Biological properties of two enanti­omorphic forms of N-(2,6-di­methyl­phen­yl)-4-hy­droxy-2,2-dioxo-1H-2λ⁶,1-benzo­thia­zine-3-carboxamide, a structural analogue of piroxicam

The title benzo­thia­zine-3-carboxamide, C₁₇H₁₆N₂O₄S, crystallized in two enanti­omorphic crystal forms with the space groups P3₂ and P3₁ despite the absence of a classic stereogenic atom. The mol­ecular structures are mirror images of each other. Only one sulfonyl O atom takes part in intra­molecular hydrogen bonding as a proton acceptor and this atom is different in the two enanti­omorphic structures. As a result, the S atom becomes a pseudo-stereogenic centre. This fact is worth taking into account due to the different biological activities of the enanti­omorphic forms. One form possesses a high analgesic activity, while the other form revealed a high anti-inflammatory activity.

Computing details

Data collection: CrysAlis CCD (Agilent, 2012) for (1A); CrysAlis PRO (Agilent, 2013) for (1B). Cell refinement: CrysAlis CCD (Agilent, 2012) for (1A); CrysAlis PRO (Agilent, 2013) for (1B). Data reduction: CrysAlis RED (Agilent, 2012) for (1A); CrysAlis PRO (Agilent, 2013) for (1B). For both structures, program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015b).

N-(2,6-Dimethylphenyl)-4-hydroxy-2,2-dioxo-1H-2λ⁶,1-\ benzothiazine-3-carboxamide (1A)

Crystal data

C17H16N2O4S	Dx = 1.411 Mg m^−3
Mr = 344.38	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P32	Cell parameters from 4175 reflections
a = 8.3729 (2) Å	θ = 3.5–30.8°
c = 20.0206 (6) Å	µ = 0.22 mm^−1
V = 1215.51 (7) Å^3	T = 293 K
Z = 3	Block, colorless
F(000) = 540	0.30 × 0.14 × 0.13 mm

Data collection

Agilent Xcalibur Sapphire3 diffractometer	4446 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3787 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm^-1	Rint = 0.022
ω scans	θmax = 30.0°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012)	h = −10→11
Tmin = 0.974, Tmax = 1.000	k = −11→9
12429 measured reflections	l = −21→28

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.036	w = 1/[σ^2(Fo^2) + (0.0521P)^2 + 0.0047P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.093	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.19 e Å^−3
4446 reflections	Δρmin = −0.26 e Å^−3
231 parameters	Absolute structure: Flack x determined using 1505 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.00 (6)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	1.00522 (10)	0.52328 (8)	0.06771 (3)	0.04135 (15)
O1	0.7732 (3)	0.0045 (2)	0.11781 (9)	0.0485 (5)
H1O	0.722 (6)	0.022 (6)	0.154 (2)	0.077 (12)*
O2	0.7127 (3)	0.1748 (2)	0.20978 (8)	0.0475 (4)
O3	1.1918 (3)	0.5878 (3)	0.08652 (10)	0.0570 (5)
O4	0.9361 (4)	0.6481 (3)	0.07392 (11)	0.0619 (6)
N1	0.9764 (4)	0.4573 (3)	−0.00925 (10)	0.0449 (5)
H1N	0.930 (6)	0.493 (6)	−0.036 (2)	0.084 (13)*
N2	0.7901 (4)	0.4729 (4)	0.19574 (11)	0.0495 (6)
H2N	0.823 (4)	0.563 (5)	0.1679 (17)	0.054 (9)*
C1	0.9804 (4)	0.2970 (4)	−0.02674 (12)	0.0399 (5)
C2	1.0313 (4)	0.2796 (4)	−0.09147 (12)	0.0522 (7)
H2	1.063178	0.373389	−0.122522	0.063*
C3	1.0338 (5)	0.1211 (5)	−0.10885 (14)	0.0585 (8)
H3	1.063457	0.106584	−0.152342	0.070*
C4	0.9929 (5)	−0.0150 (4)	−0.06268 (15)	0.0572 (7)
H4	1.000927	−0.118202	−0.074474	0.069*
C5	0.9399 (4)	0.0003 (4)	0.00128 (14)	0.0476 (6)
H5	0.910375	−0.093572	0.032098	0.057*
C6	0.9304 (3)	0.1554 (3)	0.01969 (11)	0.0370 (5)
C7	0.8568 (3)	0.1631 (3)	0.08478 (11)	0.0355 (5)
C8	0.8665 (3)	0.3195 (3)	0.11064 (11)	0.0357 (5)
C9	0.7844 (3)	0.3184 (3)	0.17522 (11)	0.0380 (5)
C10	0.7393 (4)	0.5035 (4)	0.26062 (12)	0.0465 (6)
C11	0.8485 (5)	0.5192 (4)	0.31508 (15)	0.0555 (7)
C12	0.7994 (7)	0.5637 (5)	0.37604 (16)	0.0769 (11)
H12	0.868211	0.574471	0.413963	0.092*
C13	0.6526 (7)	0.5917 (5)	0.38125 (18)	0.0800 (12)
H13	0.623733	0.622367	0.422398	0.096*
C14	0.5493 (6)	0.5754 (5)	0.32740 (18)	0.0702 (9)
H14	0.449314	0.594212	0.332012	0.084*
C15	0.5889 (5)	0.5313 (4)	0.26530 (15)	0.0558 (7)
C16	1.0125 (6)	0.4951 (6)	0.3090 (2)	0.0798 (11)
H16C	0.972589	0.366799	0.302999	0.120*
H16B	1.085557	0.539301	0.348859	0.120*
H16A	1.084992	0.563763	0.271243	0.120*
C17	0.4744 (6)	0.5181 (8)	0.2058 (2)	0.0894 (13)
H17C	0.553719	0.591218	0.169992	0.134*
H17B	0.392562	0.562898	0.217393	0.134*
H17A	0.403684	0.391825	0.191737	0.134*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0566 (4)	0.0343 (3)	0.0352 (2)	0.0242 (3)	0.0058 (2)	0.0060 (2)
O1	0.0662 (13)	0.0356 (9)	0.0441 (10)	0.0258 (9)	0.0120 (9)	0.0088 (7)
O2	0.0582 (12)	0.0434 (10)	0.0406 (9)	0.0251 (9)	0.0138 (8)	0.0080 (8)
O3	0.0507 (11)	0.0506 (12)	0.0513 (11)	0.0116 (9)	−0.0003 (9)	0.0041 (9)
O4	0.1044 (18)	0.0473 (10)	0.0526 (11)	0.0518 (12)	0.0177 (11)	0.0121 (8)
N1	0.0680 (15)	0.0482 (12)	0.0302 (10)	0.0378 (12)	0.0007 (9)	0.0068 (8)
N2	0.0709 (16)	0.0501 (13)	0.0404 (11)	0.0399 (12)	0.0142 (11)	0.0055 (9)
C1	0.0478 (14)	0.0454 (13)	0.0321 (10)	0.0276 (11)	−0.0014 (9)	−0.0003 (9)
C2	0.0662 (19)	0.0601 (17)	0.0323 (11)	0.0330 (15)	0.0038 (11)	0.0010 (11)
C3	0.072 (2)	0.0692 (19)	0.0392 (14)	0.0388 (17)	0.0070 (13)	−0.0089 (13)
C4	0.071 (2)	0.0527 (17)	0.0546 (16)	0.0357 (16)	0.0040 (14)	−0.0120 (13)
C5	0.0573 (16)	0.0422 (14)	0.0472 (13)	0.0278 (13)	0.0026 (11)	−0.0022 (11)
C6	0.0418 (12)	0.0379 (12)	0.0350 (10)	0.0225 (10)	−0.0007 (9)	−0.0010 (9)
C7	0.0403 (12)	0.0343 (11)	0.0348 (10)	0.0209 (10)	0.0018 (9)	0.0047 (8)
C8	0.0421 (12)	0.0349 (11)	0.0342 (10)	0.0224 (10)	0.0040 (9)	0.0040 (8)
C9	0.0407 (12)	0.0419 (12)	0.0350 (11)	0.0234 (11)	0.0046 (9)	0.0038 (9)
C10	0.0604 (16)	0.0419 (13)	0.0403 (12)	0.0279 (13)	0.0079 (11)	−0.0023 (10)
C11	0.074 (2)	0.0424 (15)	0.0498 (14)	0.0290 (15)	−0.0042 (13)	−0.0005 (12)
C12	0.127 (3)	0.057 (2)	0.0428 (15)	0.043 (2)	−0.0130 (19)	−0.0041 (13)
C13	0.124 (3)	0.063 (2)	0.0522 (19)	0.047 (2)	0.026 (2)	−0.0041 (15)
C14	0.082 (2)	0.063 (2)	0.069 (2)	0.0384 (19)	0.0248 (18)	−0.0076 (16)
C15	0.0611 (18)	0.0527 (16)	0.0582 (16)	0.0319 (15)	0.0080 (14)	−0.0099 (13)
C16	0.079 (3)	0.071 (2)	0.096 (3)	0.042 (2)	−0.028 (2)	−0.010 (2)
C17	0.093 (3)	0.120 (4)	0.087 (3)	0.077 (3)	−0.017 (2)	−0.028 (3)

Geometric parameters (Å, º)

S1—O3	1.425 (2)	C5—H5	0.9300
S1—O4	1.431 (2)	C6—C7	1.457 (3)
S1—N1	1.614 (2)	C7—C8	1.372 (3)
S1—C8	1.737 (2)	C8—C9	1.463 (3)
O1—C7	1.327 (3)	C10—C11	1.386 (4)
O1—H1O	0.89 (4)	C10—C15	1.394 (4)
O2—C9	1.251 (3)	C11—C12	1.397 (5)
N1—C1	1.404 (3)	C11—C16	1.489 (6)
N1—H1N	0.81 (5)	C12—C13	1.366 (6)
N2—C9	1.334 (3)	C12—H12	0.9300
N2—C10	1.429 (3)	C13—C14	1.346 (6)
N2—H2N	0.86 (4)	C13—H13	0.9300
C1—C2	1.394 (3)	C14—C15	1.384 (4)
C1—C6	1.396 (3)	C14—H14	0.9300
C2—C3	1.382 (4)	C15—C17	1.499 (5)
C2—H2	0.9300	C16—H16C	0.9600
C3—C4	1.371 (5)	C16—H16B	0.9600
C3—H3	0.9300	C16—H16A	0.9600
C4—C5	1.382 (4)	C17—H17C	0.9600
C4—H4	0.9300	C17—H17B	0.9600
C5—C6	1.390 (3)	C17—H17A	0.9600
O3—S1—O4	117.87 (15)	C7—C8—S1	116.25 (17)
O3—S1—N1	109.27 (13)	C9—C8—S1	121.66 (18)
O4—S1—N1	106.68 (13)	O2—C9—N2	122.0 (2)
O3—S1—C8	108.02 (12)	O2—C9—C8	119.5 (2)
O4—S1—C8	111.01 (13)	N2—C9—C8	118.5 (2)
N1—S1—C8	102.95 (12)	C11—C10—C15	122.6 (3)
C7—O1—H1O	107 (3)	C11—C10—N2	119.4 (3)
C1—N1—S1	119.64 (17)	C15—C10—N2	117.8 (3)
C1—N1—H1N	116 (3)	C10—C11—C12	116.4 (3)
S1—N1—H1N	122 (3)	C10—C11—C16	122.1 (3)
C9—N2—C10	125.7 (2)	C12—C11—C16	121.5 (3)
C9—N2—H2N	119 (2)	C13—C12—C11	121.5 (3)
C10—N2—H2N	115 (2)	C13—C12—H12	119.2
C2—C1—C6	120.5 (2)	C11—C12—H12	119.2
C2—C1—N1	119.1 (2)	C14—C13—C12	120.6 (3)
C6—C1—N1	120.4 (2)	C14—C13—H13	119.7
C3—C2—C1	119.1 (3)	C12—C13—H13	119.7
C3—C2—H2	120.4	C13—C14—C15	121.3 (4)
C1—C2—H2	120.4	C13—C14—H14	119.4
C4—C3—C2	120.7 (2)	C15—C14—H14	119.4
C4—C3—H3	119.6	C14—C15—C10	117.5 (3)
C2—C3—H3	119.6	C14—C15—C17	120.3 (3)
C3—C4—C5	120.4 (3)	C10—C15—C17	122.2 (3)
C3—C4—H4	119.8	C11—C16—H16C	109.5
C5—C4—H4	119.8	C11—C16—H16B	109.5
C4—C5—C6	120.2 (3)	H16C—C16—H16B	109.5
C4—C5—H5	119.9	C11—C16—H16A	109.5
C6—C5—H5	119.9	H16C—C16—H16A	109.5
C5—C6—C1	119.0 (2)	H16B—C16—H16A	109.5
C5—C6—C7	120.1 (2)	C15—C17—H17C	109.5
C1—C6—C7	120.8 (2)	C15—C17—H17B	109.5
O1—C7—C8	121.1 (2)	H17C—C17—H17B	109.5
O1—C7—C6	115.1 (2)	C15—C17—H17A	109.5
C8—C7—C6	123.7 (2)	H17C—C17—H17A	109.5
C7—C8—C9	121.6 (2)	H17B—C17—H17A	109.5
O3—S1—N1—C1	70.0 (2)	N1—S1—C8—C7	35.3 (2)
O4—S1—N1—C1	−161.5 (2)	O3—S1—C8—C9	92.1 (2)
C8—S1—N1—C1	−44.6 (2)	O4—S1—C8—C9	−38.6 (2)
S1—N1—C1—C2	−153.8 (2)	N1—S1—C8—C9	−152.4 (2)
S1—N1—C1—C6	27.5 (4)	C10—N2—C9—O2	8.2 (4)
C6—C1—C2—C3	−0.7 (4)	C10—N2—C9—C8	−171.2 (3)
N1—C1—C2—C3	−179.5 (3)	C7—C8—C9—O2	4.3 (4)
C1—C2—C3—C4	−2.2 (5)	S1—C8—C9—O2	−167.6 (2)
C2—C3—C4—C5	3.1 (5)	C7—C8—C9—N2	−176.4 (2)
C3—C4—C5—C6	−1.1 (5)	S1—C8—C9—N2	11.7 (3)
C4—C5—C6—C1	−1.8 (4)	C9—N2—C10—C11	69.3 (4)
C4—C5—C6—C7	173.8 (3)	C9—N2—C10—C15	−115.8 (3)
C2—C1—C6—C5	2.7 (4)	C15—C10—C11—C12	0.4 (4)
N1—C1—C6—C5	−178.5 (2)	N2—C10—C11—C12	175.0 (3)
C2—C1—C6—C7	−172.9 (2)	C15—C10—C11—C16	−178.0 (3)
N1—C1—C6—C7	5.9 (4)	N2—C10—C11—C16	−3.4 (4)
C5—C6—C7—O1	−11.3 (3)	C10—C11—C12—C13	−0.6 (5)
C1—C6—C7—O1	164.2 (2)	C16—C11—C12—C13	177.8 (4)
C5—C6—C7—C8	170.4 (3)	C11—C12—C13—C14	0.6 (6)
C1—C6—C7—C8	−14.1 (4)	C12—C13—C14—C15	−0.5 (6)
O1—C7—C8—C9	−0.5 (4)	C13—C14—C15—C10	0.3 (5)
C6—C7—C8—C9	177.7 (2)	C13—C14—C15—C17	−178.6 (4)
O1—C7—C8—S1	171.8 (2)	C11—C10—C15—C14	−0.3 (5)
C6—C7—C8—S1	−10.0 (3)	N2—C10—C15—C14	−175.0 (3)
O3—S1—C8—C7	−80.2 (2)	C11—C10—C15—C17	178.6 (4)
O4—S1—C8—C7	149.1 (2)	N2—C10—C15—C17	3.9 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2	0.89 (4)	1.73 (5)	2.530 (3)	148 (4)
N2—H2N···O4	0.86 (4)	2.07 (4)	2.793 (3)	141 (3)
N1—H1N···O2^i	0.81 (5)	2.07 (5)	2.855 (3)	164 (4)

Symmetry code: (i) −y+1, x−y, z−1/3.

N-(2,6-Dimethylphenyl)-4-hydroxy-2,2-dioxo-1H-2λ⁶,1-\ benzothiazine-3-carboxamide (1B)

Crystal data

C17H16N2O4S	Dx = 1.411 Mg m^−3
Mr = 344.38	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P31	Cell parameters from 2136 reflections
a = 8.3735 (3) Å	θ = 4.1–29.8°
c = 20.0299 (8) Å	µ = 0.22 mm^−1
V = 1216.25 (10) Å^3	T = 293 K
Z = 3	Block, colorless
F(000) = 540	0.20 × 0.10 × 0.10 mm

Data collection

Xcalibur, Sapphire3 diffractometer	4687 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3771 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm^-1	Rint = 0.054
ω scans	θmax = 30.0°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	h = −11→11
Tmin = 0.646, Tmax = 1.000	k = −11→11
12184 measured reflections	l = −28→27

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0406P)^2] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.045	(Δ/σ)max = 0.008
wR(F^2) = 0.102	Δρmax = 0.27 e Å^−3
S = 1.00	Δρmin = −0.21 e Å^−3
4687 reflections	Extinction correction: SHELXL2016 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
232 parameters	Extinction coefficient: 0.011 (3)
1 restraint	Absolute structure: Flack x determined using 1397 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Hydrogen site location: mixed	Absolute structure parameter: 0.00 (5)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.32812 (12)	0.14350 (10)	0.44036 (3)	0.0416 (2)
O1	0.5600 (3)	0.6621 (3)	0.39035 (12)	0.0489 (6)
H1O	0.611 (6)	0.648 (6)	0.353 (2)	0.065 (12)*
O2	0.6209 (3)	0.4920 (3)	0.29834 (10)	0.0476 (6)
O3	0.3975 (4)	0.0190 (3)	0.43428 (13)	0.0617 (7)
O4	0.1418 (3)	0.0781 (3)	0.42140 (11)	0.0569 (6)
N1	0.3562 (4)	0.2091 (4)	0.51740 (12)	0.0453 (6)
H1N	0.411 (6)	0.180 (6)	0.543 (2)	0.069 (13)*
N2	0.5431 (4)	0.1938 (4)	0.31231 (14)	0.0499 (7)
H2N	0.513 (5)	0.107 (6)	0.339 (2)	0.061 (12)*
C1	0.3526 (4)	0.3697 (4)	0.53486 (14)	0.0397 (7)
C2	0.3021 (5)	0.3878 (5)	0.59942 (15)	0.0531 (9)
H2	0.270219	0.293987	0.630462	0.064*
C3	0.2996 (6)	0.5459 (6)	0.61700 (16)	0.0585 (10)
H3	0.270322	0.560566	0.660507	0.070*
C4	0.3402 (5)	0.6812 (5)	0.57072 (18)	0.0573 (9)
H4	0.331902	0.784352	0.582398	0.069*
C5	0.3932 (5)	0.6660 (4)	0.50695 (17)	0.0478 (7)
H5	0.422781	0.760027	0.476209	0.057*
C6	0.4026 (4)	0.5110 (4)	0.48837 (13)	0.0369 (6)
C7	0.4762 (4)	0.5034 (4)	0.42343 (14)	0.0360 (6)
C8	0.4672 (4)	0.3474 (4)	0.39742 (14)	0.0360 (6)
C9	0.5490 (4)	0.3483 (4)	0.33303 (13)	0.0372 (6)
C10	0.5940 (5)	0.1636 (4)	0.24751 (15)	0.0464 (7)
C11	0.4850 (6)	0.1478 (5)	0.19313 (18)	0.0576 (9)
C12	0.5340 (8)	0.1029 (6)	0.1320 (2)	0.0773 (13)
H12	0.464938	0.091789	0.094165	0.093*
C13	0.6808 (8)	0.0753 (6)	0.1268 (2)	0.0800 (14)
H13	0.709859	0.044930	0.085694	0.096*
C14	0.7843 (6)	0.0915 (6)	0.1809 (2)	0.0697 (11)
H14	0.884443	0.073037	0.176330	0.084*
C15	0.7440 (5)	0.1350 (5)	0.24254 (18)	0.0554 (9)
C16	0.3195 (6)	0.1712 (6)	0.1990 (3)	0.0793 (13)
H16A	0.243247	0.120691	0.160201	0.119*
H16B	0.358730	0.299962	0.202585	0.119*
H16C	0.250428	0.107872	0.238123	0.119*
C17	0.8586 (7)	0.1481 (8)	0.3022 (3)	0.0888 (15)
H17A	0.942780	0.106442	0.290292	0.133*
H17B	0.779481	0.072420	0.337556	0.133*
H17C	0.926866	0.273935	0.316989	0.133*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0570 (5)	0.0346 (4)	0.0354 (3)	0.0247 (4)	0.0055 (3)	0.0055 (3)
O1	0.0650 (15)	0.0365 (12)	0.0453 (12)	0.0255 (11)	0.0128 (12)	0.0087 (10)
O2	0.0576 (14)	0.0457 (13)	0.0411 (11)	0.0270 (11)	0.0133 (10)	0.0085 (10)
O3	0.102 (2)	0.0482 (13)	0.0524 (13)	0.0509 (14)	0.0151 (13)	0.0107 (11)
O4	0.0524 (14)	0.0502 (14)	0.0506 (13)	0.0125 (11)	−0.0008 (11)	0.0046 (11)
N1	0.0666 (19)	0.0485 (15)	0.0327 (12)	0.0377 (15)	−0.0004 (12)	0.0065 (11)
N2	0.0696 (19)	0.0509 (17)	0.0417 (14)	0.0394 (15)	0.0141 (14)	0.0057 (13)
C1	0.0461 (17)	0.0440 (17)	0.0329 (12)	0.0254 (14)	−0.0019 (13)	−0.0017 (12)
C2	0.067 (2)	0.060 (2)	0.0342 (14)	0.0332 (19)	0.0037 (15)	0.0017 (15)
C3	0.072 (3)	0.067 (2)	0.0393 (17)	0.036 (2)	0.0069 (16)	−0.0093 (17)
C4	0.067 (2)	0.055 (2)	0.056 (2)	0.0348 (19)	0.0049 (18)	−0.0106 (17)
C5	0.058 (2)	0.0424 (17)	0.0477 (16)	0.0289 (16)	0.0048 (15)	−0.0006 (14)
C6	0.0396 (14)	0.0366 (14)	0.0360 (13)	0.0201 (12)	−0.0001 (12)	−0.0010 (12)
C7	0.0403 (15)	0.0327 (14)	0.0366 (13)	0.0194 (12)	0.0002 (12)	0.0048 (11)
C8	0.0438 (15)	0.0351 (14)	0.0340 (12)	0.0233 (12)	0.0035 (12)	0.0043 (11)
C9	0.0414 (15)	0.0403 (15)	0.0341 (14)	0.0236 (13)	0.0022 (12)	0.0037 (12)
C10	0.059 (2)	0.0413 (16)	0.0418 (15)	0.0270 (16)	0.0096 (15)	−0.0016 (13)
C11	0.077 (3)	0.0451 (19)	0.0514 (18)	0.0314 (19)	−0.0052 (18)	−0.0005 (16)
C12	0.127 (4)	0.057 (2)	0.0437 (19)	0.043 (3)	−0.012 (2)	−0.0032 (17)
C13	0.126 (4)	0.062 (3)	0.053 (2)	0.048 (3)	0.026 (3)	−0.0038 (19)
C14	0.077 (3)	0.064 (2)	0.070 (3)	0.037 (2)	0.022 (2)	−0.008 (2)
C15	0.059 (2)	0.0499 (19)	0.058 (2)	0.0285 (17)	0.0068 (17)	−0.0110 (16)
C16	0.077 (3)	0.071 (3)	0.097 (3)	0.043 (2)	−0.027 (3)	−0.010 (3)
C17	0.092 (3)	0.121 (4)	0.085 (3)	0.077 (3)	−0.017 (3)	−0.028 (3)

Geometric parameters (Å, º)

S1—O4	1.423 (3)	C5—H5	0.9300
S1—O3	1.430 (3)	C6—C7	1.454 (4)
S1—N1	1.615 (3)	C7—C8	1.373 (4)
S1—C8	1.739 (3)	C8—C9	1.459 (4)
O1—C7	1.329 (3)	C10—C11	1.384 (5)
O1—H1O	0.89 (4)	C10—C15	1.395 (5)
O2—C9	1.253 (3)	C11—C12	1.400 (6)
N1—C1	1.405 (4)	C11—C16	1.499 (6)
N1—H1N	0.80 (5)	C12—C13	1.364 (7)
N2—C9	1.335 (4)	C12—H12	0.9300
N2—C10	1.428 (4)	C13—C14	1.350 (7)
N2—H2N	0.84 (4)	C13—H13	0.9300
C1—C2	1.392 (4)	C14—C15	1.377 (5)
C1—C6	1.395 (4)	C14—H14	0.9300
C2—C3	1.380 (5)	C15—C17	1.502 (6)
C2—H2	0.9300	C16—H16A	0.9600
C3—C4	1.369 (5)	C16—H16B	0.9600
C3—H3	0.9300	C16—H16C	0.9600
C4—C5	1.379 (5)	C17—H17A	0.9600
C4—H4	0.9300	C17—H17B	0.9600
C5—C6	1.390 (4)	C17—H17C	0.9600
O4—S1—O3	117.65 (17)	C7—C8—S1	116.0 (2)
O4—S1—N1	109.32 (16)	C9—C8—S1	121.6 (2)
O3—S1—N1	106.64 (15)	O2—C9—N2	121.7 (3)
O4—S1—C8	108.24 (14)	O2—C9—C8	119.6 (3)
O3—S1—C8	110.91 (15)	N2—C9—C8	118.7 (3)
N1—S1—C8	103.09 (15)	C11—C10—C15	122.3 (3)
C7—O1—H1O	109 (3)	C11—C10—N2	119.4 (3)
C1—N1—S1	119.6 (2)	C15—C10—N2	118.0 (3)
C1—N1—H1N	115 (3)	C10—C11—C12	116.5 (4)
S1—N1—H1N	121 (3)	C10—C11—C16	122.3 (3)
C9—N2—C10	125.8 (3)	C12—C11—C16	121.2 (4)
C9—N2—H2N	119 (3)	C13—C12—C11	121.5 (4)
C10—N2—H2N	115 (3)	C13—C12—H12	119.3
C2—C1—C6	120.5 (3)	C11—C12—H12	119.3
C2—C1—N1	119.2 (3)	C14—C13—C12	120.6 (4)
C6—C1—N1	120.3 (3)	C14—C13—H13	119.7
C3—C2—C1	119.5 (3)	C12—C13—H13	119.7
C3—C2—H2	120.3	C13—C14—C15	121.1 (4)
C1—C2—H2	120.3	C13—C14—H14	119.5
C4—C3—C2	120.3 (3)	C15—C14—H14	119.5
C4—C3—H3	119.8	C14—C15—C10	118.0 (4)
C2—C3—H3	119.8	C14—C15—C17	120.1 (4)
C3—C4—C5	120.6 (3)	C10—C15—C17	121.9 (3)
C3—C4—H4	119.7	C11—C16—H16A	109.5
C5—C4—H4	119.7	C11—C16—H16B	109.5
C4—C5—C6	120.4 (3)	H16A—C16—H16B	109.5
C4—C5—H5	119.8	C11—C16—H16C	109.5
C6—C5—H5	119.8	H16A—C16—H16C	109.5
C5—C6—C1	118.7 (3)	H16B—C16—H16C	109.5
C5—C6—C7	120.2 (3)	C15—C17—H17A	109.5
C1—C6—C7	120.9 (3)	C15—C17—H17B	109.5
O1—C7—C8	120.9 (3)	H17A—C17—H17B	109.5
O1—C7—C6	115.2 (2)	C15—C17—H17C	109.5
C8—C7—C6	123.9 (3)	H17A—C17—H17C	109.5
C7—C8—C9	121.9 (3)	H17B—C17—H17C	109.5
O4—S1—N1—C1	−70.5 (3)	N1—S1—C8—C7	−35.3 (3)
O3—S1—N1—C1	161.3 (3)	O4—S1—C8—C9	−91.7 (3)
C8—S1—N1—C1	44.4 (3)	O3—S1—C8—C9	38.8 (3)
S1—N1—C1—C2	154.1 (3)	N1—S1—C8—C9	152.6 (2)
S1—N1—C1—C6	−27.1 (4)	C10—N2—C9—O2	−8.0 (5)
C6—C1—C2—C3	0.8 (5)	C10—N2—C9—C8	171.2 (3)
N1—C1—C2—C3	179.5 (3)	C7—C8—C9—O2	−4.1 (4)
C1—C2—C3—C4	2.3 (6)	S1—C8—C9—O2	167.6 (2)
C2—C3—C4—C5	−3.4 (6)	C7—C8—C9—N2	176.7 (3)
C3—C4—C5—C6	1.3 (6)	S1—C8—C9—N2	−11.7 (4)
C4—C5—C6—C1	1.7 (5)	C9—N2—C10—C11	−69.6 (5)
C4—C5—C6—C7	−173.7 (3)	C9—N2—C10—C15	115.9 (4)
C2—C1—C6—C5	−2.8 (5)	C15—C10—C11—C12	−0.6 (5)
N1—C1—C6—C5	178.5 (3)	N2—C10—C11—C12	−174.8 (3)
C2—C1—C6—C7	172.7 (3)	C15—C10—C11—C16	177.5 (4)
N1—C1—C6—C7	−6.0 (5)	N2—C10—C11—C16	3.3 (5)
C5—C6—C7—O1	11.2 (4)	C10—C11—C12—C13	0.4 (6)
C1—C6—C7—O1	−164.2 (3)	C16—C11—C12—C13	−177.7 (4)
C5—C6—C7—C8	−170.6 (3)	C11—C12—C13—C14	−0.4 (7)
C1—C6—C7—C8	14.0 (4)	C12—C13—C14—C15	0.5 (7)
O1—C7—C8—C9	0.3 (4)	C13—C14—C15—C10	−0.6 (6)
C6—C7—C8—C9	−177.8 (3)	C13—C14—C15—C17	178.6 (4)
O1—C7—C8—S1	−171.8 (2)	C11—C10—C15—C14	0.7 (5)
C6—C7—C8—S1	10.1 (4)	N2—C10—C15—C14	175.0 (3)
O4—S1—C8—C7	80.4 (3)	C11—C10—C15—C17	−178.5 (4)
O3—S1—C8—C7	−149.1 (2)	N2—C10—C15—C17	−4.2 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O3	0.84 (4)	2.09 (4)	2.795 (4)	141 (4)
O1—H1O···O2	0.89 (4)	1.74 (4)	2.532 (3)	146 (4)
N1—H1N···O2^i	0.80 (5)	2.09 (5)	2.857 (3)	161 (4)

Symmetry code: (i) −y+1, x−y, z+1/3.