Dicyclo­hexyl­ammonium 4-nitro­phenyl­sulfinate

In the crystal structure of the title compound, C₁₂H₂₄N⁺·NO₂–C₆H₄–SO₂⁻, dimers are formed by N—H...O and C—H...O hydrogen-bond inter­actions. These dimers are located around centres of inversion.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in main residue
• R factor = 0.082
• wR factor = 0.243
• Data-to-parameter ratio = 19.2

checkCIF/PLATON results

No syntax errors found



Alert level B
REFLT01_ALERT_1_B  The number of symmetry-independent reflections cannot
            exceed the total number of reflections measured
            Number of symmetry-independent reflections =   5011
            Total number of reflections                =   4389
REFLT03_ALERT_3_B  Reflection count > 10% excess reflns - sys abs data present?
           From the CIF: _diffrn_reflns_theta_max           27.00
           From the CIF: _diffrn_reflns_theta_full          27.00
           From the CIF: _reflns_number_total               5011
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         4435
           Completeness (_total/calc)            112.99%
PLAT021_ALERT_1_B Ratio Unique / Expected Reflections too High ...       1.13

Alert level C
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
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        C12
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C15
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.08
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.07
PLAT301_ALERT_3_C Main Residue  Disorder .........................       7.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
  10 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
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

Dicyclohexylammonium 4-nitrophenylsulfinate

Crystal data

C12H24N^+·C6H4NO4S^−	F(000) = 792
Mr = 368.48	Dx = 1.207 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 2317 reflections
a = 13.185 (7) Å	θ = 1.5–27.0°
b = 11.407 (5) Å	µ = 0.18 mm^−1
c = 16.055 (9) Å	T = 298 K
β = 122.906 (5)°	Needle, yellow
V = 2027.3 (18) Å^3	0.45 × 0.25 × 0.19 mm
Z = 4

Data collection

Nonius KappaCCD area-detector diffractometer	5011 independent reflections
Radiation source: fine-focus sealed tube	3556 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0
φ scans, and ω scans with κ offsets	θmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = 0→16
Tmin = 0.950, Tmax = 0.964	k = −14→0
4389 measured reflections	l = −20→16

Refinement

Refinement on F^2	127 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.082	w = 1/[σ^2(Fo^2) + (0.1198P)^2 + 1.1689P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.243	(Δ/σ)max = 0.025
S = 1.11	Δρmax = 0.45 e Å^−3
4389 reflections	Δρmin = −0.42 e Å^−3
229 parameters

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	Occ. (<1)
S1	0.46747 (8)	0.74752 (7)	0.91837 (7)	0.0570 (3)
O1	0.4046 (3)	0.8618 (3)	0.8759 (3)	0.0965 (12)
O2	0.5168 (3)	0.7467 (2)	1.0260 (2)	0.0782 (9)
O3	0.0844 (4)	0.3059 (3)	0.8061 (4)	0.1415 (19)
O4	−0.0396 (3)	0.4455 (3)	0.7646 (3)	0.1077 (12)
N1	0.0599 (3)	0.4089 (3)	0.7943 (3)	0.0766 (10)
N2	0.5064 (2)	0.5702 (3)	0.6392 (2)	0.0470 (6)
C1	0.3402 (3)	0.6480 (2)	0.8723 (2)	0.0422 (6)
C2	0.3635 (3)	0.5285 (3)	0.8813 (2)	0.0489 (7)
H2	0.4413	0.5014	0.9057	0.059*
C3	0.2714 (3)	0.4503 (3)	0.8541 (3)	0.0556 (8)
H3	0.2861	0.37	0.8606	0.067*
C4	0.1571 (3)	0.4928 (3)	0.8171 (2)	0.0515 (8)
C5	0.1303 (3)	0.6106 (3)	0.8045 (3)	0.0541 (8)
H5	0.0518	0.6368	0.7783	0.065*
C6	0.2236 (3)	0.6888 (3)	0.8320 (3)	0.0507 (7)
H6	0.208	0.7689	0.8234	0.061*
C7	0.6053 (3)	0.6075 (3)	0.7416 (3)	0.0648 (10)
H7	0.5833	0.6828	0.7569	0.078*
C8	0.7215 (4)	0.6233 (5)	0.7432 (3)	0.0849 (10)
H8A	0.7089	0.6822	0.6949	0.102*
H8B	0.7421	0.5501	0.7251	0.102*
C9	0.8253 (5)	0.6612 (6)	0.8466 (4)	0.1133 (18)
H9A	0.898	0.662	0.8452	0.136*
H9B	0.8096	0.7418	0.8555	0.136*
C10'	0.8523 (10)	0.6027 (13)	0.9287 (8)	0.0849 (10)	0.465 (13)
H1A'	0.9071	0.648	0.9876	0.102*	0.465 (13)
H1B'	0.8899	0.528	0.9325	0.102*	0.465 (13)
C11'	0.7336 (8)	0.5843 (15)	0.9196 (7)	0.0849 (10)	0.465 (13)
H1C'	0.7041	0.6604	0.9241	0.102*	0.465 (13)
H1D'	0.7492	0.5389	0.9765	0.102*	0.465 (13)
C10	0.8343 (9)	0.5568 (11)	0.9218 (7)	0.0849 (10)	0.535 (13)
H10A	0.8635	0.4867	0.9072	0.102*	0.535 (13)
H10B	0.896	0.5801	0.9889	0.102*	0.535 (13)
C11	0.7228 (8)	0.5227 (13)	0.9216 (6)	0.0849 (10)	0.535 (13)
H11A	0.7342	0.4468	0.9529	0.102*	0.535 (13)
H11B	0.7067	0.5803	0.9575	0.102*	0.535 (13)
C12	0.6233 (4)	0.5182 (6)	0.8181 (3)	0.0983 (17)
H12A	0.6484	0.4427	0.8075	0.118*
H12B	0.5512	0.5085	0.8196	0.118*
C13	0.3797 (3)	0.5584 (3)	0.6170 (3)	0.0580 (9)
H13	0.3828	0.5106	0.669	0.07*
C14	0.3288 (4)	0.6778 (5)	0.6162 (4)	0.0870 (14)
H14A	0.332	0.7286	0.5692	0.104*
H14B	0.377	0.7132	0.6815	0.104*
C15	0.1960 (4)	0.6653 (7)	0.5867 (4)	0.112 (2)
H15A	0.1943	0.621	0.6375	0.135*
H15B	0.163	0.7425	0.5832	0.135*
C16	0.1192 (4)	0.6049 (5)	0.4890 (4)	0.0917 (15)
H16A	0.1147	0.6526	0.4371	0.11*
H16B	0.038	0.5954	0.4744	0.11*
C17	0.1709 (4)	0.4861 (5)	0.4905 (4)	0.0955 (15)
H17A	0.1222	0.4502	0.4255	0.115*
H17B	0.1681	0.4359	0.5379	0.115*
C18	0.3013 (3)	0.4966 (4)	0.5185 (3)	0.0712 (10)
H18A	0.3335	0.4189	0.5224	0.085*
H18B	0.303	0.5398	0.4672	0.085*
H100	0.522 (3)	0.499 (3)	0.629 (2)	0.046 (9)*
H200	0.498 (3)	0.620 (3)	0.597 (3)	0.055 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0477 (5)	0.0504 (5)	0.0720 (7)	−0.0073 (3)	0.0320 (5)	−0.0076 (4)
O1	0.0726 (19)	0.0601 (17)	0.127 (3)	−0.0118 (14)	0.0350 (19)	0.0323 (17)
O2	0.0722 (19)	0.0566 (16)	0.0658 (18)	−0.0058 (12)	0.0116 (14)	−0.0108 (12)
O3	0.105 (3)	0.059 (2)	0.231 (6)	−0.033 (2)	0.072 (3)	−0.016 (2)
O4	0.063 (2)	0.106 (3)	0.143 (3)	−0.0290 (18)	0.048 (2)	−0.020 (2)
N1	0.062 (2)	0.069 (2)	0.086 (2)	−0.0243 (17)	0.0318 (19)	−0.0175 (17)
N2	0.0451 (14)	0.0461 (15)	0.0462 (15)	0.0074 (11)	0.0225 (12)	−0.0013 (12)
C1	0.0441 (15)	0.0413 (14)	0.0388 (14)	0.0001 (11)	0.0210 (12)	−0.0022 (11)
C2	0.0449 (16)	0.0452 (16)	0.0514 (17)	0.0087 (12)	0.0228 (14)	0.0019 (13)
C3	0.061 (2)	0.0352 (15)	0.062 (2)	0.0027 (13)	0.0282 (17)	−0.0027 (13)
C4	0.0483 (17)	0.0501 (17)	0.0481 (17)	−0.0092 (13)	0.0210 (14)	−0.0070 (13)
C5	0.0383 (15)	0.0559 (19)	0.0567 (18)	0.0029 (13)	0.0183 (14)	−0.0021 (14)
C6	0.0491 (17)	0.0366 (15)	0.0604 (19)	0.0057 (12)	0.0259 (15)	0.0006 (13)
C7	0.0511 (18)	0.070 (2)	0.0521 (18)	0.0190 (16)	0.0142 (15)	−0.0172 (16)
C8	0.0610 (17)	0.105 (3)	0.0605 (15)	−0.0021 (19)	0.0147 (13)	−0.0101 (18)
C9	0.065 (3)	0.130 (5)	0.101 (4)	−0.010 (3)	0.017 (3)	−0.023 (3)
C10'	0.0610 (17)	0.105 (3)	0.0605 (15)	−0.0021 (19)	0.0147 (13)	−0.0101 (18)
C11'	0.0610 (17)	0.105 (3)	0.0605 (15)	−0.0021 (19)	0.0147 (13)	−0.0101 (18)
C10	0.0610 (17)	0.105 (3)	0.0605 (15)	−0.0021 (19)	0.0147 (13)	−0.0101 (18)
C11	0.0610 (17)	0.105 (3)	0.0605 (15)	−0.0021 (19)	0.0147 (13)	−0.0101 (18)
C12	0.068 (3)	0.178 (5)	0.046 (2)	0.015 (3)	0.0282 (19)	0.018 (3)
C13	0.0454 (17)	0.079 (2)	0.0503 (18)	0.0127 (16)	0.0263 (15)	0.0085 (16)
C14	0.061 (2)	0.107 (3)	0.085 (3)	0.025 (2)	0.034 (2)	−0.023 (3)
C15	0.070 (3)	0.175 (6)	0.098 (4)	0.045 (3)	0.049 (3)	−0.003 (4)
C16	0.048 (2)	0.136 (4)	0.090 (3)	0.017 (2)	0.037 (2)	0.031 (3)
C17	0.053 (2)	0.111 (4)	0.102 (4)	−0.007 (2)	0.029 (2)	0.015 (3)
C18	0.050 (2)	0.069 (2)	0.079 (3)	−0.0013 (17)	0.0248 (18)	−0.0074 (19)

Geometric parameters (Å, º)

S1—O2	1.480 (3)	C10'—H1A'	0.97
S1—O1	1.496 (3)	C10'—H1B'	0.97
S1—C1	1.817 (3)	C11'—C12	1.663 (10)
O3—N1	1.206 (5)	C11'—H1C'	0.97
O4—N1	1.202 (5)	C11'—H1D'	0.97
N1—C4	1.477 (4)	C10—C11	1.520 (11)
N2—C7	1.502 (4)	C10—H10A	0.97
N2—C13	1.512 (4)	C10—H10B	0.97
N2—H100	0.87 (4)	C11—C12	1.455 (8)
N2—H200	0.84 (4)	C11—H11A	0.97
C1—C6	1.386 (4)	C11—H11B	0.97
C1—C2	1.387 (4)	C12—H12A	0.97
C2—C3	1.373 (5)	C12—H12B	0.97
C2—H2	0.93	C13—C18	1.514 (5)
C3—C4	1.373 (5)	C13—C14	1.516 (6)
C3—H3	0.93	C13—H13	0.98
C4—C5	1.376 (5)	C14—C15	1.552 (7)
C5—C6	1.384 (5)	C14—H14A	0.97
C5—H5	0.93	C14—H14B	0.97
C6—H6	0.93	C15—C16	1.495 (8)
C7—C12	1.512 (6)	C15—H15A	0.97
C7—C8	1.529 (6)	C15—H15B	0.97
C7—H7	0.98	C16—C17	1.511 (8)
C8—C9	1.532 (6)	C16—H16A	0.97
C8—H8A	0.97	C16—H16B	0.97
C8—H8B	0.97	C17—C18	1.526 (6)
C9—C10'	1.342 (11)	C17—H17A	0.97
C9—C10	1.653 (11)	C17—H17B	0.97
C9—H9A	0.97	C18—H18A	0.97
C9—H9B	0.97	C18—H18B	0.97
C10'—C11'	1.506 (12)
O2—S1—O1	108.7 (2)	C10'—C11'—H1D'	107.9
O2—S1—C1	101.23 (15)	C12—C11'—H1D'	107.8
O1—S1—C1	101.45 (15)	H1C'—C11'—H1D'	107.2
O4—N1—O3	122.8 (4)	C11—C10—C9	119.9 (8)
O4—N1—C4	119.1 (4)	C11—C10—H10A	107.4
O3—N1—C4	118.1 (4)	C9—C10—H10A	107.4
C7—N2—C13	118.3 (3)	C11—C10—H10B	107.4
C7—N2—H100	109 (2)	C9—C10—H10B	107.4
C13—N2—H100	102 (2)	H10A—C10—H10B	106.9
C7—N2—H200	110 (3)	C12—C11—C10	106.4 (7)
C13—N2—H200	103 (2)	C12—C11—H11A	110.5
H100—N2—H200	114 (3)	C10—C11—H11A	110.5
C6—C1—C2	120.4 (3)	C12—C11—H11B	110.5
C6—C1—S1	121.7 (2)	C10—C11—H11B	110.5
C2—C1—S1	117.9 (2)	H11A—C11—H11B	108.6
C3—C2—C1	119.9 (3)	C11—C12—C7	123.4 (7)
C3—C2—H2	120.1	C7—C12—C11'	99.1 (7)
C1—C2—H2	120.1	C11—C12—H12A	92.8
C2—C3—C4	118.8 (3)	C7—C12—H12A	112
C2—C3—H3	120.6	C11'—C12—H12A	111.9
C4—C3—H3	120.6	C11—C12—H12B	105.2
C3—C4—C5	122.8 (3)	C7—C12—H12B	112
C3—C4—N1	118.6 (3)	C11'—C12—H12B	112
C5—C4—N1	118.5 (3)	H12A—C12—H12B	109.6
C4—C5—C6	118.0 (3)	N2—C13—C18	109.2 (3)
C4—C5—H5	121	N2—C13—C14	110.5 (3)
C6—C5—H5	121	C18—C13—C14	111.2 (3)
C5—C6—C1	120.1 (3)	N2—C13—H13	108.6
C5—C6—H6	120	C18—C13—H13	108.6
C1—C6—H6	120	C14—C13—H13	108.6
N2—C7—C12	110.9 (4)	C13—C14—C15	109.9 (5)
N2—C7—C8	108.5 (3)	C13—C14—H14A	109.7
C12—C7—C8	110.6 (3)	C15—C14—H14A	109.7
N2—C7—H7	108.9	C13—C14—H14B	109.7
C12—C7—H7	108.9	C15—C14—H14B	109.7
C8—C7—H7	108.9	H14A—C14—H14B	108.2
C7—C8—C9	110.4 (4)	C16—C15—C14	111.8 (4)
C7—C8—H8A	109.6	C16—C15—H15A	109.3
C9—C8—H8A	109.6	C14—C15—H15A	109.3
C7—C8—H8B	109.6	C16—C15—H15B	109.3
C9—C8—H8B	109.6	C14—C15—H15B	109.3
H8A—C8—H8B	108.1	H15A—C15—H15B	107.9
C10'—C9—C8	121.9 (7)	C15—C16—C17	110.8 (4)
C8—C9—C10	104.8 (5)	C15—C16—H16A	109.5
C10'—C9—H9A	106.8	C17—C16—H16A	109.5
C8—C9—H9A	106.9	C15—C16—H16B	109.5
C10—C9—H9A	110.1	C17—C16—H16B	109.5
C10'—C9—H9B	106.9	H16A—C16—H16B	108.1
C8—C9—H9B	106.9	C16—C17—C18	111.2 (4)
C10—C9—H9B	120.7	C16—C17—H17A	109.4
H9A—C9—H9B	106.7	C18—C17—H17A	109.4
C9—C10'—C11'	105.5 (9)	C16—C17—H17B	109.4
C9—C10'—H1A'	110.6	C18—C17—H17B	109.4
C11'—C10'—H1A'	110.6	H17A—C17—H17B	108
C9—C10'—H1B'	110.6	C13—C18—C17	111.4 (4)
C11'—C10'—H1B'	110.6	C13—C18—H18A	109.3
H1A'—C10'—H1B'	108.8	C17—C18—H18A	109.3
C10'—C11'—C12	117.9 (8)	C13—C18—H18B	109.3
C10'—C11'—H1C'	107.8	C17—C18—H18B	109.3
C12—C11'—H1C'	107.8	H18A—C18—H18B	108
O2—S1—C1—C6	98.1 (3)	C8—C9—C10'—C11'	−47.2 (11)
O1—S1—C1—C6	−13.9 (3)	C10—C9—C10'—C11'	−67 (2)
O2—S1—C1—C2	−80.0 (3)	C9—C10'—C11'—C12	55.2 (12)
O1—S1—C1—C2	168.1 (3)	C10'—C9—C10—C11	109 (3)
C6—C1—C2—C3	−2.8 (5)	C8—C9—C10—C11	−53.8 (9)
S1—C1—C2—C3	175.3 (2)	C9—C10—C11—C12	42.7 (11)
C1—C2—C3—C4	0.8 (5)	C10—C11—C12—C7	−41.3 (10)
C2—C3—C4—C5	1.1 (5)	C10—C11—C12—C11'	−62.2 (14)
C2—C3—C4—N1	−176.0 (3)	N2—C7—C12—C11	171.7 (6)
O4—N1—C4—C3	177.9 (4)	C8—C7—C12—C11	51.2 (8)
O3—N1—C4—C3	−2.4 (6)	N2—C7—C12—C11'	−179.3 (5)
O4—N1—C4—C5	0.7 (6)	C8—C7—C12—C11'	60.1 (6)
O3—N1—C4—C5	−179.6 (4)	C10'—C11'—C12—C11	99.2 (17)
C3—C4—C5—C6	−1.1 (5)	C10'—C11'—C12—C7	−63.2 (11)
N1—C4—C5—C6	176.0 (3)	C7—N2—C13—C18	−168.3 (3)
C4—C5—C6—C1	−1.0 (5)	C7—N2—C13—C14	69.1 (4)
C2—C1—C6—C5	2.9 (5)	N2—C13—C14—C15	176.4 (4)
S1—C1—C6—C5	−175.1 (3)	C18—C13—C14—C15	55.0 (5)
C13—N2—C7—C12	63.1 (4)	C13—C14—C15—C16	−56.0 (6)
C13—N2—C7—C8	−175.1 (3)	C14—C15—C16—C17	56.6 (7)
N2—C7—C8—C9	−179.8 (4)	C15—C16—C17—C18	−56.2 (6)
C12—C7—C8—C9	−57.9 (6)	N2—C13—C18—C17	−178.0 (3)
C7—C8—C9—C10'	51.2 (10)	C14—C13—C18—C17	−55.8 (5)
C7—C8—C9—C10	57.4 (7)	C16—C17—C18—C13	55.9 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H100···O1^i	0.87 (4)	1.86 (4)	2.719 (5)	165 (4)
N2—H200···O2^ii	0.85 (4)	1.99 (4)	2.821 (5)	166 (4)
C3—H3···O2^iii	0.93	2.59	3.274 (5)	131
C5—H5···O3^iv	0.93	2.48	3.265 (7)	143
C6—H6···O1	0.93	2.49	2.874 (6)	105

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