Structures of six industrial benzimidazolone pigments from laboratory powder diffraction data

van de Streek, J.; Brüning, J.; Ivashevskaya, S.N.; Ermrich, M.; Paulus, E.F.; Bolte, M.; Schmidt, M.U.

doi:10.1107/S0108768108041529

Structures of six industrial benzimidazolone pigments from laboratory powder diffraction data

J. van de Streek, J. Brüning, S. N. Ivashevskaya, M. Ermrich, E. F. Paulus, M. Bolte and M. U. Schmidt

The crystal structures of six industrially produced benzimidazolone pigments [Pigment Orange 36 (β phase), Pigment Orange 62, Pigment Yellow 151, Pigment Yellow 154 (α phase), Pigment Yellow 181 (β phase) and Pigment Yellow 194] were determined from laboratory X-ray powder diffraction data by means of real-space methods using the programs DASH and MRIA, respectively. Subsequent Rietveld refinements were carried out with TOPAS. The crystal phases correspond to those produced industrially. Additionally, the crystal structures of the non-commercial compound `BIRZIL' (a chloro derivative of Pigment Yellow 194) and of a dimethylsulfoxide solvate of Pigment Yellow 154 were determined by single-crystal structure analyses. All eight crystal structures are different; the six industrial pigments even exhibit five different hydrogen-bond topologies. Apparently, the good application properties of the benzimidazolone pigments are not the result of one specific hydrogen-bonding pattern, but are the result of a combination of efficient molecular packing and strong intermolecular hydrogen bonds.

Keywords: benzimidazolone pigments; crystal structure determination X-ray powder diffraction; hydrogen-bond topologies.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768108041529/og5035sup1.cif Contains datablocks BIRZIL, PY154-DMSO, global, PO36, PO62, PY151, PY154, PY181, PY194
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768108041529/og5035BIRZILsup2.hkl Contains datablock BIRZIL
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768108041529/og5035PY154-DMSOsup3.fcf Contains datablock PY154-DMSO
	Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768108041529/og5035PO36sup4.rtv Contains datablock PO36
	Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768108041529/og5035PO62sup5.rtv Contains datablock PO62
	Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768108041529/og5035PY151sup6.rtv Contains datablock PY151
	Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768108041529/og5035PY154sup7.rtv Contains datablock PY154
	Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768108041529/og5035PY181sup8.rtv Contains datablock PY181
	Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768108041529/og5035PY194sup9.rtv Contains datablock PY194
	Portable Document Format (PDF) file https://doi.org/10.1107/S0108768108041529/og5035sup10.pdf Extra tables and figures

CCDC references: 737339; 737340; 737341; 737342; 737343; 737344; 737346

Computing details top

Data collection: STOE WINXPOW (STOE & CIE GmbH, 2004) for PO36, PO62, PY151, PY154, PY181, PY194; Nicolet software for BIRZIL; X-AREA (Stoe & Cie, 2001) for PY154-DMSO. Cell refinement: TOPAS (Coelho, 2006) for PO36, PO62, PY151, PY154, PY181, PY194; Nicolet software for BIRZIL; X-AREA (Stoe & Cie, 2001) for PY154-DMSO. Data reduction: DASH (David et al., 2006) for PO36, PO62, PY151, PY154, PY181, PY194; Nicolet software for BIRZIL; X-AREA (Stoe & Cie, 2001) for PY154-DMSO. Program(s) used to solve structure: DASH (David et al., 2006) for PO36, PO62, PY151, PY154, PY181, PY194; SHELXS97 (Sheldrick, 1990) for BIRZIL, PY154-DMSO. Program(s) used to refine structure: TOPAS (Coelho, 2006) for PO36, PO62, PY151, PY154, PY181, PY194; SHELXL97 (Sheldrick, 1997) for BIRZIL, PY154-DMSO. Molecular graphics: Mercury (Macrae et al., 2006) for PO36, PO62, PY151, PY154, PY181, PY194; SHELX97 (Sheldrick, 1997) for BIRZIL; XP in SHELXTL-Plus (Sheldrick, 1991) for PY154-DMSO. Software used to prepare material for publication: DASH, TOPAS, Mercury for PO36, PO62, PY151, PY154, PY181, PY194; SHELX97 (Sheldrick, 1997) for BIRZIL; SHELXL97 for PY154-DMSO.

Figures top

(PO36) top

Crystal data top

C₁₇H₁₃ClN₆O₅	Z = 2
M_r = 416.78	F(000) = 428
Triclinic, P1	D_x = 1.616 Mg m⁻³
Hall symbol: -P 1	Cu Kα₁ radiation, λ = 1.54056 Å
a = 8.6533 (7) Å	µ = 2.41 mm⁻¹
b = 9.1170 (6) Å	T = 293 K
c = 11.3831 (6) Å	Particle morphology: no specific habit
α = 74.717 (2)°	orange
β = 81.597 (4)°	cylinder, 10 × 0.7 mm
γ = 88.982 (3)°	Specimen preparation: Prepared at 293 K and 0.00 kPa
V = 856.78 (10) Å³

Data collection top

STOE-Stadi-P diffractometer	Data collection mode: transmission
Radiation source: sealed X-ray tube, laboratory diffractometer	Scan method: step
Primary focussing, Ge 111 monochromator	2θ_min = 2.00°, 2θ_max = 75.00°, 2θ_step = 0.01°
Specimen mounting: 'glass capillary'

Refinement top

Refinement on I_net	191 parameters
Least-squares matrix: full with fixed elements per cycle	116 restraints
R_p = 0.029	0 constraints
R_wp = 0.039	H-atom parameters constrained
R_exp = 0.094	Weighting scheme based on measured s.u.'s w = 1/σ[Y_obs]²
χ² = 1.103	(Δ/σ)_max = 0.001
9800 data points	Background function: Chebyshev polynomial with 20 terms
Excluded region(s): none	Preferred orientation correction: none
Profile function: modified Thompson-Cox-Hastings pseudo-Voigt (Young, 1993)

Crystal data top

C₁₇H₁₃ClN₆O₅	γ = 88.982 (3)°
M_r = 416.78	V = 856.78 (10) Å³
Triclinic, P1	Z = 2
a = 8.6533 (7) Å	Cu Kα₁ radiation, λ = 1.54056 Å
b = 9.1170 (6) Å	µ = 2.41 mm⁻¹
c = 11.3831 (6) Å	T = 293 K
α = 74.717 (2)°	cylinder, 10 × 0.7 mm
β = 81.597 (4)°

Data collection top

STOE-Stadi-P diffractometer	Scan method: step
Specimen mounting: 'glass capillary'	2θ_min = 2.00°, 2θ_max = 75.00°, 2θ_step = 0.01°
Data collection mode: transmission

Refinement top

R_p = 0.029	9800 data points
R_wp = 0.039	191 parameters
R_exp = 0.094	116 restraints
χ² = 1.103	H-atom parameters constrained

Special details top

Experimental. specimen was rotated in its plane

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2785 (6)	0.2449 (8)	0.5094 (8)	0.03645
C2	0.1249 (6)	0.1646 (8)	0.5732 (9)	0.03645
N3	0.2846 (7)	0.3689 (9)	0.4220 (8)	0.03645
C4	0.4333 (6)	0.1940 (8)	0.5449 (8)	0.03645
N5	0.1331 (6)	0.0240 (6)	0.6486 (6)	0.03645
O6	0.0048 (8)	0.2186 (9)	0.5406 (10)	0.03645
N7	0.1623 (6)	0.4383 (6)	0.3810 (5)	0.03645
O8	0.4456 (9)	0.0761 (9)	0.6222 (9)	0.03645
C9	0.5765 (6)	0.2895 (6)	0.4751 (5)	0.03645
C10	0.0091 (6)	−0.0756 (6)	0.7174 (5)	0.03645
H11	0.23794	−0.00767	0.66094	0.04374
H12	0.05829	0.39772	0.41495	0.04374
C13	0.1850 (6)	0.5706 (5)	0.2850 (4)	0.03645
H14	0.58624	0.29730	0.37705	0.04374
H15	0.56901	0.40310	0.48897	0.04374
H16	0.68120	0.23666	0.50864	0.04374
C17	−0.1470 (6)	−0.0522 (5)	0.6988 (5)	0.03645
C18	0.0528 (6)	−0.2013 (6)	0.8064 (5)	0.03645
C19	0.3352 (6)	0.6324 (5)	0.2434 (3)	0.03645
C20	0.0607 (6)	0.6434 (4)	0.2284 (4)	0.03645
C21	−0.2512 (6)	−0.1602 (4)	0.7745 (3)	0.03645
H22	−0.18369	0.03669	0.63492	0.04374
C23	−0.0542 (6)	−0.3085 (5)	0.8821 (5)	0.03645
H24	0.16770	−0.21405	0.81614	0.04374
C25	0.3592 (6)	0.7641 (5)	0.1468 (3)	0.03645
H26	0.42930	0.58324	0.28167	0.04374
C27	0.0869 (6)	0.7766 (4)	0.1312 (3)	0.03645
N28	−0.0982 (6)	0.5794 (6)	0.2718 (5)	0.03645
C29	−0.2077 (6)	−0.2909 (4)	0.8683 (3)	0.03645
N30	−0.4138 (6)	−0.1742 (5)	0.7834 (5)	0.03645
H31	−0.01912	−0.39754	0.94629	0.04374
C32	0.2356 (6)	0.8373 (4)	0.0902 (4)	0.03645
H33	0.46990	0.80748	0.11725	0.04374
H34	−0.00359	0.82930	0.09018	0.04374
O35	−0.2056 (8)	0.6568 (9)	0.2139 (8)	0.03645
O36	−0.1318 (9)	0.4806 (9)	0.3634 (7)	0.03645
N37	−0.3432 (6)	−0.3715 (6)	0.9251 (4)	0.03645
H38	−0.47536	−0.10182	0.73197	0.04374
C39	−0.4722 (6)	−0.3021 (7)	0.8737 (5)	0.03645
Cl40	0.2696 (5)	1.0008 (5)	−0.0306 (4)	0.04567
H41	−0.35016	−0.46478	0.99030	0.04374
O42	−0.6075 (8)	−0.3435 (9)	0.9003 (7)	0.03645

Geometric parameters (Å, º) top

C1—C2	1.518 (7)	C18—C23	1.382 (6)
C1—N3	1.29 (1)	C19—C25	1.395 (5)
C1—C4	1.486 (8)	C20—C27	1.408 (4)
C2—N5	1.347 (8)	C20—N28	1.467 (7)
C2—O6	1.207 (9)	C21—C29	1.461 (5)
N3—N7	1.303 (8)	C21—N30	1.402 (7)
C4—C9	1.520 (7)	C23—C29	1.361 (7)
N5—C10	1.416 (6)	C25—C32	1.400 (7)
N5—H11	0.99 (2)	C27—C32	1.375 (7)
N7—C13	1.392 (6)	N28—O35	1.305 (9)
C9—H14	1.08 (2)	N28—O36	1.186 (8)
C9—H15	1.07 (2)	C29—N37	1.374 (6)
C9—H16	1.08 (2)	N30—H38	0.98 (2)
C10—C17	1.401 (7)	N30—C39	1.383 (6)
C10—C18	1.402 (7)	C32—Cl40	1.736 (5)
C13—C19	1.391 (7)	N37—C39	1.399 (7)
C13—C20	1.403 (7)	N37—H41	0.98 (2)
C17—C21	1.372 (6)	C39—O42	1.209 (8)

C2—C1—N3	122.0 (5)	C25—C19—H26	121 (1)
C2—C1—C4	123.9 (6)	C13—C20—C27	120.8 (4)
N3—C1—C4	114.0 (5)	C13—C20—N28	119.2 (3)
C1—C2—N5	116.8 (5)	C27—C20—N28	120.0 (4)
C1—C2—O6	118.9 (7)	C17—C21—C29	124.2 (5)
N5—C2—O6	123.3 (6)	C17—C21—N30	131.0 (4)
C1—N3—N7	124.3 (5)	C29—C21—N30	104.8 (3)
C1—C4—O8	120.8 (6)	C18—C23—C29	118.3 (4)
C1—C4—C9	117.7 (5)	C18—C23—H31	120 (1)
O8—C4—C9	121.2 (6)	C29—C23—H31	122 (1)
C2—N5—C10	128.3 (5)	C19—C25—C32	121.7 (4)
C2—N5—H11	116 (1)	C19—C25—H33	118 (1)
C10—N5—H11	116 (1)	C32—C25—H33	120 (1)
N3—N7—H12	120 (1)	C20—C27—C32	120.3 (4)
N3—N7—C13	118.5 (5)	C20—C27—H34	119 (1)
H12—N7—C13	120 (1)	C32—C27—H34	120 (1)
C4—C9—H14	112 (1)	C20—N28—O35	114.3 (5)
C4—C9—H16	108 (1)	C20—N28—O36	123.3 (6)
H14—C9—H16	111 (1)	O35—N28—O36	121.3 (6)
H15—C9—H16	109 (2)	C21—C29—C23	118.4 (4)
N5—C10—C17	123.1 (4)	C21—C29—N37	106.9 (4)
N5—C10—C18	115.3 (5)	C23—C29—N37	134.6 (4)
C17—C10—C18	121.6 (4)	C21—N30—C39	111.4 (4)
N7—C13—C19	119.3 (4)	C25—C32—C27	118.7 (3)
N7—C13—C20	121.8 (4)	C25—C32—Cl40	120.6 (4)
C19—C13—C20	118.8 (3)	C27—C32—Cl40	120.6 (4)
C10—C17—C21	114.8 (4)	C29—N37—C39	110.9 (4)
C10—C17—H22	123 (1)	C29—N37—H41	127 (1)
C21—C17—H22	122 (1)	C39—N37—H41	122 (1)
C10—C18—C23	122.6 (5)	N30—C39—N37	105.9 (4)
C10—C18—H24	118 (1)	N30—C39—O42	126.0 (6)
C23—C18—H24	119 (1)	N37—C39—O42	128.1 (5)
C13—C19—C25	119.7 (4)

(PO62) top

Crystal data top

C₁₇H₁₄N₆O₅	Z = 2
M_r = 382.34	F(000) = 396
Triclinic, P1	D_x = 1.505 Mg m⁻³
Hall symbol: -P 1	Cu Kα₁ radiation, λ = 1.54056 Å
a = 7.2689 (8) Å	µ = 0.97 mm⁻¹
b = 10.3176 (14) Å	T = 293 K
c = 12.1761 (15) Å	Particle morphology: no specific habit
α = 96.462 (6)°	orange
β = 95.869 (4)°	flat_sheet, 10 × 1.2 mm
γ = 109.849 (8)°	Specimen preparation: Prepared at 293 K and 0.00 kPa
V = 843.78 (19) Å³

Data collection top

STOE-Stadi-P diffractometer	Data collection mode: transmission
Radiation source: sealed X-ray tube, laboratory diffractometer	Scan method: step
Primary focussing, Ge 111 monochromator	2θ_min = 3.00°, 2θ_max = 34.00°, 2θ_step = 0.02°
Specimen mounting: flat sample holder

Refinement top

Refinement on I_net	190 parameters
Least-squares matrix: full with fixed elements per cycle	118 restraints
R_p = 0.030	0 constraints
R_wp = 0.040	H-atom parameters constrained
R_exp = 0.055	Weighting scheme based on measured s.u.'s w = 1/σ[Y_obs]²
χ² = 1.277	(Δ/σ)_max = 0.001
1550 data points	Background function: Chebyshev polynomial with 15 terms
Excluded region(s): none	Preferred orientation correction: none
Profile function: modified Thompson-Cox-Hastings pseudo-Voigt (Young, 1993)

Crystal data top

C₁₇H₁₄N₆O₅	γ = 109.849 (8)°
M_r = 382.34	V = 843.78 (19) Å³
Triclinic, P1	Z = 2
a = 7.2689 (8) Å	Cu Kα₁ radiation, λ = 1.54056 Å
b = 10.3176 (14) Å	µ = 0.97 mm⁻¹
c = 12.1761 (15) Å	T = 293 K
α = 96.462 (6)°	flat_sheet, 10 × 1.2 mm
β = 95.869 (4)°

Data collection top

STOE-Stadi-P diffractometer	Scan method: step
Specimen mounting: flat sample holder	2θ_min = 3.00°, 2θ_max = 34.00°, 2θ_step = 0.02°
Data collection mode: transmission

Refinement top

R_p = 0.030	1550 data points
R_wp = 0.040	190 parameters
R_exp = 0.055	118 restraints
χ² = 1.277	H-atom parameters constrained

Special details top

Experimental. specimen was rotated in its plane

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	−0.418 (2)	−0.0163 (8)	−0.1595 (7)	0.03800
N2	−0.511 (3)	−0.1432 (9)	−0.2055 (8)	0.03800
C3	−0.286 (2)	0.0251 (8)	−0.0471 (7)	0.03800
C4	−0.4288 (18)	0.0815 (8)	−0.2383 (7)	0.03800
N5	−0.5307 (11)	−0.2457 (7)	−0.1517 (6)	0.03800
N6	−0.1525 (13)	0.1566 (8)	−0.0248 (6)	0.03800
O7	−0.288 (3)	−0.0629 (12)	0.0132 (12)	0.03800
O8	−0.344 (3)	0.2077 (11)	−0.2090 (11)	0.03800
C9	−0.5908 (11)	0.0225 (8)	−0.3397 (6)	0.03800
C10	−0.6518 (9)	−0.3800 (6)	−0.2040 (6)	0.03800
H11	−0.493 (7)	−0.223 (3)	−0.068 (2)	0.04559
C12	−0.0268 (12)	0.2242 (7)	0.0768 (6)	0.03800
H13	−0.134 (4)	0.208 (3)	−0.0896 (19)	0.04559
H14	−0.626 (5)	−0.090 (3)	−0.3618 (19)	0.04559
H15	−0.725 (4)	0.035 (3)	−0.321 (2)	0.04559
H16	−0.543 (4)	0.076 (3)	−0.409 (2)	0.04559
C17	−0.7483 (7)	−0.4024 (7)	−0.3130 (5)	0.03800
C18	−0.6725 (8)	−0.4920 (6)	−0.1424 (5)	0.03800
C19	−0.0054 (9)	0.1503 (7)	0.1625 (6)	0.03800
C20	0.0748 (11)	0.3683 (7)	0.0890 (6)	0.03800
C21	−0.8702 (7)	−0.5385 (7)	−0.3637 (6)	0.03800
H22	−0.726 (4)	−0.314 (3)	−0.356 (2)	0.04559
C23	−0.7923 (7)	−0.6253 (6)	−0.1933 (5)	0.03800
H24	−0.597 (4)	−0.475 (3)	−0.057 (2)	0.04559
C25	0.1228 (7)	0.2275 (6)	0.2606 (5)	0.03800
H26	−0.086 (4)	0.041 (2)	0.1513 (19)	0.04559
C27	0.2026 (9)	0.4477 (7)	0.1860 (6)	0.03800
H28	0.055 (4)	0.421 (2)	0.022 (3)	0.04559
C29	−0.8926 (7)	−0.6493 (7)	−0.3053 (5)	0.03800
H30	−0.946 (4)	−0.557 (2)	−0.447 (2)	0.04559
H31	−0.807 (4)	−0.710 (3)	−0.1474 (19)	0.04559
C32	0.2258 (8)	0.3763 (4)	0.2709 (4)	0.03800
N33	0.1857 (10)	0.1946 (7)	0.3637 (6)	0.03800
H34	0.285 (5)	0.561 (3)	0.1951 (19)	0.04559
N35	−1.0167 (11)	−0.7926 (7)	−0.3543 (7)	0.03800
N36	0.3376 (10)	0.4238 (7)	0.3739 (6)	0.03800
H37	0.144 (5)	0.100 (3)	0.3876 (19)	0.04559
C38	0.3205 (11)	0.3136 (8)	0.4365 (6)	0.03800
O39	−1.118 (2)	−0.8169 (15)	−0.4472 (10)	0.03800
O40	−0.966 (3)	−0.8797 (10)	−0.3125 (11)	0.03800
H41	0.420 (4)	0.523 (2)	0.4014 (17)	0.04559
O42	0.4031 (15)	0.3162 (12)	0.5334 (8)	0.03800

Geometric parameters (Å, º) top

C1—N2	1.28 (1)	C18—H24	1.09 (3)
C1—C3	1.52 (1)	C19—C25	1.408 (8)
C1—C4	1.48 (1)	C19—H26	1.07 (2)
N2—N5	1.28 (1)	C20—C27	1.404 (9)
C3—N6	1.35 (1)	C20—H28	1.05 (3)
C3—O7	1.23 (2)	C21—C29	1.38 (1)
C4—O8	1.23 (1)	C21—H30	1.07 (2)
C4—C9	1.53 (1)	C23—C29	1.431 (8)
N5—C10	1.399 (8)	C23—H31	1.07 (3)
N5—H11	1.00 (3)	C25—C32	1.446 (7)
N6—C12	1.412 (9)	C25—N33	1.41 (1)
N6—H13	1.00 (3)	C27—C32	1.363 (9)
C9—H14	1.09 (3)	C27—H34	1.10 (2)
C9—H15	1.07 (3)	C29—N35	1.464 (8)
C9—H16	1.08 (3)	C32—N36	1.363 (8)
C10—C17	1.392 (9)	N33—H37	1.01 (3)
C10—C18	1.422 (9)	N33—C38	1.420 (8)
C12—C19	1.38 (1)	N35—O39	1.23 (1)
C12—C20	1.400 (9)	N35—O40	1.22 (2)
C17—C21	1.409 (8)	N36—C38	1.42 (1)
C17—H22	1.07 (3)	N36—H41	0.99 (2)
C18—C23	1.385 (7)	C38—O42	1.26 (1)

N2—C1—C3	123 (1)	C25—C19—H26	124 (1)
N2—C1—C4	111.0 (9)	C12—C20—C27	123.7 (7)
C3—C1—C4	124.6 (6)	C12—C20—H28	118 (1)
C1—N2—N5	122.2 (9)	C27—C20—H28	118 (1)
C1—C3—N6	116.6 (8)	C17—C21—C29	120.0 (6)
C1—C3—O7	120.1 (9)	C17—C21—H30	120 (1)
N6—C3—O7	123 (1)	C29—C21—H30	120 (1)
C1—C4—O8	120 (1)	C18—C23—C29	120.7 (6)
C1—C4—C9	116.1 (7)	C18—C23—H31	118 (1)
O8—C4—C9	122 (1)	C29—C23—H31	121 (1)
N2—N5—C10	118.9 (7)	C19—C25—C32	121.4 (6)
N2—N5—H11	117 (2)	C19—C25—N33	134.7 (6)
C10—N5—H11	121 (2)	C32—C25—N33	103.9 (4)
C3—N6—C12	127.5 (8)	C20—C27—C32	116.1 (5)
C3—N6—H13	115 (1)	C20—C27—H34	124 (1)
C12—N6—H13	117 (1)	C32—C27—H34	120 (1)
C4—C9—H14	110 (2)	C21—C29—C23	120.0 (5)
C4—C9—H15	110 (1)	C21—C29—N35	122.1 (6)
C4—C9—H16	110 (1)	C23—C29—N35	117.9 (6)
H14—C9—H15	106 (2)	C25—C32—C27	121.4 (5)
H14—C9—H16	111 (2)	C25—C32—N36	108.9 (5)
H15—C9—H16	109 (2)	C27—C32—N36	129.7 (5)
N5—C10—C18	117.9 (6)	C25—N33—H37	127 (1)
C17—C10—C18	121.4 (5)	C25—N33—C38	112.3 (6)
N6—C12—C19	121.0 (6)	H37—N33—C38	121 (1)
N6—C12—C20	118.2 (7)	C29—N35—O39	120.2 (9)
C19—C12—C20	120.8 (6)	C29—N35—O40	113.0 (8)
C10—C17—C21	119.7 (6)	O39—N35—O40	123 (1)
C10—C17—H22	118 (1)	C32—N36—C38	111.4 (5)
C21—C17—H22	122 (1)	C32—N36—H41	124 (1)
C10—C18—C23	118.3 (5)	C38—N36—H41	124 (1)
C10—C18—H24	121 (1)	N33—C38—N36	103.5 (6)
C23—C18—H24	120 (1)	N33—C38—O42	126.6 (8)
C12—C19—C25	116.6 (6)	N36—C38—O42	129.8 (7)
C12—C19—H26	119 (1)

(PY151) top

Crystal data top

C₁₈H₁₅N₅O₅	Z = 2
M_r = 381.35	F(000) = 396
Triclinic, P1	D_x = 1.553 Mg m⁻³
Hall symbol: -P 1	Cu Kα₁ radiation, λ = 1.54056 Å
a = 5.12970 (14) Å	µ = 0.98 mm⁻¹
b = 9.2292 (3) Å	T = 293 K
c = 17.4094 (6) Å	Particle morphology: no specific habit
α = 95.857 (2)°	orange
β = 95.5056 (17)°	cylinder, 10 × 0.7 mm
γ = 91.7980 (13)°	Specimen preparation: Prepared at 293 K and 0.00 kPa
V = 815.42 (4) Å³

Data collection top

STOE-Stadi-P diffractometer	Data collection mode: transmission
Radiation source: sealed X-ray tube, laboratory diffractometer	Scan method: step
Primary focussing, Ge 111 monochromator	2θ_min = 4.00°, 2θ_max = 74.00°, 2θ_step = 0.01°
Specimen mounting: 'glass capillary'

Refinement top

Refinement on I_net	194 parameters
Least-squares matrix: full with fixed elements per cycle	118 restraints
R_p = 0.015	0 constraints
R_wp = 0.021	H-atom parameters constrained
R_exp = 0.054	Weighting scheme based on measured s.u.'s w = 1/σ[Y_obs]²
χ² = 1.369	(Δ/σ)_max = 0.001
7000 data points	Background function: Chebyshev polynomial with 20 terms
Excluded region(s): none	Preferred orientation correction: none
Profile function: modified Thompson-Cox-Hastings pseudo-Voigt (Young, 1993)

Crystal data top

C₁₈H₁₅N₅O₅	γ = 91.7980 (13)°
M_r = 381.35	V = 815.42 (4) Å³
Triclinic, P1	Z = 2
a = 5.12970 (14) Å	Cu Kα₁ radiation, λ = 1.54056 Å
b = 9.2292 (3) Å	µ = 0.98 mm⁻¹
c = 17.4094 (6) Å	T = 293 K
α = 95.857 (2)°	cylinder, 10 × 0.7 mm
β = 95.5056 (17)°

Data collection top

STOE-Stadi-P diffractometer	Scan method: step
Specimen mounting: 'glass capillary'	2θ_min = 4.00°, 2θ_max = 74.00°, 2θ_step = 0.01°
Data collection mode: transmission

Refinement top

R_p = 0.015	7000 data points
R_wp = 0.021	194 parameters
R_exp = 0.054	118 restraints
χ² = 1.369	H-atom parameters constrained

Special details top

Experimental. specimen was rotated in its plane

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.7418 (7)	0.1407 (4)	0.76861 (17)	0.03680
C2	0.5843 (7)	0.1220 (4)	0.83607 (18)	0.03680
N3	0.7080 (8)	0.0571 (4)	0.70371 (19)	0.03680
C4	0.9503 (7)	0.2575 (4)	0.76977 (17)	0.03680
N5	0.6345 (5)	0.2211 (3)	0.89847 (16)	0.03680
O6	0.3994 (8)	0.0326 (5)	0.8246 (3)	0.03680
N7	0.5357 (6)	−0.0512 (3)	0.68773 (15)	0.03680
O8	1.0236 (7)	0.3383 (5)	0.8277 (2)	0.03680
C9	1.0975 (5)	0.2516 (3)	0.69777 (16)	0.03680
C10	0.5215 (5)	0.2398 (3)	0.96951 (16)	0.03680
H11	0.77878	0.28811	0.89357	0.04416
H12	0.41875	−0.07397	0.72544	0.04416
C13	0.5197 (4)	−0.1361 (3)	0.61585 (15)	0.03680
H14	1.17303	0.14384	0.68518	0.04416
H15	0.96616	0.27735	0.64846	0.04416
H16	1.26091	0.33131	0.70694	0.04416
C17	0.6210 (5)	0.3427 (3)	1.02889 (15)	0.03680
C18	0.3042 (6)	0.1521 (3)	0.97876 (16)	0.03680
C19	0.6890 (5)	−0.1046 (2)	0.56204 (15)	0.03680
C20	0.3340 (5)	−0.2541 (3)	0.59660 (15)	0.03680
C21	0.5029 (4)	0.3546 (2)	1.09601 (13)	0.03680
H22	0.78003	0.40858	1.02301	0.04416
C23	0.1821 (5)	0.1628 (3)	1.04593 (16)	0.03680
H24	0.22751	0.07698	0.93529	0.04416
C25	0.6716 (5)	−0.1908 (3)	0.49044 (15)	0.03680
H26	0.82609	−0.02057	0.57312	0.04416
C27	0.3208 (5)	−0.3382 (3)	0.52449 (15)	0.03680
C28	0.1484 (6)	−0.2910 (3)	0.65291 (17)	0.03680
C29	0.2807 (4)	0.26350 (19)	1.10470 (14)	0.03680
N30	0.5556 (5)	0.4440 (3)	1.16446 (15)	0.03680
H31	0.02271	0.09862	1.05193	0.04416
C32	0.4907 (5)	−0.3059 (3)	0.47148 (14)	0.03680
H33	0.79742	−0.16692	0.45131	0.04416
H34	0.18753	−0.42326	0.51023	0.04416
O35	−0.0248 (7)	−0.4027 (4)	0.6268 (2)	0.03680
O36	0.1339 (7)	−0.2206 (5)	0.7143 (2)	0.03680
N37	0.2182 (5)	0.3076 (3)	1.17946 (15)	0.03680
H38	0.69762	0.51709	1.17337	0.04416
C39	0.3824 (6)	0.4172 (3)	1.21659 (16)	0.03680
H40	0.48327	−0.36620	0.41883	0.04416
H41	−0.15751	−0.43051	0.65955	0.04416
H42	0.07596	0.26638	1.20398	0.04416
O43	0.3770 (7)	0.4781 (4)	1.2817 (2)	0.03680

Geometric parameters (Å, º) top

C1—C2	1.509 (5)	C17—H22	1.05 (1)
C1—N3	1.296 (4)	C18—C23	1.374 (4)
C1—C4	1.492 (5)	C19—C25	1.402 (3)
C2—N5	1.347 (4)	C20—C27	1.402 (3)
C2—O6	1.225 (5)	C20—C28	1.486 (4)
N3—N7	1.303 (4)	C21—C29	1.423 (3)
C4—O8	1.213 (5)	C21—N30	1.378 (3)
C4—C9	1.521 (4)	C23—C29	1.356 (3)
N5—C10	1.412 (4)	C25—C32	1.379 (3)
N5—H11	0.98 (1)	C27—C32	1.376 (4)
N7—C13	1.401 (3)	C28—O35	1.352 (4)
C9—H14	1.10 (1)	C28—O36	1.203 (5)
C9—H15	1.10 (1)	C29—N37	1.393 (3)
C9—H16	1.08 (1)	N30—H38	0.99 (1)
C10—C17	1.377 (4)	N30—C39	1.365 (4)
C10—C18	1.390 (4)	O35—H41	0.94 (1)
C13—C19	1.383 (4)	N37—C39	1.364 (4)
C13—C20	1.417 (3)	N37—H42	0.97 (1)
C17—C21	1.363 (4)	C39—O43	1.215 (5)

C2—C1—N3	123.2 (3)	C13—C19—C25	118.8 (2)
C2—C1—C4	123.4 (3)	C13—C19—H26	119.4 (6)
N3—C1—C4	113.3 (3)	C25—C19—H26	121.7 (6)
C1—C2—N5	116.3 (3)	C13—C20—C27	121.0 (2)
C1—C2—O6	116.7 (3)	C13—C20—C28	120.4 (2)
N5—C2—O6	125.8 (3)	C27—C20—C28	118.6 (2)
C1—N3—N7	125.3 (4)	C17—C21—C29	121.0 (2)
C1—C4—O8	122.4 (3)	C17—C21—N30	132.2 (2)
C1—C4—C9	115.1 (2)	C29—C21—N30	106.8 (2)
O8—C4—C9	121.4 (3)	C18—C23—C29	117.9 (2)
C2—N5—C10	131.5 (3)	C18—C23—H31	119.2 (7)
C2—N5—H11	112.1 (7)	C29—C23—H31	122.9 (7)
N3—N7—H12	118.7 (7)	C19—C25—C32	122.5 (2)
N3—N7—C13	120.4 (3)	C19—C25—H33	119.4 (6)
H12—N7—C13	119.8 (7)	C32—C25—H33	118.1 (6)
C4—C9—H14	109.4 (7)	C20—C27—C32	119.5 (2)
C4—C9—H15	110.5 (7)	C20—C27—H34	119.4 (7)
C4—C9—H16	107.6 (6)	C32—C27—H34	121.1 (7)
H14—C9—H15	108.1 (8)	C20—C28—O35	114.7 (3)
H14—C9—H16	109.5 (7)	C20—C28—O36	123.7 (3)
H15—C9—H16	111.6 (9)	O35—C28—O36	121.2 (3)
N5—C10—C17	121.4 (2)	C21—C29—C23	120.4 (2)
N5—C10—C18	118.7 (2)	C21—C29—N37	104.0 (2)
C17—C10—C18	119.9 (3)	C23—C29—N37	135.5 (2)
N7—C13—C19	119.6 (2)	C25—C32—C27	119.3 (2)
N7—C13—C20	121.6 (2)	C25—C32—H40	119.4 (6)
C19—C13—C20	118.8 (2)	C27—C32—H40	121.3 (6)
C10—C17—C21	118.5 (2)	C29—N37—C39	112.8 (2)
C10—C17—H22	120.8 (7)	C29—N37—H42	127.3 (6)
C21—C17—H22	120.8 (7)	C39—N37—H42	119.9 (7)
C10—C18—C23	122.4 (2)	N30—C39—N37	104.7 (2)
C10—C18—H24	120.3 (7)	N30—C39—O43	127.4 (3)
C23—C18—H24	117.3 (7)	N37—C39—O43	127.9 (3)

(PY154) top

Crystal data top

C₁₈H₁₄F₃N₅O₃	F(000) = 832
M_r = 405.34	D_x = 1.577 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα₁ radiation, λ = 1.54056 Å
Hall symbol: -P 2ybc	µ = 1.15 mm⁻¹
a = 14.5848 (5) Å	T = 293 K
b = 8.5448 (2) Å	Particle morphology: no specific habit
c = 13.7794 (4) Å	orange
β = 96.0670 (19)°	cylinder, 10 × 0.7 mm
V = 1707.62 (9) Å³	Specimen preparation: Prepared at 293 K and 0.00 kPa
Z = 4

Data collection top

STOE-Stadi-P diffractometer	Data collection mode: transmission
Radiation source: sealed X-ray tube, laboratory diffractometer	Scan method: step
Primary focussing, Ge 111 monochromator	2θ_min = 3.00°, 2θ_max = 70.00°, 2θ_step = 0.01°
Specimen mounting: 'glass capillary'

Refinement top

Refinement on I_net	180 parameters
Least-squares matrix: full with fixed elements per cycle	120 restraints
R_p = 0.036	0 constraints
R_wp = 0.047	H-atom parameters constrained
R_exp = 0.090	Weighting scheme based on measured s.u.'s w = 1/σ[Y_obs]²
χ² = 1.369	(Δ/σ)_max = 0.001
6700 data points	Background function: Chebyshev polynomial with 20 terms
Excluded region(s): none	Preferred orientation correction: none
Profile function: modified Thompson-Cox-Hastings pseudo-Voigt (Young, 1993)

Crystal data top

C₁₈H₁₄F₃N₅O₃	V = 1707.62 (9) Å³
M_r = 405.34	Z = 4
Monoclinic, P2₁/c	Cu Kα₁ radiation, λ = 1.54056 Å
a = 14.5848 (5) Å	µ = 1.15 mm⁻¹
b = 8.5448 (2) Å	T = 293 K
c = 13.7794 (4) Å	cylinder, 10 × 0.7 mm
β = 96.0670 (19)°

Data collection top

STOE-Stadi-P diffractometer	Scan method: step
Specimen mounting: 'glass capillary'	2θ_min = 3.00°, 2θ_max = 70.00°, 2θ_step = 0.01°
Data collection mode: transmission

Refinement top

R_p = 0.036	6700 data points
R_wp = 0.047	180 parameters
R_exp = 0.090	120 restraints
χ² = 1.369	H-atom parameters constrained

Special details top

Experimental. specimen was rotated in its plane

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.0241 (3)	−0.1756 (5)	0.6301 (8)	0.03162
C2	−0.0354 (3)	−0.0265 (5)	0.6201 (8)	0.03162
N3	0.1138 (4)	−0.1724 (6)	0.6498 (7)	0.03162
C4	−0.0158 (3)	−0.3461 (6)	0.6192 (7)	0.03162
N5	−0.1277 (3)	−0.0532 (5)	0.6081 (4)	0.03162
O6	0.0011 (5)	0.1055 (6)	0.6245 (7)	0.03162
N7	0.1620 (3)	−0.0435 (5)	0.6504 (4)	0.03162
O8	−0.0989 (4)	−0.3709 (7)	0.6042 (6)	0.03162
C9	0.0563 (3)	−0.4770 (5)	0.6328 (4)	0.03162
C10	−0.2002 (3)	0.0542 (5)	0.5942 (4)	0.03162
H11	−0.14399	−0.16265	0.60749	0.03794
H12	0.13273	0.05708	0.63884	0.03794
C13	0.2569 (3)	−0.0572 (5)	0.6668 (2)	0.03162
H14	0.10141	−0.47059	0.57475	0.03794
H15	0.09758	−0.46512	0.70289	0.03794
H16	0.02215	−0.59043	0.62969	0.03794
C17	−0.1864 (3)	0.2210 (5)	0.5915 (3)	0.03162
C18	−0.2886 (3)	−0.0122 (5)	0.5801 (4)	0.03162
C19	0.2963 (3)	−0.2060 (5)	0.6766 (2)	0.03162
C20	0.3122 (3)	0.0799 (5)	0.6737 (3)	0.03162
C21	−0.2651 (3)	0.3072 (5)	0.5741 (2)	0.03162
H22	−0.12347	0.27339	0.60136	0.03794
C23	−0.3684 (3)	0.0803 (5)	0.5618 (3)	0.03162
H24	−0.29552	−0.13071	0.58245	0.03794
C25	0.3927 (3)	−0.2119 (5)	0.6935 (2)	0.03162
H26	0.25851	−0.30680	0.67203	0.03794
C27	0.4092 (3)	0.0686 (5)	0.6899 (2)	0.03162
C28	0.2660 (3)	0.2439 (6)	0.6651 (3)	0.03162
C29	−0.3539 (3)	0.2423 (5)	0.5596 (2)	0.03162
N30	−0.2743 (3)	0.4711 (5)	0.5682 (3)	0.03162
H31	−0.43270	0.03256	0.55092	0.03794
C32	0.4494 (3)	−0.0793 (5)	0.7003 (3)	0.03162
H33	0.42287	−0.31943	0.70016	0.03794
H34	0.44965	0.16573	0.69387	0.03794
F35	0.3269 (4)	0.3606 (6)	0.6775 (5)	0.03162
F36	0.2146 (4)	0.2693 (7)	0.5837 (4)	0.03162
F37	0.2071 (4)	0.2582 (7)	0.7353 (4)	0.03162
N38	−0.4136 (3)	0.3693 (5)	0.5448 (3)	0.03162
H39	−0.22260	0.54253	0.57542	0.03794
C40	−0.3660 (3)	0.5119 (5)	0.5494 (4)	0.03162
H41	0.51923	−0.09056	0.71189	0.03794
H42	−0.47969	0.36083	0.53000	0.03794
O43	−0.3975 (5)	0.6418 (6)	0.5339 (4)	0.03162

Geometric parameters (Å, º) top

C1—C2	1.540 (6)	C19—C25	1.402 (6)
C1—N3	1.308 (7)	C20—C27	1.412 (6)
C1—C4	1.570 (7)	C20—C28	1.554 (7)
C2—N5	1.357 (6)	C21—C29	1.403 (6)
C2—O6	1.246 (7)	C21—N30	1.409 (6)
C4—O8	1.226 (7)	C23—C29	1.401 (6)
C4—C9	1.534 (6)	C25—C32	1.400 (6)
N5—C10	1.398 (6)	C27—C32	1.394 (6)
C9—H14	1.07 (2)	C28—F35	1.334 (7)
C9—H15	1.07 (2)	C28—F36	1.300 (7)
C9—H16	1.09 (2)	C28—F37	1.365 (8)
C10—C17	1.441 (6)	C29—N38	1.393 (6)
C10—C18	1.402 (6)	N30—H39	1.00 (2)
C13—C19	1.396 (6)	N30—C40	1.380 (6)
C13—C20	1.419 (6)	N38—C40	1.400 (6)
C17—C21	1.364 (6)	C40—O43	1.211 (7)
C18—C23	1.408 (6)

C2—C1—N3	122.9 (4)	C13—C20—C27	120.4 (4)
C2—C1—C4	124.0 (4)	C13—C20—C28	120.0 (4)
N3—C1—C4	113.1 (4)	C27—C20—C28	119.5 (4)
C1—C2—N5	114.5 (4)	C17—C21—C29	124.0 (4)
C1—C2—O6	120.7 (5)	C17—C21—N30	128.3 (4)
N5—C2—O6	124.8 (5)	C29—C21—N30	107.7 (4)
C1—N3—N7	123.0 (5)	C18—C23—C29	115.7 (4)
C1—C4—O8	121.8 (5)	C18—C23—H31	123 (1)
C1—C4—C9	115.0 (4)	C29—C23—H31	121 (1)
O8—C4—C9	123.2 (5)	C19—C25—C32	123.8 (4)
C2—N5—C10	129.2 (4)	C19—C25—H33	118 (1)
C2—N5—H11	116 (1)	C32—C25—H33	118 (1)
C10—N5—H11	114 (1)	C20—C27—C32	118.8 (4)
N3—N7—C13	117.3 (4)	C20—C27—H34	120 (1)
C4—C9—H14	109 (1)	C32—C27—H34	121 (1)
C4—C9—H15	111 (1)	C20—C28—F35	112.7 (4)
C4—C9—H16	111 (1)	C20—C28—F36	115.0 (4)
H14—C9—H16	108 (1)	C20—C28—F37	109.1 (4)
H15—C9—H16	112 (1)	F35—C28—F36	107.5 (5)
N5—C10—C17	123.1 (4)	F35—C28—F37	107.6 (5)
N5—C10—C18	115.1 (4)	F36—C28—F37	104.3 (5)
C17—C10—C18	121.7 (4)	C21—C29—C23	121.8 (4)
N7—C13—C19	119.1 (4)	C21—C29—N38	105.4 (4)
N7—C13—C20	119.5 (4)	C23—C29—N38	132.8 (4)
C19—C13—C20	121.4 (4)	C21—N30—C40	110.2 (4)
C10—C17—C21	114.9 (4)	C25—C32—C27	119.2 (4)
C10—C17—H22	123.3 (9)	C25—C32—H41	120.7 (1)
C21—C17—H22	121.8 (9)	C27—C32—H41	120 (1)
C10—C18—C23	121.9 (4)	C29—N38—C40	111.8 (4)
C10—C18—H24	117 (1)	C29—N38—H42	126.9 (9)
C23—C18—H24	121 (1)	C40—N38—H42	121.2 (9)
C13—C19—C25	116.3 (4)	N30—C40—N38	104.8 (4)
C13—C19—H26	120 (1)	N30—C40—O43	127.3 (5)
C25—C19—H26	123 (1)	N38—C40—O43	127.8 (5)

(PY181) top

Crystal data top

C₂₅H₂₁N₇O₅	F(000) = 1040
M_r = 499.49	D_x = 1.477 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα₁ radiation, λ = 1.54056 Å
Hall symbol: -P 2ybc	µ = 0.89 mm⁻¹
a = 22.5510 (8) Å	T = 293 K
b = 4.96366 (13) Å	Particle morphology: no specific habit
c = 21.2815 (6) Å	orange
β = 109.4539 (13)°	cylinder, 10 × 0.7 mm
V = 2246.16 (12) Å³	Specimen preparation: Prepared at 293 K and 0.00 kPa
Z = 4

Data collection top

STOE-Stadi-P diffractometer	Data collection mode: transmission
Radiation source: sealed X-ray tube, laboratory diffractometer	Scan method: step
Primary focussing, Ge 111 monochromator	2θ_min = 3.00°, 2θ_max = 60.00°, 2θ_step = 0.01°
Specimen mounting: 'glass capillary'

Refinement top

Refinement on I_net	224 parameters
Least-squares matrix: full with fixed elements per cycle	162 restraints
R_p = 0.012	0 constraints
R_wp = 0.015	H-atom parameters constrained
R_exp = 0.036	Weighting scheme based on measured s.u.'s w = 1/σ[Y_obs]²
χ² = 1.188	(Δ/σ)_max = 0.001
5700 data points	Background function: Chebyshev polynomial with 20 terms
Excluded region(s): none	Preferred orientation correction: none
Profile function: modified Thompson-Cox-Hastings pseudo-Voigt (Young, 1993)

Crystal data top

C₂₅H₂₁N₇O₅	V = 2246.16 (12) Å³
M_r = 499.49	Z = 4
Monoclinic, P2₁/c	Cu Kα₁ radiation, λ = 1.54056 Å
a = 22.5510 (8) Å	µ = 0.89 mm⁻¹
b = 4.96366 (13) Å	T = 293 K
c = 21.2815 (6) Å	cylinder, 10 × 0.7 mm
β = 109.4539 (13)°

Data collection top

STOE-Stadi-P diffractometer	Scan method: step
Specimen mounting: 'glass capillary'	2θ_min = 3.00°, 2θ_max = 60.00°, 2θ_step = 0.01°
Data collection mode: transmission

Refinement top

R_p = 0.012	5700 data points
R_wp = 0.015	224 parameters
R_exp = 0.036	162 restraints
χ² = 1.188	H-atom parameters constrained

Special details top

Experimental. specimen was rotated in its plane

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	B_iso*/B_eq
C1	0.66678 (15)	0.5335 (7)	0.04782 (17)	2.50 (13)
N2	0.71619 (17)	0.5825 (9)	0.02379 (17)	2.50 (13)
C3	0.65657 (16)	0.6821 (7)	0.09860 (17)	2.50 (13)
C4	0.62626 (16)	0.3226 (6)	0.01783 (18)	2.50 (13)
N5	0.7589 (2)	0.7575 (12)	0.0517 (3)	2.50 (13)
H6	0.71967	0.47475	−0.01270	3.00 (15)
C7	0.60538 (16)	0.6173 (6)	0.11909 (14)	2.50 (13)
H8	0.68567	0.83724	0.12085	3.00 (15)
C9	0.57640 (15)	0.2614 (7)	0.03846 (16)	2.50 (13)
H10	0.63365	0.21287	−0.01947	3.00 (15)
C11	0.80788 (19)	0.7920 (10)	0.0341 (2)	2.50 (13)
C12	0.56517 (17)	0.4074 (7)	0.08941 (15)	2.50 (13)
H13	0.59799	0.72643	0.15642	3.00 (15)
H14	0.54757	0.10624	0.01590	3.00 (15)
C15	0.82224 (19)	0.6163 (10)	−0.0162 (2)	2.50 (13)
C16	0.85275 (19)	1.0001 (11)	0.0734 (2)	2.50 (13)
C17	0.50966 (18)	0.3246 (7)	0.1085 (2)	2.50 (13)
N18	0.87669 (17)	0.6653 (8)	−0.0279 (2)	2.50 (13)
O19	0.7849 (3)	0.4389 (12)	−0.0436 (3)	2.50 (13)
O20	0.9018 (2)	1.0451 (13)	0.0626 (3)	2.50 (13)
C21	0.83546 (16)	1.1592 (8)	0.12501 (18)	2.50 (13)
O22	0.4936 (3)	0.0918 (10)	0.1053 (3)	2.50 (13)
N23	0.48302 (17)	0.5249 (7)	0.1344 (2)	2.50 (13)
C24	0.90009 (17)	0.5254 (8)	−0.07246 (19)	2.50 (13)
H25	0.90195	0.81056	−0.00244	3.00 (15)
H26	0.79036	1.25763	0.10247	3.00 (15)
H27	0.83214	1.02693	0.16451	3.00 (15)
H28	0.87115	1.31160	0.14632	3.00 (15)
H29	0.50155	0.70212	0.13725	3.00 (15)
C30	0.43253 (17)	0.5046 (7)	0.15993 (17)	2.50 (13)
C31	0.86734 (17)	0.3138 (8)	−0.11406 (19)	2.50 (13)
C32	0.95801 (18)	0.6101 (8)	−0.0747 (2)	2.50 (13)
C33	0.38787 (16)	0.2995 (7)	0.13488 (14)	2.50 (13)
C34	0.42550 (16)	0.6774 (7)	0.20801 (16)	2.50 (13)
C35	0.89497 (16)	0.1938 (5)	−0.15652 (13)	2.50 (13)
H36	0.82474	0.24562	−0.11437	3.00 (15)
C37	0.98555 (18)	0.4895 (7)	−0.11712 (18)	2.50 (13)
H38	0.98113	0.76440	−0.04465	3.00 (15)
C39	0.33768 (16)	0.2704 (6)	0.15820 (16)	2.50 (13)
H40	0.39083	0.17057	0.09882	3.00 (15)
C41	0.37527 (16)	0.6467 (7)	0.23096 (17)	2.50 (13)
H42	0.45739	0.82769	0.22658	3.00 (15)
C43	0.95397 (13)	0.2823 (5)	−0.15799 (15)	2.50 (13)
N44	0.87591 (16)	−0.0158 (7)	−0.20326 (18)	2.50 (13)
H45	1.02821	0.55214	−0.11830	3.00 (15)
C46	0.33065 (17)	0.4431 (7)	0.20630 (17)	2.50 (13)
H47	0.30570	0.12034	0.13914	3.00 (15)
H48	0.37130	0.77645	0.26645	3.00 (15)
N49	0.96860 (16)	0.1249 (8)	−0.20455 (19)	2.50 (13)
H50	0.83639	−0.11026	−0.21293	3.00 (15)
C51	0.92107 (18)	−0.0618 (8)	−0.23346 (19)	2.50 (13)
C52	0.27697 (18)	0.4158 (8)	0.2321 (2)	2.50 (13)
H53	1.00673	0.14714	−0.21522	3.00 (15)
O54	0.9186 (2)	−0.2246 (10)	−0.2762 (2)	2.50 (13)
O55	0.2484 (3)	0.2070 (10)	0.2258 (3)	2.50 (13)
N56	0.26068 (18)	0.6416 (8)	0.2592 (3)	2.50 (13)
H57	0.28217	0.81088	0.25994	3.00 (15)
H58	0.22613	0.63381	0.27666	3.00 (15)

Geometric parameters (Å, º) top

C1—N2	1.394 (6)	C24—C32	1.385 (6)
C1—C3	1.386 (6)	C30—C33	1.403 (5)
N2—N5	1.285 (5)	C30—C34	1.383 (6)
N2—H6	0.99 (2)	C31—C35	1.391 (6)
C3—C7	1.404 (6)	C32—C37	1.391 (7)
C4—C9	1.371 (6)	C33—C39	1.385 (6)
N5—C11	1.299 (5)	C34—C41	1.384 (6)
C7—C12	1.389 (5)	C35—C43	1.412 (5)
C9—C12	1.397 (6)	C35—N44	1.404 (5)
C12—C17	1.496 (7)	C37—C43	1.378 (5)
C15—N18	1.346 (6)	C39—C46	1.382 (5)
C15—O19	1.220 (4)	C41—C46	1.402 (5)
C16—O20	1.228 (7)	C43—N49	1.385 (6)
C16—C21	1.502 (6)	N44—H50	1.00 (1)
C17—O22	1.202 (7)	N44—C51	1.394 (7)
C17—N23	1.367 (6)	C46—C52	1.494 (7)
N18—C24	1.414 (7)	N49—C51	1.396 (6)
N18—H25	1.00 (1)	N49—H53	0.99 (2)
C21—H26	1.09 (1)	C51—O54	1.205 (7)
C21—H27	1.08 (2)	C52—O55	1.204 (7)
C21—H28	1.08 (1)	C52—N56	1.367 (7)
N23—H29	0.99 (1)	N56—H57	0.99 (2)
N23—C30	1.420 (7)	N56—H58	0.98 (2)
C24—C31	1.413 (6)

N2—C1—C3	123.7 (3)	C31—C24—C32	120.2 (4)
N2—C1—C4	116.2 (4)	N23—C30—C33	118.1 (4)
C3—C1—C4	120.1 (4)	N23—C30—C34	122.8 (3)
C1—N2—N5	121.0 (4)	C33—C30—C34	119.1 (4)
C1—N2—H6	120.3 (9)	C24—C31—C35	118.3 (4)
N5—N2—H6	117 (1)	C24—C31—H36	120.2 (9)
C1—C3—C7	119.2 (3)	C35—C31—H36	121.5 (9)
C1—C3—H8	120 (1)	C24—C32—C37	121.5 (4)
C7—C3—H8	120 (1)	C24—C32—H38	119 (1)
C1—C4—C9	120.1 (3)	C37—C32—H38	120 (1)
C1—C4—H10	119.8 (9)	C30—C33—C39	120.5 (3)
C9—C4—H10	120.1 (8)	C30—C33—H40	119.7 (9)
N2—N5—C11	123.7 (3)	C39—C33—H40	119.7 (9)
C3—C7—C12	120.7 (3)	C30—C34—C41	120.0 (3)
C3—C7—H13	119.2 (9)	C30—C34—H42	119 (1)
C12—C7—H13	120.1 (9)	C41—C34—H42	120 (1)
C4—C9—C12	120.9 (3)	C31—C35—C43	120.6 (3)
C4—C9—H14	120 (1)	C31—C35—N44	132.9 (3)
C12—C9—H14	119 (1)	C43—C35—N44	106.5 (3)
C15—C11—C16	123.3 (3)	C32—C37—C43	118.7 (4)
C7—C12—C9	119.0 (4)	C32—C37—H45	120 (1)
C7—C12—C17	124.0 (4)	C43—C37—H45	121 (1)
C9—C12—C17	117.0 (3)	C33—C39—C46	120.6 (3)
C11—C15—O19	119.3 (4)	C33—C39—H47	120 (1)
N18—C15—O19	125.1 (4)	C46—C39—H47	120 (1)
C11—C16—O20	120.6 (4)	C34—C41—C46	121.1 (4)
C11—C16—C21	118.8 (3)	C34—C41—H48	119.5 (9)
O20—C16—C21	120.4 (4)	C46—C41—H48	119.3 (9)
C12—C17—O22	120.5 (5)	C35—C43—C37	120.7 (3)
C12—C17—N23	115.6 (3)	C35—C43—N49	106.8 (3)
O22—C17—N23	123.7 (5)	C37—C43—N49	132.5 (4)
C15—N18—C24	126.5 (4)	C35—N44—C51	110.5 (3)
C15—N18—H25	114 (1)	C39—C46—C41	118.6 (4)
C24—N18—H25	114 (1)	C39—C46—C52	121.7 (3)
C16—C21—H26	109.0 (8)	C41—C46—C52	119.7 (4)
C16—C21—H27	112 (1)	C43—N49—C51	111.2 (4)
C16—C21—H28	108.3 (9)	C43—N49—H53	126 (1)
H26—C21—H27	107 (1)	N44—C51—N49	104.9 (4)
H26—C21—H28	110 (1)	N44—C51—O54	127.3 (5)
H27—C21—H28	110 (1)	N49—C51—O54	127.8 (5)
C17—N23—H29	116 (1)	C46—C52—O55	119.9 (5)
C17—N23—C30	128.2 (4)	C46—C52—N56	116.7 (4)
H29—N23—C30	115 (1)	O55—C52—N56	123.2 (5)
N18—C24—C31	123.4 (4)	C52—N56—H57	119.9 (1)
N18—C24—C32	116.4 (4)	H57—N56—H58	116 (1)

(PY194) top

Crystal data top

C₁₈H₁₇N₅O₄	F(000) = 768
M_r = 367.37	D_x = 1.468 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα₁ radiation, λ = 1.54056 Å
Hall symbol: -P 2ybc	µ = 0.89 mm⁻¹
a = 14.7172 (16) Å	T = 293 K
b = 5.9852 (5) Å	Particle morphology: no specific habit
c = 20.7919 (13) Å	orange
β = 114.818 (4)°	flat_sheet, 10 × 1.2 mm
V = 1662.3 (2) Å³	Specimen preparation: Prepared at 293 K and 0.00 kPa
Z = 4

Data collection top

STOE-Stadi-P diffractometer	Data collection mode: transmission
Radiation source: sealed X-ray tube, laboratory diffractometer	Scan method: step
Primary focussing, Ge 111 monochromator	2θ_min = 3.00°, 2θ_max = 34.00°, 2θ_step = 0.02°
Specimen mounting: flat sample holder

Refinement top

Refinement on I_net	176 parameters
Least-squares matrix: full with fixed elements per cycle	122 restraints
R_p = 0.029	0 constraints
R_wp = 0.039	H-atom parameters constrained
R_exp = 0.048	Weighting scheme based on measured s.u.'s w = 1/σ[Y_obs]²
χ² = 1.322	(Δ/σ)_max = 0.001
1550 data points	Background function: Chebyshev polynomial with 15 terms
Excluded region(s): none	Preferred orientation correction: none
Profile function: modified Thompson-Cox-Hastings pseudo-Voigt (Young, 1993)

Crystal data top

C₁₈H₁₇N₅O₄	V = 1662.3 (2) Å³
M_r = 367.37	Z = 4
Monoclinic, P2₁/c	Cu Kα₁ radiation, λ = 1.54056 Å
a = 14.7172 (16) Å	µ = 0.89 mm⁻¹
b = 5.9852 (5) Å	T = 293 K
c = 20.7919 (13) Å	flat_sheet, 10 × 1.2 mm
β = 114.818 (4)°

Data collection top

STOE-Stadi-P diffractometer	Scan method: step
Specimen mounting: flat sample holder	2θ_min = 3.00°, 2θ_max = 34.00°, 2θ_step = 0.02°
Data collection mode: transmission

Refinement top

R_p = 0.029	1550 data points
R_wp = 0.039	176 parameters
R_exp = 0.048	122 restraints
χ² = 1.322	H-atom parameters constrained

Special details top

Experimental. specimen was rotated in its plane

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	B_iso*/B_eq
C1	0.1777 (5)	−0.8522 (9)	0.95496 (17)	2.53665
C2	0.0630 (3)	−0.8367 (10)	0.91732 (18)	2.53665
N3	0.2320 (6)	−0.6866 (13)	0.9461 (3)	2.53665
C4	0.2315 (6)	−1.0409 (15)	1.0014 (3)	2.53665
N5	0.0098 (5)	−0.9996 (12)	0.9255 (3)	2.53665
O6	0.0244 (7)	−0.6727 (15)	0.8806 (3)	2.53665
N7	0.1973 (5)	−0.5046 (12)	0.9046 (3)	2.53665
O8	0.1843 (9)	−1.1852 (19)	1.0117 (6)	2.53665
C9	0.3452 (6)	−1.0289 (15)	1.0434 (5)	2.53665
C10	−0.0911 (7)	−1.0541 (15)	0.8849 (4)	2.53665
H11	0.0495 (18)	−1.119 (4)	0.9565 (11)	3.04398
H12	0.1238 (17)	−0.471 (5)	0.8794 (14)	3.04398
C13	0.2644 (6)	−0.3865 (12)	0.8878 (3)	2.53665
H14	0.3792 (15)	−0.912 (4)	1.0201 (11)	3.04398
H15	0.3633 (17)	−0.971 (4)	1.0959 (11)	3.04398
H16	0.3761 (16)	−1.195 (4)	1.0463 (11)	3.04398
C17	−0.1164 (6)	−1.2549 (14)	0.9044 (4)	2.53665
C18	−0.1617 (6)	−0.9195 (15)	0.8336 (5)	2.53665
C19	0.3638 (6)	−0.4434 (11)	0.9122 (3)	2.53665
C20	0.2292 (6)	−0.1948 (13)	0.8479 (3)	2.53665
C21	−0.2153 (4)	−1.3147 (12)	0.8707 (3)	2.53665
H22	−0.061 (2)	−1.358 (4)	0.9442 (12)	3.04398
C23	−0.2604 (6)	−0.9783 (13)	0.7985 (4)	2.53665
H24	−0.1387 (15)	−0.767 (4)	0.8196 (10)	3.04398
C25	0.4263 (6)	−0.3070 (12)	0.8965 (3)	2.53665
H26	0.3905 (16)	−0.591 (4)	0.9424 (11)	3.04398
C27	0.2932 (6)	−0.0539 (11)	0.8318 (3)	2.53665
O28	0.1256 (7)	−0.1513 (18)	0.8238 (4)	2.53665
C29	−0.2888 (5)	−1.1746 (10)	0.8164 (2)	2.53665
N30	−0.2699 (6)	−1.5011 (14)	0.8752 (4)	2.53665
H31	−0.3120 (17)	−0.872 (5)	0.7588 (11)	3.04398
C32	0.3914 (6)	−0.1107 (11)	0.8562 (3)	2.53665
H33	0.5031 (19)	−0.356 (4)	0.9162 (10)	3.04398
H34	0.2662 (17)	0.096 (4)	0.8012 (11)	3.04398
C35	0.0875 (6)	0.0068 (14)	0.7680 (4)	2.53665
N36	−0.3802 (5)	−1.2856 (14)	0.7931 (4)	2.53665
H37	−0.2429 (17)	−1.633 (4)	0.9073 (11)	3.04398
C38	−0.3721 (6)	−1.4825 (15)	0.8272 (5)	2.53665
H39	0.4399 (17)	−0.005 (4)	0.8440 (10)	3.04398
H40	0.1422 (16)	0.135 (4)	0.7772 (12)	3.04398
H41	0.0738 (17)	−0.076 (5)	0.7196 (10)	3.04398
H42	0.020 (2)	0.081 (11)	0.7650 (13)	3.04398
H43	−0.445 (2)	−1.236 (7)	0.7565 (11)	3.04398
O44	−0.4398 (8)	−1.6082 (19)	0.8181 (5)	2.53665

Geometric parameters (Å, º) top

C1—N3	1.36 (1)	C20—C27	1.426 (9)
C4—C9	1.497 (8)	C21—C29	1.447 (6)
N5—H11	0.97 (3)	C23—C29	1.377 (8)
N7—H12	0.98 (2)	C23—H31	1.00 (2)
N7—C13	1.364 (9)	C25—C32	1.423 (7)
C9—H14	1.08 (2)	C25—H33	1.02 (2)
C9—H15	1.08 (2)	C27—H34	1.04 (2)
C9—H16	1.09 (2)	O28—C35	1.453 (9)
C10—C17	1.39 (1)	N30—H37	0.97 (2)
C10—C18	1.385 (8)	C32—H39	1.03 (2)
C13—C19	1.404 (8)	C35—H40	1.10 (2)
C17—H22	1.01 (2)	C35—H41	1.10 (2)
C18—C23	1.397 (8)	C35—H42	1.12 (3)
C18—H24	0.99 (2)	N36—C38	1.374 (9)
C19—H26	1.02 (2)	N36—H43	0.97 (2)

C2—C1—C4	125.0 (7)	C13—C20—O28	116.8 (6)
C1—C2—O6	120.7 (9)	C27—C20—O28	121.8 (5)
C1—N3—N7	127.4 (7)	C17—C21—C29	120.2 (5)
C1—C4—O8	119.6 (7)	C17—C21—N30	133.7 (5)
C2—N5—H11	114 (1)	C29—C21—N30	106.1 (4)
C10—N5—H11	114 (1)	C18—C23—C29	118.3 (5)
N3—N7—H12	117 (2)	C18—C23—H31	122 (1)
H12—N7—C13	119 (2)	C29—C23—H31	120 (1)
C4—C9—H14	110 (1)	C19—C25—C32	121.7 (5)
C4—C9—H15	111 (1)	C19—C25—H33	119 (1)
C4—C9—H16	111 (1)	C32—C25—H33	119 (1)
H14—C9—H15	108 (2)	C20—C27—C32	118.1 (4)
H14—C9—H16	108 (1)	C20—C27—H34	122 (1)
H15—C9—H16	108 (2)	C32—C27—H34	120 (1)
N5—C10—C17	113.3 (5)	C21—C29—C23	120.0 (4)
N5—C10—C18	126.0 (7)	C21—C29—N36	108.5 (4)
C17—C10—C18	120.7 (6)	C23—C29—N36	131.5 (4)
N7—C13—C19	122.8 (5)	C21—N30—H37	126 (1)
N7—C13—C20	117.6 (5)	H37—N30—C38	126 (1)
C19—C13—C20	119.5 (5)	C25—C32—C27	120.2 (5)
C10—C17—C21	118.2 (5)	C25—C32—H39	119 (1)
C10—C17—H22	120 (1)	C27—C32—H39	120 (1)
C21—C17—H22	122 (1)	O28—C35—H40	110 (1)
C10—C18—C23	122.5 (6)	O28—C35—H41	111 (1)
C10—C18—H24	119 (1)	O28—C35—H42	110 (2)
C23—C18—H24	118 (1)	H40—C35—H41	109 (1)
C13—C19—C25	119.1 (5)	H40—C35—H42	108 (1)
C13—C19—H26	121 (1)	H41—C35—H42	109 (2)
C25—C19—H26	120 (1)	C29—N36—H43	125 (2)
C13—C20—C27	121.4 (5)	N36—C38—O44	126.4 (6)

(BIRZIL) top

Crystal data top

C₁₈H₁₆ClN₅O₄	Z = 8
M_r = 401.81	F(000) = 1664
Monoclinic, C2/c	D_x = 1.470 Mg m⁻³
a = 17.126 (2) Å	Cu Kα radiation, λ = 1.54180 Å
b = 5.036 (2) Å	µ = 2.19 mm⁻¹
c = 42.45 (1) Å	T = 293 K
β = 97.36 (2)°	Needle, yellow
V = 3631 (2) Å³	0.5 × 0.25 × 0.05 mm

Data collection top

Nicolet R3 computer-controlled four circle diffractometer	R_int = 0.047
Radiation source: fine-focus sealed tube	θ_max = 55.2°, θ_min = 4.2°
Graphite monochromator	h = −18→0
2θ/θ scan	k = −5→0
2394 measured reflections	l = −44→45
2303 independent reflections	1 standard reflections every 40 reflections
971 reflections with I > 2σ(I)	intensity decay: no decay

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.078	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.198	w = 1/[σ²(F_o²) + (0.0883P)²] where P = (F_o² + 2F_c²)/3
S = 0.92	(Δ/σ)_max < 0.001
2303 reflections	Δρ_max = 0.25 e Å⁻³
254 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00042 (8)

Crystal data top

C₁₈H₁₆ClN₅O₄	V = 3631 (2) Å³
M_r = 401.81	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 17.126 (2) Å	µ = 2.19 mm⁻¹
b = 5.036 (2) Å	T = 293 K
c = 42.45 (1) Å	0.5 × 0.25 × 0.05 mm
β = 97.36 (2)°

Data collection top

Nicolet R3 computer-controlled four circle diffractometer	R_int = 0.047
2394 measured reflections	θ_max = 55.2°
2303 independent reflections	1 standard reflections every 40 reflections
971 reflections with I > 2σ(I)	intensity decay: no decay

Refinement top

R[F² > 2σ(F²)] = 0.078	0 restraints
wR(F²) = 0.198	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	Δρ_max = 0.25 e Å⁻³
2303 reflections	Δρ_min = −0.25 e Å⁻³
254 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	−0.08431 (12)	−0.7367 (6)	1.22574 (6)	0.0982 (10)
O1	−0.4148 (3)	−0.5895 (12)	1.17342 (13)	0.0805 (19)
O2	−0.2234 (3)	0.3797 (12)	1.09074 (14)	0.0737 (18)
O3	−0.4167 (3)	−0.0453 (12)	1.11704 (13)	0.0729 (18)
O4	−0.7848 (3)	0.4688 (11)	1.02475 (13)	0.0753 (18)
N1	−0.3079 (3)	−0.2890 (13)	1.15254 (14)	0.0561 (18)
H1	−0.3571	−0.2744	1.1455	0.061*
N2	−0.2565 (3)	−0.1362 (14)	1.14113 (15)	0.0553 (19)
N3	−0.3781 (3)	0.2708 (14)	1.08444 (14)	0.0619 (19)
H3	−0.3363	0.3430	1.0790	0.071*
N4	−0.6684 (3)	0.3011 (13)	1.05183 (14)	0.063 (2)
H4	−0.6873	0.1750	1.0622	0.064*
N5	−0.6601 (3)	0.6391 (13)	1.02007 (15)	0.0623 (19)
H5	−0.6730	0.7645	1.0067	0.070*
C01	−0.1839 (5)	−0.7001 (19)	1.2104 (2)	0.064 (2)
C02	−0.2043 (4)	−0.5024 (18)	1.18818 (18)	0.060 (2)
H02	−0.1664	−0.3911	1.1815	0.063*
C03	−0.2836 (4)	−0.4755 (17)	1.17614 (18)	0.053 (2)
C04	−0.3394 (4)	−0.6498 (18)	1.1868 (2)	0.059 (2)
C05	−0.3167 (5)	−0.8381 (17)	1.20906 (18)	0.062 (2)
H05	−0.3542	−0.9472	1.2165	0.067*
C06	−0.2374 (5)	−0.8677 (17)	1.2207 (2)	0.068 (3)
H06	−0.2213	−1.0006	1.2353	0.072*
C07	−0.2796 (4)	0.0410 (17)	1.11936 (19)	0.052 (2)
C08	−0.3651 (4)	0.0866 (17)	1.1067 (2)	0.054 (2)
C09	−0.4746 (5)	−0.7648 (19)	1.1819 (2)	0.091 (3)
H091	−0.5251	−0.7087	1.1716	0.091*
H092	−0.4749	−0.7608	1.2045	0.091*
H093	−0.4641	−0.9423	1.1754	0.091*
C10	−0.2131 (5)	0.2024 (17)	1.11081 (19)	0.060 (2)
C11	−0.1304 (4)	0.1397 (18)	1.12526 (19)	0.077 (3)
H111	−0.1313	−0.0022	1.1403	0.081*
H112	−0.1072	0.2944	1.1359	0.081*
H113	−0.0999	0.0871	1.1088	0.081*
C12	−0.4502 (4)	0.3694 (17)	1.06797 (17)	0.053 (2)
C13	−0.5228 (4)	0.2498 (16)	1.07110 (16)	0.053 (2)
H13	−0.5268	0.1026	1.0840	0.048*
C14	−0.5878 (4)	0.3638 (16)	1.05384 (18)	0.051 (2)
C15	−0.5833 (5)	0.5793 (18)	1.03372 (19)	0.061 (2)
C16	−0.5115 (5)	0.6936 (17)	1.02995 (19)	0.068 (3)
H16	−0.5076	0.8367	1.0164	0.067*
C17	−0.4458 (5)	0.5829 (17)	1.04749 (19)	0.065 (2)
H17	−0.3967	0.6545	1.0455	0.075*
C18	−0.7116 (5)	0.4641 (19)	1.0316 (2)	0.063 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0571 (13)	0.121 (2)	0.1124 (19)	0.0172 (16)	−0.0052 (12)	0.020 (2)
O1	0.049 (3)	0.085 (5)	0.108 (5)	−0.008 (3)	0.010 (3)	0.025 (4)
O2	0.051 (3)	0.078 (5)	0.094 (5)	−0.010 (3)	0.015 (3)	0.010 (4)
O3	0.045 (3)	0.080 (4)	0.093 (5)	−0.005 (3)	0.007 (3)	0.024 (4)
O4	0.047 (3)	0.081 (4)	0.098 (4)	0.006 (3)	0.008 (3)	0.020 (4)
N1	0.040 (3)	0.059 (5)	0.069 (5)	−0.002 (4)	0.002 (3)	0.013 (4)
N2	0.047 (4)	0.068 (5)	0.052 (4)	−0.002 (4)	0.012 (3)	0.007 (4)
N3	0.046 (4)	0.074 (5)	0.065 (5)	−0.003 (4)	0.005 (3)	0.013 (4)
N4	0.048 (4)	0.063 (5)	0.076 (5)	−0.001 (4)	−0.001 (3)	0.018 (4)
N5	0.055 (4)	0.058 (5)	0.072 (5)	0.006 (4)	0.003 (4)	0.015 (4)
C01	0.053 (5)	0.073 (7)	0.066 (6)	0.017 (5)	0.005 (4)	0.006 (6)
C02	0.049 (5)	0.067 (6)	0.063 (6)	−0.010 (5)	0.007 (4)	−0.010 (5)
C03	0.053 (5)	0.049 (6)	0.056 (5)	0.012 (5)	0.004 (4)	0.001 (5)
C04	0.046 (5)	0.059 (6)	0.072 (6)	0.006 (5)	0.008 (4)	−0.001 (5)
C05	0.060 (6)	0.052 (6)	0.073 (6)	−0.004 (5)	0.007 (5)	0.002 (5)
C06	0.073 (6)	0.052 (6)	0.077 (6)	0.018 (5)	0.003 (5)	0.011 (5)
C07	0.044 (5)	0.053 (6)	0.060 (6)	−0.002 (4)	0.008 (4)	−0.005 (5)
C08	0.047 (5)	0.052 (6)	0.063 (6)	0.010 (5)	0.005 (4)	0.006 (5)
C09	0.067 (6)	0.092 (8)	0.113 (8)	−0.008 (6)	0.005 (5)	0.027 (7)
C10	0.073 (6)	0.055 (6)	0.053 (6)	0.006 (5)	0.009 (5)	0.004 (5)
C11	0.044 (5)	0.095 (8)	0.094 (7)	0.010 (5)	0.013 (5)	−0.003 (6)
C12	0.054 (5)	0.058 (6)	0.047 (5)	0.003 (5)	0.009 (4)	−0.003 (5)
C13	0.048 (4)	0.055 (5)	0.059 (5)	0.012 (5)	0.013 (4)	0.020 (5)
C14	0.047 (5)	0.047 (5)	0.061 (5)	−0.001 (4)	0.013 (4)	0.005 (5)
C15	0.052 (5)	0.064 (7)	0.066 (6)	−0.002 (5)	0.005 (4)	0.010 (5)
C16	0.070 (6)	0.069 (7)	0.065 (6)	0.005 (5)	0.011 (5)	0.021 (5)
C17	0.060 (5)	0.058 (6)	0.077 (6)	0.007 (5)	0.013 (5)	0.011 (5)
C18	0.057 (5)	0.069 (7)	0.064 (6)	0.003 (6)	0.012 (5)	0.015 (5)

Geometric parameters (Å, º) top

Cl1—C01	1.756 (8)	C03—C04	1.415 (10)
O1—C04	1.377 (8)	C04—C05	1.359 (10)
O1—C09	1.433 (9)	C05—C06	1.393 (10)
O2—C10	1.231 (9)	C05—H05	0.9300
O3—C08	1.230 (9)	C06—H06	0.9300
O4—C18	1.250 (8)	C07—C10	1.483 (11)
N1—N2	1.309 (8)	C07—C08	1.511 (9)
N1—C03	1.397 (9)	C09—H091	0.9600
N1—H1	0.8600	C09—H092	0.9600
N2—C07	1.309 (9)	C09—H093	0.9600
N3—C08	1.324 (9)	C10—C11	1.502 (10)
N3—C12	1.428 (9)	C11—H111	0.9600
N3—H3	0.8600	C11—H112	0.9600
N4—C18	1.340 (9)	C11—H113	0.9600
N4—C14	1.408 (8)	C12—C17	1.391 (10)
N4—H4	0.8600	C12—C13	1.403 (9)
N5—C18	1.381 (9)	C13—C14	1.377 (9)
N5—C15	1.400 (9)	C13—H13	0.9300
N5—H5	0.8600	C14—C15	1.389 (10)
C01—C06	1.358 (11)	C15—C16	1.386 (10)
C01—C02	1.386 (10)	C16—C17	1.383 (10)
C02—C03	1.394 (9)	C16—H16	0.9300
C02—H02	0.9300	C17—H17	0.9300

C04—O1—C09	115.0 (7)	N3—C08—C07	115.3 (8)
N2—N1—C03	120.5 (6)	O1—C09—H091	109.5
N2—N1—H1	119.8	O1—C09—H092	109.5
C03—N1—H1	119.8	H091—C09—H092	109.5
C07—N2—N1	120.3 (6)	O1—C09—H093	109.5
C08—N3—C12	130.5 (7)	H091—C09—H093	109.5
C08—N3—H3	114.7	H092—C09—H093	109.5
C12—N3—H3	114.7	O2—C10—C07	121.3 (8)
C18—N4—C14	111.0 (7)	O2—C10—C11	118.7 (8)
C18—N4—H4	124.5	C07—C10—C11	119.9 (8)
C14—N4—H4	124.5	C10—C11—H111	109.5
C18—N5—C15	109.0 (7)	C10—C11—H112	109.5
C18—N5—H5	125.5	H111—C11—H112	109.5
C15—N5—H5	125.5	C10—C11—H113	109.5
C06—C01—C02	122.9 (8)	H111—C11—H113	109.5
C06—C01—Cl1	118.6 (7)	H112—C11—H113	109.5
C02—C01—Cl1	118.4 (7)	C17—C12—C13	120.7 (7)
C01—C02—C03	117.9 (8)	C17—C12—N3	117.6 (7)
C01—C02—H02	121.0	C13—C12—N3	121.7 (7)
C03—C02—H02	121.0	C14—C13—C12	115.9 (7)
C02—C03—N1	121.0 (8)	C14—C13—H13	122.1
C02—C03—C04	119.2 (8)	C12—C13—H13	122.1
N1—C03—C04	119.7 (7)	C13—C14—C15	123.3 (7)
C05—C04—O1	127.6 (8)	C13—C14—N4	131.2 (7)
C05—C04—C03	120.7 (8)	C15—C14—N4	105.6 (7)
O1—C04—C03	111.5 (8)	C16—C15—C14	121.0 (8)
C04—C05—C06	120.0 (8)	C16—C15—N5	131.6 (8)
C04—C05—H05	120.0	C14—C15—N5	107.4 (7)
C06—C05—H05	120.0	C17—C16—C15	116.3 (8)
C01—C06—C05	119.2 (8)	C17—C16—H16	121.9
C01—C06—H06	120.4	C15—C16—H16	121.9
C05—C06—H06	120.4	C16—C17—C12	122.9 (8)
N2—C07—C10	111.9 (7)	C16—C17—H17	118.6
N2—C07—C08	123.1 (8)	C12—C17—H17	118.6
C10—C07—C08	124.8 (8)	O4—C18—N4	128.1 (8)
O3—C08—N3	124.7 (7)	O4—C18—N5	124.9 (8)
O3—C08—C07	120.0 (8)	N4—C18—N5	107.0 (7)

C03—N1—N2—C07	−179.0 (7)	C08—C07—C10—O2	−4.5 (12)
C06—C01—C02—C03	0.4 (13)	N2—C07—C10—C11	3.9 (10)
Cl1—C01—C02—C03	179.9 (6)	C08—C07—C10—C11	179.3 (7)
C01—C02—C03—N1	−176.9 (7)	C08—N3—C12—C17	174.3 (8)
C01—C02—C03—C04	−0.3 (11)	C08—N3—C12—C13	−8.3 (12)
N2—N1—C03—C02	0.4 (11)	C17—C12—C13—C14	−2.5 (11)
N2—N1—C03—C04	−176.2 (7)	N3—C12—C13—C14	−179.8 (7)
C09—O1—C04—C05	−6.5 (12)	C12—C13—C14—C15	1.7 (11)
C09—O1—C04—C03	177.3 (7)	C12—C13—C14—N4	−178.4 (7)
C02—C03—C04—C05	1.3 (12)	C18—N4—C14—C13	−179.3 (8)
N1—C03—C04—C05	178.0 (7)	C18—N4—C14—C15	0.6 (9)
C02—C03—C04—O1	177.8 (7)	C13—C14—C15—C16	−0.1 (12)
N1—C03—C04—O1	−5.5 (10)	N4—C14—C15—C16	180.0 (8)
O1—C04—C05—C06	−178.3 (8)	C13—C14—C15—N5	179.4 (7)
C03—C04—C05—C06	−2.4 (12)	N4—C14—C15—N5	−0.5 (8)
C02—C01—C06—C05	−1.5 (13)	C18—N5—C15—C16	179.7 (9)
Cl1—C01—C06—C05	179.0 (6)	C18—N5—C15—C14	0.3 (9)
C04—C05—C06—C01	2.5 (12)	C14—C15—C16—C17	−0.7 (12)
N1—N2—C07—C10	177.1 (7)	N5—C15—C16—C17	179.9 (8)
N1—N2—C07—C08	1.6 (11)	C15—C16—C17—C12	−0.1 (12)
C12—N3—C08—O3	2.4 (14)	C13—C12—C17—C16	1.8 (12)
C12—N3—C08—C07	−178.3 (7)	N3—C12—C17—C16	179.2 (7)
N2—C07—C08—O3	0.3 (12)	C14—N4—C18—O4	−178.2 (8)
C10—C07—C08—O3	−174.5 (8)	C14—N4—C18—N5	−0.4 (9)
N2—C07—C08—N3	−179.1 (7)	C15—N5—C18—O4	178.0 (8)
C10—C07—C08—N3	6.1 (11)	C15—N5—C18—N4	0.1 (9)
N2—C07—C10—O2	−179.9 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	2.28	2.616 (9)	103
C13—H13···O3	0.93	2.32	2.899 (9)	120
N1—H1···O3	0.86	1.87	2.555 (8)	135
N3—H3···O2	0.86	1.94	2.685 (8)	144
N4—H4···O2ⁱ	0.86	2.06	2.919 (9)	174
N5—H5···O4ⁱⁱ	0.86	1.96	2.819 (8)	173

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

(PY154-DMSO) top

Crystal data top

C₂₀H₂₀F₃N₅O₄S	Z = 2
M_r = 483.47	F(000) = 500
Triclinic, P1	D_x = 1.460 Mg m⁻³
a = 7.5478 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.941 (2) Å	Cell parameters from 5696 reflections
c = 13.530 (2) Å	θ = 3.6–25.7°
α = 103.996 (14)°	µ = 0.21 mm⁻¹
β = 101.670 (15)°	T = 173 K
γ = 104.491 (14)°	Plate, dark yellow
V = 1099.9 (3) Å³	0.17 × 0.11 × 0.02 mm

Data collection top

STOE IPDS II two-circle- diffractometer	4108 independent reflections
Radiation source: fine-focus sealed tube	2452 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.091
ω scans	θ_max = 25.6°, θ_min = 3.5°
Absorption correction: multi-scan MULABS (Spek, 2003; Blessing, 1995)	h = −9→7
T_min = 0.965, T_max = 0.996	k = −14→14
11729 measured reflections	l = −16→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.166	w = 1/[σ²(F_o²) + (0.0714P)²] where P = (F_o² + 2F_c²)/3
S = 0.95	(Δ/σ)_max < 0.001
4108 reflections	Δρ_max = 0.32 e Å⁻³
316 parameters	Δρ_min = −0.36 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.023 (4)

Crystal data top

C₂₀H₂₀F₃N₅O₄S	γ = 104.491 (14)°
M_r = 483.47	V = 1099.9 (3) Å³
Triclinic, P1	Z = 2
a = 7.5478 (14) Å	Mo Kα radiation
b = 11.941 (2) Å	µ = 0.21 mm⁻¹
c = 13.530 (2) Å	T = 173 K
α = 103.996 (14)°	0.17 × 0.11 × 0.02 mm
β = 101.670 (15)°

Data collection top

STOE IPDS II two-circle- diffractometer	4108 independent reflections
Absorption correction: multi-scan MULABS (Spek, 2003; Blessing, 1995)	2452 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.996	R_int = 0.091
11729 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.166	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	Δρ_max = 0.32 e Å⁻³
4108 reflections	Δρ_min = −0.36 e Å⁻³
316 parameters

Special details top

Experimental.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.50971 (16)	0.62448 (9)	0.13129 (9)	0.0458 (3)
O1S	0.4647 (5)	0.4967 (2)	0.1358 (3)	0.0557 (8)
C1S	0.5563 (10)	0.7168 (5)	0.2632 (5)	0.0856 (19)
H1S1	0.4376	0.7044	0.2841	0.128*
H1S2	0.6083	0.8025	0.2680	0.128*
H1S3	0.6487	0.6949	0.3107	0.128*
C2S	0.7445 (7)	0.6686 (4)	0.1193 (4)	0.0541 (11)
H2S1	0.7464	0.6240	0.0487	0.081*
H2S2	0.8300	0.6500	0.1735	0.081*
H2S3	0.7871	0.7561	0.1293	0.081*
N1	0.7916 (4)	0.7730 (3)	0.6740 (3)	0.0316 (7)
H1	0.754 (6)	0.738 (4)	0.611 (3)	0.040 (12)*
N2	0.8494 (4)	0.7069 (3)	0.7317 (2)	0.0321 (7)
C3	0.8468 (5)	0.5961 (3)	0.6855 (3)	0.0326 (8)
C31	0.9199 (6)	0.5368 (4)	0.7632 (3)	0.0391 (9)
O31	0.9171 (5)	0.4300 (3)	0.7345 (2)	0.0516 (8)
C32	0.9941 (7)	0.6095 (4)	0.8792 (3)	0.0476 (11)
H32A	0.8875	0.6220	0.9066	0.071*
H32B	1.0844	0.6885	0.8879	0.071*
H32C	1.0587	0.5653	0.9186	0.071*
C4	0.7819 (5)	0.5376 (3)	0.5669 (3)	0.0331 (8)
O41	0.7212 (4)	0.5922 (2)	0.5066 (2)	0.0403 (7)
N5	0.7990 (5)	0.4258 (3)	0.5324 (2)	0.0339 (7)
H5	0.845 (6)	0.394 (4)	0.589 (3)	0.054 (13)*
C11	0.7977 (5)	0.8916 (3)	0.7249 (3)	0.0348 (9)
C12	0.7627 (5)	0.9682 (3)	0.6638 (3)	0.0361 (9)
C13	0.7635 (6)	1.0856 (4)	0.7151 (4)	0.0493 (11)
H13	0.7411	1.1378	0.6743	0.059*
C14	0.7965 (7)	1.1267 (4)	0.8239 (4)	0.0562 (12)
H14	0.7929	1.2054	0.8577	0.067*
C15	0.8348 (6)	1.0510 (4)	0.8830 (4)	0.0518 (11)
H15	0.8609	1.0793	0.9580	0.062*
C16	0.8355 (6)	0.9351 (4)	0.8346 (3)	0.0426 (10)
H16	0.8621	0.8848	0.8765	0.051*
C17	0.7271 (6)	0.9258 (4)	0.5462 (3)	0.0397 (9)
F1	0.5689 (3)	0.8273 (2)	0.49774 (17)	0.0454 (6)
F2	0.7004 (4)	1.0103 (2)	0.4994 (2)	0.0551 (7)
F3	0.8703 (3)	0.8917 (2)	0.51621 (19)	0.0479 (6)
C51	0.7531 (5)	0.3478 (3)	0.4275 (3)	0.0327 (8)
C52	0.6655 (5)	0.3738 (3)	0.3373 (3)	0.0313 (8)
H52	0.6368	0.4477	0.3421	0.038*
C53	0.6236 (5)	0.2848 (3)	0.2408 (3)	0.0317 (8)
C54	0.6653 (5)	0.1758 (3)	0.2319 (3)	0.0331 (8)
C55	0.7525 (5)	0.1505 (3)	0.3207 (3)	0.0336 (8)
H55	0.7803	0.0763	0.3150	0.040*
C56	0.7974 (5)	0.2381 (3)	0.4182 (3)	0.0333 (8)
H56	0.8596	0.2241	0.4803	0.040*
N57	0.5347 (5)	0.2801 (3)	0.1374 (2)	0.0372 (8)
H57	0.508 (6)	0.344 (4)	0.125 (3)	0.043 (11)*
C58	0.5177 (6)	0.1715 (3)	0.0662 (3)	0.0393 (9)
O58	0.4399 (5)	0.1368 (2)	−0.0309 (2)	0.0484 (8)
N59	0.6035 (5)	0.1099 (3)	0.1242 (3)	0.0369 (8)
H59	0.602 (6)	0.044 (4)	0.103 (3)	0.033 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0469 (6)	0.0313 (5)	0.0601 (7)	0.0178 (5)	0.0050 (5)	0.0182 (5)
O1S	0.072 (2)	0.0297 (15)	0.071 (2)	0.0220 (15)	0.0165 (16)	0.0208 (14)
C1S	0.097 (5)	0.058 (3)	0.086 (4)	0.019 (3)	0.034 (3)	−0.007 (3)
C2S	0.051 (3)	0.058 (3)	0.059 (3)	0.023 (2)	0.015 (2)	0.022 (2)
N1	0.0345 (18)	0.0260 (16)	0.0355 (18)	0.0111 (13)	0.0083 (14)	0.0114 (14)
N2	0.0294 (16)	0.0316 (17)	0.0409 (17)	0.0116 (13)	0.0123 (13)	0.0171 (13)
C3	0.032 (2)	0.0280 (19)	0.041 (2)	0.0115 (16)	0.0097 (16)	0.0152 (15)
C31	0.041 (2)	0.037 (2)	0.049 (2)	0.0177 (18)	0.0122 (18)	0.0246 (18)
O31	0.071 (2)	0.0423 (17)	0.0500 (17)	0.0280 (15)	0.0088 (14)	0.0250 (13)
C32	0.052 (3)	0.051 (3)	0.043 (2)	0.018 (2)	0.008 (2)	0.023 (2)
C4	0.028 (2)	0.0256 (18)	0.044 (2)	0.0070 (15)	0.0057 (16)	0.0134 (16)
O41	0.0509 (17)	0.0294 (14)	0.0387 (14)	0.0154 (12)	0.0026 (12)	0.0128 (11)
N5	0.0397 (18)	0.0257 (16)	0.0382 (17)	0.0130 (14)	0.0077 (14)	0.0131 (13)
C11	0.029 (2)	0.0265 (19)	0.048 (2)	0.0082 (15)	0.0075 (16)	0.0122 (16)
C12	0.0273 (19)	0.0269 (19)	0.054 (2)	0.0079 (15)	0.0101 (17)	0.0144 (17)
C13	0.049 (3)	0.031 (2)	0.072 (3)	0.020 (2)	0.016 (2)	0.017 (2)
C14	0.054 (3)	0.029 (2)	0.073 (3)	0.011 (2)	0.013 (2)	−0.001 (2)
C15	0.047 (3)	0.046 (3)	0.048 (2)	0.011 (2)	0.005 (2)	−0.0015 (19)
C16	0.037 (2)	0.034 (2)	0.048 (2)	0.0094 (17)	0.0050 (18)	0.0046 (17)
C17	0.037 (2)	0.035 (2)	0.057 (2)	0.0166 (18)	0.0185 (19)	0.0228 (18)
F1	0.0424 (14)	0.0451 (14)	0.0466 (13)	0.0099 (11)	0.0079 (10)	0.0182 (10)
F2	0.0686 (18)	0.0478 (14)	0.0733 (16)	0.0322 (13)	0.0274 (13)	0.0412 (13)
F3	0.0461 (14)	0.0534 (15)	0.0633 (15)	0.0276 (12)	0.0254 (11)	0.0311 (12)
C51	0.032 (2)	0.0268 (18)	0.042 (2)	0.0101 (15)	0.0087 (16)	0.0157 (15)
C52	0.030 (2)	0.0203 (17)	0.045 (2)	0.0087 (14)	0.0093 (16)	0.0126 (15)
C53	0.0303 (19)	0.0278 (18)	0.042 (2)	0.0115 (15)	0.0096 (16)	0.0165 (16)
C54	0.0300 (19)	0.0245 (18)	0.047 (2)	0.0083 (15)	0.0112 (16)	0.0143 (16)
C55	0.034 (2)	0.0241 (18)	0.052 (2)	0.0133 (15)	0.0166 (17)	0.0202 (17)
C56	0.0296 (19)	0.0302 (19)	0.046 (2)	0.0118 (15)	0.0104 (16)	0.0196 (17)
N57	0.045 (2)	0.0203 (16)	0.0464 (19)	0.0152 (14)	0.0055 (15)	0.0106 (14)
C58	0.044 (2)	0.0244 (19)	0.048 (2)	0.0124 (17)	0.0084 (18)	0.0110 (17)
O58	0.066 (2)	0.0306 (15)	0.0435 (16)	0.0199 (14)	0.0002 (14)	0.0092 (12)
N59	0.046 (2)	0.0213 (16)	0.0440 (19)	0.0158 (15)	0.0077 (15)	0.0102 (14)

Geometric parameters (Å, º) top

S1—O1S	1.497 (3)	C12—C17	1.494 (6)
S1—C1S	1.768 (6)	C13—C14	1.383 (7)
S1—C2S	1.770 (5)	C13—H13	0.9500
C1S—H1S1	0.9800	C14—C15	1.387 (7)
C1S—H1S2	0.9800	C14—H14	0.9500
C1S—H1S3	0.9800	C15—C16	1.382 (6)
C2S—H2S1	0.9800	C15—H15	0.9500
C2S—H2S2	0.9800	C16—H16	0.9500
C2S—H2S3	0.9800	C17—F3	1.348 (5)
N1—N2	1.325 (4)	C17—F2	1.349 (4)
N1—C11	1.402 (5)	C17—F1	1.359 (5)
N1—H1	0.81 (4)	C51—C52	1.408 (5)
N2—C3	1.313 (5)	C51—C56	1.415 (5)
C3—C31	1.495 (5)	C52—C53	1.387 (5)
C3—C4	1.507 (5)	C52—H52	0.9500
C31—O31	1.233 (5)	C53—C54	1.397 (5)
C31—C32	1.507 (6)	C53—N57	1.406 (5)
C32—H32A	0.9800	C54—C55	1.386 (5)
C32—H32B	0.9800	C54—N59	1.396 (5)
C32—H32C	0.9800	C55—C56	1.387 (5)
C4—O41	1.248 (4)	C55—H55	0.9500
C4—N5	1.351 (5)	C56—H56	0.9500
N5—C51	1.414 (5)	N57—C58	1.375 (5)
N5—H5	0.97 (4)	N57—H57	0.88 (5)
C11—C16	1.391 (6)	C58—O58	1.244 (5)
C11—C12	1.409 (5)	C58—N59	1.373 (5)
C12—C13	1.404 (5)	N59—H59	0.77 (4)

O1S—S1—C1S	105.4 (3)	C14—C13—H13	119.5
O1S—S1—C2S	107.5 (2)	C12—C13—H13	119.5
C1S—S1—C2S	97.9 (3)	C13—C14—C15	118.9 (4)
S1—C1S—H1S1	109.5	C13—C14—H14	120.5
S1—C1S—H1S2	109.5	C15—C14—H14	120.5
H1S1—C1S—H1S2	109.5	C16—C15—C14	121.1 (4)
S1—C1S—H1S3	109.5	C16—C15—H15	119.4
H1S1—C1S—H1S3	109.5	C14—C15—H15	119.4
H1S2—C1S—H1S3	109.5	C15—C16—C11	120.5 (4)
S1—C2S—H2S1	109.5	C15—C16—H16	119.7
S1—C2S—H2S2	109.5	C11—C16—H16	119.7
H2S1—C2S—H2S2	109.5	F3—C17—F2	106.2 (3)
S1—C2S—H2S3	109.5	F3—C17—F1	105.3 (3)
H2S1—C2S—H2S3	109.5	F2—C17—F1	105.5 (3)
H2S2—C2S—H2S3	109.5	F3—C17—C12	113.1 (3)
N2—N1—C11	119.4 (3)	F2—C17—C12	113.6 (3)
N2—N1—H1	114 (3)	F1—C17—C12	112.5 (3)
C11—N1—H1	127 (3)	C52—C51—N5	123.6 (3)
C3—N2—N1	120.3 (3)	C52—C51—C56	121.0 (3)
N2—C3—C31	112.5 (3)	N5—C51—C56	115.4 (3)
N2—C3—C4	123.3 (3)	C53—C52—C51	115.9 (3)
C31—C3—C4	124.2 (3)	C53—C52—H52	122.1
O31—C31—C3	121.4 (4)	C51—C52—H52	122.1
O31—C31—C32	120.0 (3)	C52—C53—C54	123.0 (3)
C3—C31—C32	118.6 (3)	C52—C53—N57	130.7 (3)
C31—C32—H32A	109.5	C54—C53—N57	106.3 (3)
C31—C32—H32B	109.5	C55—C54—N59	132.0 (3)
H32A—C32—H32B	109.5	C55—C54—C53	121.1 (3)
C31—C32—H32C	109.5	N59—C54—C53	106.8 (3)
H32A—C32—H32C	109.5	C54—C55—C56	117.2 (3)
H32B—C32—H32C	109.5	C54—C55—H55	121.4
O41—C4—N5	123.6 (3)	C56—C55—H55	121.4
O41—C4—C3	120.8 (3)	C55—C56—C51	121.7 (3)
N5—C4—C3	115.6 (3)	C55—C56—H56	119.2
C4—N5—C51	129.6 (3)	C51—C56—H56	119.2
C4—N5—H5	114 (3)	C58—N57—C53	110.2 (3)
C51—N5—H5	116 (3)	C58—N57—H57	129 (3)
C16—C11—N1	121.4 (3)	C53—N57—H57	121 (3)
C16—C11—C12	119.1 (4)	O58—C58—N59	127.4 (3)
N1—C11—C12	119.5 (3)	O58—C58—N57	126.5 (3)
C13—C12—C11	119.2 (4)	N59—C58—N57	106.2 (3)
C13—C12—C17	120.2 (4)	C58—N59—C54	110.4 (3)
C11—C12—C17	120.6 (3)	C58—N59—H59	125 (3)
C14—C13—C12	121.1 (4)	C54—N59—H59	123 (3)

C11—N1—N2—C3	−179.3 (3)	C13—C12—C17—F2	0.9 (5)
N1—N2—C3—C31	179.1 (3)	C11—C12—C17—F2	−178.5 (3)
N1—N2—C3—C4	0.6 (5)	C13—C12—C17—F1	−118.9 (4)
N2—C3—C31—O31	175.6 (4)	C11—C12—C17—F1	61.7 (5)
C4—C3—C31—O31	−6.0 (6)	C4—N5—C51—C52	−4.3 (6)
N2—C3—C31—C32	−3.1 (5)	C4—N5—C51—C56	177.0 (4)
C4—C3—C31—C32	175.4 (4)	N5—C51—C52—C53	−177.5 (3)
N2—C3—C4—O41	−2.1 (6)	C56—C51—C52—C53	1.1 (5)
C31—C3—C4—O41	179.5 (4)	C51—C52—C53—C54	−0.3 (6)
N2—C3—C4—N5	176.2 (4)	C51—C52—C53—N57	178.7 (4)
C31—C3—C4—N5	−2.1 (5)	C52—C53—C54—C55	−0.1 (6)
O41—C4—N5—C51	−1.2 (6)	N57—C53—C54—C55	−179.2 (3)
C3—C4—N5—C51	−179.5 (4)	C52—C53—C54—N59	−180.0 (4)
N2—N1—C11—C16	−9.7 (5)	N57—C53—C54—N59	0.9 (4)
N2—N1—C11—C12	171.0 (3)	N59—C54—C55—C56	179.5 (4)
C16—C11—C12—C13	−1.2 (6)	C53—C54—C55—C56	−0.4 (6)
N1—C11—C12—C13	178.2 (4)	C54—C55—C56—C51	1.2 (6)
C16—C11—C12—C17	178.2 (4)	C52—C51—C56—C55	−1.7 (6)
N1—C11—C12—C17	−2.4 (6)	N5—C51—C56—C55	177.0 (3)
C11—C12—C13—C14	−0.5 (6)	C52—C53—N57—C58	−178.0 (4)
C17—C12—C13—C14	−179.9 (4)	C54—C53—N57—C58	1.1 (4)
C12—C13—C14—C15	1.9 (7)	C53—N57—C58—O58	177.4 (4)
C13—C14—C15—C16	−1.7 (7)	C53—N57—C58—N59	−2.6 (4)
C14—C15—C16—C11	0.0 (7)	O58—C58—N59—C54	−176.8 (4)
N1—C11—C16—C15	−177.9 (4)	N57—C58—N59—C54	3.2 (4)
C12—C11—C16—C15	1.4 (6)	C55—C54—N59—C58	177.6 (4)
C13—C12—C17—F3	122.0 (4)	C53—C54—N59—C58	−2.5 (4)
C11—C12—C17—F3	−57.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O41	0.81 (4)	1.88 (4)	2.578 (4)	144 (4)
N5—H5···O31	0.97 (4)	1.85 (4)	2.684 (4)	143 (4)
N57—H57···O1S	0.88 (5)	1.91 (5)	2.770 (4)	165 (4)
N59—H59···O58ⁱ	0.77 (4)	2.05 (4)	2.815 (4)	172 (4)

Symmetry code: (i) −x+1, −y, −z.

Experimental details

	(PO36)	(PO62)	(PY151)	(PY154)
Crystal data
Chemical formula	C₁₇H₁₃ClN₆O₅	C₁₇H₁₄N₆O₅	C₁₈H₁₅N₅O₅	C₁₈H₁₄F₃N₅O₃
M_r	416.78	382.34	381.35	405.34
Crystal system, space group	Triclinic, P1	Triclinic, P1	Triclinic, P1	Monoclinic, P2₁/c
Temperature (K)	293	293	293	293
a, b, c (Å)	8.6533 (7), 9.1170 (6), 11.3831 (6)	7.2689 (8), 10.3176 (14), 12.1761 (15)	5.12970 (14), 9.2292 (3), 17.4094 (6)	14.5848 (5), 8.5448 (2), 13.7794 (4)
α, β, γ (°)	74.717 (2), 81.597 (4), 88.982 (3)	96.462 (6), 95.869 (4), 109.849 (8)	95.857 (2), 95.5056 (17), 91.7980 (13)	90, 96.0670 (19), 90
V (Å³)	856.78 (10)	843.78 (19)	815.42 (4)	1707.62 (9)
Z	2	2	2	4
Radiation type	Cu Kα₁, λ = 1.54056 Å	Cu Kα₁, λ = 1.54056 Å	Cu Kα₁, λ = 1.54056 Å	Cu Kα₁, λ = 1.54056 Å
µ (mm⁻¹)	2.41	0.97	0.98	1.15
Specimen shape, size (mm)	Cylinder, 10 × 0.7	Flat_sheet, 10 × 1.2	Cylinder, 10 × 0.7	Cylinder, 10 × 0.7

Data collection
Diffractometer	STOE-Stadi-P diffractometer	STOE-Stadi-P diffractometer	STOE-Stadi-P diffractometer	STOE-Stadi-P diffractometer
Specimen mounting	'glass capillary'	Flat sample holder	'glass capillary'	'glass capillary'
Data collection mode	Transmission	Transmission	Transmission	Transmission
Data collection method	Step	Step	Step	Step
Absorption correction	–	–	–	–
T_min, T_max	–	–	–	–
No. of measured, independent and observed reflections	–	–	–	–
R_int	–	–	–	–
θ values (°)	2θ_min = 2.00 2θ_max = 75.00 2θ_step = 0.01	2θ_min = 3.00 2θ_max = 34.00 2θ_step = 0.02	2θ_min = 4.00 2θ_max = 74.00 2θ_step = 0.01	2θ_min = 3.00 2θ_max = 70.00 2θ_step = 0.01
Distance from source to specimen (mm)	–	–	–	–

Refinement
R factors and goodness of fit	R_p = 0.029, R_wp = 0.039, R_exp = 0.094, χ² = 1.103	R_p = 0.030, R_wp = 0.040, R_exp = 0.055, χ² = 1.277	R_p = 0.015, R_wp = 0.021, R_exp = 0.054, χ² = 1.369	R_p = 0.036, R_wp = 0.047, R_exp = 0.090, χ² = 1.369
No. of reflections/data points	9800	1550	7000	6700
No. of parameters	191	190	194	180
No. of restraints	116	118	118	120
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	–	–	–	–

	(PY181)	(PY194)	(BIRZIL)	(PY154-DMSO)
Crystal data
Chemical formula	C₂₅H₂₁N₇O₅	C₁₈H₁₇N₅O₄	C₁₈H₁₆ClN₅O₄	C₂₀H₂₀F₃N₅O₄S
M_r	499.49	367.37	401.81	483.47
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, P2₁/c	Monoclinic, C2/c	Triclinic, P1
Temperature (K)	293	293	293	173
a, b, c (Å)	22.5510 (8), 4.96366 (13), 21.2815 (6)	14.7172 (16), 5.9852 (5), 20.7919 (13)	17.126 (2), 5.036 (2), 42.45 (1)	7.5478 (14), 11.941 (2), 13.530 (2)
α, β, γ (°)	90, 109.4539 (13), 90	90, 114.818 (4), 90	90, 97.36 (2), 90	103.996 (14), 101.670 (15), 104.491 (14)
V (Å³)	2246.16 (12)	1662.3 (2)	3631 (2)	1099.9 (3)
Z	4	4	8	2
Radiation type	Cu Kα₁, λ = 1.54056 Å	Cu Kα₁, λ = 1.54056 Å	Cu Kα	Mo Kα
µ (mm⁻¹)	0.89	0.89	2.19	0.21
Specimen shape, size (mm)	Cylinder, 10 × 0.7	Flat_sheet, 10 × 1.2	0.5 × 0.25 × 0.05	0.17 × 0.11 × 0.02

Data collection
Diffractometer	STOE-Stadi-P diffractometer	STOE-Stadi-P diffractometer	Nicolet R3 computer-controlled four circle diffractometer	STOE IPDS II two-circle- diffractometer
Specimen mounting	'glass capillary'	Flat sample holder	–	–
Data collection mode	Transmission	Transmission	–	–
Data collection method	Step	Step	2θ/θ scan	ω scans
Absorption correction	–	–	–	Multi-scan MULABS (Spek, 2003; Blessing, 1995)
T_min, T_max	–	–	–	0.965, 0.996
No. of measured, independent and observed reflections	–	–	2394, 2303, 971	11729, 4108, 2452
R_int	–	–	0.047	0.091
θ values (°)	2θ_min = 3.00 2θ_max = 60.00 2θ_step = 0.01	2θ_min = 3.00 2θ_max = 34.00 2θ_step = 0.02	θ_max = 55.2, θ_min = 4.2	θ_max = 25.6, θ_min = 3.5
Distance from source to specimen (mm)	–	–	0.532	0.608

Refinement
R factors and goodness of fit	R_p = 0.012, R_wp = 0.015, R_exp = 0.036, χ² = 1.188	R_p = 0.029, R_wp = 0.039, R_exp = 0.048, χ² = 1.322	R[F² > 2σ(F²)] = 0.078, wR(F²) = 0.198, S = 0.92	R[F² > 2σ(F²)] = 0.065, wR(F²) = 0.166, S = 0.95
No. of reflections/data points	5700	1550	2303	4108
No. of parameters	224	176	254	316
No. of restraints	162	122	0	0
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	–	–	0.25, −0.25	0.32, −0.36

Computer programs: STOE WINXPOW (STOE & CIE GmbH, 2004), Nicolet software, X-AREA (Stoe & Cie, 2001), TOPAS (Coelho, 2006), DASH (David et al., 2006), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), Mercury (Macrae et al., 2006), SHELX97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991), DASH, TOPAS, Mercury, SHELXL97.

Hydrogen-bond geometry (Å, º) for (BIRZIL) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	2.28	2.616 (9)	103.3
C13—H13···O3	0.93	2.32	2.899 (9)	119.8
N1—H1···O3	0.86	1.87	2.555 (8)	134.9
N3—H3···O2	0.86	1.94	2.685 (8)	143.7
N4—H4···O2ⁱ	0.86	2.06	2.919 (9)	174.1
N5—H5···O4ⁱⁱ	0.86	1.96	2.819 (8)	173.1

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

Hydrogen-bond geometry (Å, º) for (PY154-DMSO) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O41	0.81 (4)	1.88 (4)	2.578 (4)	144 (4)
N5—H5···O31	0.97 (4)	1.85 (4)	2.684 (4)	143 (4)
N57—H57···O1S	0.88 (5)	1.91 (5)	2.770 (4)	165 (4)
N59—H59···O58ⁱ	0.77 (4)	2.05 (4)	2.815 (4)	172 (4)

Symmetry code: (i) −x+1, −y, −z.

Format		BIBTeX
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Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text