2-[2-(2-Nitro-phen-yl)-4,5-diphenyl-1H-imidazol-1-yl]-3-phenyl-propan-1-ol.

In the title compound, C30H25N3O3, the central imidazole ring forms dihedral angles of 77.34 (6), 12.56 (6) and 87.04 (6)°, respectively, with the o-nitro-benzene ring and the phenyl substituents in the 5- and 4-positions. The mol-ecular conformation is stabilized by weak intra-molecular C-H⋯π inter-actions. In the crystal, mol-ecules are linked by O-H⋯N hydrogen bonds, forming chains running parallel to the b-axis direction.

Related literature

For the synthesis of imidazole derivatives, see: Ding et al. (2005 ▶); Heightman & Vasella (1999 ▶); Wasserscheid & Keim (2000 ▶). For related compounds synthesized by our group, see: Gao, Yang et al. (2013 ▶); Gao, Wang et al. (2013 ▶); Mao et al. (2010 ▶); Yang et al. (2012 ▶); Xiao et al. (2012 ▶).

Experimental

Crystal data

C30H25N3O3

M = 475.53

Orthorhombic,

a = 10.54812 (16) Å

b = 12.77836 (19) Å

c = 18.4800 (3) Å

V = 2490.87 (6) Å3

Z = 4

Cu Kα radiation

μ = 0.67 mm−1

T = 291 K

0.25 × 0.22 × 0.20 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.638, T max = 1.000

23649 measured reflections

4460 independent reflections

4263 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.111

S = 1.05

4460 reflections

330 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.14 e Å−3

Absolute structure: Flack (1983 ▶); 1925 Friedel pairs

Absolute structure parameter: 0.2 (2)

Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814008770/rz5116sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814008770/rz5116Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814008770/rz5116Isup3.cml

CCDC reference: 997919

Additional supporting information: crystallographic information; 3D view; checkCIF report

C30H25N3O3	Dx = 1.268 Mg m−3
Mr = 475.53	Cu Kα radiation, λ = 1.5418 Å
Orthorhombic, P212121	Cell parameters from 12200 reflections
a = 10.54812 (16) Å	θ = 4.2–72.5°
b = 12.77836 (19) Å	µ = 0.67 mm−1
c = 18.4800 (3) Å	T = 291 K
V = 2490.87 (6) Å3	, yellow
Z = 4	0.25 × 0.22 × 0.20 mm
F(000) = 1000

Agilent Xcalibur (Eos, Gemini) diffractometer	4460 independent reflections
Radiation source: Enhance (Cu) X-ray Source	4263 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
Detector resolution: 16.2312 pixels mm-1	θmax = 67.1°, θmin = 4.2°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −15→14
Tmin = 0.638, Tmax = 1.000	l = −22→21
23649 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.038	w = 1/[σ2(Fo2) + (0.0732P)2 + 0.1165P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.111	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.16 e Å−3
4460 reflections	Δρmin = −0.14 e Å−3
330 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0020 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983); 1925 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.2 (2)

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
O1	0.3588 (2)	0.84256 (18)	0.76549 (10)	0.0943 (6)
O2	0.2703 (2)	0.8468 (2)	0.86999 (14)	0.1240 (9)
O3	0.69834 (12)	0.98409 (9)	0.67498 (6)	0.0495 (3)
N1	0.42502 (13)	0.60777 (11)	0.72217 (7)	0.0421 (3)
N2	0.58116 (12)	0.71200 (10)	0.68724 (7)	0.0381 (3)
N3	0.3581 (2)	0.82279 (15)	0.82985 (10)	0.0720 (5)
C1	0.2345 (2)	0.50148 (18)	0.63890 (11)	0.0643 (5)
H1	0.2249	0.5090	0.6887	0.077*
C2	0.1417 (3)	0.4507 (2)	0.59907 (14)	0.0823 (8)
H2	0.0699	0.4249	0.6222	0.099*
C3	0.1554 (3)	0.43820 (18)	0.52542 (13)	0.0763 (7)
H3A	0.0929	0.4043	0.4988	0.092*
C4	0.2609 (2)	0.47571 (15)	0.49166 (11)	0.0629 (5)
H4	0.2704	0.4667	0.4420	0.075*
C5	0.3536 (2)	0.52686 (14)	0.53059 (10)	0.0537 (4)
H5	0.4251	0.5521	0.5068	0.064*
C6	0.34175 (17)	0.54120 (12)	0.60510 (9)	0.0450 (4)
C7	0.43445 (15)	0.60224 (12)	0.64747 (8)	0.0406 (3)
C8	0.53212 (15)	0.66520 (12)	0.62466 (8)	0.0393 (3)
C9	0.58588 (15)	0.67981 (14)	0.55083 (8)	0.0442 (4)
C10	0.54220 (18)	0.75864 (16)	0.50552 (9)	0.0537 (4)
H10	0.4809	0.8053	0.5219	0.064*
C11	0.5900 (3)	0.7680 (2)	0.43568 (10)	0.0741 (7)
H11	0.5611	0.8214	0.4058	0.089*
C12	0.6789 (3)	0.6993 (3)	0.41067 (11)	0.0847 (8)
H12	0.7111	0.7064	0.3641	0.102*
C13	0.7207 (2)	0.6199 (2)	0.45434 (13)	0.0817 (8)
H13	0.7803	0.5725	0.4370	0.098*
C14	0.6749 (2)	0.60967 (18)	0.52423 (11)	0.0624 (5)
H14	0.7039	0.5555	0.5535	0.075*
C15	0.51231 (14)	0.67378 (12)	0.74329 (8)	0.0390 (3)
C16	0.53902 (15)	0.70021 (13)	0.82028 (8)	0.0434 (3)
C17	0.46705 (19)	0.76810 (14)	0.86142 (9)	0.0518 (4)
C18	0.4959 (3)	0.78953 (19)	0.93326 (12)	0.0753 (7)
H18	0.4461	0.8357	0.9597	0.090*
C19	0.5983 (3)	0.7422 (2)	0.96475 (11)	0.0810 (8)
H19	0.6188	0.7567	1.0126	0.097*
C20	0.6698 (2)	0.6741 (2)	0.92610 (12)	0.0805 (7)
H20	0.7392	0.6419	0.9477	0.097*
C21	0.64027 (19)	0.6518 (2)	0.85425 (11)	0.0640 (5)
H21	0.6892	0.6037	0.8288	0.077*
C22	0.8477 (2)	0.58423 (16)	0.71153 (13)	0.0613 (5)
H22	0.7936	0.5592	0.6758	0.074*
C23	0.9023 (2)	0.51434 (18)	0.75950 (16)	0.0775 (7)
H23	0.8833	0.4434	0.7564	0.093*
C24	0.9841 (3)	0.5492 (2)	0.81139 (19)	0.0896 (8)
H24	1.0202	0.5026	0.8440	0.108*
C25	1.0122 (3)	0.6533 (3)	0.81481 (19)	0.0993 (9)
H25	1.0702	0.6771	0.8489	0.119*
C26	0.9552 (2)	0.7242 (2)	0.76789 (14)	0.0747 (6)
H26	0.9737	0.7951	0.7719	0.090*
C27	0.87162 (15)	0.69031 (15)	0.71554 (10)	0.0503 (4)
C28	0.80645 (16)	0.76837 (14)	0.66683 (10)	0.0488 (4)
H28A	0.7999	0.7390	0.6186	0.059*
H28B	0.8581	0.8310	0.6637	0.059*
C29	0.67331 (14)	0.79849 (12)	0.69335 (8)	0.0400 (3)
H29	0.6811	0.8145	0.7450	0.048*
C30	0.62316 (17)	0.89749 (13)	0.65685 (9)	0.0475 (4)
H30A	0.6233	0.8880	0.6048	0.057*
H30B	0.5365	0.9100	0.6721	0.057*
H3	0.658 (2)	1.023 (2)	0.7087 (16)	0.078 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.1086 (13)	0.1066 (14)	0.0678 (10)	0.0422 (12)	0.0073 (10)	0.0090 (10)
O2	0.1259 (17)	0.139 (2)	0.1075 (16)	0.0540 (16)	0.0522 (14)	0.0077 (15)
O3	0.0666 (7)	0.0394 (6)	0.0426 (6)	−0.0080 (5)	0.0105 (5)	−0.0074 (5)
N1	0.0531 (7)	0.0423 (7)	0.0309 (6)	−0.0089 (6)	−0.0013 (5)	0.0044 (5)
N2	0.0465 (6)	0.0352 (6)	0.0327 (6)	−0.0033 (5)	0.0020 (5)	0.0004 (5)
N3	0.0920 (12)	0.0620 (10)	0.0621 (11)	0.0134 (10)	0.0226 (9)	−0.0047 (9)
C1	0.0784 (12)	0.0682 (12)	0.0464 (9)	−0.0281 (11)	−0.0132 (9)	0.0115 (9)
C2	0.0859 (15)	0.0888 (17)	0.0722 (14)	−0.0435 (14)	−0.0203 (12)	0.0142 (13)
C3	0.0934 (16)	0.0622 (12)	0.0735 (14)	−0.0236 (12)	−0.0397 (13)	0.0008 (11)
C4	0.0942 (14)	0.0472 (10)	0.0472 (10)	−0.0038 (10)	−0.0249 (10)	−0.0031 (8)
C5	0.0724 (11)	0.0451 (9)	0.0437 (9)	−0.0043 (8)	−0.0091 (8)	−0.0001 (7)
C6	0.0598 (9)	0.0357 (7)	0.0394 (8)	−0.0048 (7)	−0.0119 (7)	0.0042 (6)
C7	0.0541 (8)	0.0361 (7)	0.0317 (7)	−0.0021 (7)	−0.0034 (6)	0.0030 (6)
C8	0.0513 (7)	0.0361 (7)	0.0307 (7)	−0.0014 (6)	−0.0013 (6)	−0.0003 (6)
C9	0.0524 (8)	0.0475 (8)	0.0328 (7)	−0.0097 (7)	0.0019 (6)	−0.0037 (6)
C10	0.0671 (10)	0.0579 (10)	0.0361 (8)	−0.0133 (8)	−0.0060 (7)	0.0053 (7)
C11	0.0982 (16)	0.0879 (16)	0.0363 (9)	−0.0388 (14)	−0.0085 (10)	0.0109 (10)
C12	0.0977 (16)	0.120 (2)	0.0368 (9)	−0.0439 (17)	0.0187 (11)	−0.0152 (12)
C13	0.0776 (13)	0.109 (2)	0.0584 (13)	−0.0133 (14)	0.0205 (11)	−0.0371 (14)
C14	0.0686 (11)	0.0683 (12)	0.0503 (10)	0.0008 (10)	0.0058 (8)	−0.0157 (9)
C15	0.0498 (7)	0.0369 (7)	0.0303 (7)	−0.0031 (6)	0.0016 (6)	0.0020 (6)
C16	0.0535 (8)	0.0449 (8)	0.0318 (7)	−0.0141 (7)	0.0004 (6)	0.0016 (6)
C17	0.0710 (10)	0.0452 (9)	0.0392 (8)	−0.0135 (8)	0.0101 (8)	−0.0021 (7)
C18	0.1157 (19)	0.0663 (13)	0.0440 (10)	−0.0335 (13)	0.0190 (11)	−0.0146 (9)
C19	0.1110 (18)	0.0966 (17)	0.0353 (9)	−0.0515 (16)	−0.0103 (11)	−0.0013 (10)
C20	0.0772 (13)	0.116 (2)	0.0484 (11)	−0.0226 (15)	−0.0201 (10)	0.0130 (12)
C21	0.0619 (10)	0.0845 (14)	0.0454 (10)	−0.0018 (10)	−0.0052 (8)	0.0060 (10)
C22	0.0624 (10)	0.0464 (10)	0.0753 (13)	0.0054 (8)	−0.0049 (9)	−0.0101 (9)
C23	0.0761 (13)	0.0500 (11)	0.1064 (19)	0.0169 (10)	−0.0039 (13)	−0.0032 (12)
C24	0.0769 (14)	0.0825 (17)	0.109 (2)	0.0233 (13)	−0.0197 (15)	0.0112 (16)
C25	0.0825 (16)	0.112 (2)	0.103 (2)	−0.0033 (16)	−0.0421 (16)	0.0016 (19)
C26	0.0761 (13)	0.0663 (13)	0.0817 (14)	−0.0173 (11)	−0.0171 (12)	−0.0039 (12)
C27	0.0423 (7)	0.0479 (9)	0.0606 (10)	−0.0009 (7)	0.0054 (7)	−0.0082 (8)
C28	0.0497 (8)	0.0442 (8)	0.0524 (9)	−0.0062 (7)	0.0083 (7)	−0.0017 (7)
C29	0.0486 (7)	0.0362 (7)	0.0351 (7)	−0.0058 (6)	0.0032 (6)	−0.0021 (6)
C30	0.0582 (9)	0.0385 (8)	0.0460 (8)	−0.0051 (7)	0.0000 (7)	0.0009 (7)

O1—N3	1.216 (3)	C13—C14	1.385 (3)
O2—N3	1.226 (3)	C14—H14	0.9300
O3—C30	1.402 (2)	C15—C16	1.489 (2)
O3—H3	0.90 (3)	C16—C17	1.381 (3)
N1—C7	1.3858 (18)	C16—C21	1.385 (3)
N1—C15	1.308 (2)	C17—C18	1.389 (3)
N2—C8	1.4009 (19)	C18—H18	0.9300
N2—C15	1.3561 (19)	C18—C19	1.367 (4)
N2—C29	1.4762 (19)	C19—H19	0.9300
N3—C17	1.466 (3)	C19—C20	1.355 (4)
C1—H1	0.9300	C20—H20	0.9300
C1—C2	1.386 (3)	C20—C21	1.393 (3)
C1—C6	1.388 (3)	C21—H21	0.9300
C2—H2	0.9300	C22—H22	0.9300
C2—C3	1.378 (4)	C22—C23	1.384 (3)
C3—H3A	0.9300	C22—C27	1.381 (3)
C3—C4	1.363 (4)	C23—H23	0.9300
C4—H4	0.9300	C23—C24	1.364 (4)
C4—C5	1.379 (3)	C24—H24	0.9300
C5—H5	0.9300	C24—C25	1.364 (4)
C5—C6	1.395 (2)	C25—H25	0.9300
C6—C7	1.476 (2)	C25—C26	1.390 (4)
C7—C8	1.374 (2)	C26—H26	0.9300
C8—C9	1.489 (2)	C26—C27	1.379 (3)
C9—C10	1.389 (3)	C27—C28	1.509 (3)
C9—C14	1.388 (3)	C28—H28A	0.9700
C10—H10	0.9300	C28—H28B	0.9700
C10—C11	1.391 (3)	C28—C29	1.536 (2)
C11—H11	0.9300	C29—H29	0.9800
C11—C12	1.365 (4)	C29—C30	1.528 (2)
C12—H12	0.9300	C30—H30A	0.9700
C12—C13	1.369 (4)	C30—H30B	0.9700
C13—H13	0.9300
C30—O3—H3	109.6 (17)	C17—C16—C21	117.09 (16)
C15—N1—C7	106.24 (13)	C21—C16—C15	118.52 (16)
C8—N2—C29	128.75 (12)	C16—C17—N3	120.76 (16)
C15—N2—C8	106.21 (12)	C16—C17—C18	122.0 (2)
C15—N2—C29	124.32 (12)	C18—C17—N3	117.27 (19)
O1—N3—O2	123.0 (2)	C17—C18—H18	120.2
O1—N3—C17	118.91 (17)	C19—C18—C17	119.5 (2)
O2—N3—C17	118.1 (2)	C19—C18—H18	120.2
C2—C1—H1	119.7	C18—C19—H19	120.0
C2—C1—C6	120.5 (2)	C20—C19—C18	119.94 (19)
C6—C1—H1	119.7	C20—C19—H19	120.0
C1—C2—H2	119.9	C19—C20—H20	119.7
C3—C2—C1	120.3 (2)	C19—C20—C21	120.6 (2)
C3—C2—H2	119.9	C21—C20—H20	119.7
C2—C3—H3A	120.1	C16—C21—C20	120.8 (2)
C4—C3—C2	119.8 (2)	C16—C21—H21	119.6
C4—C3—H3A	120.1	C20—C21—H21	119.6
C3—C4—H4	119.8	C23—C22—H22	119.2
C3—C4—C5	120.5 (2)	C27—C22—H22	119.2
C5—C4—H4	119.8	C27—C22—C23	121.5 (2)
C4—C5—H5	119.6	C22—C23—H23	119.9
C4—C5—C6	120.9 (2)	C24—C23—C22	120.2 (2)
C6—C5—H5	119.6	C24—C23—H23	119.9
C1—C6—C5	118.00 (17)	C23—C24—H24	120.4
C1—C6—C7	119.63 (16)	C25—C24—C23	119.2 (3)
C5—C6—C7	122.25 (17)	C25—C24—H24	120.4
N1—C7—C6	120.53 (14)	C24—C25—H25	119.6
C8—C7—N1	109.25 (13)	C24—C25—C26	120.8 (3)
C8—C7—C6	130.08 (14)	C26—C25—H25	119.6
N2—C8—C9	124.21 (14)	C25—C26—H26	119.7
C7—C8—N2	105.88 (12)	C27—C26—C25	120.6 (2)
C7—C8—C9	129.81 (14)	C27—C26—H26	119.7
C10—C9—C8	121.14 (16)	C22—C27—C28	122.24 (17)
C14—C9—C8	120.07 (16)	C26—C27—C22	117.5 (2)
C14—C9—C10	118.64 (17)	C26—C27—C28	120.17 (18)
C9—C10—H10	119.9	C27—C28—H28A	109.0
C9—C10—C11	120.1 (2)	C27—C28—H28B	109.0
C11—C10—H10	119.9	C27—C28—C29	113.05 (14)
C10—C11—H11	119.7	H28A—C28—H28B	107.8
C12—C11—C10	120.5 (2)	C29—C28—H28A	109.0
C12—C11—H11	119.7	C29—C28—H28B	109.0
C11—C12—H12	120.1	N2—C29—C28	112.95 (12)
C11—C12—C13	119.86 (19)	N2—C29—H29	106.6
C13—C12—H12	120.1	N2—C29—C30	110.98 (12)
C12—C13—H13	119.8	C28—C29—H29	106.6
C12—C13—C14	120.5 (2)	C30—C29—C28	112.52 (13)
C14—C13—H13	119.8	C30—C29—H29	106.6
C9—C14—H14	119.8	O3—C30—C29	110.62 (14)
C13—C14—C9	120.3 (2)	O3—C30—H30A	109.5
C13—C14—H14	119.8	O3—C30—H30B	109.5
N1—C15—N2	112.40 (13)	C29—C30—H30A	109.5
N1—C15—C16	124.36 (13)	C29—C30—H30B	109.5
N2—C15—C16	123.15 (13)	H30A—C30—H30B	108.1
C17—C16—C15	124.36 (16)
O1—N3—C17—C16	−28.9 (3)	C10—C9—C14—C13	1.3 (3)
O1—N3—C17—C18	149.6 (2)	C10—C11—C12—C13	0.6 (4)
O2—N3—C17—C16	151.3 (2)	C11—C12—C13—C14	−1.0 (4)
O2—N3—C17—C18	−30.2 (3)	C12—C13—C14—C9	0.0 (4)
N1—C7—C8—N2	−1.39 (18)	C14—C9—C10—C11	−1.7 (3)
N1—C7—C8—C9	174.96 (16)	C15—N1—C7—C6	−174.64 (14)
N1—C15—C16—C17	−78.5 (2)	C15—N1—C7—C8	1.39 (18)
N1—C15—C16—C21	99.5 (2)	C15—N2—C8—C7	0.87 (16)
N2—C8—C9—C10	−91.6 (2)	C15—N2—C8—C9	−175.75 (15)
N2—C8—C9—C14	92.9 (2)	C15—N2—C29—C28	123.81 (16)
N2—C15—C16—C17	105.10 (19)	C15—N2—C29—C30	−108.76 (16)
N2—C15—C16—C21	−76.9 (2)	C15—C16—C17—N3	−2.0 (2)
N2—C29—C30—O3	168.26 (12)	C15—C16—C17—C18	179.64 (17)
N3—C17—C18—C19	−178.64 (19)	C15—C16—C21—C20	179.7 (2)
C1—C2—C3—C4	0.2 (4)	C16—C17—C18—C19	−0.2 (3)
C1—C6—C7—N1	9.2 (3)	C17—C16—C21—C20	−2.2 (3)
C1—C6—C7—C8	−165.92 (19)	C17—C18—C19—C20	−0.7 (3)
C2—C1—C6—C5	−1.0 (3)	C18—C19—C20—C21	0.1 (4)
C2—C1—C6—C7	175.2 (2)	C19—C20—C21—C16	1.4 (4)
C2—C3—C4—C5	−0.5 (4)	C21—C16—C17—N3	−179.99 (17)
C3—C4—C5—C6	0.1 (3)	C21—C16—C17—C18	1.6 (3)
C4—C5—C6—C1	0.7 (3)	C22—C23—C24—C25	−0.7 (5)
C4—C5—C6—C7	−175.39 (17)	C22—C27—C28—C29	81.6 (2)
C5—C6—C7—N1	−174.82 (16)	C23—C22—C27—C26	1.9 (3)
C5—C6—C7—C8	10.1 (3)	C23—C22—C27—C28	−176.0 (2)
C6—C1—C2—C3	0.6 (4)	C23—C24—C25—C26	2.3 (5)
C6—C7—C8—N2	174.14 (16)	C24—C25—C26—C27	−1.8 (5)
C6—C7—C8—C9	−9.5 (3)	C25—C26—C27—C22	−0.3 (4)
C7—N1—C15—N2	−0.83 (18)	C25—C26—C27—C28	177.6 (2)
C7—N1—C15—C16	−177.60 (16)	C26—C27—C28—C29	−96.2 (2)
C7—C8—C9—C10	92.6 (2)	C27—C22—C23—C24	−1.4 (4)
C7—C8—C9—C14	−82.8 (2)	C27—C28—C29—N2	−69.13 (18)
C8—N2—C15—N1	−0.02 (18)	C27—C28—C29—C30	164.25 (14)
C8—N2—C15—C16	176.79 (15)	C28—C29—C30—O3	−64.08 (18)
C8—N2—C29—C28	−67.3 (2)	C29—N2—C8—C7	−169.57 (14)
C8—N2—C29—C30	60.1 (2)	C29—N2—C8—C9	13.8 (2)
C8—C9—C10—C11	−177.23 (16)	C29—N2—C15—N1	170.96 (14)
C8—C9—C14—C13	176.89 (19)	C29—N2—C15—C16	−12.2 (2)
C9—C10—C11—C12	0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg1	0.93	2.84	3.715 (2)	157
C21—H21···Cg2	0.93	2.81	3.501 (2)	132
O3—H3···N1i	0.90 (3)	1.89 (3)	2.7935 (17)	179 (3)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C9–C14 and C22–C27 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Cg1	0.93	2.84	3.715 (2)	157
C21—H21⋯Cg2	0.93	2.81	3.501 (2)	132
O3—H3⋯N1i	0.90 (3)	1.89 (3)	2.7935 (17)	179 (3)

Symmetry code: (i) .