Synthesis, spectroscopic analysis and crystal structure of (N-{2-[(2-amino­eth­yl)amino]­eth­yl}-4′-methyl-[1,1′-biphenyl]-4-sulfonamidato)tri­carb­on­ylrhenium(I)

The title complex possesses pseudo-octa­hedral geometry where one face of the octa­hedron is occupied by three carbonyl ligands and the other face is occupied by one sp² nitro­gen atom of the sulfonamide group and two sp³ nitro­gen atoms of the dien backbone.

Computing details

(N-{2-[(2-Aminoethyl)amino]ethyl}-4'-methyl-[1,1'-biphenyl]-4-sulfonamidato)tricarbonylrhenium(I)

Crystal data

[Re(C17H22N3O2S)(CO)3]	F(000) = 1176
Mr = 602.66	Dx = 1.825 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.5651 (9) Å	Cell parameters from 2346 reflections
b = 7.6604 (4) Å	θ = 2.6–24.1°
c = 15.4897 (11) Å	µ = 5.67 mm^−1
β = 95.472 (2)°	T = 296 K
V = 2192.8 (2) Å^3	Needle, colorless
Z = 4	0.22 × 0.13 × 0.05 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	4849 independent reflections
Radiation source: fine-focus sealed tube	3513 reflections with I > 2σ(I)
TRIUMPH curved graphite monochromator	Rint = 0.102
φ and ω scans	θmax = 27.2°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −23→23
Tmin = 0.572, Tmax = 0.765	k = −9→9
119413 measured reflections	l = −19→19

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.035	w = 1/[σ^2(Fo^2) + (0.0179P)^2 + 6.5423P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.071	(Δ/σ)max = 0.001
S = 1.08	Δρmax = 2.00 e Å^−3
4849 reflections	Δρmin = −1.80 e Å^−3
273 parameters	Extinction correction: SHELXL2017/1 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00017 (5)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Re1	0.86146 (2)	0.45261 (3)	0.61070 (2)	0.04344 (9)
S1	0.82122 (8)	0.3572 (2)	0.81148 (8)	0.0456 (4)
O1	0.7335 (3)	0.7018 (7)	0.5732 (4)	0.0875 (16)
O2	0.9354 (3)	0.7562 (8)	0.7131 (3)	0.104 (2)
O3	0.9230 (3)	0.6052 (8)	0.4508 (3)	0.0879 (17)
O4	0.8016 (2)	0.2083 (5)	0.8619 (2)	0.0563 (11)
O5	0.8906 (2)	0.4354 (6)	0.8338 (2)	0.0568 (11)
N1	0.9482 (3)	0.2530 (9)	0.6360 (3)	0.0769 (19)
H11N	0.991541	0.302049	0.634639	0.092*
H12N	0.945892	0.205082	0.688023	0.092*
N2	0.8135 (3)	0.2133 (6)	0.5486 (3)	0.0487 (12)
H2N	0.801808	0.237533	0.486680	0.058*
N3	0.8132 (2)	0.3099 (6)	0.7118 (2)	0.0440 (12)
C1	0.9364 (5)	0.1159 (12)	0.5660 (6)	0.099 (3)
H1C	0.949062	0.163356	0.511455	0.119*
H1D	0.967551	0.016551	0.580794	0.119*
C2	0.8629 (5)	0.0603 (10)	0.5568 (4)	0.080 (2)
H2A	0.852992	−0.008484	0.606844	0.096*
H2B	0.854413	−0.012739	0.505655	0.096*
C3	0.7445 (4)	0.1752 (9)	0.5872 (4)	0.0598 (18)
H3A	0.727485	0.059835	0.569374	0.072*
H3B	0.707984	0.259311	0.565914	0.072*
C4	0.7553 (4)	0.1838 (10)	0.6838 (4)	0.0655 (19)
H4A	0.710554	0.219162	0.706318	0.079*
H4B	0.768274	0.069138	0.706919	0.079*
C5	0.7818 (4)	0.6059 (8)	0.5873 (4)	0.0525 (16)
C6	0.9077 (4)	0.6386 (11)	0.6748 (4)	0.069 (2)
C7	0.9009 (3)	0.5469 (10)	0.5110 (4)	0.0607 (17)
C8	0.7558 (3)	0.5190 (8)	0.8291 (3)	0.0457 (14)
C9	0.6854 (3)	0.4687 (8)	0.8401 (4)	0.0550 (16)
H9	0.672952	0.351064	0.838917	0.066*
C10	0.6339 (3)	0.5938 (8)	0.8529 (4)	0.0561 (17)
H10	0.586941	0.558250	0.860192	0.067*
C11	0.6498 (3)	0.7698 (8)	0.8553 (3)	0.0492 (15)
C12	0.7211 (3)	0.8167 (8)	0.8449 (4)	0.0534 (16)
H12	0.733858	0.934122	0.846868	0.064*
C13	0.7730 (3)	0.6936 (8)	0.8319 (4)	0.0506 (15)
H13	0.820003	0.728879	0.824931	0.061*
C14	0.5948 (3)	0.9040 (8)	0.8704 (4)	0.0517 (16)
C15	0.5233 (4)	0.8895 (10)	0.8371 (4)	0.070 (2)
H15	0.508519	0.791583	0.804678	0.084*
C16	0.4733 (4)	1.0176 (11)	0.8511 (5)	0.075 (2)
H16	0.425596	1.003962	0.827930	0.090*
C17	0.4927 (4)	1.1647 (10)	0.8984 (5)	0.0662 (19)
C18	0.5630 (4)	1.1776 (9)	0.9336 (5)	0.0654 (18)
H18	0.577106	1.273921	0.967606	0.079*
C19	0.6130 (4)	1.0513 (9)	0.9197 (4)	0.0613 (16)
H19	0.660456	1.064908	0.944103	0.074*
C20	0.4383 (4)	1.3088 (11)	0.9120 (5)	0.092 (3)
H20A	0.461891	1.420204	0.911398	0.138*
H20B	0.419068	1.292329	0.966780	0.138*
H20C	0.399557	1.304649	0.866244	0.138*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Re1	0.04118 (13)	0.06022 (16)	0.02905 (11)	−0.00246 (13)	0.00405 (8)	0.00870 (12)
S1	0.0592 (9)	0.0527 (9)	0.0250 (6)	−0.0062 (8)	0.0056 (6)	0.0006 (6)
O1	0.070 (3)	0.073 (4)	0.118 (4)	0.023 (3)	0.002 (3)	−0.001 (3)
O2	0.113 (5)	0.112 (5)	0.079 (4)	−0.062 (4)	−0.029 (3)	0.013 (3)
O3	0.071 (3)	0.134 (5)	0.062 (3)	−0.002 (3)	0.023 (2)	0.050 (3)
O4	0.090 (3)	0.052 (3)	0.0283 (19)	−0.006 (2)	0.012 (2)	0.0072 (18)
O5	0.056 (2)	0.074 (3)	0.039 (2)	−0.009 (2)	−0.0056 (18)	−0.002 (2)
N1	0.044 (3)	0.138 (6)	0.049 (3)	0.022 (3)	0.008 (3)	0.029 (4)
N2	0.071 (3)	0.047 (3)	0.028 (2)	0.012 (3)	0.006 (2)	0.004 (2)
N3	0.055 (3)	0.055 (3)	0.023 (2)	−0.009 (2)	0.0078 (19)	−0.002 (2)
C1	0.085 (6)	0.093 (7)	0.126 (8)	0.017 (5)	0.041 (6)	0.006 (6)
C2	0.112 (7)	0.076 (5)	0.052 (4)	0.042 (5)	0.008 (4)	−0.002 (4)
C3	0.080 (5)	0.056 (4)	0.044 (3)	−0.025 (4)	0.010 (3)	−0.003 (3)
C4	0.070 (4)	0.087 (5)	0.041 (3)	−0.027 (4)	0.016 (3)	−0.015 (3)
C5	0.059 (4)	0.049 (4)	0.051 (4)	−0.009 (3)	0.013 (3)	−0.004 (3)
C6	0.056 (4)	0.100 (6)	0.050 (4)	−0.017 (4)	−0.004 (3)	0.027 (4)
C7	0.053 (4)	0.084 (5)	0.045 (3)	0.005 (4)	0.006 (3)	0.016 (4)
C8	0.057 (4)	0.050 (4)	0.031 (3)	−0.012 (3)	0.010 (2)	−0.005 (2)
C9	0.070 (4)	0.043 (3)	0.053 (3)	−0.019 (4)	0.016 (3)	−0.011 (3)
C10	0.050 (4)	0.055 (4)	0.065 (4)	−0.028 (3)	0.014 (3)	−0.015 (3)
C11	0.060 (4)	0.052 (4)	0.036 (3)	−0.007 (3)	0.008 (3)	−0.001 (3)
C12	0.064 (4)	0.044 (4)	0.053 (4)	−0.012 (3)	0.011 (3)	0.001 (3)
C13	0.053 (4)	0.054 (4)	0.047 (3)	−0.015 (3)	0.012 (3)	−0.001 (3)
C14	0.053 (4)	0.062 (4)	0.040 (3)	−0.006 (3)	0.008 (3)	0.009 (3)
C15	0.065 (5)	0.087 (6)	0.057 (4)	−0.003 (4)	0.001 (3)	−0.011 (4)
C16	0.053 (4)	0.109 (7)	0.063 (4)	0.001 (4)	0.002 (3)	0.005 (4)
C17	0.069 (5)	0.069 (5)	0.065 (4)	0.011 (4)	0.025 (4)	0.016 (4)
C18	0.068 (5)	0.046 (4)	0.083 (5)	0.002 (4)	0.013 (4)	−0.002 (4)
C19	0.056 (4)	0.055 (4)	0.072 (4)	−0.001 (4)	0.002 (3)	−0.003 (4)
C20	0.075 (5)	0.100 (7)	0.106 (6)	0.019 (5)	0.030 (5)	0.012 (5)

Geometric parameters (Å, º)

Re1—C6	1.895 (8)	C4—H4A	0.9700
Re1—C5	1.896 (7)	C4—H4B	0.9700
Re1—C7	1.914 (6)	C8—C13	1.375 (8)
Re1—N3	2.173 (4)	C8—C9	1.389 (8)
Re1—N2	2.217 (5)	C9—C10	1.381 (9)
Re1—N1	2.228 (6)	C9—H9	0.9300
S1—O5	1.433 (4)	C10—C11	1.381 (8)
S1—O4	1.448 (4)	C10—H10	0.9300
S1—N3	1.579 (4)	C11—C12	1.394 (8)
S1—C8	1.775 (6)	C11—C14	1.484 (8)
O1—C5	1.163 (7)	C12—C13	1.376 (8)
O2—C6	1.170 (9)	C12—H12	0.9300
O3—C7	1.143 (7)	C13—H13	0.9300
N1—C1	1.510 (10)	C14—C15	1.381 (9)
N1—H11N	0.8900	C14—C19	1.387 (9)
N1—H12N	0.8900	C15—C16	1.381 (10)
N2—C2	1.486 (8)	C15—H15	0.9300
N2—C3	1.493 (7)	C16—C17	1.372 (10)
N2—H2N	0.9800	C16—H16	0.9300
N3—C4	1.479 (7)	C17—C18	1.370 (9)
C1—C2	1.423 (10)	C17—C20	1.524 (9)
C1—H1C	0.9700	C18—C19	1.372 (9)
C1—H1D	0.9700	C18—H18	0.9300
C2—H2A	0.9700	C19—H19	0.9300
C2—H2B	0.9700	C20—H20A	0.9600
C3—C4	1.493 (8)	C20—H20B	0.9600
C3—H3A	0.9700	C20—H20C	0.9600
C3—H3B	0.9700
C6—Re1—C5	86.6 (3)	H3A—C3—H3B	108.1
C6—Re1—C7	87.1 (3)	N3—C4—C3	110.3 (5)
C5—Re1—C7	87.9 (3)	N3—C4—H4A	109.6
C6—Re1—N3	101.4 (2)	C3—C4—H4A	109.6
C5—Re1—N3	94.7 (2)	N3—C4—H4B	109.6
C7—Re1—N3	171.2 (2)	C3—C4—H4B	109.6
C6—Re1—N2	172.9 (2)	H4A—C4—H4B	108.1
C5—Re1—N2	99.0 (2)	O1—C5—Re1	179.1 (6)
C7—Re1—N2	97.5 (2)	O2—C6—Re1	178.4 (7)
N3—Re1—N2	73.78 (16)	O3—C7—Re1	178.4 (6)
C6—Re1—N1	98.1 (3)	C13—C8—C9	119.0 (6)
C5—Re1—N1	174.9 (3)	C13—C8—S1	121.6 (5)
C7—Re1—N1	94.3 (2)	C9—C8—S1	119.4 (5)
N3—Re1—N1	82.45 (18)	C10—C9—C8	119.9 (6)
N2—Re1—N1	76.3 (2)	C10—C9—H9	120.1
O5—S1—O4	117.7 (3)	C8—C9—H9	120.1
O5—S1—N3	109.4 (2)	C11—C10—C9	122.1 (6)
O4—S1—N3	110.0 (2)	C11—C10—H10	118.9
O5—S1—C8	106.5 (3)	C9—C10—H10	118.9
O4—S1—C8	104.8 (3)	C10—C11—C12	116.9 (6)
N3—S1—C8	108.0 (3)	C10—C11—C14	122.1 (6)
C1—N1—Re1	107.3 (4)	C12—C11—C14	121.0 (6)
C1—N1—H11N	110.2	C13—C12—C11	121.7 (6)
Re1—N1—H11N	110.2	C13—C12—H12	119.2
C1—N1—H12N	110.2	C11—C12—H12	119.2
Re1—N1—H12N	110.2	C8—C13—C12	120.5 (6)
H11N—N1—H12N	108.5	C8—C13—H13	119.8
C2—N2—C3	111.0 (5)	C12—C13—H13	119.8
C2—N2—Re1	113.3 (4)	C15—C14—C19	116.5 (6)
C3—N2—Re1	108.2 (3)	C15—C14—C11	122.5 (6)
C2—N2—H2N	108.1	C19—C14—C11	120.9 (6)
C3—N2—H2N	108.1	C14—C15—C16	121.4 (7)
Re1—N2—H2N	108.1	C14—C15—H15	119.3
C4—N3—S1	115.8 (3)	C16—C15—H15	119.3
C4—N3—Re1	117.1 (3)	C17—C16—C15	121.4 (7)
S1—N3—Re1	125.6 (3)	C17—C16—H16	119.3
C2—C1—N1	110.7 (6)	C15—C16—H16	119.3
C2—C1—H1C	109.5	C18—C17—C16	117.5 (7)
N1—C1—H1C	109.5	C18—C17—C20	120.8 (7)
C2—C1—H1D	109.5	C16—C17—C20	121.7 (7)
N1—C1—H1D	109.5	C17—C18—C19	121.4 (7)
H1C—C1—H1D	108.1	C17—C18—H18	119.3
C1—C2—N2	110.5 (7)	C19—C18—H18	119.3
C1—C2—H2A	109.5	C18—C19—C14	121.7 (6)
N2—C2—H2A	109.5	C18—C19—H19	119.1
C1—C2—H2B	109.5	C14—C19—H19	119.1
N2—C2—H2B	109.5	C17—C20—H20A	109.5
H2A—C2—H2B	108.1	C17—C20—H20B	109.5
N2—C3—C4	110.8 (5)	H20A—C20—H20B	109.5
N2—C3—H3A	109.5	C17—C20—H20C	109.5
C4—C3—H3A	109.5	H20A—C20—H20C	109.5
N2—C3—H3B	109.5	H20B—C20—H20C	109.5
C4—C3—H3B	109.5
O5—S1—N3—C4	162.7 (5)	C8—C9—C10—C11	0.0 (9)
O4—S1—N3—C4	32.0 (5)	C9—C10—C11—C12	−0.6 (9)
C8—S1—N3—C4	−81.8 (5)	C9—C10—C11—C14	−179.1 (6)
O5—S1—N3—Re1	−31.7 (4)	C10—C11—C12—C13	0.7 (9)
O4—S1—N3—Re1	−162.5 (3)	C14—C11—C12—C13	179.3 (5)
C8—S1—N3—Re1	83.7 (4)	C9—C8—C13—C12	−0.4 (8)
Re1—N1—C1—C2	−48.9 (8)	S1—C8—C13—C12	179.4 (4)
N1—C1—C2—N2	49.9 (9)	C11—C12—C13—C8	−0.3 (9)
C3—N2—C2—C1	−148.2 (6)	C10—C11—C14—C15	−37.0 (9)
Re1—N2—C2—C1	−26.3 (7)	C12—C11—C14—C15	144.5 (6)
C2—N2—C3—C4	76.7 (7)	C10—C11—C14—C19	142.6 (6)
Re1—N2—C3—C4	−48.2 (6)	C12—C11—C14—C19	−35.9 (8)
S1—N3—C4—C3	169.7 (5)	C19—C14—C15—C16	1.4 (10)
Re1—N3—C4—C3	2.9 (7)	C11—C14—C15—C16	−179.1 (6)
N2—C3—C4—N3	29.9 (8)	C14—C15—C16—C17	0.1 (11)
O5—S1—C8—C13	20.8 (5)	C15—C16—C17—C18	−1.9 (10)
O4—S1—C8—C13	146.3 (5)	C15—C16—C17—C20	178.3 (7)
N3—S1—C8—C13	−96.5 (5)	C16—C17—C18—C19	2.2 (10)
O5—S1—C8—C9	−159.4 (4)	C20—C17—C18—C19	−178.0 (6)
O4—S1—C8—C9	−33.9 (5)	C17—C18—C19—C14	−0.7 (11)
N3—S1—C8—C9	83.3 (5)	C15—C14—C19—C18	−1.1 (10)
C13—C8—C9—C10	0.5 (9)	C11—C14—C19—C18	179.3 (6)
S1—C8—C9—C10	−179.3 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11N···O3^i	0.89	2.27	3.053 (7)	146
N1—H12N···O2^ii	0.89	2.59	3.028 (7)	111
N2—H2N···O4^iii	0.98	1.98	2.941 (5)	167

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+2, y−1/2, −z+3/2; (iii) x, −y+1/2, z−1/2.