tert-Butyl N-[2-(N-isobutyl-4-meth-oxy-benzene-sulfonamido)-eth-yl]carbamate.

The title compound, C18H30N2O5S, was synthesized by the reaction of tert-butyl 2-(iso-butyl-amino)-ethyl-carbamate with p-meth-oxy-phenyl-sulfonyl chloride. In the mol-ecule, two intra-molecular C-H⋯O hydrogen bonds are observed. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds involving the imino group N atom and the ester group O atom into chains running parallel to the b axis. The chains are further connected by C-H⋯O hydrogen bonds, forming layers parallel to the bc plane.

Related literature

For potential HIV-1 protease inhibitors, see: Surleraux et al. (2005 ▶); Ghosh et al. (2006 ▶, 2011 ▶); Guo et al. (2010 ▶). For the structure of the meth­oxy analogue, see: Chatziefthimiou et al. (2006 ▶)

Experimental

Crystal data

C18H30N2O5S

M = 386.50

Monoclinic,

a = 19.2484 (5) Å

b = 5.29088 (12) Å

c = 20.1825 (6) Å

β = 92.497 (3)°

V = 2053.46 (9) Å3

Z = 4

Cu Kα radiation

μ = 1.65 mm−1

T = 293 K

0.28 × 0.16 × 0.14 mm

Data collection

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ▶) T min = 0.776, T max = 1.000

11865 measured reflections

3658 independent reflections

3122 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.089

S = 1.05

3658 reflections

245 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrysAlis PRO (Agilent, 2013 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814009143/rz5120sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814009143/rz5120Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814009143/rz5120Isup3.cml

CCDC reference: 998938

Additional supporting information: crystallographic information; 3D view; checkCIF report

C18H30N2O5S	F(000) = 832
Mr = 386.50	Dx = 1.250 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 5271 reflections
a = 19.2484 (5) Å	θ = 4.4–67.1°
b = 5.29088 (12) Å	µ = 1.65 mm−1
c = 20.1825 (6) Å	T = 293 K
β = 92.497 (3)°	Block, colorless
V = 2053.46 (9) Å3	0.28 × 0.16 × 0.14 mm
Z = 4

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer	3658 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	3122 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.031
Detector resolution: 10.4713 pixels mm-1	θmax = 67.2°, θmin = 4.4°
ω scans	h = −21→22
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −4→6
Tmin = 0.776, Tmax = 1.000	l = −22→24
11865 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0429P)2 + 0.3785P] where P = (Fo2 + 2Fc2)/3
3658 reflections	(Δ/σ)max = 0.001
245 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.85965 (7)	0.6201 (3)	0.54057 (7)	0.0368 (3)
C2	0.82937 (9)	0.6078 (3)	0.60169 (8)	0.0474 (4)
H2	0.7921	0.7121	0.6107	0.057*
C3	0.85494 (9)	0.4403 (4)	0.64878 (8)	0.0527 (4)
H3	0.8347	0.4314	0.6897	0.063*
C4	0.91066 (8)	0.2845 (3)	0.63579 (8)	0.0440 (4)
C5	0.94134 (8)	0.2961 (3)	0.57509 (8)	0.0435 (4)
H5	0.9788	0.1921	0.5662	0.052*
C6	0.91528 (8)	0.4657 (3)	0.52769 (7)	0.0403 (3)
H6	0.9356	0.4754	0.4868	0.048*
C7	0.98789 (12)	−0.0418 (4)	0.67445 (11)	0.0687 (6)
H7A	0.9749	−0.1530	0.6384	0.103*
H7B	0.9983	−0.1396	0.7137	0.103*
H7C	1.0282	0.0537	0.6634	0.103*
C8	0.70575 (8)	0.5843 (3)	0.45894 (8)	0.0420 (3)
H8A	0.6984	0.6863	0.4980	0.050*
H8B	0.7095	0.4093	0.4730	0.050*
C9	0.64333 (8)	0.6121 (3)	0.41093 (8)	0.0447 (4)
H9	0.6499	0.5001	0.3730	0.054*
C10	0.57790 (9)	0.5294 (4)	0.44490 (10)	0.0602 (5)
H10A	0.5853	0.3658	0.4645	0.090*
H10B	0.5397	0.5213	0.4128	0.090*
H10C	0.5675	0.6491	0.4788	0.090*
C11	0.63562 (11)	0.8797 (4)	0.38541 (12)	0.0743 (6)
H11A	0.6288	0.9921	0.4219	0.111*
H11B	0.5963	0.8894	0.3546	0.111*
H11C	0.6769	0.9276	0.3635	0.111*
C12	0.80312 (8)	0.4772 (3)	0.38535 (8)	0.0426 (3)
H12A	0.7712	0.3368	0.3783	0.051*
H12B	0.8454	0.4114	0.4069	0.051*
C13	0.82046 (9)	0.5869 (4)	0.31821 (8)	0.0517 (4)
H13A	0.8475	0.7399	0.3254	0.062*
H13B	0.8493	0.4669	0.2956	0.062*
C14	0.72163 (8)	0.4609 (3)	0.24696 (7)	0.0410 (3)
C15	0.62067 (9)	0.3966 (3)	0.17124 (8)	0.0459 (4)
C16	0.57907 (11)	0.2465 (4)	0.21953 (10)	0.0642 (5)
H16A	0.6083	0.1208	0.2407	0.096*
H16B	0.5408	0.1655	0.1961	0.096*
H16C	0.5617	0.3581	0.2525	0.096*
C17	0.65827 (11)	0.2296 (4)	0.12362 (9)	0.0646 (5)
H17A	0.6895	0.3305	0.0989	0.097*
H17B	0.6250	0.1496	0.0936	0.097*
H17C	0.6842	0.1028	0.1481	0.097*
C18	0.57448 (13)	0.5846 (4)	0.13381 (13)	0.0827 (7)
H18A	0.5534	0.6958	0.1647	0.124*
H18B	0.5388	0.4956	0.1086	0.124*
H18C	0.6019	0.6816	0.1044	0.124*
N1	0.77172 (6)	0.6617 (2)	0.42986 (6)	0.0371 (3)
N2	0.76011 (8)	0.6456 (3)	0.27567 (7)	0.0474 (3)
O1	0.93204 (7)	0.1260 (3)	0.68599 (6)	0.0611 (3)
O2	0.78598 (6)	1.0150 (2)	0.50924 (6)	0.0505 (3)
O3	0.88216 (6)	0.8952 (2)	0.43790 (5)	0.0462 (3)
O4	0.73211 (6)	0.2357 (2)	0.25588 (6)	0.0495 (3)
O5	0.67038 (6)	0.5608 (2)	0.20784 (6)	0.0511 (3)
S1	0.825787 (18)	0.82405 (6)	0.478139 (18)	0.03723 (12)
H2A	0.7503 (11)	0.793 (4)	0.2665 (10)	0.060 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0318 (7)	0.0407 (7)	0.0375 (7)	−0.0033 (6)	−0.0025 (6)	−0.0012 (6)
C2	0.0405 (8)	0.0577 (10)	0.0443 (8)	0.0031 (7)	0.0057 (7)	−0.0026 (7)
C3	0.0501 (10)	0.0697 (11)	0.0390 (8)	−0.0005 (8)	0.0101 (7)	0.0035 (8)
C4	0.0441 (8)	0.0474 (8)	0.0400 (8)	−0.0088 (7)	−0.0052 (6)	0.0062 (7)
C5	0.0372 (8)	0.0486 (9)	0.0442 (8)	0.0021 (7)	−0.0017 (6)	0.0011 (7)
C6	0.0345 (7)	0.0497 (8)	0.0366 (7)	0.0005 (6)	0.0007 (6)	0.0017 (6)
C7	0.0723 (13)	0.0631 (12)	0.0693 (12)	0.0052 (10)	−0.0139 (10)	0.0211 (10)
C8	0.0367 (8)	0.0466 (8)	0.0428 (8)	−0.0027 (7)	0.0007 (6)	0.0046 (7)
C9	0.0363 (8)	0.0500 (9)	0.0476 (8)	0.0010 (7)	−0.0013 (6)	0.0004 (7)
C10	0.0389 (9)	0.0742 (12)	0.0675 (11)	−0.0056 (9)	0.0011 (8)	0.0022 (10)
C11	0.0536 (11)	0.0713 (13)	0.0980 (16)	0.0155 (10)	0.0030 (11)	0.0339 (12)
C12	0.0400 (8)	0.0428 (8)	0.0444 (8)	0.0040 (7)	−0.0050 (6)	−0.0050 (7)
C13	0.0422 (9)	0.0688 (11)	0.0442 (8)	−0.0069 (8)	0.0024 (7)	−0.0105 (8)
C14	0.0461 (8)	0.0429 (8)	0.0342 (7)	−0.0037 (7)	0.0034 (6)	−0.0027 (6)
C15	0.0509 (9)	0.0383 (8)	0.0475 (8)	−0.0074 (7)	−0.0082 (7)	−0.0010 (7)
C16	0.0576 (11)	0.0712 (12)	0.0645 (11)	−0.0108 (10)	0.0085 (9)	0.0014 (10)
C17	0.0709 (13)	0.0721 (12)	0.0509 (10)	−0.0149 (10)	0.0038 (9)	−0.0163 (9)
C18	0.0884 (16)	0.0549 (11)	0.1003 (17)	−0.0064 (11)	−0.0478 (14)	0.0101 (11)
N1	0.0324 (6)	0.0399 (6)	0.0386 (6)	−0.0009 (5)	−0.0021 (5)	−0.0010 (5)
N2	0.0557 (8)	0.0455 (8)	0.0405 (7)	−0.0096 (7)	−0.0031 (6)	−0.0014 (6)
O1	0.0663 (8)	0.0678 (8)	0.0489 (7)	0.0010 (7)	−0.0025 (6)	0.0188 (6)
O2	0.0520 (7)	0.0400 (6)	0.0593 (7)	0.0084 (5)	−0.0007 (5)	−0.0097 (5)
O3	0.0422 (6)	0.0462 (6)	0.0502 (6)	−0.0078 (5)	0.0016 (5)	0.0059 (5)
O4	0.0555 (7)	0.0411 (6)	0.0512 (6)	0.0035 (5)	−0.0035 (5)	−0.0034 (5)
O5	0.0606 (7)	0.0367 (6)	0.0543 (6)	−0.0050 (5)	−0.0165 (5)	−0.0016 (5)
S1	0.03497 (19)	0.03481 (19)	0.0416 (2)	−0.00052 (14)	−0.00156 (14)	−0.00101 (14)

C1—C6	1.381 (2)	C11—H11C	0.9600
C1—C2	1.389 (2)	C12—N1	1.474 (2)
C1—S1	1.7621 (15)	C12—C13	1.524 (2)
C2—C3	1.375 (2)	C12—H12A	0.9700
C2—H2	0.9300	C12—H12B	0.9700
C3—C4	1.387 (3)	C13—N2	1.448 (2)
C3—H3	0.9300	C13—H13A	0.9700
C4—O1	1.365 (2)	C13—H13B	0.9700
C4—C5	1.384 (2)	C14—O4	1.2205 (19)
C5—C6	1.389 (2)	C14—N2	1.342 (2)
C5—H5	0.9300	C14—O5	1.345 (2)
C6—H6	0.9300	C15—O5	1.4677 (19)
C7—O1	1.421 (3)	C15—C17	1.513 (3)
C7—H7A	0.9600	C15—C16	1.513 (3)
C7—H7B	0.9600	C15—C18	1.514 (3)
C7—H7C	0.9600	C16—H16A	0.9600
C8—N1	1.4797 (19)	C16—H16B	0.9600
C8—C9	1.518 (2)	C16—H16C	0.9600
C8—H8A	0.9700	C17—H17A	0.9600
C8—H8B	0.9700	C17—H17B	0.9600
C9—C11	1.512 (3)	C17—H17C	0.9600
C9—C10	1.524 (2)	C18—H18A	0.9600
C9—H9	0.9800	C18—H18B	0.9600
C10—H10A	0.9600	C18—H18C	0.9600
C10—H10B	0.9600	N1—S1	1.6378 (12)
C10—H10C	0.9600	N2—H2A	0.82 (2)
C11—H11A	0.9600	O2—S1	1.4294 (12)
C11—H11B	0.9600	O3—S1	1.4338 (12)
C6—C1—C2	119.91 (14)	N1—C12—H12B	108.8
C6—C1—S1	119.56 (11)	C13—C12—H12B	108.8
C2—C1—S1	120.50 (12)	H12A—C12—H12B	107.7
C3—C2—C1	119.52 (15)	N2—C13—C12	114.06 (14)
C3—C2—H2	120.2	N2—C13—H13A	108.7
C1—C2—H2	120.2	C12—C13—H13A	108.7
C2—C3—C4	120.60 (15)	N2—C13—H13B	108.7
C2—C3—H3	119.7	C12—C13—H13B	108.7
C4—C3—H3	119.7	H13A—C13—H13B	107.6
O1—C4—C5	123.89 (16)	O4—C14—N2	124.23 (15)
O1—C4—C3	115.82 (15)	O4—C14—O5	125.63 (14)
C5—C4—C3	120.29 (15)	N2—C14—O5	110.14 (14)
C4—C5—C6	118.87 (15)	O5—C15—C17	110.24 (14)
C4—C5—H5	120.6	O5—C15—C16	109.76 (14)
C6—C5—H5	120.6	C17—C15—C16	112.57 (16)
C1—C6—C5	120.81 (14)	O5—C15—C18	102.60 (13)
C1—C6—H6	119.6	C17—C15—C18	110.70 (17)
C5—C6—H6	119.6	C16—C15—C18	110.52 (18)
O1—C7—H7A	109.5	C15—C16—H16A	109.5
O1—C7—H7B	109.5	C15—C16—H16B	109.5
H7A—C7—H7B	109.5	H16A—C16—H16B	109.5
O1—C7—H7C	109.5	C15—C16—H16C	109.5
H7A—C7—H7C	109.5	H16A—C16—H16C	109.5
H7B—C7—H7C	109.5	H16B—C16—H16C	109.5
N1—C8—C9	112.90 (12)	C15—C17—H17A	109.5
N1—C8—H8A	109.0	C15—C17—H17B	109.5
C9—C8—H8A	109.0	H17A—C17—H17B	109.5
N1—C8—H8B	109.0	C15—C17—H17C	109.5
C9—C8—H8B	109.0	H17A—C17—H17C	109.5
H8A—C8—H8B	107.8	H17B—C17—H17C	109.5
C11—C9—C8	111.82 (15)	C15—C18—H18A	109.5
C11—C9—C10	110.57 (16)	C15—C18—H18B	109.5
C8—C9—C10	109.38 (13)	H18A—C18—H18B	109.5
C11—C9—H9	108.3	C15—C18—H18C	109.5
C8—C9—H9	108.3	H18A—C18—H18C	109.5
C10—C9—H9	108.3	H18B—C18—H18C	109.5
C9—C10—H10A	109.5	C12—N1—C8	116.13 (12)
C9—C10—H10B	109.5	C12—N1—S1	116.31 (10)
H10A—C10—H10B	109.5	C8—N1—S1	116.30 (10)
C9—C10—H10C	109.5	C14—N2—C13	120.87 (16)
H10A—C10—H10C	109.5	C14—N2—H2A	118.5 (15)
H10B—C10—H10C	109.5	C13—N2—H2A	120.5 (15)
C9—C11—H11A	109.5	C4—O1—C7	117.91 (14)
C9—C11—H11B	109.5	C14—O5—C15	120.56 (12)
H11A—C11—H11B	109.5	O2—S1—O3	119.77 (7)
C9—C11—H11C	109.5	O2—S1—N1	107.05 (7)
H11A—C11—H11C	109.5	O3—S1—N1	106.12 (7)
H11B—C11—H11C	109.5	O2—S1—C1	107.89 (7)
N1—C12—C13	113.64 (13)	O3—S1—C1	107.48 (7)
N1—C12—H12A	108.8	N1—S1—C1	108.05 (7)
C13—C12—H12A	108.8
C6—C1—C2—C3	−0.4 (2)	C5—C4—O1—C7	−1.8 (2)
S1—C1—C2—C3	177.48 (13)	C3—C4—O1—C7	178.47 (16)
C1—C2—C3—C4	0.1 (3)	O4—C14—O5—C15	0.1 (2)
C2—C3—C4—O1	179.80 (16)	N2—C14—O5—C15	−179.50 (14)
C2—C3—C4—C5	0.1 (3)	C17—C15—O5—C14	−61.01 (19)
O1—C4—C5—C6	−179.78 (15)	C16—C15—O5—C14	63.5 (2)
C3—C4—C5—C6	−0.1 (2)	C18—C15—O5—C14	−178.95 (17)
C2—C1—C6—C5	0.4 (2)	C12—N1—S1—O2	171.49 (10)
S1—C1—C6—C5	−177.50 (12)	C8—N1—S1—O2	−46.10 (12)
C4—C5—C6—C1	−0.1 (2)	C12—N1—S1—O3	42.49 (12)
N1—C8—C9—C11	−57.0 (2)	C8—N1—S1—O3	−175.09 (10)
N1—C8—C9—C10	−179.83 (14)	C12—N1—S1—C1	−72.54 (12)
N1—C12—C13—N2	−70.15 (18)	C8—N1—S1—C1	69.88 (12)
C13—C12—N1—C8	127.99 (14)	C6—C1—S1—O2	−161.35 (12)
C13—C12—N1—S1	−89.53 (14)	C2—C1—S1—O2	20.79 (15)
C9—C8—N1—C12	−78.70 (17)	C6—C1—S1—O3	−30.90 (14)
C9—C8—N1—S1	138.82 (12)	C2—C1—S1—O3	151.23 (13)
O4—C14—N2—C13	2.9 (2)	C6—C1—S1—N1	83.23 (13)
O5—C14—N2—C13	−177.48 (14)	C2—C1—S1—N1	−94.64 (13)
C12—C13—N2—C14	−72.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O2	0.97	2.43	2.9106 (19)	110
C13—H13A···O3	0.97	2.48	3.107 (2)	122
C3—H3···O4i	0.93	2.59	3.402 (2)	147
N2—H2A···O4ii	0.82 (2)	2.38 (2)	3.190 (2)	171 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O2	0.97	2.43	2.9106 (19)	110
C13—H13A⋯O3	0.97	2.48	3.107 (2)	122
C3—H3⋯O4i	0.93	2.59	3.402 (2)	147
N2—H2A⋯O4ii	0.82 (2)	2.38 (2)	3.190 (2)	171 (2)

Symmetry codes: (i) ; (ii) .