Ethyl 1-(2-bromo-propano-yl)-4-hydr-oxy-2,6-diphenyl-1,2,5,6-tetra-hydro-pyridine-3-carboxylate.

The title compound, C(23)H(24)BrNO(4), crystallizes with two independent mol-ecules per asymmetric unit. The methyl group of the ethoxy-carbonyl unit is disordered over two positions, with occupancies of 0.715 (12) and 0.285 (12) in one of the independent mol-ecules, and 0.529 (11) and 0.471 (11) in the other mol-ecule. In one of the independent mol-ecules, the tetra-hydro-pyridine ring adopts a half-chair conformation, while in the other it is in a distorted envelope conformation. In each independent mol-ecule, an intra-molecular O-H⋯O hydrogen bond generates an S(6) ring motif. The two independent mol-ecules are linked via C-H⋯O hydrogen bonds, forming a chain along the c axis.

Related literature

For general background to the synthesis and properties of 2,6-diaryl­piperidin-4-one derivatives, see: Aridoss et al. (2007 ▶, 2008b ▶); Krishnakumar & Krishnapillay (1996 ▶); Krishnapillay et al. (2000 ▶); Rubiralta et al. (1991 ▶). For the biological activity of pyridine derivatives, see: Aridoss et al. (2008a ▶); Dewick (1997 ▶); Gwaltney et al. (2003 ▶); Michael (1997 ▶, 2001 ▶); Pinder (1992 ▶); Yeung et al. (1982 ▶). For a related structure, see: Subha Nandhini et al. (2003 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C23H24BrNO4

M = 458.34

Triclinic,

a = 10.3970 (4) Å

b = 14.4874 (6) Å

c = 15.8580 (7) Å

α = 65.457 (2)°

β = 89.556 (3)°

γ = 80.597 (3)°

V = 2138.80 (15) Å3

Z = 4

Mo Kα radiation

μ = 1.95 mm−1

T = 293 K

0.30 × 0.16 × 0.16 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.600, T max = 0.749

39210 measured reflections

7523 independent reflections

5075 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.138

S = 1.04

7523 reflections

545 parameters

28 restraints

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809023836/ci2830sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023836/ci2830Isup2.hkl

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

C23H24BrNO4	Z = 4
Mr = 458.34	F(000) = 944
Triclinic, P1	Dx = 1.423 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.3970 (4) Å	Cell parameters from 5388 reflections
b = 14.4874 (6) Å	θ = 1.4–25.0°
c = 15.8580 (7) Å	µ = 1.95 mm−1
α = 65.457 (2)°	T = 293 K
β = 89.556 (3)°	Prism, colourless
γ = 80.597 (3)°	0.30 × 0.16 × 0.16 mm
V = 2138.80 (15) Å3

Bruker Kappa APEXII area-detector diffractometer	7523 independent reflections
Radiation source: fine-focus sealed tube	5075 reflections with I > 2σ(I)
graphite	Rint = 0.041
ω and φ scans	θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −12→12
Tmin = 0.600, Tmax = 0.749	k = −17→17
39210 measured reflections	l = −18→18

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0745P)2 + 0.8765P] where P = (Fo2 + 2Fc2)/3
7523 reflections	(Δ/σ)max = 0.001
545 parameters	Δρmax = 0.67 e Å−3
28 restraints	Δρmin = −0.44 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	0.72815 (4)	0.34497 (3)	0.35318 (3)	0.06691 (16)
O1	0.4992 (3)	0.6538 (3)	0.4898 (2)	0.0827 (9)
H1O	0.4404	0.7031	0.4635	0.124*
O2	0.7187 (3)	0.5800 (2)	0.18232 (17)	0.0648 (7)
O3	0.3824 (3)	0.8162 (3)	0.3556 (3)	0.0932 (11)
O4	0.4572 (2)	0.8545 (2)	0.2153 (3)	0.0735 (9)
N1	0.7565 (2)	0.60133 (19)	0.31187 (18)	0.0376 (6)
C1	0.6728 (3)	0.7045 (2)	0.2704 (2)	0.0410 (8)
H1	0.6197	0.7058	0.2190	0.049*
C2	0.5780 (3)	0.7178 (3)	0.3388 (3)	0.0471 (9)
C3	0.5863 (4)	0.6480 (3)	0.4287 (3)	0.0551 (10)
C4	0.6874 (4)	0.5545 (3)	0.4684 (3)	0.0537 (9)
H4A	0.6504	0.4954	0.4730	0.064*
H4B	0.7159	0.5431	0.5306	0.064*
C5	0.8039 (3)	0.5633 (3)	0.4097 (2)	0.0413 (8)
H5	0.8540	0.4936	0.4283	0.050*
C6	0.8963 (3)	0.6295 (2)	0.4207 (2)	0.0380 (7)
C7	0.8771 (4)	0.6770 (3)	0.4803 (2)	0.0495 (9)
H7	0.8057	0.6688	0.5168	0.059*
C8	0.9650 (4)	0.7371 (3)	0.4855 (3)	0.0637 (11)
H8	0.9521	0.7689	0.5259	0.076*
C9	1.0698 (4)	0.7505 (3)	0.4326 (3)	0.0657 (11)
H9	1.1269	0.7923	0.4357	0.079*
C10	1.0901 (4)	0.7022 (3)	0.3753 (3)	0.0620 (10)
H10	1.1624	0.7101	0.3397	0.074*
C11	1.0047 (3)	0.6414 (3)	0.3693 (3)	0.0500 (9)
H11	1.0205	0.6082	0.3302	0.060*
C12	0.7539 (3)	0.7893 (2)	0.2271 (2)	0.0436 (8)
C13	0.7646 (3)	0.8605 (3)	0.2614 (3)	0.0545 (9)
H13	0.7215	0.8575	0.3138	0.065*
C14	0.8385 (4)	0.9366 (3)	0.2192 (4)	0.0774 (13)
H14	0.8435	0.9848	0.2430	0.093*
C15	0.9037 (5)	0.9417 (4)	0.1433 (4)	0.0887 (16)
H15	0.9536	0.9929	0.1153	0.106*
C16	0.8953 (5)	0.8708 (4)	0.1086 (3)	0.0835 (15)
H16	0.9405	0.8733	0.0571	0.100*
C17	0.8201 (4)	0.7953 (3)	0.1493 (3)	0.0640 (11)
H17	0.8139	0.7482	0.1244	0.077*
C18	0.4657 (4)	0.7992 (3)	0.3062 (4)	0.0636 (11)
C19	0.3441 (5)	0.9369 (5)	0.1788 (5)	0.118 (2)
H19A	0.3326	0.9762	0.2160	0.141*	0.715 (12)
H19B	0.2654	0.9089	0.1790	0.141*	0.715 (12)
H19C	0.3742	1.0012	0.1472	0.141*	0.285 (12)
H19D	0.2962	0.9402	0.2298	0.141*	0.285 (12)
C20	0.3715 (10)	1.0026 (7)	0.0831 (6)	0.129 (4)	0.715 (12)
H20A	0.2999	1.0589	0.0555	0.194*	0.715 (12)
H20B	0.3823	0.9626	0.0473	0.194*	0.715 (12)
H20C	0.4500	1.0290	0.0841	0.194*	0.715 (12)
C20'	0.261 (2)	0.924 (2)	0.1100 (16)	0.136 (11)	0.285 (12)
H20D	0.1882	0.9797	0.0870	0.204*	0.285 (12)
H20E	0.2296	0.8597	0.1393	0.204*	0.285 (12)
H20F	0.3117	0.9232	0.0593	0.204*	0.285 (12)
C21	0.7694 (3)	0.5460 (3)	0.2606 (2)	0.0429 (8)
C22	0.8512 (3)	0.4390 (3)	0.3009 (3)	0.0474 (8)
H22	0.9132	0.4323	0.3502	0.057*
C23	0.9235 (4)	0.4149 (3)	0.2283 (3)	0.0686 (12)
H23A	0.9844	0.4612	0.2030	0.103*
H23B	0.8625	0.4228	0.1796	0.103*
H23C	0.9701	0.3452	0.2559	0.103*
Br2	0.16044 (4)	0.65873 (3)	0.14248 (3)	0.07332 (17)
O5	0.0762 (3)	0.3339 (3)	0.0151 (2)	0.0923 (10)
H5O	0.0614	0.2749	0.0371	0.139*
O6	0.2515 (3)	0.4273 (2)	0.31396 (18)	0.0669 (8)
O7	0.0454 (3)	0.1660 (3)	0.1541 (3)	0.0980 (11)
O8	0.1301 (3)	0.1399 (2)	0.2932 (2)	0.0769 (9)
N2	0.3001 (3)	0.40012 (19)	0.18645 (18)	0.0390 (6)
C24	0.2625 (3)	0.2972 (2)	0.2320 (2)	0.0413 (8)
H24	0.2060	0.2995	0.2811	0.050*
C25	0.1797 (3)	0.2780 (3)	0.1653 (3)	0.0492 (9)
C26	0.1563 (3)	0.3448 (3)	0.0751 (3)	0.0600 (11)
C27	0.2110 (4)	0.4402 (3)	0.0324 (3)	0.0575 (10)
H27A	0.1458	0.4982	0.0285	0.069*
H27B	0.2332	0.4514	−0.0303	0.069*
C28	0.3323 (3)	0.4348 (3)	0.0883 (2)	0.0435 (8)
H28	0.3504	0.5050	0.0671	0.052*
C29	0.4543 (3)	0.3678 (3)	0.0788 (2)	0.0425 (8)
C30	0.4573 (4)	0.3175 (3)	0.0215 (3)	0.0553 (9)
H30	0.3833	0.3265	−0.0156	0.066*
C31	0.5702 (5)	0.2537 (3)	0.0191 (3)	0.0697 (12)
H31	0.5712	0.2196	−0.0193	0.084*
C32	0.6798 (4)	0.2401 (3)	0.0718 (3)	0.0730 (13)
H32	0.7547	0.1957	0.0708	0.088*
C33	0.6788 (4)	0.2924 (3)	0.1266 (3)	0.0662 (11)
H33	0.7542	0.2850	0.1618	0.079*
C34	0.5674 (3)	0.3556 (3)	0.1299 (3)	0.0541 (9)
H34	0.5681	0.3908	0.1672	0.065*
C35	0.3786 (3)	0.2134 (3)	0.2800 (2)	0.0465 (8)
C36	0.4310 (4)	0.1441 (3)	0.2455 (3)	0.0595 (10)
H36	0.3953	0.1492	0.1898	0.071*
C37	0.5348 (5)	0.0677 (3)	0.2912 (4)	0.0865 (15)
H37	0.5689	0.0213	0.2668	0.104*
C38	0.5885 (5)	0.0596 (4)	0.3730 (5)	0.104 (2)
H38	0.6590	0.0076	0.4044	0.125*
C39	0.5380 (5)	0.1283 (4)	0.4084 (4)	0.0985 (17)
H39	0.5745	0.1230	0.4640	0.118*
C40	0.4342 (4)	0.2048 (3)	0.3626 (3)	0.0702 (12)
H40	0.4007	0.2513	0.3871	0.084*
C41	0.1131 (4)	0.1907 (3)	0.2014 (4)	0.0667 (12)
C42	0.0768 (6)	0.0452 (4)	0.3394 (5)	0.1050 (19)
H42A	0.1356	−0.0032	0.3919	0.126*	0.529 (11)
H42B	0.0697	0.0140	0.2965	0.126*	0.529 (11)
H42C	0.0936	0.0026	0.3063	0.126*	0.471 (11)
H42D	−0.0156	0.0599	0.3445	0.126*	0.471 (11)
C43	−0.0526 (9)	0.0668 (8)	0.3720 (9)	0.111 (4)	0.529 (11)
H43A	−0.1157	0.1007	0.3198	0.166*	0.529 (11)
H43B	−0.0495	0.1106	0.4034	0.166*	0.529 (11)
H43C	−0.0772	0.0033	0.4140	0.166*	0.529 (11)
C43'	0.1487 (14)	−0.0052 (9)	0.4351 (8)	0.120 (5)	0.471 (11)
H43D	0.1197	−0.0689	0.4713	0.180*	0.471 (11)
H43E	0.1310	0.0400	0.4656	0.180*	0.471 (11)
H43F	0.2410	−0.0186	0.4287	0.180*	0.471 (11)
C44	0.2887 (3)	0.4577 (3)	0.2355 (2)	0.0455 (8)
C45	0.3253 (3)	0.5647 (3)	0.1922 (3)	0.0491 (9)
H45	0.3835	0.5701	0.1421	0.059*
C46	0.3890 (4)	0.5887 (3)	0.2638 (3)	0.0685 (12)
H46A	0.4704	0.5422	0.2879	0.103*
H46B	0.3324	0.5810	0.3135	0.103*
H46C	0.4047	0.6583	0.2356	0.103*

	U11	U22	U33	U12	U13	U23
Br1	0.0709 (3)	0.0655 (3)	0.0582 (3)	−0.0183 (2)	0.0042 (2)	−0.0177 (2)
O1	0.068 (2)	0.121 (3)	0.088 (2)	−0.0393 (17)	0.0458 (17)	−0.064 (2)
O2	0.0806 (18)	0.0687 (17)	0.0456 (16)	0.0123 (14)	−0.0223 (14)	−0.0332 (14)
O3	0.0491 (16)	0.111 (3)	0.149 (3)	−0.0072 (16)	0.0303 (19)	−0.086 (3)
O4	0.0504 (16)	0.0612 (18)	0.104 (3)	0.0143 (13)	−0.0166 (16)	−0.0380 (18)
N1	0.0404 (14)	0.0404 (15)	0.0337 (15)	−0.0042 (11)	−0.0028 (11)	−0.0182 (12)
C1	0.0370 (17)	0.0418 (18)	0.046 (2)	−0.0028 (14)	−0.0027 (15)	−0.0213 (16)
C2	0.0354 (18)	0.053 (2)	0.065 (3)	−0.0104 (16)	0.0047 (16)	−0.035 (2)
C3	0.049 (2)	0.076 (3)	0.064 (3)	−0.033 (2)	0.0231 (19)	−0.045 (2)
C4	0.061 (2)	0.064 (2)	0.044 (2)	−0.030 (2)	0.0132 (17)	−0.0229 (19)
C5	0.053 (2)	0.0428 (18)	0.0294 (17)	−0.0081 (15)	−0.0015 (14)	−0.0166 (15)
C6	0.0404 (18)	0.0398 (18)	0.0307 (17)	−0.0057 (14)	−0.0036 (14)	−0.0123 (14)
C7	0.059 (2)	0.055 (2)	0.038 (2)	−0.0136 (17)	0.0025 (16)	−0.0230 (17)
C8	0.083 (3)	0.063 (3)	0.055 (3)	−0.015 (2)	−0.011 (2)	−0.034 (2)
C9	0.060 (3)	0.063 (3)	0.071 (3)	−0.024 (2)	−0.014 (2)	−0.020 (2)
C10	0.046 (2)	0.066 (3)	0.067 (3)	−0.0143 (19)	0.0022 (19)	−0.020 (2)
C11	0.046 (2)	0.056 (2)	0.049 (2)	−0.0073 (17)	0.0026 (17)	−0.0245 (18)
C12	0.0350 (17)	0.0401 (18)	0.045 (2)	0.0019 (14)	−0.0021 (15)	−0.0109 (16)
C13	0.046 (2)	0.045 (2)	0.072 (3)	−0.0071 (16)	−0.0014 (18)	−0.024 (2)
C14	0.069 (3)	0.053 (3)	0.106 (4)	−0.016 (2)	−0.001 (3)	−0.028 (3)
C15	0.072 (3)	0.059 (3)	0.105 (4)	−0.019 (2)	0.011 (3)	−0.002 (3)
C16	0.079 (3)	0.073 (3)	0.068 (3)	−0.009 (3)	0.027 (2)	−0.002 (3)
C17	0.067 (3)	0.058 (2)	0.055 (3)	−0.005 (2)	0.007 (2)	−0.014 (2)
C18	0.042 (2)	0.065 (3)	0.102 (4)	−0.0127 (19)	0.004 (2)	−0.052 (3)
C19	0.079 (4)	0.093 (4)	0.176 (7)	0.033 (3)	−0.037 (4)	−0.069 (5)
C20	0.141 (7)	0.106 (6)	0.108 (7)	0.044 (5)	−0.038 (5)	−0.035 (5)
C20'	0.127 (13)	0.137 (13)	0.139 (13)	−0.004 (9)	−0.002 (9)	−0.058 (9)
C21	0.0409 (18)	0.051 (2)	0.041 (2)	−0.0022 (15)	−0.0047 (15)	−0.0254 (17)
C22	0.0458 (19)	0.050 (2)	0.054 (2)	−0.0019 (16)	−0.0067 (16)	−0.0311 (18)
C23	0.063 (2)	0.066 (3)	0.086 (3)	−0.006 (2)	0.018 (2)	−0.043 (2)
Br2	0.0654 (3)	0.0715 (3)	0.0637 (3)	−0.0013 (2)	0.0025 (2)	−0.0133 (2)
O5	0.0693 (19)	0.146 (3)	0.086 (2)	−0.019 (2)	−0.0188 (18)	−0.071 (2)
O6	0.107 (2)	0.0668 (17)	0.0462 (16)	−0.0365 (16)	0.0308 (15)	−0.0355 (14)
O7	0.084 (2)	0.125 (3)	0.130 (3)	−0.052 (2)	0.011 (2)	−0.086 (3)
O8	0.080 (2)	0.074 (2)	0.091 (2)	−0.0448 (16)	0.0195 (17)	−0.0374 (18)
N2	0.0472 (15)	0.0416 (15)	0.0321 (15)	−0.0098 (12)	0.0087 (12)	−0.0187 (12)
C24	0.0440 (18)	0.0433 (18)	0.045 (2)	−0.0132 (15)	0.0107 (15)	−0.0243 (16)
C25	0.0410 (19)	0.061 (2)	0.059 (2)	−0.0073 (17)	0.0024 (17)	−0.038 (2)
C26	0.042 (2)	0.086 (3)	0.068 (3)	0.000 (2)	−0.0036 (19)	−0.053 (3)
C27	0.054 (2)	0.074 (3)	0.039 (2)	0.006 (2)	−0.0034 (17)	−0.024 (2)
C28	0.055 (2)	0.0434 (19)	0.0313 (18)	−0.0079 (15)	0.0073 (15)	−0.0148 (15)
C29	0.0487 (19)	0.048 (2)	0.0326 (18)	−0.0119 (15)	0.0126 (15)	−0.0178 (16)
C30	0.061 (2)	0.067 (2)	0.042 (2)	−0.0076 (19)	0.0085 (17)	−0.0279 (19)
C31	0.086 (3)	0.071 (3)	0.063 (3)	−0.013 (2)	0.029 (2)	−0.040 (2)
C32	0.064 (3)	0.070 (3)	0.071 (3)	0.000 (2)	0.026 (2)	−0.021 (2)
C33	0.049 (2)	0.073 (3)	0.067 (3)	−0.008 (2)	0.005 (2)	−0.022 (2)
C34	0.052 (2)	0.059 (2)	0.057 (2)	−0.0147 (18)	0.0058 (18)	−0.0273 (19)
C35	0.0490 (19)	0.0395 (19)	0.049 (2)	−0.0156 (15)	0.0076 (16)	−0.0140 (17)
C36	0.059 (2)	0.048 (2)	0.069 (3)	−0.0082 (18)	0.008 (2)	−0.023 (2)
C37	0.073 (3)	0.058 (3)	0.111 (4)	0.004 (2)	0.006 (3)	−0.023 (3)
C38	0.071 (3)	0.065 (3)	0.131 (6)	0.008 (3)	−0.017 (3)	−0.004 (3)
C39	0.091 (4)	0.084 (4)	0.091 (4)	−0.007 (3)	−0.035 (3)	−0.011 (3)
C40	0.077 (3)	0.063 (3)	0.067 (3)	−0.009 (2)	−0.010 (2)	−0.025 (2)
C41	0.048 (2)	0.076 (3)	0.100 (4)	−0.017 (2)	0.010 (2)	−0.058 (3)
C42	0.108 (4)	0.078 (3)	0.142 (6)	−0.052 (3)	0.026 (4)	−0.046 (4)
C43	0.116 (7)	0.096 (7)	0.122 (8)	−0.039 (5)	0.028 (6)	−0.040 (6)
C43'	0.151 (9)	0.087 (7)	0.123 (9)	−0.039 (6)	0.007 (7)	−0.038 (6)
C44	0.050 (2)	0.050 (2)	0.044 (2)	−0.0150 (16)	0.0105 (16)	−0.0256 (17)
C45	0.050 (2)	0.048 (2)	0.059 (2)	−0.0145 (16)	0.0174 (17)	−0.0295 (18)
C46	0.065 (3)	0.069 (3)	0.087 (3)	−0.023 (2)	−0.001 (2)	−0.043 (2)

Br1—C22	1.948 (4)	Br2—C45	1.945 (4)
O1—C3	1.340 (4)	O5—C26	1.343 (4)
O1—H1O	0.82	O5—H5O	0.82
O2—C21	1.216 (4)	O6—C44	1.218 (4)
O3—C18	1.227 (5)	O7—C41	1.223 (5)
O4—C18	1.322 (5)	O8—C41	1.329 (6)
O4—C19	1.456 (5)	O8—C42	1.460 (5)
N1—C21	1.352 (4)	N2—C44	1.350 (4)
N1—C5	1.472 (4)	N2—C28	1.478 (4)
N1—C1	1.480 (4)	N2—C24	1.480 (4)
C1—C2	1.511 (5)	C24—C25	1.508 (5)
C1—C12	1.524 (5)	C24—C35	1.509 (5)
C1—H1	0.98	C24—H24	0.98
C2—C3	1.356 (5)	C25—C26	1.348 (6)
C2—C18	1.440 (5)	C25—C41	1.445 (5)
C3—C4	1.474 (6)	C26—C27	1.472 (6)
C4—C5	1.511 (5)	C27—C28	1.519 (5)
C4—H4A	0.97	C27—H27A	0.97
C4—H4B	0.97	C27—H27B	0.97
C5—C6	1.521 (4)	C28—C29	1.513 (5)
C5—H5	0.98	C28—H28	0.98
C6—C11	1.377 (5)	C29—C34	1.377 (5)
C6—C7	1.378 (5)	C29—C30	1.379 (5)
C7—C8	1.387 (5)	C30—C31	1.381 (6)
C7—H7	0.93	C30—H30	0.93
C8—C9	1.359 (6)	C31—C32	1.357 (6)
C8—H8	0.93	C31—H31	0.93
C9—C10	1.355 (6)	C32—C33	1.369 (6)
C9—H9	0.93	C32—H32	0.93
C10—C11	1.377 (5)	C33—C34	1.369 (5)
C10—H10	0.93	C33—H33	0.93
C11—H11	0.93	C34—H34	0.93
C12—C13	1.370 (5)	C35—C36	1.371 (5)
C12—C17	1.385 (5)	C35—C40	1.384 (5)
C13—C14	1.382 (6)	C36—C37	1.368 (6)
C13—H13	0.93	C36—H36	0.93
C14—C15	1.358 (7)	C37—C38	1.367 (8)
C14—H14	0.93	C37—H37	0.93
C15—C16	1.367 (7)	C38—C39	1.368 (8)
C15—H15	0.93	C38—H38	0.93
C16—C17	1.381 (6)	C39—C40	1.369 (6)
C16—H16	0.93	C39—H39	0.93
C17—H17	0.93	C40—H40	0.93
C19—C20	1.475 (8)	C42—C43	1.470 (8)
C19—C20'	1.488 (10)	C42—C43'	1.521 (9)
C19—H19A	0.97	C42—H42A	0.97
C19—H19B	0.97	C42—H42B	0.97
C19—H19C	0.96	C42—H42C	0.96
C19—H19D	0.96	C42—H42D	0.96
C20—H20A	0.96	C43—H43A	0.96
C20—H20B	0.96	C43—H43B	0.96
C20—H20C	0.96	C43—H43C	0.96
C20'—H20D	0.96	C43'—H43D	0.96
C20'—H20E	0.96	C43'—H43E	0.96
C20'—H20F	0.96	C43'—H43F	0.96
C21—C22	1.512 (5)	C44—C45	1.523 (5)
C22—C23	1.500 (5)	C45—C46	1.505 (5)
C22—H22	0.98	C45—H45	0.98
C23—H23A	0.96	C46—H46A	0.96
C23—H23B	0.96	C46—H46B	0.96
C23—H23C	0.96	C46—H46C	0.96
C3—O1—H1O	109.5	C26—O5—H5O	109.5
C18—O4—C19	115.5 (4)	C41—O8—C42	119.2 (4)
C21—N1—C5	125.7 (3)	C44—N2—C28	125.9 (3)
C21—N1—C1	117.2 (3)	C44—N2—C24	116.6 (3)
C5—N1—C1	116.6 (2)	C28—N2—C24	117.1 (2)
N1—C1—C2	110.5 (3)	N2—C24—C25	110.5 (3)
N1—C1—C12	111.4 (2)	N2—C24—C35	112.1 (2)
C2—C1—C12	115.7 (3)	C25—C24—C35	115.0 (3)
N1—C1—H1	106.2	N2—C24—H24	106.2
C2—C1—H1	106.2	C25—C24—H24	106.2
C12—C1—H1	106.2	C35—C24—H24	106.2
C3—C2—C18	118.1 (4)	C26—C25—C41	119.0 (4)
C3—C2—C1	121.9 (3)	C26—C25—C24	122.1 (3)
C18—C2—C1	119.5 (4)	C41—C25—C24	118.6 (3)
O1—C3—C2	123.5 (4)	O5—C26—C25	123.8 (4)
O1—C3—C4	112.7 (4)	O5—C26—C27	112.3 (4)
C2—C3—C4	123.7 (3)	C25—C26—C27	123.8 (3)
C3—C4—C5	111.7 (3)	C26—C27—C28	111.3 (3)
C3—C4—H4A	109.3	C26—C27—H27A	109.4
C5—C4—H4A	109.3	C28—C27—H27A	109.4
C3—C4—H4B	109.3	C26—C27—H27B	109.4
C5—C4—H4B	109.3	C28—C27—H27B	109.4
H4A—C4—H4B	107.9	H27A—C27—H27B	108.0
N1—C5—C4	108.6 (3)	N2—C28—C29	111.1 (3)
N1—C5—C6	110.8 (3)	N2—C28—C27	107.5 (3)
C4—C5—C6	114.9 (3)	C29—C28—C27	115.3 (3)
N1—C5—H5	107.4	N2—C28—H28	107.6
C4—C5—H5	107.4	C29—C28—H28	107.6
C6—C5—H5	107.4	C27—C28—H28	107.6
C11—C6—C7	118.6 (3)	C34—C29—C30	118.2 (3)
C11—C6—C5	118.3 (3)	C34—C29—C28	119.0 (3)
C7—C6—C5	123.0 (3)	C30—C29—C28	122.8 (3)
C6—C7—C8	119.5 (4)	C29—C30—C31	120.0 (4)
C6—C7—H7	120.2	C29—C30—H30	120.0
C8—C7—H7	120.2	C31—C30—H30	120.0
C9—C8—C7	121.2 (4)	C32—C31—C30	121.1 (4)
C9—C8—H8	119.4	C32—C31—H31	119.5
C7—C8—H8	119.4	C30—C31—H31	119.5
C10—C9—C8	119.3 (4)	C31—C32—C33	119.3 (4)
C10—C9—H9	120.4	C31—C32—H32	120.4
C8—C9—H9	120.4	C33—C32—H32	120.4
C9—C10—C11	120.7 (4)	C32—C33—C34	120.2 (4)
C9—C10—H10	119.7	C32—C33—H33	119.9
C11—C10—H10	119.7	C34—C33—H33	119.9
C6—C11—C10	120.6 (4)	C33—C34—C29	121.2 (4)
C6—C11—H11	119.7	C33—C34—H34	119.4
C10—C11—H11	119.7	C29—C34—H34	119.4
C13—C12—C17	118.1 (3)	C36—C35—C40	118.2 (4)
C13—C12—C1	123.0 (3)	C36—C35—C24	122.4 (3)
C17—C12—C1	118.8 (3)	C40—C35—C24	119.3 (3)
C12—C13—C14	121.0 (4)	C37—C36—C35	121.4 (5)
C12—C13—H13	119.5	C37—C36—H36	119.3
C14—C13—H13	119.5	C35—C36—H36	119.3
C15—C14—C13	120.6 (5)	C38—C37—C36	119.9 (5)
C15—C14—H14	119.7	C38—C37—H37	120.0
C13—C14—H14	119.7	C36—C37—H37	120.0
C14—C15—C16	119.3 (4)	C37—C38—C39	119.7 (5)
C14—C15—H15	120.4	C37—C38—H38	120.2
C16—C15—H15	120.4	C39—C38—H38	120.2
C15—C16—C17	120.6 (5)	C38—C39—C40	120.4 (5)
C15—C16—H16	119.7	C38—C39—H39	119.8
C17—C16—H16	119.7	C40—C39—H39	119.8
C16—C17—C12	120.4 (4)	C39—C40—C35	120.5 (5)
C16—C17—H17	119.8	C39—C40—H40	119.8
C12—C17—H17	119.8	C35—C40—H40	119.8
O3—C18—O4	121.6 (4)	O7—C41—O8	122.6 (4)
O3—C18—C2	124.8 (5)	O7—C41—C25	124.7 (5)
O4—C18—C2	113.5 (4)	O8—C41—C25	112.7 (3)
O4—C19—C20	105.7 (6)	O8—C42—C43	110.7 (6)
O4—C19—C20'	111.8 (10)	O8—C42—C43'	103.2 (6)
C20—C19—C20'	69.1 (12)	C43—C42—C43'	95.8 (9)
O4—C19—H19A	110.6	O8—C42—H42A	109.5
C20—C19—H19A	110.6	C43—C42—H42A	109.5
C20'—C19—H19A	135.7	O8—C42—H42B	109.5
O4—C19—H19B	110.6	C43—C42—H42B	109.5
C20—C19—H19B	110.6	C43'—C42—H42B	127.0
H19A—C19—H19B	108.7	H42A—C42—H42B	108.1
O4—C19—H19C	108.6	O8—C42—H42C	110.7
C20'—C19—H19C	107.3	C43—C42—H42C	122.1
H19A—C19—H19C	69.9	C43'—C42—H42C	111.8
H19B—C19—H19C	138.0	H42A—C42—H42C	92.5
O4—C19—H19D	108.9	O8—C42—H42D	111.3
C20—C19—H19D	141.1	C43'—C42—H42D	110.6
C20'—C19—H19D	112.2	H42A—C42—H42D	122.1
H19B—C19—H19D	72.8	H42B—C42—H42D	95.0
H19C—C19—H19D	107.8	H42C—C42—H42D	109.1
C19—C20—H20A	109.5	C42—C43—H43A	109.5
H19C—C20—H20A	98.0	H42D—C43—H43A	85.4
C19—C20—H20B	109.5	C42—C43—H43B	109.5
H19C—C20—H20B	146.1	H42D—C43—H43B	128.5
H20A—C20—H20B	109.5	H43A—C43—H43B	109.5
C19—C20—H20C	109.5	C42—C43—H43C	109.5
H19C—C20—H20C	78.1	H42D—C43—H43C	111.0
H20A—C20—H20C	109.5	H43A—C43—H43C	109.5
H20B—C20—H20C	109.5	H43B—C43—H43C	109.5
C19—C20'—H20D	109.5	C42—C43'—H43D	109.5
C19—C20'—H20E	109.5	C42—C43'—H43E	109.5
H20D—C20'—H20E	109.5	H43D—C43'—H43E	109.5
C19—C20'—H20F	109.5	C42—C43'—H43F	109.5
H20D—C20'—H20F	109.5	H43D—C43'—H43F	109.5
H20E—C20'—H20F	109.5	H43E—C43'—H43F	109.5
O2—C21—N1	122.1 (3)	O6—C44—N2	122.6 (3)
O2—C21—C22	118.7 (3)	O6—C44—C45	118.2 (3)
N1—C21—C22	119.2 (3)	N2—C44—C45	119.1 (3)
C23—C22—C21	112.0 (3)	C46—C45—C44	111.3 (3)
C23—C22—Br1	109.7 (2)	C46—C45—Br2	109.9 (2)
C21—C22—Br1	105.6 (2)	C44—C45—Br2	104.9 (2)
C23—C22—H22	109.8	C46—C45—H45	110.2
C21—C22—H22	109.8	C44—C45—H45	110.2
Br1—C22—H22	109.8	Br2—C45—H45	110.2
C22—C23—H23A	109.5	C45—C46—H46A	109.5
C22—C23—H23B	109.5	C45—C46—H46B	109.5
H23A—C23—H23B	109.5	H46A—C46—H46B	109.5
C22—C23—H23C	109.5	C45—C46—H46C	109.5
H23A—C23—H23C	109.5	H46A—C46—H46C	109.5
H23B—C23—H23C	109.5	H46B—C46—H46C	109.5
C21—N1—C1—C2	131.6 (3)	C44—N2—C24—C25	135.0 (3)
C5—N1—C1—C2	−40.7 (3)	C28—N2—C24—C25	−38.4 (4)
C21—N1—C1—C12	−98.3 (3)	C44—N2—C24—C35	−95.2 (3)
C5—N1—C1—C12	89.4 (3)	C28—N2—C24—C35	91.4 (3)
N1—C1—C2—C3	8.5 (4)	N2—C24—C25—C26	5.3 (4)
C12—C1—C2—C3	−119.3 (3)	C35—C24—C25—C26	−122.9 (4)
N1—C1—C2—C18	−163.3 (3)	N2—C24—C25—C41	−168.4 (3)
C12—C1—C2—C18	68.9 (4)	C35—C24—C25—C41	63.4 (4)
C18—C2—C3—O1	−3.7 (5)	C41—C25—C26—O5	−1.6 (6)
C1—C2—C3—O1	−175.6 (3)	C24—C25—C26—O5	−175.4 (3)
C18—C2—C3—C4	172.7 (3)	C41—C25—C26—C27	175.4 (3)
C1—C2—C3—C4	0.8 (5)	C24—C25—C26—C27	1.7 (5)
O1—C3—C4—C5	−163.7 (3)	O5—C26—C27—C28	−161.1 (3)
C2—C3—C4—C5	19.5 (5)	C25—C26—C27—C28	21.6 (5)
C21—N1—C5—C4	−110.1 (3)	C44—N2—C28—C29	121.8 (3)
C1—N1—C5—C4	61.6 (3)	C24—N2—C28—C29	−65.5 (4)
C21—N1—C5—C6	122.8 (3)	C44—N2—C28—C27	−111.3 (4)
C1—N1—C5—C6	−65.5 (3)	C24—N2—C28—C27	61.4 (4)
C3—C4—C5—N1	−47.5 (4)	C26—C27—C28—N2	−49.5 (4)
C3—C4—C5—C6	77.2 (4)	C26—C27—C28—C29	74.9 (4)
N1—C5—C6—C11	−56.3 (4)	N2—C28—C29—C34	−55.0 (4)
C4—C5—C6—C11	−179.9 (3)	C27—C28—C29—C34	−177.6 (3)
N1—C5—C6—C7	124.4 (3)	N2—C28—C29—C30	124.5 (3)
C4—C5—C6—C7	0.8 (5)	C27—C28—C29—C30	1.9 (5)
C11—C6—C7—C8	1.5 (5)	C34—C29—C30—C31	2.5 (5)
C5—C6—C7—C8	−179.2 (3)	C28—C29—C30—C31	−177.0 (3)
C6—C7—C8—C9	0.2 (6)	C29—C30—C31—C32	−0.6 (6)
C7—C8—C9—C10	−1.5 (6)	C30—C31—C32—C33	−1.5 (7)
C8—C9—C10—C11	1.0 (6)	C31—C32—C33—C34	1.7 (6)
C7—C6—C11—C10	−2.0 (5)	C32—C33—C34—C29	0.2 (6)
C5—C6—C11—C10	178.7 (3)	C30—C29—C34—C33	−2.3 (5)
C9—C10—C11—C6	0.7 (6)	C28—C29—C34—C33	177.2 (3)
N1—C1—C12—C13	−112.9 (3)	N2—C24—C35—C36	−106.6 (4)
C2—C1—C12—C13	14.4 (4)	C25—C24—C35—C36	20.8 (5)
N1—C1—C12—C17	67.2 (4)	N2—C24—C35—C40	74.1 (4)
C2—C1—C12—C17	−165.5 (3)	C25—C24—C35—C40	−158.5 (3)
C17—C12—C13—C14	0.5 (5)	C40—C35—C36—C37	0.5 (6)
C1—C12—C13—C14	−179.4 (3)	C24—C35—C36—C37	−178.8 (4)
C12—C13—C14—C15	−0.9 (6)	C35—C36—C37—C38	−0.2 (7)
C13—C14—C15—C16	0.3 (7)	C36—C37—C38—C39	−0.1 (8)
C14—C15—C16—C17	0.7 (7)	C37—C38—C39—C40	0.1 (9)
C15—C16—C17—C12	−1.1 (7)	C38—C39—C40—C35	0.2 (8)
C13—C12—C17—C16	0.5 (5)	C36—C35—C40—C39	−0.5 (6)
C1—C12—C17—C16	−179.6 (3)	C24—C35—C40—C39	178.8 (4)
C19—O4—C18—O3	0.8 (6)	C42—O8—C41—O7	6.0 (6)
C19—O4—C18—C2	179.2 (4)	C42—O8—C41—C25	−175.5 (4)
C3—C2—C18—O3	7.2 (6)	C26—C25—C41—O7	7.6 (6)
C1—C2—C18—O3	179.3 (3)	C24—C25—C41—O7	−178.5 (4)
C3—C2—C18—O4	−171.1 (3)	C26—C25—C41—O8	−170.9 (3)
C1—C2—C18—O4	1.0 (5)	C24—C25—C41—O8	3.1 (5)
C18—O4—C19—C20	166.3 (6)	C41—O8—C42—C43	−94.8 (8)
C18—O4—C19—C20'	−120.4 (13)	C41—O8—C42—C43'	163.7 (7)
C5—N1—C21—O2	174.0 (3)	C28—N2—C44—O6	173.9 (3)
C1—N1—C21—O2	2.4 (5)	C24—N2—C44—O6	1.1 (5)
C5—N1—C21—C22	−6.9 (5)	C28—N2—C44—C45	−7.0 (5)
C1—N1—C21—C22	−178.5 (3)	C24—N2—C44—C45	−179.7 (3)
O2—C21—C22—C23	34.5 (5)	O6—C44—C45—C46	35.6 (5)
N1—C21—C22—C23	−144.6 (3)	N2—C44—C45—C46	−143.6 (3)
O2—C21—C22—Br1	−84.9 (3)	O6—C44—C45—Br2	−83.2 (4)
N1—C21—C22—Br1	96.0 (3)	N2—C44—C45—Br2	97.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O3	0.82	1.83	2.547 (6)	146
O5—H5O···O7	0.82	1.90	2.582 (6)	140
C7—H7···O6i	0.93	2.58	3.349 (4)	141
C30—H30···O2ii	0.93	2.56	3.349 (5)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O3	0.82	1.83	2.547 (6)	146
O5—H5O⋯O7	0.82	1.90	2.582 (6)	140
C7—H7⋯O6i	0.93	2.58	3.349 (4)	141
C30—H30⋯O2ii	0.93	2.56	3.349 (5)	143

Symmetry codes: (i) ; (ii) .