4-Methyl-N-(2-methyl-phen-yl)benzamide.

The asymmetric unit of the title compound, C(15)H(15)NO, contains two independent mol-ecules, which differ in the dihedral angle between the aromatic rings [48.98 (9) and 57.48 (8)°]. The methyl groups in para positions are disordered over two equally occupied positions. An intra-molecular N-H⋯O hydrogen bond occurs. The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonds which link the mol-ecules into chains running along the b axis.

Related literature

For the preparation of the title compound, see: Gowda et al. (2003 ▶). For our study of the effect of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Bhat & Gowda (2000 ▶); Bowes et al. (2003 ▶); Gowda et al. (2008 ▶, 2009 ▶); Saeed et al. (2010 ▶).

Experimental

Crystal data

C15H15NO

M = 225.28

Triclinic,

a = 7.2964 (6) Å

b = 9.9075 (5) Å

c = 18.1347 (13) Å

α = 88.331 (5)°

β = 82.892 (6)°

γ = 79.558 (5)°

V = 1279.29 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.88 × 0.09 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector

Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009 ▶), based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.968, T max = 0.996

18269 measured reflections

4354 independent reflections

1602 reflections with I > 2σ(I)

R int = 0.088

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.097

S = 0.74

4354 reflections

311 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.11 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018770/bt5550sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018770/bt5550Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811018770/bt5550Isup3.cml

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

C15H15NO	Z = 4
Mr = 225.28	F(000) = 480
Triclinic, P1	Dx = 1.170 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2964 (6) Å	Cell parameters from 2440 reflections
b = 9.9075 (5) Å	θ = 3.5–29.3°
c = 18.1347 (13) Å	µ = 0.07 mm−1
α = 88.331 (5)°	T = 293 K
β = 82.892 (6)°	Needle, colorless
γ = 79.558 (5)°	0.88 × 0.09 × 0.06 mm
V = 1279.29 (15) Å3

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector	4354 independent reflections
Radiation source: fine-focus sealed tube	1602 reflections with I > 2σ(I)
graphite	Rint = 0.088
ω scans	θmax = 24.7°, θmin = 4.1°
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	h = −8→8
Tmin = 0.968, Tmax = 0.996	k = −11→11
18269 measured reflections	l = −21→21

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 0.74	w = 1/[σ2(Fo2) + (0.0367P)2] where P = (Fo2 + 2Fc2)/3
4354 reflections	(Δ/σ)max < 0.001
311 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.11 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived (Clark & Reid, 1995).

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	0.3561 (3)	0.83584 (15)	0.23183 (11)	0.0969 (7)
N1	0.3243 (3)	0.62248 (17)	0.26640 (11)	0.0687 (7)
H1A	0.3695	0.5366	0.2607	0.082*
C1	0.1559 (5)	0.6596 (2)	0.31651 (18)	0.0614 (8)
C2	0.1579 (5)	0.6225 (2)	0.39053 (18)	0.0622 (8)
C3	−0.0084 (6)	0.6555 (3)	0.43740 (17)	0.0776 (9)
H3A	−0.0099	0.6321	0.4875	0.093*
C4	−0.1703 (5)	0.7216 (3)	0.4122 (2)	0.0857 (10)
H4A	−0.2804	0.7421	0.4447	0.103*
C5	−0.1687 (5)	0.7572 (3)	0.3388 (2)	0.0881 (10)
H5A	−0.2783	0.8021	0.3212	0.106*
C6	−0.0056 (6)	0.7270 (3)	0.29071 (17)	0.0768 (9)
H6A	−0.0048	0.7522	0.2409	0.092*
C7	0.3332 (5)	0.5461 (3)	0.41909 (16)	0.0928 (10)
H7A	0.3634	0.4553	0.3987	0.139*
H7B	0.3129	0.5403	0.4723	0.139*
H7C	0.4352	0.5940	0.4044	0.139*
C8	0.4170 (4)	0.7118 (2)	0.22826 (14)	0.0648 (8)
C9	0.5994 (4)	0.6581 (2)	0.18350 (14)	0.0590 (7)
C10	0.6996 (5)	0.5260 (2)	0.18947 (15)	0.0772 (9)
H10A	0.6467	0.4619	0.2194	0.093*
C11	0.8757 (5)	0.4888 (3)	0.15171 (16)	0.0832 (9)
H11A	0.9396	0.3994	0.1565	0.100*
C12	0.9607 (5)	0.5800 (3)	0.10686 (15)	0.0772 (9)
C13	0.8592 (5)	0.7099 (3)	0.09924 (15)	0.0803 (10)
H13A	0.9114	0.7729	0.0682	0.096*
C14	0.6840 (5)	0.7481 (2)	0.13623 (15)	0.0736 (9)
H14A	0.6192	0.8367	0.1297	0.088*
C15	1.1607 (5)	0.5405 (3)	0.06924 (18)	0.1129 (12)
H15A	1.2388	0.4932	0.1042	0.135*	0.50
H15B	1.2072	0.6218	0.0518	0.135*	0.50
H15C	1.1624	0.4816	0.0280	0.135*	0.50
H15D	1.2459	0.5820	0.0963	0.135*	0.50
H15E	1.1741	0.5717	0.0194	0.135*	0.50
H15F	1.2029	0.4415	0.0714	0.135*	0.50
O2	0.3997 (3)	0.32712 (14)	0.26391 (11)	0.0970 (7)
N2	0.4584 (3)	0.10245 (17)	0.23914 (11)	0.0622 (6)
H2A	0.4231	0.0247	0.2478	0.075*
C16	0.6234 (4)	0.1063 (2)	0.18894 (17)	0.0541 (7)
C17	0.6124 (4)	0.1340 (2)	0.11454 (19)	0.0665 (8)
C18	0.7779 (6)	0.1290 (3)	0.06697 (17)	0.0799 (9)
H18A	0.7723	0.1486	0.0168	0.096*
C19	0.9474 (5)	0.0960 (3)	0.0923 (2)	0.0806 (9)
H19A	1.0564	0.0931	0.0595	0.097*
C20	0.9594 (5)	0.0668 (3)	0.1660 (2)	0.0866 (9)
H20A	1.0757	0.0432	0.1834	0.104*
C21	0.7952 (5)	0.0732 (2)	0.21414 (16)	0.0737 (9)
H21A	0.8018	0.0546	0.2644	0.088*
C22	0.4253 (5)	0.1644 (4)	0.08421 (19)	0.1311 (13)
H22A	0.3592	0.0897	0.0962	0.197*
H22B	0.4455	0.1755	0.0312	0.197*
H22C	0.3524	0.2473	0.1060	0.197*
C23	0.3531 (4)	0.2138 (2)	0.27375 (14)	0.0615 (8)
C24	0.1817 (4)	0.1941 (2)	0.32233 (13)	0.0551 (7)
C25	0.0317 (4)	0.3016 (2)	0.33069 (14)	0.0659 (8)
H25A	0.0424	0.3857	0.3080	0.079*
C26	−0.1335 (4)	0.2853 (2)	0.37224 (15)	0.0718 (8)
H26A	−0.2340	0.3584	0.3766	0.086*
C27	−0.1537 (4)	0.1625 (3)	0.40784 (14)	0.0667 (8)
C28	−0.0014 (4)	0.0571 (2)	0.40096 (14)	0.0663 (8)
H28A	−0.0101	−0.0255	0.4256	0.080*
C29	0.1638 (4)	0.0716 (2)	0.35820 (13)	0.0618 (8)
H29A	0.2639	−0.0017	0.3535	0.074*
C30	−0.3368 (4)	0.1441 (3)	0.45296 (17)	0.1005 (10)
H30A	−0.3499	0.1904	0.4996	0.121*	0.50
H30B	−0.3368	0.0481	0.4618	0.121*	0.50
H30C	−0.4397	0.1821	0.4260	0.121*	0.50
H30D	−0.3245	0.0952	0.4985	0.121*	0.50
H30E	−0.4078	0.0901	0.4238	0.121*	0.50
H30F	−0.4215	0.2321	0.4626	0.121*	0.50

	U11	U22	U33	U12	U13	U23
O1	0.0967 (17)	0.0388 (9)	0.1473 (19)	−0.0146 (10)	0.0214 (13)	−0.0057 (10)
N1	0.092 (2)	0.0376 (11)	0.0721 (16)	−0.0128 (12)	0.0087 (15)	−0.0023 (11)
C1	0.072 (3)	0.0414 (14)	0.071 (2)	−0.0138 (16)	−0.001 (2)	−0.0075 (14)
C2	0.075 (3)	0.0501 (14)	0.062 (2)	−0.0146 (15)	−0.006 (2)	−0.0012 (14)
C3	0.085 (3)	0.0691 (18)	0.077 (2)	−0.0195 (18)	0.007 (2)	−0.0019 (16)
C4	0.079 (3)	0.078 (2)	0.099 (3)	−0.024 (2)	0.013 (2)	−0.0113 (19)
C5	0.067 (3)	0.082 (2)	0.117 (3)	−0.0108 (17)	−0.018 (3)	−0.012 (2)
C6	0.088 (3)	0.0662 (17)	0.078 (2)	−0.0120 (18)	−0.018 (2)	−0.0020 (16)
C7	0.097 (3)	0.0908 (19)	0.088 (2)	−0.0066 (19)	−0.018 (2)	0.0073 (16)
C8	0.084 (2)	0.0408 (14)	0.071 (2)	−0.0161 (16)	−0.0057 (17)	−0.0070 (14)
C9	0.080 (2)	0.0410 (14)	0.0574 (18)	−0.0154 (15)	−0.0075 (16)	−0.0022 (13)
C10	0.091 (3)	0.0512 (16)	0.086 (2)	−0.0196 (17)	0.008 (2)	0.0036 (14)
C11	0.092 (3)	0.0567 (16)	0.094 (2)	−0.0100 (17)	0.012 (2)	−0.0026 (16)
C12	0.090 (3)	0.0732 (19)	0.067 (2)	−0.0194 (19)	0.0062 (19)	−0.0126 (16)
C13	0.105 (3)	0.0621 (18)	0.071 (2)	−0.0251 (18)	0.014 (2)	−0.0009 (15)
C14	0.104 (3)	0.0491 (15)	0.066 (2)	−0.0159 (17)	0.0013 (19)	0.0037 (14)
C15	0.113 (3)	0.106 (2)	0.112 (3)	−0.019 (2)	0.019 (3)	−0.0098 (19)
O2	0.1053 (17)	0.0411 (9)	0.1356 (17)	−0.0257 (10)	0.0425 (13)	−0.0120 (10)
N2	0.0637 (17)	0.0417 (11)	0.0764 (16)	−0.0172 (11)	0.0228 (14)	−0.0052 (10)
C16	0.057 (2)	0.0420 (13)	0.063 (2)	−0.0137 (14)	0.0015 (19)	−0.0012 (13)
C17	0.052 (2)	0.0700 (16)	0.074 (2)	−0.0101 (14)	−0.001 (2)	0.0147 (15)
C18	0.075 (3)	0.093 (2)	0.071 (2)	−0.0203 (18)	0.000 (2)	0.0133 (15)
C19	0.070 (3)	0.094 (2)	0.078 (3)	−0.0254 (19)	0.009 (2)	−0.0146 (17)
C20	0.060 (3)	0.117 (2)	0.086 (3)	−0.0205 (18)	−0.012 (2)	−0.0166 (19)
C21	0.074 (3)	0.0844 (19)	0.064 (2)	−0.0216 (18)	−0.002 (2)	−0.0082 (15)
C22	0.074 (3)	0.192 (4)	0.116 (3)	0.002 (2)	−0.012 (3)	0.040 (2)
C23	0.069 (2)	0.0423 (14)	0.0704 (19)	−0.0121 (14)	0.0078 (16)	−0.0048 (13)
C24	0.063 (2)	0.0440 (14)	0.0565 (18)	−0.0142 (14)	0.0097 (15)	−0.0070 (12)
C25	0.068 (2)	0.0494 (15)	0.076 (2)	−0.0110 (16)	0.0076 (18)	−0.0050 (13)
C26	0.066 (2)	0.0655 (17)	0.078 (2)	−0.0011 (15)	0.0018 (18)	−0.0082 (15)
C27	0.068 (2)	0.0765 (18)	0.0561 (19)	−0.0220 (18)	0.0075 (17)	−0.0103 (15)
C28	0.074 (2)	0.0588 (16)	0.064 (2)	−0.0177 (16)	0.0077 (17)	−0.0007 (13)
C29	0.070 (2)	0.0498 (15)	0.0624 (19)	−0.0120 (13)	0.0097 (16)	−0.0049 (13)
C30	0.084 (3)	0.111 (2)	0.102 (3)	−0.0272 (19)	0.022 (2)	−0.0060 (17)

O1—C8	1.229 (2)	O2—C23	1.233 (2)
N1—C8	1.336 (3)	N2—C23	1.347 (3)
N1—C1	1.432 (3)	N2—C16	1.423 (3)
N1—H1A	0.8596	N2—H2A	0.8594
C1—C6	1.374 (4)	C16—C21	1.368 (4)
C1—C2	1.383 (3)	C16—C17	1.378 (3)
C2—C3	1.385 (4)	C17—C18	1.389 (4)
C2—C7	1.506 (4)	C17—C22	1.511 (4)
C3—C4	1.367 (4)	C18—C19	1.354 (4)
C3—H3A	0.9300	C18—H18A	0.9300
C4—C5	1.367 (4)	C19—C20	1.369 (4)
C4—H4A	0.9300	C19—H19A	0.9300
C5—C6	1.376 (4)	C20—C21	1.385 (4)
C5—H5A	0.9300	C20—H20A	0.9300
C6—H6A	0.9300	C21—H21A	0.9300
C7—H7A	0.9600	C22—H22A	0.9600
C7—H7B	0.9600	C22—H22B	0.9600
C7—H7C	0.9600	C22—H22C	0.9600
C8—C9	1.488 (3)	C23—C24	1.477 (3)
C9—C10	1.387 (3)	C24—C25	1.379 (3)
C9—C14	1.391 (3)	C24—C29	1.380 (3)
C10—C11	1.372 (3)	C25—C26	1.373 (3)
C10—H10A	0.9300	C25—H25A	0.9300
C11—C12	1.378 (3)	C26—C27	1.384 (3)
C11—H11A	0.9300	C26—H26A	0.9300
C12—C13	1.375 (3)	C27—C28	1.376 (3)
C12—C15	1.520 (4)	C27—C30	1.515 (3)
C13—C14	1.362 (3)	C28—C29	1.378 (3)
C13—H13A	0.9300	C28—H28A	0.9300
C14—H14A	0.9300	C29—H29A	0.9300
C15—H15A	0.9600	C30—H30A	0.9600
C15—H15B	0.9600	C30—H30B	0.9600
C15—H15C	0.9600	C30—H30C	0.9600
C15—H15D	0.9887	C30—H30D	0.9501
C15—H15E	0.9457	C30—H30E	1.0098
C15—H15F	0.9744	C30—H30F	0.9793
C8—N1—C1	124.69 (19)	C23—N2—C16	123.84 (18)
C8—N1—H1A	117.6	C23—N2—H2A	117.9
C1—N1—H1A	117.7	C16—N2—H2A	118.3
C6—C1—C2	120.9 (3)	C21—C16—C17	119.8 (3)
C6—C1—N1	120.3 (3)	C21—C16—N2	119.3 (3)
C2—C1—N1	118.7 (3)	C17—C16—N2	120.7 (3)
C1—C2—C3	117.7 (3)	C16—C17—C18	118.6 (3)
C1—C2—C7	121.3 (3)	C16—C17—C22	121.2 (3)
C3—C2—C7	121.0 (3)	C18—C17—C22	120.2 (3)
C4—C3—C2	121.9 (3)	C19—C18—C17	121.2 (3)
C4—C3—H3A	119.0	C19—C18—H18A	119.4
C2—C3—H3A	119.0	C17—C18—H18A	119.4
C3—C4—C5	119.3 (3)	C18—C19—C20	120.5 (3)
C3—C4—H4A	120.3	C18—C19—H19A	119.7
C5—C4—H4A	120.3	C20—C19—H19A	119.7
C4—C5—C6	120.3 (3)	C19—C20—C21	118.8 (3)
C4—C5—H5A	119.8	C19—C20—H20A	120.6
C6—C5—H5A	119.8	C21—C20—H20A	120.6
C1—C6—C5	119.9 (3)	C16—C21—C20	121.1 (3)
C1—C6—H6A	120.1	C16—C21—H21A	119.5
C5—C6—H6A	120.1	C20—C21—H21A	119.5
C2—C7—H7A	109.5	C17—C22—H22A	109.5
C2—C7—H7B	109.5	C17—C22—H22B	109.5
H7A—C7—H7B	109.5	H22A—C22—H22B	109.5
C2—C7—H7C	109.5	C17—C22—H22C	109.5
H7A—C7—H7C	109.5	H22A—C22—H22C	109.5
H7B—C7—H7C	109.5	H22B—C22—H22C	109.5
O1—C8—N1	120.8 (2)	O2—C23—N2	120.2 (2)
O1—C8—C9	120.7 (2)	O2—C23—C24	122.3 (2)
N1—C8—C9	118.4 (2)	N2—C23—C24	117.5 (2)
C10—C9—C14	116.8 (3)	C25—C24—C29	118.6 (2)
C10—C9—C8	124.5 (2)	C25—C24—C23	118.6 (2)
C14—C9—C8	118.5 (2)	C29—C24—C23	122.8 (2)
C11—C10—C9	120.8 (2)	C26—C25—C24	120.4 (2)
C11—C10—H10A	119.6	C26—C25—H25A	119.8
C9—C10—H10A	119.6	C24—C25—H25A	119.8
C10—C11—C12	121.9 (3)	C25—C26—C27	121.5 (3)
C10—C11—H11A	119.1	C25—C26—H26A	119.3
C12—C11—H11A	119.1	C27—C26—H26A	119.3
C13—C12—C11	117.3 (3)	C28—C27—C26	117.7 (3)
C13—C12—C15	121.2 (3)	C28—C27—C30	120.9 (2)
C11—C12—C15	121.5 (3)	C26—C27—C30	121.4 (3)
C14—C13—C12	121.4 (3)	C27—C28—C29	121.3 (2)
C14—C13—H13A	119.3	C27—C28—H28A	119.4
C12—C13—H13A	119.3	C29—C28—H28A	119.4
C13—C14—C9	121.7 (2)	C28—C29—C24	120.5 (2)
C13—C14—H14A	119.1	C28—C29—H29A	119.7
C9—C14—H14A	119.1	C24—C29—H29A	119.7
C12—C15—H15A	109.5	C27—C30—H30A	109.5
C12—C15—H15B	109.5	C27—C30—H30B	109.5
H15A—C15—H15B	109.5	H30A—C30—H30B	109.5
C12—C15—H15C	109.5	C27—C30—H30C	109.5
H15A—C15—H15C	109.5	H30A—C30—H30C	109.5
H15B—C15—H15C	109.5	H30B—C30—H30C	109.5
C12—C15—H15D	109.4	C27—C30—H30D	115.3
H15A—C15—H15D	54.8	H30A—C30—H30D	58.1
H15B—C15—H15D	57.7	H30B—C30—H30D	52.6
H15C—C15—H15D	141.1	H30C—C30—H30D	135.2
C12—C15—H15E	112.3	C27—C30—H30E	110.2
H15A—C15—H15E	138.2	H30A—C30—H30E	140.3
H15B—C15—H15E	53.8	H30B—C30—H30E	57.9
H15C—C15—H15E	57.7	H30C—C30—H30E	54.3
H15D—C15—H15E	107.7	H30D—C30—H30E	105.2
C12—C15—H15F	110.8	C27—C30—H30F	111.6
H15A—C15—H15F	54.7	H30A—C30—H30F	58.1
H15B—C15—H15F	139.7	H30B—C30—H30F	138.8
H15C—C15—H15F	57.4	H30C—C30—H30F	53.7
H15D—C15—H15F	106.4	H30D—C30—H30F	109.3
H15E—C15—H15F	110.1	H30E—C30—H30F	104.5
C8—N1—C1—C6	63.9 (3)	C23—N2—C16—C21	97.6 (3)
C8—N1—C1—C2	−118.2 (3)	C23—N2—C16—C17	−86.8 (3)
C6—C1—C2—C3	0.1 (3)	C21—C16—C17—C18	−0.7 (3)
N1—C1—C2—C3	−177.9 (2)	N2—C16—C17—C18	−176.4 (2)
C6—C1—C2—C7	178.8 (2)	C21—C16—C17—C22	177.1 (2)
N1—C1—C2—C7	0.8 (3)	N2—C16—C17—C22	1.4 (3)
C1—C2—C3—C4	0.4 (4)	C16—C17—C18—C19	0.8 (4)
C7—C2—C3—C4	−178.2 (2)	C22—C17—C18—C19	−177.0 (3)
C2—C3—C4—C5	−0.5 (4)	C17—C18—C19—C20	−0.1 (4)
C3—C4—C5—C6	−0.1 (4)	C18—C19—C20—C21	−0.7 (4)
C2—C1—C6—C5	−0.6 (3)	C17—C16—C21—C20	0.0 (3)
N1—C1—C6—C5	177.3 (2)	N2—C16—C21—C20	175.7 (2)
C4—C5—C6—C1	0.6 (4)	C19—C20—C21—C16	0.8 (4)
C1—N1—C8—O1	−3.2 (4)	C16—N2—C23—O2	−1.5 (4)
C1—N1—C8—C9	174.6 (3)	C16—N2—C23—C24	177.9 (3)
O1—C8—C9—C10	164.4 (3)	O2—C23—C24—C25	28.9 (4)
N1—C8—C9—C10	−13.4 (4)	N2—C23—C24—C25	−150.4 (2)
O1—C8—C9—C14	−10.5 (4)	O2—C23—C24—C29	−152.7 (2)
N1—C8—C9—C14	171.7 (2)	N2—C23—C24—C29	27.9 (4)
C14—C9—C10—C11	1.7 (4)	C29—C24—C25—C26	−1.7 (4)
C8—C9—C10—C11	−173.2 (3)	C23—C24—C25—C26	176.6 (2)
C9—C10—C11—C12	0.3 (4)	C24—C25—C26—C27	1.1 (4)
C10—C11—C12—C13	−2.1 (4)	C25—C26—C27—C28	0.8 (4)
C10—C11—C12—C15	176.0 (3)	C25—C26—C27—C30	−179.3 (3)
C11—C12—C13—C14	1.9 (4)	C26—C27—C28—C29	−2.0 (4)
C15—C12—C13—C14	−176.2 (3)	C30—C27—C28—C29	178.0 (2)
C12—C13—C14—C9	0.1 (4)	C27—C28—C29—C24	1.4 (4)
C10—C9—C14—C13	−2.0 (4)	C25—C24—C29—C28	0.5 (4)
C8—C9—C14—C13	173.3 (3)	C23—C24—C29—C28	−177.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.86	2.05	2.878 (2)	163
N2—H2A···O1i	0.86	2.05	2.883 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2	0.86	2.05	2.878 (2)	163
N2—H2A⋯O1i	0.86	2.05	2.883 (2)	162

Symmetry code: (i) .