N(6)-Acetyl-5,7-di­phenyl-5,6,7,8-tetra­hydro­benzo­[b]-1,6-naphthyridine

The single-crystal X-ray diffraction study of the title mol­ecule [alternative name: N(2)-acetyl-1,3-di­phenyl-1,2,3,4-tetra­hydro­benzo­[b][1,6]naphthyridine], C₂₆H₂₂N₂O, confirms that it is a 1,6-naphthyridine derivative whose structural characterization was not possible from ¹H, ¹³C NMR and mass spectral data. The tetra­hydro-1,6-napthyridine ring has a boat conformation. The equatorial and axial orientations of the two phenyl groups and the coplanarity of the acetyl group with the tetra­hydro­naphthyridine ring are also confirmed.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.055
• wR factor = 0.167
• Data-to-parameter ratio = 16.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



WEIGH_01  Alert C Extra text has been found in the
          _refine_ls_weighting_scheme field. This should be in the
          _refine_ls_weighting_details field.
          Weighting scheme given as calc w = 1/[\s^2^(Fo^2^)+(0.0804P)^2^] wher
          Weighting scheme identified as calc


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

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S1. Comment

Naphthyridine derivatives have extensive pharmacological properties (Di Braccio et al., 1997; Hong et al., 1997; Chen et al., 1997; Mohan & Mishra, 1997; Damon & Nadelson, 1981; Singh et al., 1995). Structural data for only a few 1,6-naphthyridines are available in the literature (Balogh et al., 1986; Anderez et al., 1992; Govindasamy et al., 2000). The present investigation of N(2)-acetyl-1,3-diphenyl-1,2,3,4-tetrahydrobenzo[b]-1,6-naphthyridine, (I), was undertaken to establish the molecular structure and to determine the precise conformational changes caused by the substituents on the 1,6-naphthyridine ring system in the molecule of the crystalline acetylated product.

As shown by the X-ray analysis, the tetrahydro-1,6-naphthyridine ring has a boat conformation. The average numerical torsion angles, 43.4 (3) and 44.4 (3)°, involving the four C atoms of the plane of the boat show deviation from the ideal value of 54° (Nasipuri, 1994) due to the presence of planar coordinated N atoms. The C14—C8—C7—C24 and C14A—C8A—C7A—C24A torsion angles of -170.8 (2) and 168.8 (2)° show that the phenyl groups attached to C7 and C7A are equatorially disposed in the above ring system. The torsion angles 87.8 (3) and -85.9 (3)°, defined by the atoms C14—C13—C5—C18 and C14A—C13A—C5A—C18A, respectively, show that the phenyl groups attached to C5 and C5A are axially oriented in the naphthyridine ring. The sum of the bond angles around N6 and N6A, 358.7 (2) and 358.8 (2)°, show the near coplanar orientation of the acetyl group with the C5—N6—C7 part of the molecule. The atoms C5, C5A, C7 and C7A are chiral, their relative configurations being either SR or RS as revealed by the use of PLATON97 (Spek, 1990). The intermolecular and intramolecular C—H···O hydrogen bonds involving the acetyl O and the C atoms of the naphthyridine ring are listed in Table 2.

S2. Experimental

The title compound was obtained by the acetylation of the corresponding amine with acetic anhydride and triethylamine in benzene under reflux conditions. Diffraction quality crystals were obtained by recrystallizing the crude product from a benzene–petroleum ether mixture. The parent amine itself was obtained by the action of sodium azide with 2,4,6,8-tetraphenyl-3,7-diazabicyclo[3.3.1]nonan-9-one (Sivakumar, 2000), as a non-crystalline product.

S3. Refinement

The asymmetric unit of the cell consists of two independent molecules with a total of 58 non-H atoms. All the H atoms were included in calculated positions. While the C—H distances were refined by a riding model, the displacement parameters of the H atoms were tied to common values.

Computing details

Data collection: P3/P4 (Siemens, 1989); cell refinement: P3/P4; data reduction: P3/P4 and XDISK (Siemens, 1989); program(s) used to solve structure: SIR97 (Altomare et al., 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1983).

Figures

Fig. 1. View of the title molecule with 50% probability ellipsoids. H atoms have been omitted for clarity.

N(2)-Acetyl-1,3-diphenyl-1,2,3,4-tetrahydrobenzo[b]-1,6-naphthyridine

Crystal data

C26H22N2O	Z = 4
Mr = 378.46	F(000) = 800
Triclinic, P1	Dx = 1.239 Mg m^−3
a = 10.394 (2) Å	Mo Kα radiation, λ = 0.71069 Å
b = 10.493 (3) Å	Cell parameters from 40 reflections
c = 20.265 (4) Å	θ = 10–30°
α = 76.03 (2)°	µ = 0.08 mm^−1
β = 79.83 (2)°	T = 293 K
γ = 72.21 (2)°	Rectangular block, colorless
V = 2029.6 (8) Å^3	0.05 × 0.05 × 0.04 mm

Data collection

Siemens P3 diffractometer	Rint = 0.023
Radiation source: fine-focus sealed tube	θmax = 27.7°, θmin = 2.1°
Graphite monochromator	h = 0→13
ω–2θ scans	k = −13→13
9786 measured reflections	l = −25→26
9279 independent reflections	3 standard reflections every 300 reflections
4446 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.167	Calculated w = 1/[σ^2(Fo^2) + (0.0804P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max < 0.001
9279 reflections	Δρmax = 0.35 e Å^−3
566 parameters	Δρmin = −0.38 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0238 (18)

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.2866 (2)	0.2928 (2)	0.87272 (10)	0.0527 (5)
C2	0.1617 (3)	0.3530 (2)	0.84974 (11)	0.0504 (6)
C3	0.0925 (2)	0.2839 (2)	0.82231 (11)	0.0504 (6)
C4	0.1571 (3)	0.1458 (2)	0.81954 (12)	0.0494 (6)
H4	0.1144 (13)	0.0948 (15)	0.8008 (6)	0.0751 (14)*
C5	0.3545 (2)	−0.0612 (2)	0.84244 (12)	0.0477 (6)
H5	0.3206 (10)	−0.0852 (7)	0.8066 (10)	0.0751 (14)*
N6	0.50087 (19)	−0.07346 (19)	0.82033 (9)	0.0480 (5)
C7	0.5725 (2)	0.0041 (2)	0.84586 (12)	0.0482 (6)
H7	0.6033 (9)	0.0663 (19)	0.8066 (12)	0.0751 (14)*
C8	0.4752 (2)	0.0910 (2)	0.89515 (13)	0.0525 (6)
H8A	0.4609 (3)	0.0304 (11)	0.9407 (8)	0.0751 (14)*
H8B	0.5181 (8)	0.1596 (12)	0.90203 (19)	0.0751 (14)*
C9	0.1002 (3)	0.4916 (3)	0.85329 (14)	0.0636 (7)
H9	0.1458 (14)	0.5407 (15)	0.8727 (6)	0.0751 (14)*
C10	−0.0223 (3)	0.5564 (3)	0.82981 (14)	0.0707 (8)
H10	−0.0636 (13)	0.651 (3)	0.83219 (16)	0.0751 (14)*
C11	−0.0895 (3)	0.4880 (3)	0.80218 (15)	0.0685 (8)
H11	−0.178 (3)	0.5375 (14)	0.7854 (5)	0.0751 (14)*
C12	−0.0342 (3)	0.3545 (3)	0.79808 (13)	0.0599 (7)
H12	−0.0814 (14)	0.3085 (14)	0.7787 (6)	0.0751 (14)*
C13	0.2793 (2)	0.0853 (2)	0.84331 (11)	0.0460 (6)
C14	0.3408 (2)	0.1640 (2)	0.86932 (11)	0.0481 (6)
C15	0.5576 (3)	−0.1361 (2)	0.76624 (12)	0.0520 (6)
C16	0.6991 (3)	−0.1318 (3)	0.73460 (13)	0.0644 (8)
H16A	0.7611 (12)	−0.174 (2)	0.7682 (7)	0.120 (5)*
H16B	0.7008 (6)	−0.0390 (16)	0.7180 (10)	0.120 (5)*
H16C	0.7250 (10)	−0.179 (2)	0.6975 (9)	0.120 (5)*
O17	0.4949 (2)	−0.19456 (19)	0.74316 (9)	0.0682 (5)
C18	0.3291 (2)	−0.1627 (2)	0.90780 (13)	0.0508 (6)
C19	0.3726 (3)	−0.3005 (3)	0.90644 (17)	0.0737 (8)
H19	0.4198 (14)	−0.3291 (9)	0.8654 (12)	0.0751 (14)*
C20	0.3493 (4)	−0.3976 (3)	0.9630 (2)	0.0884 (11)
H20	0.3788 (10)	−0.489 (3)	0.9607 (2)	0.0751 (14)*
C21	0.2834 (4)	−0.3588 (4)	1.0218 (2)	0.0876 (11)
H21	0.2683 (6)	−0.423 (2)	1.0595 (13)	0.0751 (14)*
C22	0.2396 (4)	−0.2238 (4)	1.02477 (17)	0.0838 (10)
H22	0.1952 (15)	−0.1975 (9)	1.0645 (13)	0.0751 (14)*
C23	0.2621 (3)	−0.1261 (3)	0.96777 (14)	0.0662 (8)
H23	0.2309 (10)	−0.033 (3)	0.97032 (16)	0.0751 (14)*
C24	0.6952 (2)	−0.0828 (2)	0.88142 (12)	0.0484 (6)
C25	0.8124 (3)	−0.0404 (3)	0.86945 (15)	0.0639 (7)
H25	0.8178 (3)	0.040 (2)	0.8355 (10)	0.0751 (14)*
C26	0.9216 (3)	−0.1128 (4)	0.90581 (18)	0.0788 (9)
H26	0.998 (2)	−0.0835 (10)	0.8979 (3)	0.0751 (14)*
C27	0.9158 (3)	−0.2281 (3)	0.95365 (17)	0.0750 (9)
H27	0.997 (2)	−0.2813 (16)	0.9806 (8)	0.0751 (14)*
C28	0.8002 (3)	−0.2721 (3)	0.96529 (14)	0.0673 (8)
H28	0.7964 (3)	−0.354 (2)	0.9986 (10)	0.0751 (14)*
C29	0.6904 (3)	−0.2001 (3)	0.92976 (13)	0.0583 (7)
H29	0.609 (2)	−0.2317 (10)	0.9387 (3)	0.0751 (14)*
N1A	0.5157 (2)	0.1691 (2)	0.65608 (10)	0.0500 (5)
C2A	0.5050 (3)	0.2768 (2)	0.68556 (12)	0.0490 (6)
C3A	0.3821 (3)	0.3787 (2)	0.69328 (12)	0.0507 (6)
C4A	0.2676 (3)	0.3667 (2)	0.66891 (12)	0.0515 (6)
H4A	0.183 (3)	0.432 (2)	0.67391 (19)	0.0751 (14)*
C5A	0.1633 (2)	0.2383 (2)	0.61174 (12)	0.0497 (6)
H5A	0.082 (2)	0.2850 (14)	0.6353 (7)	0.0751 (14)*
N6A	0.16922 (19)	0.09069 (19)	0.63110 (9)	0.0480 (5)
C7A	0.3002 (2)	−0.0130 (2)	0.62050 (13)	0.0475 (6)
H7A	0.3194 (6)	−0.0743 (17)	0.6666 (13)	0.0751 (14)*
C8A	0.4171 (2)	0.0541 (2)	0.59562 (13)	0.0515 (6)
H8A1	0.5031 (16)	−0.0152 (13)	0.60223 (16)	0.0751 (14)*
H8A2	0.4164 (2)	0.0922 (7)	0.5469 (9)	0.0751 (14)*
C9A	0.6222 (3)	0.2863 (3)	0.70794 (14)	0.0629 (7)
H9A	0.714 (2)	0.212 (2)	0.7021 (2)	0.0751 (14)*
C10A	0.6150 (4)	0.3924 (3)	0.73710 (17)	0.0784 (9)
H10A	0.695 (3)	0.3979 (4)	0.7524 (5)	0.0751 (14)*
C11A	0.4942 (4)	0.4926 (4)	0.74516 (16)	0.0788 (10)
H11A	0.4914 (4)	0.565 (2)	0.7653 (6)	0.0751 (14)*
C12A	0.3796 (3)	0.4864 (3)	0.72392 (14)	0.0677 (8)
H12A	0.296 (2)	0.556 (2)	0.7299 (2)	0.0751 (14)*
C13A	0.2795 (2)	0.2611 (2)	0.63834 (11)	0.0466 (6)
C14A	0.4073 (2)	0.1644 (2)	0.63236 (12)	0.0465 (6)
C15A	0.0602 (3)	0.0544 (3)	0.67013 (13)	0.0589 (7)
C16A	0.0707 (3)	−0.0945 (3)	0.69625 (17)	0.0817 (10)
H16D	−0.0069 (18)	−0.1041 (4)	0.7257 (11)	0.120 (5)*
H16E	0.1471 (19)	−0.1354 (10)	0.7198 (11)	0.120 (5)*
H16F	0.079 (2)	−0.1363 (10)	0.6595 (7)	0.120 (5)*
O17A	−0.04550 (19)	0.1394 (2)	0.68440 (11)	0.0804 (6)
C18A	0.1524 (2)	0.2950 (2)	0.53592 (12)	0.0516 (6)
C19A	0.2509 (3)	0.3453 (3)	0.49173 (14)	0.0696 (8)
H19A	0.329 (2)	0.3452 (3)	0.5081 (5)	0.0751 (14)*
C20A	0.2339 (4)	0.3954 (4)	0.42356 (16)	0.0869 (10)
H20A	0.302 (2)	0.4293 (11)	0.3935 (9)	0.0751 (14)*
C21A	0.1192 (4)	0.3970 (3)	0.39869 (17)	0.0874 (11)
H21A	0.1086 (5)	0.4308 (11)	0.3515 (15)	0.0751 (14)*
C22A	0.0198 (4)	0.3498 (3)	0.44211 (16)	0.0810 (10)
H22A	−0.061 (2)	0.3517 (3)	0.4251 (5)	0.0751 (14)*
C23A	0.0356 (3)	0.2996 (3)	0.51003 (15)	0.0678 (8)
H23A	−0.036 (2)	0.2669 (10)	0.5404 (9)	0.0751 (14)*
C24A	0.2994 (2)	−0.1035 (2)	0.57260 (12)	0.0486 (6)
C25A	0.2334 (3)	−0.0564 (3)	0.51458 (14)	0.0624 (7)
H25A	0.1815 (15)	0.038 (3)	0.5037 (3)	0.0751 (14)*
C26A	0.2405 (3)	−0.1431 (4)	0.47193 (17)	0.0750 (9)
H26A	0.1959 (15)	−0.1095 (12)	0.4325 (13)	0.0751 (14)*
C27A	0.3118 (3)	−0.2767 (4)	0.48640 (17)	0.0747 (9)
H27A	0.3150 (3)	−0.3341 (19)	0.4581 (9)	0.0751 (14)*
C28A	0.3787 (3)	−0.3248 (3)	0.54367 (17)	0.0737 (9)
H28A	0.4304 (15)	−0.420 (3)	0.5541 (4)	0.0751 (14)*
C29A	0.3727 (3)	−0.2386 (3)	0.58650 (15)	0.0614 (7)
H29A	0.4226 (14)	−0.2749 (11)	0.6284 (12)	0.0751 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0600 (13)	0.0450 (12)	0.0505 (12)	−0.0050 (10)	−0.0095 (10)	−0.0147 (9)
C2	0.0565 (15)	0.0475 (14)	0.0415 (13)	−0.0067 (12)	−0.0053 (11)	−0.0080 (11)
C3	0.0529 (15)	0.0528 (15)	0.0399 (13)	−0.0097 (12)	−0.0046 (11)	−0.0054 (11)
C4	0.0531 (15)	0.0484 (14)	0.0467 (13)	−0.0130 (12)	−0.0067 (11)	−0.0102 (11)
C5	0.0499 (15)	0.0462 (14)	0.0497 (14)	−0.0117 (11)	−0.0122 (11)	−0.0116 (11)
N6	0.0517 (12)	0.0469 (11)	0.0450 (11)	−0.0100 (9)	−0.0082 (9)	−0.0112 (9)
C7	0.0540 (15)	0.0468 (14)	0.0449 (13)	−0.0139 (12)	−0.0093 (11)	−0.0082 (11)
C8	0.0541 (15)	0.0501 (14)	0.0574 (15)	−0.0094 (12)	−0.0155 (12)	−0.0181 (12)
C9	0.0715 (19)	0.0533 (16)	0.0628 (17)	−0.0044 (15)	−0.0153 (14)	−0.0163 (13)
C10	0.082 (2)	0.0515 (16)	0.0681 (18)	0.0054 (16)	−0.0175 (16)	−0.0162 (14)
C11	0.0593 (17)	0.0651 (19)	0.0676 (18)	0.0050 (15)	−0.0146 (14)	−0.0110 (14)
C12	0.0558 (16)	0.0610 (17)	0.0568 (16)	−0.0048 (14)	−0.0120 (13)	−0.0109 (13)
C13	0.0504 (14)	0.0444 (13)	0.0405 (12)	−0.0092 (11)	−0.0063 (11)	−0.0073 (10)
C14	0.0545 (15)	0.0478 (14)	0.0409 (12)	−0.0112 (12)	−0.0067 (11)	−0.0098 (11)
C15	0.0647 (17)	0.0417 (13)	0.0437 (13)	−0.0044 (12)	−0.0103 (12)	−0.0077 (11)
C16	0.0642 (18)	0.0620 (17)	0.0565 (16)	−0.0015 (14)	−0.0018 (13)	−0.0164 (13)
O17	0.0843 (14)	0.0608 (12)	0.0652 (12)	−0.0144 (10)	−0.0125 (10)	−0.0272 (9)
C18	0.0492 (14)	0.0496 (15)	0.0549 (15)	−0.0149 (12)	−0.0100 (12)	−0.0080 (12)
C19	0.087 (2)	0.0518 (17)	0.078 (2)	−0.0177 (15)	0.0027 (16)	−0.0137 (15)
C20	0.097 (3)	0.0479 (18)	0.108 (3)	−0.0184 (17)	−0.004 (2)	0.0005 (18)
C21	0.101 (3)	0.075 (2)	0.079 (2)	−0.037 (2)	−0.014 (2)	0.0195 (19)
C22	0.103 (3)	0.087 (3)	0.0584 (18)	−0.035 (2)	0.0058 (17)	−0.0065 (17)
C23	0.078 (2)	0.0606 (17)	0.0609 (17)	−0.0219 (15)	−0.0038 (15)	−0.0121 (14)
C24	0.0496 (14)	0.0522 (14)	0.0434 (13)	−0.0109 (12)	−0.0059 (11)	−0.0128 (11)
C25	0.0559 (17)	0.0673 (18)	0.0699 (18)	−0.0215 (14)	−0.0085 (14)	−0.0094 (14)
C26	0.0537 (18)	0.097 (3)	0.094 (2)	−0.0221 (18)	−0.0144 (17)	−0.028 (2)
C27	0.064 (2)	0.082 (2)	0.075 (2)	0.0002 (17)	−0.0263 (17)	−0.0233 (18)
C28	0.073 (2)	0.0676 (18)	0.0521 (16)	−0.0062 (16)	−0.0142 (14)	−0.0066 (13)
C29	0.0565 (16)	0.0627 (17)	0.0526 (15)	−0.0148 (14)	−0.0079 (12)	−0.0066 (13)
N1A	0.0461 (12)	0.0501 (12)	0.0540 (12)	−0.0146 (10)	−0.0071 (9)	−0.0078 (10)
C2A	0.0549 (15)	0.0467 (14)	0.0448 (13)	−0.0191 (12)	−0.0067 (11)	−0.0009 (11)
C3A	0.0649 (17)	0.0457 (14)	0.0422 (13)	−0.0202 (13)	−0.0057 (11)	−0.0039 (11)
C4A	0.0524 (15)	0.0465 (14)	0.0478 (14)	−0.0088 (12)	−0.0007 (11)	−0.0046 (11)
C5A	0.0406 (13)	0.0544 (15)	0.0501 (14)	−0.0070 (11)	−0.0042 (11)	−0.0113 (11)
N6A	0.0395 (11)	0.0534 (12)	0.0478 (11)	−0.0123 (9)	0.0000 (9)	−0.0078 (9)
C7A	0.0404 (13)	0.0510 (14)	0.0483 (13)	−0.0099 (11)	−0.0040 (10)	−0.0091 (11)
C8A	0.0405 (13)	0.0565 (15)	0.0573 (15)	−0.0101 (12)	−0.0007 (11)	−0.0183 (12)
C9A	0.0650 (18)	0.0588 (17)	0.0688 (18)	−0.0262 (15)	−0.0179 (14)	−0.0008 (14)
C10A	0.088 (2)	0.074 (2)	0.089 (2)	−0.040 (2)	−0.0306 (19)	−0.0095 (17)
C11A	0.113 (3)	0.068 (2)	0.074 (2)	−0.043 (2)	−0.0177 (19)	−0.0188 (16)
C12A	0.087 (2)	0.0552 (17)	0.0620 (17)	−0.0242 (16)	−0.0025 (15)	−0.0123 (13)
C13A	0.0443 (14)	0.0474 (14)	0.0436 (13)	−0.0101 (11)	−0.0017 (10)	−0.0061 (11)
C14A	0.0411 (13)	0.0516 (14)	0.0452 (13)	−0.0140 (11)	−0.0027 (10)	−0.0067 (11)
C15A	0.0507 (16)	0.0727 (18)	0.0552 (15)	−0.0218 (14)	0.0020 (12)	−0.0160 (14)
C16A	0.081 (2)	0.081 (2)	0.083 (2)	−0.0400 (18)	0.0212 (17)	−0.0144 (17)
O17A	0.0478 (11)	0.0870 (15)	0.0991 (15)	−0.0178 (11)	0.0174 (10)	−0.0244 (12)
C18A	0.0458 (14)	0.0498 (14)	0.0539 (14)	−0.0050 (12)	−0.0100 (12)	−0.0079 (11)
C19A	0.0600 (17)	0.084 (2)	0.0565 (17)	−0.0180 (16)	−0.0074 (14)	−0.0012 (15)
C20A	0.081 (2)	0.106 (3)	0.0562 (18)	−0.021 (2)	−0.0007 (17)	0.0056 (17)
C21A	0.096 (3)	0.095 (3)	0.0508 (18)	−0.001 (2)	−0.0209 (18)	0.0006 (16)
C22A	0.075 (2)	0.092 (2)	0.071 (2)	−0.0129 (18)	−0.0342 (18)	−0.0031 (18)
C23A	0.0562 (17)	0.0727 (19)	0.0672 (18)	−0.0102 (14)	−0.0181 (14)	−0.0021 (14)
C24A	0.0435 (13)	0.0545 (15)	0.0499 (14)	−0.0179 (12)	0.0007 (11)	−0.0129 (11)
C25A	0.0666 (18)	0.0626 (17)	0.0612 (17)	−0.0180 (14)	−0.0111 (14)	−0.0152 (14)
C26A	0.082 (2)	0.090 (2)	0.0674 (19)	−0.0320 (19)	−0.0125 (16)	−0.0273 (17)
C27A	0.085 (2)	0.082 (2)	0.073 (2)	−0.042 (2)	0.0167 (18)	−0.0386 (18)
C28A	0.077 (2)	0.0591 (18)	0.084 (2)	−0.0207 (16)	0.0090 (17)	−0.0231 (16)
C29A	0.0605 (17)	0.0556 (17)	0.0647 (17)	−0.0128 (14)	−0.0017 (13)	−0.0135 (13)

Geometric parameters (Å, º)

N1—C14	1.309 (3)	N1A—C14A	1.319 (3)
N1—C2	1.368 (3)	N1A—C2A	1.368 (3)
C2—C9	1.412 (3)	C2A—C3A	1.405 (3)
C2—C3	1.417 (3)	C2A—C9A	1.411 (3)
C3—C12	1.407 (3)	C3A—C12A	1.407 (3)
C3—C4	1.410 (3)	C3A—C4A	1.416 (3)
C4—C13	1.351 (3)	C4A—C13A	1.359 (3)
C4—H4	0.9639	C4A—H4A	0.9442
C5—N6	1.483 (3)	C5A—N6A	1.487 (3)
C5—C13	1.499 (3)	C5A—C13A	1.509 (3)
C5—C18	1.525 (3)	C5A—C18A	1.519 (3)
C5—H5	0.9743	C5A—H5A	0.9450
N6—C15	1.365 (3)	N6A—C15A	1.362 (3)
N6—C7	1.481 (3)	N6A—C7A	1.479 (3)
C7—C24	1.508 (3)	C7A—C24A	1.516 (3)
C7—C8	1.540 (3)	C7A—C8A	1.537 (3)
C7—H7	0.9743	C7A—H7A	1.0112
C8—C14	1.491 (3)	C8A—C14A	1.490 (3)
C8—H8A	1.0016	C8A—H8A1	0.9716
C8—H8B	1.0016	C8A—H8A2	0.9716
C9—C10	1.355 (4)	C9A—C10A	1.358 (4)
C9—H9	0.9785	C9A—H9A	1.0419
C10—C11	1.398 (4)	C10A—C11A	1.382 (4)
C10—H10	0.9644	C10A—H10A	0.9602
C11—C12	1.359 (4)	C11A—C12A	1.360 (4)
C11—H11	0.9867	C11A—H11A	0.9344
C12—H12	0.9662	C12A—H12A	0.9584
C13—C14	1.421 (3)	C13A—C14A	1.410 (3)
C15—O17	1.229 (3)	C15A—O17A	1.225 (3)
C15—C16	1.507 (4)	C15A—C16A	1.500 (4)
C16—H16A	0.9546	C16A—H16D	0.9315
C16—H16B	0.9546	C16A—H16E	0.9315
C16—H16C	0.9546	C16A—H16F	0.9315
C18—C23	1.369 (4)	C18A—C19A	1.381 (4)
C18—C19	1.383 (4)	C18A—C23A	1.388 (3)
C19—C20	1.377 (4)	C19A—C20A	1.377 (4)
C19—H19	0.9539	C19A—H19A	0.9305
C20—C21	1.354 (5)	C20A—C21A	1.368 (5)
C20—H20	0.9283	C20A—H20A	0.9490
C21—C22	1.362 (4)	C21A—C22A	1.367 (5)
C21—H21	0.9153	C21A—H21A	0.9490
C22—C23	1.385 (4)	C22A—C23A	1.370 (4)
C22—H22	0.9141	C22A—H22A	0.9522
C23—H23	0.9373	C23A—H23A	0.9679
C24—C25	1.384 (4)	C24A—C25A	1.377 (3)
C24—C29	1.384 (3)	C24A—C29A	1.375 (3)
C25—C26	1.380 (4)	C25A—C26A	1.376 (4)
C25—H25	0.9634	C25A—H25A	0.9683
C26—C27	1.366 (4)	C26A—C27A	1.358 (4)
C26—H26	0.9106	C26A—H26A	0.9340
C27—C28	1.378 (4)	C27A—C28A	1.369 (4)
C27—H27	1.0218	C27A—H27A	0.9176
C28—C29	1.376 (4)	C28A—C29A	1.379 (4)
C28—H28	0.9627	C28A—H28A	0.9671
C29—H29	0.9725	C29A—H29A	1.0071
C14—N1—C2	116.5 (2)	C14A—N1A—C2A	118.2 (2)
N1—C2—C9	117.8 (2)	N1A—C2A—C3A	122.3 (2)
N1—C2—C3	123.4 (2)	N1A—C2A—C9A	118.5 (2)
C9—C2—C3	118.8 (2)	C3A—C2A—C9A	119.2 (2)
C12—C3—C4	123.0 (2)	C2A—C3A—C12A	118.8 (3)
C12—C3—C2	119.8 (2)	C2A—C3A—C4A	117.4 (2)
C4—C3—C2	117.2 (2)	C12A—C3A—C4A	123.8 (3)
C13—C4—C3	119.5 (2)	C13A—C4A—C3A	120.1 (2)
C13—C4—H4	120.2	C13A—C4A—H4A	119.9
C3—C4—H4	120.2	C3A—C4A—H4A	119.9
N6—C5—C13	109.67 (19)	N6A—C5A—C13A	109.29 (19)
N6—C5—C18	113.21 (19)	N6A—C5A—C18A	112.41 (19)
C13—C5—C18	115.2 (2)	C13A—C5A—C18A	114.8 (2)
N6—C5—H5	106.0	N6A—C5A—H5A	106.6
C13—C5—H5	106.0	C13A—C5A—H5A	106.6
C18—C5—H5	106.0	C18A—C5A—H5A	106.6
C15—N6—C7	121.4 (2)	C15A—N6A—C7A	120.9 (2)
C15—N6—C5	116.6 (2)	C15A—N6A—C5A	118.2 (2)
C7—N6—C5	120.71 (18)	C7A—N6A—C5A	119.67 (18)
N6—C7—C24	114.60 (19)	N6A—C7A—C24A	113.91 (19)
N6—C7—C8	110.8 (2)	N6A—C7A—C8A	111.00 (19)
C24—C7—C8	108.30 (19)	C24A—C7A—C8A	110.13 (19)
N6—C7—H7	107.6	N6A—C7A—H7A	107.2
C24—C7—H7	107.6	C24A—C7A—H7A	107.2
C8—C7—H7	107.6	C8A—C7A—H7A	107.2
C14—C8—C7	112.5 (2)	C14A—C8A—C7A	112.5 (2)
C14—C8—H8A	109.1	C14A—C8A—H8A1	109.1
C7—C8—H8A	109.1	C7A—C8A—H8A1	109.1
C14—C8—H8B	109.1	C14A—C8A—H8A2	109.1
C7—C8—H8B	109.1	C7A—C8A—H8A2	109.1
H8A—C8—H8B	107.8	H8A1—C8A—H8A2	107.8
C10—C9—C2	119.9 (3)	C10A—C9A—C2A	119.9 (3)
C10—C9—H9	120.1	C10A—C9A—H9A	120.0
C2—C9—H9	120.1	C2A—C9A—H9A	120.0
C9—C10—C11	121.0 (3)	C9A—C10A—C11A	121.1 (3)
C9—C10—H10	119.5	C9A—C10A—H10A	119.4
C11—C10—H10	119.5	C11A—C10A—H10A	119.4
C12—C11—C10	121.0 (3)	C12A—C11A—C10A	120.3 (3)
C12—C11—H11	119.5	C12A—C11A—H11A	119.9
C10—C11—H11	119.5	C10A—C11A—H11A	119.9
C11—C12—C3	119.4 (3)	C11A—C12A—C3A	120.6 (3)
C11—C12—H12	120.3	C11A—C12A—H12A	119.7
C3—C12—H12	120.3	C3A—C12A—H12A	119.7
C4—C13—C14	118.8 (2)	C4A—C13A—C14A	118.4 (2)
C4—C13—C5	122.8 (2)	C4A—C13A—C5A	124.1 (2)
C14—C13—C5	118.4 (2)	C14A—C13A—C5A	117.4 (2)
N1—C14—C13	124.6 (2)	N1A—C14A—C13A	123.6 (2)
N1—C14—C8	119.3 (2)	N1A—C14A—C8A	119.9 (2)
C13—C14—C8	116.2 (2)	C13A—C14A—C8A	116.5 (2)
O17—C15—N6	121.1 (2)	O17A—C15A—N6A	122.1 (3)
O17—C15—C16	120.1 (2)	O17A—C15A—C16A	119.3 (2)
N6—C15—C16	118.8 (2)	N6A—C15A—C16A	118.7 (2)
C15—C16—H16A	109.5	C15A—C16A—H16D	109.5
C15—C16—H16B	109.5	C15A—C16A—H16E	109.5
H16A—C16—H16B	109.5	H16D—C16A—H16E	109.5
C15—C16—H16C	109.5	C15A—C16A—H16F	109.5
H16A—C16—H16C	109.5	H16D—C16A—H16F	109.5
H16B—C16—H16C	109.5	H16E—C16A—H16F	109.5
C23—C18—C19	117.4 (3)	C19A—C18A—C23A	118.3 (3)
C23—C18—C5	124.1 (2)	C19A—C18A—C5A	123.5 (2)
C19—C18—C5	118.5 (2)	C23A—C18A—C5A	118.2 (2)
C18—C19—C20	121.6 (3)	C20A—C19A—C18A	120.3 (3)
C18—C19—H19	119.2	C20A—C19A—H19A	119.9
C20—C19—H19	119.2	C18A—C19A—H19A	119.9
C21—C20—C19	119.9 (3)	C21A—C20A—C19A	120.7 (3)
C21—C20—H20	120.0	C21A—C20A—H20A	119.7
C19—C20—H20	120.0	C19A—C20A—H20A	119.7
C20—C21—C22	119.9 (3)	C22A—C21A—C20A	119.7 (3)
C20—C21—H21	120.1	C22A—C21A—H21A	120.2
C22—C21—H21	120.1	C20A—C21A—H21A	120.2
C21—C22—C23	120.2 (3)	C21A—C22A—C23A	120.2 (3)
C21—C22—H22	119.9	C21A—C22A—H22A	119.9
C23—C22—H22	119.9	C23A—C22A—H22A	119.9
C18—C23—C22	121.1 (3)	C22A—C23A—C18A	120.9 (3)
C18—C23—H23	119.5	C22A—C23A—H23A	119.5
C22—C23—H23	119.5	C18A—C23A—H23A	119.5
C25—C24—C29	118.8 (2)	C25A—C24A—C29A	118.3 (2)
C25—C24—C7	119.8 (2)	C25A—C24A—C7A	123.4 (2)
C29—C24—C7	121.2 (2)	C29A—C24A—C7A	118.2 (2)
C26—C25—C24	120.5 (3)	C24A—C25A—C26A	120.5 (3)
C26—C25—H25	119.7	C24A—C25A—H25A	119.7
C24—C25—H25	119.7	C26A—C25A—H25A	119.7
C27—C26—C25	120.4 (3)	C27A—C26A—C25A	120.8 (3)
C27—C26—H26	119.8	C27A—C26A—H26A	119.6
C25—C26—H26	119.8	C25A—C26A—H26A	119.6
C26—C27—C28	119.6 (3)	C26A—C27A—C28A	119.3 (3)
C26—C27—H27	120.2	C26A—C27A—H27A	120.3
C28—C27—H27	120.2	C28A—C27A—H27A	120.3
C27—C28—C29	120.6 (3)	C27A—C28A—C29A	120.2 (3)
C27—C28—H28	119.7	C27A—C28A—H28A	119.9
C29—C28—H28	119.7	C29A—C28A—H28A	119.9
C28—C29—C24	120.2 (3)	C24A—C29A—C28A	120.7 (3)
C28—C29—H29	119.9	C24A—C29A—H29A	119.6
C24—C29—H29	119.9	C28A—C29A—H29A	119.6
C14—N1—C2—C9	179.5 (2)	C14A—N1A—C2A—C3A	2.2 (3)
C14—N1—C2—C3	−1.0 (3)	C14A—N1A—C2A—C9A	−176.8 (2)
N1—C2—C3—C12	−178.3 (2)	N1A—C2A—C3A—C12A	−179.8 (2)
C9—C2—C3—C12	1.2 (3)	C9A—C2A—C3A—C12A	−0.7 (3)
N1—C2—C3—C4	0.5 (3)	N1A—C2A—C3A—C4A	−0.3 (3)
C9—C2—C3—C4	180.0 (2)	C9A—C2A—C3A—C4A	178.8 (2)
C12—C3—C4—C13	179.4 (2)	C2A—C3A—C4A—C13A	−1.2 (3)
C2—C3—C4—C13	0.7 (3)	C12A—C3A—C4A—C13A	178.3 (2)
C13—C5—N6—C15	−125.7 (2)	C13A—C5A—N6A—C15A	120.9 (2)
C18—C5—N6—C15	104.1 (2)	C18A—C5A—N6A—C15A	−110.4 (2)
C13—C5—N6—C7	41.7 (3)	C13A—C5A—N6A—C7A	−46.4 (3)
C18—C5—N6—C7	−88.5 (2)	C18A—C5A—N6A—C7A	82.2 (2)
C15—N6—C7—C24	−70.2 (3)	C15A—N6A—C7A—C24A	73.3 (3)
C5—N6—C7—C24	123.1 (2)	C5A—N6A—C7A—C24A	−119.6 (2)
C15—N6—C7—C8	166.9 (2)	C15A—N6A—C7A—C8A	−161.7 (2)
C5—N6—C7—C8	0.1 (3)	C5A—N6A—C7A—C8A	5.4 (3)
N6—C7—C8—C14	−44.3 (3)	N6A—C7A—C8A—C14A	41.8 (3)
C24—C7—C8—C14	−170.8 (2)	C24A—C7A—C8A—C14A	168.8 (2)
N1—C2—C9—C10	178.6 (2)	N1A—C2A—C9A—C10A	179.7 (2)
C3—C2—C9—C10	−0.9 (4)	C3A—C2A—C9A—C10A	0.6 (4)
C2—C9—C10—C11	0.3 (4)	C2A—C9A—C10A—C11A	−0.3 (4)
C9—C10—C11—C12	0.1 (4)	C9A—C10A—C11A—C12A	0.1 (5)
C10—C11—C12—C3	0.3 (4)	C10A—C11A—C12A—C3A	−0.2 (4)
C4—C3—C12—C11	−179.6 (2)	C2A—C3A—C12A—C11A	0.6 (4)
C2—C3—C12—C11	−0.9 (4)	C4A—C3A—C12A—C11A	−178.9 (2)
C3—C4—C13—C14	−1.3 (3)	C3A—C4A—C13A—C14A	0.6 (3)
C3—C4—C13—C5	179.8 (2)	C3A—C4A—C13A—C5A	179.0 (2)
N6—C5—C13—C4	137.6 (2)	N6A—C5A—C13A—C4A	−137.0 (2)
C18—C5—C13—C4	−93.3 (3)	C18A—C5A—C13A—C4A	95.7 (3)
N6—C5—C13—C14	−41.4 (3)	N6A—C5A—C13A—C14A	41.4 (3)
C18—C5—C13—C14	87.8 (3)	C18A—C5A—C13A—C14A	−85.9 (3)
C2—N1—C14—C13	0.5 (3)	C2A—N1A—C14A—C13A	−2.8 (3)
C2—N1—C14—C8	−178.5 (2)	C2A—N1A—C14A—C8A	175.8 (2)
C4—C13—C14—N1	0.7 (3)	C4A—C13A—C14A—N1A	1.4 (3)
C5—C13—C14—N1	179.7 (2)	C5A—C13A—C14A—N1A	−177.0 (2)
C4—C13—C14—C8	179.6 (2)	C4A—C13A—C14A—C8A	−177.2 (2)
C5—C13—C14—C8	−1.3 (3)	C5A—C13A—C14A—C8A	4.3 (3)
C7—C8—C14—N1	−135.0 (2)	C7A—C8A—C14A—N1A	133.3 (2)
C7—C8—C14—C13	46.0 (3)	C7A—C8A—C14A—C13A	−48.0 (3)
C7—N6—C15—O17	−176.4 (2)	C7A—N6A—C15A—O17A	173.7 (2)
C5—N6—C15—O17	−9.1 (3)	C5A—N6A—C15A—O17A	6.5 (4)
C7—N6—C15—C16	3.2 (3)	C7A—N6A—C15A—C16A	−6.3 (4)
C5—N6—C15—C16	170.5 (2)	C5A—N6A—C15A—C16A	−173.5 (2)
N6—C5—C18—C23	116.8 (3)	N6A—C5A—C18A—C19A	−116.2 (3)
C13—C5—C18—C23	−10.5 (3)	C13A—C5A—C18A—C19A	9.5 (4)
N6—C5—C18—C19	−65.2 (3)	N6A—C5A—C18A—C23A	65.3 (3)
C13—C5—C18—C19	167.5 (2)	C13A—C5A—C18A—C23A	−169.0 (2)
C23—C18—C19—C20	0.2 (4)	C23A—C18A—C19A—C20A	−1.4 (4)
C5—C18—C19—C20	−177.9 (3)	C5A—C18A—C19A—C20A	−179.9 (3)
C18—C19—C20—C21	−0.5 (5)	C18A—C19A—C20A—C21A	0.3 (5)
C19—C20—C21—C22	0.4 (6)	C19A—C20A—C21A—C22A	0.8 (5)
C20—C21—C22—C23	0.1 (5)	C20A—C21A—C22A—C23A	−0.7 (5)
C19—C18—C23—C22	0.3 (4)	C21A—C22A—C23A—C18A	−0.4 (5)
C5—C18—C23—C22	178.3 (3)	C19A—C18A—C23A—C22A	1.4 (4)
C21—C22—C23—C18	−0.4 (5)	C5A—C18A—C23A—C22A	180.0 (3)
N6—C7—C24—C25	138.5 (2)	N6A—C7A—C24A—C25A	38.6 (3)
C8—C7—C24—C25	−97.2 (3)	C8A—C7A—C24A—C25A	−86.8 (3)
N6—C7—C24—C29	−46.1 (3)	N6A—C7A—C24A—C29A	−143.9 (2)
C8—C7—C24—C29	78.1 (3)	C8A—C7A—C24A—C29A	90.6 (3)
C29—C24—C25—C26	−0.9 (4)	C29A—C24A—C25A—C26A	0.3 (4)
C7—C24—C25—C26	174.6 (2)	C7A—C24A—C25A—C26A	177.7 (2)
C24—C25—C26—C27	0.6 (5)	C24A—C25A—C26A—C27A	0.5 (4)
C25—C26—C27—C28	0.2 (5)	C25A—C26A—C27A—C28A	−1.0 (5)
C26—C27—C28—C29	−0.8 (4)	C26A—C27A—C28A—C29A	0.6 (4)
C27—C28—C29—C24	0.5 (4)	C25A—C24A—C29A—C28A	−0.7 (4)
C25—C24—C29—C28	0.3 (4)	C7A—C24A—C29A—C28A	−178.2 (2)
C7—C24—C29—C28	−175.1 (2)	C27A—C28A—C29A—C24A	0.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O17	0.98 (2)	2.21 (2)	2.685 (3)	109
C5A—H5A···O17A	0.95 (2)	2.27 (2)	2.732 (3)	110
C7A—H7A···O17	1.01 (2)	2.45 (2)	3.322 (3)	145
C9A—H9A···O17A^i	1.04 (2)	2.37 (2)	3.325 (3)	153
C11A—H11A···O17^ii	0.93 (2)	2.47 (2)	3.276 (5)	145

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