N-[2-(5-Bromo-2-morpholin-4-ylpyrim-idin-4-ylsulfan-yl)-4-meth-oxy-phen-yl]-2,4,6-trimethyl-benzene-sulfonamide.

In the title compound, C(24)H(27)BrN(4)O(4)S(2), the mol-ecule is twisted at the sulfonyl S atom with a C-S(O(2))-N(H)-C torsion angle of 62.6 (3)°. The benzene rings bridged by the sulfonamide group are tilted to each other by a dihedral angle of 60.6 (1)°. The dihedral angle between the sulfur-bridged pyrimidine and benzene rings is 62.7 (1)°. The morpholine ring adopts a chair conformation. The mol-ecular conformation is stabilized by a weak intra-molecular π-π stacking inter-action between the pyrimidine and the 2,4,6-trimethyl-benzene rings [centroid-centroid distance = 3.793 (2) Å]. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds into a chain along the b axis.

Related literature

For related structures of sulfonamides, see: Rodrigues et al. (2011 ▶); Akkurt et al. (2011 ▶); Kant et al. (2012 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ring conformations, see: Duax & Norton (1975 ▶).

Experimental

Crystal data

C24H27BrN4O4S2

M = 579.53

Monoclinic,

a = 10.2583 (4) Å

b = 17.4727 (6) Å

c = 14.4375 (7) Å

β = 97.199 (4)°

V = 2567.38 (18) Å3

Z = 4

Mo Kα radiation

μ = 1.80 mm−1

T = 293 K

0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.526, T max = 0.697

19056 measured reflections

5023 independent reflections

3359 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.105

S = 1.02

5023 reflections

321 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812040792/is5200sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040792/is5200Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812040792/is5200Isup3.cml

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

C24H27BrN4O4S2	F(000) = 1192
Mr = 579.53	Dx = 1.499 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6670 reflections
a = 10.2583 (4) Å	θ = 3.7–29.0°
b = 17.4727 (6) Å	µ = 1.80 mm−1
c = 14.4375 (7) Å	T = 293 K
β = 97.199 (4)°	Block, brown
V = 2567.38 (18) Å3	0.3 × 0.2 × 0.2 mm
Z = 4

Oxford Diffraction Xcalibur Sapphire3 diffractometer	5023 independent reflections
Radiation source: fine-focus sealed tube	3359 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.7°
ω scan	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −21→21
Tmin = 0.526, Tmax = 0.697	l = −17→17
19056 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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.105	w = 1/[σ2(Fo2) + (0.0338P)2 + 1.6315P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
5023 reflections	Δρmax = 0.31 e Å−3
321 parameters	Δρmin = −0.39 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0057 (4)

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Br1	1.02664 (4)	0.10295 (2)	0.23807 (3)	0.07706 (19)
S1	0.50455 (9)	0.24940 (6)	0.00299 (6)	0.0566 (3)
S2	0.74901 (8)	0.19238 (5)	0.24649 (6)	0.0472 (2)
N1	0.5008 (2)	0.22120 (16)	0.11087 (18)	0.0487 (7)
H1	0.4848	0.1739	0.1215	0.058*
O1	0.4808 (3)	0.18139 (17)	−0.05220 (17)	0.0788 (8)
O2	0.4152 (2)	0.31164 (17)	−0.01409 (18)	0.0774 (8)
O3	0.5639 (3)	0.42389 (15)	0.41145 (19)	0.0704 (7)
C1	0.6672 (3)	0.28269 (18)	−0.0041 (2)	0.0430 (8)
C2	0.6972 (4)	0.36148 (19)	−0.0014 (2)	0.0508 (9)
C3	0.8256 (4)	0.3831 (2)	−0.0079 (2)	0.0562 (9)
H3	0.8455	0.4350	−0.0071	0.067*
C4	0.9252 (3)	0.3316 (2)	−0.0154 (2)	0.0535 (9)
C5	0.8941 (3)	0.2553 (2)	−0.0154 (2)	0.0527 (9)
H5	0.9608	0.2197	−0.0187	0.063*
C6	0.7666 (3)	0.22861 (18)	−0.0106 (2)	0.0460 (8)
C7	0.7498 (4)	0.14289 (19)	−0.0125 (3)	0.0681 (11)
H7A	0.7078	0.1274	−0.0727	0.102*
H7B	0.6966	0.1278	0.0346	0.102*
H7C	0.8344	0.1188	−0.0005	0.102*
C8	1.0642 (4)	0.3581 (3)	−0.0207 (3)	0.0791 (12)
H8A	1.0826	0.3555	−0.0842	0.119*
H8B	1.1244	0.3257	0.0176	0.119*
H8C	1.0740	0.4100	0.0011	0.119*
C9	0.6004 (4)	0.4257 (2)	0.0093 (3)	0.0787 (13)
H9A	0.5321	0.4249	−0.0427	0.118*
H9B	0.6453	0.4739	0.0110	0.118*
H9C	0.5625	0.4187	0.0662	0.118*
C10	0.5231 (3)	0.27276 (18)	0.1873 (2)	0.0412 (7)
C11	0.4332 (3)	0.3308 (2)	0.1984 (2)	0.0532 (9)
H11	0.3594	0.3360	0.1544	0.064*
C12	0.4508 (3)	0.3801 (2)	0.2724 (3)	0.0553 (9)
H12	0.3902	0.4191	0.2774	0.066*
C13	0.5583 (3)	0.3723 (2)	0.3399 (2)	0.0503 (8)
C14	0.6476 (3)	0.31466 (18)	0.3324 (2)	0.0446 (8)
H14	0.7183	0.3082	0.3787	0.054*
C15	0.6321 (3)	0.26588 (18)	0.2552 (2)	0.0409 (7)
C16	0.8899 (3)	0.24701 (19)	0.2337 (2)	0.0404 (7)
N17	0.8793 (2)	0.32166 (15)	0.22635 (17)	0.0414 (6)
C18	0.9896 (3)	0.3618 (2)	0.2209 (2)	0.0490 (8)
N19	1.1113 (3)	0.33241 (18)	0.2232 (2)	0.0611 (8)
C20	1.1185 (3)	0.2570 (2)	0.2294 (3)	0.0614 (10)
H20	1.2006	0.2341	0.2313	0.074*
C21	1.0110 (3)	0.2104 (2)	0.2331 (2)	0.0504 (8)
N22	0.9747 (3)	0.43869 (16)	0.2097 (2)	0.0575 (8)
C23	0.8513 (3)	0.4755 (2)	0.2241 (3)	0.0623 (10)
H23A	0.7806	0.4382	0.2173	0.075*
H23B	0.8303	0.5154	0.1780	0.075*
C24	0.8650 (4)	0.5089 (2)	0.3196 (3)	0.0726 (12)
H24A	0.7834	0.5335	0.3300	0.087*
H24B	0.8829	0.4685	0.3655	0.087*
O25	0.9689 (3)	0.56335 (15)	0.3307 (2)	0.0848 (9)
C25	0.6630 (4)	0.4143 (2)	0.4887 (3)	0.0773 (12)
H25A	0.6544	0.3647	0.5158	0.116*
H25B	0.6535	0.4531	0.5345	0.116*
H25C	0.7479	0.4187	0.4679	0.116*
C26	1.0905 (4)	0.5289 (2)	0.3180 (3)	0.0808 (14)
H26A	1.1128	0.4909	0.3663	0.097*
H26B	1.1589	0.5676	0.3241	0.097*
C27	1.0850 (3)	0.4917 (2)	0.2245 (3)	0.0679 (11)
H27A	1.0756	0.5306	0.1761	0.082*
H27B	1.1663	0.4643	0.2204	0.082*

	U11	U22	U33	U12	U13	U23
Br1	0.0695 (3)	0.0623 (3)	0.1013 (4)	0.0199 (2)	0.0181 (2)	0.0000 (2)
S1	0.0426 (5)	0.0840 (7)	0.0398 (5)	−0.0032 (5)	−0.0080 (4)	−0.0043 (5)
S2	0.0379 (4)	0.0491 (5)	0.0532 (5)	−0.0001 (4)	0.0004 (4)	−0.0006 (4)
N1	0.0435 (16)	0.0588 (17)	0.0423 (16)	−0.0127 (14)	−0.0004 (12)	−0.0017 (14)
O1	0.0723 (18)	0.108 (2)	0.0522 (16)	−0.0252 (16)	−0.0088 (13)	−0.0267 (16)
O2	0.0485 (15)	0.118 (2)	0.0611 (17)	0.0205 (15)	−0.0109 (12)	0.0180 (16)
O3	0.0646 (17)	0.0829 (18)	0.0653 (18)	0.0025 (14)	0.0142 (14)	−0.0251 (15)
C1	0.0422 (18)	0.056 (2)	0.0294 (16)	0.0062 (16)	0.0000 (14)	−0.0014 (15)
C2	0.062 (2)	0.048 (2)	0.043 (2)	0.0115 (17)	0.0059 (17)	0.0018 (16)
C3	0.072 (3)	0.046 (2)	0.053 (2)	−0.0036 (19)	0.0172 (19)	0.0023 (17)
C4	0.056 (2)	0.062 (2)	0.045 (2)	−0.0007 (19)	0.0162 (16)	0.0007 (18)
C5	0.053 (2)	0.054 (2)	0.052 (2)	0.0127 (17)	0.0136 (17)	−0.0006 (17)
C6	0.057 (2)	0.0443 (18)	0.0370 (18)	0.0048 (16)	0.0079 (15)	−0.0056 (15)
C7	0.080 (3)	0.050 (2)	0.078 (3)	0.002 (2)	0.024 (2)	−0.011 (2)
C8	0.068 (3)	0.090 (3)	0.083 (3)	−0.013 (2)	0.024 (2)	−0.002 (2)
C9	0.079 (3)	0.061 (2)	0.097 (3)	0.027 (2)	0.014 (2)	0.000 (2)
C10	0.0296 (16)	0.0559 (19)	0.0381 (17)	−0.0055 (15)	0.0044 (13)	0.0027 (16)
C11	0.0321 (18)	0.072 (2)	0.054 (2)	0.0021 (17)	0.0027 (15)	0.006 (2)
C12	0.040 (2)	0.067 (2)	0.061 (2)	0.0101 (17)	0.0152 (17)	−0.003 (2)
C13	0.043 (2)	0.061 (2)	0.049 (2)	−0.0048 (17)	0.0149 (16)	−0.0064 (18)
C14	0.0362 (17)	0.062 (2)	0.0356 (18)	−0.0064 (16)	0.0027 (14)	0.0004 (16)
C15	0.0289 (16)	0.0535 (19)	0.0403 (18)	−0.0021 (14)	0.0043 (13)	0.0047 (15)
C16	0.0340 (17)	0.056 (2)	0.0294 (16)	0.0019 (15)	−0.0008 (12)	−0.0041 (15)
N17	0.0294 (14)	0.0520 (17)	0.0424 (15)	0.0012 (12)	0.0025 (11)	−0.0056 (13)
C18	0.0378 (19)	0.058 (2)	0.050 (2)	0.0022 (17)	0.0043 (15)	−0.0052 (17)
N19	0.0327 (16)	0.068 (2)	0.084 (2)	0.0034 (15)	0.0117 (15)	−0.0023 (18)
C20	0.0334 (19)	0.074 (3)	0.079 (3)	0.0102 (19)	0.0130 (18)	−0.001 (2)
C21	0.0423 (19)	0.058 (2)	0.051 (2)	0.0100 (17)	0.0057 (15)	−0.0047 (17)
N22	0.0324 (15)	0.0558 (18)	0.085 (2)	−0.0048 (14)	0.0119 (14)	−0.0099 (16)
C23	0.041 (2)	0.049 (2)	0.096 (3)	0.0003 (17)	0.007 (2)	0.002 (2)
C24	0.078 (3)	0.054 (2)	0.092 (3)	0.013 (2)	0.033 (2)	0.010 (2)
O25	0.081 (2)	0.0571 (17)	0.113 (3)	0.0073 (16)	−0.0002 (18)	−0.0187 (16)
C25	0.079 (3)	0.100 (3)	0.055 (2)	−0.021 (2)	0.014 (2)	−0.026 (2)
C26	0.065 (3)	0.057 (2)	0.112 (4)	−0.005 (2)	−0.022 (3)	0.001 (3)
C27	0.040 (2)	0.061 (2)	0.104 (3)	−0.0081 (18)	0.014 (2)	0.008 (2)

Br1—C21	1.885 (3)	C11—C12	1.368 (5)
S1—O2	1.424 (3)	C11—H11	0.9300
S1—O1	1.434 (3)	C12—C13	1.384 (5)
S1—N1	1.639 (3)	C12—H12	0.9300
S1—C1	1.782 (3)	C13—C14	1.376 (4)
S2—C16	1.761 (3)	C14—C15	1.396 (4)
S2—C15	1.772 (3)	C14—H14	0.9300
N1—C10	1.421 (4)	C16—N17	1.312 (4)
N1—H1	0.8600	C16—C21	1.399 (4)
O3—C13	1.367 (4)	N17—C18	1.342 (4)
O3—C25	1.421 (5)	C18—N19	1.347 (4)
C1—C6	1.402 (4)	C18—N22	1.359 (4)
C1—C2	1.410 (4)	N19—C20	1.322 (4)
C2—C3	1.385 (5)	C20—C21	1.377 (5)
C2—C9	1.519 (5)	C20—H20	0.9300
C3—C4	1.375 (5)	N22—C27	1.457 (4)
C3—H3	0.9300	N22—C23	1.458 (4)
C4—C5	1.371 (5)	C23—C24	1.487 (5)
C4—C8	1.511 (5)	C23—H23A	0.9700
C5—C6	1.398 (5)	C23—H23B	0.9700
C5—H5	0.9300	C24—O25	1.423 (5)
C6—C7	1.508 (4)	C24—H24A	0.9700
C7—H7A	0.9600	C24—H24B	0.9700
C7—H7B	0.9600	O25—C26	1.417 (5)
C7—H7C	0.9600	C25—H25A	0.9600
C8—H8A	0.9600	C25—H25B	0.9600
C8—H8B	0.9600	C25—H25C	0.9600
C8—H8C	0.9600	C26—C27	1.493 (6)
C9—H9A	0.9600	C26—H26A	0.9700
C9—H9B	0.9600	C26—H26B	0.9700
C9—H9C	0.9600	C27—H27A	0.9700
C10—C11	1.393 (4)	C27—H27B	0.9700
C10—C15	1.396 (4)
O2—S1—O1	118.40 (17)	O3—C13—C12	115.0 (3)
O2—S1—N1	107.62 (16)	C14—C13—C12	119.8 (3)
O1—S1—N1	104.85 (16)	C13—C14—C15	120.0 (3)
O2—S1—C1	109.14 (16)	C13—C14—H14	120.0
O1—S1—C1	109.49 (16)	C15—C14—H14	120.0
N1—S1—C1	106.67 (13)	C14—C15—C10	120.6 (3)
C16—S2—C15	100.73 (15)	C14—C15—S2	119.2 (2)
C10—N1—S1	121.8 (2)	C10—C15—S2	120.1 (2)
C10—N1—H1	119.1	N17—C16—C21	121.2 (3)
S1—N1—H1	119.1	N17—C16—S2	119.1 (2)
C13—O3—C25	118.3 (3)	C21—C16—S2	119.6 (3)
C6—C1—C2	120.1 (3)	C16—N17—C18	117.6 (3)
C6—C1—S1	118.6 (2)	N17—C18—N19	125.8 (3)
C2—C1—S1	121.3 (2)	N17—C18—N22	116.2 (3)
C3—C2—C1	118.0 (3)	N19—C18—N22	118.1 (3)
C3—C2—C9	116.5 (3)	C20—N19—C18	115.2 (3)
C1—C2—C9	125.5 (3)	N19—C20—C21	123.6 (3)
C4—C3—C2	123.3 (3)	N19—C20—H20	118.2
C4—C3—H3	118.3	C21—C20—H20	118.2
C2—C3—H3	118.3	C20—C21—C16	116.5 (3)
C5—C4—C3	117.4 (3)	C20—C21—Br1	121.7 (3)
C5—C4—C8	121.3 (3)	C16—C21—Br1	121.8 (3)
C3—C4—C8	121.3 (3)	C18—N22—C27	122.5 (3)
C4—C5—C6	122.9 (3)	C18—N22—C23	120.3 (3)
C4—C5—H5	118.6	C27—N22—C23	111.8 (3)
C6—C5—H5	118.6	N22—C23—C24	108.8 (3)
C5—C6—C1	118.1 (3)	N22—C23—H23A	109.9
C5—C6—C7	115.8 (3)	C24—C23—H23A	109.9
C1—C6—C7	126.0 (3)	N22—C23—H23B	109.9
C6—C7—H7A	109.5	C24—C23—H23B	109.9
C6—C7—H7B	109.5	H23A—C23—H23B	108.3
H7A—C7—H7B	109.5	O25—C24—C23	110.5 (3)
C6—C7—H7C	109.5	O25—C24—H24A	109.6
H7A—C7—H7C	109.5	C23—C24—H24A	109.6
H7B—C7—H7C	109.5	O25—C24—H24B	109.6
C4—C8—H8A	109.5	C23—C24—H24B	109.6
C4—C8—H8B	109.5	H24A—C24—H24B	108.1
H8A—C8—H8B	109.5	C26—O25—C24	111.1 (3)
C4—C8—H8C	109.5	O3—C25—H25A	109.5
H8A—C8—H8C	109.5	O3—C25—H25B	109.5
H8B—C8—H8C	109.5	H25A—C25—H25B	109.5
C2—C9—H9A	109.5	O3—C25—H25C	109.5
C2—C9—H9B	109.5	H25A—C25—H25C	109.5
H9A—C9—H9B	109.5	H25B—C25—H25C	109.5
C2—C9—H9C	109.5	O25—C26—C27	111.6 (3)
H9A—C9—H9C	109.5	O25—C26—H26A	109.3
H9B—C9—H9C	109.5	C27—C26—H26A	109.3
C11—C10—C15	117.7 (3)	O25—C26—H26B	109.3
C11—C10—N1	120.4 (3)	C27—C26—H26B	109.3
C15—C10—N1	121.9 (3)	H26A—C26—H26B	108.0
C12—C11—C10	121.6 (3)	N22—C27—C26	110.5 (3)
C12—C11—H11	119.2	N22—C27—H27A	109.6
C10—C11—H11	119.2	C26—C27—H27A	109.6
C11—C12—C13	120.2 (3)	N22—C27—H27B	109.6
C11—C12—H12	119.9	C26—C27—H27B	109.6
C13—C12—H12	119.9	H27A—C27—H27B	108.1
O3—C13—C14	125.2 (3)
O2—S1—N1—C10	−54.4 (3)	C13—C14—C15—C10	−3.0 (5)
O1—S1—N1—C10	178.7 (2)	C13—C14—C15—S2	179.5 (2)
C1—S1—N1—C10	62.6 (3)	C11—C10—C15—C14	1.5 (4)
O2—S1—C1—C6	−165.8 (2)	N1—C10—C15—C14	−176.3 (3)
O1—S1—C1—C6	−34.8 (3)	C11—C10—C15—S2	179.0 (2)
N1—S1—C1—C6	78.2 (3)	N1—C10—C15—S2	1.2 (4)
O2—S1—C1—C2	15.5 (3)	C16—S2—C15—C14	−65.8 (3)
O1—S1—C1—C2	146.6 (3)	C16—S2—C15—C10	116.7 (3)
N1—S1—C1—C2	−100.5 (3)	C15—S2—C16—N17	−4.9 (3)
C6—C1—C2—C3	1.8 (5)	C15—S2—C16—C21	174.0 (3)
S1—C1—C2—C3	−179.6 (2)	C21—C16—N17—C18	−1.8 (4)
C6—C1—C2—C9	−177.5 (3)	S2—C16—N17—C18	177.1 (2)
S1—C1—C2—C9	1.2 (5)	C16—N17—C18—N19	−0.7 (5)
C1—C2—C3—C4	−1.0 (5)	C16—N17—C18—N22	177.5 (3)
C9—C2—C3—C4	178.3 (3)	N17—C18—N19—C20	1.6 (5)
C2—C3—C4—C5	−0.7 (5)	N22—C18—N19—C20	−176.6 (3)
C2—C3—C4—C8	−179.0 (3)	C18—N19—C20—C21	0.1 (6)
C3—C4—C5—C6	1.8 (5)	N19—C20—C21—C16	−2.4 (5)
C8—C4—C5—C6	180.0 (3)	N19—C20—C21—Br1	178.1 (3)
C4—C5—C6—C1	−1.0 (5)	N17—C16—C21—C20	3.3 (5)
C4—C5—C6—C7	179.3 (3)	S2—C16—C21—C20	−175.6 (3)
C2—C1—C6—C5	−0.8 (5)	N17—C16—C21—Br1	−177.2 (2)
S1—C1—C6—C5	−179.5 (2)	S2—C16—C21—Br1	3.9 (4)
C2—C1—C6—C7	178.9 (3)	N17—C18—N22—C27	165.2 (3)
S1—C1—C6—C7	0.2 (4)	N19—C18—N22—C27	−16.4 (5)
S1—N1—C10—C11	67.5 (4)	N17—C18—N22—C23	13.2 (5)
S1—N1—C10—C15	−114.8 (3)	N19—C18—N22—C23	−168.4 (3)
C15—C10—C11—C12	0.7 (5)	C18—N22—C23—C24	98.4 (4)
N1—C10—C11—C12	178.5 (3)	C27—N22—C23—C24	−56.4 (4)
C10—C11—C12—C13	−1.4 (5)	N22—C23—C24—O25	59.2 (4)
C25—O3—C13—C14	−5.5 (5)	C23—C24—O25—C26	−60.5 (4)
C25—O3—C13—C12	173.0 (3)	C24—O25—C26—C27	57.3 (5)
C11—C12—C13—O3	−178.6 (3)	C18—N22—C27—C26	−100.5 (4)
C11—C12—C13—C14	−0.1 (5)	C23—N22—C27—C26	53.6 (4)
O3—C13—C14—C15	−179.3 (3)	O25—C26—C27—N22	−53.4 (4)
C12—C13—C14—C15	2.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O25i	0.86	2.09	2.890 (4)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O25i	0.86	2.09	2.890 (4)	155

Symmetry code: (i) .