(1R,2R)-1,2-Di­phenyl-1,2-bis(8-quinoline­sulfonyl­amino)ethyl­enedi­amine-acetone (1/1)

The crystal structure of the new chiral complex (1R,2R)-1,2-di­phenyl-1,2-bis(8-quinoline­sulfonyl­amino)- ethyl­enedi­amine-acetone (1/1), C₃₂H₂₆N₄O₄S₂^.C₃H₆O, is reported. The conformation of the C₃₂H₂₆N₄O₄S₂ (BQSDA) mol­ecule is determined by a bifurcated N-H...N hydrogen-bond system. The acetone of solvation is linked to the BQSDA mol­ecule by an N-H...O hydrogen bond.

S1. Comment

The structure of the title compound, (I), has been determined as part of a study into asymmetric catalysis in transfer hydrogenation reaction and addition of dialkylzinc to aldehydes. Further study shows that BQSDA as chiral catalyst has high enantioselectivity. Therefore the structure of this new ligand can help us know of its catalytic mechanism in asymmetric reaction.

S2. Experimental

A mixture of 1 mmol (1R,2R)-diphenylethylenediamine and 2 mmol 8-quinolinesulfonyl chloride in 10 ml dichloroethane was stirred for 24 h at room temperature. Then the resulting white solid was collected by evaporation of the solution. The yield of analytically pure product was 100%. The single-crystal was obtained from acetone at room temperature.

S3. Refinement

The H atoms bonded to N1 and N3 were refined isotropically; all other H atoms were allowed for as riding atoms. N—H dimensions are 0.78 (3) and 0.80 (3) Å.

Computing details

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS (Siemens, 1994); data reduction: SHELXTL (Sheldrick, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: SHELXTL (Sheldrick, 1994); software used to prepare material for publication: SHELXTL (Sheldrick, 1994).

(1R,2R)-N,N-bis(8-quinoline sulfonylamino)-1,2-diphenylethylenediamine acetone (1\1)

Crystal data

C32H26N4O4S2·C3H6O	F(000) = 684
Mr = 652.77	Dx = 1.350 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 9.717 (2) Å	Cell parameters from 33 reflections
b = 9.495 (1) Å	θ = 3.2–16.5°
c = 17.542 (3) Å	µ = 0.22 mm^−1
β = 97.13 (1)°	T = 296 K
V = 1606.0 (5) Å^3	Flake, colorless
Z = 2	0.48 × 0.40 × 0.36 mm

Data collection

P4 diffractometer	Rint = 0.012
Radiation source: fine-focus sealed tube	θmax = 27°, θmin = 2.1°
Graphite monochromator	h = −1→12
ω scans	k = −1→12
5056 measured reflections	l = −22→22
4159 independent reflections	3 standard reflections every 97 reflections
3405 reflections with I > 2σ(I)	intensity decay: 1.4%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.032	w = 1/[σ^2(Fo^2) + (0.0439P)^2] where P = Fo^2 + 2Fc^2)/3
wR(F^2) = 0.074	(Δ/σ)max < 0.001
S = 0.94	Δρmax = 0.21 e Å^−3
4159 reflections	Δρmin = −0.18 e Å^−3
426 parameters	Extinction correction: SHELXL, Fc^* = kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0146 (11)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 433 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.05 (6)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.77133 (6)	0.13569 (7)	0.29480 (3)	0.03750 (16)
S2	0.46361 (7)	0.59288 (7)	0.24829 (3)	0.04496 (18)
O1	0.81699 (18)	0.1436 (2)	0.37498 (9)	0.0511 (5)
O2	0.63801 (16)	0.0750 (2)	0.26972 (10)	0.0504 (5)
O3	0.32708 (19)	0.5603 (3)	0.26519 (11)	0.0649 (6)
O4	0.4834 (2)	0.7064 (2)	0.19724 (11)	0.0638 (6)
N1	0.7677 (2)	0.2949 (3)	0.26177 (12)	0.0373 (5)
N2	1.0766 (2)	0.1945 (3)	0.29681 (12)	0.0423 (5)
N3	0.5276 (2)	0.4517 (3)	0.21404 (13)	0.0399 (5)
N4	0.5346 (2)	0.3919 (2)	0.37985 (12)	0.0420 (5)
C1	0.8464 (3)	0.2347 (4)	0.06880 (16)	0.0570 (8)
H1	0.7695	0.1781	0.0541	0.068*
C2	0.9575 (4)	0.2344 (4)	0.02586 (19)	0.0795 (11)
H2	0.9554	0.1766	−0.0171	0.095*
C3	1.0703 (4)	0.3193 (4)	0.0468 (2)	0.0746 (11)
H3	1.1431	0.3210	0.0170	0.090*
C4	1.0758 (3)	0.4011 (4)	0.11105 (18)	0.0616 (9)
H4	1.1536	0.4563	0.1259	0.074*
C5	0.9655 (3)	0.4021 (3)	0.15418 (15)	0.0481 (7)
H5	0.9691	0.4591	0.1975	0.058*
C6	0.8503 (3)	0.3192 (3)	0.13343 (13)	0.0384 (6)
C7	0.7269 (2)	0.3202 (3)	0.17945 (13)	0.0341 (6)
H7	0.6639	0.2444	0.1598	0.041*
C8	0.8923 (2)	0.0335 (3)	0.25102 (13)	0.0369 (6)
C9	0.8478 (3)	−0.0844 (3)	0.21041 (16)	0.0491 (7)
H9	0.7542	−0.1077	0.2045	0.059*
C10	0.9418 (4)	−0.1705 (4)	0.17759 (18)	0.0641 (9)
H10	0.9100	−0.2489	0.1489	0.077*
C11	1.0787 (3)	−0.1398 (4)	0.18756 (18)	0.0636 (9)
H11	1.1406	−0.2005	0.1679	0.076*
C12	1.1292 (3)	−0.0186 (4)	0.22689 (15)	0.0476 (7)
C13	1.0358 (2)	0.0723 (3)	0.25941 (13)	0.0363 (6)
C14	1.2098 (3)	0.2253 (4)	0.30157 (15)	0.0541 (8)
H14	1.2395	0.3096	0.3251	0.065*
C15	1.3095 (3)	0.1395 (5)	0.27354 (17)	0.0636 (9)
H15	1.4024	0.1659	0.2803	0.076*
C16	1.2710 (3)	0.0198 (4)	0.23711 (17)	0.0589 (9)
H16	1.3368	−0.0379	0.2186	0.071*
C17	0.6778 (3)	0.5524 (3)	0.03745 (14)	0.0526 (7)
H17	0.7598	0.5949	0.0589	0.063*
C18	0.6392 (3)	0.5595 (4)	−0.04114 (15)	0.0603 (8)
H18	0.6952	0.6067	−0.0720	0.072*
C19	0.5200 (3)	0.4979 (4)	−0.07322 (14)	0.0553 (8)
H19	0.4942	0.5027	−0.1260	0.066*
C20	0.4380 (3)	0.4288 (5)	−0.02752 (16)	0.0683 (10)
H20	0.3564	0.3863	−0.0495	0.082*
C21	0.4749 (3)	0.4211 (4)	0.05077 (14)	0.0540 (8)
H21	0.4179	0.3740	0.0812	0.065*
C22	0.5961 (2)	0.4832 (3)	0.08436 (13)	0.0356 (5)
C23	0.6458 (2)	0.4613 (3)	0.16909 (12)	0.0338 (5)
H23	0.7064	0.5393	0.1883	0.041*
C24	0.5654 (3)	0.6295 (3)	0.33742 (13)	0.0409 (6)
C25	0.6184 (3)	0.7616 (3)	0.34956 (17)	0.0524 (8)
H25	0.6031	0.8294	0.3111	0.063*
C26	0.6964 (4)	0.7955 (4)	0.42025 (18)	0.0653 (9)
H26	0.7331	0.8855	0.4283	0.078*
C27	0.7181 (3)	0.6976 (4)	0.47662 (18)	0.0622 (9)
H27	0.7695	0.7213	0.5231	0.075*
C28	0.6639 (3)	0.5600 (3)	0.46587 (15)	0.0487 (7)
C29	0.5862 (3)	0.5236 (3)	0.39472 (14)	0.0404 (6)
C30	0.5557 (3)	0.2990 (3)	0.43453 (15)	0.0505 (7)
H30	0.5220	0.2084	0.4243	0.061*
C31	0.6259 (3)	0.3262 (4)	0.50787 (17)	0.0589 (9)
H31	0.6346	0.2562	0.5452	0.071*
C32	0.6800 (3)	0.4539 (4)	0.52334 (15)	0.0580 (8)
H32	0.7280	0.4732	0.5714	0.070*
O5	0.9053 (2)	0.5499 (3)	0.32269 (12)	0.0704 (6)
C33	0.9916 (3)	0.5811 (4)	0.37568 (17)	0.0598 (8)
C34	1.0509 (4)	0.7258 (5)	0.3805 (2)	0.0843 (12)
H34A	1.1350	0.7273	0.3570	0.101*	.001
H34B	1.0707	0.7530	0.4335	0.101*	.001
H34C	0.9854	0.7904	0.3543	0.101*	.001
C35	1.0382 (5)	0.4750 (6)	0.4339 (2)	0.1198 (18)
H35A	0.9856	0.3901	0.4234	0.144*	.001
H35B	1.0247	0.5098	0.4838	0.144*	.001
H35C	1.1348	0.4555	0.4325	0.144*	.001
H1N	0.834 (3)	0.341 (3)	0.2766 (15)	0.043 (9)*
H3N	0.535 (3)	0.390 (3)	0.2437 (15)	0.036 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0318 (3)	0.0398 (4)	0.0419 (3)	0.0042 (3)	0.0083 (2)	0.0107 (3)
S2	0.0509 (4)	0.0448 (4)	0.0393 (3)	0.0147 (3)	0.0061 (3)	0.0040 (3)
O1	0.0535 (10)	0.0607 (12)	0.0403 (9)	0.0161 (11)	0.0111 (8)	0.0147 (10)
O2	0.0311 (8)	0.0480 (12)	0.0727 (11)	0.0004 (9)	0.0090 (8)	0.0158 (11)
O3	0.0449 (10)	0.0844 (17)	0.0652 (12)	0.0186 (12)	0.0062 (9)	−0.0043 (13)
O4	0.1001 (16)	0.0482 (13)	0.0443 (10)	0.0238 (13)	0.0133 (11)	0.0122 (10)
N1	0.0387 (12)	0.0382 (13)	0.0341 (11)	−0.0002 (11)	0.0012 (10)	0.0028 (10)
N2	0.0362 (11)	0.0438 (13)	0.0471 (11)	−0.0011 (11)	0.0055 (9)	0.0008 (11)
N3	0.0497 (14)	0.0369 (13)	0.0340 (11)	0.0040 (11)	0.0085 (10)	0.0043 (11)
N4	0.0472 (13)	0.0416 (13)	0.0385 (11)	−0.0017 (11)	0.0098 (10)	0.0042 (11)
C1	0.0639 (18)	0.0533 (19)	0.0555 (16)	−0.0044 (17)	0.0142 (15)	−0.0107 (15)
C2	0.108 (3)	0.075 (3)	0.063 (2)	0.006 (3)	0.040 (2)	−0.015 (2)
C3	0.068 (2)	0.083 (3)	0.079 (2)	0.009 (2)	0.0377 (19)	0.007 (2)
C4	0.0457 (17)	0.077 (2)	0.0638 (19)	−0.0001 (17)	0.0134 (14)	0.0147 (19)
C5	0.0454 (16)	0.0552 (19)	0.0435 (14)	−0.0019 (15)	0.0047 (12)	0.0054 (14)
C6	0.0445 (14)	0.0376 (14)	0.0336 (12)	0.0065 (12)	0.0070 (11)	0.0045 (11)
C7	0.0399 (13)	0.0312 (14)	0.0301 (11)	−0.0007 (11)	−0.0005 (10)	0.0008 (10)
C8	0.0361 (13)	0.0366 (14)	0.0376 (12)	0.0030 (12)	0.0034 (10)	0.0038 (11)
C9	0.0475 (16)	0.0473 (18)	0.0518 (15)	−0.0037 (14)	0.0027 (13)	−0.0025 (14)
C10	0.076 (2)	0.053 (2)	0.0628 (19)	−0.0006 (19)	0.0047 (17)	−0.0224 (17)
C11	0.066 (2)	0.061 (2)	0.068 (2)	0.0153 (19)	0.0209 (17)	−0.0122 (18)
C12	0.0423 (14)	0.0588 (19)	0.0434 (14)	0.0093 (15)	0.0115 (11)	0.0027 (14)
C13	0.0332 (12)	0.0410 (15)	0.0347 (11)	0.0059 (12)	0.0041 (9)	0.0057 (12)
C14	0.0410 (15)	0.066 (2)	0.0542 (16)	−0.0124 (16)	0.0008 (13)	0.0035 (16)
C15	0.0311 (13)	0.098 (3)	0.0620 (17)	−0.0035 (19)	0.0072 (12)	0.011 (2)
C16	0.0419 (16)	0.081 (2)	0.0563 (17)	0.0144 (17)	0.0170 (13)	0.0078 (18)
C17	0.0607 (17)	0.0518 (18)	0.0433 (13)	−0.0188 (16)	−0.0018 (12)	0.0103 (14)
C18	0.076 (2)	0.064 (2)	0.0408 (13)	−0.0149 (19)	0.0085 (13)	0.0138 (16)
C19	0.0639 (19)	0.070 (2)	0.0303 (12)	0.0047 (18)	−0.0013 (12)	0.0014 (14)
C20	0.0527 (18)	0.103 (3)	0.0452 (15)	−0.017 (2)	−0.0095 (13)	0.0049 (19)
C21	0.0414 (15)	0.080 (2)	0.0399 (14)	−0.0151 (16)	0.0007 (12)	0.0094 (16)
C22	0.0390 (13)	0.0327 (13)	0.0349 (11)	0.0029 (12)	0.0028 (10)	0.0026 (11)
C23	0.0368 (13)	0.0320 (13)	0.0319 (11)	−0.0035 (12)	0.0020 (9)	0.0009 (11)
C24	0.0476 (13)	0.0413 (15)	0.0361 (11)	0.0025 (14)	0.0143 (10)	0.0012 (12)
C25	0.070 (2)	0.0404 (17)	0.0508 (16)	0.0020 (16)	0.0221 (15)	−0.0003 (14)
C26	0.083 (2)	0.0497 (19)	0.065 (2)	−0.0160 (19)	0.0177 (18)	−0.0113 (17)
C27	0.069 (2)	0.067 (2)	0.0502 (16)	−0.0122 (19)	0.0054 (15)	−0.0164 (18)
C28	0.0482 (16)	0.058 (2)	0.0411 (13)	0.0009 (15)	0.0103 (11)	−0.0023 (14)
C29	0.0402 (14)	0.0447 (16)	0.0388 (13)	0.0017 (13)	0.0147 (11)	0.0008 (12)
C30	0.0544 (17)	0.0473 (17)	0.0511 (16)	−0.0023 (15)	0.0112 (14)	0.0102 (14)
C31	0.0618 (19)	0.066 (2)	0.0496 (17)	0.0072 (18)	0.0086 (15)	0.0199 (16)
C32	0.0618 (19)	0.075 (2)	0.0366 (14)	−0.0003 (19)	0.0026 (13)	0.0025 (16)
O5	0.0738 (15)	0.0680 (16)	0.0654 (13)	−0.0070 (13)	−0.0069 (11)	−0.0121 (12)
C33	0.0586 (18)	0.065 (2)	0.0538 (16)	0.0028 (18)	−0.0011 (14)	−0.0121 (17)
C34	0.080 (3)	0.082 (3)	0.085 (2)	−0.022 (2)	−0.013 (2)	−0.001 (2)
C35	0.170 (5)	0.097 (4)	0.081 (3)	0.056 (4)	−0.027 (3)	0.005 (3)

Geometric parameters (Å, º)

S1—O1	1.4234 (17)	C10—C11	1.352 (4)
S1—O2	1.4360 (19)	C11—C12	1.399 (5)
S1—N1	1.617 (2)	C12—C16	1.416 (4)
S1—C8	1.771 (3)	C12—C13	1.422 (4)
S2—O3	1.429 (2)	C14—C15	1.401 (5)
S2—O4	1.429 (2)	C15—C16	1.334 (5)
S2—N3	1.624 (2)	C17—C22	1.379 (3)
S2—C24	1.778 (3)	C17—C18	1.385 (3)
N1—C7	1.469 (3)	C18—C19	1.356 (4)
N2—C14	1.319 (3)	C19—C20	1.366 (4)
N2—C13	1.367 (3)	C20—C21	1.377 (4)
N3—C23	1.474 (3)	C21—C22	1.382 (3)
N4—C30	1.300 (3)	C22—C23	1.519 (3)
N4—C29	1.360 (3)	C24—C25	1.362 (4)
C1—C6	1.386 (4)	C24—C29	1.419 (4)
C1—C2	1.391 (4)	C25—C26	1.408 (4)
C2—C3	1.373 (5)	C26—C27	1.355 (5)
C3—C4	1.365 (5)	C27—C28	1.413 (5)
C4—C5	1.387 (4)	C28—C29	1.419 (4)
C5—C6	1.380 (4)	C28—C32	1.420 (4)
C6—C7	1.526 (3)	C30—C31	1.403 (4)
C7—C23	1.553 (4)	C31—C32	1.336 (5)
C8—C9	1.368 (4)	O5—C33	1.209 (3)
C8—C13	1.432 (3)	C33—C35	1.465 (5)
C9—C10	1.401 (4)	C33—C34	1.488 (5)
O1—S1—O2	118.85 (11)	N2—C13—C12	123.1 (2)
O1—S1—N1	107.16 (13)	N2—C13—C8	119.2 (2)
O2—S1—N1	106.63 (12)	C12—C13—C8	117.7 (2)
O1—S1—C8	108.36 (11)	N2—C14—C15	124.3 (3)
O2—S1—C8	105.63 (12)	C16—C15—C14	119.9 (3)
N1—S1—C8	110.07 (11)	C15—C16—C12	119.4 (3)
O3—S2—O4	119.60 (14)	C22—C17—C18	120.8 (3)
O3—S2—N3	107.82 (14)	C19—C18—C17	120.3 (3)
O4—S2—N3	107.64 (12)	C18—C19—C20	119.6 (2)
O3—S2—C24	106.83 (11)	C19—C20—C21	120.8 (3)
O4—S2—C24	107.45 (14)	C20—C21—C22	120.3 (3)
N3—S2—C24	106.87 (12)	C17—C22—C21	118.2 (2)
C7—N1—S1	119.77 (19)	C17—C22—C23	120.9 (2)
C14—N2—C13	116.3 (2)	C21—C22—C23	120.6 (2)
C23—N3—S2	120.41 (19)	N3—C23—C22	110.97 (19)
C30—N4—C29	117.5 (2)	N3—C23—C7	107.6 (2)
C6—C1—C2	120.0 (3)	C22—C23—C7	109.12 (19)
C3—C2—C1	120.1 (3)	C25—C24—C29	121.6 (2)
C4—C3—C2	120.2 (3)	C25—C24—S2	118.4 (2)
C3—C4—C5	120.0 (3)	C29—C24—S2	119.9 (2)
C6—C5—C4	120.6 (3)	C24—C25—C26	120.0 (3)
C5—C6—C1	119.0 (3)	C27—C26—C25	120.3 (3)
C5—C6—C7	121.4 (2)	C26—C27—C28	121.0 (3)
C1—C6—C7	119.5 (2)	C27—C28—C29	119.4 (3)
N1—C7—C6	112.67 (19)	C27—C28—C32	123.7 (3)
N1—C7—C23	109.10 (19)	C29—C28—C32	116.8 (3)
C6—C7—C23	111.4 (2)	N4—C29—C24	120.0 (2)
C9—C8—C13	120.3 (2)	N4—C29—C28	122.4 (2)
C9—C8—S1	119.4 (2)	C24—C29—C28	117.6 (3)
C13—C8—S1	120.3 (2)	N4—C30—C31	124.4 (3)
C8—C9—C10	120.8 (3)	C32—C31—C30	119.2 (3)
C11—C10—C9	120.1 (3)	C31—C32—C28	119.6 (3)
C10—C11—C12	121.4 (3)	O5—C33—C35	119.5 (4)
C11—C12—C16	123.4 (3)	O5—C33—C34	119.8 (3)
C11—C12—C13	119.7 (3)	C35—C33—C34	120.7 (3)
C16—C12—C13	116.9 (3)
O1—S1—N1—C7	178.71 (18)	C13—C12—C16—C15	−2.4 (4)
O2—S1—N1—C7	−53.0 (2)	C22—C17—C18—C19	−0.1 (5)
C8—S1—N1—C7	61.1 (2)	C17—C18—C19—C20	0.0 (5)
O3—S2—N3—C23	160.61 (18)	C18—C19—C20—C21	0.1 (6)
O4—S2—N3—C23	30.3 (2)	C19—C20—C21—C22	−0.2 (6)
C24—S2—N3—C23	−84.9 (2)	C18—C17—C22—C21	0.0 (4)
C6—C1—C2—C3	−1.0 (5)	C18—C17—C22—C23	173.2 (3)
C1—C2—C3—C4	2.0 (6)	C20—C21—C22—C17	0.2 (5)
C2—C3—C4—C5	−2.0 (6)	C20—C21—C22—C23	−173.0 (3)
C3—C4—C5—C6	1.0 (5)	S2—N3—C23—C22	−88.4 (2)
C4—C5—C6—C1	0.1 (4)	S2—N3—C23—C7	152.26 (17)
C4—C5—C6—C7	−179.2 (3)	C17—C22—C23—N3	152.2 (3)
C2—C1—C6—C5	−0.1 (5)	C21—C22—C23—N3	−34.8 (3)
C2—C1—C6—C7	179.2 (3)	C17—C22—C23—C7	−89.4 (3)
S1—N1—C7—C6	−90.6 (3)	C21—C22—C23—C7	83.6 (3)
S1—N1—C7—C23	145.18 (18)	N1—C7—C23—N3	−56.1 (2)
C5—C6—C7—N1	−52.6 (3)	C6—C7—C23—N3	178.87 (19)
C1—C6—C7—N1	128.2 (3)	N1—C7—C23—C22	−176.6 (2)
C5—C6—C7—C23	70.3 (3)	C6—C7—C23—C22	58.4 (2)
C1—C6—C7—C23	−108.9 (3)	O3—S2—C24—C25	−116.2 (2)
O1—S1—C8—C9	122.4 (2)	O4—S2—C24—C25	13.3 (3)
O2—S1—C8—C9	−6.0 (2)	N3—S2—C24—C25	128.6 (2)
N1—S1—C8—C9	−120.7 (2)	O3—S2—C24—C29	61.9 (2)
O1—S1—C8—C13	−56.3 (2)	O4—S2—C24—C29	−168.61 (19)
O2—S1—C8—C13	175.29 (19)	N3—S2—C24—C29	−53.3 (2)
N1—S1—C8—C13	60.5 (2)	C29—C24—C25—C26	0.2 (4)
C13—C8—C9—C10	1.2 (4)	S2—C24—C25—C26	178.3 (2)
S1—C8—C9—C10	−177.5 (2)	C24—C25—C26—C27	−0.5 (5)
C8—C9—C10—C11	1.8 (5)	C25—C26—C27—C28	0.2 (5)
C9—C10—C11—C12	−3.5 (5)	C26—C27—C28—C29	0.4 (5)
C10—C11—C12—C16	−178.4 (3)	C26—C27—C28—C32	−178.3 (3)
C10—C11—C12—C13	2.1 (5)	C30—N4—C29—C24	−179.5 (2)
C14—N2—C13—C12	0.0 (3)	C30—N4—C29—C28	1.9 (4)
C14—N2—C13—C8	−179.0 (2)	C25—C24—C29—N4	−178.3 (3)
C11—C12—C13—N2	−178.1 (2)	S2—C24—C29—N4	3.6 (3)
C16—C12—C13—N2	2.3 (4)	C25—C24—C29—C28	0.4 (4)
C11—C12—C13—C8	0.8 (4)	S2—C24—C29—C28	−177.69 (19)
C16—C12—C13—C8	−178.7 (2)	C27—C28—C29—N4	178.0 (3)
C9—C8—C13—N2	176.6 (2)	C32—C28—C29—N4	−3.2 (4)
S1—C8—C13—N2	−4.7 (3)	C27—C28—C29—C24	−0.6 (4)
C9—C8—C13—C12	−2.4 (3)	C32—C28—C29—C24	178.1 (2)
S1—C8—C13—C12	176.27 (18)	C29—N4—C30—C31	1.0 (4)
C13—N2—C14—C15	−2.3 (4)	N4—C30—C31—C32	−2.5 (5)
N2—C14—C15—C16	2.2 (5)	C30—C31—C32—C28	0.9 (5)
C14—C15—C16—C12	0.3 (4)	C27—C28—C32—C31	−179.6 (3)
C11—C12—C16—C15	178.1 (3)	C29—C28—C32—C31	1.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O5	0.80 (3)	2.22 (3)	2.905 (4)	145 (3)
N3—H3N···N1	0.78 (3)	2.42 (3)	2.806 (3)	112 (2)
N3—H3N···N4	0.78 (3)	2.39 (3)	2.956 (3)	130 (3)