A second polymorph of carvedilol

A second polymorph of the title compound [systematic name: 1-(9H-carbazol-4-yl­oxy)-3-[2-(2-methoxy­phen­oxy)ethyl­amino]­propan-2-ol], C₂₄H₂₆N₂O₄, is described. The other polymorph [Chen, Zeng, Yu & Xu (1998). Jiegou Huaxue (Chin. J. Struct. Chem.), 17, 325-328] also crystallizes in the space group P2₁/c, but differs in two torsion angles of the chain connecting the aromatic residues. On the other hand, the hydrogen-bond patterns of the two polymorphs are rather similar.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.106
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.93 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.31 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: PLATON and SHELXL97.

1-(9H-carbazol-4-yloxy)-3-[2-(2-methoxyphenoxy)ethylamino]propan-2-ol

Crystal data

C24H26N2O4	F(000) = 864
Mr = 406.47	Dx = 1.275 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11701 reflections
a = 15.5414 (14) Å	θ = 3.6–25.6°
b = 15.2050 (12) Å	µ = 0.09 mm^−1
c = 9.1174 (8) Å	T = 173 K
β = 100.730 (7)°	Block, colourless
V = 2116.8 (3) Å^3	0.36 × 0.33 × 0.32 mm
Z = 4

Data collection

Stoe IPDS-II two-circle diffractometer	3060 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
Graphite monochromator	θmax = 25.7°, θmin = 3.5°
ω scans	h = −18→17
12521 measured reflections	k = −18→18
3956 independent reflections	l = −11→11

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.106	w = 1/[σ^2(Fo^2) + (0.0583P)^2 + 0.3118P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3956 reflections	Δρmax = 0.29 e Å^−3
285 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0127 (14)

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
N1	0.79794 (9)	0.45572 (9)	1.00209 (15)	0.0337 (3)
H1	0.8386 (15)	0.4802 (13)	1.080 (2)	0.054 (6)*
O1	0.57727 (7)	0.28121 (6)	0.74549 (10)	0.0249 (2)
C2	0.54590 (10)	0.19722 (9)	0.68829 (15)	0.0248 (3)
H2A	0.5220	0.1640	0.7651	0.030*
H2B	0.5943	0.1627	0.6601	0.030*
C3	0.47465 (10)	0.21288 (9)	0.55219 (15)	0.0240 (3)
H3	0.4979	0.2532	0.4822	0.029*
C4	0.45150 (10)	0.12518 (9)	0.47455 (15)	0.0252 (3)
H4A	0.5041	0.1007	0.4426	0.030*
H4B	0.4331	0.0833	0.5460	0.030*
N5	0.38070 (9)	0.13415 (8)	0.34361 (13)	0.0256 (3)
H5	0.3338 (13)	0.1578 (11)	0.3760 (19)	0.033 (4)*
C6	0.35366 (10)	0.04768 (10)	0.27956 (17)	0.0285 (3)
H6A	0.3434	0.0074	0.3598	0.034*
H6B	0.4010	0.0226	0.2334	0.034*
C7	0.27093 (11)	0.05529 (12)	0.16310 (18)	0.0353 (4)
H7A	0.2795	0.0976	0.0846	0.042*
H7B	0.2554	−0.0026	0.1157	0.042*
O8	0.20205 (7)	0.08546 (8)	0.23780 (12)	0.0336 (3)
C11	0.64875 (9)	0.28176 (9)	0.86056 (15)	0.0228 (3)
C12	0.69113 (9)	0.36316 (9)	0.88714 (14)	0.0227 (3)
C13	0.76470 (10)	0.37090 (10)	1.00426 (16)	0.0277 (3)
C14	0.79510 (10)	0.29981 (12)	1.09711 (16)	0.0340 (4)
H14	0.8435	0.3057	1.1772	0.041*
C15	0.75182 (11)	0.22088 (11)	1.06741 (17)	0.0331 (4)
H15	0.7714	0.1716	1.1287	0.040*
C16	0.67959 (10)	0.21021 (10)	0.94964 (16)	0.0275 (3)
H16	0.6522	0.1544	0.9314	0.033*
C21	0.61951 (10)	0.48026 (10)	0.68870 (16)	0.0282 (3)
H21	0.5740	0.4441	0.6368	0.034*
C22	0.67916 (10)	0.44755 (9)	0.81189 (15)	0.0250 (3)
C23	0.74650 (10)	0.50272 (10)	0.88753 (17)	0.0300 (4)
C24	0.75577 (12)	0.58960 (11)	0.8424 (2)	0.0403 (4)
H24	0.8012	0.6263	0.8932	0.048*
C25	0.69615 (13)	0.62004 (11)	0.7208 (2)	0.0422 (4)
H25	0.7010	0.6788	0.6879	0.051*
C26	0.62877 (12)	0.56653 (10)	0.64484 (19)	0.0367 (4)
H26	0.5889	0.5897	0.5622	0.044*
O31	0.39653 (7)	0.25044 (7)	0.58808 (12)	0.0293 (3)
H31	0.4074 (15)	0.2858 (14)	0.671 (3)	0.060 (6)*
C81	0.12906 (11)	0.12093 (10)	0.14651 (16)	0.0311 (4)
C82	0.04736 (11)	0.08810 (11)	0.16397 (17)	0.0340 (4)
C83	−0.02822 (13)	0.12558 (15)	0.0817 (2)	0.0539 (5)
H83	−0.0842	0.1043	0.0926	0.065*
C84	−0.02162 (17)	0.19448 (17)	−0.0169 (2)	0.0665 (7)
H84	−0.0733	0.2201	−0.0726	0.080*
C85	0.05890 (19)	0.22567 (15)	−0.0343 (2)	0.0650 (7)
H85	0.0626	0.2722	−0.1025	0.078*
C86	0.13505 (15)	0.18920 (12)	0.0479 (2)	0.0480 (5)
H86	0.1907	0.2109	0.0365	0.058*
O87	0.04953 (8)	0.02091 (9)	0.26613 (13)	0.0432 (3)
C87	−0.03261 (14)	−0.01816 (17)	0.2804 (3)	0.0642 (6)
H87A	−0.0704	0.0266	0.3128	0.096*
H87B	−0.0224	−0.0656	0.3543	0.096*
H87C	−0.0611	−0.0421	0.1837	0.096*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0250 (7)	0.0405 (8)	0.0349 (7)	−0.0053 (6)	0.0036 (6)	−0.0123 (6)
O1	0.0220 (5)	0.0245 (5)	0.0264 (5)	−0.0011 (4)	0.0003 (4)	−0.0005 (4)
C2	0.0248 (8)	0.0224 (7)	0.0273 (7)	−0.0012 (6)	0.0046 (6)	−0.0004 (5)
C3	0.0214 (7)	0.0253 (7)	0.0265 (7)	−0.0011 (6)	0.0076 (6)	0.0010 (5)
C4	0.0229 (8)	0.0258 (7)	0.0266 (7)	−0.0002 (6)	0.0039 (6)	0.0011 (6)
N5	0.0214 (7)	0.0276 (6)	0.0271 (6)	−0.0012 (5)	0.0027 (5)	−0.0001 (5)
C6	0.0244 (8)	0.0297 (8)	0.0321 (8)	−0.0027 (6)	0.0072 (6)	−0.0045 (6)
C7	0.0264 (8)	0.0437 (9)	0.0353 (8)	−0.0025 (7)	0.0044 (7)	−0.0104 (7)
O8	0.0210 (6)	0.0472 (7)	0.0323 (6)	0.0002 (5)	0.0040 (5)	0.0057 (5)
C11	0.0185 (7)	0.0303 (7)	0.0203 (6)	0.0020 (6)	0.0057 (5)	−0.0007 (5)
C12	0.0192 (7)	0.0300 (7)	0.0198 (6)	0.0021 (6)	0.0058 (5)	−0.0021 (5)
C13	0.0204 (8)	0.0389 (8)	0.0250 (7)	−0.0001 (6)	0.0070 (6)	−0.0072 (6)
C14	0.0218 (8)	0.0549 (10)	0.0240 (7)	0.0053 (8)	0.0007 (6)	0.0010 (7)
C15	0.0261 (8)	0.0466 (9)	0.0277 (8)	0.0096 (7)	0.0080 (6)	0.0111 (7)
C16	0.0236 (8)	0.0314 (8)	0.0293 (7)	0.0023 (6)	0.0096 (6)	0.0055 (6)
C21	0.0303 (8)	0.0290 (8)	0.0267 (7)	0.0048 (6)	0.0096 (6)	−0.0017 (6)
C22	0.0245 (8)	0.0269 (7)	0.0261 (7)	0.0012 (6)	0.0110 (6)	−0.0044 (6)
C23	0.0269 (8)	0.0318 (8)	0.0340 (8)	−0.0008 (7)	0.0128 (7)	−0.0087 (6)
C24	0.0406 (10)	0.0296 (8)	0.0564 (11)	−0.0080 (7)	0.0233 (9)	−0.0151 (8)
C25	0.0543 (12)	0.0265 (8)	0.0536 (11)	0.0034 (8)	0.0303 (9)	0.0005 (7)
C26	0.0463 (11)	0.0321 (8)	0.0363 (8)	0.0104 (8)	0.0191 (8)	0.0037 (7)
O31	0.0226 (6)	0.0341 (6)	0.0312 (6)	0.0016 (5)	0.0048 (4)	−0.0056 (5)
C81	0.0307 (9)	0.0329 (8)	0.0279 (8)	0.0051 (7)	0.0006 (6)	−0.0011 (6)
C82	0.0277 (9)	0.0459 (9)	0.0268 (8)	0.0062 (7)	0.0010 (6)	−0.0046 (7)
C83	0.0315 (10)	0.0875 (16)	0.0396 (10)	0.0201 (10)	−0.0017 (8)	−0.0081 (10)
C84	0.0664 (16)	0.0873 (17)	0.0397 (11)	0.0463 (14)	−0.0061 (10)	0.0037 (11)
C85	0.090 (2)	0.0566 (13)	0.0475 (11)	0.0324 (13)	0.0105 (12)	0.0143 (10)
C86	0.0613 (13)	0.0365 (9)	0.0466 (10)	0.0062 (9)	0.0110 (9)	0.0073 (8)
O87	0.0228 (6)	0.0614 (8)	0.0454 (7)	−0.0064 (6)	0.0067 (5)	0.0071 (6)
C87	0.0343 (11)	0.0948 (17)	0.0671 (13)	−0.0243 (11)	0.0193 (10)	−0.0069 (12)

Geometric parameters (Å, º)

N1—C23	1.389 (2)	C15—C16	1.411 (2)
N1—C13	1.391 (2)	C15—H15	0.9500
N1—H1	0.94 (2)	C16—H16	0.9500
O1—C11	1.3787 (17)	C21—C26	1.387 (2)
O1—C2	1.4304 (16)	C21—C22	1.407 (2)
C2—C3	1.520 (2)	C21—H21	0.9500
C2—H2A	0.9900	C22—C23	1.416 (2)
C2—H2B	0.9900	C23—C24	1.399 (2)
C3—O31	1.4335 (18)	C24—C25	1.385 (3)
C3—C4	1.521 (2)	C24—H24	0.9500
C3—H3	1.0000	C25—C26	1.403 (3)
C4—N5	1.4716 (19)	C25—H25	0.9500
C4—H4A	0.9900	C26—H26	0.9500
C4—H4B	0.9900	O31—H31	0.92 (2)
N5—C6	1.4679 (19)	C81—C86	1.388 (2)
N5—H5	0.910 (19)	C81—C82	1.401 (2)
C6—C7	1.512 (2)	C82—O87	1.379 (2)
C6—H6A	0.9900	C82—C83	1.392 (2)
C6—H6B	0.9900	C83—C84	1.397 (3)
C7—O8	1.4462 (19)	C83—H83	0.9500
C7—H7A	0.9900	C84—C85	1.375 (4)
C7—H7B	0.9900	C84—H84	0.9500
O8—C81	1.3853 (19)	C85—C86	1.393 (3)
C11—C16	1.388 (2)	C85—H85	0.9500
C11—C12	1.402 (2)	C86—H86	0.9500
C12—C13	1.417 (2)	O87—C87	1.436 (2)
C12—C22	1.451 (2)	C87—H87A	0.9800
C13—C14	1.400 (2)	C87—H87B	0.9800
C14—C15	1.378 (2)	C87—H87C	0.9800
C14—H14	0.9500
C23—N1—C13	108.93 (13)	C14—C15—C16	122.67 (14)
C23—N1—H1	125.5 (13)	C14—C15—H15	118.7
C13—N1—H1	123.8 (13)	C16—C15—H15	118.7
C11—O1—C2	117.04 (11)	C11—C16—C15	119.61 (14)
O1—C2—C3	107.74 (11)	C11—C16—H16	120.2
O1—C2—H2A	110.2	C15—C16—H16	120.2
C3—C2—H2A	110.2	C26—C21—C22	118.43 (15)
O1—C2—H2B	110.2	C26—C21—H21	120.8
C3—C2—H2B	110.2	C22—C21—H21	120.8
H2A—C2—H2B	108.5	C21—C22—C23	119.78 (14)
O31—C3—C2	113.28 (11)	C21—C22—C12	134.22 (14)
O31—C3—C4	108.57 (12)	C23—C22—C12	105.99 (13)
C2—C3—C4	108.40 (11)	N1—C23—C24	129.09 (16)
O31—C3—H3	108.8	N1—C23—C22	109.34 (13)
C2—C3—H3	108.8	C24—C23—C22	121.55 (16)
C4—C3—H3	108.8	C25—C24—C23	117.44 (17)
N5—C4—C3	111.88 (12)	C25—C24—H24	121.3
N5—C4—H4A	109.2	C23—C24—H24	121.3
C3—C4—H4A	109.2	C24—C25—C26	121.85 (16)
N5—C4—H4B	109.2	C24—C25—H25	119.1
C3—C4—H4B	109.2	C26—C25—H25	119.1
H4A—C4—H4B	107.9	C21—C26—C25	120.95 (17)
C6—N5—C4	110.81 (11)	C21—C26—H26	119.5
C6—N5—H5	107.2 (11)	C25—C26—H26	119.5
C4—N5—H5	107.2 (11)	C3—O31—H31	112.8 (15)
N5—C6—C7	110.73 (13)	O8—C81—C86	122.30 (16)
N5—C6—H6A	109.5	O8—C81—C82	116.82 (14)
C7—C6—H6A	109.5	C86—C81—C82	120.79 (16)
N5—C6—H6B	109.5	O87—C82—C83	125.40 (17)
C7—C6—H6B	109.5	O87—C82—C81	115.61 (14)
H6A—C6—H6B	108.1	C83—C82—C81	118.98 (17)
O8—C7—C6	107.50 (12)	C82—C83—C84	119.9 (2)
O8—C7—H7A	110.2	C82—C83—H83	120.1
C6—C7—H7A	110.2	C84—C83—H83	120.1
O8—C7—H7B	110.2	C85—C84—C83	120.69 (19)
C6—C7—H7B	110.2	C85—C84—H84	119.7
H7A—C7—H7B	108.5	C83—C84—H84	119.7
C81—O8—C7	115.83 (11)	C84—C85—C86	120.1 (2)
O1—C11—C16	125.58 (13)	C84—C85—H85	120.0
O1—C11—C12	115.03 (12)	C86—C85—H85	120.0
C16—C11—C12	119.39 (13)	C81—C86—C85	119.6 (2)
C11—C12—C13	119.40 (13)	C81—C86—H86	120.2
C11—C12—C22	133.20 (13)	C85—C86—H86	120.2
C13—C12—C22	107.31 (13)	C82—O87—C87	117.22 (15)
N1—C13—C14	129.82 (14)	O87—C87—H87A	109.5
N1—C13—C12	108.42 (13)	O87—C87—H87B	109.5
C14—C13—C12	121.73 (14)	H87A—C87—H87B	109.5
C15—C14—C13	117.15 (14)	O87—C87—H87C	109.5
C15—C14—H14	121.4	H87A—C87—H87C	109.5
C13—C14—H14	121.4	H87B—C87—H87C	109.5
C11—O1—C2—C3	−173.50 (11)	C13—C12—C22—C21	178.97 (15)
O1—C2—C3—O31	−68.99 (15)	C11—C12—C22—C23	−176.34 (15)
O1—C2—C3—C4	170.44 (11)	C13—C12—C22—C23	0.00 (15)
O31—C3—C4—N5	54.77 (15)	C13—N1—C23—C24	−179.01 (15)
C2—C3—C4—N5	178.21 (12)	C13—N1—C23—C22	−0.84 (16)
C3—C4—N5—C6	−174.39 (12)	C21—C22—C23—N1	−178.64 (12)
C4—N5—C6—C7	169.95 (12)	C12—C22—C23—N1	0.51 (15)
N5—C6—C7—O8	−63.66 (16)	C21—C22—C23—C24	−0.3 (2)
C6—C7—O8—C81	161.69 (13)	C12—C22—C23—C24	178.84 (13)
C2—O1—C11—C16	−16.78 (19)	N1—C23—C24—C25	178.27 (15)
C2—O1—C11—C12	164.14 (11)	C22—C23—C24—C25	0.3 (2)
O1—C11—C12—C13	179.23 (12)	C23—C24—C25—C26	0.0 (2)
C16—C11—C12—C13	0.1 (2)	C22—C21—C26—C25	0.3 (2)
O1—C11—C12—C22	−4.8 (2)	C24—C25—C26—C21	−0.3 (2)
C16—C11—C12—C22	176.07 (14)	C7—O8—C81—C86	−54.2 (2)
C23—N1—C13—C14	178.73 (15)	C7—O8—C81—C82	129.41 (15)
C23—N1—C13—C12	0.84 (16)	O8—C81—C82—O87	−2.9 (2)
C11—C12—C13—N1	176.43 (12)	C86—C81—C82—O87	−179.37 (15)
C22—C12—C13—N1	−0.51 (15)	O8—C81—C82—C83	175.89 (14)
C11—C12—C13—C14	−1.7 (2)	C86—C81—C82—C83	−0.6 (2)
C22—C12—C13—C14	−178.61 (13)	O87—C82—C83—C84	178.99 (17)
N1—C13—C14—C15	−175.93 (15)	C81—C82—C83—C84	0.4 (3)
C12—C13—C14—C15	1.7 (2)	C82—C83—C84—C85	0.3 (3)
C13—C14—C15—C16	−0.2 (2)	C83—C84—C85—C86	−0.6 (3)
O1—C11—C16—C15	−177.70 (13)	O8—C81—C86—C85	−176.07 (16)
C12—C11—C16—C15	1.3 (2)	C82—C81—C86—C85	0.2 (3)
C14—C15—C16—C11	−1.3 (2)	C84—C85—C86—C81	0.4 (3)
C26—C21—C22—C23	0.0 (2)	C83—C82—O87—C87	5.1 (2)
C26—C21—C22—C12	−178.84 (14)	C81—C82—O87—C87	−176.22 (16)
C11—C12—C22—C21	2.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O31—H31···N5^i	0.92 (2)	2.09 (2)	2.9633 (16)	158 (2)
N1—H1···O87^ii	0.94 (2)	2.11 (2)	3.0336 (19)	167.4 (18)
N5—H5···O8	0.910 (19)	2.456 (18)	2.8619 (17)	107.3 (13)
N5—H5···O31	0.910 (19)	2.443 (17)	2.8198 (17)	105.0 (13)

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