N-(2-Meth-oxy-phen-yl)benzene-sulfonamide.

The asymmetric unit of the title compound, C(13)H(13)NO(3)S, contains two crystallographically independent mol-ecules in which the dihedral angles between the phenyl and benzene rings are 88.16 (12) and 44.50 (12)°. One of the mol-ecules features an intra-molecular N-H⋯O hydrogen bond. In the crystal, the mol-ecules are linked into dimers by pairs of N-H⋯O hydrogen bonds. The dimers are further connected by C-H⋯O and C-H⋯π inter-actions, forming a three-dimensional network.

Related literature

For the biological activity of sulfonamides, see: Arshad et al. (2008 ▶); Gennarti et al. (1994 ▶); Kayser et al. (2004 ▶); Rough et al. (1998 ▶).

Experimental

Crystal data

C13H13NO3S

M = 263.31

Monoclinic,

a = 8.7705 (2) Å

b = 28.1684 (7) Å

c = 10.7256 (3) Å

β = 105.968 (1)°

V = 2547.53 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.25 mm−1

T = 296 K

0.25 × 0.17 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer

24823 measured reflections

6318 independent reflections

4145 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.113

S = 1.02

6318 reflections

333 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.29 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 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023871/hb5501sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023871/hb5501Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H13NO3S	F(000) = 1104
Mr = 263.31	Dx = 1.373 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5117 reflections
a = 8.7705 (2) Å	θ = 2.5–23.9°
b = 28.1684 (7) Å	µ = 0.25 mm−1
c = 10.7256 (3) Å	T = 296 K
β = 105.968 (1)°	Block, colourless
V = 2547.53 (11) Å3	0.25 × 0.17 × 0.07 mm
Z = 8

Bruker APEXII CCD diffractometer	4145 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.043
graphite	θmax = 28.3°, θmin = 3.3°
φ and ω scans	h = −11→11
24823 measured reflections	k = −37→37
6318 independent reflections	l = −14→14

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0488P)2 + 0.3381P] where P = (Fo2 + 2Fc2)/3
6318 reflections	(Δ/σ)max = 0.001
333 parameters	Δρmax = 0.29 e Å−3
2 restraints	Δρmin = −0.29 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.33115 (5)	0.81887 (2)	0.56961 (5)	0.0412 (2)
O1	0.29814 (16)	0.77142 (5)	0.59898 (15)	0.0561 (5)
O2	0.21225 (14)	0.84480 (5)	0.47617 (14)	0.0518 (5)
O3	0.68975 (15)	0.82034 (5)	0.38159 (14)	0.0507 (5)
N1	0.48440 (18)	0.81979 (6)	0.51516 (16)	0.0430 (5)
C1	0.3503 (3)	0.83266 (9)	0.8243 (2)	0.0681 (9)
C2	0.3878 (4)	0.85873 (11)	0.9379 (3)	0.0865 (11)
C3	0.4523 (3)	0.90282 (11)	0.9397 (3)	0.0764 (10)
C4	0.4848 (3)	0.92123 (8)	0.8326 (3)	0.0663 (9)
C5	0.4496 (2)	0.89536 (7)	0.7189 (2)	0.0511 (7)
C6	0.3823 (2)	0.85108 (7)	0.71581 (19)	0.0424 (6)
C7	0.6322 (2)	0.79744 (6)	0.57144 (18)	0.0388 (6)
C8	0.6717 (3)	0.77602 (7)	0.6914 (2)	0.0536 (7)
C9	0.8209 (3)	0.75621 (9)	0.7392 (3)	0.0681 (9)
C10	0.9276 (3)	0.75748 (9)	0.6684 (3)	0.0728 (9)
C11	0.8897 (2)	0.77854 (8)	0.5478 (3)	0.0596 (8)
C12	0.7411 (2)	0.79839 (6)	0.4983 (2)	0.0417 (6)
C13	0.7966 (3)	0.82674 (9)	0.3050 (2)	0.0653 (9)
S1'	0.31232 (5)	0.92918 (2)	0.25688 (5)	0.0434 (2)
O1'	0.41671 (16)	0.89021 (5)	0.30204 (16)	0.0599 (5)
O2'	0.37153 (17)	0.97058 (5)	0.21000 (15)	0.0587 (5)
O3'	−0.07087 (16)	0.95549 (5)	0.29180 (16)	0.0619 (5)
N1'	0.24881 (18)	0.94574 (6)	0.37937 (16)	0.0432 (6)
C1'	0.1023 (3)	0.86096 (7)	0.1393 (2)	0.0540 (7)
C2'	−0.0250 (3)	0.84437 (9)	0.0434 (3)	0.0675 (9)
C3'	−0.1041 (3)	0.87391 (10)	−0.0551 (2)	0.0720 (10)
C4'	−0.0567 (3)	0.92019 (9)	−0.0586 (2)	0.0687 (9)
C5'	0.0710 (3)	0.93721 (8)	0.0355 (2)	0.0542 (7)
C6'	0.1504 (2)	0.90740 (7)	0.13445 (18)	0.0412 (6)
C7'	0.1746 (2)	0.99118 (7)	0.37841 (18)	0.0415 (6)
C8'	0.2668 (3)	1.02998 (7)	0.4245 (2)	0.0570 (8)
C9'	0.1992 (3)	1.07399 (8)	0.4279 (3)	0.0711 (10)
C10'	0.0390 (3)	1.07863 (9)	0.3853 (3)	0.0694 (10)
C11'	−0.0561 (3)	1.04027 (8)	0.3392 (2)	0.0593 (8)
C12'	0.0103 (2)	0.99586 (7)	0.33485 (19)	0.0453 (7)
C13'	−0.2368 (3)	0.95970 (11)	0.2309 (3)	0.0931 (13)
H1	0.30370	0.80290	0.82150	0.0820*
H1N	0.476 (2)	0.8381 (6)	0.4514 (17)	0.0520*
H2	0.36910	0.84620	1.01260	0.1040*
H3	0.47460	0.92060	1.01560	0.0910*
H4	0.53060	0.95110	0.83600	0.0800*
H5	0.47120	0.90770	0.64510	0.0610*
H8	0.59870	0.77490	0.74000	0.0640*
H9	0.84830	0.74190	0.82050	0.0820*
H10	1.02730	0.74400	0.70170	0.0870*
H11	0.96360	0.77940	0.50010	0.0710*
H13A	0.88270	0.84670	0.35050	0.0980*
H13B	0.74210	0.84140	0.22420	0.0980*
H13C	0.83730	0.79650	0.28840	0.0980*
H1'	0.15550	0.84110	0.20650	0.0650*
H1N'	0.210 (2)	0.9225 (6)	0.4068 (19)	0.0520*
H2'	−0.05770	0.81300	0.04530	0.0810*
H3'	−0.19020	0.86250	−0.11970	0.0860*
H4'	−0.11130	0.94010	−0.12520	0.0820*
H5'	0.10370	0.96850	0.03280	0.0650*
H8'	0.37640	1.02660	0.45380	0.0680*
H9'	0.26260	1.10020	0.45910	0.0850*
H10'	−0.00680	1.10830	0.38740	0.0830*
H11'	−0.16560	1.04410	0.31080	0.0710*
H13D	−0.28950	0.97050	0.29310	0.1400*
H13E	−0.27860	0.92930	0.19770	0.1400*
H13F	−0.25390	0.98210	0.16090	0.1400*

	U11	U22	U33	U12	U13	U23
S1	0.0350 (2)	0.0431 (3)	0.0485 (3)	0.0004 (2)	0.0165 (2)	−0.0006 (2)
O1	0.0577 (9)	0.0437 (8)	0.0721 (11)	−0.0080 (7)	0.0265 (8)	−0.0027 (7)
O2	0.0329 (7)	0.0658 (9)	0.0574 (9)	0.0070 (6)	0.0137 (6)	0.0053 (7)
O3	0.0403 (7)	0.0654 (9)	0.0508 (8)	0.0048 (7)	0.0200 (6)	0.0008 (7)
N1	0.0351 (8)	0.0546 (10)	0.0419 (9)	0.0105 (7)	0.0148 (7)	0.0079 (7)
C1	0.0940 (18)	0.0595 (15)	0.0663 (16)	−0.0063 (13)	0.0479 (14)	−0.0035 (12)
C2	0.114 (2)	0.098 (2)	0.0639 (18)	0.0013 (19)	0.0522 (17)	−0.0102 (16)
C3	0.0722 (17)	0.093 (2)	0.0642 (17)	0.0062 (15)	0.0193 (14)	−0.0275 (15)
C4	0.0516 (13)	0.0576 (15)	0.0858 (19)	−0.0042 (11)	0.0126 (13)	−0.0189 (13)
C5	0.0466 (11)	0.0494 (12)	0.0588 (14)	−0.0019 (10)	0.0169 (10)	0.0001 (10)
C6	0.0410 (10)	0.0436 (11)	0.0469 (11)	0.0050 (8)	0.0195 (9)	0.0004 (9)
C7	0.0333 (9)	0.0354 (10)	0.0463 (11)	0.0035 (8)	0.0084 (8)	−0.0031 (8)
C8	0.0521 (12)	0.0505 (13)	0.0560 (13)	0.0049 (10)	0.0114 (10)	0.0089 (10)
C9	0.0635 (15)	0.0601 (15)	0.0686 (16)	0.0082 (12)	−0.0022 (13)	0.0190 (12)
C10	0.0448 (12)	0.0618 (16)	0.101 (2)	0.0167 (11)	0.0017 (13)	0.0162 (14)
C11	0.0365 (11)	0.0537 (13)	0.0886 (18)	0.0076 (10)	0.0174 (11)	−0.0007 (12)
C12	0.0328 (9)	0.0362 (10)	0.0543 (12)	0.0000 (8)	0.0091 (8)	−0.0062 (9)
C13	0.0596 (13)	0.0753 (16)	0.0730 (16)	−0.0073 (12)	0.0383 (13)	−0.0062 (13)
S1'	0.0351 (2)	0.0419 (3)	0.0543 (3)	0.0050 (2)	0.0143 (2)	0.0066 (2)
O1'	0.0452 (8)	0.0579 (9)	0.0768 (11)	0.0199 (7)	0.0172 (7)	0.0121 (8)
O2'	0.0542 (8)	0.0521 (9)	0.0770 (11)	−0.0079 (7)	0.0304 (8)	0.0062 (8)
O3'	0.0368 (7)	0.0664 (10)	0.0780 (11)	−0.0051 (7)	0.0085 (7)	−0.0066 (8)
N1'	0.0405 (9)	0.0425 (10)	0.0463 (10)	0.0013 (7)	0.0113 (7)	0.0067 (7)
C1'	0.0641 (13)	0.0433 (12)	0.0555 (13)	0.0007 (10)	0.0178 (11)	0.0076 (10)
C2'	0.0769 (16)	0.0555 (15)	0.0686 (16)	−0.0142 (12)	0.0174 (14)	−0.0068 (12)
C3'	0.0709 (16)	0.0831 (19)	0.0549 (15)	−0.0082 (14)	0.0053 (12)	−0.0136 (13)
C4'	0.0729 (16)	0.0741 (17)	0.0503 (14)	0.0100 (13)	0.0023 (12)	0.0064 (12)
C5'	0.0635 (13)	0.0466 (12)	0.0515 (13)	0.0081 (10)	0.0141 (11)	0.0089 (10)
C6'	0.0431 (10)	0.0406 (11)	0.0429 (11)	0.0061 (8)	0.0168 (9)	0.0027 (8)
C7'	0.0403 (10)	0.0456 (11)	0.0391 (10)	0.0035 (8)	0.0120 (8)	0.0001 (8)
C8'	0.0460 (11)	0.0542 (13)	0.0696 (15)	−0.0039 (10)	0.0141 (11)	−0.0114 (11)
C9'	0.0695 (16)	0.0507 (14)	0.094 (2)	−0.0067 (12)	0.0242 (14)	−0.0202 (13)
C10'	0.0766 (17)	0.0563 (15)	0.0807 (18)	0.0155 (13)	0.0306 (14)	−0.0106 (13)
C11'	0.0474 (12)	0.0714 (16)	0.0611 (15)	0.0170 (11)	0.0183 (11)	−0.0006 (12)
C12'	0.0389 (10)	0.0543 (13)	0.0433 (11)	0.0013 (9)	0.0122 (9)	−0.0005 (9)
C13'	0.0414 (13)	0.098 (2)	0.123 (3)	−0.0113 (13)	−0.0060 (14)	−0.0054 (18)

S1—O1	1.4212 (15)	C5—H5	0.9300
S1—O2	1.4319 (15)	C8—H8	0.9300
S1—N1	1.6063 (17)	C9—H9	0.9300
S1—C6	1.760 (2)	C10—H10	0.9300
S1'—C6'	1.7582 (19)	C11—H11	0.9300
S1'—N1'	1.6299 (17)	C13—H13A	0.9600
S1'—O1'	1.4260 (15)	C13—H13C	0.9600
S1'—O2'	1.4235 (15)	C13—H13B	0.9600
O3—C12	1.357 (2)	C1'—C2'	1.375 (4)
O3—C13	1.417 (3)	C1'—C6'	1.380 (3)
O3'—C12'	1.354 (2)	C2'—C3'	1.374 (4)
O3'—C13'	1.427 (3)	C3'—C4'	1.372 (4)
N1—C7	1.418 (2)	C4'—C5'	1.372 (3)
N1—H1N	0.843 (17)	C5'—C6'	1.382 (3)
N1'—C7'	1.435 (3)	C7'—C12'	1.394 (3)
N1'—H1N'	0.828 (18)	C7'—C8'	1.369 (3)
C1—C2	1.383 (4)	C8'—C9'	1.379 (3)
C1—C6	1.372 (3)	C9'—C10'	1.359 (4)
C2—C3	1.363 (4)	C10'—C11'	1.371 (4)
C3—C4	1.360 (4)	C11'—C12'	1.386 (3)
C4—C5	1.381 (4)	C1'—H1'	0.9300
C5—C6	1.376 (3)	C2'—H2'	0.9300
C7—C12	1.393 (3)	C3'—H3'	0.9300
C7—C8	1.376 (3)	C4'—H4'	0.9300
C8—C9	1.385 (4)	C5'—H5'	0.9300
C9—C10	1.358 (4)	C8'—H8'	0.9300
C10—C11	1.378 (4)	C9'—H9'	0.9300
C11—C12	1.383 (3)	C10'—H10'	0.9300
C1—H1	0.9300	C11'—H11'	0.9300
C2—H2	0.9300	C13'—H13D	0.9600
C3—H3	0.9300	C13'—H13E	0.9600
C4—H4	0.9300	C13'—H13F	0.9600
O1—S1—O2	118.77 (9)	C9—C10—H10	120.00
O1—S1—N1	109.73 (9)	C11—C10—H10	120.00
O1—S1—C6	107.75 (9)	C10—C11—H11	120.00
O2—S1—N1	104.98 (9)	C12—C11—H11	120.00
O2—S1—C6	108.59 (9)	O3—C13—H13A	109.00
N1—S1—C6	106.38 (9)	H13A—C13—H13C	109.00
O1'—S1'—O2'	119.21 (9)	H13B—C13—H13C	109.00
O1'—S1'—N1'	106.05 (9)	H13A—C13—H13B	109.00
O1'—S1'—C6'	107.24 (9)	O3—C13—H13B	109.00
O2'—S1'—N1'	106.80 (9)	O3—C13—H13C	110.00
O2'—S1'—C6'	108.68 (9)	C2'—C1'—C6'	119.2 (2)
N1'—S1'—C6'	108.48 (9)	C1'—C2'—C3'	120.3 (2)
C12—O3—C13	119.21 (16)	C2'—C3'—C4'	120.3 (2)
C12'—O3'—C13'	117.44 (18)	C3'—C4'—C5'	120.3 (2)
S1—N1—C7	126.62 (14)	C4'—C5'—C6'	119.3 (2)
C7—N1—H1N	118.8 (12)	S1'—C6'—C5'	119.63 (16)
S1—N1—H1N	114.2 (12)	C1'—C6'—C5'	120.68 (19)
S1'—N1'—C7'	120.30 (13)	S1'—C6'—C1'	119.68 (15)
C7'—N1'—H1N'	118.5 (13)	C8'—C7'—C12'	119.96 (19)
S1'—N1'—H1N'	109.0 (13)	N1'—C7'—C8'	119.22 (18)
C2—C1—C6	119.5 (2)	N1'—C7'—C12'	120.80 (17)
C1—C2—C3	119.6 (3)	C7'—C8'—C9'	120.8 (2)
C2—C3—C4	121.2 (3)	C8'—C9'—C10'	119.3 (2)
C3—C4—C5	119.8 (2)	C9'—C10'—C11'	121.0 (2)
C4—C5—C6	119.3 (2)	C10'—C11'—C12'	120.3 (2)
C1—C6—C5	120.58 (19)	C7'—C12'—C11'	118.65 (19)
S1—C6—C1	119.96 (16)	O3'—C12'—C7'	115.67 (17)
S1—C6—C5	119.42 (15)	O3'—C12'—C11'	125.68 (18)
C8—C7—C12	119.97 (19)	C2'—C1'—H1'	120.00
N1—C7—C8	123.93 (19)	C6'—C1'—H1'	120.00
N1—C7—C12	116.10 (16)	C1'—C2'—H2'	120.00
C7—C8—C9	119.5 (2)	C3'—C2'—H2'	120.00
C8—C9—C10	120.6 (3)	C2'—C3'—H3'	120.00
C9—C10—C11	120.7 (3)	C4'—C3'—H3'	120.00
C10—C11—C12	119.5 (2)	C3'—C4'—H4'	120.00
C7—C12—C11	119.7 (2)	C5'—C4'—H4'	120.00
O3—C12—C7	115.04 (16)	C4'—C5'—H5'	120.00
O3—C12—C11	125.23 (19)	C6'—C5'—H5'	120.00
C6—C1—H1	120.00	C7'—C8'—H8'	120.00
C2—C1—H1	120.00	C9'—C8'—H8'	120.00
C3—C2—H2	120.00	C8'—C9'—H9'	120.00
C1—C2—H2	120.00	C10'—C9'—H9'	120.00
C4—C3—H3	119.00	C9'—C10'—H10'	119.00
C2—C3—H3	119.00	C11'—C10'—H10'	120.00
C5—C4—H4	120.00	C10'—C11'—H11'	120.00
C3—C4—H4	120.00	C12'—C11'—H11'	120.00
C4—C5—H5	120.00	O3'—C13'—H13D	109.00
C6—C5—H5	120.00	O3'—C13'—H13E	109.00
C7—C8—H8	120.00	O3'—C13'—H13F	109.00
C9—C8—H8	120.00	H13D—C13'—H13E	109.00
C10—C9—H9	120.00	H13D—C13'—H13F	109.00
C8—C9—H9	120.00	H13E—C13'—H13F	110.00
O1—S1—N1—C7	−49.05 (18)	C4—C5—C6—S1	177.86 (17)
O2—S1—N1—C7	−177.75 (15)	C4—C5—C6—C1	0.0 (3)
C6—S1—N1—C7	67.25 (18)	C12—C7—C8—C9	1.0 (3)
O1—S1—C6—C1	−14.8 (2)	N1—C7—C12—O3	−0.7 (2)
O1—S1—C6—C5	167.32 (15)	N1—C7—C8—C9	−178.4 (2)
O2—S1—C6—C1	115.07 (18)	C8—C7—C12—O3	179.93 (17)
O2—S1—C6—C5	−62.83 (17)	C8—C7—C12—C11	−1.2 (3)
N1—S1—C6—C1	−132.41 (18)	N1—C7—C12—C11	178.21 (18)
N1—S1—C6—C5	49.70 (18)	C7—C8—C9—C10	−0.5 (4)
N1'—S1'—C6'—C5'	95.33 (18)	C8—C9—C10—C11	0.1 (4)
O1'—S1'—N1'—C7'	163.92 (14)	C9—C10—C11—C12	−0.3 (4)
O2'—S1'—N1'—C7'	35.80 (17)	C10—C11—C12—C7	0.8 (3)
C6'—S1'—N1'—C7'	−81.17 (16)	C10—C11—C12—O3	179.6 (2)
O1'—S1'—C6'—C1'	30.5 (2)	C6'—C1'—C2'—C3'	−0.7 (4)
O1'—S1'—C6'—C5'	−150.54 (17)	C2'—C1'—C6'—S1'	179.66 (19)
O2'—S1'—C6'—C1'	160.64 (17)	C2'—C1'—C6'—C5'	0.7 (3)
O2'—S1'—C6'—C5'	−20.4 (2)	C1'—C2'—C3'—C4'	0.0 (4)
N1'—S1'—C6'—C1'	−83.61 (19)	C2'—C3'—C4'—C5'	0.7 (4)
C13—O3—C12—C7	174.60 (17)	C3'—C4'—C5'—C6'	−0.6 (4)
C13—O3—C12—C11	−4.2 (3)	C4'—C5'—C6'—S1'	−179.01 (18)
C13'—O3'—C12'—C7'	−172.1 (2)	C4'—C5'—C6'—C1'	−0.1 (3)
C13'—O3'—C12'—C11'	8.2 (3)	N1'—C7'—C8'—C9'	−178.5 (2)
S1—N1—C7—C8	−8.1 (3)	C12'—C7'—C8'—C9'	−0.3 (3)
S1—N1—C7—C12	172.47 (14)	N1'—C7'—C12'—O3'	−1.5 (3)
S1'—N1'—C7'—C8'	−88.1 (2)	N1'—C7'—C12'—C11'	178.22 (18)
S1'—N1'—C7'—C12'	93.8 (2)	C8'—C7'—C12'—O3'	−179.62 (18)
C2—C1—C6—C5	−0.7 (4)	C8'—C7'—C12'—C11'	0.1 (3)
C6—C1—C2—C3	1.6 (4)	C7'—C8'—C9'—C10'	0.3 (4)
C2—C1—C6—S1	−178.6 (2)	C8'—C9'—C10'—C11'	0.1 (4)
C1—C2—C3—C4	−1.9 (5)	C9'—C10'—C11'—C12'	−0.3 (4)
C2—C3—C4—C5	1.2 (4)	C10'—C11'—C12'—O3'	179.9 (2)
C3—C4—C5—C6	−0.2 (4)	C10'—C11'—C12'—C7'	0.2 (3)

Cg4 is the centroid of the C7'–C12' phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1'—H1N'···O2	0.828 (18)	2.310 (17)	3.074 (2)	153.6 (17)
N1—H1N···O1'	0.843 (17)	2.129 (17)	2.961 (2)	168.7 (17)
N1—H1N···O3	0.843 (17)	2.258 (18)	2.592 (2)	103.8 (14)
C4—H4···O2'i	0.93	2.47	3.377 (3)	167
C4'—H4'···Cg4ii	0.93	2.85	3.601 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C7′–C12′ phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1′—H1N′⋯O2	0.828 (18)	2.310 (17)	3.074 (2)	153.6 (17)
N1—H1N⋯O1′	0.843 (17)	2.129 (17)	2.961 (2)	168.7 (17)
N1—H1N⋯O3	0.843 (17)	2.258 (18)	2.592 (2)	103.8 (14)
C4—H4⋯O2′i	0.93	2.47	3.377 (3)	167
C4′—H4′⋯Cg4ii	0.93	2.85	3.601 (2)	138

Symmetry codes: (i) ; (ii) .