Crystal structure of 2-[(5-amino-1-tosyl-1H-pyrazol-3-yl)­oxy]-1-(4-meth­oxy­phen­yl)ethan-1-one 1,4-dioxane monosolvate

In the mol­ecular structure of the title compound, the pyrazole and its oxy-ethanone substituent lie parallel to each other, whereas the sulfonyl ring is roughly perpendicular to the pyrazole. The residues form a layer structure by hydrogen bonding.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.001 Å
• Disorder in solvent or counterion
• R factor = 0.027
• wR factor = 0.087
• Data-to-parameter ratio = 55.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report
                1 -7  1,   1 -6  2,  -1  7  2,  -4  1  3,  -2 -1  6,  -4 -5 12,

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          9 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          6 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          1 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  3  )       100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  4  )       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  3  )      13.03 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  4  )       0.97 Check
PLAT398_ALERT_2_G Deviating  C-O-C   Angle From 120 for O81      .      109.3 Degree
PLAT398_ALERT_2_G Deviating  C-O-C   Angle From 120 for O91'     .      108.6 Degree
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          2 Note
              H031    H032
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         22 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
                0  1  0,   0 -1  1,   0  0  1,
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         13 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          6 Note
                1 -7  1,   1 -6  2,  -1  7  2,  -2 -1  6,  -4  1  3,  -4 -5 12,
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         17 Info
PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by          2 Check

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

   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
   3 ALERT type 3 Indicator that the structure quality may be low
   9 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

2-[(5-Amino-1-tosyl-1H-pyrazol-3-yl)oxy]-1-(4-methoxyphenyl)ethan-1-one 1,4-dioxane monosolvate

Crystal data

C19H19N3O5S·C4H8O2	Z = 2
Mr = 489.53	F(000) = 516
Triclinic, P1	Dx = 1.447 Mg m^−3
a = 8.26968 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.50096 (14) Å	Cell parameters from 105453 reflections
c = 12.76743 (16) Å	θ = 2.6–45.0°
α = 116.9553 (12)°	µ = 0.20 mm^−1
β = 104.8418 (10)°	T = 100 K
γ = 91.0281 (10)°	Block, colourless
V = 1123.39 (3) Å^3	0.2 × 0.2 × 0.15 mm

Data collection

XtaLAB Synergy diffractometer	18415 independent reflections
Radiation source: micro-focus sealed X-ray tube	16161 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	Rint = 0.027
ω scans	θmax = 44.9°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2022)	h = −16→16
Tmin = 0.914, Tmax = 1.000	k = −24→24
187554 measured reflections	l = −25→25

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.087	w = 1/[σ^2(Fo^2) + (0.0517P)^2 + 0.0976P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.002
18415 reflections	Δρmax = 0.67 e Å^−3
330 parameters	Δρmin = −0.38 e Å^−3
22 restraints

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	Occ. (<1)
C1	0.38399 (4)	0.77886 (3)	0.26518 (3)	0.01184 (4)
C2	0.40834 (5)	0.66456 (3)	0.27750 (3)	0.01258 (5)
H2A	0.494861	0.684712	0.356158	0.015*
H2B	0.300694	0.628434	0.277334	0.015*
O1	0.41714 (4)	0.79016 (3)	0.18236 (3)	0.01691 (5)
O2	0.46134 (4)	0.58006 (3)	0.17697 (3)	0.01403 (4)
N1	0.40343 (4)	0.30638 (3)	0.17661 (3)	0.01166 (4)
N2	0.40577 (4)	0.43334 (3)	0.23487 (3)	0.01164 (4)
C3	0.45301 (4)	0.46582 (3)	0.16098 (3)	0.01109 (4)
C4	0.48807 (5)	0.36967 (3)	0.05888 (3)	0.01274 (5)
H4	0.523520	0.374279	−0.004293	0.015*
C5	0.45919 (4)	0.26833 (3)	0.07193 (3)	0.01129 (4)
N3	0.47670 (5)	0.15066 (3)	0.00274 (3)	0.01555 (5)
H031	0.4134 (12)	0.0953 (9)	0.0048 (9)	0.029 (2)*
H032	0.4995 (12)	0.1375 (9)	−0.0649 (8)	0.024 (2)*
C11	0.32316 (4)	0.87608 (3)	0.35963 (3)	0.01120 (4)
C12	0.32181 (4)	0.98963 (3)	0.36261 (3)	0.01213 (5)
H12	0.355545	1.001617	0.302459	0.015*
C13	0.27183 (5)	1.08435 (3)	0.45230 (3)	0.01318 (5)
H13	0.269231	1.160437	0.452620	0.016*
C14	0.22495 (4)	1.06787 (3)	0.54284 (3)	0.01214 (5)
C15	0.22215 (5)	0.95479 (3)	0.53954 (3)	0.01378 (5)
H15	0.187272	0.942595	0.599186	0.017*
C16	0.27095 (5)	0.86004 (3)	0.44803 (3)	0.01366 (5)
H16	0.268743	0.782921	0.445597	0.016*
O3	0.18634 (4)	1.16720 (3)	0.63073 (3)	0.01711 (5)
C17	0.14669 (6)	1.15468 (4)	0.72774 (4)	0.01942 (6)
H17A	0.047427	1.091958	0.692996	0.029*
H17B	0.122138	1.232228	0.785483	0.029*
H17C	0.243352	1.131273	0.771163	0.029*
S1	0.43246 (2)	0.24477 (2)	0.27095 (2)	0.01097 (2)
O4	0.41689 (4)	0.11676 (3)	0.19275 (3)	0.01594 (5)
O5	0.31959 (4)	0.29146 (3)	0.34374 (3)	0.01605 (5)
C21	0.64132 (4)	0.29968 (3)	0.36666 (3)	0.01082 (4)
C22	0.67431 (4)	0.39426 (3)	0.48634 (3)	0.01175 (4)
H22	0.584626	0.431238	0.515766	0.014*
C23	0.84106 (4)	0.43351 (3)	0.56194 (3)	0.01265 (5)
H23	0.864873	0.498109	0.643528	0.015*
C24	0.97428 (4)	0.37942 (3)	0.51979 (3)	0.01249 (5)
C25	0.93733 (5)	0.28592 (3)	0.39821 (4)	0.01400 (5)
H25	1.027019	0.249828	0.368074	0.017*
C26	0.77178 (4)	0.24513 (3)	0.32102 (3)	0.01313 (5)
H26	0.747761	0.181499	0.238932	0.016*
C27	1.15349 (5)	0.41935 (4)	0.60318 (4)	0.01590 (5)
H27A	1.177536	0.369938	0.645265	0.024*
H27B	1.168027	0.505056	0.664270	0.024*
H27C	1.231683	0.409081	0.554338	0.024*
O81	0.12771 (5)	−0.00966 (4)	−0.05908 (4)	0.02415 (7)
C81	0.07517 (8)	−0.10432 (6)	−0.03646 (7)	0.03059 (11)
H81A	0.171885	−0.146721	−0.022534	0.037*
H81B	−0.015447	−0.164162	−0.109485	0.037*
C82	−0.01034 (7)	0.05411 (7)	−0.07474 (6)	0.02876 (10)
H82A	−0.103225	−0.001640	−0.148717	0.035*
H82B	0.027099	0.121680	−0.087683	0.035*
O91	0.04584 (6)	0.61849 (4)	0.10107 (4)	0.02249 (9)	0.931 (2)
C91	−0.07460 (7)	0.52971 (6)	0.09340 (5)	0.02309 (11)	0.931 (2)
H91A	−0.190244	0.538072	0.054417	0.028*	0.931 (2)
H91B	−0.068248	0.543917	0.177303	0.028*	0.931 (2)
C92	0.04101 (7)	0.59715 (5)	−0.01928 (6)	0.02259 (10)	0.931 (2)
H92A	0.127446	0.657086	−0.013383	0.027*	0.931 (2)
H92B	−0.071504	0.607473	−0.061132	0.027*	0.931 (2)
O91'	0.0276 (9)	0.5939 (7)	0.1194 (7)	0.0265 (13)*	0.069 (2)
C91'	−0.0678 (12)	0.4761 (10)	0.0740 (9)	0.0297 (17)*	0.069 (2)
H91C	−0.050956	0.455740	0.142058	0.036*	0.069 (2)
H91D	−0.189840	0.478789	0.044301	0.036*	0.069 (2)
C92'	0.0187 (13)	0.6148 (10)	0.0222 (10)	0.0312 (18)*	0.069 (2)
H92C	0.091514	0.692745	0.052555	0.037*	0.069 (2)
H92D	−0.099241	0.623833	−0.011040	0.037*	0.069 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.01442 (11)	0.01135 (10)	0.01179 (10)	0.00285 (9)	0.00588 (9)	0.00610 (9)
C2	0.01679 (12)	0.01137 (11)	0.01192 (10)	0.00442 (9)	0.00707 (9)	0.00592 (9)
O1	0.02551 (13)	0.01563 (11)	0.01559 (10)	0.00521 (9)	0.01201 (10)	0.00921 (9)
O2	0.02105 (11)	0.01078 (9)	0.01466 (9)	0.00525 (8)	0.01076 (9)	0.00670 (8)
N1	0.01493 (10)	0.01194 (10)	0.01105 (9)	0.00369 (8)	0.00563 (8)	0.00690 (8)
N2	0.01435 (10)	0.01179 (10)	0.01129 (9)	0.00381 (8)	0.00585 (8)	0.00643 (8)
C3	0.01304 (10)	0.01109 (10)	0.01116 (10)	0.00323 (8)	0.00541 (8)	0.00594 (8)
C4	0.01717 (12)	0.01201 (11)	0.01200 (11)	0.00383 (9)	0.00776 (9)	0.00628 (9)
C5	0.01295 (11)	0.01167 (10)	0.01045 (10)	0.00282 (8)	0.00444 (8)	0.00569 (8)
N3	0.02191 (13)	0.01141 (10)	0.01416 (11)	0.00400 (9)	0.00808 (10)	0.00526 (9)
C11	0.01324 (11)	0.01081 (10)	0.01189 (10)	0.00300 (8)	0.00540 (9)	0.00641 (9)
C12	0.01438 (11)	0.01145 (11)	0.01278 (11)	0.00217 (9)	0.00468 (9)	0.00725 (9)
C13	0.01621 (12)	0.01050 (10)	0.01455 (11)	0.00268 (9)	0.00521 (10)	0.00700 (9)
C14	0.01351 (11)	0.01032 (10)	0.01294 (11)	0.00290 (8)	0.00475 (9)	0.00532 (9)
C15	0.01852 (13)	0.01216 (11)	0.01507 (12)	0.00501 (10)	0.00930 (10)	0.00776 (10)
C16	0.01935 (13)	0.01153 (11)	0.01547 (12)	0.00551 (10)	0.00982 (10)	0.00828 (10)
O3	0.02369 (13)	0.01157 (9)	0.01659 (11)	0.00557 (9)	0.00988 (10)	0.00497 (8)
C17	0.02350 (16)	0.01854 (15)	0.01523 (13)	0.00552 (13)	0.00945 (12)	0.00517 (12)
S1	0.01077 (3)	0.01276 (3)	0.01195 (3)	0.00076 (2)	0.00380 (2)	0.00779 (3)
O4	0.01896 (11)	0.01203 (9)	0.01620 (10)	−0.00143 (8)	0.00272 (9)	0.00760 (8)
O5	0.01293 (9)	0.02379 (13)	0.01726 (11)	0.00318 (9)	0.00781 (8)	0.01279 (10)
C21	0.01101 (10)	0.01183 (10)	0.01159 (10)	0.00221 (8)	0.00432 (8)	0.00666 (9)
C22	0.01253 (10)	0.01267 (11)	0.01202 (10)	0.00323 (8)	0.00491 (8)	0.00677 (9)
C23	0.01372 (11)	0.01260 (11)	0.01227 (11)	0.00202 (9)	0.00366 (9)	0.00652 (9)
C24	0.01179 (10)	0.01305 (11)	0.01505 (11)	0.00145 (9)	0.00357 (9)	0.00888 (10)
C25	0.01213 (11)	0.01514 (12)	0.01644 (12)	0.00372 (9)	0.00603 (9)	0.00792 (10)
C26	0.01300 (11)	0.01351 (11)	0.01350 (11)	0.00308 (9)	0.00568 (9)	0.00597 (9)
C27	0.01265 (11)	0.01752 (13)	0.01942 (14)	0.00062 (10)	0.00188 (10)	0.01186 (12)
O81	0.01741 (12)	0.03412 (18)	0.02501 (15)	−0.00010 (12)	0.00789 (11)	0.01670 (14)
C81	0.0258 (2)	0.0336 (3)	0.0431 (3)	0.00625 (19)	0.0175 (2)	0.0232 (2)
C82	0.02010 (17)	0.0471 (3)	0.0310 (2)	0.00227 (18)	0.00602 (16)	0.0293 (2)
O91	0.02279 (16)	0.01833 (15)	0.01779 (15)	0.00159 (12)	0.00519 (12)	0.00195 (12)
C91	0.02285 (19)	0.0278 (3)	0.01701 (17)	0.00463 (16)	0.00868 (14)	0.00778 (16)
C92	0.02260 (19)	0.0223 (2)	0.0241 (2)	0.00333 (15)	0.00477 (16)	0.01313 (17)

Geometric parameters (Å, º)

C1—O1	1.2229 (4)	C21—C22	1.3944 (5)
C1—C11	1.4793 (5)	C21—C26	1.3988 (5)
C1—C2	1.5182 (5)	C22—C23	1.3923 (5)
C2—O2	1.4251 (4)	C22—H22	0.9500
C2—H2A	0.9900	C23—C24	1.4004 (5)
C2—H2B	0.9900	C23—H23	0.9500
O2—C3	1.3457 (4)	C24—C25	1.4030 (5)
N1—C5	1.4044 (4)	C24—C27	1.5042 (5)
N1—N2	1.4121 (4)	C25—C26	1.3906 (5)
N1—S1	1.6737 (3)	C25—H25	0.9500
N2—C3	1.3183 (4)	C26—H26	0.9500
C3—C4	1.4190 (5)	C27—H27A	0.9800
C4—C5	1.3749 (5)	C27—H27B	0.9800
C4—H4	0.9500	C27—H27C	0.9800
C5—N3	1.3639 (5)	O81—C81	1.4241 (7)
N3—H031	0.874 (9)	O81—C82	1.4279 (7)
N3—H032	0.875 (9)	C81—C82^i	1.5137 (9)
C11—C16	1.3973 (5)	C81—H81A	0.9900
C11—C12	1.4030 (5)	C81—H81B	0.9900
C12—C13	1.3839 (5)	C82—H82A	0.9900
C12—H12	0.9500	C82—H82B	0.9900
C13—C14	1.4040 (5)	O91—C92	1.4249 (8)
C13—H13	0.9500	O91—C91	1.4301 (8)
C14—O3	1.3555 (4)	C91—C92^ii	1.5091 (8)
C14—C15	1.3947 (5)	C91—H91A	0.9900
C15—C16	1.3911 (5)	C91—H91B	0.9900
C15—H15	0.9500	C92—H92A	0.9900
C16—H16	0.9500	C92—H92B	0.9900
O3—C17	1.4310 (5)	O91'—C92'	1.364 (11)
C17—H17A	0.9800	O91'—C91'	1.441 (11)
C17—H17B	0.9800	C91'—C92'^ii	1.404 (15)
C17—H17C	0.9800	C91'—H91C	0.9900
S1—O5	1.4310 (3)	C91'—H91D	0.9900
S1—O4	1.4326 (3)	C92'—H92C	0.9900
S1—C21	1.7502 (3)	C92'—H92D	0.9900
O1—C1—C11	122.11 (3)	C23—C22—C21	118.80 (3)
O1—C1—C2	121.06 (3)	C23—C22—H22	120.6
C11—C1—C2	116.81 (3)	C21—C22—H22	120.6
O2—C2—C1	108.97 (3)	C22—C23—C24	121.14 (3)
O2—C2—H2A	109.9	C22—C23—H23	119.4
C1—C2—H2A	109.9	C24—C23—H23	119.4
O2—C2—H2B	109.9	C23—C24—C25	118.70 (3)
C1—C2—H2B	109.9	C23—C24—C27	120.92 (3)
H2A—C2—H2B	108.3	C25—C24—C27	120.38 (3)
C3—O2—C2	115.38 (3)	C26—C25—C24	121.18 (3)
C5—N1—N2	111.05 (3)	C26—C25—H25	119.4
C5—N1—S1	126.29 (2)	C24—C25—H25	119.4
N2—N1—S1	114.68 (2)	C25—C26—C21	118.67 (3)
C3—N2—N1	102.75 (3)	C25—C26—H26	120.7
N2—C3—O2	123.26 (3)	C21—C26—H26	120.7
N2—C3—C4	114.91 (3)	C24—C27—H27A	109.5
O2—C3—C4	121.78 (3)	C24—C27—H27B	109.5
C5—C4—C3	104.48 (3)	H27A—C27—H27B	109.5
C5—C4—H4	127.8	C24—C27—H27C	109.5
C3—C4—H4	127.8	H27A—C27—H27C	109.5
N3—C5—C4	130.68 (3)	H27B—C27—H27C	109.5
N3—C5—N1	122.63 (3)	C81—O81—C82	109.31 (4)
C4—C5—N1	106.70 (3)	O81—C81—C82^i	110.95 (5)
C5—N3—H031	116.3 (6)	O81—C81—H81A	109.4
C5—N3—H032	113.2 (6)	C82^i—C81—H81A	109.4
H031—N3—H032	121.0 (9)	O81—C81—H81B	109.4
C16—C11—C12	118.70 (3)	C82^i—C81—H81B	109.4
C16—C11—C1	122.44 (3)	H81A—C81—H81B	108.0
C12—C11—C1	118.84 (3)	O81—C82—C81^i	111.17 (4)
C13—C12—C11	120.65 (3)	O81—C82—H82A	109.4
C13—C12—H12	119.7	C81^i—C82—H82A	109.4
C11—C12—H12	119.7	O81—C82—H82B	109.4
C12—C13—C14	119.93 (3)	C81^i—C82—H82B	109.4
C12—C13—H13	120.0	H82A—C82—H82B	108.0
C14—C13—H13	120.0	C92—O91—C91	110.01 (4)
O3—C14—C15	123.98 (3)	O91—C91—C92^ii	110.96 (4)
O3—C14—C13	115.95 (3)	O91—C91—H91A	109.4
C15—C14—C13	120.06 (3)	C92^ii—C91—H91A	109.4
C16—C15—C14	119.33 (3)	O91—C91—H91B	109.4
C16—C15—H15	120.3	C92^ii—C91—H91B	109.4
C14—C15—H15	120.3	H91A—C91—H91B	108.0
C15—C16—C11	121.28 (3)	O91—C92—C91^ii	110.33 (4)
C15—C16—H16	119.4	O91—C92—H92A	109.6
C11—C16—H16	119.4	C91^ii—C92—H92A	109.6
C14—O3—C17	117.13 (3)	O91—C92—H92B	109.6
O3—C17—H17A	109.5	C91^ii—C92—H92B	109.6
O3—C17—H17B	109.5	H92A—C92—H92B	108.1
H17A—C17—H17B	109.5	C92'—O91'—C91'	108.6 (7)
O3—C17—H17C	109.5	C92'^ii—C91'—O91'	111.9 (8)
H17A—C17—H17C	109.5	C92'^ii—C91'—H91C	109.2
H17B—C17—H17C	109.5	O91'—C91'—H91C	109.2
O5—S1—O4	120.39 (2)	C92'^ii—C91'—H91D	109.2
O5—S1—N1	106.165 (17)	O91'—C91'—H91D	109.2
O4—S1—N1	105.240 (17)	H91C—C91'—H91D	107.9
O5—S1—C21	108.966 (18)	O91'—C92'—H92C	108.5
O4—S1—C21	108.862 (18)	C91'^ii—C92'—H92C	108.5
N1—S1—C21	106.306 (16)	O91'—C92'—H92D	108.5
C22—C21—C26	121.49 (3)	C91'^ii—C92'—H92D	108.5
C22—C21—S1	119.94 (3)	H92C—C92'—H92D	107.5
C26—C21—S1	118.56 (3)
O1—C1—C2—O2	−3.58 (5)	C15—C14—O3—C17	2.39 (6)
C11—C1—C2—O2	178.02 (3)	C13—C14—O3—C17	−176.83 (4)
C1—C2—O2—C3	−166.35 (3)	C5—N1—S1—O5	−165.61 (3)
C5—N1—N2—C3	3.25 (4)	N2—N1—S1—O5	48.49 (3)
S1—N1—N2—C3	154.29 (2)	C5—N1—S1—O4	−36.94 (4)
N1—N2—C3—O2	175.41 (3)	N2—N1—S1—O4	177.16 (3)
N1—N2—C3—C4	−1.98 (4)	C5—N1—S1—C21	78.45 (3)
C2—O2—C3—N2	−2.54 (5)	N2—N1—S1—C21	−67.45 (3)
C2—O2—C3—C4	174.67 (3)	O5—S1—C21—C22	−12.84 (3)
N2—C3—C4—C5	0.01 (4)	O4—S1—C21—C22	−145.89 (3)
O2—C3—C4—C5	−177.41 (3)	N1—S1—C21—C22	101.19 (3)
C3—C4—C5—N3	−178.08 (4)	O5—S1—C21—C26	165.95 (3)
C3—C4—C5—N1	2.01 (4)	O4—S1—C21—C26	32.90 (3)
N2—N1—C5—N3	176.69 (3)	N1—S1—C21—C26	−80.02 (3)
S1—N1—C5—N3	29.78 (5)	C26—C21—C22—C23	−0.89 (5)
N2—N1—C5—C4	−3.38 (4)	S1—C21—C22—C23	177.87 (3)
S1—N1—C5—C4	−150.30 (3)	C21—C22—C23—C24	−0.25 (5)
O1—C1—C11—C16	174.25 (4)	C22—C23—C24—C25	1.37 (5)
C2—C1—C11—C16	−7.36 (5)	C22—C23—C24—C27	−177.93 (3)
O1—C1—C11—C12	−7.40 (6)	C23—C24—C25—C26	−1.40 (5)
C2—C1—C11—C12	170.98 (3)	C27—C24—C25—C26	177.90 (3)
C16—C11—C12—C13	0.82 (5)	C24—C25—C26—C21	0.32 (5)
C1—C11—C12—C13	−177.59 (3)	C22—C21—C26—C25	0.85 (5)
C11—C12—C13—C14	1.22 (5)	S1—C21—C26—C25	−177.92 (3)
C12—C13—C14—O3	176.66 (3)	C82—O81—C81—C82^i	−57.05 (7)
C12—C13—C14—C15	−2.59 (6)	C81—O81—C82—C81^i	57.18 (7)
O3—C14—C15—C16	−177.31 (4)	C92—O91—C91—C92^ii	57.63 (6)
C13—C14—C15—C16	1.88 (6)	C91—O91—C92—C91^ii	−57.25 (6)
C14—C15—C16—C11	0.19 (6)	C92'—O91'—C91'—C92'^ii	52.2 (12)
C12—C11—C16—C15	−1.54 (6)	C91'—O91'—C92'—C91'^ii	−53.9 (12)
C1—C11—C16—C15	176.81 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1^iii	0.95	2.45	3.1317 (4)	129
C4—H4···O2^iii	0.95	2.55	3.4625 (4)	162
N3—H031···O4	0.87 (1)	2.28 (1)	2.8015 (5)	118 (1)
N3—H031···O81	0.87 (1)	2.43 (1)	3.1875 (5)	145 (1)
N3—H032···O1^iii	0.88 (1)	2.30 (1)	3.0867 (4)	150 (1)
C17—H17B···O91^iv	0.98	2.49	3.4174 (6)	159
C12—H12···O4^v	0.95	2.54	3.4351 (4)	157
C25—H25···O5^vi	0.95	2.59	3.4122 (4)	145
C27—H27A···O3^vii	0.98	2.46	3.3348 (5)	149

Symmetry codes: (iii) −x+1, −y+1, −z; (iv) −x, −y+2, −z+1; (v) x, y+1, z; (vi) x+1, y, z; (vii) x+1, y−1, z.