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The title compound, C26H26N2O3, crystallizes as a racemic mixture of R,R and S,S enantiomers. The two independent mol­ecules show a similar conformation. They are connected via C—H...O and C—H...π inter­actions to form ribbons along the a axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805019239/ob6537sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805019239/ob6537Isup2.hkl
Contains datablock I

CCDC reference: 277741

Key indicators

  • Single-crystal X-ray study
  • T = 290 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.055
  • wR factor = 0.129
  • Data-to-parameter ratio = 7.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C113 PLAT331_ALERT_2_B Small Average Phenyl C-C Dist. C113 -C118 1.36 Ang.
Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.76 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.97 Ratio PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.74 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.02 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C117 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C118 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C126 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C225 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C119 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C213 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10 PLAT411_ALERT_2_C Short Inter H...H Contact H17 .. H27 .. 2.11 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H121 .. CG2 .. 2.89 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H221 .. CG1 .. 2.92 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.97 From the CIF: _reflns_number_total 4339 Count of symmetry unique reflns 4336 Completeness (_total/calc) 100.07% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3 Fraction of Friedel pairs measured 0.001 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 14 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 11 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

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: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) Mercury (Version 1.3; Bruno et al., 2002); software used to prepare material for publication: WinGX (Farrugia, 1999).

(3RS,4RS)-3-(2-Furyl)-2-phenetyl-4-(pyrrolidin-1-ylcarbonyl)-3,4- dihydroisoquinolin-1(2H)-one top
Crystal data top
C26H26N2O3Dx = 1.268 Mg m3
Mr = 414.49Melting point: 413 K
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 22 reflections
a = 11.9675 (15) Åθ = 16.1–17.3°
b = 11.066 (2) ŵ = 0.08 mm1
c = 32.7891 (14) ÅT = 290 K
V = 4342.3 (10) Å3Prism, yellow
Z = 80.26 × 0.2 × 0.2 mm
F(000) = 1760
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.076
Radiation source: fine-focus sealed tubeθmax = 26.0°, θmin = 1.2°
Graphite monochromatorh = 014
non–profiled ω/2θ scansk = 013
8655 measured reflectionsl = 4040
4339 independent reflections3 standard reflections every 120 min
2189 reflections with I > 2σ(I) intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.129 w = 1/[σ2(Fo2) + (0.0463P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
4339 reflectionsΔρmax = 0.16 e Å3
559 parametersΔρmin = 0.18 e Å3
1 restraintAbsolute structure: see text
Primary atom site location: structure-invariant direct methods
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
C110.4414 (5)0.7522 (5)0.67879 (18)0.0412 (15)
C130.2644 (5)0.6743 (5)0.70754 (19)0.0411 (15)
H130.23980.66480.73590.049*
C140.2937 (5)0.5481 (5)0.69051 (16)0.0377 (15)
H140.22480.50270.68540.045*
C150.3587 (5)0.5611 (5)0.65120 (19)0.0396 (15)
C160.4303 (5)0.6564 (5)0.64675 (17)0.0396 (15)
C170.4967 (5)0.6665 (6)0.61218 (19)0.0519 (17)
H170.54490.73180.60930.062*
C180.4911 (7)0.5798 (7)0.5822 (2)0.063 (2)
H180.53730.58470.55940.076*
C190.4168 (8)0.4858 (7)0.5860 (3)0.067 (3)
H190.41090.42910.56520.081*
C210.8062 (5)0.7539 (5)0.51181 (19)0.0410 (15)
C230.9802 (5)0.8404 (5)0.48521 (19)0.0413 (15)
H231.00720.85500.45740.050*
C240.9477 (5)0.9625 (5)0.50395 (19)0.0416 (16)
H241.01601.00810.50990.050*
C250.8842 (5)0.9448 (5)0.54278 (17)0.0349 (14)
C260.8135 (5)0.8440 (5)0.54549 (18)0.0393 (15)
C270.7482 (5)0.8294 (5)0.5800 (2)0.0525 (17)
H270.70170.76230.58200.063*
C280.7507 (6)0.9116 (6)0.6113 (2)0.0605 (19)
H280.70550.90090.63410.073*
C290.8202 (8)1.0095 (6)0.6087 (3)0.060 (2)
H290.82161.06560.62980.072*
C1100.3517 (7)0.4746 (6)0.6199 (2)0.058 (2)
H1100.30260.40980.62230.069*
C1110.3694 (6)0.8459 (5)0.73988 (18)0.0491 (18)
H11A0.29520.86920.74880.059*
H11B0.40700.91750.72970.059*
C1120.4346 (6)0.7947 (5)0.7761 (2)0.0538 (18)
H11C0.39820.72190.78580.065*
H11D0.50950.77340.76740.065*
C1130.4413 (5)0.8859 (5)0.81054 (19)0.0461 (16)
C1140.3612 (7)0.8948 (7)0.8394 (2)0.077 (2)
H1140.30150.84120.83820.092*
C1150.3624 (10)0.9782 (8)0.8705 (3)0.087 (3)
H1150.30430.98090.88940.105*
C1160.4472 (9)1.0545 (9)0.8733 (3)0.092 (3)
H1160.45051.10970.89460.111*
C1170.5299 (9)1.0518 (10)0.8445 (3)0.113 (4)
H1170.58841.10700.84570.136*
C1180.5259 (7)0.9660 (9)0.8135 (3)0.102 (4)
H1180.58310.96380.79440.122*
C1190.1685 (5)0.7281 (5)0.68311 (19)0.0413 (15)
C1200.0997 (6)0.6908 (6)0.6544 (2)0.070 (2)
H1200.09860.61410.64270.084*
C1210.0277 (6)0.7880 (6)0.6443 (2)0.069 (2)
H1210.02880.78730.62480.083*
C1220.0555 (6)0.8782 (6)0.6674 (2)0.0599 (19)
H1220.02130.95370.66710.072*
C1230.3666 (6)0.4791 (5)0.7213 (2)0.0443 (18)
C1240.2349 (7)0.3022 (5)0.7159 (2)0.064 (2)
H12A0.23390.30350.68640.077*
H12B0.16520.33550.72610.077*
C1250.2538 (7)0.1753 (5)0.7320 (3)0.084 (3)
H12C0.18330.13510.73730.101*
H12D0.29630.12750.71260.101*
C1260.3163 (9)0.1929 (6)0.7694 (3)0.096 (3)
H12E0.35900.12090.77590.115*
H12F0.26590.20980.79180.115*
C1270.3947 (7)0.3002 (6)0.7623 (2)0.073 (2)
H12G0.40630.34620.78710.088*
H12H0.46640.27420.75160.088*
C2100.8887 (7)1.0260 (5)0.5749 (2)0.0493 (19)
H2100.93751.09140.57390.059*
C2110.8766 (6)0.6757 (5)0.44841 (18)0.0485 (17)
H21A0.84170.60130.45740.058*
H21B0.95160.65620.43930.058*
C2120.8108 (6)0.7259 (6)0.4126 (2)0.064 (2)
H21C0.73590.74690.42140.077*
H21D0.84670.79860.40250.077*
C2130.8049 (6)0.6339 (6)0.37929 (19)0.0510 (17)
C2140.8875 (6)0.6227 (6)0.3504 (2)0.065 (2)
H2140.94610.67780.35040.078*
C2150.8863 (9)0.5334 (9)0.3216 (3)0.089 (3)
H2150.94330.52620.30240.106*
C2160.7974 (9)0.4545 (9)0.3221 (3)0.090 (3)
H2160.79500.39330.30270.108*
C2170.7134 (8)0.4618 (9)0.3496 (3)0.095 (3)
H2170.65490.40650.34940.114*
C2180.7173 (7)0.5536 (8)0.3778 (2)0.076 (2)
H2180.65910.56170.39640.091*
C2191.0725 (5)0.7821 (5)0.50893 (19)0.0409 (14)
C2201.1428 (6)0.8173 (6)0.5393 (2)0.063 (2)
H2201.14570.89280.55170.075*
C2211.2106 (6)0.7158 (6)0.5482 (2)0.066 (2)
H2211.26680.71230.56770.079*
C2221.1798 (6)0.6270 (6)0.5237 (2)0.062 (2)
H2221.21110.55000.52350.074*
C2230.8760 (6)1.0358 (5)0.47367 (18)0.0407 (16)
C2240.8413 (5)1.2244 (5)0.4377 (2)0.0484 (16)
H22A0.77081.24820.44990.058*
H22B0.82661.18140.41250.058*
C2250.9147 (7)1.3328 (6)0.4303 (3)0.084 (3)
H22C0.96241.31970.40680.101*
H22D0.86981.40440.42560.101*
C2260.9825 (7)1.3459 (6)0.4679 (2)0.070 (2)
H22E0.94291.39340.48810.084*
H22F1.05321.38490.46190.084*
C2271.0012 (6)1.2171 (5)0.4832 (2)0.0510 (18)
H22G1.07181.18520.47340.061*
H22H1.00031.21410.51270.061*
N110.3319 (4)0.3692 (4)0.73213 (15)0.0476 (13)
N120.3603 (4)0.7566 (4)0.70693 (14)0.0420 (12)
N210.9066 (4)1.1498 (4)0.46591 (14)0.0391 (11)
N220.8842 (4)0.7580 (4)0.48290 (14)0.0387 (12)
O110.5199 (4)0.8240 (4)0.67821 (15)0.0588 (13)
O120.1431 (4)0.8458 (4)0.69241 (14)0.0610 (13)
O130.4511 (5)0.5252 (4)0.73539 (18)0.0660 (16)
O210.7307 (4)0.6782 (4)0.51179 (14)0.0596 (13)
O221.0955 (4)0.6646 (3)0.49873 (14)0.0591 (12)
O230.7911 (5)0.9915 (4)0.45902 (18)0.0637 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.043 (4)0.031 (3)0.049 (4)0.000 (3)0.007 (3)0.009 (3)
C130.047 (4)0.034 (3)0.042 (4)0.007 (3)0.000 (3)0.003 (3)
C140.043 (4)0.032 (3)0.039 (4)0.008 (3)0.012 (3)0.008 (3)
C150.044 (4)0.029 (3)0.046 (4)0.010 (3)0.015 (3)0.006 (3)
C160.039 (4)0.043 (3)0.037 (4)0.002 (3)0.003 (3)0.001 (3)
C170.060 (4)0.046 (4)0.050 (4)0.007 (3)0.003 (4)0.008 (3)
C180.077 (6)0.068 (5)0.046 (4)0.028 (4)0.005 (4)0.003 (4)
C190.095 (8)0.054 (5)0.053 (6)0.017 (5)0.005 (5)0.016 (4)
C210.042 (4)0.029 (3)0.053 (4)0.003 (3)0.014 (3)0.001 (3)
C230.043 (4)0.041 (3)0.040 (4)0.002 (3)0.000 (3)0.000 (3)
C240.042 (4)0.028 (3)0.054 (4)0.004 (3)0.005 (3)0.002 (3)
C250.041 (4)0.033 (3)0.030 (3)0.009 (3)0.004 (3)0.003 (3)
C260.037 (3)0.029 (3)0.051 (4)0.004 (3)0.003 (3)0.002 (3)
C270.046 (4)0.053 (4)0.058 (5)0.002 (3)0.003 (4)0.007 (4)
C280.065 (5)0.073 (5)0.044 (4)0.013 (4)0.006 (4)0.001 (4)
C290.076 (7)0.065 (5)0.040 (5)0.022 (4)0.011 (5)0.015 (4)
C1100.082 (6)0.036 (4)0.055 (5)0.006 (4)0.013 (5)0.003 (4)
C1110.066 (5)0.033 (3)0.048 (4)0.007 (3)0.020 (4)0.015 (3)
C1120.062 (5)0.045 (4)0.054 (4)0.016 (3)0.007 (4)0.005 (3)
C1130.048 (4)0.048 (4)0.043 (4)0.005 (3)0.008 (3)0.008 (3)
C1140.084 (6)0.065 (5)0.082 (6)0.017 (4)0.025 (5)0.018 (4)
C1150.127 (9)0.076 (6)0.059 (6)0.013 (6)0.041 (6)0.032 (5)
C1160.096 (8)0.101 (7)0.080 (7)0.021 (6)0.014 (6)0.057 (6)
C1170.071 (7)0.141 (9)0.127 (10)0.018 (7)0.004 (7)0.085 (8)
C1180.055 (5)0.134 (8)0.115 (8)0.015 (6)0.010 (6)0.080 (7)
C1190.042 (4)0.029 (3)0.053 (4)0.000 (3)0.006 (3)0.004 (3)
C1200.060 (5)0.046 (4)0.104 (6)0.007 (4)0.028 (5)0.018 (4)
C1210.068 (5)0.054 (4)0.084 (6)0.016 (4)0.032 (4)0.001 (4)
C1220.054 (4)0.052 (4)0.074 (5)0.015 (4)0.009 (4)0.005 (4)
C1230.046 (4)0.035 (3)0.052 (4)0.001 (3)0.007 (4)0.004 (3)
C1240.066 (5)0.038 (3)0.089 (6)0.007 (3)0.002 (4)0.021 (4)
C1250.086 (6)0.038 (4)0.128 (8)0.020 (4)0.014 (6)0.033 (4)
C1260.160 (9)0.051 (4)0.077 (6)0.020 (5)0.024 (6)0.030 (4)
C1270.096 (6)0.058 (4)0.065 (5)0.010 (4)0.009 (5)0.009 (4)
C2100.060 (5)0.040 (4)0.048 (5)0.001 (4)0.008 (4)0.007 (4)
C2110.064 (4)0.035 (3)0.047 (4)0.015 (3)0.006 (3)0.008 (3)
C2120.082 (6)0.060 (4)0.049 (4)0.005 (4)0.007 (4)0.015 (4)
C2130.062 (5)0.052 (4)0.039 (4)0.007 (4)0.005 (3)0.005 (3)
C2140.079 (5)0.060 (4)0.057 (5)0.010 (4)0.011 (4)0.004 (4)
C2150.102 (9)0.090 (6)0.074 (7)0.009 (6)0.026 (6)0.006 (6)
C2160.129 (9)0.093 (6)0.049 (5)0.020 (7)0.017 (6)0.023 (5)
C2170.066 (6)0.112 (7)0.106 (8)0.026 (6)0.003 (6)0.053 (7)
C2180.054 (5)0.101 (6)0.072 (6)0.002 (5)0.004 (4)0.025 (5)
C2190.035 (3)0.038 (3)0.050 (4)0.005 (3)0.005 (3)0.003 (3)
C2200.065 (5)0.047 (4)0.075 (5)0.015 (4)0.022 (4)0.011 (4)
C2210.049 (4)0.063 (5)0.087 (6)0.007 (4)0.016 (4)0.006 (4)
C2220.040 (4)0.050 (4)0.095 (6)0.008 (3)0.005 (4)0.022 (4)
C2230.052 (4)0.033 (3)0.037 (4)0.008 (3)0.002 (3)0.000 (3)
C2240.056 (4)0.038 (3)0.051 (4)0.013 (3)0.012 (3)0.009 (3)
C2250.127 (8)0.036 (4)0.089 (6)0.007 (4)0.032 (6)0.010 (4)
C2260.090 (5)0.051 (4)0.069 (5)0.018 (4)0.019 (5)0.007 (4)
C2270.058 (4)0.038 (3)0.057 (4)0.013 (3)0.016 (4)0.003 (3)
N110.060 (4)0.033 (3)0.050 (3)0.002 (3)0.009 (3)0.013 (3)
N120.049 (3)0.033 (3)0.044 (3)0.001 (2)0.004 (3)0.009 (2)
N210.043 (3)0.034 (3)0.040 (3)0.000 (2)0.004 (3)0.000 (2)
N220.041 (3)0.031 (3)0.044 (3)0.003 (2)0.011 (3)0.007 (2)
O110.051 (3)0.046 (3)0.079 (3)0.017 (2)0.003 (2)0.004 (2)
O120.065 (3)0.044 (2)0.075 (3)0.006 (2)0.012 (3)0.005 (2)
O130.069 (4)0.046 (3)0.083 (4)0.010 (3)0.031 (4)0.015 (3)
O210.053 (3)0.046 (2)0.080 (3)0.019 (2)0.014 (3)0.003 (2)
O220.052 (3)0.040 (2)0.084 (3)0.008 (2)0.010 (3)0.001 (2)
O230.065 (4)0.042 (2)0.084 (4)0.011 (2)0.038 (3)0.010 (2)
Geometric parameters (Å, º) top
C11—O111.231 (7)C121—C1221.296 (9)
C11—N121.340 (7)C121—H1210.9300
C11—C161.498 (8)C122—O121.379 (8)
C13—N121.466 (7)C122—H1220.9300
C13—C1191.521 (8)C123—O131.223 (8)
C13—C141.544 (7)C123—N111.333 (7)
C13—H130.9800C124—N111.476 (8)
C14—C151.513 (8)C124—C1251.517 (8)
C14—C1231.538 (9)C124—H12A0.9700
C14—H140.9800C124—H12B0.9700
C15—C161.367 (8)C125—C1261.450 (10)
C15—C1101.406 (9)C125—H12C0.9700
C16—C171.389 (8)C125—H12D0.9700
C17—C181.376 (9)C126—C1271.531 (10)
C17—H170.9300C126—H12E0.9700
C18—C191.373 (11)C126—H12F0.9700
C18—H180.9300C127—N111.458 (8)
C19—C1101.363 (12)C127—H12G0.9700
C19—H190.9300C127—H12H0.9700
C21—O211.232 (7)C210—H2100.9300
C21—N221.332 (7)C211—N221.455 (7)
C21—C261.490 (8)C211—C2121.519 (8)
C23—N221.469 (7)C211—H21A0.9700
C23—C2191.497 (8)C211—H21B0.9700
C23—C241.534 (8)C212—C2131.495 (8)
C23—H230.9800C212—H21C0.9700
C24—C251.496 (8)C212—H21D0.9700
C24—C2231.543 (8)C213—C2181.374 (10)
C24—H240.9800C213—C2141.375 (9)
C25—C2101.386 (9)C214—C2151.367 (10)
C25—C261.404 (7)C214—H2140.9300
C26—C271.384 (8)C215—C2161.377 (13)
C27—C281.372 (9)C215—H2150.9300
C27—H270.9300C216—C2171.351 (11)
C28—C291.368 (10)C216—H2160.9300
C28—H280.9300C217—C2181.376 (10)
C29—C2101.392 (11)C217—H2170.9300
C29—H290.9300C218—H2180.9300
C110—H1100.9300C219—C2201.361 (8)
C111—N121.468 (6)C219—O221.370 (6)
C111—C1121.530 (8)C220—C2211.416 (9)
C111—H11A0.9700C220—H2200.9300
C111—H11B0.9700C221—C2221.321 (9)
C112—C1131.516 (8)C221—H2210.9300
C112—H11C0.9700C222—O221.365 (8)
C112—H11D0.9700C222—H2220.9300
C113—C1181.349 (10)C223—O231.226 (8)
C113—C1141.351 (9)C223—N211.337 (7)
C114—C1151.375 (10)C224—N211.465 (7)
C114—H1140.9300C224—C2251.506 (9)
C115—C1161.324 (13)C224—H22A0.9700
C115—H1150.9300C224—H22B0.9700
C116—C1171.367 (12)C225—C2261.482 (10)
C116—H1160.9300C225—H22C0.9700
C117—C1181.392 (11)C225—H22D0.9700
C117—H1170.9300C226—C2271.527 (8)
C118—H1180.9300C226—H22E0.9700
C119—C1201.318 (8)C226—H22F0.9700
C119—O121.373 (6)C227—N211.468 (8)
C120—C1211.419 (9)C227—H22G0.9700
C120—H1200.9300C227—H22H0.9700
O11—C11—N12122.7 (6)N11—C124—H12A111.2
O11—C11—C16120.9 (6)C125—C124—H12A111.2
N12—C11—C16116.4 (5)N11—C124—H12B111.2
N12—C13—C119109.9 (4)C125—C124—H12B111.2
N12—C13—C14112.3 (5)H12A—C124—H12B109.1
C119—C13—C14109.6 (5)C126—C125—C124104.2 (6)
N12—C13—H13108.3C126—C125—H12C110.9
C119—C13—H13108.3C124—C125—H12C110.9
C14—C13—H13108.3C126—C125—H12D110.9
C15—C14—C123108.4 (5)C124—C125—H12D110.9
C15—C14—C13109.8 (4)H12C—C125—H12D108.9
C123—C14—C13109.9 (5)C125—C126—C127107.0 (6)
C15—C14—H14109.6C125—C126—H12E110.3
C123—C14—H14109.6C127—C126—H12E110.3
C13—C14—H14109.6C125—C126—H12F110.3
C16—C15—C110119.0 (7)C127—C126—H12F110.3
C16—C15—C14119.1 (5)H12E—C126—H12F108.6
C110—C15—C14121.8 (6)N11—C127—C126101.1 (6)
C15—C16—C17120.5 (6)N11—C127—H12G111.5
C15—C16—C11121.8 (5)C126—C127—H12G111.5
C17—C16—C11117.7 (5)N11—C127—H12H111.5
C18—C17—C16120.0 (6)C126—C127—H12H111.5
C18—C17—H17120.0H12G—C127—H12H109.4
C16—C17—H17120.0C25—C210—C29119.8 (7)
C19—C18—C17119.6 (7)C25—C210—H210120.1
C19—C18—H18120.2C29—C210—H210120.1
C17—C18—H18120.2N22—C211—C212113.9 (5)
C110—C19—C18120.9 (8)N22—C211—H21A108.8
C110—C19—H19119.6C212—C211—H21A108.8
C18—C19—H19119.6N22—C211—H21B108.8
O21—C21—N22122.5 (6)C212—C211—H21B108.8
O21—C21—C26119.9 (6)H21A—C211—H21B107.7
N22—C21—C26117.6 (5)C213—C212—C211109.9 (5)
N22—C23—C219109.6 (5)C213—C212—H21C109.7
N22—C23—C24111.7 (5)C211—C212—H21C109.7
C219—C23—C24111.0 (5)C213—C212—H21D109.7
N22—C23—H23108.1C211—C212—H21D109.7
C219—C23—H23108.1H21C—C212—H21D108.2
C24—C23—H23108.1C218—C213—C214117.7 (6)
C25—C24—C23110.8 (5)C218—C213—C212120.1 (7)
C25—C24—C223109.5 (5)C214—C213—C212122.1 (7)
C23—C24—C223110.3 (5)C215—C214—C213122.3 (8)
C25—C24—H24108.8C215—C214—H214118.9
C23—C24—H24108.8C213—C214—H214118.9
C223—C24—H24108.8C214—C215—C216117.2 (9)
C210—C25—C26119.4 (6)C214—C215—H215121.4
C210—C25—C24122.9 (6)C216—C215—H215121.4
C26—C25—C24117.7 (5)C217—C216—C215123.1 (8)
C27—C26—C25119.0 (6)C217—C216—H216118.5
C27—C26—C21119.6 (5)C215—C216—H216118.5
C25—C26—C21121.3 (5)C216—C217—C218117.8 (8)
C28—C27—C26121.4 (6)C216—C217—H217121.1
C28—C27—H27119.3C218—C217—H217121.1
C26—C27—H27119.3C213—C218—C217121.9 (8)
C29—C28—C27119.5 (7)C213—C218—H218119.1
C29—C28—H28120.2C217—C218—H218119.1
C27—C28—H28120.2C220—C219—O22109.1 (5)
C28—C29—C210120.7 (7)C220—C219—C23135.4 (5)
C28—C29—H29119.6O22—C219—C23115.5 (5)
C210—C29—H29119.6C219—C220—C221106.1 (6)
C19—C110—C15119.9 (8)C219—C220—H220127.0
C19—C110—H110120.0C221—C220—H220127.0
C15—C110—H110120.0C222—C221—C220107.8 (6)
N12—C111—C112111.1 (4)C222—C221—H221126.1
N12—C111—H11A109.4C220—C221—H221126.1
C112—C111—H11A109.4C221—C222—O22110.1 (6)
N12—C111—H11B109.4C221—C222—H222125.0
C112—C111—H11B109.4O22—C222—H222125.0
H11A—C111—H11B108.0O23—C223—N21122.0 (6)
C113—C112—C111111.0 (5)O23—C223—C24120.2 (6)
C113—C112—H11C109.4N21—C223—C24117.8 (6)
C111—C112—H11C109.4N21—C224—C225103.9 (5)
C113—C112—H11D109.4N21—C224—H22A111.0
C111—C112—H11D109.4C225—C224—H22A111.0
H11C—C112—H11D108.0N21—C224—H22B111.0
C118—C113—C114115.6 (7)C225—C224—H22B111.0
C118—C113—C112122.1 (7)H22A—C224—H22B109.0
C114—C113—C112122.3 (6)C226—C225—C224105.2 (6)
C113—C114—C115124.2 (8)C226—C225—H22C110.7
C113—C114—H114117.9C224—C225—H22C110.7
C115—C114—H114117.9C226—C225—H22D110.7
C116—C115—C114119.1 (9)C224—C225—H22D110.7
C116—C115—H115120.5H22C—C225—H22D108.8
C114—C115—H115120.5C225—C226—C227105.2 (6)
C115—C116—C117119.6 (8)C225—C226—H22E110.7
C115—C116—H116120.2C227—C226—H22E110.7
C117—C116—H116120.2C225—C226—H22F110.7
C116—C117—C118119.6 (9)C227—C226—H22F110.7
C116—C117—H117120.2H22E—C226—H22F108.8
C118—C117—H117120.2N21—C227—C226103.5 (5)
C113—C118—C117121.8 (9)N21—C227—H22G111.1
C113—C118—H118119.1C226—C227—H22G111.1
C117—C118—H118119.1N21—C227—H22H111.1
C120—C119—O12108.5 (6)C226—C227—H22H111.1
C120—C119—C13136.5 (5)H22G—C227—H22H109.0
O12—C119—C13115.0 (5)C123—N11—C127119.8 (6)
C119—C120—C121108.0 (6)C123—N11—C124127.4 (6)
C119—C120—H120126.0C127—N11—C124112.7 (5)
C121—C120—H120126.0C11—N12—C13123.7 (5)
C122—C121—C120106.9 (6)C11—N12—C111118.5 (5)
C122—C121—H121126.5C13—N12—C111117.8 (5)
C120—C121—H121126.5C223—N21—C224120.4 (5)
C121—C122—O12110.1 (6)C223—N21—C227128.0 (5)
C121—C122—H122124.9C224—N21—C227111.6 (4)
O12—C122—H122124.9C21—N22—C211119.2 (5)
O13—C123—N11122.5 (7)C21—N22—C23122.2 (5)
O13—C123—C14120.7 (6)C211—N22—C23118.5 (5)
N11—C123—C14116.8 (6)C119—O12—C122106.4 (5)
N11—C124—C125102.9 (6)C222—O22—C219106.9 (5)
O11—C11—N12—C13178.2 (5)O21—C21—N22—C23173.8 (5)
O11—C11—N12—C1114.0 (8)O21—C21—N22—C2114.2 (8)
C16—C11—N12—C130.1 (8)C26—C21—N22—C235.2 (8)
C16—C11—N12—C111177.7 (5)C26—C21—N22—C211176.8 (5)
O11—C11—C16—C15166.1 (6)O21—C21—C26—C25167.7 (5)
O11—C11—C16—C1713.1 (8)O21—C21—C26—C2711.3 (8)
N12—C11—C16—C1515.6 (8)N22—C21—C26—C2513.3 (8)
N12—C11—C16—C17165.2 (5)N22—C21—C26—C27167.7 (5)
C14—C13—N12—C1131.5 (8)C24—C23—N22—C2136.8 (7)
C14—C13—N12—C111146.3 (5)C24—C23—N22—C211145.2 (5)
C119—C13—N12—C1190.7 (6)C219—C23—N22—C2186.7 (6)
C119—C13—N12—C11191.5 (6)C219—C23—N22—C21191.4 (6)
N12—C13—C14—C1546.2 (6)N22—C23—C24—C2549.4 (7)
N12—C13—C14—C12372.9 (6)N22—C23—C24—C22372.0 (6)
C119—C13—C14—C1576.2 (6)C219—C23—C24—C2573.3 (6)
C119—C13—C14—C123164.7 (5)C219—C23—C24—C223165.4 (5)
C13—C14—C15—C1633.9 (7)C23—C24—C25—C2634.0 (7)
C13—C14—C15—C110149.2 (6)C23—C24—C25—C210148.9 (6)
C123—C14—C15—C1686.1 (6)C223—C24—C25—C2687.9 (6)
C123—C14—C15—C11090.7 (7)C223—C24—C25—C21089.2 (7)
C14—C15—C16—C113.5 (8)C24—C25—C26—C213.1 (8)
C14—C15—C16—C17175.7 (5)C24—C25—C26—C27175.9 (5)
C110—C15—C16—C11179.6 (5)C210—C25—C26—C21179.7 (5)
C110—C15—C16—C171.2 (9)C210—C25—C26—C271.3 (9)
C11—C16—C17—C18178.9 (5)C21—C26—C27—C28178.6 (6)
C15—C16—C17—C180.3 (9)C25—C26—C27—C280.5 (9)
C16—C17—C18—C192.3 (10)C26—C27—C28—C290.9 (10)
C17—C18—C19—C1102.7 (12)C27—C28—C29—C2100.4 (11)
C19—C110—C15—C14176.0 (7)C29—C210—C25—C24174.5 (6)
C19—C110—C15—C160.9 (11)C29—C210—C25—C262.6 (10)
C15—C110—C19—C181.1 (13)C25—C210—C29—C282.2 (11)
C112—C111—N12—C1188.6 (7)C212—C211—N22—C2190.1 (7)
C112—C111—N12—C1389.4 (7)C212—C211—N22—C2391.8 (7)
N12—C111—C112—C113178.5 (6)N22—C211—C212—C213178.4 (6)
C111—C112—C113—C11487.4 (8)C211—C212—C213—C21486.2 (8)
C111—C112—C113—C11890.4 (9)C211—C212—C213—C21891.2 (8)
C112—C113—C114—C115178.2 (8)C212—C213—C214—C215175.3 (7)
C118—C113—C114—C1150.3 (13)C218—C213—C214—C2152.1 (12)
C112—C113—C118—C117178.1 (8)C212—C213—C218—C217174.8 (8)
C114—C113—C118—C1170.2 (14)C214—C213—C218—C2172.6 (13)
C113—C114—C115—C1160.9 (16)C213—C214—C215—C2160.9 (14)
C114—C115—C116—C1172.1 (18)C214—C215—C216—C2170.3 (17)
C115—C116—C117—C1182.3 (18)C215—C216—C217—C2180.8 (17)
C116—C117—C118—C1131.1 (17)C216—C217—C218—C2132.0 (16)
C13—C119—O12—C122179.8 (5)C23—C219—O22—C222179.2 (5)
C120—C119—O12—C1220.5 (7)C220—C219—O22—C2221.0 (7)
O12—C119—C13—N1249.2 (7)O22—C219—C23—N2246.1 (7)
O12—C119—C13—C14173.0 (5)O22—C219—C23—C24169.9 (5)
C120—C119—C13—N12131.3 (8)C220—C219—C23—N22134.1 (7)
C120—C119—C13—C147.5 (10)C220—C219—C23—C2410.3 (10)
O12—C119—C120—C1210.6 (8)O22—C219—C220—C2210.7 (7)
C13—C119—C120—C121179.9 (7)C23—C219—C220—C221179.6 (6)
C119—C120—C121—C1220.5 (9)C219—C220—C221—C2220.1 (8)
C120—C121—C122—O120.2 (9)C220—C221—C222—O220.5 (9)
C121—C122—O12—C1190.2 (8)C221—C222—O22—C2190.9 (8)
O13—C123—N11—C124176.9 (7)O23—C223—N21—C2242.9 (10)
O13—C123—N11—C1271.0 (11)O23—C223—N21—C227175.7 (7)
C14—C123—N11—C1244.3 (10)C24—C223—N21—C224179.4 (5)
C14—C123—N11—C127177.9 (6)C24—C223—N21—C2270.8 (9)
O13—C123—C14—C1351.9 (9)O23—C223—C24—C2354.3 (8)
O13—C123—C14—C1568.1 (8)O23—C223—C24—C2567.8 (8)
N11—C123—C14—C13127.0 (6)N21—C223—C24—C23129.1 (6)
N11—C123—C14—C15113.0 (6)N21—C223—C24—C25108.8 (6)
C125—C124—N11—C123167.2 (7)C225—C224—N21—C223168.1 (6)
C125—C124—N11—C12710.8 (8)C225—C224—N21—C22713.1 (7)
N11—C124—C125—C12628.3 (9)N21—C224—C225—C22628.4 (8)
C124—C125—C126—C12736.0 (10)C224—C225—C226—C22733.2 (8)
C125—C126—C127—N1128.4 (9)C225—C226—C227—N2124.6 (8)
C126—C127—N11—C123171.9 (6)C226—C227—N21—C223171.8 (6)
C126—C127—N11—C12410.0 (8)C226—C227—N21—C2246.9 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C122—H122···O11i0.932.493.342 (8)153
C222—H222···O21ii0.932.573.454 (8)160
C121—H121···Cg2iii0.932.893.681 (6)147
C221—H221···Cg1iv0.932.923.756 (5)149
Symmetry codes: (i) x1/2, y+2, z; (ii) x+1/2, y+1, z; (iii) x1, y, z; (iv) x+1, y, z.
 

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