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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3290.
Published online 2010 November 24. doi:  10.1107/S1600536810044028
PMCID: PMC3011503

Phenyl 3,5-di-tert-butyl-2-hy­droxy­benzoate

Abstract

The title mol­ecule, C21H26O3, has a six-membered planar carbon ring as the central core, substituted at position 1 with phen­oxy­carbonyl, at position 2 with hy­droxy and at positions 3 and 5 with tert-butyl groups. The structure shows two independent but very similar mol­ecules within the asymmetric unit. For both independent mol­ecules, the ester carboxyl­ate group is coplanar with the central core, as reflected by the small C—C—O—C torsion angles [179.95 (17) and 173.70 (17)°]. In contrast, the phenyl substituent is almost perpendicular to the carboxyl­ate –CO2 fragment, as reflected by C—O—C—C torsion angles, ranging from 74 to 80°. The coplanarity between the central aromatic ring and the ester carboxyl­ate –CO2– group allows the formation of an intra­molecular hydrogen bond, with O(...)O distances of 2.563 (2) and 2.604 (2) Å.

Related literature

For the synthesis of the title compound, see: Moore et al. (2008 [triangle]); Benisvy et al. (2004 [triangle]). For similar mol­ecules, see: Baptista (1966 [triangle]); Bilgram et al. (1982 [triangle]); Hammond et al. (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3290-scheme1.jpg

Experimental

Crystal data

  • C21H26O3
  • M r = 326.42
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3290-efi1.jpg
  • a = 10.5691 (11) Å
  • b = 12.2590 (13) Å
  • c = 15.0534 (16) Å
  • α = 96.400 (2)°
  • β = 93.813 (2)°
  • γ = 92.728 (2)°
  • V = 1931.0 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 297 K
  • 0.50 × 0.21 × 0.20 mm

Data collection

  • Siemens SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.964, T max = 0.985
  • 12058 measured reflections
  • 6736 independent reflections
  • 4140 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.053
  • wR(F 2) = 0.153
  • S = 1.01
  • 6736 reflections
  • 445 parameters
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.12 e Å−3

Data collection: SMART-NT (Bruker, 2001 [triangle]); cell refinement: SAINT-NT (Bruker, 1999 [triangle]); data reduction: SAINT-NT; program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT; software used to prepare material for publication: SHELXTL-NT.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810044028/om2371sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044028/om2371Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors acknowledge financial support from UNAB-DI-28-10/I and Millenium Project No. P07-006-F. AV is a member of Financiamiento Basal para Centros Científicos y Tecnológicos de Excelencia FB0807. AC acknowledges Universidad Andres Bello for a Doctoral Fellowship.

supplementary crystallographic information

Comment

Benzoate phenyl esters have been described to be precursors of benzimidazole molecules by reaction with 1,2-phenylenediamine (Moore et al., 2008). The crystal shows two independent but very similar molecules within the asymmetric unit. For both independent molecules, the carboxylic acid group from ester is coplanar with the central core, as reflected by the small C—C—O—C torsion angles (C1—C7—O3—C16, 179.95 (17)°; C22—C28—O6—C37 173.70 (17)°), while the phenyl substituent is almost perpendicular to the carboxylate CO2 fragment (C7—O3—C16—C21 110.4 (2)°; C7—O3—C16—C17 - 74.1 (3)° and C28—O6—C37—C38 - 69.2 (3)°; C28—O6—C37—C42 117.4 (2)°). The co-planarity between the central aromatic ring and the carboxylate CO2 group from ester allows the definition of a intramolecular hydrogen bond, with O···O 2.563 (2) and 2.604 (2) Å.

The structure is closely related to that of the unsubstituted 2-hydroxybenzoic acid phenyl ester (Baptista, 1966; Bilgram et al. 1982; Hammond et al., 2002), where the carboxylate group is almost coplanar to the phenyl ring where is attached (C—C—O—C less than 2° deviated from 180°) and the benzoate phenyl almost perpendicular to the carboxylate (C—O—C—C 75.8° and -100.5°).

The phenyl rings from the benzoate from each of the two molecules within the asymmetric unit defines a weak π···π interaction with Cg1(C16, C17, C18, C19, C20, C21)···Cg2(C37, C38, C39, C40, C41, C41) 3.903 (2) Å].

Experimental

The compound was prepared by methods described in literature (Benisvy et al., 2004) slighty modified by using CHCl3 for crystallization instead of pentane. The title compound was prepared in a 40% yield.

Refinement

The H-atoms positions were calculated after each cycle of refinement using a riding model for each structure, with C—H distances in the range 0.93 to 0.96 Å. Uiso(H) values were set equal to 1.5Ueq of the parent carbon atom for methyl groups and 1.2Ueq for the others. The hydroxyl hydrogen atoms were located in the difference Fourier map, but were subsequentely refined with constraints, O—H 0.82 Å and Uiso(H) 1.5Ueq of the parent oxygen atom.

Figures

Fig. 1.
Molecular structure diagram showing the two independent molecules of I within the crystal, with atom numbering scheme. Displacement ellipsoids are at 25% probability level and H atoms are shown as spheres of arbitrary radii. Intramolecular hydrogen bonds ...

Crystal data

C21H26O3Z = 4
Mr = 326.42F(000) = 704
Triclinic, P1Dx = 1.123 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.5691 (11) ÅCell parameters from 2560 reflections
b = 12.2590 (13) Åθ = 2.3–22.7°
c = 15.0534 (16) ŵ = 0.07 mm1
α = 96.400 (2)°T = 297 K
β = 93.813 (2)°Colourless, block
γ = 92.728 (2)°0.50 × 0.21 × 0.20 mm
V = 1931.0 (4) Å3

Data collection

Siemens SMART CCD area-detector diffractometer6736 independent reflections
Radiation source: fine-focus sealed tube4140 reflections with I > 2σ(I)
graphiteRint = 0.023
[var phi] and ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −12→12
Tmin = 0.964, Tmax = 0.985k = −14→14
12058 measured reflectionsl = −17→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0783P)2] where P = (Fo2 + 2Fc2)/3
6736 reflections(Δ/σ)max < 0.001
445 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = −0.12 e Å3

Special details

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)

xyzUiso*/Ueq
C10.28649 (18)0.60650 (15)0.14800 (13)0.0465 (5)
C20.39947 (18)0.55813 (15)0.17139 (13)0.0477 (5)
C30.43181 (18)0.54106 (16)0.26117 (13)0.0492 (5)
C40.34696 (19)0.57713 (16)0.32313 (13)0.0520 (5)
H4A0.36660.56720.38270.062*
C50.23390 (18)0.62743 (15)0.30273 (13)0.0489 (5)
C60.20550 (18)0.64095 (16)0.21424 (13)0.0497 (5)
H60.13100.67360.19810.060*
C70.2566 (2)0.62093 (16)0.05325 (14)0.0524 (5)
C80.5538 (2)0.48601 (18)0.28850 (14)0.0587 (6)
C90.5530 (3)0.3694 (2)0.23936 (18)0.0877 (8)
H9A0.55130.37310.17590.131*
H9B0.47930.32740.25290.131*
H9C0.62810.33480.25850.131*
C100.6714 (2)0.5544 (3)0.26778 (19)0.0925 (9)
H10A0.66880.56060.20470.139*
H10B0.74670.51900.28540.139*
H10C0.67230.62640.30030.139*
C110.5654 (2)0.4759 (2)0.38918 (15)0.0798 (7)
H11A0.64250.44160.40410.120*
H11B0.49410.43210.40450.120*
H11C0.56680.54780.42210.120*
C120.1488 (2)0.66550 (18)0.37777 (14)0.0579 (6)
C130.0264 (3)0.7094 (3)0.34080 (18)0.0984 (10)
H13A0.04610.77050.30840.148*
H13B−0.02400.73310.38940.148*
H13C−0.02040.65240.30130.148*
C140.1143 (3)0.5700 (2)0.42967 (18)0.0903 (8)
H14A0.06610.51360.39040.135*
H14B0.06450.59530.47810.135*
H14C0.19050.54070.45330.135*
C150.2221 (3)0.7569 (2)0.4411 (2)0.1051 (10)
H15A0.29820.72900.46630.158*
H15B0.17010.78180.48840.158*
H15C0.24390.81710.40830.158*
C160.1065 (2)0.67878 (19)−0.05259 (14)0.0563 (5)
C170.1612 (2)0.7639 (2)−0.08992 (16)0.0721 (7)
H170.22600.8094−0.05840.086*
C180.1182 (3)0.7812 (2)−0.17584 (17)0.0811 (7)
H180.15490.8385−0.20270.097*
C190.0230 (3)0.7153 (2)−0.22116 (17)0.0859 (8)
H19−0.00480.7269−0.27910.103*
C20−0.0319 (3)0.6321 (2)−0.18181 (18)0.0956 (9)
H20−0.09860.5881−0.21240.115*
C210.0109 (2)0.6127 (2)−0.09681 (17)0.0801 (7)
H21−0.02540.5551−0.07020.096*
C220.12793 (17)0.97781 (16)0.23838 (13)0.0473 (5)
C230.13758 (18)1.04161 (16)0.32194 (13)0.0496 (5)
C240.25789 (19)1.07809 (16)0.36367 (13)0.0505 (5)
C250.36198 (19)1.04615 (16)0.31783 (13)0.0519 (5)
H250.44211.06890.34470.062*
C260.35629 (18)0.98219 (15)0.23419 (13)0.0490 (5)
C270.23656 (18)0.94917 (16)0.19592 (13)0.0485 (5)
H270.22820.90680.14040.058*
C280.00075 (19)0.93956 (16)0.19638 (14)0.0514 (5)
C290.2727 (2)1.14813 (18)0.45578 (14)0.0600 (6)
C300.2086 (2)1.25680 (19)0.44900 (17)0.0786 (7)
H30A0.24641.29510.40430.118*
H30B0.21961.30140.50590.118*
H30C0.11961.24190.43260.118*
C310.2142 (2)1.0855 (2)0.52725 (15)0.0811 (7)
H31A0.12571.06800.51050.122*
H31B0.22331.13050.58400.122*
H31C0.25701.01880.53200.122*
C320.4136 (2)1.1771 (2)0.48629 (16)0.0781 (7)
H32A0.45661.11070.49190.117*
H32B0.41961.22160.54320.117*
H32C0.45231.21690.44280.117*
C330.47866 (18)0.94936 (17)0.19175 (14)0.0564 (6)
C340.5428 (2)0.8673 (2)0.24641 (18)0.0914 (9)
H34A0.56880.90240.30540.137*
H34B0.61580.84150.21760.137*
H34C0.48410.80610.25070.137*
C350.5688 (2)1.0500 (2)0.1888 (2)0.0921 (9)
H35A0.52791.10120.15410.138*
H35B0.64451.02760.16180.138*
H35C0.59051.08450.24870.138*
C360.4521 (2)0.8948 (2)0.09531 (16)0.0810 (7)
H36A0.40050.82820.09510.122*
H36B0.53090.87810.07010.122*
H36C0.40820.94400.06030.122*
C37−0.10673 (18)0.83525 (18)0.06791 (14)0.0545 (5)
C38−0.1617 (2)0.74454 (19)0.09664 (15)0.0671 (6)
H38−0.13170.71980.14990.081*
C39−0.2638 (2)0.6893 (2)0.04492 (17)0.0752 (7)
H39−0.30310.62710.06350.090*
C40−0.3064 (2)0.7267 (2)−0.03333 (17)0.0750 (7)
H40−0.37490.6900−0.06790.090*
C41−0.2489 (2)0.8176 (2)−0.06085 (17)0.0782 (7)
H41−0.27790.8421−0.11440.094*
C42−0.1484 (2)0.87318 (19)−0.01006 (16)0.0678 (6)
H42−0.10930.9356−0.02850.081*
O10.48062 (13)0.52679 (12)0.10891 (9)0.0666 (4)
H10.45160.53990.05960.100*
O20.32547 (15)0.59790 (14)−0.00665 (10)0.0731 (5)
O30.14275 (14)0.66219 (13)0.03719 (9)0.0661 (4)
O40.03285 (13)1.06905 (12)0.36496 (10)0.0678 (4)
H4−0.03061.03900.33640.102*
O5−0.09842 (14)0.95344 (13)0.23141 (10)0.0669 (4)
O60.00567 (13)0.88675 (13)0.11387 (10)0.0666 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0491 (12)0.0432 (11)0.0472 (12)0.0004 (9)0.0068 (9)0.0040 (9)
C20.0475 (12)0.0450 (12)0.0509 (12)0.0014 (9)0.0123 (10)0.0015 (9)
C30.0493 (12)0.0464 (12)0.0512 (12)0.0012 (9)0.0036 (10)0.0034 (9)
C40.0572 (13)0.0521 (13)0.0464 (12)0.0001 (10)0.0019 (10)0.0069 (10)
C50.0543 (13)0.0459 (12)0.0473 (12)0.0017 (10)0.0080 (9)0.0068 (9)
C60.0458 (11)0.0493 (12)0.0552 (13)0.0050 (9)0.0053 (9)0.0090 (10)
C70.0574 (13)0.0492 (13)0.0507 (13)0.0018 (10)0.0068 (11)0.0049 (10)
C80.0543 (13)0.0634 (14)0.0575 (13)0.0105 (11)−0.0014 (10)0.0038 (11)
C90.0928 (19)0.0795 (18)0.0883 (19)0.0381 (15)−0.0122 (15)−0.0038 (15)
C100.0503 (15)0.123 (2)0.106 (2)−0.0012 (14)−0.0013 (13)0.0260 (18)
C110.0799 (17)0.0903 (19)0.0696 (17)0.0216 (14)−0.0084 (13)0.0117 (14)
C120.0620 (14)0.0644 (14)0.0506 (12)0.0107 (11)0.0144 (10)0.0115 (11)
C130.090 (2)0.138 (3)0.0796 (18)0.0518 (19)0.0366 (15)0.0316 (17)
C140.100 (2)0.100 (2)0.0811 (18)0.0157 (16)0.0397 (15)0.0321 (16)
C150.111 (2)0.101 (2)0.096 (2)−0.0011 (18)0.0316 (18)−0.0324 (17)
C160.0592 (13)0.0633 (14)0.0469 (12)0.0070 (11)0.0015 (10)0.0093 (11)
C170.0699 (16)0.0745 (17)0.0712 (16)−0.0074 (13)−0.0078 (12)0.0183 (13)
C180.0847 (18)0.0844 (18)0.0784 (18)−0.0052 (15)−0.0023 (15)0.0365 (15)
C190.102 (2)0.092 (2)0.0635 (16)−0.0005 (17)−0.0178 (15)0.0251 (15)
C200.117 (2)0.088 (2)0.0746 (18)−0.0269 (17)−0.0302 (16)0.0170 (16)
C210.0974 (19)0.0727 (17)0.0687 (16)−0.0194 (14)−0.0103 (14)0.0219 (13)
C220.0419 (11)0.0487 (12)0.0511 (12)−0.0020 (9)0.0008 (9)0.0079 (9)
C230.0445 (12)0.0524 (12)0.0528 (12)0.0011 (9)0.0067 (10)0.0082 (10)
C240.0491 (12)0.0516 (12)0.0499 (12)−0.0010 (10)0.0004 (10)0.0051 (10)
C250.0458 (12)0.0541 (13)0.0534 (12)−0.0059 (9)−0.0044 (10)0.0040 (10)
C260.0465 (12)0.0471 (12)0.0531 (12)−0.0034 (9)0.0026 (9)0.0083 (10)
C270.0481 (12)0.0497 (12)0.0464 (11)−0.0018 (9)0.0022 (9)0.0035 (9)
C280.0473 (13)0.0517 (13)0.0554 (13)−0.0019 (10)0.0039 (10)0.0080 (10)
C290.0639 (14)0.0613 (14)0.0524 (13)0.0021 (11)−0.0011 (10)−0.0007 (11)
C300.0900 (18)0.0670 (16)0.0741 (16)0.0089 (13)−0.0019 (14)−0.0093 (13)
C310.0917 (19)0.097 (2)0.0540 (14)−0.0001 (15)0.0044 (13)0.0074 (13)
C320.0756 (17)0.0820 (17)0.0690 (16)−0.0014 (13)−0.0111 (13)−0.0137 (13)
C330.0455 (12)0.0562 (13)0.0666 (14)−0.0007 (10)0.0067 (10)0.0030 (11)
C340.0792 (18)0.103 (2)0.097 (2)0.0371 (16)0.0107 (15)0.0182 (17)
C350.0641 (16)0.0845 (19)0.125 (2)−0.0144 (14)0.0310 (15)−0.0090 (17)
C360.0643 (16)0.103 (2)0.0730 (17)0.0057 (14)0.0162 (12)−0.0098 (14)
C370.0394 (11)0.0659 (14)0.0553 (13)−0.0075 (10)0.0004 (10)−0.0003 (11)
C380.0653 (15)0.0770 (17)0.0575 (14)−0.0098 (13)−0.0042 (11)0.0129 (12)
C390.0727 (16)0.0735 (17)0.0770 (17)−0.0200 (13)0.0010 (14)0.0104 (13)
C400.0592 (15)0.0844 (19)0.0752 (17)−0.0148 (13)−0.0154 (12)0.0018 (14)
C410.0771 (17)0.0809 (18)0.0742 (16)−0.0055 (14)−0.0209 (13)0.0182 (14)
C420.0648 (15)0.0634 (15)0.0736 (16)−0.0117 (12)−0.0096 (12)0.0165 (12)
O10.0627 (9)0.0829 (11)0.0561 (9)0.0173 (8)0.0136 (7)0.0047 (8)
O20.0808 (11)0.0938 (12)0.0486 (9)0.0266 (9)0.0174 (8)0.0093 (8)
O30.0598 (9)0.0918 (11)0.0493 (9)0.0173 (8)0.0047 (7)0.0145 (8)
O40.0505 (9)0.0833 (11)0.0667 (10)0.0006 (8)0.0095 (7)−0.0061 (8)
O50.0442 (9)0.0794 (11)0.0739 (10)−0.0023 (7)0.0051 (7)−0.0037 (8)
O60.0474 (9)0.0892 (11)0.0579 (9)−0.0118 (8)0.0004 (7)−0.0066 (8)

Geometric parameters (Å, °)

C1—C61.400 (3)C22—C271.391 (3)
C1—C21.400 (3)C22—C231.400 (3)
C1—C71.472 (3)C22—C281.479 (3)
C2—O11.351 (2)C23—O41.356 (2)
C2—C31.413 (3)C23—C241.410 (3)
O1—H10.8200O4—H40.8200
C3—C41.388 (3)C24—C251.386 (3)
C3—C81.537 (3)C24—C291.542 (3)
C8—C91.534 (3)C28—O51.215 (2)
C8—C111.532 (3)C28—O61.340 (2)
C8—C101.535 (3)C29—C301.533 (3)
C9—H9A0.9600C29—C311.535 (3)
C9—H9B0.9600C29—C321.542 (3)
C9—H9C0.9600C30—H30A0.9600
C10—H10A0.9600C30—H30B0.9600
C10—H10B0.9600C30—H30C0.9600
C10—H10C0.9600C31—H31A0.9600
C11—H11A0.9600C31—H31B0.9600
C11—H11B0.9600C31—H31C0.9600
C11—H11C0.9600C25—C261.403 (3)
C4—C51.402 (3)C25—H250.9300
C4—H4A0.9300C26—C271.378 (3)
C5—C61.376 (3)C26—C331.531 (3)
C5—C121.536 (3)C27—H270.9300
C12—C131.520 (3)C32—H32A0.9600
C12—C141.522 (3)C32—H32B0.9600
C12—C151.531 (3)C32—H32C0.9600
C13—H13A0.9600C33—C341.525 (3)
C13—H13B0.9600C33—C351.529 (3)
C13—H13C0.9600C33—C361.531 (3)
C14—H14A0.9600C34—H34A0.9600
C14—H14B0.9600C34—H34B0.9600
C14—H14C0.9600C34—H34C0.9600
C15—H15A0.9600C35—H35A0.9600
C15—H15B0.9600C35—H35B0.9600
C15—H15C0.9600C35—H35C0.9600
C6—H60.9300O6—C371.418 (2)
C7—O21.213 (2)C36—H36A0.9600
C7—O31.345 (2)C36—H36B0.9600
O3—C161.419 (2)C36—H36C0.9600
C16—C211.354 (3)C37—C381.357 (3)
C16—C171.362 (3)C37—C421.364 (3)
C17—C181.384 (3)C38—C391.389 (3)
C17—H170.9300C38—H380.9300
C18—C191.357 (3)C39—C401.368 (3)
C18—H180.9300C39—H390.9300
C19—C201.361 (3)C40—C411.361 (3)
C19—H190.9300C40—H400.9300
C20—C211.378 (3)C41—C421.373 (3)
C20—H200.9300C41—H410.9300
C21—H210.9300C42—H420.9300
C6—C1—C2119.99 (18)C27—C22—C23120.52 (18)
C6—C1—C7121.49 (18)C27—C22—C28120.31 (18)
C2—C1—C7118.51 (17)C23—C22—C28119.17 (18)
O1—C2—C1121.01 (18)O4—C23—C22121.38 (18)
O1—C2—C3118.21 (17)O4—C23—C24118.46 (18)
C1—C2—C3120.78 (17)C22—C23—C24120.16 (18)
C2—O1—H1109.5C23—O4—H4109.5
C4—C3—C2116.01 (18)C25—C24—C23116.26 (18)
C4—C3—C8122.06 (18)C25—C24—C29121.95 (18)
C2—C3—C8121.93 (17)C23—C24—C29121.78 (18)
C9—C8—C11107.30 (19)O5—C28—O6122.67 (18)
C9—C8—C10110.2 (2)O5—C28—C22124.8 (2)
C11—C8—C10107.08 (19)O6—C28—C22112.52 (18)
C9—C8—C3110.12 (18)C30—C29—C31110.5 (2)
C11—C8—C3111.52 (17)C30—C29—C24109.31 (17)
C10—C8—C3110.54 (19)C31—C29—C24110.49 (18)
C8—C9—H9A109.5C30—C29—C32107.23 (19)
C8—C9—H9B109.5C31—C29—C32107.82 (18)
H9A—C9—H9B109.5C24—C29—C32111.45 (18)
C8—C9—H9C109.5C29—C30—H30A109.5
H9A—C9—H9C109.5C29—C30—H30B109.5
H9B—C9—H9C109.5H30A—C30—H30B109.5
C8—C10—H10A109.5C29—C30—H30C109.5
C8—C10—H10B109.5H30A—C30—H30C109.5
H10A—C10—H10B109.5H30B—C30—H30C109.5
C8—C10—H10C109.5C29—C31—H31A109.5
H10A—C10—H10C109.5C29—C31—H31B109.5
H10B—C10—H10C109.5H31A—C31—H31B109.5
C8—C11—H11A109.5C29—C31—H31C109.5
C8—C11—H11B109.5H31A—C31—H31C109.5
H11A—C11—H11B109.5H31B—C31—H31C109.5
C8—C11—H11C109.5C24—C25—C26125.29 (18)
H11A—C11—H11C109.5C24—C25—H25117.4
H11B—C11—H11C109.5C26—C25—H25117.4
C3—C4—C5124.99 (18)C27—C26—C25116.23 (18)
C3—C4—H4A117.5C27—C26—C33123.47 (18)
C5—C4—H4A117.5C25—C26—C33120.26 (18)
C6—C5—C4116.93 (18)C26—C27—C22121.53 (19)
C6—C5—C12123.04 (18)C26—C27—H27119.2
C4—C5—C12120.03 (17)C22—C27—H27119.2
C13—C12—C14108.2 (2)C29—C32—H32A109.5
C13—C12—C15109.0 (2)C29—C32—H32B109.5
C14—C12—C15109.5 (2)H32A—C32—H32B109.5
C13—C12—C5111.69 (18)C29—C32—H32C109.5
C14—C12—C5110.08 (18)H32A—C32—H32C109.5
C15—C12—C5108.38 (18)H32B—C32—H32C109.5
C12—C13—H13A109.5C34—C33—C35110.0 (2)
C12—C13—H13B109.5C34—C33—C36108.1 (2)
H13A—C13—H13B109.5C35—C33—C36107.2 (2)
C12—C13—H13C109.5C34—C33—C26108.84 (18)
H13A—C13—H13C109.5C35—C33—C26110.91 (17)
H13B—C13—H13C109.5C36—C33—C26111.75 (17)
C12—C14—H14A109.5C33—C34—H34A109.5
C12—C14—H14B109.5C33—C34—H34B109.5
H14A—C14—H14B109.5H34A—C34—H34B109.5
C12—C14—H14C109.5C33—C34—H34C109.5
H14A—C14—H14C109.5H34A—C34—H34C109.5
H14B—C14—H14C109.5H34B—C34—H34C109.5
C12—C15—H15A109.5C33—C35—H35A109.5
C12—C15—H15B109.5C33—C35—H35B109.5
H15A—C15—H15B109.5H35A—C35—H35B109.5
C12—C15—H15C109.5C33—C35—H35C109.5
H15A—C15—H15C109.5H35A—C35—H35C109.5
H15B—C15—H15C109.5H35B—C35—H35C109.5
C5—C6—C1121.29 (18)C28—O6—C37119.58 (16)
C5—C6—H6119.4C33—C36—H36A109.5
C1—C6—H6119.4C33—C36—H36B109.5
O2—C7—O3121.45 (19)H36A—C36—H36B109.5
O2—C7—C1124.78 (19)C33—C36—H36C109.5
O3—C7—C1113.76 (18)H36A—C36—H36C109.5
C7—O3—C16117.41 (15)H36B—C36—H36C109.5
C21—C16—C17121.7 (2)C38—C37—C42122.0 (2)
C21—C16—O3118.0 (2)C38—C37—O6120.11 (19)
C17—C16—O3120.1 (2)C42—C37—O6117.56 (19)
C16—C17—C18118.4 (2)C37—C38—C39118.7 (2)
C16—C17—H17120.8C37—C38—H38120.7
C18—C17—H17120.8C39—C38—H38120.7
C19—C18—C17120.5 (2)C40—C39—C38119.8 (2)
C19—C18—H18119.7C40—C39—H39120.1
C17—C18—H18119.7C38—C39—H39120.1
C18—C19—C20120.0 (2)C41—C40—C39120.3 (2)
C18—C19—H19120.0C41—C40—H40119.9
C20—C19—H19120.0C39—C40—H40119.9
C19—C20—C21120.3 (2)C40—C41—C42120.4 (2)
C19—C20—H20119.9C40—C41—H41119.8
C21—C20—H20119.9C42—C41—H41119.8
C16—C21—C20119.1 (2)C37—C42—C41118.8 (2)
C16—C21—H21120.5C37—C42—H42120.6
C20—C21—H21120.5C41—C42—H42120.6
C6—C1—C2—O1−178.32 (17)C27—C22—C23—O4−179.05 (17)
C7—C1—C2—O11.0 (3)C28—C22—C23—O4−0.1 (3)
C6—C1—C2—C31.5 (3)C27—C22—C23—C240.4 (3)
C7—C1—C2—C3−179.15 (17)C28—C22—C23—C24179.38 (17)
O1—C2—C3—C4178.44 (17)O4—C23—C24—C25178.80 (17)
C1—C2—C3—C4−1.4 (3)C22—C23—C24—C25−0.7 (3)
O1—C2—C3—C8−1.4 (3)O4—C23—C24—C29−0.3 (3)
C1—C2—C3—C8178.72 (18)C22—C23—C24—C29−179.78 (18)
C4—C3—C8—C9119.9 (2)C27—C22—C28—O5174.2 (2)
C2—C3—C8—C9−60.2 (3)C23—C22—C28—O5−4.8 (3)
C4—C3—C8—C110.9 (3)C27—C22—C28—O6−5.8 (3)
C2—C3—C8—C11−179.18 (19)C23—C22—C28—O6175.22 (17)
C4—C3—C8—C10−118.1 (2)C25—C24—C29—C30119.3 (2)
C2—C3—C8—C1061.8 (3)C23—C24—C29—C30−61.6 (3)
C2—C3—C4—C50.4 (3)C25—C24—C29—C31−118.9 (2)
C8—C3—C4—C5−179.69 (18)C23—C24—C29—C3160.2 (3)
C3—C4—C5—C60.5 (3)C25—C24—C29—C320.9 (3)
C3—C4—C5—C12−179.01 (18)C23—C24—C29—C32−179.98 (19)
C6—C5—C12—C135.1 (3)C23—C24—C25—C260.6 (3)
C4—C5—C12—C13−175.5 (2)C29—C24—C25—C26179.70 (18)
C6—C5—C12—C14125.3 (2)C24—C25—C26—C27−0.2 (3)
C4—C5—C12—C14−55.3 (3)C24—C25—C26—C33−178.11 (18)
C6—C5—C12—C15−115.0 (2)C25—C26—C27—C22−0.1 (3)
C4—C5—C12—C1564.4 (3)C33—C26—C27—C22177.72 (18)
C4—C5—C6—C1−0.4 (3)C23—C22—C27—C260.0 (3)
C12—C5—C6—C1179.08 (18)C28—C22—C27—C26−178.95 (18)
C2—C1—C6—C5−0.6 (3)C27—C26—C33—C34−108.6 (2)
C7—C1—C6—C5−179.91 (18)C25—C26—C33—C3469.1 (2)
C6—C1—C7—O2176.21 (19)C27—C26—C33—C35130.3 (2)
C2—C1—C7—O2−3.1 (3)C25—C26—C33—C35−52.0 (3)
C6—C1—C7—O3−4.3 (3)C27—C26—C33—C3610.7 (3)
C2—C1—C7—O3176.35 (17)C25—C26—C33—C36−171.57 (19)
O2—C7—O3—C16−0.6 (3)O5—C28—O6—C37−6.3 (3)
C1—C7—O3—C16179.95 (17)C22—C28—O6—C37173.70 (17)
C7—O3—C16—C21110.4 (2)C28—O6—C37—C38−69.2 (3)
C7—O3—C16—C17−74.1 (3)C28—O6—C37—C42117.4 (2)
C21—C16—C17—C18−1.0 (4)C42—C37—C38—C39−0.3 (3)
O3—C16—C17—C18−176.3 (2)O6—C37—C38—C39−173.3 (2)
C16—C17—C18—C190.6 (4)C37—C38—C39—C400.2 (4)
C17—C18—C19—C200.7 (4)C38—C39—C40—C410.2 (4)
C18—C19—C20—C21−1.6 (5)C39—C40—C41—C42−0.6 (4)
C17—C16—C21—C200.1 (4)C38—C37—C42—C41−0.1 (4)
O3—C16—C21—C20175.6 (2)O6—C37—C42—C41173.2 (2)
C19—C20—C21—C161.2 (4)C40—C41—C42—C370.5 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O20.821.832.563 (2)148
O4—H4···O50.821.882.604 (2)147

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OM2371).

References

  • Baptista, A. (1966). An. Acad. Bras. Cienc.38, 415.
  • Benisvy, L., Bill, E., Blake, A. J., Collison, D., Davies, E. S., Garner, C. D., Guindy, C. I., McInnes, E. J. L., McArdle, G., McMaster, J., Wilson, C. & Woloska, J. (2004). Dalton Trans. pp. 3647–3653. [PubMed]
  • Bilgram, J. H., Durig, U., Wachter, M. & Seiler, P. (1982). J. Cryst. Growth, 57, 1–5.
  • Bruker (1999). SAINT-NT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2001). SADABS and SMART-NT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Hammond, R. B., Jones, M. J., Roberts, K. J., Kutzke, H. & Klapper, H. (2002). Z. Kristallogr.217, 484–485.
  • Moore, G. F., Hambourger, M., Gervaldo, M., Poluektov, O. G., Rajh, T., Gust, D., Moore, T. A. & Moore, A. L. (2008). J. Am. Chem. Soc.130, 10466–10467. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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