using a Bruker SMART APEXII CCD area detector equipped with graphite-monochromated Mo Kα radiation (λ = 0.71073 Å) at room temperature. Absorption correction was applied by SADABS (Bruker, 2016). The structure was solved by direct methods and refined on F2 by full-matrix least-squares using Bruker SHELXTL97 (Sheldrick, 2015), operating within the OLEX2 program (Dolomanov et al., 2009). All non-H atoms were refined anisotropically. The details of the crystallographic data are summarized in Table 1. Crystallographic data for the structural analysis have been deposited to the Cambridge Crystallographic Data Center (CCDC 1523181–1523183 for 24). Copy of this information can be obtained free of charge from The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: (+44) 1223-336033; E-mail: deposit@ccdc.cam.ac.uk or www.ccdc.cam.ac.uk/data_request/cif). ORTEP views were drawn using OLEX2 software (Dolomanov et al., 2009).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.24488 (10)0.87305 (6)0.63611 (8)0.0963 (4)
Cl20.38524 (8)0.66698 (3)0.25768 (7)0.0682 (3)
O10.5186 (3)0.96553 (11)0.71645 (19)0.0900 (8)
O20.19073 (19)0.75530 (9)0.11081 (16)0.0606 (5)
H20.2084650.7136800.1003760.091*
O30.6277 (2)0.87499 (9)0.51819 (15)0.0588 (5)
C10.5284 (3)0.87510 (14)0.8534 (2)0.0535 (6)
C20.5174 (3)0.80689 (17)0.8749 (3)0.0697 (8)
H2A0.4871060.7778870.8123500.084*
C30.5513 (4)0.7813 (2)0.9896 (3)0.0897 (11)
H30.5452430.7351031.0036830.108*
C40.5934 (4)0.8237 (3)1.0813 (3)0.0956 (13)
H40.6150530.8063471.1583400.115*
C50.6043 (4)0.8911 (3)1.0621 (3)0.0896 (11)
H50.6328190.9196981.1257380.107*
C60.5730 (3)0.91718 (18)0.9483 (2)0.0703 (8)
H60.5819570.9633570.9349890.084*
C70.4973 (3)0.90655 (14)0.7334 (2)0.0582 (7)
C80.4311 (3)0.86385 (14)0.6290 (2)0.0562 (7)
H80.4572650.8163310.6418780.067*
C90.4790 (3)0.88716 (13)0.5073 (2)0.0522 (6)
H90.4623270.9358810.4989500.063*
C100.4049 (3)0.85116 (12)0.4009 (2)0.0493 (5)
C110.3101 (3)0.88559 (13)0.3229 (2)0.0497 (5)
H110.2952000.9313070.3369240.060*
C120.2362 (3)0.85555 (13)0.2249 (2)0.0521 (4)
C130.2610 (3)0.78690 (12)0.2057 (2)0.0466 (5)
C140.3566 (3)0.75237 (13)0.2839 (2)0.0482 (5)
C150.4285 (3)0.78350 (12)0.3806 (2)0.0499 (5)
H150.4921110.7592460.4315070.060*
C160.7039 (14)0.9057 (9)0.4296 (9)0.079 (5)0.53 (4)
H16A0.6508410.9444080.3975250.095*0.53 (4)
H16B0.7129650.8739760.3637580.095*0.53 (4)
C170.8426 (17)0.9275 (10)0.4734 (14)0.109 (5)0.53 (4)
H17A0.8896490.9481130.4085430.164*0.53 (4)
H17B0.8345220.9597320.5373190.164*0.53 (4)
H17C0.8966800.8892610.5035330.164*0.53 (4)
C17'0.848 (3)0.908 (2)0.449 (3)0.205 (14)0.47 (4)
H17D0.8956780.9368450.3957580.308*0.47 (4)
H17E0.8822000.9163560.5312280.308*0.47 (4)
H17F0.8664440.8613660.4293110.308*0.47 (4)
C16'0.707 (2)0.9194 (12)0.437 (2)0.120 (9)0.47 (4)
H16C0.6729030.9113280.3533220.144*0.47 (4)
H16D0.6886730.9663710.4553370.144*0.47 (4)
C180.1320 (3)0.89641 (14)0.1377 (2)0.0580 (4)
C190.1224 (3)0.96988 (14)0.1807 (3)0.0657 (5)
H19A0.0917150.9706640.2616190.099*
H19B0.0555020.9940940.1279170.099*
H19C0.2139440.9908440.1795990.099*
C200.0161 (3)0.86616 (16)0.1369 (3)0.0688 (6)
H20A0.0804730.8928370.0858840.103*
H20B0.0468960.8658200.2177400.103*
H20C0.0143730.8207360.1065330.103*
C210.1862 (3)0.89659 (17)0.0118 (2)0.0689 (6)
H21A0.1191960.9194350.0429890.103*
H21B0.1978700.8508810.0148780.103*
H21C0.2758060.9195830.0135850.103*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0675 (6)0.1426 (9)0.0784 (6)0.0109 (5)0.0009 (4)0.0293 (5)
Cl20.0785 (5)0.0533 (4)0.0699 (5)0.0106 (3)0.0165 (4)0.0122 (3)
O10.146 (2)0.0521 (12)0.0667 (13)0.0168 (13)0.0297 (13)0.0032 (10)
O20.0624 (10)0.0635 (8)0.0530 (7)0.0020 (7)0.0180 (7)0.0097 (6)
O30.0582 (12)0.0671 (12)0.0487 (10)0.0090 (9)0.0143 (8)0.0087 (8)
C10.0511 (16)0.0656 (16)0.0435 (13)0.0005 (12)0.0007 (11)0.0051 (11)
C20.081 (2)0.0748 (19)0.0529 (16)0.0000 (16)0.0037 (15)0.0039 (14)
C30.092 (3)0.102 (3)0.075 (2)0.000 (2)0.0016 (19)0.029 (2)
C40.073 (2)0.163 (4)0.0503 (18)0.009 (2)0.0038 (16)0.026 (2)
C50.077 (2)0.144 (4)0.0457 (17)0.019 (2)0.0058 (15)0.006 (2)
C60.0668 (19)0.093 (2)0.0507 (15)0.0081 (16)0.0017 (13)0.0107 (15)
C70.0689 (18)0.0551 (16)0.0492 (14)0.0027 (13)0.0069 (13)0.0063 (12)
C80.0653 (18)0.0543 (15)0.0473 (13)0.0050 (13)0.0093 (12)0.0048 (11)
C90.0620 (17)0.0464 (13)0.0461 (13)0.0012 (12)0.0137 (11)0.0010 (10)
C100.0516 (10)0.0514 (7)0.0435 (8)0.0012 (6)0.0071 (7)0.0007 (5)
C110.0523 (10)0.0506 (7)0.0449 (7)0.0011 (6)0.0078 (7)0.0006 (5)
C120.0521 (8)0.0564 (6)0.0461 (6)0.0021 (5)0.0090 (6)0.0028 (4)
C130.0427 (9)0.0557 (6)0.0404 (7)0.0020 (5)0.0038 (6)0.0026 (4)
C140.0461 (9)0.0551 (7)0.0424 (7)0.0006 (5)0.0047 (7)0.0033 (5)
C150.0525 (10)0.0516 (7)0.0438 (7)0.0019 (6)0.0098 (7)0.0012 (6)
C160.067 (9)0.131 (11)0.038 (4)0.040 (8)0.009 (4)0.022 (4)
C170.079 (9)0.169 (10)0.081 (6)0.074 (9)0.018 (5)0.009 (6)
C17'0.15 (2)0.35 (3)0.124 (15)0.09 (2)0.033 (12)0.113 (19)
C16'0.112 (18)0.096 (9)0.154 (17)0.022 (10)0.019 (11)0.046 (9)
C180.0552 (7)0.0648 (7)0.0519 (7)0.0045 (6)0.0121 (6)0.0021 (6)
C190.0654 (13)0.0648 (7)0.0639 (11)0.0100 (7)0.0176 (11)0.0013 (7)
C200.0541 (8)0.0718 (11)0.0780 (15)0.0043 (8)0.0131 (7)0.0066 (10)
C210.0698 (13)0.0815 (13)0.0541 (7)0.0187 (11)0.0064 (8)0.0098 (8)
Geometric parameters (Å, º) top
Cl1—C81.776 (3)C12—C131.397 (4)
Cl2—C141.738 (3)C12—C181.559 (3)
O1—C71.201 (3)C13—C141.388 (3)
O2—H20.8497C14—C151.375 (3)
O2—C131.358 (3)C15—H150.9300
O3—C91.422 (3)C16—H16A0.9700
O3—C161.394 (13)C16—H16B0.9700
O3—C16'1.50 (2)C16—C171.434 (19)
C1—C21.375 (4)C17—H17A0.9600
C1—C61.384 (4)C17—H17B0.9600
C1—C71.479 (4)C17—H17C0.9600
C2—H2A0.9300C17'—H17D0.9600
C2—C31.385 (4)C17'—H17E0.9600
C3—H30.9300C17'—H17F0.9600
C3—C41.357 (6)C17'—C16'1.35 (3)
C4—H40.9300C16'—H16C0.9700
C4—C51.354 (6)C16'—H16D0.9700
C5—H50.9300C18—C191.534 (4)
C5—C61.376 (5)C18—C201.521 (4)
C6—H60.9300C18—C211.517 (4)
C7—C81.532 (3)C19—H19A0.9600
C8—H80.9800C19—H19B0.9600
C8—C91.521 (4)C19—H19C0.9600
C9—H90.9800C20—H20A0.9600
C9—C101.509 (3)C20—H20B0.9600
C10—C111.381 (3)C20—H20C0.9600
C10—C151.378 (3)C21—H21A0.9600
C11—H110.9300C21—H21B0.9600
C11—C121.385 (3)C21—H21C0.9600
C13—O2—H2117.4C10—C15—H15120.5
C9—O3—C16'112.4 (8)C14—C15—C10119.1 (2)
C16—O3—C9114.8 (6)C14—C15—H15120.5
C2—C1—C6118.7 (3)O3—C16—H16A108.9
C2—C1—C7123.8 (2)O3—C16—H16B108.9
C6—C1—C7117.5 (3)O3—C16—C17113.4 (9)
C1—C2—H2A119.9H16A—C16—H16B107.7
C1—C2—C3120.1 (3)C17—C16—H16A108.9
C3—C2—H2A119.9C17—C16—H16B108.9
C2—C3—H3120.0C16—C17—H17A109.5
C4—C3—C2120.0 (4)C16—C17—H17B109.5
C4—C3—H3120.0C16—C17—H17C109.5
C3—C4—H4119.6H17A—C17—H17B109.5
C5—C4—C3120.8 (3)H17A—C17—H17C109.5
C5—C4—H4119.6H17B—C17—H17C109.5
C4—C5—H5120.0H17D—C17'—H17E109.5
C4—C5—C6120.0 (3)H17D—C17'—H17F109.5
C6—C5—H5120.0H17E—C17'—H17F109.5
C1—C6—H6119.8C16'—C17'—H17D109.5
C5—C6—C1120.4 (3)C16'—C17'—H17E109.5
C5—C6—H6119.8C16'—C17'—H17F109.5
O1—C7—C1121.6 (2)O3—C16'—H16C109.3
O1—C7—C8118.8 (2)O3—C16'—H16D109.3
C1—C7—C8119.5 (2)C17'—C16'—O3111.5 (18)
Cl1—C8—H8109.4C17'—C16'—H16C109.3
C7—C8—Cl1105.42 (19)C17'—C16'—H16D109.3
C7—C8—H8109.4H16C—C16'—H16D108.0
C9—C8—Cl1111.25 (19)C19—C18—C12110.3 (2)
C9—C8—C7111.8 (2)C20—C18—C12110.0 (2)
C9—C8—H8109.4C20—C18—C19107.5 (2)
O3—C9—C8102.96 (19)C21—C18—C12109.5 (2)
O3—C9—H9109.1C21—C18—C19108.3 (2)
O3—C9—C10113.0 (2)C21—C18—C20111.2 (2)
C8—C9—H9109.1C18—C19—H19A109.5
C10—C9—C8113.5 (2)C18—C19—H19B109.5
C10—C9—H9109.1C18—C19—H19C109.5
C11—C10—C9120.2 (2)H19A—C19—H19B109.5
C15—C10—C9121.0 (2)H19A—C19—H19C109.5
C15—C10—C11118.8 (2)H19B—C19—H19C109.5
C10—C11—H11118.3C18—C20—H20A109.5
C10—C11—C12123.4 (2)C18—C20—H20B109.5
C12—C11—H11118.3C18—C20—H20C109.5
C11—C12—C13117.1 (2)H20A—C20—H20B109.5
C11—C12—C18121.9 (2)H20A—C20—H20C109.5
C13—C12—C18121.0 (2)H20B—C20—H20C109.5
O2—C13—C12119.1 (2)C18—C21—H21A109.5
O2—C13—C14121.4 (2)C18—C21—H21B109.5
C14—C13—C12119.5 (2)C18—C21—H21C109.5
C13—C14—Cl2118.43 (18)H21A—C21—H21B109.5
C15—C14—Cl2119.42 (19)H21A—C21—H21C109.5
C15—C14—C13122.1 (2)H21B—C21—H21C109.5
Cl1—C8—C9—O3179.02 (16)C8—C9—C10—C1568.1 (3)
Cl1—C8—C9—C1056.5 (3)C9—O3—C16—C17145.5 (14)
Cl2—C14—C15—C10179.8 (2)C9—O3—C16'—C17'179 (3)
O1—C7—C8—Cl187.0 (3)C9—C10—C11—C12178.7 (3)
O1—C7—C8—C934.0 (4)C9—C10—C15—C14178.8 (2)
O2—C13—C14—Cl20.1 (3)C10—C11—C12—C130.2 (4)
O2—C13—C14—C15179.8 (2)C10—C11—C12—C18179.0 (3)
O3—C9—C10—C11132.2 (2)C11—C10—C15—C140.3 (4)
O3—C9—C10—C1548.7 (3)C11—C12—C13—O2179.9 (2)
C1—C2—C3—C41.0 (5)C11—C12—C13—C140.0 (4)
C1—C7—C8—Cl190.7 (3)C11—C12—C18—C192.3 (4)
C1—C7—C8—C9148.3 (3)C11—C12—C18—C20120.8 (3)
C2—C1—C6—C50.7 (5)C11—C12—C18—C21116.7 (3)
C2—C1—C7—O1174.2 (3)C12—C13—C14—Cl2180.0 (2)
C2—C1—C7—C88.1 (4)C12—C13—C14—C150.1 (4)
C2—C3—C4—C50.7 (6)C13—C12—C18—C19179.0 (3)
C3—C4—C5—C60.3 (6)C13—C12—C18—C2060.5 (3)
C4—C5—C6—C11.0 (5)C13—C12—C18—C2162.0 (3)
C6—C1—C2—C30.3 (5)C13—C14—C15—C100.1 (4)
C6—C1—C7—O14.8 (4)C15—C10—C11—C120.4 (4)
C6—C1—C7—C8172.8 (3)C16—O3—C9—C8166.3 (8)
C7—C1—C2—C3178.7 (3)C16—O3—C9—C1070.9 (8)
C7—C1—C6—C5179.7 (3)C16'—O3—C9—C8155.2 (11)
C7—C8—C9—O363.4 (3)C16'—O3—C9—C1082.0 (11)
C7—C8—C9—C10174.1 (2)C18—C12—C13—O21.3 (4)
C8—C9—C10—C11111.0 (3)C18—C12—C13—C14178.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···Cl20.852.512.9456 (19)113
O2—H2···O3i0.852.102.823 (3)143
Symmetry code: (i) x1/2, y+3/2, z1/2.
2-Bromo-3-(3-tert-butyl-5-bromo-4-hydroxyphenyl)-3-methoxy-1-phenylpropan-1-one (3) top
Crystal data top
C20H22Br2O3F(000) = 944
Mr = 470.19Dx = 1.509 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 9.6343 (5) ÅCell parameters from 2692 reflections
b = 19.5472 (10) Åθ = 2.4–25.6°
c = 10.9965 (6) ŵ = 3.93 mm1
β = 91.584 (2)°T = 296 K
V = 2070.11 (19) Å3Prism, colorless
Z = 40.25 × 0.22 × 0.22 mm
Data collection top
Bruker APEXII CCD
diffractometer
3201 reflections with I > 2σ(I)
φ and ω scansRint = 0.024
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
θmax = 28.4°, θmin = 2.1°
Tmin = 0.387, Tmax = 0.420h = 612
9119 measured reflectionsk = 2526
5067 independent reflectionsl = 1411
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.0591P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
5067 reflectionsΔρmax = 0.80 e Å3
230 parametersΔρmin = 0.69 e Å3
Special details top

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

Refinement. In the case of compound 3, the completeness was 0.979. The data for this compound,were collected properly. However, we have some problems with data processing, due to the crystal quality is not properly than the other samples.

In fact, this sample have decomposed during the measurement. We have made several attemps with this sample obtaining the same results.

The X-ray diffraction patterns of 24 were collected using a Bruker SMART APEXII CCD area detector equipped with graphite-monochromated Mo Kα radiation (λ = 0.71073 Å) at room temperature. Absorption correction was applied by SADABS (Bruker, 2016). The structure was solved by direct methods and refined on F2 by full-matrix least-squares using Bruker SHELXTL97 (Sheldrick, 2015), operating within the OLEX2 program (Dolomanov et al., 2009). All non-H atoms were refined anisotropically. The details of the crystallographic data are summarized in Table 1. Crystallographic data for the structural analysis have been deposited to the Cambridge Crystallographic Data Center (CCDC 1523181–1523183 for 24). Copy of this information can be obtained free of charge from The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: (+44) 1223-336033; E-mail: deposit@ccdc.cam.ac.uk or www.ccdc.cam.ac.uk/data_request/cif). ORTEP views were drawn using OLEX2 software (Dolomanov et al., 2009).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.72394 (4)0.37888 (3)0.14883 (4)0.0998 (2)
Br20.86866 (3)0.15806 (2)0.24734 (3)0.05642 (13)
O11.0189 (3)0.46627 (12)0.2145 (2)0.0828 (8)
O20.6728 (2)0.25862 (10)0.38036 (19)0.0534 (5)
H20.6947380.2166860.3868480.080*
O31.1145 (2)0.36877 (11)0.0156 (2)0.0541 (5)
C11.0156 (3)0.37549 (17)0.3543 (3)0.0504 (7)
C20.9967 (4)0.3075 (2)0.3778 (3)0.0689 (9)
H2A0.9617890.2787250.3169870.083*
C31.0298 (5)0.2812 (2)0.4933 (4)0.0886 (13)
H31.0172050.2348320.5087750.106*
C41.0796 (4)0.3225 (3)0.5821 (4)0.0969 (15)
H41.1029550.3044650.6582770.116*
C51.0962 (4)0.3914 (3)0.5604 (4)0.0894 (14)
H51.1271200.4201490.6228580.107*
C61.0674 (4)0.4174 (2)0.4479 (3)0.0698 (10)
H61.0824230.4635890.4330090.084*
C70.9895 (3)0.40743 (17)0.2342 (3)0.0550 (8)
C80.9214 (3)0.36509 (16)0.1318 (3)0.0517 (8)
H80.9431520.3166500.1451780.062*
C90.9706 (3)0.38605 (14)0.0075 (3)0.0470 (7)
H90.9610660.4357150.0016700.056*
C100.8949 (3)0.35106 (13)0.0970 (3)0.0429 (7)
C110.8015 (3)0.38703 (14)0.1692 (3)0.0466 (7)
H110.7894870.4333360.1531010.056*
C120.7237 (3)0.35821 (13)0.2648 (3)0.0412 (7)
C130.7453 (3)0.28845 (14)0.2869 (3)0.0416 (6)
C140.8396 (3)0.25255 (13)0.2145 (3)0.0405 (6)
C150.9147 (3)0.28183 (14)0.1195 (3)0.0448 (7)
H150.9766680.2560870.0720580.054*
C161.1976 (4)0.4048 (3)0.0655 (4)0.0906 (13)
H16A1.2925770.3908120.0542050.136*
H16B1.1900150.4529830.0501780.136*
H16C1.1669390.3952230.1475530.136*
C170.6211 (3)0.40095 (15)0.3431 (3)0.0537 (8)
C180.6134 (4)0.47467 (17)0.2953 (4)0.0825 (13)
H18A0.5466560.5000400.3435030.124*
H18B0.7028990.4958890.3004100.124*
H18C0.5858150.4741360.2120660.124*
C190.6699 (4)0.40251 (19)0.4744 (3)0.0742 (11)
H19A0.6702840.3568510.5065560.111*
H19B0.7619670.4211800.4760410.111*
H19C0.6079800.4304700.5229400.111*
C200.4752 (3)0.3707 (2)0.3379 (4)0.0757 (11)
H20A0.4752070.3253070.3711870.114*
H20B0.4115280.3988230.3843880.114*
H20C0.4470260.3689980.2548960.114*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0553 (2)0.1649 (5)0.0793 (3)0.0111 (3)0.0019 (2)0.0321 (3)
Br20.0547 (2)0.04056 (17)0.0733 (3)0.00571 (13)0.00985 (16)0.00330 (15)
O10.126 (2)0.0566 (14)0.0644 (16)0.0193 (15)0.0299 (16)0.0011 (13)
O20.0561 (12)0.0463 (10)0.0564 (13)0.0008 (9)0.0213 (11)0.0054 (10)
O30.0475 (12)0.0580 (12)0.0559 (14)0.0007 (10)0.0149 (11)0.0089 (11)
C10.0438 (16)0.065 (2)0.0421 (18)0.0001 (14)0.0010 (14)0.0022 (15)
C20.072 (2)0.081 (2)0.054 (2)0.002 (2)0.0041 (18)0.003 (2)
C30.106 (3)0.100 (3)0.060 (3)0.001 (3)0.006 (2)0.021 (2)
C40.068 (3)0.171 (5)0.051 (3)0.004 (3)0.002 (2)0.024 (3)
C50.069 (3)0.145 (4)0.054 (3)0.013 (3)0.007 (2)0.010 (3)
C60.064 (2)0.093 (3)0.052 (2)0.0047 (19)0.0052 (18)0.012 (2)
C70.0581 (19)0.0570 (18)0.0495 (19)0.0020 (15)0.0081 (16)0.0061 (15)
C80.0506 (18)0.0547 (16)0.0493 (19)0.0068 (14)0.0085 (15)0.0039 (15)
C90.0463 (16)0.0461 (15)0.0478 (18)0.0011 (12)0.0126 (14)0.0009 (13)
C100.0431 (15)0.0445 (15)0.0404 (16)0.0010 (12)0.0093 (13)0.0028 (12)
C110.0477 (17)0.0387 (13)0.0528 (18)0.0015 (12)0.0080 (14)0.0011 (13)
C120.0391 (14)0.0414 (13)0.0424 (17)0.0023 (11)0.0095 (13)0.0047 (12)
C130.0382 (14)0.0457 (14)0.0407 (16)0.0028 (12)0.0050 (13)0.0024 (13)
C140.0410 (14)0.0343 (12)0.0460 (16)0.0009 (11)0.0027 (13)0.0009 (12)
C150.0438 (15)0.0436 (15)0.0465 (17)0.0027 (12)0.0101 (14)0.0079 (13)
C160.065 (2)0.121 (3)0.086 (3)0.005 (2)0.010 (2)0.037 (3)
C170.0491 (17)0.0458 (15)0.065 (2)0.0064 (13)0.0213 (16)0.0026 (15)
C180.087 (3)0.0505 (18)0.107 (3)0.0199 (18)0.046 (2)0.001 (2)
C190.082 (3)0.076 (2)0.063 (2)0.007 (2)0.022 (2)0.022 (2)
C200.0476 (19)0.078 (2)0.100 (3)0.0113 (17)0.018 (2)0.001 (2)
Geometric parameters (Å, º) top
Br1—C81.936 (3)C10—C111.377 (4)
Br2—C141.904 (3)C10—C151.390 (4)
O1—C71.206 (4)C11—H110.9300
O2—H20.8499C11—C121.393 (4)
O2—C131.358 (3)C12—C131.402 (4)
O3—C91.427 (3)C12—C171.540 (4)
O3—C161.404 (4)C13—C141.382 (4)
C1—C21.367 (5)C14—C151.378 (4)
C1—C61.396 (5)C15—H150.9300
C1—C71.476 (4)C16—H16A0.9600
C2—H2A0.9300C16—H16B0.9600
C2—C31.399 (5)C16—H16C0.9600
C3—H30.9300C17—C181.536 (4)
C3—C41.346 (6)C17—C191.531 (5)
C4—H40.9300C17—C201.528 (5)
C4—C51.378 (7)C18—H18A0.9600
C5—H50.9300C18—H18B0.9600
C5—C61.359 (6)C18—H18C0.9600
C6—H60.9300C19—H19A0.9600
C7—C81.531 (4)C19—H19B0.9600
C8—H80.9800C19—H19C0.9600
C8—C91.516 (5)C20—H20A0.9600
C9—H90.9800C20—H20B0.9600
C9—C101.508 (4)C20—H20C0.9600
C13—O2—H2110.7C11—C12—C17121.8 (2)
C16—O3—C9114.3 (3)C13—C12—C17121.8 (2)
C2—C1—C6118.5 (3)O2—C13—C12118.2 (2)
C2—C1—C7124.1 (3)O2—C13—C14122.3 (2)
C6—C1—C7117.4 (3)C14—C13—C12119.5 (2)
C1—C2—H2A120.0C13—C14—Br2118.7 (2)
C1—C2—C3120.1 (4)C15—C14—Br2118.01 (19)
C3—C2—H2A120.0C15—C14—C13123.3 (2)
C2—C3—H3119.8C10—C15—H15121.1
C4—C3—C2120.4 (4)C14—C15—C10117.9 (2)
C4—C3—H3119.8C14—C15—H15121.1
C3—C4—H4120.0O3—C16—H16A109.5
C3—C4—C5120.1 (4)O3—C16—H16B109.5
C5—C4—H4120.0O3—C16—H16C109.5
C4—C5—H5120.0H16A—C16—H16B109.5
C6—C5—C4120.1 (4)H16A—C16—H16C109.5
C6—C5—H5120.0H16B—C16—H16C109.5
C1—C6—H6119.6C18—C17—C12110.7 (2)
C5—C6—C1120.8 (4)C19—C17—C12109.2 (3)
C5—C6—H6119.6C19—C17—C18108.8 (3)
O1—C7—C1121.9 (3)C20—C17—C12110.3 (3)
O1—C7—C8118.8 (3)C20—C17—C18107.3 (3)
C1—C7—C8119.3 (3)C20—C17—C19110.5 (3)
Br1—C8—H8109.0C17—C18—H18A109.5
C7—C8—Br1104.8 (2)C17—C18—H18B109.5
C7—C8—H8109.0C17—C18—H18C109.5
C9—C8—Br1112.5 (2)H18A—C18—H18B109.5
C9—C8—C7112.3 (3)H18A—C18—H18C109.5
C9—C8—H8109.0H18B—C18—H18C109.5
O3—C9—C8101.9 (2)C17—C19—H19A109.5
O3—C9—H9109.2C17—C19—H19B109.5
O3—C9—C10112.9 (2)C17—C19—H19C109.5
C8—C9—H9109.2H19A—C19—H19B109.5
C10—C9—C8114.1 (2)H19A—C19—H19C109.5
C10—C9—H9109.2H19B—C19—H19C109.5
C11—C10—C9120.2 (2)C17—C20—H20A109.5
C11—C10—C15119.0 (2)C17—C20—H20B109.5
C15—C10—C9120.8 (2)C17—C20—H20C109.5
C10—C11—H11118.0H20A—C20—H20B109.5
C10—C11—C12123.9 (3)H20A—C20—H20C109.5
C12—C11—H11118.0H20B—C20—H20C109.5
C11—C12—C13116.4 (2)
Br1—C8—C9—O3177.73 (17)C7—C8—C9—C10173.7 (2)
Br1—C8—C9—C1055.7 (3)C8—C9—C10—C11107.5 (3)
Br2—C14—C15—C10179.0 (2)C8—C9—C10—C1570.4 (4)
O1—C7—C8—Br189.9 (3)C9—C10—C11—C12177.8 (3)
O1—C7—C8—C932.5 (4)C9—C10—C15—C14178.3 (3)
O2—C13—C14—Br20.1 (4)C10—C11—C12—C130.5 (5)
O2—C13—C14—C15179.7 (3)C10—C11—C12—C17179.7 (3)
O3—C9—C10—C11136.8 (3)C11—C10—C15—C140.4 (5)
O3—C9—C10—C1545.3 (4)C11—C12—C13—O2179.2 (3)
C1—C2—C3—C40.4 (6)C11—C12—C13—C140.2 (4)
C1—C7—C8—Br189.4 (3)C11—C12—C17—C183.3 (5)
C1—C7—C8—C9148.2 (3)C11—C12—C17—C19116.5 (3)
C2—C1—C6—C51.1 (5)C11—C12—C17—C20121.9 (3)
C2—C1—C7—O1173.4 (4)C12—C13—C14—Br2179.3 (2)
C2—C1—C7—C87.4 (5)C12—C13—C14—C150.3 (5)
C2—C3—C4—C51.1 (7)C13—C12—C17—C18177.5 (3)
C3—C4—C5—C62.6 (7)C13—C12—C17—C1962.7 (4)
C4—C5—C6—C12.6 (6)C13—C12—C17—C2058.9 (4)
C6—C1—C2—C30.4 (5)C13—C14—C15—C100.6 (5)
C6—C1—C7—O14.3 (5)C15—C10—C11—C120.1 (5)
C6—C1—C7—C8174.9 (3)C16—O3—C9—C8157.1 (3)
C7—C1—C2—C3177.3 (4)C16—O3—C9—C1080.1 (4)
C7—C1—C6—C5178.9 (4)C17—C12—C13—O20.1 (4)
C7—C8—C9—O364.3 (3)C17—C12—C13—C14179.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···Br20.852.523.0676 (19)123
O2—H2···O3i0.852.122.791 (3)136
Symmetry code: (i) x1/2, y+1/2, z1/2.
2-Bromo-3-(3-tert-butyl-5-bromo-4-hydroxyphenyl)-3-ethoxy-1-phenylpropan-1-one (4) top
Crystal data top
C21H24Br2O3F(000) = 976
Mr = 484.22Dx = 1.515 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 9.6342 (4) ÅCell parameters from 8670 reflections
b = 19.8082 (8) Åθ = 2.4–27.2°
c = 11.1545 (5) ŵ = 3.83 mm1
β = 94.076 (1)°T = 296 K
V = 2123.30 (16) Å3Plate, colorless
Z = 40.17 × 0.14 × 0.14 mm
Data collection top
Bruker APEXII CCD
diffractometer
4192 reflections with I > 2σ(I)
φ and ω scansRint = 0.028
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
θmax = 28.3°, θmin = 2.1°
Tmin = 0.534, Tmax = 0.587h = 1212
24293 measured reflectionsk = 2626
5285 independent reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: difference Fourier map
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: mixed
wR(F2) = 0.091H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0421P)2 + 1.0628P]
where P = (Fo2 + 2Fc2)/3
5285 reflections(Δ/σ)max = 0.001
239 parametersΔρmax = 0.62 e Å3
2 restraintsΔρmin = 0.42 e Å3
Special details top

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

Refinement. The C16 and C17 atoms of the ethyl fragment are disordered over two position. The disorder was modeled and refined including alternative positions with relative occupancies of 0.671 (12):0.329 (12).

The X-ray diffraction patterns of 24 were collected using a Bruker SMART APEXII CCD area detector equipped with graphite-monochromated Mo Kα radiation (λ = 0.71073 Å) at room temperature. Absorption correction was applied by SADABS (Bruker, 2016). The structure was solved by direct methods and refined on F2 by full-matrix least-squares using Bruker SHELXTL97 (Sheldrick, 2015), operating within the OLEX2 program (Dolomanov et al., 2009). All non-H atoms were refined anisotropically. The details of the crystallographic data are summarized in Table 1. Crystallographic data for the structural analysis have been deposited to the Cambridge Crystallographic Data Center (CCDC 1523181–1523183 for 24). Copy of this information can be obtained free of charge from The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: (+44) 1223-336033; E-mail: deposit@ccdc.cam.ac.uk or www.ccdc.cam.ac.uk/data_request/cif). ORTEP views were drawn using OLEX2 software (Dolomanov et al., 2009).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Br10.73651 (3)0.37129 (2)1.14539 (3)0.08009 (13)
Br20.88337 (3)0.15837 (2)0.76290 (2)0.05127 (9)
O11.0271 (3)0.46527 (9)1.21533 (17)0.0682 (6)
O20.68872 (17)0.25493 (8)0.61647 (14)0.0468 (4)
H2O0.71080.21500.61550.070*
O31.12383 (17)0.37515 (9)1.01606 (14)0.0468 (4)
C11.0272 (2)0.37619 (13)1.3550 (2)0.0419 (5)
C21.0118 (3)0.30851 (15)1.3783 (2)0.0574 (7)
H2A0.98100.27931.31670.069*
C31.0422 (4)0.28382 (19)1.4938 (3)0.0759 (9)
H3A1.03240.23801.50910.091*
C41.0862 (4)0.3263 (2)1.5845 (3)0.0796 (10)
H4A1.10550.30941.66180.096*
C51.1021 (3)0.3934 (2)1.5625 (3)0.0749 (10)
H5A1.13240.42221.62490.090*
C61.0736 (3)0.41907 (16)1.4483 (2)0.0552 (6)
H6A1.08530.46491.43380.066*
C71.0006 (3)0.40688 (12)1.2337 (2)0.0440 (5)
C80.9362 (2)0.36353 (12)1.1309 (2)0.0425 (5)
H8A0.96480.31641.14340.051*
C90.9777 (2)0.38723 (12)1.0088 (2)0.0412 (5)
H9A0.96050.43581.00100.049*
C100.9023 (2)0.35086 (11)0.90430 (19)0.0382 (5)
C110.8087 (2)0.38528 (11)0.82635 (19)0.0391 (5)
H11A0.79490.43110.83970.047*
C120.7345 (2)0.35504 (11)0.72937 (19)0.0352 (4)
C130.7588 (2)0.28615 (11)0.71097 (18)0.0348 (4)
C140.8531 (2)0.25180 (11)0.78932 (19)0.0355 (4)
C150.9255 (2)0.28292 (11)0.88480 (19)0.0389 (5)
H15A0.98870.25880.93510.047*
C161.1948 (7)0.4069 (6)0.9213 (10)0.0798 (16)0.671 (12)
H16A1.14020.44500.89030.096*0.671 (12)
H16B1.20200.37490.85620.096*0.671 (12)
C171.3361 (6)0.4306 (5)0.9629 (6)0.0798 (16)0.671 (12)
H17A1.37910.45120.89710.120*0.671 (12)
H17B1.32940.46291.02620.120*0.671 (12)
H17C1.39120.39290.99220.120*0.671 (12)
C16'1.1907 (14)0.4227 (11)0.940 (2)0.0798 (16)0.329 (12)
H16C1.19150.46780.97400.096*0.329 (12)
H16D1.14410.42400.85990.096*0.329 (12)
C17'1.3360 (11)0.3953 (9)0.9370 (14)0.0798 (16)0.329 (12)
H17D1.38900.42390.88790.120*0.329 (12)
H17E1.37930.39401.01720.120*0.329 (12)
H17F1.33230.35050.90400.120*0.329 (12)
C180.6336 (2)0.39565 (12)0.6438 (2)0.0427 (5)
C190.6227 (3)0.46929 (13)0.6853 (3)0.0599 (7)
H19A0.58850.47040.76410.090*
H19B0.56000.49350.63010.090*
H19C0.71300.49000.68780.090*
C200.4870 (3)0.36535 (15)0.6401 (3)0.0594 (7)
H20A0.45600.36400.72000.089*
H20B0.48870.32040.60810.089*
H20C0.42450.39270.58990.089*
C210.6866 (3)0.39604 (16)0.5171 (2)0.0587 (7)
H21A0.62280.42080.46370.088*
H21B0.69360.35050.48880.088*
H21C0.77650.41710.51960.088*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.04824 (17)0.1229 (3)0.0683 (2)0.00845 (17)0.00130 (14)0.02581 (19)
Br20.05516 (16)0.03929 (13)0.05715 (16)0.00762 (10)0.01154 (11)0.00774 (10)
O10.1073 (17)0.0435 (10)0.0498 (11)0.0143 (10)0.0212 (10)0.0021 (8)
O20.0496 (9)0.0446 (9)0.0432 (9)0.0005 (7)0.0179 (7)0.0097 (7)
O30.0460 (9)0.0544 (10)0.0381 (8)0.0084 (7)0.0105 (7)0.0081 (7)
C10.0359 (11)0.0553 (14)0.0340 (11)0.0007 (10)0.0010 (9)0.0030 (10)
C20.0690 (18)0.0609 (17)0.0417 (14)0.0002 (13)0.0002 (12)0.0036 (12)
C30.086 (2)0.081 (2)0.0601 (19)0.0001 (18)0.0022 (16)0.0247 (16)
C40.067 (2)0.131 (3)0.0400 (16)0.004 (2)0.0047 (13)0.0195 (18)
C50.0642 (19)0.123 (3)0.0367 (14)0.0144 (19)0.0029 (13)0.0090 (17)
C60.0514 (15)0.0742 (18)0.0394 (13)0.0061 (13)0.0019 (11)0.0083 (12)
C70.0488 (13)0.0441 (13)0.0376 (12)0.0006 (10)0.0082 (10)0.0061 (9)
C80.0451 (13)0.0434 (12)0.0374 (12)0.0041 (10)0.0071 (9)0.0050 (9)
C90.0454 (12)0.0386 (11)0.0372 (11)0.0022 (9)0.0141 (9)0.0001 (9)
C100.0414 (12)0.0409 (12)0.0306 (10)0.0037 (9)0.0090 (8)0.0008 (8)
C110.0438 (12)0.0352 (11)0.0369 (11)0.0008 (9)0.0068 (9)0.0001 (8)
C120.0325 (10)0.0394 (11)0.0329 (10)0.0002 (8)0.0048 (8)0.0014 (8)
C130.0329 (10)0.0415 (11)0.0291 (10)0.0041 (8)0.0034 (8)0.0024 (8)
C140.0377 (11)0.0341 (10)0.0342 (11)0.0003 (8)0.0014 (8)0.0013 (8)
C150.0419 (12)0.0391 (11)0.0341 (11)0.0020 (9)0.0084 (9)0.0038 (9)
C160.0758 (17)0.098 (5)0.066 (3)0.022 (2)0.0065 (15)0.017 (3)
C170.0758 (17)0.098 (5)0.066 (3)0.022 (2)0.0065 (15)0.017 (3)
C16'0.0758 (17)0.098 (5)0.066 (3)0.022 (2)0.0065 (15)0.017 (3)
C17'0.0758 (17)0.098 (5)0.066 (3)0.022 (2)0.0065 (15)0.017 (3)
C180.0392 (12)0.0459 (12)0.0408 (12)0.0057 (9)0.0125 (9)0.0017 (10)
C190.0612 (17)0.0476 (14)0.0670 (17)0.0113 (12)0.0221 (13)0.0022 (13)
C200.0384 (13)0.0682 (17)0.0697 (18)0.0038 (12)0.0095 (12)0.0061 (14)
C210.0605 (16)0.0700 (18)0.0432 (14)0.0061 (13)0.0125 (12)0.0117 (12)
Geometric parameters (Å, º) top
Br1—C81.948 (2)C12—C131.402 (3)
Br2—C141.900 (2)C12—C181.541 (3)
O1—C71.205 (3)C13—C141.393 (3)
O2—H2O0.8199C14—C151.377 (3)
O2—C131.360 (2)C15—H15A0.9300
O3—C91.425 (3)C16—H16A0.9700
O3—C161.443 (11)C16—H16B0.9700
O3—C16'1.45 (3)C16—C171.482 (8)
C1—C21.375 (4)C17—H17A0.9600
C1—C61.392 (3)C17—H17B0.9600
C1—C71.489 (3)C17—H17C0.9600
C2—H2A0.9300C16'—H16C0.9700
C2—C31.390 (4)C16'—H16D0.9700
C3—H3A0.9300C16'—C17'1.504 (10)
C3—C41.360 (5)C17'—H17D0.9600
C4—H4A0.9300C17'—H17E0.9600
C4—C51.363 (5)C17'—H17F0.9600
C5—H5A0.9300C18—C191.536 (4)
C5—C61.381 (4)C18—C201.532 (4)
C6—H6A0.9300C18—C211.536 (4)
C7—C81.529 (3)C19—H19A0.9600
C8—H8A0.9800C19—H19B0.9600
C8—C91.520 (3)C19—H19C0.9600
C9—H9A0.9800C20—H20A0.9600
C9—C101.512 (3)C20—H20B0.9600
C10—C111.386 (3)C20—H20C0.9600
C10—C151.384 (3)C21—H21A0.9600
C11—H11A0.9300C21—H21B0.9600
C11—C121.389 (3)C21—H21C0.9600
C13—O2—H2O109.5C10—C15—H15A120.7
C9—O3—C16113.8 (4)C14—C15—C10118.58 (19)
C9—O3—C16'109.6 (6)C14—C15—H15A120.7
C2—C1—C6119.1 (2)O3—C16—H16A109.1
C2—C1—C7123.7 (2)O3—C16—H16B109.1
C6—C1—C7117.1 (2)O3—C16—C17112.4 (8)
C1—C2—H2A120.0H16A—C16—H16B107.9
C1—C2—C3120.0 (3)C17—C16—H16A109.1
C3—C2—H2A120.0C17—C16—H16B109.1
C2—C3—H3A119.8C16—C17—H17A109.5
C4—C3—C2120.4 (3)C16—C17—H17B109.5
C4—C3—H3A119.8C16—C17—H17C109.5
C3—C4—H4A119.9H17A—C17—H17B109.5
C3—C4—C5120.1 (3)H17A—C17—H17C109.5
C5—C4—H4A119.9H17B—C17—H17C109.5
C4—C5—H5A119.7O3—C16'—H16C111.1
C4—C5—C6120.5 (3)O3—C16'—H16D111.1
C6—C5—H5A119.7O3—C16'—C17'103.3 (16)
C1—C6—H6A120.1H16C—C16'—H16D109.1
C5—C6—C1119.8 (3)C17'—C16'—H16C111.1
C5—C6—H6A120.1C17'—C16'—H16D111.1
O1—C7—C1121.5 (2)C16'—C17'—H17D109.5
O1—C7—C8119.4 (2)C16'—C17'—H17E109.5
C1—C7—C8119.1 (2)C16'—C17'—H17F109.5
Br1—C8—H8A109.4H17D—C17'—H17E109.5
C7—C8—Br1104.12 (16)H17D—C17'—H17F109.5
C7—C8—H8A109.4H17E—C17'—H17F109.5
C9—C8—Br1111.95 (15)C19—C18—C12111.22 (18)
C9—C8—C7112.3 (2)C20—C18—C12110.6 (2)
C9—C8—H8A109.4C20—C18—C19107.3 (2)
O3—C9—C8102.64 (17)C20—C18—C21110.1 (2)
O3—C9—H9A109.3C21—C18—C12109.6 (2)
O3—C9—C10112.46 (19)C21—C18—C19107.9 (2)
C8—C9—H9A109.3C18—C19—H19A109.5
C10—C9—C8113.66 (19)C18—C19—H19B109.5
C10—C9—H9A109.3C18—C19—H19C109.5
C11—C10—C9120.3 (2)H19A—C19—H19B109.5
C15—C10—C9120.69 (19)H19A—C19—H19C109.5
C15—C10—C11119.01 (19)H19B—C19—H19C109.5
C10—C11—H11A118.3C18—C20—H20A109.5
C10—C11—C12123.5 (2)C18—C20—H20B109.5
C12—C11—H11A118.3C18—C20—H20C109.5
C11—C12—C13116.85 (19)H20A—C20—H20B109.5
C11—C12—C18121.7 (2)H20A—C20—H20C109.5
C13—C12—C18121.47 (18)H20B—C20—H20C109.5
O2—C13—C12118.52 (18)C18—C21—H21A109.5
O2—C13—C14122.02 (19)C18—C21—H21B109.5
C14—C13—C12119.47 (18)C18—C21—H21C109.5
C13—C14—Br2118.62 (15)H21A—C21—H21B109.5
C15—C14—Br2118.78 (16)H21A—C21—H21C109.5
C15—C14—C13122.59 (19)H21B—C21—H21C109.5
Br1—C8—C9—O3178.02 (14)C8—C9—C10—C1566.9 (3)
Br1—C8—C9—C1056.3 (2)C9—O3—C16—C17144.9 (9)
Br2—C14—C15—C10179.46 (17)C9—O3—C16'—C17'168.9 (12)
O1—C7—C8—Br192.8 (3)C9—C10—C11—C12179.2 (2)
O1—C7—C8—C928.6 (3)C9—C10—C15—C14179.2 (2)
O2—C13—C14—Br20.3 (3)C10—C11—C12—C130.7 (3)
O2—C13—C14—C15179.5 (2)C10—C11—C12—C18178.9 (2)
O3—C9—C10—C11130.8 (2)C11—C10—C15—C140.9 (3)
O3—C9—C10—C1549.2 (3)C11—C12—C13—O2179.6 (2)
C1—C2—C3—C40.5 (5)C11—C12—C13—C140.5 (3)
C1—C7—C8—Br186.3 (2)C11—C12—C18—C193.2 (3)
C1—C7—C8—C9152.4 (2)C11—C12—C18—C20122.4 (2)
C2—C1—C6—C50.6 (4)C11—C12—C18—C21116.0 (3)
C2—C1—C7—O1173.4 (3)C12—C13—C14—Br2179.65 (16)
C2—C1—C7—C87.6 (4)C12—C13—C14—C150.6 (3)
C2—C3—C4—C50.6 (5)C13—C12—C18—C19178.6 (2)
C3—C4—C5—C60.1 (5)C13—C12—C18—C2059.4 (3)
C4—C5—C6—C10.5 (5)C13—C12—C18—C2162.2 (3)
C6—C1—C2—C30.1 (4)C13—C14—C15—C100.7 (4)
C6—C1—C7—O14.9 (4)C15—C10—C11—C120.9 (4)
C6—C1—C7—C8174.1 (2)C16—O3—C9—C8167.1 (5)
C7—C1—C2—C3178.4 (3)C16—O3—C9—C1070.3 (5)
C7—C1—C6—C5179.0 (3)C16'—O3—C9—C8151.5 (9)
C7—C8—C9—O365.2 (2)C16'—O3—C9—C1085.9 (9)
C7—C8—C9—C10173.05 (19)C18—C12—C13—O21.4 (3)
C8—C9—C10—C11113.1 (2)C18—C12—C13—C14178.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···Br20.822.523.0671 (16)126
O2—H2O···O3i0.822.232.861 (2)134
Symmetry code: (i) x1/2, y+1/2, z1/2.
Hydrogen (ad) and halogen (e) bond lengths (Å) in 24 (as drawn in Fig. 5) top
Compoundabcde
22.655 (16)2.098 (16)2.663 (16)2.643 (2)3.820 (11)
32.807 (2)2.120 (2)2.677 (19)3.709 (5)
42.707 (15)2.234 (17)2.614 (16)2.622 (2)3.778 (4)
 

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