Crystal structure of 4-{[(naphthalen-2-yl)sulfonyl-amino]-meth-yl}cyclo-hexa-necarb-oxy-lic acid.

The title compound, C18H21NO4S, is a new sulfonamide derivative of tranexamic acid. In the crystal, mol-ecules form inversion dimers via O-H⋯O hydrogen bonds involving the carb-oxy-lic acid groups. Hydrogen bonding between the sulfonamide N-H group and the carb-oxy-lic acid O atom assembles the dimers into thick layers parallel to (100). The naphthalene groups of adjacent layers are arranged in a herring-bone motif. There are C-H⋯π inter-actions between the naphthalene rings of neighbouring layers.

Related literature

For related structures, see: Ashfaq et al. (2011a ▸,b ▸).

Experimental

Crystal data

C18H21NO4S

M = 347.42

Monoclinic,

a = 16.5301 (13) Å

b = 6.0573 (4) Å

c = 17.0036 (12) Å

β = 100.810 (4)°

V = 1672.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.40 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▸) T min = 0.920, T max = 0.956

13364 measured reflections

3636 independent reflections

2315 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.117

S = 1.02

3636 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2007 ▸); cell refinement: SAINT (Bruker, 2007 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015002054/gk2626sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015002054/gk2626Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015002054/gk2626Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015002054/gk2626fig1.tif

View of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii.

Click here for additional data file.

. DOI: 10.1107/S2056989015002054/gk2626fig2.tif

View of the crystal packing in the title compound with hydrogen bonds shown as dashed lines.

CCDC reference: 1046512

Additional supporting information: crystallographic information; 3D view; checkCIF report

C18H21NO4S	F(000) = 736
Mr = 347.42	Dx = 1.380 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.5301 (13) Å	Cell parameters from 2315 reflections
b = 6.0573 (4) Å	θ = 1.3–27.0°
c = 17.0036 (12) Å	µ = 0.22 mm−1
β = 100.810 (4)°	T = 296 K
V = 1672.3 (2) Å3	Needle, colourless
Z = 4	0.40 × 0.22 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	3636 independent reflections
Radiation source: fine-focus sealed tube	2315 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 7.80 pixels mm-1	θmax = 27.0°, θmin = 1.3°
ω scans	h = −21→20
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −7→6
Tmin = 0.920, Tmax = 0.956	l = −21→21
13364 measured reflections

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.049P)2 + 0.3363P] where P = (Fo2 + 2Fc2)/3
3636 reflections	(Δ/σ)max < 0.001
218 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.22360 (4)	1.11590 (10)	−0.03913 (3)	0.04790 (19)
O1	0.46462 (13)	1.1212 (3)	0.40940 (10)	0.0784 (6)
H1	0.4886	1.1331	0.4560	0.118*
O2	0.43679 (11)	0.7932 (3)	0.45431 (9)	0.0664 (5)
O3	0.16554 (11)	1.1324 (3)	0.01273 (9)	0.0690 (5)
O4	0.25871 (12)	1.3099 (3)	−0.06651 (9)	0.0676 (5)
N1	0.29769 (11)	0.9664 (3)	0.00539 (10)	0.0494 (5)
H1A	0.3455	0.9895	−0.0061	0.059*
C1	0.42778 (14)	0.9398 (4)	0.40022 (12)	0.0481 (6)
C2	0.37262 (13)	0.8893 (3)	0.32200 (12)	0.0407 (5)
H2	0.3195	0.8392	0.3331	0.049*
C3	0.40971 (15)	0.7018 (4)	0.28063 (13)	0.0513 (6)
H3A	0.4646	0.7433	0.2737	0.062*
H3B	0.4146	0.5715	0.3144	0.062*
C4	0.35752 (15)	0.6468 (4)	0.19930 (12)	0.0493 (6)
H4A	0.3848	0.5332	0.1737	0.059*
H4B	0.3047	0.5891	0.2067	0.059*
C5	0.34370 (13)	0.8489 (3)	0.14548 (12)	0.0404 (5)
H5	0.3975	0.9008	0.1370	0.048*
C6	0.30492 (14)	1.0314 (4)	0.18683 (11)	0.0436 (5)
H6A	0.2508	0.9847	0.1944	0.052*
H6B	0.2980	1.1615	0.1530	0.052*
C7	0.35715 (14)	1.0900 (3)	0.26754 (12)	0.0440 (5)
H7A	0.3293	1.2029	0.2930	0.053*
H7B	0.4094	1.1498	0.2596	0.053*
C8	0.29161 (15)	0.7938 (4)	0.06398 (12)	0.0484 (6)
H8A	0.3099	0.6546	0.0452	0.058*
H8B	0.2345	0.7769	0.0693	0.058*
C9	0.17432 (12)	0.9711 (4)	−0.12510 (11)	0.0388 (5)
C10	0.14017 (14)	0.7621 (4)	−0.11635 (13)	0.0484 (6)
H10	0.1453	0.6988	−0.0658	0.058*
C11	0.09970 (14)	0.6527 (4)	−0.18159 (13)	0.0483 (6)
H11	0.0769	0.5149	−0.1753	0.058*
C12	0.09160 (12)	0.7449 (4)	−0.25889 (12)	0.0405 (5)
C13	0.04936 (14)	0.6359 (4)	−0.32851 (14)	0.0514 (6)
H13	0.0258	0.4982	−0.3240	0.062*
C14	0.04315 (15)	0.7311 (4)	−0.40141 (14)	0.0577 (7)
H14	0.0150	0.6586	−0.4466	0.069*
C15	0.07844 (14)	0.9367 (4)	−0.40943 (13)	0.0546 (6)
H15	0.0742	0.9988	−0.4600	0.066*
C16	0.11865 (13)	1.0470 (4)	−0.34486 (12)	0.0465 (6)
H16	0.1413	1.1849	−0.3513	0.056*
C17	0.12663 (12)	0.9548 (3)	−0.26764 (11)	0.0379 (5)
C18	0.16767 (12)	1.0656 (4)	−0.19883 (11)	0.0389 (5)
H18	0.1904	1.2042	−0.2037	0.047*

	U11	U22	U33	U12	U13	U23
S1	0.0589 (4)	0.0505 (4)	0.0310 (3)	0.0083 (3)	0.0001 (2)	−0.0049 (2)
O1	0.0973 (15)	0.0765 (13)	0.0477 (10)	−0.0415 (11)	−0.0217 (10)	0.0108 (9)
O2	0.0784 (13)	0.0717 (12)	0.0406 (9)	−0.0267 (9)	−0.0110 (8)	0.0139 (8)
O3	0.0673 (12)	0.0963 (14)	0.0427 (9)	0.0280 (10)	0.0083 (8)	−0.0136 (9)
O4	0.1019 (15)	0.0441 (11)	0.0472 (9)	−0.0130 (9)	−0.0105 (9)	−0.0006 (8)
N1	0.0459 (11)	0.0638 (13)	0.0364 (10)	0.0060 (9)	0.0022 (8)	0.0065 (9)
C1	0.0510 (14)	0.0551 (16)	0.0358 (12)	−0.0152 (11)	0.0021 (10)	0.0050 (11)
C2	0.0390 (12)	0.0473 (14)	0.0335 (10)	−0.0092 (10)	0.0007 (9)	0.0025 (9)
C3	0.0609 (16)	0.0422 (14)	0.0439 (12)	0.0037 (11)	−0.0079 (11)	0.0061 (10)
C4	0.0592 (15)	0.0416 (14)	0.0416 (12)	0.0057 (11)	−0.0050 (11)	−0.0024 (10)
C5	0.0429 (13)	0.0418 (13)	0.0338 (10)	0.0015 (10)	0.0006 (9)	0.0004 (9)
C6	0.0484 (13)	0.0421 (13)	0.0366 (11)	0.0051 (10)	−0.0015 (10)	0.0008 (10)
C7	0.0519 (14)	0.0405 (13)	0.0375 (11)	0.0018 (10)	0.0027 (10)	−0.0035 (9)
C8	0.0590 (15)	0.0462 (15)	0.0357 (11)	0.0009 (11)	−0.0019 (10)	−0.0015 (10)
C9	0.0398 (12)	0.0422 (13)	0.0337 (11)	0.0049 (9)	0.0048 (9)	−0.0018 (9)
C10	0.0567 (15)	0.0465 (14)	0.0408 (12)	0.0049 (11)	0.0062 (11)	0.0099 (11)
C11	0.0517 (14)	0.0387 (14)	0.0546 (14)	−0.0024 (10)	0.0102 (11)	0.0059 (11)
C12	0.0355 (12)	0.0427 (13)	0.0437 (12)	0.0011 (10)	0.0083 (9)	−0.0036 (10)
C13	0.0475 (14)	0.0488 (15)	0.0576 (15)	−0.0080 (11)	0.0087 (11)	−0.0147 (12)
C14	0.0552 (16)	0.0710 (18)	0.0440 (13)	−0.0046 (13)	0.0022 (12)	−0.0222 (12)
C15	0.0532 (15)	0.0743 (19)	0.0362 (12)	−0.0012 (13)	0.0079 (11)	−0.0049 (11)
C16	0.0507 (14)	0.0538 (15)	0.0349 (11)	−0.0045 (11)	0.0076 (10)	0.0005 (10)
C17	0.0366 (12)	0.0407 (13)	0.0367 (11)	0.0007 (9)	0.0074 (9)	−0.0023 (9)
C18	0.0395 (12)	0.0412 (13)	0.0351 (11)	−0.0033 (9)	0.0049 (9)	−0.0010 (9)

S1—O3	1.4235 (17)	C6—H6B	0.9700
S1—O4	1.4267 (17)	C7—H7A	0.9700
S1—N1	1.5955 (19)	C7—H7B	0.9700
S1—C9	1.767 (2)	C8—H8A	0.9700
O1—C1	1.252 (3)	C8—H8B	0.9700
O1—H1	0.8200	C9—C18	1.364 (3)
O2—C1	1.267 (3)	C9—C10	1.405 (3)
N1—C8	1.461 (3)	C10—C11	1.356 (3)
N1—H1A	0.8600	C10—H10	0.9300
C1—C2	1.496 (3)	C11—C12	1.411 (3)
C2—C7	1.521 (3)	C11—H11	0.9300
C2—C3	1.524 (3)	C12—C17	1.416 (3)
C2—H2	0.9800	C12—C13	1.420 (3)
C3—C4	1.523 (3)	C13—C14	1.353 (3)
C3—H3A	0.9700	C13—H13	0.9300
C3—H3B	0.9700	C14—C15	1.392 (3)
C4—C5	1.520 (3)	C14—H14	0.9300
C4—H4A	0.9700	C15—C16	1.349 (3)
C4—H4B	0.9700	C15—H15	0.9300
C5—C6	1.515 (3)	C16—C17	1.410 (3)
C5—C8	1.525 (3)	C16—H16	0.9300
C5—H5	0.9800	C17—C18	1.408 (3)
C6—C7	1.520 (3)	C18—H18	0.9300
C6—H6A	0.9700
O3—S1—O4	120.48 (11)	C6—C7—C2	111.43 (17)
O3—S1—N1	107.01 (10)	C6—C7—H7A	109.3
O4—S1—N1	107.41 (11)	C2—C7—H7A	109.3
O3—S1—C9	106.71 (10)	C6—C7—H7B	109.3
O4—S1—C9	106.94 (10)	C2—C7—H7B	109.3
N1—S1—C9	107.73 (10)	H7A—C7—H7B	108.0
C1—O1—H1	109.5	N1—C8—C5	111.32 (18)
C8—N1—S1	125.80 (16)	N1—C8—H8A	109.4
C8—N1—H1A	117.1	C5—C8—H8A	109.4
S1—N1—H1A	117.1	N1—C8—H8B	109.4
O1—C1—O2	122.5 (2)	C5—C8—H8B	109.4
O1—C1—C2	119.4 (2)	H8A—C8—H8B	108.0
O2—C1—C2	118.1 (2)	C18—C9—C10	120.71 (19)
C1—C2—C7	112.50 (18)	C18—C9—S1	119.82 (17)
C1—C2—C3	109.38 (18)	C10—C9—S1	119.44 (16)
C7—C2—C3	110.55 (16)	C11—C10—C9	120.0 (2)
C1—C2—H2	108.1	C11—C10—H10	120.0
C7—C2—H2	108.1	C9—C10—H10	120.0
C3—C2—H2	108.1	C10—C11—C12	121.0 (2)
C4—C3—C2	111.94 (18)	C10—C11—H11	119.5
C4—C3—H3A	109.2	C12—C11—H11	119.5
C2—C3—H3A	109.2	C11—C12—C17	118.95 (19)
C4—C3—H3B	109.2	C11—C12—C13	122.6 (2)
C2—C3—H3B	109.2	C17—C12—C13	118.5 (2)
H3A—C3—H3B	107.9	C14—C13—C12	120.4 (2)
C5—C4—C3	111.48 (18)	C14—C13—H13	119.8
C5—C4—H4A	109.3	C12—C13—H13	119.8
C3—C4—H4A	109.3	C13—C14—C15	120.6 (2)
C5—C4—H4B	109.3	C13—C14—H14	119.7
C3—C4—H4B	109.3	C15—C14—H14	119.7
H4A—C4—H4B	108.0	C16—C15—C14	121.0 (2)
C6—C5—C4	109.71 (17)	C16—C15—H15	119.5
C6—C5—C8	111.43 (18)	C14—C15—H15	119.5
C4—C5—C8	111.49 (17)	C15—C16—C17	120.5 (2)
C6—C5—H5	108.0	C15—C16—H16	119.8
C4—C5—H5	108.0	C17—C16—H16	119.8
C8—C5—H5	108.0	C18—C17—C16	122.1 (2)
C5—C6—C7	111.78 (17)	C18—C17—C12	118.91 (18)
C5—C6—H6A	109.3	C16—C17—C12	119.00 (19)
C7—C6—H6A	109.3	C9—C18—C17	120.5 (2)
C5—C6—H6B	109.3	C9—C18—H18	119.8
C7—C6—H6B	109.3	C17—C18—H18	119.8
H6A—C6—H6B	107.9
O3—S1—N1—C8	28.1 (2)	O3—S1—C9—C10	−55.32 (19)
O4—S1—N1—C8	158.77 (17)	O4—S1—C9—C10	174.51 (17)
C9—S1—N1—C8	−86.34 (19)	N1—S1—C9—C10	59.31 (19)
O1—C1—C2—C7	−10.3 (3)	C18—C9—C10—C11	−0.4 (3)
O2—C1—C2—C7	171.3 (2)	S1—C9—C10—C11	177.71 (17)
O1—C1—C2—C3	112.9 (3)	C9—C10—C11—C12	0.4 (3)
O2—C1—C2—C3	−65.4 (3)	C10—C11—C12—C17	0.1 (3)
C1—C2—C3—C4	−178.34 (18)	C10—C11—C12—C13	−179.7 (2)
C7—C2—C3—C4	−53.9 (3)	C11—C12—C13—C14	180.0 (2)
C2—C3—C4—C5	55.6 (3)	C17—C12—C13—C14	0.2 (3)
C3—C4—C5—C6	−56.2 (3)	C12—C13—C14—C15	0.4 (4)
C3—C4—C5—C8	179.88 (19)	C13—C14—C15—C16	−0.9 (4)
C4—C5—C6—C7	57.0 (2)	C14—C15—C16—C17	0.7 (4)
C8—C5—C6—C7	−179.07 (18)	C15—C16—C17—C18	−179.6 (2)
C5—C6—C7—C2	−56.8 (2)	C15—C16—C17—C12	−0.2 (3)
C1—C2—C7—C6	176.83 (18)	C11—C12—C17—C18	−0.6 (3)
C3—C2—C7—C6	54.2 (2)	C13—C12—C17—C18	179.13 (19)
S1—N1—C8—C5	−117.30 (19)	C11—C12—C17—C16	179.93 (19)
C6—C5—C8—N1	73.3 (2)	C13—C12—C17—C16	−0.3 (3)
C4—C5—C8—N1	−163.77 (18)	C10—C9—C18—C17	−0.2 (3)
O3—S1—C9—C18	122.76 (18)	S1—C9—C18—C17	−178.28 (15)
O4—S1—C9—C18	−7.4 (2)	C16—C17—C18—C9	−179.9 (2)
N1—S1—C9—C18	−122.61 (17)	C12—C17—C18—C9	0.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.83	2.623 (2)	163
N1—H1A···O2ii	0.86	2.46	3.043 (2)	124
C11—H11···Cg1iii	0.93	2.91	3.639 (3)	137
C13—H13···Cg2iii	0.93	2.82	3.527 (3)	134

Table 1

Hydrogen-bond geometry (, )

Cg1 and Cg2 are the centroids of the C9C12/C17/C18 and C12C17 rings, respectively.

DHA	DH	HA	D A	DHA
O1H1O2i	0.82	1.83	2.623(2)	163
N1H1AO2ii	0.86	2.46	3.043(2)	124
C11H11Cg1iii	0.93	2.91	3.639(3)	137
C13H13Cg2iii	0.93	2.82	3.527(3)	134

Symmetry codes: (i) ; (ii) ; (iii) .