Download citation
Download citation
link to html
The X-ray crystal structure of the title compound, C47H37NO3, has been determined. The zigzag packing of the mol­ecules is stabilized by intermolecular O—H...O hydrogen bonds between the host and guest mol­ecules, and intramolecular C—H...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801019845/na6077sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801019845/na6077Isup2.hkl
Contains datablock I

CCDC reference: 180768

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.058
  • wR factor = 0.176
  • Data-to-parameter ratio = 14.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Red Alert Alert Level A:
SYMMG_02 From the CIF: _symmetry_equiv_pos_as_xyz x, y, z -x+1/2, y+1/2, -z+1/2 -x, -y, -z x-1/2, -y-1/2, z-1/2 These symops generate the Hall space group symbol -p_2yn From the CIF: _symmetry_space_group_name_H-M p_21/c From the xyz: _symmetry_space_group_name_H-M p_1_21/n_1 Alert A The _symmetry_equiv_pos_as_xyz values are inconsistent with the H-M symbol given
Yellow Alert Alert Level C:
ABSTM_02 Alert C The ratio of Tmax/Tmin expected RT(exp) is > 1.10 Absorption corrections should be applied. Tmin and Tmax expected: 0.782 0.874 RT(exp) = 1.118 DIFMX_01 Alert C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.606 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. SHFSU_01 Alert C The absolute value of parameter shift to su ratio > 0.05 Absolute value of the parameter shift to su ratio given 0.062 Additional refinement cycles may be required. PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(9) - C(30) = 1.44 Ang. PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(10) - C(15) = 1.43 Ang. PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 39 C13 -C10 -C15 -C16 -168.90 1.50 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 40 C11 -C10 -C15 -C16 9.80 1.60 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 41 C10 -C15 -C16 -C17 36.00 2.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 42 C15 -C16 -C17 -O1 -33.90 1.30 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 43 C15 -C16 -C17 -C18 -154.00 1.20 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 44 C15 -C16 -C17 -C24 82.50 1.20 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 73 C14 -C9 -C30 -C31 -174.00 3.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 74 C12 -C9 -C30 -C31 6.00 3.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 75 C9 -C30 -C31 -C32 50.00 5.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 76 C30 -C31 -C32 -O2 -43.00 3.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 77 C30 -C31 -C32 -C39 -164.00 3.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 78 C30 -C31 -C32 -C33 73.00 3.00 1.555 1.555 1.555 1.555
1 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
18 Alert Level C = Please check

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SDP (Frenz ,1978); data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1995); software used to prepare material for publication: PARST (Nardelli, 1995).

9,10-Bis(3-hydroxy-3,3-diphenylprop-1-ynyl)anthracene N,N'dimethylformamide solvate top
Crystal data top
C47H37NO3F(000) = 1400
Mr = 663.78Dx = 1.214 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 16.290 (3) ÅCell parameters from 26 reflections
b = 11.837 (2) Åθ = 5–20°
c = 19.426 (4) ŵ = 0.59 mm1
β = 104.11 (3)°T = 293 K
V = 3632.8 (12) Å3Rectangular, yellow-brown
Z = 40.53 × 0.40 × 0.23 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.015
Radiation source: fine-focus sealed tubeθmax = 70.1°, θmin = 3.2°
Graphite monochromatorh = 019
ω/2θ scansk = 014
7151 measured reflectionsl = 2322
6910 independent reflections3 standard reflections every 200 reflections
5927 reflections with I > 2σ(I) intensity decay: <1.5%
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)] = 0.058H-atom parameters constrained
wR(F2) = 0.176 w = 1/[σ2(Fo2) + (0.0989P)2 + 1.1549P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.062
6910 reflectionsΔρmax = 0.61 e Å3
465 parametersΔρmin = 0.37 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0049 (4)
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
O10.97718 (8)0.08492 (12)0.33001 (8)0.0520 (3)
H10.96800.12290.36260.078*
O20.68044 (9)0.88981 (12)0.06549 (7)0.0512 (3)
H20.64820.83560.05870.077*
C10.75743 (12)0.55950 (17)0.17886 (10)0.0477 (4)
H1A0.72870.62140.15490.057*
C20.71994 (13)0.4963 (2)0.22060 (11)0.0560 (5)
H2A0.66610.51530.22510.067*
C30.76179 (14)0.40185 (19)0.25730 (11)0.0556 (5)
H30.73510.35830.28520.067*
C40.84071 (13)0.37428 (16)0.25212 (10)0.0480 (4)
H40.86800.31260.27740.058*
C51.08582 (13)0.44449 (18)0.14725 (12)0.0547 (5)
H51.11530.38400.17220.066*
C61.12163 (15)0.5052 (2)0.10320 (14)0.0676 (6)
H61.17560.48660.09880.081*
C71.07803 (16)0.5962 (2)0.06408 (14)0.0658 (6)
H71.10300.63660.03350.079*
C80.99976 (13)0.62543 (16)0.07066 (11)0.0518 (5)
H80.97170.68570.04440.062*
C90.87928 (11)0.59571 (13)0.12585 (8)0.0384 (4)
C100.96502 (11)0.40958 (13)0.20151 (9)0.0382 (4)
C110.88296 (11)0.43800 (14)0.20864 (8)0.0377 (4)
C120.83990 (11)0.53323 (14)0.17080 (8)0.0381 (4)
C131.00378 (11)0.47153 (14)0.15610 (9)0.0405 (4)
C140.95984 (11)0.56541 (14)0.11709 (9)0.0402 (4)
C151.00660 (11)0.31449 (14)0.24080 (9)0.0420 (4)
C161.03343 (11)0.23320 (14)0.27499 (9)0.0431 (4)
C171.05286 (10)0.12398 (14)0.31271 (9)0.0392 (4)
C181.12256 (10)0.13315 (14)0.38101 (9)0.0372 (4)
C191.14088 (12)0.03777 (16)0.42346 (10)0.0490 (4)
H191.11390.03010.40800.059*
C201.19885 (14)0.04251 (19)0.48847 (11)0.0582 (5)
H201.21010.02170.51680.070*
C211.23993 (14)0.14241 (19)0.51134 (11)0.0581 (5)
H211.27810.14620.55550.070*
C221.22426 (14)0.23600 (18)0.46880 (12)0.0592 (5)
H221.25330.30280.48350.071*
C231.16511 (12)0.23172 (15)0.40376 (11)0.0500 (5)
H231.15430.29600.37550.060*
C241.07643 (12)0.03877 (14)0.26123 (9)0.0425 (4)
C251.15366 (16)0.0466 (2)0.24425 (12)0.0627 (6)
H251.19170.10290.26480.075*
C261.1751 (2)0.0286 (2)0.19675 (15)0.0804 (8)
H261.22730.02280.18560.097*
C271.1194 (2)0.1117 (2)0.16622 (13)0.0771 (8)
H271.13400.16280.13490.093*
C281.04244 (19)0.1188 (2)0.18212 (13)0.0711 (7)
H281.00430.17440.16070.085*
C291.02027 (14)0.04463 (17)0.22965 (12)0.0569 (5)
H290.96780.05080.24030.068*
C300.83531 (11)0.69189 (14)0.08903 (9)0.0427 (4)
C310.79588 (12)0.77042 (14)0.06061 (9)0.0432 (4)
C320.74636 (11)0.87155 (14)0.03015 (9)0.0387 (4)
C330.80634 (11)0.97344 (14)0.04665 (9)0.0397 (4)
C340.86492 (12)0.99401 (16)0.00708 (11)0.0495 (4)
H340.86630.94800.03140.059*
C350.92173 (14)1.08321 (19)0.02480 (13)0.0599 (5)
H350.96061.09710.00220.072*
C360.92067 (15)1.15095 (18)0.08201 (12)0.0627 (6)
H360.95941.20970.09420.075*
C370.86250 (16)1.13162 (18)0.12091 (11)0.0622 (6)
H370.86151.17790.15940.075*
C380.80485 (14)1.04343 (16)0.10340 (10)0.0514 (5)
H380.76521.03140.12990.062*
C390.70815 (11)0.85851 (14)0.04973 (9)0.0416 (4)
C400.65493 (14)0.94308 (18)0.08403 (11)0.0568 (5)
H400.64521.00630.05880.068*
C410.61631 (17)0.9343 (2)0.15531 (13)0.0729 (7)
H410.58040.99150.17770.087*
C420.6303 (2)0.8423 (2)0.19341 (12)0.0813 (8)
H420.60370.83630.24140.098*
C430.6839 (2)0.7592 (2)0.16021 (13)0.0901 (10)
H430.69450.69680.18590.108*
C440.72250 (18)0.76755 (18)0.08840 (12)0.0677 (7)
H440.75860.71040.06630.081*
O1A0.55518 (14)0.7170 (2)0.05586 (13)0.0931 (6)
N1A0.46411 (15)0.7528 (2)0.05206 (13)0.0777 (6)
C1A0.5137 (3)0.6843 (3)0.0021 (3)0.1059 (12)
H1A10.51620.60790.01270.127*
C2A0.4581 (3)0.8667 (3)0.0378 (3)0.1328 (16)
H2A10.47440.87870.01260.199*
H2A20.40080.89150.05610.199*
H2A30.49500.90880.06000.199*
C3A0.4212 (4)0.7036 (6)0.1176 (3)0.182 (3)
H3A10.43630.62530.11810.273*
H3A20.43710.74220.15590.273*
H3A30.36120.71020.12320.273*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0401 (7)0.0508 (8)0.0624 (9)0.0071 (6)0.0070 (6)0.0022 (6)
O20.0525 (8)0.0481 (7)0.0536 (8)0.0019 (6)0.0138 (6)0.0006 (6)
C10.0500 (10)0.0471 (10)0.0424 (9)0.0156 (8)0.0042 (8)0.0052 (8)
C20.0496 (10)0.0680 (13)0.0504 (11)0.0128 (9)0.0119 (9)0.0054 (9)
C30.0604 (12)0.0609 (12)0.0471 (10)0.0048 (10)0.0161 (9)0.0108 (9)
C40.0569 (11)0.0437 (10)0.0406 (9)0.0087 (8)0.0066 (8)0.0089 (7)
C50.0475 (10)0.0472 (11)0.0664 (13)0.0080 (8)0.0082 (9)0.0000 (9)
C60.0527 (12)0.0658 (14)0.0883 (17)0.0020 (10)0.0251 (12)0.0006 (12)
C70.0693 (14)0.0571 (13)0.0782 (15)0.0053 (11)0.0317 (12)0.0052 (11)
C80.0604 (12)0.0391 (10)0.0547 (11)0.0025 (8)0.0117 (9)0.0037 (8)
C90.0467 (9)0.0276 (8)0.0343 (8)0.0028 (7)0.0028 (7)0.0006 (6)
C100.0420 (9)0.0292 (8)0.0360 (8)0.0046 (6)0.0049 (7)0.0011 (6)
C110.0452 (9)0.0316 (8)0.0308 (8)0.0049 (7)0.0018 (6)0.0001 (6)
C120.0437 (9)0.0328 (8)0.0319 (8)0.0063 (7)0.0020 (7)0.0006 (6)
C130.0422 (9)0.0317 (8)0.0420 (9)0.0012 (7)0.0003 (7)0.0040 (7)
C140.0472 (9)0.0304 (8)0.0382 (8)0.0009 (7)0.0010 (7)0.0025 (6)
C150.0436 (9)0.0334 (9)0.0411 (9)0.0031 (7)0.0048 (7)0.0007 (7)
C160.0420 (9)0.0338 (9)0.0451 (9)0.0042 (7)0.0056 (7)0.0001 (7)
C170.0373 (8)0.0307 (8)0.0444 (9)0.0002 (6)0.0000 (7)0.0031 (7)
C180.0356 (8)0.0333 (8)0.0399 (8)0.0042 (6)0.0036 (7)0.0023 (6)
C190.0542 (11)0.0366 (9)0.0502 (10)0.0002 (8)0.0012 (8)0.0081 (8)
C200.0650 (12)0.0545 (12)0.0480 (11)0.0078 (10)0.0002 (9)0.0156 (9)
C210.0561 (11)0.0643 (13)0.0442 (10)0.0073 (10)0.0066 (9)0.0007 (9)
C220.0576 (12)0.0490 (11)0.0587 (12)0.0038 (9)0.0094 (9)0.0057 (9)
C230.0515 (10)0.0346 (9)0.0545 (11)0.0008 (8)0.0051 (8)0.0036 (8)
C240.0521 (10)0.0310 (8)0.0388 (9)0.0038 (7)0.0001 (7)0.0046 (7)
C250.0744 (14)0.0548 (12)0.0634 (13)0.0096 (11)0.0256 (11)0.0079 (10)
C260.100 (2)0.0784 (18)0.0746 (16)0.0000 (15)0.0446 (15)0.0061 (14)
C270.125 (2)0.0579 (14)0.0499 (12)0.0108 (15)0.0235 (14)0.0072 (10)
C280.0997 (19)0.0473 (12)0.0547 (13)0.0003 (12)0.0036 (12)0.0116 (10)
C290.0605 (12)0.0435 (10)0.0569 (12)0.0004 (9)0.0043 (9)0.0046 (9)
C300.0502 (10)0.0320 (8)0.0394 (9)0.0020 (7)0.0018 (7)0.0020 (7)
C310.0508 (10)0.0326 (9)0.0396 (9)0.0003 (7)0.0021 (7)0.0026 (7)
C320.0439 (9)0.0308 (8)0.0377 (8)0.0043 (7)0.0030 (7)0.0038 (6)
C330.0465 (9)0.0294 (8)0.0361 (8)0.0048 (7)0.0040 (7)0.0045 (6)
C340.0503 (10)0.0409 (10)0.0550 (11)0.0003 (8)0.0088 (8)0.0043 (8)
C350.0515 (11)0.0524 (12)0.0725 (14)0.0060 (9)0.0087 (10)0.0029 (10)
C360.0674 (13)0.0430 (11)0.0631 (13)0.0116 (10)0.0124 (11)0.0005 (9)
C370.0881 (16)0.0440 (11)0.0442 (10)0.0087 (10)0.0036 (10)0.0074 (8)
C380.0710 (13)0.0400 (10)0.0384 (9)0.0020 (9)0.0041 (9)0.0006 (7)
C390.0470 (9)0.0314 (8)0.0400 (9)0.0016 (7)0.0019 (7)0.0031 (7)
C400.0668 (13)0.0449 (10)0.0492 (11)0.0134 (9)0.0043 (9)0.0055 (8)
C410.0819 (16)0.0614 (14)0.0569 (13)0.0063 (12)0.0190 (11)0.0135 (11)
C420.116 (2)0.0609 (14)0.0457 (12)0.0142 (14)0.0224 (13)0.0031 (10)
C430.150 (3)0.0514 (13)0.0510 (13)0.0050 (15)0.0098 (15)0.0140 (10)
C440.1019 (18)0.0384 (10)0.0502 (11)0.0145 (11)0.0056 (11)0.0044 (9)
O1A0.0860 (13)0.0960 (15)0.0995 (15)0.0252 (12)0.0269 (11)0.0015 (12)
N1A0.0759 (14)0.0705 (14)0.0899 (15)0.0071 (11)0.0267 (12)0.0147 (12)
C1A0.115 (3)0.0684 (19)0.153 (4)0.0100 (19)0.068 (3)0.013 (2)
C2A0.129 (3)0.082 (2)0.198 (5)0.004 (2)0.061 (3)0.018 (3)
C3A0.207 (6)0.223 (6)0.124 (4)0.067 (5)0.053 (4)0.081 (4)
Geometric parameters (Å, º) top
O1—C171.431 (2)C25—C261.387 (3)
O1—H10.8200C25—H250.9300
O2—C321.425 (2)C26—C271.370 (4)
O2—H20.8200C26—H260.9300
C1—C21.353 (3)C27—C281.365 (4)
C1—C121.424 (3)C27—H270.9300
C1—H1A0.9300C28—C291.384 (3)
C2—C31.409 (3)C28—H280.9300
C2—H2A0.9300C29—H290.9300
C3—C41.354 (3)C30—C311.187 (2)
C3—H30.9300C31—C321.484 (2)
C4—C111.428 (3)C32—C391.532 (2)
C4—H40.9300C32—C331.536 (2)
C5—C61.354 (3)C33—C381.384 (3)
C5—C131.425 (3)C33—C341.385 (3)
C5—H50.9300C34—C351.391 (3)
C6—C71.407 (3)C34—H340.9300
C6—H60.9300C35—C361.374 (3)
C7—C81.357 (3)C35—H350.9300
C7—H70.9300C36—C371.368 (4)
C8—C141.424 (3)C36—H360.9300
C8—H80.9300C37—C381.390 (3)
C9—C141.410 (3)C37—H370.9300
C9—C121.412 (2)C38—H380.9300
C9—C301.439 (2)C39—C441.365 (3)
C10—C131.409 (3)C39—C401.384 (2)
C10—C111.418 (2)C40—C411.378 (3)
C10—C151.434 (2)C40—H400.9300
C11—C121.432 (2)C41—C421.366 (4)
C13—C141.434 (2)C41—H410.9300
C15—C161.190 (2)C42—C431.368 (4)
C16—C171.482 (2)C42—H420.9300
C17—C181.525 (2)C43—C441.387 (3)
C17—C241.534 (3)C43—H430.9300
C18—C231.374 (2)C44—H440.9300
C18—C191.387 (2)O1A—C1A1.225 (5)
C19—C201.381 (3)N1A—C1A1.368 (5)
C19—H190.9300N1A—C2A1.385 (4)
C20—C211.378 (3)N1A—C3A1.419 (5)
C20—H200.9300C1A—H1A10.9300
C21—C221.368 (3)C2A—H2A10.9600
C21—H210.9300C2A—H2A20.9600
C22—C231.391 (3)C2A—H2A30.9600
C22—H220.9300C3A—H3A10.9600
C23—H230.9300C3A—H3A20.9600
C24—C251.379 (3)C3A—H3A30.9600
C24—C291.384 (3)
C17—O1—H1109.5C26—C25—H25119.7
C32—O2—H2109.5C27—C26—C25120.1 (3)
C2—C1—C12121.37 (17)C27—C26—H26120.0
C2—C1—H1A119.3C25—C26—H26120.0
C12—C1—H1A119.3C28—C27—C26119.6 (2)
C1—C2—C3120.56 (19)C28—C27—H27120.2
C1—C2—H2A119.7C26—C27—H27120.2
C3—C2—H2A119.7C27—C28—C29121.0 (2)
C4—C3—C2120.30 (19)C27—C28—H28119.5
C4—C3—H3119.8C29—C28—H28119.5
C2—C3—H3119.8C24—C29—C28119.8 (2)
C3—C4—C11121.34 (17)C24—C29—H29120.1
C3—C4—H4119.3C28—C29—H29120.1
C11—C4—H4119.3C31—C30—C9176.5 (2)
C6—C5—C13121.2 (2)C30—C31—C32175.93 (19)
C6—C5—H5119.4O2—C32—C31109.31 (14)
C13—C5—H5119.4O2—C32—C39109.59 (14)
C5—C6—C7120.6 (2)C31—C32—C39111.70 (14)
C5—C6—H6119.7O2—C32—C33107.22 (14)
C7—C6—H6119.7C31—C32—C33107.10 (14)
C8—C7—C6120.4 (2)C39—C32—C33111.78 (14)
C8—C7—H7119.8C38—C33—C34119.02 (17)
C6—C7—H7119.8C38—C33—C32120.16 (17)
C7—C8—C14121.15 (19)C34—C33—C32120.77 (16)
C7—C8—H8119.4C33—C34—C35120.20 (19)
C14—C8—H8119.4C33—C34—H34119.9
C14—C9—C12121.19 (15)C35—C34—H34119.9
C14—C9—C30120.42 (16)C36—C35—C34120.3 (2)
C12—C9—C30118.39 (16)C36—C35—H35119.9
C13—C10—C11120.98 (15)C34—C35—H35119.9
C13—C10—C15121.07 (16)C37—C36—C35119.8 (2)
C11—C10—C15117.94 (16)C37—C36—H36120.1
C10—C11—C4122.31 (15)C35—C36—H36120.1
C10—C11—C12119.47 (16)C36—C37—C38120.6 (2)
C4—C11—C12118.22 (16)C36—C37—H37119.7
C9—C12—C1122.45 (15)C38—C37—H37119.7
C9—C12—C11119.34 (15)C33—C38—C37120.2 (2)
C1—C12—C11118.19 (16)C33—C38—H38119.9
C10—C13—C5122.36 (16)C37—C38—H38119.9
C10—C13—C14119.46 (16)C44—C39—C40118.46 (18)
C5—C13—C14118.18 (17)C44—C39—C32123.70 (16)
C9—C14—C8122.13 (16)C40—C39—C32117.83 (16)
C9—C14—C13119.50 (16)C41—C40—C39120.5 (2)
C8—C14—C13118.37 (17)C41—C40—H40119.7
C16—C15—C10173.3 (2)C39—C40—H40119.7
C15—C16—C17170.59 (18)C42—C41—C40120.6 (2)
O1—C17—C16107.79 (14)C42—C41—H41119.7
O1—C17—C18108.66 (14)C40—C41—H41119.7
C16—C17—C18113.08 (14)C41—C42—C43119.3 (2)
O1—C17—C24107.91 (14)C41—C42—H42120.4
C16—C17—C24107.98 (14)C43—C42—H42120.4
C18—C17—C24111.24 (13)C42—C43—C44120.2 (2)
C23—C18—C19118.77 (16)C42—C43—H43119.9
C23—C18—C17123.39 (15)C44—C43—H43119.9
C19—C18—C17117.77 (15)C39—C44—C43120.9 (2)
C20—C19—C18120.71 (18)C39—C44—H44119.6
C20—C19—H19119.6C43—C44—H44119.6
C18—C19—H19119.6C1A—N1A—C2A119.5 (3)
C21—C20—C19119.97 (18)C1A—N1A—C3A118.1 (4)
C21—C20—H20120.0C2A—N1A—C3A122.4 (4)
C19—C20—H20120.0O1A—C1A—N1A124.2 (3)
C22—C21—C20119.71 (18)O1A—C1A—H1A1117.9
C22—C21—H21120.1N1A—C1A—H1A1117.9
C20—C21—H21120.1N1A—C2A—H2A1109.5
C21—C22—C23120.34 (19)N1A—C2A—H2A2109.5
C21—C22—H22119.8H2A1—C2A—H2A2109.5
C23—C22—H22119.8N1A—C2A—H2A3109.5
C18—C23—C22120.44 (18)H2A1—C2A—H2A3109.5
C18—C23—H23119.8H2A2—C2A—H2A3109.5
C22—C23—H23119.8N1A—C3A—H3A1109.5
C25—C24—C29119.02 (19)N1A—C3A—H3A2109.5
C25—C24—C17119.97 (17)H3A1—C3A—H3A2109.5
C29—C24—C17120.98 (18)N1A—C3A—H3A3109.5
C24—C25—C26120.5 (2)H3A1—C3A—H3A3109.5
C24—C25—H25119.7H3A2—C3A—H3A3109.5
C12—C1—C2—C30.2 (3)C20—C21—C22—C232.1 (4)
C1—C2—C3—C41.1 (3)C19—C18—C23—C221.2 (3)
C2—C3—C4—C111.2 (3)C17—C18—C23—C22175.90 (19)
C13—C5—C6—C70.8 (4)C21—C22—C23—C180.9 (3)
C5—C6—C7—C80.9 (4)O1—C17—C24—C25170.24 (17)
C6—C7—C8—C140.1 (3)C16—C17—C24—C2573.5 (2)
C13—C10—C11—C4177.57 (16)C18—C17—C24—C2551.1 (2)
C15—C10—C11—C41.2 (2)O1—C17—C24—C2911.6 (2)
C13—C10—C11—C121.9 (2)C16—C17—C24—C29104.62 (19)
C15—C10—C11—C12179.31 (14)C18—C17—C24—C29130.74 (17)
C3—C4—C11—C10178.95 (18)C29—C24—C25—C260.7 (3)
C3—C4—C11—C120.6 (3)C17—C24—C25—C26178.8 (2)
C14—C9—C12—C1177.84 (16)C24—C25—C26—C270.0 (4)
C30—C9—C12—C12.3 (2)C25—C26—C27—C280.9 (4)
C14—C9—C12—C110.6 (2)C26—C27—C28—C291.2 (4)
C30—C9—C12—C11179.24 (14)C25—C24—C29—C280.4 (3)
C2—C1—C12—C9177.96 (18)C17—C24—C29—C28178.51 (18)
C2—C1—C12—C110.5 (3)C27—C28—C29—C240.5 (3)
C10—C11—C12—C91.3 (2)C14—C9—C30—C31174 (3)
C4—C11—C12—C9178.19 (15)C12—C9—C30—C316 (3)
C10—C11—C12—C1179.82 (15)C9—C30—C31—C3250 (5)
C4—C11—C12—C10.3 (2)C30—C31—C32—O243 (3)
C11—C10—C13—C5179.40 (16)C30—C31—C32—C39164 (3)
C15—C10—C13—C50.7 (3)C30—C31—C32—C3373 (3)
C11—C10—C13—C140.6 (2)O2—C32—C33—C3818.1 (2)
C15—C10—C13—C14179.34 (15)C31—C32—C33—C3899.12 (19)
C6—C5—C13—C10179.9 (2)C39—C32—C33—C38138.23 (17)
C6—C5—C13—C140.1 (3)O2—C32—C33—C34164.61 (15)
C12—C9—C14—C8178.35 (16)C31—C32—C33—C3478.17 (19)
C30—C9—C14—C81.8 (2)C39—C32—C33—C3444.5 (2)
C12—C9—C14—C131.9 (2)C38—C33—C34—C350.6 (3)
C30—C9—C14—C13177.93 (15)C32—C33—C34—C35176.75 (17)
C7—C8—C14—C9178.69 (19)C33—C34—C35—C360.6 (3)
C7—C8—C14—C131.1 (3)C34—C35—C36—C371.1 (3)
C10—C13—C14—C91.3 (2)C35—C36—C37—C380.5 (3)
C5—C13—C14—C9178.69 (16)C34—C33—C38—C371.2 (3)
C10—C13—C14—C8178.95 (16)C32—C33—C38—C37176.17 (17)
C5—C13—C14—C81.1 (2)C36—C37—C38—C330.6 (3)
C13—C10—C15—C16168.9 (15)O2—C32—C39—C44124.9 (2)
C11—C10—C15—C169.8 (16)C31—C32—C39—C443.7 (3)
C10—C15—C16—C1736 (2)C33—C32—C39—C44116.3 (2)
C15—C16—C17—O133.9 (13)O2—C32—C39—C4053.9 (2)
C15—C16—C17—C18154.0 (12)C31—C32—C39—C40175.15 (18)
C15—C16—C17—C2482.5 (12)C33—C32—C39—C4064.9 (2)
O1—C17—C18—C23121.96 (18)C44—C39—C40—C411.1 (4)
C16—C17—C18—C232.3 (3)C32—C39—C40—C41177.7 (2)
C24—C17—C18—C23119.39 (19)C39—C40—C41—C420.4 (4)
O1—C17—C18—C1955.2 (2)C40—C41—C42—C430.7 (5)
C16—C17—C18—C19174.81 (17)C41—C42—C43—C441.0 (5)
C24—C17—C18—C1963.5 (2)C40—C39—C44—C430.8 (4)
C23—C18—C19—C202.1 (3)C32—C39—C44—C43178.0 (2)
C17—C18—C19—C20175.22 (18)C42—C43—C44—C390.2 (5)
C18—C19—C20—C210.8 (3)C2A—N1A—C1A—O1A0.7 (5)
C19—C20—C21—C221.3 (4)C3A—N1A—C1A—O1A178.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1A0.822.062.863 (3)168
C29—H29···O10.932.352.704 (3)102
C38—H38···O20.932.332.689 (2)102
C2A—H2A1···O1A0.962.362.747 (5)104
O1—H1···O1Ai0.822.042.865 (3)180
C2—H2A···O1ii0.932.463.292 (2)149
Symmetry codes: (i) x+3/2, y1/2, z+1/2; (ii) x+3/2, y+1/2, z+1/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds