10-[2-(9-Anthryl­oxy)­ethyl]-9-acridone

The title compound, C₂₉H₂₁NO₂, is an acridone derivative which crystallizes with two almost identical mol­ecules in the asymmetric unit. The angles between the two aromatic planes in the two mol­ecules in the asymmetric unit are 54.22 (3) and 54.04 (3)°.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.052
• wR factor = 0.125
• Data-to-parameter ratio = 13.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.10
         From the CIF: _reflns_number_total               7927
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         8947
         Completeness (_total/calc)             88.60%
          Alert B: < 90% complete (theta max?)

Author response: ... The data are 99% complete to 25 degrees in theta.

 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 0 Alert Level C = Please check

---

S1. Comment

Acridone derivatives are well known for their biological properties (Blanchard et al., 1978). They have been reported to be anticancer active and to be applicable as antimicrobial and antiparasitic agents (Nishi et al., 1981). This kind of compound is prepared by condensation of 9(10H)-acridanone and alkylhalogenderivates using phase transfer catalysis. The X-ray structure analysis has been carried out to determine unambiguously the nature of the reaction product.

The title compound, (I), crystallizes with two molecules in the asymmetric unit, which are almost identical. A least-squares fit of all non-H atoms gives an r.m.s. deviation of 0.180 Å. Bond lengths and angles do not show unusual values. The angle between the acridone and the anthracene planes are 54.22 (3) and 54.04 (3)° for the two molecules in the asymmetric unit.

S2. Experimental

The title compound was prepared in a three-necked flask containing sodium hydroxide (8 g, 200 mmol), triethylbenzylammonium chloride (0.25 g, 1 mmol) and water (25 ml). A solution of 9(10H)-acridone (5 mmol) in dichloromethane (125 ml) was added to 2-(9-anthryloxy)ethyl bromide (3 g, 10 mmol). At the end of the addition, the mixture was stirred and cooled in an ice water bath over 5 d. The solution was filtered and neutralized with aqueous hydrochloric acid (50 ml, 10%), sodium bicarbonate (50 ml, 5%) and water. The dichloromethane was removed on a rotary evaporator. The residue, recrystallized from ethyl ether and hexane (2/3), led to yellow crystals.

S3. Refinement

All H atoms were located by difference Fourier synthesis and refined with fixed individual displacement parameters [U(H) = 1.2U_eq(C)] using a riding model with aromatic C—H = 0.95 Å or methylene C—H = 0.99 Å.

Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991).

Figures

;

Crystal data

C29H21NO2	Z = 4
Mr = 415.47	F(000) = 872
Triclinic, P1	Dx = 1.360 Mg m^−3
a = 7.9833 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.6168 (8) Å	Cell parameters from 512 reflections
c = 18.744 (2) Å	θ = 1–20°
α = 107.180 (5)°	µ = 0.09 mm^−1
β = 96.514 (5)°	T = 173 K
γ = 99.570 (5)°	Plate, yellow
V = 2029.7 (3) Å^3	0.51 × 0.38 × 0.14 mm

Data collection

Siemens CCD three-circle diffractometer	7927 independent reflections
Radiation source: fine-focus sealed tube	4798 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
ω scans	θmax = 27.1°, θmin = 1.2°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −10→9
Tmin = 0.958, Tmax = 0.988	k = −18→17
22246 measured reflections	l = −23→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0533P)^2 + 0.2959P] where P = (Fo^2 + 2Fc^2)/3
7927 reflections	(Δ/σ)max = 0.001
577 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Special details

Experimental. ;

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
O1	0.27949 (17)	0.27535 (10)	0.18761 (8)	0.0342 (4)
C1	0.3113 (3)	0.21240 (15)	0.22828 (12)	0.0319 (5)
C2	0.3963 (3)	0.25213 (17)	0.30307 (12)	0.0396 (6)
C3	0.4461 (3)	0.3547 (2)	0.34079 (14)	0.0547 (7)
H3	0.4302	0.3993	0.3139	0.066*
C4	0.5177 (3)	0.3889 (2)	0.41644 (16)	0.0753 (9)
H4	0.5502	0.4574	0.4423	0.090*
C5	0.5430 (4)	0.3204 (3)	0.45626 (16)	0.0816 (11)
H5	0.5891	0.3445	0.5089	0.098*
C6	0.5032 (3)	0.2241 (3)	0.42092 (17)	0.0725 (9)
H6	0.5264	0.1813	0.4485	0.087*
C7	0.4277 (3)	0.1842 (2)	0.34373 (13)	0.0505 (7)
C8	0.3772 (3)	0.0839 (2)	0.30709 (16)	0.0539 (7)
H8	0.4046	0.0402	0.3332	0.065*
C9	0.2886 (3)	0.04634 (18)	0.23394 (15)	0.0467 (6)
C10	0.2281 (4)	−0.05682 (18)	0.19613 (19)	0.0592 (8)
H10	0.2563	−0.1016	0.2210	0.071*
C11	0.1327 (4)	−0.0914 (2)	0.12656 (19)	0.0713 (9)
H11	0.0945	−0.1601	0.1027	0.086*
C12	0.0890 (4)	−0.02647 (19)	0.08880 (16)	0.0609 (7)
H12	0.0179	−0.0518	0.0402	0.073*
C13	0.1466 (3)	0.07187 (16)	0.12063 (13)	0.0436 (6)
H13	0.1173	0.1143	0.0936	0.052*
C14	0.2503 (3)	0.11209 (15)	0.19383 (12)	0.0349 (5)
C15	0.4121 (3)	0.29040 (15)	0.14411 (12)	0.0343 (5)
H15A	0.4285	0.2268	0.1113	0.041*
H15B	0.5228	0.3261	0.1780	0.041*
C16	0.3518 (3)	0.35028 (15)	0.09647 (12)	0.0335 (5)
H16A	0.2381	0.3151	0.0651	0.040*
H16B	0.3379	0.4139	0.1303	0.040*
N17	0.4748 (2)	0.36787 (12)	0.04693 (9)	0.0308 (4)
C18	0.4563 (3)	0.30264 (15)	−0.02586 (12)	0.0319 (5)
C19	0.3378 (3)	0.21200 (15)	−0.05010 (13)	0.0393 (5)
H19	0.2696	0.1943	−0.0160	0.047*
C20	0.3200 (3)	0.14924 (16)	−0.12218 (14)	0.0451 (6)
H20	0.2387	0.0888	−0.1374	0.054*
C21	0.4183 (3)	0.17188 (17)	−0.17388 (13)	0.0463 (6)
H21	0.4045	0.1276	−0.2238	0.056*
C22	0.5352 (3)	0.25927 (16)	−0.15132 (12)	0.0405 (6)
H22	0.6025	0.2755	−0.1862	0.049*
C23	0.5575 (3)	0.32535 (15)	−0.07771 (12)	0.0322 (5)
C24	0.6830 (3)	0.41800 (15)	−0.05659 (12)	0.0323 (5)
O24	0.76190 (18)	0.44363 (11)	−0.10304 (8)	0.0407 (4)
C25	0.7112 (3)	0.47748 (14)	0.02314 (12)	0.0302 (5)
C26	0.8428 (3)	0.56241 (15)	0.05064 (13)	0.0360 (5)
H26	0.9126	0.5800	0.0170	0.043*
C27	0.8725 (3)	0.62018 (16)	0.12477 (13)	0.0396 (6)
H27	0.9626	0.6770	0.1426	0.048*
C28	0.7690 (3)	0.59479 (15)	0.17389 (13)	0.0394 (6)
H28	0.7882	0.6353	0.2253	0.047*
C29	0.6397 (3)	0.51233 (15)	0.14923 (12)	0.0350 (5)
H29	0.5716	0.4960	0.1839	0.042*
C30	0.6069 (2)	0.45158 (14)	0.07310 (12)	0.0294 (5)
O1A	−0.15790 (17)	0.24023 (10)	0.32763 (8)	0.0367 (4)
C1A	−0.1203 (2)	0.28802 (15)	0.27553 (12)	0.0300 (5)
C2A	−0.1767 (2)	0.23783 (15)	0.19863 (12)	0.0319 (5)
C3A	−0.2762 (3)	0.13987 (15)	0.17098 (14)	0.0406 (6)
H3A	−0.3021	0.1056	0.2056	0.049*
C4A	−0.3342 (3)	0.09533 (17)	0.09551 (15)	0.0482 (6)
H4A	−0.4012	0.0304	0.0778	0.058*
C5A	−0.2955 (3)	0.14501 (17)	0.04309 (14)	0.0472 (6)
H5A	−0.3373	0.1131	−0.0095	0.057*
C6A	−0.1996 (3)	0.23750 (16)	0.06700 (12)	0.0392 (5)
H6A	−0.1735	0.2690	0.0307	0.047*
C7A	−0.1373 (3)	0.28827 (15)	0.14520 (12)	0.0318 (5)
C8A	−0.0415 (3)	0.38433 (15)	0.17134 (12)	0.0315 (5)
H8A	−0.0122	0.4164	0.1357	0.038*
C9A	0.0118 (3)	0.43404 (14)	0.24825 (12)	0.0304 (5)
C10A	0.1097 (3)	0.53256 (15)	0.27671 (13)	0.0381 (5)
H10A	0.1448	0.5651	0.2422	0.046*
C11A	0.1530 (3)	0.58013 (16)	0.35221 (14)	0.0454 (6)
H11A	0.2192	0.6453	0.3700	0.054*
C12A	0.1006 (3)	0.53398 (17)	0.40491 (13)	0.0465 (6)
H12A	0.1281	0.5693	0.4576	0.056*
C13A	0.0118 (3)	0.44002 (16)	0.38108 (12)	0.0379 (5)
H13A	−0.0213	0.4098	0.4173	0.045*
C14A	−0.0327 (3)	0.38586 (14)	0.30233 (11)	0.0298 (5)
C15A	−0.0148 (3)	0.20431 (15)	0.35478 (12)	0.0326 (5)
H15C	0.0879	0.2582	0.3770	0.039*
H15D	0.0146	0.1532	0.3130	0.039*
C16A	−0.0741 (3)	0.16179 (15)	0.41476 (12)	0.0333 (5)
H16C	−0.1071	0.2133	0.4549	0.040*
H16D	−0.1771	0.1084	0.3915	0.040*
N17A	0.0618 (2)	0.12345 (12)	0.44865 (9)	0.0314 (4)
C18A	0.1734 (3)	0.18252 (15)	0.51470 (12)	0.0338 (5)
C19A	0.1742 (3)	0.28314 (16)	0.54476 (13)	0.0411 (6)
H19A	0.0985	0.3117	0.5193	0.049*
C20A	0.2833 (3)	0.34004 (17)	0.61039 (14)	0.0482 (6)
H20A	0.2814	0.4076	0.6300	0.058*
C21A	0.3965 (3)	0.30130 (19)	0.64892 (14)	0.0503 (6)
H21A	0.4718	0.3417	0.6943	0.060*
C22A	0.3976 (3)	0.20368 (17)	0.62034 (13)	0.0417 (6)
H22A	0.4745	0.1765	0.6465	0.050*
C23A	0.2882 (3)	0.14305 (15)	0.55345 (12)	0.0331 (5)
C24A	0.2934 (3)	0.03923 (16)	0.52560 (12)	0.0342 (5)
O24A	0.38123 (18)	0.00069 (11)	0.56277 (8)	0.0427 (4)
C25A	0.1882 (3)	−0.01602 (15)	0.45165 (11)	0.0310 (5)
C26A	0.1978 (3)	−0.11372 (16)	0.41668 (13)	0.0386 (6)
H26A	0.2752	−0.1424	0.4411	0.046*
C27A	0.0980 (3)	−0.16869 (17)	0.34812 (13)	0.0424 (6)
H27A	0.1066	−0.2346	0.3250	0.051*
C28A	−0.0160 (3)	−0.12658 (16)	0.31296 (13)	0.0393 (5)
H28A	−0.0869	−0.1647	0.2658	0.047*
C29A	−0.0283 (3)	−0.03147 (15)	0.34483 (12)	0.0341 (5)
H29A	−0.1060	−0.0041	0.3193	0.041*
C30A	0.0735 (3)	0.02628 (15)	0.41520 (12)	0.0308 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0328 (8)	0.0444 (9)	0.0411 (9)	0.0177 (7)	0.0165 (7)	0.0283 (7)
C1	0.0286 (11)	0.0452 (13)	0.0347 (13)	0.0148 (10)	0.0134 (10)	0.0251 (11)
C2	0.0286 (12)	0.0621 (16)	0.0352 (14)	0.0119 (11)	0.0135 (10)	0.0217 (12)
C3	0.0447 (15)	0.0750 (19)	0.0409 (16)	0.0046 (13)	0.0183 (12)	0.0135 (14)
C4	0.0505 (17)	0.104 (2)	0.0471 (18)	−0.0081 (16)	0.0174 (15)	−0.0021 (18)
C5	0.0412 (17)	0.165 (4)	0.0338 (17)	0.001 (2)	0.0089 (13)	0.035 (2)
C6	0.0354 (16)	0.145 (3)	0.0499 (19)	0.0150 (18)	0.0103 (14)	0.052 (2)
C7	0.0243 (12)	0.109 (2)	0.0376 (15)	0.0203 (13)	0.0144 (11)	0.0461 (15)
C8	0.0425 (15)	0.079 (2)	0.073 (2)	0.0280 (14)	0.0297 (14)	0.0580 (17)
C9	0.0387 (14)	0.0642 (16)	0.0619 (17)	0.0234 (12)	0.0301 (13)	0.0424 (14)
C10	0.0641 (18)	0.0497 (17)	0.099 (2)	0.0313 (14)	0.0547 (18)	0.0510 (17)
C11	0.083 (2)	0.0499 (17)	0.090 (2)	0.0125 (16)	0.048 (2)	0.0235 (18)
C12	0.0646 (18)	0.0513 (17)	0.0645 (19)	0.0026 (14)	0.0257 (15)	0.0147 (15)
C13	0.0428 (14)	0.0463 (14)	0.0468 (15)	0.0077 (11)	0.0166 (12)	0.0204 (12)
C14	0.0332 (12)	0.0426 (13)	0.0440 (14)	0.0160 (10)	0.0210 (11)	0.0265 (11)
C15	0.0331 (12)	0.0429 (12)	0.0400 (13)	0.0140 (10)	0.0153 (10)	0.0264 (11)
C16	0.0310 (12)	0.0396 (12)	0.0392 (13)	0.0106 (10)	0.0100 (10)	0.0235 (11)
N17	0.0310 (10)	0.0361 (10)	0.0329 (11)	0.0096 (8)	0.0080 (8)	0.0202 (9)
C18	0.0313 (12)	0.0369 (12)	0.0353 (13)	0.0136 (10)	0.0045 (10)	0.0204 (11)
C19	0.0382 (13)	0.0404 (13)	0.0435 (15)	0.0081 (11)	0.0052 (11)	0.0206 (12)
C20	0.0424 (14)	0.0386 (13)	0.0549 (17)	0.0083 (11)	−0.0006 (12)	0.0194 (13)
C21	0.0475 (15)	0.0478 (15)	0.0411 (15)	0.0148 (12)	0.0024 (12)	0.0096 (12)
C22	0.0398 (13)	0.0514 (14)	0.0382 (14)	0.0189 (12)	0.0070 (11)	0.0210 (12)
C23	0.0309 (12)	0.0403 (12)	0.0349 (13)	0.0165 (10)	0.0064 (10)	0.0208 (11)
C24	0.0265 (11)	0.0417 (13)	0.0403 (14)	0.0159 (10)	0.0074 (10)	0.0252 (11)
O24	0.0379 (9)	0.0537 (9)	0.0437 (9)	0.0147 (7)	0.0165 (7)	0.0291 (8)
C25	0.0300 (11)	0.0339 (11)	0.0366 (13)	0.0153 (9)	0.0068 (10)	0.0211 (10)
C26	0.0297 (12)	0.0395 (13)	0.0481 (15)	0.0119 (10)	0.0089 (10)	0.0248 (12)
C27	0.0294 (12)	0.0355 (12)	0.0561 (16)	0.0078 (10)	0.0026 (11)	0.0192 (12)
C28	0.0404 (14)	0.0383 (13)	0.0407 (14)	0.0162 (11)	0.0028 (11)	0.0116 (11)
C29	0.0359 (13)	0.0410 (13)	0.0366 (13)	0.0153 (10)	0.0090 (10)	0.0200 (11)
C30	0.0265 (11)	0.0335 (11)	0.0362 (13)	0.0132 (9)	0.0031 (9)	0.0203 (10)
O1A	0.0302 (8)	0.0499 (9)	0.0468 (9)	0.0142 (7)	0.0133 (7)	0.0347 (8)
C1A	0.0261 (11)	0.0389 (12)	0.0381 (13)	0.0136 (9)	0.0115 (10)	0.0258 (11)
C2A	0.0252 (11)	0.0359 (12)	0.0415 (14)	0.0127 (9)	0.0077 (10)	0.0186 (11)
C3A	0.0313 (12)	0.0378 (13)	0.0562 (16)	0.0100 (10)	0.0030 (11)	0.0202 (12)
C4A	0.0369 (14)	0.0377 (13)	0.0650 (18)	0.0108 (11)	−0.0006 (13)	0.0111 (13)
C5A	0.0404 (14)	0.0542 (16)	0.0425 (15)	0.0188 (12)	0.0004 (11)	0.0064 (13)
C6A	0.0366 (13)	0.0490 (14)	0.0360 (14)	0.0168 (11)	0.0060 (11)	0.0152 (12)
C7A	0.0283 (11)	0.0398 (12)	0.0345 (13)	0.0178 (10)	0.0078 (10)	0.0161 (10)
C8A	0.0299 (11)	0.0393 (12)	0.0367 (13)	0.0158 (10)	0.0118 (10)	0.0222 (11)
C9A	0.0296 (11)	0.0345 (12)	0.0367 (13)	0.0138 (9)	0.0091 (10)	0.0206 (10)
C10A	0.0386 (13)	0.0368 (12)	0.0473 (15)	0.0105 (10)	0.0066 (11)	0.0249 (12)
C11A	0.0454 (14)	0.0370 (13)	0.0514 (16)	0.0073 (11)	−0.0015 (12)	0.0152 (12)
C12A	0.0536 (16)	0.0453 (14)	0.0387 (15)	0.0165 (12)	0.0037 (12)	0.0091 (12)
C13A	0.0412 (13)	0.0473 (14)	0.0337 (13)	0.0174 (11)	0.0092 (10)	0.0205 (11)
C14A	0.0293 (11)	0.0368 (12)	0.0317 (12)	0.0144 (9)	0.0091 (9)	0.0183 (10)
C15A	0.0298 (12)	0.0396 (12)	0.0417 (13)	0.0150 (9)	0.0118 (10)	0.0264 (11)
C16A	0.0317 (12)	0.0393 (12)	0.0415 (13)	0.0146 (10)	0.0143 (10)	0.0249 (11)
N17A	0.0324 (10)	0.0355 (10)	0.0363 (11)	0.0121 (8)	0.0103 (8)	0.0221 (9)
C18A	0.0322 (12)	0.0411 (13)	0.0381 (13)	0.0092 (10)	0.0143 (10)	0.0239 (11)
C19A	0.0429 (14)	0.0424 (13)	0.0460 (15)	0.0129 (11)	0.0149 (12)	0.0213 (12)
C20A	0.0528 (16)	0.0430 (14)	0.0503 (16)	0.0091 (12)	0.0190 (13)	0.0138 (13)
C21A	0.0450 (15)	0.0593 (17)	0.0430 (15)	0.0029 (13)	0.0103 (12)	0.0146 (13)
C22A	0.0340 (13)	0.0573 (16)	0.0415 (14)	0.0100 (11)	0.0118 (11)	0.0252 (13)
C23A	0.0295 (12)	0.0437 (13)	0.0344 (13)	0.0075 (10)	0.0134 (10)	0.0221 (11)
C24A	0.0272 (11)	0.0498 (14)	0.0418 (14)	0.0131 (10)	0.0176 (10)	0.0320 (12)
O24A	0.0364 (9)	0.0580 (10)	0.0503 (10)	0.0164 (7)	0.0106 (7)	0.0373 (9)
C25A	0.0313 (12)	0.0382 (12)	0.0347 (13)	0.0108 (9)	0.0146 (10)	0.0233 (10)
C26A	0.0419 (13)	0.0445 (13)	0.0467 (15)	0.0183 (11)	0.0204 (12)	0.0306 (12)
C27A	0.0511 (15)	0.0385 (13)	0.0468 (15)	0.0157 (11)	0.0204 (12)	0.0197 (12)
C28A	0.0409 (13)	0.0423 (13)	0.0406 (14)	0.0092 (11)	0.0137 (11)	0.0192 (11)
C29A	0.0318 (12)	0.0415 (13)	0.0382 (13)	0.0111 (10)	0.0102 (10)	0.0232 (11)
C30A	0.0303 (11)	0.0367 (12)	0.0354 (13)	0.0094 (9)	0.0152 (10)	0.0217 (11)

Geometric parameters (Å, º)

O1—C1	1.393 (2)	O1A—C1A	1.390 (2)
O1—C15	1.435 (2)	O1A—C15A	1.437 (2)
C1—C2	1.391 (3)	C1A—C2A	1.392 (3)
C1—C14	1.391 (3)	C1A—C14A	1.397 (3)
C2—C3	1.420 (3)	C2A—C3A	1.428 (3)
C2—C7	1.455 (3)	C2A—C7A	1.441 (3)
C3—C4	1.374 (3)	C3A—C4A	1.359 (3)
C3—H3	0.9500	C3A—H3A	0.9500
C4—C5	1.440 (4)	C4A—C5A	1.416 (3)
C4—H4	0.9500	C4A—H4A	0.9500
C5—C6	1.332 (4)	C5A—C6A	1.354 (3)
C5—H5	0.9500	C5A—H5A	0.9500
C6—C7	1.408 (4)	C6A—C7A	1.420 (3)
C6—H6	0.9500	C6A—H6A	0.9500
C7—C8	1.389 (4)	C7A—C8A	1.396 (3)
C8—C9	1.374 (3)	C8A—C9A	1.388 (3)
C8—H8	0.9500	C8A—H8A	0.9500
C9—C14	1.433 (3)	C9A—C10A	1.430 (3)
C9—C10	1.435 (3)	C9A—C14A	1.439 (3)
C10—C11	1.339 (4)	C10A—C11A	1.354 (3)
C10—H10	0.9500	C10A—H10A	0.9500
C11—C12	1.405 (4)	C11A—C12A	1.414 (3)
C11—H11	0.9500	C11A—H11A	0.9500
C12—C13	1.358 (3)	C12A—C13A	1.353 (3)
C12—H12	0.9500	C12A—H12A	0.9500
C13—C14	1.420 (3)	C13A—C14A	1.424 (3)
C13—H13	0.9500	C13A—H13A	0.9500
C15—C16	1.516 (3)	C15A—C16A	1.520 (2)
C15—H15A	0.9900	C15A—H15C	0.9900
C15—H15B	0.9900	C15A—H15D	0.9900
C16—N17	1.468 (2)	C16A—N17A	1.466 (2)
C16—H16A	0.9900	C16A—H16C	0.9900
C16—H16B	0.9900	C16A—H16D	0.9900
N17—C18	1.390 (3)	N17A—C18A	1.391 (3)
N17—C30	1.396 (2)	N17A—C30A	1.397 (2)
C18—C19	1.410 (3)	C18A—C23A	1.405 (3)
C18—C23	1.409 (3)	C18A—C19A	1.410 (3)
C19—C20	1.367 (3)	C19A—C20A	1.369 (3)
C19—H19	0.9500	C19A—H19A	0.9500
C20—C21	1.393 (3)	C20A—C21A	1.386 (3)
C20—H20	0.9500	C20A—H20A	0.9500
C21—C22	1.370 (3)	C21A—C22A	1.370 (3)
C21—H21	0.9500	C21A—H21A	0.9500
C22—C23	1.403 (3)	C22A—C23A	1.399 (3)
C22—H22	0.9500	C22A—H22A	0.9500
C23—C24	1.462 (3)	C23A—C24A	1.461 (3)
C24—O24	1.238 (2)	C24A—O24A	1.244 (2)
C24—C25	1.460 (3)	C24A—C25A	1.459 (3)
C25—C26	1.406 (3)	C25A—C26A	1.403 (3)
C25—C30	1.412 (3)	C25A—C30A	1.409 (3)
C26—C27	1.366 (3)	C26A—C27A	1.370 (3)
C26—H26	0.9500	C26A—H26A	0.9500
C27—C28	1.393 (3)	C27A—C28A	1.390 (3)
C27—H27	0.9500	C27A—H27A	0.9500
C28—C29	1.371 (3)	C28A—C29A	1.366 (3)
C28—H28	0.9500	C28A—H28A	0.9500
C29—C30	1.408 (3)	C29A—C30A	1.408 (3)
C29—H29	0.9500	C29A—H29A	0.9500
C1—O1—C15	111.77 (14)	C1A—O1A—C15A	112.82 (14)
C2—C1—C14	122.15 (19)	O1A—C1A—C2A	118.88 (18)
C2—C1—O1	118.91 (19)	O1A—C1A—C14A	118.80 (19)
C14—C1—O1	118.87 (19)	C2A—C1A—C14A	122.28 (18)
C1—C2—C3	122.6 (2)	C1A—C2A—C3A	122.65 (19)
C1—C2—C7	117.4 (2)	C1A—C2A—C7A	118.34 (18)
C3—C2—C7	119.9 (2)	C3A—C2A—C7A	119.0 (2)
C4—C3—C2	119.6 (3)	C4A—C3A—C2A	120.5 (2)
C4—C3—H3	120.2	C4A—C3A—H3A	119.8
C2—C3—H3	120.2	C2A—C3A—H3A	119.8
C3—C4—C5	119.6 (3)	C3A—C4A—C5A	120.5 (2)
C3—C4—H4	120.2	C3A—C4A—H4A	119.8
C5—C4—H4	120.2	C5A—C4A—H4A	119.8
C6—C5—C4	121.5 (3)	C6A—C5A—C4A	120.8 (2)
C6—C5—H5	119.3	C6A—C5A—H5A	119.6
C4—C5—H5	119.3	C4A—C5A—H5A	119.6
C5—C6—C7	121.7 (3)	C5A—C6A—C7A	121.3 (2)
C5—C6—H6	119.1	C5A—C6A—H6A	119.4
C7—C6—H6	119.1	C7A—C6A—H6A	119.4
C8—C7—C6	122.4 (3)	C8A—C7A—C6A	122.34 (19)
C8—C7—C2	120.0 (2)	C8A—C7A—C2A	119.69 (19)
C6—C7—C2	117.6 (3)	C6A—C7A—C2A	117.97 (19)
C9—C8—C7	121.6 (2)	C9A—C8A—C7A	121.37 (18)
C9—C8—H8	119.2	C9A—C8A—H8A	119.3
C7—C8—H8	119.2	C7A—C8A—H8A	119.3
C8—C9—C14	119.3 (2)	C8A—C9A—C10A	122.62 (18)
C8—C9—C10	122.6 (2)	C8A—C9A—C14A	119.48 (18)
C14—C9—C10	118.1 (2)	C10A—C9A—C14A	117.9 (2)
C11—C10—C9	121.5 (2)	C11A—C10A—C9A	120.9 (2)
C11—C10—H10	119.3	C11A—C10A—H10A	119.5
C9—C10—H10	119.3	C9A—C10A—H10A	119.5
C10—C11—C12	120.2 (3)	C10A—C11A—C12A	120.8 (2)
C10—C11—H11	119.9	C10A—C11A—H11A	119.6
C12—C11—H11	119.9	C12A—C11A—H11A	119.6
C13—C12—C11	121.1 (3)	C13A—C12A—C11A	120.7 (2)
C13—C12—H12	119.5	C13A—C12A—H12A	119.7
C11—C12—H12	119.5	C11A—C12A—H12A	119.7
C12—C13—C14	120.8 (2)	C12A—C13A—C14A	120.7 (2)
C12—C13—H13	119.6	C12A—C13A—H13A	119.6
C14—C13—H13	119.6	C14A—C13A—H13A	119.6
C1—C14—C13	122.41 (19)	C1A—C14A—C13A	122.44 (18)
C1—C14—C9	119.3 (2)	C1A—C14A—C9A	118.67 (19)
C13—C14—C9	118.2 (2)	C13A—C14A—C9A	118.88 (19)
O1—C15—C16	106.17 (16)	O1A—C15A—C16A	105.49 (15)
O1—C15—H15A	110.5	O1A—C15A—H15C	110.6
C16—C15—H15A	110.5	C16A—C15A—H15C	110.6
O1—C15—H15B	110.5	O1A—C15A—H15D	110.6
C16—C15—H15B	110.5	C16A—C15A—H15D	110.6
H15A—C15—H15B	108.7	H15C—C15A—H15D	108.8
N17—C16—C15	111.50 (16)	N17A—C16A—C15A	111.46 (16)
N17—C16—H16A	109.3	N17A—C16A—H16C	109.3
C15—C16—H16A	109.3	C15A—C16A—H16C	109.3
N17—C16—H16B	109.3	N17A—C16A—H16D	109.3
C15—C16—H16B	109.3	C15A—C16A—H16D	109.3
H16A—C16—H16B	108.0	H16C—C16A—H16D	108.0
C18—N17—C30	120.73 (17)	C18A—N17A—C30A	120.73 (17)
C18—N17—C16	119.92 (17)	C18A—N17A—C16A	120.10 (17)
C30—N17—C16	119.34 (17)	C30A—N17A—C16A	119.13 (17)
N17—C18—C19	121.51 (19)	N17A—C18A—C23A	120.63 (19)
N17—C18—C23	120.55 (18)	N17A—C18A—C19A	121.17 (19)
C19—C18—C23	117.9 (2)	C23A—C18A—C19A	118.2 (2)
C20—C19—C18	120.7 (2)	C20A—C19A—C18A	120.5 (2)
C20—C19—H19	119.7	C20A—C19A—H19A	119.8
C18—C19—H19	119.7	C18A—C19A—H19A	119.8
C19—C20—C21	121.6 (2)	C19A—C20A—C21A	121.5 (2)
C19—C20—H20	119.2	C19A—C20A—H20A	119.2
C21—C20—H20	119.2	C21A—C20A—H20A	119.2
C22—C21—C20	118.7 (2)	C22A—C21A—C20A	118.7 (2)
C22—C21—H21	120.6	C22A—C21A—H21A	120.6
C20—C21—H21	120.6	C20A—C21A—H21A	120.6
C21—C22—C23	121.4 (2)	C21A—C22A—C23A	121.5 (2)
C21—C22—H22	119.3	C21A—C22A—H22A	119.2
C23—C22—H22	119.3	C23A—C22A—H22A	119.2
C22—C23—C18	119.7 (2)	C22A—C23A—C18A	119.6 (2)
C22—C23—C24	119.25 (19)	C22A—C23A—C24A	119.43 (19)
C18—C23—C24	121.0 (2)	C18A—C23A—C24A	121.0 (2)
O24—C24—C25	122.28 (19)	O24A—C24A—C25A	122.4 (2)
O24—C24—C23	122.2 (2)	O24A—C24A—C23A	122.1 (2)
C25—C24—C23	115.52 (18)	C25A—C24A—C23A	115.54 (18)
C26—C25—C30	119.3 (2)	C26A—C25A—C30A	119.1 (2)
C26—C25—C24	119.67 (19)	C26A—C25A—C24A	119.79 (19)
C30—C25—C24	120.99 (19)	C30A—C25A—C24A	121.10 (19)
C27—C26—C25	121.4 (2)	C27A—C26A—C25A	121.5 (2)
C27—C26—H26	119.3	C27A—C26A—H26A	119.3
C25—C26—H26	119.3	C25A—C26A—H26A	119.3
C26—C27—C28	119.2 (2)	C26A—C27A—C28A	119.0 (2)
C26—C27—H27	120.4	C26A—C27A—H27A	120.5
C28—C27—H27	120.4	C28A—C27A—H27A	120.5
C29—C28—C27	121.1 (2)	C29A—C28A—C27A	121.3 (2)
C29—C28—H28	119.4	C29A—C28A—H28A	119.3
C27—C28—H28	119.4	C27A—C28A—H28A	119.3
C28—C29—C30	120.7 (2)	C28A—C29A—C30A	120.5 (2)
C28—C29—H29	119.7	C28A—C29A—H29A	119.7
C30—C29—H29	119.7	C30A—C29A—H29A	119.7
N17—C30—C29	121.39 (18)	N17A—C30A—C25A	120.26 (19)
N17—C30—C25	120.32 (19)	N17A—C30A—C29A	121.17 (18)
C29—C30—C25	118.29 (19)	C25A—C30A—C29A	118.57 (19)
C15—O1—C1—C2	94.4 (2)	C15A—O1A—C1A—C2A	100.3 (2)
C15—O1—C1—C14	−88.5 (2)	C15A—O1A—C1A—C14A	−82.0 (2)
C14—C1—C2—C3	−174.52 (19)	O1A—C1A—C2A—C3A	1.9 (3)
O1—C1—C2—C3	2.5 (3)	C14A—C1A—C2A—C3A	−175.75 (19)
C14—C1—C2—C7	3.1 (3)	O1A—C1A—C2A—C7A	179.83 (17)
O1—C1—C2—C7	−179.86 (17)	C14A—C1A—C2A—C7A	2.2 (3)
C1—C2—C3—C4	175.0 (2)	C1A—C2A—C3A—C4A	177.3 (2)
C7—C2—C3—C4	−2.6 (3)	C7A—C2A—C3A—C4A	−0.6 (3)
C2—C3—C4—C5	0.7 (4)	C2A—C3A—C4A—C5A	0.6 (3)
C3—C4—C5—C6	2.0 (4)	C3A—C4A—C5A—C6A	0.3 (3)
C4—C5—C6—C7	−2.8 (4)	C4A—C5A—C6A—C7A	−1.1 (3)
C5—C6—C7—C8	−176.6 (2)	C5A—C6A—C7A—C8A	−178.6 (2)
C5—C6—C7—C2	0.8 (4)	C5A—C6A—C7A—C2A	1.0 (3)
C1—C2—C7—C8	1.6 (3)	C1A—C2A—C7A—C8A	1.4 (3)
C3—C2—C7—C8	179.3 (2)	C3A—C2A—C7A—C8A	179.41 (19)
C1—C2—C7—C6	−175.8 (2)	C1A—C2A—C7A—C6A	−178.18 (18)
C3—C2—C7—C6	1.8 (3)	C3A—C2A—C7A—C6A	−0.2 (3)
C6—C7—C8—C9	173.5 (2)	C6A—C7A—C8A—C9A	177.20 (19)
C2—C7—C8—C9	−3.8 (3)	C2A—C7A—C8A—C9A	−2.4 (3)
C7—C8—C9—C14	1.3 (3)	C7A—C8A—C9A—C10A	−179.82 (19)
C7—C8—C9—C10	−177.0 (2)	C7A—C8A—C9A—C14A	−0.2 (3)
C8—C9—C10—C11	175.7 (2)	C8A—C9A—C10A—C11A	177.1 (2)
C14—C9—C10—C11	−2.6 (3)	C14A—C9A—C10A—C11A	−2.6 (3)
C9—C10—C11—C12	−0.2 (4)	C9A—C10A—C11A—C12A	−0.8 (3)
C10—C11—C12—C13	2.2 (4)	C10A—C11A—C12A—C13A	2.5 (3)
C11—C12—C13—C14	−1.3 (4)	C11A—C12A—C13A—C14A	−0.7 (3)
C2—C1—C14—C13	172.7 (2)	O1A—C1A—C14A—C13A	−3.3 (3)
O1—C1—C14—C13	−4.4 (3)	C2A—C1A—C14A—C13A	174.34 (19)
C2—C1—C14—C9	−5.6 (3)	O1A—C1A—C14A—C9A	177.66 (17)
O1—C1—C14—C9	177.34 (17)	C2A—C1A—C14A—C9A	−4.7 (3)
C12—C13—C14—C1	−179.9 (2)	C12A—C13A—C14A—C1A	178.3 (2)
C12—C13—C14—C9	−1.6 (3)	C12A—C13A—C14A—C9A	−2.7 (3)
C8—C9—C14—C1	3.4 (3)	C8A—C9A—C14A—C1A	3.6 (3)
C10—C9—C14—C1	−178.26 (19)	C10A—C9A—C14A—C1A	−176.69 (18)
C8—C9—C14—C13	−175.0 (2)	C8A—C9A—C14A—C13A	−175.42 (19)
C10—C9—C14—C13	3.4 (3)	C10A—C9A—C14A—C13A	4.2 (3)
C1—O1—C15—C16	173.84 (17)	C1A—O1A—C15A—C16A	175.82 (17)
O1—C15—C16—N17	−178.01 (16)	O1A—C15A—C16A—N17A	−179.05 (16)
C15—C16—N17—C18	90.9 (2)	C15A—C16A—N17A—C18A	93.3 (2)
C15—C16—N17—C30	−90.6 (2)	C15A—C16A—N17A—C30A	−88.8 (2)
C30—N17—C18—C19	172.05 (18)	C30A—N17A—C18A—C23A	−6.6 (3)
C16—N17—C18—C19	−9.5 (3)	C16A—N17A—C18A—C23A	171.19 (17)
C30—N17—C18—C23	−7.5 (3)	C30A—N17A—C18A—C19A	173.62 (17)
C16—N17—C18—C23	170.94 (17)	C16A—N17A—C18A—C19A	−8.6 (3)
N17—C18—C19—C20	179.25 (18)	N17A—C18A—C19A—C20A	179.13 (19)
C23—C18—C19—C20	−1.2 (3)	C23A—C18A—C19A—C20A	−0.6 (3)
C18—C19—C20—C21	0.5 (3)	C18A—C19A—C20A—C21A	0.4 (3)
C19—C20—C21—C22	0.0 (3)	C19A—C20A—C21A—C22A	−0.3 (3)
C20—C21—C22—C23	0.2 (3)	C20A—C21A—C22A—C23A	0.2 (3)
C21—C22—C23—C18	−1.0 (3)	C21A—C22A—C23A—C18A	−0.4 (3)
C21—C22—C23—C24	−179.55 (19)	C21A—C22A—C23A—C24A	−179.51 (19)
N17—C18—C23—C22	−179.01 (17)	N17A—C18A—C23A—C22A	−179.14 (17)
C19—C18—C23—C22	1.4 (3)	C19A—C18A—C23A—C22A	0.6 (3)
N17—C18—C23—C24	−0.5 (3)	N17A—C18A—C23A—C24A	−0.1 (3)
C19—C18—C23—C24	179.97 (18)	C19A—C18A—C23A—C24A	179.67 (18)
C22—C23—C24—O24	5.4 (3)	C22A—C23A—C24A—O24A	6.4 (3)
C18—C23—C24—O24	−173.20 (18)	C18A—C23A—C24A—O24A	−172.68 (18)
C22—C23—C24—C25	−173.70 (17)	C22A—C23A—C24A—C25A	−173.88 (17)
C18—C23—C24—C25	7.7 (3)	C18A—C23A—C24A—C25A	7.1 (3)
O24—C24—C25—C26	−6.0 (3)	O24A—C24A—C25A—C26A	−6.6 (3)
C23—C24—C25—C26	173.01 (17)	C23A—C24A—C25A—C26A	173.67 (17)
O24—C24—C25—C30	173.30 (18)	O24A—C24A—C25A—C30A	171.88 (18)
C23—C24—C25—C30	−7.6 (3)	C23A—C24A—C25A—C30A	−7.9 (3)
C30—C25—C26—C27	0.3 (3)	C30A—C25A—C26A—C27A	−0.1 (3)
C24—C25—C26—C27	179.66 (18)	C24A—C25A—C26A—C27A	178.41 (18)
C25—C26—C27—C28	−0.6 (3)	C25A—C26A—C27A—C28A	−0.5 (3)
C26—C27—C28—C29	0.8 (3)	C26A—C27A—C28A—C29A	1.0 (3)
C27—C28—C29—C30	−0.8 (3)	C27A—C28A—C29A—C30A	−0.9 (3)
C18—N17—C30—C29	−172.57 (17)	C18A—N17A—C30A—C25A	5.8 (3)
C16—N17—C30—C29	9.0 (3)	C16A—N17A—C30A—C25A	−172.03 (16)
C18—N17—C30—C25	7.6 (3)	C18A—N17A—C30A—C29A	−174.23 (17)
C16—N17—C30—C25	−170.86 (16)	C16A—N17A—C30A—C29A	7.9 (3)
C28—C29—C30—N17	−179.40 (18)	C26A—C25A—C30A—N17A	−179.81 (17)
C28—C29—C30—C25	0.4 (3)	C24A—C25A—C30A—N17A	1.7 (3)
C26—C25—C30—N17	179.63 (17)	C26A—C25A—C30A—C29A	0.2 (3)
C24—C25—C30—N17	0.3 (3)	C24A—C25A—C30A—C29A	−178.25 (17)
C26—C25—C30—C29	−0.2 (3)	C28A—C29A—C30A—N17A	−179.69 (17)
C24—C25—C30—C29	−179.56 (17)	C28A—C29A—C30A—C25A	0.3 (3)