In the title compound, C
12H
11NO
3, the molecules have two intramolecular C—H

O hydrogen bonds that define an
S(6)
S(5) pattern. The molecules are linked by N—H

O hydrogen bonds into a centrosymmetric dimer. These dimers are linked by further C—H

O hydrogen bonds, so forming a [100] ribbon of
R22(8)
R44(18)[
R44(20)] rings, a [1


] chain of alternating
R22(8) and
R22(22) rings, and an [010] complex chain of
R42(18) rings. The combination of the [100] ribbon, the [1


] chain and the [010] chain results in the formation of a three-dimensional network structure.
Supporting information
CCDC reference: 626367
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.005 Å
- R factor = 0.045
- wR factor = 0.124
- Data-to-parameter ratio = 12.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12 .. O2 .. 2.72 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 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
1 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
Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
4-Methyl-7-phenylsulfonamido-2
H-1-benzopyran-2-one
top
Crystal data top
C16H13NO4S | Z = 2 |
Mr = 315.33 | F(000) = 328 |
Triclinic, P1 | Dx = 1.461 Mg m−3 |
Hall symbol: -P 1 | Melting point: 518 K |
a = 8.040 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.193 (3) Å | Cell parameters from 1538 reflections |
c = 11.656 (5) Å | θ = 2.7–26.4° |
α = 83.246 (5)° | µ = 0.24 mm−1 |
β = 85.316 (5)° | T = 298 K |
γ = 70.287 (4)° | Block, yellow |
V = 717.0 (5) Å3 | 0.42 × 0.25 × 0.21 mm |
Data collection top
Siemens SMART 1000 CCD area-detector diffractometer | 2493 independent reflections |
Radiation source: fine-focus sealed tube | 1853 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
φ and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.905, Tmax = 0.951 | k = −9→9 |
3735 measured reflections | l = −12→13 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0566P)2 + 0.2626P] where P = (Fo2 + 2Fc2)/3 |
2493 reflections | (Δ/σ)max < 0.001 |
200 parameters | Δρmax = 0.24 e Å−3 |
6 restraints | Δρmin = −0.34 e Å−3 |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.6429 (3) | 0.7223 (2) | 0.45846 (15) | 0.0564 (5) | |
O2 | 0.7076 (3) | 0.6107 (3) | 0.29165 (19) | 0.0858 (8) | |
O3 | 0.8542 (3) | 0.9148 (2) | 0.78300 (17) | 0.0607 (5) | |
O4 | 0.7141 (3) | 0.9654 (2) | 0.97720 (16) | 0.0561 (5) | |
N1 | 0.5329 (3) | 0.9637 (3) | 0.82199 (18) | 0.0485 (6) | |
H1 | 0.4588 | 0.9541 | 0.8826 | 0.058* | |
S1 | 0.73206 (9) | 0.88610 (8) | 0.87159 (6) | 0.0462 (2) | |
C1 | 0.5938 (5) | 0.6607 (4) | 0.3657 (2) | 0.0622 (8) | |
C2 | 0.4156 (5) | 0.6617 (4) | 0.3674 (2) | 0.0633 (8) | |
H2 | 0.3804 | 0.6217 | 0.3052 | 0.076* | |
C3 | 0.2958 (4) | 0.7175 (4) | 0.4542 (2) | 0.0553 (7) | |
C4 | 0.3509 (3) | 0.7829 (3) | 0.5494 (2) | 0.0452 (6) | |
C5 | 0.5244 (3) | 0.7819 (3) | 0.5484 (2) | 0.0452 (6) | |
C6 | 0.5893 (4) | 0.8398 (3) | 0.6354 (2) | 0.0457 (6) | |
H6 | 0.7057 | 0.8386 | 0.6311 | 0.055* | |
C7 | 0.4780 (3) | 0.8998 (3) | 0.7296 (2) | 0.0429 (6) | |
C8 | 0.3032 (4) | 0.9036 (3) | 0.7332 (2) | 0.0480 (7) | |
H8 | 0.2278 | 0.9453 | 0.7960 | 0.058* | |
C9 | 0.2415 (4) | 0.8465 (3) | 0.6453 (2) | 0.0497 (7) | |
H9 | 0.1244 | 0.8500 | 0.6492 | 0.060* | |
C10 | 0.1119 (5) | 0.7116 (5) | 0.4550 (3) | 0.0778 (10) | |
H10A | 0.0991 | 0.6595 | 0.3881 | 0.117* | |
H10B | 0.0290 | 0.8278 | 0.4537 | 0.117* | |
H10C | 0.0896 | 0.6437 | 0.5237 | 0.117* | |
C11 | 0.7784 (3) | 0.6610 (3) | 0.9037 (2) | 0.0426 (6) | |
C12 | 0.9009 (4) | 0.5469 (4) | 0.8365 (3) | 0.0615 (8) | |
H12 | 0.9605 | 0.5874 | 0.7739 | 0.074* | |
C13 | 0.9337 (5) | 0.3706 (4) | 0.8640 (3) | 0.0767 (10) | |
H13 | 1.0152 | 0.2913 | 0.8188 | 0.092* | |
C14 | 0.8474 (5) | 0.3120 (4) | 0.9569 (4) | 0.0771 (11) | |
H14 | 0.8697 | 0.1931 | 0.9747 | 0.093* | |
C15 | 0.7279 (5) | 0.4286 (5) | 1.0241 (4) | 0.0865 (11) | |
H15 | 0.6703 | 0.3883 | 1.0878 | 0.104* | |
C16 | 0.6927 (4) | 0.6039 (4) | 0.9978 (3) | 0.0669 (9) | |
H16 | 0.6117 | 0.6830 | 1.0433 | 0.080* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0560 (12) | 0.0579 (12) | 0.0462 (11) | −0.0108 (10) | 0.0179 (9) | −0.0072 (9) |
O2 | 0.0931 (19) | 0.0940 (17) | 0.0568 (13) | −0.0149 (14) | 0.0284 (13) | −0.0246 (12) |
O3 | 0.0567 (13) | 0.0576 (12) | 0.0684 (13) | −0.0261 (10) | 0.0211 (10) | −0.0040 (10) |
O4 | 0.0564 (12) | 0.0554 (11) | 0.0646 (12) | −0.0252 (10) | 0.0119 (10) | −0.0283 (9) |
N1 | 0.0446 (13) | 0.0460 (12) | 0.0506 (13) | −0.0111 (10) | 0.0123 (10) | −0.0088 (10) |
S1 | 0.0445 (4) | 0.0415 (4) | 0.0542 (4) | −0.0175 (3) | 0.0120 (3) | −0.0117 (3) |
C1 | 0.076 (2) | 0.0532 (17) | 0.0436 (17) | −0.0071 (16) | 0.0087 (16) | −0.0027 (14) |
C2 | 0.076 (2) | 0.0574 (18) | 0.0468 (17) | −0.0097 (16) | −0.0055 (16) | −0.0041 (14) |
C3 | 0.0609 (19) | 0.0472 (16) | 0.0489 (16) | −0.0079 (14) | −0.0066 (14) | 0.0036 (13) |
C4 | 0.0453 (16) | 0.0379 (13) | 0.0430 (14) | −0.0051 (12) | 0.0028 (12) | 0.0041 (11) |
C5 | 0.0463 (16) | 0.0373 (13) | 0.0402 (14) | −0.0033 (12) | 0.0114 (12) | 0.0022 (11) |
C6 | 0.0405 (15) | 0.0423 (14) | 0.0478 (15) | −0.0094 (12) | 0.0097 (12) | −0.0001 (12) |
C7 | 0.0439 (15) | 0.0349 (13) | 0.0433 (14) | −0.0074 (11) | 0.0063 (11) | 0.0006 (11) |
C8 | 0.0453 (16) | 0.0453 (15) | 0.0460 (15) | −0.0085 (12) | 0.0143 (12) | −0.0054 (12) |
C9 | 0.0404 (15) | 0.0486 (15) | 0.0530 (16) | −0.0090 (12) | 0.0069 (13) | 0.0000 (13) |
C10 | 0.068 (2) | 0.085 (2) | 0.079 (2) | −0.0194 (19) | −0.0138 (18) | −0.0121 (19) |
C11 | 0.0416 (15) | 0.0424 (14) | 0.0477 (14) | −0.0177 (12) | −0.0013 (12) | −0.0085 (11) |
C12 | 0.069 (2) | 0.0501 (17) | 0.0570 (18) | −0.0078 (15) | 0.0006 (15) | −0.0083 (14) |
C13 | 0.092 (3) | 0.0463 (18) | 0.081 (2) | −0.0037 (18) | −0.020 (2) | −0.0137 (17) |
C14 | 0.080 (3) | 0.0440 (18) | 0.115 (3) | −0.0271 (18) | −0.039 (2) | 0.0065 (19) |
C15 | 0.080 (3) | 0.069 (2) | 0.112 (3) | −0.037 (2) | 0.002 (2) | 0.020 (2) |
C16 | 0.066 (2) | 0.0589 (19) | 0.076 (2) | −0.0265 (16) | 0.0153 (17) | −0.0036 (16) |
Geometric parameters (Å, º) top
O1—C5 | 1.374 (3) | C7—C8 | 1.393 (4) |
O1—C1 | 1.382 (4) | C8—C9 | 1.366 (4) |
O2—C1 | 1.205 (3) | C8—H8 | 0.9300 |
O3—S1 | 1.4207 (19) | C9—H9 | 0.9300 |
O4—S1 | 1.4331 (19) | C10—H10A | 0.9600 |
N1—C7 | 1.412 (3) | C10—H10B | 0.9600 |
N1—S1 | 1.637 (2) | C10—H10C | 0.9600 |
N1—H1 | 0.9000 | C11—C16 | 1.367 (4) |
S1—C11 | 1.754 (3) | C11—C12 | 1.372 (4) |
C1—C2 | 1.429 (5) | C12—C13 | 1.380 (4) |
C2—C3 | 1.346 (4) | C12—H12 | 0.9300 |
C2—H2 | 0.9300 | C13—C14 | 1.366 (5) |
C3—C4 | 1.448 (4) | C13—H13 | 0.9300 |
C3—C10 | 1.495 (4) | C14—C15 | 1.372 (5) |
C4—C5 | 1.391 (4) | C14—H14 | 0.9300 |
C4—C9 | 1.400 (3) | C15—C16 | 1.369 (5) |
C5—C6 | 1.376 (4) | C15—H15 | 0.9300 |
C6—C7 | 1.385 (3) | C16—H16 | 0.9300 |
C6—H6 | 0.9300 | | |
| | | |
C5—O1—C1 | 121.1 (2) | C9—C8—C7 | 120.5 (2) |
C7—N1—S1 | 124.25 (17) | C9—C8—H8 | 119.8 |
C7—N1—H1 | 105.8 | C7—C8—H8 | 119.8 |
S1—N1—H1 | 105.9 | C8—C9—C4 | 121.4 (3) |
O3—S1—O4 | 119.09 (12) | C8—C9—H9 | 119.3 |
O3—S1—N1 | 108.72 (12) | C4—C9—H9 | 119.3 |
O4—S1—N1 | 103.70 (11) | C3—C10—H10A | 109.5 |
O3—S1—C11 | 108.81 (12) | C3—C10—H10B | 109.5 |
O4—S1—C11 | 109.15 (12) | H10A—C10—H10B | 109.5 |
N1—S1—C11 | 106.65 (11) | C3—C10—H10C | 109.5 |
O2—C1—O1 | 115.9 (3) | H10A—C10—H10C | 109.5 |
O2—C1—C2 | 126.8 (3) | H10B—C10—H10C | 109.5 |
O1—C1—C2 | 117.3 (3) | C16—C11—C12 | 121.6 (3) |
C3—C2—C1 | 123.5 (3) | C16—C11—S1 | 118.4 (2) |
C3—C2—H2 | 118.2 | C12—C11—S1 | 120.0 (2) |
C1—C2—H2 | 118.2 | C11—C12—C13 | 118.5 (3) |
C2—C3—C4 | 117.8 (3) | C11—C12—H12 | 120.8 |
C2—C3—C10 | 122.2 (3) | C13—C12—H12 | 120.8 |
C4—C3—C10 | 120.0 (3) | C14—C13—C12 | 120.4 (3) |
C5—C4—C9 | 116.5 (3) | C14—C13—H13 | 119.8 |
C5—C4—C3 | 118.9 (2) | C12—C13—H13 | 119.8 |
C9—C4—C3 | 124.5 (3) | C13—C14—C15 | 120.0 (3) |
O1—C5—C6 | 115.5 (2) | C13—C14—H14 | 120.0 |
O1—C5—C4 | 121.4 (2) | C15—C14—H14 | 120.0 |
C6—C5—C4 | 123.2 (2) | C16—C15—C14 | 120.5 (3) |
C5—C6—C7 | 118.7 (3) | C16—C15—H15 | 119.8 |
C5—C6—H6 | 120.6 | C14—C15—H15 | 119.8 |
C7—C6—H6 | 120.6 | C11—C16—C15 | 119.0 (3) |
C6—C7—C8 | 119.7 (3) | C11—C16—H16 | 120.5 |
C6—C7—N1 | 122.5 (2) | C15—C16—H16 | 120.5 |
C8—C7—N1 | 117.8 (2) | | |
| | | |
C7—N1—S1—O3 | 63.8 (2) | C5—C6—C7—N1 | −179.1 (2) |
C7—N1—S1—O4 | −168.56 (19) | S1—N1—C7—C6 | −35.5 (3) |
C7—N1—S1—C11 | −53.4 (2) | S1—N1—C7—C8 | 146.5 (2) |
C5—O1—C1—O2 | −179.7 (2) | C6—C7—C8—C9 | 0.8 (4) |
C5—O1—C1—C2 | 0.0 (4) | N1—C7—C8—C9 | 178.8 (2) |
O2—C1—C2—C3 | 179.0 (3) | C7—C8—C9—C4 | 0.0 (4) |
O1—C1—C2—C3 | −0.6 (4) | C5—C4—C9—C8 | −0.4 (4) |
C1—C2—C3—C4 | 1.2 (4) | C3—C4—C9—C8 | 178.9 (2) |
C1—C2—C3—C10 | −178.0 (3) | O3—S1—C11—C16 | 170.9 (2) |
C2—C3—C4—C5 | −1.3 (4) | O4—S1—C11—C16 | 39.5 (3) |
C10—C3—C4—C5 | 178.0 (3) | N1—S1—C11—C16 | −71.9 (2) |
C2—C3—C4—C9 | 179.5 (3) | O3—S1—C11—C12 | −7.7 (3) |
C10—C3—C4—C9 | −1.2 (4) | O4—S1—C11—C12 | −139.1 (2) |
C1—O1—C5—C6 | −180.0 (2) | N1—S1—C11—C12 | 109.4 (2) |
C1—O1—C5—C4 | −0.1 (3) | C16—C11—C12—C13 | 1.7 (5) |
C9—C4—C5—O1 | −180.0 (2) | S1—C11—C12—C13 | −179.8 (2) |
C3—C4—C5—O1 | 0.8 (3) | C11—C12—C13—C14 | −0.9 (5) |
C9—C4—C5—C6 | −0.1 (4) | C12—C13—C14—C15 | −0.3 (5) |
C3—C4—C5—C6 | −179.4 (2) | C13—C14—C15—C16 | 0.7 (6) |
O1—C5—C6—C7 | −179.2 (2) | C12—C11—C16—C15 | −1.2 (5) |
C4—C5—C6—C7 | 0.9 (4) | S1—C11—C16—C15 | −179.8 (3) |
C5—C6—C7—C8 | −1.2 (4) | C14—C15—C16—C11 | 0.0 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O3 | 0.93 | 2.46 | 3.099 (4) | 126 |
N1—H1···O4i | 0.90 | 2.07 | 2.923 (3) | 157 |
C9—H9···O3ii | 0.93 | 2.51 | 3.287 (3) | 141 |
C12—H12···O2iii | 0.93 | 2.72 | 3.278 (4) | 120 |
C14—H14···O4iv | 0.93 | 2.57 | 3.336 (4) | 140 |
Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) x−1, y, z; (iii) −x+2, −y+1, −z+1; (iv) x, y−1, z. |