9-(3-Bromo-5-chloro-2-hy-droxy-phen-yl)-10-(2-hy-droxy-eth-yl)-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridine-1,8-dione.

In the title compound, C21H21BrClNO4, the dihydro-pyridine ring adopts a flattened boat conformation. The 3-bromo-5-chloro-2-hy-droxy-phenyl ring forms a dihedral angles of 84.44 (7)° with the dihydro-pyridine mean plane. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯O hydrogen bond, with an S(8) ring motif. In the crystal, O-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules, forming a three-dimensional network.

Related literature

For the synthesis and bioactivity of acridines, see, for example: Karolak-Wojciechowska et al. (1996 ▶). For related structures, see: Abdelhamid et al. (2011a ▶,b ▶); Mohamed et al. (2012 ▶); Guo et al. (2004 ▶); Sughanya & Sureshbabu (2012 ▶); Yogavel et al. (2005 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C21H21BrClNO4

M = 466.74

Monoclinic,

a = 8.810 (2) Å

b = 13.809 (3) Å

c = 15.797 (4) Å

β = 100.026 (4)°

V = 1892.5 (8) Å3

Z = 4

Mo Kα radiation

μ = 2.34 mm−1

T = 100 K

0.22 × 0.14 × 0.03 mm

Data collection

Rigaku AFC12 (Right) diffractometer

Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012 ▶) T min = 0.627, T max = 0.933

14959 measured reflections

4299 independent reflections

4126 reflections with I > 2σ(i)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.077

S = 1.03

4299 reflections

255 parameters

H-atom parameters constrained

Δρmax = 0.86 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CrystalClear-SM Expert (Rigaku, 2012 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812050222/hg5278sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050222/hg5278Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812050222/hg5278Isup3.cml

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

C21H21BrClNO4	F(000) = 952
Mr = 466.74	Dx = 1.638 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yn	Cell parameters from 4812 reflections
a = 8.810 (2) Å	θ = 2.5–27.5°
b = 13.809 (3) Å	µ = 2.34 mm−1
c = 15.797 (4) Å	T = 100 K
β = 100.026 (4)°	Plate, yellow
V = 1892.5 (8) Å3	0.22 × 0.14 × 0.03 mm
Z = 4

Rigaku AFC12 (Right) diffractometer	4299 independent reflections
Radiation source: Rotating Anode	4126 reflections with I > 2σ(i)
Detector resolution: 28.5714 pixels mm-1	Rint = 0.024
profile data from ω–scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012)	h = −10→11
Tmin = 0.627, Tmax = 0.933	k = −17→14
14959 measured reflections	l = −20→20

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0485P)2 + 1.1263P] where P = (Fo2 + 2Fc2)/3
4299 reflections	(Δ/σ)max = 0.003
255 parameters	Δρmax = 0.86 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

Experimental. Rigaku CrystalClear-SM Expert 3.1 b5

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Br1	1.02039 (2)	1.02608 (1)	0.11100 (1)	0.0178 (1)
Cl2	0.89028 (5)	1.13026 (3)	0.42922 (3)	0.0206 (1)
O1	0.85205 (14)	0.84648 (9)	0.14843 (8)	0.0171 (3)
O2	0.91879 (13)	0.68133 (9)	0.23546 (7)	0.0155 (3)
O3	0.44222 (13)	0.87300 (9)	0.18903 (8)	0.0175 (3)
O4	0.69992 (16)	0.85677 (12)	0.68490 (9)	0.0294 (4)
N1	0.65599 (15)	0.75304 (10)	0.46456 (8)	0.0125 (4)
C1	0.69843 (17)	0.79777 (11)	0.29224 (10)	0.0113 (4)
C2	0.79574 (17)	0.72563 (11)	0.34966 (10)	0.0114 (4)
C3	0.90436 (17)	0.66869 (11)	0.31212 (10)	0.0124 (4)
C4	0.99634 (19)	0.59201 (12)	0.36547 (11)	0.0169 (4)
C5	1.03428 (19)	0.62450 (13)	0.45893 (11)	0.0165 (4)
C6	0.88912 (18)	0.65080 (12)	0.49409 (11)	0.0152 (4)
C7	0.77954 (17)	0.71276 (11)	0.43370 (10)	0.0121 (4)
C8	0.54946 (17)	0.81352 (11)	0.32480 (10)	0.0114 (4)
C9	0.42314 (18)	0.85498 (12)	0.26225 (10)	0.0134 (4)
C10	0.27404 (19)	0.87759 (14)	0.29195 (11)	0.0202 (5)
C11	0.24551 (19)	0.80920 (14)	0.36209 (11)	0.0203 (5)
C12	0.38110 (18)	0.80674 (14)	0.43714 (11)	0.0165 (4)
C13	0.53272 (17)	0.79239 (11)	0.40620 (10)	0.0122 (4)
C14	0.78575 (17)	0.89267 (11)	0.28563 (10)	0.0113 (4)
C15	0.85590 (17)	0.91091 (12)	0.21354 (10)	0.0128 (4)
C16	0.93144 (18)	0.99934 (13)	0.20933 (10)	0.0135 (4)
C17	0.94463 (17)	1.06742 (12)	0.27456 (11)	0.0143 (4)
C18	0.87751 (19)	1.04633 (12)	0.34544 (11)	0.0146 (4)
C19	0.79829 (18)	0.96063 (12)	0.35129 (10)	0.0131 (4)
C20	0.65018 (19)	0.75423 (14)	0.55771 (10)	0.0168 (4)
C21	0.6898 (2)	0.85513 (15)	0.59499 (12)	0.0242 (5)
H1	0.67320	0.76910	0.23330	0.0140*
H1A	0.85100	0.78990	0.16790	0.0260*
H4	0.61310	0.84430	0.69740	0.0440*
H4A	1.09300	0.57970	0.34330	0.0200*
H4B	0.93660	0.53100	0.36150	0.0200*
H5A	1.10350	0.68140	0.46340	0.0200*
H5B	1.08930	0.57180	0.49410	0.0200*
H6A	0.83570	0.59050	0.50590	0.0180*
H6B	0.91900	0.68570	0.54920	0.0180*
H10A	0.18800	0.87260	0.24270	0.0240*
H10B	0.27710	0.94490	0.31370	0.0240*
H11A	0.22750	0.74320	0.33800	0.0240*
H11B	0.15140	0.82970	0.38350	0.0240*
H12A	0.38450	0.86830	0.46960	0.0200*
H12B	0.36580	0.75330	0.47660	0.0200*
H17	0.99800	1.12660	0.27080	0.0170*
H19	0.75240	0.94830	0.40040	0.0160*
H20A	0.72430	0.70640	0.58780	0.0200*
H20B	0.54570	0.73570	0.56680	0.0200*
H21A	0.78940	0.87620	0.58030	0.0290*
H21B	0.60970	0.90150	0.56860	0.0290*

	U11	U22	U33	U12	U13	U23
Br1	0.0204 (1)	0.0193 (1)	0.0158 (1)	0.0017 (1)	0.0089 (1)	0.0053 (1)
Cl2	0.0244 (2)	0.0190 (2)	0.0201 (2)	−0.0061 (2)	0.0086 (2)	−0.0083 (2)
O1	0.0224 (6)	0.0168 (6)	0.0136 (5)	−0.0002 (5)	0.0072 (5)	−0.0009 (5)
O2	0.0148 (5)	0.0180 (6)	0.0145 (5)	0.0010 (4)	0.0048 (4)	−0.0014 (5)
O3	0.0163 (6)	0.0228 (6)	0.0126 (5)	0.0012 (5)	0.0006 (4)	0.0024 (5)
O4	0.0222 (7)	0.0506 (9)	0.0163 (6)	−0.0094 (6)	0.0056 (5)	−0.0090 (6)
N1	0.0129 (6)	0.0163 (7)	0.0084 (6)	0.0000 (5)	0.0021 (5)	−0.0004 (5)
C1	0.0106 (7)	0.0136 (7)	0.0096 (7)	0.0000 (5)	0.0016 (5)	−0.0002 (6)
C2	0.0101 (7)	0.0114 (7)	0.0123 (7)	−0.0003 (5)	0.0011 (5)	−0.0008 (6)
C3	0.0107 (7)	0.0114 (7)	0.0150 (7)	−0.0021 (5)	0.0020 (5)	−0.0024 (6)
C4	0.0164 (7)	0.0155 (8)	0.0192 (8)	0.0035 (6)	0.0045 (6)	0.0019 (7)
C5	0.0138 (7)	0.0182 (8)	0.0168 (8)	0.0026 (6)	0.0005 (6)	0.0028 (6)
C6	0.0154 (7)	0.0158 (8)	0.0142 (7)	0.0012 (6)	0.0020 (6)	0.0026 (6)
C7	0.0106 (7)	0.0116 (7)	0.0137 (7)	−0.0021 (5)	0.0013 (5)	−0.0012 (6)
C8	0.0108 (7)	0.0117 (7)	0.0116 (7)	−0.0006 (5)	0.0020 (5)	−0.0017 (6)
C9	0.0126 (7)	0.0134 (7)	0.0136 (7)	−0.0010 (6)	0.0009 (6)	−0.0012 (6)
C10	0.0130 (7)	0.0288 (9)	0.0183 (8)	0.0048 (7)	0.0017 (6)	0.0013 (7)
C11	0.0134 (7)	0.0293 (9)	0.0182 (8)	−0.0011 (7)	0.0027 (6)	−0.0009 (7)
C12	0.0116 (7)	0.0262 (9)	0.0127 (7)	−0.0004 (6)	0.0047 (6)	−0.0018 (7)
C13	0.0110 (7)	0.0120 (7)	0.0132 (7)	−0.0010 (5)	0.0011 (6)	−0.0020 (6)
C14	0.0085 (6)	0.0134 (7)	0.0115 (7)	0.0013 (5)	0.0005 (5)	0.0018 (6)
C15	0.0105 (7)	0.0166 (8)	0.0110 (7)	0.0027 (6)	0.0012 (5)	−0.0001 (6)
C16	0.0114 (7)	0.0170 (7)	0.0126 (7)	0.0031 (6)	0.0038 (6)	0.0059 (6)
C17	0.0109 (7)	0.0141 (7)	0.0176 (8)	0.0011 (6)	0.0015 (6)	0.0025 (6)
C18	0.0138 (7)	0.0155 (7)	0.0142 (7)	0.0012 (6)	0.0015 (6)	−0.0029 (6)
C19	0.0114 (7)	0.0168 (8)	0.0114 (7)	0.0007 (6)	0.0029 (6)	0.0008 (6)
C20	0.0149 (7)	0.0271 (9)	0.0083 (7)	0.0013 (6)	0.0018 (6)	0.0002 (6)
C21	0.0209 (9)	0.0358 (11)	0.0163 (8)	−0.0070 (7)	0.0044 (7)	−0.0073 (8)

Br1—C16	1.8939 (17)	C14—C19	1.389 (2)
Cl2—C18	1.7480 (18)	C14—C15	1.410 (2)
O1—C15	1.356 (2)	C15—C16	1.398 (2)
O2—C3	1.2517 (19)	C16—C17	1.385 (2)
O3—C9	1.223 (2)	C17—C18	1.385 (2)
O4—C21	1.408 (2)	C18—C19	1.385 (2)
O1—H1A	0.8400	C20—C21	1.529 (3)
O4—H4	0.8400	C1—H1	1.0000
N1—C20	1.481 (2)	C4—H4A	0.9900
N1—C7	1.384 (2)	C4—H4B	0.9900
N1—C13	1.406 (2)	C5—H5A	0.9900
C1—C14	1.532 (2)	C5—H5B	0.9900
C1—C2	1.510 (2)	C6—H6A	0.9900
C1—C8	1.506 (2)	C6—H6B	0.9900
C2—C3	1.443 (2)	C10—H10A	0.9900
C2—C7	1.371 (2)	C10—H10B	0.9900
C3—C4	1.500 (2)	C11—H11A	0.9900
C4—C5	1.524 (2)	C11—H11B	0.9900
C5—C6	1.524 (2)	C12—H12A	0.9900
C6—C7	1.501 (2)	C12—H12B	0.9900
C8—C13	1.351 (2)	C17—H17	0.9500
C8—C9	1.470 (2)	C19—H19	0.9500
C9—C10	1.503 (2)	C20—H20A	0.9900
C10—C11	1.510 (3)	C20—H20B	0.9900
C11—C12	1.530 (2)	C21—H21A	0.9900
C12—C13	1.513 (2)	C21—H21B	0.9900
C15—O1—H1A	109.00	C2—C1—H1	108.00
C21—O4—H4	109.00	C8—C1—H1	108.00
C13—N1—C20	119.40 (13)	C14—C1—H1	108.00
C7—N1—C20	121.30 (13)	C3—C4—H4A	110.00
C7—N1—C13	119.30 (13)	C3—C4—H4B	110.00
C2—C1—C14	111.47 (13)	C5—C4—H4A	110.00
C2—C1—C8	109.12 (13)	C5—C4—H4B	110.00
C8—C1—C14	112.17 (13)	H4A—C4—H4B	108.00
C1—C2—C7	121.55 (14)	C4—C5—H5A	109.00
C1—C2—C3	117.41 (13)	C4—C5—H5B	109.00
C3—C2—C7	121.02 (14)	C6—C5—H5A	109.00
O2—C3—C4	120.40 (14)	C6—C5—H5B	109.00
C2—C3—C4	119.06 (14)	H5A—C5—H5B	108.00
O2—C3—C2	120.52 (14)	C5—C6—H6A	109.00
C3—C4—C5	110.03 (14)	C5—C6—H6B	109.00
C4—C5—C6	111.52 (14)	C7—C6—H6A	109.00
C5—C6—C7	113.07 (14)	C7—C6—H6B	109.00
C2—C7—C6	121.69 (14)	H6A—C6—H6B	108.00
N1—C7—C6	117.60 (13)	C9—C10—H10A	109.00
N1—C7—C2	120.64 (14)	C9—C10—H10B	109.00
C1—C8—C13	122.65 (14)	C11—C10—H10A	109.00
C9—C8—C13	121.91 (14)	C11—C10—H10B	109.00
C1—C8—C9	115.43 (13)	H10A—C10—H10B	108.00
C8—C9—C10	118.16 (14)	C10—C11—H11A	109.00
O3—C9—C8	120.16 (15)	C10—C11—H11B	109.00
O3—C9—C10	121.64 (15)	C12—C11—H11A	109.00
C9—C10—C11	111.44 (15)	C12—C11—H11B	109.00
C10—C11—C12	112.04 (14)	H11A—C11—H11B	108.00
C11—C12—C13	111.51 (14)	C11—C12—H12A	109.00
N1—C13—C8	120.51 (14)	C11—C12—H12B	109.00
N1—C13—C12	117.61 (13)	C13—C12—H12A	109.00
C8—C13—C12	121.85 (14)	C13—C12—H12B	109.00
C1—C14—C15	120.25 (14)	H12A—C12—H12B	108.00
C15—C14—C19	119.57 (14)	C16—C17—H17	121.00
C1—C14—C19	120.17 (14)	C18—C17—H17	121.00
O1—C15—C16	119.10 (14)	C14—C19—H19	120.00
C14—C15—C16	118.28 (14)	C18—C19—H19	120.00
O1—C15—C14	122.61 (14)	N1—C20—H20A	110.00
C15—C16—C17	122.46 (15)	N1—C20—H20B	110.00
Br1—C16—C15	118.54 (12)	C21—C20—H20A	110.00
Br1—C16—C17	119.00 (13)	C21—C20—H20B	110.00
C16—C17—C18	117.80 (15)	H20A—C20—H20B	108.00
Cl2—C18—C19	118.86 (13)	O4—C21—H21A	109.00
C17—C18—C19	121.64 (15)	O4—C21—H21B	109.00
Cl2—C18—C17	119.50 (13)	C20—C21—H21A	109.00
C14—C19—C18	120.20 (15)	C20—C21—H21B	109.00
N1—C20—C21	110.34 (14)	H21A—C21—H21B	108.00
O4—C21—C20	111.92 (16)
C7—N1—C13—C12	161.29 (14)	C5—C6—C7—C2	12.9 (2)
C7—N1—C20—C21	103.01 (17)	C5—C6—C7—N1	−170.23 (14)
C13—N1—C20—C21	−77.86 (18)	C1—C8—C13—C12	−178.67 (15)
C7—N1—C13—C8	−16.8 (2)	C9—C8—C13—N1	−179.81 (14)
C13—N1—C7—C2	11.4 (2)	C1—C8—C9—O3	1.0 (2)
C20—N1—C7—C2	−169.52 (15)	C1—C8—C9—C10	−176.73 (14)
C20—N1—C13—C12	−17.9 (2)	C13—C8—C9—O3	−179.82 (15)
C20—N1—C13—C8	164.11 (15)	C9—C8—C13—C12	2.2 (2)
C20—N1—C7—C6	13.6 (2)	C13—C8—C9—C10	2.4 (2)
C13—N1—C7—C6	−165.53 (14)	C1—C8—C13—N1	−0.7 (2)
C14—C1—C2—C7	98.95 (17)	O3—C9—C10—C11	151.65 (16)
C8—C1—C14—C15	−137.57 (15)	C8—C9—C10—C11	−30.6 (2)
C2—C1—C8—C13	20.3 (2)	C9—C10—C11—C12	54.0 (2)
C14—C1—C8—C9	75.41 (17)	C10—C11—C12—C13	−49.4 (2)
C2—C1—C8—C9	−160.57 (13)	C11—C12—C13—N1	−156.62 (15)
C2—C1—C14—C15	99.74 (17)	C11—C12—C13—C8	21.4 (2)
C2—C1—C14—C19	−79.27 (18)	C1—C14—C15—O1	−1.0 (2)
C8—C1—C14—C19	43.4 (2)	C19—C14—C15—C16	−2.4 (2)
C8—C1—C2—C7	−25.5 (2)	C1—C14—C19—C18	179.85 (15)
C14—C1—C2—C3	−82.55 (17)	C15—C14—C19—C18	0.8 (2)
C14—C1—C8—C13	−103.74 (17)	C1—C14—C15—C16	178.62 (14)
C8—C1—C2—C3	153.02 (13)	C19—C14—C15—O1	177.99 (15)
C1—C2—C7—C6	−172.02 (14)	C14—C15—C16—Br1	−178.05 (12)
C1—C2—C3—O2	1.8 (2)	O1—C15—C16—Br1	1.6 (2)
C7—C2—C3—C4	2.2 (2)	O1—C15—C16—C17	−177.82 (15)
C1—C2—C7—N1	11.2 (2)	C14—C15—C16—C17	2.5 (2)
C7—C2—C3—O2	−179.65 (15)	C15—C16—C17—C18	−1.1 (2)
C3—C2—C7—C6	9.5 (2)	Br1—C16—C17—C18	179.52 (12)
C1—C2—C3—C4	−176.32 (14)	C16—C17—C18—Cl2	−179.70 (13)
C3—C2—C7—N1	−167.22 (14)	C16—C17—C18—C19	−0.6 (2)
C2—C3—C4—C5	−34.7 (2)	C17—C18—C19—C14	0.7 (3)
O2—C3—C4—C5	147.20 (15)	Cl2—C18—C19—C14	179.80 (12)
C3—C4—C5—C6	55.54 (18)	N1—C20—C21—O4	−174.31 (14)
C4—C5—C6—C7	−45.49 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.84	1.88	2.6749 (19)	158
O4—H4···O2i	0.84	1.94	2.782 (2)	176
C1—H1···O1	1.00	2.48	2.918 (2)	106
C6—H6B···O3ii	0.99	2.33	3.051 (2)	129
C20—H20A···O3ii	0.99	2.53	3.486 (2)	163
C20—H20B···O1i	0.99	2.57	3.492 (2)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2	0.84	1.88	2.6749 (19)	158
O4—H4⋯O2i	0.84	1.94	2.782 (2)	176
C6—H6B⋯O3ii	0.99	2.33	3.051 (2)	129
C20—H20A⋯O3ii	0.99	2.53	3.486 (2)	163
C20—H20B⋯O1i	0.99	2.57	3.492 (2)	154

Symmetry codes: (i) ; (ii) .