Atalaphylline.

THE TITLE ACRIDONE ALKALOID [SYSTEMATIC NAME: 1,3,5-trihydr-oxy-2,4-bis-(3-methyl-but-2-en-yl)acridin-9(10H)-one], C(23)H(25)NO(4), known as atalaphylline, was isolated from Atalantia monophylla Corrêa, a mangrove plant. The mol-ecule contains three fused planar rings with an r.m.s. deviation of 0.026 (2) Å. Both 3-methyl-but-2-enyl substituents are in a (-)anticlinal conformation. An intra-molecular N-H⋯O hydrogen bond generates an S(5) ring motif, while an intra-molecular O-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal structure, the mol-ecules are linked into screw chains along [010] by inter-molecular O-H⋯O hydrogen bonds. These chains are stacked along the a axis by π-π inter-actions with centroid-centroid distances of 3.6695 (13) and 3.6696 (13) Å.

Related literature

For hydrogen-bond motifs, see Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For details of acridone alkaloids and their biological activity, see: Basu & Basa (1972 ▶); Itoigawa et al. (2003 ▶); Kawaii et al. (1999a ▶,b ▶). For a related structure, see: Chukaew et al. (2007 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C23H25NO4

M = 379.44

Orthorhombic,

a = 5.0650 (1) Å

b = 15.0131 (4) Å

c = 24.5813 (5) Å

V = 1869.20 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.40 × 0.21 × 0.04 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.964, T max = 0.996

17852 measured reflections

3142 independent reflections

2525 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.118

S = 1.03

3142 reflections

257 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809051885/sj2692sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051885/sj2692Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H25NO4	Dx = 1.348 Mg m−3
Mr = 379.44	Melting point = 518–520 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3142 reflections
a = 5.0650 (1) Å	θ = 1.6–30.0°
b = 15.0131 (4) Å	µ = 0.09 mm−1
c = 24.5813 (5) Å	T = 100 K
V = 1869.20 (7) Å3	Plate, brown
Z = 4	0.40 × 0.21 × 0.04 mm
F(000) = 808

Bruker APEXII CCD area-detector diffractometer	3142 independent reflections
Radiation source: sealed tube	2525 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 30.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −6→7
Tmin = 0.964, Tmax = 0.996	k = −21→15
17852 measured reflections	l = −34→34

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0588P)2 + 0.5624P] where P = (Fo2 + 2Fc2)/3
3142 reflections	(Δ/σ)max < 0.001
257 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
O1	0.3340 (3)	0.33730 (11)	0.16280 (7)	0.0193 (4)
H1O1	0.4552	0.3307	0.1845	0.029*
O2	0.7218 (3)	0.37946 (11)	0.22404 (6)	0.0183 (4)
O3	0.9035 (4)	0.77231 (10)	0.22808 (6)	0.0187 (4)
H1O3	1.0112	0.8067	0.2415	0.028*
O4	−0.0692 (3)	0.56738 (12)	0.05943 (7)	0.0220 (4)
H1O4	−0.1545	0.5244	0.0487	0.026*
N1	0.6177 (4)	0.64068 (12)	0.18267 (8)	0.0150 (4)
H1N1	0.6002	0.6956	0.1734	0.018*
C1	0.1293 (5)	0.44831 (15)	0.11046 (9)	0.0149 (5)
C2	0.3171 (5)	0.42414 (15)	0.14846 (9)	0.0148 (5)
C3	0.4888 (4)	0.48744 (14)	0.17270 (9)	0.0137 (4)
C4	0.6867 (5)	0.46079 (15)	0.21169 (9)	0.0141 (4)
C5	0.8434 (5)	0.53044 (15)	0.23695 (9)	0.0152 (5)
C6	1.0356 (5)	0.51065 (15)	0.27656 (9)	0.0193 (5)
H6A	1.0648	0.4519	0.2868	0.023*
C7	1.1794 (5)	0.57750 (17)	0.29992 (10)	0.0226 (5)
H7A	1.3061	0.5639	0.3260	0.027*
C8	1.1368 (5)	0.66664 (16)	0.28480 (9)	0.0198 (5)
H8A	1.2342	0.7116	0.3014	0.024*
C9	0.9534 (5)	0.68805 (15)	0.24586 (9)	0.0159 (5)
C10	0.8024 (5)	0.61953 (15)	0.22133 (9)	0.0147 (4)
C11	0.4593 (4)	0.57851 (14)	0.15804 (9)	0.0143 (4)
C12	0.2707 (5)	0.60543 (15)	0.11958 (9)	0.0149 (5)
C13	0.1139 (5)	0.53968 (15)	0.09674 (9)	0.0167 (5)
C14	0.2242 (5)	0.70302 (15)	0.10646 (10)	0.0176 (5)
H14A	0.0747	0.7072	0.0819	0.021*
H14B	0.1765	0.7336	0.1398	0.021*
C15	0.4547 (5)	0.75103 (16)	0.08107 (9)	0.0185 (5)
H15A	0.5447	0.7210	0.0537	0.022*
C16	0.5433 (5)	0.83205 (16)	0.09377 (10)	0.0214 (5)
C17	0.7643 (6)	0.87496 (19)	0.06275 (13)	0.0337 (7)
H17A	0.8238	0.8353	0.0347	0.051*
H17B	0.9077	0.8877	0.0871	0.051*
H17C	0.7028	0.9294	0.0466	0.051*
C18	0.4340 (6)	0.88750 (17)	0.13926 (11)	0.0284 (6)
H18A	0.2903	0.8564	0.1562	0.043*
H18B	0.3717	0.9432	0.1250	0.043*
H18C	0.5700	0.8984	0.1656	0.043*
C19	−0.0597 (5)	0.38065 (15)	0.08666 (9)	0.0179 (5)
H19A	−0.0638	0.3287	0.1101	0.022*
H19B	−0.2358	0.4060	0.0862	0.022*
C20	0.0113 (5)	0.35141 (15)	0.02980 (9)	0.0190 (5)
H20A	0.1620	0.3164	0.0266	0.023*
C21	−0.1154 (5)	0.36960 (16)	−0.01649 (10)	0.0219 (5)
C22	−0.0143 (7)	0.3355 (2)	−0.07035 (10)	0.0323 (7)
H22A	0.1369	0.2982	−0.0643	0.049*
H22B	0.0349	0.3850	−0.0929	0.049*
H22C	−0.1502	0.3017	−0.0880	0.049*
C23	−0.3584 (6)	0.4259 (2)	−0.02118 (12)	0.0333 (6)
H23A	−0.4316	0.4356	0.0143	0.050*
H23B	−0.4859	0.3961	−0.0436	0.050*
H23C	−0.3134	0.4821	−0.0373	0.050*

	U11	U22	U33	U12	U13	U23
O1	0.0209 (8)	0.0137 (8)	0.0235 (8)	−0.0020 (7)	−0.0046 (7)	0.0007 (7)
O2	0.0205 (8)	0.0100 (7)	0.0243 (8)	−0.0001 (7)	−0.0030 (7)	0.0012 (7)
O3	0.0236 (9)	0.0098 (7)	0.0227 (8)	−0.0018 (7)	−0.0055 (7)	−0.0001 (6)
O4	0.0206 (8)	0.0205 (8)	0.0251 (9)	−0.0028 (8)	−0.0084 (7)	0.0007 (7)
N1	0.0153 (9)	0.0083 (9)	0.0214 (9)	0.0004 (8)	−0.0029 (8)	0.0009 (7)
C1	0.0155 (10)	0.0137 (10)	0.0155 (10)	−0.0026 (9)	0.0010 (9)	−0.0029 (9)
C2	0.0167 (11)	0.0107 (10)	0.0169 (11)	−0.0015 (9)	0.0031 (9)	−0.0020 (9)
C3	0.0143 (10)	0.0110 (9)	0.0158 (10)	−0.0010 (9)	0.0004 (9)	−0.0014 (8)
C4	0.0147 (10)	0.0133 (10)	0.0141 (10)	0.0009 (9)	−0.0006 (9)	−0.0013 (9)
C5	0.0169 (11)	0.0121 (10)	0.0164 (10)	−0.0003 (9)	0.0003 (9)	−0.0013 (9)
C6	0.0255 (12)	0.0112 (10)	0.0213 (12)	0.0022 (10)	−0.0066 (10)	0.0013 (9)
C7	0.0264 (13)	0.0179 (11)	0.0236 (12)	0.0013 (11)	−0.0108 (11)	0.0011 (10)
C8	0.0246 (12)	0.0135 (11)	0.0211 (12)	−0.0040 (10)	−0.0063 (10)	−0.0031 (9)
C9	0.0194 (11)	0.0113 (10)	0.0170 (11)	−0.0017 (9)	0.0008 (10)	−0.0021 (9)
C10	0.0152 (10)	0.0144 (10)	0.0145 (10)	0.0006 (9)	0.0003 (9)	−0.0003 (9)
C11	0.0125 (10)	0.0115 (9)	0.0190 (11)	−0.0019 (9)	0.0013 (9)	−0.0006 (9)
C12	0.0161 (10)	0.0099 (10)	0.0186 (11)	0.0000 (9)	−0.0008 (9)	0.0011 (9)
C13	0.0159 (11)	0.0176 (11)	0.0167 (10)	0.0012 (10)	0.0006 (9)	0.0014 (9)
C14	0.0154 (11)	0.0121 (10)	0.0252 (12)	−0.0004 (9)	−0.0036 (10)	0.0024 (9)
C15	0.0200 (11)	0.0174 (11)	0.0181 (11)	0.0026 (10)	−0.0021 (9)	0.0023 (9)
C16	0.0192 (11)	0.0191 (11)	0.0258 (12)	−0.0022 (10)	−0.0084 (10)	0.0073 (10)
C17	0.0237 (13)	0.0263 (14)	0.0510 (18)	−0.0056 (13)	−0.0017 (14)	0.0111 (13)
C18	0.0376 (15)	0.0150 (11)	0.0326 (14)	−0.0031 (12)	−0.0083 (13)	−0.0037 (11)
C19	0.0172 (11)	0.0155 (10)	0.0211 (11)	−0.0045 (10)	−0.0004 (9)	0.0005 (9)
C20	0.0202 (11)	0.0148 (10)	0.0220 (12)	−0.0034 (10)	0.0012 (10)	−0.0033 (9)
C21	0.0283 (13)	0.0170 (11)	0.0205 (12)	−0.0085 (11)	0.0017 (11)	−0.0007 (10)
C22	0.0453 (17)	0.0313 (14)	0.0204 (13)	−0.0074 (15)	0.0010 (13)	−0.0022 (11)
C23	0.0268 (14)	0.0446 (17)	0.0287 (14)	−0.0006 (14)	−0.0086 (12)	0.0017 (13)

O1—C2	1.353 (3)	C12—C14	1.519 (3)
O1—H1O1	0.8200	C14—C15	1.508 (3)
O2—C4	1.271 (3)	C14—H14A	0.9700
O3—C9	1.362 (3)	C14—H14B	0.9700
O3—H1O3	0.8200	C15—C16	1.334 (3)
O4—C13	1.369 (3)	C15—H15A	0.9300
O4—H1O4	0.8200	C16—C17	1.500 (4)
N1—C10	1.371 (3)	C16—C18	1.500 (4)
N1—C11	1.372 (3)	C17—H17A	0.9600
N1—H1N1	0.8600	C17—H17B	0.9600
C1—C2	1.381 (3)	C17—H17C	0.9600
C1—C13	1.415 (3)	C18—H18A	0.9600
C1—C19	1.514 (3)	C18—H18B	0.9600
C2—C3	1.419 (3)	C18—H18C	0.9600
C3—C11	1.422 (3)	C19—C20	1.508 (3)
C3—C4	1.443 (3)	C19—H19A	0.9700
C4—C5	1.452 (3)	C19—H19B	0.9700
C5—C10	1.407 (3)	C20—C21	1.335 (3)
C5—C6	1.408 (3)	C20—H20A	0.9300
C6—C7	1.366 (3)	C21—C23	1.497 (4)
C6—H6A	0.9300	C21—C22	1.509 (3)
C7—C8	1.406 (3)	C22—H22A	0.9600
C7—H7A	0.9300	C22—H22B	0.9600
C8—C9	1.372 (3)	C22—H22C	0.9600
C8—H8A	0.9300	C23—H23A	0.9600
C9—C10	1.417 (3)	C23—H23B	0.9600
C11—C12	1.404 (3)	C23—H23C	0.9600
C12—C13	1.386 (3)
C2—O1—H1O1	109.5	C12—C14—H14A	108.4
C9—O3—H1O3	109.5	C15—C14—H14B	108.4
C13—O4—H1O4	109.5	C12—C14—H14B	108.4
C10—N1—C11	123.20 (19)	H14A—C14—H14B	107.5
C10—N1—H1N1	118.4	C16—C15—C14	126.8 (2)
C11—N1—H1N1	118.4	C16—C15—H15A	116.6
C2—C1—C13	117.0 (2)	C14—C15—H15A	116.6
C2—C1—C19	121.4 (2)	C15—C16—C17	121.6 (3)
C13—C1—C19	121.6 (2)	C15—C16—C18	123.8 (2)
O1—C2—C1	118.2 (2)	C17—C16—C18	114.6 (2)
O1—C2—C3	119.8 (2)	C16—C17—H17A	109.5
C1—C2—C3	122.0 (2)	C16—C17—H17B	109.5
C2—C3—C11	118.2 (2)	H17A—C17—H17B	109.5
C2—C3—C4	121.2 (2)	C16—C17—H17C	109.5
C11—C3—C4	120.5 (2)	H17A—C17—H17C	109.5
O2—C4—C3	121.5 (2)	H17B—C17—H17C	109.5
O2—C4—C5	120.9 (2)	C16—C18—H18A	109.5
C3—C4—C5	117.64 (19)	C16—C18—H18B	109.5
C10—C5—C6	119.4 (2)	H18A—C18—H18B	109.5
C10—C5—C4	119.1 (2)	C16—C18—H18C	109.5
C6—C5—C4	121.4 (2)	H18A—C18—H18C	109.5
C7—C6—C5	120.3 (2)	H18B—C18—H18C	109.5
C7—C6—H6A	119.9	C20—C19—C1	113.73 (19)
C5—C6—H6A	119.9	C20—C19—H19A	108.8
C6—C7—C8	120.4 (2)	C1—C19—H19A	108.8
C6—C7—H7A	119.8	C20—C19—H19B	108.8
C8—C7—H7A	119.8	C1—C19—H19B	108.8
C9—C8—C7	120.8 (2)	H19A—C19—H19B	107.7
C9—C8—H8A	119.6	C21—C20—C19	128.0 (2)
C7—C8—H8A	119.6	C21—C20—H20A	116.0
O3—C9—C8	124.5 (2)	C19—C20—H20A	116.0
O3—C9—C10	116.0 (2)	C20—C21—C23	125.2 (2)
C8—C9—C10	119.5 (2)	C20—C21—C22	121.0 (2)
N1—C10—C5	120.7 (2)	C23—C21—C22	113.8 (2)
N1—C10—C9	119.7 (2)	C21—C22—H22A	109.5
C5—C10—C9	119.6 (2)	C21—C22—H22B	109.5
N1—C11—C12	119.97 (19)	H22A—C22—H22B	109.5
N1—C11—C3	118.7 (2)	C21—C22—H22C	109.5
C12—C11—C3	121.3 (2)	H22A—C22—H22C	109.5
C13—C12—C11	117.3 (2)	H22B—C22—H22C	109.5
C13—C12—C14	120.8 (2)	C21—C23—H23A	109.5
C11—C12—C14	121.8 (2)	C21—C23—H23B	109.5
O4—C13—C12	116.3 (2)	H23A—C23—H23B	109.5
O4—C13—C1	119.5 (2)	C21—C23—H23C	109.5
C12—C13—C1	124.2 (2)	H23A—C23—H23C	109.5
C15—C14—C12	115.4 (2)	H23B—C23—H23C	109.5
C15—C14—H14A	108.4
C13—C1—C2—O1	179.2 (2)	O3—C9—C10—C5	179.3 (2)
C19—C1—C2—O1	2.1 (3)	C8—C9—C10—C5	−0.4 (3)
C13—C1—C2—C3	−0.3 (3)	C10—N1—C11—C12	178.7 (2)
C19—C1—C2—C3	−177.5 (2)	C10—N1—C11—C3	−0.6 (3)
O1—C2—C3—C11	−177.9 (2)	C2—C3—C11—N1	177.7 (2)
C1—C2—C3—C11	1.7 (3)	C4—C3—C11—N1	−1.7 (3)
O1—C2—C3—C4	1.4 (3)	C2—C3—C11—C12	−1.7 (3)
C1—C2—C3—C4	−179.0 (2)	C4—C3—C11—C12	179.0 (2)
C2—C3—C4—O2	3.0 (3)	N1—C11—C12—C13	−179.0 (2)
C11—C3—C4—O2	−177.7 (2)	C3—C11—C12—C13	0.3 (3)
C2—C3—C4—C5	−176.4 (2)	N1—C11—C12—C14	−3.6 (3)
C11—C3—C4—C5	2.9 (3)	C3—C11—C12—C14	175.7 (2)
O2—C4—C5—C10	178.7 (2)	C11—C12—C13—O4	179.85 (19)
C3—C4—C5—C10	−2.0 (3)	C14—C12—C13—O4	4.4 (3)
O2—C4—C5—C6	−1.2 (3)	C11—C12—C13—C1	1.2 (3)
C3—C4—C5—C6	178.2 (2)	C14—C12—C13—C1	−174.3 (2)
C10—C5—C6—C7	0.5 (4)	C2—C1—C13—O4	−179.8 (2)
C4—C5—C6—C7	−179.6 (2)	C19—C1—C13—O4	−2.7 (3)
C5—C6—C7—C8	0.1 (4)	C2—C1—C13—C12	−1.2 (3)
C6—C7—C8—C9	−0.9 (4)	C19—C1—C13—C12	176.0 (2)
C7—C8—C9—O3	−178.7 (2)	C13—C12—C14—C15	−120.8 (2)
C7—C8—C9—C10	1.0 (4)	C11—C12—C14—C15	64.0 (3)
C11—N1—C10—C5	1.6 (3)	C12—C14—C15—C16	−136.1 (2)
C11—N1—C10—C9	−178.3 (2)	C14—C15—C16—C17	−175.8 (2)
C6—C5—C10—N1	179.6 (2)	C14—C15—C16—C18	4.2 (4)
C4—C5—C10—N1	−0.2 (3)	C2—C1—C19—C20	−103.0 (3)
C6—C5—C10—C9	−0.4 (3)	C13—C1—C19—C20	79.9 (3)
C4—C5—C10—C9	179.7 (2)	C1—C19—C20—C21	−110.2 (3)
O3—C9—C10—N1	−0.7 (3)	C19—C20—C21—C23	1.2 (4)
C8—C9—C10—N1	179.6 (2)	C19—C20—C21—C22	179.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2	0.82	1.82	2.554 (2)	149
O3—H1O3···O2i	0.82	1.93	2.752 (2)	175
N1—H1N1···O3	0.86	2.34	2.692 (3)	105
C14—H14A···O4	0.97	2.29	2.773 (3)	110
C19—H19A···O1	0.97	2.40	2.811 (3)	105

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2	0.82	1.82	2.554 (2)	149
O3—H1O3⋯O2i	0.82	1.93	2.752 (2)	175
N1—H1N1⋯O3	0.86	2.34	2.692 (3)	105

Symmetry code: (i) .