Two benzoyl­aminoacridinedione derivatives

The title compounds, 10-benzoyl­amino-1,2,3,4,5,6,7,8,9,10-deca­hydroacridine-1,8-dione monohydrate, C₂₀H₂₀N₂O₃·H₂O, and 10-p-toluoylamino-1,2,3,4,5,6,7,8,9,10-deca­hydroacridine-1,8-dione monohydrate, C₂₁H₂₂N₂O₃·H₂O, consist of partially hydrogenated acridine moieties with one benzoyl­amino substituent on the central ring. The acridine moiety suffers considerable deviations from planarity. The central ring in the acridine moiety is a boat, while the outer rings adopt sofa conformations.

Computing details

Data collection: SMART (Siemens, 1996) for (I). Cell refinement: SAINT (Siemens, 1996) for (I). Data reduction: SAINT for (I). Program(s) used to solve structure: SHELXS97 (Sheldrick, 1997) for (I); SHELXS97 (Sheldrick, 1990) for (II). For both compounds, 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, 1995).

(I) 10-(benzoylamino)-3,4,6,7,9,10-hexahydro-1,8-(2H,5H)-acridinedione (I)

Crystal data

C20H20N2O3·H2O	F(000) = 752
Mr = 354.40	Dx = 1.279 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.4056 (2) Å	Cell parameters from 6167 reflections
b = 12.2501 (1) Å	θ = 1.8–28.3°
c = 13.1746 (3) Å	µ = 0.09 mm^−1
β = 91.497 (1)°	T = 293 K
V = 1840.12 (5) Å^3	Slab, yellow
Z = 4	0.48 × 0.40 × 0.08 mm

Data collection

Siemens SMART CCD area detector Diffractometer	3066 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 28.4°, θmin = 1.8°
Detector resolution: 8.33 pixels mm^-1	h = −15→13
ω scans	k = −15→16
12199 measured reflections	l = −15→17
4512 independent reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.167	H-atom parameters constrained
S = 1.03	Calculated w = 1/[σ^2(Fo^2) + (0.0755P)^2 + 0.5302P] where P = (Fo^2 + 2Fc^2)/3
4512 reflections	(Δ/σ)max < 0.001
243 parameters	Δρmax = 0.52 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

Experimental. Data were collected over a hemisphere of reciproal space, by a combination of three sets of exposures. Each set had a different φ angle (0, 88 and 180 °) for the crystal and each exposure of 30 s(I) and (II) covered 0.3° in ω. The crystal-to-detector distance was 4 cm (I) and (II) the detector swing angle was -35°. Coverage of the unique set is over 99% complete. The first 30 frames of data were recollected at the end of data collection to monitor crystal decay.

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	1.23695 (13)	0.72286 (15)	−0.12058 (14)	0.0765 (5)
O2	0.94941 (15)	0.44042 (15)	−0.25585 (12)	0.0753 (5)
O3	0.71019 (13)	0.83820 (13)	−0.03779 (10)	0.0628 (4)
C1	1.16121 (17)	0.75573 (17)	−0.06314 (16)	0.0530 (5)
C1A	1.05034 (15)	0.69651 (15)	−0.05398 (13)	0.0421 (4)
C2	1.1774 (2)	0.8579 (2)	−0.0029 (2)	0.0729 (7)
H2A	1.1501	0.9194	−0.0434	0.088*
H2B	1.2604	0.8684	0.0119	0.088*
C3	1.1133 (2)	0.8566 (2)	0.0950 (2)	0.0802 (8)
H3A	1.1188	0.9283	0.1258	0.096*
H3B	1.1516	0.8052	0.1410	0.096*
C4	0.98483 (18)	0.82563 (18)	0.08270 (17)	0.0589 (5)
H4A	0.9544	0.8068	0.1485	0.071*
H4B	0.9408	0.8879	0.0568	0.071*
C4A	0.96784 (15)	0.73105 (14)	0.01163 (13)	0.0418 (4)
C5	0.87640 (18)	0.47744 (17)	−0.19661 (15)	0.0539 (5)
C5A	0.90911 (15)	0.55826 (15)	−0.12073 (13)	0.0427 (4)
C6	0.7503 (2)	0.4434 (2)	−0.2046 (2)	0.0749 (7)
H6A	0.7461	0.3694	−0.2307	0.090*
H6B	0.7095	0.4905	−0.2530	0.090*
C7	0.6883 (2)	0.4478 (2)	−0.1055 (2)	0.0771 (7)
H7A	0.7173	0.3891	−0.0622	0.093*
H7B	0.6052	0.4356	−0.1183	0.093*
C8	0.70433 (18)	0.55438 (18)	−0.05035 (18)	0.0596 (5)
H8A	0.6518	0.6083	−0.0805	0.072*
H8B	0.6833	0.5449	0.0200	0.072*
C8A	0.82820 (15)	0.59571 (15)	−0.05409 (13)	0.0420 (4)
C9	1.03328 (16)	0.59835 (17)	−0.12132 (14)	0.0485 (4)
H9A	1.0535	0.6172	−0.1902	0.058*
H9B	1.0855	0.5404	−0.0982	0.058*
N10	0.85975 (12)	0.67670 (13)	0.01556 (11)	0.0455 (4)
N11	0.77321 (13)	0.71683 (13)	0.08003 (11)	0.0468 (4)
H11	0.7667	0.6907	0.1402	0.056*
C12	0.70035 (15)	0.79687 (15)	0.04634 (13)	0.0448 (4)
C13	0.60590 (14)	0.82915 (15)	0.11858 (13)	0.0421 (4)
C14	0.55390 (16)	0.93074 (17)	0.10426 (15)	0.0503 (4)
H14	0.5800	0.9770	0.0536	0.060*
C15	0.46231 (18)	0.96351 (19)	0.16583 (17)	0.0590 (5)
H15	0.4276	1.0315	0.1557	0.071*
C16	0.42296 (17)	0.8957 (2)	0.24160 (17)	0.0619 (6)
H16	0.3613	0.9176	0.2817	0.074*
C17	0.47542 (19)	0.7956 (2)	0.25751 (18)	0.0650 (6)
H17	0.4501	0.7504	0.3092	0.078*
C18	0.56660 (17)	0.76214 (17)	0.19593 (17)	0.0551 (5)
H18	0.6014	0.6943	0.2067	0.066*
O1W	0.18109 (18)	0.1329 (2)	0.22943 (13)	0.0907 (7)
HWA	0.108 (3)	0.113 (2)	0.230 (2)	0.084 (9)*
HWB	0.204 (3)	0.152 (3)	0.169 (3)	0.100 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0532 (9)	0.0927 (12)	0.0853 (12)	−0.0016 (8)	0.0344 (8)	−0.0126 (10)
O2	0.0673 (10)	0.0932 (12)	0.0659 (10)	0.0120 (8)	0.0077 (8)	−0.0333 (9)
O3	0.0659 (9)	0.0797 (10)	0.0437 (7)	0.0212 (8)	0.0186 (6)	0.0158 (7)
C1	0.0469 (10)	0.0619 (12)	0.0509 (10)	0.0031 (9)	0.0133 (8)	0.0060 (9)
C1A	0.0408 (9)	0.0508 (10)	0.0351 (8)	0.0088 (7)	0.0073 (6)	0.0032 (7)
C2	0.0644 (14)	0.0745 (15)	0.0809 (16)	−0.0154 (12)	0.0201 (12)	−0.0113 (13)
C3	0.0730 (16)	0.0899 (18)	0.0785 (16)	−0.0181 (13)	0.0203 (12)	−0.0283 (15)
C4	0.0568 (12)	0.0592 (12)	0.0615 (12)	0.0016 (9)	0.0150 (9)	−0.0142 (10)
C4A	0.0422 (9)	0.0456 (9)	0.0378 (8)	0.0075 (7)	0.0072 (7)	0.0031 (7)
C5	0.0547 (11)	0.0589 (11)	0.0479 (10)	0.0120 (9)	−0.0010 (8)	−0.0061 (9)
C5A	0.0443 (9)	0.0483 (9)	0.0355 (8)	0.0116 (7)	0.0029 (7)	0.0014 (7)
C6	0.0633 (14)	0.0833 (16)	0.0777 (16)	0.0006 (12)	−0.0061 (12)	−0.0240 (14)
C7	0.0605 (14)	0.0816 (16)	0.0895 (18)	−0.0084 (12)	0.0052 (12)	−0.0146 (14)
C8	0.0459 (11)	0.0681 (13)	0.0653 (13)	0.0023 (9)	0.0097 (9)	−0.0065 (11)
C8A	0.0418 (9)	0.0465 (9)	0.0380 (8)	0.0084 (7)	0.0037 (7)	0.0032 (7)
C9	0.0433 (9)	0.0632 (11)	0.0394 (9)	0.0117 (8)	0.0091 (7)	−0.0050 (8)
N10	0.0391 (7)	0.0565 (9)	0.0415 (7)	0.0075 (6)	0.0140 (6)	−0.0053 (7)
N11	0.0439 (8)	0.0601 (9)	0.0372 (7)	0.0128 (7)	0.0153 (6)	0.0018 (7)
C12	0.0413 (9)	0.0534 (10)	0.0402 (9)	0.0055 (8)	0.0101 (7)	0.0008 (8)
C13	0.0338 (8)	0.0518 (10)	0.0411 (8)	0.0031 (7)	0.0076 (6)	−0.0030 (8)
C14	0.0455 (10)	0.0581 (11)	0.0475 (10)	0.0080 (8)	0.0065 (8)	0.0038 (9)
C15	0.0489 (11)	0.0645 (12)	0.0639 (12)	0.0166 (9)	0.0073 (9)	−0.0068 (10)
C16	0.0426 (10)	0.0802 (15)	0.0636 (13)	0.0080 (10)	0.0194 (9)	−0.0093 (11)
C17	0.0524 (12)	0.0765 (14)	0.0675 (13)	0.0016 (10)	0.0296 (10)	0.0088 (11)
C18	0.0477 (10)	0.0547 (11)	0.0640 (12)	0.0064 (8)	0.0218 (9)	0.0082 (9)
O1W	0.0780 (12)	0.1477 (19)	0.0473 (9)	−0.0488 (13)	0.0173 (8)	−0.0219 (11)

Geometric parameters (Å, º)

O1—C1	1.231 (2)	C7—C8	1.503 (3)
O2—C5	1.242 (2)	C7—H7A	0.9700
O3—C12	1.226 (2)	C7—H7B	0.9700
C1—C1A	1.465 (3)	C8—C8A	1.503 (3)
C1—C2	1.491 (3)	C8—H8A	0.9700
C1A—C4A	1.362 (2)	C8—H8B	0.9700
C1A—C9	1.504 (3)	C8A—N10	1.392 (2)
C2—C3	1.499 (3)	C9—H9A	0.9700
C2—H2A	0.9700	C9—H9B	0.9700
C2—H2B	0.9700	N10—N11	1.4075 (18)
C3—C4	1.518 (3)	N11—C12	1.353 (2)
C3—H3A	0.9700	N11—H11	0.8600
C3—H3B	0.9700	C12—C13	1.509 (2)
C4—C4A	1.499 (3)	C13—C14	1.389 (3)
C4—H4A	0.9700	C13—C18	1.392 (3)
C4—H4B	0.9700	C14—C15	1.398 (3)
C4A—N10	1.403 (2)	C14—H14	0.9300
C5—C5A	1.449 (3)	C15—C16	1.383 (3)
C5—C6	1.499 (3)	C15—H15	0.9300
C5A—C8A	1.369 (2)	C16—C17	1.378 (3)
C5A—C9	1.499 (3)	C16—H16	0.9300
C6—C7	1.501 (4)	C17—C18	1.397 (3)
C6—H6A	0.9700	C17—H17	0.9300
C6—H6B	0.9700	C18—H18	0.9300
O1—C1—C1A	120.64 (19)	H7A—C7—H7B	107.7
O1—C1—C2	121.50 (19)	C8A—C8—C7	112.28 (17)
C1A—C1—C2	117.84 (17)	C8A—C8—H8A	109.1
C4A—C1A—C1	120.70 (17)	C7—C8—H8A	109.1
C4A—C1A—C9	122.82 (16)	C8A—C8—H8B	109.1
C1—C1A—C9	116.47 (15)	C7—C8—H8B	109.1
C1—C2—C3	113.1 (2)	H8A—C8—H8B	107.9
C1—C2—H2A	109.0	C5A—C8A—N10	119.63 (16)
C3—C2—H2A	109.0	C5A—C8A—C8	123.92 (17)
C1—C2—H2B	109.0	N10—C8A—C8	116.45 (15)
C3—C2—H2B	109.0	C5A—C9—C1A	111.50 (14)
H2A—C2—H2B	107.8	C5A—C9—H9A	109.3
C2—C3—C4	113.7 (2)	C1A—C9—H9A	109.3
C2—C3—H3A	108.8	C5A—C9—H9B	109.3
C4—C3—H3A	108.8	C1A—C9—H9B	109.3
C2—C3—H3B	108.8	H9A—C9—H9B	108.0
C4—C3—H3B	108.8	C8A—N10—C4A	121.74 (14)
H3A—C3—H3B	107.7	C8A—N10—N11	118.25 (14)
C4A—C4—C3	111.61 (17)	C4A—N10—N11	119.15 (15)
C4A—C4—H4A	109.3	C12—N11—N10	119.32 (14)
C3—C4—H4A	109.3	C12—N11—H11	120.3
C4A—C4—H4B	109.3	N10—N11—H11	120.3
C3—C4—H4B	109.3	O3—C12—N11	121.73 (16)
H4A—C4—H4B	108.0	O3—C12—C13	123.07 (16)
C1A—C4A—N10	119.89 (16)	N11—C12—C13	115.20 (15)
C1A—C4A—C4	123.81 (17)	C14—C13—C18	118.90 (16)
N10—C4A—C4	116.30 (15)	C14—C13—C12	117.28 (16)
O2—C5—C5A	121.22 (19)	C18—C13—C12	123.79 (16)
O2—C5—C6	120.83 (19)	C13—C14—C15	120.08 (19)
C5A—C5—C6	117.89 (17)	C13—C14—H14	120.0
C8A—C5A—C5	120.37 (17)	C15—C14—H14	120.0
C8A—C5A—C9	123.10 (16)	C16—C15—C14	120.54 (19)
C5—C5A—C9	116.52 (15)	C16—C15—H15	119.7
C5—C6—C7	113.70 (19)	C14—C15—H15	119.7
C5—C6—H6A	108.8	C17—C16—C15	119.77 (18)
C7—C6—H6A	108.8	C17—C16—H16	120.1
C5—C6—H6B	108.8	C15—C16—H16	120.1
C7—C6—H6B	108.8	C16—C17—C18	120.0 (2)
H6A—C6—H6B	107.7	C16—C17—H17	120.0
C6—C7—C8	113.4 (2)	C18—C17—H17	120.0
C6—C7—H7A	108.9	C13—C18—C17	120.71 (19)
C8—C7—H7A	108.9	C13—C18—H18	119.6
C6—C7—H7B	108.9	C17—C18—H18	119.6
C8—C7—H7B	108.9
O1—C1—C1A—C4A	178.15 (19)	C8A—C5A—C9—C1A	−10.1 (2)
C2—C1—C1A—C4A	−3.4 (3)	C5—C5A—C9—C1A	168.82 (15)
O1—C1—C1A—C9	−2.7 (3)	C4A—C1A—C9—C5A	10.5 (2)
C2—C1—C1A—C9	175.76 (19)	C1—C1A—C9—C5A	−168.61 (16)
O1—C1—C2—C3	−151.0 (2)	C5A—C8A—N10—C4A	8.0 (3)
C1A—C1—C2—C3	30.5 (3)	C8—C8A—N10—C4A	−172.16 (17)
C1—C2—C3—C4	−51.0 (3)	C5A—C8A—N10—N11	177.27 (15)
C2—C3—C4—C4A	43.4 (3)	C8—C8A—N10—N11	−2.9 (2)
C1—C1A—C4A—N10	176.68 (16)	C1A—C4A—N10—C8A	−7.6 (3)
C9—C1A—C4A—N10	−2.4 (3)	C4—C4A—N10—C8A	172.72 (16)
C1—C1A—C4A—C4	−3.7 (3)	C1A—C4A—N10—N11	−176.78 (15)
C9—C1A—C4A—C4	177.25 (17)	C4—C4A—N10—N11	3.5 (2)
C3—C4—C4A—C1A	−16.5 (3)	C8A—N10—N11—C12	−84.2 (2)
C3—C4—C4A—N10	163.2 (2)	C4A—N10—N11—C12	85.3 (2)
O2—C5—C5A—C8A	−178.04 (19)	N10—N11—C12—O3	−2.6 (3)
C6—C5—C5A—C8A	4.6 (3)	N10—N11—C12—C13	176.27 (15)
O2—C5—C5A—C9	3.0 (3)	O3—C12—C13—C14	−21.3 (3)
C6—C5—C5A—C9	−174.36 (19)	N11—C12—C13—C14	159.89 (17)
O2—C5—C6—C7	151.7 (2)	O3—C12—C13—C18	156.9 (2)
C5A—C5—C6—C7	−31.0 (3)	N11—C12—C13—C18	−21.9 (3)
C5—C6—C7—C8	50.0 (3)	C18—C13—C14—C15	−1.1 (3)
C6—C7—C8—C8A	−42.0 (3)	C12—C13—C14—C15	177.21 (18)
C5—C5A—C8A—N10	−177.31 (16)	C13—C14—C15—C16	0.3 (3)
C9—C5A—C8A—N10	1.6 (3)	C14—C15—C16—C17	0.9 (3)
C5—C5A—C8A—C8	2.9 (3)	C15—C16—C17—C18	−1.2 (4)
C9—C5A—C8A—C8	−178.24 (18)	C14—C13—C18—C17	0.8 (3)
C7—C8—C8A—C5A	16.2 (3)	C12—C13—C18—C17	−177.4 (2)
C7—C8—C8A—N10	−163.60 (19)	C16—C17—C18—C13	0.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O1W^i	0.86	1.94	2.750 (2)	157
C16—H16···O1^ii	0.93	2.59	3.180 (3)	122
C17—H17···O1^ii	0.93	2.64	3.203 (3)	119
C18—H18···O1W^i	0.93	2.71	3.407 (3)	133
O1W—HWA···O2^iii	0.87	1.937	2.802 (3)	173.9
O1W—HWB···O3^iv	0.88	2.012	2.864 (2)	163.7

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x−1, −y+3/2, z+1/2; (iii) x−1, −y+1/2, z+1/2; (iv) −x+1, −y+1, −z.

(II) 10-(4-methylbenzoylamino)-3,4,6,7,9,10-hexahydro-1,8-(2H,5H)-acridinedione(II)

Crystal data

C21H22N2O3·H2O	F(000) = 1568
Mr = 368.42	Dx = 1.258 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 23.2343 (10) Å	Cell parameters from 6666 reflections
b = 13.8327 (6) Å	θ = 1.9–28.3°
c = 16.3286 (7) Å	µ = 0.09 mm^−1
β = 132.140 (1)°	T = 293 K
V = 3891.4 (3) Å^3	Block, yellow
Z = 8	0.48 × 0.44 × 0.36 mm

Data collection

Siemens SMART CCD area detector Diffractometer	2634 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 25.0°, θmin = 1.9°
Detector resolution: 8.33 pixels mm^-1	h = −27→20
ω scans	k = −14→16
10281 measured reflections	l = −19→19
3424 independent reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.190	Constrained(execpt water molecule)
S = 0.95	Calculated w = 1/[σ^2(Fo^2) + (0.1225P)^2 + 2.3517P] where P = (Fo^2 + 2Fc^2)/3
3424 reflections	(Δ/σ)max = 0.003
253 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

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
O1	0.19154 (13)	0.35055 (13)	0.14221 (17)	0.0917 (6)
O2	0.14732 (16)	0.41574 (14)	0.39752 (19)	0.1088 (8)
O3	0.01368 (10)	0.01930 (11)	0.11193 (14)	0.0711 (5)
O1W	0.27048 (12)	−0.07556 (15)	0.47128 (16)	0.0761 (5)
HWA	0.3006 (18)	−0.025 (2)	0.509 (3)	0.085 (9)*
HWB	0.294 (2)	−0.098 (2)	0.446 (3)	0.114 (12)*
C1	0.19224 (15)	0.26294 (18)	0.1572 (2)	0.0676 (6)
C1A	0.17132 (13)	0.22895 (14)	0.21847 (17)	0.0558 (5)
C2	0.2088 (2)	0.1891 (2)	0.1077 (3)	0.0911 (9)
H2A	0.1614	0.1763	0.0322	0.109*
H2B	0.2464	0.2156	0.1055	0.109*
C3	0.2390 (2)	0.0973 (2)	0.1697 (3)	0.0950 (9)
H3A	0.2910	0.1077	0.2403	0.114*
H3B	0.2423	0.0502	0.1290	0.114*
C4	0.18877 (16)	0.05684 (17)	0.1894 (2)	0.0677 (6)
H4A	0.1416	0.0303	0.1210	0.081*
H4B	0.2162	0.0048	0.2429	0.081*
C4A	0.16805 (12)	0.13331 (14)	0.23127 (16)	0.0527 (5)
C5	0.13821 (16)	0.32860 (19)	0.4007 (2)	0.0752 (7)
C5A	0.14027 (12)	0.26131 (16)	0.33461 (17)	0.0573 (5)
C6	0.1286 (3)	0.2902 (3)	0.4756 (3)	0.1134 (12)
H6A	0.1781	0.2955	0.5508	0.136*
H6B	0.0921	0.3313	0.4695	0.136*
C7	0.1032 (3)	0.1953 (3)	0.4580 (4)	0.153 (2)
H7A	0.0471	0.1974	0.4081	0.183*
H7B	0.1220	0.1710	0.5280	0.183*
C8	0.12297 (17)	0.12158 (19)	0.4140 (2)	0.0735 (7)
H8A	0.0813	0.0746	0.3709	0.088*
H8B	0.1697	0.0877	0.4752	0.088*
C8A	0.13548 (11)	0.16539 (15)	0.34328 (16)	0.0522 (5)
C9	0.14962 (18)	0.30370 (16)	0.2601 (2)	0.0739 (7)
H9A	0.1895	0.3532	0.2999	0.089*
H9B	0.1014	0.3343	0.1978	0.089*
N10	0.14564 (11)	0.10201 (11)	0.28778 (15)	0.0575 (5)
N11	0.13047 (11)	0.00379 (11)	0.28438 (15)	0.0568 (5)
H11	0.1626	−0.0326	0.3410	0.068*
C12	0.06327 (12)	−0.03293 (14)	0.18885 (16)	0.0510 (5)
C13	0.05681 (11)	−0.13969 (14)	0.18533 (15)	0.0481 (5)
C14	0.01321 (13)	−0.18396 (16)	0.08280 (18)	0.0620 (6)
H14	−0.0110	−0.1465	0.0199	0.074*
C15	0.00567 (15)	−0.28268 (17)	0.0739 (2)	0.0698 (6)
H15	−0.0231	−0.3112	0.0047	0.084*
C16	0.03971 (14)	−0.34104 (16)	0.1652 (2)	0.0673 (6)
C17	0.08318 (16)	−0.29647 (17)	0.2667 (2)	0.0740 (7)
H17	0.1069	−0.3340	0.3294	0.089*
C18	0.09226 (14)	−0.19757 (16)	0.27738 (18)	0.0639 (6)
H18	0.1224	−0.1694	0.3470	0.077*
C19	0.0291 (2)	−0.44942 (19)	0.1527 (3)	0.1095 (12)
H19A	0.0484	−0.4740	0.1199	0.164*
H19B	−0.0250	−0.4647	0.1062	0.164*
H19C	0.0573	−0.4784	0.2240	0.164*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.1211 (16)	0.0650 (11)	0.0996 (14)	−0.0179 (10)	0.0784 (13)	0.0095 (10)
O2	0.156 (2)	0.0601 (12)	0.1017 (15)	0.0000 (12)	0.0827 (16)	−0.0231 (10)
O3	0.0722 (10)	0.0569 (9)	0.0708 (10)	0.0182 (8)	0.0425 (9)	0.0156 (8)
O1W	0.0780 (11)	0.0680 (11)	0.0724 (11)	0.0048 (9)	0.0464 (10)	−0.0097 (9)
C1	0.0706 (14)	0.0634 (14)	0.0644 (14)	−0.0104 (11)	0.0434 (12)	0.0054 (11)
C1A	0.0644 (12)	0.0465 (11)	0.0515 (11)	−0.0038 (9)	0.0368 (10)	0.0009 (8)
C2	0.118 (2)	0.089 (2)	0.114 (2)	−0.0013 (17)	0.097 (2)	0.0096 (17)
C3	0.123 (2)	0.086 (2)	0.129 (3)	0.0077 (17)	0.106 (2)	0.0054 (18)
C4	0.0876 (16)	0.0526 (13)	0.0862 (16)	0.0046 (11)	0.0679 (15)	0.0018 (11)
C4A	0.0583 (11)	0.0478 (11)	0.0529 (11)	−0.0002 (9)	0.0377 (10)	0.0010 (8)
C5	0.0818 (16)	0.0657 (16)	0.0636 (14)	0.0055 (12)	0.0428 (13)	−0.0125 (11)
C5A	0.0573 (12)	0.0529 (12)	0.0492 (11)	−0.0014 (9)	0.0306 (10)	−0.0081 (9)
C6	0.163 (4)	0.104 (3)	0.115 (3)	0.021 (2)	0.110 (3)	−0.005 (2)
C7	0.257 (6)	0.129 (3)	0.206 (5)	−0.084 (3)	0.210 (5)	−0.082 (3)
C8	0.0814 (16)	0.0799 (17)	0.0794 (16)	−0.0027 (13)	0.0622 (14)	−0.0007 (13)
C8A	0.0501 (11)	0.0533 (12)	0.0489 (11)	−0.0005 (9)	0.0314 (9)	−0.0033 (8)
C9	0.109 (2)	0.0422 (11)	0.0741 (15)	−0.0055 (12)	0.0629 (15)	−0.0046 (10)
N10	0.0808 (12)	0.0381 (9)	0.0689 (11)	−0.0011 (8)	0.0564 (10)	0.0005 (8)
N11	0.0708 (11)	0.0383 (9)	0.0604 (10)	0.0004 (7)	0.0437 (10)	0.0058 (7)
C12	0.0597 (12)	0.0465 (11)	0.0575 (12)	0.0079 (9)	0.0437 (11)	0.0071 (9)
C13	0.0487 (10)	0.0468 (11)	0.0525 (11)	0.0026 (8)	0.0356 (9)	0.0043 (8)
C14	0.0615 (12)	0.0590 (13)	0.0505 (11)	0.0041 (10)	0.0314 (10)	0.0065 (9)
C15	0.0710 (15)	0.0594 (14)	0.0594 (13)	−0.0045 (11)	0.0357 (12)	−0.0071 (10)
C16	0.0658 (13)	0.0497 (12)	0.0764 (15)	−0.0026 (10)	0.0436 (12)	0.0009 (11)
C17	0.0856 (17)	0.0538 (13)	0.0682 (15)	−0.0027 (11)	0.0457 (14)	0.0146 (11)
C18	0.0748 (14)	0.0577 (13)	0.0523 (12)	−0.0067 (10)	0.0398 (12)	0.0034 (9)
C19	0.127 (3)	0.0533 (16)	0.121 (3)	−0.0095 (16)	0.072 (2)	−0.0022 (16)

Geometric parameters (Å, º)

O1—C1	1.234 (3)	C7—H7B	0.9700
O2—C5	1.231 (3)	C8—C8A	1.495 (3)
O3—C12	1.219 (2)	C8—H8A	0.9700
C1—C1A	1.453 (3)	C8—H8B	0.9700
C1—C2	1.504 (4)	C8A—N10	1.390 (3)
C1A—C4A	1.350 (3)	C9—H9A	0.9700
C1A—C9	1.499 (3)	C9—H9B	0.9700
C2—C3	1.476 (4)	N10—N11	1.395 (2)
C2—H2A	0.9700	N11—C12	1.364 (3)
C2—H2B	0.9700	N11—H11	0.8600
C3—C4	1.511 (4)	C12—C13	1.482 (3)
C3—H3A	0.9700	C13—C18	1.385 (3)
C3—H3B	0.9700	C13—C14	1.389 (3)
C4—C4A	1.503 (3)	C14—C15	1.372 (3)
C4—H4A	0.9700	C14—H14	0.9300
C4—H4B	0.9700	C15—C16	1.384 (3)
C4A—N10	1.398 (3)	C15—H15	0.9300
C5—C5A	1.450 (3)	C16—C17	1.379 (3)
C5—C6	1.480 (5)	C16—C19	1.511 (3)
C5A—C8A	1.347 (3)	C17—C18	1.377 (3)
C5A—C9	1.491 (3)	C17—H17	0.9300
C6—C7	1.389 (5)	C18—H18	0.9300
C6—H6A	0.9700	C19—H19A	0.9600
C6—H6B	0.9700	C19—H19B	0.9600
C7—C8	1.487 (4)	C19—H19C	0.9600
C7—H7A	0.9700
O1—C1—C1A	119.2 (2)	C8A—C8—H8A	109.2
O1—C1—C2	122.3 (2)	C7—C8—H8B	109.2
C1A—C1—C2	118.4 (2)	C8A—C8—H8B	109.2
C4A—C1A—C1	120.2 (2)	H8A—C8—H8B	107.9
C4A—C1A—C9	122.3 (2)	C5A—C8A—N10	119.38 (19)
C1—C1A—C9	117.34 (19)	C5A—C8A—C8	123.6 (2)
C3—C2—C1	113.0 (2)	N10—C8A—C8	116.99 (19)
C3—C2—H2A	109.0	C5A—C9—C1A	112.11 (18)
C1—C2—H2A	109.0	C5A—C9—H9A	109.2
C3—C2—H2B	109.0	C1A—C9—H9A	109.2
C1—C2—H2B	109.0	C5A—C9—H9B	109.2
H2A—C2—H2B	107.8	C1A—C9—H9B	109.2
C2—C3—C4	112.7 (3)	H9A—C9—H9B	107.9
C2—C3—H3A	109.1	C8A—N10—N11	119.41 (17)
C4—C3—H3A	109.1	C8A—N10—C4A	122.43 (16)
C2—C3—H3B	109.1	N11—N10—C4A	118.12 (16)
C4—C3—H3B	109.1	C12—N11—N10	118.22 (17)
H3A—C3—H3B	107.8	C12—N11—H11	120.9
C4A—C4—C3	111.4 (2)	N10—N11—H11	120.9
C4A—C4—H4A	109.3	O3—C12—N11	121.54 (19)
C3—C4—H4A	109.3	O3—C12—C13	123.35 (19)
C4A—C4—H4B	109.3	N11—C12—C13	115.09 (16)
C3—C4—H4B	109.3	C18—C13—C14	118.37 (19)
H4A—C4—H4B	108.0	C18—C13—C12	124.28 (18)
C1A—C4A—N10	119.36 (19)	C14—C13—C12	117.34 (17)
C1A—C4A—C4	123.5 (2)	C15—C14—C13	120.3 (2)
N10—C4A—C4	117.18 (17)	C15—C14—H14	119.9
O2—C5—C5A	120.3 (3)	C13—C14—H14	119.9
O2—C5—C6	120.8 (2)	C14—C15—C16	121.8 (2)
C5A—C5—C6	118.9 (3)	C14—C15—H15	119.1
C8A—C5A—C5	120.5 (2)	C16—C15—H15	119.1
C8A—C5A—C9	122.71 (19)	C17—C16—C15	117.5 (2)
C5—C5A—C9	116.8 (2)	C17—C16—C19	121.9 (2)
C7—C6—C5	116.6 (3)	C15—C16—C19	120.6 (2)
C7—C6—H6A	108.1	C18—C17—C16	121.5 (2)
C5—C6—H6A	108.1	C18—C17—H17	119.3
C7—C6—H6B	108.1	C16—C17—H17	119.3
C5—C6—H6B	108.1	C17—C18—C13	120.5 (2)
H6A—C6—H6B	107.3	C17—C18—H18	119.7
C6—C7—C8	121.5 (3)	C13—C18—H18	119.7
C6—C7—H7A	107.0	C16—C19—H19A	109.5
C8—C7—H7A	107.0	C16—C19—H19B	109.5
C6—C7—H7B	107.0	H19A—C19—H19B	109.5
C8—C7—H7B	107.0	C16—C19—H19C	109.5
H7A—C7—H7B	106.7	H19A—C19—H19C	109.5
C7—C8—C8A	112.2 (2)	H19B—C19—H19C	109.5
C7—C8—H8A	109.2
O1—C1—C1A—C4A	176.8 (2)	C5—C5A—C9—C1A	165.3 (2)
C2—C1—C1A—C4A	0.9 (3)	C4A—C1A—C9—C5A	11.4 (3)
O1—C1—C1A—C9	0.1 (3)	C1—C1A—C9—C5A	−172.0 (2)
C2—C1—C1A—C9	−175.8 (2)	C5A—C8A—N10—N11	−171.42 (19)
O1—C1—C2—C3	155.7 (3)	C8—C8A—N10—N11	11.1 (3)
C1A—C1—C2—C3	−28.5 (4)	C5A—C8A—N10—C4A	6.2 (3)
C1—C2—C3—C4	51.7 (4)	C8—C8A—N10—C4A	−171.2 (2)
C2—C3—C4—C4A	−47.1 (4)	C1A—C4A—N10—C8A	−8.0 (3)
C1—C1A—C4A—N10	−178.2 (2)	C4—C4A—N10—C8A	171.0 (2)
C9—C1A—C4A—N10	−1.7 (3)	C1A—C4A—N10—N11	169.70 (19)
C1—C1A—C4A—C4	2.9 (3)	C4—C4A—N10—N11	−11.4 (3)
C9—C1A—C4A—C4	179.4 (2)	C8A—N10—N11—C12	103.8 (2)
C3—C4—C4A—C1A	20.2 (3)	C4A—N10—N11—C12	−74.0 (2)
C3—C4—C4A—N10	−158.7 (2)	N10—N11—C12—O3	−7.5 (3)
O2—C5—C5A—C8A	175.6 (2)	N10—N11—C12—C13	170.87 (17)
C6—C5—C5A—C8A	−1.6 (4)	O3—C12—C13—C18	−152.9 (2)
O2—C5—C5A—C9	−3.1 (4)	N11—C12—C13—C18	28.8 (3)
C6—C5—C5A—C9	179.7 (3)	O3—C12—C13—C14	28.2 (3)
O2—C5—C6—C7	167.4 (4)	N11—C12—C13—C14	−150.11 (19)
C5A—C5—C6—C7	−15.4 (5)	C18—C13—C14—C15	0.2 (3)
C5—C6—C7—C8	31.1 (7)	C12—C13—C14—C15	179.2 (2)
C6—C7—C8—C8A	−27.9 (6)	C13—C14—C15—C16	1.0 (4)
C5—C5A—C8A—N10	−173.4 (2)	C14—C15—C16—C17	−1.2 (4)
C9—C5A—C8A—N10	5.2 (3)	C14—C15—C16—C19	178.8 (3)
C5—C5A—C8A—C8	3.9 (3)	C15—C16—C17—C18	0.3 (4)
C9—C5A—C8A—C8	−177.5 (2)	C19—C16—C17—C18	−179.7 (3)
C7—C8—C8A—C5A	9.7 (4)	C16—C17—C18—C13	0.8 (4)
C7—C8—C8A—N10	−173.0 (3)	C14—C13—C18—C17	−1.1 (3)
C8A—C5A—C9—C1A	−13.3 (3)	C12—C13—C18—C17	180.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O1W	0.86	2.00	2.789 (2)	152
C8—H8A···O3^i	0.97	2.52	3.234 (1)	130
O1W—HWB···O1^ii	0.93	1.828	2.730 (5)	162.0
O1W—HWA···O2^iii	0.88	1.897	2.763 (3)	166.2

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