N,N'-Diethyl-4-nitro­benzene-1,3-diamine, 2,6-bis­(ethyl­amino)-3-nitro­benzonitrile and bis­(4-ethyl­amino-3-nitro­phenyl) sulfone

N,N'-Diethyl-4-nitro­benzene-1,3-diamine, C₁₀H₁₅N₃O₂, (I), crystallizes with two independent mol­ecules in the asymmetric unit, both of which are nearly planar. The mol­ecules differ in the conformation of the ethyl­amine group trans to the nitro group. Both mol­ecules contain intra­molecular N-H...O hydrogen bonds between the adjacent amine and nitro groups and are linked into one-dimensional chains by inter­molecular N-H...O hydrogen bonds. The chains are organized in layers parallel to (101) with separations of ca 3.4 Å between adjacent sheets. The packing is quite different from what was observed in isomeric 1,3-bis­(ethyl­amino)-2-nitro­benzene. 2,6-Bis(ethyl­amino)-3-nitro­benzonitrile, C₁₁H₁₄N₄O₂, (II), differs from (I) only in the presence of the nitrile functionality between the two ethyl­amine groups. Compound (II) crystallizes with one unique mol­ecule in the asymmetric unit. In contrast with (I), one of the ethyl­amine groups, which is disordered over two sites with occupancies of 0.75 and 0.25, is positioned so that the methyl group is directed out of the plane of the ring by approximately 85°. This ethyl­amine group forms an intra­molecular N-H...O hydrogen bond with the adjacent nitro group. The packing in (II) is very different from that in (I). Mol­ecules of (II) are linked by both inter­molecular amine-nitro N-H...O and amine-nitrile N-H...N hydrogen bonds into a two-dimensional network in the (10) plane. Alternating mol­ecules are approximately orthogonal to one another, indicating that [pi]-[pi] inter­actions are not a significant factor in the packing. Bis(4-ethyl­amino-3-nitro­phenyl) sul­fone, C₁₆H₁₈N₄O₆S, (III), contains the same ortho nitro/ethyl­amine pairing as in (I), with the position para to the nitro group occupied by the sulfone instead of a second ethyl­amine group. Each 4-ethyl­amino-3-nitro­benzene moiety is nearly planar and contains the typical intra­molecular N-H...O hydrogen bond. Due to the tetra­hedral geometry about the S atom, the mol­ecules of (III) adopt an overall V shape. There are no inter­molecular amine-nitro hydrogen bonds. Rather, each amine H atom has a long (H...O ca 2.8 Å) inter­action with one of the sulfone O atoms. Mol­ecules of (III) are thus linked by amine-sulfone N-H...O hydrogen bonds into zigzag double chains running along [001]. Taken together, these structures demonstrate that small changes in the functionalization of ethyl­amine-nitro­arenes cause significant differences in the inter­molecular inter­actions and packing.

Computing details

For all compounds, data collection: SMART (Bruker, 2003); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalMaker (Palmer, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

(I) N,N'-Diethyl-4-nitrobenzene-1,3-diamine

Crystal data

C10H15N3O2	F(000) = 896
Mr = 209.25	Dx = 1.280 Mg m^−3
Monoclinic, P21/c	Melting point: 381 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.8148 (5) Å	Cell parameters from 5295 reflections
b = 20.9889 (14) Å	θ = 2.5–30.0°
c = 13.2464 (9) Å	µ = 0.09 mm^−1
β = 91.210 (2)°	T = 140 K
V = 2172.2 (2) Å^3	Thin plate, yellow
Z = 8	0.22 × 0.18 × 0.04 mm

Data collection

Bruker SMART 6000 CCD area-detector diffractometer	4717 independent reflections
Radiation source: sealed tube	3307 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
ω scans	θmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.559, Tmax = 1.000	k = −26→26
23033 measured reflections	l = −15→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: difference Fourier map
wR(F^2) = 0.139	All H-atom parameters refined
S = 0.97	w = 1/[σ^2(Fo^2) + (0.0898P)^2] where P = (Fo^2 + 2Fc^2)/3
4717 reflections	(Δ/σ)max = 0.001
391 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.63355 (16)	0.35444 (6)	0.45013 (9)	0.0443 (3)
O2	0.68500 (16)	0.26199 (6)	0.38341 (9)	0.0426 (3)
O3	0.15779 (15)	0.37249 (5)	0.88626 (9)	0.0396 (3)
O4	0.13061 (14)	0.27486 (5)	0.93728 (8)	0.0353 (3)
N1	0.57409 (17)	0.15831 (7)	0.46880 (10)	0.0327 (3)
H1N	0.623 (2)	0.1747 (9)	0.4172 (16)	0.046 (5)*
N2	0.29478 (16)	0.19290 (6)	0.78284 (10)	0.0302 (3)
H2N	0.260 (2)	0.2209 (8)	0.8272 (14)	0.039 (5)*
N3	0.62171 (16)	0.29501 (7)	0.45286 (10)	0.0331 (3)
N4	−0.03406 (16)	0.24834 (6)	1.10349 (9)	0.0256 (3)
H4N	0.029 (2)	0.2352 (7)	1.0560 (13)	0.023 (4)*
N5	−0.23966 (17)	0.42974 (6)	1.27911 (11)	0.0312 (3)
H5N	−0.275 (2)	0.4031 (8)	1.3256 (14)	0.031 (4)*
N6	0.10800 (15)	0.33338 (6)	0.95034 (9)	0.0287 (3)
C1	0.51748 (17)	0.19849 (7)	0.54033 (11)	0.0270 (3)
C2	0.43502 (18)	0.17483 (7)	0.62573 (12)	0.0273 (3)
H2	0.425 (2)	0.1302 (8)	0.6310 (13)	0.033 (4)*
C3	0.37305 (17)	0.21530 (7)	0.70053 (11)	0.0259 (3)
C4	0.39349 (18)	0.28247 (7)	0.69040 (12)	0.0285 (3)
H4	0.357 (2)	0.3114 (8)	0.7459 (13)	0.035 (4)*
C5	0.47428 (19)	0.30596 (8)	0.60924 (12)	0.0291 (3)
H5	0.489 (2)	0.3494 (8)	0.6026 (12)	0.030 (4)*
C6	0.53809 (18)	0.26590 (7)	0.53286 (11)	0.0278 (3)
C7	0.5517 (2)	0.08965 (8)	0.46965 (13)	0.0374 (4)
H7B	0.430 (2)	0.0799 (8)	0.4721 (13)	0.038 (5)*
H7A	0.608 (2)	0.0719 (7)	0.5306 (14)	0.030 (4)*
C8	0.6307 (3)	0.06151 (11)	0.37664 (17)	0.0522 (5)
H8C	0.578 (3)	0.0780 (9)	0.3171 (17)	0.054 (6)*
H8B	0.751 (3)	0.0719 (11)	0.3751 (19)	0.076 (7)*
H8A	0.612 (3)	0.0142 (11)	0.3727 (16)	0.062 (6)*
C9	0.2685 (2)	0.12618 (8)	0.80404 (13)	0.0332 (4)
H9B	0.384 (2)	0.1041 (7)	0.8120 (12)	0.029 (4)*
H9A	0.206 (2)	0.1051 (7)	0.7462 (13)	0.031 (4)*
C10	0.1652 (3)	0.11873 (9)	0.89908 (14)	0.0430 (4)
H10C	0.235 (3)	0.1353 (9)	0.9561 (16)	0.050 (5)*
H10B	0.145 (2)	0.0720 (9)	0.9110 (15)	0.047 (5)*
H10A	0.047 (3)	0.1402 (10)	0.8899 (16)	0.058 (6)*
C11	−0.04718 (17)	0.31209 (7)	1.11016 (10)	0.0234 (3)
C12	−0.13377 (18)	0.34025 (7)	1.19008 (11)	0.0249 (3)
H12	−0.189 (2)	0.3130 (7)	1.2394 (13)	0.026 (4)*
C13	−0.14897 (18)	0.40569 (7)	1.20148 (11)	0.0266 (3)
C14	−0.0687 (2)	0.44721 (7)	1.13121 (12)	0.0317 (4)
H14	−0.066 (2)	0.4926 (8)	1.1394 (12)	0.030 (4)*
C15	0.0135 (2)	0.42091 (8)	1.05125 (12)	0.0312 (4)
H15	0.067 (2)	0.4482 (9)	1.0051 (15)	0.041 (5)*
C16	0.02458 (17)	0.35485 (7)	1.03691 (11)	0.0263 (3)
C17	−0.0861 (2)	0.20518 (7)	1.18347 (12)	0.0270 (3)
H17B	−0.022 (2)	0.2152 (7)	1.2466 (13)	0.030 (4)*
H17A	−0.208 (2)	0.2112 (7)	1.1962 (11)	0.024 (4)*
C18	−0.0550 (3)	0.13704 (8)	1.15234 (14)	0.0367 (4)
H18C	0.066 (3)	0.1310 (8)	1.1371 (15)	0.050 (5)*
H18B	−0.085 (2)	0.1086 (9)	1.2086 (16)	0.047 (5)*
H18A	−0.121 (3)	0.1255 (9)	1.0945 (18)	0.053 (6)*
C19	−0.2385 (2)	0.49620 (8)	1.30884 (15)	0.0402 (4)
H19B	−0.122 (3)	0.5078 (9)	1.3259 (15)	0.051 (5)*
H19A	−0.273 (3)	0.5236 (10)	1.2515 (18)	0.067 (6)*
C20	−0.3581 (3)	0.50703 (9)	1.39423 (19)	0.0538 (6)
H20C	−0.354 (2)	0.5499 (10)	1.4134 (15)	0.045 (5)*
H20B	−0.322 (3)	0.4814 (12)	1.449 (2)	0.083 (8)*
H20A	−0.473 (4)	0.4959 (11)	1.374 (2)	0.085 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0557 (8)	0.0405 (7)	0.0372 (7)	−0.0124 (6)	0.0086 (6)	0.0075 (5)
O2	0.0445 (7)	0.0570 (8)	0.0267 (6)	−0.0027 (6)	0.0136 (5)	0.0021 (5)
O3	0.0446 (7)	0.0476 (7)	0.0271 (6)	−0.0039 (5)	0.0118 (5)	0.0098 (5)
O4	0.0422 (7)	0.0361 (7)	0.0279 (6)	−0.0003 (5)	0.0101 (5)	−0.0008 (5)
N1	0.0343 (7)	0.0385 (8)	0.0256 (7)	0.0033 (6)	0.0079 (6)	−0.0007 (6)
N2	0.0294 (7)	0.0332 (7)	0.0281 (7)	0.0001 (5)	0.0065 (6)	0.0025 (6)
N3	0.0307 (7)	0.0428 (8)	0.0259 (7)	−0.0049 (6)	0.0023 (6)	0.0059 (6)
N4	0.0282 (6)	0.0273 (7)	0.0214 (6)	0.0006 (5)	0.0060 (5)	0.0018 (5)
N5	0.0367 (7)	0.0241 (7)	0.0334 (8)	0.0001 (5)	0.0116 (6)	0.0030 (5)
N6	0.0257 (6)	0.0375 (7)	0.0229 (7)	−0.0017 (5)	0.0019 (5)	0.0049 (5)
C1	0.0198 (7)	0.0371 (8)	0.0242 (7)	0.0040 (6)	−0.0010 (6)	0.0001 (6)
C2	0.0243 (7)	0.0287 (8)	0.0289 (8)	0.0016 (6)	0.0011 (6)	0.0026 (6)
C3	0.0184 (7)	0.0352 (8)	0.0242 (7)	0.0021 (6)	0.0005 (6)	0.0023 (6)
C4	0.0228 (7)	0.0344 (8)	0.0282 (8)	0.0025 (6)	0.0018 (6)	−0.0011 (6)
C5	0.0260 (8)	0.0307 (8)	0.0306 (8)	−0.0004 (6)	−0.0002 (6)	0.0020 (6)
C6	0.0226 (7)	0.0382 (8)	0.0225 (8)	−0.0012 (6)	0.0009 (6)	0.0050 (6)
C7	0.0408 (10)	0.0372 (9)	0.0344 (10)	0.0079 (7)	0.0033 (8)	−0.0008 (7)
C8	0.0692 (15)	0.0481 (12)	0.0395 (12)	0.0126 (10)	0.0070 (10)	−0.0078 (9)
C9	0.0329 (9)	0.0353 (9)	0.0313 (9)	−0.0011 (7)	0.0012 (7)	0.0064 (7)
C10	0.0519 (12)	0.0488 (11)	0.0284 (9)	−0.0150 (9)	0.0028 (8)	0.0079 (8)
C11	0.0206 (7)	0.0287 (7)	0.0209 (7)	−0.0010 (5)	−0.0005 (5)	0.0046 (5)
C12	0.0230 (7)	0.0286 (8)	0.0233 (7)	−0.0014 (6)	0.0030 (6)	0.0058 (6)
C13	0.0231 (7)	0.0293 (8)	0.0274 (8)	0.0015 (6)	0.0025 (6)	0.0054 (6)
C14	0.0359 (8)	0.0262 (8)	0.0331 (9)	0.0022 (6)	0.0066 (7)	0.0088 (6)
C15	0.0307 (8)	0.0338 (8)	0.0293 (8)	0.0012 (6)	0.0051 (6)	0.0121 (7)
C16	0.0226 (7)	0.0345 (8)	0.0220 (7)	0.0008 (6)	0.0022 (6)	0.0059 (6)
C17	0.0291 (8)	0.0277 (8)	0.0243 (8)	−0.0017 (6)	0.0031 (6)	0.0037 (6)
C18	0.0462 (10)	0.0281 (8)	0.0359 (10)	−0.0003 (7)	0.0074 (8)	0.0034 (7)
C19	0.0437 (10)	0.0252 (8)	0.0520 (11)	0.0004 (7)	0.0120 (9)	−0.0005 (8)
C20	0.0760 (16)	0.0283 (10)	0.0579 (14)	−0.0012 (10)	0.0241 (12)	−0.0115 (9)

Geometric parameters (Å, º)

O1—N3	1.2514 (18)	C8—H8C	0.95 (2)
O2—N3	1.2611 (17)	C8—H8B	0.97 (2)
O3—N6	1.2490 (16)	C8—H8A	1.00 (2)
O4—N6	1.2534 (16)	C9—C10	1.518 (2)
N1—C1	1.3498 (19)	C9—H9B	1.021 (16)
N1—C7	1.452 (2)	C9—H9A	1.002 (17)
N1—H1N	0.86 (2)	C10—H10C	0.98 (2)
N2—C3	1.3462 (19)	C10—H10B	1.005 (19)
N2—C9	1.444 (2)	C10—H10A	1.03 (2)
N2—H2N	0.878 (19)	C11—C12	1.399 (2)
N3—C6	1.3974 (18)	C11—C16	1.4438 (19)
N4—C11	1.3449 (18)	C12—C13	1.387 (2)
N4—C17	1.4583 (18)	C12—H12	0.975 (16)
N4—H4N	0.854 (17)	C13—C14	1.430 (2)
N5—C13	1.3584 (19)	C14—C15	1.367 (2)
N5—C19	1.449 (2)	C14—H14	0.960 (16)
N5—H5N	0.881 (18)	C15—C16	1.402 (2)
N6—C16	1.4053 (19)	C15—H15	0.944 (19)
C1—C2	1.404 (2)	C17—C18	1.510 (2)
C1—C6	1.428 (2)	C17—H17B	0.989 (17)
C2—C3	1.399 (2)	C17—H17A	0.977 (16)
C2—H2	0.942 (17)	C18—H18C	0.98 (2)
C3—C4	1.426 (2)	C18—H18B	0.99 (2)
C4—C5	1.351 (2)	C18—H18A	0.95 (2)
C4—H4	0.998 (17)	C19—C20	1.500 (3)
C5—C6	1.414 (2)	C19—H19B	0.96 (2)
C5—H5	0.923 (17)	C19—H19A	0.99 (2)
C7—C8	1.510 (3)	C20—H20C	0.93 (2)
C7—H7B	0.974 (18)	C20—H20B	0.94 (3)
C7—H7A	0.985 (18)	C20—H20A	0.96 (3)
C1—N1—C7	124.98 (14)	N2—C9—H9A	110.4 (9)
C1—N1—H1N	117.7 (12)	C10—C9—H9A	109.2 (9)
C7—N1—H1N	117.2 (12)	H9B—C9—H9A	107.1 (13)
C3—N2—C9	124.42 (14)	C9—C10—H10C	107.9 (12)
C3—N2—H2N	117.5 (12)	C9—C10—H10B	108.5 (11)
C9—N2—H2N	118.1 (12)	H10C—C10—H10B	108.0 (16)
O1—N3—O2	119.76 (12)	C9—C10—H10A	110.3 (12)
O1—N3—C6	119.59 (13)	H10C—C10—H10A	114.4 (17)
O2—N3—C6	120.65 (13)	H10B—C10—H10A	107.6 (15)
C11—N4—C17	123.19 (12)	N4—C11—C12	120.57 (12)
C11—N4—H4N	114.5 (10)	N4—C11—C16	122.90 (13)
C17—N4—H4N	120.7 (10)	C12—C11—C16	116.53 (13)
C13—N5—C19	124.26 (13)	C13—C12—C11	122.99 (13)
C13—N5—H5N	118.1 (11)	C13—C12—H12	117.9 (9)
C19—N5—H5N	114.9 (11)	C11—C12—H12	119.1 (9)
O3—N6—O4	120.23 (12)	N5—C13—C12	119.84 (13)
O3—N6—C16	120.02 (13)	N5—C13—C14	120.64 (13)
O4—N6—C16	119.75 (12)	C12—C13—C14	119.52 (13)
N1—C1—C2	120.48 (14)	C15—C14—C13	118.58 (14)
N1—C1—C6	122.10 (13)	C15—C14—H14	118.7 (10)
C2—C1—C6	117.42 (13)	C13—C14—H14	122.7 (10)
C3—C2—C1	121.82 (14)	C14—C15—C16	122.39 (14)
C3—C2—H2	121.3 (11)	C14—C15—H15	118.7 (11)
C1—C2—H2	116.8 (11)	C16—C15—H15	118.9 (11)
N2—C3—C2	122.11 (14)	C15—C16—N6	117.30 (13)
N2—C3—C4	118.38 (13)	C15—C16—C11	119.85 (13)
C2—C3—C4	119.51 (13)	N6—C16—C11	122.85 (13)
C5—C4—C3	119.40 (14)	N4—C17—C18	109.94 (13)
C5—C4—H4	120.6 (10)	N4—C17—H17B	109.8 (9)
C3—C4—H4	119.8 (10)	C18—C17—H17B	110.5 (9)
C4—C5—C6	121.99 (15)	N4—C17—H17A	109.4 (9)
C4—C5—H5	119.9 (10)	C18—C17—H17A	109.4 (8)
C6—C5—H5	118.1 (10)	H17B—C17—H17A	107.8 (13)
N3—C6—C5	117.39 (14)	C17—C18—H18C	109.9 (11)
N3—C6—C1	122.76 (13)	C17—C18—H18B	108.9 (11)
C5—C6—C1	119.84 (13)	H18C—C18—H18B	109.0 (16)
N1—C7—C8	109.30 (15)	C17—C18—H18A	112.0 (12)
N1—C7—H7B	109.1 (10)	H18C—C18—H18A	108.2 (17)
C8—C7—H7B	111.2 (11)	H18B—C18—H18A	108.8 (17)
N1—C7—H7A	109.3 (9)	N5—C19—C20	110.51 (14)
C8—C7—H7A	109.7 (9)	N5—C19—H19B	107.9 (11)
H7B—C7—H7A	108.2 (14)	C20—C19—H19B	112.6 (12)
C7—C8—H8C	111.0 (12)	N5—C19—H19A	110.6 (13)
C7—C8—H8B	110.1 (15)	C20—C19—H19A	109.1 (13)
H8C—C8—H8B	108 (2)	H19B—C19—H19A	106.0 (17)
C7—C8—H8A	111.6 (13)	C19—C20—H20C	109.3 (12)
H8C—C8—H8A	104.9 (17)	C19—C20—H20B	108.3 (16)
H8B—C8—H8A	111.2 (18)	H20C—C20—H20B	109.4 (19)
N2—C9—C10	109.98 (14)	C19—C20—H20A	110.0 (17)
N2—C9—H9B	109.3 (9)	H20C—C20—H20A	109.9 (18)
C10—C9—H9B	110.7 (9)	H20B—C20—H20A	110 (2)
N6—O4—H2N—N2	−142 (7)	C3—N2—C9—C10	−175.97 (15)
O4—H2N—N2—C3	143 (7)	C11—C12—C13—C14	−2.2 (2)
O4—H2N—N2—C9	−38 (8)	C12—C13—C14—C15	3.5 (2)
C1—C2—C3—C4	0.0 (2)	C13—C14—C15—C16	−1.3 (2)
C2—C3—C4—C5	−0.8 (2)	C14—C15—C16—C11	−2.3 (2)
C3—C4—C5—C6	0.7 (2)	C15—C16—C11—C12	3.5 (2)
C4—C5—C6—C1	0.1 (2)	C16—C11—C12—C13	−1.3 (2)
C5—C6—C1—C2	−0.8 (2)	C11—C16—N6—O3	175.36 (13)
C6—C1—C2—C3	0.8 (2)	C11—C16—N6—O4	−3.9 (2)
C1—C6—N3—O1	179.09 (13)	C15—C16—N6—O3	−5.1 (2)
C1—C6—N3—O2	−0.8 (2)	C15—C16—N6—O4	175.59 (13)
C5—C6—N3—O1	−1.7 (2)	C12—C11—N4—C17	−8.6 (2)
C5—C6—N3—O2	178.42 (14)	C16—C11—N4—C17	171.70 (14)
C2—C1—N1—C7	2.4 (2)	C11—N4—C17—C18	179.93 (14)
C6—C1—N1—C7	−177.53 (15)	C12—C13—N5—C19	168.42 (16)
C1—N1—C7—C8	179.41 (16)	C14—C13—N5—C19	−11.5 (2)
C2—C3—N2—C9	1.0 (2)	C13—N5—C19—C20	177.56 (18)
C4—C3—N2—C9	−178.67 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2	0.86 (2)	1.950 (19)	2.6091 (18)	132.3 (17)
N2—H2N···O4	0.878 (19)	2.12 (2)	2.9835 (18)	167.8 (16)
N4—H4N···O4	0.854 (17)	1.961 (17)	2.6330 (16)	134.8 (13)
N5—H5N···O1^i	0.881 (18)	2.079 (18)	2.9507 (18)	170.0 (15)

Symmetry code: (i) x−1, y, z+1.

(II) 2,6-bis(ethylamino)-3-nitrobenzonitrile

Crystal data

C11H14N4O2	F(000) = 496
Mr = 234.26	Dx = 1.372 Mg m^−3
Monoclinic, P21/c	Melting point: 420 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.988 (8) Å	Cell parameters from 1800 reflections
b = 4.865 (4) Å	θ = 2.6–33.0°
c = 21.220 (18) Å	µ = 0.10 mm^−1
β = 91.62 (4)°	T = 150 K
V = 1133.9 (17) Å^3	Parallelepiped, yellow
Z = 4	0.55 × 0.40 × 0.18 mm

Data collection

Bruker SMART 6000 CCD area-detector diffractometer	2745 independent reflections
Radiation source: sealed tube	2346 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
ω scans	θmax = 28.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.819, Tmax = 1.000	k = −6→6
11551 measured reflections	l = −28→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: difference Fourier map
wR(F^2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0676P)^2 + 0.4024P] where P = (Fo^2 + 2Fc^2)/3
2745 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.40 e Å^−3
0 restraints	Δρmin = −0.39 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.16723 (11)	−0.0579 (3)	0.18323 (5)	0.0577 (3)
O2	0.07049 (9)	0.2693 (3)	0.22861 (5)	0.0503 (3)
N1	0.38855 (11)	0.6007 (3)	0.46717 (6)	0.0475 (3)
N2	0.15835 (11)	0.4849 (3)	0.33291 (6)	0.0484 (3)
H2N	0.099 (2)	0.462 (4)	0.3041 (10)	0.068 (6)*
N3	0.15951 (10)	0.1123 (3)	0.22631 (5)	0.0387 (3)
N4	0.55259 (9)	0.1149 (2)	0.39957 (6)	0.0338 (3)
H4N	0.5517 (15)	0.213 (4)	0.4340 (8)	0.042 (4)*
C1	0.35495 (10)	0.2972 (3)	0.36893 (6)	0.0299 (3)
C2	0.25174 (11)	0.3112 (3)	0.32603 (6)	0.0319 (3)
C3	0.25533 (11)	0.1278 (3)	0.27327 (6)	0.0317 (3)
C4	0.35196 (12)	−0.0547 (3)	0.26620 (6)	0.0365 (3)
H4	0.3481 (16)	−0.176 (4)	0.2316 (8)	0.049 (5)*
C5	0.44946 (12)	−0.0650 (3)	0.30750 (6)	0.0358 (3)
H5	0.5142 (16)	−0.192 (4)	0.3011 (8)	0.047 (4)*
C6	0.45423 (11)	0.1149 (2)	0.35995 (6)	0.0298 (3)
C7	0.36767 (11)	0.4716 (3)	0.42273 (6)	0.0337 (3)
C8A	0.13650 (16)	0.6884 (4)	0.38084 (9)	0.0376 (4)	0.75
H8AB	0.210 (2)	0.786 (4)	0.3940 (10)	0.040 (5)*	0.75
H8AA	0.081 (2)	0.832 (5)	0.3602 (10)	0.042 (6)*	0.75
C9A	0.0773 (2)	0.5509 (7)	0.43544 (14)	0.0539 (6)	0.75
H9AC	0.129 (2)	0.411 (5)	0.4545 (12)	0.058 (7)*	0.75
H9AB	0.003 (2)	0.465 (5)	0.4220 (12)	0.058 (7)*	0.75
H9AA	0.062 (3)	0.699 (7)	0.4676 (15)	0.078 (9)*	0.75
C8B	0.0986 (5)	0.5105 (12)	0.4037 (3)	0.0309 (11)	0.25
H8BA	0.0152	0.4335	0.4036	0.037*	0.25
H8BB	0.1495	0.4142	0.4360	0.037*	0.25
C9B	0.0972 (4)	0.8183 (12)	0.4156 (2)	0.0349 (10)	0.25
H9BA	0.0631	0.8548	0.4570	0.052*	0.25
H9BB	0.0471	0.9089	0.3828	0.052*	0.25
H9BC	0.1805	0.8898	0.4148	0.052*	0.25
C10	0.65577 (13)	−0.0717 (3)	0.39138 (7)	0.0408 (3)
H10A	0.6904 (17)	−0.046 (4)	0.3459 (9)	0.053 (5)*
H10B	0.6260 (16)	−0.260 (4)	0.3964 (8)	0.049 (5)*
C11	0.75812 (14)	−0.0090 (4)	0.43797 (8)	0.0502 (4)
H11A	0.8283 (19)	−0.126 (4)	0.4292 (9)	0.060 (5)*
H11B	0.7862 (18)	0.185 (4)	0.4321 (9)	0.062 (6)*
H11C	0.732 (2)	−0.025 (5)	0.4802 (11)	0.074 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0524 (7)	0.0781 (8)	0.0418 (6)	−0.0049 (6)	−0.0143 (5)	−0.0215 (6)
O2	0.0388 (5)	0.0625 (7)	0.0481 (6)	0.0005 (5)	−0.0225 (4)	−0.0053 (5)
N1	0.0373 (6)	0.0621 (8)	0.0423 (6)	0.0125 (6)	−0.0161 (5)	−0.0161 (6)
N2	0.0343 (6)	0.0622 (8)	0.0473 (7)	0.0136 (6)	−0.0225 (5)	−0.0172 (6)
N3	0.0342 (6)	0.0498 (7)	0.0314 (5)	−0.0114 (5)	−0.0084 (4)	−0.0014 (5)
N4	0.0266 (5)	0.0373 (6)	0.0370 (6)	0.0044 (4)	−0.0075 (4)	−0.0014 (5)
C1	0.0260 (5)	0.0343 (6)	0.0290 (6)	−0.0002 (5)	−0.0067 (4)	−0.0003 (5)
C2	0.0270 (5)	0.0369 (6)	0.0313 (6)	−0.0017 (5)	−0.0074 (4)	0.0008 (5)
C3	0.0295 (6)	0.0378 (6)	0.0275 (6)	−0.0080 (5)	−0.0067 (4)	0.0015 (5)
C4	0.0377 (7)	0.0384 (7)	0.0331 (6)	−0.0055 (5)	−0.0014 (5)	−0.0051 (5)
C5	0.0328 (6)	0.0359 (6)	0.0387 (7)	0.0015 (5)	−0.0020 (5)	−0.0034 (5)
C6	0.0260 (5)	0.0310 (6)	0.0321 (6)	−0.0021 (4)	−0.0041 (4)	0.0030 (5)
C7	0.0249 (5)	0.0417 (7)	0.0339 (6)	0.0061 (5)	−0.0095 (4)	−0.0011 (5)
C8A	0.0285 (8)	0.0434 (10)	0.0403 (9)	0.0049 (8)	−0.0123 (7)	−0.0001 (8)
C9A	0.0304 (10)	0.0867 (19)	0.0443 (13)	0.0015 (11)	−0.0041 (10)	0.0067 (14)
C8B	0.021 (2)	0.050 (3)	0.022 (2)	0.001 (2)	0.0011 (19)	0.004 (2)
C9B	0.025 (2)	0.046 (3)	0.033 (2)	0.006 (2)	−0.0010 (18)	−0.002 (2)
C10	0.0313 (6)	0.0417 (7)	0.0491 (8)	0.0087 (6)	−0.0054 (6)	0.0014 (6)
C11	0.0330 (7)	0.0664 (11)	0.0507 (9)	0.0147 (7)	−0.0092 (6)	0.0017 (8)

Geometric parameters (Å, º)

O1—N3	1.2378 (18)	C5—H5	0.953 (18)
O2—N3	1.2431 (18)	C8A—C9A	1.502 (3)
N1—C7	1.1506 (19)	C8A—H8AB	0.97 (2)
N2—C2	1.3404 (19)	C8A—H8AA	1.02 (2)
N2—C8A	1.444 (2)	C9A—H9AC	0.97 (3)
N2—C8B	1.661 (7)	C9A—H9AB	0.95 (3)
N2—H2N	0.89 (2)	C9A—H9AA	1.01 (3)
N3—C3	1.4311 (18)	C8B—C9B	1.518 (8)
N4—C6	1.3504 (18)	C8B—H8BA	0.9900
N4—C10	1.4664 (19)	C8B—H8BB	0.9900
N4—H4N	0.873 (18)	C9B—H9BA	0.9800
C1—C6	1.4230 (19)	C9B—H9BB	0.9800
C1—C7	1.426 (2)	C9B—H9BC	0.9800
C1—C2	1.4357 (18)	C10—C11	1.507 (2)
C2—C3	1.433 (2)	C10—H10A	1.055 (19)
C3—C4	1.395 (2)	C10—H10B	0.981 (19)
C4—C5	1.366 (2)	C11—H11A	0.98 (2)
C4—H4	0.944 (18)	C11—H11B	1.00 (2)
C5—C6	1.416 (2)	C11—H11C	0.95 (2)
C2—N2—C8A	130.67 (13)	N2—C8A—H8AA	106.1 (13)
C2—N2—C8B	118.0 (2)	C9A—C8A—H8AA	111.7 (12)
C2—N2—H2N	113.4 (14)	H8AB—C8A—H8AA	105.9 (18)
C8A—N2—H2N	115.9 (14)	C8A—C9A—H9AC	112.1 (15)
C8B—N2—H2N	109.3 (14)	C8A—C9A—H9AB	110.5 (15)
O1—N3—O2	120.68 (12)	H9AC—C9A—H9AB	107 (2)
O1—N3—C3	119.01 (13)	C8A—C9A—H9AA	106.8 (18)
O2—N3—C3	120.31 (12)	H9AC—C9A—H9AA	109 (2)
C6—N4—C10	122.29 (12)	H9AB—C9A—H9AA	111 (2)
C6—N4—H4N	119.5 (11)	C9B—C8B—N2	103.3 (4)
C10—N4—H4N	117.7 (11)	C9B—C8B—H8BA	111.1
C6—C1—C7	114.83 (11)	N2—C8B—H8BA	111.1
C6—C1—C2	122.64 (12)	C9B—C8B—H8BB	111.1
C7—C1—C2	122.50 (12)	N2—C8B—H8BB	111.1
N2—C2—C3	121.03 (12)	H8BA—C8B—H8BB	109.1
N2—C2—C1	123.66 (12)	C8B—C9B—H9BA	109.5
C3—C2—C1	115.30 (12)	C8B—C9B—H9BB	109.5
C4—C3—N3	116.03 (12)	H9BA—C9B—H9BB	109.5
C4—C3—C2	121.19 (12)	C8B—C9B—H9BC	109.5
N3—C3—C2	122.74 (12)	H9BA—C9B—H9BC	109.5
C5—C4—C3	122.68 (13)	H9BB—C9B—H9BC	109.5
C5—C4—H4	119.6 (11)	N4—C10—C11	111.24 (14)
C3—C4—H4	117.7 (11)	N4—C10—H10A	109.6 (10)
C4—C5—C6	119.51 (13)	C11—C10—H10A	107.2 (10)
C4—C5—H5	120.5 (11)	N4—C10—H10B	107.8 (10)
C6—C5—H5	120.0 (11)	C11—C10—H10B	111.3 (11)
N4—C6—C5	120.04 (12)	H10A—C10—H10B	109.7 (15)
N4—C6—C1	121.32 (12)	C10—C11—H11A	109.6 (12)
C5—C6—C1	118.63 (12)	C10—C11—H11B	109.6 (12)
N1—C7—C1	173.47 (13)	H11A—C11—H11B	106.0 (16)
N2—C8A—C9A	108.8 (2)	C10—C11—H11C	111.3 (14)
N2—C8A—H8AB	112.5 (13)	H11A—C11—H11C	113.0 (18)
C9A—C8A—H8AB	111.8 (13)	H11B—C11—H11C	107.1 (18)
C1—C2—C3—C4	1.67 (18)	C3—C2—N2—C8A	−178.77 (16)
C2—C3—C4—C5	−1.8 (2)	C1—C2—N2—C8B	−46.6 (3)
C3—C4—C5—C6	0.1 (2)	C3—C2—N2—C8B	134.6 (2)
C4—C5—C6—C1	1.64 (19)	C2—N2—C8A—C9A	−85.4 (2)
C5—C6—C1—C2	−1.73 (19)	C2—N2—C8B—C9B	129.2 (3)
C6—C1—C2—C3	0.09 (18)	C2—C3—N3—O1	−177.59 (12)
C5—C6—N4—C10	−1.47 (19)	C2—C3—N3—O2	3.01 (19)
C1—C6—N4—C10	179.79 (12)	C4—C3—N3—O1	0.14 (18)
C1—C2—N2—C8A	−0.1 (3)	C4—C3—N3—O2	−179.26 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O2	0.89 (2)	1.88 (2)	2.610 (2)	138.8 (19)
N2—H2N···O2^i	0.89 (2)	2.47 (2)	3.123 (2)	130.7 (17)
N4—H4N···N1^ii	0.873 (18)	2.361 (19)	3.198 (3)	160.7 (15)

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z+1.

(III) bis(4-ethylamino-3-nitrophenyl) sulfone

Crystal data

C16H18N4O6S	F(000) = 824
Mr = 394.40	Dx = 1.456 Mg m^−3
Monoclinic, P21/c	Melting point: 574 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.514 (5) Å	Cell parameters from 874 reflections
b = 8.573 (4) Å	θ = 2–56°
c = 15.012 (5) Å	µ = 0.22 mm^−1
β = 115.647 (12)°	T = 210 K
V = 1799.8 (11) Å^3	Trapezoid, yellow-orange
Z = 4	0.20 × 0.15 × 0.09 mm

Data collection

Bruker SMART 6000 CCD area-detector diffractometer	3539 independent reflections
Radiation source: sealed tube	3011 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω scans	θmax = 26.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→18
Tmin = 0.793, Tmax = 1.000	k = −10→10
14699 measured reflections	l = −14→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: difference Fourier map
wR(F^2) = 0.095	All H-atom parameters refined
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0544P)^2 + 0.4673P] where P = (Fo^2 + 2Fc^2)/3
3539 reflections	(Δ/σ)max = 0.001
316 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.30295 (3)	0.20618 (4)	0.06821 (3)	0.03319 (13)
N1	0.29145 (11)	0.59772 (17)	0.38929 (10)	0.0390 (3)
H1N	0.2385 (14)	0.596 (2)	0.3929 (14)	0.044 (5)*
N2	0.11761 (10)	0.4433 (2)	0.24413 (11)	0.0453 (4)
N3	0.18583 (10)	0.59468 (18)	−0.29296 (10)	0.0410 (3)
H3N	0.2287 (16)	0.620 (3)	−0.3126 (16)	0.059 (6)*
N4	0.38853 (9)	0.51205 (16)	−0.17556 (9)	0.0346 (3)
O1	0.40029 (8)	0.15725 (14)	0.09813 (9)	0.0430 (3)
O2	0.22787 (9)	0.09193 (13)	0.04533 (9)	0.0442 (3)
O3	0.10816 (9)	0.52119 (19)	0.30876 (10)	0.0619 (4)
O4	0.04976 (9)	0.3747 (2)	0.18008 (12)	0.0781 (5)
O5	0.47038 (8)	0.47050 (18)	−0.12189 (10)	0.0577 (4)
O6	0.37070 (9)	0.59833 (17)	−0.24709 (9)	0.0532 (4)
C1	0.29244 (11)	0.51239 (18)	0.31485 (11)	0.0317 (3)
C2	0.21037 (10)	0.43338 (19)	0.24358 (11)	0.0332 (3)
C3	0.21516 (11)	0.34098 (19)	0.16978 (11)	0.0325 (3)
H3	0.1610 (14)	0.284 (2)	0.1257 (14)	0.043 (5)*
C4	0.29997 (11)	0.32660 (17)	0.16185 (11)	0.0305 (3)
C5	0.38194 (11)	0.40640 (19)	0.22851 (12)	0.0344 (3)
H5	0.4389 (13)	0.398 (2)	0.2239 (13)	0.038 (5)*
C6	0.37794 (11)	0.4952 (2)	0.30230 (12)	0.0350 (4)
H6	0.4296 (14)	0.549 (2)	0.3446 (14)	0.044 (5)*
C7	0.21493 (10)	0.50875 (18)	−0.21056 (11)	0.0319 (3)
C8	0.31179 (10)	0.46316 (18)	−0.15161 (10)	0.0290 (3)
C9	0.33818 (10)	0.37282 (18)	−0.06701 (11)	0.0293 (3)
H9	0.4028 (12)	0.3462 (19)	−0.0309 (12)	0.033 (4)*
C10	0.26990 (10)	0.32403 (17)	−0.03760 (11)	0.0302 (3)
C11	0.17391 (12)	0.3671 (2)	−0.09329 (13)	0.0400 (4)
H11	0.1261 (14)	0.335 (2)	−0.0746 (14)	0.052 (5)*
C12	0.14766 (12)	0.4560 (2)	−0.17612 (13)	0.0407 (4)
H12	0.0869 (14)	0.479 (2)	−0.2090 (14)	0.047 (5)*
C13	0.37502 (14)	0.6672 (2)	0.46937 (13)	0.0416 (4)
H13B	0.4216 (13)	0.587 (2)	0.5024 (14)	0.044 (5)*
H13A	0.4048 (13)	0.744 (2)	0.4420 (13)	0.043 (5)*
C14	0.34374 (19)	0.7486 (2)	0.53982 (15)	0.0531 (5)
H14C	0.3119 (16)	0.675 (3)	0.5645 (15)	0.062 (6)*
H14B	0.3977 (18)	0.794 (3)	0.5913 (18)	0.070 (7)*
H14A	0.2986 (17)	0.833 (3)	0.5068 (18)	0.069 (7)*
C15	0.08615 (14)	0.6323 (3)	−0.35703 (15)	0.0548 (5)
H15B	0.0640 (16)	0.700 (3)	−0.3184 (17)	0.068 (7)*
H15A	0.0491 (16)	0.533 (3)	−0.3785 (17)	0.062 (6)*
C16	0.0803 (2)	0.7242 (4)	−0.44532 (18)	0.0707 (7)
H16C	0.105 (2)	0.668 (3)	−0.483 (2)	0.089 (9)*
H16B	0.014 (2)	0.748 (3)	−0.485 (2)	0.102 (9)*
H16A	0.123 (3)	0.824 (4)	−0.422 (3)	0.144 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0386 (2)	0.0292 (2)	0.0389 (2)	0.00409 (15)	0.02355 (18)	0.00262 (15)
N1	0.0373 (7)	0.0475 (9)	0.0338 (7)	−0.0001 (6)	0.0168 (6)	−0.0026 (6)
N2	0.0285 (7)	0.0683 (10)	0.0399 (8)	0.0056 (7)	0.0154 (6)	−0.0066 (7)
N3	0.0351 (7)	0.0562 (9)	0.0323 (7)	0.0053 (7)	0.0152 (6)	0.0044 (6)
N4	0.0308 (7)	0.0454 (8)	0.0316 (7)	−0.0040 (6)	0.0171 (6)	−0.0046 (6)
O1	0.0462 (7)	0.0407 (6)	0.0497 (7)	0.0155 (5)	0.0278 (6)	0.0075 (5)
O2	0.0573 (7)	0.0324 (6)	0.0534 (7)	−0.0065 (5)	0.0338 (6)	−0.0016 (5)
O3	0.0391 (7)	0.0995 (11)	0.0530 (8)	0.0036 (7)	0.0256 (6)	−0.0246 (8)
O4	0.0278 (7)	0.1314 (15)	0.0728 (10)	−0.0091 (8)	0.0197 (7)	−0.0473 (10)
O5	0.0291 (6)	0.0890 (11)	0.0588 (8)	0.0043 (6)	0.0228 (6)	0.0208 (7)
O6	0.0452 (7)	0.0792 (10)	0.0403 (7)	−0.0041 (6)	0.0233 (6)	0.0165 (6)
C1	0.0332 (8)	0.0332 (8)	0.0295 (7)	0.0031 (6)	0.0144 (6)	0.0058 (6)
C2	0.0261 (7)	0.0432 (9)	0.0315 (8)	0.0050 (6)	0.0136 (6)	0.0034 (7)
C3	0.0283 (7)	0.0376 (8)	0.0314 (8)	0.0015 (7)	0.0127 (6)	0.0010 (7)
C4	0.0336 (8)	0.0307 (8)	0.0322 (8)	0.0036 (6)	0.0190 (6)	0.0050 (6)
C5	0.0293 (7)	0.0402 (9)	0.0400 (8)	0.0006 (6)	0.0209 (7)	0.0066 (7)
C6	0.0306 (8)	0.0392 (9)	0.0357 (8)	−0.0054 (7)	0.0148 (7)	0.0029 (7)
C7	0.0308 (8)	0.0370 (8)	0.0293 (7)	0.0016 (6)	0.0142 (6)	−0.0044 (6)
C8	0.0265 (7)	0.0359 (8)	0.0287 (7)	−0.0029 (6)	0.0158 (6)	−0.0070 (6)
C9	0.0259 (7)	0.0323 (8)	0.0308 (7)	0.0004 (6)	0.0134 (6)	−0.0056 (6)
C10	0.0324 (7)	0.0306 (8)	0.0325 (8)	0.0011 (6)	0.0186 (6)	−0.0012 (6)
C11	0.0318 (8)	0.0511 (10)	0.0452 (9)	0.0001 (7)	0.0242 (7)	0.0022 (8)
C12	0.0261 (8)	0.0558 (11)	0.0414 (9)	0.0059 (7)	0.0157 (7)	0.0027 (8)
C13	0.0501 (10)	0.0360 (9)	0.0364 (9)	−0.0097 (8)	0.0165 (8)	0.0021 (7)
C14	0.0823 (15)	0.0411 (11)	0.0419 (10)	−0.0220 (11)	0.0326 (11)	−0.0081 (9)
C15	0.0410 (10)	0.0757 (15)	0.0431 (10)	0.0170 (10)	0.0137 (8)	0.0103 (10)
C16	0.0637 (14)	0.095 (2)	0.0467 (12)	0.0296 (15)	0.0178 (11)	0.0231 (13)

Geometric parameters (Å, º)

S1—O1	1.4390 (13)	C5—H5	0.919 (18)
S1—O2	1.4449 (13)	C6—H6	0.90 (2)
S1—C4	1.7608 (16)	C7—C12	1.424 (2)
S1—C10	1.7612 (16)	C7—C8	1.429 (2)
N1—C1	1.341 (2)	C8—C9	1.389 (2)
N1—C13	1.460 (2)	C9—C10	1.377 (2)
N1—H1N	0.846 (19)	C9—H9	0.938 (17)
N2—O4	1.226 (2)	C10—C11	1.405 (2)
N2—O3	1.2375 (19)	C11—C12	1.361 (2)
N2—C2	1.4451 (19)	C11—H11	0.94 (2)
N3—C7	1.339 (2)	C12—H12	0.88 (2)
N3—C15	1.460 (2)	C13—C14	1.512 (3)
N3—H3N	0.86 (2)	C13—H13B	0.966 (19)
N4—O5	1.2259 (18)	C13—H13A	0.992 (19)
N4—O6	1.2327 (18)	C14—H14C	0.97 (2)
N4—C8	1.4466 (18)	C14—H14B	0.94 (3)
C1—C6	1.426 (2)	C14—H14A	0.98 (2)
C1—C2	1.430 (2)	C15—C16	1.511 (3)
C2—C3	1.390 (2)	C15—H15B	0.98 (2)
C3—C4	1.377 (2)	C15—H15A	1.00 (2)
C3—H3	0.95 (2)	C16—H16C	0.94 (3)
C4—C5	1.409 (2)	C16—H16B	0.96 (3)
C5—C6	1.367 (2)	C16—H16A	1.05 (4)
O1—S1—O2	120.38 (8)	C9—C8—C7	122.23 (13)
O1—S1—C4	107.96 (7)	C9—C8—N4	116.11 (13)
O2—S1—C4	106.87 (7)	C7—C8—N4	121.65 (13)
O1—S1—C10	107.77 (7)	C10—C9—C8	119.94 (14)
O2—S1—C10	106.52 (8)	C10—C9—H9	121.2 (10)
C4—S1—C10	106.60 (8)	C8—C9—H9	118.8 (10)
C1—N1—C13	125.61 (15)	C9—C10—C11	119.57 (14)
C1—N1—H1N	114.0 (13)	C9—C10—S1	119.95 (12)
C13—N1—H1N	119.6 (13)	C11—C10—S1	120.48 (11)
O4—N2—O3	121.39 (14)	C12—C11—C10	120.76 (14)
O4—N2—C2	119.10 (14)	C12—C11—H11	118.2 (12)
O3—N2—C2	119.51 (14)	C10—C11—H11	121.0 (12)
C7—N3—C15	124.57 (15)	C11—C12—C7	122.19 (15)
C7—N3—H3N	116.8 (15)	C11—C12—H12	117.6 (12)
C15—N3—H3N	118.2 (15)	C7—C12—H12	120.2 (13)
O5—N4—O6	121.66 (13)	N1—C13—C14	108.96 (16)
O5—N4—C8	118.83 (13)	N1—C13—H13B	109.4 (11)
O6—N4—C8	119.46 (13)	C14—C13—H13B	111.5 (11)
N1—C1—C6	120.87 (15)	N1—C13—H13A	109.7 (11)
N1—C1—C2	123.65 (14)	C14—C13—H13A	109.2 (11)
C6—C1—C2	115.48 (14)	H13B—C13—H13A	108.0 (15)
C3—C2—C1	121.92 (13)	C13—C14—H14C	109.6 (13)
C3—C2—N2	115.80 (14)	C13—C14—H14B	108.9 (14)
C1—C2—N2	122.28 (14)	H14C—C14—H14B	112.1 (18)
C4—C3—C2	120.18 (15)	C13—C14—H14A	111.3 (14)
C4—C3—H3	119.0 (11)	H14C—C14—H14A	107.9 (19)
C2—C3—H3	120.8 (11)	H14B—C14—H14A	107.1 (19)
C3—C4—C5	119.84 (14)	N3—C15—C16	109.70 (18)
C3—C4—S1	118.54 (12)	N3—C15—H15B	106.4 (14)
C5—C4—S1	121.62 (11)	C16—C15—H15B	107.9 (13)
C6—C5—C4	120.15 (14)	N3—C15—H15A	108.7 (13)
C6—C5—H5	119.3 (11)	C16—C15—H15A	110.8 (13)
C4—C5—H5	120.5 (11)	H15B—C15—H15A	113.3 (18)
C5—C6—C1	122.37 (15)	C15—C16—H16C	112.0 (17)
C5—C6—H6	121.0 (12)	C15—C16—H16B	107.2 (18)
C1—C6—H6	116.6 (12)	H16C—C16—H16B	110 (2)
N3—C7—C12	120.20 (14)	C15—C16—H16A	110 (2)
N3—C7—C8	124.48 (14)	H16C—C16—H16A	105 (3)
C12—C7—C8	115.31 (14)	H16B—C16—H16A	113 (3)
C7—C8—C9—C10	0.1 (2)	O1—S1—C4—C5	23.23 (15)
C8—C9—C10—C11	−0.4 (2)	O1—S1—C4—C3	−156.21 (12)
C9—C10—C11—C12	0.3 (3)	O2—S1—C4—C5	154.05 (13)
C10—C11—C12—C7	0.2 (3)	O2—S1—C4—C3	−25.39 (14)
C11—C12—C7—C8	−0.6 (2)	C1—C2—C3—C4	−1.8 (2)
C12—C7—C8—C9	0.4 (2)	C2—C3—C4—C5	−0.3 (2)
C16—C15—N3—C7	−177.21 (19)	C3—C4—C5—C6	1.4 (2)
C15—N3—C7—C8	175.54 (17)	C4—C5—C6—C1	−0.5 (2)
C15—N3—C7—C12	−4.4 (3)	C5—C6—C1—C2	−1.4 (2)
O5—N4—C8—C9	0.9 (2)	C6—C1—C2—C3	2.6 (2)
O6—N4—C8—C9	−176.72 (14)	C14—C13—N1—C1	−177.91 (16)
O5—N4—C8—C7	179.40 (15)	C13—N1—C1—C2	173.40 (16)
O6—N4—C8—C7	1.8 (2)	C13—N1—C1—C6	−6.6 (2)
O1—S1—C10—C9	−9.97 (15)	O3—N2—C2—C1	−0.8 (3)
O1—S1—C10—C11	169.15 (13)	O4—N2—C2—C1	178.90 (17)
O2—S1—C10—C9	−140.44 (12)	O3—N2—C2—C3	178.70 (16)
O2—S1—C10—C11	38.68 (15)	O4—N2—C2—C3	−1.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3	0.846 (19)	1.972 (19)	2.646 (2)	135.9 (17)
N3—H3N···O6	0.86 (2)	2.00 (2)	2.644 (2)	131.2 (19)
N1—H1N···O2^i	0.846 (19)	2.862 (19)	3.332 (2)	117.0 (15)
N3—H3N···O2^ii	0.86 (2)	2.80 (2)	3.201 (2)	110.4 (17)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2.