N-(3-Chloro-phen-yl)-4-nitro-benzene-sulfonamide.

There are two independent mol-ecules in the asymmetric unit of the title compound, C12H9ClN2O4S, in which the dihedral angles between the planes of the benzene rings are 46.90 (14) and 44.50 (14)°. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into zigzag chains parallel to the a axis.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-aryl­sulfonamides, see: Chaithanya et al. (2012 ▶); Gowda et al. (2002 ▶) and of N-chloro­aryl­amides, see: Gowda & Shetty (2004 ▶); Gowda & Weiss (1994 ▶); Shetty & Gowda (2004 ▶).

Experimental

Crystal data

C12H9ClN2O4S

M = 312.72

Monoclinic,

a = 14.3419 (8) Å

b = 7.7579 (4) Å

c = 23.895 (1) Å

β = 90.345 (5)°

V = 2658.6 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.46 mm−1

T = 293 K

0.48 × 0.40 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.810, T max = 0.914

9649 measured reflections

4839 independent reflections

3112 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.163

S = 1.05

4839 reflections

367 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.83 e Å−3

Δρmin = −0.29 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812047496/bt6857sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047496/bt6857Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812047496/bt6857Isup3.cml

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

C12H9ClN2O4S	F(000) = 1280
Mr = 312.72	Dx = 1.563 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3273 reflections
a = 14.3419 (8) Å	θ = 2.6–27.8°
b = 7.7579 (4) Å	µ = 0.46 mm−1
c = 23.895 (1) Å	T = 293 K
β = 90.345 (5)°	Prism, colourless
V = 2658.6 (2) Å3	0.48 × 0.40 × 0.20 mm
Z = 8

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	4839 independent reflections
Radiation source: fine-focus sealed tube	3112 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Rotation method data acquisition using ω scans	θmax = 25.4°, θmin = 2.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→17
Tmin = 0.810, Tmax = 0.914	k = −9→5
9649 measured reflections	l = −27→28

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0682P)2 + 2.2606P] where P = (Fo2 + 2Fc2)/3
4839 reflections	(Δ/σ)max = 0.009
367 parameters	Δρmax = 0.83 e Å−3
2 restraints	Δρmin = −0.29 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.09787 (10)	−0.35505 (17)	0.01810 (6)	0.0946 (5)
S1	0.16559 (6)	0.12543 (12)	0.20178 (4)	0.0434 (3)
O1	0.11688 (19)	−0.0333 (3)	0.20733 (11)	0.0562 (7)
O2	0.22431 (18)	0.1878 (4)	0.24582 (11)	0.0627 (8)
O3	−0.1904 (2)	0.6207 (4)	0.12567 (15)	0.0788 (10)
O4	−0.0928 (2)	0.8146 (4)	0.14880 (15)	0.0823 (10)
N1	0.23212 (19)	0.1114 (4)	0.14670 (14)	0.0452 (8)
H1N	0.272 (2)	0.194 (4)	0.1439 (15)	0.054*
N2	−0.1143 (2)	0.6643 (5)	0.14311 (14)	0.0566 (9)
C1	0.0817 (2)	0.2853 (4)	0.18560 (14)	0.0353 (8)
C2	0.1026 (2)	0.4570 (4)	0.19499 (15)	0.0423 (9)
H2	0.1599	0.4877	0.2104	0.051*
C3	0.0387 (2)	0.5819 (4)	0.18147 (15)	0.0442 (9)
H3	0.0514	0.6978	0.1878	0.053*
C4	−0.0450 (2)	0.5309 (4)	0.15819 (14)	0.0405 (8)
C5	−0.0679 (2)	0.3612 (5)	0.14868 (16)	0.0500 (10)
H5	−0.1253	0.3313	0.1332	0.060*
C6	−0.0030 (2)	0.2365 (5)	0.16275 (16)	0.0469 (9)
H6	−0.0163	0.1205	0.1569	0.056*
C7	0.1911 (2)	0.0681 (5)	0.09334 (15)	0.0413 (9)
C8	0.1675 (2)	−0.1024 (5)	0.08276 (17)	0.0482 (10)
H8	0.1777	−0.1874	0.1095	0.058*
C9	0.1285 (3)	−0.1422 (5)	0.03155 (18)	0.0544 (10)
C10	0.1144 (3)	−0.0199 (7)	−0.00864 (18)	0.0658 (12)
H10	0.0883	−0.0494	−0.0431	0.079*
C11	0.1395 (3)	0.1489 (6)	0.00264 (18)	0.0668 (12)
H11	0.1305	0.2334	−0.0245	0.080*
C12	0.1773 (3)	0.1921 (5)	0.05326 (17)	0.0549 (10)
H12	0.1937	0.3058	0.0606	0.066*
Cl2	0.61875 (14)	1.53899 (18)	0.02541 (7)	0.1192 (6)
S2	0.66256 (6)	1.03064 (12)	0.20747 (4)	0.0478 (3)
O5	0.61482 (19)	1.1899 (3)	0.21387 (12)	0.0583 (7)
O6	0.72154 (19)	0.9650 (4)	0.25102 (12)	0.0703 (9)
O7	0.3061 (2)	0.5453 (4)	0.12695 (15)	0.0789 (10)
O8	0.4020 (2)	0.3483 (4)	0.15000 (17)	0.0907 (11)
N3	0.7282 (2)	1.0461 (4)	0.15232 (15)	0.0503 (8)
H3N	0.762 (2)	0.958 (4)	0.1481 (16)	0.060*
N4	0.3811 (2)	0.4986 (5)	0.14497 (14)	0.0568 (9)
C13	0.5779 (2)	0.8725 (4)	0.19141 (14)	0.0373 (8)
C14	0.5992 (2)	0.6997 (5)	0.19794 (16)	0.0470 (9)
H14	0.6570	0.6670	0.2122	0.056*
C15	0.5345 (2)	0.5764 (5)	0.18336 (16)	0.0486 (10)
H15	0.5474	0.4598	0.1880	0.058*
C16	0.4501 (2)	0.6303 (5)	0.16172 (15)	0.0421 (9)
C17	0.4269 (2)	0.8010 (5)	0.15583 (15)	0.0464 (9)
H17	0.3685	0.8331	0.1423	0.056*
C18	0.4919 (2)	0.9235 (5)	0.17029 (15)	0.0437 (9)
H18	0.4783	1.0400	0.1660	0.052*
C19	0.6866 (2)	1.0996 (5)	0.10019 (16)	0.0448 (9)
C20	0.6731 (3)	1.2725 (5)	0.08980 (18)	0.0516 (10)
H20	0.6901	1.3547	0.1163	0.062*
C21	0.6343 (3)	1.3211 (5)	0.0398 (2)	0.0633 (12)
C22	0.6084 (3)	1.2024 (6)	0.00016 (19)	0.0672 (12)
H22	0.5809	1.2385	−0.0332	0.081*
C23	0.6231 (3)	1.0320 (6)	0.0097 (2)	0.0692 (13)
H23	0.6067	0.9511	−0.0173	0.083*
C24	0.6630 (3)	0.9787 (5)	0.06058 (19)	0.0592 (11)
H24	0.6734	0.8623	0.0674	0.071*

	U11	U22	U33	U12	U13	U23
Cl1	0.1078 (11)	0.0610 (8)	0.1148 (11)	−0.0144 (7)	−0.0227 (9)	−0.0310 (8)
S1	0.0416 (5)	0.0361 (5)	0.0524 (6)	0.0073 (4)	−0.0107 (4)	0.0001 (4)
O1	0.0621 (17)	0.0330 (15)	0.0736 (19)	0.0044 (13)	0.0006 (14)	0.0137 (13)
O2	0.0595 (17)	0.0634 (19)	0.0648 (18)	0.0187 (15)	−0.0274 (14)	−0.0094 (15)
O3	0.0481 (18)	0.075 (2)	0.113 (3)	0.0106 (16)	−0.0208 (18)	0.0294 (19)
O4	0.087 (2)	0.0378 (18)	0.122 (3)	0.0197 (17)	−0.020 (2)	0.0079 (18)
N1	0.0314 (16)	0.0350 (18)	0.069 (2)	−0.0020 (13)	−0.0051 (15)	−0.0042 (16)
N2	0.056 (2)	0.053 (2)	0.061 (2)	0.0157 (18)	0.0009 (17)	0.0160 (18)
C1	0.0341 (18)	0.0297 (19)	0.042 (2)	0.0035 (15)	−0.0032 (15)	−0.0025 (16)
C2	0.0317 (18)	0.038 (2)	0.057 (2)	−0.0035 (16)	−0.0079 (16)	−0.0043 (18)
C3	0.046 (2)	0.0253 (19)	0.061 (2)	−0.0012 (16)	−0.0008 (19)	0.0000 (17)
C4	0.0397 (19)	0.035 (2)	0.047 (2)	0.0074 (16)	0.0010 (16)	0.0079 (17)
C5	0.038 (2)	0.045 (2)	0.067 (3)	−0.0046 (17)	−0.0137 (18)	−0.002 (2)
C6	0.042 (2)	0.033 (2)	0.066 (3)	−0.0026 (17)	−0.0122 (19)	−0.0047 (18)
C7	0.0292 (18)	0.040 (2)	0.055 (2)	0.0028 (16)	0.0045 (16)	−0.0034 (18)
C8	0.043 (2)	0.037 (2)	0.065 (3)	0.0010 (17)	0.0002 (19)	0.0002 (19)
C9	0.046 (2)	0.050 (3)	0.066 (3)	−0.0033 (19)	0.001 (2)	−0.013 (2)
C10	0.061 (3)	0.083 (4)	0.053 (3)	0.007 (3)	−0.002 (2)	−0.009 (3)
C11	0.074 (3)	0.069 (3)	0.057 (3)	0.007 (3)	0.001 (2)	0.013 (2)
C12	0.059 (3)	0.042 (2)	0.063 (3)	0.001 (2)	0.007 (2)	0.002 (2)
Cl2	0.1649 (16)	0.0543 (8)	0.1379 (14)	−0.0001 (9)	−0.0415 (12)	0.0214 (9)
S2	0.0420 (5)	0.0396 (6)	0.0615 (6)	−0.0079 (4)	−0.0109 (5)	−0.0029 (5)
O5	0.0621 (17)	0.0346 (15)	0.0783 (19)	−0.0044 (13)	0.0024 (14)	−0.0155 (14)
O6	0.0623 (18)	0.072 (2)	0.0765 (19)	−0.0191 (16)	−0.0324 (16)	0.0079 (16)
O7	0.0486 (17)	0.076 (2)	0.112 (3)	−0.0156 (16)	−0.0221 (18)	−0.0165 (19)
O8	0.083 (2)	0.0390 (19)	0.150 (3)	−0.0190 (17)	−0.019 (2)	−0.006 (2)
N3	0.0324 (17)	0.0358 (19)	0.083 (2)	0.0028 (13)	−0.0023 (16)	0.0026 (17)
N4	0.052 (2)	0.050 (2)	0.068 (2)	−0.0148 (18)	−0.0021 (18)	−0.0091 (19)
C13	0.0332 (18)	0.0322 (19)	0.046 (2)	0.0006 (15)	−0.0018 (15)	−0.0003 (16)
C14	0.037 (2)	0.041 (2)	0.063 (2)	0.0035 (17)	−0.0058 (18)	0.0061 (19)
C15	0.045 (2)	0.030 (2)	0.071 (3)	0.0015 (17)	0.002 (2)	0.0024 (18)
C16	0.0378 (19)	0.039 (2)	0.049 (2)	−0.0060 (17)	0.0010 (17)	−0.0050 (17)
C17	0.0353 (19)	0.045 (2)	0.058 (2)	0.0016 (17)	−0.0088 (17)	−0.0015 (19)
C18	0.043 (2)	0.0287 (19)	0.060 (2)	0.0035 (16)	−0.0083 (18)	0.0019 (17)
C19	0.0335 (19)	0.039 (2)	0.062 (3)	−0.0053 (16)	0.0090 (18)	0.0008 (19)
C20	0.046 (2)	0.034 (2)	0.075 (3)	−0.0039 (17)	−0.001 (2)	−0.001 (2)
C21	0.066 (3)	0.043 (2)	0.082 (3)	−0.003 (2)	0.000 (2)	0.013 (2)
C22	0.071 (3)	0.064 (3)	0.066 (3)	−0.005 (3)	−0.006 (2)	0.001 (3)
C23	0.071 (3)	0.064 (3)	0.073 (3)	−0.011 (3)	0.011 (3)	−0.023 (3)
C24	0.057 (3)	0.041 (2)	0.080 (3)	−0.005 (2)	0.012 (2)	−0.012 (2)

Cl1—C9	1.738 (4)	Cl2—C21	1.739 (4)
S1—O1	1.423 (3)	S2—O5	1.421 (3)
S1—O2	1.428 (3)	S2—O6	1.431 (3)
S1—N1	1.634 (3)	S2—N3	1.629 (3)
S1—C1	1.770 (3)	S2—C13	1.767 (3)
O3—N2	1.215 (4)	O7—N4	1.211 (4)
O4—N2	1.214 (4)	O8—N4	1.209 (4)
N1—C7	1.441 (5)	N3—C19	1.439 (5)
N1—H1N	0.865 (18)	N3—H3N	0.845 (18)
N2—C4	1.478 (4)	N4—C16	1.476 (4)
C1—C6	1.382 (4)	C13—C14	1.383 (5)
C1—C2	1.383 (5)	C13—C18	1.388 (5)
C2—C3	1.371 (5)	C14—C15	1.376 (5)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.377 (5)	C15—C16	1.379 (5)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.375 (5)	C16—C17	1.373 (5)
C5—C6	1.382 (5)	C17—C18	1.373 (5)
C5—H5	0.9300	C17—H17	0.9300
C6—H6	0.9300	C18—H18	0.9300
C7—C12	1.371 (5)	C19—C24	1.373 (5)
C7—C8	1.388 (5)	C19—C20	1.378 (5)
C8—C9	1.377 (5)	C20—C21	1.368 (6)
C8—H8	0.9300	C20—H20	0.9300
C9—C10	1.364 (6)	C21—C22	1.371 (6)
C10—C11	1.384 (6)	C22—C23	1.358 (6)
C10—H10	0.9300	C22—H22	0.9300
C11—C12	1.364 (6)	C23—C24	1.402 (6)
C11—H11	0.9300	C23—H23	0.9300
C12—H12	0.9300	C24—H24	0.9300
O1—S1—O2	120.83 (17)	O5—S2—O6	120.94 (18)
O1—S1—N1	107.88 (16)	O5—S2—N3	107.70 (17)
O2—S1—N1	105.75 (17)	O6—S2—N3	105.83 (18)
O1—S1—C1	107.07 (16)	O5—S2—C13	107.24 (16)
O2—S1—C1	108.70 (16)	O6—S2—C13	108.26 (17)
N1—S1—C1	105.68 (16)	N3—S2—C13	105.98 (16)
C7—N1—S1	119.4 (2)	C19—N3—S2	118.9 (2)
C7—N1—H1N	112 (3)	C19—N3—H3N	111 (3)
S1—N1—H1N	114 (3)	S2—N3—H3N	112 (3)
O3—N2—O4	122.2 (3)	O8—N4—O7	122.9 (3)
O3—N2—C4	119.4 (4)	O8—N4—C16	118.3 (3)
O4—N2—C4	118.4 (3)	O7—N4—C16	118.8 (4)
C6—C1—C2	121.2 (3)	C14—C13—C18	120.8 (3)
C6—C1—S1	119.3 (3)	C14—C13—S2	119.9 (3)
C2—C1—S1	119.5 (3)	C18—C13—S2	119.3 (3)
C3—C2—C1	119.9 (3)	C15—C14—C13	119.9 (3)
C3—C2—H2	120.1	C15—C14—H14	120.1
C1—C2—H2	120.1	C13—C14—H14	120.1
C2—C3—C4	118.1 (3)	C14—C15—C16	118.2 (3)
C2—C3—H3	120.9	C14—C15—H15	120.9
C4—C3—H3	120.9	C16—C15—H15	120.9
C5—C4—C3	123.2 (3)	C17—C16—C15	122.8 (3)
C5—C4—N2	118.0 (3)	C17—C16—N4	118.6 (3)
C3—C4—N2	118.7 (3)	C15—C16—N4	118.5 (3)
C4—C5—C6	118.0 (3)	C16—C17—C18	118.6 (3)
C4—C5—H5	121.0	C16—C17—H17	120.7
C6—C5—H5	121.0	C18—C17—H17	120.7
C1—C6—C5	119.5 (3)	C17—C18—C13	119.6 (3)
C1—C6—H6	120.2	C17—C18—H18	120.2
C5—C6—H6	120.2	C13—C18—H18	120.2
C12—C7—C8	120.5 (4)	C24—C19—C20	120.5 (4)
C12—C7—N1	120.7 (3)	C24—C19—N3	120.0 (4)
C8—C7—N1	118.8 (3)	C20—C19—N3	119.6 (4)
C9—C8—C7	118.2 (4)	C21—C20—C19	118.8 (4)
C9—C8—H8	120.9	C21—C20—H20	120.6
C7—C8—H8	120.9	C19—C20—H20	120.6
C10—C9—C8	121.8 (4)	C20—C21—C22	121.7 (4)
C10—C9—Cl1	119.6 (3)	C20—C21—Cl2	119.4 (4)
C8—C9—Cl1	118.6 (3)	C22—C21—Cl2	118.8 (4)
C9—C10—C11	118.9 (4)	C23—C22—C21	119.8 (4)
C9—C10—H10	120.5	C23—C22—H22	120.1
C11—C10—H10	120.5	C21—C22—H22	120.1
C12—C11—C10	120.4 (4)	C22—C23—C24	119.7 (4)
C12—C11—H11	119.8	C22—C23—H23	120.2
C10—C11—H11	119.8	C24—C23—H23	120.2
C11—C12—C7	120.1 (4)	C19—C24—C23	119.6 (4)
C11—C12—H12	119.9	C19—C24—H24	120.2
C7—C12—H12	119.9	C23—C24—H24	120.2
O1—S1—N1—C7	55.6 (3)	O5—S2—N3—C19	−53.0 (3)
O2—S1—N1—C7	−173.8 (3)	O6—S2—N3—C19	176.3 (3)
C1—S1—N1—C7	−58.7 (3)	C13—S2—N3—C19	61.5 (3)
O1—S1—C1—C6	−21.6 (3)	O5—S2—C13—C14	−162.2 (3)
O2—S1—C1—C6	−153.6 (3)	O6—S2—C13—C14	−30.2 (4)
N1—S1—C1—C6	93.2 (3)	N3—S2—C13—C14	83.0 (3)
O1—S1—C1—C2	159.7 (3)	O5—S2—C13—C18	20.2 (3)
O2—S1—C1—C2	27.6 (3)	O6—S2—C13—C18	152.3 (3)
N1—S1—C1—C2	−85.5 (3)	N3—S2—C13—C18	−94.6 (3)
C6—C1—C2—C3	−0.1 (6)	C18—C13—C14—C15	0.1 (6)
S1—C1—C2—C3	178.6 (3)	S2—C13—C14—C15	−177.5 (3)
C1—C2—C3—C4	−0.6 (5)	C13—C14—C15—C16	0.9 (6)
C2—C3—C4—C5	1.0 (6)	C14—C15—C16—C17	−2.1 (6)
C2—C3—C4—N2	−179.6 (3)	C14—C15—C16—N4	178.8 (3)
O3—N2—C4—C5	3.8 (5)	O8—N4—C16—C17	179.6 (4)
O4—N2—C4—C5	−176.4 (4)	O7—N4—C16—C17	−0.5 (5)
O3—N2—C4—C3	−175.6 (4)	O8—N4—C16—C15	−1.3 (5)
O4—N2—C4—C3	4.2 (5)	O7—N4—C16—C15	178.6 (4)
C3—C4—C5—C6	−0.7 (6)	C15—C16—C17—C18	2.3 (6)
N2—C4—C5—C6	179.9 (3)	N4—C16—C17—C18	−178.6 (3)
C2—C1—C6—C5	0.4 (6)	C16—C17—C18—C13	−1.3 (6)
S1—C1—C6—C5	−178.3 (3)	C14—C13—C18—C17	0.2 (6)
C4—C5—C6—C1	0.0 (6)	S2—C13—C18—C17	177.7 (3)
S1—N1—C7—C12	104.1 (4)	S2—N3—C19—C24	−99.5 (4)
S1—N1—C7—C8	−77.1 (4)	S2—N3—C19—C20	82.3 (4)
C12—C7—C8—C9	−1.1 (5)	C24—C19—C20—C21	1.2 (6)
N1—C7—C8—C9	−179.9 (3)	N3—C19—C20—C21	179.3 (3)
C7—C8—C9—C10	1.1 (6)	C19—C20—C21—C22	0.3 (6)
C7—C8—C9—Cl1	−179.5 (3)	C19—C20—C21—Cl2	−178.8 (3)
C8—C9—C10—C11	−0.4 (6)	C20—C21—C22—C23	−1.5 (7)
Cl1—C9—C10—C11	−179.8 (3)	Cl2—C21—C22—C23	177.6 (4)
C9—C10—C11—C12	−0.3 (7)	C21—C22—C23—C24	1.2 (7)
C10—C11—C12—C7	0.3 (6)	C20—C19—C24—C23	−1.4 (6)
C8—C7—C12—C11	0.4 (6)	N3—C19—C24—C23	−179.5 (3)
N1—C7—C12—C11	179.2 (3)	C22—C23—C24—C19	0.2 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O8	0.87 (2)	2.22 (2)	3.052 (4)	163 (3)
N3—H3N···O4i	0.85 (2)	2.36 (2)	3.135 (4)	153 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O8	0.87 (2)	2.22 (2)	3.052 (4)	163 (3)
N3—H3N⋯O4i	0.85 (2)	2.36 (2)	3.135 (4)	153 (4)

Symmetry code: (i) .