Phenyl 3-nitro­benzene­sulfonate

In the title mol­ecule, C₁₂H₉NO₅S, there are weak C—H...O interactions which generate rings of motifs S(5), S(6), R²₁(4), R¹₂(5), R²₂(7) and R²₂(13). The supramolecular aggregation is completed by the presence of C—H...π interactions.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.043
• wR factor = 0.060
• Data-to-parameter ratio = 12.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.51
         From the CIF: _reflns_number_total               2392
         Count of symmetry unique reflns         1495
         Completeness (_total/calc)            160.00%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured       897
         Fraction of Friedel pairs measured     0.600
         Are heavy atom types Z>Si present          yes
          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.

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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.

Phenyl 3-nitrobenzenesulfonate

Crystal data

C12H9NO5S	Dx = 1.575 Mg m^−3
Mr = 279.26	Melting point = 363–365 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 713 reflections
a = 17.458 (4) Å	θ = 2.9–25.7°
b = 12.287 (3) Å	µ = 0.29 mm^−1
c = 5.4891 (14) Å	T = 120 K
V = 1177.4 (5) Å^3	Block, colourless
Z = 4	0.16 × 0.14 × 0.09 mm
F(000) = 576

Data collection

Bruker Proteum M diffractometer	1838 reflections with I > 2σ(I)
Radiation source: Bede microsource	Rint = 0.059
Graphite monochromator	θmax = 27.5°, θmin = 2.9°
Detector resolution: 8 pixels mm^-1	h = −22→22
/w scans	k = −15→12
7868 measured reflections	l = −7→5
2392 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Only H-atom coordinates refined
wR(F^2) = 0.060	w = 1/[σ^2(Fo^2) + (0.0153P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.91	(Δ/σ)max < 0.001
2392 reflections	Δρmax = 0.44 e Å^−3
199 parameters	Δρmin = −0.47 e Å^−3
1 restraint	Absolute structure: (Flack, 1983), 897 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (8)

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
C1	0.11247 (15)	0.0630 (2)	0.7016 (6)	0.0182 (6)
C2	0.11324 (17)	0.1622 (2)	0.5871 (5)	0.0199 (7)
H2	0.0838 (16)	0.217 (2)	0.639 (5)	0.024*
C3	0.15896 (17)	0.1769 (2)	0.3843 (5)	0.0217 (8)
H3	0.1607 (14)	0.2488 (19)	0.299 (5)	0.026*
C4	0.20411 (15)	0.0918 (2)	0.3034 (6)	0.0184 (6)
H4	0.2345 (14)	0.099 (2)	0.171 (5)	0.022*
C5	0.20319 (15)	−0.0061 (2)	0.4260 (5)	0.0160 (6)
C6	0.15734 (16)	−0.0239 (2)	0.6291 (5)	0.0159 (6)
H6	0.1562 (13)	−0.089 (2)	0.724 (5)	0.019*
C7	0.37909 (15)	0.0097 (2)	0.4286 (6)	0.0176 (6)
C8	0.36942 (16)	0.0896 (2)	0.6005 (6)	0.0212 (7)
H8	0.3416 (15)	0.074 (2)	0.734 (5)	0.025*
C9	0.40583 (17)	0.1882 (2)	0.5661 (6)	0.0231 (7)
H9	0.4006 (15)	0.2436 (19)	0.681 (6)	0.028*
C10	0.44987 (16)	0.2057 (2)	0.3633 (6)	0.0220 (7)
H10	0.4720 (14)	0.276 (2)	0.336 (6)	0.026*
C11	0.45943 (16)	0.1234 (2)	0.1933 (6)	0.0234 (7)
H11	0.4901 (15)	0.136 (2)	0.061 (5)	0.028*
C12	0.42409 (16)	0.0234 (2)	0.2258 (6)	0.0206 (7)
H12	0.4291 (14)	−0.031 (2)	0.112 (5)	0.025*
N1	0.06214 (13)	0.0485 (2)	0.9160 (4)	0.0238 (6)
O1	0.02181 (11)	0.12588 (16)	0.9769 (4)	0.0314 (6)
O2	0.06358 (11)	−0.03936 (16)	1.0221 (4)	0.0287 (5)
O3	0.23727 (11)	−0.21412 (14)	0.4141 (3)	0.0249 (5)
O4	0.27614 (11)	−0.09700 (14)	0.0710 (3)	0.0251 (5)
O5	0.34119 (11)	−0.09175 (14)	0.4680 (3)	0.0198 (5)
S1	0.26294 (4)	−0.11242 (5)	0.32360 (13)	0.01894 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0139 (15)	0.0243 (16)	0.0163 (15)	−0.0034 (11)	−0.0031 (14)	−0.0026 (14)
C2	0.0197 (17)	0.0186 (16)	0.0214 (18)	0.0025 (13)	−0.0037 (15)	−0.0052 (14)
C3	0.0210 (16)	0.0164 (15)	0.028 (2)	−0.0033 (12)	−0.0079 (14)	0.0023 (13)
C4	0.0167 (14)	0.0229 (15)	0.0155 (14)	−0.0031 (11)	−0.0021 (14)	−0.0011 (15)
C5	0.0131 (14)	0.0168 (14)	0.0180 (16)	0.0011 (11)	−0.0039 (13)	−0.0034 (12)
C6	0.0167 (15)	0.0162 (14)	0.0148 (16)	−0.0020 (12)	−0.0051 (12)	−0.0020 (12)
C7	0.0149 (14)	0.0172 (14)	0.0208 (17)	0.0029 (12)	−0.0011 (14)	0.0039 (13)
C8	0.0191 (16)	0.0296 (17)	0.0147 (16)	−0.0006 (13)	0.0003 (14)	0.0036 (14)
C9	0.0193 (17)	0.0271 (18)	0.023 (2)	0.0014 (13)	−0.0037 (15)	−0.0044 (14)
C10	0.0173 (15)	0.0222 (15)	0.026 (2)	−0.0026 (12)	−0.0031 (14)	0.0054 (14)
C11	0.0210 (17)	0.0300 (18)	0.0193 (16)	0.0029 (13)	0.0053 (15)	0.0020 (16)
C12	0.0193 (16)	0.0213 (16)	0.0211 (18)	0.0060 (12)	0.0002 (15)	−0.0014 (13)
N1	0.0198 (14)	0.0341 (15)	0.0174 (14)	−0.0037 (12)	−0.0021 (12)	−0.0067 (12)
O1	0.0266 (13)	0.0356 (13)	0.0321 (14)	0.0070 (10)	0.0039 (11)	−0.0120 (11)
O2	0.0294 (13)	0.0319 (12)	0.0249 (12)	−0.0061 (10)	0.0051 (11)	0.0028 (10)
O3	0.0254 (11)	0.0193 (10)	0.0301 (13)	−0.0028 (9)	−0.0015 (11)	−0.0031 (8)
O4	0.0297 (12)	0.0261 (11)	0.0195 (11)	0.0043 (9)	−0.0003 (10)	−0.0042 (10)
O5	0.0174 (10)	0.0206 (10)	0.0214 (11)	0.0012 (8)	−0.0017 (9)	0.0049 (8)
S1	0.0206 (3)	0.0175 (3)	0.0187 (3)	0.0016 (3)	0.0006 (4)	−0.0016 (4)

Geometric parameters (Å, º)

C1—C2	1.371 (4)	C8—C9	1.382 (4)
C1—C6	1.382 (4)	C8—H8	0.90 (3)
C1—N1	1.480 (4)	C9—C10	1.370 (4)
C2—C3	1.382 (4)	C9—H9	0.93 (3)
C2—H2	0.89 (3)	C10—C11	1.386 (4)
C3—C4	1.382 (4)	C10—H10	0.95 (2)
C3—H3	1.00 (2)	C11—C12	1.387 (4)
C4—C5	1.379 (4)	C11—H11	0.91 (3)
C4—H4	0.90 (3)	C12—H12	0.92 (3)
C5—C6	1.390 (4)	N1—O2	1.226 (3)
C5—S1	1.763 (3)	N1—O1	1.230 (3)
C6—H6	0.96 (3)	O3—S1	1.4175 (18)
C7—C8	1.372 (4)	O4—S1	1.418 (2)
C7—C12	1.373 (4)	O5—S1	1.600 (2)
C7—O5	1.427 (3)
C2—C1—C6	123.3 (3)	C9—C8—H8	123.0 (17)
C2—C1—N1	118.5 (3)	C10—C9—C8	120.5 (3)
C6—C1—N1	118.2 (2)	C10—C9—H9	119.4 (17)
C1—C2—C3	119.4 (3)	C8—C9—H9	120.1 (17)
C1—C2—H2	121.1 (18)	C9—C10—C11	120.0 (3)
C3—C2—H2	119.5 (18)	C9—C10—H10	119.9 (18)
C2—C3—C4	119.3 (3)	C11—C10—H10	120.1 (18)
C2—C3—H3	120.7 (15)	C12—C11—C10	120.4 (3)
C4—C3—H3	120.0 (15)	C12—C11—H11	120.6 (17)
C5—C4—C3	119.8 (3)	C10—C11—H11	119.0 (17)
C5—C4—H4	118.7 (17)	C7—C12—C11	117.9 (3)
C3—C4—H4	121.6 (17)	C7—C12—H12	121.2 (17)
C4—C5—C6	122.4 (3)	C11—C12—H12	120.8 (17)
C4—C5—S1	118.9 (2)	O2—N1—O1	124.3 (3)
C6—C5—S1	118.7 (2)	O2—N1—C1	118.1 (2)
C1—C6—C5	115.9 (3)	O1—N1—C1	117.6 (2)
C1—C6—H6	118.7 (15)	C7—O5—S1	117.36 (16)
C5—C6—H6	125.4 (16)	O3—S1—O4	120.78 (11)
C8—C7—C12	122.7 (3)	O3—S1—O5	103.67 (10)
C8—C7—O5	117.6 (3)	O4—S1—O5	108.94 (11)
C12—C7—O5	119.7 (3)	O3—S1—C5	110.74 (13)
C7—C8—C9	118.5 (3)	O4—S1—C5	107.98 (13)
C7—C8—H8	118.4 (17)	O5—S1—C5	103.28 (11)
C6—C1—C2—C3	2.1 (4)	C10—C11—C12—C7	0.8 (4)
N1—C1—C2—C3	−179.0 (2)	C2—C1—N1—O2	−177.7 (3)
C1—C2—C3—C4	−1.2 (4)	C6—C1—N1—O2	1.3 (4)
C2—C3—C4—C5	−0.2 (4)	C2—C1—N1—O1	1.9 (4)
C3—C4—C5—C6	0.8 (4)	C6—C1—N1—O1	−179.1 (2)
C3—C4—C5—S1	−178.5 (2)	C8—C7—O5—S1	100.0 (3)
C2—C1—C6—C5	−1.4 (4)	C12—C7—O5—S1	−80.9 (3)
N1—C1—C6—C5	179.6 (2)	C7—O5—S1—O3	−175.80 (19)
C4—C5—C6—C1	0.0 (4)	C7—O5—S1—O4	54.4 (2)
S1—C5—C6—C1	179.3 (2)	C7—O5—S1—C5	−60.2 (2)
C12—C7—C8—C9	0.8 (4)	C4—C5—S1—O3	−160.8 (2)
O5—C7—C8—C9	179.8 (2)	C6—C5—S1—O3	19.8 (2)
C7—C8—C9—C10	0.6 (5)	C4—C5—S1—O4	−26.5 (2)
C8—C9—C10—C11	−1.3 (5)	C6—C5—S1—O4	154.1 (2)
C9—C10—C11—C12	0.5 (4)	C4—C5—S1—O5	88.8 (2)
C8—C7—C12—C11	−1.5 (4)	C6—C5—S1—O5	−90.6 (2)
O5—C7—C12—C11	179.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.89 (2)	2.42 (3)	2.707 (4)	98.8 (18)
C4—H4···O4	0.90 (2)	2.57 (2)	2.932 (3)	104.5 (17)
C6—H6···O2	0.94 (2)	2.39 (2)	2.715 (4)	100.2 (15)
C6—H6···O3	0.94 (2)	2.69 (2)	2.968 (3)	97.7 (16)
C12—H12···O4	0.90 (3)	2.80 (2)	3.095 (3)	100.4 (18)
C3—H3···O3^i	1.00 (2)	2.80 (3)	3.426 (4)	121.2 (17)
C3—H3···O5^i	1.00 (2)	2.67 (3)	3.647 (3)	165 (2)
C9—H9···O2^i	0.93 (3)	2.87 (2)	3.399 (4)	117 (2)
C10—H10···O2^i	0.94 (2)	2.58 (2)	3.260 (3)	129.6 (19)
C4—H4···O3^i	0.90 (2)	2.75 (2)	3.364 (4)	127.0 (18)
C9—H9···O3^ii	0.93 (3)	2.78 (3)	3.366 (4)	121.7 (19)
C3—H3···O4^ii	1.00 (2)	2.65 (2)	3.170 (3)	112.2 (19)
C6—H6···O4^iii	0.94 (2)	2.84 (2)	3.317 (3)	112.9 (15)
C10—H10···O1^iv	0.94 (2)	2.48 (3)	3.219 (4)	135 (2)
C4—H4···Cg2	0.90 (2)	3.38	3.72	105
C12—H12···Cg2^v	0.90 (3)	3.13	3.71	124

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