[5-Fluoro-2-(4-iodo-2-nitro­phenyl­sulfan­yl)phen­yl]-N,N-dimethyl­methanamine

In the title compound, two aromatic rings are almost perpendicular to each other with a dihedral angle of 72.4 (1)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• R factor = 0.022
• wR factor = 0.057
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT'; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

[5-Fluoro-2-(4-iodo-2-nitrophenylsulfanyl)phenyl]-N,N-dimethylmethanamine

Crystal data

C15H14N2O2FIS	F(000) = 848
Mr = 432.24	Dx = 1.770 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.7213 (17) Å	Cell parameters from 4524 reflections
b = 12.530 (3) Å	θ = 1.4–27.9°
c = 15.135 (3) Å	µ = 2.12 mm^−1
β = 101.29 (3)°	T = 293 K
V = 1622.0 (6) Å^3	Block, colorless
Z = 4	0.22 × 0.20 × 0.16 mm

Data collection

Bruker P4 diffractometer	2859 independent reflections
Radiation source: fine-focus sealed tube	2586 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.653, Tmax = 0.728	k = −14→11
9624 measured reflections	l = −18→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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.057	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0335P)^2] where P = (Fo^2 + 2Fc^2)/3
2859 reflections	(Δ/σ)max = 0.002
201 parameters	Δρmax = 0.43 e Å^−3
0 restraints	Δρmin = −0.58 e Å^−3

Special details

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
I1	0.676858 (17)	0.359553 (14)	1.062889 (10)	0.02679 (8)
S1	0.87276 (7)	0.64199 (4)	0.72728 (4)	0.01893 (14)
F1	0.76836 (19)	0.36721 (12)	0.40767 (9)	0.0331 (4)
O1	0.9569 (2)	0.73551 (15)	1.00677 (12)	0.0332 (4)
O2	0.91565 (19)	0.77778 (13)	0.86539 (11)	0.0257 (4)
N1	0.9082 (2)	0.71516 (16)	0.92705 (13)	0.0212 (4)
N2	1.1233 (2)	0.32525 (16)	0.70949 (12)	0.0186 (4)
C1	0.8368 (2)	0.61038 (18)	0.90414 (16)	0.0166 (5)
C2	0.7985 (2)	0.55249 (19)	0.97514 (15)	0.0188 (5)
H2	0.8203	0.5797	1.0334	0.023*
C3	0.7280 (2)	0.45449 (19)	0.95795 (15)	0.0197 (5)
C4	0.6940 (2)	0.41587 (19)	0.87036 (15)	0.0201 (5)
H4	0.6434	0.3506	0.8585	0.024*
C5	0.7346 (2)	0.47342 (19)	0.80063 (15)	0.0191 (5)
H5	0.7117	0.4456	0.7426	0.023*
C6	0.8094 (2)	0.57271 (18)	0.81503 (15)	0.0165 (5)
C7	0.8391 (2)	0.54910 (18)	0.63653 (14)	0.0160 (5)
C8	0.9379 (2)	0.46184 (18)	0.63142 (14)	0.0167 (5)
C9	0.9107 (3)	0.4005 (2)	0.55352 (15)	0.0200 (5)
H9	0.9730	0.3415	0.5483	0.024*
C10	0.7897 (3)	0.4283 (2)	0.48369 (15)	0.0221 (5)
C11	0.6941 (3)	0.5137 (2)	0.48648 (15)	0.0254 (6)
H11	0.6155	0.5309	0.4377	0.030*
C12	0.7184 (3)	0.5738 (2)	0.56459 (15)	0.0220 (5)
H12	0.6533	0.6315	0.5691	0.026*
C13	1.0778 (2)	0.43755 (19)	0.70495 (15)	0.0185 (5)
H13A	1.1657	0.4802	0.6950	0.022*
H13B	1.0541	0.4585	0.7625	0.022*
C14	1.0133 (3)	0.2618 (2)	0.74903 (16)	0.0251 (5)
H14A	1.0445	0.1882	0.7513	0.038*
H14B	0.9104	0.2687	0.7128	0.038*
H14C	1.0129	0.2868	0.8089	0.038*
C15	1.2819 (3)	0.3150 (2)	0.76285 (16)	0.0280 (6)
H15A	1.2852	0.3438	0.8220	0.042*
H15B	1.3536	0.3534	0.7339	0.042*
H15C	1.3109	0.2410	0.7677	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.03029 (11)	0.02798 (12)	0.02461 (12)	−0.00346 (7)	0.01156 (7)	0.00507 (7)
S1	0.0243 (3)	0.0129 (3)	0.0213 (3)	−0.0010 (2)	0.0087 (2)	0.0005 (2)
F1	0.0448 (8)	0.0394 (10)	0.0143 (7)	−0.0106 (7)	0.0040 (7)	−0.0063 (6)
O1	0.0421 (10)	0.0330 (11)	0.0253 (9)	−0.0172 (9)	0.0086 (8)	−0.0137 (8)
O2	0.0311 (9)	0.0140 (9)	0.0340 (10)	−0.0047 (7)	0.0110 (7)	−0.0014 (8)
N1	0.0192 (9)	0.0182 (11)	0.0276 (11)	−0.0035 (8)	0.0081 (8)	−0.0060 (9)
N2	0.0183 (9)	0.0199 (11)	0.0183 (10)	0.0062 (8)	0.0051 (8)	0.0030 (9)
C1	0.0157 (10)	0.0118 (12)	0.0228 (12)	−0.0017 (9)	0.0051 (9)	−0.0040 (10)
C2	0.0180 (10)	0.0227 (13)	0.0159 (11)	0.0022 (10)	0.0040 (9)	−0.0021 (10)
C3	0.0200 (11)	0.0201 (13)	0.0211 (12)	0.0006 (10)	0.0093 (9)	0.0035 (10)
C4	0.0205 (11)	0.0142 (12)	0.0268 (12)	−0.0034 (9)	0.0076 (9)	−0.0042 (10)
C5	0.0206 (11)	0.0176 (12)	0.0190 (11)	−0.0030 (9)	0.0035 (9)	−0.0045 (10)
C6	0.0139 (10)	0.0146 (12)	0.0217 (11)	0.0039 (9)	0.0056 (9)	0.0013 (10)
C7	0.0183 (10)	0.0158 (12)	0.0149 (11)	−0.0013 (9)	0.0055 (9)	0.0029 (9)
C8	0.0181 (10)	0.0173 (12)	0.0154 (11)	−0.0015 (9)	0.0053 (9)	0.0032 (9)
C9	0.0233 (11)	0.0193 (13)	0.0189 (12)	0.0000 (10)	0.0082 (10)	0.0011 (10)
C10	0.0263 (12)	0.0239 (14)	0.0161 (11)	−0.0112 (11)	0.0038 (10)	−0.0023 (10)
C11	0.0199 (11)	0.0358 (16)	0.0189 (12)	−0.0042 (11)	0.0002 (9)	0.0080 (12)
C12	0.0174 (11)	0.0233 (14)	0.0260 (13)	0.0037 (10)	0.0060 (10)	0.0067 (11)
C13	0.0185 (11)	0.0195 (13)	0.0170 (11)	0.0024 (10)	0.0021 (9)	0.0020 (10)
C14	0.0273 (12)	0.0243 (14)	0.0238 (12)	0.0028 (11)	0.0053 (10)	0.0062 (11)
C15	0.0213 (12)	0.0356 (16)	0.0272 (13)	0.0122 (11)	0.0052 (10)	0.0047 (12)

Geometric parameters (Å, º)

I1—C3	2.101 (2)	C7—C12	1.393 (3)
S1—C6	1.764 (2)	C7—C8	1.404 (3)
S1—C7	1.780 (2)	C8—C9	1.388 (3)
F1—C10	1.364 (3)	C8—C13	1.513 (3)
O1—N1	1.225 (2)	C9—C10	1.384 (3)
O2—N1	1.231 (3)	C9—H9	0.9300
N1—C1	1.465 (3)	C10—C11	1.362 (3)
N2—C13	1.460 (3)	C11—C12	1.383 (3)
N2—C14	1.461 (3)	C11—H11	0.9300
N2—C15	1.464 (3)	C12—H12	0.9300
C1—C2	1.390 (3)	C13—H13A	0.9700
C1—C6	1.404 (3)	C13—H13B	0.9700
C2—C3	1.375 (3)	C14—H14A	0.9600
C2—H2	0.9300	C14—H14B	0.9600
C3—C4	1.388 (3)	C14—H14C	0.9600
C4—C5	1.380 (3)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C6	1.402 (3)	C15—H15C	0.9600
C5—H5	0.9300
C6—S1—C7	103.33 (11)	C10—C9—C8	119.2 (2)
O1—N1—O2	123.7 (2)	C10—C9—H9	120.4
O1—N1—C1	118.0 (2)	C8—C9—H9	120.4
O2—N1—C1	118.35 (19)	C11—C10—F1	118.9 (2)
C13—N2—C14	110.45 (18)	C11—C10—C9	123.6 (2)
C13—N2—C15	109.24 (19)	F1—C10—C9	117.4 (2)
C14—N2—C15	110.56 (18)	C10—C11—C12	117.6 (2)
C2—C1—C6	123.0 (2)	C10—C11—H11	121.2
C2—C1—N1	116.1 (2)	C12—C11—H11	121.2
C6—C1—N1	120.9 (2)	C11—C12—C7	120.8 (2)
C3—C2—C1	119.1 (2)	C11—C12—H12	119.6
C3—C2—H2	120.5	C7—C12—H12	119.6
C1—C2—H2	120.5	N2—C13—C8	113.66 (18)
C2—C3—C4	119.7 (2)	N2—C13—H13A	108.8
C2—C3—I1	121.06 (17)	C8—C13—H13A	108.8
C4—C3—I1	119.18 (17)	N2—C13—H13B	108.8
C5—C4—C3	120.6 (2)	C8—C13—H13B	108.8
C5—C4—H4	119.7	H13A—C13—H13B	107.7
C3—C4—H4	119.7	N2—C14—H14A	109.5
C4—C5—C6	121.7 (2)	N2—C14—H14B	109.5
C4—C5—H5	119.1	H14A—C14—H14B	109.5
C6—C5—H5	119.1	N2—C14—H14C	109.5
C5—C6—C1	115.7 (2)	H14A—C14—H14C	109.5
C5—C6—S1	121.64 (17)	H14B—C14—H14C	109.5
C1—C6—S1	122.56 (18)	N2—C15—H15A	109.5
C12—C7—C8	120.6 (2)	N2—C15—H15B	109.5
C12—C7—S1	116.28 (18)	H15A—C15—H15B	109.5
C8—C7—S1	122.78 (16)	N2—C15—H15C	109.5
C9—C8—C7	118.24 (19)	H15A—C15—H15C	109.5
C9—C8—C13	119.5 (2)	H15B—C15—H15C	109.5
C7—C8—C13	122.1 (2)
O1—N1—C1—C2	14.1 (3)	C6—S1—C7—C12	109.83 (18)
O2—N1—C1—C2	−165.81 (19)	C6—S1—C7—C8	−77.3 (2)
O1—N1—C1—C6	−166.2 (2)	C12—C7—C8—C9	−0.8 (3)
O2—N1—C1—C6	13.9 (3)	S1—C7—C8—C9	−173.43 (17)
C6—C1—C2—C3	−1.2 (3)	C12—C7—C8—C13	175.1 (2)
N1—C1—C2—C3	178.56 (19)	S1—C7—C8—C13	2.5 (3)
C1—C2—C3—C4	−1.0 (3)	C7—C8—C9—C10	1.0 (3)
C1—C2—C3—I1	177.00 (16)	C13—C8—C9—C10	−175.0 (2)
C2—C3—C4—C5	2.0 (3)	C8—C9—C10—C11	0.2 (4)
I1—C3—C4—C5	−176.10 (17)	C8—C9—C10—F1	178.9 (2)
C3—C4—C5—C6	−0.7 (3)	F1—C10—C11—C12	179.8 (2)
C4—C5—C6—C1	−1.4 (3)	C9—C10—C11—C12	−1.5 (4)
C4—C5—C6—S1	175.75 (17)	C10—C11—C12—C7	1.7 (3)
C2—C1—C6—C5	2.3 (3)	C8—C7—C12—C11	−0.5 (3)
N1—C1—C6—C5	−177.40 (19)	S1—C7—C12—C11	172.55 (18)
C2—C1—C6—S1	−174.74 (17)	C14—N2—C13—C8	−74.5 (2)
N1—C1—C6—S1	5.5 (3)	C15—N2—C13—C8	163.68 (19)
C7—S1—C6—C5	−6.8 (2)	C9—C8—C13—N2	−29.8 (3)
C7—S1—C6—C1	170.08 (18)	C7—C8—C13—N2	154.3 (2)