N-(1,3-Benzo­thia­zol-2-yl)-4-(di­methyl­amino)­benzyl­amine

The title compound, C₁₆H₁₅N₃S, crystallizes with Z = 8 in space group P2₁/c. The two crystallographically independent mol­ecules, A and B, are rotational isomers around the C—N bond joining the benzo­thia­zole and di­methyl­amino­aryl moieties. Molecules A and B have different intramolecular hydrogen bonds: C—H...N for mol­ecule A and C—H...S for mol­ecule B. For both mol­ecules, intermolecular C—H...π interactions are found between molecular pairs related by a centre of symmetry. The molecular packing is stabilized by C—H...π and π–π intermolecular interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.076
• Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.95
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N1     -   C7      ..       7.09 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C8     -   C9      ..       7.85 su

Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               4662
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         4928
           Completeness (_total/calc)             94.60%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.95
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.66 mm
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     -   C7      ..       5.66 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2     -   C7      ..       5.25 su
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT322_ALERT_2_C Check Hybridisation of  S2     in Main Residue .          ?

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS90 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

N-(1,3-Benzothiazol-2-yl)-4-(dimethylamino)benzylamine

Crystal data

C16H15N3S	F(000) = 1184
Mr = 281.37	Dx = 1.332 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.7771 (8) Å	Cell parameters from 14170 reflections
b = 22.6876 (12) Å	θ = 1.8–27.1°
c = 11.7725 (9) Å	µ = 0.22 mm^−1
β = 116.822 (5)°	T = 293 K
V = 2807.1 (3) Å^3	Plate, orange
Z = 8	0.66 × 0.37 × 0.11 mm

Data collection

Stoe IPDS-2 diffractometer	4662 independent reflections
Radiation source: fine-focus sealed tube	2653 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
Detector resolution: 6.67 pixels mm^-1	θmax = 25.0°, θmin = 1.8°
rotation method scans	h = −14→13
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −26→26
Tmin = 0.899, Tmax = 0.979	l = −13→13
17481 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.076	H-atom parameters constrained
S = 0.81	w = 1/[σ^2(Fo^2) + (0.0358P)^2] where P = (Fo^2 + 2Fc^2)/3
4662 reflections	(Δ/σ)max = 0.010
365 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

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
C1	0.4724 (2)	0.19599 (9)	0.6255 (2)	0.0460 (5)
C2	0.3916 (2)	0.23861 (10)	0.6339 (2)	0.0550 (6)
H2	0.3066	0.2400	0.5737	0.066*
C3	0.4383 (2)	0.27850 (10)	0.7316 (2)	0.0599 (7)
H3	0.3848	0.3074	0.7366	0.072*
C4	0.5641 (2)	0.27646 (10)	0.8231 (2)	0.0620 (7)
H4	0.5940	0.3040	0.8887	0.074*
C5	0.6449 (2)	0.23427 (11)	0.8179 (2)	0.0629 (7)
H5	0.7292	0.2327	0.8798	0.075*
C6	0.5989 (2)	0.19405 (9)	0.7188 (2)	0.0505 (6)
C7	0.5383 (2)	0.12156 (9)	0.5504 (2)	0.0507 (6)
C8	0.4602 (2)	0.06873 (9)	0.3652 (2)	0.0520 (6)
H8	0.3896	0.0934	0.3369	0.062*
C9	0.4651 (2)	0.02333 (9)	0.2806 (2)	0.0463 (5)
C10	0.5647 (2)	−0.01741 (10)	0.3210 (2)	0.0518 (6)
H10	0.6285	−0.0160	0.4045	0.062*
C11	0.5698 (2)	−0.05915 (10)	0.2400 (2)	0.0550 (6)
H11	0.6367	−0.0860	0.2696	0.066*
C12	0.4766 (2)	−0.06244 (9)	0.1131 (2)	0.0488 (6)
C13	0.3771 (2)	−0.02110 (10)	0.0739 (2)	0.0526 (6)
H13	0.3131	−0.0220	−0.0095	0.063*
C14	0.3726 (2)	0.02022 (10)	0.1554 (2)	0.0517 (6)
H14	0.3057	0.0470	0.1262	0.062*
C15	0.5866 (3)	−0.14482 (12)	0.0714 (3)	0.0928 (10)
H15A	0.6617	−0.1238	0.0825	0.139*
H15B	0.5672	−0.1745	0.0073	0.139*
H15C	0.6010	−0.1631	0.1504	0.139*
C16	0.3909 (3)	−0.10423 (12)	−0.1008 (2)	0.0787 (8)
H16A	0.3062	−0.1072	−0.1091	0.118*
H16B	0.4073	−0.1372	−0.1425	0.118*
H16C	0.3991	−0.0683	−0.1394	0.118*
C17	0.0819 (2)	0.19480 (9)	1.1825 (2)	0.0454 (5)
C18	0.1517 (2)	0.23661 (10)	1.2742 (2)	0.0571 (6)
H18	0.2386	0.2409	1.3007	0.068*
C19	0.0905 (2)	0.27139 (10)	1.3249 (2)	0.0581 (6)
H19	0.1364	0.2996	1.3857	0.070*
C20	−0.0375 (2)	0.26508 (11)	1.2870 (2)	0.0651 (7)
H20	−0.0771	0.2893	1.3221	0.078*
C21	−0.1079 (2)	0.22367 (11)	1.1982 (2)	0.0675 (7)
H21	−0.1945	0.2194	1.1733	0.081*
C22	−0.0470 (2)	0.18833 (9)	1.1465 (2)	0.0483 (6)
C23	0.04248 (19)	0.12523 (9)	1.03786 (19)	0.0432 (5)
C24	−0.0235 (2)	0.05282 (9)	0.88438 (19)	0.0463 (6)
H24	−0.0993	0.0520	0.8909	0.056*
C25	−0.0118 (2)	0.01506 (9)	0.7927 (2)	0.0450 (5)
C26	−0.1091 (2)	−0.02473 (9)	0.7219 (2)	0.0512 (6)
H26	−0.1824	−0.0252	0.7332	0.061*
C27	−0.0996 (2)	−0.06284 (10)	0.6369 (2)	0.0557 (6)
H27	−0.1661	−0.0887	0.5917	0.067*
C28	0.0093 (2)	−0.06354 (9)	0.6167 (2)	0.0507 (6)
C29	0.1044 (2)	−0.02154 (10)	0.6839 (2)	0.0539 (6)
H29	0.1759	−0.0192	0.6698	0.065*
C30	0.0934 (2)	0.01561 (10)	0.7690 (2)	0.0514 (6)
H30	0.1586	0.0423	0.8128	0.062*
C31	−0.0759 (3)	−0.14438 (12)	0.4642 (3)	0.0880 (9)
H31A	−0.0975	−0.1667	0.5210	0.132*
H31B	−0.0462	−0.1706	0.4194	0.132*
H31C	−0.1497	−0.1236	0.4043	0.132*
C32	0.1363 (3)	−0.10326 (13)	0.5171 (3)	0.0854 (9)
H32A	0.1466	−0.0655	0.4861	0.128*
H32B	0.1281	−0.1331	0.4561	0.128*
H32C	0.2093	−0.1116	0.5964	0.128*
N1	0.43897 (17)	0.15387 (8)	0.52883 (16)	0.0515 (5)
N2	0.54966 (18)	0.07569 (8)	0.47674 (18)	0.0548 (5)
N3	0.4816 (2)	−0.10437 (9)	0.03266 (19)	0.0663 (6)
N4	0.13106 (16)	0.15870 (8)	1.11979 (16)	0.0483 (5)
N5	0.06540 (16)	0.08792 (7)	0.95841 (16)	0.0479 (5)
N6	0.0227 (2)	−0.10267 (9)	0.53628 (19)	0.0658 (6)
S1	0.67699 (6)	0.13715 (3)	0.68563 (6)	0.0630 (2)
S2	−0.10981 (5)	0.13386 (3)	1.03141 (6)	0.05742 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0487 (13)	0.0424 (12)	0.0506 (13)	−0.0022 (10)	0.0256 (12)	0.0060 (10)
C2	0.0467 (13)	0.0526 (14)	0.0637 (15)	0.0032 (11)	0.0231 (12)	0.0083 (12)
C3	0.0610 (16)	0.0484 (14)	0.0845 (18)	0.0071 (12)	0.0452 (15)	0.0018 (13)
C4	0.0636 (16)	0.0546 (15)	0.0717 (16)	−0.0034 (12)	0.0341 (15)	−0.0164 (13)
C5	0.0509 (14)	0.0655 (16)	0.0654 (16)	0.0031 (12)	0.0203 (13)	−0.0145 (13)
C6	0.0492 (14)	0.0493 (13)	0.0573 (14)	0.0036 (10)	0.0279 (12)	−0.0041 (11)
C7	0.0630 (15)	0.0432 (13)	0.0559 (14)	0.0029 (11)	0.0357 (13)	0.0030 (11)
C8	0.0491 (14)	0.0489 (14)	0.0625 (16)	−0.0067 (11)	0.0293 (13)	0.0040 (12)
C9	0.0523 (14)	0.0415 (12)	0.0537 (14)	−0.0047 (10)	0.0314 (12)	−0.0001 (11)
C10	0.0558 (14)	0.0533 (14)	0.0453 (13)	−0.0041 (11)	0.0218 (12)	0.0012 (11)
C11	0.0588 (15)	0.0512 (14)	0.0560 (15)	0.0097 (11)	0.0268 (13)	0.0071 (12)
C12	0.0604 (14)	0.0431 (12)	0.0494 (14)	−0.0038 (11)	0.0305 (12)	−0.0007 (10)
C13	0.0525 (14)	0.0572 (14)	0.0457 (13)	−0.0036 (11)	0.0200 (11)	0.0003 (11)
C14	0.0493 (14)	0.0473 (13)	0.0599 (15)	0.0010 (10)	0.0260 (13)	0.0020 (11)
C15	0.131 (3)	0.0687 (19)	0.086 (2)	0.0313 (18)	0.055 (2)	−0.0046 (16)
C16	0.0820 (19)	0.094 (2)	0.0683 (18)	−0.0216 (15)	0.0414 (17)	−0.0292 (15)
C17	0.0462 (13)	0.0453 (13)	0.0480 (13)	0.0004 (10)	0.0242 (11)	0.0015 (11)
C18	0.0486 (13)	0.0648 (15)	0.0591 (15)	−0.0079 (12)	0.0255 (13)	−0.0110 (12)
C19	0.0568 (15)	0.0603 (16)	0.0546 (14)	−0.0018 (12)	0.0228 (13)	−0.0110 (12)
C20	0.0605 (16)	0.0693 (17)	0.0662 (16)	0.0065 (13)	0.0292 (14)	−0.0169 (14)
C21	0.0454 (14)	0.0808 (19)	0.0787 (18)	0.0004 (13)	0.0301 (14)	−0.0185 (15)
C22	0.0450 (13)	0.0487 (13)	0.0517 (13)	0.0009 (10)	0.0223 (12)	−0.0027 (11)
C23	0.0439 (12)	0.0437 (13)	0.0425 (12)	0.0043 (10)	0.0199 (11)	0.0060 (10)
C24	0.0465 (13)	0.0460 (13)	0.0485 (13)	0.0032 (10)	0.0233 (12)	0.0059 (11)
C25	0.0434 (13)	0.0447 (12)	0.0450 (12)	0.0029 (10)	0.0184 (11)	0.0035 (10)
C26	0.0460 (13)	0.0553 (14)	0.0559 (14)	−0.0038 (11)	0.0262 (12)	−0.0020 (12)
C27	0.0563 (15)	0.0541 (15)	0.0520 (14)	−0.0057 (11)	0.0204 (13)	−0.0028 (12)
C28	0.0620 (16)	0.0455 (13)	0.0442 (13)	0.0081 (11)	0.0236 (13)	0.0048 (10)
C29	0.0501 (14)	0.0605 (15)	0.0584 (14)	0.0024 (12)	0.0309 (12)	0.0016 (13)
C30	0.0488 (14)	0.0524 (14)	0.0529 (14)	−0.0048 (11)	0.0228 (12)	−0.0001 (11)
C31	0.108 (2)	0.0735 (19)	0.0775 (18)	−0.0069 (17)	0.0374 (18)	−0.0232 (16)
C32	0.097 (2)	0.095 (2)	0.0753 (19)	0.0201 (17)	0.0482 (18)	−0.0087 (16)
N1	0.0577 (12)	0.0502 (11)	0.0464 (10)	−0.0075 (9)	0.0234 (10)	0.0015 (9)
N2	0.0554 (12)	0.0559 (12)	0.0551 (12)	−0.0029 (9)	0.0268 (11)	−0.0015 (10)
N3	0.0895 (16)	0.0579 (13)	0.0548 (13)	0.0060 (11)	0.0355 (12)	−0.0052 (10)
N4	0.0437 (10)	0.0525 (11)	0.0500 (11)	−0.0027 (9)	0.0222 (10)	−0.0045 (9)
N5	0.0481 (11)	0.0474 (11)	0.0493 (11)	0.0023 (8)	0.0231 (10)	−0.0015 (9)
N6	0.0818 (16)	0.0580 (13)	0.0648 (14)	0.0026 (11)	0.0393 (13)	−0.0084 (11)
S1	0.0540 (4)	0.0626 (4)	0.0689 (4)	0.0076 (3)	0.0246 (3)	−0.0144 (3)
S2	0.0435 (3)	0.0624 (4)	0.0661 (4)	−0.0047 (3)	0.0245 (3)	−0.0146 (3)

Geometric parameters (Å, º)

C1—C2	1.390 (3)	C17—C22	1.387 (3)
C1—C6	1.397 (3)	C17—N4	1.391 (3)
C1—N1	1.400 (3)	C17—C18	1.393 (3)
C2—C3	1.369 (3)	C18—C19	1.374 (3)
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.384 (3)	C19—C20	1.373 (3)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.371 (3)	C20—C21	1.371 (3)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.384 (3)	C21—C22	1.387 (3)
C5—H5	0.9300	C21—H21	0.9300
C6—S1	1.729 (2)	C22—S2	1.733 (2)
C7—N1	1.305 (3)	C23—N4	1.299 (2)
C7—N2	1.399 (3)	C23—N5	1.376 (3)
C7—S1	1.726 (2)	C23—S2	1.771 (2)
C8—N2	1.269 (2)	C24—N5	1.291 (2)
C8—C9	1.452 (3)	C24—C25	1.432 (3)
C8—H8	0.9300	C24—H24	0.9300
C9—C14	1.384 (3)	C25—C30	1.387 (3)
C9—C10	1.398 (3)	C25—C26	1.401 (3)
C10—C11	1.365 (3)	C26—C27	1.365 (3)
C10—H10	0.9300	C26—H26	0.9300
C11—C12	1.401 (3)	C27—C28	1.405 (3)
C11—H11	0.9300	C27—H27	0.9300
C12—N3	1.362 (3)	C28—N6	1.358 (3)
C12—C13	1.406 (3)	C28—C29	1.411 (3)
C13—C14	1.359 (3)	C29—C30	1.360 (3)
C13—H13	0.9300	C29—H29	0.9300
C14—H14	0.9300	C30—H30	0.9300
C15—N3	1.439 (3)	C31—N6	1.441 (3)
C15—H15A	0.9600	C31—H31A	0.9600
C15—H15B	0.9600	C31—H31B	0.9600
C15—H15C	0.9600	C31—H31C	0.9600
C16—N3	1.448 (3)	C32—N6	1.454 (3)
C16—H16A	0.9600	C32—H32A	0.9600
C16—H16B	0.9600	C32—H32B	0.9600
C16—H16C	0.9600	C32—H32C	0.9600
C2—C1—C6	119.2 (2)	C20—C19—C18	120.9 (2)
C2—C1—N1	125.6 (2)	C20—C19—H19	119.5
C6—C1—N1	115.2 (2)	C18—C19—H19	119.5
C3—C2—C1	119.4 (2)	C21—C20—C19	121.1 (2)
C3—C2—H2	120.3	C21—C20—H20	119.4
C1—C2—H2	120.3	C19—C20—H20	119.4
C2—C3—C4	121.0 (2)	C20—C21—C22	118.4 (2)
C2—C3—H3	119.5	C20—C21—H21	120.8
C4—C3—H3	119.5	C22—C21—H21	120.8
C5—C4—C3	120.6 (2)	C17—C22—C21	121.1 (2)
C5—C4—H4	119.7	C17—C22—S2	109.68 (17)
C3—C4—H4	119.7	C21—C22—S2	129.23 (18)
C4—C5—C6	118.8 (2)	N4—C23—N5	121.8 (2)
C4—C5—H5	120.6	N4—C23—S2	115.19 (16)
C6—C5—H5	120.6	N5—C23—S2	122.99 (16)
C5—C6—C1	121.0 (2)	N5—C24—C25	123.6 (2)
C5—C6—S1	129.54 (17)	N5—C24—H24	118.2
C1—C6—S1	109.48 (16)	C25—C24—H24	118.2
N1—C7—N2	128.7 (2)	C30—C25—C26	116.9 (2)
N1—C7—S1	117.18 (17)	C30—C25—C24	123.0 (2)
N2—C7—S1	114.13 (17)	C26—C25—C24	120.2 (2)
N2—C8—C9	121.8 (2)	C27—C26—C25	121.9 (2)
N2—C8—H8	119.1	C27—C26—H26	119.1
C9—C8—H8	119.1	C25—C26—H26	119.1
C14—C9—C10	117.7 (2)	C26—C27—C28	121.0 (2)
C14—C9—C8	120.7 (2)	C26—C27—H27	119.5
C10—C9—C8	121.5 (2)	C28—C27—H27	119.5
C11—C10—C9	121.1 (2)	N6—C28—C27	121.8 (2)
C11—C10—H10	119.5	N6—C28—C29	121.3 (2)
C9—C10—H10	119.5	C27—C28—C29	116.8 (2)
C10—C11—C12	121.4 (2)	C30—C29—C28	121.1 (2)
C10—C11—H11	119.3	C30—C29—H29	119.4
C12—C11—H11	119.3	C28—C29—H29	119.4
N3—C12—C11	121.3 (2)	C29—C30—C25	122.2 (2)
N3—C12—C13	121.9 (2)	C29—C30—H30	118.9
C11—C12—C13	116.8 (2)	C25—C30—H30	118.9
C14—C13—C12	121.4 (2)	N6—C31—H31A	109.5
C14—C13—H13	119.3	N6—C31—H31B	109.5
C12—C13—H13	119.3	H31A—C31—H31B	109.5
C13—C14—C9	121.6 (2)	N6—C31—H31C	109.5
C13—C14—H14	119.2	H31A—C31—H31C	109.5
C9—C14—H14	119.2	H31B—C31—H31C	109.5
N3—C15—H15A	109.5	N6—C32—H32A	109.5
N3—C15—H15B	109.5	N6—C32—H32B	109.5
H15A—C15—H15B	109.5	H32A—C32—H32B	109.5
N3—C15—H15C	109.5	N6—C32—H32C	109.5
H15A—C15—H15C	109.5	H32A—C32—H32C	109.5
H15B—C15—H15C	109.5	H32B—C32—H32C	109.5
N3—C16—H16A	109.5	C7—N1—C1	109.08 (18)
N3—C16—H16B	109.5	C8—N2—C7	117.8 (2)
H16A—C16—H16B	109.5	C12—N3—C15	121.7 (2)
N3—C16—H16C	109.5	C12—N3—C16	120.7 (2)
H16A—C16—H16C	109.5	C15—N3—C16	116.9 (2)
H16B—C16—H16C	109.5	C23—N4—C17	110.53 (18)
C22—C17—N4	115.82 (19)	C24—N5—C23	119.38 (19)
C22—C17—C18	119.4 (2)	C28—N6—C31	121.5 (2)
N4—C17—C18	124.8 (2)	C28—N6—C32	121.3 (2)
C19—C18—C17	119.1 (2)	C31—N6—C32	117.2 (2)
C19—C18—H18	120.5	C7—S1—C6	89.02 (11)
C17—C18—H18	120.5	C22—S2—C23	88.76 (11)
C6—C1—C2—C3	1.4 (3)	C25—C26—C27—C28	−0.1 (3)
N1—C1—C2—C3	−177.7 (2)	C26—C27—C28—N6	177.3 (2)
C1—C2—C3—C4	−1.0 (4)	C26—C27—C28—C29	−2.7 (3)
C2—C3—C4—C5	0.0 (4)	N6—C28—C29—C30	−176.7 (2)
C3—C4—C5—C6	0.6 (4)	C27—C28—C29—C30	3.3 (3)
C4—C5—C6—C1	−0.2 (4)	C28—C29—C30—C25	−1.1 (3)
C4—C5—C6—S1	179.1 (2)	C26—C25—C30—C29	−1.7 (3)
C2—C1—C6—C5	−0.8 (3)	C24—C25—C30—C29	178.3 (2)
N1—C1—C6—C5	178.3 (2)	N2—C7—N1—C1	−177.8 (2)
C2—C1—C6—S1	179.80 (18)	S1—C7—N1—C1	0.8 (3)
N1—C1—C6—S1	−1.0 (2)	C2—C1—N1—C7	179.3 (2)
N2—C8—C9—C14	−173.6 (2)	C6—C1—N1—C7	0.2 (3)
N2—C8—C9—C10	4.3 (3)	C9—C8—N2—C7	178.4 (2)
C14—C9—C10—C11	−0.6 (3)	N1—C7—N2—C8	11.5 (4)
C8—C9—C10—C11	−178.6 (2)	S1—C7—N2—C8	−167.18 (16)
C9—C10—C11—C12	0.7 (4)	C11—C12—N3—C15	−4.0 (4)
C10—C11—C12—N3	−179.6 (2)	C13—C12—N3—C15	177.0 (2)
C10—C11—C12—C13	−0.6 (3)	C11—C12—N3—C16	−174.7 (2)
N3—C12—C13—C14	179.4 (2)	C13—C12—N3—C16	6.3 (4)
C11—C12—C13—C14	0.4 (3)	N5—C23—N4—C17	176.17 (18)
C12—C13—C14—C9	−0.3 (4)	S2—C23—N4—C17	−1.0 (2)
C10—C9—C14—C13	0.4 (3)	C22—C17—N4—C23	−0.1 (3)
C8—C9—C14—C13	178.4 (2)	C18—C17—N4—C23	−178.6 (2)
C22—C17—C18—C19	−1.4 (3)	C25—C24—N5—C23	175.93 (18)
N4—C17—C18—C19	177.1 (2)	N4—C23—N5—C24	175.59 (19)
C17—C18—C19—C20	0.5 (4)	S2—C23—N5—C24	−7.5 (3)
C18—C19—C20—C21	0.5 (4)	C27—C28—N6—C31	2.0 (3)
C19—C20—C21—C22	−0.5 (4)	C29—C28—N6—C31	−177.9 (2)
N4—C17—C22—C21	−177.2 (2)	C27—C28—N6—C32	−179.5 (2)
C18—C17—C22—C21	1.4 (3)	C29—C28—N6—C32	0.6 (3)
N4—C17—C22—S2	1.2 (2)	N1—C7—S1—C6	−1.2 (2)
C18—C17—C22—S2	179.76 (17)	N2—C7—S1—C6	177.59 (18)
C20—C21—C22—C17	−0.5 (4)	C5—C6—S1—C7	−178.1 (2)
C20—C21—C22—S2	−178.5 (2)	C1—C6—S1—C7	1.18 (18)
N5—C24—C25—C30	−4.5 (3)	C17—C22—S2—C23	−1.37 (17)
N5—C24—C25—C26	175.60 (19)	C21—C22—S2—C23	176.8 (2)
C30—C25—C26—C27	2.4 (3)	N4—C23—S2—C22	1.43 (17)
C24—C25—C26—C27	−177.70 (19)	N5—C23—S2—C22	−175.71 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N1	0.93	2.48	2.818 (3)	102
C24—H24···S2	0.93	2.53	3.000 (2)	112