Crystal structure analysis of ebastine [4-(4-benzhydryloxy-1-piperidyl)-1-(4-tert-butylphenyl) butan-1-one]: an oral histamine antagonist

Ebastine belongs to the category of second-generation non-sedating H1 receptor antagonists and is chiefly used for the treatment of allergic rhinitis and chronic urticaria. The present paper reports findings on the crystal and molecular structure of ebastine, employing the technique of single-crystal X-ray diffraction. Ebastine crystallizes in the monoclinic P2₁/c space group with unit-cell dimensions a = 16.5890 (12), b = 10.9575 (8), c = 16.6795 (11) Å, β = 113.623 (2)°, V = 2777.8 (3) ų, Z = 4 and calculated density amounting to 1.123 Mg m⁻³. The structure factor value was observed 1016 and final R = 0.0496 for 4360 unique reflections. The piperidine ring in the ebastine molecule was found to exist in a chair conformation, and the C—N bond length was 1.459 (3) Å, thereby showing good agreement with the standard C—N bond length of 1.472 Å.

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2/SAINT (Bruker, 2004); data reduction: SAINT/XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008, 2014); molecular graphics: ORTEP 32 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008, 2014).

(I)

Crystal data

C32H39NO2	F(000) = 1016
Mr = 469.64	Dx = 1.123 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.5890 (12) Å	Cell parameters from 6607 reflections
b = 10.9575 (8) Å	θ = 2.2–22.1°
c = 16.6795 (11) Å	µ = 0.07 mm^−1
β = 113.623 (2)°	T = 293 K
V = 2777.8 (3) Å^3	Block, colourless
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection

Bruker axs kappa apex2 CCD Diffractometer	4360 independent reflections
Radiation source: fine-focus sealed tube	2798 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
ω and φ scan	θmax = 24.0°, θmin = 2.3°
Absorption correction: multi-scan SADABS(Bruker,1999)	h = −18→16
Tmin = 0.969, Tmax = 0.997	k = −12→11
22144 measured reflections	l = −13→19

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.155	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0732P)^2 + 0.5535P] where P = (Fo^2 + 2Fc^2)/3
4360 reflections	(Δ/σ)max < 0.001
316 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

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
C1	1.28905 (15)	−0.1957 (2)	0.48514 (15)	0.0676 (7)
H1	1.3304	−0.2521	0.5195	0.081*
C2	1.29079 (16)	−0.1583 (2)	0.40708 (15)	0.0706 (7)
H2	1.3329	−0.1895	0.3890	0.085*
C3	1.23043 (16)	−0.0753 (2)	0.35620 (15)	0.0683 (7)
H3	1.2314	−0.0499	0.3034	0.082*
C4	1.16870 (16)	−0.0297 (2)	0.38303 (15)	0.0687 (7)
H4	1.1278	0.0271	0.3486	0.082*
C5	1.16673 (15)	−0.0676 (2)	0.46089 (15)	0.0617 (6)
H5	1.1241	−0.0364	0.4783	0.074*
C6	1.22698 (14)	−0.15100 (19)	0.51343 (13)	0.0547 (6)
C7	1.34001 (19)	−0.3380 (3)	0.69630 (18)	0.0869 (9)
H7	1.3037	−0.4039	0.6700	0.104*
C8	1.4220 (3)	−0.3583 (5)	0.7626 (3)	0.1299 (16)
H8	1.4405	−0.4376	0.7805	0.156*
C9	1.4752 (3)	−0.2632 (7)	0.8015 (3)	0.153 (3)
H9	1.5303	−0.2772	0.8459	0.183*
C10	1.4484 (3)	−0.1472 (5)	0.7758 (3)	0.1369 (16)
H10	1.4850	−0.0819	0.8028	0.164*
C11	1.3667 (2)	−0.1264 (3)	0.7095 (2)	0.1007 (10)
H11	1.3487	−0.0468	0.6921	0.121*
C12	1.31197 (16)	−0.2216 (2)	0.66895 (15)	0.0659 (7)
C13	1.22271 (15)	−0.1987 (2)	0.59675 (14)	0.0593 (6)
H13	1.1904	−0.2761	0.5833	0.071*
C14	1.13530 (15)	−0.1672 (2)	0.67884 (14)	0.0592 (6)
H14	1.1743	−0.2315	0.7145	0.071*
C15	1.12615 (17)	−0.0707 (2)	0.73836 (16)	0.0717 (7)
H15A	1.0908	−0.0040	0.7037	0.086*
H15B	1.1838	−0.0387	0.7748	0.086*
C16	1.08316 (15)	−0.1223 (2)	0.79580 (15)	0.0665 (6)
H16A	1.1206	−0.1852	0.8333	0.080*
H16B	1.0768	−0.0581	0.8329	0.080*
C17	1.00460 (16)	−0.2686 (2)	0.68549 (16)	0.0696 (7)
H17A	0.9465	−0.3003	0.6502	0.084*
H17B	1.0397	−0.3352	0.7205	0.084*
C18	1.04633 (16)	−0.2218 (2)	0.62613 (15)	0.0701 (7)
H18A	1.0526	−0.2883	0.5907	0.084*
H18B	1.0086	−0.1604	0.5871	0.084*
C19	0.95458 (16)	−0.2239 (2)	0.79770 (16)	0.0674 (6)
H19A	0.9935	−0.2842	0.8368	0.081*
H19B	0.9012	−0.2657	0.7602	0.081*
C20	0.93144 (16)	−0.1317 (2)	0.85136 (16)	0.0708 (7)
H20A	0.9005	−0.0641	0.8142	0.085*
H20B	0.9850	−0.1000	0.8964	0.085*
C21	0.87461 (15)	−0.1858 (2)	0.89369 (15)	0.0642 (6)
H21A	0.8244	−0.2251	0.8487	0.077*
H21B	0.9081	−0.2486	0.9345	0.077*
C22	0.84187 (17)	−0.0978 (2)	0.94110 (17)	0.0716 (7)
C23	0.77777 (14)	−0.1366 (2)	0.97738 (14)	0.0591 (6)
C24	0.74514 (17)	−0.0520 (2)	1.01783 (18)	0.0791 (8)
H24	0.7633	0.0288	1.0215	0.095*
C25	0.68638 (16)	−0.0854 (2)	1.05275 (17)	0.0757 (7)
H25	0.6652	−0.0259	1.0790	0.091*
C26	0.65752 (14)	−0.2039 (2)	1.05036 (13)	0.0564 (6)
C27	0.69059 (16)	−0.2877 (2)	1.00971 (16)	0.0689 (7)
H27	0.6728	−0.3687	1.0064	0.083*
C28	0.74927 (15)	−0.2552 (2)	0.97381 (16)	0.0663 (7)
H28	0.7699	−0.3143	0.9467	0.080*
C29	0.59613 (16)	−0.2388 (2)	1.09456 (15)	0.0671 (7)
C30	0.52232 (19)	−0.1459 (3)	1.0735 (2)	0.1030 (10)
H30A	0.5468	−0.0674	1.0958	0.154*
H30B	0.4833	−0.1706	1.1003	0.154*
H30C	0.4902	−0.1410	1.0113	0.154*
C31	0.6512 (2)	−0.2454 (4)	1.19272 (18)	0.1227 (13)
H31A	0.7070	−0.2824	1.2031	0.184*
H31B	0.6209	−0.2934	1.2201	0.184*
H31C	0.6605	−0.1645	1.2168	0.184*
C32	0.55232 (19)	−0.3632 (3)	1.0635 (2)	0.0926 (9)
H32A	0.5968	−0.4251	1.0771	0.139*
H32B	0.5186	−0.3608	1.0015	0.139*
H32C	0.5142	−0.3814	1.0926	0.139*
N1	0.99695 (12)	−0.17383 (16)	0.74325 (12)	0.0576 (5)
O1	1.17409 (11)	−0.11368 (14)	0.62459 (10)	0.0712 (5)
O2	0.86762 (16)	0.00780 (19)	0.95050 (17)	0.1245 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0575 (15)	0.0866 (17)	0.0639 (14)	0.0116 (13)	0.0298 (12)	0.0086 (13)
C2	0.0570 (15)	0.0967 (19)	0.0655 (15)	−0.0004 (14)	0.0324 (13)	−0.0007 (14)
C3	0.0678 (17)	0.0790 (17)	0.0563 (14)	−0.0124 (14)	0.0230 (13)	−0.0010 (13)
C4	0.0704 (17)	0.0674 (16)	0.0610 (15)	0.0036 (13)	0.0187 (13)	0.0070 (12)
C5	0.0577 (15)	0.0627 (14)	0.0655 (14)	0.0037 (12)	0.0257 (12)	−0.0015 (12)
C6	0.0522 (14)	0.0582 (14)	0.0560 (12)	0.0006 (11)	0.0243 (11)	0.0001 (11)
C7	0.084 (2)	0.112 (2)	0.0794 (18)	0.0351 (17)	0.0482 (17)	0.0343 (16)
C8	0.110 (3)	0.203 (5)	0.096 (3)	0.075 (3)	0.062 (3)	0.075 (3)
C9	0.082 (3)	0.319 (9)	0.065 (2)	0.037 (4)	0.037 (2)	0.031 (4)
C10	0.091 (3)	0.234 (6)	0.082 (3)	−0.023 (3)	0.031 (2)	−0.044 (3)
C11	0.091 (2)	0.124 (3)	0.083 (2)	−0.005 (2)	0.0308 (19)	−0.0188 (19)
C12	0.0673 (17)	0.0841 (18)	0.0571 (14)	0.0098 (15)	0.0361 (13)	0.0039 (14)
C13	0.0611 (15)	0.0586 (14)	0.0677 (14)	0.0108 (11)	0.0355 (13)	0.0044 (11)
C14	0.0585 (15)	0.0628 (14)	0.0653 (14)	0.0104 (11)	0.0343 (12)	0.0091 (11)
C15	0.0719 (17)	0.0758 (16)	0.0826 (16)	−0.0059 (13)	0.0468 (14)	−0.0077 (13)
C16	0.0652 (16)	0.0732 (16)	0.0689 (15)	−0.0033 (13)	0.0351 (13)	−0.0077 (12)
C17	0.0594 (15)	0.0787 (17)	0.0722 (15)	−0.0028 (13)	0.0279 (13)	−0.0095 (13)
C18	0.0672 (16)	0.0862 (17)	0.0605 (14)	0.0093 (14)	0.0293 (13)	−0.0034 (13)
C19	0.0626 (15)	0.0702 (15)	0.0788 (16)	0.0035 (12)	0.0380 (13)	0.0079 (13)
C20	0.0678 (16)	0.0785 (17)	0.0770 (16)	0.0025 (13)	0.0404 (14)	0.0104 (13)
C21	0.0569 (14)	0.0772 (16)	0.0624 (14)	0.0029 (12)	0.0279 (12)	0.0091 (12)
C22	0.0708 (17)	0.0644 (17)	0.0900 (18)	0.0039 (13)	0.0433 (15)	0.0110 (14)
C23	0.0536 (14)	0.0628 (15)	0.0645 (14)	0.0040 (11)	0.0277 (12)	0.0104 (12)
C24	0.0856 (19)	0.0650 (16)	0.104 (2)	−0.0127 (14)	0.0558 (17)	−0.0097 (14)
C25	0.0766 (18)	0.0726 (18)	0.0948 (19)	−0.0075 (14)	0.0520 (16)	−0.0140 (14)
C26	0.0491 (13)	0.0661 (15)	0.0534 (12)	0.0034 (11)	0.0199 (11)	0.0081 (11)
C27	0.0723 (17)	0.0590 (15)	0.0860 (17)	0.0033 (12)	0.0428 (15)	0.0100 (13)
C28	0.0702 (16)	0.0646 (16)	0.0783 (16)	0.0092 (12)	0.0445 (14)	0.0090 (12)
C29	0.0600 (15)	0.0809 (17)	0.0678 (15)	0.0028 (13)	0.0334 (13)	0.0085 (13)
C30	0.082 (2)	0.099 (2)	0.154 (3)	0.0089 (17)	0.074 (2)	0.010 (2)
C31	0.101 (2)	0.206 (4)	0.0650 (18)	−0.021 (2)	0.0381 (18)	0.015 (2)
C32	0.084 (2)	0.093 (2)	0.116 (2)	−0.0119 (16)	0.0563 (18)	0.0118 (17)
N1	0.0497 (11)	0.0654 (12)	0.0616 (11)	0.0057 (9)	0.0265 (9)	0.0049 (9)
O1	0.0865 (12)	0.0655 (10)	0.0854 (11)	0.0196 (9)	0.0592 (10)	0.0147 (8)
O2	0.153 (2)	0.0784 (15)	0.206 (3)	−0.0167 (14)	0.138 (2)	−0.0074 (15)

Geometric parameters (Å, º)

C1—C2	1.376 (3)	C17—H17B	0.9700
C1—C6	1.383 (3)	C18—H18A	0.9700
C1—H1	0.9300	C18—H18B	0.9700
C2—C3	1.368 (3)	C19—N1	1.460 (3)
C2—H2	0.9300	C19—C20	1.498 (3)
C3—C4	1.366 (3)	C19—H19A	0.9700
C3—H3	0.9300	C19—H19B	0.9700
C4—C5	1.376 (3)	C20—C21	1.507 (3)
C4—H4	0.9300	C20—H20A	0.9700
C5—C6	1.379 (3)	C20—H20B	0.9700
C5—H5	0.9300	C21—C22	1.482 (3)
C6—C13	1.513 (3)	C21—H21A	0.9700
C7—C12	1.372 (4)	C21—H21B	0.9700
C7—C8	1.385 (5)	C22—O2	1.221 (3)
C7—H7	0.9300	C22—C23	1.481 (3)
C8—C9	1.352 (7)	C23—C28	1.376 (3)
C8—H8	0.9300	C23—C24	1.378 (3)
C9—C10	1.358 (6)	C24—C25	1.371 (3)
C9—H9	0.9300	C24—H24	0.9300
C10—C11	1.382 (5)	C25—C26	1.379 (3)
C10—H10	0.9300	C25—H25	0.9300
C11—C12	1.371 (4)	C26—C27	1.379 (3)
C11—H11	0.9300	C26—C29	1.526 (3)
C12—C13	1.509 (3)	C27—C28	1.379 (3)
C13—O1	1.427 (2)	C27—H27	0.9300
C13—H13	0.9800	C28—H28	0.9300
C14—O1	1.430 (2)	C29—C30	1.522 (3)
C14—C15	1.500 (3)	C29—C31	1.524 (4)
C14—C18	1.506 (3)	C29—C32	1.533 (4)
C14—H14	0.9800	C30—H30A	0.9600
C15—C16	1.515 (3)	C30—H30B	0.9600
C15—H15A	0.9700	C30—H30C	0.9600
C15—H15B	0.9700	C31—H31A	0.9600
C16—N1	1.459 (3)	C31—H31B	0.9600
C16—H16A	0.9700	C31—H31C	0.9600
C16—H16B	0.9700	C32—H32A	0.9600
C17—N1	1.456 (3)	C32—H32B	0.9600
C17—C18	1.507 (3)	C32—H32C	0.9600
C17—H17A	0.9700
C2—C1—C6	121.2 (2)	C17—C18—H18B	109.5
C2—C1—H1	119.4	H18A—C18—H18B	108.1
C6—C1—H1	119.4	N1—C19—C20	114.87 (19)
C3—C2—C1	119.8 (2)	N1—C19—H19A	108.5
C3—C2—H2	120.1	C20—C19—H19A	108.5
C1—C2—H2	120.1	N1—C19—H19B	108.5
C4—C3—C2	119.9 (2)	C20—C19—H19B	108.5
C4—C3—H3	120.0	H19A—C19—H19B	107.5
C2—C3—H3	120.0	C19—C20—C21	111.9 (2)
C3—C4—C5	120.2 (2)	C19—C20—H20A	109.2
C3—C4—H4	119.9	C21—C20—H20A	109.2
C5—C4—H4	119.9	C19—C20—H20B	109.2
C4—C5—C6	121.0 (2)	C21—C20—H20B	109.2
C4—C5—H5	119.5	H20A—C20—H20B	107.9
C6—C5—H5	119.5	C22—C21—C20	115.2 (2)
C5—C6—C1	117.9 (2)	C22—C21—H21A	108.5
C5—C6—C13	121.62 (19)	C20—C21—H21A	108.5
C1—C6—C13	120.4 (2)	C22—C21—H21B	108.5
C12—C7—C8	120.6 (4)	C20—C21—H21B	108.5
C12—C7—H7	119.7	H21A—C21—H21B	107.5
C8—C7—H7	119.7	O2—C22—C23	119.4 (2)
C9—C8—C7	120.2 (5)	O2—C22—C21	120.1 (2)
C9—C8—H8	119.9	C23—C22—C21	120.5 (2)
C7—C8—H8	119.9	C28—C23—C24	117.4 (2)
C8—C9—C10	120.1 (5)	C28—C23—C22	123.0 (2)
C8—C9—H9	119.9	C24—C23—C22	119.6 (2)
C10—C9—H9	119.9	C25—C24—C23	121.0 (2)
C9—C10—C11	119.9 (5)	C25—C24—H24	119.5
C9—C10—H10	120.0	C23—C24—H24	119.5
C11—C10—H10	120.0	C24—C25—C26	122.5 (2)
C12—C11—C10	120.8 (4)	C24—C25—H25	118.8
C12—C11—H11	119.6	C26—C25—H25	118.8
C10—C11—H11	119.6	C25—C26—C27	116.1 (2)
C11—C12—C7	118.3 (3)	C25—C26—C29	120.9 (2)
C11—C12—C13	120.8 (3)	C27—C26—C29	123.0 (2)
C7—C12—C13	120.9 (3)	C28—C27—C26	122.0 (2)
O1—C13—C12	110.54 (18)	C28—C27—H27	119.0
O1—C13—C6	108.28 (17)	C26—C27—H27	119.0
C12—C13—C6	113.48 (18)	C23—C28—C27	121.0 (2)
O1—C13—H13	108.1	C23—C28—H28	119.5
C12—C13—H13	108.1	C27—C28—H28	119.5
C6—C13—H13	108.1	C30—C29—C31	111.1 (2)
O1—C14—C15	108.66 (18)	C30—C29—C26	110.6 (2)
O1—C14—C18	112.19 (18)	C31—C29—C26	107.6 (2)
C15—C14—C18	109.33 (18)	C30—C29—C32	106.8 (2)
O1—C14—H14	108.9	C31—C29—C32	108.7 (2)
C15—C14—H14	108.9	C26—C29—C32	112.2 (2)
C18—C14—H14	108.9	C29—C30—H30A	109.5
C14—C15—C16	110.69 (19)	C29—C30—H30B	109.5
C14—C15—H15A	109.5	H30A—C30—H30B	109.5
C16—C15—H15A	109.5	C29—C30—H30C	109.5
C14—C15—H15B	109.5	H30A—C30—H30C	109.5
C16—C15—H15B	109.5	H30B—C30—H30C	109.5
H15A—C15—H15B	108.1	C29—C31—H31A	109.5
N1—C16—C15	111.18 (19)	C29—C31—H31B	109.5
N1—C16—H16A	109.4	H31A—C31—H31B	109.5
C15—C16—H16A	109.4	C29—C31—H31C	109.5
N1—C16—H16B	109.4	H31A—C31—H31C	109.5
C15—C16—H16B	109.4	H31B—C31—H31C	109.5
H16A—C16—H16B	108.0	C29—C32—H32A	109.5
N1—C17—C18	112.2 (2)	C29—C32—H32B	109.5
N1—C17—H17A	109.2	H32A—C32—H32B	109.5
C18—C17—H17A	109.2	C29—C32—H32C	109.5
N1—C17—H17B	109.2	H32A—C32—H32C	109.5
C18—C17—H17B	109.2	H32B—C32—H32C	109.5
H17A—C17—H17B	107.9	C17—N1—C16	110.42 (17)
C14—C18—C17	110.61 (18)	C17—N1—C19	109.58 (18)
C14—C18—H18A	109.5	C16—N1—C19	111.85 (17)
C17—C18—H18A	109.5	C13—O1—C14	113.23 (16)
C14—C18—H18B	109.5
C6—C1—C2—C3	0.2 (4)	C20—C21—C22—O2	−6.5 (4)
C1—C2—C3—C4	0.0 (4)	C20—C21—C22—C23	173.4 (2)
C2—C3—C4—C5	−0.3 (4)	O2—C22—C23—C28	−176.3 (3)
C3—C4—C5—C6	0.5 (4)	C21—C22—C23—C28	3.8 (4)
C4—C5—C6—C1	−0.3 (3)	O2—C22—C23—C24	2.8 (4)
C4—C5—C6—C13	−176.6 (2)	C21—C22—C23—C24	−177.1 (2)
C2—C1—C6—C5	0.0 (3)	C28—C23—C24—C25	−0.2 (4)
C2—C1—C6—C13	176.4 (2)	C22—C23—C24—C25	−179.4 (2)
C12—C7—C8—C9	0.3 (5)	C23—C24—C25—C26	0.7 (4)
C7—C8—C9—C10	0.2 (6)	C24—C25—C26—C27	−0.7 (4)
C8—C9—C10—C11	−0.3 (6)	C24—C25—C26—C29	176.5 (2)
C9—C10—C11—C12	0.0 (5)	C25—C26—C27—C28	0.2 (3)
C10—C11—C12—C7	0.5 (4)	C29—C26—C27—C28	−176.8 (2)
C10—C11—C12—C13	179.8 (2)	C24—C23—C28—C27	−0.2 (4)
C8—C7—C12—C11	−0.6 (4)	C22—C23—C28—C27	178.9 (2)
C8—C7—C12—C13	−179.9 (2)	C26—C27—C28—C23	0.2 (4)
C11—C12—C13—O1	−52.7 (3)	C25—C26—C29—C30	45.2 (3)
C7—C12—C13—O1	126.7 (2)	C27—C26—C29—C30	−137.9 (3)
C11—C12—C13—C6	69.2 (3)	C25—C26—C29—C31	−76.3 (3)
C7—C12—C13—C6	−111.5 (2)	C27—C26—C29—C31	100.6 (3)
C5—C6—C13—O1	−21.7 (3)	C25—C26—C29—C32	164.2 (2)
C1—C6—C13—O1	162.1 (2)	C27—C26—C29—C32	−18.8 (3)
C5—C6—C13—C12	−144.8 (2)	C18—C17—N1—C16	−57.5 (2)
C1—C6—C13—C12	39.0 (3)	C18—C17—N1—C19	178.86 (19)
O1—C14—C15—C16	178.60 (19)	C15—C16—N1—C17	57.7 (2)
C18—C14—C15—C16	55.8 (3)	C15—C16—N1—C19	−179.95 (19)
C14—C15—C16—N1	−57.9 (3)	C20—C19—N1—C17	−171.9 (2)
O1—C14—C18—C17	−175.63 (18)	C20—C19—N1—C16	65.3 (3)
C15—C14—C18—C17	−55.0 (3)	C12—C13—O1—C14	−78.9 (2)
N1—C17—C18—C14	56.6 (3)	C6—C13—O1—C14	156.18 (18)
N1—C19—C20—C21	170.28 (19)	C15—C14—O1—C13	152.28 (19)
C19—C20—C21—C22	−174.5 (2)	C18—C14—O1—C13	−86.7 (2)