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The title compound, C30H26N2O4, crystallizes in space group P21/n, with two crystallographically independent mol­ecules in the asymmetric unit. Two of the phenyl rings are perpendicular to one another. The molecular structure is influenced by strong N—H...O, N—H...N and C—H...O intramolecular interactions, and the crystal structure is stabilized by C—H...O and C—H...π intermolecular interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803018634/bt6331sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803018634/bt6331Isup2.hkl
Contains datablock I

CCDC reference: 222920

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • R factor = 0.056
  • wR factor = 0.166
  • Data-to-parameter ratio = 17.6

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Comment top

Cyclophane derivatives constitute a novel building block for the potent human immuno deficiency virus (HIV) protease inhibitor (Ettmayer et al., 1996). Cyclophane derivatives act catalytically as cholesterol shuttles to accelerate the exchange of free cholesterol between cells and serum lipo proteins (Christian et al., 1999). Cyclophane derivatives act as potential reversal agents of muscle relaxants by chemical chelation (Cameron et al., 2002). The importance of cyclophane derivatives prompted us to undertake the structure analysis of the title compound, (I).

The asymmetric unit of (I) contains two molecules (A and B), with similar bond lengths and angles.

The C—C bond lengths in the phenyl rings (A, B, C and D) are comparable to the reported literature value of 1.384 (13) Å. All of the C—N bond lengths in both of the molecules also agree with the reported literature values [Csp2—N = 1.339 (16) Å and Cphenyl—N = 1.419 (17) Å; Allen et al., 1987].

The exocyclic angles around atoms C16 and C24 show considerable asymmetry, with the O17—C16—C15 angle [122.4 (2)° for molecule A and 122.9 (2)° for molecule B] being wider than the O17—C16—C11 angle [117.2 (2)° for molecule A and 117.8 (2)° for molecule B], and the C19—C24—C25 angle [124.5 (2)° for molecule A and 122.6 (2)° for molecule B] being wider than the C23—C24—C25 angle [117.3 (2) for molecule A and 118.9 (2)° for molecule B]. This asymmetry may be due to the short contacts between H15A—H18B (2.19 Å), H15B—H18C (1.90 Å), H18A—H25B (2.11 Å) and H25C—H18B (2.14 Å).

The values of the C33—N1—C2—C3 [−40.3 (3) for molecule A and 64.6 (3) for molecule B] and C6—C7—N8—C9 [45.2 (3) for molecule A and −13.5 (3) for molecule B] torsion angles indicate that the two amide groups are twisted from the plane of phenyl ring A, with dihedral angles of 39.6 (1) and 44.3 (2)° for molecule A and 66.5 (2) and 14.9 (1)° for molecule B.

Rings B and D are perpendicular to one another, the dihedral angle between their planes being 87.0 (1)° for molecule A and 90.0 (1)° for molecule B. The dihedral angle between rings B and C is 84.8 (1)° for molecule A and 86.8 (1)° for molecule B, indicating that these two phenyl rings are almost perpendicular to one another.

In addition to the van der Waals interactions, the molecular structure is influenced by N—H···O, N—H···N and C—H···O intramolecular interactions. The packing of the molecule is stabilized by C—H···O intermolecular interactions which run along the ab plane (Fig. 2). In addition, symmetry-related molecules are also linked by weak C—H···π intermolecular interactions, such that atom H5B is 2.91 Å from the centroid of ring D at (3/2 − x,1/2 + y,1/2 − z), with a C5—H5B···Centroid angle of 161° and a C5—H5B···Centroid distance of 3.801 (3) Å.

Experimental top

In high-dilution conditions, benzene 1,2-dioxy bis(ethanoyl chloride) (1 mmol) and ortho phenylene diamine (1 mmol) were cyclized in chloroform in the presence of triethylamine, affording the title compound. A single-crystal of (I) suitable for X-ray analysis was obtained by recrystallization from chloroform/methanol (1:1) by slow evaporation.

Refinement top

H atoms were positioned geometrically and were treated as riding on their parent C atoms, with aromatic C—H distances of 0.93 Å, methyl C—H distances of 0.96 Å, ethylene C—H distances of 0.97 Å and N—H distances of 0.86 Å, and with Uiso(H) values of 1.5Ueq(C) for methyl H atoms and 1.2Ueq(N,C) for other H atoms. The methyl groups were allowed to rotate but not to tip.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: 'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)'; software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids and the atom-labelling scheme.
[Figure 2] Fig. 2. The packing of the molecules of (I), viewed along the b axis.
30,31-Dimethyl-3,26-dioxa-11,18- diazapentacyclo[26.4.0.04,9.012,17.020,25]dotriconta- 1(32),4,6,8,12,14,16,20,22,24,28,30-dodecaene-10,19-dione top
Crystal data top
C30H26N2O4F(000) = 2016
Mr = 478.53Dx = 1.288 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5463 reflections
a = 15.5767 (9) Åθ = 2.3–21.7°
b = 15.7746 (9) ŵ = 0.09 mm1
c = 20.5721 (12) ÅT = 293 K
β = 102.541 (1)°Block, colourless
V = 4934.3 (5) Å30.24 × 0.20 × 0.16 mm
Z = 8
Data collection top
CCD Area Detector
diffractometer
6259 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
Graphite monochromatorθmax = 28.1°, θmin = 1.5°
ω scansh = 1920
30895 measured reflectionsk = 1820
11480 independent reflectionsl = 2027
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0872P)2 + 0.0307P]
where P = (Fo2 + 2Fc2)/3
11480 reflections(Δ/σ)max < 0.001
653 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C30H26N2O4V = 4934.3 (5) Å3
Mr = 478.53Z = 8
Monoclinic, P21/nMo Kα radiation
a = 15.5767 (9) ŵ = 0.09 mm1
b = 15.7746 (9) ÅT = 293 K
c = 20.5721 (12) Å0.24 × 0.20 × 0.16 mm
β = 102.541 (1)°
Data collection top
CCD Area Detector
diffractometer
6259 reflections with I > 2σ(I)
30895 measured reflectionsRint = 0.031
11480 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.166H-atom parameters constrained
S = 0.99Δρmax = 0.30 e Å3
11480 reflectionsΔρmin = 0.22 e Å3
653 parameters
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
N1A1.41506 (10)0.26652 (10)0.20245 (9)0.0563 (4)
H1A1.37060.27030.22080.068*
C2A1.49701 (13)0.24200 (12)0.24294 (11)0.0542 (5)
C3A1.55136 (15)0.18642 (13)0.21823 (13)0.0682 (6)
H3A1.53290.16470.17550.082*
C4A1.63108 (17)0.16332 (16)0.25554 (16)0.0816 (8)
H4A1.66760.12760.23780.098*
C5A1.65724 (16)0.19269 (16)0.31909 (16)0.0827 (8)
H5A1.71180.17710.34460.099*
C6A1.60285 (14)0.24586 (15)0.34607 (13)0.0720 (6)
H6A1.62010.26400.39000.086*
C7A1.52261 (12)0.27191 (12)0.30736 (11)0.0549 (5)
N8A1.46891 (10)0.33039 (10)0.33343 (9)0.0570 (4)
H8A1.41360.31960.32720.068*
C9A1.49889 (13)0.40151 (14)0.36718 (11)0.0592 (5)
O10A1.57672 (11)0.41851 (12)0.38070 (11)0.1051 (7)
C11A1.43422 (13)0.46196 (13)0.38580 (10)0.0537 (5)
C12A1.46969 (15)0.53779 (15)0.41337 (12)0.0719 (6)
H12A1.53010.54600.42040.086*
C13A1.41855 (17)0.60089 (16)0.43058 (13)0.0815 (7)
H13A1.44410.65070.44980.098*
C14A1.32947 (17)0.58986 (15)0.41915 (13)0.0777 (7)
H14A1.29420.63320.42960.093*
C15A1.29151 (15)0.51564 (13)0.39251 (12)0.0694 (6)
H15A1.23090.50860.38530.083*
C16A1.34357 (13)0.45106 (12)0.37634 (11)0.0556 (5)
O17A1.30940 (9)0.37462 (8)0.35071 (8)0.0691 (4)
C18A1.21888 (14)0.35825 (14)0.35052 (15)0.0810 (8)
H18A1.18140.39250.31670.097*
H18B1.20680.37280.39340.097*
C19A1.20025 (13)0.26572 (13)0.33624 (13)0.0603 (6)
C20A1.20751 (14)0.21119 (14)0.38939 (12)0.0651 (6)
H20A1.22770.23260.43210.078*
C21A1.18620 (14)0.12599 (14)0.38216 (11)0.0610 (6)
C22A1.15514 (14)0.09469 (13)0.31802 (12)0.0607 (6)
C23A1.14963 (14)0.14877 (14)0.26506 (11)0.0605 (5)
H23A1.13040.12720.22230.073*
C24A1.17141 (12)0.23407 (13)0.27226 (12)0.0597 (6)
C25A1.15893 (14)0.28620 (15)0.21030 (13)0.0751 (7)
H25A1.11210.26250.17630.090*
H25B1.14280.34370.21940.090*
O26A1.24030 (8)0.28655 (9)0.18736 (8)0.0655 (4)
C27A1.23625 (13)0.31209 (12)0.12305 (11)0.0550 (5)
C28A1.15879 (15)0.33791 (15)0.08110 (13)0.0757 (7)
H28A1.10700.33920.09670.091*
C29A1.15754 (19)0.36159 (17)0.01695 (14)0.0874 (8)
H29A1.10470.37730.01110.105*
C30A1.2330 (2)0.36229 (18)0.00600 (13)0.0899 (8)
H30A1.23230.38030.04920.108*
C31A1.30961 (17)0.33647 (15)0.03457 (12)0.0732 (7)
H31A1.36070.33630.01810.088*
C32A1.31416 (13)0.31043 (12)0.09975 (10)0.0540 (5)
C33A1.40273 (13)0.28413 (13)0.13726 (11)0.0580 (5)
O34A1.46308 (10)0.28107 (14)0.10817 (9)0.1012 (6)
C35A1.1961 (2)0.06967 (17)0.44247 (13)0.0960 (9)
H35A1.21850.10230.48190.144*
H35B1.23620.02450.43930.144*
H35C1.13980.04640.44470.144*
C36A1.1282 (2)0.00294 (15)0.30620 (14)0.0945 (9)
H36A1.10050.00500.26020.142*
H36B1.08760.01180.33350.142*
H36C1.17930.03260.31750.142*
N1B0.88809 (10)0.40621 (10)0.13123 (8)0.0505 (4)
H1B0.83800.42130.13850.061*
C2B0.95973 (11)0.46529 (12)0.14452 (10)0.0475 (5)
C3B0.99447 (14)0.49495 (14)0.09276 (11)0.0631 (6)
H3B0.96990.47790.04950.076*
C4B1.06496 (16)0.54942 (15)0.10411 (12)0.0720 (7)
H4B1.08740.56990.06880.086*
C5B1.10161 (14)0.57313 (13)0.16786 (13)0.0662 (6)
H5B1.15020.60890.17580.079*
C6B1.06844 (13)0.54542 (13)0.22019 (11)0.0584 (5)
H6B1.09420.56270.26320.070*
C7B0.99572 (12)0.49097 (12)0.20941 (10)0.0468 (5)
N8B0.95594 (10)0.46265 (10)0.26080 (8)0.0536 (4)
H8B0.90530.43900.24850.064*
C9B0.98793 (12)0.46823 (12)0.32704 (10)0.0499 (5)
O10B1.06118 (10)0.49574 (12)0.35058 (8)0.0830 (5)
C11B0.93044 (12)0.43761 (11)0.37200 (9)0.0471 (4)
C12B0.97500 (14)0.42029 (13)0.43672 (10)0.0615 (6)
H12B1.03550.42860.44820.074*
C13B0.93258 (18)0.39137 (15)0.48411 (11)0.0748 (7)
H13B0.96380.38030.52720.090*
C14B0.84369 (17)0.37911 (15)0.46705 (12)0.0728 (7)
H14B0.81440.35910.49880.087*
C15B0.79676 (14)0.39594 (14)0.40363 (11)0.0630 (6)
H15B0.73630.38700.39290.076*
C16B0.83928 (12)0.42612 (11)0.35563 (10)0.0482 (5)
O17B0.79584 (8)0.44641 (9)0.29236 (7)0.0611 (4)
C18B0.70183 (13)0.43428 (16)0.27477 (13)0.0807 (7)
H18C0.67730.44290.31370.097*
H18D0.68880.37670.25920.097*
C19B0.66083 (12)0.49536 (13)0.22132 (11)0.0553 (5)
C20B0.64862 (14)0.57815 (15)0.24098 (11)0.0629 (6)
H20B0.66950.59300.28540.075*
C21B0.60674 (14)0.63908 (13)0.19726 (12)0.0612 (6)
C22B0.57653 (13)0.61750 (13)0.13133 (11)0.0561 (5)
C23B0.58890 (13)0.53525 (14)0.11191 (11)0.0579 (5)
H23B0.56880.52090.06740.069*
C24B0.62958 (12)0.47352 (12)0.15534 (11)0.0529 (5)
C25B0.63240 (13)0.38470 (13)0.13043 (13)0.0712 (7)
H25C0.61510.34540.16150.085*
H25D0.59170.37870.08770.085*
O26B0.72018 (8)0.36591 (8)0.12353 (8)0.0620 (4)
C27B0.73532 (12)0.28645 (12)0.10082 (10)0.0490 (5)
C28B0.67016 (14)0.22507 (13)0.08635 (11)0.0632 (6)
H28B0.61330.23730.09080.076*
C29B0.69013 (15)0.14582 (14)0.06528 (11)0.0683 (6)
H29B0.64680.10420.05680.082*
C30B0.77274 (16)0.12772 (14)0.05678 (12)0.0737 (7)
H30B0.78570.07450.04210.088*
C31B0.83654 (15)0.18956 (13)0.07031 (12)0.0688 (6)
H31B0.89260.17730.06410.083*
C32B0.81995 (12)0.26955 (12)0.09296 (10)0.0508 (5)
C33B0.89683 (13)0.32842 (13)0.10781 (12)0.0621 (6)
O34B0.96723 (11)0.30439 (11)0.09933 (15)0.1351 (10)
C35B0.5943 (2)0.72788 (15)0.22187 (16)0.1033 (10)
H35D0.61440.72990.26940.155*
H35E0.53310.74270.21020.155*
H35F0.62750.76730.20160.155*
C36B0.52947 (17)0.68101 (17)0.08125 (13)0.0884 (8)
H36D0.50960.65360.03900.133*
H36E0.56900.72620.07670.133*
H36F0.47990.70360.09620.133*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0443 (9)0.0631 (11)0.0662 (12)0.0092 (8)0.0223 (8)0.0008 (9)
C2A0.0427 (11)0.0493 (12)0.0750 (15)0.0038 (9)0.0225 (10)0.0068 (11)
C3A0.0622 (14)0.0558 (13)0.0956 (17)0.0138 (11)0.0365 (13)0.0066 (12)
C4A0.0652 (16)0.0695 (16)0.121 (2)0.0260 (13)0.0443 (16)0.0229 (16)
C5A0.0488 (14)0.0816 (18)0.119 (2)0.0239 (12)0.0214 (15)0.0359 (17)
C6A0.0513 (13)0.0757 (16)0.0872 (17)0.0092 (11)0.0112 (12)0.0212 (13)
C7A0.0392 (11)0.0502 (11)0.0780 (15)0.0052 (9)0.0183 (10)0.0126 (11)
N8A0.0365 (9)0.0571 (10)0.0771 (12)0.0004 (7)0.0119 (8)0.0037 (9)
C9A0.0417 (12)0.0742 (14)0.0642 (13)0.0079 (10)0.0173 (10)0.0047 (11)
O10A0.0477 (10)0.1178 (15)0.1543 (18)0.0185 (9)0.0318 (11)0.0527 (13)
C11A0.0489 (12)0.0578 (12)0.0566 (12)0.0074 (9)0.0161 (9)0.0001 (10)
C12A0.0594 (14)0.0723 (16)0.0857 (17)0.0161 (12)0.0197 (12)0.0149 (13)
C13A0.0814 (18)0.0646 (15)0.103 (2)0.0197 (13)0.0302 (15)0.0248 (14)
C14A0.0825 (18)0.0551 (14)0.106 (2)0.0027 (12)0.0435 (15)0.0084 (13)
C15A0.0578 (13)0.0544 (13)0.1035 (19)0.0026 (10)0.0342 (13)0.0023 (12)
C16A0.0505 (12)0.0493 (12)0.0711 (14)0.0048 (9)0.0222 (10)0.0004 (10)
O17A0.0430 (8)0.0535 (9)0.1170 (13)0.0083 (6)0.0310 (8)0.0137 (8)
C18A0.0462 (13)0.0594 (14)0.145 (2)0.0071 (10)0.0374 (14)0.0100 (14)
C19A0.0394 (11)0.0535 (13)0.0945 (18)0.0049 (9)0.0289 (11)0.0040 (12)
C20A0.0548 (13)0.0679 (15)0.0768 (16)0.0085 (11)0.0237 (11)0.0154 (12)
C21A0.0607 (13)0.0609 (14)0.0674 (15)0.0000 (10)0.0271 (11)0.0004 (11)
C22A0.0628 (14)0.0529 (12)0.0721 (15)0.0021 (10)0.0272 (11)0.0048 (11)
C23A0.0560 (13)0.0664 (14)0.0627 (14)0.0003 (10)0.0208 (10)0.0009 (11)
C24A0.0369 (11)0.0592 (13)0.0891 (17)0.0034 (9)0.0269 (11)0.0104 (12)
C25A0.0494 (13)0.0790 (16)0.1055 (19)0.0147 (11)0.0359 (13)0.0319 (14)
O26A0.0419 (8)0.0758 (10)0.0832 (11)0.0064 (7)0.0230 (7)0.0221 (8)
C27A0.0496 (12)0.0446 (11)0.0723 (14)0.0010 (9)0.0168 (10)0.0078 (10)
C28A0.0520 (14)0.0741 (16)0.100 (2)0.0104 (11)0.0149 (13)0.0258 (14)
C29A0.0741 (19)0.0882 (18)0.090 (2)0.0060 (14)0.0033 (15)0.0157 (16)
C30A0.096 (2)0.107 (2)0.0629 (16)0.0003 (17)0.0076 (15)0.0001 (15)
C31A0.0741 (17)0.0861 (17)0.0627 (15)0.0037 (13)0.0221 (13)0.0130 (13)
C32A0.0508 (12)0.0508 (11)0.0622 (14)0.0061 (9)0.0164 (10)0.0099 (10)
C33A0.0435 (11)0.0645 (13)0.0703 (15)0.0076 (9)0.0220 (10)0.0118 (11)
O34A0.0494 (10)0.1789 (19)0.0812 (12)0.0041 (11)0.0271 (9)0.0058 (12)
C35A0.123 (3)0.093 (2)0.0774 (18)0.0022 (17)0.0316 (17)0.0133 (16)
C36A0.132 (3)0.0547 (15)0.101 (2)0.0114 (15)0.0346 (18)0.0093 (14)
N1B0.0390 (9)0.0563 (10)0.0585 (10)0.0017 (7)0.0160 (7)0.0051 (8)
C2B0.0367 (10)0.0502 (11)0.0580 (12)0.0002 (8)0.0155 (9)0.0008 (9)
C3B0.0653 (14)0.0712 (14)0.0576 (13)0.0074 (11)0.0241 (11)0.0002 (11)
C4B0.0747 (16)0.0763 (16)0.0765 (17)0.0141 (13)0.0412 (13)0.0042 (13)
C5B0.0533 (13)0.0632 (14)0.0890 (18)0.0152 (10)0.0309 (12)0.0008 (12)
C6B0.0482 (12)0.0635 (13)0.0663 (14)0.0104 (10)0.0184 (10)0.0027 (11)
C7B0.0393 (10)0.0485 (11)0.0559 (12)0.0021 (8)0.0173 (9)0.0025 (9)
N8B0.0461 (9)0.0642 (10)0.0518 (10)0.0174 (8)0.0133 (8)0.0002 (8)
C9B0.0387 (11)0.0546 (11)0.0558 (13)0.0003 (9)0.0086 (9)0.0014 (10)
O10B0.0442 (9)0.1323 (15)0.0684 (10)0.0206 (9)0.0032 (7)0.0109 (10)
C11B0.0509 (11)0.0417 (10)0.0490 (12)0.0006 (8)0.0119 (9)0.0007 (9)
C12B0.0611 (14)0.0678 (14)0.0533 (13)0.0074 (11)0.0071 (10)0.0017 (11)
C13B0.0875 (19)0.0886 (17)0.0458 (13)0.0125 (14)0.0089 (12)0.0045 (12)
C14B0.0871 (18)0.0809 (16)0.0587 (15)0.0070 (13)0.0343 (13)0.0082 (12)
C15B0.0562 (13)0.0712 (14)0.0666 (15)0.0014 (11)0.0247 (11)0.0108 (11)
C16B0.0477 (11)0.0466 (11)0.0521 (12)0.0026 (8)0.0145 (9)0.0041 (9)
O17B0.0356 (7)0.0847 (10)0.0632 (9)0.0008 (6)0.0112 (6)0.0241 (8)
C18B0.0411 (12)0.0984 (18)0.1003 (19)0.0049 (12)0.0103 (12)0.0401 (15)
C19B0.0335 (10)0.0616 (13)0.0722 (15)0.0013 (9)0.0148 (10)0.0169 (11)
C20B0.0535 (13)0.0773 (16)0.0590 (13)0.0089 (11)0.0147 (10)0.0020 (12)
C21B0.0548 (13)0.0577 (13)0.0754 (16)0.0006 (10)0.0239 (11)0.0006 (12)
C22B0.0434 (11)0.0581 (13)0.0708 (15)0.0054 (9)0.0210 (10)0.0116 (11)
C23B0.0450 (11)0.0729 (15)0.0570 (13)0.0023 (10)0.0138 (9)0.0028 (11)
C24B0.0328 (10)0.0537 (12)0.0753 (15)0.0016 (8)0.0185 (10)0.0010 (11)
C25B0.0405 (12)0.0618 (14)0.116 (2)0.0016 (10)0.0268 (12)0.0124 (13)
O26B0.0394 (8)0.0512 (8)0.1001 (11)0.0010 (6)0.0255 (7)0.0127 (8)
C27B0.0417 (10)0.0474 (11)0.0575 (12)0.0026 (8)0.0102 (9)0.0008 (9)
C28B0.0472 (12)0.0588 (13)0.0845 (16)0.0041 (10)0.0166 (11)0.0073 (11)
C29B0.0620 (15)0.0581 (14)0.0822 (16)0.0113 (11)0.0097 (12)0.0074 (12)
C30B0.0699 (16)0.0510 (13)0.0987 (18)0.0043 (11)0.0150 (13)0.0148 (12)
C31B0.0525 (13)0.0562 (13)0.0996 (18)0.0078 (10)0.0209 (12)0.0087 (12)
C32B0.0418 (11)0.0494 (11)0.0605 (12)0.0037 (8)0.0098 (9)0.0006 (9)
C33B0.0384 (11)0.0563 (13)0.0929 (16)0.0031 (9)0.0172 (10)0.0056 (12)
O34B0.0498 (11)0.0799 (12)0.286 (3)0.0069 (9)0.0598 (15)0.0536 (15)
C35B0.126 (3)0.0609 (16)0.130 (3)0.0005 (16)0.043 (2)0.0191 (16)
C36B0.0767 (18)0.0877 (18)0.104 (2)0.0227 (14)0.0268 (15)0.0353 (16)
Geometric parameters (Å, º) top
N1A—C33A1.342 (3)N1B—C33B1.336 (2)
N1A—C2A1.418 (2)N1B—C2B1.434 (2)
N1A—H1A0.8600N1B—H1B0.8600
C2A—C7A1.381 (3)C2B—C3B1.377 (3)
C2A—C3A1.389 (3)C2B—C7B1.391 (3)
C3A—C4A1.360 (3)C3B—C4B1.374 (3)
C3A—H3A0.9300C3B—H3B0.9300
C4A—C5A1.363 (4)C4B—C5B1.364 (3)
C4A—H4A0.9300C4B—H4B0.9300
C5A—C6A1.390 (3)C5B—C6B1.363 (3)
C5A—H5A0.9300C5B—H5B0.9300
C6A—C7A1.390 (3)C6B—C7B1.400 (3)
C6A—H6A0.9300C6B—H6B0.9300
C7A—N8A1.426 (2)C7B—N8B1.409 (2)
N8A—C9A1.348 (3)N8B—C9B1.348 (2)
N8A—H8A0.8600N8B—H8B0.8600
C9A—O10A1.213 (2)C9B—O10B1.218 (2)
C9A—C11A1.496 (3)C9B—C11B1.500 (3)
C11A—C12A1.386 (3)C11B—C12B1.388 (3)
C11A—C16A1.394 (3)C11B—C16B1.398 (3)
C12A—C13A1.368 (3)C12B—C13B1.369 (3)
C12A—H12A0.9300C12B—H12B0.9300
C13A—C14A1.367 (3)C13B—C14B1.366 (3)
C13A—H13A0.9300C13B—H13B0.9300
C14A—C15A1.371 (3)C14B—C15B1.376 (3)
C14A—H14A0.9300C14B—H14B0.9300
C15A—C16A1.387 (3)C15B—C16B1.387 (3)
C15A—H15A0.9300C15B—H15B0.9300
C16A—O17A1.376 (2)C16B—O17B1.368 (2)
O17A—C18A1.433 (2)O17B—C18B1.443 (2)
C18A—C19A1.505 (3)C18B—C19B1.497 (3)
C18A—H18A0.9700C18B—H18C0.9700
C18A—H18B0.9700C18B—H18D0.9700
C19A—C20A1.376 (3)C19B—C24B1.382 (3)
C19A—C24A1.388 (3)C19B—C20B1.392 (3)
C20A—C21A1.385 (3)C20B—C21B1.380 (3)
C20A—H20A0.9300C20B—H20B0.9300
C21A—C22A1.393 (3)C21B—C22B1.378 (3)
C21A—C35A1.506 (3)C21B—C35B1.516 (3)
C22A—C23A1.372 (3)C22B—C23B1.383 (3)
C22A—C36A1.512 (3)C22B—C36B1.508 (3)
C23A—C24A1.388 (3)C23B—C24B1.379 (3)
C23A—H23A0.9300C23B—H23B0.9300
C24A—C25A1.494 (3)C24B—C25B1.496 (3)
C25A—O26A1.445 (2)C25B—O26B1.436 (2)
C25A—H25A0.9700C25B—H25C0.9700
C25A—H25B0.9700C25B—H25D0.9700
O26A—C27A1.371 (2)O26B—C27B1.376 (2)
C27A—C28A1.384 (3)C27B—C28B1.387 (3)
C27A—C32A1.398 (3)C27B—C32B1.388 (2)
C28A—C29A1.368 (3)C28B—C29B1.381 (3)
C28A—H28A0.9300C28B—H28B0.9300
C29A—C30A1.358 (4)C29B—C30B1.366 (3)
C29A—H29A0.9300C29B—H29B0.9300
C30A—C31A1.362 (4)C30B—C31B1.377 (3)
C30A—H30A0.9300C30B—H30B0.9300
C31A—C32A1.389 (3)C31B—C32B1.389 (3)
C31A—H31A0.9300C31B—H31B0.9300
C32A—C33A1.486 (3)C32B—C33B1.494 (3)
C33A—O34A1.220 (2)C33B—O34B1.208 (2)
C35A—H35A0.9600C35B—H35D0.9600
C35A—H35B0.9600C35B—H35E0.9600
C35A—H35C0.9600C35B—H35F0.9600
C36A—H36A0.9600C36B—H36D0.9600
C36A—H36B0.9600C36B—H36E0.9600
C36A—H36C0.9600C36B—H36F0.9600
C33A—N1A—C2A123.96 (16)C33B—N1B—C2B121.99 (15)
C33A—N1A—H1A118.0C33B—N1B—H1B119.0
C2A—N1A—H1A118.0C2B—N1B—H1B119.0
C7A—C2A—C3A119.6 (2)C3B—C2B—C7B119.9 (2)
C7A—C2A—N1A120.4 (2)C3B—C2B—N1B119.6 (2)
C3A—C2A—N1A120.0 (2)C7B—C2B—N1B120.5 (2)
C4A—C3A—C2A121.1 (2)C4B—C3B—C2B121.0 (2)
C4A—C3A—H3A119.4C4B—C3B—H3B119.5
C2A—C3A—H3A119.4C2B—C3B—H3B119.5
C5A—C4A—C3A119.8 (2)C5B—C4B—C3B119.2 (2)
C5A—C4A—H4A120.1C5B—C4B—H4B120.4
C3A—C4A—H4A120.1C3B—C4B—H4B120.4
C4A—C5A—C6A120.4 (2)C4B—C5B—C6B121.3 (2)
C4A—C5A—H5A119.8C4B—C5B—H5B119.3
C6A—C5A—H5A119.8C6B—C5B—H5B119.3
C5A—C6A—C7A120.0 (2)C5B—C6B—C7B120.3 (2)
C5A—C6A—H6A120.0C5B—C6B—H6B119.9
C7A—C6A—H6A120.0C7B—C6B—H6B119.9
C2A—C7A—C6A119.00 (19)C2B—C7B—C6B118.3 (2)
C2A—C7A—N8A120.7 (2)C2B—C7B—N8B118.4 (2)
C6A—C7A—N8A120.2 (2)C6B—C7B—N8B123.2 (2)
C9A—N8A—C7A124.48 (17)C9B—N8B—C7B127.67 (16)
C9A—N8A—H8A117.8C9B—N8B—H8B116.2
C7A—N8A—H8A117.8C7B—N8B—H8B116.2
O10A—C9A—N8A121.26 (19)O10B—C9B—N8B122.25 (18)
O10A—C9A—C11A119.7 (2)O10B—C9B—C11B120.16 (18)
N8A—C9A—C11A119.02 (17)N8B—C9B—C11B117.58 (17)
C12A—C11A—C16A117.73 (19)C12B—C11B—C16B118.40 (18)
C12A—C11A—C9A115.1 (2)C12B—C11B—C9B114.4 (2)
C16A—C11A—C9A127.1 (2)C16B—C11B—C9B127.2 (2)
C13A—C12A—C11A122.1 (2)C13B—C12B—C11B122.0 (2)
C13A—C12A—H12A119.0C13B—C12B—H12B119.0
C11A—C12A—H12A119.0C11B—C12B—H12B119.0
C12A—C13A—C14A119.3 (2)C14B—C13B—C12B118.9 (2)
C12A—C13A—H13A120.4C14B—C13B—H13B120.6
C14A—C13A—H13A120.4C12B—C13B—H13B120.6
C15A—C14A—C13A120.7 (2)C13B—C14B—C15B121.1 (2)
C15A—C14A—H14A119.6C13B—C14B—H14B119.5
C13A—C14A—H14A119.6C15B—C14B—H14B119.5
C14A—C15A—C16A119.9 (2)C14B—C15B—C16B120.3 (2)
C14A—C15A—H15A120.0C14B—C15B—H15B119.9
C16A—C15A—H15A120.0C16B—C15B—H15B119.9
O17A—C16A—C15A122.5 (2)O17B—C16B—C15B122.9 (2)
O17A—C16A—C11A117.2 (2)O17B—C16B—C11B117.8 (2)
C15A—C16A—C11A120.23 (19)C15B—C16B—C11B119.33 (18)
C16A—O17A—C18A117.2 (2)C16B—O17B—C18B118.2 (2)
O17A—C18A—C19A108.87 (16)O17B—C18B—C19B110.29 (16)
O17A—C18A—H18A109.9O17B—C18B—H18C109.6
C19A—C18A—H18A109.9C19B—C18B—H18C109.6
O17A—C18A—H18B109.9O17B—C18B—H18D109.6
C19A—C18A—H18B109.9C19B—C18B—H18D109.6
H18A—C18A—H18B108.3H18C—C18B—H18D108.1
C20A—C19A—C24A118.84 (19)C24B—C19B—C20B118.53 (19)
C20A—C19A—C18A118.2 (2)C24B—C19B—C18B124.3 (2)
C24A—C19A—C18A122.9 (2)C20B—C19B—C18B117.0 (2)
C19A—C20A—C21A123.0 (2)C21B—C20B—C19B122.6 (2)
C19A—C20A—H20A118.5C21B—C20B—H20B118.7
C21A—C20A—H20A118.5C19B—C20B—H20B118.7
C20A—C21A—C22A118.1 (2)C20B—C21B—C22B118.8 (2)
C20A—C21A—C35A120.3 (2)C20B—C21B—C35B120.2 (2)
C22A—C21A—C35A121.5 (2)C22B—C21B—C35B121.0 (2)
C23A—C22A—C21A118.7 (2)C21B—C22B—C23B118.5 (2)
C23A—C22A—C36A120.0 (2)C21B—C22B—C36B121.3 (2)
C21A—C22A—C36A121.2 (2)C23B—C22B—C36B120.2 (2)
C22A—C23A—C24A123.1 (2)C24B—C23B—C22B123.3 (2)
C22A—C23A—H23A118.4C24B—C23B—H23B118.4
C24A—C23A—H23A118.4C22B—C23B—H23B118.4
C23A—C24A—C19A118.1 (2)C23B—C24B—C19B118.32 (19)
C23A—C24A—C25A117.3 (2)C23B—C24B—C25B118.9 (2)
C19A—C24A—C25A124.5 (2)C19B—C24B—C25B122.6 (2)
O26A—C25A—C24A108.66 (16)O26B—C25B—C24B109.06 (16)
O26A—C25A—H25A110.0O26B—C25B—H25C109.9
C24A—C25A—H25A110.0C24B—C25B—H25C109.9
O26A—C25A—H25B110.0O26B—C25B—H25D109.9
C24A—C25A—H25B110.0C24B—C25B—H25D109.9
H25A—C25A—H25B108.3H25C—C25B—H25D108.3
C27A—O26A—C25A117.2 (2)C27B—O26B—C25B117.3 (1)
O26A—C27A—C28A122.7 (2)O26B—C27B—C28B122.5 (2)
O26A—C27A—C32A117.6 (2)O26B—C27B—C32B116.8 (2)
C28A—C27A—C32A119.7 (2)C28B—C27B—C32B120.65 (18)
C29A—C28A—C27A120.7 (2)C29B—C28B—C27B119.7 (2)
C29A—C28A—H28A119.7C29B—C28B—H28B120.2
C27A—C28A—H28A119.7C27B—C28B—H28B120.2
C30A—C29A—C28A120.4 (3)C30B—C29B—C28B120.8 (2)
C30A—C29A—H29A119.8C30B—C29B—H29B119.6
C28A—C29A—H29A119.8C28B—C29B—H29B119.6
C29A—C30A—C31A119.6 (3)C29B—C30B—C31B119.0 (2)
C29A—C30A—H30A120.2C29B—C30B—H30B120.5
C31A—C30A—H30A120.2C31B—C30B—H30B120.5
C30A—C31A—C32A122.3 (2)C30B—C31B—C32B122.2 (2)
C30A—C31A—H31A118.9C30B—C31B—H31B118.9
C32A—C31A—H31A118.9C32B—C31B—H31B118.9
C31A—C32A—C27A117.3 (2)C27B—C32B—C31B117.66 (18)
C31A—C32A—C33A115.5 (2)C27B—C32B—C33B126.6 (2)
C27A—C32A—C33A127.2 (2)C31B—C32B—C33B115.7 (2)
O34A—C33A—N1A121.6 (2)O34B—C33B—N1B120.46 (19)
O34A—C33A—C32A118.9 (2)O34B—C33B—C32B119.20 (19)
N1A—C33A—C32A119.47 (16)N1B—C33B—C32B120.33 (16)
C21A—C35A—H35A109.5C21B—C35B—H35D109.5
C21A—C35A—H35B109.5C21B—C35B—H35E109.5
H35A—C35A—H35B109.5H35D—C35B—H35E109.5
C21A—C35A—H35C109.5C21B—C35B—H35F109.5
H35A—C35A—H35C109.5H35D—C35B—H35F109.5
H35B—C35A—H35C109.5H35E—C35B—H35F109.5
C22A—C36A—H36A109.5C22B—C36B—H36D109.5
C22A—C36A—H36B109.5C22B—C36B—H36E109.5
H36A—C36A—H36B109.5H36D—C36B—H36E109.5
C22A—C36A—H36C109.5C22B—C36B—H36F109.5
H36A—C36A—H36C109.5H36D—C36B—H36F109.5
H36B—C36A—H36C109.5H36E—C36B—H36F109.5
C33A—N1A—C2A—C7A140.8 (2)C33B—N1B—C2B—C3B64.6 (3)
C33A—N1A—C2A—C3A40.3 (3)C33B—N1B—C2B—C7B113.7 (2)
C7A—C2A—C3A—C4A2.5 (3)C7B—C2B—C3B—C4B0.4 (3)
N1A—C2A—C3A—C4A178.60 (19)N1B—C2B—C3B—C4B177.8 (2)
C2A—C3A—C4A—C5A2.2 (4)C2B—C3B—C4B—C5B1.0 (4)
C3A—C4A—C5A—C6A0.2 (4)C3B—C4B—C5B—C6B1.5 (4)
C4A—C5A—C6A—C7A2.4 (4)C4B—C5B—C6B—C7B0.5 (3)
C3A—C2A—C7A—C6A0.3 (3)C3B—C2B—C7B—C6B1.5 (3)
N1A—C2A—C7A—C6A179.21 (18)N1B—C2B—C7B—C6B176.82 (17)
C3A—C2A—C7A—N8A178.65 (17)C3B—C2B—C7B—N8B177.00 (18)
N1A—C2A—C7A—N8A2.5 (3)N1B—C2B—C7B—N8B4.7 (3)
C5A—C6A—C7A—C2A2.1 (3)C5B—C6B—C7B—C2B1.0 (3)
C5A—C6A—C7A—N8A176.27 (19)C5B—C6B—C7B—N8B177.37 (19)
C2A—C7A—N8A—C9A133.1 (2)C2B—C7B—N8B—C9B168.17 (19)
C6A—C7A—N8A—C9A45.2 (3)C6B—C7B—N8B—C9B13.5 (3)
C7A—N8A—C9A—O10A3.8 (3)C7B—N8B—C9B—O10B4.5 (3)
C7A—N8A—C9A—C11A173.82 (18)C7B—N8B—C9B—C11B176.59 (17)
O10A—C9A—C11A—C12A4.9 (3)O10B—C9B—C11B—C12B18.0 (3)
N8A—C9A—C11A—C12A172.78 (19)N8B—C9B—C11B—C12B160.96 (17)
O10A—C9A—C11A—C16A177.4 (2)O10B—C9B—C11B—C16B161.3 (2)
N8A—C9A—C11A—C16A4.9 (3)N8B—C9B—C11B—C16B19.7 (3)
C16A—C11A—C12A—C13A0.5 (3)C16B—C11B—C12B—C13B1.0 (3)
C9A—C11A—C12A—C13A177.4 (2)C9B—C11B—C12B—C13B179.7 (2)
C11A—C12A—C13A—C14A1.3 (4)C11B—C12B—C13B—C14B0.1 (4)
C12A—C13A—C14A—C15A1.8 (4)C12B—C13B—C14B—C15B0.5 (4)
C13A—C14A—C15A—C16A0.5 (4)C13B—C14B—C15B—C16B0.2 (4)
C14A—C15A—C16A—O17A178.7 (2)C14B—C15B—C16B—O17B177.97 (19)
C14A—C15A—C16A—C11A1.3 (3)C14B—C15B—C16B—C11B1.3 (3)
C12A—C11A—C16A—O17A178.19 (19)C12B—C11B—C16B—O17B177.64 (17)
C9A—C11A—C16A—O17A4.2 (3)C9B—C11B—C16B—O17B1.6 (3)
C12A—C11A—C16A—C15A1.8 (3)C12B—C11B—C16B—C15B1.6 (3)
C9A—C11A—C16A—C15A175.8 (2)C9B—C11B—C16B—C15B179.08 (19)
C15A—C16A—O17A—C18A9.4 (3)C15B—C16B—O17B—C18B1.1 (3)
C11A—C16A—O17A—C18A170.6 (2)C11B—C16B—O17B—C18B179.60 (18)
C16A—O17A—C18A—C19A166.8 (2)C16B—O17B—C18B—C19B151.96 (19)
O17A—C18A—C19A—C20A93.2 (2)O17B—C18B—C19B—C24B105.4 (2)
O17A—C18A—C19A—C24A90.5 (3)O17B—C18B—C19B—C20B79.0 (2)
C24A—C19A—C20A—C21A0.9 (3)C24B—C19B—C20B—C21B0.1 (3)
C18A—C19A—C20A—C21A175.51 (19)C18B—C19B—C20B—C21B175.94 (19)
C19A—C20A—C21A—C22A0.7 (3)C19B—C20B—C21B—C22B0.7 (3)
C19A—C20A—C21A—C35A179.7 (2)C19B—C20B—C21B—C35B179.1 (2)
C20A—C21A—C22A—C23A2.0 (3)C20B—C21B—C22B—C23B0.5 (3)
C35A—C21A—C22A—C23A178.5 (2)C35B—C21B—C22B—C23B179.3 (2)
C20A—C21A—C22A—C36A178.3 (2)C20B—C21B—C22B—C36B179.4 (2)
C35A—C21A—C22A—C36A1.3 (3)C35B—C21B—C22B—C36B0.4 (3)
C21A—C22A—C23A—C24A1.7 (3)C21B—C22B—C23B—C24B0.4 (3)
C36A—C22A—C23A—C24A178.5 (2)C36B—C22B—C23B—C24B178.5 (2)
C22A—C23A—C24A—C19A0.1 (3)C22B—C23B—C24B—C19B1.1 (3)
C22A—C23A—C24A—C25A177.69 (18)C22B—C23B—C24B—C25B174.56 (17)
C20A—C19A—C24A—C23A1.2 (3)C20B—C19B—C24B—C23B0.9 (3)
C18A—C19A—C24A—C23A175.05 (17)C18B—C19B—C24B—C23B176.48 (18)
C20A—C19A—C24A—C25A178.83 (17)C20B—C19B—C24B—C25B174.56 (17)
C18A—C19A—C24A—C25A2.6 (3)C18B—C19B—C24B—C25B1.0 (3)
C23A—C24A—C25A—O26A92.3 (2)C23B—C24B—C25B—O26B106.7 (2)
C19A—C24A—C25A—O26A90.1 (2)C19B—C24B—C25B—O26B77.8 (2)
C24A—C25A—O26A—C27A163.72 (18)C24B—C25B—O26B—C27B179.83 (18)
C25A—O26A—C27A—C28A0.9 (3)C25B—O26B—C27B—C28B1.5 (3)
C25A—O26A—C27A—C32A178.26 (18)C25B—O26B—C27B—C32B178.65 (19)
O26A—C27A—C28A—C29A179.0 (2)O26B—C27B—C28B—C29B178.41 (19)
C32A—C27A—C28A—C29A0.2 (3)C32B—C27B—C28B—C29B1.4 (3)
C27A—C28A—C29A—C30A1.8 (4)C27B—C28B—C29B—C30B1.8 (4)
C28A—C29A—C30A—C31A2.2 (4)C28B—C29B—C30B—C31B0.8 (4)
C29A—C30A—C31A—C32A1.1 (4)C29B—C30B—C31B—C32B0.6 (4)
C30A—C31A—C32A—C27A0.4 (3)O26B—C27B—C32B—C31B179.77 (18)
C30A—C31A—C32A—C33A179.9 (2)C28B—C27B—C32B—C31B0.0 (3)
O26A—C27A—C32A—C31A179.93 (18)O26B—C27B—C32B—C33B1.2 (3)
C28A—C27A—C32A—C31A0.9 (3)C28B—C27B—C32B—C33B178.6 (2)
O26A—C27A—C32A—C33A0.3 (3)C30B—C31B—C32B—C27B1.0 (3)
C28A—C27A—C32A—C33A179.5 (2)C30B—C31B—C32B—C33B177.8 (2)
C2A—N1A—C33A—O34A0.9 (3)C2B—N1B—C33B—O34B2.7 (4)
C2A—N1A—C33A—C32A179.15 (17)C2B—N1B—C33B—C32B178.43 (18)
C31A—C32A—C33A—O34A5.2 (3)C27B—C32B—C33B—O34B179.0 (2)
C27A—C32A—C33A—O34A175.2 (2)C31B—C32B—C33B—O34B0.3 (3)
C31A—C32A—C33A—N1A173.10 (19)C27B—C32B—C33B—N1B0.1 (3)
C27A—C32A—C33A—N1A6.5 (3)C31B—C32B—C33B—N1B178.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O26A0.862.012.691 (2)135
N1B—H1B···O26B0.862.002.662 (2)134
N8A—H8A···O17A0.861.992.677 (2)136
N8B—H8B···O17B0.862.102.722 (2)129
N8B—H8B···N1B0.862.422.791 (3)106
C3A—H3A···O34A0.932.412.809 (4)106
C6A—H6A···O10A0.932.532.866 (4)102
C6B—H6B···O10B0.932.242.820 (3)120
C12A—H12A···O10A0.932.342.694 (3)102
C12B—H12B···O10B0.932.382.719 (3)101
C15A—H15A···O10B0.932.593.517 (3)173
C28A—H28A···O34B0.932.253.132 (3)156
C15B—H15B···O10Ai0.932.493.376 (3)158
C18B—H18C···O10Ai0.972.333.233 (3)154
C25B—H25C···O34Ai0.972.593.052 (3)109
Symmetry code: (i) x1, y, z.

Experimental details

Crystal data
Chemical formulaC30H26N2O4
Mr478.53
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)15.5767 (9), 15.7746 (9), 20.5721 (12)
β (°) 102.541 (1)
V3)4934.3 (5)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.24 × 0.20 × 0.16
Data collection
DiffractometerCCD Area Detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
30895, 11480, 6259
Rint0.031
(sin θ/λ)max1)0.662
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.166, 0.99
No. of reflections11480
No. of parameters653
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.22

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), 'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)', SHELXL97 and PARST (Nardelli, 1995).

Selected geometric parameters (Å, º) top
N1A—C33A1.342 (3)N1B—C33B1.336 (2)
N1A—C2A1.418 (2)N1B—C2B1.434 (2)
C7A—N8A1.426 (2)C7B—N8B1.409 (2)
N8A—C9A1.348 (3)N8B—C9B1.348 (2)
C9A—O10A1.213 (2)C9B—O10B1.218 (2)
C33A—O34A1.220 (2)C33B—O34B1.208 (2)
O17A—C16A—C15A122.5 (2)O17B—C16B—C15B122.9 (2)
O17A—C16A—C11A117.2 (2)O17B—C16B—C11B117.8 (2)
C23A—C24A—C25A117.3 (2)C23B—C24B—C25B118.9 (2)
C19A—C24A—C25A124.5 (2)C19B—C24B—C25B122.6 (2)
C33A—N1A—C2A—C3A40.3 (3)C33B—N1B—C2B—C3B64.6 (3)
C6A—C7A—N8A—C9A45.2 (3)C6B—C7B—N8B—C9B13.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O26A0.862.012.691 (2)135
N1B—H1B···O26B0.862.002.662 (2)134
N8A—H8A···O17A0.861.992.677 (2)136
N8B—H8B···O17B0.862.102.722 (2)129
N8B—H8B···N1B0.862.422.791 (3)106
C3A—H3A···O34A0.932.412.809 (4)106
C6A—H6A···O10A0.932.532.866 (4)102
C6B—H6B···O10B0.932.242.820 (3)120
C12A—H12A···O10A0.932.342.694 (3)102
C12B—H12B···O10B0.932.382.719 (3)101
C15A—H15A···O10B0.932.593.517 (3)173
C28A—H28A···O34B0.932.253.132 (3)156
C15B—H15B···O10Ai0.932.493.376 (3)158
C18B—H18C···O10Ai0.972.333.233 (3)154
C25B—H25C···O34Ai0.972.593.052 (3)109
Symmetry code: (i) x1, y, z.
 

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