Crystal structure and Hirshfeld surface analysis of 1-methyl-4-(2-methyl-10H-benzo[b]thieno[2,3-e][1,4]diazepin-4-yl)piperazin-1-ium 2,5-di­hydroxy­benzoate propan-2-ol monosolvate

The asymmetric unit of the title salt consists of an olanzapinium cation, an independent 2,5 di­hydroxy­benzoate anion and a solvent isopropyl alcohol mol­ecule. The central seven-membered heterocycle is in a boat conformation, while the piperazine ring displays a distorted chair conformation. The dihedral angle between the benzene and thiene rings flanking the diazepine ring is 52.58 (19)°. In the crystal, the anions and cations are connected by N—H...O and O—H...O hydrogen bonds, forming a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.069
• wR factor = 0.143
• Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5882
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of        C26 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00423 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A      ..O1       .       2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13A     ..O4       .       2.62 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H17B     ..O2       .       2.63 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     11.318 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.566 Check

Alert level G
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        94% Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT954_ALERT_1_G Reported (CIF) and Actual (FCF) Kmax Differ by .          1 Units
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   8 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

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

---

Computing details

Data collection: SMART (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2018); molecular graphics: QMOL (Gans & Shalloway, 2001), Mercury (Macrae et al., 2020); software used to prepare material for publication: ORTEPIII (Burnett & Johnson, 1996), WinGX publication routines (Farrugia, 2012) and PLATON (Spek, 2020).

1-Methyl-4-(2-methyl-10H-benzo[b]thieno[2,3-e][1,4]diazepin-4-yl)piperazin-1-ium 2,5-dihydroxybenzoate propan-2-ol monosolvate

Crystal data

C17H21N4S^+·C7H5O4^−·C3H8O	F(000) = 1120
Mr = 526.64	Dx = 1.306 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.4867 (6) Å	Cell parameters from 4689 reflections
b = 29.764 (2) Å	θ = 2.3–24.2°
c = 10.6334 (8) Å	µ = 0.17 mm^−1
β = 94.381 (1)°	T = 294 K
V = 2678.1 (3) Å^3	Solid, white
Z = 4	0.15 × 0.14 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer	4081 reflections with I > 2σ(I)
Radiation source: fine focus sealed tube	Rint = 0.040
ω and φ scan	θmax = 24.7°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→9
Tmin = 0.96, Tmax = 0.98	k = −35→35
25175 measured reflections	l = −12→12
4560 independent 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)] = 0.069	Hydrogen site location: mixed
wR(F^2) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 1.31	w = 1/[σ^2(Fo^2) + (0.0423P)^2 + 1.7858P] where P = (Fo^2 + 2Fc^2)/3
4560 reflections	(Δ/σ)max = 0.001
358 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

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
C1	−0.3762 (4)	0.47317 (12)	0.3380 (4)	0.0585 (9)
H1A	−0.390099	0.447460	0.283753	0.088*
H1B	−0.459922	0.494268	0.317993	0.088*
H1C	−0.378228	0.463851	0.424267	0.088*
C2	−0.2208 (3)	0.49488 (10)	0.3192 (3)	0.0406 (7)
C3	−0.1143 (3)	0.48603 (10)	0.2353 (3)	0.0385 (7)
H3	−0.128823	0.463584	0.174715	0.046*
C4	0.0236 (3)	0.51399 (9)	0.2470 (3)	0.0352 (7)
C5	0.0161 (3)	0.54454 (9)	0.3420 (3)	0.0350 (7)
C6	0.1609 (3)	0.60738 (10)	0.2772 (3)	0.0366 (7)
C7	0.1472 (4)	0.65330 (10)	0.2934 (3)	0.0430 (7)
H7	0.110794	0.664279	0.367734	0.052*
C8	0.1862 (4)	0.68310 (11)	0.2016 (3)	0.0489 (8)
H8	0.176887	0.713877	0.214109	0.059*
C9	0.2390 (4)	0.66693 (11)	0.0915 (3)	0.0524 (9)
H9	0.264640	0.686670	0.028400	0.063*
C10	0.2537 (4)	0.62100 (11)	0.0749 (3)	0.0467 (8)
H10	0.290372	0.610411	0.000239	0.056*
C11	0.2157 (3)	0.59022 (10)	0.1660 (3)	0.0379 (7)
C12	0.1630 (3)	0.51169 (10)	0.1725 (3)	0.0374 (7)
C13	0.1896 (4)	0.42917 (9)	0.2035 (3)	0.0395 (7)
H13A	0.108954	0.432885	0.262627	0.047*
H13B	0.290178	0.424550	0.251401	0.047*
C14	0.1511 (4)	0.38905 (10)	0.1209 (3)	0.0446 (8)
H14A	0.149251	0.362254	0.172674	0.054*
H14B	0.047123	0.392826	0.077708	0.054*
C15	0.2881 (4)	0.42556 (11)	−0.0459 (3)	0.0491 (8)
H15A	0.192261	0.430932	−0.099538	0.059*
H15B	0.374372	0.422019	−0.099854	0.059*
C16	0.3204 (4)	0.46547 (10)	0.0388 (3)	0.0440 (8)
H16A	0.422192	0.461909	0.085780	0.053*
H16B	0.323924	0.492549	−0.011672	0.053*
C17	0.2321 (5)	0.34478 (12)	−0.0581 (4)	0.0658 (11)
H17A	0.130021	0.349145	−0.101715	0.099*
H17B	0.231500	0.317686	−0.009157	0.099*
H17C	0.310467	0.342428	−0.118316	0.099*
N1	0.2492 (3)	0.54488 (8)	0.1415 (2)	0.0422 (6)
N2	0.1266 (3)	0.57751 (9)	0.3767 (2)	0.0401 (6)
H2	0.104 (3)	0.5922 (10)	0.443 (3)	0.038 (9)*
N3	0.1973 (3)	0.46954 (8)	0.1257 (2)	0.0401 (6)
N4	0.2699 (3)	0.38349 (9)	0.0266 (2)	0.0426 (6)
H4	0.359 (4)	0.3785 (12)	0.075 (3)	0.062 (11)*
S1	−0.15686 (9)	0.53903 (3)	0.41676 (8)	0.0417 (2)
C18	0.5648 (4)	0.32953 (11)	0.1890 (3)	0.0392 (7)
C19	0.7193 (3)	0.31664 (9)	0.2566 (3)	0.0323 (6)
C20	0.8224 (3)	0.34904 (9)	0.3104 (3)	0.0333 (6)
H20	0.795966	0.379278	0.302211	0.040*
C21	0.9623 (3)	0.33711 (9)	0.3753 (3)	0.0332 (6)
C22	1.0032 (4)	0.29233 (10)	0.3851 (3)	0.0431 (8)
H22	1.098573	0.284064	0.427658	0.052*
C23	0.9038 (4)	0.25982 (10)	0.3322 (3)	0.0466 (8)
H23	0.932732	0.229732	0.338820	0.056*
C24	0.7613 (3)	0.27150 (10)	0.2692 (3)	0.0380 (7)
O1	0.5341 (2)	0.37036 (7)	0.1732 (2)	0.0469 (6)
O2	0.4736 (3)	0.29822 (8)	0.1504 (2)	0.0603 (7)
O3	0.6639 (3)	0.23843 (8)	0.2203 (3)	0.0571 (7)
H3A	0.581 (5)	0.2537 (13)	0.186 (4)	0.071 (13)*
O4	1.0557 (3)	0.37078 (7)	0.4286 (2)	0.0442 (5)
H4A	1.127 (5)	0.3588 (13)	0.478 (4)	0.071 (13)*
C25	0.4829 (5)	0.37490 (14)	0.5193 (4)	0.0740 (12)
H25A	0.463666	0.400651	0.570276	0.111*
H25B	0.421761	0.377329	0.439808	0.111*
H25C	0.593185	0.373497	0.505130	0.111*
C26	0.4367 (4)	0.33350 (12)	0.5852 (3)	0.0519 (9)
H26	0.493746	0.332991	0.668868	0.062*
C27	0.4755 (6)	0.29132 (15)	0.5177 (4)	0.0808 (13)
H27A	0.426807	0.292136	0.433192	0.121*
H27B	0.436502	0.265885	0.561363	0.121*
H27C	0.587968	0.288851	0.515149	0.121*
O5	0.2703 (3)	0.33712 (9)	0.6017 (2)	0.0548 (6)
H5	0.238 (4)	0.3130 (12)	0.641 (3)	0.058 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.046 (2)	0.052 (2)	0.078 (3)	−0.0084 (16)	0.0086 (18)	−0.0055 (19)
C2	0.0369 (17)	0.0321 (16)	0.0523 (19)	0.0018 (13)	−0.0002 (14)	0.0041 (14)
C3	0.0413 (17)	0.0286 (15)	0.0445 (17)	0.0018 (13)	−0.0032 (14)	−0.0019 (13)
C4	0.0381 (17)	0.0292 (15)	0.0377 (16)	0.0041 (12)	−0.0004 (13)	0.0056 (13)
C5	0.0369 (16)	0.0324 (16)	0.0353 (16)	0.0010 (13)	0.0001 (13)	0.0057 (13)
C6	0.0335 (16)	0.0379 (17)	0.0378 (16)	−0.0064 (13)	−0.0003 (13)	0.0048 (13)
C7	0.0422 (18)	0.0393 (18)	0.0476 (18)	−0.0023 (14)	0.0044 (14)	−0.0037 (15)
C8	0.0488 (19)	0.0377 (18)	0.061 (2)	0.0000 (15)	0.0075 (16)	0.0042 (16)
C9	0.058 (2)	0.0422 (19)	0.058 (2)	−0.0043 (16)	0.0106 (17)	0.0165 (16)
C10	0.051 (2)	0.047 (2)	0.0431 (18)	−0.0029 (15)	0.0104 (15)	0.0032 (15)
C11	0.0324 (16)	0.0384 (17)	0.0429 (17)	−0.0023 (13)	0.0021 (13)	0.0042 (14)
C12	0.0416 (17)	0.0363 (17)	0.0336 (16)	0.0058 (14)	−0.0014 (13)	0.0027 (13)
C13	0.0405 (17)	0.0361 (17)	0.0424 (17)	0.0082 (13)	0.0064 (14)	0.0051 (14)
C14	0.0391 (17)	0.0388 (17)	0.055 (2)	0.0058 (14)	0.0006 (15)	−0.0009 (15)
C15	0.057 (2)	0.054 (2)	0.0368 (17)	0.0186 (17)	0.0026 (15)	0.0040 (15)
C16	0.0481 (19)	0.0451 (19)	0.0397 (17)	0.0075 (15)	0.0088 (14)	0.0053 (14)
C17	0.077 (3)	0.057 (2)	0.060 (2)	0.012 (2)	−0.017 (2)	−0.0209 (19)
N1	0.0428 (15)	0.0379 (15)	0.0469 (15)	0.0026 (12)	0.0090 (12)	0.0031 (12)
N2	0.0490 (16)	0.0389 (15)	0.0321 (14)	−0.0091 (12)	0.0011 (12)	−0.0037 (12)
N3	0.0484 (15)	0.0334 (14)	0.0396 (14)	0.0055 (11)	0.0096 (12)	0.0037 (11)
N4	0.0431 (15)	0.0422 (15)	0.0408 (15)	0.0124 (12)	−0.0072 (13)	−0.0056 (12)
S1	0.0447 (5)	0.0361 (4)	0.0455 (5)	−0.0030 (3)	0.0105 (4)	−0.0033 (3)
C18	0.0372 (17)	0.0459 (19)	0.0346 (16)	0.0043 (15)	0.0032 (13)	−0.0043 (14)
C19	0.0315 (15)	0.0368 (16)	0.0294 (14)	0.0039 (12)	0.0063 (12)	−0.0023 (12)
C20	0.0379 (16)	0.0268 (14)	0.0354 (15)	0.0050 (12)	0.0047 (13)	0.0017 (12)
C21	0.0363 (16)	0.0327 (16)	0.0307 (14)	−0.0023 (12)	0.0028 (12)	0.0000 (12)
C22	0.0397 (17)	0.0405 (18)	0.0472 (18)	0.0078 (14)	−0.0085 (14)	0.0035 (14)
C23	0.0491 (19)	0.0253 (16)	0.064 (2)	0.0052 (14)	−0.0056 (16)	−0.0023 (15)
C24	0.0359 (16)	0.0348 (16)	0.0430 (17)	−0.0012 (13)	0.0022 (13)	−0.0060 (13)
O1	0.0411 (12)	0.0462 (14)	0.0518 (13)	0.0106 (10)	−0.0059 (10)	0.0003 (10)
O2	0.0412 (13)	0.0572 (15)	0.0789 (18)	−0.0010 (12)	−0.0182 (12)	−0.0084 (13)
O3	0.0453 (14)	0.0362 (13)	0.0874 (19)	−0.0014 (11)	−0.0101 (13)	−0.0156 (12)
O4	0.0440 (13)	0.0357 (12)	0.0507 (13)	−0.0039 (10)	−0.0116 (11)	0.0016 (10)
C25	0.051 (2)	0.083 (3)	0.089 (3)	−0.008 (2)	0.006 (2)	0.022 (2)
C26	0.0376 (18)	0.065 (2)	0.052 (2)	−0.0007 (16)	−0.0038 (15)	0.0092 (17)
C27	0.087 (3)	0.077 (3)	0.083 (3)	−0.001 (2)	0.034 (3)	−0.006 (2)
O5	0.0398 (13)	0.0617 (16)	0.0624 (16)	−0.0048 (11)	−0.0001 (11)	0.0184 (13)

Geometric parameters (Å, º)

C1—C2	1.496 (4)	C16—N3	1.452 (4)
C1—H1A	0.9600	C16—H16A	0.9700
C1—H1B	0.9600	C16—H16B	0.9700
C1—H1C	0.9600	C17—N4	1.483 (4)
C2—C3	1.343 (4)	C17—H17A	0.9600
C2—S1	1.736 (3)	C17—H17B	0.9600
C3—C4	1.434 (4)	C17—H17C	0.9600
C3—H3	0.9300	N2—H2	0.87 (3)
C4—C5	1.365 (4)	N4—H4	0.89 (4)
C4—C12	1.474 (4)	C18—O1	1.252 (4)
C5—N2	1.388 (4)	C18—O2	1.260 (4)
C5—S1	1.729 (3)	C18—C19	1.496 (4)
C6—C7	1.383 (4)	C19—C24	1.394 (4)
C6—C11	1.400 (4)	C19—C20	1.395 (4)
C6—N2	1.429 (4)	C20—C21	1.373 (4)
C7—C8	1.378 (4)	C20—H20	0.9300
C7—H7	0.9300	C21—O4	1.373 (3)
C8—C9	1.372 (5)	C21—C22	1.379 (4)
C8—H8	0.9300	C22—C23	1.376 (4)
C9—C10	1.385 (4)	C22—H22	0.9300
C9—H9	0.9300	C23—C24	1.381 (4)
C10—C11	1.388 (4)	C23—H23	0.9300
C10—H10	0.9300	C24—O3	1.363 (4)
C11—N1	1.408 (4)	O3—H3A	0.89 (4)
C12—N1	1.287 (4)	O4—H4A	0.85 (4)
C12—N3	1.389 (4)	C25—C26	1.485 (5)
C13—N3	1.463 (4)	C25—H25A	0.9600
C13—C14	1.503 (4)	C25—H25B	0.9600
C13—H13A	0.9700	C25—H25C	0.9600
C13—H13B	0.9700	C26—O5	1.440 (4)
C14—N4	1.484 (4)	C26—C27	1.495 (5)
C14—H14A	0.9700	C26—H26	0.9800
C14—H14B	0.9700	C27—H27A	0.9600
C15—N4	1.485 (4)	C27—H27B	0.9600
C15—C16	1.503 (4)	C27—H27C	0.9600
C15—H15A	0.9700	O5—H5	0.88 (4)
C15—H15B	0.9700
C2—C1—H1A	109.5	N4—C17—H17A	109.5
C2—C1—H1B	109.5	N4—C17—H17B	109.5
H1A—C1—H1B	109.5	H17A—C17—H17B	109.5
C2—C1—H1C	109.5	N4—C17—H17C	109.5
H1A—C1—H1C	109.5	H17A—C17—H17C	109.5
H1B—C1—H1C	109.5	H17B—C17—H17C	109.5
C3—C2—C1	130.5 (3)	C12—N1—C11	124.2 (3)
C3—C2—S1	110.5 (2)	C5—N2—C6	114.5 (2)
C1—C2—S1	119.1 (2)	C5—N2—H2	113 (2)
C2—C3—C4	114.5 (3)	C6—N2—H2	111 (2)
C2—C3—H3	122.7	C12—N3—C16	119.0 (2)
C4—C3—H3	122.7	C12—N3—C13	121.3 (2)
C5—C4—C3	111.5 (3)	C16—N3—C13	110.9 (2)
C5—C4—C12	120.9 (3)	C17—N4—C14	111.8 (3)
C3—C4—C12	127.6 (3)	C17—N4—C15	111.5 (3)
C4—C5—N2	126.8 (3)	C14—N4—C15	111.1 (2)
C4—C5—S1	111.5 (2)	C17—N4—H4	111 (2)
N2—C5—S1	121.7 (2)	C14—N4—H4	103 (2)
C7—C6—C11	120.1 (3)	C15—N4—H4	109 (2)
C7—C6—N2	119.9 (3)	C5—S1—C2	91.97 (14)
C11—C6—N2	119.9 (3)	O1—C18—O2	123.9 (3)
C8—C7—C6	121.4 (3)	O1—C18—C19	118.6 (3)
C8—C7—H7	119.3	O2—C18—C19	117.5 (3)
C6—C7—H7	119.3	C24—C19—C20	118.6 (3)
C9—C8—C7	119.4 (3)	C24—C19—C18	120.1 (3)
C9—C8—H8	120.3	C20—C19—C18	121.3 (3)
C7—C8—H8	120.3	C21—C20—C19	121.2 (3)
C8—C9—C10	119.5 (3)	C21—C20—H20	119.4
C8—C9—H9	120.2	C19—C20—H20	119.4
C10—C9—H9	120.2	O4—C21—C20	117.9 (3)
C9—C10—C11	122.3 (3)	O4—C21—C22	122.7 (3)
C9—C10—H10	118.8	C20—C21—C22	119.4 (3)
C11—C10—H10	118.8	C23—C22—C21	120.4 (3)
C10—C11—C6	117.3 (3)	C23—C22—H22	119.8
C10—C11—N1	116.3 (3)	C21—C22—H22	119.8
C6—C11—N1	126.2 (3)	C22—C23—C24	120.5 (3)
N1—C12—N3	117.6 (3)	C22—C23—H23	119.7
N1—C12—C4	126.6 (3)	C24—C23—H23	119.7
N3—C12—C4	115.7 (3)	O3—C24—C23	119.1 (3)
N3—C13—C14	109.8 (2)	O3—C24—C19	121.1 (3)
N3—C13—H13A	109.7	C23—C24—C19	119.8 (3)
C14—C13—H13A	109.7	C24—O3—H3A	103 (2)
N3—C13—H13B	109.7	C21—O4—H4A	108 (3)
C14—C13—H13B	109.7	C26—C25—H25A	109.5
H13A—C13—H13B	108.2	C26—C25—H25B	109.5
N4—C14—C13	110.8 (2)	H25A—C25—H25B	109.5
N4—C14—H14A	109.5	C26—C25—H25C	109.5
C13—C14—H14A	109.5	H25A—C25—H25C	109.5
N4—C14—H14B	109.5	H25B—C25—H25C	109.5
C13—C14—H14B	109.5	O5—C26—C25	107.0 (3)
H14A—C14—H14B	108.1	O5—C26—C27	112.0 (3)
N4—C15—C16	112.1 (3)	C25—C26—C27	113.2 (3)
N4—C15—H15A	109.2	O5—C26—H26	108.1
C16—C15—H15A	109.2	C25—C26—H26	108.1
N4—C15—H15B	109.2	C27—C26—H26	108.1
C16—C15—H15B	109.2	C26—C27—H27A	109.5
H15A—C15—H15B	107.9	C26—C27—H27B	109.5
N3—C16—C15	109.9 (3)	H27A—C27—H27B	109.5
N3—C16—H16A	109.7	C26—C27—H27C	109.5
C15—C16—H16A	109.7	H27A—C27—H27C	109.5
N3—C16—H16B	109.7	H27B—C27—H27C	109.5
C15—C16—H16B	109.7	C26—O5—H5	110 (2)
H16A—C16—H16B	108.2
C1—C2—C3—C4	−179.3 (3)	N1—C12—N3—C16	−3.9 (4)
S1—C2—C3—C4	0.6 (3)	C4—C12—N3—C16	172.5 (3)
C2—C3—C4—C5	−0.6 (4)	N1—C12—N3—C13	140.6 (3)
C2—C3—C4—C12	177.8 (3)	C4—C12—N3—C13	−42.9 (4)
C3—C4—C5—N2	−178.0 (3)	C15—C16—N3—C12	−152.5 (3)
C12—C4—C5—N2	3.5 (4)	C15—C16—N3—C13	59.5 (3)
C3—C4—C5—S1	0.3 (3)	C14—C13—N3—C12	151.8 (3)
C12—C4—C5—S1	−178.3 (2)	C14—C13—N3—C16	−61.1 (3)
C11—C6—C7—C8	0.1 (5)	C13—C14—N4—C17	−178.6 (3)
N2—C6—C7—C8	177.0 (3)	C13—C14—N4—C15	−53.4 (3)
C6—C7—C8—C9	0.4 (5)	C16—C15—N4—C17	177.9 (3)
C7—C8—C9—C10	−0.7 (5)	C16—C15—N4—C14	52.5 (4)
C8—C9—C10—C11	0.5 (5)	C4—C5—S1—C2	0.1 (2)
C9—C10—C11—C6	0.0 (5)	N2—C5—S1—C2	178.4 (2)
C9—C10—C11—N1	−174.7 (3)	C3—C2—S1—C5	−0.4 (2)
C7—C6—C11—C10	−0.3 (4)	C1—C2—S1—C5	179.6 (3)
N2—C6—C11—C10	−177.2 (3)	O1—C18—C19—C24	−176.1 (3)
C7—C6—C11—N1	173.8 (3)	O2—C18—C19—C24	3.3 (4)
N2—C6—C11—N1	−3.1 (5)	O1—C18—C19—C20	5.2 (4)
C5—C4—C12—N1	−34.3 (4)	O2—C18—C19—C20	−175.4 (3)
C3—C4—C12—N1	147.5 (3)	C24—C19—C20—C21	−0.4 (4)
C5—C4—C12—N3	149.7 (3)	C18—C19—C20—C21	178.3 (3)
C3—C4—C12—N3	−28.6 (4)	C19—C20—C21—O4	−178.3 (2)
N3—C13—C14—N4	57.4 (3)	C19—C20—C21—C22	1.5 (4)
N4—C15—C16—N3	−55.2 (3)	O4—C21—C22—C23	178.6 (3)
N3—C12—N1—C11	170.5 (3)	C20—C21—C22—C23	−1.1 (5)
C4—C12—N1—C11	−5.5 (5)	C21—C22—C23—C24	−0.4 (5)
C10—C11—N1—C12	−144.3 (3)	C22—C23—C24—O3	−178.5 (3)
C6—C11—N1—C12	41.5 (5)	C22—C23—C24—C19	1.5 (5)
C4—C5—N2—C6	56.1 (4)	C20—C19—C24—O3	178.9 (3)
S1—C5—N2—C6	−121.9 (3)	C18—C19—C24—O3	0.2 (4)
C7—C6—N2—C5	125.9 (3)	C20—C19—C24—C23	−1.1 (4)
C11—C6—N2—C5	−57.2 (4)	C18—C19—C24—C23	−179.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1^i	0.96	2.64	3.579 (4)	168
C10—H10···O1^ii	0.93	2.52	3.316 (4)	143
C13—H13A···O4^i	0.97	2.62	3.233 (4)	122
C17—H17B···O2	0.96	2.63	3.216 (4)	120
N2—H2···O4^iii	0.87 (3)	2.28 (3)	3.088 (4)	156 (3)
N4—H4···O1	0.89 (4)	1.77 (4)	2.660 (3)	178 (4)
O3—H3A···O2	0.89 (4)	1.63 (4)	2.479 (3)	156 (4)
O4—H4A···O5^iv	0.85 (4)	1.84 (4)	2.682 (3)	173 (4)
O5—H5···O3^v	0.88 (4)	1.88 (4)	2.764 (3)	178 (3)

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z; (iii) −x+1, −y+1, −z+1; (iv) x+1, y, z; (v) x−1/2, −y+1/2, z+1/2.