8-Methyl-4-phenyl-2,3,3a,4,5,9b-hexa-hydro-furo[3,2-c]quinoline.

The title compound, C(18)H(19)NO, was synthesized from the multi-component one-pot reaction between p-toluidine, benzaldehyde and 2,3-dihydro-furan in the presence of palladium dichloride. There are two mol-ecules in the asymmetric unit. The crystal packing is stabilized by classical inter-molecular N-H⋯O hydrogen bonds.

Related literature

For heterocyclic scaffolds of biologically active alkaloids, see: Johnson et al. (1989 ▶); Yamada et al. (1992 ▶); Katritzky & Rachwal (1996 ▶). For the synthesis of related compounds, see: Buonora et al. (2001 ▶); Syamala (2005 ▶).

Experimental

Crystal data

C18H19NO

M = 265.34

Monoclinic,

a = 12.751 (4) Å

b = 17.780 (5) Å

c = 17.516 (4) Å

β = 132.426 (14)°

V = 2931.3 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 295 K

0.30 × 0.15 × 0.15 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.987, T max = 0.989

14911 measured reflections

5280 independent reflections

2114 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.186

S = 1.17

5280 reflections

315 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809051125/rk2180sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051125/rk2180Isup2.hkl

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

C18H19NO	F(000) = 1136
Mr = 265.34	Dx = 1.202 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1233 reflections
a = 12.751 (4) Å	θ = 2.3–18.3°
b = 17.780 (5) Å	µ = 0.07 mm−1
c = 17.516 (4) Å	T = 295 K
β = 132.426 (14)°	Block, colourless
V = 2931.3 (15) Å3	0.30 × 0.15 × 0.15 mm
Z = 8

Bruker APEXII area-detector diffractometer	5280 independent reflections
Radiation source: fine-focus sealed tube	2114 reflections with I > 2σ(I)
graphite	Rint = 0.067
φ and ω scans	θmax = 25.2°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −15→13
Tmin = 0.987, Tmax = 0.989	k = −19→21
14911 measured reflections	l = −19→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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186	H-atom parameters constrained
S = 1.17	w = 1/[σ2(Fo2) + (0.045P)2 + 0.45P] where P = (Fo2 + 2Fc2)/3
5280 reflections	(Δ/σ)max < 0.001
315 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. All s.u.'s (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
N1	0.6400 (3)	0.92041 (17)	0.1751 (2)	0.0704 (9)
H1	0.6805	0.8939	0.1601	0.084*
C1	0.8237 (5)	1.2230 (2)	0.3116 (3)	0.1063 (16)
H1A	0.8247	1.2483	0.2637	0.159*
H1B	0.9177	1.2230	0.3790	0.159*
H1C	0.7600	1.2485	0.3144	0.159*
C2	0.7734 (4)	1.14134 (12)	0.2756 (2)	0.0783 (12)
C3	0.8651 (2)	1.08924 (18)	0.28789 (19)	0.0806 (12)
H3	0.9558	1.1038	0.3175	0.097*
C4	0.8212 (3)	1.01531 (16)	0.2559 (2)	0.0746 (11)
H4	0.8825	0.9804	0.2641	0.090*
C5	0.6856 (3)	0.99347 (11)	0.2116 (2)	0.0636 (10)
C6	0.5939 (2)	1.04557 (16)	0.19939 (19)	0.0698 (11)
C7	0.6378 (3)	1.11950 (14)	0.2314 (2)	0.0787 (12)
H7	0.5765	1.1544	0.2232	0.094*
O1	0.3443 (3)	1.07237 (16)	0.0794 (3)	0.1021 (10)
C8	0.4479 (5)	1.0230 (2)	0.1582 (3)	0.0808 (12)
H8	0.4482	1.0236	0.2143	0.097*
C9	0.4029 (4)	0.9456 (2)	0.1070 (3)	0.0746 (11)
H9	0.3305	0.9255	0.1061	0.090*
C10	0.3334 (5)	0.9635 (2)	−0.0018 (3)	0.0834 (12)
H10A	0.2570	0.9284	−0.0501	0.100*
H10B	0.4017	0.9616	−0.0097	0.100*
C11	0.2772 (5)	1.0417 (3)	−0.0188 (4)	0.1070 (15)
H11A	0.2980	1.0721	−0.0532	0.128*
H11B	0.1750	1.0405	−0.0618	0.128*
C12	0.5249 (4)	0.8892 (2)	0.1623 (3)	0.0691 (11)
H12	0.5598	0.8810	0.2315	0.083*
C13	0.4766 (3)	0.81442 (12)	0.10806 (19)	0.0670 (10)
C14	0.4233 (3)	0.76150 (17)	0.13274 (19)	0.0819 (12)
H14	0.4225	0.7717	0.1844	0.098*
C15	0.3711 (3)	0.69334 (14)	0.0802 (2)	0.0932 (14)
H15	0.3354	0.6579	0.0967	0.112*
C16	0.3723 (3)	0.67811 (13)	0.0029 (2)	0.0945 (14)
H16	0.3374	0.6325	−0.0322	0.113*
C17	0.4257 (3)	0.73103 (17)	−0.02174 (18)	0.0928 (14)
H17	0.4265	0.7208	−0.0734	0.111*
C18	0.4778 (3)	0.79919 (15)	0.0308 (2)	0.0805 (12)
H18	0.5135	0.8346	0.0143	0.097*
O2	0.8981 (3)	0.82604 (14)	0.2907 (2)	0.0841 (8)
N2	0.7998 (3)	0.68166 (16)	0.3925 (2)	0.0739 (9)
H2	0.7892	0.6442	0.4179	0.089*
C19	0.7740 (5)	0.9864 (2)	0.4799 (4)	0.1011 (15)
H19A	0.7976	0.9903	0.5447	0.152*
H19B	0.6787	1.0040	0.4252	0.152*
H19C	0.8387	1.0164	0.4823	0.152*
C20	0.7851 (3)	0.90401 (11)	0.46008 (18)	0.0713 (11)
C21	0.7154 (3)	0.84833 (16)	0.46715 (19)	0.0805 (12)
H21	0.6648	0.8609	0.4861	0.097*
C22	0.7215 (3)	0.77394 (14)	0.4459 (2)	0.0766 (12)
H22	0.6749	0.7367	0.4507	0.092*
C23	0.7971 (3)	0.75522 (10)	0.41766 (18)	0.0646 (10)
C24	0.8668 (2)	0.81089 (14)	0.41060 (18)	0.0607 (10)
C25	0.8607 (2)	0.88529 (12)	0.43181 (19)	0.0695 (11)
H25	0.9073	0.9225	0.4271	0.083*
C26	0.9540 (4)	0.7911 (2)	0.3858 (3)	0.0722 (11)
H26	1.0510	0.8094	0.4417	0.087*
C27	0.9609 (4)	0.7077 (2)	0.3691 (3)	0.0779 (12)
H27	1.0399	0.6837	0.4350	0.093*
C28	0.9901 (5)	0.7086 (2)	0.2974 (4)	0.1086 (16)
H28A	1.0894	0.6983	0.3359	0.130*
H28B	0.9324	0.6713	0.2431	0.130*
C29	0.9512 (6)	0.7860 (3)	0.2531 (4)	0.1208 (19)
H29A	1.0341	0.8114	0.2733	0.145*
H29B	0.8796	0.7836	0.1782	0.145*
C30	0.8210 (4)	0.67054 (19)	0.3224 (3)	0.0657 (10)
H30	0.7451	0.6977	0.2586	0.079*
C31	0.8059 (4)	0.58845 (13)	0.2948 (3)	0.0754 (12)
C32	0.6928 (3)	0.56536 (18)	0.1940 (2)	0.1154 (18)
H32	0.6292	0.6007	0.1436	0.138*
C33	0.6748 (4)	0.4895 (2)	0.1684 (3)	0.140 (2)
H33	0.5992	0.4741	0.1009	0.168*
C34	0.7699 (5)	0.43679 (13)	0.2437 (4)	0.1257 (19)
H34	0.7579	0.3861	0.2266	0.151*
C35	0.8830 (4)	0.45988 (17)	0.3446 (3)	0.133 (2)
H35	0.9466	0.4246	0.3950	0.159*
C36	0.9010 (3)	0.5357 (2)	0.3702 (2)	0.1198 (18)
H36	0.9766	0.5511	0.4377	0.144*

	U11	U22	U33	U12	U13	U23
C23	0.066 (3)	0.060 (3)	0.070 (3)	0.000 (2)	0.047 (2)	0.002 (2)
C24	0.058 (3)	0.059 (2)	0.063 (2)	−0.0010 (19)	0.040 (2)	0.0028 (19)
C25	0.073 (3)	0.066 (3)	0.071 (3)	−0.006 (2)	0.049 (2)	−0.002 (2)
C20	0.075 (3)	0.065 (3)	0.065 (3)	−0.004 (2)	0.044 (2)	−0.010 (2)
C21	0.092 (3)	0.085 (3)	0.079 (3)	−0.002 (2)	0.063 (3)	−0.010 (2)
C22	0.085 (3)	0.078 (3)	0.088 (3)	−0.010 (2)	0.066 (3)	−0.006 (2)
C5	0.066 (3)	0.063 (3)	0.054 (2)	0.005 (2)	0.037 (2)	0.004 (2)
C6	0.075 (3)	0.064 (3)	0.065 (3)	−0.004 (2)	0.045 (3)	−0.004 (2)
C7	0.087 (3)	0.073 (3)	0.076 (3)	0.000 (2)	0.055 (3)	−0.007 (2)
C2	0.107 (4)	0.066 (3)	0.064 (3)	−0.010 (3)	0.058 (3)	0.003 (2)
C3	0.081 (3)	0.086 (3)	0.072 (3)	−0.007 (3)	0.051 (3)	0.011 (2)
C4	0.071 (3)	0.077 (3)	0.078 (3)	0.000 (2)	0.051 (3)	0.009 (2)
C13	0.059 (3)	0.072 (3)	0.058 (3)	0.004 (2)	0.035 (2)	−0.006 (2)
C14	0.088 (3)	0.074 (3)	0.084 (3)	−0.004 (2)	0.058 (3)	−0.003 (2)
C15	0.112 (4)	0.070 (3)	0.093 (3)	−0.009 (3)	0.067 (3)	−0.004 (3)
C16	0.099 (4)	0.074 (3)	0.088 (4)	−0.004 (2)	0.054 (3)	−0.014 (3)
C17	0.106 (4)	0.086 (3)	0.080 (3)	0.001 (3)	0.060 (3)	−0.015 (3)
C18	0.097 (3)	0.076 (3)	0.077 (3)	−0.007 (2)	0.062 (3)	−0.010 (2)
C31	0.086 (3)	0.065 (3)	0.086 (3)	0.011 (2)	0.062 (3)	0.004 (2)
C36	0.127 (4)	0.068 (3)	0.105 (4)	0.022 (3)	0.054 (4)	0.006 (3)
C35	0.156 (5)	0.082 (4)	0.130 (5)	0.027 (3)	0.084 (5)	0.011 (3)
C34	0.161 (6)	0.071 (3)	0.148 (5)	0.016 (4)	0.105 (5)	−0.012 (4)
C33	0.163 (6)	0.091 (4)	0.111 (5)	0.001 (4)	0.070 (4)	−0.029 (4)
C32	0.131 (5)	0.085 (4)	0.090 (4)	0.021 (3)	0.058 (4)	−0.012 (3)
O1	0.100 (2)	0.084 (2)	0.111 (3)	0.0195 (18)	0.067 (2)	−0.007 (2)
N1	0.078 (2)	0.068 (2)	0.080 (2)	−0.0036 (17)	0.060 (2)	−0.0116 (17)
C1	0.131 (4)	0.080 (3)	0.096 (4)	−0.023 (3)	0.072 (3)	−0.002 (3)
C8	0.090 (4)	0.074 (3)	0.076 (3)	0.002 (3)	0.055 (3)	−0.001 (3)
C9	0.081 (3)	0.076 (3)	0.079 (3)	−0.003 (2)	0.059 (3)	−0.003 (2)
C10	0.105 (3)	0.068 (3)	0.082 (3)	0.010 (2)	0.065 (3)	0.001 (2)
C11	0.119 (4)	0.093 (4)	0.100 (4)	0.006 (3)	0.070 (4)	0.002 (3)
C12	0.072 (3)	0.066 (3)	0.069 (3)	0.001 (2)	0.047 (2)	−0.002 (2)
O2	0.101 (2)	0.0803 (19)	0.106 (2)	0.0212 (15)	0.084 (2)	0.0236 (17)
N2	0.099 (3)	0.058 (2)	0.089 (2)	−0.0049 (17)	0.074 (2)	−0.0011 (18)
C19	0.124 (4)	0.081 (3)	0.111 (4)	0.007 (3)	0.085 (3)	−0.010 (3)
C26	0.069 (3)	0.067 (3)	0.086 (3)	0.002 (2)	0.054 (3)	0.005 (2)
C27	0.073 (3)	0.075 (3)	0.088 (3)	0.012 (2)	0.056 (3)	0.012 (2)
C28	0.135 (4)	0.091 (4)	0.162 (5)	0.015 (3)	0.126 (4)	0.006 (3)
C29	0.169 (5)	0.113 (4)	0.159 (5)	0.049 (4)	0.142 (5)	0.037 (4)
C30	0.069 (3)	0.061 (2)	0.070 (3)	0.007 (2)	0.048 (2)	0.000 (2)

C23—N2	1.388 (3)	C35—H35	0.9300
C23—C24	1.3900	C34—C33	1.3900
C23—C22	1.3900	C34—H34	0.9300
C24—C25	1.3900	C33—C32	1.3900
C24—C26	1.484 (4)	C33—H33	0.9300
C25—C20	1.3900	C32—H32	0.9300
C25—H25	0.9300	O1—C8	1.400 (4)
C20—C21	1.3900	O1—C11	1.415 (5)
C20—C19	1.534 (4)	N1—C12	1.438 (4)
C21—C22	1.3900	N1—H1	0.8600
C21—H21	0.9300	C1—H1A	0.9600
C22—H22	0.9300	C1—H1B	0.9600
C5—C6	1.3900	C1—H1C	0.9600
C5—C4	1.3900	C8—C9	1.526 (5)
C5—N1	1.391 (3)	C8—H8	0.9800
C6—C7	1.3900	C9—C10	1.497 (5)
C6—C8	1.528 (5)	C9—C12	1.527 (5)
C7—C2	1.3900	C9—H9	0.9800
C7—H7	0.9300	C10—C11	1.500 (5)
C2—C3	1.3900	C10—H10A	0.9700
C2—C1	1.539 (4)	C10—H10B	0.9700
C3—C4	1.3900	C11—H11A	0.9700
C3—H3	0.9300	C11—H11B	0.9700
C4—H4	0.9300	C12—H12	0.9800
C13—C14	1.3900	O2—C29	1.415 (9)
C13—C18	1.3900	O2—C26	1.438 (4)
C13—C12	1.504 (4)	N2—C30	1.438 (4)
C14—C15	1.3900	N2—H2	0.8599
C14—H14	0.9300	C19—H19A	0.9600
C15—C16	1.3900	C19—H19B	0.9600
C15—H15	0.9300	C19—H19C	0.9600
C16—C17	1.3900	C26—C27	1.525 (5)
C16—H16	0.9300	C26—H26	0.9800
C17—C18	1.3900	C27—C30	1.522 (5)
C17—H17	0.9300	C27—C28	1.532 (5)
C18—H18	0.9300	C27—H27	0.9800
C31—C36	1.3900	C28—C29	1.491 (5)
C31—C32	1.3900	C28—H28A	0.9700
C31—C30	1.508 (4)	C28—H28B	0.9700
C36—C35	1.3900	C29—H29A	0.9700
C36—H36	0.9300	C29—H29B	0.9700
C35—C34	1.3900	C30—H30	0.9800
N2—C23—C24	119.3 (2)	C2—C1—H1A	109.5
N2—C23—C22	120.7 (2)	C2—C1—H1B	109.5
C24—C23—C22	120.0	H1A—C1—H1B	109.5
C25—C24—C23	120.0	C2—C1—H1C	109.5
C25—C24—C26	119.5 (2)	H1A—C1—H1C	109.5
C23—C24—C26	120.5 (2)	H1B—C1—H1C	109.5
C24—C25—C20	120.0	O1—C8—C9	104.8 (3)
C24—C25—H25	120.0	O1—C8—C6	109.8 (3)
C20—C25—H25	120.0	C9—C8—C6	111.7 (3)
C21—C20—C25	120.0	O1—C8—H8	110.1
C21—C20—C19	119.9 (2)	C9—C8—H8	110.1
C25—C20—C19	120.1 (2)	C6—C8—H8	110.1
C20—C21—C22	120.0	C10—C9—C8	102.8 (3)
C20—C21—H21	120.0	C10—C9—C12	114.9 (3)
C22—C21—H21	120.0	C8—C9—C12	113.6 (3)
C21—C22—C23	120.0	C10—C9—H9	108.4
C21—C22—H22	120.0	C8—C9—H9	108.4
C23—C22—H22	120.0	C12—C9—H9	108.4
C6—C5—C4	120.0	C9—C10—C11	104.0 (3)
C6—C5—N1	120.3 (2)	C9—C10—H10A	111.0
C4—C5—N1	119.6 (2)	C11—C10—H10A	111.0
C5—C6—C7	120.0	C9—C10—H10B	111.0
C5—C6—C8	121.8 (2)	C11—C10—H10B	111.0
C7—C6—C8	118.0 (2)	H10A—C10—H10B	109.0
C2—C7—C6	120.0	O1—C11—C10	107.5 (4)
C2—C7—H7	120.0	O1—C11—H11A	110.2
C6—C7—H7	120.0	C10—C11—H11A	110.2
C7—C2—C3	120.0	O1—C11—H11B	110.2
C7—C2—C1	120.6 (3)	C10—C11—H11B	110.2
C3—C2—C1	119.4 (3)	H11A—C11—H11B	108.5
C4—C3—C2	120.0	N1—C12—C13	112.3 (3)
C4—C3—H3	120.0	N1—C12—C9	109.9 (3)
C2—C3—H3	120.0	C13—C12—C9	111.9 (3)
C3—C4—C5	120.0	N1—C12—H12	107.5
C3—C4—H4	120.0	C13—C12—H12	107.5
C5—C4—H4	120.0	C9—C12—H12	107.5
C14—C13—C18	120.0	C29—O2—C26	107.6 (3)
C14—C13—C12	118.6 (2)	C23—N2—C30	117.3 (3)
C18—C13—C12	121.3 (2)	C23—N2—H2	121.3
C15—C14—C13	120.0	C30—N2—H2	121.3
C15—C14—H14	120.0	C20—C19—H19A	109.5
C13—C14—H14	120.0	C20—C19—H19B	109.5
C14—C15—C16	120.0	H19A—C19—H19B	109.5
C14—C15—H15	120.0	C20—C19—H19C	109.5
C16—C15—H15	120.0	H19A—C19—H19C	109.5
C17—C16—C15	120.0	H19B—C19—H19C	109.5
C17—C16—H16	120.0	O2—C26—C24	110.7 (3)
C15—C16—H16	120.0	O2—C26—C27	104.3 (3)
C16—C17—C18	120.0	C24—C26—C27	116.0 (3)
C16—C17—H17	120.0	O2—C26—H26	108.6
C18—C17—H17	120.0	C24—C26—H26	108.6
C17—C18—C13	120.0	C27—C26—H26	108.6
C17—C18—H18	120.0	C30—C27—C26	109.1 (3)
C13—C18—H18	120.0	C30—C27—C28	114.1 (4)
C36—C31—C32	120.0	C26—C27—C28	102.9 (3)
C36—C31—C30	120.5 (3)	C30—C27—H27	110.2
C32—C31—C30	119.5 (3)	C26—C27—H27	110.2
C31—C36—C35	120.0	C28—C27—H27	110.2
C31—C36—H36	120.0	C29—C28—C27	104.9 (3)
C35—C36—H36	120.0	C29—C28—H28A	110.8
C34—C35—C36	120.0	C27—C28—H28A	110.8
C34—C35—H35	120.0	C29—C28—H28B	110.8
C36—C35—H35	120.0	C27—C28—H28B	110.8
C35—C34—C33	120.0	H28A—C28—H28B	108.8
C35—C34—H34	120.0	O2—C29—C28	108.5 (4)
C33—C34—H34	120.0	O2—C29—H29A	110.0
C32—C33—C34	120.0	C28—C29—H29A	110.0
C32—C33—H33	120.0	O2—C29—H29B	110.0
C34—C33—H33	120.0	C28—C29—H29B	110.0
C33—C32—C31	120.0	H29A—C29—H29B	108.4
C33—C32—H32	120.0	N2—C30—C31	110.4 (3)
C31—C32—H32	120.0	N2—C30—C27	108.0 (3)
C8—O1—C11	110.5 (3)	C31—C30—C27	116.2 (3)
C5—N1—C12	119.9 (3)	N2—C30—H30	107.3
C5—N1—H1	120.1	C31—C30—H30	107.3
C12—N1—H1	120.1	C27—C30—H30	107.3
N2—C23—C24—C25	177.6 (2)	C7—C6—C8—O1	53.0 (4)
C22—C23—C24—C25	0.0	C5—C6—C8—C9	−15.4 (4)
N2—C23—C24—C26	−5.5 (3)	C7—C6—C8—C9	168.8 (3)
C22—C23—C24—C26	176.8 (3)	O1—C8—C9—C10	32.1 (4)
C23—C24—C25—C20	0.0	C6—C8—C9—C10	−86.8 (4)
C26—C24—C25—C20	−176.9 (3)	O1—C8—C9—C12	157.0 (3)
C24—C25—C20—C21	0.0	C6—C8—C9—C12	38.1 (4)
C24—C25—C20—C19	−177.9 (3)	C8—C9—C10—C11	−28.3 (4)
C25—C20—C21—C22	0.0	C12—C9—C10—C11	−152.3 (4)
C19—C20—C21—C22	177.9 (3)	C8—O1—C11—C10	5.3 (5)
C20—C21—C22—C23	0.0	C9—C10—C11—O1	15.4 (5)
N2—C23—C22—C21	−177.6 (2)	C5—N1—C12—C13	171.8 (3)
C24—C23—C22—C21	0.0	C5—N1—C12—C9	46.5 (4)
C4—C5—C6—C7	0.0	C14—C13—C12—N1	148.6 (2)
N1—C5—C6—C7	−176.7 (3)	C18—C13—C12—N1	−34.7 (4)
C4—C5—C6—C8	−175.7 (3)	C14—C13—C12—C9	−87.2 (3)
N1—C5—C6—C8	7.6 (3)	C18—C13—C12—C9	89.4 (3)
C5—C6—C7—C2	0.0	C10—C9—C12—N1	64.8 (4)
C8—C6—C7—C2	175.8 (3)	C8—C9—C12—N1	−53.2 (4)
C6—C7—C2—C3	0.0	C10—C9—C12—C13	−60.6 (4)
C6—C7—C2—C1	−179.9 (3)	C8—C9—C12—C13	−178.7 (3)
C7—C2—C3—C4	0.0	C24—C23—N2—C30	−25.0 (4)
C1—C2—C3—C4	179.9 (3)	C22—C23—N2—C30	152.6 (2)
C2—C3—C4—C5	0.0	C29—O2—C26—C24	−160.0 (3)
C6—C5—C4—C3	0.0	C29—O2—C26—C27	−34.6 (4)
N1—C5—C4—C3	176.8 (3)	C25—C24—C26—O2	−64.7 (3)
C18—C13—C14—C15	0.0	C23—C24—C26—O2	118.5 (3)
C12—C13—C14—C15	176.7 (3)	C25—C24—C26—C27	176.9 (3)
C13—C14—C15—C16	0.0	C23—C24—C26—C27	0.1 (4)
C14—C15—C16—C17	0.0	O2—C26—C27—C30	−89.9 (4)
C15—C16—C17—C18	0.0	C24—C26—C27—C30	32.0 (5)
C16—C17—C18—C13	0.0	O2—C26—C27—C28	31.6 (4)
C14—C13—C18—C17	0.0	C24—C26—C27—C28	153.5 (4)
C12—C13—C18—C17	−176.6 (3)	C30—C27—C28—C29	100.3 (4)
C32—C31—C36—C35	0.0	C26—C27—C28—C29	−17.7 (5)
C30—C31—C36—C35	177.7 (3)	C26—O2—C29—C28	23.5 (5)
C31—C36—C35—C34	0.0	C27—C28—C29—O2	−2.5 (6)
C36—C35—C34—C33	0.0	C23—N2—C30—C31	−174.1 (3)
C35—C34—C33—C32	0.0	C23—N2—C30—C27	57.8 (4)
C34—C33—C32—C31	0.0	C36—C31—C30—N2	−64.4 (3)
C36—C31—C32—C33	0.0	C32—C31—C30—N2	113.3 (3)
C30—C31—C32—C33	−177.7 (3)	C36—C31—C30—C27	59.0 (4)
C6—C5—N1—C12	−24.4 (4)	C32—C31—C30—C27	−123.2 (3)
C4—C5—N1—C12	158.8 (3)	C26—C27—C30—N2	−58.8 (4)
C11—O1—C8—C9	−23.5 (5)	C28—C27—C30—N2	−173.2 (3)
C11—O1—C8—C6	96.6 (4)	C26—C27—C30—C31	176.5 (3)
C5—C6—C8—O1	−131.3 (3)	C28—C27—C30—C31	62.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	2.41	2.959 (4)	122
N2—H2···O1i	0.86	2.15	2.934 (4)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86	2.41	2.959 (4)	122
N2—H2⋯O1i	0.86	2.15	2.934 (4)	151

Symmetry code: (i) .