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The title compound, C25H31NO2, crystallizes with two molecules in the asymmetric unit. In both mol­ecules, the central dihydropyridine ring adopts a flattened boat conformation. In mol­ecule A, the outer rings adopt sofa conformations, whereas in mol­ecule B, one of the outer rings is disordered and the other ring adopts a sofa conformation. In the crystal structure, C—H...O inter­actions link the mol­ecules to form a tape that runs along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805023500/bt6699sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805023500/bt6699Isup2.hkl
Contains datablock I

CCDC reference: 282255

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in main residue
  • R factor = 0.065
  • wR factor = 0.197
  • Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.70 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C7B PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3B PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6B PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C20B PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C20A PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C11B - C12B ... 1.36 Ang. PLAT410_ALERT_2_C Short Intra H...H Contact H5B2 .. H19D .. 1.95 Ang. PLAT410_ALERT_2_C Short Intra H...H Contact H4A1 .. H19A .. 1.98 Ang. PLAT410_ALERT_2_C Short Intra H...H Contact H5A2 .. H19B .. 1.95 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact C15C .. C15C .. 3.15 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 18
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 20 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

10-Benzyl-3,3,6,6,9-pentamethyl-3,4,6,7,9,10-hexahydroacridine- 1,8(2H,5H)-dione top
Crystal data top
C25H31NO2Z = 4
Mr = 377.51F(000) = 816
Triclinic, P1Dx = 1.167 Mg m3
a = 10.3359 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.8339 (3) ÅCell parameters from 4761 reflections
c = 16.2254 (4) Åθ = 1.3–28.4°
α = 101.153 (1)°µ = 0.07 mm1
β = 90.934 (1)°T = 293 K
γ = 108.687 (1)°Plate, yellow
V = 2148.53 (8) Å30.46 × 0.24 × 0.08 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
7331 independent reflections
Radiation source: fine-focus sealed tube4386 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω scansθmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1210
Tmin = 0.967, Tmax = 0.994k = 1616
11586 measured reflectionsl = 1916
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.197H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0876P)2 + 0.573P]
where P = (Fo2 + 2Fc2)/3
7331 reflections(Δ/σ)max < 0.001
563 parametersΔρmax = 0.39 e Å3
4 restraintsΔρmin = 0.21 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*/UeqOcc. (<1)
O1A0.4722 (2)0.90723 (17)0.22055 (17)0.0772 (7)
O2A0.9312 (3)1.05147 (18)0.37877 (16)0.0901 (8)
C1A0.5003 (3)0.8293 (2)0.18803 (19)0.0538 (7)
C2A0.3930 (3)0.7363 (2)0.1354 (2)0.0619 (8)
H2A10.39370.74360.07710.074*
H2A20.30360.73460.15390.074*
C3A0.4143 (3)0.6331 (2)0.14045 (18)0.0493 (7)
C4A0.5595 (3)0.6410 (2)0.11735 (17)0.0463 (7)
H4A10.57970.58090.12890.056*
H4A20.56330.63850.05730.056*
C5A1.0218 (3)0.7900 (2)0.26339 (18)0.0541 (7)
H5A11.09080.81290.22510.065*
H5A21.00060.71530.25750.065*
C6A1.0814 (3)0.8439 (2)0.35341 (18)0.0554 (8)
C7A1.0905 (4)0.9571 (3)0.3688 (2)0.0708 (10)
H7A11.16310.99360.33770.085*
H7A21.11550.98760.42830.085*
C8A0.9594 (4)0.9744 (2)0.3435 (2)0.0626 (9)
C9A0.7486 (3)0.9251 (2)0.24202 (17)0.0481 (7)
H9A0.71060.95710.29070.058*
N10A0.8009 (2)0.73471 (16)0.17648 (13)0.0419 (5)
C11A0.6388 (3)0.8260 (2)0.19721 (16)0.0442 (7)
C12A0.6681 (3)0.7388 (2)0.16439 (15)0.0402 (6)
C13A0.8681 (3)0.8985 (2)0.27382 (16)0.0476 (7)
C14A0.8948 (3)0.8111 (2)0.23800 (16)0.0438 (7)
C15A0.3947 (3)0.6133 (3)0.2293 (2)0.0665 (9)
H15A0.45970.66930.26870.100*
H15B0.40860.54860.23220.100*
H15C0.30340.60940.24290.100*
C16A0.3121 (3)0.5418 (2)0.0785 (2)0.0708 (10)
H16A0.22090.53290.09500.106*
H16B0.33320.47920.07870.106*
H16C0.31790.55610.02280.106*
C17A0.9860 (4)0.7895 (3)0.4149 (2)0.0765 (10)
H17A1.02250.82290.47190.115*
H17B0.97970.71740.40520.115*
H17C0.89640.79440.40600.115*
C18A1.2208 (4)0.8325 (3)0.3690 (2)0.0820 (11)
H18A1.28260.86550.33150.123*
H18B1.21150.75980.35920.123*
H18C1.25630.86510.42630.123*
C19A0.8460 (3)0.6574 (2)0.12045 (16)0.0461 (7)
H19A0.76600.60220.09050.055*
H19B0.89340.62650.15430.055*
C20A0.9404 (3)0.7026 (2)0.05654 (16)0.0439 (7)
C21A1.0332 (3)0.6548 (3)0.0253 (2)0.0667 (9)
H21A1.04010.59820.04580.080*
C22A1.1160 (4)0.6903 (4)0.0360 (2)0.0873 (12)
H22A1.17750.65700.05690.105*
C23A1.1080 (4)0.7742 (4)0.0661 (2)0.0877 (12)
H23A1.16400.79830.10720.105*
C24A1.0170 (4)0.8222 (3)0.0354 (2)0.0841 (11)
H24A1.01160.87960.05530.101*
C25A0.9328 (3)0.7860 (3)0.0250 (2)0.0665 (9)
H25A0.87000.81860.04460.080*
C26A0.7945 (3)1.0037 (2)0.1845 (2)0.0669 (9)
H26A0.83550.97470.13750.100*
H26B0.86021.06700.21570.100*
H26C0.71651.01840.16420.100*
O1B1.0154 (14)0.5503 (8)0.2621 (7)0.085 (3)0.591 (8)
O1C1.0131 (18)0.5191 (13)0.2229 (9)0.081 (4)0.409 (8)
O2B0.5422 (3)0.39163 (19)0.10778 (16)0.0900 (8)
C1B0.9887 (8)0.4786 (6)0.2998 (6)0.0598 (19)0.591 (8)
C2B1.0937 (6)0.4729 (5)0.3621 (5)0.070 (2)0.591 (8)
H2B11.08210.50760.41810.084*0.591 (8)
H2B21.18490.50880.34770.084*0.591 (8)
C1C0.9858 (11)0.4425 (9)0.2549 (8)0.063 (3)0.409 (8)
C2C1.0951 (8)0.4015 (8)0.2801 (7)0.080 (4)0.409 (8)
H2C11.18290.45660.28530.096*0.409 (8)
H2C21.09770.34490.23500.096*0.409 (8)
C3B1.0791 (3)0.3619 (3)0.3619 (2)0.0664 (9)
C4B0.9347 (3)0.2928 (3)0.3690 (2)0.0678 (9)
H4B10.92950.22060.35040.081*
H4B20.91650.30280.42800.081*
C5B0.4637 (3)0.1477 (2)0.2327 (2)0.0649 (9)
H5B10.40350.15490.27690.078*
H5B20.48670.08520.23370.078*
C6B0.3864 (3)0.1335 (3)0.1481 (2)0.0675 (9)
C7B0.3792 (4)0.2352 (3)0.1336 (3)0.0907 (12)
H7B10.31670.25680.17100.109*
H7B20.34200.22530.07610.109*
C8B0.5168 (4)0.3210 (3)0.1481 (2)0.0682 (9)
C9B0.7371 (3)0.4195 (2)0.24051 (19)0.0531 (7)
H9B0.77020.44590.19020.064*
N10B0.6923 (2)0.23894 (17)0.31107 (14)0.0470 (6)
C11B0.8495 (3)0.3946 (2)0.2814 (2)0.0591 (8)
C12B0.8244 (3)0.3118 (2)0.31939 (18)0.0502 (7)
C13B0.6157 (3)0.3227 (2)0.21331 (18)0.0518 (7)
C14B0.5933 (3)0.2405 (2)0.25176 (17)0.0481 (7)
C15B1.1193 (7)0.3085 (5)0.2790 (3)0.092 (3)0.591 (8)
H15D1.21190.34650.27040.138*0.591 (8)
H15E1.05880.30720.23300.138*0.591 (8)
H15F1.11240.23830.28180.138*0.591 (8)
C16B1.1783 (11)0.3579 (10)0.4314 (6)0.100 (4)0.591 (8)
H16D1.16570.28640.43300.151*0.591 (8)
H16E1.16040.39290.48490.151*0.591 (8)
H16F1.27090.39170.42000.151*0.591 (8)
C15C1.0842 (11)0.4562 (7)0.4313 (6)0.111 (5)0.409 (8)
H15G1.08490.43780.48540.167*0.409 (8)
H15H1.00510.47640.42280.167*0.409 (8)
H15I1.16570.51340.42910.167*0.409 (8)
C16C1.1882 (16)0.3152 (16)0.3830 (13)0.117 (7)0.409 (8)
H16G1.17970.25370.34100.176*0.409 (8)
H16H1.17570.29720.43730.176*0.409 (8)
H16I1.27770.36540.38400.176*0.409 (8)
C17B0.4652 (5)0.0897 (4)0.0788 (3)0.1104 (15)
H17D0.41680.07720.02480.166*
H17E0.47260.02540.08870.166*
H17F0.55520.13910.07990.166*
C18B0.2454 (4)0.0513 (3)0.1425 (3)0.1157 (17)
H18D0.19260.07500.18500.174*
H18E0.25540.01280.15120.174*
H18F0.19940.03970.08790.174*
C19B0.6519 (3)0.1646 (2)0.36738 (19)0.0553 (8)
H19C0.73390.15980.39380.066*
H19D0.60080.09610.33400.066*
C20B0.5660 (3)0.1950 (3)0.43488 (18)0.0554 (8)
C21B0.4697 (4)0.1179 (3)0.4655 (2)0.0867 (13)
H21B0.45650.04800.44290.104*
C22B0.3925 (4)0.1448 (5)0.5301 (3)0.123 (2)
H22B0.32770.09260.55020.147*
C23B0.4112 (5)0.2467 (6)0.5640 (3)0.130 (2)
H23B0.35970.26400.60740.156*
C24B0.5042 (5)0.3226 (4)0.5347 (3)0.1116 (16)
H24B0.51680.39230.55770.134*
C25B0.5811 (4)0.2966 (3)0.4702 (2)0.0819 (11)
H25B0.64470.34970.45030.098*
C26B0.6971 (4)0.5045 (3)0.2999 (2)0.0760 (10)
H26D0.62550.51950.27190.114*
H26E0.77550.56670.31490.114*
H26F0.66540.48040.34990.114*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0722 (15)0.0482 (13)0.1143 (19)0.0307 (12)0.0095 (13)0.0057 (13)
O2A0.131 (2)0.0534 (14)0.0774 (16)0.0403 (15)0.0334 (15)0.0194 (12)
C1A0.0606 (19)0.0413 (17)0.0641 (19)0.0224 (15)0.0064 (15)0.0120 (14)
C2A0.059 (2)0.0567 (19)0.072 (2)0.0248 (16)0.0042 (16)0.0097 (16)
C3A0.0442 (16)0.0462 (16)0.0543 (17)0.0123 (13)0.0010 (13)0.0080 (13)
C4A0.0510 (17)0.0416 (15)0.0436 (15)0.0138 (13)0.0006 (13)0.0055 (12)
C5A0.0565 (18)0.0489 (17)0.0543 (17)0.0159 (14)0.0014 (14)0.0075 (14)
C6A0.0527 (18)0.0536 (19)0.0512 (17)0.0085 (14)0.0076 (14)0.0066 (14)
C7A0.078 (2)0.057 (2)0.064 (2)0.0105 (17)0.0172 (17)0.0038 (16)
C8A0.086 (2)0.0390 (17)0.0554 (18)0.0162 (16)0.0155 (17)0.0016 (14)
C9A0.0636 (19)0.0352 (15)0.0460 (16)0.0187 (13)0.0028 (13)0.0059 (12)
N10A0.0436 (13)0.0367 (12)0.0416 (12)0.0124 (10)0.0031 (10)0.0011 (10)
C11A0.0521 (17)0.0384 (15)0.0432 (15)0.0153 (13)0.0050 (12)0.0101 (12)
C12A0.0486 (16)0.0369 (15)0.0341 (13)0.0123 (12)0.0055 (12)0.0079 (11)
C13A0.0625 (18)0.0364 (15)0.0419 (15)0.0156 (13)0.0020 (13)0.0053 (12)
C14A0.0512 (16)0.0397 (15)0.0383 (14)0.0115 (13)0.0010 (12)0.0091 (12)
C15A0.061 (2)0.067 (2)0.072 (2)0.0173 (17)0.0169 (17)0.0217 (17)
C16A0.055 (2)0.057 (2)0.090 (2)0.0148 (16)0.0155 (18)0.0006 (18)
C17A0.085 (3)0.082 (3)0.060 (2)0.019 (2)0.0021 (18)0.0234 (18)
C18A0.067 (2)0.079 (3)0.091 (3)0.0182 (19)0.023 (2)0.009 (2)
C19A0.0476 (16)0.0399 (15)0.0456 (15)0.0124 (12)0.0002 (13)0.0004 (12)
C20A0.0408 (15)0.0496 (17)0.0368 (14)0.0143 (13)0.0041 (12)0.0003 (12)
C21A0.070 (2)0.076 (2)0.064 (2)0.0398 (19)0.0112 (17)0.0112 (17)
C22A0.073 (2)0.137 (4)0.068 (2)0.058 (3)0.025 (2)0.017 (2)
C23A0.076 (3)0.131 (4)0.060 (2)0.031 (3)0.0192 (19)0.032 (2)
C24A0.101 (3)0.100 (3)0.067 (2)0.041 (2)0.025 (2)0.038 (2)
C25A0.077 (2)0.073 (2)0.063 (2)0.0377 (19)0.0190 (17)0.0232 (18)
C26A0.076 (2)0.0485 (18)0.075 (2)0.0150 (16)0.0049 (18)0.0220 (16)
O1B0.077 (4)0.058 (5)0.126 (8)0.013 (4)0.014 (6)0.050 (5)
O1C0.062 (5)0.071 (9)0.122 (11)0.013 (6)0.026 (8)0.064 (7)
O2B0.124 (2)0.0712 (16)0.0807 (17)0.0293 (15)0.0188 (15)0.0371 (14)
C1B0.065 (4)0.044 (4)0.075 (5)0.016 (3)0.011 (4)0.025 (4)
C2B0.060 (4)0.057 (4)0.086 (5)0.005 (3)0.006 (3)0.024 (3)
C1C0.057 (6)0.051 (7)0.074 (8)0.005 (5)0.006 (6)0.019 (6)
C2C0.049 (5)0.085 (8)0.118 (9)0.018 (5)0.016 (5)0.054 (7)
C3B0.055 (2)0.069 (2)0.074 (2)0.0107 (17)0.0010 (17)0.0275 (18)
C4B0.0551 (19)0.064 (2)0.093 (2)0.0173 (16)0.0044 (17)0.0397 (19)
C5B0.067 (2)0.0486 (18)0.074 (2)0.0102 (16)0.0048 (17)0.0181 (16)
C6B0.067 (2)0.059 (2)0.071 (2)0.0180 (17)0.0070 (17)0.0080 (17)
C7B0.091 (3)0.079 (3)0.102 (3)0.026 (2)0.023 (2)0.024 (2)
C8B0.090 (3)0.056 (2)0.062 (2)0.0270 (18)0.0095 (18)0.0157 (17)
C9B0.0643 (19)0.0430 (16)0.0589 (18)0.0206 (14)0.0093 (15)0.0218 (14)
N10B0.0518 (14)0.0402 (13)0.0522 (14)0.0140 (11)0.0077 (11)0.0194 (11)
C11B0.0518 (18)0.0520 (18)0.084 (2)0.0186 (15)0.0161 (16)0.0362 (17)
C12B0.0494 (17)0.0464 (17)0.0597 (18)0.0172 (14)0.0115 (14)0.0197 (14)
C13B0.0664 (19)0.0447 (17)0.0489 (16)0.0213 (14)0.0063 (14)0.0151 (13)
C14B0.0568 (18)0.0429 (16)0.0469 (16)0.0184 (14)0.0045 (14)0.0118 (13)
C15B0.077 (4)0.105 (6)0.109 (6)0.043 (4)0.038 (4)0.032 (4)
C16B0.052 (5)0.098 (9)0.159 (9)0.015 (4)0.001 (6)0.061 (7)
C15C0.098 (8)0.103 (9)0.101 (9)0.008 (6)0.031 (7)0.019 (7)
C16C0.053 (7)0.120 (16)0.206 (19)0.039 (9)0.012 (11)0.080 (14)
C17B0.134 (4)0.109 (4)0.081 (3)0.048 (3)0.004 (3)0.009 (3)
C18B0.091 (3)0.086 (3)0.147 (4)0.001 (2)0.045 (3)0.028 (3)
C19B0.0564 (18)0.0469 (17)0.0658 (19)0.0109 (14)0.0023 (15)0.0299 (15)
C20B0.0437 (17)0.070 (2)0.0471 (16)0.0053 (15)0.0040 (14)0.0234 (15)
C21B0.065 (2)0.103 (3)0.067 (2)0.015 (2)0.0019 (19)0.032 (2)
C22B0.067 (3)0.191 (6)0.070 (3)0.025 (3)0.008 (2)0.046 (3)
C23B0.069 (3)0.217 (7)0.062 (3)0.008 (4)0.004 (2)0.000 (4)
C24B0.112 (4)0.139 (4)0.071 (3)0.040 (3)0.018 (3)0.008 (3)
C25B0.087 (3)0.084 (3)0.067 (2)0.019 (2)0.015 (2)0.013 (2)
C26B0.082 (2)0.056 (2)0.091 (3)0.0281 (18)0.005 (2)0.0092 (18)
Geometric parameters (Å, º) top
O1A—C1A1.229 (3)C2B—H2B20.9700
O2A—C8A1.232 (4)C1C—C11B1.463 (12)
C1A—C11A1.452 (4)C1C—C2C1.501 (15)
C1A—C2A1.499 (4)C2C—C3B1.522 (10)
C2A—C3A1.530 (4)C2C—H2C10.9700
C2A—H2A10.9700C2C—H2C20.9700
C2A—H2A20.9700C3B—C16C1.533 (2)
C3A—C15A1.524 (4)C3B—C4B1.512 (4)
C3A—C4A1.527 (4)C3B—C15B1.536 (2)
C3A—C16A1.530 (4)C3B—C15C1.536 (2)
C4A—C12A1.508 (3)C3B—C16B1.534 (2)
C4A—H4A10.9700C4B—C12B1.503 (4)
C4A—H4A20.9700C4B—H4B10.9700
C5A—C14A1.501 (4)C4B—H4B20.9700
C5A—C6A1.524 (4)C5B—C14B1.506 (4)
C5A—H5A10.9700C5B—C6B1.523 (4)
C5A—H5A20.9700C5B—H5B10.9700
C6A—C7A1.509 (4)C5B—H5B20.9700
C6A—C18A1.521 (5)C6B—C7B1.495 (5)
C6A—C17A1.544 (4)C6B—C18B1.523 (5)
C7A—C8A1.513 (5)C6B—C17B1.541 (5)
C7A—H7A10.9700C7B—C8B1.513 (5)
C7A—H7A20.9700C7B—H7B10.9700
C8A—C13A1.463 (4)C7B—H7B20.9700
C9A—C13A1.507 (4)C8B—C13B1.451 (4)
C9A—C11A1.512 (4)C9B—C11B1.493 (4)
C9A—C26A1.535 (4)C9B—C13B1.497 (4)
C9A—H9A0.9800C9B—C26B1.539 (4)
N10A—C14A1.399 (3)C9B—H9B0.9800
N10A—C12A1.404 (3)N10B—C12B1.399 (3)
N10A—C19A1.465 (3)N10B—C14B1.402 (4)
C11A—C12A1.349 (4)N10B—C19B1.472 (3)
C13A—C14A1.350 (4)C11B—C12B1.359 (4)
C15A—H15A0.9600C13B—C14B1.359 (4)
C15A—H15B0.9600C15B—H15D0.9600
C15A—H15C0.9600C15B—H15E0.9600
C16A—H16A0.9600C15B—H15F0.9600
C16A—H16B0.9600C16B—H16D0.9600
C16A—H16C0.9600C16B—H16E0.9600
C17A—H17A0.9600C16B—H16F0.9600
C17A—H17B0.9600C15C—H15G0.9600
C17A—H17C0.9600C15C—H15H0.9600
C18A—H18A0.9600C15C—H15I0.9600
C18A—H18B0.9600C16C—H16G0.9600
C18A—H18C0.9600C16C—H16H0.9600
C19A—C20A1.520 (4)C16C—H16I0.9600
C19A—H19A0.9700C17B—H17D0.9600
C19A—H19B0.9700C17B—H17E0.9600
C20A—C25A1.373 (4)C17B—H17F0.9600
C20A—C21A1.380 (4)C18B—H18D0.9600
C21A—C22A1.383 (5)C18B—H18E0.9600
C21A—H21A0.9300C18B—H18F0.9600
C22A—C23A1.368 (6)C19B—C20B1.503 (4)
C22A—H22A0.9300C19B—H19C0.9700
C23A—C24A1.364 (5)C19B—H19D0.9700
C23A—H23A0.9300C20B—C25B1.369 (5)
C24A—C25A1.381 (5)C20B—C21B1.383 (4)
C24A—H24A0.9300C21B—C22B1.393 (6)
C25A—H25A0.9300C21B—H21B0.9300
C26A—H26A0.9600C22B—C23B1.360 (8)
C26A—H26B0.9600C22B—H22B0.9300
C26A—H26C0.9600C23B—C24B1.346 (7)
O1B—C1B1.225 (13)C23B—H23B0.9300
O1C—C1C1.223 (19)C24B—C25B1.386 (5)
O2B—C8B1.241 (4)C24B—H24B0.9300
C1B—C2B1.501 (11)C25B—H25B0.9300
C1B—C11B1.514 (8)C26B—H26D0.9600
C2B—C3B1.494 (7)C26B—H26E0.9600
C2B—H2B10.9700C26B—H26F0.9600
O1A—C1A—C11A121.2 (3)C3B—C2C—H2C2108.3
O1A—C1A—C2A120.6 (3)H2C1—C2C—H2C2107.4
C11A—C1A—C2A118.3 (3)C16C—C3B—C2B129.2 (9)
C1A—C2A—C3A113.0 (2)C16C—C3B—C4B113.0 (8)
C1A—C2A—H2A1109.0C2B—C3B—C4B114.8 (3)
C3A—C2A—H2A1109.0C16C—C3B—C2C114.4 (9)
C1A—C2A—H2A2109.0C2B—C3B—C2C59.6 (5)
C3A—C2A—H2A2109.0C4B—C3B—C2C113.1 (4)
H2A1—C2A—H2A2107.8C16C—C3B—C15B71.6 (8)
C15A—C3A—C4A110.7 (2)C2B—C3B—C15B111.6 (5)
C15A—C3A—C2A109.8 (3)C4B—C3B—C15B104.0 (4)
C4A—C3A—C2A107.9 (2)C2C—C3B—C15B53.8 (5)
C15A—C3A—C16A108.6 (3)C16C—C3B—C15C110.5 (9)
C4A—C3A—C16A108.8 (2)C2B—C3B—C15C46.2 (5)
C2A—C3A—C16A111.0 (2)C4B—C3B—C15C98.6 (5)
C12A—C4A—C3A113.7 (2)C2C—C3B—C15C105.8 (7)
C12A—C4A—H4A1108.8C15B—C3B—C15C154.3 (6)
C3A—C4A—H4A1108.8C2B—C3B—C16B109.6 (6)
C12A—C4A—H4A2108.8C4B—C3B—C16B110.8 (5)
C3A—C4A—H4A2108.8C2C—C3B—C16B134.9 (6)
H4A1—C4A—H4A2107.7C15B—C3B—C16B105.7 (6)
C14A—C5A—C6A113.9 (2)C15C—C3B—C16B76.9 (6)
C14A—C5A—H5A1108.8C12B—C4B—C3B115.0 (3)
C6A—C5A—H5A1108.8C12B—C4B—H4B1108.5
C14A—C5A—H5A2108.8C3B—C4B—H4B1108.5
C6A—C5A—H5A2108.8C12B—C4B—H4B2108.5
H5A1—C5A—H5A2107.7C3B—C4B—H4B2108.5
C7A—C6A—C18A111.5 (3)H4B1—C4B—H4B2107.5
C7A—C6A—C5A109.7 (3)C14B—C5B—C6B114.4 (3)
C18A—C6A—C5A110.2 (3)C14B—C5B—H5B1108.7
C7A—C6A—C17A109.2 (3)C6B—C5B—H5B1108.7
C18A—C6A—C17A107.4 (3)C14B—C5B—H5B2108.7
C5A—C6A—C17A108.7 (2)C6B—C5B—H5B2108.7
C6A—C7A—C8A114.2 (3)H5B1—C5B—H5B2107.6
C6A—C7A—H7A1108.7C7B—C6B—C5B111.2 (3)
C8A—C7A—H7A1108.7C7B—C6B—C18B112.5 (3)
C6A—C7A—H7A2108.7C5B—C6B—C18B109.9 (3)
C8A—C7A—H7A2108.7C7B—C6B—C17B109.0 (4)
H7A1—C7A—H7A2107.6C5B—C6B—C17B107.5 (3)
O2A—C8A—C13A120.5 (3)C18B—C6B—C17B106.4 (4)
O2A—C8A—C7A121.3 (3)C6B—C7B—C8B113.2 (3)
C13A—C8A—C7A118.2 (3)C6B—C7B—H7B1108.9
C13A—C9A—C11A109.4 (2)C8B—C7B—H7B1108.9
C13A—C9A—C26A111.0 (2)C6B—C7B—H7B2108.9
C11A—C9A—C26A111.5 (2)C8B—C7B—H7B2108.9
C13A—C9A—H9A108.3H7B1—C7B—H7B2107.8
C11A—C9A—H9A108.3O2B—C8B—C13B120.5 (3)
C26A—C9A—H9A108.3O2B—C8B—C7B120.5 (3)
C14A—N10A—C12A119.4 (2)C13B—C8B—C7B118.8 (3)
C14A—N10A—C19A119.6 (2)C11B—C9B—C13B110.0 (2)
C12A—N10A—C19A120.7 (2)C11B—C9B—C26B111.2 (3)
C12A—C11A—C1A121.0 (3)C13B—C9B—C26B110.8 (3)
C12A—C11A—C9A121.7 (3)C11B—C9B—H9B108.2
C1A—C11A—C9A117.2 (2)C13B—C9B—H9B108.2
C11A—C12A—N10A120.7 (2)C26B—C9B—H9B108.2
C11A—C12A—C4A121.8 (2)C12B—N10B—C14B119.8 (2)
N10A—C12A—C4A117.4 (2)C12B—N10B—C19B121.3 (2)
C14A—C13A—C8A120.7 (3)C14B—N10B—C19B118.8 (2)
C14A—C13A—C9A122.2 (2)C12B—C11B—C1C120.5 (5)
C8A—C13A—C9A117.1 (3)C12B—C11B—C9B122.2 (3)
C13A—C14A—N10A120.2 (2)C1C—C11B—C9B114.6 (5)
C13A—C14A—C5A122.3 (2)C12B—C11B—C1B118.5 (4)
N10A—C14A—C5A117.4 (2)C9B—C11B—C1B117.5 (4)
C3A—C15A—H15A109.5C11B—C12B—N10B119.7 (3)
C3A—C15A—H15B109.5C11B—C12B—C4B122.6 (3)
H15A—C15A—H15B109.5N10B—C12B—C4B117.7 (2)
C3A—C15A—H15C109.5C14B—C13B—C8B120.3 (3)
H15A—C15A—H15C109.5C14B—C13B—C9B121.3 (3)
H15B—C15A—H15C109.5C8B—C13B—C9B118.2 (2)
C3A—C16A—H16A109.5C13B—C14B—N10B120.5 (3)
C3A—C16A—H16B109.5C13B—C14B—C5B122.3 (3)
H16A—C16A—H16B109.5N10B—C14B—C5B117.2 (2)
C3A—C16A—H16C109.5C3B—C15B—H15D109.5
H16A—C16A—H16C109.5C3B—C15B—H15E109.5
H16B—C16A—H16C109.5C3B—C15B—H15F109.5
C6A—C17A—H17A109.5C3B—C16B—H16D109.5
C6A—C17A—H17B109.5C3B—C16B—H16E109.5
H17A—C17A—H17B109.5C3B—C16B—H16F109.5
C6A—C17A—H17C109.5C3B—C15C—H15G109.5
H17A—C17A—H17C109.5C3B—C15C—H15H109.5
H17B—C17A—H17C109.5H15G—C15C—H15H109.5
C6A—C18A—H18A109.5C3B—C15C—H15I109.5
C6A—C18A—H18B109.5H15G—C15C—H15I109.5
H18A—C18A—H18B109.5H15H—C15C—H15I109.5
C6A—C18A—H18C109.5C3B—C16C—H16G109.5
H18A—C18A—H18C109.5C3B—C16C—H16H109.5
H18B—C18A—H18C109.5H16G—C16C—H16H109.5
N10A—C19A—C20A113.5 (2)C3B—C16C—H16I109.5
N10A—C19A—H19A108.9H16G—C16C—H16I109.5
C20A—C19A—H19A108.9H16H—C16C—H16I109.5
N10A—C19A—H19B108.9C6B—C17B—H17D109.5
C20A—C19A—H19B108.9C6B—C17B—H17E109.5
H19A—C19A—H19B107.7H17D—C17B—H17E109.5
C25A—C20A—C21A118.1 (3)C6B—C17B—H17F109.5
C25A—C20A—C19A122.8 (3)H17D—C17B—H17F109.5
C21A—C20A—C19A118.9 (3)H17E—C17B—H17F109.5
C20A—C21A—C22A120.7 (3)C6B—C18B—H18D109.5
C20A—C21A—H21A119.6C6B—C18B—H18E109.5
C22A—C21A—H21A119.6H18D—C18B—H18E109.5
C23A—C22A—C21A120.3 (4)C6B—C18B—H18F109.5
C23A—C22A—H22A119.8H18D—C18B—H18F109.5
C21A—C22A—H22A119.8H18E—C18B—H18F109.5
C24A—C23A—C22A119.4 (4)N10B—C19B—C20B113.1 (2)
C24A—C23A—H23A120.3N10B—C19B—H19C109.0
C22A—C23A—H23A120.3C20B—C19B—H19C109.0
C23A—C24A—C25A120.4 (4)N10B—C19B—H19D109.0
C23A—C24A—H24A119.8C20B—C19B—H19D109.0
C25A—C24A—H24A119.8H19C—C19B—H19D107.8
C20A—C25A—C24A121.0 (3)C25B—C20B—C21B117.6 (3)
C20A—C25A—H25A119.5C25B—C20B—C19B123.0 (3)
C24A—C25A—H25A119.5C21B—C20B—C19B119.4 (3)
C9A—C26A—H26A109.5C20B—C21B—C22B120.1 (4)
C9A—C26A—H26B109.5C20B—C21B—H21B119.9
H26A—C26A—H26B109.5C22B—C21B—H21B119.9
C9A—C26A—H26C109.5C23B—C22B—C21B120.6 (4)
H26A—C26A—H26C109.5C23B—C22B—H22B119.7
H26B—C26A—H26C109.5C21B—C22B—H22B119.7
O1B—C1B—C2B120.5 (9)C24B—C23B—C22B120.0 (5)
O1B—C1B—C11B119.1 (9)C24B—C23B—H23B120.0
C2B—C1B—C11B120.4 (5)C22B—C23B—H23B120.0
C1B—C2B—C3B110.5 (5)C23B—C24B—C25B119.9 (5)
C1B—C2B—H2B1109.5C23B—C24B—H24B120.1
C3B—C2B—H2B1109.5C25B—C24B—H24B120.1
C1B—C2B—H2B2109.5C20B—C25B—C24B121.8 (4)
C3B—C2B—H2B2109.5C20B—C25B—H25B119.1
H2B1—C2B—H2B2108.1C24B—C25B—H25B119.1
O1C—C1C—C11B122.2 (13)C9B—C26B—H26D109.5
O1C—C1C—C2C121.6 (12)C9B—C26B—H26E109.5
C11B—C1C—C2C115.7 (8)H26D—C26B—H26E109.5
C1C—C2C—C3B116.0 (8)C9B—C26B—H26F109.5
C1C—C2C—H2C1108.3H26D—C26B—H26F109.5
C3B—C2C—H2C1108.3H26E—C26B—H26F109.5
C1C—C2C—H2C2108.3
O1A—C1A—C2A—C3A148.3 (3)C1C—C2C—C3B—C15B136.4 (11)
C11A—C1A—C2A—C3A33.6 (4)C1C—C2C—C3B—C15C61.3 (10)
C1A—C2A—C3A—C15A66.2 (3)C1C—C2C—C3B—C16B148.5 (10)
C1A—C2A—C3A—C4A54.6 (3)C16C—C3B—C4B—C12B157.8 (9)
C1A—C2A—C3A—C16A173.7 (3)C2B—C3B—C4B—C12B40.1 (5)
C15A—C3A—C4A—C12A70.6 (3)C2C—C3B—C4B—C12B25.8 (6)
C2A—C3A—C4A—C12A49.5 (3)C15B—C3B—C4B—C12B82.1 (5)
C16A—C3A—C4A—C12A170.1 (2)C15C—C3B—C4B—C12B85.5 (6)
C14A—C5A—C6A—C7A48.0 (3)C16B—C3B—C4B—C12B164.8 (6)
C14A—C5A—C6A—C18A171.1 (3)C14B—C5B—C6B—C7B44.0 (4)
C14A—C5A—C6A—C17A71.4 (3)C14B—C5B—C6B—C18B169.3 (3)
C18A—C6A—C7A—C8A172.4 (3)C14B—C5B—C6B—C17B75.3 (4)
C5A—C6A—C7A—C8A50.1 (4)C5B—C6B—C7B—C8B50.0 (5)
C17A—C6A—C7A—C8A69.0 (4)C18B—C6B—C7B—C8B173.8 (4)
C6A—C7A—C8A—O2A152.0 (3)C17B—C6B—C7B—C8B68.3 (4)
C6A—C7A—C8A—C13A29.9 (4)C6B—C7B—C8B—O2B149.5 (4)
O1A—C1A—C11A—C12A177.2 (3)C6B—C7B—C8B—C13B34.0 (5)
C2A—C1A—C11A—C12A4.7 (4)O1C—C1C—C11B—C12B177.7 (10)
O1A—C1A—C11A—C9A5.0 (4)C2C—C1C—C11B—C12B5.9 (13)
C2A—C1A—C11A—C9A173.1 (2)O1C—C1C—C11B—C9B20.8 (14)
C13A—C9A—C11A—C12A23.1 (3)C2C—C1C—C11B—C9B167.5 (8)
C26A—C9A—C11A—C12A100.2 (3)O1C—C1C—C11B—C1B82.2 (16)
C13A—C9A—C11A—C1A159.2 (2)C2C—C1C—C11B—C1B89.6 (16)
C26A—C9A—C11A—C1A77.6 (3)C13B—C9B—C11B—C12B25.6 (4)
C1A—C11A—C12A—N10A177.3 (2)C26B—C9B—C11B—C12B97.5 (4)
C9A—C11A—C12A—N10A5.0 (4)C13B—C9B—C11B—C1C135.6 (6)
C1A—C11A—C12A—C4A0.4 (4)C26B—C9B—C11B—C1C101.3 (6)
C9A—C11A—C12A—C4A178.1 (2)C13B—C9B—C11B—C1B169.9 (4)
C14A—N10A—C12A—C11A14.6 (4)C26B—C9B—C11B—C1B66.9 (5)
C19A—N10A—C12A—C11A159.7 (2)O1B—C1B—C11B—C12B175.6 (7)
C14A—N10A—C12A—C4A162.5 (2)C2B—C1B—C11B—C12B3.1 (9)
C19A—N10A—C12A—C4A23.2 (3)O1B—C1B—C11B—C1C73.2 (14)
C3A—C4A—C12A—C11A23.7 (4)C2B—C1B—C11B—C1C105.6 (16)
C3A—C4A—C12A—N10A153.3 (2)O1B—C1B—C11B—C9B19.4 (10)
O2A—C8A—C13A—C14A176.4 (3)C2B—C1B—C11B—C9B161.9 (6)
C7A—C8A—C13A—C14A5.5 (4)C1C—C11B—C12B—N10B151.5 (6)
O2A—C8A—C13A—C9A6.4 (4)C9B—C11B—C12B—N10B8.7 (5)
C7A—C8A—C13A—C9A171.8 (3)C1B—C11B—C12B—N10B172.9 (4)
C11A—C9A—C13A—C14A24.9 (4)C1C—C11B—C12B—C4B26.8 (8)
C26A—C9A—C13A—C14A98.6 (3)C9B—C11B—C12B—C4B173.0 (3)
C11A—C9A—C13A—C8A157.9 (2)C1B—C11B—C12B—C4B8.7 (6)
C26A—C9A—C13A—C8A78.6 (3)C14B—N10B—C12B—C11B11.7 (4)
C8A—C13A—C14A—N10A174.4 (2)C19B—N10B—C12B—C11B164.1 (3)
C9A—C13A—C14A—N10A8.5 (4)C14B—N10B—C12B—C4B166.7 (3)
C8A—C13A—C14A—C5A3.8 (4)C19B—N10B—C12B—C4B17.4 (4)
C9A—C13A—C14A—C5A173.3 (3)C3B—C4B—C12B—C11B9.6 (5)
C12A—N10A—C14A—C13A12.8 (4)C3B—C4B—C12B—N10B168.8 (3)
C19A—N10A—C14A—C13A161.5 (2)O2B—C8B—C13B—C14B173.7 (3)
C12A—N10A—C14A—C5A165.5 (2)C7B—C8B—C13B—C14B9.8 (5)
C19A—N10A—C14A—C5A20.2 (3)O2B—C8B—C13B—C9B10.1 (5)
C6A—C5A—C14A—C13A26.2 (4)C7B—C8B—C13B—C9B166.4 (3)
C6A—C5A—C14A—N10A152.1 (2)C11B—C9B—C13B—C14B25.1 (4)
C14A—N10A—C19A—C20A70.8 (3)C26B—C9B—C13B—C14B98.2 (3)
C12A—N10A—C19A—C20A103.5 (3)C11B—C9B—C13B—C8B158.8 (3)
N10A—C19A—C20A—C25A30.2 (4)C26B—C9B—C13B—C8B77.9 (3)
N10A—C19A—C20A—C21A153.2 (2)C8B—C13B—C14B—N10B176.0 (3)
C25A—C20A—C21A—C22A0.0 (5)C9B—C13B—C14B—N10B8.0 (4)
C19A—C20A—C21A—C22A176.7 (3)C8B—C13B—C14B—C5B3.4 (5)
C20A—C21A—C22A—C23A0.6 (6)C9B—C13B—C14B—C5B172.6 (3)
C21A—C22A—C23A—C24A0.3 (6)C12B—N10B—C14B—C13B12.1 (4)
C22A—C23A—C24A—C25A0.6 (6)C19B—N10B—C14B—C13B163.9 (3)
C21A—C20A—C25A—C24A0.9 (5)C12B—N10B—C14B—C5B167.4 (3)
C19A—C20A—C25A—C24A177.5 (3)C19B—N10B—C14B—C5B16.6 (4)
C23A—C24A—C25A—C20A1.2 (6)C6B—C5B—C14B—C13B21.2 (5)
O1B—C1B—C2B—C3B146.9 (8)C6B—C5B—C14B—N10B158.3 (3)
C11B—C1B—C2B—C3B31.8 (9)C12B—N10B—C19B—C20B102.5 (3)
O1C—C1C—C2C—C3B141.5 (11)C14B—N10B—C19B—C20B73.4 (3)
C11B—C1C—C2C—C3B30.4 (14)N10B—C19B—C20B—C25B32.5 (4)
C1B—C2B—C3B—C16C151.8 (12)N10B—C19B—C20B—C21B149.6 (3)
C1B—C2B—C3B—C4B49.5 (7)C25B—C20B—C21B—C22B0.2 (5)
C1B—C2B—C3B—C2C53.8 (6)C19B—C20B—C21B—C22B177.8 (3)
C1B—C2B—C3B—C15B68.4 (7)C20B—C21B—C22B—C23B0.3 (7)
C1B—C2B—C3B—C15C127.2 (9)C21B—C22B—C23B—C24B0.5 (8)
C1B—C2B—C3B—C16B174.9 (7)C22B—C23B—C24B—C25B0.2 (8)
C1C—C2C—C3B—C16C176.8 (12)C21B—C20B—C25B—C24B0.5 (6)
C1C—C2C—C3B—C2B60.6 (9)C19B—C20B—C25B—C24B177.4 (4)
C1C—C2C—C3B—C4B45.6 (10)C23B—C24B—C25B—C20B0.3 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4A—H4A1···O2B0.972.473.369 (4)153
C5A—H5A2···O1B0.972.353.291 (12)163
C4B—H4B1···O2Ai0.972.483.362 (4)152
C5B—H5B2···O1Ai0.972.393.324 (4)163
Symmetry code: (i) x, y1, z.
 

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