4-Chloro-N-(3,5-dimethyl-phen-yl)benzene-sulfonamide.

The asymmetric unit of the title compound, C(14)H(14)ClNO(2)S, contains two independent mol-ecules, which are twisted at the S atoms with C-SO(2)-NH-C torsion angles of -69.4 (7)° and 66.0 (8)°. The sulfonyl and the anilino benzene rings are tilted relative to each other by 49.0 (4) and 61.7 (3)° in the two mol-ecules. In the crystal, the mol-ecules are linked into chains by N-H⋯O hydrogen bonds.

Related literature

For hydrogen-bonding modes of sulfonamides, see: Adsmond & Grant (2001 ▶). For our studies of the effect of substituents on the structures of N-(ar­yl)-amides, see: Gowda et al. (2006 ▶), on N-(ar­yl)aryl­sulfonamides, see: Nirmala et al. (2009 ▶); Shakuntala et al. (2011 ▶) and on N-(ar­yl)methane­sulfonamides, see: Gowda et al. (2007 ▶).

Experimental

Crystal data

C14H14ClNO2S

M = 295.77

Orthorhombic,

a = 21.990 (2) Å

b = 10.0470 (8) Å

c = 26.408 (2) Å

V = 5834.4 (8) Å3

Z = 16

Mo Kα radiation

μ = 0.40 mm−1

T = 293 K

0.40 × 0.20 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.856, T max = 0.976

21403 measured reflections

5320 independent reflections

2694 reflections with I > 2σ(I)

R int = 0.106

Refinement

R[F 2 > 2σ(F 2)] = 0.128

wR(F 2) = 0.345

S = 1.07

5320 reflections

347 parameters

1 restraint

H-atom parameters constrained

Δρmax = 1.06 e Å−3

Δρmin = −0.41 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; 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 datablock(s) I, global. DOI: 10.1107/S1600536811028819/ds2123sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028819/ds2123Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811028819/ds2123Isup3.cml

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

C14H14ClNO2S	F(000) = 2464
Mr = 295.77	Dx = 1.347 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2329 reflections
a = 21.990 (2) Å	θ = 2.5–27.8°
b = 10.0470 (8) Å	µ = 0.40 mm−1
c = 26.408 (2) Å	T = 293 K
V = 5834.4 (8) Å3	Prism, colourless
Z = 16	0.40 × 0.20 × 0.06 mm

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	5320 independent reflections
Radiation source: fine-focus sealed tube	2694 reflections with I > 2σ(I)
graphite	Rint = 0.106
Rotation method data acquisition using ω scans.	θmax = 25.4°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −26→26
Tmin = 0.856, Tmax = 0.976	k = −9→12
21403 measured reflections	l = −25→31

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)] = 0.128	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.345	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.1148P)2 + 41.4199P] where P = (Fo2 + 2Fc2)/3
5320 reflections	(Δ/σ)max = 0.003
347 parameters	Δρmax = 1.06 e Å−3
1 restraint	Δρmin = −0.41 e Å−3

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
Cl1	0.00034 (14)	0.0421 (4)	0.59314 (17)	0.1103 (14)
S1	0.26317 (10)	0.0246 (2)	0.50757 (9)	0.0454 (6)
O1	0.3036 (3)	0.0914 (6)	0.5418 (2)	0.0544 (17)
O2	0.2769 (3)	−0.1061 (6)	0.4911 (3)	0.0547 (17)
N1	0.2594 (3)	0.1192 (7)	0.4583 (3)	0.0456 (18)
H1A	0.2778	0.1947	0.4587	0.055*
C1	0.1902 (4)	0.0237 (9)	0.5340 (3)	0.047 (2)
C2	0.1472 (5)	−0.0646 (11)	0.5157 (5)	0.070 (3)
H2	0.1570	−0.1267	0.4910	0.084*
C3	0.0889 (5)	−0.0574 (12)	0.5355 (5)	0.082 (4)
H3	0.0593	−0.1163	0.5242	0.098*
C4	0.0746 (5)	0.0348 (11)	0.5713 (5)	0.065 (3)
C5	0.1174 (5)	0.1204 (11)	0.5888 (4)	0.069 (3)
H5	0.1075	0.1818	0.6138	0.083*
C6	0.1749 (4)	0.1166 (10)	0.5699 (4)	0.056 (3)
H6	0.2039	0.1770	0.5814	0.068*
C7	0.2264 (3)	0.0807 (8)	0.4140 (3)	0.037 (2)
C8	0.1732 (4)	0.1481 (9)	0.4019 (3)	0.044 (2)
H8	0.1583	0.2126	0.4239	0.053*
C9	0.1421 (4)	0.1212 (10)	0.3577 (4)	0.049 (2)
C10	0.1645 (4)	0.0205 (10)	0.3270 (4)	0.054 (2)
H10	0.1435	−0.0003	0.2974	0.065*
C11	0.2166 (5)	−0.0504 (10)	0.3383 (4)	0.057 (3)
C12	0.2471 (4)	−0.0189 (9)	0.3823 (3)	0.049 (2)
H12	0.2822	−0.0655	0.3907	0.058*
C13	0.0873 (4)	0.2025 (12)	0.3421 (4)	0.074 (3)
H13A	0.0989	0.2941	0.3383	0.088*
H13B	0.0563	0.1954	0.3676	0.088*
H13C	0.0717	0.1697	0.3105	0.088*
C14	0.2416 (5)	−0.1558 (11)	0.3035 (4)	0.070 (3)
H14A	0.2404	−0.1242	0.2693	0.084*
H14B	0.2174	−0.2350	0.3064	0.084*
H14C	0.2828	−0.1754	0.3128	0.084*
Cl2	0.09120 (19)	0.4163 (3)	0.22721 (16)	0.1050 (13)
S2	0.13516 (12)	1.0127 (3)	0.17349 (10)	0.0600 (8)
O3	0.1989 (3)	1.0367 (8)	0.1698 (3)	0.085 (2)
O4	0.0976 (4)	1.0924 (8)	0.2066 (3)	0.081 (2)
N2	0.1092 (3)	1.0317 (8)	0.1159 (3)	0.0504 (19)
H2A	0.1342	1.0514	0.0920	0.061*
C15	0.1242 (4)	0.8416 (10)	0.1887 (3)	0.048 (2)
C16	0.1665 (5)	0.7509 (12)	0.1776 (4)	0.065 (3)
H16	0.2030	0.7759	0.1625	0.078*
C17	0.1549 (5)	0.6177 (11)	0.1893 (4)	0.069 (3)
H17	0.1832	0.5524	0.1809	0.083*
C18	0.1036 (5)	0.5848 (11)	0.2123 (4)	0.062 (3)
C19	0.0606 (5)	0.6750 (12)	0.2248 (4)	0.071 (3)
H19	0.0243	0.6488	0.2398	0.085*
C20	0.0720 (4)	0.8036 (11)	0.2150 (4)	0.058 (3)
H20	0.0447	0.8683	0.2258	0.070*
C21	0.0456 (4)	1.0162 (9)	0.1041 (3)	0.042 (2)
C22	0.0300 (4)	0.9218 (9)	0.0686 (3)	0.044 (2)
H22	0.0596	0.8654	0.0556	0.053*
C23	−0.0305 (4)	0.9104 (9)	0.0518 (3)	0.046 (2)
C24	−0.0726 (4)	0.9957 (9)	0.0725 (4)	0.052 (2)
H24	−0.1127	0.9909	0.0615	0.063*
C25	−0.0572 (4)	1.0907 (9)	0.1101 (4)	0.050 (2)
C26	0.0030 (4)	1.0975 (9)	0.1251 (3)	0.044 (2)
H26	0.0144	1.1584	0.1498	0.053*
C27	−0.0480 (4)	0.8106 (10)	0.0130 (4)	0.057 (3)
H27A	−0.0597	0.7292	0.0293	0.068*
H27B	−0.0141	0.7940	−0.0090	0.068*
H27C	−0.0815	0.8440	−0.0066	0.068*
C28	−0.1049 (5)	1.1804 (13)	0.1316 (5)	0.086 (4)
H28A	−0.1370	1.1277	0.1459	0.104*
H28B	−0.1210	1.2359	0.1052	0.104*
H28C	−0.0872	1.2352	0.1575	0.104*

	U11	U22	U33	U12	U13	U23
Cl1	0.0679 (19)	0.107 (3)	0.156 (4)	−0.008 (2)	0.046 (2)	0.006 (3)
S1	0.0432 (12)	0.0429 (13)	0.0501 (13)	0.0036 (10)	−0.0105 (10)	−0.0032 (11)
O1	0.046 (4)	0.060 (4)	0.057 (4)	0.001 (3)	−0.022 (3)	−0.009 (3)
O2	0.065 (4)	0.039 (4)	0.061 (4)	0.008 (3)	−0.010 (3)	−0.001 (3)
N1	0.047 (4)	0.053 (5)	0.037 (4)	−0.011 (3)	−0.007 (3)	−0.006 (4)
C1	0.049 (5)	0.041 (5)	0.051 (5)	−0.003 (4)	−0.013 (4)	0.000 (5)
C2	0.053 (6)	0.066 (7)	0.091 (8)	−0.006 (5)	−0.001 (6)	−0.022 (6)
C3	0.058 (7)	0.069 (8)	0.119 (11)	−0.021 (6)	−0.001 (7)	−0.015 (8)
C4	0.059 (6)	0.046 (6)	0.091 (8)	0.005 (5)	0.013 (6)	0.011 (6)
C5	0.076 (8)	0.064 (7)	0.067 (7)	−0.007 (6)	0.013 (6)	−0.013 (6)
C6	0.054 (6)	0.067 (7)	0.048 (6)	−0.004 (5)	0.002 (5)	−0.005 (5)
C7	0.031 (4)	0.036 (5)	0.044 (5)	−0.004 (4)	−0.008 (4)	0.005 (4)
C8	0.043 (5)	0.046 (5)	0.043 (5)	0.001 (4)	−0.004 (4)	−0.005 (4)
C9	0.038 (5)	0.063 (6)	0.046 (5)	0.002 (4)	0.000 (4)	0.006 (5)
C10	0.053 (6)	0.065 (7)	0.044 (5)	−0.002 (5)	−0.014 (4)	0.004 (5)
C11	0.066 (6)	0.061 (6)	0.045 (6)	−0.003 (5)	0.000 (5)	−0.006 (5)
C12	0.049 (5)	0.053 (6)	0.044 (5)	0.008 (5)	−0.006 (4)	0.004 (5)
C13	0.049 (6)	0.094 (9)	0.079 (8)	0.009 (6)	−0.012 (5)	0.016 (7)
C14	0.080 (7)	0.075 (8)	0.054 (6)	0.009 (6)	−0.010 (6)	−0.021 (6)
Cl2	0.124 (3)	0.075 (2)	0.116 (3)	−0.007 (2)	−0.004 (2)	0.035 (2)
S2	0.0554 (15)	0.0633 (17)	0.0614 (16)	−0.0026 (13)	−0.0178 (13)	−0.0092 (14)
O3	0.048 (4)	0.096 (6)	0.111 (6)	−0.020 (4)	−0.028 (4)	0.009 (5)
O4	0.103 (6)	0.087 (6)	0.052 (4)	0.022 (5)	−0.020 (4)	−0.028 (4)
N2	0.038 (4)	0.068 (5)	0.046 (4)	−0.007 (4)	−0.002 (3)	0.007 (4)
C15	0.049 (5)	0.053 (6)	0.041 (5)	0.004 (5)	−0.019 (4)	0.002 (5)
C16	0.061 (6)	0.072 (8)	0.063 (7)	−0.004 (6)	−0.001 (5)	−0.012 (6)
C17	0.075 (8)	0.063 (7)	0.070 (8)	0.021 (6)	0.010 (6)	−0.004 (6)
C18	0.069 (7)	0.069 (7)	0.049 (6)	0.004 (6)	0.001 (5)	0.008 (5)
C19	0.058 (6)	0.079 (6)	0.074 (8)	−0.003 (6)	0.003 (6)	0.017 (7)
C20	0.051 (6)	0.066 (5)	0.059 (6)	0.005 (5)	0.010 (5)	−0.012 (5)
C21	0.041 (5)	0.042 (5)	0.044 (5)	−0.002 (4)	0.004 (4)	0.007 (4)
C22	0.044 (5)	0.046 (5)	0.043 (5)	0.005 (4)	0.005 (4)	0.004 (4)
C23	0.037 (5)	0.052 (6)	0.048 (5)	0.000 (4)	0.001 (4)	0.002 (5)
C24	0.042 (5)	0.057 (6)	0.057 (6)	0.000 (4)	−0.002 (4)	0.004 (5)
C25	0.042 (5)	0.058 (6)	0.050 (6)	0.010 (4)	0.009 (4)	−0.005 (5)
C26	0.045 (5)	0.046 (6)	0.042 (5)	0.000 (4)	0.003 (4)	−0.009 (4)
C27	0.054 (6)	0.058 (6)	0.058 (6)	0.002 (5)	−0.008 (5)	−0.005 (5)
C28	0.065 (7)	0.093 (9)	0.102 (10)	0.019 (7)	−0.003 (7)	−0.021 (8)

Cl1—C4	1.732 (10)	Cl2—C18	1.760 (11)
S1—O2	1.416 (6)	S2—O3	1.425 (7)
S1—O1	1.434 (6)	S2—O4	1.445 (8)
S1—N1	1.613 (7)	S2—N2	1.636 (7)
S1—C1	1.750 (9)	S2—C15	1.782 (10)
N1—C7	1.429 (10)	N2—C21	1.442 (10)
N1—H1A	0.8600	N2—H2A	0.8600
C1—C6	1.374 (13)	C15—C16	1.335 (13)
C1—C2	1.383 (13)	C15—C20	1.394 (13)
C2—C3	1.384 (14)	C16—C17	1.396 (15)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.361 (16)	C17—C18	1.323 (15)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.357 (15)	C18—C19	1.351 (15)
C5—C6	1.360 (13)	C19—C20	1.342 (14)
C5—H5	0.9300	C19—H19	0.9300
C6—H6	0.9300	C20—H20	0.9300
C7—C12	1.382 (12)	C21—C26	1.361 (11)
C7—C8	1.390 (11)	C21—C22	1.378 (12)
C8—C9	1.380 (12)	C22—C23	1.406 (12)
C8—H8	0.9300	C22—H22	0.9300
C9—C10	1.387 (13)	C23—C24	1.376 (12)
C9—C13	1.513 (12)	C23—C27	1.485 (12)
C10—C11	1.382 (13)	C24—C25	1.417 (13)
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.377 (12)	C25—C26	1.383 (12)
C11—C14	1.505 (13)	C25—C28	1.495 (13)
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	119.7 (4)	O3—S2—O4	120.6 (5)
O2—S1—N1	108.0 (4)	O3—S2—N2	105.0 (5)
O1—S1—N1	105.4 (4)	O4—S2—N2	107.4 (4)
O2—S1—C1	108.2 (4)	O3—S2—C15	108.2 (5)
O1—S1—C1	108.6 (4)	O4—S2—C15	108.7 (5)
N1—S1—C1	106.1 (4)	N2—S2—C15	106.0 (4)
C7—N1—S1	121.8 (6)	C21—N2—S2	121.8 (6)
C7—N1—H1A	119.1	C21—N2—H2A	119.1
S1—N1—H1A	119.1	S2—N2—H2A	119.1
C6—C1—C2	120.6 (9)	C16—C15—C20	119.8 (10)
C6—C1—S1	119.7 (7)	C16—C15—S2	120.9 (8)
C2—C1—S1	119.5 (8)	C20—C15—S2	119.2 (8)
C3—C2—C1	117.9 (10)	C15—C16—C17	118.6 (10)
C3—C2—H2	121.1	C15—C16—H16	120.7
C1—C2—H2	121.1	C17—C16—H16	120.7
C4—C3—C2	120.8 (10)	C18—C17—C16	119.7 (10)
C4—C3—H3	119.6	C18—C17—H17	120.1
C2—C3—H3	119.6	C16—C17—H17	120.1
C5—C4—C3	120.4 (10)	C17—C18—C19	122.8 (11)
C5—C4—Cl1	121.0 (9)	C17—C18—Cl2	118.4 (9)
C3—C4—Cl1	118.6 (9)	C19—C18—Cl2	118.7 (9)
C4—C5—C6	120.3 (11)	C20—C19—C18	117.8 (11)
C4—C5—H5	119.9	C20—C19—H19	121.1
C6—C5—H5	119.9	C18—C19—H19	121.1
C5—C6—C1	119.9 (10)	C19—C20—C15	120.9 (10)
C5—C6—H6	120.0	C19—C20—H20	119.5
C1—C6—H6	120.0	C15—C20—H20	119.5
C12—C7—C8	119.3 (8)	C26—C21—C22	121.3 (8)
C12—C7—N1	121.7 (7)	C26—C21—N2	121.0 (8)
C8—C7—N1	119.0 (8)	C22—C21—N2	117.6 (8)
C9—C8—C7	121.2 (8)	C21—C22—C23	120.4 (8)
C9—C8—H8	119.4	C21—C22—H22	119.8
C7—C8—H8	119.4	C23—C22—H22	119.8
C8—C9—C10	117.4 (8)	C24—C23—C22	117.3 (9)
C8—C9—C13	121.3 (9)	C24—C23—C27	121.5 (8)
C10—C9—C13	121.2 (9)	C22—C23—C27	121.2 (8)
C11—C10—C9	122.9 (9)	C23—C24—C25	122.6 (8)
C11—C10—H10	118.5	C23—C24—H24	118.7
C9—C10—H10	118.5	C25—C24—H24	118.7
C12—C11—C10	117.9 (9)	C26—C25—C24	117.5 (8)
C12—C11—C14	119.9 (9)	C26—C25—C28	122.2 (9)
C10—C11—C14	122.2 (9)	C24—C25—C28	120.3 (9)
C11—C12—C7	121.2 (9)	C21—C26—C25	120.8 (8)
C11—C12—H12	119.4	C21—C26—H26	119.6
C7—C12—H12	119.4	C25—C26—H26	119.6
C9—C13—H13A	109.5	C23—C27—H27A	109.5
C9—C13—H13B	109.5	C23—C27—H27B	109.5
H13A—C13—H13B	109.5	H27A—C27—H27B	109.5
C9—C13—H13C	109.5	C23—C27—H27C	109.5
H13A—C13—H13C	109.5	H27A—C27—H27C	109.5
H13B—C13—H13C	109.5	H27B—C27—H27C	109.5
C11—C14—H14A	109.5	C25—C28—H28A	109.5
C11—C14—H14B	109.5	C25—C28—H28B	109.5
H14A—C14—H14B	109.5	H28A—C28—H28B	109.5
C11—C14—H14C	109.5	C25—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	46.5 (7)	O3—S2—N2—C21	−179.5 (7)
O1—S1—N1—C7	175.5 (6)	O4—S2—N2—C21	−50.1 (8)
C1—S1—N1—C7	−69.4 (7)	C15—S2—N2—C21	66.0 (8)
O2—S1—C1—C6	153.8 (7)	O3—S2—C15—C16	−23.8 (9)
O1—S1—C1—C6	22.4 (9)	O4—S2—C15—C16	−156.4 (8)
N1—S1—C1—C6	−90.5 (8)	N2—S2—C15—C16	88.4 (8)
O2—S1—C1—C2	−30.9 (9)	O3—S2—C15—C20	152.8 (8)
O1—S1—C1—C2	−162.3 (8)	O4—S2—C15—C20	20.2 (9)
N1—S1—C1—C2	84.8 (9)	N2—S2—C15—C20	−95.0 (8)
C6—C1—C2—C3	−1.1 (16)	C20—C15—C16—C17	5.0 (15)
S1—C1—C2—C3	−176.4 (9)	S2—C15—C16—C17	−178.4 (8)
C1—C2—C3—C4	0.8 (19)	C15—C16—C17—C18	−2.1 (17)
C2—C3—C4—C5	−0.9 (19)	C16—C17—C18—C19	0.9 (18)
C2—C3—C4—Cl1	178.0 (10)	C16—C17—C18—Cl2	−179.0 (9)
C3—C4—C5—C6	1.3 (18)	C17—C18—C19—C20	−2.5 (18)
Cl1—C4—C5—C6	−177.5 (9)	Cl2—C18—C19—C20	177.3 (9)
C4—C5—C6—C1	−1.7 (17)	C18—C19—C20—C15	5.4 (17)
C2—C1—C6—C5	1.6 (15)	C16—C15—C20—C19	−6.8 (15)
S1—C1—C6—C5	176.9 (8)	S2—C15—C20—C19	176.5 (9)
S1—N1—C7—C12	−71.4 (10)	S2—N2—C21—C26	62.2 (11)
S1—N1—C7—C8	110.6 (8)	S2—N2—C21—C22	−121.8 (8)
C12—C7—C8—C9	−2.7 (13)	C26—C21—C22—C23	2.1 (13)
N1—C7—C8—C9	175.3 (8)	N2—C21—C22—C23	−173.9 (8)
C7—C8—C9—C10	2.7 (13)	C21—C22—C23—C24	−0.5 (13)
C7—C8—C9—C13	−174.6 (9)	C21—C22—C23—C27	179.1 (8)
C8—C9—C10—C11	−1.5 (14)	C22—C23—C24—C25	−1.2 (14)
C13—C9—C10—C11	175.9 (10)	C27—C23—C24—C25	179.2 (9)
C9—C10—C11—C12	0.2 (15)	C23—C24—C25—C26	1.2 (14)
C9—C10—C11—C14	−177.6 (9)	C23—C24—C25—C28	−179.6 (10)
C10—C11—C12—C7	−0.2 (15)	C22—C21—C26—C25	−2.1 (14)
C14—C11—C12—C7	177.7 (9)	N2—C21—C26—C25	173.8 (8)
C8—C7—C12—C11	1.4 (13)	C24—C25—C26—C21	0.4 (14)
N1—C7—C12—C11	−176.6 (9)	C28—C25—C26—C21	−178.7 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.86	2.49	3.001 (9)	119.
N2—H2A···O1ii	0.86	2.39	3.006 (9)	130.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.86	2.49	3.001 (9)	119
N2—H2A⋯O1ii	0.86	2.39	3.006 (9)	130

Symmetry codes: (i) ; (ii) .