4-(4-Methylbenzenesulfonamido)benzoic acid N,N-dimethyl­formamide mono­solvate

Huang, M.-L.; Lin, Z.-Y.

doi:10.1107/S1600536811011949

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1062

doi:10.1107/S1600536811011949

Open

access

4-(4-Methylbenzenesulfonamido)benzoic acid N,N-dimethylformamide monosolvate

Miao-Ling Huang ^a ^* and Zhi-Yang Lin ^a

^aCollege of Chemistry and Science of Life, Quanzhou Normal University, Fujian 362000, People's Republic of China
^*Correspondence e-mail: hml301@163.com

(Received 18 March 2011; accepted 31 March 2011; online 7 April 2011)

In the title compound, C₁₄H₁₃NO₄S·C₃H₇NO, the C—S—N—C torsion angle of −64.55 (17)° defines the folded conformation of the molecule. The dihedral angle between the benzene rings is 83.367 (6)°. In a crystal, molecules are linked into a chain along a axis through intermolecular N—H⋯O and O—H⋯O hydrogen bonds. There is also an intramolecular C—H⋯π interaction.

Related literature

N-protected amino acids possess an R-CONH-R′ group analogous to the structure of O-terminal peptides and proteins, see: Antolini et al. (1984 ); Menabue & Saladini (1988 ).

Experimental

Crystal data

C₁₄H₁₃NO₄S·C₃H₇NO
M_r = 364.41
Monoclinic, P 2₁ /n
a = 8.0953 (10) Å
b = 25.151 (3) Å
c = 8.8840 (11) Å
β = 98.010 (1)°
V = 1791.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.39 × 0.29 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.923, T_max = 0.949
9993 measured reflections
3336 independent reflections
2570 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.111
S = 1.04
3336 reflections
230 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.27	2.903 (2)	131
O2—H2A⋯O5ⁱⁱ	0.82	1.79	2.598 (2)	168
C16—H16C⋯Cg1	0.96	2.98	3.576 (3)	121
Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y, -z+1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2003 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811011949/kp2315sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811011949/kp2315Isup2.hkl

checkCIF report

Comment top

N-Protected amino acids possess R-CONH-R' group analogous to the structure of O-terminal peptides and proteins (Menabue, et al., 1988, Antolini, et al., 1984). The substitution of an Ar—SO₂-group on amine addes to 4-aminobenzeoic acid the coordination donors of three types-O, N donors from carboxyl, sulfoxyl and amine respectively, which may result in different coordination modes. In this paper, we synthesized the desired ligand in N,N-dimethylformamide solvent.

The title compound contains one N-p-tolysulfonyl-4-aminobenzoic acid molecule and a solvent N, N-dimethylformamide in the asymmetric unit (Fig. 1). The molecule has a C1—N1—S1—C8 of 64.552 (2) °, and the dihedral angle between the benzene rings is 83.367 (6) °. There are intermolecular hydrogen bonds between carboxylate group oxygen atoms, nitrogen atoms and solvent oxygen atoms of the types N—H···O and O—H···O generating a chain along a axis (Figs. 2 and 3, Table 1). There are intramolecular CH···π interactions between H(16 C) and H(17B) of solvent and the centre of two aromatic rings of the title molecule(C16—H16C···C1—C2—C3—C4—C5—C6 and C17—H17B···C8—C9—C10—C11—C12—C13; the distances of H to the centre of the aromatic rings are 2.982 (3) and 3.84 (3) Å, respectively).

Related literature top

N-protected amino acids possess an R-CONH-R' group analogous to the structure of O-terminal peptides and proteins, see: Antolini et al. (1984); Menabue & Saladini (1988).

Experimental top

A mixture of N-p-tolysulfonylchloride (1 mmol) and 4-aminobenzoic acid (1 mmol) in water(20 ml) was stirred at room temperature for 10 h. Then HCl (12 mol/L) was slowly added to the resulting solution. The mixture was stirred for 5 min and filtrated. The block colourless single crystals suitable for X-ray analysis were obtained by recrystallization from N,N-dimethylformamide. IR(KBr): 3423(s), 3198(versus), 3059(w), 2928(s), 2510(m), 1693(versus), 1635(versus), 1607(s), 1512(m), 1433(m), 1405(s), 1383(s), 1334(s), 1291(s), 1231(m), 1159(versus), 1092(s), 1021(w), 923(s), 862(m), 827(m), 765(m), 674(s), 5757(s), 547(s), 525(m), 503(w)cm^-1.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The ORTEP drawing of the title compound (I). Displacement ellipsoids are drawn at 30% probability level. All hydrogen atams have been omitted for clarity.
	Fig. 2. A view of the hydrogen bonds (dotted lines) in the crystal structure of the title compound (I).
	Fig. 3. The crystal packing of the title compound (I), viewed along the c axis.

4-(4-Methylbenzenesulfonamido)benzoic acid N,N-dimethylformamide monosolvate top

Crystal data top

C₁₄H₁₃NO₄S·C₃H₇NO	F(000) = 768
M_r = 364.41	D_x = 1.351 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3230 reflections
a = 8.0953 (10) Å	θ = 2.5–25.0°
b = 25.151 (3) Å	µ = 0.21 mm⁻¹
c = 8.8840 (11) Å	T = 296 K
β = 98.010 (1)°	Block, colourless
V = 1791.1 (4) Å³	0.39 × 0.29 × 0.25 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3336 independent reflections
Radiation source: fine-focus sealed tube	2570 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
phi and ω scans	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −9→9
T_min = 0.923, T_max = 0.949	k = −23→30
9993 measured reflections	l = −10→10

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0517P)² + 0.5453P] where P = (F_o² + 2F_c²)/3
3336 reflections	(Δ/σ)_max < 0.001
230 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₄H₁₃NO₄S·C₃H₇NO	V = 1791.1 (4) Å³
M_r = 364.41	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.0953 (10) Å	µ = 0.21 mm⁻¹
b = 25.151 (3) Å	T = 296 K
c = 8.8840 (11) Å	0.39 × 0.29 × 0.25 mm
β = 98.010 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3336 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2570 reflections with I > 2σ(I)
T_min = 0.923, T_max = 0.949	R_int = 0.024
9993 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.04	Δρ_max = 0.35 e Å⁻³
3336 reflections	Δρ_min = −0.37 e Å⁻³
230 parameters

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	U_iso*/U_eq
C1	0.3556 (2)	0.05871 (7)	0.1256 (2)	0.0380 (4)
C2	0.4907 (2)	0.07414 (9)	0.0562 (2)	0.0498 (5)
H2	0.4753	0.0971	−0.0266	0.060*
C3	0.6483 (2)	0.05551 (9)	0.1098 (2)	0.0488 (5)
H3	0.7388	0.0665	0.0637	0.059*
C4	0.6733 (2)	0.02077 (8)	0.2312 (2)	0.0400 (4)
C5	0.5375 (2)	0.00633 (8)	0.3018 (2)	0.0449 (5)
H5	0.5529	−0.0167	0.3846	0.054*
C6	0.3800 (2)	0.02563 (8)	0.2509 (2)	0.0451 (5)
H6	0.2905	0.0164	0.3008	0.054*
C7	0.8422 (2)	−0.00147 (8)	0.2797 (2)	0.0452 (5)
C8	0.1600 (2)	0.17188 (8)	0.1824 (2)	0.0459 (5)
C9	0.2493 (3)	0.21904 (9)	0.1886 (3)	0.0560 (6)
H9	0.2980	0.2302	0.1052	0.067*
C10	0.2656 (3)	0.24944 (9)	0.3195 (3)	0.0632 (6)
H10	0.3253	0.2811	0.3230	0.076*
C11	0.1950 (3)	0.23365 (9)	0.4452 (3)	0.0602 (6)
C12	0.1080 (3)	0.18598 (10)	0.4370 (3)	0.0625 (6)
H12	0.0610	0.1745	0.5211	0.075*
C13	0.0896 (3)	0.15518 (9)	0.3078 (3)	0.0555 (6)
H13	0.0303	0.1234	0.3047	0.067*
C14	0.2119 (4)	0.26663 (12)	0.5889 (4)	0.0878 (9)
H14A	0.1492	0.2989	0.5700	0.132*
H14B	0.3273	0.2750	0.6199	0.132*
H14C	0.1699	0.2469	0.6679	0.132*
C15	0.7728 (3)	0.09910 (9)	0.6138 (2)	0.0540 (6)
H15	0.7882	0.0853	0.7119	0.065*
C16	0.6101 (3)	0.15217 (11)	0.4239 (3)	0.0717 (7)
H16A	0.7017	0.1442	0.3698	0.108*
H16B	0.5986	0.1900	0.4319	0.108*
H16C	0.5092	0.1375	0.3702	0.108*
C17	0.5200 (4)	0.13996 (13)	0.6762 (4)	0.0936 (10)
H17A	0.5620	0.1273	0.7761	0.140*
H17B	0.4173	0.1221	0.6400	0.140*
H17C	0.5005	0.1776	0.6802	0.140*
N1	0.18945 (19)	0.07351 (7)	0.06580 (18)	0.0446 (4)
H1	0.1149	0.0489	0.0558	0.054*
N2	0.6410 (2)	0.12933 (7)	0.5741 (2)	0.0518 (4)
O1	0.96596 (17)	0.01262 (6)	0.22823 (18)	0.0589 (4)
O2	0.84373 (17)	−0.03862 (7)	0.38401 (19)	0.0628 (4)
H2A	0.9385	−0.0505	0.4047	0.094*
O3	0.2361 (2)	0.15441 (7)	−0.08607 (17)	0.0661 (5)
O4	−0.04468 (18)	0.12891 (6)	−0.03477 (18)	0.0621 (4)
O5	0.87652 (19)	0.08779 (7)	0.53101 (19)	0.0625 (4)
S1	0.13037 (6)	0.13338 (2)	0.01515 (6)	0.04889 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0357 (10)	0.0379 (10)	0.0400 (10)	0.0011 (8)	0.0036 (8)	−0.0049 (8)
C2	0.0447 (12)	0.0610 (14)	0.0444 (11)	0.0025 (10)	0.0084 (9)	0.0134 (10)
C3	0.0369 (11)	0.0612 (14)	0.0501 (12)	−0.0020 (9)	0.0124 (9)	0.0063 (10)
C4	0.0336 (10)	0.0438 (11)	0.0424 (10)	−0.0017 (8)	0.0044 (8)	−0.0040 (9)
C5	0.0387 (11)	0.0504 (12)	0.0459 (11)	0.0025 (9)	0.0073 (8)	0.0092 (9)
C6	0.0348 (11)	0.0506 (12)	0.0517 (12)	0.0004 (9)	0.0122 (9)	0.0067 (9)
C7	0.0353 (10)	0.0476 (12)	0.0522 (12)	−0.0024 (9)	0.0046 (8)	−0.0041 (9)
C8	0.0364 (11)	0.0419 (12)	0.0582 (12)	0.0028 (8)	0.0025 (9)	0.0042 (9)
C9	0.0480 (13)	0.0471 (13)	0.0736 (15)	−0.0006 (10)	0.0112 (11)	0.0114 (11)
C10	0.0536 (14)	0.0423 (13)	0.0934 (18)	−0.0078 (10)	0.0091 (13)	−0.0037 (12)
C11	0.0488 (13)	0.0527 (14)	0.0794 (16)	−0.0030 (11)	0.0103 (11)	−0.0146 (12)
C12	0.0592 (14)	0.0635 (15)	0.0682 (15)	−0.0128 (12)	0.0207 (11)	−0.0104 (12)
C13	0.0540 (13)	0.0482 (13)	0.0659 (14)	−0.0130 (10)	0.0142 (11)	−0.0056 (11)
C14	0.083 (2)	0.0776 (19)	0.106 (2)	−0.0165 (16)	0.0240 (17)	−0.0388 (17)
C15	0.0571 (14)	0.0541 (14)	0.0479 (12)	−0.0114 (11)	−0.0028 (10)	0.0104 (10)
C16	0.0728 (17)	0.0799 (18)	0.0596 (14)	0.0280 (14)	−0.0006 (12)	0.0042 (13)
C17	0.091 (2)	0.102 (2)	0.100 (2)	0.0006 (17)	0.0533 (18)	−0.0015 (18)
N1	0.0352 (9)	0.0432 (10)	0.0532 (10)	−0.0005 (7)	−0.0017 (7)	−0.0013 (7)
N2	0.0465 (10)	0.0578 (11)	0.0517 (10)	0.0023 (8)	0.0088 (8)	0.0015 (8)
O1	0.0336 (8)	0.0704 (11)	0.0740 (10)	−0.0024 (7)	0.0121 (7)	0.0075 (8)
O2	0.0371 (8)	0.0679 (11)	0.0827 (11)	0.0070 (7)	0.0059 (8)	0.0237 (9)
O3	0.0747 (11)	0.0672 (11)	0.0587 (9)	0.0091 (8)	0.0173 (8)	0.0190 (8)
O4	0.0481 (9)	0.0665 (11)	0.0659 (10)	0.0111 (7)	−0.0123 (7)	0.0033 (8)
O5	0.0456 (9)	0.0688 (11)	0.0723 (10)	0.0096 (7)	0.0055 (8)	0.0127 (8)
S1	0.0447 (3)	0.0511 (3)	0.0492 (3)	0.0066 (2)	0.0007 (2)	0.0071 (2)

Geometric parameters (Å, º) top

C1—C6	1.381 (3)	C12—C13	1.375 (3)
C1—C2	1.384 (3)	C12—H12	0.9300
C1—N1	1.425 (2)	C13—H13	0.9300
C2—C3	1.380 (3)	C14—H14A	0.9600
C2—H2	0.9300	C14—H14B	0.9600
C3—C4	1.380 (3)	C14—H14C	0.9600
C3—H3	0.9300	C15—O5	1.224 (3)
C4—C5	1.388 (2)	C15—N2	1.317 (3)
C4—C7	1.485 (3)	C15—H15	0.9300
C5—C6	1.380 (3)	C16—N2	1.442 (3)
C5—H5	0.9300	C16—H16A	0.9600
C6—H6	0.9300	C16—H16B	0.9600
C7—O1	1.211 (2)	C16—H16C	0.9600
C7—O2	1.315 (2)	C17—N2	1.450 (3)
C8—C13	1.386 (3)	C17—H17A	0.9600
C8—C9	1.386 (3)	C17—H17B	0.9600
C8—S1	1.762 (2)	C17—H17C	0.9600
C9—C10	1.382 (3)	N1—S1	1.6243 (17)
C9—H9	0.9300	N1—H1	0.8600
C10—C11	1.382 (3)	O2—H2A	0.8200
C10—H10	0.9300	O3—S1	1.4266 (16)
C11—C12	1.387 (3)	O4—S1	1.4291 (15)
C11—C14	1.512 (3)

C6—C1—C2	119.62 (17)	C12—C13—H13	120.3
C6—C1—N1	118.66 (16)	C8—C13—H13	120.3
C2—C1—N1	121.62 (17)	C11—C14—H14A	109.5
C3—C2—C1	120.08 (18)	C11—C14—H14B	109.5
C3—C2—H2	120.0	H14A—C14—H14B	109.5
C1—C2—H2	120.0	C11—C14—H14C	109.5
C2—C3—C4	120.81 (18)	H14A—C14—H14C	109.5
C2—C3—H3	119.6	H14B—C14—H14C	109.5
C4—C3—H3	119.6	O5—C15—N2	124.8 (2)
C3—C4—C5	118.68 (17)	O5—C15—H15	117.6
C3—C4—C7	119.61 (17)	N2—C15—H15	117.6
C5—C4—C7	121.68 (18)	N2—C16—H16A	109.5
C6—C5—C4	120.87 (18)	N2—C16—H16B	109.5
C6—C5—H5	119.6	H16A—C16—H16B	109.5
C4—C5—H5	119.6	N2—C16—H16C	109.5
C5—C6—C1	119.87 (17)	H16A—C16—H16C	109.5
C5—C6—H6	120.1	H16B—C16—H16C	109.5
C1—C6—H6	120.1	N2—C17—H17A	109.5
O1—C7—O2	123.18 (18)	N2—C17—H17B	109.5
O1—C7—C4	123.84 (19)	H17A—C17—H17B	109.5
O2—C7—C4	112.97 (16)	N2—C17—H17C	109.5
C13—C8—C9	119.9 (2)	H17A—C17—H17C	109.5
C13—C8—S1	119.26 (16)	H17B—C17—H17C	109.5
C9—C8—S1	120.86 (17)	C1—N1—S1	124.87 (13)
C10—C9—C8	119.7 (2)	C1—N1—H1	117.6
C10—C9—H9	120.2	S1—N1—H1	117.6
C8—C9—H9	120.2	C15—N2—C16	120.48 (18)
C11—C10—C9	121.2 (2)	C15—N2—C17	122.1 (2)
C11—C10—H10	119.4	C16—N2—C17	117.4 (2)
C9—C10—H10	119.4	C7—O2—H2A	109.5
C10—C11—C12	118.0 (2)	O3—S1—O4	119.31 (10)
C10—C11—C14	121.7 (2)	O3—S1—N1	109.82 (9)
C12—C11—C14	120.3 (2)	O4—S1—N1	104.71 (9)
C13—C12—C11	121.7 (2)	O3—S1—C8	107.75 (10)
C13—C12—H12	119.1	O4—S1—C8	108.51 (9)
C11—C12—H12	119.1	N1—S1—C8	106.00 (9)
C12—C13—C8	119.4 (2)

C6—C1—C2—C3	1.5 (3)	C10—C11—C12—C13	−0.8 (4)
N1—C1—C2—C3	−174.66 (19)	C14—C11—C12—C13	179.6 (2)
C1—C2—C3—C4	1.0 (3)	C11—C12—C13—C8	0.3 (4)
C2—C3—C4—C5	−2.2 (3)	C9—C8—C13—C12	0.6 (3)
C2—C3—C4—C7	175.86 (19)	S1—C8—C13—C12	−177.99 (18)
C3—C4—C5—C6	0.9 (3)	C6—C1—N1—S1	135.20 (17)
C7—C4—C5—C6	−177.16 (19)	C2—C1—N1—S1	−48.6 (2)
C4—C5—C6—C1	1.7 (3)	O5—C15—N2—C16	−0.3 (4)
C2—C1—C6—C5	−2.9 (3)	O5—C15—N2—C17	178.1 (2)
N1—C1—C6—C5	173.46 (18)	C1—N1—S1—O3	51.58 (18)
C3—C4—C7—O1	7.1 (3)	C1—N1—S1—O4	−179.18 (15)
C5—C4—C7—O1	−174.9 (2)	C1—N1—S1—C8	−64.55 (17)
C3—C4—C7—O2	−172.33 (19)	C13—C8—S1—O3	−170.90 (16)
C5—C4—C7—O2	5.7 (3)	C9—C8—S1—O3	10.6 (2)
C13—C8—C9—C10	−0.8 (3)	C13—C8—S1—O4	58.62 (19)
S1—C8—C9—C10	177.71 (17)	C9—C8—S1—O4	−119.92 (17)
C8—C9—C10—C11	0.2 (3)	C13—C8—S1—N1	−53.38 (19)
C9—C10—C11—C12	0.6 (4)	C9—C8—S1—N1	128.09 (17)
C9—C10—C11—C14	−179.9 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.27	2.903 (2)	131
O2—H2A···O5ⁱⁱ	0.82	1.79	2.598 (2)	168
C16—H16C···Cg1	0.96	2.98	3.576 (3)	121

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₄S·C₃H₇NO
M_r	364.41
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	8.0953 (10), 25.151 (3), 8.8840 (11)
β (°)	98.010 (1)
V (Å³)	1791.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.39 × 0.29 × 0.25

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.923, 0.949
No. of measured, independent and observed [I > 2σ(I)] reflections	9993, 3336, 2570
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.111, 1.04
No. of reflections	3336
No. of parameters	230
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.37

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.27	2.903 (2)	131
O2—H2A···O5ⁱⁱ	0.82	1.79	2.598 (2)	168
C16—H16C···Cg1	0.96	2.98	3.576 (3)	121

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

Acknowledgements

This work was supported by the Education Department Foundation of Fujian Province of China (grant No. 2008 F5053) and the Master Construction Project of Quanzhou Normal University.

References

Antolini, L., Menabue, L., Saladini, M., Pellacani, G. C., Battaglia, L. P., Sola, M. & Bonamartini Corradi, A. (1984). J. Chem. Soc. Dalton Trans. pp. 2319–2323. CSD CrossRef Web of Science Google Scholar
Bruker (2001). SMART. Bruker AXS Inc., Madison,Wisconsin,USA. Google Scholar
Bruker (2003). SAINT. Bruker AXS Inc., Madison, Wisconsin,USA. Google Scholar
Menabue, L. & Saladini, M. (1988). Acta Cryst. C44, 2087–2089. CSD CrossRef Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1062

doi:10.1107/S1600536811011949

Open

access