N,N′-Bis(4-methyl-2-benzothia­zolyl)pyridine-2,6-dicarboxamide N,N-dimethyl­formamide solvate

In the title compound, C₂₃H₁₇N₅O₂S₂·C₃H₇NO, hydrogen bonds involving the amide groups and the pyridine N atoms force the two carboxamide groups and the central pyridine ring into the same plane. The solvent mol­ecule is stabilized in the cavity formed by the two arms of the mol­ecule by N—H...O hydrogen bonds. The mol­ecules are linked into ribbons along the a axis via C—H...O hydrogen bonds and π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.053
• wR factor = 0.106
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low ....       0.87

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N5     -   C15     ..       5.47 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N5     -   C16     ..       6.46 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C9     -   C22     ..       5.36 su
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT322_ALERT_2_C Check Hybridisation of  S2     in Main Residue .          ?

Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           27.45
           From the CIF: _reflns_number_total               5107
           From the CIF: _diffrn_reflns_limit_ max hkl   20.    9.   25.
           From the CIF: _diffrn_reflns_limit_ min hkl  -19.    0.  -23.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl   22.    9.   25.
           Calculated minimum hkl  -22.   -9.  -25.
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: XSCANS (Bruker, 2000); cell refinement: XSCANS; data reduction: XPREP (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXL97.

N,N'-Bis(4-methyl-2-benzothiazolyl)pyridine-2,6-dicarboxamide N,N-dimethylformamide solvate

Crystal data

C23H17N5O2S2·C3H7NO	F(000) = 1112
Mr = 532.65	Dx = 1.372 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 224 reflections
a = 17.346 (4) Å	θ = 2.1–25.0°
b = 7.6140 (15) Å	µ = 0.25 mm^−1
c = 19.734 (4) Å	T = 293 K
β = 98.22 (3)°	Block, light yellow
V = 2579.5 (10) Å^3	0.35 × 0.25 × 0.24 mm
Z = 4

Data collection

Siemens P4 diffractometer	3082 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.066
Graphite monochromator	θmax = 27.5°, θmin = 1.5°
2θ/ω scans	h = −19→20
Absorption correction: ψ scan (North et al., 1968)	k = 0→9
Tmin = 0.929, Tmax = 0.942	l = −23→25
6231 measured reflections	3 standard reflections every 97 reflections
5107 independent reflections	intensity decay: 0.1%

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	H-atom parameters constrained
S = 0.93	w = 1/[σ^2(Fo^2) + (0.0511P)^2] where P = (Fo^2 + 2Fc^2)/3
5107 reflections	(Δ/σ)max = 0.001
338 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

Experimental. IR (cm^-1): 3452, 3170, 2921, 3178, 1676, 1655, 1586, 1534, 1427, 1257, 1119, 1072, 999, 768, 741.

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
S1	0.51044 (5)	0.29013 (10)	0.77438 (4)	0.0582 (2)
S2	0.75724 (4)	1.03409 (8)	1.17014 (3)	0.04509 (16)
C1	0.57867 (15)	0.3510 (3)	1.00586 (13)	0.0481 (6)
C2	0.56012 (16)	0.2204 (3)	1.05046 (15)	0.0516 (6)
H2	0.5357	0.1174	1.0336	0.062*
C3	0.57846 (17)	0.2467 (3)	1.11877 (15)	0.0561 (7)
H3	0.5664	0.1620	1.1496	0.067*
C4	0.61538 (15)	0.4012 (4)	1.14227 (13)	0.0505 (6)
H4	0.6287	0.4220	1.1889	0.061*
C5	0.63205 (14)	0.5251 (3)	1.09409 (12)	0.0431 (5)
C6	0.55910 (15)	0.3262 (3)	0.93117 (14)	0.0498 (6)
C7	0.55480 (15)	0.4678 (4)	0.82019 (13)	0.0485 (6)
C8	0.53613 (16)	0.5838 (4)	0.71730 (13)	0.0513 (6)
C9	0.53435 (16)	0.7143 (4)	0.66618 (15)	0.0570 (7)
C10	0.50249 (18)	0.6677 (4)	0.60171 (14)	0.0612 (7)
H10	0.5002	0.7514	0.5672	0.073*
C11	0.47312 (17)	0.5008 (4)	0.58491 (16)	0.0610 (8)
H11	0.4527	0.4753	0.5398	0.073*
C12	0.47402 (16)	0.3714 (4)	0.63496 (15)	0.0580 (7)
H12	0.4545	0.2595	0.6243	0.070*
C13	0.50513 (15)	0.4163 (4)	0.70135 (13)	0.0538 (7)
C14	0.67207 (14)	0.6889 (3)	1.12021 (12)	0.0440 (6)
C15	0.72945 (14)	0.9619 (3)	1.08653 (11)	0.0406 (5)
C16	0.78007 (14)	1.2191 (3)	1.06515 (12)	0.0415 (5)
C17	0.80227 (15)	1.3575 (3)	1.02597 (13)	0.0475 (6)
C18	0.83533 (17)	1.5008 (3)	1.06162 (15)	0.0567 (7)
H18	0.8522	1.5945	1.0373	0.068*
C19	0.84432 (16)	1.5103 (3)	1.13212 (15)	0.0541 (7)
H19	0.8656	1.6113	1.1537	0.065*
C20	0.82263 (15)	1.3744 (3)	1.17143 (13)	0.0504 (6)
H20	0.8288	1.3814	1.2190	0.060*
C21	0.79106 (14)	1.2263 (3)	1.13670 (12)	0.0411 (5)
C22	0.56544 (15)	0.8940 (3)	0.68476 (12)	0.0435 (6)
H22A	0.5427	0.9374	0.7231	0.065*
H22B	0.5526	0.9714	0.6464	0.065*
H22C	0.6210	0.8884	0.6967	0.065*
C23	0.79074 (15)	1.3490 (3)	0.95008 (12)	0.0443 (6)
H23A	0.7935	1.4653	0.9317	0.066*
H23B	0.7406	1.2990	0.9341	0.066*
H23C	0.8307	1.2772	0.9353	0.066*
N6	0.73798 (12)	0.9303 (3)	0.85503 (10)	0.0464 (5)
C24	0.81175 (15)	0.8486 (3)	0.87963 (13)	0.0496 (6)
H24A	0.8454	0.9324	0.9054	0.074*
H24B	0.8355	0.8082	0.8414	0.074*
H24C	0.8035	0.7507	0.9084	0.074*
C25	0.73741 (16)	1.0654 (3)	0.80313 (12)	0.0473 (6)
H25A	0.6864	1.1164	0.7939	0.071*
H25B	0.7509	1.0143	0.7619	0.071*
H25C	0.7746	1.1548	0.8192	0.071*
C26	0.67643 (15)	0.8832 (3)	0.88048 (12)	0.0435 (5)
H26	0.6305	0.9438	0.8657	0.052*
N1	0.61461 (12)	0.5007 (2)	1.02716 (10)	0.0421 (5)
N2	0.57614 (13)	0.4608 (3)	0.89063 (11)	0.0507 (5)
H2A	0.6020	0.5480	0.9100	0.061*
N3	0.56459 (13)	0.6094 (3)	0.78592 (10)	0.0505 (5)
N4	0.69110 (12)	0.8018 (3)	1.07152 (10)	0.0460 (5)
H4A	0.6788	0.7730	1.0292	0.055*
N5	0.74519 (12)	1.0637 (3)	1.03739 (9)	0.0425 (5)
O1	0.52798 (10)	0.1901 (2)	0.90622 (8)	0.0469 (4)
O2	0.68777 (10)	0.7208 (2)	1.18044 (8)	0.0450 (4)
O5	0.67350 (10)	0.7648 (2)	0.92271 (8)	0.0476 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0637 (5)	0.0474 (4)	0.0632 (4)	−0.0106 (3)	0.0080 (3)	−0.0176 (3)
S2	0.0561 (4)	0.0367 (3)	0.0419 (3)	−0.0055 (3)	0.0049 (3)	0.0013 (3)
C1	0.0446 (15)	0.0380 (14)	0.0600 (15)	−0.0001 (12)	0.0016 (11)	−0.0063 (11)
C2	0.0505 (16)	0.0321 (12)	0.0711 (17)	−0.0087 (12)	0.0045 (12)	−0.0069 (12)
C3	0.0640 (19)	0.0438 (16)	0.0624 (16)	−0.0099 (13)	0.0158 (14)	0.0139 (12)
C4	0.0516 (15)	0.0488 (15)	0.0502 (13)	0.0005 (12)	0.0041 (11)	0.0033 (12)
C5	0.0411 (14)	0.0372 (13)	0.0516 (13)	−0.0007 (11)	0.0089 (10)	−0.0010 (10)
C6	0.0474 (15)	0.0368 (14)	0.0628 (15)	−0.0019 (12)	−0.0001 (12)	−0.0091 (12)
C7	0.0472 (15)	0.0413 (13)	0.0558 (14)	−0.0027 (12)	0.0037 (11)	−0.0172 (12)
C8	0.0518 (15)	0.0506 (16)	0.0523 (14)	0.0034 (13)	0.0099 (11)	−0.0137 (12)
C9	0.0513 (17)	0.0497 (17)	0.0717 (18)	0.0097 (14)	0.0149 (13)	−0.0055 (15)
C10	0.0713 (19)	0.0579 (19)	0.0547 (16)	0.0060 (16)	0.0101 (13)	−0.0002 (14)
C11	0.0531 (17)	0.0589 (19)	0.0731 (19)	0.0076 (14)	0.0168 (14)	−0.0088 (15)
C12	0.0514 (16)	0.0513 (17)	0.0716 (18)	0.0066 (14)	0.0099 (13)	−0.0113 (14)
C13	0.0491 (15)	0.0587 (18)	0.0562 (15)	−0.0010 (13)	0.0167 (12)	−0.0145 (13)
C14	0.0487 (15)	0.0348 (13)	0.0488 (14)	0.0038 (11)	0.0080 (10)	−0.0034 (11)
C15	0.0484 (14)	0.0334 (11)	0.0419 (11)	0.0022 (11)	0.0129 (10)	−0.0004 (9)
C16	0.0338 (13)	0.0418 (13)	0.0494 (13)	0.0069 (11)	0.0072 (9)	0.0012 (11)
C17	0.0478 (15)	0.0440 (14)	0.0505 (14)	0.0032 (12)	0.0059 (11)	0.0080 (11)
C18	0.0571 (17)	0.0340 (15)	0.082 (2)	−0.0032 (12)	0.0206 (14)	0.0116 (13)
C19	0.0567 (17)	0.0327 (14)	0.0754 (18)	−0.0015 (12)	0.0183 (14)	−0.0069 (12)
C20	0.0536 (16)	0.0497 (16)	0.0475 (13)	−0.0031 (13)	0.0060 (11)	−0.0083 (12)
C21	0.0416 (13)	0.0314 (12)	0.0508 (13)	0.0005 (10)	0.0086 (10)	−0.0014 (10)
C22	0.0477 (14)	0.0366 (13)	0.0472 (12)	0.0058 (11)	0.0104 (10)	0.0040 (10)
C23	0.0491 (15)	0.0384 (13)	0.0458 (13)	0.0004 (11)	0.0085 (10)	−0.0005 (10)
N6	0.0472 (13)	0.0422 (12)	0.0500 (11)	0.0009 (10)	0.0082 (9)	0.0004 (9)
C24	0.0553 (16)	0.0397 (13)	0.0542 (14)	0.0039 (12)	0.0094 (12)	0.0018 (11)
C25	0.0572 (15)	0.0413 (14)	0.0433 (12)	0.0010 (12)	0.0068 (11)	0.0030 (10)
C26	0.0476 (14)	0.0382 (14)	0.0455 (12)	0.0018 (11)	0.0092 (10)	0.0021 (11)
N1	0.0371 (11)	0.0282 (10)	0.0613 (12)	0.0022 (8)	0.0081 (9)	−0.0072 (9)
N2	0.0504 (13)	0.0421 (12)	0.0575 (12)	−0.0038 (10)	0.0006 (10)	−0.0124 (10)
N3	0.0565 (13)	0.0449 (13)	0.0508 (12)	−0.0012 (10)	0.0096 (10)	−0.0119 (10)
N4	0.0564 (13)	0.0330 (10)	0.0461 (11)	−0.0050 (10)	−0.0010 (9)	−0.0068 (9)
N5	0.0447 (11)	0.0383 (11)	0.0440 (10)	−0.0021 (9)	0.0051 (8)	−0.0045 (8)
O1	0.0521 (10)	0.0379 (10)	0.0495 (9)	−0.0029 (8)	0.0033 (7)	−0.0002 (7)
O2	0.0496 (10)	0.0387 (10)	0.0467 (9)	−0.0009 (8)	0.0066 (8)	−0.0003 (7)
O5	0.0559 (11)	0.0406 (10)	0.0459 (9)	−0.0019 (8)	0.0056 (8)	−0.0012 (8)

Geometric parameters (Å, º)

S1—C13	1.724 (3)	C15—N5	1.300 (3)
S1—C7	1.743 (3)	C15—N4	1.400 (3)
S2—C15	1.741 (2)	C16—C17	1.393 (3)
S2—C21	1.741 (2)	C16—C21	1.399 (3)
C1—N1	1.338 (3)	C16—N5	1.404 (3)
C1—C2	1.396 (4)	C17—C18	1.378 (4)
C1—C6	1.477 (4)	C17—C23	1.484 (3)
C2—C3	1.355 (4)	C18—C19	1.379 (4)
C2—H2	0.93	C18—H18	0.93
C3—C4	1.388 (4)	C19—C20	1.377 (4)
C3—H3	0.93	C19—H19	0.93
C4—C5	1.398 (4)	C20—C21	1.391 (3)
C4—H4	0.93	C20—H20	0.93
C5—N1	1.325 (3)	C22—H22A	0.96
C5—C14	1.484 (3)	C22—H22B	0.96
C6—O1	1.238 (3)	C22—H22C	0.96
C6—N2	1.358 (3)	C23—H23A	0.96
C7—N3	1.297 (3)	C23—H23B	0.96
C7—N2	1.388 (3)	C23—H23C	0.96
C8—N3	1.387 (3)	N6—C26	1.294 (3)
C8—C13	1.402 (4)	N6—C24	1.443 (3)
C8—C9	1.413 (4)	N6—C25	1.450 (3)
C9—C10	1.360 (4)	C24—H24A	0.96
C9—C22	1.497 (4)	C24—H24B	0.96
C10—C11	1.392 (4)	C24—H24C	0.96
C10—H10	0.93	C25—H25A	0.96
C11—C12	1.393 (4)	C25—H25B	0.96
C11—H11	0.93	C25—H25C	0.96
C12—C13	1.386 (4)	C26—O5	1.234 (3)
C12—H12	0.93	C26—H26	0.93
C14—O2	1.206 (3)	N2—H2A	0.86
C14—N4	1.365 (3)	N4—H4A	0.86
C13—S1—C7	88.16 (14)	C16—C17—C23	121.3 (2)
C15—S2—C21	88.21 (11)	C17—C18—C19	122.3 (2)
N1—C1—C2	123.2 (3)	C17—C18—H18	118.8
N1—C1—C6	116.9 (2)	C19—C18—H18	118.8
C2—C1—C6	119.8 (2)	C20—C19—C18	121.9 (3)
C3—C2—C1	118.7 (3)	C20—C19—H19	119.1
C3—C2—H2	120.7	C18—C19—H19	119.1
C1—C2—H2	120.7	C19—C20—C21	116.8 (2)
C2—C3—C4	119.3 (2)	C19—C20—H20	121.6
C2—C3—H3	120.4	C21—C20—H20	121.6
C4—C3—H3	120.4	C20—C21—C16	121.1 (2)
C3—C4—C5	118.4 (2)	C20—C21—S2	128.68 (19)
C3—C4—H4	120.8	C16—C21—S2	110.18 (18)
C5—C4—H4	120.8	C9—C22—H22A	109.5
N1—C5—C4	122.9 (2)	C9—C22—H22B	109.5
N1—C5—C14	119.5 (2)	H22A—C22—H22B	109.5
C4—C5—C14	117.6 (2)	C9—C22—H22C	109.5
O1—C6—N2	121.1 (2)	H22A—C22—H22C	109.5
O1—C6—C1	121.9 (2)	H22B—C22—H22C	109.5
N2—C6—C1	116.9 (2)	C17—C23—H23A	109.5
N3—C7—N2	121.2 (2)	C17—C23—H23B	109.5
N3—C7—S1	117.1 (2)	H23A—C23—H23B	109.5
N2—C7—S1	121.6 (2)	C17—C23—H23C	109.5
N3—C8—C13	114.8 (3)	H23A—C23—H23C	109.5
N3—C8—C9	124.5 (3)	H23B—C23—H23C	109.5
C13—C8—C9	120.7 (3)	C26—N6—C24	119.4 (2)
C10—C9—C8	116.7 (3)	C26—N6—C25	123.2 (2)
C10—C9—C22	123.5 (3)	C24—N6—C25	117.4 (2)
C8—C9—C22	119.8 (2)	N6—C24—H24A	109.5
C9—C10—C11	123.2 (3)	N6—C24—H24B	109.5
C9—C10—H10	118.4	H24A—C24—H24B	109.5
C11—C10—H10	118.4	N6—C24—H24C	109.5
C10—C11—C12	120.7 (3)	H24A—C24—H24C	109.5
C10—C11—H11	119.7	H24B—C24—H24C	109.5
C12—C11—H11	119.7	N6—C25—H25A	109.5
C13—C12—C11	117.3 (3)	N6—C25—H25B	109.5
C13—C12—H12	121.3	H25A—C25—H25B	109.5
C11—C12—H12	121.3	N6—C25—H25C	109.5
C12—C13—C8	121.4 (3)	H25A—C25—H25C	109.5
C12—C13—S1	128.3 (2)	H25B—C25—H25C	109.5
C8—C13—S1	110.3 (2)	O5—C26—N6	125.5 (2)
O2—C14—N4	121.6 (2)	O5—C26—H26	117.2
O2—C14—C5	122.7 (2)	N6—C26—H26	117.2
N4—C14—C5	115.7 (2)	C5—N1—C1	117.5 (2)
N5—C15—N4	120.3 (2)	C6—N2—C7	124.7 (2)
N5—C15—S2	117.35 (19)	C6—N2—H2A	117.6
N4—C15—S2	122.30 (17)	C7—N2—H2A	117.6
C17—C16—C21	121.5 (2)	C7—N3—C8	109.7 (2)
C17—C16—N5	124.0 (2)	C14—N4—C15	123.7 (2)
C21—C16—N5	114.6 (2)	C14—N4—H4A	118.1
C18—C17—C16	116.3 (2)	C15—N4—H4A	118.1
C18—C17—C23	122.4 (2)	C15—N5—C16	109.64 (19)
N1—C1—C2—C3	0.8 (4)	C21—C16—C17—C23	179.8 (2)
C6—C1—C2—C3	−179.8 (2)	N5—C16—C17—C23	−0.5 (4)
C1—C2—C3—C4	−0.4 (4)	C16—C17—C18—C19	−1.7 (4)
C2—C3—C4—C5	0.2 (4)	C23—C17—C18—C19	178.4 (3)
C3—C4—C5—N1	−0.4 (4)	C17—C18—C19—C20	1.8 (4)
C3—C4—C5—C14	−179.5 (2)	C18—C19—C20—C21	0.0 (4)
N1—C1—C6—O1	177.8 (2)	C19—C20—C21—C16	−1.8 (4)
C2—C1—C6—O1	−1.7 (4)	C19—C20—C21—S2	−179.4 (2)
N1—C1—C6—N2	−2.9 (4)	C17—C16—C21—C20	1.9 (4)
C2—C1—C6—N2	177.7 (2)	N5—C16—C21—C20	−177.9 (2)
C13—S1—C7—N3	0.7 (2)	C17—C16—C21—S2	179.9 (2)
C13—S1—C7—N2	178.3 (2)	N5—C16—C21—S2	0.2 (3)
N3—C8—C9—C10	−178.3 (3)	C15—S2—C21—C20	176.7 (3)
C13—C8—C9—C10	−1.0 (4)	C15—S2—C21—C16	−1.17 (19)
N3—C8—C9—C22	0.7 (4)	C24—N6—C26—O5	−4.1 (4)
C13—C8—C9—C22	178.0 (2)	C25—N6—C26—O5	177.1 (2)
C8—C9—C10—C11	−0.5 (4)	C4—C5—N1—C1	0.8 (4)
C22—C9—C10—C11	−179.5 (3)	C14—C5—N1—C1	179.9 (2)
C9—C10—C11—C12	1.0 (5)	C2—C1—N1—C5	−1.0 (4)
C10—C11—C12—C13	0.0 (4)	C6—C1—N1—C5	179.6 (2)
C11—C12—C13—C8	−1.5 (4)	O1—C6—N2—C7	6.3 (4)
C11—C12—C13—S1	176.8 (2)	C1—C6—N2—C7	−173.1 (2)
N3—C8—C13—C12	179.6 (2)	N3—C7—N2—C6	171.4 (3)
C9—C8—C13—C12	2.0 (4)	S1—C7—N2—C6	−6.2 (4)
N3—C8—C13—S1	1.0 (3)	N2—C7—N3—C8	−177.9 (2)
C9—C8—C13—S1	−176.6 (2)	S1—C7—N3—C8	−0.2 (3)
C7—S1—C13—C12	−179.3 (3)	C13—C8—N3—C7	−0.5 (3)
C7—S1—C13—C8	−0.9 (2)	C9—C8—N3—C7	177.0 (3)
N1—C5—C14—O2	178.1 (2)	O2—C14—N4—C15	−0.3 (4)
C4—C5—C14—O2	−2.8 (4)	C5—C14—N4—C15	−179.6 (2)
N1—C5—C14—N4	−2.6 (3)	N5—C15—N4—C14	−179.5 (2)
C4—C5—C14—N4	176.5 (2)	S2—C15—N4—C14	0.1 (3)
C21—S2—C15—N5	2.2 (2)	N4—C15—N5—C16	177.1 (2)
C21—S2—C15—N4	−177.4 (2)	S2—C15—N5—C16	−2.4 (3)
C21—C16—C17—C18	−0.1 (4)	C17—C16—N5—C15	−178.4 (2)
N5—C16—C17—C18	179.6 (2)	C21—C16—N5—C15	1.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1	0.86	2.32	2.699 (3)	107
N4—H4A···N1	0.86	2.35	2.730 (3)	107
N2—H2A···O5	0.86	2.06	2.882 (3)	160
N4—H4A···O5	0.86	2.09	2.922 (3)	162
C20—H20···O2^i	0.93	2.38	3.178 (3)	143
C12—H12···Cg1^ii	0.93	2.62	3.318 (3)	133

Symmetry codes: (i) −x+3/2, y+1/2, −z+5/2; (ii) x−1/2, −y+3/2, z−1/2.