Carvedilol dihydrogen phosphate propan-2-ol solvate from powder diffraction data.

In the cation of the title compound, C(24)H(27)N(2)O(4) (+)·H(2)PO(4) (-)·C(3)H(8)O [systematic name: 3-(9H-carbazol-4-yl-oxy)-2-hydr-oxy-N-[2-(2-methoxy-phen-oxy)eth-yl]propan-1-aminium dihydro-gen phosphate propan-2-ol solvate], the mean planes of the tricyclic carbazole system and the benzene ring form a dihedral angle of 42.00 (16)°. In the crystal structure, classical inter-molecular O-H⋯O and N-H⋯O hydrogen bonds link the cations, anions and solvent mol-ecules into layers parallel to the ac plane.

Related literature

For details of the synthesis, see: Brook et al. (2005 ▶). For the indexing algorithm, see: Werner et al. (1985 ▶). For the crystal structures of carvedilol as a free base and a cation, see: Chen et al. (1998 ▶); Yathirajan et al. (2007 ▶); Chernyshev et al. (2009 ▶).

Experimental

Crystal data

C24H27N2O4 +·H2PO4 −·C3H8O

M = 564.56

Triclinic,

a = 11.5516 (11) Å

b = 16.6523 (19) Å

c = 7.8643 (8) Å

α = 95.404 (15)°

β = 94.635 (16)°

γ = 71.247 (14)°

V = 1424.1 (3) Å3

Z = 2

Cu Kα1 radiation, λ = 1.54059 Å

μ = 1.32 mm−1

T = 295 K

flat_sheet, 15 × 1 mm

Data collection

G670 Guinier camera imaging plate diffractometer

Specimen mounting: thin layer in the specimen holder of the camera

Data collection mode: transmission

Scan method: continuous

2θmin = 3.50°, 2θmax = 85.00°, 2θstep = 0.01°

Refinement

R p = 0.020

R wp = 0.026

R exp = 0.012

R Bragg = 0.051

χ2 = 4.516

8151 data points

183 parameters

134 restraints

H-atom parameters constrained

Data collection: G670 Imaging Plate Guinier Camera Software (Huber, 2002 ▶); cell refinement: MRIA (Zlokazov & Chernyshev, 1992 ▶); data reduction: G670 Imaging Plate Guinier Camera Software; method used to solve structure: simulated annealing (Zhukov et al., 2001 ▶); program(s) used to refine structure: MRIA; molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: MRIA and SHELXL97 (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810005349/ya2118sup1.cif

Rietveld powder data: contains datablocks I. DOI: 10.1107/S1600536810005349/ya2118Isup2.rtv

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

C24H27N2O4+·H2PO4−·C3H8O	Z = 2
Mr = 564.56	F(000) = 600
Triclinic, P1	Dx = 1.317 Mg m−3
a = 11.5516 (11) Å	Cu Kα1 radiation, λ = 1.54059 Å
b = 16.6523 (19) Å	µ = 1.32 mm−1
c = 7.8643 (8) Å	T = 295 K
α = 95.404 (15)°	Particle morphology: no specific habit
β = 94.635 (16)°	light grey
γ = 71.247 (14)°	flat_sheet, 15 × 1 mm
V = 1424.1 (3) Å3	Specimen preparation: Prepared at 295 K and 101 kPa

G670 Guinier camera imaging plate diffractometer	Data collection mode: transmission
Radiation source: line-focus sealed tube	Scan method: continuous
Curved Germanium (111)	2θmin = 3.50°, 2θmax = 85.00°, 2θstep = 0.01°
Specimen mounting: thin layer in the specimen holder of the camera

Refinement on Inet	Profile function: split-type pseudo-Voigt (Toraya, 1986)
Least-squares matrix: full with fixed elements per cycle	183 parameters
Rp = 0.020	134 restraints
Rwp = 0.026	0 constraints
Rexp = 0.012	H-atom parameters constrained
RBragg = 0.051	Weighting scheme based on measured s.u.'s
χ2 = 4.516	(Δ/σ)max = 0.002
8151 data points	Background function: Chebyshev polynomial up to the 5th order
Excluded region(s): none	Preferred orientation correction: March-Dollase (Dollase, 1986); direction of preferred orientation 001, texture parameter r = 0.978(4).

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
C1	0.1569 (9)	0.4372 (6)	0.1923 (11)	0.081 (5)*
H1A	0.2323	0.3959	0.2322	0.097*
H1B	0.1532	0.4318	0.0682	0.097*
C2	0.0481 (8)	0.4175 (5)	0.2558 (11)	0.060 (4)*
H2	0.0602	0.4105	0.3790	0.072*
C3	0.0364 (9)	0.3355 (5)	0.1605 (11)	0.075 (5)*
H3A	−0.0284	0.3196	0.2051	0.090*
H3B	0.0184	0.3429	0.0393	0.090*
C4	0.1649 (9)	0.1898 (5)	0.1249 (12)	0.074 (4)*
C5	0.0787 (9)	0.1645 (6)	0.0178 (11)	0.082 (5)*
H5	0.0051	0.2044	−0.0149	0.098*
C6	0.1032 (9)	0.0783 (5)	−0.0411 (11)	0.073 (5)*
H6	0.0436	0.0621	−0.1089	0.087*
C7	0.2137 (9)	0.0168 (6)	−0.0007 (13)	0.081 (4)*
H7	0.2283	−0.0400	−0.0383	0.097*
C8	0.3021 (8)	0.0440 (6)	0.0988 (11)	0.063 (4)*
N9	0.4179 (7)	−0.0027 (4)	0.1591 (9)	0.059 (3)*
H9	0.4523	−0.0562	0.1356	0.071*
C10	0.4702 (9)	0.0498 (6)	0.2632 (11)	0.078 (5)*
C11	0.5820 (9)	0.0296 (6)	0.3584 (12)	0.077 (5)*
H11	0.6350	−0.0259	0.3570	0.092*
C12	0.6116 (9)	0.0955 (6)	0.4557 (12)	0.090 (5)*
H12	0.6876	0.0842	0.5148	0.108*
C13	0.5289 (9)	0.1788 (6)	0.4663 (12)	0.077 (4)*
H13	0.5490	0.2209	0.5370	0.093*
C14	0.4171 (9)	0.1988 (6)	0.3720 (11)	0.068 (4)*
H14	0.3638	0.2543	0.3766	0.082*
C15	0.3860 (8)	0.1341 (5)	0.2696 (11)	0.062 (4)*
C16	0.2776 (9)	0.1293 (5)	0.1691 (12)	0.073 (5)*
O17	0.1515 (5)	0.2726 (4)	0.1889 (7)	0.070 (3)*
O18	−0.0596 (6)	0.4879 (4)	0.2224 (7)	0.079 (3)*
H18	−0.1171	0.4835	0.2714	0.119*
N19	0.1589 (7)	0.5250 (5)	0.2533 (9)	0.085 (4)*
H19A	0.1570	0.5309	0.3680	0.102*
H19B	0.0910	0.5632	0.2106	0.102*
C20	0.2692 (9)	0.5444 (6)	0.2024 (12)	0.074 (4)*
H20A	0.2722	0.5381	0.0788	0.089*
H20B	0.3429	0.5043	0.2500	0.089*
C21	0.2643 (9)	0.6346 (6)	0.2664 (12)	0.086 (5)*
H21A	0.2850	0.6378	0.3883	0.103*
H21B	0.3210	0.6529	0.2076	0.103*
O22	0.1417 (6)	0.6860 (4)	0.2302 (7)	0.070 (3)*
C23	0.0870 (9)	0.7546 (6)	0.3420 (12)	0.080 (5)*
C24	−0.0359 (9)	0.7649 (6)	0.3745 (12)	0.088 (5)*
C25	−0.1014 (9)	0.8340 (6)	0.4794 (11)	0.091 (5)*
H25	−0.1817	0.8403	0.5024	0.109*
C26	−0.0462 (9)	0.8941 (6)	0.5502 (12)	0.079 (4)*
H26	−0.0902	0.9404	0.6197	0.095*
C27	0.0740 (9)	0.8846 (6)	0.5168 (13)	0.090 (5)*
H27	0.1095	0.9255	0.5613	0.108*
C28	0.1419 (9)	0.8137 (6)	0.4164 (12)	0.089 (5)*
H28	0.2236	0.8060	0.3994	0.107*
O29	−0.0815 (6)	0.7013 (4)	0.3012 (8)	0.073 (3)*
C30	−0.2122 (9)	0.7240 (6)	0.2683 (12)	0.093 (5)*
H30A	−0.2328	0.6752	0.2179	0.140*
H30B	−0.2387	0.7686	0.1913	0.140*
H30C	−0.2521	0.7432	0.3739	0.140*
P31	−0.3639 (3)	0.52870 (19)	0.3615 (4)	0.0600 (14)*
O32	−0.4390 (6)	0.5878 (4)	0.4988 (9)	0.115 (3)*
H32	−0.4775	0.5615	0.5402	0.173*
O33	−0.4183 (6)	0.4583 (4)	0.3049 (8)	0.101 (3)*
O34	−0.2334 (7)	0.4907 (4)	0.4313 (8)	0.127 (3)*
O35	−0.3653 (6)	0.5787 (4)	0.2088 (8)	0.092 (3)*
H35	−0.4098	0.5644	0.1337	0.138*
O36	−0.4622 (6)	0.3709 (4)	0.0315 (8)	0.085 (3)*
H36	−0.4178	0.3987	0.0706	0.128*
C37	−0.4205 (9)	0.2878 (6)	0.0907 (12)	0.089 (5)*
H37	−0.4595	0.2880	0.1970	0.107*
C38	−0.2846 (9)	0.2616 (6)	0.1240 (13)	0.093 (5)*
H38A	−0.2642	0.3007	0.2095	0.140*
H38B	−0.2464	0.2619	0.0202	0.140*
H38C	−0.2561	0.2054	0.1635	0.140*
C39	−0.4550 (10)	0.2278 (6)	−0.0426 (13)	0.105 (5)*
H39A	−0.5424	0.2455	−0.0623	0.158*
H39B	−0.4272	0.1714	−0.0037	0.158*
H39C	−0.4175	0.2280	−0.1471	0.158*

C1—N19	1.502 (12)	C20—H20A	0.97
C1—C2	1.528 (15)	C20—H20B	0.97
C1—H1A	0.97	C21—O22	1.421 (10)
C1—H1B	0.97	C21—H21A	0.97
C2—O18	1.435 (9)	C21—H21B	0.97
C2—C3	1.533 (13)	O22—C23	1.383 (10)
C2—H2	0.98	C23—C28	1.395 (15)
C3—O17	1.420 (10)	C23—C24	1.415 (15)
C3—H3A	0.97	C24—O29	1.388 (13)
C3—H3B	0.97	C24—C25	1.392 (12)
C4—O17	1.387 (11)	C25—C26	1.402 (16)
C4—C5	1.395 (14)	C25—H25	0.93
C4—C16	1.407 (12)	C26—C27	1.390 (15)
C5—C6	1.410 (13)	C26—H26	0.93
C5—H5	0.93	C27—C28	1.400 (12)
C6—C7	1.390 (12)	C27—H27	0.93
C6—H6	0.93	C28—H28	0.93
C7—C8	1.401 (14)	O29—C30	1.441 (12)
C7—H7	0.93	C30—H30A	0.96
C8—N9	1.385 (10)	C30—H30B	0.96
C8—C16	1.422 (12)	C30—H30C	0.96
N9—C10	1.387 (13)	P31—O32	1.513 (7)
N9—H9	0.86	P31—O34	1.514 (8)
C10—C11	1.398 (13)	P31—O33	1.516 (8)
C10—C15	1.427 (11)	P31—O35	1.520 (7)
C11—C12	1.395 (14)	O32—H32	0.82
C11—H11	0.93	O35—H35	0.82
C12—C13	1.408 (12)	O36—C37	1.421 (11)
C12—H12	0.93	O36—H36	0.82
C13—C14	1.394 (13)	C37—C38	1.496 (14)
C13—H13	0.93	C37—C39	1.499 (14)
C14—C15	1.406 (13)	C37—H37	0.98
C14—H14	0.93	C38—H38A	0.96
C15—C16	1.447 (14)	C38—H38B	0.96
O18—H18	0.82	C38—H38C	0.96
N19—C20	1.503 (14)	C39—H39A	0.96
N19—H19A	0.90	C39—H39B	0.96
N19—H19B	0.90	C39—H39C	0.96
C20—C21	1.523 (13)
N19—C1—C2	112.3 (7)	N19—C20—C21	110.7 (7)
N19—C1—H1A	109.2	N19—C20—H20A	109.5
C2—C1—H1A	109.2	C21—C20—H20A	109.5
N19—C1—H1B	109.1	N19—C20—H20B	109.5
C2—C1—H1B	109.1	C21—C20—H20B	109.5
H1A—C1—H1B	107.9	H20A—C20—H20B	108.1
O18—C2—C1	107.6 (7)	O22—C21—C20	105.5 (8)
O18—C2—C3	110.5 (7)	O22—C21—H21A	110.6
C1—C2—C3	109.4 (7)	C20—C21—H21A	110.7
O18—C2—H2	109.7	O22—C21—H21B	110.6
C1—C2—H2	109.7	C20—C21—H21B	110.6
C3—C2—H2	109.8	H21A—C21—H21B	108.7
O17—C3—C2	105.5 (7)	C23—O22—C21	119.7 (7)
O17—C3—H3A	110.6	O22—C23—C28	125.2 (9)
C2—C3—H3A	110.6	O22—C23—C24	115.2 (9)
O17—C3—H3B	110.6	C28—C23—C24	119.6 (8)
C2—C3—H3B	110.7	O29—C24—C25	124.2 (10)
H3A—C3—H3B	108.7	O29—C24—C23	115.7 (7)
O17—C4—C5	125.1 (7)	C25—C24—C23	120.0 (10)
O17—C4—C16	115.3 (8)	C24—C25—C26	119.9 (10)
C5—C4—C16	119.6 (8)	C24—C25—H25	120.1
C4—C5—C6	120.0 (8)	C26—C25—H25	120.0
C4—C5—H5	120.0	C27—C26—C25	120.1 (8)
C6—C5—H5	120.0	C27—C26—H26	119.9
C7—C6—C5	122.1 (9)	C25—C26—H26	120.0
C7—C6—H6	119.0	C26—C27—C28	120.3 (10)
C5—C6—H6	119.0	C26—C27—H27	119.9
C6—C7—C8	117.3 (9)	C28—C27—H27	119.9
C6—C7—H7	121.4	C23—C28—C27	120.0 (10)
C8—C7—H7	121.3	C23—C28—H28	120.0
N9—C8—C7	129.6 (8)	C27—C28—H28	120.0
N9—C8—C16	108.1 (8)	C24—O29—C30	117.0 (7)
C7—C8—C16	122.0 (8)	O29—C30—H30A	109.5
C8—N9—C10	109.8 (7)	O29—C30—H30B	109.5
C8—N9—H9	125.1	H30A—C30—H30B	109.5
C10—N9—H9	125.1	O29—C30—H30C	109.5
N9—C10—C11	129.7 (8)	H30A—C30—H30C	109.5
N9—C10—C15	108.6 (8)	H30B—C30—H30C	109.5
C11—C10—C15	121.6 (9)	O32—P31—O34	109.5 (4)
C12—C11—C10	117.9 (8)	O32—P31—O33	109.8 (4)
C12—C11—H11	121.1	O34—P31—O33	109.7 (4)
C10—C11—H11	121.1	O32—P31—O35	109.2 (4)
C11—C12—C13	121.3 (9)	O34—P31—O35	109.6 (5)
C11—C12—H12	119.3	O33—P31—O35	109.1 (4)
C13—C12—H12	119.3	P31—O32—H32	107
C14—C13—C12	120.7 (9)	P31—O35—H35	106
C14—C13—H13	119.6	C37—O36—H36	111
C12—C13—H13	119.7	O36—C37—C38	109.2 (9)
C13—C14—C15	119.1 (8)	O36—C37—C39	108.8 (8)
C13—C14—H14	120.4	C38—C37—C39	110.6 (8)
C15—C14—H14	120.4	O36—C37—H37	109.4
C14—C15—C10	119.2 (8)	C38—C37—H37	109.4
C14—C15—C16	134.5 (7)	C39—C37—H37	109.4
C10—C15—C16	106.1 (8)	C37—C38—H38A	109.5
C4—C16—C8	118.8 (9)	C37—C38—H38B	109.5
C4—C16—C15	133.7 (8)	H38A—C38—H38B	109.5
C8—C16—C15	107.3 (7)	C37—C38—H38C	109.5
C4—O17—C3	118.1 (7)	H38A—C38—H38C	109.4
C2—O18—H18	110	H38B—C38—H38C	109.5
C1—N19—C20	113.6 (7)	C37—C39—H39A	109.5
C1—N19—H19A	108.8	C37—C39—H39B	109.5
C20—N19—H19A	108.9	H39A—C39—H39B	109.5
C1—N19—H19B	108.9	C37—C39—H39C	109.5
C20—N19—H19B	108.9	H39A—C39—H39C	109.5
H19A—N19—H19B	107.7	H39B—C39—H39C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O18—H18···O34	0.82	1.89	2.681 (10)	165
N19—H19A···O34i	0.90	1.75	2.568 (10)	149
N19—H19B···O18	0.90	2.46	2.772 (11)	101
N19—H19B···O22	0.90	2.29	2.646 (10)	103
O32—H32···O33ii	0.82	1.90	2.672 (10)	156
O35—H35···O36iii	0.82	1.99	2.619 (9)	132
O36—H36···O33	0.82	2.00	2.590 (9)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O18—H18⋯O34	0.82	1.89	2.681 (10)	165
N19—H19A⋯O34i	0.90	1.75	2.568 (10)	149
N19—H19B⋯O18	0.90	2.46	2.772 (11)	101
N19—H19B⋯O22	0.90	2.29	2.646 (10)	103
O32—H32⋯O33ii	0.82	1.90	2.672 (10)	156
O35—H35⋯O36iii	0.82	1.99	2.619 (9)	132
O36—H36⋯O33	0.82	2.00	2.590 (9)	128

Symmetry codes: (i) ; (ii) ; (iii) .