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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270199016455/ka1336sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270199016455/ka1336Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270199016455/ka1336IIsup3.hkl
Contains datablock II

CCDC references: 150776; 150777

Computing details top

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) top
Crystal data top
C20H20N2O3·H2OF(000) = 752
Mr = 354.40Dx = 1.279 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.4056 (2) ÅCell parameters from 6167 reflections
b = 12.2501 (1) Åθ = 1.8–28.3°
c = 13.1746 (3) ŵ = 0.09 mm1
β = 91.497 (1)°T = 293 K
V = 1840.12 (5) Å3Slab, yellow
Z = 40.48 × 0.40 × 0.08 mm
Data collection top
Siemens SMART CCD area detector Diffractometer3066 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 28.4°, θmin = 1.8°
Detector resolution: 8.33 pixels mm-1h = 1513
ω scansk = 1516
12199 measured reflectionsl = 1517
4512 independent reflections
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) = 0.167H-atom parameters constrained
S = 1.03Calculated w = 1/[σ2(Fo2) + (0.0755P)2 + 0.5302P]
where P = (Fo2 + 2Fc2)/3
4512 reflections(Δ/σ)max < 0.001
243 parametersΔρmax = 0.52 e Å3
0 restraintsΔρmin = 0.30 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
O11.23695 (13)0.72286 (15)0.12058 (14)0.0765 (5)
O20.94941 (15)0.44042 (15)0.25585 (12)0.0753 (5)
O30.71019 (13)0.83820 (13)0.03779 (10)0.0628 (4)
C11.16121 (17)0.75573 (17)0.06314 (16)0.0530 (5)
C1A1.05034 (15)0.69651 (15)0.05398 (13)0.0421 (4)
C21.1774 (2)0.8579 (2)0.0029 (2)0.0729 (7)
H2A1.15010.91940.04340.088*
H2B1.26040.86840.01190.088*
C31.1133 (2)0.8566 (2)0.0950 (2)0.0802 (8)
H3A1.11880.92830.12580.096*
H3B1.15160.80520.14100.096*
C40.98483 (18)0.82563 (18)0.08270 (17)0.0589 (5)
H4A0.95440.80680.14850.071*
H4B0.94080.88790.05680.071*
C4A0.96784 (15)0.73105 (14)0.01163 (13)0.0418 (4)
C50.87640 (18)0.47744 (17)0.19661 (15)0.0539 (5)
C5A0.90911 (15)0.55826 (15)0.12073 (13)0.0427 (4)
C60.7503 (2)0.4434 (2)0.2046 (2)0.0749 (7)
H6A0.74610.36940.23070.090*
H6B0.70950.49050.25300.090*
C70.6883 (2)0.4478 (2)0.1055 (2)0.0771 (7)
H7A0.71730.38910.06220.093*
H7B0.60520.43560.11830.093*
C80.70433 (18)0.55438 (18)0.05035 (18)0.0596 (5)
H8A0.65180.60830.08050.072*
H8B0.68330.54490.02000.072*
C8A0.82820 (15)0.59571 (15)0.05409 (13)0.0420 (4)
C91.03328 (16)0.59835 (17)0.12132 (14)0.0485 (4)
H9A1.05350.61720.19020.058*
H9B1.08550.54040.09820.058*
N100.85975 (12)0.67670 (13)0.01556 (11)0.0455 (4)
N110.77321 (13)0.71683 (13)0.08003 (11)0.0468 (4)
H110.76670.69070.14020.056*
C120.70035 (15)0.79687 (15)0.04634 (13)0.0448 (4)
C130.60590 (14)0.82915 (15)0.11858 (13)0.0421 (4)
C140.55390 (16)0.93074 (17)0.10426 (15)0.0503 (4)
H140.58000.97700.05360.060*
C150.46231 (18)0.96351 (19)0.16583 (17)0.0590 (5)
H150.42761.03150.15570.071*
C160.42296 (17)0.8957 (2)0.24160 (17)0.0619 (6)
H160.36130.91760.28170.074*
C170.47542 (19)0.7956 (2)0.25751 (18)0.0650 (6)
H170.45010.75040.30920.078*
C180.56660 (17)0.76214 (17)0.19593 (17)0.0551 (5)
H180.60140.69430.20670.066*
O1W0.18109 (18)0.1329 (2)0.22943 (13)0.0907 (7)
HWA0.108 (3)0.113 (2)0.230 (2)0.084 (9)*
HWB0.204 (3)0.152 (3)0.169 (3)0.100 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0532 (9)0.0927 (12)0.0853 (12)0.0016 (8)0.0344 (8)0.0126 (10)
O20.0673 (10)0.0932 (12)0.0659 (10)0.0120 (8)0.0077 (8)0.0333 (9)
O30.0659 (9)0.0797 (10)0.0437 (7)0.0212 (8)0.0186 (6)0.0158 (7)
C10.0469 (10)0.0619 (12)0.0509 (10)0.0031 (9)0.0133 (8)0.0060 (9)
C1A0.0408 (9)0.0508 (10)0.0351 (8)0.0088 (7)0.0073 (6)0.0032 (7)
C20.0644 (14)0.0745 (15)0.0809 (16)0.0154 (12)0.0201 (12)0.0113 (13)
C30.0730 (16)0.0899 (18)0.0785 (16)0.0181 (13)0.0203 (12)0.0283 (15)
C40.0568 (12)0.0592 (12)0.0615 (12)0.0016 (9)0.0150 (9)0.0142 (10)
C4A0.0422 (9)0.0456 (9)0.0378 (8)0.0075 (7)0.0072 (7)0.0031 (7)
C50.0547 (11)0.0589 (11)0.0479 (10)0.0120 (9)0.0010 (8)0.0061 (9)
C5A0.0443 (9)0.0483 (9)0.0355 (8)0.0116 (7)0.0029 (7)0.0014 (7)
C60.0633 (14)0.0833 (16)0.0777 (16)0.0006 (12)0.0061 (12)0.0240 (14)
C70.0605 (14)0.0816 (16)0.0895 (18)0.0084 (12)0.0052 (12)0.0146 (14)
C80.0459 (11)0.0681 (13)0.0653 (13)0.0023 (9)0.0097 (9)0.0065 (11)
C8A0.0418 (9)0.0465 (9)0.0380 (8)0.0084 (7)0.0037 (7)0.0032 (7)
C90.0433 (9)0.0632 (11)0.0394 (9)0.0117 (8)0.0091 (7)0.0050 (8)
N100.0391 (7)0.0565 (9)0.0415 (7)0.0075 (6)0.0140 (6)0.0053 (7)
N110.0439 (8)0.0601 (9)0.0372 (7)0.0128 (7)0.0153 (6)0.0018 (7)
C120.0413 (9)0.0534 (10)0.0402 (9)0.0055 (8)0.0101 (7)0.0008 (8)
C130.0338 (8)0.0518 (10)0.0411 (8)0.0031 (7)0.0076 (6)0.0030 (8)
C140.0455 (10)0.0581 (11)0.0475 (10)0.0080 (8)0.0065 (8)0.0038 (9)
C150.0489 (11)0.0645 (12)0.0639 (12)0.0166 (9)0.0073 (9)0.0068 (10)
C160.0426 (10)0.0802 (15)0.0636 (13)0.0080 (10)0.0194 (9)0.0093 (11)
C170.0524 (12)0.0765 (14)0.0675 (13)0.0016 (10)0.0296 (10)0.0088 (11)
C180.0477 (10)0.0547 (11)0.0640 (12)0.0064 (8)0.0218 (9)0.0082 (9)
O1W0.0780 (12)0.1477 (19)0.0473 (9)0.0488 (13)0.0173 (8)0.0219 (11)
Geometric parameters (Å, º) top
O1—C11.231 (2)C7—C81.503 (3)
O2—C51.242 (2)C7—H7A0.9700
O3—C121.226 (2)C7—H7B0.9700
C1—C1A1.465 (3)C8—C8A1.503 (3)
C1—C21.491 (3)C8—H8A0.9700
C1A—C4A1.362 (2)C8—H8B0.9700
C1A—C91.504 (3)C8A—N101.392 (2)
C2—C31.499 (3)C9—H9A0.9700
C2—H2A0.9700C9—H9B0.9700
C2—H2B0.9700N10—N111.4075 (18)
C3—C41.518 (3)N11—C121.353 (2)
C3—H3A0.9700N11—H110.8600
C3—H3B0.9700C12—C131.509 (2)
C4—C4A1.499 (3)C13—C141.389 (3)
C4—H4A0.9700C13—C181.392 (3)
C4—H4B0.9700C14—C151.398 (3)
C4A—N101.403 (2)C14—H140.9300
C5—C5A1.449 (3)C15—C161.383 (3)
C5—C61.499 (3)C15—H150.9300
C5A—C8A1.369 (2)C16—C171.378 (3)
C5A—C91.499 (3)C16—H160.9300
C6—C71.501 (4)C17—C181.397 (3)
C6—H6A0.9700C17—H170.9300
C6—H6B0.9700C18—H180.9300
O1—C1—C1A120.64 (19)H7A—C7—H7B107.7
O1—C1—C2121.50 (19)C8A—C8—C7112.28 (17)
C1A—C1—C2117.84 (17)C8A—C8—H8A109.1
C4A—C1A—C1120.70 (17)C7—C8—H8A109.1
C4A—C1A—C9122.82 (16)C8A—C8—H8B109.1
C1—C1A—C9116.47 (15)C7—C8—H8B109.1
C1—C2—C3113.1 (2)H8A—C8—H8B107.9
C1—C2—H2A109.0C5A—C8A—N10119.63 (16)
C3—C2—H2A109.0C5A—C8A—C8123.92 (17)
C1—C2—H2B109.0N10—C8A—C8116.45 (15)
C3—C2—H2B109.0C5A—C9—C1A111.50 (14)
H2A—C2—H2B107.8C5A—C9—H9A109.3
C2—C3—C4113.7 (2)C1A—C9—H9A109.3
C2—C3—H3A108.8C5A—C9—H9B109.3
C4—C3—H3A108.8C1A—C9—H9B109.3
C2—C3—H3B108.8H9A—C9—H9B108.0
C4—C3—H3B108.8C8A—N10—C4A121.74 (14)
H3A—C3—H3B107.7C8A—N10—N11118.25 (14)
C4A—C4—C3111.61 (17)C4A—N10—N11119.15 (15)
C4A—C4—H4A109.3C12—N11—N10119.32 (14)
C3—C4—H4A109.3C12—N11—H11120.3
C4A—C4—H4B109.3N10—N11—H11120.3
C3—C4—H4B109.3O3—C12—N11121.73 (16)
H4A—C4—H4B108.0O3—C12—C13123.07 (16)
C1A—C4A—N10119.89 (16)N11—C12—C13115.20 (15)
C1A—C4A—C4123.81 (17)C14—C13—C18118.90 (16)
N10—C4A—C4116.30 (15)C14—C13—C12117.28 (16)
O2—C5—C5A121.22 (19)C18—C13—C12123.79 (16)
O2—C5—C6120.83 (19)C13—C14—C15120.08 (19)
C5A—C5—C6117.89 (17)C13—C14—H14120.0
C8A—C5A—C5120.37 (17)C15—C14—H14120.0
C8A—C5A—C9123.10 (16)C16—C15—C14120.54 (19)
C5—C5A—C9116.52 (15)C16—C15—H15119.7
C5—C6—C7113.70 (19)C14—C15—H15119.7
C5—C6—H6A108.8C17—C16—C15119.77 (18)
C7—C6—H6A108.8C17—C16—H16120.1
C5—C6—H6B108.8C15—C16—H16120.1
C7—C6—H6B108.8C16—C17—C18120.0 (2)
H6A—C6—H6B107.7C16—C17—H17120.0
C6—C7—C8113.4 (2)C18—C17—H17120.0
C6—C7—H7A108.9C13—C18—C17120.71 (19)
C8—C7—H7A108.9C13—C18—H18119.6
C6—C7—H7B108.9C17—C18—H18119.6
C8—C7—H7B108.9
O1—C1—C1A—C4A178.15 (19)C8A—C5A—C9—C1A10.1 (2)
C2—C1—C1A—C4A3.4 (3)C5—C5A—C9—C1A168.82 (15)
O1—C1—C1A—C92.7 (3)C4A—C1A—C9—C5A10.5 (2)
C2—C1—C1A—C9175.76 (19)C1—C1A—C9—C5A168.61 (16)
O1—C1—C2—C3151.0 (2)C5A—C8A—N10—C4A8.0 (3)
C1A—C1—C2—C330.5 (3)C8—C8A—N10—C4A172.16 (17)
C1—C2—C3—C451.0 (3)C5A—C8A—N10—N11177.27 (15)
C2—C3—C4—C4A43.4 (3)C8—C8A—N10—N112.9 (2)
C1—C1A—C4A—N10176.68 (16)C1A—C4A—N10—C8A7.6 (3)
C9—C1A—C4A—N102.4 (3)C4—C4A—N10—C8A172.72 (16)
C1—C1A—C4A—C43.7 (3)C1A—C4A—N10—N11176.78 (15)
C9—C1A—C4A—C4177.25 (17)C4—C4A—N10—N113.5 (2)
C3—C4—C4A—C1A16.5 (3)C8A—N10—N11—C1284.2 (2)
C3—C4—C4A—N10163.2 (2)C4A—N10—N11—C1285.3 (2)
O2—C5—C5A—C8A178.04 (19)N10—N11—C12—O32.6 (3)
C6—C5—C5A—C8A4.6 (3)N10—N11—C12—C13176.27 (15)
O2—C5—C5A—C93.0 (3)O3—C12—C13—C1421.3 (3)
C6—C5—C5A—C9174.36 (19)N11—C12—C13—C14159.89 (17)
O2—C5—C6—C7151.7 (2)O3—C12—C13—C18156.9 (2)
C5A—C5—C6—C731.0 (3)N11—C12—C13—C1821.9 (3)
C5—C6—C7—C850.0 (3)C18—C13—C14—C151.1 (3)
C6—C7—C8—C8A42.0 (3)C12—C13—C14—C15177.21 (18)
C5—C5A—C8A—N10177.31 (16)C13—C14—C15—C160.3 (3)
C9—C5A—C8A—N101.6 (3)C14—C15—C16—C170.9 (3)
C5—C5A—C8A—C82.9 (3)C15—C16—C17—C181.2 (4)
C9—C5A—C8A—C8178.24 (18)C14—C13—C18—C170.8 (3)
C7—C8—C8A—C5A16.2 (3)C12—C13—C18—C17177.4 (2)
C7—C8—C8A—N10163.60 (19)C16—C17—C18—C130.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O1Wi0.861.942.750 (2)157
C16—H16···O1ii0.932.593.180 (3)122
C17—H17···O1ii0.932.643.203 (3)119
C18—H18···O1Wi0.932.713.407 (3)133
O1W—HWA···O2iii0.871.9372.802 (3)173.9
O1W—HWB···O3iv0.882.0122.864 (2)163.7
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x1, y+3/2, z+1/2; (iii) x1, 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) top
Crystal data top
C21H22N2O3·H2OF(000) = 1568
Mr = 368.42Dx = 1.258 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 23.2343 (10) ÅCell parameters from 6666 reflections
b = 13.8327 (6) Åθ = 1.9–28.3°
c = 16.3286 (7) ŵ = 0.09 mm1
β = 132.140 (1)°T = 293 K
V = 3891.4 (3) Å3Block, yellow
Z = 80.48 × 0.44 × 0.36 mm
Data collection top
Siemens SMART CCD area detector Diffractometer2634 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
Graphite monochromatorθmax = 25.0°, θmin = 1.9°
Detector resolution: 8.33 pixels mm-1h = 2720
ω scansk = 1416
10281 measured reflectionsl = 1919
3424 independent reflections
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190Constrained(execpt water molecule)
S = 0.95Calculated w = 1/[σ2(Fo2) + (0.1225P)2 + 2.3517P]
where P = (Fo2 + 2Fc2)/3
3424 reflections(Δ/σ)max = 0.003
253 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.32 e Å3
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
O10.19154 (13)0.35055 (13)0.14221 (17)0.0917 (6)
O20.14732 (16)0.41574 (14)0.39752 (19)0.1088 (8)
O30.01368 (10)0.01930 (11)0.11193 (14)0.0711 (5)
O1W0.27048 (12)0.07556 (15)0.47128 (16)0.0761 (5)
HWA0.3006 (18)0.025 (2)0.509 (3)0.085 (9)*
HWB0.294 (2)0.098 (2)0.446 (3)0.114 (12)*
C10.19224 (15)0.26294 (18)0.1572 (2)0.0676 (6)
C1A0.17132 (13)0.22895 (14)0.21847 (17)0.0558 (5)
C20.2088 (2)0.1891 (2)0.1077 (3)0.0911 (9)
H2A0.16140.17630.03220.109*
H2B0.24640.21560.10550.109*
C30.2390 (2)0.0973 (2)0.1697 (3)0.0950 (9)
H3A0.29100.10770.24030.114*
H3B0.24230.05020.12900.114*
C40.18877 (16)0.05684 (17)0.1894 (2)0.0677 (6)
H4A0.14160.03030.12100.081*
H4B0.21620.00480.24290.081*
C4A0.16805 (12)0.13331 (14)0.23127 (16)0.0527 (5)
C50.13821 (16)0.32860 (19)0.4007 (2)0.0752 (7)
C5A0.14027 (12)0.26131 (16)0.33461 (17)0.0573 (5)
C60.1286 (3)0.2902 (3)0.4756 (3)0.1134 (12)
H6A0.17810.29550.55080.136*
H6B0.09210.33130.46950.136*
C70.1032 (3)0.1953 (3)0.4580 (4)0.153 (2)
H7A0.04710.19740.40810.183*
H7B0.12200.17100.52800.183*
C80.12297 (17)0.12158 (19)0.4140 (2)0.0735 (7)
H8A0.08130.07460.37090.088*
H8B0.16970.08770.47520.088*
C8A0.13548 (11)0.16539 (15)0.34328 (16)0.0522 (5)
C90.14962 (18)0.30370 (16)0.2601 (2)0.0739 (7)
H9A0.18950.35320.29990.089*
H9B0.10140.33430.19780.089*
N100.14564 (11)0.10201 (11)0.28778 (15)0.0575 (5)
N110.13047 (11)0.00379 (11)0.28438 (15)0.0568 (5)
H110.16260.03260.34100.068*
C120.06327 (12)0.03293 (14)0.18885 (16)0.0510 (5)
C130.05681 (11)0.13969 (14)0.18533 (15)0.0481 (5)
C140.01321 (13)0.18396 (16)0.08280 (18)0.0620 (6)
H140.01100.14650.01990.074*
C150.00567 (15)0.28268 (17)0.0739 (2)0.0698 (6)
H150.02310.31120.00470.084*
C160.03971 (14)0.34104 (16)0.1652 (2)0.0673 (6)
C170.08318 (16)0.29647 (17)0.2667 (2)0.0740 (7)
H170.10690.33400.32940.089*
C180.09226 (14)0.19757 (16)0.27738 (18)0.0639 (6)
H180.12240.16940.34700.077*
C190.0291 (2)0.44942 (19)0.1527 (3)0.1095 (12)
H19A0.04840.47400.11990.164*
H19B0.02500.46470.10620.164*
H19C0.05730.47840.22400.164*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1211 (16)0.0650 (11)0.0996 (14)0.0179 (10)0.0784 (13)0.0095 (10)
O20.156 (2)0.0601 (12)0.1017 (15)0.0000 (12)0.0827 (16)0.0231 (10)
O30.0722 (10)0.0569 (9)0.0708 (10)0.0182 (8)0.0425 (9)0.0156 (8)
O1W0.0780 (11)0.0680 (11)0.0724 (11)0.0048 (9)0.0464 (10)0.0097 (9)
C10.0706 (14)0.0634 (14)0.0644 (14)0.0104 (11)0.0434 (12)0.0054 (11)
C1A0.0644 (12)0.0465 (11)0.0515 (11)0.0038 (9)0.0368 (10)0.0009 (8)
C20.118 (2)0.089 (2)0.114 (2)0.0013 (17)0.097 (2)0.0096 (17)
C30.123 (2)0.086 (2)0.129 (3)0.0077 (17)0.106 (2)0.0054 (18)
C40.0876 (16)0.0526 (13)0.0862 (16)0.0046 (11)0.0679 (15)0.0018 (11)
C4A0.0583 (11)0.0478 (11)0.0529 (11)0.0002 (9)0.0377 (10)0.0010 (8)
C50.0818 (16)0.0657 (16)0.0636 (14)0.0055 (12)0.0428 (13)0.0125 (11)
C5A0.0573 (12)0.0529 (12)0.0492 (11)0.0014 (9)0.0306 (10)0.0081 (9)
C60.163 (4)0.104 (3)0.115 (3)0.021 (2)0.110 (3)0.005 (2)
C70.257 (6)0.129 (3)0.206 (5)0.084 (3)0.210 (5)0.082 (3)
C80.0814 (16)0.0799 (17)0.0794 (16)0.0027 (13)0.0622 (14)0.0007 (13)
C8A0.0501 (11)0.0533 (12)0.0489 (11)0.0005 (9)0.0314 (9)0.0033 (8)
C90.109 (2)0.0422 (11)0.0741 (15)0.0055 (12)0.0629 (15)0.0046 (10)
N100.0808 (12)0.0381 (9)0.0689 (11)0.0011 (8)0.0564 (10)0.0005 (8)
N110.0708 (11)0.0383 (9)0.0604 (10)0.0004 (7)0.0437 (10)0.0058 (7)
C120.0597 (12)0.0465 (11)0.0575 (12)0.0079 (9)0.0437 (11)0.0071 (9)
C130.0487 (10)0.0468 (11)0.0525 (11)0.0026 (8)0.0356 (9)0.0043 (8)
C140.0615 (12)0.0590 (13)0.0505 (11)0.0041 (10)0.0314 (10)0.0065 (9)
C150.0710 (15)0.0594 (14)0.0594 (13)0.0045 (11)0.0357 (12)0.0071 (10)
C160.0658 (13)0.0497 (12)0.0764 (15)0.0026 (10)0.0436 (12)0.0009 (11)
C170.0856 (17)0.0538 (13)0.0682 (15)0.0027 (11)0.0457 (14)0.0146 (11)
C180.0748 (14)0.0577 (13)0.0523 (12)0.0067 (10)0.0398 (12)0.0034 (9)
C190.127 (3)0.0533 (16)0.121 (3)0.0095 (16)0.072 (2)0.0022 (16)
Geometric parameters (Å, º) top
O1—C11.234 (3)C7—H7B0.9700
O2—C51.231 (3)C8—C8A1.495 (3)
O3—C121.219 (2)C8—H8A0.9700
C1—C1A1.453 (3)C8—H8B0.9700
C1—C21.504 (4)C8A—N101.390 (3)
C1A—C4A1.350 (3)C9—H9A0.9700
C1A—C91.499 (3)C9—H9B0.9700
C2—C31.476 (4)N10—N111.395 (2)
C2—H2A0.9700N11—C121.364 (3)
C2—H2B0.9700N11—H110.8600
C3—C41.511 (4)C12—C131.482 (3)
C3—H3A0.9700C13—C181.385 (3)
C3—H3B0.9700C13—C141.389 (3)
C4—C4A1.503 (3)C14—C151.372 (3)
C4—H4A0.9700C14—H140.9300
C4—H4B0.9700C15—C161.384 (3)
C4A—N101.398 (3)C15—H150.9300
C5—C5A1.450 (3)C16—C171.379 (3)
C5—C61.480 (5)C16—C191.511 (3)
C5A—C8A1.347 (3)C17—C181.377 (3)
C5A—C91.491 (3)C17—H170.9300
C6—C71.389 (5)C18—H180.9300
C6—H6A0.9700C19—H19A0.9600
C6—H6B0.9700C19—H19B0.9600
C7—C81.487 (4)C19—H19C0.9600
C7—H7A0.9700
O1—C1—C1A119.2 (2)C8A—C8—H8A109.2
O1—C1—C2122.3 (2)C7—C8—H8B109.2
C1A—C1—C2118.4 (2)C8A—C8—H8B109.2
C4A—C1A—C1120.2 (2)H8A—C8—H8B107.9
C4A—C1A—C9122.3 (2)C5A—C8A—N10119.38 (19)
C1—C1A—C9117.34 (19)C5A—C8A—C8123.6 (2)
C3—C2—C1113.0 (2)N10—C8A—C8116.99 (19)
C3—C2—H2A109.0C5A—C9—C1A112.11 (18)
C1—C2—H2A109.0C5A—C9—H9A109.2
C3—C2—H2B109.0C1A—C9—H9A109.2
C1—C2—H2B109.0C5A—C9—H9B109.2
H2A—C2—H2B107.8C1A—C9—H9B109.2
C2—C3—C4112.7 (3)H9A—C9—H9B107.9
C2—C3—H3A109.1C8A—N10—N11119.41 (17)
C4—C3—H3A109.1C8A—N10—C4A122.43 (16)
C2—C3—H3B109.1N11—N10—C4A118.12 (16)
C4—C3—H3B109.1C12—N11—N10118.22 (17)
H3A—C3—H3B107.8C12—N11—H11120.9
C4A—C4—C3111.4 (2)N10—N11—H11120.9
C4A—C4—H4A109.3O3—C12—N11121.54 (19)
C3—C4—H4A109.3O3—C12—C13123.35 (19)
C4A—C4—H4B109.3N11—C12—C13115.09 (16)
C3—C4—H4B109.3C18—C13—C14118.37 (19)
H4A—C4—H4B108.0C18—C13—C12124.28 (18)
C1A—C4A—N10119.36 (19)C14—C13—C12117.34 (17)
C1A—C4A—C4123.5 (2)C15—C14—C13120.3 (2)
N10—C4A—C4117.18 (17)C15—C14—H14119.9
O2—C5—C5A120.3 (3)C13—C14—H14119.9
O2—C5—C6120.8 (2)C14—C15—C16121.8 (2)
C5A—C5—C6118.9 (3)C14—C15—H15119.1
C8A—C5A—C5120.5 (2)C16—C15—H15119.1
C8A—C5A—C9122.71 (19)C17—C16—C15117.5 (2)
C5—C5A—C9116.8 (2)C17—C16—C19121.9 (2)
C7—C6—C5116.6 (3)C15—C16—C19120.6 (2)
C7—C6—H6A108.1C18—C17—C16121.5 (2)
C5—C6—H6A108.1C18—C17—H17119.3
C7—C6—H6B108.1C16—C17—H17119.3
C5—C6—H6B108.1C17—C18—C13120.5 (2)
H6A—C6—H6B107.3C17—C18—H18119.7
C6—C7—C8121.5 (3)C13—C18—H18119.7
C6—C7—H7A107.0C16—C19—H19A109.5
C8—C7—H7A107.0C16—C19—H19B109.5
C6—C7—H7B107.0H19A—C19—H19B109.5
C8—C7—H7B107.0C16—C19—H19C109.5
H7A—C7—H7B106.7H19A—C19—H19C109.5
C7—C8—C8A112.2 (2)H19B—C19—H19C109.5
C7—C8—H8A109.2
O1—C1—C1A—C4A176.8 (2)C5—C5A—C9—C1A165.3 (2)
C2—C1—C1A—C4A0.9 (3)C4A—C1A—C9—C5A11.4 (3)
O1—C1—C1A—C90.1 (3)C1—C1A—C9—C5A172.0 (2)
C2—C1—C1A—C9175.8 (2)C5A—C8A—N10—N11171.42 (19)
O1—C1—C2—C3155.7 (3)C8—C8A—N10—N1111.1 (3)
C1A—C1—C2—C328.5 (4)C5A—C8A—N10—C4A6.2 (3)
C1—C2—C3—C451.7 (4)C8—C8A—N10—C4A171.2 (2)
C2—C3—C4—C4A47.1 (4)C1A—C4A—N10—C8A8.0 (3)
C1—C1A—C4A—N10178.2 (2)C4—C4A—N10—C8A171.0 (2)
C9—C1A—C4A—N101.7 (3)C1A—C4A—N10—N11169.70 (19)
C1—C1A—C4A—C42.9 (3)C4—C4A—N10—N1111.4 (3)
C9—C1A—C4A—C4179.4 (2)C8A—N10—N11—C12103.8 (2)
C3—C4—C4A—C1A20.2 (3)C4A—N10—N11—C1274.0 (2)
C3—C4—C4A—N10158.7 (2)N10—N11—C12—O37.5 (3)
O2—C5—C5A—C8A175.6 (2)N10—N11—C12—C13170.87 (17)
C6—C5—C5A—C8A1.6 (4)O3—C12—C13—C18152.9 (2)
O2—C5—C5A—C93.1 (4)N11—C12—C13—C1828.8 (3)
C6—C5—C5A—C9179.7 (3)O3—C12—C13—C1428.2 (3)
O2—C5—C6—C7167.4 (4)N11—C12—C13—C14150.11 (19)
C5A—C5—C6—C715.4 (5)C18—C13—C14—C150.2 (3)
C5—C6—C7—C831.1 (7)C12—C13—C14—C15179.2 (2)
C6—C7—C8—C8A27.9 (6)C13—C14—C15—C161.0 (4)
C5—C5A—C8A—N10173.4 (2)C14—C15—C16—C171.2 (4)
C9—C5A—C8A—N105.2 (3)C14—C15—C16—C19178.8 (3)
C5—C5A—C8A—C83.9 (3)C15—C16—C17—C180.3 (4)
C9—C5A—C8A—C8177.5 (2)C19—C16—C17—C18179.7 (3)
C7—C8—C8A—C5A9.7 (4)C16—C17—C18—C130.8 (4)
C7—C8—C8A—N10173.0 (3)C14—C13—C18—C171.1 (3)
C8A—C5A—C9—C1A13.3 (3)C12—C13—C18—C17180.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O1W0.862.002.789 (2)152
C8—H8A···O3i0.972.523.234 (1)130
O1W—HWB···O1ii0.931.8282.730 (5)162.0
O1W—HWA···O2iii0.881.8972.763 (3)166.2
Symmetry codes: (i) x, y, z+1/2; (ii) x+1/2, y1/2, z+1/2; (iii) x+1/2, y+1/2, z+1.
 

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