Crystal structure and Hirshfeld surface analysis of N,N′-[ethane-1,2-diylbis(­oxy)]bis­(4-methyl­benzene­sulfonamide)

In the crystal, the mol­ecules are linked by N—H...O hydrogen bonds into supra­molecular chains propagating along the [101] direction.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.047
• wR factor = 0.116
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         C6 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C2 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C5 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including        S1      0.092 Check
PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C2       -C7              1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00538 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C16 H20 N2 O6 S2
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     23.657 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.862 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT128_ALERT_4_G Alternate Setting for Input Space Group     C2/c       I2/a Note
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O1             109.0 Degree

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
  11 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: WinGX (Farrugia, 2012); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

N,N'-[Ethane-1,2-diylbis(oxy)]bis(4-methylbenzenesulfonamide)

Crystal data

C16H20N2O6S2	F(000) = 840
Mr = 400.46	Dx = 1.349 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.3393 (18) Å	Cell parameters from 6407 reflections
b = 13.4977 (19) Å	θ = 2.0–27.2°
c = 9.7461 (11) Å	µ = 0.30 mm^−1
β = 113.442 (8)°	T = 296 K
V = 1972.0 (4) Å^3	Prism, colorless
Z = 4	0.56 × 0.36 × 0.13 mm

Data collection

Stoe IPDS 2 diffractometer	1938 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1070 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm^-1	Rint = 0.086
rotation method scans	θmax = 26.0°, θmin = 2.0°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −20→20
Tmin = 0.873, Tmax = 0.973	k = −16→16
6561 measured reflections	l = −12→9

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.0562P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.90	(Δ/σ)max < 0.001
1938 reflections	Δρmax = 0.14 e Å^−3
123 parameters	Δρmin = −0.25 e Å^−3

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
S1	0.19812 (4)	0.13241 (6)	0.11223 (9)	0.0759 (3)
O1	0.04273 (10)	0.15963 (13)	−0.0863 (2)	0.0722 (5)
C1	0.00029 (17)	0.0748 (2)	−0.1731 (3)	0.0698 (7)
H1A	−0.060770	0.071765	−0.181199	0.084*
H1B	0.030688	0.015643	−0.121023	0.084*
O3	0.28617 (11)	0.15543 (15)	0.1220 (3)	0.0907 (7)
O2	0.17825 (13)	0.03371 (14)	0.1379 (3)	0.0928 (7)
N1	0.13462 (14)	0.1594 (2)	−0.0629 (3)	0.0751 (7)
C2	0.16891 (16)	0.2121 (2)	0.2267 (3)	0.0705 (8)
C5	0.1182 (2)	0.3366 (3)	0.4043 (4)	0.0929 (10)
C7	0.1370 (2)	0.1733 (3)	0.3271 (4)	0.1030 (11)
H7	0.131947	0.105133	0.335264	0.124*
C4	0.1518 (2)	0.3736 (3)	0.3067 (4)	0.1041 (11)
H4	0.157573	0.441748	0.299978	0.125*
C6	0.1129 (3)	0.2367 (4)	0.4145 (5)	0.1153 (13)
H6	0.092328	0.210422	0.483059	0.138*
C3	0.1774 (2)	0.3119 (3)	0.2180 (4)	0.0954 (10)
H3	0.200335	0.338428	0.152627	0.115*
C8	0.0890 (3)	0.4066 (4)	0.4973 (5)	0.1375 (16)
H8A	0.083016	0.370639	0.577813	0.206*
H8B	0.032607	0.435597	0.435712	0.206*
H8C	0.132692	0.457942	0.537350	0.206*
H1	0.146 (2)	0.217 (2)	−0.080 (4)	0.089 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0600 (4)	0.0881 (5)	0.0859 (6)	−0.0056 (4)	0.0356 (4)	0.0138 (4)
O1	0.0565 (9)	0.0901 (13)	0.0773 (13)	−0.0033 (9)	0.0344 (9)	−0.0099 (10)
C1	0.0658 (14)	0.0790 (17)	0.0728 (19)	−0.0063 (14)	0.0365 (15)	0.0007 (16)
O3	0.0572 (11)	0.1173 (16)	0.1016 (17)	−0.0056 (10)	0.0358 (11)	0.0226 (13)
O2	0.0875 (13)	0.0809 (13)	0.1204 (19)	−0.0012 (10)	0.0523 (13)	0.0201 (13)
N1	0.0571 (13)	0.0913 (19)	0.0849 (19)	−0.0072 (12)	0.0367 (12)	0.0028 (15)
C2	0.0576 (14)	0.084 (2)	0.0694 (19)	−0.0124 (13)	0.0251 (13)	0.0098 (15)
C5	0.0732 (19)	0.131 (3)	0.065 (2)	−0.008 (2)	0.0175 (16)	−0.010 (2)
C7	0.122 (3)	0.108 (2)	0.100 (3)	−0.038 (2)	0.066 (2)	0.000 (2)
C4	0.124 (3)	0.089 (2)	0.100 (3)	−0.008 (2)	0.044 (2)	0.000 (2)
C6	0.127 (3)	0.148 (4)	0.097 (3)	−0.040 (3)	0.071 (3)	−0.014 (3)
C3	0.107 (2)	0.094 (2)	0.101 (3)	−0.0100 (18)	0.059 (2)	0.011 (2)
C8	0.123 (3)	0.192 (4)	0.093 (3)	0.006 (3)	0.038 (2)	−0.044 (3)

Geometric parameters (Å, º)

S1—O2	1.4168 (19)	C5—C6	1.357 (5)
S1—O3	1.4376 (17)	C5—C4	1.368 (5)
S1—N1	1.647 (3)	C5—C8	1.512 (5)
S1—C2	1.747 (3)	C7—C6	1.371 (5)
O1—N1	1.426 (2)	C7—H7	0.9300
O1—C1	1.429 (3)	C4—C3	1.379 (5)
C1—C1^i	1.494 (5)	C4—H4	0.9300
C1—H1A	0.9700	C6—H6	0.9300
C1—H1B	0.9700	C3—H3	0.9300
N1—H1	0.83 (3)	C8—H8A	0.9600
C2—C3	1.361 (4)	C8—H8B	0.9600
C2—C7	1.381 (4)	C8—H8C	0.9600
O2—S1—O3	119.02 (12)	C6—C5—C8	122.2 (4)
O2—S1—N1	107.29 (15)	C4—C5—C8	120.0 (4)
O3—S1—N1	102.83 (12)	C6—C7—C2	119.1 (3)
O2—S1—C2	109.02 (13)	C6—C7—H7	120.5
O3—S1—C2	110.20 (13)	C2—C7—H7	120.5
N1—S1—C2	107.80 (13)	C5—C4—C3	121.4 (3)
N1—O1—C1	108.99 (19)	C5—C4—H4	119.3
O1—C1—C1^i	113.68 (15)	C3—C4—H4	119.3
O1—C1—H1A	108.8	C5—C6—C7	122.2 (3)
C1^i—C1—H1A	108.8	C5—C6—H6	118.9
O1—C1—H1B	108.8	C7—C6—H6	118.9
C1^i—C1—H1B	108.8	C2—C3—C4	119.7 (3)
H1A—C1—H1B	107.7	C2—C3—H3	120.2
O1—N1—S1	110.82 (17)	C4—C3—H3	120.2
O1—N1—H1	106 (2)	C5—C8—H8A	109.5
S1—N1—H1	108 (2)	C5—C8—H8B	109.5
C3—C2—C7	119.7 (3)	H8A—C8—H8B	109.5
C3—C2—S1	120.6 (2)	C5—C8—H8C	109.5
C7—C2—S1	119.7 (3)	H8A—C8—H8C	109.5
C6—C5—C4	117.9 (3)	H8B—C8—H8C	109.5
N1—O1—C1—C1^i	−63.7 (3)	C3—C2—C7—C6	1.2 (5)
C1—O1—N1—S1	−108.3 (2)	S1—C2—C7—C6	−178.9 (3)
O2—S1—N1—O1	65.1 (2)	C6—C5—C4—C3	1.8 (6)
O3—S1—N1—O1	−168.64 (18)	C8—C5—C4—C3	−178.7 (3)
C2—S1—N1—O1	−52.2 (2)	C4—C5—C6—C7	−2.4 (6)
O2—S1—C2—C3	−176.8 (3)	C8—C5—C6—C7	178.1 (3)
O3—S1—C2—C3	50.9 (3)	C2—C7—C6—C5	0.9 (6)
N1—S1—C2—C3	−60.6 (3)	C7—C2—C3—C4	−1.7 (5)
O2—S1—C2—C7	3.3 (3)	S1—C2—C3—C4	178.4 (3)
O3—S1—C2—C7	−129.0 (2)	C5—C4—C3—C2	0.2 (6)
N1—S1—C2—C7	119.5 (3)

Symmetry code: (i) −x, y, −z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3^ii	0.83 (3)	2.17 (3)	2.974 (3)	162 (3)
C1—H1A···O2^iii	0.97	2.56	3.401 (4)	146

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