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In the title compound, C33H25NO, the β-lactam is planar in the two crystallographically independent mol­ecules in the asymmetric unit. The phenyl ring attached at the N atom is coplanar with the β-lactam, while the orientations of the two phenyl rings attached at each of the two C atoms of the β-lactam are determined by the Csp3 nature of these atoms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802018974/cv6154sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802018974/cv6154Isup2.hkl
Contains datablock I

CCDC reference: 200792

Key indicators

  • Single-crystal X-ray study
  • T = 183 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.105
  • wR factor = 0.266
  • Data-to-parameter ratio = 13.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
DIFMN_02 Alert C The minimum difference density is < -0.1*ZMAX*0.75 _refine_diff_density_min given = -0.643 Test value = -0.600 DIFMN_03 Alert C The minimum difference density is < -0.1*ZMAX*0.75 The relevant atom site should be identified. DIFMX_01 Alert C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.676 Test value = 0.600 DIFMX_02 Alert C The minimum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. RFACG_01 Alert C The value of the R factor is > 0.10 R factor given 0.105 RFACR_01 Alert C The value of the weighted R factor is > 0.25 Weighted R factor given 0.266 PLAT_361 Alert C Long C(sp3)-C(sp3) Bond C(2A) - C(3A) = 1.65 Ang. PLAT_361 Alert C Long C(sp3)-C(sp3) Bond C(2B) - C(3B) = 1.65 Ang.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
8 Alert Level C = Please check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT and SADABS; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

1,3,3,4,4-Pentaphenyl-β-lactam top
Crystal data top
C33H25NOF(000) = 952
Mr = 451.54Dx = 1.249 Mg m3
Triclinic, P1Melting point: 465(1) K
a = 10.3827 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.5395 (2) ÅCell parameters from 8086 reflections
c = 17.3675 (1) Åθ = 2.5–28.3°
α = 105.145 (1)°µ = 0.07 mm1
β = 102.943 (1)°T = 183 K
γ = 98.9522 (5)°Block, colorless
V = 2401.68 (4) Å30.50 × 0.48 × 0.40 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer
8200 independent reflections
Radiation source: fine-focus sealed tube4864 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.083
Detector resolution: 8.33 pixels mm-1θmax = 25.0°, θmin = 2.5°
ω scansh = 1112
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 1717
Tmin = 0.903, Tmax = 0.964l = 1620
11565 measured reflections
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)] = 0.105H-atom parameters constrained
wR(F2) = 0.266 w = 1/[σ2(Fo2) + (0.1362P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max < 0.001
8200 reflectionsΔρmax = 0.68 e Å3
632 parametersΔρmin = 0.64 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.030 (4)
Special details top

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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
O1A0.8219 (3)0.5719 (2)0.39538 (18)0.0392 (8)
N1A0.7977 (3)0.5473 (2)0.2540 (2)0.0274 (8)
C1A0.8611 (4)0.5799 (3)0.3365 (2)0.0278 (9)
C2A0.9954 (4)0.6307 (3)0.3259 (2)0.0230 (9)
C3A0.9180 (4)0.5818 (3)0.2261 (2)0.0228 (8)
C4A1.1198 (4)0.5928 (3)0.3579 (2)0.0251 (9)
C5A1.1302 (4)0.5540 (3)0.4225 (2)0.0314 (10)
H5A1.05870.54820.44620.038*
C6A1.2456 (5)0.5232 (3)0.4529 (3)0.0385 (11)
H6A1.24910.49450.49510.046*
C7A1.3553 (5)0.5350 (3)0.4210 (3)0.0418 (11)
H7A1.43440.51730.44330.050*
C8A1.3463 (4)0.5732 (3)0.3559 (3)0.0378 (11)
H8A1.41860.57960.33290.045*
C9A1.2300 (4)0.6021 (3)0.3244 (2)0.0299 (9)
H9A1.22510.62790.28050.036*
C10A1.0194 (4)0.7416 (3)0.3592 (2)0.0288 (9)
C11A0.9075 (4)0.7846 (3)0.3584 (2)0.0334 (10)
H11A0.82000.74540.33840.040*
C12A0.9272 (5)0.8860 (3)0.3874 (3)0.0427 (12)
H12A0.85230.91370.38730.051*
C13A1.0552 (6)0.9457 (3)0.4162 (3)0.0471 (12)
H13A1.06701.01330.43380.056*
C14A1.1656 (5)0.9039 (3)0.4185 (3)0.0455 (12)
H14A1.25290.94340.43910.055*
C15A1.1468 (5)0.8021 (3)0.3900 (3)0.0377 (10)
H15A1.22230.77480.39200.045*
C16A0.8993 (4)0.6563 (3)0.1807 (2)0.0232 (9)
C17A0.7731 (4)0.6786 (3)0.1558 (3)0.0320 (10)
H17A0.69780.64570.16620.038*
C18A0.7588 (4)0.7488 (3)0.1160 (3)0.0372 (11)
H18A0.67420.76260.09980.045*
C19A0.8700 (5)0.7986 (3)0.1002 (3)0.0382 (11)
H19A0.86040.84550.07310.046*
C20A0.9953 (4)0.7778 (3)0.1252 (3)0.0323 (10)
H20A1.07000.81090.11430.039*
C21A1.0114 (4)0.7092 (3)0.1657 (2)0.0273 (9)
H21A1.09710.69770.18340.033*
C22A0.9658 (4)0.4929 (2)0.1811 (2)0.0213 (8)
C23A0.9590 (4)0.4116 (3)0.2101 (2)0.0285 (9)
H23A0.92550.41260.25560.034*
C24A1.0012 (4)0.3294 (3)0.1724 (3)0.0342 (10)
H24A0.99600.27620.19280.041*
C25A1.0506 (4)0.3272 (3)0.1049 (3)0.0337 (10)
H25A1.07930.27240.07960.040*
C26A1.0576 (4)0.4063 (3)0.0748 (2)0.0314 (10)
H26A1.09110.40480.02930.038*
C27A1.0149 (4)0.4875 (3)0.1121 (2)0.0270 (9)
H27A1.01900.53990.09070.032*
C28A0.6692 (4)0.4820 (3)0.2058 (3)0.0286 (9)
C29A0.5769 (4)0.4538 (3)0.2478 (3)0.0389 (11)
H29A0.59910.47440.30550.047*
C30A0.4508 (5)0.3939 (3)0.2002 (3)0.0462 (13)
H30A0.38870.37340.22690.055*
C31A0.4159 (5)0.3642 (3)0.1149 (3)0.0480 (13)
H31A0.33030.32560.08430.058*
C32A0.5094 (5)0.3924 (3)0.0752 (3)0.0462 (12)
H32A0.48740.37120.01750.055*
C33A0.6359 (4)0.4522 (3)0.1208 (3)0.0363 (10)
H33A0.69780.47190.09380.044*
O1B0.5922 (3)0.0367 (2)0.39261 (17)0.0365 (7)
N1B0.4973 (3)0.0500 (2)0.25346 (19)0.0225 (7)
C1B0.5551 (4)0.0046 (3)0.3365 (2)0.0241 (9)
C2B0.5544 (4)0.0997 (3)0.3298 (2)0.0239 (8)
C3B0.4781 (4)0.0400 (3)0.2308 (2)0.0232 (8)
C4B0.4684 (4)0.1535 (3)0.3784 (2)0.0246 (9)
C5B0.4553 (4)0.1386 (3)0.4522 (2)0.0319 (10)
H5B0.49920.09520.47260.038*
C6B0.3763 (4)0.1885 (3)0.4958 (3)0.0387 (11)
H6B0.36540.17630.54430.046*
C7B0.3143 (4)0.2553 (3)0.4682 (3)0.0365 (10)
H7B0.26420.28980.49850.044*
C8B0.3275 (4)0.2708 (3)0.3943 (3)0.0314 (10)
H8B0.28370.31420.37390.038*
C9B0.4059 (4)0.2214 (3)0.3511 (2)0.0280 (9)
H9B0.41700.23400.30290.034*
C10B0.6963 (4)0.1603 (3)0.3462 (2)0.0269 (9)
C11B0.8063 (4)0.1173 (3)0.3399 (3)0.0357 (10)
H11B0.79280.04970.32690.043*
C12B0.9340 (5)0.1719 (3)0.3524 (3)0.0460 (12)
H12B1.00510.14110.34730.055*
C13B0.9571 (4)0.2733 (3)0.3725 (3)0.0413 (11)
H13B1.04320.31050.38060.050*
C14B0.8513 (4)0.3180 (3)0.3803 (2)0.0339 (10)
H14B0.86600.38570.39360.041*
C15B0.7237 (4)0.2633 (3)0.3686 (3)0.0316 (10)
H15B0.65400.29500.37570.038*
C16B0.5594 (4)0.0625 (3)0.1727 (2)0.0249 (9)
C17B0.5808 (4)0.1570 (3)0.1648 (3)0.0321 (10)
H17B0.54370.20420.19400.039*
C18B0.6570 (4)0.1802 (3)0.1137 (3)0.0389 (11)
H18B0.67180.24330.10970.047*
C19B0.7108 (4)0.1113 (3)0.0690 (3)0.0387 (11)
H19B0.76120.12740.03450.046*
C20B0.6900 (4)0.0181 (3)0.0756 (3)0.0358 (10)
H20B0.72640.02880.04540.043*
C21B0.6147 (4)0.0063 (3)0.1272 (2)0.0273 (9)
H21B0.60130.06940.13130.033*
C22B0.3266 (4)0.0401 (3)0.2035 (2)0.0232 (8)
C23B0.2733 (4)0.0752 (3)0.1396 (3)0.0349 (10)
H23B0.32820.09580.10900.042*
C24B0.1359 (5)0.0797 (3)0.1209 (3)0.0452 (12)
H24B0.10020.10310.07760.054*
C25B0.0545 (5)0.0499 (3)0.1659 (3)0.0469 (12)
H25B0.03520.05580.15500.056*
C26B0.1051 (4)0.0115 (3)0.2267 (3)0.0392 (11)
H26B0.04890.01060.25610.047*
C27B0.2396 (4)0.0051 (3)0.2451 (2)0.0296 (9)
H27B0.27210.02300.28580.035*
C28B0.4456 (4)0.1509 (3)0.2072 (2)0.0229 (9)
C29B0.4830 (4)0.2221 (3)0.2421 (3)0.0326 (10)
H29B0.53990.20430.29580.039*
C30B0.4341 (5)0.3200 (3)0.1957 (3)0.0420 (12)
H30B0.45680.36800.21910.050*
C31B0.3527 (5)0.3472 (3)0.1154 (3)0.0386 (11)
H31B0.32270.41310.08480.046*
C32B0.3156 (4)0.2773 (3)0.0804 (3)0.0368 (10)
H32B0.25900.29540.02660.044*
C33B0.3647 (4)0.1778 (3)0.1273 (3)0.0316 (10)
H33B0.34190.12990.10380.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0413 (19)0.0418 (17)0.0404 (19)0.0050 (15)0.0269 (15)0.0121 (14)
N1A0.0210 (18)0.0287 (17)0.037 (2)0.0031 (16)0.0172 (16)0.0109 (15)
C1A0.035 (2)0.028 (2)0.029 (2)0.014 (2)0.019 (2)0.0100 (18)
C2A0.028 (2)0.0203 (18)0.024 (2)0.0063 (18)0.0149 (17)0.0066 (16)
C3A0.0121 (19)0.0265 (19)0.030 (2)0.0013 (17)0.0096 (16)0.0083 (17)
C4A0.026 (2)0.0227 (18)0.025 (2)0.0021 (18)0.0082 (17)0.0045 (16)
C5A0.037 (3)0.029 (2)0.026 (2)0.002 (2)0.0089 (19)0.0066 (18)
C6A0.049 (3)0.040 (2)0.030 (3)0.011 (2)0.007 (2)0.019 (2)
C7A0.043 (3)0.048 (3)0.039 (3)0.022 (2)0.006 (2)0.018 (2)
C8A0.032 (3)0.049 (3)0.038 (3)0.015 (2)0.013 (2)0.016 (2)
C9A0.033 (2)0.036 (2)0.025 (2)0.012 (2)0.0110 (19)0.0133 (18)
C10A0.039 (3)0.029 (2)0.020 (2)0.006 (2)0.0126 (19)0.0079 (17)
C11A0.038 (3)0.026 (2)0.033 (3)0.008 (2)0.013 (2)0.0008 (18)
C12A0.059 (3)0.034 (2)0.040 (3)0.020 (3)0.020 (2)0.008 (2)
C13A0.071 (4)0.029 (2)0.039 (3)0.011 (3)0.015 (3)0.007 (2)
C14A0.053 (3)0.026 (2)0.042 (3)0.007 (2)0.005 (2)0.001 (2)
C15A0.035 (3)0.030 (2)0.042 (3)0.001 (2)0.009 (2)0.006 (2)
C16A0.019 (2)0.0193 (18)0.029 (2)0.0036 (17)0.0091 (17)0.0033 (16)
C17A0.023 (2)0.033 (2)0.042 (3)0.008 (2)0.0094 (19)0.013 (2)
C18A0.028 (2)0.030 (2)0.047 (3)0.011 (2)0.002 (2)0.008 (2)
C19A0.047 (3)0.025 (2)0.045 (3)0.012 (2)0.009 (2)0.016 (2)
C20A0.037 (3)0.025 (2)0.034 (3)0.004 (2)0.012 (2)0.0082 (18)
C21A0.022 (2)0.0260 (19)0.034 (2)0.0060 (18)0.0093 (18)0.0077 (17)
C22A0.018 (2)0.0182 (17)0.023 (2)0.0013 (16)0.0038 (16)0.0018 (15)
C23A0.030 (2)0.0254 (19)0.030 (2)0.0049 (19)0.0124 (18)0.0060 (17)
C24A0.032 (2)0.025 (2)0.050 (3)0.005 (2)0.017 (2)0.0141 (19)
C25A0.037 (3)0.023 (2)0.042 (3)0.013 (2)0.016 (2)0.0034 (18)
C26A0.036 (2)0.032 (2)0.029 (2)0.013 (2)0.0159 (19)0.0057 (18)
C27A0.030 (2)0.0236 (19)0.030 (2)0.0077 (19)0.0114 (18)0.0089 (17)
C28A0.019 (2)0.025 (2)0.047 (3)0.0051 (18)0.0169 (19)0.0135 (19)
C29A0.026 (2)0.034 (2)0.066 (3)0.007 (2)0.026 (2)0.019 (2)
C30A0.026 (3)0.042 (3)0.077 (4)0.001 (2)0.026 (3)0.022 (3)
C31A0.023 (2)0.042 (3)0.072 (4)0.000 (2)0.013 (2)0.009 (2)
C32A0.029 (3)0.042 (3)0.056 (3)0.001 (2)0.012 (2)0.001 (2)
C33A0.026 (2)0.036 (2)0.046 (3)0.004 (2)0.017 (2)0.008 (2)
O1B0.0450 (19)0.0342 (16)0.0310 (18)0.0118 (15)0.0053 (14)0.0142 (14)
N1B0.0186 (17)0.0221 (16)0.027 (2)0.0037 (15)0.0054 (14)0.0094 (14)
C1B0.021 (2)0.028 (2)0.027 (2)0.0080 (18)0.0073 (17)0.0125 (18)
C2B0.022 (2)0.027 (2)0.025 (2)0.0086 (18)0.0067 (17)0.0109 (17)
C3B0.020 (2)0.0235 (19)0.026 (2)0.0052 (17)0.0064 (17)0.0081 (16)
C4B0.018 (2)0.0255 (19)0.025 (2)0.0006 (17)0.0043 (16)0.0033 (16)
C5B0.030 (2)0.036 (2)0.029 (2)0.008 (2)0.0081 (19)0.0100 (19)
C6B0.038 (3)0.047 (3)0.032 (3)0.008 (2)0.016 (2)0.008 (2)
C7B0.031 (2)0.041 (2)0.040 (3)0.011 (2)0.017 (2)0.008 (2)
C8B0.020 (2)0.029 (2)0.042 (3)0.0061 (19)0.0072 (19)0.0074 (19)
C9B0.026 (2)0.027 (2)0.030 (2)0.0026 (19)0.0096 (18)0.0069 (17)
C10B0.029 (2)0.026 (2)0.025 (2)0.0063 (19)0.0088 (18)0.0058 (17)
C11B0.028 (2)0.029 (2)0.047 (3)0.008 (2)0.010 (2)0.0055 (19)
C12B0.031 (3)0.040 (3)0.070 (4)0.011 (2)0.022 (2)0.012 (2)
C13B0.027 (2)0.040 (2)0.051 (3)0.004 (2)0.015 (2)0.006 (2)
C14B0.033 (2)0.025 (2)0.038 (3)0.000 (2)0.013 (2)0.0002 (18)
C15B0.023 (2)0.026 (2)0.044 (3)0.0042 (19)0.0125 (19)0.0050 (18)
C16B0.020 (2)0.030 (2)0.029 (2)0.0089 (18)0.0076 (17)0.0138 (17)
C17B0.037 (3)0.028 (2)0.037 (3)0.011 (2)0.015 (2)0.0126 (18)
C18B0.039 (3)0.039 (2)0.039 (3)0.001 (2)0.010 (2)0.019 (2)
C19B0.033 (3)0.057 (3)0.033 (3)0.008 (2)0.013 (2)0.022 (2)
C20B0.030 (2)0.046 (3)0.035 (3)0.015 (2)0.014 (2)0.012 (2)
C21B0.027 (2)0.027 (2)0.027 (2)0.0064 (19)0.0079 (17)0.0073 (17)
C22B0.020 (2)0.0190 (17)0.027 (2)0.0035 (17)0.0040 (16)0.0039 (16)
C23B0.032 (2)0.031 (2)0.041 (3)0.012 (2)0.006 (2)0.0122 (19)
C24B0.037 (3)0.036 (2)0.056 (3)0.015 (2)0.002 (2)0.014 (2)
C25B0.022 (2)0.034 (2)0.073 (4)0.009 (2)0.004 (2)0.003 (2)
C26B0.023 (2)0.031 (2)0.056 (3)0.001 (2)0.014 (2)0.002 (2)
C27B0.025 (2)0.028 (2)0.031 (2)0.0041 (19)0.0067 (18)0.0040 (18)
C28B0.020 (2)0.0201 (18)0.030 (2)0.0041 (17)0.0108 (17)0.0080 (17)
C29B0.038 (3)0.026 (2)0.040 (3)0.010 (2)0.018 (2)0.0144 (19)
C30B0.054 (3)0.030 (2)0.063 (4)0.016 (2)0.040 (3)0.025 (2)
C31B0.034 (3)0.027 (2)0.055 (3)0.001 (2)0.025 (2)0.007 (2)
C32B0.027 (2)0.032 (2)0.041 (3)0.001 (2)0.007 (2)0.001 (2)
C33B0.031 (2)0.0187 (19)0.045 (3)0.0082 (19)0.013 (2)0.0061 (18)
Geometric parameters (Å, º) top
O1A—C1A1.209 (4)O1B—C1B1.201 (4)
N1A—C1A1.355 (5)N1B—C1B1.367 (5)
N1A—C28A1.440 (5)N1B—C28B1.425 (4)
N1A—C3A1.500 (4)N1B—C3B1.491 (4)
C1A—C2A1.546 (5)C1B—C2B1.551 (5)
C2A—C10A1.523 (5)C2B—C10B1.518 (5)
C2A—C4A1.529 (5)C2B—C4B1.528 (5)
C2A—C3A1.647 (5)C2B—C3B1.652 (5)
C3A—C16A1.508 (5)C3B—C16B1.519 (5)
C3A—C22A1.540 (5)C3B—C22B1.538 (5)
C4A—C5A1.373 (5)C4B—C5B1.385 (5)
C4A—C9A1.398 (5)C4B—C9B1.389 (5)
C5A—C6A1.386 (6)C5B—C6B1.397 (5)
C5A—H5A0.9300C5B—H5B0.9300
C6A—C7A1.381 (6)C6B—C7B1.374 (6)
C6A—H6A0.9300C6B—H6B0.9300
C7A—C8A1.376 (5)C7B—C8B1.392 (5)
C7A—H7A0.9300C7B—H7B0.9300
C8A—C9A1.384 (5)C8B—C9B1.383 (5)
C8A—H8A0.9300C8B—H8B0.9300
C9A—H9A0.9300C9B—H9B0.9300
C10A—C15A1.373 (6)C10B—C11B1.396 (5)
C10A—C11A1.402 (5)C10B—C15B1.409 (5)
C11A—C12A1.393 (5)C11B—C12B1.375 (6)
C11A—H11A0.9300C11B—H11B0.9300
C12A—C13A1.373 (7)C12B—C13B1.392 (6)
C12A—H12A0.9300C12B—H12B0.9300
C13A—C14A1.376 (6)C13B—C14B1.374 (6)
C13A—H13A0.9300C13B—H13B0.9300
C14A—C15A1.399 (5)C14B—C15B1.377 (5)
C14A—H14A0.9300C14B—H14B0.9300
C15A—H15A0.9300C15B—H15B0.9300
C16A—C17A1.401 (5)C16B—C21B1.387 (5)
C16A—C21A1.406 (5)C16B—C17B1.404 (5)
C17A—C18A1.382 (5)C17B—C18B1.383 (5)
C17A—H17A0.9300C17B—H17B0.9300
C18A—C19A1.385 (6)C18B—C19B1.371 (6)
C18A—H18A0.9300C18B—H18B0.9300
C19A—C20A1.382 (6)C19B—C20B1.378 (6)
C19A—H19A0.9300C19B—H19B0.9300
C20A—C21A1.373 (5)C20B—C21B1.390 (5)
C20A—H20A0.9300C20B—H20B0.9300
C21A—H21A0.9300C21B—H21B0.9300
C22A—C27A1.392 (5)C22B—C23B1.380 (5)
C22A—C23A1.399 (5)C22B—C27B1.394 (5)
C23A—C24A1.389 (5)C23B—C24B1.406 (6)
C23A—H23A0.9300C23B—H23B0.9300
C24A—C25A1.377 (5)C24B—C25B1.369 (6)
C24A—H24A0.9300C24B—H24B0.9300
C25A—C26A1.380 (5)C25B—C26B1.361 (6)
C25A—H25A0.9300C25B—H25B0.9300
C26A—C27A1.380 (5)C26B—C27B1.384 (6)
C26A—H26A0.9300C26B—H26B0.9300
C27A—H27A0.9300C27B—H27B0.9300
C28A—C33A1.369 (6)C28B—C33B1.370 (6)
C28A—C29A1.402 (5)C28B—C29B1.392 (5)
C29A—C30A1.392 (7)C29B—C30B1.389 (6)
C29A—H29A0.9300C29B—H29B0.9300
C30A—C31A1.375 (7)C30B—C31B1.376 (7)
C30A—H30A0.9300C30B—H30B0.9300
C31A—C32A1.383 (6)C31B—C32B1.376 (6)
C31A—H31A0.9300C31B—H31B0.9300
C32A—C33A1.388 (6)C32B—C33B1.408 (5)
C32A—H32A0.9300C32B—H32B0.9300
C33A—H33A0.9300C33B—H33B0.9300
C1A—N1A—C28A132.6 (3)C1B—N1B—C28B131.3 (3)
C1A—N1A—C3A96.7 (3)C1B—N1B—C3B96.5 (3)
C28A—N1A—C3A129.4 (3)C28B—N1B—C3B130.9 (3)
O1A—C1A—N1A131.3 (4)O1B—C1B—N1B131.3 (4)
O1A—C1A—C2A134.5 (4)O1B—C1B—C2B134.5 (4)
N1A—C1A—C2A94.2 (3)N1B—C1B—C2B94.2 (3)
C10A—C2A—C4A112.7 (3)C10B—C2B—C4B113.3 (3)
C10A—C2A—C1A111.2 (3)C10B—C2B—C1B112.4 (3)
C4A—C2A—C1A115.3 (3)C4B—C2B—C1B114.2 (3)
C10A—C2A—C3A115.5 (3)C10B—C2B—C3B114.4 (3)
C4A—C2A—C3A115.4 (3)C4B—C2B—C3B115.8 (3)
C1A—C2A—C3A83.8 (3)C1B—C2B—C3B83.5 (3)
N1A—C3A—C16A114.2 (3)N1B—C3B—C16B113.5 (3)
N1A—C3A—C22A109.5 (3)N1B—C3B—C22B111.1 (3)
C16A—C3A—C22A115.4 (3)C16B—C3B—C22B115.1 (3)
N1A—C3A—C2A85.0 (2)N1B—C3B—C2B85.7 (2)
C16A—C3A—C2A113.6 (3)C16B—C3B—C2B113.5 (3)
C22A—C3A—C2A115.4 (3)C22B—C3B—C2B114.5 (3)
C5A—C4A—C9A118.1 (3)C5B—C4B—C9B118.6 (3)
C5A—C4A—C2A121.7 (3)C5B—C4B—C2B120.9 (3)
C9A—C4A—C2A120.2 (3)C9B—C4B—C2B120.4 (3)
C4A—C5A—C6A121.2 (4)C4B—C5B—C6B120.1 (4)
C4A—C5A—H5A119.4C4B—C5B—H5B119.9
C6A—C5A—H5A119.4C6B—C5B—H5B119.9
C7A—C6A—C5A120.3 (4)C7B—C6B—C5B120.9 (4)
C7A—C6A—H6A119.8C7B—C6B—H6B119.6
C5A—C6A—H6A119.8C5B—C6B—H6B119.6
C8A—C7A—C6A119.2 (4)C6B—C7B—C8B119.2 (4)
C8A—C7A—H7A120.4C6B—C7B—H7B120.4
C6A—C7A—H7A120.4C8B—C7B—H7B120.4
C7A—C8A—C9A120.3 (4)C9B—C8B—C7B119.9 (4)
C7A—C8A—H8A119.8C9B—C8B—H8B120.1
C9A—C8A—H8A119.8C7B—C8B—H8B120.1
C8A—C9A—C4A120.8 (3)C8B—C9B—C4B121.2 (4)
C8A—C9A—H9A119.6C8B—C9B—H9B119.4
C4A—C9A—H9A119.6C4B—C9B—H9B119.4
C15A—C10A—C11A118.0 (4)C11B—C10B—C15B116.5 (4)
C15A—C10A—C2A122.8 (4)C11B—C10B—C2B122.0 (3)
C11A—C10A—C2A119.2 (4)C15B—C10B—C2B121.5 (3)
C12A—C11A—C10A120.1 (4)C12B—C11B—C10B122.0 (4)
C12A—C11A—H11A120.0C12B—C11B—H11B119.0
C10A—C11A—H11A120.0C10B—C11B—H11B119.0
C13A—C12A—C11A121.2 (4)C11B—C12B—C13B120.1 (4)
C13A—C12A—H12A119.4C11B—C12B—H12B120.0
C11A—C12A—H12A119.4C13B—C12B—H12B120.0
C12A—C13A—C14A119.0 (4)C14B—C13B—C12B119.3 (4)
C12A—C13A—H13A120.5C14B—C13B—H13B120.3
C14A—C13A—H13A120.5C12B—C13B—H13B120.3
C13A—C14A—C15A120.1 (5)C13B—C14B—C15B120.6 (4)
C13A—C14A—H14A119.9C13B—C14B—H14B119.7
C15A—C14A—H14A119.9C15B—C14B—H14B119.7
C10A—C15A—C14A121.5 (4)C14B—C15B—C10B121.5 (3)
C10A—C15A—H15A119.3C14B—C15B—H15B119.3
C14A—C15A—H15A119.3C10B—C15B—H15B119.3
C17A—C16A—C21A117.8 (3)C21B—C16B—C17B118.3 (3)
C17A—C16A—C3A121.9 (3)C21B—C16B—C3B122.7 (3)
C21A—C16A—C3A120.2 (3)C17B—C16B—C3B119.0 (3)
C18A—C17A—C16A121.0 (4)C18B—C17B—C16B120.2 (3)
C18A—C17A—H17A119.5C18B—C17B—H17B119.9
C16A—C17A—H17A119.5C16B—C17B—H17B119.9
C17A—C18A—C19A120.3 (4)C19B—C18B—C17B120.8 (4)
C17A—C18A—H18A119.9C19B—C18B—H18B119.6
C19A—C18A—H18A119.9C17B—C18B—H18B119.6
C20A—C19A—C18A119.3 (4)C18B—C19B—C20B119.6 (4)
C20A—C19A—H19A120.4C18B—C19B—H19B120.2
C18A—C19A—H19A120.4C20B—C19B—H19B120.2
C21A—C20A—C19A121.1 (4)C19B—C20B—C21B120.3 (4)
C21A—C20A—H20A119.5C19B—C20B—H20B119.8
C19A—C20A—H20A119.5C21B—C20B—H20B119.8
C20A—C21A—C16A120.5 (4)C16B—C21B—C20B120.7 (4)
C20A—C21A—H21A119.7C16B—C21B—H21B119.7
C16A—C21A—H21A119.7C20B—C21B—H21B119.7
C27A—C22A—C23A117.2 (3)C23B—C22B—C27B118.3 (4)
C27A—C22A—C3A124.0 (3)C23B—C22B—C3B122.4 (3)
C23A—C22A—C3A118.8 (3)C27B—C22B—C3B119.3 (3)
C24A—C23A—C22A121.5 (3)C22B—C23B—C24B120.1 (4)
C24A—C23A—H23A119.3C22B—C23B—H23B120.0
C22A—C23A—H23A119.3C24B—C23B—H23B120.0
C25A—C24A—C23A119.7 (3)C25B—C24B—C23B120.3 (4)
C25A—C24A—H24A120.1C25B—C24B—H24B119.8
C23A—C24A—H24A120.1C23B—C24B—H24B119.8
C24A—C25A—C26A119.9 (3)C26B—C25B—C24B119.9 (4)
C24A—C25A—H25A120.1C26B—C25B—H25B120.1
C26A—C25A—H25A120.1C24B—C25B—H25B120.1
C27A—C26A—C25A120.2 (3)C25B—C26B—C27B120.6 (4)
C27A—C26A—H26A119.9C25B—C26B—H26B119.7
C25A—C26A—H26A119.9C27B—C26B—H26B119.7
C26A—C27A—C22A121.5 (3)C26B—C27B—C22B120.7 (4)
C26A—C27A—H27A119.3C26B—C27B—H27B119.6
C22A—C27A—H27A119.3C22B—C27B—H27B119.6
C33A—C28A—C29A121.0 (4)C33B—C28B—C29B120.0 (4)
C33A—C28A—N1A120.5 (3)C33B—C28B—N1B120.3 (3)
C29A—C28A—N1A118.4 (4)C29B—C28B—N1B119.7 (3)
C30A—C29A—C28A117.8 (4)C30B—C29B—C28B119.1 (4)
C30A—C29A—H29A121.1C30B—C29B—H29B120.5
C28A—C29A—H29A121.1C28B—C29B—H29B120.5
C31A—C30A—C29A121.7 (4)C31B—C30B—C29B121.0 (4)
C31A—C30A—H30A119.1C31B—C30B—H30B119.5
C29A—C30A—H30A119.1C29B—C30B—H30B119.5
C30A—C31A—C32A119.2 (4)C30B—C31B—C32B120.3 (4)
C30A—C31A—H31A120.4C30B—C31B—H31B119.9
C32A—C31A—H31A120.4C32B—C31B—H31B119.9
C31A—C32A—C33A120.4 (5)C31B—C32B—C33B119.0 (4)
C31A—C32A—H32A119.8C31B—C32B—H32B120.5
C33A—C32A—H32A119.8C33B—C32B—H32B120.5
C28A—C33A—C32A119.8 (4)C28B—C33B—C32B120.7 (4)
C28A—C33A—H33A120.1C28B—C33B—H33B119.7
C32A—C33A—H33A120.1C32B—C33B—H33B119.7
C28A—N1A—C1A—O1A9.2 (7)C28B—N1B—C1B—O1B9.4 (6)
C3A—N1A—C1A—O1A176.4 (4)C3B—N1B—C1B—O1B177.4 (4)
C28A—N1A—C1A—C2A172.0 (4)C28B—N1B—C1B—C2B170.8 (3)
C3A—N1A—C1A—C2A4.8 (3)C3B—N1B—C1B—C2B2.8 (3)
O1A—C1A—C2A—C10A68.1 (5)O1B—C1B—C2B—C10B68.6 (5)
N1A—C1A—C2A—C10A110.6 (3)N1B—C1B—C2B—C10B111.2 (3)
O1A—C1A—C2A—C4A61.6 (5)O1B—C1B—C2B—C4B62.3 (6)
N1A—C1A—C2A—C4A119.6 (3)N1B—C1B—C2B—C4B118.0 (3)
O1A—C1A—C2A—C3A176.9 (4)O1B—C1B—C2B—C3B177.7 (4)
N1A—C1A—C2A—C3A4.3 (2)N1B—C1B—C2B—C3B2.6 (2)
C1A—N1A—C3A—C16A118.1 (3)C1B—N1B—C3B—C16B116.5 (3)
C28A—N1A—C3A—C16A74.1 (4)C28B—N1B—C3B—C16B75.5 (4)
C1A—N1A—C3A—C22A110.7 (3)C1B—N1B—C3B—C22B111.9 (3)
C28A—N1A—C3A—C22A57.1 (4)C28B—N1B—C3B—C22B56.1 (4)
C1A—N1A—C3A—C2A4.5 (3)C1B—N1B—C3B—C2B2.7 (3)
C28A—N1A—C3A—C2A172.3 (3)C28B—N1B—C3B—C2B170.7 (3)
C10A—C2A—C3A—N1A106.6 (3)C10B—C2B—C3B—N1B109.4 (3)
C4A—C2A—C3A—N1A119.0 (3)C4B—C2B—C3B—N1B116.2 (3)
C1A—C2A—C3A—N1A3.9 (2)C1B—C2B—C3B—N1B2.4 (2)
C10A—C2A—C3A—C16A7.7 (4)C10B—C2B—C3B—C16B4.4 (4)
C4A—C2A—C3A—C16A126.7 (3)C4B—C2B—C3B—C16B130.1 (3)
C1A—C2A—C3A—C16A118.2 (3)C1B—C2B—C3B—C16B116.1 (3)
C10A—C2A—C3A—C22A144.1 (3)C10B—C2B—C3B—C22B139.4 (3)
C4A—C2A—C3A—C22A9.8 (4)C4B—C2B—C3B—C22B4.9 (4)
C1A—C2A—C3A—C22A105.3 (3)C1B—C2B—C3B—C22B108.9 (3)
C10A—C2A—C4A—C5A99.9 (4)C10B—C2B—C4B—C5B97.7 (4)
C1A—C2A—C4A—C5A29.1 (5)C1B—C2B—C4B—C5B32.7 (5)
C3A—C2A—C4A—C5A124.5 (4)C3B—C2B—C4B—C5B127.3 (4)
C10A—C2A—C4A—C9A76.6 (4)C10B—C2B—C4B—C9B79.7 (4)
C1A—C2A—C4A—C9A154.4 (3)C1B—C2B—C4B—C9B149.8 (4)
C3A—C2A—C4A—C9A59.1 (5)C3B—C2B—C4B—C9B55.3 (5)
C9A—C4A—C5A—C6A1.1 (6)C9B—C4B—C5B—C6B2.5 (6)
C2A—C4A—C5A—C6A177.6 (4)C2B—C4B—C5B—C6B180.0 (4)
C4A—C5A—C6A—C7A2.8 (7)C4B—C5B—C6B—C7B2.3 (7)
C5A—C6A—C7A—C8A3.2 (7)C5B—C6B—C7B—C8B2.0 (7)
C6A—C7A—C8A—C9A1.9 (7)C6B—C7B—C8B—C9B2.1 (6)
C7A—C8A—C9A—C4A0.2 (7)C7B—C8B—C9B—C4B2.4 (6)
C5A—C4A—C9A—C8A0.2 (6)C5B—C4B—C9B—C8B2.6 (6)
C2A—C4A—C9A—C8A176.3 (4)C2B—C4B—C9B—C8B179.9 (4)
C4A—C2A—C10A—C15A20.5 (5)C4B—C2B—C10B—C11B151.4 (4)
C1A—C2A—C10A—C15A151.7 (4)C1B—C2B—C10B—C11B20.0 (5)
C3A—C2A—C10A—C15A115.0 (4)C3B—C2B—C10B—C11B73.0 (4)
C4A—C2A—C10A—C11A159.7 (3)C4B—C2B—C10B—C15B28.7 (5)
C1A—C2A—C10A—C11A28.5 (5)C1B—C2B—C10B—C15B160.0 (3)
C3A—C2A—C10A—C11A64.8 (4)C3B—C2B—C10B—C15B106.9 (4)
C15A—C10A—C11A—C12A0.7 (6)C15B—C10B—C11B—C12B1.9 (6)
C2A—C10A—C11A—C12A179.1 (3)C2B—C10B—C11B—C12B178.0 (4)
C10A—C11A—C12A—C13A0.9 (6)C10B—C11B—C12B—C13B0.5 (7)
C11A—C12A—C13A—C14A2.0 (6)C11B—C12B—C13B—C14B0.5 (7)
C12A—C13A—C14A—C15A1.5 (6)C12B—C13B—C14B—C15B0.2 (7)
C11A—C10A—C15A—C14A1.2 (6)C13B—C14B—C15B—C10B1.8 (6)
C2A—C10A—C15A—C14A178.6 (4)C11B—C10B—C15B—C14B2.6 (6)
C13A—C14A—C15A—C10A0.0 (6)C2B—C10B—C15B—C14B177.4 (4)
N1A—C3A—C16A—C17A9.7 (5)N1B—C3B—C16B—C21B17.0 (5)
C22A—C3A—C16A—C17A118.6 (4)C22B—C3B—C16B—C21B112.6 (4)
C2A—C3A—C16A—C17A104.9 (4)C2B—C3B—C16B—C21B112.7 (4)
N1A—C3A—C16A—C21A167.3 (3)N1B—C3B—C16B—C17B162.5 (4)
C22A—C3A—C16A—C21A64.4 (5)C22B—C3B—C16B—C17B67.9 (5)
C2A—C3A—C16A—C21A72.0 (4)C2B—C3B—C16B—C17B66.8 (5)
C21A—C16A—C17A—C18A1.5 (6)C21B—C16B—C17B—C18B1.0 (6)
C3A—C16A—C17A—C18A178.5 (4)C3B—C16B—C17B—C18B178.6 (4)
C16A—C17A—C18A—C19A0.1 (6)C16B—C17B—C18B—C19B1.1 (7)
C17A—C18A—C19A—C20A0.5 (6)C17B—C18B—C19B—C20B0.6 (7)
C18A—C19A—C20A—C21A0.4 (6)C18B—C19B—C20B—C21B0.0 (7)
C19A—C20A—C21A—C16A1.8 (6)C17B—C16B—C21B—C20B0.4 (6)
C17A—C16A—C21A—C20A2.3 (6)C3B—C16B—C21B—C20B179.1 (4)
C3A—C16A—C21A—C20A179.4 (4)C19B—C20B—C21B—C16B0.1 (7)
N1A—C3A—C22A—C27A142.9 (4)N1B—C3B—C22B—C23B142.1 (3)
C16A—C3A—C22A—C27A12.3 (5)C16B—C3B—C22B—C23B11.4 (5)
C2A—C3A—C22A—C27A123.3 (4)C2B—C3B—C22B—C23B122.9 (4)
N1A—C3A—C22A—C23A36.5 (5)N1B—C3B—C22B—C27B39.0 (4)
C16A—C3A—C22A—C23A167.1 (3)C16B—C3B—C22B—C27B169.7 (3)
C2A—C3A—C22A—C23A57.2 (4)C2B—C3B—C22B—C27B56.0 (4)
C27A—C22A—C23A—C24A0.8 (6)C27B—C22B—C23B—C24B3.3 (6)
C3A—C22A—C23A—C24A179.7 (4)C3B—C22B—C23B—C24B175.6 (4)
C22A—C23A—C24A—C25A0.1 (7)C22B—C23B—C24B—C25B0.3 (7)
C23A—C24A—C25A—C26A0.2 (7)C23B—C24B—C25B—C26B3.0 (7)
C24A—C25A—C26A—C27A0.1 (7)C24B—C25B—C26B—C27B2.0 (7)
C25A—C26A—C27A—C22A0.9 (7)C25B—C26B—C27B—C22B1.8 (6)
C23A—C22A—C27A—C26A1.2 (6)C23B—C22B—C27B—C26B4.4 (6)
C3A—C22A—C27A—C26A179.4 (4)C3B—C22B—C27B—C26B174.6 (4)
C1A—N1A—C28A—C33A172.3 (4)C1B—N1B—C28B—C33B165.0 (4)
C3A—N1A—C28A—C33A8.9 (6)C3B—N1B—C28B—C33B0.9 (5)
C1A—N1A—C28A—C29A10.7 (6)C1B—N1B—C28B—C29B18.1 (5)
C3A—N1A—C28A—C29A174.2 (3)C3B—N1B—C28B—C29B177.8 (3)
C33A—C28A—C29A—C30A0.5 (6)C33B—C28B—C29B—C30B1.8 (5)
N1A—C28A—C29A—C30A177.4 (3)N1B—C28B—C29B—C30B178.6 (3)
C28A—C29A—C30A—C31A1.1 (6)C28B—C29B—C30B—C31B1.7 (6)
C29A—C30A—C31A—C32A1.7 (7)C29B—C30B—C31B—C32B1.5 (6)
C30A—C31A—C32A—C33A1.7 (7)C30B—C31B—C32B—C33B1.4 (6)
C29A—C28A—C33A—C32A0.5 (6)C29B—C28B—C33B—C32B1.7 (5)
N1A—C28A—C33A—C32A177.4 (3)N1B—C28B—C33B—C32B178.5 (3)
C31A—C32A—C33A—C28A1.1 (6)C31B—C32B—C33B—C28B1.5 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5A—H5A···O1A0.932.533.191 (5)128
C5B—H5B···O1B0.932.523.162 (5)127
C6A—H6A···O1Ai0.932.543.432 (6)160
C6B—H6B···O1Bii0.932.603.303 (6)133
C29A—H29A···O1A0.932.453.067 (6)124
C29B—H29B···O1B0.932.473.070 (6)122
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+1, y, z+1.
 

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