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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\overline{2}) 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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270110023188/sk3377sup1.cif
Contains datablocks I, II, III, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270110023188/sk3377Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270110023188/sk3377IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270110023188/sk3377IIIsup4.hkl
Contains datablock III

CCDC references: 786823; 786824; 786825

Computing details top

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 top
Crystal data top
C10H15N3O2F(000) = 896
Mr = 209.25Dx = 1.280 Mg m3
Monoclinic, P21/cMelting point: 381 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 7.8148 (5) ÅCell parameters from 5295 reflections
b = 20.9889 (14) Åθ = 2.5–30.0°
c = 13.2464 (9) ŵ = 0.09 mm1
β = 91.210 (2)°T = 140 K
V = 2172.2 (2) Å3Thin plate, yellow
Z = 80.22 × 0.18 × 0.04 mm
Data collection top
Bruker SMART 6000 CCD area-detector
diffractometer
4717 independent reflections
Radiation source: sealed tube3307 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.059
ω scansθmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.559, Tmax = 1.000k = 2626
23033 measured reflectionsl = 1516
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: difference Fourier map
wR(F2) = 0.139All H-atom parameters refined
S = 0.97 w = 1/[σ2(Fo2) + (0.0898P)2]
where P = (Fo2 + 2Fc2)/3
4717 reflections(Δ/σ)max = 0.001
391 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.26 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
O10.63355 (16)0.35444 (6)0.45013 (9)0.0443 (3)
O20.68500 (16)0.26199 (6)0.38341 (9)0.0426 (3)
O30.15779 (15)0.37249 (5)0.88626 (9)0.0396 (3)
O40.13061 (14)0.27486 (5)0.93728 (8)0.0353 (3)
N10.57409 (17)0.15831 (7)0.46880 (10)0.0327 (3)
H1N0.623 (2)0.1747 (9)0.4172 (16)0.046 (5)*
N20.29478 (16)0.19290 (6)0.78284 (10)0.0302 (3)
H2N0.260 (2)0.2209 (8)0.8272 (14)0.039 (5)*
N30.62171 (16)0.29501 (7)0.45286 (10)0.0331 (3)
N40.03406 (16)0.24834 (6)1.10349 (9)0.0256 (3)
H4N0.029 (2)0.2352 (7)1.0560 (13)0.023 (4)*
N50.23966 (17)0.42974 (6)1.27911 (11)0.0312 (3)
H5N0.275 (2)0.4031 (8)1.3256 (14)0.031 (4)*
N60.10800 (15)0.33338 (6)0.95034 (9)0.0287 (3)
C10.51748 (17)0.19849 (7)0.54033 (11)0.0270 (3)
C20.43502 (18)0.17483 (7)0.62573 (12)0.0273 (3)
H20.425 (2)0.1302 (8)0.6310 (13)0.033 (4)*
C30.37305 (17)0.21530 (7)0.70053 (11)0.0259 (3)
C40.39349 (18)0.28247 (7)0.69040 (12)0.0285 (3)
H40.357 (2)0.3114 (8)0.7459 (13)0.035 (4)*
C50.47428 (19)0.30596 (8)0.60924 (12)0.0291 (3)
H50.489 (2)0.3494 (8)0.6026 (12)0.030 (4)*
C60.53809 (18)0.26590 (7)0.53286 (11)0.0278 (3)
C70.5517 (2)0.08965 (8)0.46965 (13)0.0374 (4)
H7B0.430 (2)0.0799 (8)0.4721 (13)0.038 (5)*
H7A0.608 (2)0.0719 (7)0.5306 (14)0.030 (4)*
C80.6307 (3)0.06151 (11)0.37664 (17)0.0522 (5)
H8C0.578 (3)0.0780 (9)0.3171 (17)0.054 (6)*
H8B0.751 (3)0.0719 (11)0.3751 (19)0.076 (7)*
H8A0.612 (3)0.0142 (11)0.3727 (16)0.062 (6)*
C90.2685 (2)0.12618 (8)0.80404 (13)0.0332 (4)
H9B0.384 (2)0.1041 (7)0.8120 (12)0.029 (4)*
H9A0.206 (2)0.1051 (7)0.7462 (13)0.031 (4)*
C100.1652 (3)0.11873 (9)0.89908 (14)0.0430 (4)
H10C0.235 (3)0.1353 (9)0.9561 (16)0.050 (5)*
H10B0.145 (2)0.0720 (9)0.9110 (15)0.047 (5)*
H10A0.047 (3)0.1402 (10)0.8899 (16)0.058 (6)*
C110.04718 (17)0.31209 (7)1.11016 (10)0.0234 (3)
C120.13377 (18)0.34025 (7)1.19008 (11)0.0249 (3)
H120.189 (2)0.3130 (7)1.2394 (13)0.026 (4)*
C130.14897 (18)0.40569 (7)1.20148 (11)0.0266 (3)
C140.0687 (2)0.44721 (7)1.13121 (12)0.0317 (4)
H140.066 (2)0.4926 (8)1.1394 (12)0.030 (4)*
C150.0135 (2)0.42091 (8)1.05125 (12)0.0312 (4)
H150.067 (2)0.4482 (9)1.0051 (15)0.041 (5)*
C160.02458 (17)0.35485 (7)1.03691 (11)0.0263 (3)
C170.0861 (2)0.20518 (7)1.18347 (12)0.0270 (3)
H17B0.022 (2)0.2152 (7)1.2466 (13)0.030 (4)*
H17A0.208 (2)0.2112 (7)1.1962 (11)0.024 (4)*
C180.0550 (3)0.13704 (8)1.15234 (14)0.0367 (4)
H18C0.066 (3)0.1310 (8)1.1371 (15)0.050 (5)*
H18B0.085 (2)0.1086 (9)1.2086 (16)0.047 (5)*
H18A0.121 (3)0.1255 (9)1.0945 (18)0.053 (6)*
C190.2385 (2)0.49620 (8)1.30884 (15)0.0402 (4)
H19B0.122 (3)0.5078 (9)1.3259 (15)0.051 (5)*
H19A0.273 (3)0.5236 (10)1.2515 (18)0.067 (6)*
C200.3581 (3)0.50703 (9)1.39423 (19)0.0538 (6)
H20C0.354 (2)0.5499 (10)1.4134 (15)0.045 (5)*
H20B0.322 (3)0.4814 (12)1.449 (2)0.083 (8)*
H20A0.473 (4)0.4959 (11)1.374 (2)0.085 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0557 (8)0.0405 (7)0.0372 (7)0.0124 (6)0.0086 (6)0.0075 (5)
O20.0445 (7)0.0570 (8)0.0267 (6)0.0027 (6)0.0136 (5)0.0021 (5)
O30.0446 (7)0.0476 (7)0.0271 (6)0.0039 (5)0.0118 (5)0.0098 (5)
O40.0422 (7)0.0361 (7)0.0279 (6)0.0003 (5)0.0101 (5)0.0008 (5)
N10.0343 (7)0.0385 (8)0.0256 (7)0.0033 (6)0.0079 (6)0.0007 (6)
N20.0294 (7)0.0332 (7)0.0281 (7)0.0001 (5)0.0065 (6)0.0025 (6)
N30.0307 (7)0.0428 (8)0.0259 (7)0.0049 (6)0.0023 (6)0.0059 (6)
N40.0282 (6)0.0273 (7)0.0214 (6)0.0006 (5)0.0060 (5)0.0018 (5)
N50.0367 (7)0.0241 (7)0.0334 (8)0.0001 (5)0.0116 (6)0.0030 (5)
N60.0257 (6)0.0375 (7)0.0229 (7)0.0017 (5)0.0019 (5)0.0049 (5)
C10.0198 (7)0.0371 (8)0.0242 (7)0.0040 (6)0.0010 (6)0.0001 (6)
C20.0243 (7)0.0287 (8)0.0289 (8)0.0016 (6)0.0011 (6)0.0026 (6)
C30.0184 (7)0.0352 (8)0.0242 (7)0.0021 (6)0.0005 (6)0.0023 (6)
C40.0228 (7)0.0344 (8)0.0282 (8)0.0025 (6)0.0018 (6)0.0011 (6)
C50.0260 (8)0.0307 (8)0.0306 (8)0.0004 (6)0.0002 (6)0.0020 (6)
C60.0226 (7)0.0382 (8)0.0225 (8)0.0012 (6)0.0009 (6)0.0050 (6)
C70.0408 (10)0.0372 (9)0.0344 (10)0.0079 (7)0.0033 (8)0.0008 (7)
C80.0692 (15)0.0481 (12)0.0395 (12)0.0126 (10)0.0070 (10)0.0078 (9)
C90.0329 (9)0.0353 (9)0.0313 (9)0.0011 (7)0.0012 (7)0.0064 (7)
C100.0519 (12)0.0488 (11)0.0284 (9)0.0150 (9)0.0028 (8)0.0079 (8)
C110.0206 (7)0.0287 (7)0.0209 (7)0.0010 (5)0.0005 (5)0.0046 (5)
C120.0230 (7)0.0286 (8)0.0233 (7)0.0014 (6)0.0030 (6)0.0058 (6)
C130.0231 (7)0.0293 (8)0.0274 (8)0.0015 (6)0.0025 (6)0.0054 (6)
C140.0359 (8)0.0262 (8)0.0331 (9)0.0022 (6)0.0066 (7)0.0088 (6)
C150.0307 (8)0.0338 (8)0.0293 (8)0.0012 (6)0.0051 (6)0.0121 (7)
C160.0226 (7)0.0345 (8)0.0220 (7)0.0008 (6)0.0022 (6)0.0059 (6)
C170.0291 (8)0.0277 (8)0.0243 (8)0.0017 (6)0.0031 (6)0.0037 (6)
C180.0462 (10)0.0281 (8)0.0359 (10)0.0003 (7)0.0074 (8)0.0034 (7)
C190.0437 (10)0.0252 (8)0.0520 (11)0.0004 (7)0.0120 (9)0.0005 (8)
C200.0760 (16)0.0283 (10)0.0579 (14)0.0012 (10)0.0241 (12)0.0115 (9)
Geometric parameters (Å, º) top
O1—N31.2514 (18)C8—H8C0.95 (2)
O2—N31.2611 (17)C8—H8B0.97 (2)
O3—N61.2490 (16)C8—H8A1.00 (2)
O4—N61.2534 (16)C9—C101.518 (2)
N1—C11.3498 (19)C9—H9B1.021 (16)
N1—C71.452 (2)C9—H9A1.002 (17)
N1—H1N0.86 (2)C10—H10C0.98 (2)
N2—C31.3462 (19)C10—H10B1.005 (19)
N2—C91.444 (2)C10—H10A1.03 (2)
N2—H2N0.878 (19)C11—C121.399 (2)
N3—C61.3974 (18)C11—C161.4438 (19)
N4—C111.3449 (18)C12—C131.387 (2)
N4—C171.4583 (18)C12—H120.975 (16)
N4—H4N0.854 (17)C13—C141.430 (2)
N5—C131.3584 (19)C14—C151.367 (2)
N5—C191.449 (2)C14—H140.960 (16)
N5—H5N0.881 (18)C15—C161.402 (2)
N6—C161.4053 (19)C15—H150.944 (19)
C1—C21.404 (2)C17—C181.510 (2)
C1—C61.428 (2)C17—H17B0.989 (17)
C2—C31.399 (2)C17—H17A0.977 (16)
C2—H20.942 (17)C18—H18C0.98 (2)
C3—C41.426 (2)C18—H18B0.99 (2)
C4—C51.351 (2)C18—H18A0.95 (2)
C4—H40.998 (17)C19—C201.500 (3)
C5—C61.414 (2)C19—H19B0.96 (2)
C5—H50.923 (17)C19—H19A0.99 (2)
C7—C81.510 (3)C20—H20C0.93 (2)
C7—H7B0.974 (18)C20—H20B0.94 (3)
C7—H7A0.985 (18)C20—H20A0.96 (3)
C1—N1—C7124.98 (14)N2—C9—H9A110.4 (9)
C1—N1—H1N117.7 (12)C10—C9—H9A109.2 (9)
C7—N1—H1N117.2 (12)H9B—C9—H9A107.1 (13)
C3—N2—C9124.42 (14)C9—C10—H10C107.9 (12)
C3—N2—H2N117.5 (12)C9—C10—H10B108.5 (11)
C9—N2—H2N118.1 (12)H10C—C10—H10B108.0 (16)
O1—N3—O2119.76 (12)C9—C10—H10A110.3 (12)
O1—N3—C6119.59 (13)H10C—C10—H10A114.4 (17)
O2—N3—C6120.65 (13)H10B—C10—H10A107.6 (15)
C11—N4—C17123.19 (12)N4—C11—C12120.57 (12)
C11—N4—H4N114.5 (10)N4—C11—C16122.90 (13)
C17—N4—H4N120.7 (10)C12—C11—C16116.53 (13)
C13—N5—C19124.26 (13)C13—C12—C11122.99 (13)
C13—N5—H5N118.1 (11)C13—C12—H12117.9 (9)
C19—N5—H5N114.9 (11)C11—C12—H12119.1 (9)
O3—N6—O4120.23 (12)N5—C13—C12119.84 (13)
O3—N6—C16120.02 (13)N5—C13—C14120.64 (13)
O4—N6—C16119.75 (12)C12—C13—C14119.52 (13)
N1—C1—C2120.48 (14)C15—C14—C13118.58 (14)
N1—C1—C6122.10 (13)C15—C14—H14118.7 (10)
C2—C1—C6117.42 (13)C13—C14—H14122.7 (10)
C3—C2—C1121.82 (14)C14—C15—C16122.39 (14)
C3—C2—H2121.3 (11)C14—C15—H15118.7 (11)
C1—C2—H2116.8 (11)C16—C15—H15118.9 (11)
N2—C3—C2122.11 (14)C15—C16—N6117.30 (13)
N2—C3—C4118.38 (13)C15—C16—C11119.85 (13)
C2—C3—C4119.51 (13)N6—C16—C11122.85 (13)
C5—C4—C3119.40 (14)N4—C17—C18109.94 (13)
C5—C4—H4120.6 (10)N4—C17—H17B109.8 (9)
C3—C4—H4119.8 (10)C18—C17—H17B110.5 (9)
C4—C5—C6121.99 (15)N4—C17—H17A109.4 (9)
C4—C5—H5119.9 (10)C18—C17—H17A109.4 (8)
C6—C5—H5118.1 (10)H17B—C17—H17A107.8 (13)
N3—C6—C5117.39 (14)C17—C18—H18C109.9 (11)
N3—C6—C1122.76 (13)C17—C18—H18B108.9 (11)
C5—C6—C1119.84 (13)H18C—C18—H18B109.0 (16)
N1—C7—C8109.30 (15)C17—C18—H18A112.0 (12)
N1—C7—H7B109.1 (10)H18C—C18—H18A108.2 (17)
C8—C7—H7B111.2 (11)H18B—C18—H18A108.8 (17)
N1—C7—H7A109.3 (9)N5—C19—C20110.51 (14)
C8—C7—H7A109.7 (9)N5—C19—H19B107.9 (11)
H7B—C7—H7A108.2 (14)C20—C19—H19B112.6 (12)
C7—C8—H8C111.0 (12)N5—C19—H19A110.6 (13)
C7—C8—H8B110.1 (15)C20—C19—H19A109.1 (13)
H8C—C8—H8B108 (2)H19B—C19—H19A106.0 (17)
C7—C8—H8A111.6 (13)C19—C20—H20C109.3 (12)
H8C—C8—H8A104.9 (17)C19—C20—H20B108.3 (16)
H8B—C8—H8A111.2 (18)H20C—C20—H20B109.4 (19)
N2—C9—C10109.98 (14)C19—C20—H20A110.0 (17)
N2—C9—H9B109.3 (9)H20C—C20—H20A109.9 (18)
C10—C9—H9B110.7 (9)H20B—C20—H20A110 (2)
N6—O4—H2N—N2142 (7)C3—N2—C9—C10175.97 (15)
O4—H2N—N2—C3143 (7)C11—C12—C13—C142.2 (2)
O4—H2N—N2—C938 (8)C12—C13—C14—C153.5 (2)
C1—C2—C3—C40.0 (2)C13—C14—C15—C161.3 (2)
C2—C3—C4—C50.8 (2)C14—C15—C16—C112.3 (2)
C3—C4—C5—C60.7 (2)C15—C16—C11—C123.5 (2)
C4—C5—C6—C10.1 (2)C16—C11—C12—C131.3 (2)
C5—C6—C1—C20.8 (2)C11—C16—N6—O3175.36 (13)
C6—C1—C2—C30.8 (2)C11—C16—N6—O43.9 (2)
C1—C6—N3—O1179.09 (13)C15—C16—N6—O35.1 (2)
C1—C6—N3—O20.8 (2)C15—C16—N6—O4175.59 (13)
C5—C6—N3—O11.7 (2)C12—C11—N4—C178.6 (2)
C5—C6—N3—O2178.42 (14)C16—C11—N4—C17171.70 (14)
C2—C1—N1—C72.4 (2)C11—N4—C17—C18179.93 (14)
C6—C1—N1—C7177.53 (15)C12—C13—N5—C19168.42 (16)
C1—N1—C7—C8179.41 (16)C14—C13—N5—C1911.5 (2)
C2—C3—N2—C91.0 (2)C13—N5—C19—C20177.56 (18)
C4—C3—N2—C9178.67 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O20.86 (2)1.950 (19)2.6091 (18)132.3 (17)
N2—H2N···O40.878 (19)2.12 (2)2.9835 (18)167.8 (16)
N4—H4N···O40.854 (17)1.961 (17)2.6330 (16)134.8 (13)
N5—H5N···O1i0.881 (18)2.079 (18)2.9507 (18)170.0 (15)
Symmetry code: (i) x1, y, z+1.
(II) 2,6-bis(ethylamino)-3-nitrobenzonitrile top
Crystal data top
C11H14N4O2F(000) = 496
Mr = 234.26Dx = 1.372 Mg m3
Monoclinic, P21/cMelting point: 420 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 10.988 (8) ÅCell parameters from 1800 reflections
b = 4.865 (4) Åθ = 2.6–33.0°
c = 21.220 (18) ŵ = 0.10 mm1
β = 91.62 (4)°T = 150 K
V = 1133.9 (17) Å3Parallelepiped, yellow
Z = 40.55 × 0.40 × 0.18 mm
Data collection top
Bruker SMART 6000 CCD area-detector
diffractometer
2745 independent reflections
Radiation source: sealed tube2346 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
ω scansθmax = 28.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.819, Tmax = 1.000k = 66
11551 measured reflectionsl = 2821
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: difference Fourier map
wR(F2) = 0.131H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0676P)2 + 0.4024P]
where P = (Fo2 + 2Fc2)/3
2745 reflections(Δ/σ)max < 0.001
228 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.39 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.16723 (11)0.0579 (3)0.18323 (5)0.0577 (3)
O20.07049 (9)0.2693 (3)0.22861 (5)0.0503 (3)
N10.38855 (11)0.6007 (3)0.46717 (6)0.0475 (3)
N20.15835 (11)0.4849 (3)0.33291 (6)0.0484 (3)
H2N0.099 (2)0.462 (4)0.3041 (10)0.068 (6)*
N30.15951 (10)0.1123 (3)0.22631 (5)0.0387 (3)
N40.55259 (9)0.1149 (2)0.39957 (6)0.0338 (3)
H4N0.5517 (15)0.213 (4)0.4340 (8)0.042 (4)*
C10.35495 (10)0.2972 (3)0.36893 (6)0.0299 (3)
C20.25174 (11)0.3112 (3)0.32603 (6)0.0319 (3)
C30.25533 (11)0.1278 (3)0.27327 (6)0.0317 (3)
C40.35196 (12)0.0547 (3)0.26620 (6)0.0365 (3)
H40.3481 (16)0.176 (4)0.2316 (8)0.049 (5)*
C50.44946 (12)0.0650 (3)0.30750 (6)0.0358 (3)
H50.5142 (16)0.192 (4)0.3011 (8)0.047 (4)*
C60.45423 (11)0.1149 (2)0.35995 (6)0.0298 (3)
C70.36767 (11)0.4716 (3)0.42273 (6)0.0337 (3)
C8A0.13650 (16)0.6884 (4)0.38084 (9)0.0376 (4)0.75
H8AB0.210 (2)0.786 (4)0.3940 (10)0.040 (5)*0.75
H8AA0.081 (2)0.832 (5)0.3602 (10)0.042 (6)*0.75
C9A0.0773 (2)0.5509 (7)0.43544 (14)0.0539 (6)0.75
H9AC0.129 (2)0.411 (5)0.4545 (12)0.058 (7)*0.75
H9AB0.003 (2)0.465 (5)0.4220 (12)0.058 (7)*0.75
H9AA0.062 (3)0.699 (7)0.4676 (15)0.078 (9)*0.75
C8B0.0986 (5)0.5105 (12)0.4037 (3)0.0309 (11)0.25
H8BA0.01520.43350.40360.037*0.25
H8BB0.14950.41420.43600.037*0.25
C9B0.0972 (4)0.8183 (12)0.4156 (2)0.0349 (10)0.25
H9BA0.06310.85480.45700.052*0.25
H9BB0.04710.90890.38280.052*0.25
H9BC0.18050.88980.41480.052*0.25
C100.65577 (13)0.0717 (3)0.39138 (7)0.0408 (3)
H10A0.6904 (17)0.046 (4)0.3459 (9)0.053 (5)*
H10B0.6260 (16)0.260 (4)0.3964 (8)0.049 (5)*
C110.75812 (14)0.0090 (4)0.43797 (8)0.0502 (4)
H11A0.8283 (19)0.126 (4)0.4292 (9)0.060 (5)*
H11B0.7862 (18)0.185 (4)0.4321 (9)0.062 (6)*
H11C0.732 (2)0.025 (5)0.4802 (11)0.074 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0524 (7)0.0781 (8)0.0418 (6)0.0049 (6)0.0143 (5)0.0215 (6)
O20.0388 (5)0.0625 (7)0.0481 (6)0.0005 (5)0.0225 (4)0.0053 (5)
N10.0373 (6)0.0621 (8)0.0423 (6)0.0125 (6)0.0161 (5)0.0161 (6)
N20.0343 (6)0.0622 (8)0.0473 (7)0.0136 (6)0.0225 (5)0.0172 (6)
N30.0342 (6)0.0498 (7)0.0314 (5)0.0114 (5)0.0084 (4)0.0014 (5)
N40.0266 (5)0.0373 (6)0.0370 (6)0.0044 (4)0.0075 (4)0.0014 (5)
C10.0260 (5)0.0343 (6)0.0290 (6)0.0002 (5)0.0067 (4)0.0003 (5)
C20.0270 (5)0.0369 (6)0.0313 (6)0.0017 (5)0.0074 (4)0.0008 (5)
C30.0295 (6)0.0378 (6)0.0275 (6)0.0080 (5)0.0067 (4)0.0015 (5)
C40.0377 (7)0.0384 (7)0.0331 (6)0.0055 (5)0.0014 (5)0.0051 (5)
C50.0328 (6)0.0359 (6)0.0387 (7)0.0015 (5)0.0020 (5)0.0034 (5)
C60.0260 (5)0.0310 (6)0.0321 (6)0.0021 (4)0.0041 (4)0.0030 (5)
C70.0249 (5)0.0417 (7)0.0339 (6)0.0061 (5)0.0095 (4)0.0011 (5)
C8A0.0285 (8)0.0434 (10)0.0403 (9)0.0049 (8)0.0123 (7)0.0001 (8)
C9A0.0304 (10)0.0867 (19)0.0443 (13)0.0015 (11)0.0041 (10)0.0067 (14)
C8B0.021 (2)0.050 (3)0.022 (2)0.001 (2)0.0011 (19)0.004 (2)
C9B0.025 (2)0.046 (3)0.033 (2)0.006 (2)0.0010 (18)0.002 (2)
C100.0313 (6)0.0417 (7)0.0491 (8)0.0087 (6)0.0054 (6)0.0014 (6)
C110.0330 (7)0.0664 (11)0.0507 (9)0.0147 (7)0.0092 (6)0.0017 (8)
Geometric parameters (Å, º) top
O1—N31.2378 (18)C5—H50.953 (18)
O2—N31.2431 (18)C8A—C9A1.502 (3)
N1—C71.1506 (19)C8A—H8AB0.97 (2)
N2—C21.3404 (19)C8A—H8AA1.02 (2)
N2—C8A1.444 (2)C9A—H9AC0.97 (3)
N2—C8B1.661 (7)C9A—H9AB0.95 (3)
N2—H2N0.89 (2)C9A—H9AA1.01 (3)
N3—C31.4311 (18)C8B—C9B1.518 (8)
N4—C61.3504 (18)C8B—H8BA0.9900
N4—C101.4664 (19)C8B—H8BB0.9900
N4—H4N0.873 (18)C9B—H9BA0.9800
C1—C61.4230 (19)C9B—H9BB0.9800
C1—C71.426 (2)C9B—H9BC0.9800
C1—C21.4357 (18)C10—C111.507 (2)
C2—C31.433 (2)C10—H10A1.055 (19)
C3—C41.395 (2)C10—H10B0.981 (19)
C4—C51.366 (2)C11—H11A0.98 (2)
C4—H40.944 (18)C11—H11B1.00 (2)
C5—C61.416 (2)C11—H11C0.95 (2)
C2—N2—C8A130.67 (13)N2—C8A—H8AA106.1 (13)
C2—N2—C8B118.0 (2)C9A—C8A—H8AA111.7 (12)
C2—N2—H2N113.4 (14)H8AB—C8A—H8AA105.9 (18)
C8A—N2—H2N115.9 (14)C8A—C9A—H9AC112.1 (15)
C8B—N2—H2N109.3 (14)C8A—C9A—H9AB110.5 (15)
O1—N3—O2120.68 (12)H9AC—C9A—H9AB107 (2)
O1—N3—C3119.01 (13)C8A—C9A—H9AA106.8 (18)
O2—N3—C3120.31 (12)H9AC—C9A—H9AA109 (2)
C6—N4—C10122.29 (12)H9AB—C9A—H9AA111 (2)
C6—N4—H4N119.5 (11)C9B—C8B—N2103.3 (4)
C10—N4—H4N117.7 (11)C9B—C8B—H8BA111.1
C6—C1—C7114.83 (11)N2—C8B—H8BA111.1
C6—C1—C2122.64 (12)C9B—C8B—H8BB111.1
C7—C1—C2122.50 (12)N2—C8B—H8BB111.1
N2—C2—C3121.03 (12)H8BA—C8B—H8BB109.1
N2—C2—C1123.66 (12)C8B—C9B—H9BA109.5
C3—C2—C1115.30 (12)C8B—C9B—H9BB109.5
C4—C3—N3116.03 (12)H9BA—C9B—H9BB109.5
C4—C3—C2121.19 (12)C8B—C9B—H9BC109.5
N3—C3—C2122.74 (12)H9BA—C9B—H9BC109.5
C5—C4—C3122.68 (13)H9BB—C9B—H9BC109.5
C5—C4—H4119.6 (11)N4—C10—C11111.24 (14)
C3—C4—H4117.7 (11)N4—C10—H10A109.6 (10)
C4—C5—C6119.51 (13)C11—C10—H10A107.2 (10)
C4—C5—H5120.5 (11)N4—C10—H10B107.8 (10)
C6—C5—H5120.0 (11)C11—C10—H10B111.3 (11)
N4—C6—C5120.04 (12)H10A—C10—H10B109.7 (15)
N4—C6—C1121.32 (12)C10—C11—H11A109.6 (12)
C5—C6—C1118.63 (12)C10—C11—H11B109.6 (12)
N1—C7—C1173.47 (13)H11A—C11—H11B106.0 (16)
N2—C8A—C9A108.8 (2)C10—C11—H11C111.3 (14)
N2—C8A—H8AB112.5 (13)H11A—C11—H11C113.0 (18)
C9A—C8A—H8AB111.8 (13)H11B—C11—H11C107.1 (18)
C1—C2—C3—C41.67 (18)C3—C2—N2—C8A178.77 (16)
C2—C3—C4—C51.8 (2)C1—C2—N2—C8B46.6 (3)
C3—C4—C5—C60.1 (2)C3—C2—N2—C8B134.6 (2)
C4—C5—C6—C11.64 (19)C2—N2—C8A—C9A85.4 (2)
C5—C6—C1—C21.73 (19)C2—N2—C8B—C9B129.2 (3)
C6—C1—C2—C30.09 (18)C2—C3—N3—O1177.59 (12)
C5—C6—N4—C101.47 (19)C2—C3—N3—O23.01 (19)
C1—C6—N4—C10179.79 (12)C4—C3—N3—O10.14 (18)
C1—C2—N2—C8A0.1 (3)C4—C3—N3—O2179.26 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O20.89 (2)1.88 (2)2.610 (2)138.8 (19)
N2—H2N···O2i0.89 (2)2.47 (2)3.123 (2)130.7 (17)
N4—H4N···N1ii0.873 (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 top
Crystal data top
C16H18N4O6SF(000) = 824
Mr = 394.40Dx = 1.456 Mg m3
Monoclinic, P21/cMelting point: 574 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 15.514 (5) ÅCell parameters from 874 reflections
b = 8.573 (4) Åθ = 2–56°
c = 15.012 (5) ŵ = 0.22 mm1
β = 115.647 (12)°T = 210 K
V = 1799.8 (11) Å3Trapezoid, yellow-orange
Z = 40.20 × 0.15 × 0.09 mm
Data collection top
Bruker SMART 6000 CCD area-detector
diffractometer
3539 independent reflections
Radiation source: sealed tube3011 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ω scansθmax = 26.0°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1918
Tmin = 0.793, Tmax = 1.000k = 1010
14699 measured reflectionsl = 1418
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: difference Fourier map
wR(F2) = 0.095All H-atom parameters refined
S = 1.02 w = 1/[σ2(Fo2) + (0.0544P)2 + 0.4673P]
where P = (Fo2 + 2Fc2)/3
3539 reflections(Δ/σ)max = 0.001
316 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.27 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
S10.30295 (3)0.20618 (4)0.06821 (3)0.03319 (13)
N10.29145 (11)0.59772 (17)0.38929 (10)0.0390 (3)
H1N0.2385 (14)0.596 (2)0.3929 (14)0.044 (5)*
N20.11761 (10)0.4433 (2)0.24413 (11)0.0453 (4)
N30.18583 (10)0.59468 (18)0.29296 (10)0.0410 (3)
H3N0.2287 (16)0.620 (3)0.3126 (16)0.059 (6)*
N40.38853 (9)0.51205 (16)0.17556 (9)0.0346 (3)
O10.40029 (8)0.15725 (14)0.09813 (9)0.0430 (3)
O20.22787 (9)0.09193 (13)0.04533 (9)0.0442 (3)
O30.10816 (9)0.52119 (19)0.30876 (10)0.0619 (4)
O40.04976 (9)0.3747 (2)0.18008 (12)0.0781 (5)
O50.47038 (8)0.47050 (18)0.12189 (10)0.0577 (4)
O60.37070 (9)0.59833 (17)0.24709 (9)0.0532 (4)
C10.29244 (11)0.51239 (18)0.31485 (11)0.0317 (3)
C20.21037 (10)0.43338 (19)0.24358 (11)0.0332 (3)
C30.21516 (11)0.34098 (19)0.16978 (11)0.0325 (3)
H30.1610 (14)0.284 (2)0.1257 (14)0.043 (5)*
C40.29997 (11)0.32660 (17)0.16185 (11)0.0305 (3)
C50.38194 (11)0.40640 (19)0.22851 (12)0.0344 (3)
H50.4389 (13)0.398 (2)0.2239 (13)0.038 (5)*
C60.37794 (11)0.4952 (2)0.30230 (12)0.0350 (4)
H60.4296 (14)0.549 (2)0.3446 (14)0.044 (5)*
C70.21493 (10)0.50875 (18)0.21056 (11)0.0319 (3)
C80.31179 (10)0.46316 (18)0.15161 (10)0.0290 (3)
C90.33818 (10)0.37282 (18)0.06701 (11)0.0293 (3)
H90.4028 (12)0.3462 (19)0.0309 (12)0.033 (4)*
C100.26990 (10)0.32403 (17)0.03760 (11)0.0302 (3)
C110.17391 (12)0.3671 (2)0.09329 (13)0.0400 (4)
H110.1261 (14)0.335 (2)0.0746 (14)0.052 (5)*
C120.14766 (12)0.4560 (2)0.17612 (13)0.0407 (4)
H120.0869 (14)0.479 (2)0.2090 (14)0.047 (5)*
C130.37502 (14)0.6672 (2)0.46937 (13)0.0416 (4)
H13B0.4216 (13)0.587 (2)0.5024 (14)0.044 (5)*
H13A0.4048 (13)0.744 (2)0.4420 (13)0.043 (5)*
C140.34374 (19)0.7486 (2)0.53982 (15)0.0531 (5)
H14C0.3119 (16)0.675 (3)0.5645 (15)0.062 (6)*
H14B0.3977 (18)0.794 (3)0.5913 (18)0.070 (7)*
H14A0.2986 (17)0.833 (3)0.5068 (18)0.069 (7)*
C150.08615 (14)0.6323 (3)0.35703 (15)0.0548 (5)
H15B0.0640 (16)0.700 (3)0.3184 (17)0.068 (7)*
H15A0.0491 (16)0.533 (3)0.3785 (17)0.062 (6)*
C160.0803 (2)0.7242 (4)0.44532 (18)0.0707 (7)
H16C0.105 (2)0.668 (3)0.483 (2)0.089 (9)*
H16B0.014 (2)0.748 (3)0.485 (2)0.102 (9)*
H16A0.123 (3)0.824 (4)0.422 (3)0.144 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0386 (2)0.0292 (2)0.0389 (2)0.00409 (15)0.02355 (18)0.00262 (15)
N10.0373 (7)0.0475 (9)0.0338 (7)0.0001 (6)0.0168 (6)0.0026 (6)
N20.0285 (7)0.0683 (10)0.0399 (8)0.0056 (7)0.0154 (6)0.0066 (7)
N30.0351 (7)0.0562 (9)0.0323 (7)0.0053 (7)0.0152 (6)0.0044 (6)
N40.0308 (7)0.0454 (8)0.0316 (7)0.0040 (6)0.0171 (6)0.0046 (6)
O10.0462 (7)0.0407 (6)0.0497 (7)0.0155 (5)0.0278 (6)0.0075 (5)
O20.0573 (7)0.0324 (6)0.0534 (7)0.0065 (5)0.0338 (6)0.0016 (5)
O30.0391 (7)0.0995 (11)0.0530 (8)0.0036 (7)0.0256 (6)0.0246 (8)
O40.0278 (7)0.1314 (15)0.0728 (10)0.0091 (8)0.0197 (7)0.0473 (10)
O50.0291 (6)0.0890 (11)0.0588 (8)0.0043 (6)0.0228 (6)0.0208 (7)
O60.0452 (7)0.0792 (10)0.0403 (7)0.0041 (6)0.0233 (6)0.0165 (6)
C10.0332 (8)0.0332 (8)0.0295 (7)0.0031 (6)0.0144 (6)0.0058 (6)
C20.0261 (7)0.0432 (9)0.0315 (8)0.0050 (6)0.0136 (6)0.0034 (7)
C30.0283 (7)0.0376 (8)0.0314 (8)0.0015 (7)0.0127 (6)0.0010 (7)
C40.0336 (8)0.0307 (8)0.0322 (8)0.0036 (6)0.0190 (6)0.0050 (6)
C50.0293 (7)0.0402 (9)0.0400 (8)0.0006 (6)0.0209 (7)0.0066 (7)
C60.0306 (8)0.0392 (9)0.0357 (8)0.0054 (7)0.0148 (7)0.0029 (7)
C70.0308 (8)0.0370 (8)0.0293 (7)0.0016 (6)0.0142 (6)0.0044 (6)
C80.0265 (7)0.0359 (8)0.0287 (7)0.0029 (6)0.0158 (6)0.0070 (6)
C90.0259 (7)0.0323 (8)0.0308 (7)0.0004 (6)0.0134 (6)0.0056 (6)
C100.0324 (7)0.0306 (8)0.0325 (8)0.0011 (6)0.0186 (6)0.0012 (6)
C110.0318 (8)0.0511 (10)0.0452 (9)0.0001 (7)0.0242 (7)0.0022 (8)
C120.0261 (8)0.0558 (11)0.0414 (9)0.0059 (7)0.0157 (7)0.0027 (8)
C130.0501 (10)0.0360 (9)0.0364 (9)0.0097 (8)0.0165 (8)0.0021 (7)
C140.0823 (15)0.0411 (11)0.0419 (10)0.0220 (11)0.0326 (11)0.0081 (9)
C150.0410 (10)0.0757 (15)0.0431 (10)0.0170 (10)0.0137 (8)0.0103 (10)
C160.0637 (14)0.095 (2)0.0467 (12)0.0296 (15)0.0178 (11)0.0231 (13)
Geometric parameters (Å, º) top
S1—O11.4390 (13)C5—H50.919 (18)
S1—O21.4449 (13)C6—H60.90 (2)
S1—C41.7608 (16)C7—C121.424 (2)
S1—C101.7612 (16)C7—C81.429 (2)
N1—C11.341 (2)C8—C91.389 (2)
N1—C131.460 (2)C9—C101.377 (2)
N1—H1N0.846 (19)C9—H90.938 (17)
N2—O41.226 (2)C10—C111.405 (2)
N2—O31.2375 (19)C11—C121.361 (2)
N2—C21.4451 (19)C11—H110.94 (2)
N3—C71.339 (2)C12—H120.88 (2)
N3—C151.460 (2)C13—C141.512 (3)
N3—H3N0.86 (2)C13—H13B0.966 (19)
N4—O51.2259 (18)C13—H13A0.992 (19)
N4—O61.2327 (18)C14—H14C0.97 (2)
N4—C81.4466 (18)C14—H14B0.94 (3)
C1—C61.426 (2)C14—H14A0.98 (2)
C1—C21.430 (2)C15—C161.511 (3)
C2—C31.390 (2)C15—H15B0.98 (2)
C3—C41.377 (2)C15—H15A1.00 (2)
C3—H30.95 (2)C16—H16C0.94 (3)
C4—C51.409 (2)C16—H16B0.96 (3)
C5—C61.367 (2)C16—H16A1.05 (4)
O1—S1—O2120.38 (8)C9—C8—C7122.23 (13)
O1—S1—C4107.96 (7)C9—C8—N4116.11 (13)
O2—S1—C4106.87 (7)C7—C8—N4121.65 (13)
O1—S1—C10107.77 (7)C10—C9—C8119.94 (14)
O2—S1—C10106.52 (8)C10—C9—H9121.2 (10)
C4—S1—C10106.60 (8)C8—C9—H9118.8 (10)
C1—N1—C13125.61 (15)C9—C10—C11119.57 (14)
C1—N1—H1N114.0 (13)C9—C10—S1119.95 (12)
C13—N1—H1N119.6 (13)C11—C10—S1120.48 (11)
O4—N2—O3121.39 (14)C12—C11—C10120.76 (14)
O4—N2—C2119.10 (14)C12—C11—H11118.2 (12)
O3—N2—C2119.51 (14)C10—C11—H11121.0 (12)
C7—N3—C15124.57 (15)C11—C12—C7122.19 (15)
C7—N3—H3N116.8 (15)C11—C12—H12117.6 (12)
C15—N3—H3N118.2 (15)C7—C12—H12120.2 (13)
O5—N4—O6121.66 (13)N1—C13—C14108.96 (16)
O5—N4—C8118.83 (13)N1—C13—H13B109.4 (11)
O6—N4—C8119.46 (13)C14—C13—H13B111.5 (11)
N1—C1—C6120.87 (15)N1—C13—H13A109.7 (11)
N1—C1—C2123.65 (14)C14—C13—H13A109.2 (11)
C6—C1—C2115.48 (14)H13B—C13—H13A108.0 (15)
C3—C2—C1121.92 (13)C13—C14—H14C109.6 (13)
C3—C2—N2115.80 (14)C13—C14—H14B108.9 (14)
C1—C2—N2122.28 (14)H14C—C14—H14B112.1 (18)
C4—C3—C2120.18 (15)C13—C14—H14A111.3 (14)
C4—C3—H3119.0 (11)H14C—C14—H14A107.9 (19)
C2—C3—H3120.8 (11)H14B—C14—H14A107.1 (19)
C3—C4—C5119.84 (14)N3—C15—C16109.70 (18)
C3—C4—S1118.54 (12)N3—C15—H15B106.4 (14)
C5—C4—S1121.62 (11)C16—C15—H15B107.9 (13)
C6—C5—C4120.15 (14)N3—C15—H15A108.7 (13)
C6—C5—H5119.3 (11)C16—C15—H15A110.8 (13)
C4—C5—H5120.5 (11)H15B—C15—H15A113.3 (18)
C5—C6—C1122.37 (15)C15—C16—H16C112.0 (17)
C5—C6—H6121.0 (12)C15—C16—H16B107.2 (18)
C1—C6—H6116.6 (12)H16C—C16—H16B110 (2)
N3—C7—C12120.20 (14)C15—C16—H16A110 (2)
N3—C7—C8124.48 (14)H16C—C16—H16A105 (3)
C12—C7—C8115.31 (14)H16B—C16—H16A113 (3)
C7—C8—C9—C100.1 (2)O1—S1—C4—C523.23 (15)
C8—C9—C10—C110.4 (2)O1—S1—C4—C3156.21 (12)
C9—C10—C11—C120.3 (3)O2—S1—C4—C5154.05 (13)
C10—C11—C12—C70.2 (3)O2—S1—C4—C325.39 (14)
C11—C12—C7—C80.6 (2)C1—C2—C3—C41.8 (2)
C12—C7—C8—C90.4 (2)C2—C3—C4—C50.3 (2)
C16—C15—N3—C7177.21 (19)C3—C4—C5—C61.4 (2)
C15—N3—C7—C8175.54 (17)C4—C5—C6—C10.5 (2)
C15—N3—C7—C124.4 (3)C5—C6—C1—C21.4 (2)
O5—N4—C8—C90.9 (2)C6—C1—C2—C32.6 (2)
O6—N4—C8—C9176.72 (14)C14—C13—N1—C1177.91 (16)
O5—N4—C8—C7179.40 (15)C13—N1—C1—C2173.40 (16)
O6—N4—C8—C71.8 (2)C13—N1—C1—C66.6 (2)
O1—S1—C10—C99.97 (15)O3—N2—C2—C10.8 (3)
O1—S1—C10—C11169.15 (13)O4—N2—C2—C1178.90 (17)
O2—S1—C10—C9140.44 (12)O3—N2—C2—C3178.70 (16)
O2—S1—C10—C1138.68 (15)O4—N2—C2—C31.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O30.846 (19)1.972 (19)2.646 (2)135.9 (17)
N3—H3N···O60.86 (2)2.00 (2)2.644 (2)131.2 (19)
N1—H1N···O2i0.846 (19)2.862 (19)3.332 (2)117.0 (15)
N3—H3N···O2ii0.86 (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, z1/2.
 

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