4-Methyl­phenyl 3-nitro­benzene­sulfonate

In C₁₃H₁₁NO₅S, there are weak C—H...O interactions which generate rings of motifs S(5), S(6), R²₂(8), R²₂(11) and R²₂(14).

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.033
• wR factor = 0.091
• Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.90

Author Response: Please refer _exptl_special_details

Alert level B
PLAT391_ALERT_3_B Deviating Methyl C13     H-C-H Bond Angle ......      96.00 Deg.

Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           28.37
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               2864
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         3165
           Completeness (_total/calc)             90.49%
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT432_ALERT_2_C Short Inter X...Y Contact  O3     ..  C4       =       3.01 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2     ..  O4       =       2.73 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12    ..  O3       =       2.87 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8     ..  O4       =       2.71 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11    ..  O4       =       2.74 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13C   ..  O3       =       2.83 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13B   ..  O2       =       2.79 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9     ..  O1       =       2.69 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13A   ..  O1       =       2.79 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5     ..  O4       =       2.73 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C13    ..  O2       =       3.73 Ang.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C2     ..  O1       =      97.30 Deg.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C2     ..  O4       =      97.90 Deg.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C12    ..  O3       =      98.30 Deg.

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
  13 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, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

4-Methylphenyl 3-nitrobenzenesulfonate

Crystal data

C13H11NO5S	F(000) = 608
Mr = 293.29	Dx = 1.539 Mg m^−3
Monoclinic, P21/n	Melting point = 393–395 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.2127 (13) Å	Cell parameters from 6112 reflections
b = 12.9944 (19) Å	θ = 2.5–28.3°
c = 10.5892 (15) Å	µ = 0.28 mm^−1
β = 93.267 (2)°	T = 100 K
V = 1265.6 (3) Å^3	Block, colorless
Z = 4	0.41 × 0.27 × 0.24 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2864 independent reflections
Radiation source: fine-focus sealed tube	2611 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 28.4°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.896, Tmax = 0.937	k = −16→14
7309 measured reflections	l = −14→13

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.091	All H-atom parameters refined
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0489P)^2 + 0.5196P] where P = (Fo^2 + 2Fc^2)/3
2864 reflections	(Δ/σ)max < 0.001
225 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

Experimental. "The Tmin and Tmax values obtained from the SIZE instruction are listed above. The absorption correction was applied using SADABS and it gives 0.892917 ratio of min/max transmission. The _diffrn_measured_ fraction_theta_full is low as the diffraction geometry does not allow us to go beyond this value."

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	0.06680 (3)	0.93041 (3)	0.30458 (3)	0.01784 (11)
O1	0.41790 (11)	1.02520 (8)	0.69085 (9)	0.0248 (2)
O2	0.58241 (12)	0.90676 (9)	0.71275 (10)	0.0291 (3)
O3	0.04280 (11)	0.87660 (8)	0.18808 (9)	0.0233 (2)
O4	0.07248 (11)	1.03981 (8)	0.30668 (9)	0.0231 (2)
O5	−0.06041 (10)	0.90461 (7)	0.39520 (9)	0.0204 (2)
N	0.47364 (13)	0.94429 (9)	0.65927 (11)	0.0205 (3)
C1	0.22184 (14)	0.87864 (10)	0.38559 (12)	0.0174 (3)
C2	0.28348 (15)	0.93167 (10)	0.48895 (12)	0.0179 (3)
C3	0.40617 (14)	0.88908 (10)	0.54934 (12)	0.0178 (3)
C4	0.46872 (15)	0.79852 (11)	0.51013 (13)	0.0207 (3)
C5	0.40270 (16)	0.74664 (11)	0.40794 (14)	0.0223 (3)
C6	0.27922 (15)	0.78605 (11)	0.34485 (13)	0.0201 (3)
C7	−0.10320 (14)	0.80050 (11)	0.41111 (13)	0.0192 (3)
C8	−0.05293 (16)	0.74991 (12)	0.51959 (13)	0.0228 (3)
C9	−0.10083 (16)	0.65048 (12)	0.53991 (14)	0.0235 (3)
C10	−0.19800 (15)	0.60201 (11)	0.45383 (13)	0.0209 (3)
C11	−0.24677 (15)	0.65614 (11)	0.34562 (13)	0.0213 (3)
C12	−0.19974 (14)	0.75554 (11)	0.32324 (13)	0.0207 (3)
C13	−0.25024 (18)	0.49443 (12)	0.47685 (16)	0.0272 (3)
H2	0.2415 (18)	0.9932 (14)	0.5188 (16)	0.023 (4)*
H4	0.553 (2)	0.7755 (14)	0.5540 (17)	0.031 (5)*
H5	0.444 (2)	0.6825 (15)	0.3824 (18)	0.035 (5)*
H6	0.2358 (19)	0.7536 (13)	0.2753 (16)	0.026 (4)*
H8	0.013 (2)	0.7845 (13)	0.5808 (17)	0.027 (4)*
H9	−0.068 (2)	0.6167 (15)	0.6142 (18)	0.034 (5)*
H11	−0.316 (2)	0.6252 (14)	0.2858 (17)	0.030 (5)*
H12	−0.2315 (19)	0.7916 (14)	0.2512 (17)	0.026 (4)*
H13A	−0.241 (3)	0.4502 (18)	0.405 (2)	0.056 (7)*
H13B	−0.210 (3)	0.4673 (18)	0.554 (2)	0.055 (6)*
H13C	−0.353 (3)	0.4910 (17)	0.477 (2)	0.052 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01849 (18)	0.01647 (19)	0.01831 (18)	0.00143 (11)	−0.00119 (12)	−0.00057 (11)
O1	0.0287 (5)	0.0233 (6)	0.0222 (5)	−0.0009 (4)	−0.0010 (4)	−0.0033 (4)
O2	0.0248 (5)	0.0310 (6)	0.0302 (6)	0.0002 (4)	−0.0092 (4)	0.0040 (5)
O3	0.0252 (5)	0.0241 (5)	0.0204 (5)	0.0009 (4)	−0.0017 (4)	−0.0031 (4)
O4	0.0255 (5)	0.0176 (5)	0.0258 (5)	0.0019 (4)	−0.0028 (4)	0.0010 (4)
O5	0.0186 (5)	0.0172 (5)	0.0255 (5)	0.0015 (4)	0.0024 (4)	−0.0026 (4)
N	0.0201 (6)	0.0220 (6)	0.0194 (6)	−0.0036 (4)	−0.0005 (5)	0.0040 (4)
C1	0.0170 (6)	0.0167 (6)	0.0185 (6)	0.0006 (5)	0.0011 (5)	0.0017 (5)
C2	0.0184 (6)	0.0163 (7)	0.0191 (6)	0.0000 (5)	0.0024 (5)	0.0009 (5)
C3	0.0184 (6)	0.0178 (7)	0.0172 (6)	−0.0029 (5)	0.0010 (5)	0.0022 (5)
C4	0.0185 (6)	0.0187 (7)	0.0249 (7)	0.0017 (5)	0.0013 (5)	0.0063 (5)
C5	0.0243 (7)	0.0158 (7)	0.0269 (7)	0.0034 (5)	0.0037 (5)	0.0012 (5)
C6	0.0217 (7)	0.0170 (7)	0.0219 (7)	−0.0013 (5)	0.0027 (5)	−0.0014 (5)
C7	0.0176 (6)	0.0168 (7)	0.0234 (6)	0.0008 (5)	0.0035 (5)	−0.0026 (5)
C8	0.0227 (7)	0.0240 (7)	0.0215 (7)	−0.0009 (5)	−0.0013 (5)	−0.0036 (5)
C9	0.0250 (7)	0.0251 (8)	0.0202 (7)	0.0010 (6)	0.0001 (6)	0.0012 (5)
C10	0.0190 (6)	0.0210 (7)	0.0231 (7)	0.0008 (5)	0.0044 (5)	−0.0024 (5)
C11	0.0169 (6)	0.0235 (7)	0.0233 (7)	0.0000 (5)	−0.0001 (5)	−0.0049 (5)
C12	0.0173 (6)	0.0234 (7)	0.0213 (7)	0.0030 (5)	0.0000 (5)	−0.0003 (5)
C13	0.0302 (8)	0.0220 (8)	0.0297 (8)	−0.0036 (6)	0.0046 (6)	−0.0006 (6)

Geometric parameters (Å, º)

S1—O3	1.4243 (10)	C5—H5	0.962 (19)
S1—O4	1.4227 (11)	C6—H6	0.920 (18)
S1—O5	1.5921 (10)	C7—C12	1.380 (2)
S1—C1	1.7575 (14)	C7—C8	1.380 (2)
O1—N	1.2249 (16)	C8—C9	1.386 (2)
O2—N	1.2239 (16)	C8—H8	0.975 (18)
O5—C7	1.4218 (17)	C9—C10	1.391 (2)
N—C3	1.4744 (17)	C9—H9	0.936 (19)
C1—C2	1.3872 (19)	C10—C11	1.397 (2)
C1—C6	1.3926 (19)	C10—C13	1.503 (2)
C2—C3	1.3822 (19)	C11—C12	1.387 (2)
C2—H2	0.950 (17)	C11—H11	0.962 (19)
C3—C4	1.3843 (19)	C12—H12	0.928 (18)
C4—C5	1.386 (2)	C13—H13A	0.96 (2)
C4—H4	0.93 (2)	C13—H13B	0.95 (3)
C5—C6	1.384 (2)	C13—H13C	0.94 (2)
O4—S1—O3	120.52 (6)	C5—C6—H6	121.6 (11)
O4—S1—O5	103.23 (6)	C1—C6—H6	119.2 (11)
O3—S1—O5	109.60 (6)	C12—C7—C8	122.16 (14)
O4—S1—C1	110.29 (6)	C12—C7—O5	119.69 (13)
O3—S1—C1	108.45 (6)	C8—C7—O5	118.01 (12)
O5—S1—C1	103.35 (6)	C7—C8—C9	118.58 (13)
C7—O5—S1	119.37 (8)	C7—C8—H8	120.1 (10)
O2—N—O1	124.10 (12)	C9—C8—H8	121.3 (10)
O2—N—C3	117.95 (12)	C8—C9—C10	121.26 (14)
O1—N—C3	117.96 (11)	C8—C9—H9	118.5 (12)
C2—C1—C6	121.87 (13)	C10—C9—H9	120.2 (12)
C2—C1—S1	118.67 (10)	C9—C10—C11	118.32 (13)
C6—C1—S1	119.46 (11)	C9—C10—C13	120.99 (14)
C3—C2—C1	116.96 (12)	C11—C10—C13	120.70 (13)
C3—C2—H2	121.4 (10)	C12—C11—C10	121.34 (13)
C1—C2—H2	121.6 (10)	C12—C11—H11	118.6 (11)
C2—C3—C4	123.03 (13)	C10—C11—H11	120.0 (11)
C2—C3—N	117.86 (12)	C7—C12—C11	118.34 (13)
C4—C3—N	119.11 (12)	C7—C12—H12	120.1 (11)
C3—C4—C5	118.43 (13)	C11—C12—H12	121.5 (11)
C3—C4—H4	118.2 (11)	C10—C13—H13A	112.6 (14)
C5—C4—H4	123.4 (11)	C10—C13—H13B	112.0 (14)
C6—C5—C4	120.59 (13)	H13A—C13—H13B	115 (2)
C6—C5—H5	121.0 (11)	C10—C13—H13C	111.9 (14)
C4—C5—H5	118.5 (11)	H13A—C13—H13C	96.0 (19)
C5—C6—C1	119.09 (13)	H13B—C13—H13C	109 (2)
O4—S1—O5—C7	176.65 (10)	N—C3—C4—C5	178.96 (12)
O3—S1—O5—C7	47.05 (11)	C3—C4—C5—C6	1.6 (2)
C1—S1—O5—C7	−68.40 (11)	C4—C5—C6—C1	−0.1 (2)
O4—S1—C1—C2	33.29 (12)	C2—C1—C6—C5	−1.1 (2)
O3—S1—C1—C2	167.24 (10)	S1—C1—C6—C5	178.98 (10)
O5—S1—C1—C2	−76.49 (11)	S1—O5—C7—C12	−83.03 (14)
O4—S1—C1—C6	−146.80 (10)	S1—O5—C7—C8	101.09 (13)
O3—S1—C1—C6	−12.85 (13)	C12—C7—C8—C9	0.4 (2)
O5—S1—C1—C6	103.42 (11)	O5—C7—C8—C9	176.16 (11)
C6—C1—C2—C3	0.77 (19)	C7—C8—C9—C10	−0.3 (2)
S1—C1—C2—C3	−179.33 (9)	C8—C9—C10—C11	−0.1 (2)
C1—C2—C3—C4	0.81 (19)	C8—C9—C10—C13	−179.61 (13)
C1—C2—C3—N	179.87 (11)	C9—C10—C11—C12	0.3 (2)
O2—N—C3—C2	−179.90 (12)	C13—C10—C11—C12	179.87 (13)
O1—N—C3—C2	−0.38 (17)	C8—C7—C12—C11	−0.1 (2)
O2—N—C3—C4	−0.81 (18)	O5—C7—C12—C11	−175.84 (11)
O1—N—C3—C4	178.72 (12)	C10—C11—C12—C7	−0.2 (2)
C2—C3—C4—C5	−2.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2	0.93 (2)	2.400 (18)	2.7244 (19)	100.4 (13)
C2—H2···O1	0.950 (17)	2.407 (17)	2.6981 (17)	97.3 (12)
C2—H2···O4	0.950 (17)	2.727 (17)	3.0085 (17)	97.9 (11)
C12—H12···O3	0.928 (18)	2.872 (17)	3.1433 (17)	98.3 (12)
C6—H6···O3	0.920 (18)	2.526 (17)	2.9107 (18)	105.5 (12)
C4—H4···O3^i	0.93 (2)	2.438 (18)	3.0081 (17)	119.7 (14)
C2—H2···O5^ii	0.950 (17)	2.356 (17)	3.2469 (16)	156.0 (14)
C8—H8···O4^ii	0.975 (18)	2.714 (17)	3.3047 (18)	119.4 (13)
C11—H11···O4^iii	0.962 (19)	2.739 (19)	3.6521 (18)	158.7 (14)
C13—H13C···O3^iii	0.94 (2)	2.83 (2)	3.482 (2)	127.5 (17)
C13—H13B···O2^iv	0.95 (3)	2.79 (3)	3.730 (2)	174.4 (19)
C9—H9···O1^iv	0.936 (19)	2.695 (19)	3.6154 (18)	167.9 (15)
C6—H6···O2^v	0.920 (18)	2.583 (18)	3.3515 (18)	141.4 (14)
C13—H13A···O1^v	0.96 (2)	2.79 (2)	3.4887 (19)	130.5 (17)
C5—H5···O4^vi	0.962 (19)	2.727 (19)	3.5354 (18)	142.0 (14)

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