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There are two independent mol­ecules in the asymmetric unit of the title N-substituted oxindole, C22H26N2O2, which was obtained unexpectedly. The heterocyclic rings in both mol­ecules adopt N-envelope conformations and the isoindole ring systems are essentially planar.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807002085/lh2289sup1.cif
Contains datablocks global, 4b

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807002085/lh22894bsup2.hkl
Contains datablock 4b

CCDC reference: 636745

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.054
  • wR factor = 0.145
  • Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found



Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.143 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.14 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.24 Ratio PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.98 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.05 Ratio PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.20 PLAT413_ALERT_2_C Short Inter XH3 .. XHn H4C .. H4C .. 2.14 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

5-methyl-1-(3,3,5-trimethyl-2-p-tolyl-1,2-oxazolidin-5-yl)-1H-indol-3(2H)-one top
Crystal data top
C22H26N2O2F(000) = 1504
Mr = 350.45Dx = 1.206 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 32322 reflections
a = 19.390 (3) Åθ = 2.8–27.4°
b = 14.037 (3) ŵ = 0.08 mm1
c = 14.266 (5) ÅT = 173 K
β = 96.057 (8)°Block, colorless
V = 3861.2 (17) Å30.24 × 0.22 × 0.18 mm
Z = 8
Data collection top
Nonius KappaCCD
diffractometer
8752 independent reflections
Radiation source: fine-focus sealed tube3897 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.143
ω and φ scansθmax = 27.4°, θmin = 2.8°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
h = 2525
Tmin = 0.982, Tmax = 0.986k = 1818
32322 measured reflectionsl = 1718
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.06P)2]
where P = (Fo2 + 2Fc2)/3
8752 reflections(Δ/σ)max = 0.001
479 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.32 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.44225 (7)0.62775 (11)0.83886 (9)0.0444 (4)
O20.25011 (7)0.50396 (11)0.88091 (9)0.0445 (4)
N10.43897 (9)0.61052 (12)0.73666 (11)0.0372 (5)
N20.32321 (8)0.63167 (13)0.86456 (10)0.0345 (4)
C10.38682 (11)0.57223 (16)0.86811 (14)0.0411 (6)
C20.37772 (12)0.49014 (16)0.79706 (14)0.0444 (6)
H2A0.38210.42790.82970.053*
H2B0.33180.49350.75970.053*
C30.43595 (12)0.50368 (15)0.73392 (14)0.0422 (6)
C40.40759 (12)0.5441 (2)0.96945 (14)0.0620 (8)
H4A0.36820.51380.99530.074*
H4B0.42160.60091.00650.074*
H4C0.44650.49920.97230.074*
C50.41468 (13)0.47047 (17)0.63323 (14)0.0555 (7)
H5A0.40550.40180.63310.067*
H5B0.45220.48390.59420.067*
H5C0.37260.50440.60770.067*
C60.50321 (12)0.45589 (18)0.77373 (16)0.0562 (7)
H6A0.49600.38690.77730.067*
H6B0.51750.48090.83700.067*
H6C0.53950.46910.73260.067*
C70.49840 (12)0.65435 (16)0.70256 (15)0.0431 (6)
C80.49241 (14)0.67518 (17)0.60675 (16)0.0556 (7)
H8A0.44990.66320.56910.067*
C90.54760 (17)0.71301 (19)0.5661 (2)0.0695 (8)
H9A0.54270.72560.50030.083*
C100.60921 (17)0.73297 (19)0.6179 (2)0.0698 (9)
C110.61402 (14)0.71581 (18)0.7149 (2)0.0672 (8)
H11A0.65570.73170.75280.081*
C120.55934 (12)0.67598 (17)0.75749 (18)0.0534 (7)
H12A0.56390.66390.82340.064*
C130.25987 (11)0.58980 (17)0.87571 (12)0.0342 (5)
C140.20735 (10)0.66829 (14)0.88163 (13)0.0336 (5)
H14A0.17060.66510.82790.040*
H14B0.18560.66430.94120.040*
C150.24879 (11)0.75707 (15)0.87804 (12)0.0314 (5)
C160.22894 (12)0.85102 (16)0.88018 (12)0.0383 (6)
H16A0.18140.86660.88180.046*
C170.27795 (13)0.92347 (16)0.87994 (14)0.0444 (6)
C180.34625 (13)0.89743 (17)0.87672 (14)0.0491 (6)
H18A0.38030.94630.87830.059*
C190.36791 (12)0.80311 (17)0.87121 (14)0.0455 (6)
H19A0.41520.78770.86720.055*
C200.31786 (11)0.73262 (16)0.87172 (12)0.0345 (5)
C210.67054 (17)0.7724 (2)0.5720 (2)0.1019 (12)
H21A0.70630.79420.62100.122*
H21B0.65510.82600.53110.122*
H21C0.68970.72240.53440.122*
C220.25677 (14)1.02618 (17)0.88451 (16)0.0624 (7)
H22A0.29041.06610.85600.075*
H22B0.25541.04480.95050.075*
H22C0.21071.03460.85010.075*
O1'0.04778 (7)0.66518 (9)0.66785 (8)0.0344 (4)
O2'0.23338 (7)0.52758 (11)0.61424 (9)0.0418 (4)
N1'0.04802 (8)0.63046 (12)0.76539 (10)0.0321 (4)
N2'0.16636 (8)0.65966 (11)0.63872 (10)0.0286 (4)
C1'0.09873 (10)0.60879 (15)0.62836 (13)0.0321 (5)
C2'0.10210 (11)0.51568 (15)0.68555 (13)0.0371 (5)
H2C0.09390.45990.64340.045*
H2D0.14790.50860.72270.045*
C3'0.04472 (11)0.52487 (15)0.75030 (13)0.0347 (5)
C4'0.07507 (11)0.59882 (16)0.52427 (12)0.0430 (6)
H4D0.10740.55760.49480.052*
H4E0.07390.66180.49440.052*
H4F0.02860.57060.51610.052*
C6'0.02510 (11)0.49005 (16)0.70353 (14)0.0438 (6)
H6D0.02210.42200.68930.053*
H6E0.03730.52550.64500.053*
H6F0.06080.50030.74630.053*
C5'0.06274 (12)0.47386 (16)0.84412 (13)0.0453 (6)
H5D0.06710.40540.83290.054*
H5E0.02590.48490.88490.054*
H5F0.10670.49860.87480.054*
C7'0.00959 (11)0.67316 (14)0.80430 (14)0.0344 (5)
C8'0.00602 (13)0.67675 (16)0.90212 (14)0.0473 (6)
H8B0.03380.65280.93920.057*
C9'0.05983 (15)0.71484 (19)0.94553 (18)0.0600 (7)
H9B0.05750.71391.01240.072*
C10'0.11647 (15)0.75392 (17)0.89506 (19)0.0568 (7)
C11'0.11992 (13)0.75240 (17)0.79699 (18)0.0556 (7)
H11B0.15890.77940.76060.067*
C12'0.06666 (12)0.71158 (16)0.75165 (16)0.0442 (6)
H12B0.06970.71030.68480.053*
C13'0.22753 (11)0.61367 (16)0.62476 (13)0.0323 (5)
C14'0.28425 (10)0.68730 (14)0.62381 (13)0.0320 (5)
H14C0.31920.68010.67920.038*
H14D0.30770.68250.56560.038*
C15'0.24614 (10)0.77932 (14)0.62739 (12)0.0288 (5)
C16'0.26977 (11)0.87179 (15)0.62464 (12)0.0344 (5)
H16B0.31790.88400.62420.041*
C17'0.22291 (12)0.94767 (15)0.62250 (13)0.0364 (5)
C18'0.15322 (11)0.92652 (15)0.62377 (13)0.0388 (6)
H18B0.12090.97760.62020.047*
C19'0.12823 (11)0.83401 (14)0.63003 (13)0.0344 (5)
H19B0.08030.82190.63280.041*
C20'0.17579 (10)0.76044 (14)0.63208 (12)0.0274 (5)
C21'0.17547 (15)0.79733 (19)0.9430 (2)0.0816 (10)
H21D0.19230.75070.98640.098*
H21E0.21340.81510.89520.098*
H21F0.15880.85420.97830.098*
C22'0.24768 (13)1.04884 (16)0.61666 (16)0.0532 (7)
H22D0.21741.09100.64870.064*
H22E0.24651.06770.55040.064*
H22F0.29531.05380.64710.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0320 (9)0.0660 (11)0.0367 (8)0.0038 (8)0.0113 (7)0.0083 (7)
O20.0445 (10)0.0419 (11)0.0495 (9)0.0037 (8)0.0161 (7)0.0014 (7)
N10.0376 (11)0.0456 (12)0.0304 (10)0.0056 (9)0.0131 (8)0.0012 (8)
N20.0284 (11)0.0441 (12)0.0317 (9)0.0065 (9)0.0070 (7)0.0044 (8)
C10.0302 (13)0.0587 (16)0.0362 (12)0.0085 (12)0.0123 (10)0.0051 (11)
C20.0454 (14)0.0440 (15)0.0467 (13)0.0115 (12)0.0194 (11)0.0066 (11)
C30.0471 (15)0.0375 (15)0.0453 (13)0.0122 (12)0.0198 (11)0.0053 (10)
C40.0400 (15)0.107 (2)0.0399 (14)0.0226 (15)0.0079 (11)0.0138 (13)
C50.0683 (18)0.0484 (16)0.0542 (15)0.0046 (14)0.0265 (13)0.0087 (12)
C60.0520 (17)0.0579 (17)0.0636 (15)0.0226 (14)0.0293 (13)0.0147 (13)
C70.0408 (15)0.0391 (15)0.0524 (14)0.0093 (12)0.0192 (11)0.0005 (11)
C80.0647 (19)0.0528 (17)0.0538 (16)0.0045 (14)0.0263 (13)0.0059 (12)
C90.088 (2)0.0553 (19)0.0736 (19)0.0042 (17)0.0474 (18)0.0051 (14)
C100.074 (2)0.0400 (17)0.107 (2)0.0085 (16)0.061 (2)0.0056 (16)
C110.0434 (17)0.0509 (18)0.112 (2)0.0011 (14)0.0284 (16)0.0053 (16)
C120.0376 (15)0.0550 (17)0.0702 (17)0.0065 (13)0.0181 (13)0.0002 (13)
C130.0325 (13)0.0464 (16)0.0243 (11)0.0022 (11)0.0064 (9)0.0020 (10)
C140.0296 (12)0.0467 (15)0.0250 (11)0.0043 (11)0.0053 (9)0.0041 (9)
C150.0325 (13)0.0419 (15)0.0208 (10)0.0031 (11)0.0072 (9)0.0006 (9)
C160.0433 (14)0.0470 (16)0.0262 (11)0.0062 (12)0.0111 (10)0.0002 (10)
C170.0588 (17)0.0435 (16)0.0345 (12)0.0009 (13)0.0219 (11)0.0013 (10)
C180.0589 (18)0.0493 (17)0.0431 (14)0.0138 (14)0.0245 (12)0.0076 (11)
C190.0396 (15)0.0590 (18)0.0403 (13)0.0041 (13)0.0151 (11)0.0077 (11)
C200.0338 (13)0.0459 (15)0.0250 (11)0.0012 (11)0.0082 (9)0.0043 (9)
C210.097 (3)0.053 (2)0.172 (3)0.0007 (18)0.095 (2)0.001 (2)
C220.086 (2)0.0483 (17)0.0597 (15)0.0018 (15)0.0368 (14)0.0022 (13)
O1'0.0359 (9)0.0395 (9)0.0294 (7)0.0017 (7)0.0115 (6)0.0044 (6)
O2'0.0466 (10)0.0330 (10)0.0487 (9)0.0004 (8)0.0185 (7)0.0012 (7)
N1'0.0371 (11)0.0343 (11)0.0263 (9)0.0045 (8)0.0104 (7)0.0002 (7)
N2'0.0303 (10)0.0285 (11)0.0282 (9)0.0048 (8)0.0081 (7)0.0014 (7)
C1'0.0310 (12)0.0358 (13)0.0312 (11)0.0040 (10)0.0108 (9)0.0034 (9)
C2'0.0437 (14)0.0336 (13)0.0363 (11)0.0068 (11)0.0151 (10)0.0025 (9)
C3'0.0409 (13)0.0318 (13)0.0327 (11)0.0073 (10)0.0102 (9)0.0011 (9)
C4'0.0456 (15)0.0536 (16)0.0306 (12)0.0133 (12)0.0079 (10)0.0065 (10)
C6'0.0485 (15)0.0450 (15)0.0405 (12)0.0152 (12)0.0164 (10)0.0064 (10)
C5'0.0578 (16)0.0404 (14)0.0403 (12)0.0048 (12)0.0176 (11)0.0046 (10)
C7'0.0368 (13)0.0316 (13)0.0365 (12)0.0062 (11)0.0115 (10)0.0032 (9)
C8'0.0579 (16)0.0487 (16)0.0378 (13)0.0066 (13)0.0166 (11)0.0090 (11)
C9'0.081 (2)0.0552 (18)0.0496 (15)0.0041 (16)0.0328 (15)0.0090 (12)
C10'0.070 (2)0.0343 (15)0.0750 (19)0.0071 (14)0.0476 (16)0.0053 (13)
C11'0.0451 (16)0.0458 (17)0.0789 (19)0.0032 (13)0.0208 (13)0.0073 (13)
C12'0.0441 (15)0.0431 (15)0.0481 (14)0.0015 (12)0.0177 (12)0.0035 (11)
C13'0.0379 (14)0.0345 (14)0.0259 (11)0.0007 (11)0.0101 (9)0.0011 (9)
C14'0.0306 (12)0.0413 (14)0.0250 (11)0.0013 (10)0.0064 (9)0.0025 (9)
C15'0.0317 (13)0.0346 (14)0.0204 (10)0.0028 (10)0.0045 (8)0.0005 (8)
C16'0.0370 (13)0.0397 (15)0.0277 (11)0.0087 (11)0.0094 (9)0.0025 (9)
C17'0.0479 (15)0.0302 (13)0.0334 (12)0.0044 (12)0.0155 (10)0.0030 (9)
C18'0.0428 (15)0.0338 (14)0.0421 (13)0.0034 (11)0.0155 (10)0.0002 (10)
C19'0.0337 (13)0.0361 (14)0.0352 (12)0.0017 (11)0.0117 (9)0.0003 (9)
C20'0.0319 (13)0.0308 (13)0.0202 (10)0.0026 (10)0.0055 (8)0.0005 (8)
C21'0.091 (2)0.0499 (18)0.117 (2)0.0037 (17)0.071 (2)0.0021 (16)
C22'0.0627 (17)0.0409 (15)0.0608 (15)0.0079 (13)0.0282 (13)0.0058 (12)
Geometric parameters (Å, º) top
O1—C11.425 (2)O1'—C1'1.427 (2)
O1—N11.473 (2)O1'—N1'1.474 (2)
O2—C131.223 (2)O2'—C13'1.224 (2)
N1—C71.436 (3)N1'—C7'1.430 (2)
N1—C31.501 (3)N1'—C3'1.498 (3)
N2—C131.386 (3)N2'—C13'1.383 (2)
N2—C201.425 (3)N2'—C20'1.431 (2)
N2—C11.486 (3)N2'—C1'1.487 (2)
C1—C41.512 (3)C1'—C4'1.514 (3)
C1—C21.532 (3)C1'—C2'1.539 (3)
C2—C31.529 (3)C2'—C3'1.525 (3)
C2—H2A0.9900C2'—H2C0.9900
C2—H2B0.9900C2'—H2D0.9900
C3—C61.522 (3)C3'—C6'1.525 (3)
C3—C51.525 (3)C3'—C5'1.526 (3)
C4—H4A0.9800C4'—H4D0.9800
C4—H4B0.9800C4'—H4E0.9800
C4—H4C0.9800C4'—H4F0.9800
C5—H5A0.9800C6'—H6D0.9800
C5—H5B0.9800C6'—H6E0.9800
C5—H5C0.9800C6'—H6F0.9800
C6—H6A0.9800C5'—H5D0.9800
C6—H6B0.9800C5'—H5E0.9800
C6—H6C0.9800C5'—H5F0.9800
C7—C121.381 (3)C7'—C12'1.380 (3)
C7—C81.391 (3)C7'—C8'1.391 (3)
C8—C91.376 (3)C8'—C9'1.376 (3)
C8—H8A0.9500C8'—H8B0.9500
C9—C101.366 (4)C9'—C10'1.363 (4)
C9—H9A0.9500C9'—H9B0.9500
C10—C111.397 (4)C10'—C11'1.394 (3)
C10—C211.521 (3)C10'—C21'1.521 (3)
C11—C121.394 (3)C11'—C12'1.398 (3)
C11—H11A0.9500C11'—H11B0.9500
C12—H12A0.9500C12'—H12B0.9500
C13—C141.509 (3)C13'—C14'1.510 (3)
C14—C151.487 (3)C14'—C15'1.492 (3)
C14—H14A0.9900C14'—H14C0.9900
C14—H14B0.9900C14'—H14D0.9900
C15—C161.375 (3)C15'—C16'1.378 (3)
C15—C201.395 (3)C15'—C20'1.398 (3)
C16—C171.392 (3)C16'—C17'1.398 (3)
C16—H16A0.9500C16'—H16B0.9500
C17—C181.379 (3)C17'—C18'1.385 (3)
C17—C221.502 (3)C17'—C22'1.504 (3)
C18—C191.394 (3)C18'—C19'1.392 (3)
C18—H18A0.9500C18'—H18B0.9500
C19—C201.386 (3)C19'—C20'1.383 (3)
C19—H19A0.9500C19'—H19B0.9500
C21—H21A0.9800C21'—H21D0.9800
C21—H21B0.9800C21'—H21E0.9800
C21—H21C0.9800C21'—H21F0.9800
C22—H22A0.9800C22'—H22D0.9800
C22—H22B0.9800C22'—H22E0.9800
C22—H22C0.9800C22'—H22F0.9800
C1—O1—N1104.18 (14)C1'—O1'—N1'104.82 (13)
C7—N1—O1108.22 (15)C7'—N1'—O1'107.64 (14)
C7—N1—C3116.73 (16)C7'—N1'—C3'116.56 (16)
O1—N1—C3100.80 (14)O1'—N1'—C3'101.29 (12)
C13—N2—C20109.96 (17)C13'—N2'—C20'109.53 (16)
C13—N2—C1120.04 (18)C13'—N2'—C1'121.49 (17)
C20—N2—C1128.49 (18)C20'—N2'—C1'125.86 (16)
O1—C1—N2109.38 (17)O1'—C1'—N2'109.53 (15)
O1—C1—C4106.86 (17)O1'—C1'—C4'106.72 (16)
N2—C1—C4108.42 (16)N2'—C1'—C4'108.35 (15)
O1—C1—C2104.79 (16)O1'—C1'—C2'104.73 (15)
N2—C1—C2111.26 (17)N2'—C1'—C2'111.57 (16)
C4—C1—C2115.9 (2)C4'—C1'—C2'115.67 (17)
C3—C2—C1104.81 (18)C3'—C2'—C1'104.86 (16)
C3—C2—H2A110.8C3'—C2'—H2C110.8
C1—C2—H2A110.8C1'—C2'—H2C110.8
C3—C2—H2B110.8C3'—C2'—H2D110.8
C1—C2—H2B110.8C1'—C2'—H2D110.8
H2A—C2—H2B108.9H2C—C2'—H2D108.8
N1—C3—C6113.64 (19)N1'—C3'—C2'98.51 (15)
N1—C3—C5109.62 (17)N1'—C3'—C6'113.73 (18)
C6—C3—C5110.65 (18)C2'—C3'—C6'112.25 (17)
N1—C3—C297.93 (16)N1'—C3'—C5'109.63 (16)
C6—C3—C2112.48 (18)C2'—C3'—C5'112.18 (18)
C5—C3—C2111.95 (19)C6'—C3'—C5'110.12 (17)
C1—C4—H4A109.5C1'—C4'—H4D109.5
C1—C4—H4B109.5C1'—C4'—H4E109.5
H4A—C4—H4B109.5H4D—C4'—H4E109.5
C1—C4—H4C109.5C1'—C4'—H4F109.5
H4A—C4—H4C109.5H4D—C4'—H4F109.5
H4B—C4—H4C109.5H4E—C4'—H4F109.5
C3—C5—H5A109.5C3'—C6'—H6D109.5
C3—C5—H5B109.5C3'—C6'—H6E109.5
H5A—C5—H5B109.5H6D—C6'—H6E109.5
C3—C5—H5C109.5C3'—C6'—H6F109.5
H5A—C5—H5C109.5H6D—C6'—H6F109.5
H5B—C5—H5C109.5H6E—C6'—H6F109.5
C3—C6—H6A109.5C3'—C5'—H5D109.5
C3—C6—H6B109.5C3'—C5'—H5E109.5
H6A—C6—H6B109.5H5D—C5'—H5E109.5
C3—C6—H6C109.5C3'—C5'—H5F109.5
H6A—C6—H6C109.5H5D—C5'—H5F109.5
H6B—C6—H6C109.5H5E—C5'—H5F109.5
C12—C7—C8119.3 (2)C12'—C7'—C8'119.0 (2)
C12—C7—N1124.8 (2)C12'—C7'—N1'124.52 (18)
C8—C7—N1115.9 (2)C8'—C7'—N1'116.51 (19)
C9—C8—C7120.5 (3)C9'—C8'—C7'120.4 (2)
C9—C8—H8A119.8C9'—C8'—H8B119.8
C7—C8—H8A119.8C7'—C8'—H8B119.8
C10—C9—C8121.7 (3)C10'—C9'—C8'121.7 (2)
C10—C9—H9A119.1C10'—C9'—H9B119.2
C8—C9—H9A119.1C8'—C9'—H9B119.2
C9—C10—C11117.6 (3)C9'—C10'—C11'118.3 (2)
C9—C10—C21121.4 (3)C9'—C10'—C21'121.7 (3)
C11—C10—C21121.0 (3)C11'—C10'—C21'119.9 (3)
C12—C11—C10121.8 (3)C10'—C11'—C12'120.7 (2)
C12—C11—H11A119.1C10'—C11'—H11B119.6
C10—C11—H11A119.1C12'—C11'—H11B119.6
C7—C12—C11119.0 (2)C7'—C12'—C11'119.8 (2)
C7—C12—H12A120.5C7'—C12'—H12B120.1
C11—C12—H12A120.5C11'—C12'—H12B120.1
O2—C13—N2124.7 (2)O2'—C13'—N2'124.77 (19)
O2—C13—C14127.3 (2)O2'—C13'—C14'126.7 (2)
N2—C13—C14107.96 (19)N2'—C13'—C14'108.56 (18)
C15—C14—C13103.87 (17)C15'—C14'—C13'103.20 (17)
C15—C14—H14A111.0C15'—C14'—H14C111.1
C13—C14—H14A111.0C13'—C14'—H14C111.1
C15—C14—H14B111.0C15'—C14'—H14D111.1
C13—C14—H14B111.0C13'—C14'—H14D111.1
H14A—C14—H14B109.0H14C—C14'—H14D109.1
C16—C15—C20120.7 (2)C16'—C15'—C20'120.59 (19)
C16—C15—C14130.51 (19)C16'—C15'—C14'130.32 (19)
C20—C15—C14108.79 (18)C20'—C15'—C14'109.07 (17)
C15—C16—C17120.5 (2)C15'—C16'—C17'120.0 (2)
C15—C16—H16A119.7C15'—C16'—H16B120.0
C17—C16—H16A119.7C17'—C16'—H16B120.0
C18—C17—C16117.7 (2)C18'—C17'—C16'117.96 (19)
C18—C17—C22121.6 (2)C18'—C17'—C22'121.4 (2)
C16—C17—C22120.7 (2)C16'—C17'—C22'120.7 (2)
C17—C18—C19123.4 (2)C17'—C18'—C19'123.2 (2)
C17—C18—H18A118.3C17'—C18'—H18B118.4
C19—C18—H18A118.3C19'—C18'—H18B118.4
C20—C19—C18117.5 (2)C20'—C19'—C18'117.5 (2)
C20—C19—H19A121.2C20'—C19'—H19B121.2
C18—C19—H19A121.2C18'—C19'—H19B121.2
C19—C20—C15120.1 (2)C19'—C20'—C15'120.61 (19)
C19—C20—N2130.8 (2)C19'—C20'—N2'130.55 (19)
C15—C20—N2109.08 (18)C15'—C20'—N2'108.84 (17)
C10—C21—H21A109.5C10'—C21'—H21D109.5
C10—C21—H21B109.5C10'—C21'—H21E109.5
H21A—C21—H21B109.5H21D—C21'—H21E109.5
C10—C21—H21C109.5C10'—C21'—H21F109.5
H21A—C21—H21C109.5H21D—C21'—H21F109.5
H21B—C21—H21C109.5H21E—C21'—H21F109.5
C17—C22—H22A109.5C17'—C22'—H22D109.5
C17—C22—H22B109.5C17'—C22'—H22E109.5
H22A—C22—H22B109.5H22D—C22'—H22E109.5
C17—C22—H22C109.5C17'—C22'—H22F109.5
H22A—C22—H22C109.5H22D—C22'—H22F109.5
H22B—C22—H22C109.5H22E—C22'—H22F109.5
C1—O1—N1—C7172.94 (16)C1'—O1'—N1'—C7'170.79 (15)
C1—O1—N1—C349.92 (18)C1'—O1'—N1'—C3'47.98 (17)
N1—O1—C1—N291.77 (17)N1'—O1'—C1'—N2'94.07 (16)
N1—O1—C1—C4151.06 (16)N1'—O1'—C1'—C4'148.85 (15)
N1—O1—C1—C227.59 (19)N1'—O1'—C1'—C2'25.71 (18)
C13—N2—C1—O1170.00 (15)C13'—N2'—C1'—O1'166.29 (15)
C20—N2—C1—O125.5 (2)C20'—N2'—C1'—O1'35.8 (2)
C13—N2—C1—C473.8 (2)C13'—N2'—C1'—C4'77.7 (2)
C20—N2—C1—C490.7 (2)C20'—N2'—C1'—C4'80.2 (2)
C13—N2—C1—C254.7 (2)C13'—N2'—C1'—C2'50.8 (2)
C20—N2—C1—C2140.79 (18)C20'—N2'—C1'—C2'151.31 (16)
O1—C1—C2—C34.1 (2)O1'—C1'—C2'—C3'5.2 (2)
N2—C1—C2—C3122.16 (18)N2'—C1'—C2'—C3'123.58 (17)
C4—C1—C2—C3113.4 (2)C4'—C1'—C2'—C3'111.98 (19)
C7—N1—C3—C647.6 (2)C7'—N1'—C3'—C2'164.90 (16)
O1—N1—C3—C669.31 (19)O1'—N1'—C3'—C2'48.46 (16)
C7—N1—C3—C576.8 (2)C7'—N1'—C3'—C6'46.0 (2)
O1—N1—C3—C5166.30 (16)O1'—N1'—C3'—C6'70.48 (18)
C7—N1—C3—C2166.44 (17)C7'—N1'—C3'—C5'77.8 (2)
O1—N1—C3—C249.53 (18)O1'—N1'—C3'—C5'165.76 (15)
C1—C2—C3—N132.8 (2)C1'—C2'—C3'—N1'32.80 (19)
C1—C2—C3—C687.0 (2)C1'—C2'—C3'—C6'87.2 (2)
C1—C2—C3—C5147.72 (18)C1'—C2'—C3'—C5'148.13 (17)
O1—N1—C7—C1222.3 (3)O1'—N1'—C7'—C12'20.1 (3)
C3—N1—C7—C1290.5 (3)C3'—N1'—C7'—C12'92.8 (2)
O1—N1—C7—C8158.02 (18)O1'—N1'—C7'—C8'158.76 (17)
C3—N1—C7—C889.2 (2)C3'—N1'—C7'—C8'88.4 (2)
C12—C7—C8—C92.9 (4)C12'—C7'—C8'—C9'2.4 (3)
N1—C7—C8—C9176.8 (2)N1'—C7'—C8'—C9'178.6 (2)
C7—C8—C9—C101.2 (4)C7'—C8'—C9'—C10'3.0 (4)
C8—C9—C10—C111.5 (4)C8'—C9'—C10'—C11'1.7 (4)
C8—C9—C10—C21178.4 (2)C8'—C9'—C10'—C21'179.1 (2)
C9—C10—C11—C122.7 (4)C9'—C10'—C11'—C12'0.1 (4)
C21—C10—C11—C12177.3 (2)C21'—C10'—C11'—C12'179.1 (2)
C8—C7—C12—C111.7 (3)C8'—C7'—C12'—C11'0.6 (3)
N1—C7—C12—C11178.0 (2)N1'—C7'—C12'—C11'179.4 (2)
C10—C11—C12—C71.1 (4)C10'—C11'—C12'—C7'0.7 (4)
C20—N2—C13—O2173.54 (18)C20'—N2'—C13'—O2'170.16 (17)
C1—N2—C13—O26.4 (3)C1'—N2'—C13'—O2'9.0 (3)
C20—N2—C13—C145.5 (2)C20'—N2'—C13'—C14'9.24 (19)
C1—N2—C13—C14172.68 (15)C1'—N2'—C13'—C14'170.36 (15)
O2—C13—C14—C15176.01 (18)O2'—C13'—C14'—C15'173.00 (18)
N2—C13—C14—C153.04 (19)N2'—C13'—C14'—C15'6.39 (19)
C13—C14—C15—C16179.57 (18)C13'—C14'—C15'—C16'177.19 (18)
C13—C14—C15—C200.56 (19)C13'—C14'—C15'—C20'1.22 (19)
C20—C15—C16—C172.6 (3)C20'—C15'—C16'—C17'2.7 (3)
C14—C15—C16—C17177.24 (18)C14'—C15'—C16'—C17'175.56 (17)
C15—C16—C17—C180.5 (3)C15'—C16'—C17'—C18'0.3 (3)
C15—C16—C17—C22178.60 (18)C15'—C16'—C17'—C22'178.22 (17)
C16—C17—C18—C191.8 (3)C16'—C17'—C18'—C19'2.1 (3)
C22—C17—C18—C19179.1 (2)C22'—C17'—C18'—C19'179.36 (18)
C17—C18—C19—C201.9 (3)C17'—C18'—C19'—C20'2.0 (3)
C18—C19—C20—C150.3 (3)C18'—C19'—C20'—C15'0.4 (3)
C18—C19—C20—N2178.12 (18)C18'—C19'—C20'—N2'179.55 (17)
C16—C15—C20—C192.5 (3)C16'—C15'—C20'—C19'2.7 (3)
C14—C15—C20—C19177.39 (17)C14'—C15'—C20'—C19'175.86 (16)
C16—C15—C20—N2176.23 (15)C16'—C15'—C20'—N2'177.21 (15)
C14—C15—C20—N23.9 (2)C14'—C15'—C20'—N2'4.19 (19)
C13—N2—C20—C19175.44 (19)C13'—N2'—C20'—C19'171.53 (18)
C1—N2—C20—C199.7 (3)C1'—N2'—C20'—C19'11.4 (3)
C13—N2—C20—C156.0 (2)C13'—N2'—C20'—C15'8.52 (19)
C1—N2—C20—C15171.75 (17)C1'—N2'—C20'—C15'168.62 (15)
 

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