2,4-Dimethyl-N-phenyl-benzene-sulfonamide.

The asymmetric unit of the crystal structure of the title compound, C(14)H(15)NO(2)S, contains two mol-ecules. The conformations of the N-C bonds in the C-SO(2)-NH-C segments of the structure have trans and gauche torsion angles with the S=O bonds. Furthermore, the torsion angles of the C-SO(2)-NH-C groups in the two mol-ecules are 46.1 (3) (glide image of mol-ecule 1) and 47.7 (3)° (mol-ecule 2). The ortho-methyl groups in the sulfonyl benzene ring are oriented away from the S=O bonds. The two benzene rings are tilted relative to each other by 67.5 (1) and 72.9 (1)° in the two mol-ecules. N-H⋯O and C-H⋯O hydrogen bonds pack the mol-ecules into one-dimensional chains in different directions, resulting in a two-dimensional network.

Related literature

For related structures, see: Gelbrich et al. (2007 ▶); Gowda et al. (2008 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C14H15NO2S

M = 261.33

Orthorhombic,

a = 19.113 (3) Å

b = 8.9290 (8) Å

c = 15.781 (1) Å

V = 2693.2 (5) Å3

Z = 8

Cu Kα radiation

μ = 2.09 mm−1

T = 299 K

0.50 × 0.43 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.401, T max = 0.593

4916 measured reflections

2505 independent reflections

2421 reflections with I > 2σ(I)

R int = 0.050

3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.090

S = 1.09

2505 reflections

330 parameters

7 restraints

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), no Friedel pairs

Flack parameter: 0.008 (17)

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680900573X/kj2115sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900573X/kj2115Isup2.hkl

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

C14H15NO2S	F(000) = 1104
Mr = 261.33	Dx = 1.289 Mg m−3
Orthorhombic, Pca21	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2c -2ac	Cell parameters from 25 reflections
a = 19.113 (3) Å	θ = 4.6–19.0°
b = 8.9290 (8) Å	µ = 2.09 mm−1
c = 15.781 (1) Å	T = 299 K
V = 2693.2 (5) Å3	Prism, colourless
Z = 8	0.50 × 0.43 × 0.25 mm

Enraf–Nonius CAD-4 diffractometer	2421 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.050
graphite	θmax = 66.9°, θmin = 4.6°
ω/2θ scans	h = −22→22
Absorption correction: ψ scan (North et al., 1968)	k = −10→0
Tmin = 0.401, Tmax = 0.593	l = −18→0
4916 measured reflections	3 standard reflections every 120 min
2505 independent reflections	intensity decay: 1.0%

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034	w = 1/[σ2(Fo2) + (0.0565P)2 + 0.1061P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.090	(Δ/σ)max = 0.012
S = 1.09	Δρmax = 0.26 e Å−3
2505 reflections	Δρmin = −0.23 e Å−3
330 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
7 restraints	Extinction coefficient: 0.0032 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), no Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.008 (17)

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
S1	0.25250 (4)	0.26684 (7)	0.22911 (5)	0.05031 (19)
O1	0.18269 (11)	0.3237 (2)	0.23659 (15)	0.0594 (5)
O2	0.26004 (13)	0.1099 (2)	0.21441 (18)	0.0702 (7)
N1	0.29100 (14)	0.3475 (3)	0.14888 (15)	0.0544 (5)
H1N	0.3002	0.2948	0.1046	0.065*
C1	0.29873 (15)	0.3238 (3)	0.32001 (19)	0.0520 (6)
C2	0.36811 (17)	0.2791 (4)	0.3346 (2)	0.0603 (7)
C3	0.39906 (19)	0.3302 (5)	0.4076 (3)	0.0763 (10)
H3	0.4448	0.3004	0.4188	0.092*
C4	0.36652 (19)	0.4232 (5)	0.4657 (2)	0.0767 (9)
C5	0.2984 (2)	0.4650 (4)	0.4490 (2)	0.0737 (9)
H5	0.2748	0.5266	0.4869	0.088*
C6	0.26517 (16)	0.4164 (3)	0.3769 (2)	0.0587 (6)
H6	0.2194	0.4464	0.3663	0.070*
C7	0.31002 (15)	0.5019 (3)	0.14938 (15)	0.0472 (5)
C8	0.37518 (17)	0.5411 (3)	0.11944 (17)	0.0559 (6)
H8	0.4067	0.4679	0.1022	0.067*
C9	0.3931 (2)	0.6918 (4)	0.1154 (2)	0.0679 (9)
H9	0.4363	0.7200	0.0935	0.081*
C10	0.3472 (2)	0.7996 (3)	0.1438 (2)	0.0693 (9)
H10	0.3596	0.9003	0.1414	0.083*
C11	0.2844 (2)	0.7591 (3)	0.1749 (3)	0.0706 (8)
H11	0.2539	0.8323	0.1947	0.085*
C12	0.26465 (19)	0.6103 (3)	0.1777 (2)	0.0633 (7)
H12	0.2209	0.5836	0.1987	0.076*
C13	0.4085 (2)	0.1767 (5)	0.2756 (3)	0.0844 (12)
H13A	0.4131	0.2237	0.2211	0.101*
H13B	0.3838	0.0837	0.2695	0.101*
H13C	0.4541	0.1579	0.2987	0.101*
C14	0.4032 (3)	0.4784 (9)	0.5438 (3)	0.1129 (18)
H14A	0.4524	0.4585	0.5392	0.135*
H14B	0.3848	0.4278	0.5927	0.135*
H14C	0.3959	0.5843	0.5497	0.135*
S2	0.58393 (3)	0.79647 (7)	0.45792 (4)	0.04598 (18)
O3	0.61521 (12)	0.8591 (3)	0.53213 (13)	0.0605 (5)
O4	0.59126 (13)	0.6383 (2)	0.44450 (15)	0.0665 (6)
N2	0.61782 (13)	0.8727 (3)	0.37433 (15)	0.0509 (5)
H2N	0.6431	0.8164	0.3424	0.061*
C15	0.49526 (13)	0.8489 (3)	0.45929 (17)	0.0496 (5)
C16	0.44843 (19)	0.7964 (4)	0.3987 (2)	0.0673 (9)
C17	0.3784 (2)	0.8473 (6)	0.4075 (3)	0.0906 (14)
H17	0.3454	0.8140	0.3684	0.109*
C18	0.35654 (19)	0.9422 (6)	0.4700 (3)	0.0949 (15)
C19	0.4042 (2)	0.9912 (6)	0.5270 (3)	0.0854 (12)
H19	0.3904	1.0567	0.5697	0.102*
C20	0.47306 (17)	0.9454 (4)	0.52259 (19)	0.0634 (8)
H20	0.5050	0.9797	0.5626	0.076*
C21	0.60945 (12)	1.0244 (3)	0.34916 (17)	0.0451 (5)
C22	0.60950 (17)	1.1394 (3)	0.4086 (2)	0.0569 (6)
H22	0.6138	1.1185	0.4660	0.068*
C23	0.6030 (2)	1.2854 (4)	0.3806 (3)	0.0678 (9)
H23	0.6019	1.3629	0.4199	0.081*
C24	0.5981 (2)	1.3182 (4)	0.2961 (3)	0.0686 (9)
H24	0.5945	1.4172	0.2782	0.082*
C25	0.5986 (2)	1.2031 (4)	0.2377 (3)	0.0692 (8)
H25	0.5956	1.2244	0.1801	0.083*
C26	0.60355 (16)	1.0569 (3)	0.26450 (18)	0.0555 (7)
H26	0.6029	0.9797	0.2250	0.067*
C27	0.4682 (3)	0.6917 (6)	0.3282 (3)	0.1016 (16)
H27A	0.4895	0.6034	0.3516	0.122*
H27B	0.5008	0.7405	0.2910	0.122*
H27C	0.4271	0.6641	0.2970	0.122*
C28	0.2808 (2)	0.9939 (10)	0.4738 (4)	0.136 (2)
H28A	0.2542	0.9255	0.5079	0.164*
H28B	0.2617	0.9966	0.4175	0.164*
H28C	0.2787	1.0922	0.4983	0.164*

	U11	U22	U33	U12	U13	U23
S1	0.0539 (3)	0.0320 (3)	0.0650 (4)	−0.0034 (3)	0.0112 (3)	0.0002 (3)
O1	0.0510 (9)	0.0539 (10)	0.0733 (12)	−0.0010 (9)	0.0070 (10)	0.0024 (11)
O2	0.0789 (14)	0.0290 (9)	0.1028 (18)	−0.0078 (10)	0.0143 (12)	−0.0020 (11)
N1	0.0726 (13)	0.0345 (10)	0.0562 (11)	−0.0029 (11)	0.0167 (11)	−0.0072 (9)
C1	0.0531 (13)	0.0439 (13)	0.0591 (14)	−0.0029 (12)	0.0083 (12)	0.0089 (11)
C2	0.0536 (14)	0.0536 (15)	0.0736 (18)	0.0048 (12)	0.0098 (13)	0.0140 (14)
C3	0.0591 (16)	0.086 (3)	0.084 (2)	−0.0040 (18)	−0.0014 (16)	0.021 (2)
C4	0.0737 (18)	0.087 (2)	0.0698 (18)	−0.0161 (18)	−0.0008 (17)	0.0115 (19)
C5	0.0827 (19)	0.073 (2)	0.0654 (17)	−0.0087 (18)	0.0111 (16)	−0.0025 (17)
C6	0.0586 (14)	0.0540 (15)	0.0634 (15)	−0.0009 (13)	0.0099 (12)	−0.0011 (13)
C7	0.0647 (14)	0.0334 (11)	0.0434 (10)	−0.0016 (11)	0.0072 (11)	−0.0012 (9)
C8	0.0702 (15)	0.0467 (15)	0.0509 (12)	−0.0030 (14)	0.0146 (12)	−0.0053 (11)
C9	0.084 (2)	0.0538 (18)	0.0657 (17)	−0.0167 (17)	0.0161 (17)	0.0060 (14)
C10	0.101 (2)	0.0387 (13)	0.0684 (17)	−0.0104 (15)	0.0068 (18)	0.0037 (13)
C11	0.094 (2)	0.0341 (13)	0.084 (2)	0.0069 (16)	0.0097 (19)	−0.0004 (14)
C12	0.0739 (18)	0.0386 (13)	0.0774 (19)	0.0019 (14)	0.0182 (15)	0.0022 (14)
C13	0.0657 (19)	0.079 (2)	0.109 (3)	0.023 (2)	0.0120 (19)	0.004 (2)
C14	0.118 (3)	0.141 (5)	0.080 (2)	−0.039 (4)	−0.019 (3)	0.003 (3)
S2	0.0532 (3)	0.0368 (3)	0.0479 (3)	0.0046 (2)	−0.0059 (2)	0.0046 (2)
O3	0.0603 (11)	0.0653 (13)	0.0561 (10)	0.0023 (10)	−0.0154 (9)	0.0038 (10)
O4	0.0918 (14)	0.0341 (9)	0.0735 (13)	0.0111 (10)	−0.0019 (11)	0.0091 (10)
N2	0.0620 (12)	0.0344 (10)	0.0564 (11)	0.0082 (10)	0.0091 (10)	−0.0013 (9)
C15	0.0500 (11)	0.0483 (12)	0.0505 (12)	−0.0020 (11)	−0.0022 (11)	0.0131 (11)
C16	0.0647 (17)	0.0704 (19)	0.0669 (17)	−0.0195 (16)	−0.0227 (15)	0.0204 (15)
C17	0.063 (2)	0.107 (3)	0.102 (3)	−0.021 (2)	−0.027 (2)	0.044 (3)
C18	0.0586 (17)	0.117 (4)	0.109 (3)	0.010 (2)	0.013 (2)	0.062 (3)
C19	0.073 (2)	0.097 (3)	0.086 (2)	0.021 (2)	0.0239 (19)	0.028 (2)
C20	0.0652 (17)	0.0663 (18)	0.0587 (15)	0.0104 (15)	0.0058 (12)	0.0105 (14)
C21	0.0425 (10)	0.0360 (12)	0.0569 (13)	0.0015 (10)	0.0081 (10)	0.0029 (10)
C22	0.0685 (16)	0.0403 (14)	0.0618 (14)	−0.0002 (13)	0.0056 (13)	−0.0040 (12)
C23	0.077 (2)	0.0372 (13)	0.089 (2)	−0.0024 (14)	0.0117 (18)	−0.0048 (15)
C24	0.0722 (18)	0.0446 (17)	0.089 (2)	−0.0011 (15)	0.0141 (18)	0.0130 (16)
C25	0.0773 (18)	0.0575 (19)	0.073 (2)	0.0020 (15)	0.0124 (17)	0.0208 (17)
C26	0.0635 (14)	0.0470 (15)	0.0559 (14)	0.0000 (13)	0.0099 (12)	0.0021 (12)
C27	0.125 (4)	0.095 (3)	0.084 (3)	−0.024 (3)	−0.038 (3)	−0.015 (2)
C28	0.065 (2)	0.177 (5)	0.167 (5)	0.019 (3)	0.018 (3)	0.071 (5)

S1—O2	1.4278 (19)	S2—O3	1.429 (2)
S1—O1	1.433 (2)	S2—O4	1.435 (2)
S1—N1	1.632 (2)	S2—N2	1.619 (2)
S1—C1	1.760 (3)	S2—C15	1.758 (3)
N1—C7	1.426 (3)	N2—C21	1.421 (3)
N1—H1N	0.8600	N2—H2N	0.8600
C1—C6	1.379 (4)	C15—C20	1.386 (4)
C1—C2	1.404 (4)	C15—C16	1.391 (4)
C2—C3	1.373 (6)	C16—C17	1.421 (6)
C2—C13	1.517 (5)	C16—C27	1.501 (6)
C3—C4	1.384 (6)	C17—C18	1.366 (8)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.380 (6)	C18—C19	1.354 (7)
C4—C14	1.502 (6)	C18—C28	1.520 (6)
C5—C6	1.373 (5)	C19—C20	1.379 (5)
C5—H5	0.9300	C19—H19	0.9300
C6—H6	0.9300	C20—H20	0.9300
C7—C12	1.374 (4)	C21—C26	1.372 (4)
C7—C8	1.377 (4)	C21—C22	1.390 (4)
C8—C9	1.390 (4)	C22—C23	1.382 (4)
C8—H8	0.9300	C22—H22	0.9300
C9—C10	1.377 (6)	C23—C24	1.367 (6)
C9—H9	0.9300	C23—H23	0.9300
C10—C11	1.347 (6)	C24—C25	1.381 (6)
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.382 (4)	C25—C26	1.375 (4)
C11—H11	0.9300	C25—H25	0.9300
C12—H12	0.9300	C26—H26	0.9300
C13—H13A	0.9600	C27—H27A	0.9600
C13—H13B	0.9600	C27—H27B	0.9600
C13—H13C	0.9600	C27—H27C	0.9600
C14—H14A	0.9600	C28—H28A	0.9600
C14—H14B	0.9600	C28—H28B	0.9600
C14—H14C	0.9600	C28—H28C	0.9600
O2—S1—O1	117.09 (14)	O3—S2—O4	117.71 (14)
O2—S1—N1	105.17 (14)	O3—S2—N2	109.64 (12)
O1—S1—N1	109.11 (13)	O4—S2—N2	104.73 (13)
O2—S1—C1	111.43 (15)	O3—S2—C15	106.81 (14)
O1—S1—C1	107.33 (13)	O4—S2—C15	110.97 (14)
N1—S1—C1	106.18 (12)	N2—S2—C15	106.48 (12)
C7—N1—S1	122.50 (18)	C21—N2—S2	125.67 (18)
C7—N1—H1N	118.7	C21—N2—H2N	117.2
S1—N1—H1N	118.7	S2—N2—H2N	117.2
C6—C1—C2	120.2 (3)	C20—C15—C16	120.5 (3)
C6—C1—S1	118.1 (2)	C20—C15—S2	118.0 (2)
C2—C1—S1	121.7 (2)	C16—C15—S2	121.5 (3)
C3—C2—C1	116.8 (3)	C15—C16—C17	115.6 (4)
C3—C2—C13	119.8 (3)	C15—C16—C27	123.8 (4)
C1—C2—C13	123.4 (3)	C17—C16—C27	120.6 (4)
C2—C3—C4	124.1 (3)	C18—C17—C16	123.8 (4)
C2—C3—H3	117.9	C18—C17—H17	118.1
C4—C3—H3	117.9	C16—C17—H17	118.1
C5—C4—C3	117.4 (4)	C19—C18—C17	118.4 (4)
C5—C4—C14	120.6 (4)	C19—C18—C28	121.1 (6)
C3—C4—C14	122.0 (4)	C17—C18—C28	120.5 (5)
C6—C5—C4	120.6 (4)	C18—C19—C20	120.9 (5)
C6—C5—H5	119.7	C18—C19—H19	119.6
C4—C5—H5	119.7	C20—C19—H19	119.6
C5—C6—C1	120.9 (3)	C19—C20—C15	120.8 (4)
C5—C6—H6	119.5	C19—C20—H20	119.6
C1—C6—H6	119.5	C15—C20—H20	119.6
C12—C7—C8	120.2 (3)	C26—C21—C22	120.0 (3)
C12—C7—N1	121.4 (3)	C26—C21—N2	118.9 (2)
C8—C7—N1	118.3 (2)	C22—C21—N2	121.0 (3)
C7—C8—C9	118.9 (3)	C23—C22—C21	118.8 (3)
C7—C8—H8	120.5	C23—C22—H22	120.6
C9—C8—H8	120.5	C21—C22—H22	120.6
C10—C9—C8	120.4 (3)	C24—C23—C22	121.3 (3)
C10—C9—H9	119.8	C24—C23—H23	119.3
C8—C9—H9	119.8	C22—C23—H23	119.3
C11—C10—C9	119.9 (3)	C23—C24—C25	119.4 (3)
C11—C10—H10	120.1	C23—C24—H24	120.3
C9—C10—H10	120.1	C25—C24—H24	120.3
C10—C11—C12	120.9 (3)	C26—C25—C24	120.1 (4)
C10—C11—H11	119.6	C26—C25—H25	120.0
C12—C11—H11	119.6	C24—C25—H25	120.0
C7—C12—C11	119.6 (3)	C21—C26—C25	120.4 (3)
C7—C12—H12	120.2	C21—C26—H26	119.8
C11—C12—H12	120.2	C25—C26—H26	119.8
C2—C13—H13A	109.5	C16—C27—H27A	109.5
C2—C13—H13B	109.5	C16—C27—H27B	109.5
H13A—C13—H13B	109.5	H27A—C27—H27B	109.5
C2—C13—H13C	109.5	C16—C27—H27C	109.5
H13A—C13—H13C	109.5	H27A—C27—H27C	109.5
H13B—C13—H13C	109.5	H27B—C27—H27C	109.5
C4—C14—H14A	109.5	C18—C28—H28A	109.5
C4—C14—H14B	109.5	C18—C28—H28B	109.5
H14A—C14—H14B	109.5	H28A—C28—H28B	109.5
C4—C14—H14C	109.5	C18—C28—H28C	109.5
H14A—C14—H14C	109.5	H28A—C28—H28C	109.5
H14B—C14—H14C	109.5	H28B—C28—H28C	109.5
O2—S1—N1—C7	−164.3 (2)	O3—S2—N2—C21	−67.5 (3)
O1—S1—N1—C7	69.3 (3)	O4—S2—N2—C21	165.3 (2)
C1—S1—N1—C7	−46.1 (3)	C15—S2—N2—C21	47.7 (3)
O2—S1—C1—C6	−133.9 (2)	O3—S2—C15—C20	5.2 (3)
O1—S1—C1—C6	−4.5 (3)	O4—S2—C15—C20	134.7 (2)
N1—S1—C1—C6	112.1 (2)	N2—S2—C15—C20	−111.9 (2)
O2—S1—C1—C2	47.0 (3)	O3—S2—C15—C16	−175.1 (2)
O1—S1—C1—C2	176.5 (2)	O4—S2—C15—C16	−45.6 (3)
N1—S1—C1—C2	−67.0 (3)	N2—S2—C15—C16	67.8 (3)
C6—C1—C2—C3	1.0 (4)	C20—C15—C16—C17	−0.5 (4)
S1—C1—C2—C3	−180.0 (3)	S2—C15—C16—C17	179.8 (2)
C6—C1—C2—C13	179.5 (3)	C20—C15—C16—C27	−180.0 (3)
S1—C1—C2—C13	−1.4 (4)	S2—C15—C16—C27	0.4 (5)
C1—C2—C3—C4	−1.0 (5)	C15—C16—C17—C18	0.4 (6)
C13—C2—C3—C4	−179.6 (4)	C27—C16—C17—C18	179.9 (4)
C2—C3—C4—C5	0.8 (6)	C16—C17—C18—C19	0.1 (6)
C2—C3—C4—C14	−178.8 (4)	C16—C17—C18—C28	178.7 (4)
C3—C4—C5—C6	−0.6 (5)	C17—C18—C19—C20	−0.6 (6)
C14—C4—C5—C6	179.0 (4)	C28—C18—C19—C20	−179.2 (4)
C4—C5—C6—C1	0.6 (5)	C18—C19—C20—C15	0.5 (6)
C2—C1—C6—C5	−0.8 (5)	C16—C15—C20—C19	0.1 (5)
S1—C1—C6—C5	−179.9 (3)	S2—C15—C20—C19	179.8 (3)
S1—N1—C7—C12	−45.2 (4)	S2—N2—C21—C26	−142.9 (2)
S1—N1—C7—C8	135.7 (2)	S2—N2—C21—C22	39.2 (4)
C12—C7—C8—C9	−2.4 (5)	C26—C21—C22—C23	0.5 (4)
N1—C7—C8—C9	176.7 (3)	N2—C21—C22—C23	178.4 (3)
C7—C8—C9—C10	2.2 (5)	C21—C22—C23—C24	−1.5 (6)
C8—C9—C10—C11	−0.5 (6)	C22—C23—C24—C25	1.0 (6)
C9—C10—C11—C12	−1.0 (6)	C23—C24—C25—C26	0.4 (6)
C8—C7—C12—C11	1.0 (5)	C22—C21—C26—C25	0.9 (4)
N1—C7—C12—C11	−178.1 (3)	N2—C21—C26—C25	−177.0 (3)
C10—C11—C12—C7	0.8 (6)	C24—C25—C26—C21	−1.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3i	0.86	2.41	3.164 (3)	147
N2—H2N···O1ii	0.86	2.22	3.056 (3)	164
C11—H11···O2iii	0.93	2.50	3.227 (4)	135
C23—H23···O4iii	0.93	2.50	3.316 (4)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.86	2.41	3.164 (3)	147
N2—H2N⋯O1ii	0.86	2.22	3.056 (3)	164
C11—H11⋯O2iii	0.93	2.50	3.227 (4)	135
C23—H23⋯O4iii	0.93	2.50	3.316 (4)	147

Symmetry codes: (i) ; (ii) ; (iii) .