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In the title compound, C19H28BrNO3, which crystallizes with two mol­ecules in the asymmetric unit, the six-membered cyclo­hexa­none ring exists in a sightly distorted chair conformation. The bromo and methoxy­ethoxy groups are oriented axially, whereas the phenyl group and tert-butyl adopt equatorial positions. The crystal structure is stabilized by O—H...O inter­molecular hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806043236/bt2208sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806043236/bt2208Isup2.hkl
Contains datablock I

CCDC reference: 627360

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.033
  • wR factor = 0.100
  • Data-to-parameter ratio = 15.8

checkCIF/PLATON results

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Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.94 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.95 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.38 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O3A PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13B PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 8
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.940 Tmax scaled 0.688 Tmin scaled 0.613 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL/PC (Bruker, 2000); program(s) used to refine structure: SHELXTL/PC; molecular graphics: SHELXTL/PC and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL/PC.

3-Bromo-5-tert-butyl-2-(methoxyethoxy)-2-phenylcyclohexanone oxime top
Crystal data top
C19H28BrNO3Z = 4
Mr = 398.33F(000) = 832
Triclinic, P1Dx = 1.326 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 12.296 (5) ÅCell parameters from 25 reflections
b = 12.635 (5) Åθ = 9.4–13.2°
c = 14.067 (5) ŵ = 2.08 mm1
α = 91.085 (5)°T = 293 K
β = 109.570 (5)°Block, colourless
γ = 103.076 (5)°0.24 × 0.19 × 0.18 mm
V = 1995.1 (13) Å3
Data collection top
Nonius MACH3
diffractometer
4533 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.016
Graphite monochromatorθmax = 25.0°, θmin = 2.1°
ω–2θ scansh = 114
Absorption correction: ψ scan
(North et al., 1968)
k = 1514
Tmin = 0.652, Tmax = 0.732l = 1616
8074 measured reflections3 standard reflections every 60 min
7000 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.054P)2 + 0.0267P]
where P = (Fo2 + 2Fc2)/3
7000 reflections(Δ/σ)max < 0.001
443 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.44 e Å3
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.49691 (3)0.01375 (3)0.65342 (3)0.06180 (13)
C1A0.6449 (3)0.2309 (2)0.5667 (2)0.0411 (7)
C2A0.6744 (2)0.2170 (2)0.6789 (2)0.0397 (7)
C3A0.5592 (3)0.1702 (2)0.7015 (2)0.0431 (7)
H3A0.57940.17770.77530.052*
C4A0.4624 (3)0.2291 (2)0.6560 (2)0.0458 (7)
H4A10.48900.30390.68730.055*
H4A20.39200.19390.67090.055*
C5A0.4299 (3)0.2295 (2)0.5419 (2)0.0438 (7)
H5A0.40330.15270.51360.053*
C6A0.5415 (3)0.2786 (3)0.5168 (2)0.0531 (8)
H6A10.52160.26840.44390.064*
H6A20.56540.35660.53700.064*
C7A0.7686 (3)0.1548 (2)0.7290 (2)0.0436 (7)
C8A0.7906 (3)0.0705 (2)0.6784 (2)0.0561 (8)
H8A0.74940.05180.60920.067*
C9A0.8734 (3)0.0146 (3)0.7303 (3)0.0659 (10)
H9A0.88800.04070.69540.079*
C10A0.9340 (3)0.0398 (3)0.8322 (3)0.0708 (11)
H10A0.98960.00190.86660.085*
C11A0.9120 (3)0.1215 (3)0.8832 (3)0.0638 (10)
H11A0.95240.13880.95260.077*
C12A0.8301 (3)0.1779 (3)0.8319 (2)0.0535 (8)
H12A0.81600.23290.86760.064*
C13A0.3247 (3)0.2819 (2)0.4905 (2)0.0512 (8)
C14A0.3017 (3)0.2787 (3)0.3762 (3)0.0754 (11)
H14A0.22620.29460.34210.113*
H14B0.30080.20740.35070.113*
H14C0.36370.33210.36440.113*
C15A0.2115 (3)0.2145 (3)0.5048 (3)0.0665 (10)
H15A0.21990.22230.57510.100*
H15B0.19970.13900.48320.100*
H15C0.14410.24020.46510.100*
C16A0.3483 (3)0.4000 (3)0.5344 (3)0.0776 (11)
H16A0.35320.40120.60400.116*
H16B0.28450.43100.49640.116*
H16C0.42200.44180.53050.116*
C17A0.8138 (3)0.3970 (2)0.7182 (2)0.0552 (8)
H17A0.79980.40560.64700.066*
H17B0.88180.36580.74440.066*
C18A0.8370 (3)0.5044 (3)0.7753 (2)0.0639 (9)
H18A0.90090.55600.76270.077*
H18B0.76620.53220.75230.077*
C19A0.9070 (5)0.5957 (3)0.9401 (3)0.1170 (18)
H19A0.98070.63620.93520.176*
H19B0.91850.58291.00940.176*
H19C0.84780.63660.91670.176*
N1A0.7189 (2)0.21523 (19)0.52591 (17)0.0452 (6)
O1A0.6881 (2)0.24457 (19)0.42584 (15)0.0565 (6)
H1A0.73850.23640.40210.085*
O2A0.71064 (17)0.32714 (14)0.72993 (14)0.0429 (5)
O3A0.8685 (2)0.49425 (17)0.87935 (17)0.0660 (6)
Br20.51278 (3)0.49951 (3)0.16708 (3)0.06388 (13)
C1B0.6614 (3)0.3495 (2)0.0780 (2)0.0425 (7)
C2B0.6961 (2)0.3824 (2)0.19124 (19)0.0399 (7)
C3B0.5828 (2)0.3774 (2)0.2175 (2)0.0429 (7)
H3B0.60570.38400.29150.051*
C4B0.4878 (3)0.2708 (2)0.1752 (2)0.0484 (7)
H4B10.51830.21090.20700.058*
H4B20.41850.27370.19250.058*
C5B0.4505 (3)0.2483 (2)0.0610 (2)0.0467 (7)
H5B0.41910.30980.03210.056*
C6B0.5600 (3)0.2516 (3)0.0320 (2)0.0586 (9)
H6B10.58780.18660.05220.070*
H6B20.53660.24880.04120.070*
C7B0.7889 (3)0.4892 (2)0.2394 (2)0.0445 (7)
C8B0.8046 (3)0.5812 (3)0.1885 (3)0.0576 (9)
H8B0.75990.57870.12010.069*
C9B0.8867 (3)0.6771 (3)0.2391 (3)0.0702 (10)
H9B0.89680.73820.20420.084*
C10B0.9527 (3)0.6829 (3)0.3395 (3)0.0717 (11)
H10B1.00880.74690.37250.086*
C11B0.9357 (3)0.5933 (3)0.3909 (3)0.0712 (10)
H11B0.97920.59720.45970.085*
C12B0.8542 (3)0.4974 (3)0.3416 (2)0.0557 (8)
H12B0.84330.43740.37770.067*
C13B0.3489 (3)0.1440 (3)0.0142 (3)0.0600 (9)
C14B0.2367 (3)0.1591 (4)0.0330 (3)0.0930 (14)
H14D0.17080.09840.00140.140*
H14E0.21880.22550.00770.140*
H14F0.25050.16280.10450.140*
C15B0.3202 (4)0.1293 (3)0.1008 (3)0.0847 (12)
H15D0.38230.10460.11460.127*
H15E0.31470.19780.12790.127*
H15F0.24580.07620.13170.127*
C16B0.3801 (4)0.0420 (3)0.0598 (3)0.0861 (12)
H16D0.45580.03740.05680.129*
H16E0.32000.02140.02220.129*
H16F0.38420.04550.12920.129*
C17B0.8390 (3)0.2682 (3)0.2297 (3)0.0610 (9)
H17C0.90920.32520.26710.073*
H17D0.83140.26380.15870.073*
C18B0.8485 (3)0.1616 (3)0.2704 (2)0.0633 (9)
H18C0.77550.10640.23580.076*
H18D0.91360.13890.25850.076*
C19B0.8719 (4)0.0702 (3)0.4167 (3)0.0843 (13)
H19D0.79790.01770.38260.126*
H19E0.88400.08020.48770.126*
H19F0.93610.04430.40820.126*
N1B0.7297 (2)0.3987 (2)0.03358 (17)0.0496 (6)
O1B0.6948 (2)0.35223 (18)0.06716 (15)0.0627 (6)
H1B0.74190.38350.09330.094*
O2B0.73507 (17)0.29090 (15)0.24124 (14)0.0445 (5)
O3B0.8688 (2)0.17141 (17)0.37479 (16)0.0588 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0575 (2)0.04427 (19)0.0704 (2)0.00240 (15)0.01156 (18)0.01282 (16)
C1A0.0455 (18)0.0429 (16)0.0369 (16)0.0070 (14)0.0195 (14)0.0033 (13)
C2A0.0442 (17)0.0378 (15)0.0381 (16)0.0073 (13)0.0175 (14)0.0025 (12)
C3A0.0489 (18)0.0441 (16)0.0347 (15)0.0038 (14)0.0175 (14)0.0038 (12)
C4A0.0467 (18)0.0466 (17)0.0473 (17)0.0073 (14)0.0233 (15)0.0055 (14)
C5A0.0456 (18)0.0425 (16)0.0443 (17)0.0120 (14)0.0161 (15)0.0069 (13)
C6A0.056 (2)0.068 (2)0.0459 (18)0.0234 (17)0.0251 (16)0.0178 (16)
C7A0.0426 (17)0.0434 (16)0.0440 (17)0.0052 (14)0.0175 (14)0.0065 (13)
C8A0.065 (2)0.0482 (19)0.0506 (19)0.0126 (17)0.0160 (17)0.0014 (15)
C9A0.066 (2)0.049 (2)0.080 (3)0.0197 (18)0.018 (2)0.0026 (18)
C10A0.048 (2)0.062 (2)0.086 (3)0.0155 (18)0.002 (2)0.011 (2)
C11A0.055 (2)0.069 (2)0.052 (2)0.0125 (19)0.0004 (17)0.0062 (18)
C12A0.058 (2)0.0555 (19)0.0453 (19)0.0137 (16)0.0159 (16)0.0031 (15)
C13A0.0474 (19)0.0457 (17)0.060 (2)0.0129 (15)0.0175 (16)0.0119 (15)
C14A0.068 (2)0.092 (3)0.069 (2)0.034 (2)0.018 (2)0.034 (2)
C15A0.049 (2)0.074 (2)0.078 (2)0.0179 (18)0.0217 (18)0.0179 (19)
C16A0.075 (3)0.055 (2)0.112 (3)0.029 (2)0.037 (2)0.013 (2)
C17A0.062 (2)0.0519 (19)0.0547 (19)0.0015 (16)0.0341 (17)0.0025 (15)
C18A0.078 (3)0.0476 (19)0.065 (2)0.0013 (18)0.033 (2)0.0089 (16)
C19A0.159 (5)0.077 (3)0.100 (3)0.005 (3)0.050 (3)0.033 (3)
N1A0.0488 (15)0.0515 (15)0.0360 (13)0.0099 (12)0.0172 (12)0.0052 (11)
O1A0.0693 (16)0.0735 (15)0.0418 (12)0.0260 (13)0.0328 (11)0.0136 (11)
O2A0.0503 (12)0.0387 (11)0.0437 (11)0.0059 (9)0.0250 (10)0.0004 (8)
O3A0.0787 (17)0.0533 (13)0.0576 (14)0.0033 (12)0.0266 (13)0.0095 (11)
Br20.0630 (2)0.0596 (2)0.0689 (2)0.02973 (18)0.01391 (18)0.00569 (17)
C1B0.0509 (18)0.0453 (17)0.0383 (16)0.0152 (15)0.0222 (15)0.0072 (13)
C2B0.0451 (17)0.0434 (16)0.0346 (15)0.0142 (14)0.0160 (13)0.0050 (12)
C3B0.0442 (17)0.0531 (17)0.0350 (15)0.0174 (14)0.0149 (13)0.0040 (13)
C4B0.0447 (18)0.0584 (19)0.0454 (17)0.0131 (15)0.0198 (15)0.0045 (14)
C5B0.0536 (19)0.0471 (17)0.0415 (17)0.0154 (15)0.0171 (15)0.0026 (13)
C6B0.070 (2)0.060 (2)0.0456 (19)0.0037 (18)0.0275 (17)0.0072 (15)
C7B0.0461 (18)0.0486 (17)0.0455 (18)0.0154 (14)0.0220 (15)0.0046 (14)
C8B0.069 (2)0.053 (2)0.055 (2)0.0149 (18)0.0270 (18)0.0042 (16)
C9B0.078 (3)0.053 (2)0.090 (3)0.011 (2)0.045 (2)0.005 (2)
C10B0.052 (2)0.061 (2)0.097 (3)0.0002 (18)0.029 (2)0.018 (2)
C11B0.052 (2)0.083 (3)0.067 (2)0.011 (2)0.0120 (19)0.010 (2)
C12B0.054 (2)0.059 (2)0.051 (2)0.0111 (17)0.0154 (16)0.0024 (16)
C13B0.056 (2)0.056 (2)0.064 (2)0.0095 (17)0.0190 (18)0.0076 (17)
C14B0.045 (2)0.113 (3)0.105 (3)0.007 (2)0.015 (2)0.027 (3)
C15B0.077 (3)0.085 (3)0.067 (3)0.007 (2)0.004 (2)0.022 (2)
C16B0.089 (3)0.054 (2)0.110 (3)0.010 (2)0.033 (3)0.006 (2)
C17B0.067 (2)0.074 (2)0.067 (2)0.0370 (19)0.0420 (19)0.0234 (18)
C18B0.072 (2)0.069 (2)0.064 (2)0.039 (2)0.0283 (19)0.0067 (18)
C19B0.088 (3)0.080 (3)0.106 (3)0.042 (2)0.044 (3)0.048 (2)
N1B0.0628 (17)0.0522 (15)0.0399 (14)0.0148 (13)0.0254 (13)0.0041 (12)
O1B0.0852 (18)0.0683 (15)0.0426 (13)0.0118 (13)0.0376 (12)0.0002 (11)
O2B0.0484 (12)0.0508 (12)0.0459 (11)0.0213 (10)0.0251 (10)0.0139 (9)
O3B0.0664 (15)0.0590 (13)0.0607 (14)0.0270 (12)0.0265 (12)0.0205 (11)
Geometric parameters (Å, º) top
Br1—C3A1.967 (3)Br2—C3B1.964 (3)
C1A—N1A1.274 (4)C1B—N1B1.270 (4)
C1A—C6A1.497 (4)C1B—C6B1.495 (4)
C1A—C2A1.520 (4)C1B—C2B1.527 (4)
C2A—O2A1.455 (3)C2B—O2B1.455 (3)
C2A—C7A1.530 (4)C2B—C7B1.527 (4)
C2A—C3A1.545 (4)C2B—C3B1.545 (4)
C3A—C4A1.513 (4)C3B—C4B1.525 (4)
C3A—H3A0.9800C3B—H3B0.9800
C4A—C5A1.519 (4)C4B—C5B1.517 (4)
C4A—H4A10.9700C4B—H4B10.9700
C4A—H4A20.9700C4B—H4B20.9700
C5A—C6A1.530 (4)C5B—C6B1.525 (4)
C5A—C13A1.554 (4)C5B—C13B1.550 (4)
C5A—H5A0.9800C5B—H5B0.9800
C6A—H6A10.9700C6B—H6B10.9700
C6A—H6A20.9700C6B—H6B20.9700
C7A—C12A1.380 (4)C7B—C12B1.380 (4)
C7A—C8A1.395 (4)C7B—C8B1.388 (4)
C8A—C9A1.383 (4)C8B—C9B1.388 (5)
C8A—H8A0.9300C8B—H8B0.9300
C9A—C10A1.369 (5)C9B—C10B1.363 (5)
C9A—H9A0.9300C9B—H9B0.9300
C10A—C11A1.372 (5)C10B—C11B1.369 (5)
C10A—H10A0.9300C10B—H10B0.9300
C11A—C12A1.378 (4)C11B—C12B1.381 (5)
C11A—H11A0.9300C11B—H11B0.9300
C12A—H12A0.9300C12B—H12B0.9300
C13A—C16A1.530 (4)C13B—C16B1.520 (5)
C13A—C14A1.533 (4)C13B—C15B1.534 (5)
C13A—C15A1.536 (4)C13B—C14B1.540 (5)
C14A—H14A0.9600C14B—H14D0.9600
C14A—H14B0.9600C14B—H14E0.9600
C14A—H14C0.9600C14B—H14F0.9600
C15A—H15A0.9600C15B—H15D0.9600
C15A—H15B0.9600C15B—H15E0.9600
C15A—H15C0.9600C15B—H15F0.9600
C16A—H16A0.9600C16B—H16D0.9600
C16A—H16B0.9600C16B—H16E0.9600
C16A—H16C0.9600C16B—H16F0.9600
C17A—O2A1.433 (3)C17B—O2B1.430 (4)
C17A—C18A1.482 (4)C17B—C18B1.487 (4)
C17A—H17A0.9700C17B—H17C0.9700
C17A—H17B0.9700C17B—H17D0.9700
C18A—O3A1.399 (4)C18B—O3B1.403 (4)
C18A—H18A0.9700C18B—H18C0.9700
C18A—H18B0.9700C18B—H18D0.9700
C19A—O3A1.417 (4)C19B—O3B1.421 (4)
C19A—H19A0.9600C19B—H19D0.9600
C19A—H19B0.9600C19B—H19E0.9600
C19A—H19C0.9600C19B—H19F0.9600
N1A—O1A1.410 (3)N1B—O1B1.409 (3)
O1A—H1A0.8200O1B—H1B0.8200
N1A—C1A—C6A124.5 (3)N1B—C1B—C6B125.0 (3)
N1A—C1A—C2A117.6 (3)N1B—C1B—C2B117.3 (3)
C6A—C1A—C2A117.2 (2)C6B—C1B—C2B117.1 (2)
O2A—C2A—C1A105.5 (2)O2B—C2B—C7B110.2 (2)
O2A—C2A—C7A109.7 (2)O2B—C2B—C1B105.3 (2)
C1A—C2A—C7A118.5 (2)C7B—C2B—C1B119.2 (2)
O2A—C2A—C3A100.9 (2)O2B—C2B—C3B100.6 (2)
C1A—C2A—C3A110.2 (2)C7B—C2B—C3B110.2 (2)
C7A—C2A—C3A110.5 (2)C1B—C2B—C3B109.6 (2)
C4A—C3A—C2A113.6 (2)C4B—C3B—C2B113.1 (2)
C4A—C3A—Br1109.16 (19)C4B—C3B—Br2108.61 (19)
C2A—C3A—Br1110.56 (19)C2B—C3B—Br2110.82 (19)
C4A—C3A—H3A107.8C4B—C3B—H3B108.0
C2A—C3A—H3A107.8C2B—C3B—H3B108.0
Br1—C3A—H3A107.8Br2—C3B—H3B108.0
C3A—C4A—C5A112.3 (2)C5B—C4B—C3B112.8 (2)
C3A—C4A—H4A1109.1C5B—C4B—H4B1109.0
C5A—C4A—H4A1109.1C3B—C4B—H4B1109.0
C3A—C4A—H4A2109.1C5B—C4B—H4B2109.0
C5A—C4A—H4A2109.1C3B—C4B—H4B2109.0
H4A1—C4A—H4A2107.9H4B1—C4B—H4B2107.8
C4A—C5A—C6A109.8 (2)C4B—C5B—C6B109.6 (2)
C4A—C5A—C13A114.3 (2)C4B—C5B—C13B114.4 (3)
C6A—C5A—C13A113.3 (2)C6B—C5B—C13B113.4 (2)
C4A—C5A—H5A106.3C4B—C5B—H5B106.3
C6A—C5A—H5A106.3C6B—C5B—H5B106.3
C13A—C5A—H5A106.3C13B—C5B—H5B106.3
C1A—C6A—C5A114.4 (2)C1B—C6B—C5B115.0 (3)
C1A—C6A—H6A1108.7C1B—C6B—H6B1108.5
C5A—C6A—H6A1108.7C5B—C6B—H6B1108.5
C1A—C6A—H6A2108.7C1B—C6B—H6B2108.5
C5A—C6A—H6A2108.7C5B—C6B—H6B2108.5
H6A1—C6A—H6A2107.6H6B1—C6B—H6B2107.5
C12A—C7A—C8A117.6 (3)C12B—C7B—C8B118.0 (3)
C12A—C7A—C2A118.3 (3)C12B—C7B—C2B118.0 (3)
C8A—C7A—C2A123.9 (3)C8B—C7B—C2B123.8 (3)
C9A—C8A—C7A120.4 (3)C9B—C8B—C7B120.3 (3)
C9A—C8A—H8A119.8C9B—C8B—H8B119.8
C7A—C8A—H8A119.8C7B—C8B—H8B119.8
C10A—C9A—C8A120.9 (3)C10B—C9B—C8B120.8 (3)
C10A—C9A—H9A119.6C10B—C9B—H9B119.6
C8A—C9A—H9A119.6C8B—C9B—H9B119.6
C9A—C10A—C11A119.3 (3)C9B—C10B—C11B119.2 (3)
C9A—C10A—H10A120.4C9B—C10B—H10B120.4
C11A—C10A—H10A120.4C11B—C10B—H10B120.4
C10A—C11A—C12A120.2 (3)C10B—C11B—C12B120.5 (4)
C10A—C11A—H11A119.9C10B—C11B—H11B119.7
C12A—C11A—H11A119.9C12B—C11B—H11B119.7
C11A—C12A—C7A121.7 (3)C7B—C12B—C11B121.0 (3)
C11A—C12A—H12A119.2C7B—C12B—H12B119.5
C7A—C12A—H12A119.2C11B—C12B—H12B119.5
C16A—C13A—C14A109.4 (3)C16B—C13B—C15B109.4 (3)
C16A—C13A—C15A108.6 (3)C16B—C13B—C14B108.9 (3)
C14A—C13A—C15A107.8 (3)C15B—C13B—C14B108.0 (3)
C16A—C13A—C5A112.5 (3)C16B—C13B—C5B112.5 (3)
C14A—C13A—C5A109.3 (3)C15B—C13B—C5B109.5 (3)
C15A—C13A—C5A109.2 (2)C14B—C13B—C5B108.5 (3)
C13A—C14A—H14A109.5C13B—C14B—H14D109.5
C13A—C14A—H14B109.5C13B—C14B—H14E109.5
H14A—C14A—H14B109.5H14D—C14B—H14E109.5
C13A—C14A—H14C109.5C13B—C14B—H14F109.5
H14A—C14A—H14C109.5H14D—C14B—H14F109.5
H14B—C14A—H14C109.5H14E—C14B—H14F109.5
C13A—C15A—H15A109.5C13B—C15B—H15D109.5
C13A—C15A—H15B109.5C13B—C15B—H15E109.5
H15A—C15A—H15B109.5H15D—C15B—H15E109.5
C13A—C15A—H15C109.5C13B—C15B—H15F109.5
H15A—C15A—H15C109.5H15D—C15B—H15F109.5
H15B—C15A—H15C109.5H15E—C15B—H15F109.5
C13A—C16A—H16A109.5C13B—C16B—H16D109.5
C13A—C16A—H16B109.5C13B—C16B—H16E109.5
H16A—C16A—H16B109.5H16D—C16B—H16E109.5
C13A—C16A—H16C109.5C13B—C16B—H16F109.5
H16A—C16A—H16C109.5H16D—C16B—H16F109.5
H16B—C16A—H16C109.5H16E—C16B—H16F109.5
O2A—C17A—C18A107.7 (3)O2B—C17B—C18B106.4 (3)
O2A—C17A—H17A110.2O2B—C17B—H17C110.4
C18A—C17A—H17A110.2C18B—C17B—H17C110.4
O2A—C17A—H17B110.2O2B—C17B—H17D110.4
C18A—C17A—H17B110.2C18B—C17B—H17D110.4
H17A—C17A—H17B108.5H17C—C17B—H17D108.6
O3A—C18A—C17A110.4 (3)O3B—C18B—C17B109.8 (3)
O3A—C18A—H18A109.6O3B—C18B—H18C109.7
C17A—C18A—H18A109.6C17B—C18B—H18C109.7
O3A—C18A—H18B109.6O3B—C18B—H18D109.7
C17A—C18A—H18B109.6C17B—C18B—H18D109.7
H18A—C18A—H18B108.1H18C—C18B—H18D108.2
O3A—C19A—H19A109.5O3B—C19B—H19D109.5
O3A—C19A—H19B109.5O3B—C19B—H19E109.5
H19A—C19A—H19B109.5H19D—C19B—H19E109.5
O3A—C19A—H19C109.5O3B—C19B—H19F109.5
H19A—C19A—H19C109.5H19D—C19B—H19F109.5
H19B—C19A—H19C109.5H19E—C19B—H19F109.5
C1A—N1A—O1A111.3 (2)C1B—N1B—O1B111.3 (2)
N1A—O1A—H1A109.5N1B—O1B—H1B109.5
C17A—O2A—C2A115.5 (2)C17B—O2B—C2B116.3 (2)
C18A—O3A—C19A113.6 (3)C18B—O3B—C19B112.2 (3)
N1A—C1A—C2A—O2A105.9 (3)N1B—C1B—C2B—O2B108.4 (3)
C6A—C1A—C2A—O2A64.8 (3)C6B—C1B—C2B—O2B63.0 (3)
N1A—C1A—C2A—C7A17.3 (4)N1B—C1B—C2B—C7B15.8 (4)
C6A—C1A—C2A—C7A172.0 (2)C6B—C1B—C2B—C7B172.8 (3)
N1A—C1A—C2A—C3A145.9 (3)N1B—C1B—C2B—C3B144.1 (3)
C6A—C1A—C2A—C3A43.4 (3)C6B—C1B—C2B—C3B44.5 (3)
O2A—C2A—C3A—C4A62.9 (3)O2B—C2B—C3B—C4B61.5 (3)
C1A—C2A—C3A—C4A48.3 (3)C7B—C2B—C3B—C4B177.8 (2)
C7A—C2A—C3A—C4A178.9 (2)C1B—C2B—C3B—C4B49.1 (3)
O2A—C2A—C3A—Br1173.96 (16)O2B—C2B—C3B—Br2176.23 (16)
C1A—C2A—C3A—Br174.9 (2)C7B—C2B—C3B—Br260.0 (3)
C7A—C2A—C3A—Br158.0 (3)C1B—C2B—C3B—Br273.2 (2)
C2A—C3A—C4A—C5A56.7 (3)C2B—C3B—C4B—C5B57.1 (3)
Br1—C3A—C4A—C5A67.2 (3)Br2—C3B—C4B—C5B66.4 (3)
C3A—C4A—C5A—C6A55.5 (3)C3B—C4B—C5B—C6B54.7 (3)
C3A—C4A—C5A—C13A176.0 (2)C3B—C4B—C5B—C13B176.7 (3)
N1A—C1A—C6A—C5A143.9 (3)N1B—C1B—C6B—C5B142.9 (3)
C2A—C1A—C6A—C5A46.1 (4)C2B—C1B—C6B—C5B46.4 (4)
C4A—C5A—C6A—C1A50.0 (3)C4B—C5B—C6B—C1B49.2 (4)
C13A—C5A—C6A—C1A179.0 (2)C13B—C5B—C6B—C1B178.4 (3)
O2A—C2A—C7A—C12A33.1 (3)O2B—C2B—C7B—C12B32.1 (4)
C1A—C2A—C7A—C12A154.2 (3)C1B—C2B—C7B—C12B153.9 (3)
C3A—C2A—C7A—C12A77.3 (3)C3B—C2B—C7B—C12B78.0 (3)
O2A—C2A—C7A—C8A151.6 (3)O2B—C2B—C7B—C8B153.2 (3)
C1A—C2A—C7A—C8A30.5 (4)C1B—C2B—C7B—C8B31.5 (4)
C3A—C2A—C7A—C8A98.0 (3)C3B—C2B—C7B—C8B96.6 (3)
C12A—C7A—C8A—C9A1.4 (5)C12B—C7B—C8B—C9B2.0 (5)
C2A—C7A—C8A—C9A176.8 (3)C2B—C7B—C8B—C9B176.6 (3)
C7A—C8A—C9A—C10A0.9 (5)C7B—C8B—C9B—C10B0.3 (5)
C8A—C9A—C10A—C11A0.1 (6)C8B—C9B—C10B—C11B1.3 (6)
C9A—C10A—C11A—C12A0.4 (6)C9B—C10B—C11B—C12B1.3 (6)
C10A—C11A—C12A—C7A0.2 (5)C8B—C7B—C12B—C11B2.1 (5)
C8A—C7A—C12A—C11A1.1 (5)C2B—C7B—C12B—C11B177.0 (3)
C2A—C7A—C12A—C11A176.7 (3)C10B—C11B—C12B—C7B0.4 (5)
C4A—C5A—C13A—C16A57.6 (4)C4B—C5B—C13B—C16B57.4 (4)
C6A—C5A—C13A—C16A69.1 (4)C6B—C5B—C13B—C16B69.3 (4)
C4A—C5A—C13A—C14A179.3 (3)C4B—C5B—C13B—C15B179.3 (3)
C6A—C5A—C13A—C14A52.6 (3)C6B—C5B—C13B—C15B52.6 (4)
C4A—C5A—C13A—C15A63.1 (3)C4B—C5B—C13B—C14B63.1 (4)
C6A—C5A—C13A—C15A170.2 (3)C6B—C5B—C13B—C14B170.2 (3)
O2A—C17A—C18A—O3A65.5 (4)O2B—C17B—C18B—O3B64.7 (4)
C6A—C1A—N1A—O1A2.4 (4)C6B—C1B—N1B—O1B2.7 (4)
C2A—C1A—N1A—O1A172.3 (2)C2B—C1B—N1B—O1B173.3 (2)
C18A—C17A—O2A—C2A179.7 (2)C18B—C17B—O2B—C2B170.1 (2)
C1A—C2A—O2A—C17A61.4 (3)C7B—C2B—O2B—C17B65.7 (3)
C7A—C2A—O2A—C17A67.2 (3)C1B—C2B—O2B—C17B64.0 (3)
C3A—C2A—O2A—C17A176.2 (2)C3B—C2B—O2B—C17B178.0 (2)
C17A—C18A—O3A—C19A172.3 (3)C17B—C18B—O3B—C19B176.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···O3B0.822.092.878 (3)160
O1A—H1A···O2B0.822.372.886 (3)122
O1B—H1B···O3Ai0.821.992.783 (3)162
O1B—H1B···O2Ai0.822.452.942 (3)120
Symmetry code: (i) x, y, z1.
 

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