2,4,6-Trimethyl-1,3,5-tris-(morpholino-meth-yl)benzene.

In the title compound, C(24)H(39)N(3)O(3), the H atoms of the methyl groups are disordered over two positions, with site-occupation factors fixed at 0.5. The three morpholino groups are arranged in an asymmetrical fashion with respect to the anchoring mesitylene ring and adopt chair conformations. Inter-molecular C-H⋯π inter-actions link the mol-ecules into a one-dimensional chain structure.

Related literature

For related literature, see: Blackman (2005 ▶); Nakai et al. (2003 ▶); Van der Made & Van der Made (1993 ▶); Zeng & Zimmerman (1997 ▶).

Experimental

Crystal data

C24H39N3O3

M = 417.58

Monoclinic,

a = 11.0139 (10) Å

b = 24.131 (2) Å

c = 9.2941 (8) Å

β = 108.2330 (10)°

V = 2346.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 291 (2) K

0.49 × 0.37 × 0.34 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.963, T max = 0.974

16860 measured reflections

4350 independent reflections

3409 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.125

S = 1.03

4350 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); 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/S1600536808008763/fj2099sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008763/fj2099Isup2.hkl

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

C24H39N3O3	F000 = 912
Mr = 417.58	Dx = 1.182 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
a = 11.0139 (10) Å	Cell parameters from 6077 reflections
b = 24.131 (2) Å	θ = 2.5–28.1º
c = 9.2941 (8) Å	µ = 0.08 mm−1
β = 108.2330 (10)º	T = 291 (2) K
V = 2346.2 (4) Å3	Block, colourless
Z = 4	0.49 × 0.37 × 0.34 mm

Bruker SMART APEXII CCD area-detector diffractometer	4350 independent reflections
Radiation source: fine-focus sealed tube	3409 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.019
T = 291(2) K	θmax = 25.5º
φ and ω scans	θmin = 2.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.963, Tmax = 0.974	k = −29→28
16860 measured reflections	l = −11→11

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.125	w = 1/[σ2(Fo2) + (0.061P)2 + 0.5317P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
4350 reflections	Δρmax = 0.20 e Å−3
271 parameters	Δρmin = −0.16 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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)
O1	−0.47311 (11)	0.13824 (5)	0.54089 (16)	0.0666 (4)
O2	0.46925 (15)	0.21500 (6)	1.12778 (16)	0.0820 (4)
O3	0.11437 (19)	−0.24231 (5)	0.84017 (19)	0.0984 (6)
N1	−0.25289 (11)	0.07200 (5)	0.56752 (14)	0.0428 (3)
N2	0.33067 (12)	0.13735 (5)	0.90381 (14)	0.0437 (3)
N3	0.06308 (13)	−0.12834 (5)	0.87425 (15)	0.0481 (3)
C1	−0.02514 (13)	0.03908 (6)	0.65905 (15)	0.0377 (3)
C2	0.08664 (13)	0.07108 (5)	0.69121 (16)	0.0381 (3)
C3	0.19919 (13)	0.05277 (5)	0.80117 (16)	0.0373 (3)
C4	0.19841 (13)	0.00444 (5)	0.88471 (16)	0.0391 (3)
C5	0.08374 (13)	−0.02549 (5)	0.85949 (16)	0.0380 (3)
C6	−0.02704 (13)	−0.00860 (6)	0.74496 (16)	0.0383 (3)
C7	−0.14249 (14)	0.05271 (6)	0.52502 (16)	0.0449 (4)
H7A	−0.1197	0.0811	0.4642	0.054*
H7B	−0.1671	0.0199	0.4624	0.054*
C8	0.08791 (17)	0.12500 (7)	0.6081 (2)	0.0544 (4)
H8A	0.1715	0.1413	0.6443	0.082*	0.50
H8B	0.0264	0.1500	0.6259	0.082*	0.50
H8C	0.0666	0.1178	0.5015	0.082*	0.50
H8D	0.0048	0.1315	0.5368	0.082*	0.50
H8E	0.1499	0.1227	0.5552	0.082*	0.50
H8F	0.1098	0.1549	0.6796	0.082*	0.50
C9	0.32124 (14)	0.08548 (6)	0.81870 (18)	0.0441 (4)
H9A	0.3940	0.0623	0.8696	0.053*
H9B	0.3263	0.0940	0.7187	0.053*
C10	0.32062 (15)	−0.01643 (7)	0.9995 (2)	0.0551 (4)
H10A	0.3029	−0.0497	1.0460	0.083*	0.50
H10B	0.3533	0.0113	1.0759	0.083*	0.50
H10C	0.3829	−0.0241	0.9494	0.083*	0.50
H10D	0.3898	0.0081	1.0015	0.083*	0.50
H10E	0.3394	−0.0530	0.9716	0.083*	0.50
H10F	0.3099	−0.0176	1.0981	0.083*	0.50
C11	0.07458 (16)	−0.07542 (6)	0.95527 (18)	0.0463 (4)
H11A	0.1501	−0.0766	1.0437	0.056*
H11B	0.0009	−0.0709	0.9903	0.056*
C12	−0.14914 (15)	−0.04149 (6)	0.7153 (2)	0.0541 (4)
H12A	−0.1345	−0.0726	0.7831	0.081*	0.50
H12B	−0.1761	−0.0545	0.6126	0.081*	0.50
H12C	−0.2145	−0.0183	0.7315	0.081*	0.50
H12D	−0.2155	−0.0243	0.6350	0.081*	0.50
H12E	−0.1739	−0.0424	0.8055	0.081*	0.50
H12F	−0.1355	−0.0786	0.6866	0.081*	0.50
C13	−0.37183 (15)	0.06447 (7)	0.4433 (2)	0.0557 (4)
H13A	−0.3815	0.0259	0.4127	0.067*
H13B	−0.3700	0.0866	0.3569	0.067*
C14	−0.48270 (17)	0.08214 (8)	0.4958 (3)	0.0687 (5)
H14A	−0.5620	0.0766	0.4142	0.082*
H14B	−0.4852	0.0590	0.5803	0.082*
C15	−0.35579 (17)	0.14720 (8)	0.6582 (2)	0.0615 (5)
H15A	−0.3560	0.1262	0.7471	0.074*
H15B	−0.3483	0.1862	0.6854	0.074*
C16	−0.24239 (15)	0.13020 (6)	0.61083 (19)	0.0481 (4)
H16A	−0.2385	0.1528	0.5260	0.058*
H16B	−0.1643	0.1361	0.6940	0.058*
C17	0.43157 (18)	0.17266 (7)	0.8820 (2)	0.0610 (5)
H17A	0.4125	0.1811	0.7752	0.073*
H17B	0.5125	0.1530	0.9151	0.073*
C18	0.4424 (2)	0.22552 (8)	0.9701 (2)	0.0802 (6)
H18A	0.5100	0.2481	0.9546	0.096*
H18B	0.3629	0.2460	0.9329	0.096*
C19	0.3719 (2)	0.18151 (8)	1.1505 (2)	0.0746 (6)
H19A	0.2914	0.2014	1.1171	0.090*
H19B	0.3913	0.1739	1.2577	0.090*
C20	0.35830 (18)	0.12758 (7)	1.06520 (19)	0.0548 (4)
H20A	0.4368	0.1065	1.1029	0.066*
H20B	0.2898	0.1060	1.0822	0.066*
C21	0.18365 (18)	−0.14662 (7)	0.8563 (2)	0.0583 (4)
H21A	0.2464	−0.1519	0.9552	0.070*
H21B	0.2156	−0.1184	0.8030	0.070*
C22	0.1652 (2)	−0.20017 (8)	0.7689 (3)	0.0819 (7)
H22A	0.1076	−0.1940	0.6674	0.098*
H22B	0.2466	−0.2123	0.7606	0.098*
C23	−0.0016 (3)	−0.22429 (8)	0.8599 (3)	0.0983 (8)
H23A	−0.0344	−0.2532	0.9103	0.118*
H23B	−0.0641	−0.2179	0.7615	0.118*
C24	0.0157 (2)	−0.17187 (7)	0.9519 (3)	0.0706 (5)
H24A	−0.0652	−0.1607	0.9638	0.085*
H24B	0.0762	−0.1781	1.0518	0.085*

	U11	U22	U33	U12	U13	U23
O1	0.0535 (7)	0.0607 (8)	0.0796 (9)	0.0192 (6)	0.0119 (6)	0.0079 (6)
O2	0.1027 (11)	0.0632 (8)	0.0669 (9)	−0.0336 (8)	0.0078 (8)	−0.0112 (7)
O3	0.1412 (15)	0.0329 (7)	0.1057 (12)	0.0187 (8)	0.0165 (11)	0.0031 (7)
N1	0.0403 (7)	0.0374 (6)	0.0435 (7)	0.0050 (5)	0.0026 (5)	0.0000 (5)
N2	0.0441 (7)	0.0375 (6)	0.0465 (7)	−0.0053 (5)	0.0100 (6)	−0.0001 (5)
N3	0.0563 (8)	0.0282 (6)	0.0533 (8)	0.0020 (5)	0.0077 (6)	0.0027 (5)
C1	0.0403 (8)	0.0338 (7)	0.0366 (7)	0.0064 (6)	0.0084 (6)	−0.0055 (6)
C2	0.0435 (8)	0.0328 (7)	0.0367 (7)	0.0034 (6)	0.0106 (6)	−0.0026 (6)
C3	0.0401 (8)	0.0313 (7)	0.0394 (8)	0.0018 (6)	0.0107 (6)	−0.0053 (6)
C4	0.0409 (8)	0.0314 (7)	0.0410 (8)	0.0046 (6)	0.0074 (6)	−0.0037 (6)
C5	0.0453 (8)	0.0274 (7)	0.0401 (8)	0.0033 (6)	0.0117 (6)	−0.0038 (6)
C6	0.0388 (8)	0.0313 (7)	0.0436 (8)	0.0024 (6)	0.0108 (6)	−0.0076 (6)
C7	0.0450 (8)	0.0455 (8)	0.0384 (8)	0.0043 (6)	0.0047 (6)	−0.0054 (6)
C8	0.0579 (10)	0.0461 (9)	0.0549 (10)	0.0020 (7)	0.0116 (8)	0.0113 (7)
C9	0.0418 (8)	0.0413 (8)	0.0480 (9)	0.0017 (6)	0.0124 (7)	−0.0014 (6)
C10	0.0475 (9)	0.0420 (8)	0.0644 (11)	0.0031 (7)	0.0010 (8)	0.0068 (8)
C11	0.0560 (9)	0.0341 (8)	0.0470 (9)	0.0000 (6)	0.0135 (7)	0.0000 (6)
C12	0.0465 (9)	0.0391 (8)	0.0721 (11)	−0.0027 (7)	0.0121 (8)	−0.0037 (8)
C13	0.0426 (9)	0.0508 (9)	0.0622 (11)	−0.0019 (7)	−0.0003 (8)	−0.0053 (8)
C14	0.0437 (10)	0.0677 (12)	0.0866 (14)	−0.0008 (8)	0.0086 (9)	0.0056 (10)
C15	0.0647 (11)	0.0527 (10)	0.0638 (11)	0.0154 (8)	0.0155 (9)	−0.0023 (8)
C16	0.0492 (9)	0.0409 (8)	0.0482 (9)	0.0018 (7)	0.0065 (7)	−0.0026 (7)
C17	0.0642 (11)	0.0580 (10)	0.0578 (10)	−0.0192 (8)	0.0148 (9)	0.0045 (8)
C18	0.1019 (16)	0.0556 (11)	0.0723 (13)	−0.0325 (11)	0.0117 (12)	0.0004 (10)
C19	0.1005 (16)	0.0594 (11)	0.0640 (12)	−0.0135 (11)	0.0257 (11)	−0.0139 (9)
C20	0.0662 (11)	0.0467 (9)	0.0513 (9)	−0.0085 (8)	0.0183 (8)	−0.0014 (7)
C21	0.0679 (11)	0.0450 (9)	0.0562 (10)	0.0109 (8)	0.0113 (9)	0.0005 (8)
C22	0.1139 (18)	0.0472 (11)	0.0763 (14)	0.0241 (11)	0.0178 (13)	−0.0038 (10)
C23	0.120 (2)	0.0357 (10)	0.125 (2)	−0.0137 (12)	0.0169 (17)	0.0026 (11)
C24	0.0800 (13)	0.0394 (9)	0.0888 (14)	−0.0077 (9)	0.0214 (11)	0.0096 (9)

O1—C14	1.411 (2)	C10—H10E	0.9600
O1—C15	1.423 (2)	C10—H10F	0.9600
O2—C19	1.410 (2)	C11—H11A	0.9700
O2—C18	1.424 (2)	C11—H11B	0.9700
O3—C23	1.415 (3)	C12—H12A	0.9600
O3—C22	1.420 (3)	C12—H12B	0.9600
N1—C16	1.4555 (19)	C12—H12C	0.9600
N1—C13	1.4612 (19)	C12—H12D	0.9600
N1—C7	1.4669 (19)	C12—H12E	0.9600
N2—C20	1.453 (2)	C12—H12F	0.9600
N2—C17	1.464 (2)	C13—C14	1.511 (3)
N2—C9	1.4670 (19)	C13—H13A	0.9700
N3—C21	1.458 (2)	C13—H13B	0.9700
N3—C24	1.460 (2)	C14—H14A	0.9700
N3—C11	1.4676 (19)	C14—H14B	0.9700
C1—C6	1.404 (2)	C15—C16	1.505 (2)
C1—C2	1.404 (2)	C15—H15A	0.9700
C1—C7	1.5241 (19)	C15—H15B	0.9700
C2—C3	1.408 (2)	C16—H16A	0.9700
C2—C8	1.515 (2)	C16—H16B	0.9700
C3—C4	1.403 (2)	C17—C18	1.500 (3)
C3—C9	1.523 (2)	C17—H17A	0.9700
C4—C5	1.409 (2)	C17—H17B	0.9700
C4—C10	1.518 (2)	C18—H18A	0.9700
C5—C6	1.4054 (19)	C18—H18B	0.9700
C5—C11	1.520 (2)	C19—C20	1.507 (2)
C6—C12	1.511 (2)	C19—H19A	0.9700
C7—H7A	0.9700	C19—H19B	0.9700
C7—H7B	0.9700	C20—H20A	0.9700
C8—H8A	0.9600	C20—H20B	0.9700
C8—H8B	0.9600	C21—C22	1.506 (2)
C8—H8C	0.9600	C21—H21A	0.9700
C8—H8D	0.9600	C21—H21B	0.9700
C8—H8E	0.9600	C22—H22A	0.9700
C8—H8F	0.9600	C22—H22B	0.9700
C9—H9A	0.9700	C23—C24	1.505 (3)
C9—H9B	0.9700	C23—H23A	0.9700
C10—H10A	0.9600	C23—H23B	0.9700
C10—H10B	0.9600	C24—H24A	0.9700
C10—H10C	0.9600	C24—H24B	0.9700
C10—H10D	0.9600
C14—O1—C15	109.82 (13)	H12A—C12—H12B	109.5
C19—O2—C18	109.45 (15)	C6—C12—H12C	109.5
C23—O3—C22	110.11 (16)	H12A—C12—H12C	109.5
C16—N1—C13	108.21 (12)	H12B—C12—H12C	109.5
C16—N1—C7	112.33 (12)	C6—C12—H12D	109.5
C13—N1—C7	111.20 (12)	H12A—C12—H12D	141.1
C20—N2—C17	108.33 (13)	H12B—C12—H12D	56.3
C20—N2—C9	112.00 (12)	H12C—C12—H12D	56.3
C17—N2—C9	110.53 (13)	C6—C12—H12E	109.5
C21—N3—C24	108.54 (13)	H12A—C12—H12E	56.3
C21—N3—C11	112.74 (13)	H12B—C12—H12E	141.1
C24—N3—C11	111.04 (13)	H12C—C12—H12E	56.3
C6—C1—C2	119.84 (13)	H12D—C12—H12E	109.5
C6—C1—C7	118.80 (13)	C6—C12—H12F	109.5
C2—C1—C7	121.22 (13)	H12A—C12—H12F	56.3
C1—C2—C3	119.75 (13)	H12B—C12—H12F	56.3
C1—C2—C8	120.73 (13)	H12C—C12—H12F	141.1
C3—C2—C8	119.52 (13)	H12D—C12—H12F	109.5
C4—C3—C2	120.40 (13)	H12E—C12—H12F	109.5
C4—C3—C9	121.99 (13)	N1—C13—C14	108.98 (15)
C2—C3—C9	117.52 (13)	N1—C13—H13A	109.9
C3—C4—C5	119.64 (13)	C14—C13—H13A	109.9
C3—C4—C10	120.48 (13)	N1—C13—H13B	109.9
C5—C4—C10	119.87 (13)	C14—C13—H13B	109.9
C6—C5—C4	119.85 (13)	H13A—C13—H13B	108.3
C6—C5—C11	118.19 (13)	O1—C14—C13	111.93 (15)
C4—C5—C11	121.94 (13)	O1—C14—H14A	109.2
C1—C6—C5	120.29 (13)	C13—C14—H14A	109.2
C1—C6—C12	119.83 (13)	O1—C14—H14B	109.2
C5—C6—C12	119.87 (13)	C13—C14—H14B	109.2
N1—C7—C1	114.26 (12)	H14A—C14—H14B	107.9
N1—C7—H7A	108.7	O1—C15—C16	111.83 (15)
C1—C7—H7A	108.7	O1—C15—H15A	109.2
N1—C7—H7B	108.7	C16—C15—H15A	109.2
C1—C7—H7B	108.7	O1—C15—H15B	109.2
H7A—C7—H7B	107.6	C16—C15—H15B	109.2
C2—C8—H8A	109.5	H15A—C15—H15B	107.9
C2—C8—H8B	109.5	N1—C16—C15	110.03 (14)
H8A—C8—H8B	109.5	N1—C16—H16A	109.7
C2—C8—H8C	109.5	C15—C16—H16A	109.7
H8A—C8—H8C	109.5	N1—C16—H16B	109.7
H8B—C8—H8C	109.5	C15—C16—H16B	109.7
C2—C8—H8D	109.5	H16A—C16—H16B	108.2
H8A—C8—H8D	141.1	N2—C17—C18	110.69 (16)
H8B—C8—H8D	56.3	N2—C17—H17A	109.5
H8C—C8—H8D	56.3	C18—C17—H17A	109.5
C2—C8—H8E	109.5	N2—C17—H17B	109.5
H8A—C8—H8E	56.3	C18—C17—H17B	109.5
H8B—C8—H8E	141.1	H17A—C17—H17B	108.1
H8C—C8—H8E	56.3	O2—C18—C17	111.44 (16)
H8D—C8—H8E	109.5	O2—C18—H18A	109.3
C2—C8—H8F	109.5	C17—C18—H18A	109.3
H8A—C8—H8F	56.3	O2—C18—H18B	109.3
H8B—C8—H8F	56.3	C17—C18—H18B	109.3
H8C—C8—H8F	141.1	H18A—C18—H18B	108.0
H8D—C8—H8F	109.5	O2—C19—C20	111.81 (17)
H8E—C8—H8F	109.5	O2—C19—H19A	109.3
N2—C9—C3	114.27 (12)	C20—C19—H19A	109.3
N2—C9—H9A	108.7	O2—C19—H19B	109.3
C3—C9—H9A	108.7	C20—C19—H19B	109.3
N2—C9—H9B	108.7	H19A—C19—H19B	107.9
C3—C9—H9B	108.7	N2—C20—C19	110.91 (14)
H9A—C9—H9B	107.6	N2—C20—H20A	109.5
C4—C10—H10A	109.5	C19—C20—H20A	109.5
C4—C10—H10B	109.5	N2—C20—H20B	109.5
H10A—C10—H10B	109.5	C19—C20—H20B	109.5
C4—C10—H10C	109.5	H20A—C20—H20B	108.0
H10A—C10—H10C	109.5	N3—C21—C22	110.32 (16)
H10B—C10—H10C	109.5	N3—C21—H21A	109.6
C4—C10—H10D	109.5	C22—C21—H21A	109.6
H10A—C10—H10D	141.1	N3—C21—H21B	109.6
H10B—C10—H10D	56.3	C22—C21—H21B	109.6
H10C—C10—H10D	56.3	H21A—C21—H21B	108.1
C4—C10—H10E	109.5	O3—C22—C21	111.68 (18)
H10A—C10—H10E	56.3	O3—C22—H22A	109.3
H10B—C10—H10E	141.1	C21—C22—H22A	109.3
H10C—C10—H10E	56.3	O3—C22—H22B	109.3
H10D—C10—H10E	109.5	C21—C22—H22B	109.3
C4—C10—H10F	109.5	H22A—C22—H22B	107.9
H10A—C10—H10F	56.3	O3—C23—C24	111.9 (2)
H10B—C10—H10F	56.3	O3—C23—H23A	109.2
H10C—C10—H10F	141.1	C24—C23—H23A	109.2
H10D—C10—H10F	109.5	O3—C23—H23B	109.2
H10E—C10—H10F	109.5	C24—C23—H23B	109.2
N3—C11—C5	113.58 (12)	H23A—C23—H23B	107.9
N3—C11—H11A	108.8	N3—C24—C23	108.98 (18)
C5—C11—H11A	108.8	N3—C24—H24A	109.9
N3—C11—H11B	108.8	C23—C24—H24A	109.9
C5—C11—H11B	108.8	N3—C24—H24B	109.9
H11A—C11—H11B	107.7	C23—C24—H24B	109.9
C6—C12—H12A	109.5	H24A—C24—H24B	108.3
C6—C12—H12B	109.5
C6—C1—C2—C3	5.1 (2)	C4—C3—C9—N2	−105.37 (15)
C7—C1—C2—C3	−170.54 (13)	C2—C3—C9—N2	77.97 (16)
C6—C1—C2—C8	−175.31 (13)	C21—N3—C11—C5	75.51 (16)
C7—C1—C2—C8	9.0 (2)	C24—N3—C11—C5	−162.43 (14)
C1—C2—C3—C4	−3.6 (2)	C6—C5—C11—N3	72.68 (17)
C8—C2—C3—C4	176.80 (13)	C4—C5—C11—N3	−108.64 (15)
C1—C2—C3—C9	173.10 (12)	C16—N1—C13—C14	−59.13 (18)
C8—C2—C3—C9	−6.48 (19)	C7—N1—C13—C14	177.05 (14)
C2—C3—C4—C5	−0.8 (2)	C15—O1—C14—C13	−57.6 (2)
C9—C3—C4—C5	−177.38 (13)	N1—C13—C14—O1	59.8 (2)
C2—C3—C4—C10	177.94 (14)	C14—O1—C15—C16	56.5 (2)
C9—C3—C4—C10	1.4 (2)	C13—N1—C16—C15	58.77 (17)
C3—C4—C5—C6	3.7 (2)	C7—N1—C16—C15	−178.10 (12)
C10—C4—C5—C6	−175.03 (14)	O1—C15—C16—N1	−58.12 (18)
C3—C4—C5—C11	−174.93 (12)	C20—N2—C17—C18	−56.39 (19)
C10—C4—C5—C11	6.3 (2)	C9—N2—C17—C18	−179.45 (14)
C2—C1—C6—C5	−2.2 (2)	C19—O2—C18—C17	−58.3 (2)
C7—C1—C6—C5	173.55 (12)	N2—C17—C18—O2	58.7 (2)
C2—C1—C6—C12	177.06 (13)	C18—O2—C19—C20	57.9 (2)
C7—C1—C6—C12	−7.2 (2)	C17—N2—C20—C19	55.92 (19)
C4—C5—C6—C1	−2.2 (2)	C9—N2—C20—C19	178.08 (15)
C11—C5—C6—C1	176.48 (12)	O2—C19—C20—N2	−58.3 (2)
C4—C5—C6—C12	178.50 (13)	C24—N3—C21—C22	58.08 (19)
C11—C5—C6—C12	−2.8 (2)	C11—N3—C21—C22	−178.46 (14)
C16—N1—C7—C1	79.92 (16)	C23—O3—C22—C21	56.2 (2)
C13—N1—C7—C1	−158.63 (13)	N3—C21—C22—O3	−57.3 (2)
C6—C1—C7—N1	71.62 (16)	C22—O3—C23—C24	−57.9 (3)
C2—C1—C7—N1	−112.69 (15)	C21—N3—C24—C23	−58.8 (2)
C20—N2—C9—C3	73.86 (16)	C11—N3—C24—C23	176.75 (17)
C17—N2—C9—C3	−165.24 (13)	O3—C23—C24—N3	59.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···Cg1i	0.97	2.90	3.731 (2)	144
C7—H7B···Cg1ii	0.97	2.80	3.528 (2)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯Cg1i	0.97	2.90	3.731 (2)	144
C7—H7B⋯Cg1ii	0.97	2.80	3.528 (2)	132

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the benzene ring.