N-Cyclo­hexyl-2-nitro­benzene­sulfonamide

The cyclo­hexane ring of the title compound, C₁₂H₁₆N₂O₄S, adopts a chair conformation. The NH group forms a bifurcated hydrogen bond to two O atoms.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.043
• wR factor = 0.105
• Data-to-parameter ratio = 20.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.35 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.22 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C9
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C11
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      32.00 A   3  

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.32
           From the CIF: _reflns_number_total               3598
           Count of symmetry unique reflns         2179
           Completeness (_total/calc)            165.12%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1419
           Fraction of Friedel pairs measured     0.651
           Are heavy atom types Z>Si present        yes

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

N-cyclohexyl-2-nitrobenzenesulfonamide

Crystal data

C12H16N2O4S	Dx = 1.305 Mg m^−3
Mr = 284.33	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41212	Cell parameters from 3598 reflections
a = 9.6392 (13) Å	θ = 2.2–28.3°
c = 31.162 (6) Å	µ = 0.24 mm^−1
V = 2895.4 (8) Å^3	T = 294 K
Z = 8	Prism, colourless
F(000) = 1200	0.24 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3598 independent reflections
Radiation source: fine-focus sealed tube	2528 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
Detector resolution: 8.26 pixels mm^-1	θmax = 28.3°, θmin = 2.2°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −6→12
Tmin = 0.946, Tmax = 0.977	l = −40→41
18343 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.0509P)^2 + 0.3079P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
3598 reflections	Δρmax = 0.18 e Å^−3
176 parameters	Δρmin = −0.22 e Å^−3
0 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.06 (10)

Special details

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.

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

	x	y	z	Uiso*/Ueq
S1	0.35221 (6)	0.08754 (6)	0.111724 (16)	0.04062 (15)
N1	0.2007 (2)	0.1524 (2)	0.11290 (7)	0.0487 (5)
H1	0.203 (3)	0.227 (3)	0.1037 (8)	0.050 (8)*
N2	0.4593 (2)	0.2875 (2)	0.03810 (6)	0.0501 (5)
O1	0.34763 (18)	−0.04153 (16)	0.13391 (5)	0.0536 (4)
O2	0.44605 (17)	0.19086 (18)	0.12594 (5)	0.0528 (4)
O3	0.3543 (2)	0.34162 (18)	0.05151 (5)	0.0614 (5)
O4	0.5646 (2)	0.3499 (2)	0.03015 (7)	0.0878 (7)
C1	0.4013 (2)	0.0446 (2)	0.05790 (6)	0.0399 (5)
C2	0.4560 (2)	0.1390 (2)	0.02905 (6)	0.0418 (5)
C3	0.5079 (3)	0.0985 (3)	−0.01007 (7)	0.0625 (7)
H3	0.5467	0.1636	−0.0286	0.075*
C4	0.5022 (4)	−0.0367 (3)	−0.02145 (9)	0.0836 (10)
H4	0.5360	−0.0646	−0.0480	0.100*
C5	0.4474 (4)	−0.1318 (3)	0.00584 (9)	0.0860 (10)
H5	0.4441	−0.2246	−0.0022	0.103*
C6	0.3960 (3)	−0.0924 (3)	0.04566 (8)	0.0598 (7)
H6	0.3582	−0.1584	0.0640	0.072*
C7	0.0730 (2)	0.0722 (3)	0.10532 (8)	0.0516 (6)
H7	0.0943	−0.0259	0.1103	0.062*
C8	0.0225 (4)	0.0865 (5)	0.06053 (10)	0.1061 (14)
H8A	0.0926	0.0518	0.0409	0.127*
H8B	0.0074	0.1838	0.0541	0.127*
C9	−0.1120 (4)	0.0067 (6)	0.05384 (13)	0.1342 (19)
H9A	−0.1451	0.0225	0.0249	0.161*
H9B	−0.0939	−0.0918	0.0570	0.161*
C10	−0.2218 (3)	0.0486 (5)	0.08485 (13)	0.1055 (13)
H10A	−0.2488	0.1440	0.0795	0.127*
H10B	−0.3029	−0.0097	0.0811	0.127*
C11	−0.1692 (3)	0.0348 (5)	0.12952 (12)	0.1094 (14)
H11A	−0.1538	−0.0626	0.1358	0.131*
H11B	−0.2393	0.0687	0.1492	0.131*
C12	−0.0343 (3)	0.1146 (4)	0.13706 (10)	0.0818 (10)
H12A	−0.0517	0.2133	0.1345	0.098*
H12B	−0.0009	0.0964	0.1659	0.098*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0420 (3)	0.0409 (3)	0.0390 (2)	−0.0037 (3)	0.0025 (2)	0.0027 (2)
N1	0.0474 (11)	0.0382 (11)	0.0605 (12)	−0.0002 (10)	0.0113 (9)	0.0043 (11)
N2	0.0571 (13)	0.0475 (12)	0.0456 (10)	−0.0036 (10)	0.0081 (10)	0.0062 (9)
O1	0.0592 (10)	0.0474 (9)	0.0543 (9)	−0.0014 (8)	0.0032 (8)	0.0146 (8)
O2	0.0564 (10)	0.0577 (10)	0.0444 (8)	−0.0143 (7)	−0.0014 (7)	−0.0045 (8)
O3	0.0698 (12)	0.0495 (10)	0.0649 (10)	0.0110 (10)	0.0188 (9)	0.0054 (8)
O4	0.0783 (15)	0.0762 (14)	0.1089 (17)	−0.0290 (13)	0.0319 (13)	−0.0033 (13)
C1	0.0375 (12)	0.0421 (12)	0.0403 (11)	0.0024 (9)	−0.0035 (9)	−0.0046 (10)
C2	0.0398 (12)	0.0460 (12)	0.0396 (10)	0.0052 (10)	0.0018 (9)	−0.0007 (10)
C3	0.078 (2)	0.0668 (18)	0.0430 (13)	0.0137 (16)	0.0093 (12)	0.0000 (12)
C4	0.124 (3)	0.077 (2)	0.0495 (16)	0.018 (2)	0.0037 (17)	−0.0164 (16)
C5	0.130 (3)	0.0589 (19)	0.0690 (18)	0.0065 (19)	−0.0062 (19)	−0.0266 (17)
C6	0.0721 (18)	0.0446 (13)	0.0628 (15)	−0.0031 (13)	−0.0062 (13)	−0.0045 (12)
C7	0.0414 (13)	0.0491 (14)	0.0643 (15)	−0.0011 (11)	0.0014 (12)	0.0034 (12)
C8	0.066 (2)	0.187 (4)	0.0647 (19)	−0.010 (3)	−0.0036 (16)	0.000 (2)
C9	0.066 (2)	0.236 (6)	0.100 (3)	−0.015 (3)	−0.023 (2)	−0.029 (3)
C10	0.049 (2)	0.131 (4)	0.136 (4)	0.000 (2)	−0.019 (2)	0.019 (3)
C11	0.054 (2)	0.161 (4)	0.113 (3)	−0.027 (2)	0.013 (2)	0.011 (3)
C12	0.0518 (16)	0.113 (3)	0.0804 (19)	−0.0135 (18)	0.0164 (15)	−0.003 (2)

Geometric parameters (Å, º)

S1—O2	1.4164 (16)	C6—H6	0.9300
S1—O1	1.4239 (16)	C7—C8	1.484 (4)
S1—N1	1.589 (2)	C7—C12	1.488 (4)
S1—C1	1.791 (2)	C7—H7	0.9800
N1—C7	1.473 (3)	C8—C9	1.522 (5)
N1—H1	0.78 (3)	C8—H8A	0.9700
N2—O4	1.205 (3)	C8—H8B	0.9700
N2—O3	1.213 (3)	C9—C10	1.489 (5)
N2—C2	1.459 (3)	C9—H9A	0.9700
C1—C6	1.375 (3)	C9—H9B	0.9700
C1—C2	1.383 (3)	C10—C11	1.487 (5)
C2—C3	1.375 (3)	C10—H10A	0.9700
C3—C4	1.352 (4)	C10—H10B	0.9700
C3—H3	0.9300	C11—C12	1.529 (4)
C4—C5	1.358 (4)	C11—H11A	0.9700
C4—H4	0.9300	C11—H11B	0.9700
C5—C6	1.389 (4)	C12—H12A	0.9700
C5—H5	0.9300	C12—H12B	0.9700
O2—S1—O1	118.84 (11)	N1—C7—H7	107.8
O2—S1—N1	107.64 (11)	C8—C7—H7	107.8
O1—S1—N1	107.71 (11)	C12—C7—H7	107.8
O2—S1—C1	106.66 (10)	C7—C8—C9	111.1 (3)
O1—S1—C1	105.12 (10)	C7—C8—H8A	109.4
N1—S1—C1	110.80 (11)	C9—C8—H8A	109.4
C7—N1—S1	123.92 (17)	C7—C8—H8B	109.4
C7—N1—H1	117 (2)	C9—C8—H8B	109.4
S1—N1—H1	109.2 (19)	H8A—C8—H8B	108.0
O4—N2—O3	123.9 (2)	C10—C9—C8	112.3 (4)
O4—N2—C2	118.0 (2)	C10—C9—H9A	109.1
O3—N2—C2	118.0 (2)	C8—C9—H9A	109.1
C6—C1—C2	117.7 (2)	C10—C9—H9B	109.1
C6—C1—S1	118.16 (19)	C8—C9—H9B	109.1
C2—C1—S1	123.86 (17)	H9A—C9—H9B	107.9
C3—C2—C1	121.9 (2)	C11—C10—C9	109.9 (3)
C3—C2—N2	116.2 (2)	C11—C10—H10A	109.7
C1—C2—N2	121.87 (19)	C9—C10—H10A	109.7
C4—C3—C2	119.4 (3)	C11—C10—H10B	109.7
C4—C3—H3	120.3	C9—C10—H10B	109.7
C2—C3—H3	120.3	H10A—C10—H10B	108.2
C3—C4—C5	120.2 (3)	C10—C11—C12	112.9 (3)
C3—C4—H4	119.9	C10—C11—H11A	109.0
C5—C4—H4	119.9	C12—C11—H11A	109.0
C4—C5—C6	120.9 (3)	C10—C11—H11B	109.0
C4—C5—H5	119.6	C12—C11—H11B	109.0
C6—C5—H5	119.6	H11A—C11—H11B	107.8
C1—C6—C5	119.8 (3)	C7—C12—C11	110.5 (3)
C1—C6—H6	120.1	C7—C12—H12A	109.5
C5—C6—H6	120.1	C11—C12—H12A	109.5
N1—C7—C8	112.1 (2)	C7—C12—H12B	109.5
N1—C7—C12	109.3 (2)	C11—C12—H12B	109.5
C8—C7—C12	111.8 (3)	H12A—C12—H12B	108.1
O2—S1—N1—C7	−172.45 (18)	C1—C2—C3—C4	1.9 (4)
O1—S1—N1—C7	−43.2 (2)	N2—C2—C3—C4	−177.0 (3)
C1—S1—N1—C7	71.3 (2)	C2—C3—C4—C5	−0.9 (5)
O2—S1—C1—C6	140.3 (2)	C3—C4—C5—C6	0.2 (6)
O1—S1—C1—C6	13.3 (2)	C2—C1—C6—C5	1.3 (4)
N1—S1—C1—C6	−102.8 (2)	S1—C1—C6—C5	−173.0 (2)
O2—S1—C1—C2	−33.6 (2)	C4—C5—C6—C1	−0.4 (5)
O1—S1—C1—C2	−160.68 (19)	S1—N1—C7—C8	−97.9 (3)
N1—S1—C1—C2	83.2 (2)	S1—N1—C7—C12	137.5 (2)
C6—C1—C2—C3	−2.1 (4)	N1—C7—C8—C9	−178.1 (3)
S1—C1—C2—C3	171.9 (2)	C12—C7—C8—C9	−55.0 (5)
C6—C1—C2—N2	176.7 (2)	C7—C8—C9—C10	55.5 (6)
S1—C1—C2—N2	−9.3 (3)	C8—C9—C10—C11	−54.7 (6)
O4—N2—C2—C3	−45.6 (3)	C9—C10—C11—C12	54.7 (5)
O3—N2—C2—C3	131.4 (2)	N1—C7—C12—C11	179.0 (3)
O4—N2—C2—C1	135.5 (2)	C8—C7—C12—C11	54.3 (4)
O3—N2—C2—C1	−47.5 (3)	C10—C11—C12—C7	−54.8 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.78 (3)	2.45 (3)	3.030 (3)	133 (2)
N1—H1···O1^i	0.78 (3)	2.31 (3)	2.989 (3)	146 (2)

Symmetry code: (i) −x+1/2, y+1/2, −z+1/4.