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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o245–o246.
Published online 2007 December 12. doi:  10.1107/S1600536807065348
PMCID: PMC2915303

cis-3-Methyl-1-phenyl-8a,9,10,11,12,12a,12b-hexa­hydro-1H,3bH-pyrazolo[3,4:2′,3′]pyrano[4′,5′,6′-kl]xanthene

Abstract

The asymmetric unit of the title compound, C23H22N2O2, contains two independent mol­ecules, A and B. The cyclo­hexane ring of mol­ecule B is disordered, with occupancies for the major and minor conformers of 0.570 (9) and 0.430 (9), respectively. The cyclo­hexane ring adopts a boat conformation in mol­ecule A and in the major conformer of mol­ecule B, and a chair conformation in the minor conformer of mol­ecule B. In both independent mol­ecules, one of the dihydro­pyran rings adopts a boat conformation while the other is in a half-chair conformation. The dihedral angle between the pyrazole and phenyl rings is 16.0 (1)° in mol­ecule A and 12.9 (1)° in mol­ecule B. The crystal packing is stabilized by C—H(...)O and C—H(...)N inter­molecular hydrogen bonds.

Related literature

For related literature, see: Barbieri (1928 [triangle]); Bigdeli et al. (2007 [triangle]). Ion & Fara (1995 [triangle]); Sirkecioglu et al. (1995 [triangle]). For ring conformations, see: Cremer & Pople (1975 [triangle]); Nardelli (1983 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o245-scheme1.jpg

Experimental

Crystal data

  • C23H22N2O2
  • M r = 358.43
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o245-efi1.jpg
  • a = 9.8050 (3) Å
  • b = 18.8687 (6) Å
  • c = 19.9641 (8) Å
  • V = 3693.5 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 (2) K
  • 0.30 × 0.20 × 0.20 mm

Data collection

  • Bruker Kappa APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS: Sheldrick, 1996 [triangle]) T min = 0.976, T max = 0.984
  • 23902 measured reflections
  • 4888 independent reflections
  • 3380 reflections with I > 2σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.104
  • S = 1.07
  • 4888 reflections
  • 509 parameters
  • 45 restraints
  • H-atom parameters constrained
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807065348/ci2533sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065348/ci2533Isup2.hkl

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

Acknowledgments

ETSK thanks Professor M. N. Ponnuswamy, Department of Crystallography and Biophysics, University of Madras, India, for his guidance and valuable suggestions. ETSK also thanks SRM Management for their support.

supplementary crystallographic information

Comment

Xanthene derivatives find wide range of applications as biological stains, sensitizers, tracing agents, photochromic and thermochromic agents. Halogenated xanthene dyes possess light dependent insecticidial properties (Barbieri et al., 1928). Owing to their spectroscopic properties, xanthenes have interesting applications in laser technologies (Sirkecioglu et al., 1995; Ion et al., 1995). In view of this importance, an X-ray crystal structure determination of the title compound was carried out and the results are presented here.

The asymmetric unit of the title compound contains two independent molecules, A and B, with similar geometric parameters. Bond lengths and angles are comparable with those of a related structure (Bigdeli et al.,2007). The cyclohexane ring adopts a boat conformation in molecule A and also in the major conformer of molecule B; the ring adopts a chair conformation in the minor conformer of molecule B. One of the dihydropyran ring (O1/C9/C4/C3/C15/C10) adopts a boat conformation, and the other (O2/C14/C15/C3/C3/C16) adopts a half-chair conformation in both molecule A and molecule B (Nardelli, 1983; Cremer and Pople, 1975). The dihedral angle between the pyrazole and phenyl rings is 16.0 (1)° in molecule A and 12.9 (1)° in molecule B.

Intramolecular C—H···O hydrogen bonds are observed. The crystal packing is stabilized by C—H···O and C—H···N intermolecular hydrogen bonds (Table 1).

Experimental

2-(Cyclohexenyloxy)benzaldehyde (2 mmol) and EDDA (2 mmol) were added to a solution of 3-methyl-1-phenyl-pyrazol-5-one (1 mmol) in ethanol (10 ml). The mixture was refluxed until the disappearance of the starting materials, as evidenced by thin-layer chromatography. After the completion of the reaction, the solvent was evaporated under vacuum and the residue was then subjected to flash column chromatography with a hexane-ethyl acetate mixture (8:2 v/v) to obtain the title compound, which was recrystallized from ethyl acetate.

Refinement

Atoms C11 and C12 in molecule B are disordered over two positions (C11B/C12B and C11C/C12C), with refined occupancies of 0.570 (9) and 0.430 (9). The displacement parameters of disordered atoms were restrained to an approximate isotropic behaviour. The distances involving disordered C-atoms were restrained to be equal. H atoms were placed in idealized positions and allowed to ride on their parent atoms, with C—H = 0.93–0.98 Å and Uiso(H)= 1.2–1.5Ueq(C). In the absence of significant anomalous dispersion effects, Friedel pairs were merged before the final refinement.

Figures

Fig. 1.
The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level. Both disorder components are shown, and H atoms have been omitted for clarity.
Fig. 2.
The packing of the molecules viewed down the a axis.

Crystal data

C23H22N2O2F000 = 1520
Mr = 358.43Dx = 1.289 Mg m3
Orthorhombic, P212121Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 23902 reflections
a = 9.8050 (3) Åθ = 2.3–27.9º
b = 18.8687 (6) ŵ = 0.08 mm1
c = 19.9641 (8) ÅT = 293 (2) K
V = 3693.5 (2) Å3Prism, colourless
Z = 80.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer4888 independent reflections
Radiation source: fine-focus sealed tube3380 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.033
T = 293(2) Kθmax = 27.9º
ω and [var phi] scansθmin = 2.3º
Absorption correction: multi-scan(SADABS: Sheldrick, 1996)h = −12→10
Tmin = 0.976, Tmax = 0.984k = −15→24
23902 measured reflectionsl = −24→26

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.104  w = 1/[σ2(Fo2) + (0.0528P)2 + 0.0802P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
4888 reflectionsΔρmax = 0.22 e Å3
509 parametersΔρmin = −0.13 e Å3
45 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0022 (6)

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*/UeqOcc. (<1)
O1B0.2168 (2)0.56539 (9)0.28390 (10)0.0684 (5)
O2B0.21954 (17)0.40373 (8)0.19723 (8)0.0555 (4)
N1B0.4657 (2)0.35148 (10)0.31589 (9)0.0533 (5)
N2B0.41590 (19)0.35816 (9)0.25145 (9)0.0480 (5)
C1B0.3689 (3)0.37822 (13)0.35474 (12)0.0542 (6)
C2B0.2560 (2)0.40253 (11)0.31781 (11)0.0471 (5)
C3B0.1250 (2)0.43982 (12)0.33602 (12)0.0534 (6)
H3B0.06460.40650.35930.064*
C4B0.1569 (3)0.50154 (13)0.38226 (13)0.0583 (6)
C5B0.1444 (3)0.49972 (16)0.45098 (15)0.0781 (8)
H5B0.10340.46090.47140.094*
C6B0.1917 (4)0.5545 (2)0.48974 (17)0.0965 (11)
H6B0.18340.55270.53610.116*
C7B0.2516 (4)0.61211 (19)0.45937 (19)0.0970 (11)
H7B0.28710.64830.48570.116*
C8B0.2599 (3)0.61702 (15)0.39076 (17)0.0813 (9)
H8B0.29710.65700.37050.098*
C9B0.2119 (3)0.56159 (13)0.35275 (14)0.0607 (7)
C10B0.0893 (3)0.54334 (13)0.25511 (14)0.0733 (8)
H10B0.01510.57520.26820.088*0.570 (9)
H10C0.02560.56800.28320.088*0.430 (9)
C11B0.1326 (7)0.5556 (3)0.1798 (2)0.0705 (19)0.570 (9)
H11C0.14180.60590.17070.085*0.570 (9)
H11D0.21920.53280.17080.085*0.570 (9)
C12B0.0211 (8)0.5237 (3)0.1361 (5)0.089 (3)0.570 (9)
H12C0.04050.53330.08930.107*0.570 (9)
H12D−0.06600.54520.14710.107*0.570 (9)
C11C0.0371 (8)0.5653 (3)0.1871 (3)0.065 (2)0.430 (9)
H11E0.06990.61260.17690.078*0.430 (9)
H11F−0.06180.56700.18820.078*0.430 (9)
C12C0.0823 (9)0.5147 (3)0.1316 (5)0.067 (3)0.430 (9)
H12E0.18080.50990.13130.081*0.430 (9)
H12F0.05300.53200.08820.081*0.430 (9)
C13B0.0140 (3)0.44301 (14)0.14769 (14)0.0724 (8)
H13C−0.08110.42880.14650.087*0.570 (9)
H13D0.05950.41970.11060.087*0.570 (9)
H13E0.02890.40930.11240.087*0.430 (9)
H13F−0.08240.45080.15230.087*0.430 (9)
C14B0.0757 (2)0.41616 (13)0.21218 (13)0.0554 (6)
H14B0.03340.37050.22300.066*
C15B0.0541 (2)0.46588 (12)0.27109 (13)0.0563 (6)
H15B−0.04400.46510.28050.068*
C16B0.2901 (2)0.38925 (10)0.25352 (11)0.0457 (5)
C17B0.5004 (2)0.33943 (11)0.19663 (11)0.0459 (5)
C18B0.4515 (3)0.33534 (14)0.13270 (12)0.0627 (7)
H18B0.35960.34380.12440.075*
C19B0.5377 (3)0.31875 (16)0.08037 (13)0.0770 (8)
H19B0.50390.31680.03690.092*
C20B0.6727 (3)0.30509 (14)0.09214 (15)0.0738 (8)
H20B0.73090.29420.05680.089*
C21B0.7212 (3)0.30753 (14)0.15646 (15)0.0718 (8)
H21B0.81250.29730.16480.086*
C22B0.6363 (3)0.32496 (13)0.20884 (13)0.0610 (7)
H22B0.67020.32700.25230.073*
C23B0.3934 (3)0.37998 (18)0.42916 (12)0.0795 (8)
H23D0.46750.34880.44020.119*
H23E0.31250.36480.45210.119*
H23F0.41580.42740.44260.119*
O1A0.28163 (18)0.01702 (8)0.22341 (8)0.0553 (4)
O2A0.30478 (17)0.17572 (9)0.32648 (8)0.0565 (4)
N1A0.0423 (2)0.23226 (10)0.21904 (10)0.0538 (5)
N2A0.1013 (2)0.22336 (9)0.28119 (9)0.0482 (5)
C1A0.1325 (3)0.20775 (12)0.17563 (12)0.0516 (6)
C2A0.2510 (2)0.18142 (11)0.20765 (11)0.0465 (5)
C3A0.3792 (2)0.14560 (11)0.18298 (11)0.0483 (5)
H3A0.43900.18120.16260.058*
C4A0.3474 (2)0.08915 (13)0.13172 (11)0.0503 (6)
C5A0.3621 (3)0.09738 (16)0.06323 (13)0.0712 (8)
H5A0.40060.13870.04630.085*
C6A0.3202 (4)0.04481 (19)0.01978 (14)0.0855 (10)
H6A0.32920.0511−0.02620.103*
C7A0.2650 (3)−0.0169 (2)0.04454 (16)0.0849 (9)
H7A0.2357−0.05190.01510.102*
C8A0.2529 (3)−0.02709 (15)0.11252 (14)0.0709 (8)
H8A0.2174−0.06920.12930.085*
C9A0.2943 (2)0.02610 (12)0.15548 (12)0.0527 (6)
C10A0.4048 (3)0.03596 (12)0.25862 (12)0.0547 (6)
H10A0.47750.00370.24430.066*
C11A0.3751 (3)0.02188 (15)0.33230 (14)0.0735 (8)
H11A0.29010.04460.34470.088*
H11B0.3651−0.02870.33950.088*
C12A0.4873 (4)0.04944 (17)0.37496 (15)0.0902 (10)
H12A0.57020.02370.36450.108*
H12B0.46520.04030.42150.108*
C13A0.5138 (3)0.12822 (15)0.36626 (14)0.0749 (8)
H13A0.48240.15280.40600.090*
H13B0.61140.13570.36280.090*
C14A0.4457 (2)0.16051 (13)0.30581 (12)0.0560 (6)
H14A0.49120.20540.29520.067*
C15A0.4520 (2)0.11287 (11)0.24473 (11)0.0494 (5)
H15A0.54860.10960.23260.059*
C16A0.2256 (2)0.19265 (10)0.27361 (11)0.0450 (5)
C17A0.0289 (3)0.24384 (11)0.33924 (12)0.0497 (6)
C18A0.0930 (3)0.25198 (13)0.40004 (13)0.0641 (7)
H18A0.18590.24310.40380.077*
C19A0.0194 (4)0.27338 (16)0.45541 (14)0.0792 (9)
H19A0.06320.27910.49640.095*
C20A−0.1176 (4)0.28617 (15)0.45039 (16)0.0804 (9)
H20A−0.16700.30010.48790.096*
C21A−0.1819 (3)0.27838 (14)0.38969 (17)0.0764 (9)
H21A−0.27480.28760.38610.092*
C22A−0.1094 (3)0.25704 (13)0.33428 (14)0.0611 (7)
H22A−0.15350.25150.29340.073*
C23A0.0994 (3)0.21042 (17)0.10262 (12)0.0774 (9)
H23A0.01380.23420.09630.116*
H23B0.09320.16310.08530.116*
H23C0.16980.23570.07930.116*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1B0.0666 (12)0.0546 (9)0.0839 (13)−0.0046 (9)0.0256 (11)−0.0007 (9)
O2B0.0525 (10)0.0615 (9)0.0525 (9)0.0149 (8)−0.0014 (8)−0.0001 (7)
N1B0.0537 (12)0.0601 (11)0.0463 (11)0.0070 (9)−0.0029 (10)−0.0003 (9)
N2B0.0503 (12)0.0464 (10)0.0473 (11)0.0080 (9)0.0001 (9)−0.0012 (8)
C1B0.0592 (15)0.0552 (13)0.0481 (14)−0.0004 (12)0.0019 (12)−0.0003 (11)
C2B0.0471 (14)0.0432 (11)0.0509 (13)−0.0030 (10)0.0050 (11)0.0010 (10)
C3B0.0459 (13)0.0532 (13)0.0610 (14)−0.0048 (11)0.0149 (12)0.0038 (11)
C4B0.0504 (14)0.0564 (15)0.0679 (17)−0.0002 (12)0.0163 (13)−0.0088 (12)
C5B0.087 (2)0.0772 (18)0.0697 (19)−0.0013 (16)0.0265 (17)−0.0091 (16)
C6B0.108 (3)0.102 (2)0.080 (2)0.002 (2)0.019 (2)−0.025 (2)
C7B0.089 (2)0.093 (2)0.109 (3)−0.010 (2)0.012 (2)−0.049 (2)
C8B0.071 (2)0.0642 (17)0.109 (2)−0.0098 (15)0.0253 (19)−0.0212 (17)
C9B0.0499 (14)0.0567 (14)0.0756 (18)−0.0002 (12)0.0187 (14)−0.0097 (13)
C10B0.082 (2)0.0527 (15)0.085 (2)0.0182 (14)−0.0041 (17)−0.0037 (14)
C11B0.067 (4)0.062 (3)0.083 (4)0.002 (3)0.008 (3)0.021 (3)
C12B0.072 (5)0.089 (5)0.107 (5)0.003 (4)−0.015 (5)0.017 (4)
C11C0.047 (4)0.055 (3)0.093 (5)0.007 (3)0.002 (4)0.018 (3)
C12C0.061 (5)0.069 (5)0.072 (5)0.014 (4)−0.007 (5)0.020 (4)
C13B0.0637 (17)0.0737 (18)0.080 (2)−0.0011 (15)−0.0177 (15)0.0078 (15)
C14B0.0432 (13)0.0523 (13)0.0705 (17)−0.0051 (10)−0.0026 (12)0.0044 (12)
C15B0.0380 (12)0.0578 (14)0.0731 (17)0.0017 (11)0.0099 (12)0.0056 (12)
C16B0.0482 (13)0.0374 (11)0.0514 (13)0.0022 (10)0.0002 (11)0.0015 (9)
C17B0.0511 (13)0.0372 (11)0.0494 (13)0.0050 (10)0.0025 (11)0.0008 (9)
C18B0.0585 (15)0.0715 (16)0.0581 (16)0.0131 (13)0.0027 (13)0.0001 (13)
C19B0.091 (2)0.089 (2)0.0509 (16)0.0254 (18)0.0092 (16)0.0040 (14)
C20B0.079 (2)0.0733 (18)0.0685 (19)0.0241 (15)0.0251 (16)0.0064 (14)
C21B0.0570 (16)0.0726 (17)0.086 (2)0.0153 (14)0.0144 (16)0.0011 (15)
C22B0.0579 (16)0.0606 (15)0.0646 (16)0.0160 (12)0.0001 (14)−0.0028 (13)
C23B0.080 (2)0.107 (2)0.0514 (16)0.0110 (18)−0.0035 (15)−0.0047 (15)
O1A0.0589 (10)0.0563 (9)0.0506 (10)−0.0068 (8)0.0046 (8)−0.0045 (8)
O2A0.0574 (10)0.0623 (10)0.0498 (9)0.0163 (8)−0.0063 (8)−0.0070 (8)
N1A0.0515 (12)0.0575 (11)0.0525 (12)0.0107 (10)−0.0041 (10)−0.0020 (9)
N2A0.0512 (12)0.0481 (10)0.0455 (11)0.0102 (9)0.0010 (9)−0.0041 (8)
C1A0.0543 (14)0.0516 (13)0.0489 (14)0.0070 (11)−0.0012 (12)−0.0019 (10)
C2A0.0498 (14)0.0427 (11)0.0471 (13)0.0021 (10)0.0020 (11)−0.0013 (10)
C3A0.0431 (12)0.0498 (12)0.0519 (14)−0.0024 (10)0.0066 (11)0.0029 (10)
C4A0.0449 (13)0.0595 (14)0.0466 (13)0.0081 (11)0.0067 (11)−0.0046 (11)
C5A0.0761 (19)0.0848 (19)0.0526 (16)0.0123 (16)0.0129 (14)0.0012 (14)
C6A0.098 (3)0.113 (3)0.0460 (16)0.023 (2)0.0048 (16)−0.0185 (17)
C7A0.087 (2)0.100 (2)0.068 (2)0.006 (2)−0.0067 (17)−0.0346 (18)
C8A0.0676 (18)0.0724 (17)0.0726 (19)−0.0074 (15)0.0026 (15)−0.0216 (14)
C9A0.0460 (13)0.0586 (14)0.0534 (15)0.0039 (11)0.0037 (11)−0.0090 (11)
C10A0.0561 (15)0.0495 (13)0.0585 (15)0.0101 (11)−0.0027 (12)−0.0047 (11)
C11A0.087 (2)0.0682 (17)0.0660 (17)0.0043 (16)−0.0094 (17)0.0080 (14)
C12A0.103 (3)0.096 (2)0.0715 (19)0.005 (2)−0.0242 (19)0.0100 (16)
C13A0.0642 (17)0.087 (2)0.0734 (19)0.0123 (16)−0.0257 (15)−0.0178 (15)
C14A0.0447 (13)0.0585 (14)0.0649 (15)−0.0008 (11)−0.0057 (12)−0.0108 (12)
C15A0.0347 (11)0.0558 (13)0.0578 (14)0.0031 (10)0.0030 (11)−0.0051 (11)
C16A0.0494 (13)0.0389 (11)0.0466 (13)0.0044 (10)−0.0019 (11)−0.0016 (9)
C17A0.0597 (15)0.0380 (11)0.0515 (14)0.0066 (10)0.0106 (12)0.0030 (10)
C18A0.0673 (17)0.0716 (17)0.0533 (16)0.0125 (14)0.0060 (14)−0.0058 (12)
C19A0.094 (2)0.090 (2)0.0536 (17)0.0166 (18)0.0119 (16)−0.0093 (14)
C20A0.095 (2)0.0783 (19)0.068 (2)0.0177 (17)0.0329 (19)0.0012 (15)
C21A0.0666 (19)0.0690 (18)0.094 (2)0.0146 (15)0.0250 (17)0.0024 (16)
C22A0.0561 (16)0.0602 (15)0.0670 (17)0.0102 (12)0.0050 (14)−0.0011 (12)
C23A0.076 (2)0.106 (2)0.0496 (16)0.0238 (17)−0.0069 (14)0.0007 (15)

Geometric parameters (Å, °)

O1B—C9B1.377 (3)C21B—H21B0.93
O1B—C10B1.438 (3)C22B—H22B0.93
O2B—C16B1.348 (3)C23B—H23D0.96
O2B—C14B1.461 (3)C23B—H23E0.96
N1B—C1B1.325 (3)C23B—H23F0.96
N1B—N2B1.382 (3)O1A—C9A1.373 (3)
N2B—C16B1.366 (3)O1A—C10A1.443 (3)
N2B—C17B1.418 (3)O2A—C16A1.349 (3)
C1B—C2B1.407 (3)O2A—C14A1.470 (3)
C1B—C23B1.505 (3)N1A—C1A1.322 (3)
C2B—C16B1.350 (3)N1A—N2A1.379 (3)
C2B—C3B1.509 (3)N2A—C16A1.358 (3)
C3B—C4B1.519 (3)N2A—C17A1.413 (3)
C3B—C15B1.551 (3)C1A—C2A1.416 (3)
C3B—H3B0.98C1A—C23A1.494 (3)
C4B—C5B1.378 (4)C2A—C16A1.357 (3)
C4B—C9B1.387 (3)C2A—C3A1.510 (3)
C5B—C6B1.372 (4)C3A—C4A1.510 (3)
C5B—H5B0.93C3A—C15A1.553 (3)
C6B—C7B1.376 (5)C3A—H3A0.98
C6B—H6B0.93C4A—C9A1.383 (3)
C7B—C8B1.375 (4)C4A—C5A1.384 (3)
C7B—H7B0.93C5A—C6A1.380 (4)
C8B—C9B1.375 (4)C5A—H5A0.93
C8B—H8B0.93C6A—C7A1.375 (4)
C10B—C11C1.510 (5)C6A—H6A0.93
C10B—C15B1.535 (3)C7A—C8A1.376 (4)
C10B—C11B1.579 (5)C7A—H7A0.93
C10B—H10B0.98C8A—C9A1.381 (3)
C10B—H10C0.96C8A—H8A0.93
C11B—C12B1.522 (6)C10A—C11A1.523 (4)
C11B—H11C0.97C10A—C15A1.548 (3)
C11B—H11D0.97C10A—H10A0.98
C12B—C13B1.542 (6)C11A—C12A1.485 (4)
C12B—H12C0.97C11A—H11A0.97
C12B—H12D0.97C11A—H11B0.97
C11C—C12C1.528 (7)C12A—C13A1.519 (4)
C11C—H11E0.97C12A—H12A0.97
C11C—H11F0.97C12A—H12B0.97
C12C—C13B1.543 (6)C13A—C14A1.508 (4)
C12C—H12E0.97C13A—H13A0.97
C12C—H12F0.97C13A—H13B0.97
C13B—C14B1.510 (3)C14A—C15A1.516 (3)
C13B—H13C0.97C14A—H14A0.98
C13B—H13D0.97C15A—H15A0.98
C13B—H13E0.96C17A—C18A1.375 (4)
C13B—H13F0.96C17A—C22A1.382 (4)
C14B—C15B1.519 (3)C18A—C19A1.380 (4)
C14B—H14B0.98C18A—H18A0.93
C15B—H15B0.98C19A—C20A1.369 (5)
C17B—C18B1.366 (3)C19A—H19A0.93
C17B—C22B1.381 (3)C20A—C21A1.374 (4)
C18B—C19B1.380 (4)C20A—H20A0.93
C18B—H18B0.93C21A—C22A1.375 (4)
C19B—C20B1.369 (4)C21A—H21A0.93
C19B—H19B0.93C22A—H22A0.93
C20B—C21B1.370 (4)C23A—H23A0.96
C20B—H20B0.93C23A—H23B0.96
C21B—C22B1.377 (4)C23A—H23C0.96
C9B—O1B—C10B110.7 (2)C19B—C20B—H20B120.3
C16B—O2B—C14B110.97 (18)C21B—C20B—H20B120.3
C1B—N1B—N2B104.91 (18)C20B—C21B—C22B120.6 (3)
C16B—N2B—N1B109.26 (18)C20B—C21B—H21B119.7
C16B—N2B—C17B131.16 (19)C22B—C21B—H21B119.7
N1B—N2B—C17B119.31 (18)C21B—C22B—C17B119.8 (3)
N1B—C1B—C2B112.4 (2)C21B—C22B—H22B120.1
N1B—C1B—C23B118.2 (2)C17B—C22B—H22B120.1
C2B—C1B—C23B129.5 (2)C1B—C23B—H23D109.5
C16B—C2B—C1B104.0 (2)C1B—C23B—H23E109.5
C16B—C2B—C3B121.8 (2)H23D—C23B—H23E109.5
C1B—C2B—C3B134.1 (2)C1B—C23B—H23F109.5
C2B—C3B—C4B109.2 (2)H23D—C23B—H23F109.5
C2B—C3B—C15B109.15 (19)H23E—C23B—H23F109.5
C4B—C3B—C15B110.9 (2)C9A—O1A—C10A112.02 (19)
C2B—C3B—H3B109.2C16A—O2A—C14A111.58 (18)
C4B—C3B—H3B109.2C1A—N1A—N2A105.45 (19)
C15B—C3B—H3B109.2C16A—N2A—N1A109.16 (18)
C5B—C4B—C9B118.6 (3)C16A—N2A—C17A131.2 (2)
C5B—C4B—C3B124.6 (2)N1A—N2A—C17A119.59 (18)
C9B—C4B—C3B116.7 (2)N1A—C1A—C2A112.1 (2)
C6B—C5B—C4B120.9 (3)N1A—C1A—C23A118.8 (2)
C6B—C5B—H5B119.6C2A—C1A—C23A129.1 (2)
C4B—C5B—H5B119.6C16A—C2A—C1A103.5 (2)
C5B—C6B—C7B119.4 (3)C16A—C2A—C3A122.7 (2)
C5B—C6B—H6B120.3C1A—C2A—C3A133.9 (2)
C7B—C6B—H6B120.3C4A—C3A—C2A111.42 (18)
C8B—C7B—C6B121.1 (3)C4A—C3A—C15A110.65 (18)
C8B—C7B—H7B119.4C2A—C3A—C15A107.56 (17)
C6B—C7B—H7B119.4C4A—C3A—H3A109.1
C9B—C8B—C7B118.6 (3)C2A—C3A—H3A109.1
C9B—C8B—H8B120.7C15A—C3A—H3A109.1
C7B—C8B—H8B120.7C9A—C4A—C5A118.4 (2)
C8B—C9B—O1B120.0 (3)C9A—C4A—C3A116.9 (2)
C8B—C9B—C4B121.3 (3)C5A—C4A—C3A124.7 (2)
O1B—C9B—C4B118.7 (2)C6A—C5A—C4A120.6 (3)
O1B—C10B—C11C125.1 (4)C6A—C5A—H5A119.7
O1B—C10B—C15B112.8 (2)C4A—C5A—H5A119.7
C11C—C10B—C15B111.8 (3)C7A—C6A—C5A120.0 (3)
O1B—C10B—C11B96.0 (3)C7A—C6A—H6A120.0
C15B—C10B—C11B113.5 (3)C5A—C6A—H6A120.0
O1B—C10B—H10B111.2C6A—C7A—C8A120.5 (3)
C15B—C10B—H10B111.2C6A—C7A—H7A119.8
C11B—C10B—H10B111.2C8A—C7A—H7A119.8
O1B—C10B—H10C101.1C7A—C8A—C9A119.0 (3)
C15B—C10B—H10C101.2C7A—C8A—H8A120.5
C11B—C10B—H10C131.3C9A—C8A—H8A120.5
C12B—C11B—C10B107.2 (6)O1A—C9A—C8A119.8 (2)
C12B—C11B—H11C110.3O1A—C9A—C4A118.7 (2)
C10B—C11B—H11C110.3C8A—C9A—C4A121.5 (2)
C12B—C11B—H11D110.3O1A—C10A—C11A105.5 (2)
C10B—C11B—H11D110.3O1A—C10A—C15A113.26 (19)
H11C—C11B—H11D108.5C11A—C10A—C15A113.2 (2)
C11B—C12B—C13B109.7 (5)O1A—C10A—H10A108.2
C11B—C12B—H12C109.7C11A—C10A—H10A108.2
C13B—C12B—H12C109.7C15A—C10A—H10A108.2
C11B—C12B—H12D109.7C12A—C11A—C10A110.6 (3)
C13B—C12B—H12D109.7C12A—C11A—H11A109.5
H12C—C12B—H12D108.2C10A—C11A—H11A109.5
C10B—C11C—C12C112.5 (6)C12A—C11A—H11B109.5
C10B—C11C—H11E109.1C10A—C11A—H11B109.5
C12C—C11C—H11E109.1H11A—C11A—H11B108.1
C10B—C11C—H11F109.1C11A—C12A—C13A113.8 (2)
C12C—C11C—H11F109.1C11A—C12A—H12A108.8
H11E—C11C—H11F107.8C13A—C12A—H12A108.8
C11C—C12C—C13B105.7 (5)C11A—C12A—H12B108.8
C11C—C12C—H12E110.6C13A—C12A—H12B108.8
C13B—C12C—H12E110.6H12A—C12A—H12B107.7
C11C—C12C—H12F110.6C14A—C13A—C12A114.3 (2)
C13B—C12C—H12F110.6C14A—C13A—H13A108.7
H12E—C12C—H12F108.7C12A—C13A—H13A108.7
C14B—C13B—C12B116.2 (4)C14A—C13A—H13B108.7
C14B—C13B—C12C107.3 (4)C12A—C13A—H13B108.7
C14B—C13B—H13C108.2H13A—C13A—H13B107.6
C12B—C13B—H13C108.2O2A—C14A—C13A105.7 (2)
C12C—C13B—H13C130.9O2A—C14A—C15A112.32 (18)
C14B—C13B—H13D108.2C13A—C14A—C15A112.7 (2)
C12B—C13B—H13D108.2O2A—C14A—H14A108.7
H13C—C13B—H13D107.4C13A—C14A—H14A108.7
C14B—C13B—H13E109.9C15A—C14A—H14A108.7
C12B—C13B—H13E122.5C14A—C15A—C10A113.5 (2)
C12C—C13B—H13E111.2C14A—C15A—C3A112.59 (18)
H13C—C13B—H13E86.9C10A—C15A—C3A112.20 (19)
C14B—C13B—H13F111.4C14A—C15A—H15A105.9
C12B—C13B—H13F84.8C10A—C15A—H15A105.9
C12C—C13B—H13F108.3C3A—C15A—H15A105.9
H13D—C13B—H13F126.5O2A—C16A—C2A128.1 (2)
H13E—C13B—H13F108.7O2A—C16A—N2A122.1 (2)
O2B—C14B—C13B105.5 (2)C2A—C16A—N2A109.9 (2)
O2B—C14B—C15B113.08 (19)C18A—C17A—C22A119.4 (2)
C13B—C14B—C15B113.4 (2)C18A—C17A—N2A121.7 (2)
O2B—C14B—H14B108.2C22A—C17A—N2A118.9 (2)
C13B—C14B—H14B108.2C17A—C18A—C19A120.0 (3)
C15B—C14B—H14B108.2C17A—C18A—H18A120.0
C14B—C15B—C10B113.3 (2)C19A—C18A—H18A120.0
C14B—C15B—C3B112.87 (19)C20A—C19A—C18A120.4 (3)
C10B—C15B—C3B112.0 (2)C20A—C19A—H19A119.8
C14B—C15B—H15B106.0C18A—C19A—H19A119.8
C10B—C15B—H15B106.0C19A—C20A—C21A119.7 (3)
C3B—C15B—H15B106.0C19A—C20A—H20A120.1
O2B—C16B—C2B128.9 (2)C21A—C20A—H20A120.1
O2B—C16B—N2B121.7 (2)C20A—C21A—C22A120.3 (3)
C2B—C16B—N2B109.4 (2)C20A—C21A—H21A119.9
C18B—C17B—C22B119.5 (2)C22A—C21A—H21A119.9
C18B—C17B—N2B122.0 (2)C21A—C22A—C17A120.1 (3)
C22B—C17B—N2B118.5 (2)C21A—C22A—H22A119.9
C17B—C18B—C19B120.3 (3)C17A—C22A—H22A119.9
C17B—C18B—H18B119.8C1A—C23A—H23A109.5
C19B—C18B—H18B119.8C1A—C23A—H23B109.5
C20B—C19B—C18B120.3 (3)H23A—C23A—H23B109.5
C20B—C19B—H19B119.8C1A—C23A—H23C109.5
C18B—C19B—H19B119.8H23A—C23A—H23C109.5
C19B—C20B—C21B119.4 (3)H23B—C23A—H23C109.5
C1B—N1B—N2B—C16B0.3 (2)C17B—C18B—C19B—C20B1.1 (5)
C1B—N1B—N2B—C17B174.95 (19)C18B—C19B—C20B—C21B0.5 (5)
N2B—N1B—C1B—C2B0.0 (3)C19B—C20B—C21B—C22B−1.3 (4)
N2B—N1B—C1B—C23B−178.9 (2)C20B—C21B—C22B—C17B0.7 (4)
N1B—C1B—C2B—C16B−0.3 (3)C18B—C17B—C22B—C21B0.9 (4)
C23B—C1B—C2B—C16B178.5 (3)N2B—C17B—C22B—C21B−179.2 (2)
N1B—C1B—C2B—C3B−176.4 (2)C1A—N1A—N2A—C16A−0.8 (2)
C23B—C1B—C2B—C3B2.3 (4)C1A—N1A—N2A—C17A−179.2 (2)
C16B—C2B—C3B—C4B−128.2 (2)N2A—N1A—C1A—C2A0.9 (3)
C1B—C2B—C3B—C4B47.4 (3)N2A—N1A—C1A—C23A−179.5 (2)
C16B—C2B—C3B—C15B−6.7 (3)N1A—C1A—C2A—C16A−0.6 (3)
C1B—C2B—C3B—C15B168.8 (2)C23A—C1A—C2A—C16A179.8 (3)
C2B—C3B—C4B—C5B−98.7 (3)N1A—C1A—C2A—C3A176.9 (2)
C15B—C3B—C4B—C5B141.0 (3)C23A—C1A—C2A—C3A−2.7 (4)
C2B—C3B—C4B—C9B76.3 (3)C16A—C2A—C3A—C4A132.9 (2)
C15B—C3B—C4B—C9B−44.1 (3)C1A—C2A—C3A—C4A−44.2 (3)
C9B—C4B—C5B—C6B−3.3 (5)C16A—C2A—C3A—C15A11.4 (3)
C3B—C4B—C5B—C6B171.5 (3)C1A—C2A—C3A—C15A−165.7 (2)
C4B—C5B—C6B—C7B0.4 (5)C2A—C3A—C4A—C9A−75.7 (2)
C5B—C6B—C7B—C8B2.7 (6)C15A—C3A—C4A—C9A43.9 (3)
C6B—C7B—C8B—C9B−2.7 (5)C2A—C3A—C4A—C5A101.4 (3)
C7B—C8B—C9B—O1B179.0 (3)C15A—C3A—C4A—C5A−139.0 (2)
C7B—C8B—C9B—C4B−0.3 (5)C9A—C4A—C5A—C6A2.3 (4)
C10B—O1B—C9B—C8B−133.9 (3)C3A—C4A—C5A—C6A−174.8 (2)
C10B—O1B—C9B—C4B45.5 (3)C4A—C5A—C6A—C7A−1.0 (5)
C5B—C4B—C9B—C8B3.3 (4)C5A—C6A—C7A—C8A−0.9 (5)
C3B—C4B—C9B—C8B−172.0 (2)C6A—C7A—C8A—C9A1.4 (5)
C5B—C4B—C9B—O1B−176.1 (2)C10A—O1A—C9A—C8A132.4 (2)
C3B—C4B—C9B—O1B8.7 (4)C10A—O1A—C9A—C4A−48.3 (3)
C9B—O1B—C10B—C11C155.7 (4)C7A—C8A—C9A—O1A179.4 (3)
C9B—O1B—C10B—C15B−62.2 (3)C7A—C8A—C9A—C4A0.0 (4)
C9B—O1B—C10B—C11B179.2 (3)C5A—C4A—C9A—O1A178.8 (2)
O1B—C10B—C11B—C12B170.4 (5)C3A—C4A—C9A—O1A−3.9 (3)
C11C—C10B—C11B—C12B−43.1 (5)C5A—C4A—C9A—C8A−1.8 (4)
C15B—C10B—C11B—C12B52.3 (6)C3A—C4A—C9A—C8A175.5 (2)
C10B—C11B—C12B—C13B−63.6 (9)C9A—O1A—C10A—C11A−179.09 (19)
O1B—C10B—C11C—C12C89.8 (6)C9A—O1A—C10A—C15A56.6 (2)
C15B—C10B—C11C—C12C−52.6 (7)O1A—C10A—C11A—C12A−171.6 (2)
C11B—C10B—C11C—C12C47.7 (6)C15A—C10A—C11A—C12A−47.2 (3)
C10B—C11C—C12C—C13B64.4 (9)C10A—C11A—C12A—C13A57.8 (4)
C11B—C12B—C13B—C14B20.3 (10)C11A—C12A—C13A—C14A−13.3 (4)
C11B—C12B—C13B—C12C−52.4 (11)C16A—O2A—C14A—C13A−168.59 (19)
C11C—C12C—C13B—C14B−66.1 (7)C16A—O2A—C14A—C15A−45.3 (3)
C11C—C12C—C13B—C12B50.1 (12)C12A—C13A—C14A—O2A82.6 (3)
C16B—O2B—C14B—C13B171.14 (18)C12A—C13A—C14A—C15A−40.5 (4)
C16B—O2B—C14B—C15B46.7 (3)O2A—C14A—C15A—C10A−69.3 (3)
C12B—C13B—C14B—O2B−87.8 (5)C13A—C14A—C15A—C10A50.0 (3)
C12C—C13B—C14B—O2B−64.2 (4)O2A—C14A—C15A—C3A59.6 (3)
C12B—C13B—C14B—C15B36.5 (6)C13A—C14A—C15A—C3A178.8 (2)
C12C—C13B—C14B—C15B60.1 (4)O1A—C10A—C15A—C14A114.3 (2)
O2B—C14B—C15B—C10B71.9 (3)C11A—C10A—C15A—C14A−5.7 (3)
C13B—C14B—C15B—C10B−48.1 (3)O1A—C10A—C15A—C3A−14.8 (3)
O2B—C14B—C15B—C3B−56.7 (3)C11A—C10A—C15A—C3A−134.8 (2)
C13B—C14B—C15B—C3B−176.7 (2)C4A—C3A—C15A—C14A−161.57 (19)
O1B—C10B—C15B—C14B−104.6 (3)C2A—C3A—C15A—C14A−39.7 (2)
C11C—C10B—C15B—C14B42.7 (4)C4A—C3A—C15A—C10A−32.0 (2)
C11B—C10B—C15B—C14B3.3 (4)C2A—C3A—C15A—C10A89.9 (2)
O1B—C10B—C15B—C3B24.5 (3)C14A—O2A—C16A—C2A16.4 (3)
C11C—C10B—C15B—C3B171.8 (4)C14A—O2A—C16A—N2A−165.43 (19)
C11B—C10B—C15B—C3B132.3 (3)C1A—C2A—C16A—O2A178.4 (2)
C2B—C3B—C15B—C14B34.1 (3)C3A—C2A—C16A—O2A0.6 (4)
C4B—C3B—C15B—C14B154.5 (2)C1A—C2A—C16A—N2A0.1 (2)
C2B—C3B—C15B—C10B−95.2 (2)C3A—C2A—C16A—N2A−177.80 (18)
C4B—C3B—C15B—C10B25.2 (3)N1A—N2A—C16A—O2A−178.00 (18)
C14B—O2B—C16B—C2B−18.7 (3)C17A—N2A—C16A—O2A0.1 (3)
C14B—O2B—C16B—N2B162.71 (19)N1A—N2A—C16A—C2A0.5 (2)
C1B—C2B—C16B—O2B−178.2 (2)C17A—N2A—C16A—C2A178.6 (2)
C3B—C2B—C16B—O2B−1.5 (4)C16A—N2A—C17A—C18A17.7 (4)
C1B—C2B—C16B—N2B0.5 (2)N1A—N2A—C17A—C18A−164.3 (2)
C3B—C2B—C16B—N2B177.20 (18)C16A—N2A—C17A—C22A−163.4 (2)
N1B—N2B—C16B—O2B178.31 (19)N1A—N2A—C17A—C22A14.6 (3)
C17B—N2B—C16B—O2B4.5 (3)C22A—C17A—C18A—C19A−0.2 (4)
N1B—N2B—C16B—C2B−0.5 (2)N2A—C17A—C18A—C19A178.8 (2)
C17B—N2B—C16B—C2B−174.3 (2)C17A—C18A—C19A—C20A0.4 (4)
C16B—N2B—C17B—C18B−16.1 (4)C18A—C19A—C20A—C21A−0.7 (5)
N1B—N2B—C17B—C18B170.7 (2)C19A—C20A—C21A—C22A0.7 (5)
C16B—N2B—C17B—C22B164.0 (2)C20A—C21A—C22A—C17A−0.5 (4)
N1B—N2B—C17B—C22B−9.3 (3)C18A—C17A—C22A—C21A0.2 (4)
C22B—C17B—C18B—C19B−1.7 (4)N2A—C17A—C22A—C21A−178.8 (2)
N2B—C17B—C18B—C19B178.3 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C15A—H15A···O1Bi0.982.473.417 (3)163
C15B—H15B···O1Aii0.982.533.432 (3)153
C18A—H18A···O2A0.932.312.922 (3)123
C18B—H18B···O2B0.932.302.915 (3)123
C14B—H14B···N1A0.982.613.488 (3)149

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2533).

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