N-[4-(Ethoxy­carbon­yl)phen­yl]-p-tolyl­sulfonamide

In the mol­ecule of the title compound {systematic name: ethyl 4-[(4-methyl­phen­yl)sulfonyl­amino]benzoate}, C₁₆H₁₇NO₄S, the dihedral angle between the two benzene rings is 93.4 (1)°. The C—N—S—C torsion angle in the central part of the mol­ecule is 71.09 (16)°. The crystal structure is stabilized by inter­molecular N—H...O inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.129
• Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.70 mm
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O3     -   C14     ..       5.22 su
PLAT318_ALERT_2_C Check Hybridisation of  N1     in Main Residue .          ?
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C16 H17 N O4 S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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.

Ethyl 4-[(4-methylphenyl)sulfonylamino]benzoate

Crystal data

C16H17NO4S	F(000) = 672
Mr = 319.37	Dx = 1.342 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 15144 reflections
a = 7.8159 (16) Å	θ = 3.0–27.5°
b = 8.0701 (16) Å	µ = 0.22 mm^−1
c = 25.165 (5) Å	T = 293 K
β = 95.36 (3)°	Rod, white
V = 1580.3 (5) Å^3	0.70 × 0.63 × 0.59 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer	3624 independent reflections
Radiation source: rotating anode	2706 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
oscillation scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.860, Tmax = 0.880	k = −10→10
15144 measured reflections	l = −32→32

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.129	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0774P)^2 + 0.0238P] where P = (Fo^2 + 2Fc^2)/3
3624 reflections	(Δ/σ)max = 0.005
199 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−3

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

	x	y	z	Uiso*/Ueq
S1	0.47158 (5)	0.89716 (5)	0.135352 (16)	0.05363 (16)
N1	0.40689 (18)	0.94647 (16)	0.07428 (5)	0.0547 (4)
H1A	0.4015	0.8668	0.0515	0.066*
O1	0.59587 (15)	1.01544 (15)	0.15668 (5)	0.0680 (4)
O2	0.51902 (18)	0.72649 (15)	0.13287 (5)	0.0686 (4)
O3	0.24438 (19)	1.70099 (13)	0.00595 (5)	0.0741 (4)
O4	0.14276 (16)	1.55942 (14)	−0.06596 (5)	0.0593 (3)
C1	−0.1387 (3)	0.9082 (3)	0.26568 (8)	0.0775 (6)
H1C	−0.1109	0.9713	0.2977	0.116*
H1D	−0.1629	0.7957	0.2749	0.116*
H1E	−0.2377	0.9555	0.2458	0.116*
C2	0.0104 (2)	0.91150 (19)	0.23233 (7)	0.0571 (4)
C3	0.0025 (2)	0.8306 (2)	0.18360 (7)	0.0611 (4)
H3A	−0.0980	0.7759	0.1711	0.073*
C4	0.1401 (2)	0.8295 (2)	0.15329 (7)	0.0585 (4)
H4A	0.1325	0.7742	0.1207	0.070*
C5	0.2903 (2)	0.91131 (16)	0.17150 (6)	0.0477 (4)
C6	0.3003 (2)	0.9941 (2)	0.21957 (6)	0.0579 (4)
H6A	0.4003	1.0502	0.2317	0.070*
C7	0.1622 (3)	0.9933 (2)	0.24941 (7)	0.0633 (5)
H7A	0.1702	1.0489	0.2819	0.076*
C8	0.3584 (2)	1.10448 (17)	0.05411 (6)	0.0455 (3)
C9	0.2703 (2)	1.10989 (18)	0.00365 (7)	0.0550 (4)
H9A	0.2419	1.0118	−0.0144	0.066*
C10	0.2249 (2)	1.25936 (19)	−0.01980 (6)	0.0557 (4)
H10A	0.1671	1.2618	−0.0538	0.067*
C11	0.2649 (2)	1.40688 (16)	0.00704 (6)	0.0472 (3)
C12	0.3512 (2)	1.40127 (19)	0.05746 (7)	0.0553 (4)
H12A	0.3781	1.4995	0.0757	0.066*
C13	0.3981 (2)	1.2514 (2)	0.08127 (7)	0.0573 (4)
H13A	0.4560	1.2491	0.1153	0.069*
C14	0.2186 (2)	1.57086 (19)	−0.01675 (7)	0.0519 (4)
C15	0.0936 (3)	1.7134 (2)	−0.09315 (8)	0.0631 (5)
H15A	0.1945	1.7805	−0.0973	0.076*
H15B	0.0164	1.7759	−0.0728	0.076*
C16	0.0067 (3)	1.6692 (3)	−0.14627 (8)	0.0805 (6)
H16A	−0.0274	1.7686	−0.1654	0.121*
H16B	−0.0930	1.6032	−0.1417	0.121*
H16C	0.0844	1.6074	−0.1661	0.121*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0555 (3)	0.0488 (2)	0.0547 (3)	0.00840 (16)	−0.00483 (18)	0.00949 (16)
N1	0.0715 (9)	0.0432 (7)	0.0486 (7)	0.0125 (6)	0.0019 (6)	0.0046 (6)
O1	0.0560 (7)	0.0699 (8)	0.0743 (8)	−0.0039 (6)	−0.0133 (6)	0.0121 (6)
O2	0.0787 (9)	0.0543 (7)	0.0716 (8)	0.0226 (6)	0.0001 (7)	0.0114 (6)
O3	0.1001 (11)	0.0400 (6)	0.0779 (9)	0.0033 (6)	−0.0147 (8)	−0.0011 (6)
O4	0.0774 (8)	0.0441 (6)	0.0551 (6)	0.0083 (5)	−0.0014 (6)	0.0086 (5)
C1	0.0779 (14)	0.0900 (15)	0.0653 (12)	0.0156 (11)	0.0108 (10)	0.0113 (10)
C2	0.0672 (11)	0.0544 (9)	0.0484 (8)	0.0137 (8)	−0.0020 (8)	0.0088 (7)
C3	0.0565 (10)	0.0664 (10)	0.0582 (10)	−0.0025 (8)	−0.0061 (8)	−0.0031 (8)
C4	0.0609 (10)	0.0646 (10)	0.0476 (8)	0.0012 (8)	−0.0082 (8)	−0.0107 (7)
C5	0.0566 (9)	0.0400 (7)	0.0442 (7)	0.0040 (6)	−0.0077 (7)	0.0037 (6)
C6	0.0668 (11)	0.0531 (9)	0.0511 (9)	−0.0036 (7)	−0.0094 (8)	−0.0054 (7)
C7	0.0803 (13)	0.0608 (10)	0.0467 (9)	0.0056 (9)	−0.0048 (8)	−0.0074 (7)
C8	0.0485 (8)	0.0423 (7)	0.0460 (8)	0.0053 (6)	0.0067 (6)	0.0048 (6)
C9	0.0746 (11)	0.0393 (7)	0.0497 (8)	0.0040 (7)	−0.0012 (8)	−0.0012 (6)
C10	0.0732 (11)	0.0477 (8)	0.0444 (8)	0.0056 (7)	−0.0033 (8)	0.0032 (6)
C11	0.0515 (9)	0.0400 (7)	0.0504 (8)	0.0028 (6)	0.0057 (7)	0.0048 (6)
C12	0.0667 (10)	0.0409 (8)	0.0567 (9)	−0.0004 (7)	−0.0039 (8)	−0.0011 (7)
C13	0.0678 (11)	0.0512 (9)	0.0506 (8)	0.0056 (7)	−0.0069 (8)	0.0003 (7)
C14	0.0548 (9)	0.0449 (8)	0.0557 (9)	0.0040 (7)	0.0042 (7)	0.0059 (7)
C15	0.0741 (12)	0.0477 (8)	0.0674 (11)	0.0109 (8)	0.0063 (9)	0.0177 (8)
C16	0.1006 (17)	0.0817 (13)	0.0591 (11)	0.0234 (12)	0.0061 (11)	0.0173 (10)

Geometric parameters (Å, º)

S1—O2	1.4292 (12)	C6—C7	1.372 (3)
S1—O1	1.4302 (13)	C6—H6A	0.9300
S1—N1	1.6219 (14)	C7—H7A	0.9300
S1—C5	1.7573 (18)	C8—C9	1.387 (2)
N1—C8	1.4112 (18)	C8—C13	1.389 (2)
N1—H1A	0.8600	C9—C10	1.375 (2)
O3—C14	1.2035 (18)	C9—H9A	0.9300
O4—C14	1.325 (2)	C10—C11	1.390 (2)
O4—C15	1.4526 (19)	C10—H10A	0.9300
C1—C2	1.499 (3)	C11—C12	1.381 (2)
C1—H1C	0.9600	C11—C14	1.4833 (19)
C1—H1D	0.9600	C12—C13	1.384 (2)
C1—H1E	0.9600	C12—H12A	0.9300
C2—C3	1.385 (2)	C13—H13A	0.9300
C2—C7	1.390 (3)	C15—C16	1.485 (3)
C3—C4	1.376 (3)	C15—H15A	0.9700
C3—H3A	0.9300	C15—H15B	0.9700
C4—C5	1.387 (2)	C16—H16A	0.9600
C4—H4A	0.9300	C16—H16B	0.9600
C5—C6	1.378 (2)	C16—H16C	0.9600
O2—S1—O1	119.32 (8)	C9—C8—C13	119.50 (13)
O2—S1—N1	104.73 (7)	C9—C8—N1	116.83 (13)
O1—S1—N1	109.42 (8)	C13—C8—N1	123.64 (15)
O2—S1—C5	108.07 (8)	C10—C9—C8	120.44 (14)
O1—S1—C5	108.33 (8)	C10—C9—H9A	119.8
N1—S1—C5	106.23 (7)	C8—C9—H9A	119.8
C8—N1—S1	127.74 (11)	C9—C10—C11	120.37 (15)
C8—N1—H1A	116.1	C9—C10—H10A	119.8
S1—N1—H1A	116.1	C11—C10—H10A	119.8
C14—O4—C15	117.14 (13)	C12—C11—C10	119.13 (13)
C2—C1—H1C	109.5	C12—C11—C14	118.68 (13)
C2—C1—H1D	109.5	C10—C11—C14	122.19 (15)
H1C—C1—H1D	109.5	C11—C12—C13	120.90 (15)
C2—C1—H1E	109.5	C11—C12—H12A	119.6
H1C—C1—H1E	109.5	C13—C12—H12A	119.6
H1D—C1—H1E	109.5	C12—C13—C8	119.65 (15)
C3—C2—C7	117.64 (17)	C12—C13—H13A	120.2
C3—C2—C1	120.95 (17)	C8—C13—H13A	120.2
C7—C2—C1	121.40 (17)	O3—C14—O4	123.01 (14)
C4—C3—C2	121.41 (17)	O3—C14—C11	124.28 (15)
C4—C3—H3A	119.3	O4—C14—C11	112.70 (13)
C2—C3—H3A	119.3	O4—C15—C16	107.31 (15)
C3—C4—C5	119.69 (16)	O4—C15—H15A	110.3
C3—C4—H4A	120.2	C16—C15—H15A	110.3
C5—C4—H4A	120.2	O4—C15—H15B	110.3
C6—C5—C4	119.84 (17)	C16—C15—H15B	110.3
C6—C5—S1	120.26 (13)	H15A—C15—H15B	108.5
C4—C5—S1	119.77 (12)	C15—C16—H16A	109.5
C7—C6—C5	119.72 (16)	C15—C16—H16B	109.5
C7—C6—H6A	120.1	H16A—C16—H16B	109.5
C5—C6—H6A	120.1	C15—C16—H16C	109.5
C6—C7—C2	121.71 (16)	H16A—C16—H16C	109.5
C6—C7—H7A	119.1	H16B—C16—H16C	109.5
C2—C7—H7A	119.1
O2—S1—N1—C8	−174.66 (14)	S1—N1—C8—C9	−165.37 (12)
O1—S1—N1—C8	−45.65 (16)	S1—N1—C8—C13	16.4 (2)
C5—S1—N1—C8	71.09 (16)	C13—C8—C9—C10	1.0 (3)
C7—C2—C3—C4	0.6 (2)	N1—C8—C9—C10	−177.25 (16)
C1—C2—C3—C4	−178.41 (16)	C8—C9—C10—C11	−0.8 (3)
C2—C3—C4—C5	−0.2 (3)	C9—C10—C11—C12	0.2 (3)
C3—C4—C5—C6	−0.5 (2)	C9—C10—C11—C14	179.91 (16)
C3—C4—C5—S1	175.24 (13)	C10—C11—C12—C13	0.1 (3)
O2—S1—C5—C6	115.66 (13)	C14—C11—C12—C13	−179.62 (16)
O1—S1—C5—C6	−14.94 (14)	C11—C12—C13—C8	0.2 (3)
N1—S1—C5—C6	−132.40 (13)	C9—C8—C13—C12	−0.7 (3)
O2—S1—C5—C4	−60.06 (14)	N1—C8—C13—C12	177.43 (16)
O1—S1—C5—C4	169.34 (12)	C15—O4—C14—O3	1.4 (3)
N1—S1—C5—C4	51.88 (13)	C15—O4—C14—C11	−179.39 (14)
C4—C5—C6—C7	0.8 (2)	C12—C11—C14—O3	−3.5 (3)
S1—C5—C6—C7	−174.91 (12)	C10—C11—C14—O3	176.78 (18)
C5—C6—C7—C2	−0.4 (2)	C12—C11—C14—O4	177.36 (14)
C3—C2—C7—C6	−0.3 (2)	C10—C11—C14—O4	−2.4 (2)
C1—C2—C7—C6	178.72 (16)	C14—O4—C15—C16	−178.08 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3^i	0.86	2.09	2.844 (2)	147

Symmetry code: (i) x, y−1, z.