N-[(R)-(6-Bromo-2-meth-oxy-quinolin-3-yl)(phen-yl)meth-yl]-N-[(S)-1-(4-meth-oxy-phen-yl)eth-yl]-2-(piperazin-1-yl)acetamide.

In the title compound, C(32)H(35)BrN(4)O(3), the piperazine ring exists in a chair conformation. The quinoline ring system is oriented at dihedral angles of 82.70 (17) and 19.54 (17)° to the phenyl and meth-oxy-phenyl rings, respectively. Weak inter-molecular C-H⋯π inter-actions are present in the crystal structure.

Related literature

For the synthesis of other phamaceutically active derivatives through conventional and other synthetic routes, see: Andries et al. (2005 ▶); Gaurrand et al. (2006 ▶); Mao et al. (2007 ▶); Dalla Via et al. (2008 ▶). For related structures, see: Cai et al. (2009 ▶); Petit et al. (2007 ▶).

Experimental

Crystal data

C32H35BrN4O3

M = 603.55

Orthorhombic,

a = 9.9738 (9) Å

b = 10.9397 (10) Å

c = 27.910 (3) Å

V = 3045.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.39 mm−1

T = 293 K

0.26 × 0.21 × 0.13 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.712, T max = 0.835

18937 measured reflections

5999 independent reflections

4518 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.170

S = 1.02

5999 reflections

361 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.56 e Å−3

Absolute structure: Flack (1983 ▶), 2585 Friedel pairs

Flack parameter: 0.011 (12)

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811040955/xu5339sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040955/xu5339Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811040955/xu5339Isup3.cml

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

C32H35BrN4O3	F(000) = 1256
Mr = 603.55	Dx = 1.316 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2354 reflections
a = 9.9738 (9) Å	θ = 2.0–25.0°
b = 10.9397 (10) Å	µ = 1.39 mm−1
c = 27.910 (3) Å	T = 293 K
V = 3045.3 (5) Å3	Block, colourless
Z = 4	0.26 × 0.21 × 0.13 mm

Bruker APEXII diffractometer	5999 independent reflections
Radiation source: fine-focus sealed tube	4518 reflections with I > 2σ(I)
graphite	Rint = 0.035
Detector resolution: 10.0 pixels mm-1	θmax = 26.0°, θmin = 1.5°
ω scans	h = −12→11
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	k = −13→13
Tmin = 0.712, Tmax = 0.835	l = −32→34
18937 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056	H-atom parameters constrained
wR(F2) = 0.170	w = 1/[σ2(Fo2) + (0.109P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
5999 reflections	Δρmax = 0.34 e Å−3
361 parameters	Δρmin = −0.56 e Å−3
0 restraints	Absolute structure: Flack (1983), 2585 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.011 (12)

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.

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 > 2sigma(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
Br	1.16448 (6)	−0.50994 (6)	0.67941 (2)	0.0885 (3)
O2	0.5985 (3)	−0.1119 (3)	0.63967 (10)	0.0483 (7)
N2	0.6854 (3)	0.0788 (3)	0.64410 (10)	0.0371 (7)
O3	0.5042 (4)	0.5855 (3)	0.55607 (14)	0.0717 (10)
O1	1.0020 (3)	0.1519 (3)	0.56260 (13)	0.0601 (8)
N3	0.4433 (3)	0.0798 (3)	0.71731 (11)	0.0407 (7)
N1	1.1268 (3)	−0.0147 (3)	0.58380 (12)	0.0447 (8)
C12	0.6723 (4)	0.0284 (3)	0.55538 (13)	0.0379 (8)
C8	0.8885 (4)	−0.0074 (3)	0.60224 (12)	0.0366 (8)
C4	1.1325 (4)	−0.1290 (3)	0.60612 (12)	0.0382 (8)
C17	0.7336 (4)	−0.0184 (4)	0.51555 (13)	0.0463 (9)
H17	0.8258	−0.0311	0.5157	0.056*
C11	0.7584 (4)	0.0681 (3)	0.59812 (12)	0.0360 (8)
H11	0.7878	0.1514	0.5905	0.043*
C7	0.8947 (4)	−0.1195 (4)	0.62209 (13)	0.0419 (9)
H7	0.8170	−0.1554	0.6340	0.050*
C5	1.0190 (4)	−0.1841 (4)	0.62510 (13)	0.0408 (9)
C25	0.7040 (4)	0.1975 (4)	0.67042 (14)	0.0438 (9)
H25	0.6443	0.1949	0.6983	0.053*
C6	1.0297 (4)	−0.3000 (4)	0.64702 (14)	0.0486 (10)
H6	0.9539	−0.3391	0.6590	0.058*
C26	0.6586 (4)	0.3032 (4)	0.64005 (13)	0.0414 (8)
C2	1.2674 (4)	−0.2991 (4)	0.63264 (15)	0.0490 (10)
H2	1.3500	−0.3375	0.6360	0.059*
C19	0.5536 (4)	−0.0052 (5)	0.71269 (14)	0.0530 (11)
H19A	0.5233	−0.0853	0.7229	0.064*
H19B	0.6246	0.0200	0.7343	0.064*
C3	1.2584 (4)	−0.1884 (4)	0.61003 (14)	0.0464 (10)
H3	1.3348	−0.1522	0.5972	0.056*
C16	0.6590 (4)	−0.0473 (4)	0.47472 (15)	0.0567 (11)
H16	0.7017	−0.0794	0.4479	0.068*
C9	1.0115 (4)	0.0395 (3)	0.58310 (14)	0.0414 (9)
C13	0.5344 (4)	0.0471 (4)	0.55422 (15)	0.0482 (10)
H13	0.4913	0.0802	0.5808	0.058*
C27	0.7433 (4)	0.3932 (4)	0.62201 (16)	0.0522 (11)
H27	0.8347	0.3882	0.6283	0.063*
C29	0.5599 (4)	0.4968 (4)	0.58342 (16)	0.0514 (10)
C31	0.5236 (4)	0.3155 (4)	0.62922 (17)	0.0496 (10)
H31	0.4634	0.2582	0.6412	0.060*
C28	0.6960 (4)	0.4898 (4)	0.59510 (17)	0.0554 (11)
H28	0.7547	0.5504	0.5847	0.066*
C18	0.6126 (4)	−0.0162 (4)	0.66139 (14)	0.0418 (9)
C15	0.5229 (5)	−0.0284 (4)	0.47393 (16)	0.0564 (11)
H15	0.4734	−0.0462	0.4466	0.068*
C30	0.4758 (5)	0.4090 (4)	0.60162 (18)	0.0581 (12)
H30	0.3845	0.4132	0.5950	0.070*
C24	0.8467 (5)	0.2064 (5)	0.68981 (17)	0.0624 (12)
H24A	0.8662	0.1354	0.7088	0.094*
H24B	0.8550	0.2783	0.7093	0.094*
H24C	0.9087	0.2110	0.6636	0.094*
C1	1.1521 (5)	−0.3534 (4)	0.65043 (13)	0.0505 (10)
C23	0.4107 (5)	0.0920 (6)	0.76822 (15)	0.0657 (14)
H23A	0.4881	0.1228	0.7854	0.079*
H23B	0.3881	0.0124	0.7813	0.079*
C20	0.3260 (4)	0.0351 (5)	0.69106 (16)	0.0595 (12)
H20A	0.3012	−0.0448	0.7032	0.071*
H20B	0.3489	0.0261	0.6575	0.071*
C14	0.4610 (5)	0.0170 (5)	0.51402 (16)	0.0605 (12)
H14	0.3685	0.0276	0.5141	0.073*
C22	0.2923 (5)	0.1794 (6)	0.77515 (19)	0.0723 (15)
H22A	0.2710	0.1854	0.8090	0.087*
H22B	0.3168	0.2602	0.7638	0.087*
N4	0.1719 (5)	0.1351 (6)	0.74826 (18)	0.0963 (17)
H4A	0.0942	0.1210	0.7604	0.116*
C21	0.2101 (5)	0.1193 (7)	0.69568 (18)	0.0829 (19)
H21A	0.1343	0.0867	0.6780	0.100*
H21B	0.2330	0.1981	0.6820	0.100*
C10	1.1213 (5)	0.1999 (5)	0.5407 (3)	0.0880 (19)
H10A	1.1025	0.2788	0.5272	0.132*
H10B	1.1504	0.1455	0.5158	0.132*
H10C	1.1906	0.2073	0.5644	0.132*
C32	0.5833 (7)	0.6817 (5)	0.5379 (2)	0.0825 (16)
H32A	0.5281	0.7354	0.5191	0.124*
H32B	0.6533	0.6488	0.5181	0.124*
H32C	0.6222	0.7265	0.5640	0.124*

	U11	U22	U33	U12	U13	U23
Br	0.0962 (5)	0.0790 (4)	0.0903 (4)	0.0348 (3)	0.0057 (3)	0.0237 (3)
O2	0.0438 (15)	0.0432 (16)	0.0578 (16)	0.0021 (13)	0.0115 (13)	0.0067 (14)
N2	0.0342 (17)	0.0399 (16)	0.0371 (15)	0.0056 (14)	0.0051 (13)	−0.0013 (13)
O3	0.065 (2)	0.053 (2)	0.097 (2)	0.0068 (16)	−0.0065 (19)	0.0160 (18)
O1	0.0421 (16)	0.0471 (17)	0.091 (2)	0.0057 (14)	0.0201 (15)	0.0181 (16)
N3	0.0303 (16)	0.052 (2)	0.0395 (17)	0.0027 (14)	0.0058 (13)	−0.0062 (15)
N1	0.0298 (16)	0.0457 (18)	0.0586 (19)	0.0010 (14)	0.0049 (14)	−0.0059 (16)
C12	0.039 (2)	0.0334 (18)	0.0411 (18)	0.0038 (16)	0.0024 (16)	0.0054 (14)
C8	0.0315 (18)	0.0396 (19)	0.0386 (18)	0.0056 (16)	0.0041 (14)	0.0014 (16)
C4	0.036 (2)	0.040 (2)	0.0389 (19)	0.0040 (16)	−0.0022 (15)	−0.0102 (15)
C17	0.038 (2)	0.056 (2)	0.045 (2)	0.0102 (19)	0.0055 (16)	0.0024 (19)
C11	0.0310 (19)	0.041 (2)	0.0360 (19)	0.0076 (16)	0.0088 (15)	0.0030 (15)
C7	0.0311 (18)	0.050 (2)	0.045 (2)	0.0083 (17)	0.0079 (16)	0.0051 (17)
C5	0.042 (2)	0.044 (2)	0.0373 (19)	0.0103 (17)	0.0066 (16)	0.0013 (16)
C25	0.037 (2)	0.051 (2)	0.043 (2)	0.0068 (17)	0.0039 (16)	−0.0121 (17)
C6	0.050 (2)	0.049 (2)	0.046 (2)	0.014 (2)	0.0122 (19)	0.0105 (18)
C26	0.035 (2)	0.044 (2)	0.0448 (19)	0.0037 (18)	0.0023 (17)	−0.0102 (16)
C2	0.041 (2)	0.050 (2)	0.056 (2)	0.0195 (19)	−0.009 (2)	−0.015 (2)
C19	0.045 (2)	0.068 (3)	0.045 (2)	0.020 (2)	0.0138 (17)	0.019 (2)
C3	0.030 (2)	0.053 (2)	0.056 (2)	0.0023 (18)	−0.0011 (17)	−0.016 (2)
C16	0.056 (3)	0.066 (3)	0.048 (2)	0.006 (2)	0.003 (2)	−0.011 (2)
C9	0.038 (2)	0.039 (2)	0.047 (2)	0.0015 (17)	0.0038 (17)	0.0021 (16)
C13	0.037 (2)	0.061 (3)	0.046 (2)	0.0158 (19)	0.0006 (18)	0.0003 (18)
C27	0.031 (2)	0.055 (3)	0.070 (3)	−0.0005 (19)	0.002 (2)	−0.003 (2)
C29	0.049 (2)	0.043 (2)	0.062 (2)	0.007 (2)	0.0042 (19)	0.001 (2)
C31	0.028 (2)	0.043 (2)	0.078 (3)	0.0025 (17)	0.0074 (19)	0.007 (2)
C28	0.043 (2)	0.045 (2)	0.079 (3)	−0.006 (2)	0.014 (2)	−0.001 (2)
C18	0.0315 (18)	0.049 (2)	0.0449 (19)	0.0122 (17)	0.0053 (16)	0.0067 (18)
C15	0.056 (3)	0.064 (3)	0.049 (2)	0.004 (2)	−0.011 (2)	−0.004 (2)
C30	0.037 (2)	0.050 (3)	0.087 (3)	−0.0009 (19)	−0.005 (2)	0.003 (2)
C24	0.051 (3)	0.074 (3)	0.062 (3)	0.008 (2)	−0.014 (2)	−0.012 (2)
C1	0.062 (3)	0.053 (2)	0.037 (2)	0.021 (2)	−0.0003 (19)	−0.0004 (17)
C23	0.045 (3)	0.109 (4)	0.043 (2)	0.000 (3)	0.002 (2)	−0.011 (3)
C20	0.043 (2)	0.079 (3)	0.056 (2)	0.001 (2)	0.0051 (19)	−0.024 (2)
C14	0.037 (2)	0.073 (3)	0.071 (3)	0.005 (2)	−0.005 (2)	0.006 (3)
C22	0.047 (3)	0.102 (4)	0.068 (3)	−0.002 (3)	0.011 (2)	−0.041 (3)
N4	0.059 (3)	0.143 (5)	0.087 (3)	0.010 (3)	0.013 (2)	−0.045 (3)
C21	0.043 (3)	0.141 (6)	0.065 (3)	0.025 (3)	−0.004 (2)	−0.032 (3)
C10	0.058 (3)	0.066 (3)	0.140 (5)	0.000 (3)	0.041 (3)	0.032 (3)
C32	0.112 (5)	0.051 (3)	0.085 (3)	−0.003 (3)	0.009 (4)	0.013 (3)

Br—C1	1.898 (4)	C19—H19B	0.9700
O2—C18	1.217 (5)	C3—H3	0.9300
N2—C18	1.357 (5)	C16—C15	1.373 (6)
N2—C11	1.480 (4)	C16—H16	0.9300
N2—C25	1.504 (5)	C13—C14	1.379 (6)
O3—C29	1.353 (5)	C13—H13	0.9300
O3—C32	1.410 (6)	C27—C28	1.379 (6)
O1—C9	1.360 (5)	C27—H27	0.9300
O1—C10	1.437 (6)	C29—C30	1.373 (6)
N3—C19	1.446 (5)	C29—C28	1.398 (6)
N3—C23	1.464 (5)	C31—C30	1.366 (6)
N3—C20	1.464 (5)	C31—H31	0.9300
N1—C9	1.294 (5)	C28—H28	0.9300
N1—C4	1.399 (5)	C15—C14	1.371 (7)
C12—C17	1.368 (5)	C15—H15	0.9300
C12—C13	1.391 (5)	C30—H30	0.9300
C12—C11	1.533 (5)	C24—H24A	0.9600
C8—C7	1.346 (5)	C24—H24B	0.9600
C8—C9	1.433 (5)	C24—H24C	0.9600
C8—C11	1.543 (5)	C23—C22	1.531 (7)
C4—C5	1.388 (5)	C23—H23A	0.9700
C4—C3	1.418 (5)	C23—H23B	0.9700
C17—C16	1.398 (6)	C20—C21	1.483 (7)
C17—H17	0.9300	C20—H20A	0.9700
C11—H11	0.9800	C20—H20B	0.9700
C7—C5	1.429 (5)	C14—H14	0.9300
C7—H7	0.9300	C22—N4	1.497 (7)
C5—C6	1.412 (6)	C22—H22A	0.9700
C25—C26	1.503 (6)	C22—H22B	0.9700
C25—C24	1.526 (6)	N4—C21	1.526 (7)
C25—H25	0.9800	N4—H4A	0.8600
C6—C1	1.357 (6)	C21—H21A	0.9700
C6—H6	0.9300	C21—H21B	0.9700
C26—C31	1.387 (6)	C10—H10A	0.9600
C26—C27	1.392 (6)	C10—H10B	0.9600
C2—C3	1.368 (6)	C10—H10C	0.9600
C2—C1	1.387 (6)	C32—H32A	0.9600
C2—H2	0.9300	C32—H32B	0.9600
C19—C18	1.553 (5)	C32—H32C	0.9600
C19—H19A	0.9700
C18—N2—C11	120.8 (3)	O3—C29—C30	117.3 (4)
C18—N2—C25	123.6 (3)	O3—C29—C28	124.7 (4)
C11—N2—C25	115.5 (3)	C30—C29—C28	118.0 (4)
C29—O3—C32	120.6 (4)	C30—C31—C26	122.3 (4)
C9—O1—C10	116.8 (3)	C30—C31—H31	118.8
C19—N3—C23	108.3 (3)	C26—C31—H31	118.8
C19—N3—C20	110.4 (3)	C27—C28—C29	120.1 (4)
C23—N3—C20	109.8 (3)	C27—C28—H28	120.0
C9—N1—C4	116.9 (3)	C29—C28—H28	120.0
C17—C12—C13	118.6 (4)	O2—C18—N2	122.9 (3)
C17—C12—C11	119.2 (3)	O2—C18—C19	118.9 (4)
C13—C12—C11	122.0 (3)	N2—C18—C19	118.1 (4)
C7—C8—C9	116.1 (3)	C14—C15—C16	119.1 (4)
C7—C8—C11	123.8 (3)	C14—C15—H15	120.5
C9—C8—C11	120.0 (3)	C16—C15—H15	120.5
C5—C4—N1	121.7 (3)	C31—C30—C29	121.3 (4)
C5—C4—C3	119.7 (4)	C31—C30—H30	119.4
N1—C4—C3	118.7 (3)	C29—C30—H30	119.4
C12—C17—C16	120.6 (4)	C25—C24—H24A	109.5
C12—C17—H17	119.7	C25—C24—H24B	109.5
C16—C17—H17	119.7	H24A—C24—H24B	109.5
N2—C11—C12	114.9 (3)	C25—C24—H24C	109.5
N2—C11—C8	113.0 (3)	H24A—C24—H24C	109.5
C12—C11—C8	112.2 (3)	H24B—C24—H24C	109.5
N2—C11—H11	105.2	C6—C1—C2	122.4 (4)
C12—C11—H11	105.2	C6—C1—Br	118.5 (3)
C8—C11—H11	105.2	C2—C1—Br	119.0 (3)
C8—C7—C5	120.9 (4)	N3—C23—C22	110.5 (4)
C8—C7—H7	119.5	N3—C23—H23A	109.5
C5—C7—H7	119.5	C22—C23—H23A	109.5
C4—C5—C6	119.5 (4)	N3—C23—H23B	109.5
C4—C5—C7	118.1 (4)	C22—C23—H23B	109.5
C6—C5—C7	122.4 (4)	H23A—C23—H23B	108.1
C26—C25—N2	110.6 (3)	N3—C20—C21	111.8 (4)
C26—C25—C24	115.6 (4)	N3—C20—H20A	109.3
N2—C25—C24	110.1 (3)	C21—C20—H20A	109.3
C26—C25—H25	106.7	N3—C20—H20B	109.3
N2—C25—H25	106.7	C21—C20—H20B	109.3
C24—C25—H25	106.7	H20A—C20—H20B	107.9
C1—C6—C5	119.1 (4)	C15—C14—C13	120.8 (4)
C1—C6—H6	120.5	C15—C14—H14	119.6
C5—C6—H6	120.5	C13—C14—H14	119.6
C31—C26—C27	116.2 (4)	N4—C22—C23	110.7 (4)
C31—C26—C25	119.4 (4)	N4—C22—H22A	109.5
C27—C26—C25	124.5 (4)	C23—C22—H22A	109.5
C3—C2—C1	119.4 (4)	N4—C22—H22B	109.5
C3—C2—H2	120.3	C23—C22—H22B	109.5
C1—C2—H2	120.3	H22A—C22—H22B	108.1
N3—C19—C18	114.9 (3)	C22—N4—C21	108.6 (4)
N3—C19—H19A	108.5	C22—N4—H4A	125.7
C18—C19—H19A	108.5	C21—N4—H4A	125.7
N3—C19—H19B	108.5	C20—C21—N4	110.4 (5)
C18—C19—H19B	108.5	C20—C21—H21A	109.6
H19A—C19—H19B	107.5	N4—C21—H21A	109.6
C2—C3—C4	119.9 (4)	C20—C21—H21B	109.6
C2—C3—H3	120.0	N4—C21—H21B	109.6
C4—C3—H3	120.0	H21A—C21—H21B	108.1
C15—C16—C17	120.4 (4)	O1—C10—H10A	109.5
C15—C16—H16	119.8	O1—C10—H10B	109.5
C17—C16—H16	119.8	H10A—C10—H10B	109.5
N1—C9—O1	118.8 (3)	O1—C10—H10C	109.5
N1—C9—C8	126.3 (4)	H10A—C10—H10C	109.5
O1—C9—C8	114.9 (3)	H10B—C10—H10C	109.5
C14—C13—C12	120.5 (4)	O3—C32—H32A	109.5
C14—C13—H13	119.7	O3—C32—H32B	109.5
C12—C13—H13	119.7	H32A—C32—H32B	109.5
C28—C27—C26	122.1 (4)	O3—C32—H32C	109.5
C28—C27—H27	118.9	H32A—C32—H32C	109.5
C26—C27—H27	118.9	H32B—C32—H32C	109.5

Cg is the centroid of the C12–C17 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···Cgi	0.96	2.69	3.639 (6)	170.

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C12–C17 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯Cgi	0.96	2.69	3.639 (6)	170

Symmetry code: (i) .