A series of N-(2-phenyl­ethyl)nitro­aniline derivatives as precursors for slow and sustained nitric oxide release agents

2,4-Di­nitro-N-(2-phenyl­ethyl)aniline, C₁₄H₁₃N₃O₄, (I), crystallizes with one independent mol­ecule in the asymmetric unit. The adjacent amine and nitro groups form an intra­molecular N—H...O hydrogen bond. The anti conformation about the ethyl C—C bond leads to the phenyl and aniline rings being essentially parallel. Mol­ecules are linked into dimers by inter­molecular N—H...O hydrogen bonds, such that each amine H atom participates in a three-centre inter­action with two nitro O atoms. Though the dimers pack so that the arene rings of adjacent mol­ecules are parallel, the rings are staggered and π–π inter­actions do not appear to be favoured. 4,6-Di­nitro-N,N′-bis­(2-phenyl­ethyl)benzene-1,3-di­amine, C₂₂H₂₂N₄O₄, (II), differs from (I) in the presence of a second 2-phenyl­ethyl­amine group on the substituted ring. Compound (II) also crystallizes with one unique mol­ecule in the asymmetric unit. Both amine groups are involved in intra­molecular N—H...O hydrogen bonds with adjacent nitro groups. Although one ethyl group adopts an anti conformation as in (I), the other is gauche, with the result that the pendant phenyl rings are not parallel. The amine group that is part of the gauche conformation participates in a three-centre N—H...O hydrogen bond with the nitro group of a neighbouring mol­ecule, leading to dimers as in (I). The other amine H atom does not form any inter­molecular hydrogen bonds. The packing leads to separations of ca 3.4 Å of the parallel anti phenyl and amino­benzene rings. 2-Cyano-4-nitro-N-(2-phenyl­ethyl)aniline, C₁₅H₁₃N₃O₂, (III), differs from (I) only in having a cyano group in place of the 2-nitro group. The absence of the adjacent nitro group eliminates the intra­molecular N—H...O hydrogen bond. Mol­ecules of (III) adopt the same anti conformation about the ethyl group as in (I), but crystallize in the higher-symmetry monoclinic space group P2₁/n. The mol­ecules are linked into dimers via N—H...N amine–cyano hydrogen bonds, while the nitro groups are not involved in any N—H...O inter­actions. Owing to the different symmetry, the mol­ecules pack in a herringbone pattern with fewer face-to-face inter­actions between the rings. The closest such inter­actions are about 3.5 Å between rings that are largely slipped past one another. 4-Methyl­sulfonyl-2-nitro-N-(2-phenyl­ethyl)aniline, C₁₅H₁₆N₂O₄S, (IV), differs from (I) in having a methyl­sulfonyl group in place of the 4-nitro group. The intra­molecular N—H...O hydrogen bond is present as in (I). However, unlike (I), the conformation about the ethyl group is gauche, so the two arene rings are nearly per­pen­dicular rather than parallel. The packing is significantly different from the other three structures in that there are no inter­molecular hydrogen bonds involving the N—H groups. The mol­ecules are arranged in tetra­gonal columns running along the c axis, with the aniline rings mostly parallel and separated by ca 3.7 Å. Taken together, these structures demonstrate that modest changes in functional groups cause significant differences in mol­ecular conformation, inter­molecular inter­actions and packing.

Computing details

For all compounds, data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: APEX2 (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalMaker (Palmer, 2013); software used to prepare material for publication: APEX2 (Bruker, 2005).

(C14H13N3O4) 2,4-Dinitro-N-(2-phenylethyl)aniline

Crystal data

C14H13N3O4	Z = 2
Mr = 287.27	F(000) = 300
Triclinic, P1	Dx = 1.459 Mg m^−3
Hall symbol: -P 1	Melting point: 425 K
a = 7.235 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.282 (2) Å	Cell parameters from 11611 reflections
c = 13.512 (4) Å	θ = 3.0–32.1°
α = 88.714 (5)°	µ = 0.11 mm^−1
β = 85.131 (5)°	T = 100 K
γ = 67.239 (5)°	Plate, orange
V = 654.0 (4) Å^3	0.20 × 0.10 × 0.02 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer	3158 independent reflections
Radiation source: sealed tube	2288 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω scans	θmax = 28.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.978, Tmax = 0.998	k = −9→9
9039 measured reflections	l = −17→17

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)] = 0.040	Hydrogen site location: difference Fourier map
wR(F^2) = 0.104	All H-atom parameters refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0523P)^2 + 0.1059P] where P = (Fo^2 + 2Fc^2)/3
3158 reflections	(Δ/σ)max < 0.001
242 parameters	Δρmax = 0.29 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
O21	0.47421 (16)	0.19492 (14)	0.46231 (7)	0.0226 (3)
O22	0.30058 (15)	0.48827 (14)	0.40811 (8)	0.0218 (2)
O41	0.35861 (18)	0.39571 (17)	−0.04202 (8)	0.0288 (3)
O42	0.17704 (17)	0.61028 (16)	0.07262 (8)	0.0304 (3)
N1	0.69604 (18)	−0.09321 (17)	0.33654 (9)	0.0162 (3)
H1	0.654 (3)	−0.062 (3)	0.3982 (14)	0.032 (5)*
N2	0.41095 (17)	0.31155 (16)	0.39279 (8)	0.0150 (3)
N4	0.31213 (19)	0.44961 (18)	0.04614 (9)	0.0212 (3)
C1	0.61056 (19)	0.04072 (19)	0.26771 (10)	0.0137 (3)
C2	0.46755 (19)	0.23875 (19)	0.29173 (10)	0.0132 (3)
C3	0.3740 (2)	0.3712 (2)	0.21903 (10)	0.0141 (3)
H3	0.280 (2)	0.497 (2)	0.2391 (11)	0.018 (4)*
C4	0.4213 (2)	0.3149 (2)	0.12088 (10)	0.0166 (3)
C5	0.5681 (2)	0.1266 (2)	0.09314 (11)	0.0179 (3)
H5	0.599 (2)	0.092 (2)	0.0257 (13)	0.021 (4)*
C6	0.6582 (2)	−0.0059 (2)	0.16413 (11)	0.0167 (3)
H6	0.756 (3)	−0.133 (3)	0.1449 (13)	0.027 (4)*
C7	0.8410 (2)	−0.2971 (2)	0.31717 (12)	0.0178 (3)
H7A	0.932 (2)	−0.299 (2)	0.2580 (12)	0.018 (4)*
H7B	0.920 (2)	−0.336 (2)	0.3754 (12)	0.021 (4)*
C8	0.7394 (2)	−0.4436 (2)	0.30299 (12)	0.0169 (3)
H8B	0.641 (2)	−0.429 (2)	0.3592 (12)	0.015 (4)*
H8A	0.662 (2)	−0.411 (2)	0.2453 (12)	0.014 (4)*
C9	0.8931 (2)	−0.65607 (19)	0.29443 (10)	0.0151 (3)
C10	0.9689 (2)	−0.7611 (2)	0.37972 (11)	0.0185 (3)
H10	0.917 (2)	−0.699 (2)	0.4453 (13)	0.025 (4)*
C11	1.1134 (2)	−0.9552 (2)	0.37235 (13)	0.0221 (3)
H11	1.161 (3)	−1.025 (3)	0.4326 (14)	0.034 (5)*
C12	1.1825 (2)	−1.0461 (2)	0.27972 (13)	0.0237 (3)
H12	1.277 (3)	−1.178 (3)	0.2770 (12)	0.026 (4)*
C13	1.1069 (2)	−0.9442 (2)	0.19510 (12)	0.0225 (3)
H13	1.155 (3)	−1.014 (3)	0.1310 (14)	0.031 (5)*
C14	0.9635 (2)	−0.7496 (2)	0.20191 (11)	0.0182 (3)
H14	0.914 (2)	−0.682 (2)	0.1425 (13)	0.025 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O21	0.0317 (6)	0.0159 (5)	0.0157 (5)	−0.0043 (4)	−0.0026 (4)	0.0024 (4)
O22	0.0234 (6)	0.0124 (5)	0.0224 (5)	0.0007 (4)	0.0012 (4)	−0.0048 (4)
O41	0.0441 (7)	0.0303 (6)	0.0144 (5)	−0.0161 (5)	−0.0063 (5)	0.0025 (4)
O42	0.0346 (7)	0.0196 (6)	0.0282 (6)	−0.0002 (5)	−0.0069 (5)	0.0043 (5)
N1	0.0168 (6)	0.0101 (6)	0.0190 (6)	−0.0023 (5)	−0.0014 (5)	−0.0008 (5)
N2	0.0154 (6)	0.0131 (6)	0.0154 (6)	−0.0046 (5)	−0.0004 (5)	−0.0009 (5)
N4	0.0282 (7)	0.0195 (7)	0.0180 (6)	−0.0109 (6)	−0.0052 (5)	0.0036 (5)
C1	0.0113 (6)	0.0122 (6)	0.0191 (7)	−0.0061 (5)	−0.0008 (5)	−0.0012 (5)
C2	0.0140 (7)	0.0112 (6)	0.0143 (7)	−0.0050 (5)	0.0010 (5)	−0.0027 (5)
C3	0.0129 (6)	0.0108 (6)	0.0186 (7)	−0.0047 (5)	0.0002 (5)	−0.0014 (5)
C4	0.0182 (7)	0.0151 (7)	0.0180 (7)	−0.0080 (6)	−0.0021 (6)	0.0020 (5)
C5	0.0217 (7)	0.0183 (7)	0.0155 (7)	−0.0104 (6)	0.0029 (6)	−0.0045 (6)
C6	0.0152 (7)	0.0127 (7)	0.0214 (7)	−0.0049 (6)	0.0028 (6)	−0.0047 (5)
C7	0.0135 (7)	0.0108 (7)	0.0263 (8)	−0.0011 (5)	−0.0042 (6)	−0.0003 (6)
C8	0.0130 (7)	0.0121 (7)	0.0235 (8)	−0.0024 (5)	−0.0018 (6)	−0.0014 (5)
C9	0.0119 (6)	0.0126 (7)	0.0214 (7)	−0.0055 (5)	−0.0002 (5)	−0.0017 (5)
C10	0.0188 (7)	0.0167 (7)	0.0203 (8)	−0.0077 (6)	−0.0003 (6)	0.0010 (6)
C11	0.0190 (8)	0.0156 (7)	0.0326 (9)	−0.0073 (6)	−0.0052 (6)	0.0062 (6)
C12	0.0138 (7)	0.0110 (7)	0.0451 (10)	−0.0040 (6)	0.0009 (6)	−0.0032 (6)
C13	0.0172 (7)	0.0196 (7)	0.0311 (9)	−0.0088 (6)	0.0068 (6)	−0.0120 (6)
C14	0.0177 (7)	0.0188 (7)	0.0200 (7)	−0.0091 (6)	−0.0007 (6)	−0.0021 (6)

Geometric parameters (Å, º)

O21—N2	1.2448 (15)	C7—C8	1.534 (2)
O22—N2	1.2350 (14)	C7—H7A	0.989 (16)
O41—N4	1.2398 (16)	C7—H7B	0.984 (16)
O42—N4	1.2356 (16)	C8—C9	1.5161 (19)
N1—C1	1.3374 (18)	C8—H8B	0.974 (16)
N1—C7	1.4622 (17)	C8—H8A	0.967 (16)
N1—H1	0.867 (19)	C9—C14	1.396 (2)
N2—C2	1.4433 (17)	C9—C10	1.399 (2)
N4—C4	1.4482 (18)	C10—C11	1.395 (2)
C1—C6	1.429 (2)	C10—H10	0.980 (17)
C1—C2	1.4369 (18)	C11—C12	1.389 (2)
C2—C3	1.3850 (19)	C11—H11	0.966 (19)
C3—C4	1.372 (2)	C12—C13	1.382 (2)
C3—H3	0.932 (16)	C12—H12	0.938 (17)
C4—C5	1.406 (2)	C13—C14	1.395 (2)
C5—C6	1.362 (2)	C13—H13	0.979 (18)
C5—H5	0.937 (17)	C14—H14	0.955 (17)
C6—H6	0.948 (17)
C1—N1—C7	125.87 (13)	C8—C7—H7A	110.3 (9)
C1—N1—H1	117.6 (12)	N1—C7—H7B	106.3 (9)
C7—N1—H1	116.2 (12)	C8—C7—H7B	109.5 (9)
O22—N2—O21	121.63 (11)	H7A—C7—H7B	108.7 (13)
O22—N2—C2	119.07 (11)	C9—C8—C7	111.05 (11)
O21—N2—C2	119.30 (11)	C9—C8—H8B	110.6 (9)
O42—N4—O41	123.20 (12)	C7—C8—H8B	108.5 (9)
O42—N4—C4	119.13 (12)	C9—C8—H8A	110.1 (9)
O41—N4—C4	117.66 (12)	C7—C8—H8A	111.3 (9)
N1—C1—C6	121.24 (12)	H8B—C8—H8A	105.1 (12)
N1—C1—C2	123.14 (12)	C14—C9—C10	118.80 (13)
C6—C1—C2	115.62 (12)	C14—C9—C8	120.97 (13)
C3—C2—C1	121.89 (12)	C10—C9—C8	120.23 (13)
C3—C2—N2	115.84 (11)	C11—C10—C9	120.58 (14)
C1—C2—N2	122.28 (12)	C11—C10—H10	119.7 (10)
C4—C3—C2	119.61 (12)	C9—C10—H10	119.7 (10)
C4—C3—H3	122.3 (9)	C12—C11—C10	119.96 (15)
C2—C3—H3	118.1 (9)	C12—C11—H11	121.3 (11)
C3—C4—C5	120.74 (13)	C10—C11—H11	118.7 (11)
C3—C4—N4	118.95 (12)	C13—C12—C11	119.87 (14)
C5—C4—N4	120.27 (12)	C13—C12—H12	121.9 (11)
C6—C5—C4	120.01 (13)	C11—C12—H12	118.2 (11)
C6—C5—H5	120.6 (10)	C12—C13—C14	120.46 (14)
C4—C5—H5	119.3 (10)	C12—C13—H13	118.1 (10)
C5—C6—C1	122.00 (13)	C14—C13—H13	121.4 (10)
C5—C6—H6	119.6 (10)	C13—C14—C9	120.33 (14)
C1—C6—H6	118.4 (10)	C13—C14—H14	119.1 (10)
N1—C7—C8	112.67 (12)	C9—C14—H14	120.6 (10)
N1—C7—H7A	109.2 (9)
C7—N1—C1—C6	−0.9 (2)	C3—C4—C5—C6	3.2 (2)
C7—N1—C1—C2	179.47 (12)	N4—C4—C5—C6	−174.48 (13)
N1—C1—C2—C3	−176.80 (13)	C4—C5—C6—C1	−0.9 (2)
C6—C1—C2—C3	3.52 (19)	N1—C1—C6—C5	177.98 (13)
N1—C1—C2—N2	2.6 (2)	C2—C1—C6—C5	−2.33 (19)
C6—C1—C2—N2	−177.05 (12)	C1—N1—C7—C8	−85.52 (17)
O22—N2—C2—C3	−6.70 (18)	N1—C7—C8—C9	−173.75 (12)
O21—N2—C2—C3	173.22 (12)	C7—C8—C9—C14	−99.44 (16)
O22—N2—C2—C1	173.85 (12)	C7—C8—C9—C10	79.65 (16)
O21—N2—C2—C1	−6.24 (18)	C14—C9—C10—C11	0.4 (2)
C1—C2—C3—C4	−1.4 (2)	C8—C9—C10—C11	−178.69 (13)
N2—C2—C3—C4	179.12 (12)	C9—C10—C11—C12	−0.2 (2)
C2—C3—C4—C5	−2.0 (2)	C10—C11—C12—C13	−0.4 (2)
C2—C3—C4—N4	175.69 (12)	C11—C12—C13—C14	0.9 (2)
O42—N4—C4—C3	−1.2 (2)	C12—C13—C14—C9	−0.7 (2)
O41—N4—C4—C3	179.53 (13)	C10—C9—C14—C13	0.0 (2)
O42—N4—C4—C5	176.52 (13)	C8—C9—C14—C13	179.15 (13)
O41—N4—C4—C5	−2.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O21	0.867 (19)	1.983 (19)	2.6377 (16)	131.5 (16)
N1—H1···O21^i	0.867 (19)	2.381 (19)	3.0823 (18)	138.3 (16)

Symmetry code: (i) −x+1, −y, −z+1.

(C22H22N4O4) 4,6-Dinitro-N,N'-bis(2-phenylethyl)benzene-1,3-diamine

Crystal data

C22H22N4O4	Z = 2
Mr = 406.44	F(000) = 428
Triclinic, P1	Dx = 1.378 Mg m^−3
Hall symbol: -P 1	Melting point: 408 K
a = 8.1121 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1819 (8) Å	Cell parameters from 17364 reflections
c = 13.1018 (11) Å	θ = 2.5–32.7°
α = 93.466 (1)°	µ = 0.10 mm^−1
β = 106.595 (1)°	T = 100 K
γ = 106.932 (1)°	Parallelpiped, orange
V = 979.88 (14) Å^3	0.20 × 0.10 × 0.05 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer	6868 independent reflections
Radiation source: sealed tube	5289 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
ω scans	θmax = 33.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.981, Tmax = 0.995	k = −15→15
17364 measured reflections	l = −19→19

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)] = 0.043	Hydrogen site location: difference Fourier map
wR(F^2) = 0.121	All H-atom parameters refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0693P)^2 + 0.148P] where P = (Fo^2 + 2Fc^2)/3
6868 reflections	(Δ/σ)max = 0.001
359 parameters	Δρmax = 0.57 e Å^−3
0 restraints	Δρmin = −0.21 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
O21	0.23044 (11)	0.49365 (8)	−0.03714 (6)	0.02254 (17)
O22	0.20579 (10)	0.44974 (8)	0.11874 (6)	0.02074 (16)
O41	0.80203 (11)	0.91022 (8)	0.45448 (6)	0.02101 (16)
O42	0.57135 (10)	0.72779 (8)	0.43962 (6)	0.02098 (16)
N1	0.51043 (11)	0.69381 (9)	−0.05088 (6)	0.01446 (15)
H1	0.410 (2)	0.6227 (15)	−0.0847 (12)	0.029 (4)*
N2	0.28480 (11)	0.52119 (8)	0.06328 (7)	0.01512 (16)
N4	0.67006 (11)	0.80913 (9)	0.39872 (6)	0.01476 (16)
N5	0.86876 (11)	1.00007 (8)	0.28122 (7)	0.01354 (15)
H5	0.905 (2)	1.0156 (17)	0.3538 (14)	0.039 (4)*
C1	0.54668 (12)	0.72552 (9)	0.05682 (7)	0.01225 (16)
C2	0.44289 (12)	0.63957 (9)	0.11528 (7)	0.01285 (16)
C3	0.48939 (12)	0.67177 (9)	0.22604 (7)	0.01303 (16)
H3	0.4177 (19)	0.6132 (15)	0.2631 (11)	0.026 (4)*
C4	0.63377 (12)	0.78684 (9)	0.28394 (7)	0.01247 (16)
C5	0.73706 (12)	0.88063 (9)	0.22938 (7)	0.01228 (16)
C6	0.69047 (12)	0.84309 (9)	0.11745 (7)	0.01281 (16)
H6	0.7613 (18)	0.9005 (14)	0.0809 (11)	0.020 (3)*
C7	0.60110 (13)	0.78288 (10)	−0.11463 (8)	0.01417 (17)
H7A	0.5825 (17)	0.7264 (13)	−0.1818 (10)	0.015 (3)*
H7B	0.7300 (18)	0.8193 (13)	−0.0770 (10)	0.017 (3)*
C8	0.52363 (14)	0.90188 (11)	−0.14096 (8)	0.01701 (18)
H8B	0.5228 (19)	0.9459 (15)	−0.0728 (12)	0.025 (4)*
H8A	0.396 (2)	0.8610 (15)	−0.1902 (12)	0.027 (4)*
C9	0.63215 (12)	1.00500 (10)	−0.19438 (7)	0.01360 (17)
C10	0.59759 (13)	0.98259 (10)	−0.30591 (8)	0.01541 (17)
H10	0.501 (2)	0.9015 (16)	−0.3492 (12)	0.029 (4)*
C11	0.70127 (14)	1.07599 (11)	−0.35487 (8)	0.01895 (19)
H11	0.677 (2)	1.0608 (16)	−0.4351 (13)	0.032 (4)*
C12	0.84093 (14)	1.19286 (11)	−0.29268 (9)	0.0209 (2)
H12	0.915 (2)	1.2594 (18)	−0.3244 (14)	0.042 (4)*
C13	0.87739 (14)	1.21631 (11)	−0.18180 (9)	0.0208 (2)
H13	0.974 (2)	1.2986 (18)	−0.1407 (14)	0.039 (4)*
C14	0.77321 (14)	1.12241 (10)	−0.13291 (8)	0.01714 (18)
H14	0.796 (2)	1.1411 (16)	−0.0549 (13)	0.031 (4)*
C15	0.97367 (13)	1.09930 (10)	0.22897 (8)	0.01359 (16)
H15A	1.0524 (17)	1.0589 (13)	0.2021 (10)	0.013 (3)*
H15B	0.8901 (18)	1.1204 (14)	0.1646 (11)	0.019 (3)*
C16	1.08512 (12)	1.23457 (10)	0.30761 (8)	0.01436 (17)
H16B	1.1659 (18)	1.2924 (14)	0.2730 (11)	0.021 (3)*
H16A	1.1643 (18)	1.2117 (14)	0.3725 (11)	0.022 (3)*
C17	0.96790 (12)	1.31233 (9)	0.33662 (7)	0.01351 (17)
C18	0.90244 (13)	1.28766 (10)	0.42395 (8)	0.01619 (18)
H18	0.9416 (18)	1.2227 (14)	0.4720 (11)	0.021 (3)*
C19	0.78662 (14)	1.35502 (11)	0.44617 (8)	0.01860 (19)
H19	0.7421 (18)	1.3349 (14)	0.5078 (11)	0.022 (3)*
C20	0.73618 (14)	1.44989 (11)	0.38173 (9)	0.01931 (19)
H20	0.658 (2)	1.4978 (15)	0.4001 (12)	0.028 (4)*
C21	0.80260 (14)	1.47698 (10)	0.29578 (8)	0.01828 (19)
H21	0.7735 (19)	1.5465 (15)	0.2518 (12)	0.024 (3)*
C22	0.91731 (13)	1.40873 (10)	0.27311 (8)	0.01578 (18)
H22	0.9588 (18)	1.4296 (14)	0.2116 (11)	0.019 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O21	0.0230 (4)	0.0213 (4)	0.0153 (3)	−0.0007 (3)	0.0019 (3)	0.0029 (3)
O22	0.0209 (4)	0.0182 (3)	0.0231 (4)	0.0014 (3)	0.0112 (3)	0.0063 (3)
O41	0.0254 (4)	0.0195 (3)	0.0137 (3)	0.0027 (3)	0.0045 (3)	0.0013 (3)
O42	0.0231 (4)	0.0255 (4)	0.0163 (3)	0.0058 (3)	0.0102 (3)	0.0083 (3)
N1	0.0166 (4)	0.0142 (3)	0.0116 (3)	0.0029 (3)	0.0051 (3)	0.0021 (3)
N2	0.0149 (4)	0.0137 (3)	0.0168 (4)	0.0042 (3)	0.0053 (3)	0.0036 (3)
N4	0.0178 (4)	0.0165 (4)	0.0129 (3)	0.0083 (3)	0.0062 (3)	0.0043 (3)
N5	0.0148 (4)	0.0133 (3)	0.0123 (3)	0.0037 (3)	0.0048 (3)	0.0025 (3)
C1	0.0134 (4)	0.0130 (4)	0.0128 (4)	0.0063 (3)	0.0053 (3)	0.0037 (3)
C2	0.0125 (4)	0.0123 (4)	0.0138 (4)	0.0038 (3)	0.0042 (3)	0.0030 (3)
C3	0.0139 (4)	0.0136 (4)	0.0147 (4)	0.0066 (3)	0.0064 (3)	0.0047 (3)
C4	0.0150 (4)	0.0141 (4)	0.0107 (4)	0.0067 (3)	0.0054 (3)	0.0035 (3)
C5	0.0127 (4)	0.0126 (4)	0.0136 (4)	0.0064 (3)	0.0047 (3)	0.0032 (3)
C6	0.0139 (4)	0.0137 (4)	0.0127 (4)	0.0049 (3)	0.0064 (3)	0.0032 (3)
C7	0.0157 (4)	0.0159 (4)	0.0130 (4)	0.0061 (3)	0.0065 (3)	0.0037 (3)
C8	0.0165 (4)	0.0198 (4)	0.0201 (4)	0.0090 (4)	0.0097 (4)	0.0083 (4)
C9	0.0130 (4)	0.0148 (4)	0.0160 (4)	0.0070 (3)	0.0060 (3)	0.0043 (3)
C10	0.0148 (4)	0.0148 (4)	0.0155 (4)	0.0041 (3)	0.0038 (3)	0.0021 (3)
C11	0.0209 (5)	0.0220 (5)	0.0179 (4)	0.0090 (4)	0.0093 (4)	0.0066 (4)
C12	0.0181 (4)	0.0186 (4)	0.0304 (5)	0.0069 (4)	0.0121 (4)	0.0101 (4)
C13	0.0149 (4)	0.0137 (4)	0.0306 (5)	0.0034 (3)	0.0043 (4)	0.0010 (4)
C14	0.0174 (4)	0.0180 (4)	0.0156 (4)	0.0080 (4)	0.0028 (3)	0.0007 (3)
C15	0.0138 (4)	0.0142 (4)	0.0147 (4)	0.0052 (3)	0.0064 (3)	0.0038 (3)
C16	0.0123 (4)	0.0152 (4)	0.0151 (4)	0.0039 (3)	0.0041 (3)	0.0029 (3)
C17	0.0126 (4)	0.0125 (4)	0.0134 (4)	0.0027 (3)	0.0026 (3)	0.0008 (3)
C18	0.0176 (4)	0.0150 (4)	0.0154 (4)	0.0041 (3)	0.0054 (3)	0.0030 (3)
C19	0.0195 (4)	0.0186 (4)	0.0178 (4)	0.0045 (4)	0.0081 (4)	0.0013 (3)
C20	0.0177 (4)	0.0177 (4)	0.0221 (5)	0.0066 (4)	0.0057 (4)	−0.0016 (4)
C21	0.0192 (4)	0.0155 (4)	0.0191 (4)	0.0067 (4)	0.0035 (4)	0.0021 (3)
C22	0.0170 (4)	0.0154 (4)	0.0145 (4)	0.0049 (3)	0.0045 (3)	0.0030 (3)

Geometric parameters (Å, º)

O21—N2	1.2475 (11)	C9—C10	1.3980 (13)
O22—N2	1.2354 (10)	C10—C11	1.3925 (13)
O41—N4	1.2489 (11)	C10—H10	0.966 (15)
O42—N4	1.2356 (10)	C11—C12	1.3905 (15)
N1—C1	1.3544 (12)	C11—H11	1.006 (16)
N1—C7	1.4543 (12)	C12—C13	1.3880 (16)
N1—H1	0.891 (15)	C12—H12	0.965 (17)
N2—C2	1.4363 (12)	C13—C14	1.3968 (15)
N4—C4	1.4376 (12)	C13—H13	0.963 (17)
N5—C5	1.3456 (12)	C14—H14	0.980 (16)
N5—C15	1.4592 (12)	C15—C16	1.5320 (13)
N5—H5	0.900 (17)	C15—H15A	0.983 (13)
C1—C6	1.4025 (13)	C15—H15B	0.999 (13)
C1—C2	1.4428 (12)	C16—C17	1.5113 (13)
C2—C3	1.3832 (13)	C16—H16B	0.979 (14)
C3—C4	1.3805 (13)	C16—H16A	0.994 (14)
C3—H3	0.961 (14)	C17—C18	1.3995 (13)
C4—C5	1.4434 (12)	C17—C22	1.4009 (13)
C5—C6	1.4039 (13)	C18—C19	1.3948 (14)
C6—H6	0.947 (14)	C18—H18	0.996 (14)
C7—C8	1.5337 (14)	C19—C20	1.3945 (15)
C7—H7A	0.969 (13)	C19—H19	0.983 (14)
C7—H7B	0.965 (13)	C20—C21	1.3900 (15)
C8—C9	1.5065 (13)	C20—H20	0.974 (15)
C8—H8B	0.977 (14)	C21—C22	1.3952 (14)
C8—H8A	1.000 (15)	C21—H21	0.978 (14)
C9—C14	1.3956 (13)	C22—H22	0.971 (13)
C1—N1—C7	124.07 (8)	C11—C10—C9	120.67 (9)
C1—N1—H1	115.8 (10)	C11—C10—H10	119.9 (9)
C7—N1—H1	119.0 (10)	C9—C10—H10	119.4 (9)
O22—N2—O21	121.71 (8)	C12—C11—C10	119.99 (9)
O22—N2—C2	119.42 (8)	C12—C11—H11	118.8 (9)
O21—N2—C2	118.88 (8)	C10—C11—H11	121.2 (9)
O42—N4—O41	121.81 (8)	C13—C12—C11	120.05 (9)
O42—N4—C4	119.44 (8)	C13—C12—H12	118.1 (10)
O41—N4—C4	118.75 (8)	C11—C12—H12	121.8 (10)
C5—N5—C15	124.42 (8)	C12—C13—C14	119.84 (9)
C5—N5—H5	118.4 (10)	C12—C13—H13	118.5 (10)
C15—N5—H5	116.8 (10)	C14—C13—H13	121.7 (10)
N1—C1—C6	121.20 (8)	C9—C14—C13	120.72 (9)
N1—C1—C2	122.14 (8)	C9—C14—H14	119.6 (9)
C6—C1—C2	116.66 (8)	C13—C14—H14	119.6 (9)
C3—C2—N2	116.57 (8)	N5—C15—C16	110.11 (8)
C3—C2—C1	120.46 (8)	N5—C15—H15A	110.3 (7)
N2—C2—C1	122.94 (8)	C16—C15—H15A	111.1 (7)
C4—C3—C2	121.62 (8)	N5—C15—H15B	109.9 (8)
C4—C3—H3	119.5 (8)	C16—C15—H15B	108.9 (8)
C2—C3—H3	118.9 (9)	H15A—C15—H15B	106.3 (11)
C3—C4—N4	116.64 (8)	C17—C16—C15	112.77 (8)
C3—C4—C5	120.48 (8)	C17—C16—H16B	109.9 (8)
N4—C4—C5	122.85 (8)	C15—C16—H16B	107.2 (8)
N5—C5—C6	120.81 (8)	C17—C16—H16A	111.8 (8)
N5—C5—C4	122.58 (8)	C15—C16—H16A	108.2 (8)
C6—C5—C4	116.58 (8)	H16B—C16—H16A	106.7 (11)
C1—C6—C5	124.07 (8)	C18—C17—C22	118.37 (9)
C1—C6—H6	118.1 (8)	C18—C17—C16	121.76 (8)
C5—C6—H6	117.8 (8)	C22—C17—C16	119.84 (8)
N1—C7—C8	111.96 (8)	C19—C18—C17	121.00 (9)
N1—C7—H7A	107.9 (7)	C19—C18—H18	119.6 (8)
C8—C7—H7A	108.4 (8)	C17—C18—H18	119.4 (8)
N1—C7—H7B	109.8 (8)	C20—C19—C18	120.00 (9)
C8—C7—H7B	110.4 (8)	C20—C19—H19	121.0 (8)
H7A—C7—H7B	108.2 (11)	C18—C19—H19	119.0 (8)
C9—C8—C7	112.29 (8)	C21—C20—C19	119.56 (9)
C9—C8—H8B	111.3 (8)	C21—C20—H20	121.8 (9)
C7—C8—H8B	106.6 (8)	C19—C20—H20	118.6 (9)
C9—C8—H8A	109.2 (8)	C20—C21—C22	120.38 (9)
C7—C8—H8A	108.3 (8)	C20—C21—H21	120.7 (8)
H8B—C8—H8A	109.0 (12)	C22—C21—H21	118.8 (8)
C14—C9—C10	118.74 (9)	C21—C22—C17	120.68 (9)
C14—C9—C8	120.54 (9)	C21—C22—H22	117.6 (8)
C10—C9—C8	120.69 (9)	C17—C22—H22	121.7 (8)
C7—N1—C1—C6	−6.57 (14)	N5—C5—C6—C1	−175.36 (8)
C7—N1—C1—C2	174.69 (8)	C4—C5—C6—C1	3.10 (13)
O22—N2—C2—C3	−4.46 (12)	C1—N1—C7—C8	−79.33 (11)
O21—N2—C2—C3	175.24 (8)	N1—C7—C8—C9	172.60 (8)
O22—N2—C2—C1	177.78 (8)	C7—C8—C9—C14	−92.60 (11)
O21—N2—C2—C1	−2.53 (13)	C7—C8—C9—C10	85.24 (11)
N1—C1—C2—C3	176.93 (8)	C14—C9—C10—C11	−0.33 (14)
C6—C1—C2—C3	−1.86 (13)	C8—C9—C10—C11	−178.21 (9)
N1—C1—C2—N2	−5.39 (14)	C9—C10—C11—C12	0.07 (15)
C6—C1—C2—N2	175.82 (8)	C10—C11—C12—C13	0.16 (15)
N2—C2—C3—C4	−177.06 (8)	C11—C12—C13—C14	−0.14 (15)
C1—C2—C3—C4	0.76 (14)	C10—C9—C14—C13	0.36 (14)
C2—C3—C4—N4	−179.52 (8)	C8—C9—C14—C13	178.24 (9)
C2—C3—C4—C5	2.36 (13)	C12—C13—C14—C9	−0.13 (15)
O42—N4—C4—C3	−1.13 (12)	C5—N5—C15—C16	169.34 (8)
O41—N4—C4—C3	178.37 (8)	N5—C15—C16—C17	−66.94 (10)
O42—N4—C4—C5	176.93 (8)	C15—C16—C17—C18	89.20 (11)
O41—N4—C4—C5	−3.57 (13)	C15—C16—C17—C22	−88.67 (10)
C15—N5—C5—C6	−0.22 (13)	C22—C17—C18—C19	1.31 (14)
C15—N5—C5—C4	−178.58 (8)	C16—C17—C18—C19	−176.60 (9)
C3—C4—C5—N5	174.25 (8)	C17—C18—C19—C20	−0.80 (15)
N4—C4—C5—N5	−3.74 (13)	C18—C19—C20—C21	−0.24 (15)
C3—C4—C5—C6	−4.17 (13)	C19—C20—C21—C22	0.74 (15)
N4—C4—C5—C6	177.83 (8)	C20—C21—C22—C17	−0.22 (15)
N1—C1—C6—C5	−178.97 (8)	C18—C17—C22—C21	−0.80 (14)
C2—C1—C6—C5	−0.17 (13)	C16—C17—C22—C21	177.15 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O21	0.891 (15)	1.935 (15)	2.6318 (11)	133.8 (13)
N5—H5···O41	0.900 (17)	1.967 (16)	2.6358 (11)	129.8 (14)
N5—H5···O41^i	0.900 (17)	2.800 (17)	3.5877 (11)	146.8 (13)

Symmetry code: (i) −x+2, −y+2, −z+1.

(C15H13N3O2) 2-cyano-4-nitro-N-(2-phenylethyl)aniline

Crystal data

C15H13N3O2	F(000) = 560
Mr = 267.28	Dx = 1.348 Mg m^−3
Monoclinic, P21/n	Melting point: 427 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.4871 (5) Å	Cell parameters from 23429 reflections
b = 16.270 (1) Å	θ = 2.3–33.0°
c = 10.8432 (7) Å	µ = 0.09 mm^−1
β = 94.384 (1)°	T = 100 K
V = 1317.00 (15) Å^3	Parallelpiped, yellow
Z = 4	0.40 × 0.20 × 0.10 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer	4732 independent reflections
Radiation source: sealed tube	4189 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
ω scans	θmax = 32.9°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.964, Tmax = 0.991	k = −24→24
23007 measured reflections	l = −16→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)] = 0.038	Hydrogen site location: difference Fourier map
wR(F^2) = 0.113	All H-atom parameters refined
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0687P)^2 + 0.3103P] where P = (Fo^2 + 2Fc^2)/3
4732 reflections	(Δ/σ)max = 0.001
233 parameters	Δρmax = 0.56 e Å^−3
0 restraints	Δρmin = −0.20 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
O41	0.28684 (9)	0.12353 (4)	0.29556 (6)	0.02323 (14)
O42	0.10504 (8)	0.03747 (4)	0.37421 (6)	0.02067 (13)
N1	0.65662 (8)	0.09507 (4)	0.83376 (6)	0.01439 (12)
H1	0.6214 (19)	0.0666 (9)	0.8948 (14)	0.033 (3)*
N2	0.33192 (10)	−0.05113 (4)	0.89432 (7)	0.02022 (14)
N4	0.23997 (8)	0.08139 (4)	0.38232 (6)	0.01466 (13)
C1	0.55906 (9)	0.09106 (4)	0.72443 (6)	0.01199 (13)
C2	0.40849 (9)	0.03712 (4)	0.70702 (6)	0.01168 (13)
C3	0.30296 (9)	0.03411 (4)	0.59568 (7)	0.01221 (13)
H3	0.2029 (15)	−0.0007 (7)	0.5865 (11)	0.019 (3)*
C4	0.34763 (9)	0.08426 (4)	0.49902 (6)	0.01264 (13)
C5	0.49621 (10)	0.13679 (5)	0.51165 (7)	0.01499 (14)
H5	0.5272 (16)	0.1712 (8)	0.4445 (11)	0.021 (3)*
C6	0.59954 (10)	0.13990 (5)	0.62209 (7)	0.01514 (14)
H6	0.6992 (17)	0.1754 (8)	0.6296 (12)	0.024 (3)*
C7	0.80953 (9)	0.14949 (5)	0.86030 (7)	0.01465 (14)
H7A	0.7833 (16)	0.2054 (7)	0.8259 (11)	0.020 (3)*
H7B	0.8227 (16)	0.1545 (8)	0.9503 (12)	0.022 (3)*
C8	0.98355 (10)	0.11550 (5)	0.81298 (8)	0.01875 (15)
H8B	0.9959 (18)	0.0584 (8)	0.8430 (13)	0.029 (3)*
H8A	0.9744 (18)	0.1137 (8)	0.7233 (13)	0.030 (3)*
C9	1.14367 (9)	0.16670 (5)	0.85827 (7)	0.01476 (14)
C10	1.22232 (10)	0.15533 (5)	0.97834 (7)	0.01569 (14)
H10	1.1749 (18)	0.1134 (8)	1.0314 (13)	0.027 (3)*
C11	1.36857 (10)	0.20255 (5)	1.02246 (7)	0.01573 (14)
H11	1.4201 (18)	0.1936 (8)	1.1055 (12)	0.026 (3)*
C12	1.43693 (10)	0.26274 (5)	0.94762 (7)	0.01653 (14)
H12	1.5371 (18)	0.2976 (8)	0.9811 (13)	0.030 (3)*
C13	1.36012 (10)	0.27489 (5)	0.82797 (7)	0.01769 (15)
H13	1.4088 (18)	0.3160 (8)	0.7747 (13)	0.028 (3)*
C14	1.21486 (10)	0.22666 (5)	0.78384 (7)	0.01678 (14)
H14	1.1657 (16)	0.2334 (8)	0.6966 (12)	0.024 (3)*
C15	0.36369 (9)	−0.01308 (4)	0.80896 (7)	0.01396 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O41	0.0262 (3)	0.0287 (3)	0.0145 (3)	−0.0025 (2)	−0.0005 (2)	0.0067 (2)
O42	0.0176 (3)	0.0243 (3)	0.0194 (3)	−0.0046 (2)	−0.0032 (2)	−0.0013 (2)
N1	0.0130 (3)	0.0174 (3)	0.0126 (3)	−0.0041 (2)	−0.0002 (2)	0.0009 (2)
N2	0.0213 (3)	0.0208 (3)	0.0186 (3)	−0.0022 (2)	0.0014 (2)	0.0046 (2)
N4	0.0147 (3)	0.0157 (3)	0.0134 (3)	0.0021 (2)	0.0001 (2)	−0.0006 (2)
C1	0.0101 (3)	0.0129 (3)	0.0131 (3)	−0.0004 (2)	0.0014 (2)	0.0003 (2)
C2	0.0109 (3)	0.0117 (3)	0.0126 (3)	−0.0003 (2)	0.0017 (2)	0.0009 (2)
C3	0.0109 (3)	0.0123 (3)	0.0135 (3)	0.0000 (2)	0.0014 (2)	−0.0001 (2)
C4	0.0119 (3)	0.0141 (3)	0.0118 (3)	0.0008 (2)	0.0001 (2)	0.0006 (2)
C5	0.0142 (3)	0.0161 (3)	0.0148 (3)	−0.0016 (2)	0.0018 (2)	0.0030 (2)
C6	0.0131 (3)	0.0172 (3)	0.0152 (3)	−0.0040 (2)	0.0012 (2)	0.0026 (2)
C7	0.0120 (3)	0.0162 (3)	0.0157 (3)	−0.0023 (2)	0.0002 (2)	−0.0024 (2)
C8	0.0123 (3)	0.0198 (3)	0.0238 (4)	−0.0008 (2)	−0.0008 (3)	−0.0089 (3)
C9	0.0105 (3)	0.0159 (3)	0.0178 (3)	0.0012 (2)	0.0001 (2)	−0.0052 (2)
C10	0.0148 (3)	0.0147 (3)	0.0175 (3)	−0.0009 (2)	0.0006 (2)	−0.0014 (2)
C11	0.0140 (3)	0.0173 (3)	0.0155 (3)	0.0000 (2)	−0.0012 (2)	−0.0019 (2)
C12	0.0128 (3)	0.0176 (3)	0.0189 (3)	−0.0020 (2)	−0.0001 (2)	−0.0022 (3)
C13	0.0161 (3)	0.0190 (3)	0.0181 (3)	−0.0004 (2)	0.0022 (3)	0.0010 (3)
C14	0.0142 (3)	0.0208 (3)	0.0151 (3)	0.0027 (2)	−0.0006 (2)	−0.0022 (3)
C15	0.0126 (3)	0.0137 (3)	0.0154 (3)	−0.0012 (2)	0.0003 (2)	0.0001 (2)

Geometric parameters (Å, º)

O41—N4	1.2364 (9)	C7—C8	1.5391 (11)
O42—N4	1.2351 (9)	C7—H7A	0.997 (12)
N1—C1	1.3456 (9)	C7—H7B	0.976 (13)
N1—C7	1.4585 (9)	C8—C9	1.5107 (10)
N1—H1	0.866 (15)	C8—H8B	0.986 (14)
N2—C15	1.1534 (10)	C8—H8A	0.970 (14)
N4—C4	1.4481 (9)	C9—C14	1.3975 (11)
C1—C6	1.4163 (10)	C9—C10	1.3995 (11)
C1—C2	1.4298 (9)	C10—C11	1.3921 (10)
C2—C3	1.3923 (10)	C10—H10	0.977 (13)
C2—C15	1.4346 (10)	C11—C12	1.3938 (11)
C3—C4	1.3892 (10)	C11—H11	0.963 (13)
C3—H3	0.938 (12)	C12—C13	1.3925 (11)
C4—C5	1.4013 (10)	C12—H12	0.987 (14)
C5—C6	1.3761 (10)	C13—C14	1.3957 (11)
C5—H5	0.961 (12)	C13—H13	0.972 (14)
C6—H6	0.942 (13)	C14—H14	0.994 (13)
C1—N1—C7	124.63 (6)	C8—C7—H7B	109.9 (7)
C1—N1—H1	118.1 (10)	H7A—C7—H7B	107.4 (10)
C7—N1—H1	117.0 (10)	C9—C8—C7	111.37 (6)
O42—N4—O41	123.01 (7)	C9—C8—H8B	111.1 (8)
O42—N4—C4	118.59 (6)	C7—C8—H8B	106.8 (8)
O41—N4—C4	118.40 (6)	C9—C8—H8A	109.7 (8)
N1—C1—C6	121.93 (6)	C7—C8—H8A	110.4 (8)
N1—C1—C2	121.03 (6)	H8B—C8—H8A	107.4 (11)
C6—C1—C2	117.04 (6)	C14—C9—C10	118.53 (7)
C3—C2—C1	121.71 (6)	C14—C9—C8	121.69 (7)
C3—C2—C15	119.83 (6)	C10—C9—C8	119.77 (7)
C1—C2—C15	118.43 (6)	C11—C10—C9	120.71 (7)
C4—C3—C2	118.70 (6)	C11—C10—H10	119.6 (8)
C4—C3—H3	120.7 (7)	C9—C10—H10	119.6 (8)
C2—C3—H3	120.6 (7)	C10—C11—C12	120.12 (7)
C3—C4—C5	121.31 (7)	C10—C11—H11	119.1 (8)
C3—C4—N4	119.36 (6)	C12—C11—H11	120.8 (8)
C5—C4—N4	119.32 (6)	C13—C12—C11	119.89 (7)
C6—C5—C4	119.78 (7)	C13—C12—H12	120.6 (8)
C6—C5—H5	119.1 (7)	C11—C12—H12	119.5 (8)
C4—C5—H5	121.1 (7)	C12—C13—C14	119.67 (7)
C5—C6—C1	121.44 (7)	C12—C13—H13	120.3 (8)
C5—C6—H6	119.1 (8)	C14—C13—H13	120.0 (8)
C1—C6—H6	119.5 (8)	C13—C14—C9	121.07 (7)
N1—C7—C8	112.82 (6)	C13—C14—H14	119.1 (7)
N1—C7—H7A	110.5 (7)	C9—C14—H14	119.8 (7)
C8—C7—H7A	110.5 (7)	N2—C15—C2	177.02 (8)
N1—C7—H7B	105.4 (7)
C7—N1—C1—C6	1.06 (11)	C4—C5—C6—C1	−0.14 (11)
C7—N1—C1—C2	−178.63 (6)	N1—C1—C6—C5	−178.37 (7)
N1—C1—C2—C3	178.00 (7)	C2—C1—C6—C5	1.33 (11)
C6—C1—C2—C3	−1.70 (10)	C1—N1—C7—C8	−81.27 (9)
N1—C1—C2—C15	−0.18 (10)	N1—C7—C8—C9	−171.53 (6)
C6—C1—C2—C15	−179.88 (6)	C7—C8—C9—C14	−98.73 (8)
C1—C2—C3—C4	0.87 (10)	C7—C8—C9—C10	80.25 (9)
C15—C2—C3—C4	179.03 (6)	C14—C9—C10—C11	−0.20 (11)
C2—C3—C4—C5	0.39 (11)	C8—C9—C10—C11	−179.21 (7)
C2—C3—C4—N4	179.54 (6)	C9—C10—C11—C12	0.90 (11)
O42—N4—C4—C3	3.91 (10)	C10—C11—C12—C13	−0.82 (11)
O41—N4—C4—C3	−176.58 (7)	C11—C12—C13—C14	0.06 (12)
O42—N4—C4—C5	−176.93 (7)	C12—C13—C14—C9	0.65 (12)
O41—N4—C4—C5	2.58 (10)	C10—C9—C14—C13	−0.58 (11)
C3—C4—C5—C6	−0.76 (11)	C8—C9—C14—C13	178.41 (7)
N4—C4—C5—C6	−179.91 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2^i	0.866 (15)	2.300 (15)	3.0287 (10)	141.9 (12)

Symmetry code: (i) −x+1, −y, −z+2.

(C15H16N2O4S) 4-(methylsulfonyl)-2-nitro-N-(2-phenylethyl)aniline

Crystal data

C15H16N2O4S	Dx = 1.412 Mg m^−3
Mr = 320.36	Melting point: 414 K
Tetragonal, I41/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -I 4ad	Cell parameters from 53474 reflections
a = 20.4639 (13) Å	θ = 2.6–32.9°
c = 14.3952 (14) Å	µ = 0.24 mm^−1
V = 6028.3 (10) Å^3	T = 100 K
Z = 16	Cuboid, yellow
F(000) = 2688	0.40 × 0.20 × 0.20 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer	5524 independent reflections
Radiation source: sealed tube	5155 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
ω scans	θmax = 32.9°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −30→31
Tmin = 0.912, Tmax = 0.955	k = −31→30
52424 measured reflections	l = −21→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)] = 0.029	Hydrogen site location: difference Fourier map
wR(F^2) = 0.086	All H-atom parameters refined
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0494P)^2 + 3.0117P] where P = (Fo^2 + 2Fc^2)/3
5524 reflections	(Δ/σ)max = 0.002
263 parameters	Δρmax = 0.51 e Å^−3
0 restraints	Δρmin = −0.31 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	0.918999 (8)	0.384073 (8)	0.115221 (13)	0.01486 (5)
O21	0.72956 (3)	0.62358 (3)	0.13034 (5)	0.02619 (14)
O22	0.83430 (3)	0.61924 (3)	0.15113 (5)	0.02251 (12)
O41	0.91451 (3)	0.33599 (3)	0.04188 (4)	0.02179 (12)
O42	0.96848 (3)	0.43425 (3)	0.10731 (5)	0.02180 (12)
N1	0.66040 (3)	0.51537 (3)	0.11584 (5)	0.01679 (12)
H1	0.6604 (7)	0.5584 (8)	0.1202 (10)	0.038 (4)*
N2	0.78132 (3)	0.59202 (3)	0.13760 (5)	0.01652 (11)
C1	0.71927 (3)	0.48639 (3)	0.12182 (5)	0.01391 (12)
C2	0.77942 (3)	0.52165 (3)	0.13051 (5)	0.01370 (12)
C3	0.84001 (3)	0.49002 (3)	0.13130 (5)	0.01447 (12)
H3	0.8791 (7)	0.5168 (6)	0.1359 (9)	0.026 (3)*
C4	0.84249 (3)	0.42282 (3)	0.12432 (5)	0.01465 (12)
C5	0.78421 (4)	0.38584 (4)	0.11955 (5)	0.01666 (13)
H5	0.7859 (6)	0.3384 (6)	0.1168 (8)	0.023 (3)*
C6	0.72458 (4)	0.41678 (4)	0.11892 (5)	0.01637 (13)
H6	0.6879 (6)	0.3928 (6)	0.1145 (9)	0.023 (3)*
C7	0.59791 (4)	0.48089 (4)	0.11108 (5)	0.01798 (13)
H7A	0.5906 (5)	0.4561 (5)	0.1693 (8)	0.015 (2)*
H7B	0.5982 (6)	0.4507 (6)	0.0597 (8)	0.018 (3)*
C8	0.54312 (4)	0.53117 (4)	0.09737 (5)	0.01863 (13)
H8A	0.5029 (6)	0.5080 (6)	0.0915 (9)	0.021 (3)*
H8B	0.5525 (6)	0.5542 (6)	0.0391 (9)	0.025 (3)*
C9	0.53881 (3)	0.57928 (4)	0.17680 (5)	0.01547 (12)
C10	0.56452 (4)	0.64241 (4)	0.17008 (5)	0.01871 (13)
H10	0.5853 (6)	0.6565 (7)	0.1136 (9)	0.026 (3)*
C11	0.56197 (4)	0.68488 (4)	0.24613 (6)	0.02200 (15)
H11	0.5775 (6)	0.7276 (7)	0.2407 (10)	0.029 (3)*
C12	0.53446 (4)	0.66439 (4)	0.32954 (6)	0.02297 (15)
H12	0.5339 (7)	0.6937 (7)	0.3812 (10)	0.034 (4)*
C13	0.50872 (4)	0.60148 (4)	0.33686 (5)	0.02155 (14)
H13	0.4898 (7)	0.5856 (7)	0.3950 (10)	0.031 (3)*
C14	0.51036 (4)	0.55957 (4)	0.26071 (5)	0.01777 (13)
H14	0.4927 (6)	0.5155 (6)	0.2656 (9)	0.022 (3)*
C15	0.92951 (4)	0.34181 (4)	0.22080 (6)	0.02208 (14)
H15A	0.9299 (6)	0.3726 (7)	0.2701 (10)	0.031 (3)*
H15B	0.8929 (7)	0.3095 (7)	0.2271 (10)	0.034 (3)*
H15C	0.9713 (7)	0.3212 (7)	0.2172 (10)	0.037 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01361 (8)	0.01350 (8)	0.01747 (9)	0.00014 (5)	0.00355 (5)	−0.00138 (5)
O21	0.0209 (3)	0.0141 (2)	0.0435 (4)	0.0033 (2)	−0.0035 (2)	−0.0016 (2)
O22	0.0192 (3)	0.0156 (2)	0.0328 (3)	−0.00497 (19)	0.0030 (2)	−0.0024 (2)
O41	0.0247 (3)	0.0191 (2)	0.0216 (3)	0.0014 (2)	0.0052 (2)	−0.0065 (2)
O42	0.0150 (2)	0.0172 (2)	0.0332 (3)	−0.00241 (19)	0.0043 (2)	−0.0003 (2)
N1	0.0135 (3)	0.0149 (3)	0.0220 (3)	0.0003 (2)	−0.0005 (2)	−0.0027 (2)
N2	0.0184 (3)	0.0123 (2)	0.0188 (3)	−0.0008 (2)	0.0017 (2)	−0.0005 (2)
C1	0.0138 (3)	0.0140 (3)	0.0140 (3)	−0.0006 (2)	0.0006 (2)	−0.0017 (2)
C2	0.0149 (3)	0.0105 (3)	0.0156 (3)	−0.0010 (2)	0.0010 (2)	−0.0012 (2)
C3	0.0142 (3)	0.0135 (3)	0.0157 (3)	−0.0011 (2)	0.0011 (2)	−0.0015 (2)
C4	0.0138 (3)	0.0128 (3)	0.0173 (3)	−0.0002 (2)	0.0014 (2)	−0.0016 (2)
C5	0.0159 (3)	0.0131 (3)	0.0210 (3)	−0.0010 (2)	0.0007 (2)	−0.0022 (2)
C6	0.0148 (3)	0.0133 (3)	0.0210 (3)	−0.0019 (2)	0.0006 (2)	−0.0024 (2)
C7	0.0140 (3)	0.0191 (3)	0.0209 (3)	−0.0016 (2)	0.0003 (2)	−0.0048 (2)
C8	0.0142 (3)	0.0259 (3)	0.0159 (3)	0.0013 (2)	−0.0016 (2)	−0.0044 (3)
C9	0.0116 (3)	0.0203 (3)	0.0145 (3)	0.0027 (2)	−0.0010 (2)	−0.0006 (2)
C10	0.0176 (3)	0.0209 (3)	0.0176 (3)	0.0014 (2)	−0.0006 (2)	0.0027 (2)
C11	0.0242 (3)	0.0178 (3)	0.0240 (4)	0.0021 (3)	−0.0030 (3)	0.0002 (3)
C12	0.0270 (4)	0.0221 (3)	0.0198 (3)	0.0072 (3)	−0.0021 (3)	−0.0044 (3)
C13	0.0225 (3)	0.0256 (4)	0.0166 (3)	0.0053 (3)	0.0033 (3)	−0.0006 (3)
C14	0.0155 (3)	0.0202 (3)	0.0175 (3)	0.0018 (2)	0.0020 (2)	0.0002 (2)
C15	0.0201 (3)	0.0257 (4)	0.0205 (3)	0.0041 (3)	0.0026 (3)	0.0032 (3)

Geometric parameters (Å, º)

S1—O41	1.4462 (6)	C7—H7A	0.992 (11)
S1—O42	1.4467 (6)	C7—H7B	0.964 (12)
S1—C4	1.7599 (7)	C8—C9	1.5114 (10)
S1—C15	1.7619 (8)	C8—H8A	0.954 (12)
O21—N2	1.2449 (9)	C8—H8B	0.982 (13)
O22—N2	1.2345 (9)	C9—C10	1.3983 (11)
N1—C1	1.3454 (9)	C9—C14	1.4002 (10)
N1—C7	1.4623 (10)	C10—C11	1.3989 (11)
N1—H1	0.882 (16)	C10—H10	0.962 (13)
N2—C2	1.4441 (9)	C11—C12	1.3909 (12)
C1—C6	1.4293 (10)	C11—H11	0.934 (13)
C1—C2	1.4322 (10)	C12—C13	1.3949 (12)
C2—C3	1.3989 (10)	C12—H12	0.955 (14)
C3—C4	1.3797 (10)	C13—C14	1.3922 (11)
C3—H3	0.973 (14)	C13—H13	0.977 (14)
C4—C5	1.4142 (10)	C14—H14	0.974 (12)
C5—C6	1.3746 (10)	C15—H15A	0.949 (14)
C5—H5	0.972 (13)	C15—H15B	1.003 (14)
C6—H6	0.898 (13)	C15—H15C	0.955 (14)
C7—C8	1.5344 (11)
O41—S1—O42	118.03 (4)	N1—C7—H7B	109.8 (7)
O41—S1—C4	107.72 (4)	C8—C7—H7B	109.6 (7)
O42—S1—C4	107.99 (3)	H7A—C7—H7B	108.8 (10)
O41—S1—C15	107.66 (4)	C9—C8—C7	112.47 (6)
O42—S1—C15	109.33 (4)	C9—C8—H8A	109.9 (7)
C4—S1—C15	105.40 (4)	C7—C8—H8A	108.0 (7)
C1—N1—C7	125.00 (6)	C9—C8—H8B	110.2 (8)
C1—N1—H1	115.8 (10)	C7—C8—H8B	106.9 (7)
C7—N1—H1	118.9 (10)	H8A—C8—H8B	109.3 (10)
O22—N2—O21	121.76 (7)	C10—C9—C14	118.84 (7)
O22—N2—C2	119.00 (6)	C10—C9—C8	121.84 (7)
O21—N2—C2	119.24 (6)	C14—C9—C8	119.29 (7)
N1—C1—C6	120.36 (7)	C9—C10—C11	120.39 (7)
N1—C1—C2	123.58 (7)	C9—C10—H10	120.1 (8)
C6—C1—C2	116.06 (6)	C11—C10—H10	119.4 (8)
C3—C2—C1	121.96 (6)	C12—C11—C10	120.22 (8)
C3—C2—N2	115.91 (6)	C12—C11—H11	119.5 (8)
C1—C2—N2	122.12 (6)	C10—C11—H11	120.3 (9)
C4—C3—C2	119.55 (6)	C11—C12—C13	119.76 (7)
C4—C3—H3	122.5 (8)	C11—C12—H12	119.2 (9)
C2—C3—H3	117.9 (8)	C13—C12—H12	121.0 (9)
C3—C4—C5	120.39 (7)	C14—C13—C12	120.00 (7)
C3—C4—S1	119.15 (5)	C14—C13—H13	118.6 (8)
C5—C4—S1	120.37 (5)	C12—C13—H13	121.4 (8)
C6—C5—C4	120.17 (7)	C13—C14—C9	120.78 (7)
C6—C5—H5	119.5 (8)	C13—C14—H14	120.3 (7)
C4—C5—H5	120.4 (8)	C9—C14—H14	118.9 (7)
C5—C6—C1	121.75 (7)	S1—C15—H15A	108.7 (8)
C5—C6—H6	119.4 (8)	S1—C15—H15B	108.1 (8)
C1—C6—H6	118.9 (8)	H15A—C15—H15B	112.0 (11)
N1—C7—C8	108.76 (6)	S1—C15—H15C	106.2 (9)
N1—C7—H7A	109.9 (6)	H15A—C15—H15C	109.1 (12)
C8—C7—H7A	110.0 (6)	H15B—C15—H15C	112.6 (12)
C7—N1—C1—C6	3.38 (11)	C15—S1—C4—C5	−72.35 (7)
C7—N1—C1—C2	−177.13 (7)	C3—C4—C5—C6	2.03 (11)
N1—C1—C2—C3	−176.34 (7)	S1—C4—C5—C6	−174.59 (6)
C6—C1—C2—C3	3.18 (10)	C4—C5—C6—C1	0.80 (11)
N1—C1—C2—N2	2.73 (11)	N1—C1—C6—C5	176.24 (7)
C6—C1—C2—N2	−177.76 (6)	C2—C1—C6—C5	−3.29 (10)
O22—N2—C2—C3	−5.65 (10)	C1—N1—C7—C8	−175.70 (7)
O21—N2—C2—C3	174.68 (7)	N1—C7—C8—C9	−61.20 (8)
O22—N2—C2—C1	175.24 (7)	C7—C8—C9—C10	101.15 (8)
O21—N2—C2—C1	−4.44 (10)	C7—C8—C9—C14	−76.55 (8)
C1—C2—C3—C4	−0.55 (10)	C14—C9—C10—C11	0.21 (11)
N2—C2—C3—C4	−179.66 (6)	C8—C9—C10—C11	−177.50 (7)
C2—C3—C4—C5	−2.14 (10)	C9—C10—C11—C12	0.74 (12)
C2—C3—C4—S1	174.53 (5)	C10—C11—C12—C13	−0.70 (12)
O41—S1—C4—C3	−134.28 (6)	C11—C12—C13—C14	−0.30 (12)
O42—S1—C4—C3	−5.78 (7)	C12—C13—C14—C9	1.27 (12)
C15—S1—C4—C3	110.98 (6)	C10—C9—C14—C13	−1.21 (11)
O41—S1—C4—C5	42.39 (7)	C8—C9—C14—C13	176.56 (7)
O42—S1—C4—C5	170.88 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O21	0.882 (16)	1.951 (16)	2.6364 (9)	133.4 (14)