Polymorphs, hydrates and solvates of a co-crystal of caffeine with anthranilic acid

A polymorph screen on a new 1:1 co-crystal of caffeine, C₈H₁₀N₄O₂, with anthranilic acid, C₇H₇NO₂, has revealed a rich diversity of crystal forms (two polymorphs, two hydrates and seven solvates, including two sets of isostructural solvates). These forms were prepared by liquid-assisted grinding and solution crystallization, and the crystal structures of nine of these forms have been solved using either single-crystal or powder X-ray data. The structures contain O—H...N and N—H...O hydrogen bonds through which caffeine and anthranilic acid molecules assemble to form zigzag-type chains. These chains can interact in an anti-parallel and offset manner to form cage- or channel-type skeletons within which solvent molecules can be located, giving rise to the diversity of forms observed for this co-crystal. In contrast, an equivalent series of liquid-assisted grinding and solution crystallization experiments with the closely related system of theobromine, C₇H₈N₄O₂, and anthranilic acid resulted in the formation of only one 1:1 co-crystal form.

S1. Experimental

S1.1. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1.

S2. Results and discussion

Computing details

Data collection: X'Pert Data Collector (Panalytical, 2010) for Form1, Form2, Bromobenzene_Hemisolvate, Toluene_Hemisolvate, Theobromine_AA; Collect (Nonius, 1998) for Chlorobenzene_Hemisolvate, Toluene_Monosolvate, o_Xylene_Monosolvate, p_Xylene_Sesquisolvate, Monohydrate. Cell refinement: DASH 3.3 (David et al., 2006) and DICVOL 06 (Boultif & Louer, 2004) for Form1, Form2, Bromobenzene_Hemisolvate, Toluene_Hemisolvate, Theobromine_AA; HKL SCALEPACK (Otwinowski & Minor, 1997) for Chlorobenzene_Hemisolvate, Toluene_Monosolvate, o_Xylene_Monosolvate, p_Xylene_Sesquisolvate, Monohydrate. Data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997) for Chlorobenzene_Hemisolvate, Toluene_Monosolvate, o_Xylene_Monosolvate, p_Xylene_Sesquisolvate, Monohydrate. Program(s) used to solve structure: TOPAS Academic (Coelho, 2007) for Form1, Form2, Bromobenzene_Hemisolvate, Toluene_Hemisolvate, Theobromine_AA; SIR92 (Altomare et al., 1994) for Chlorobenzene_Hemisolvate, Toluene_Monosolvate, o_Xylene_Monosolvate, p_Xylene_Sesquisolvate, Monohydrate. Program(s) used to refine structure: TOPAS Academic for Form1, Form2, Bromobenzene_Hemisolvate, Toluene_Hemisolvate, Theobromine_AA; SHELXL97 (Sheldrick, 2008) for Chlorobenzene_Hemisolvate, Toluene_Monosolvate, o_Xylene_Monosolvate, p_Xylene_Sesquisolvate, Monohydrate. Software used to prepare material for publication: SHELXL97 for Chlorobenzene_Hemisolvate, Toluene_Monosolvate, o_Xylene_Monosolvate, p_Xylene_Sesquisolvate, Monohydrate.

Figures

(Form1)

Crystal data

C8H10N4O2·C7H7NO2	γ = 93.5278 (9)°
Mr = 331.33	V = 1567.35 (7) Å^3
Triclinic, P1	Z = 4
a = 8.4853 (2) Å	F(000) = 696
b = 13.4240 (3) Å	Dx = 1.404 Mg m^−3
c = 14.8856 (4) Å	Synchrotron radiation, λ = 1.033787 Å
α = 111.7249 (16)°	T = 293 K
β = 92.8464 (15)°	white

Data collection

Diamond Light Source beamline I11 diffractometer	Data collection mode: transmission
Radiation source: synchrotron	Scan method: continuous
Si(111) monochromator	2θmin = 3.000°, 2θmax = 40.000°, 2θstep = 0.004°
Specimen mounting: glass capillary

Refinement

Rp = 0.014	310 parameters
Rwp = 0.019	224 restraints
Rexp = 0.010	0 constraints
RBragg = 0.003
χ^2 = 3.587
9251 data points	Background function: Chebyshev polynomial
Profile function: pseudo-Voigt	Preferred orientation correction: spherical harmonics

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.6670 (5)	0.2757 (3)	0.8500 (3)	0.069
C2	0.5384 (5)	0.3460 (4)	0.8572 (5)	0.069
C3	0.8129 (5)	0.3035 (3)	0.8231 (5)	0.069
C4	0.6467 (5)	0.1789 (3)	0.8680 (4)	0.069
O5	0.5913 (6)	0.4391 (4)	0.8481 (6)	0.069
O6	0.4019 (8)	0.3256 (7)	0.8779 (6)	0.069
C7	0.9404 (5)	0.2385 (3)	0.8138 (5)	0.069
H8	0.825 (3)	0.3700 (14)	0.8128 (13)	0.082
C9	0.7730 (5)	0.1143 (3)	0.8562 (5)	0.069
N10	0.5137 (5)	0.1447 (3)	0.8967 (5)	0.069
H11	0.513 (3)	0.4828 (14)	0.8425 (15)	0.082
C12	0.9139 (6)	0.1391 (3)	0.8248 (5)	0.069
H13	1.042 (3)	0.2598 (13)	0.7985 (16)	0.082
H14	0.755 (2)	0.0511 (14)	0.8687 (14)	0.082
H15	0.427 (3)	0.1855 (14)	0.8997 (15)	0.082
H16	0.505 (3)	0.0764 (14)	0.9022 (14)	0.082
H17	1.000 (3)	0.0982 (14)	0.8253 (13)	0.082
C18	0.1523 (6)	0.5198 (3)	0.6438 (3)	0.069
C19	0.2851 (6)	0.4499 (4)	0.6316 (5)	0.069
C20	0.0001 (5)	0.4852 (3)	0.6610 (5)	0.069
C21	0.1753 (5)	0.6223 (3)	0.6391 (4)	0.069
O22	0.2360 (7)	0.3542 (4)	0.6340 (5)	0.069
O23	0.4245 (8)	0.4699 (6)	0.6134 (7)	0.069
C24	−0.1305 (5)	0.5468 (3)	0.6701 (6)	0.069
H25	−0.014 (3)	0.4158 (14)	0.6637 (12)	0.082
C26	0.0476 (5)	0.6857 (3)	0.6554 (5)	0.069
N27	0.3154 (5)	0.6630 (3)	0.6223 (5)	0.069
H28	0.320 (3)	0.3109 (14)	0.6288 (14)	0.082
C29	−0.0995 (5)	0.6504 (3)	0.6734 (6)	0.069
H30	−0.236 (3)	0.5213 (14)	0.6805 (14)	0.082
H31	0.065 (3)	0.7520 (15)	0.6490 (14)	0.082
H32	0.401 (3)	0.6206 (14)	0.6167 (14)	0.082
H33	0.326 (3)	0.7334 (14)	0.6227 (14)	0.082
H34	−0.183 (2)	0.6954 (15)	0.6830 (15)	0.082
C35	0.1660 (5)	0.6970 (3)	0.9007 (3)	0.069
C36	0.3225 (5)	0.6747 (3)	0.8849 (4)	0.069
C37	0.1097 (5)	0.7955 (3)	0.9039 (5)	0.069
N38	0.0891 (5)	0.6065 (3)	0.9093 (4)	0.069
N39	0.4342 (5)	0.7452 (3)	0.8737 (5)	0.069
N40	0.3462 (7)	0.5751 (4)	0.8828 (6)	0.069
N41	0.2344 (5)	0.8650 (3)	0.8922 (5)	0.069
O42	−0.0292 (8)	0.8213 (6)	0.9147 (9)	0.069
C43	0.2025 (5)	0.5362 (3)	0.8978 (5)	0.069
C44	−0.0786 (5)	0.5895 (4)	0.9290 (3)	0.069
C45	0.3911 (6)	0.8428 (3)	0.8753 (6)	0.069
C46	0.5944 (6)	0.7162 (3)	0.8621 (3)	0.069
C47	0.2030 (6)	0.9771 (3)	0.9085 (3)	0.069
H48	0.183 (2)	0.4666 (15)	0.9004 (14)	0.082
H49	−0.099 (3)	0.6421 (13)	0.9900 (13)	0.082
H50	−0.150 (2)	0.5926 (14)	0.8775 (14)	0.082
H51	−0.097 (3)	0.5204 (15)	0.9309 (14)	0.082
O52	0.4893 (9)	0.9138 (6)	0.8732 (8)	0.069
H53	0.625 (3)	0.6967 (14)	0.9151 (14)	0.082
H54	0.594 (3)	0.6570 (15)	0.8023 (15)	0.082
H55	0.664 (3)	0.7737 (13)	0.8621 (14)	0.082
H56	0.234 (2)	0.9929 (14)	0.8551 (15)	0.082
H57	0.093 (3)	0.9830 (16)	0.9157 (13)	0.082
H58	0.262 (2)	1.0249 (15)	0.9654 (14)	0.082
C59	0.6614 (5)	0.1021 (3)	0.5992 (3)	0.069
C60	0.5097 (5)	0.1278 (3)	0.6213 (4)	0.069
C61	0.7217 (6)	0.0082 (3)	0.6030 (5)	0.069
N62	0.7340 (5)	0.1826 (3)	0.5757 (4)	0.069
N63	0.4029 (5)	0.0600 (3)	0.6450 (5)	0.069
N64	0.4870 (7)	0.2247 (4)	0.6143 (5)	0.069
N65	0.6067 (5)	−0.0555 (3)	0.6278 (5)	0.069
O66	0.8583 (8)	−0.0177 (6)	0.5894 (8)	0.069
C67	0.6274 (5)	0.2555 (3)	0.5861 (4)	0.069
C68	0.8975 (5)	0.1872 (3)	0.5491 (3)	0.069
C69	0.4528 (5)	−0.0340 (3)	0.6502 (5)	0.069
C70	0.2399 (5)	0.0844 (3)	0.6643 (3)	0.069
C71	0.6560 (6)	−0.1575 (3)	0.6308 (3)	0.069
H72	0.648 (2)	0.3208 (14)	0.5755 (15)	0.082
H73	0.970 (3)	0.2047 (14)	0.6040 (14)	0.082
H74	0.917 (3)	0.1200 (13)	0.5032 (15)	0.082
H75	0.910 (3)	0.2407 (14)	0.5223 (14)	0.082
O76	0.3591 (10)	−0.1046 (6)	0.6601 (8)	0.069
H77	0.243 (2)	0.1449 (15)	0.7225 (15)	0.082
H78	0.192 (3)	0.0968 (15)	0.6112 (15)	0.082
H79	0.183 (3)	0.0257 (15)	0.6704 (14)	0.082
H80	0.598 (3)	−0.2175 (14)	0.5809 (14)	0.082
H81	0.766 (3)	−0.1584 (16)	0.6218 (15)	0.082
H82	0.636 (2)	−0.1595 (14)	0.6918 (14)	0.082

Geometric parameters (Å, º)

C1—C2	1.469 (7)	N38—C44	1.488 (6)
C1—C3	1.392 (7)	N39—C45	1.375 (7)
C1—C4	1.422 (7)	N39—C46	1.438 (7)
C2—O5	1.357 (9)	N40—C43	1.358 (8)
C2—O6	1.253 (9)	N41—C45	1.395 (7)
C3—C7	1.412 (6)	N41—C47	1.476 (6)
C3—H8	0.96 (2)	C43—H48	0.95 (2)
C4—C9	1.397 (7)	C44—H49	0.95 (2)
C4—N10	1.341 (7)	C44—H50	0.96 (2)
O5—H11	0.93 (2)	C44—H51	0.94 (2)
C7—C12	1.410 (8)	C45—O52	1.237 (10)
C7—H13	0.95 (2)	C46—H53	0.95 (2)
C9—C12	1.371 (8)	C46—H54	0.95 (2)
C9—H14	0.94 (2)	C46—H55	0.94 (2)
N10—H15	0.94 (2)	C47—H56	0.94 (2)
N10—H16	0.95 (2)	C47—H57	0.95 (2)
C12—H17	0.94 (2)	C47—H58	0.95 (2)
C18—C19	1.486 (7)	C59—C60	1.377 (7)
C18—C20	1.414 (7)	C59—C61	1.409 (7)
C18—C21	1.405 (7)	C59—N62	1.374 (7)
C19—O22	1.341 (8)	C60—N63	1.393 (8)
C19—O23	1.261 (9)	C60—N64	1.367 (8)
C20—C24	1.405 (6)	C61—N65	1.410 (8)
C20—H25	0.95 (2)	C61—O66	1.236 (8)
C21—C26	1.394 (6)	N62—C67	1.346 (7)
C21—N27	1.351 (7)	N62—C68	1.465 (6)
O22—H28	0.94 (2)	N63—C69	1.383 (8)
C24—C29	1.382 (7)	N63—C70	1.459 (6)
C24—H30	0.98 (2)	N64—C67	1.372 (8)
C26—C29	1.383 (7)	N65—C69	1.385 (7)
C26—H31	0.93 (2)	N65—C71	1.472 (7)
N27—H32	0.94 (2)	C67—H72	0.95 (2)
N27—H33	0.94 (2)	C68—H73	0.95 (2)
C29—H34	0.94 (2)	C68—H74	0.94 (2)
C35—C36	1.392 (6)	C68—H75	0.94 (2)
C35—C37	1.419 (7)	C69—O76	1.254 (10)
C35—N38	1.395 (7)	C70—H77	0.94 (2)
C36—N39	1.358 (7)	C70—H78	0.95 (2)
C36—N40	1.354 (8)	C70—H79	0.94 (2)
C37—N41	1.428 (7)	C71—H80	0.95 (2)
C37—O42	1.250 (9)	C71—H81	0.95 (2)
N38—C43	1.361 (7)	C71—H82	0.94 (2)
C2—C1—C3	119.0 (5)	C45—N41—C47	114.2 (4)
C2—C1—C4	122.3 (4)	N38—C43—N40	113.5 (5)
C3—C1—C4	118.8 (4)	N38—C43—H48	123 (1)
C1—C2—O5	111.3 (5)	N40—C43—H48	123 (1)
C1—C2—O6	123.4 (6)	N38—C44—H49	110 (1)
O5—C2—O6	125.1 (6)	N38—C44—H50	111 (1)
C1—C3—C7	121.6 (5)	N38—C44—H51	109 (1)
C1—C3—H8	117 (1)	H49—C44—H50	111 (2)
C7—C3—H8	121 (1)	H49—C44—H51	109 (2)
C1—C4—C9	118.8 (5)	H50—C44—H51	107 (2)
C1—C4—N10	124.5 (4)	N39—C45—N41	117.2 (5)
C9—C4—N10	116.7 (5)	N39—C45—O52	122.1 (6)
C2—O5—H11	116 (1)	N41—C45—O52	120.2 (6)
C3—C7—C12	118.5 (5)	N39—C46—H53	107 (1)
C3—C7—H13	121 (1)	N39—C46—H54	107 (2)
C12—C7—H13	120 (1)	N39—C46—H55	112 (1)
C4—C9—C12	122.3 (5)	H53—C46—H54	111 (2)
C4—C9—H14	116 (1)	H53—C46—H55	109 (2)
C12—C9—H14	121 (1)	H54—C46—H55	110 (2)
C4—N10—H15	116 (1)	N41—C47—H56	109 (1)
C4—N10—H16	120 (1)	N41—C47—H57	108 (1)
H15—N10—H16	123 (2)	N41—C47—H58	110 (1)
C7—C12—C9	119.5 (4)	H56—C47—H57	111 (2)
C7—C12—H17	119 (1)	H56—C47—H58	109 (2)
C9—C12—H17	119 (1)	H57—C47—H58	110 (2)
C19—C18—C20	120.8 (4)	C60—C59—C61	122.5 (5)
C19—C18—C21	120.8 (4)	C60—C59—N62	108.0 (4)
C20—C18—C21	118.4 (4)	C61—C59—N62	129.5 (5)
C18—C19—O22	111.1 (4)	C59—C60—N63	122.1 (5)
C18—C19—O23	127.1 (7)	C59—C60—N64	109.2 (5)
O22—C19—O23	121.6 (6)	N63—C60—N64	128.7 (5)
C18—C20—C24	123.1 (5)	C59—C61—N65	111.7 (4)
C18—C20—H25	118 (1)	C59—C61—O66	126.5 (7)
C24—C20—H25	119 (1)	N65—C61—O66	121.7 (7)
C18—C21—C26	117.9 (5)	C59—N62—C67	106.1 (4)
C18—C21—N27	123.2 (4)	C59—N62—C68	125.5 (4)
C26—C21—N27	118.8 (5)	C67—N62—C68	128.4 (5)
C19—O22—H28	111 (1)	C60—N63—C69	118.9 (4)
C20—C24—C29	116.4 (4)	C60—N63—C70	122.4 (5)
C20—C24—H30	122 (1)	C69—N63—C70	118.7 (5)
C29—C24—H30	121 (1)	C60—N64—C67	104.9 (5)
C21—C26—C29	122.4 (5)	C61—N65—C69	128.1 (5)
C21—C26—H31	116 (1)	C61—N65—C71	116.2 (4)
C29—C26—H31	121 (1)	C69—N65—C71	115.7 (5)
C21—N27—H32	117 (1)	N62—C67—N64	111.8 (5)
C21—N27—H33	120 (1)	N62—C67—H72	124 (1)
H32—N27—H33	123 (2)	N64—C67—H72	125 (1)
C24—C29—C26	121.2 (4)	N62—C68—H73	111 (1)
C24—C29—H34	119 (1)	N62—C68—H74	109 (1)
C26—C29—H34	120 (1)	N62—C68—H75	108 (1)
C36—C35—C37	122.0 (5)	H73—C68—H74	109 (2)
C36—C35—N38	106.5 (4)	H73—C68—H75	109 (2)
C37—C35—N38	131.4 (4)	H74—C68—H75	110 (2)
C35—C36—N39	123.4 (5)	N63—C69—N65	116.5 (5)
C35—C36—N40	110.9 (5)	N63—C69—O76	122.4 (6)
N39—C36—N40	125.6 (5)	N65—C69—O76	120.2 (6)
C35—C37—N41	110.9 (4)	N63—C70—H77	108 (1)
C35—C37—O42	126.5 (6)	N63—C70—H78	109 (1)
N41—C37—O42	122.5 (6)	N63—C70—H79	110 (1)
C35—N38—C43	104.9 (4)	H77—C70—H78	112 (2)
C35—N38—C44	128.3 (4)	H77—C70—H79	110 (2)
C43—N38—C44	126.8 (5)	H78—C70—H79	108 (2)
C36—N39—C45	118.9 (4)	N65—C71—H80	111 (1)
C36—N39—C46	119.1 (4)	N65—C71—H81	107 (1)
C45—N39—C46	122.0 (5)	N65—C71—H82	108 (1)
C36—N40—C43	104.2 (5)	H80—C71—H81	110 (2)
C37—N41—C45	127.4 (5)	H80—C71—H82	109 (2)
C37—N41—C47	118.1 (4)	H81—C71—H82	111 (2)

(Form2)

Crystal data

C8H10N4O2·C7H7NO2	Z = 4
Mr = 331.33	F(000) = 696
Orthorhombic, Pna21	Dx = 1.363 Mg m^−3
a = 14.53798 (14) Å	Synchrotron radiation, λ = 1.033787 Å
b = 11.07930 (8) Å	T = 293 K
c = 10.02456 (7) Å	white
V = 1614.66 (2) Å^3

Data collection

Diamond Light Source beamline I11 diffractometer	Data collection mode: transmission
Radiation source: synchrotron	Scan method: continuous
Si(111) monochromator	2θmin = 3.000°, 2θmax = 40.000°, 2θstep = 0.004°
Specimen mounting: glass capillary

Refinement

Rp = 0.010	158 parameters
Rwp = 0.013	112 restraints
Rexp = 0.010	0 constraints
RBragg = 0.002
χ^2 = 1.680
9251 data points	Background function: Chebyshev polynomial
Profile function: pseudo-Voigt	Preferred orientation correction: spherical harmonics

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2841 (2)	0.2263 (3)	0.5133 (3)	0.059
C2	0.3110 (2)	0.2754 (5)	0.6469 (3)	0.059
C3	0.1898 (2)	0.2239 (4)	0.4785 (3)	0.059
C4	0.3527 (2)	0.1864 (4)	0.4217 (3)	0.059
O5	0.2381 (2)	0.3110 (4)	0.7185 (3)	0.059
O6	0.3906 (3)	0.2718 (4)	0.6899 (4)	0.059
C7	0.1592 (2)	0.1840 (4)	0.3551 (3)	0.059
H8	0.1445 (10)	0.2506 (13)	0.5421 (14)	0.070
C9	0.32135 (19)	0.1454 (4)	0.2956 (3)	0.059
N10	0.44572 (17)	0.1795 (4)	0.4493 (3)	0.059
H11	0.2569 (10)	0.3344 (15)	0.8048 (14)	0.070
C12	0.22692 (19)	0.1452 (4)	0.2652 (3)	0.059
H13	0.0934 (11)	0.1819 (14)	0.3363 (13)	0.070
H14	0.3694 (10)	0.1213 (12)	0.2336 (13)	0.070
H15	0.4676 (9)	0.2084 (13)	0.5341 (14)	0.070
H16	0.4873 (10)	0.1555 (13)	0.3833 (16)	0.070
H17	0.2072 (9)	0.1175 (12)	0.1823 (15)	0.070
C18	0.6797 (2)	0.5386 (3)	0.6642 (3)	0.059
C19	0.7432 (2)	0.5845 (4)	0.5770 (3)	0.059
C20	0.7042 (2)	0.4917 (4)	0.7925 (3)	0.059
N21	0.5956 (2)	0.5507 (3)	0.6018 (3)	0.059
N22	0.8347 (2)	0.5891 (4)	0.6037 (3)	0.059
N23	0.7005 (2)	0.6228 (4)	0.4640 (3)	0.059
N24	0.7998 (2)	0.4983 (4)	0.8138 (3)	0.059
O25	0.6488 (3)	0.4511 (4)	0.8730 (4)	0.059
C26	0.6100 (2)	0.6022 (4)	0.4826 (3)	0.059
C27	0.5071 (2)	0.5109 (2)	0.6513 (3)	0.059
C28	0.8668 (2)	0.5442 (4)	0.7256 (3)	0.059
C29	0.90036 (19)	0.6416 (2)	0.5107 (3)	0.059
C30	0.83876 (18)	0.4453 (3)	0.9355 (3)	0.059
H31	0.5595 (10)	0.6179 (12)	0.4201 (13)	0.070
H32	0.5006 (9)	0.5361 (13)	0.7451 (13)	0.070
H33	0.5031 (8)	0.4208 (14)	0.6458 (15)	0.070
H34	0.4607 (9)	0.5465 (14)	0.5945 (16)	0.070
O35	0.9496 (3)	0.5420 (4)	0.7520 (4)	0.059
H36	0.9103 (10)	0.7259 (13)	0.5299 (13)	0.070
H37	0.8760 (10)	0.6343 (12)	0.4222 (13)	0.070
H38	0.9583 (10)	0.5979 (12)	0.5190 (13)	0.070
H39	0.8947 (10)	0.3996 (12)	0.9134 (13)	0.070
H40	0.7890 (10)	0.3956 (11)	0.9710 (13)	0.070
H41	0.8572 (10)	0.5079 (11)	0.9987 (12)	0.070

Geometric parameters (Å, º)

C1—C2	1.498 (5)	C19—N23	1.360 (5)
C1—C3	1.416 (4)	C20—N24	1.408 (4)
C1—C4	1.426 (4)	C20—O25	1.225 (5)
C2—O5	1.340 (5)	N21—C26	1.340 (5)
C2—O6	1.236 (5)	N21—C27	1.449 (4)
C3—C7	1.387 (5)	N22—C28	1.399 (5)
C3—H8	0.962 (15)	N22—C29	1.455 (4)
C4—C9	1.418 (5)	N23—C26	1.349 (4)
C4—N10	1.382 (4)	N24—C28	1.411 (5)
O5—H11	0.944 (15)	N24—C30	1.467 (4)
C7—C12	1.402 (4)	C26—H31	0.990 (14)
C7—H13	0.976 (16)	C27—H32	0.985 (15)
C9—C12	1.406 (4)	C27—H33	1.001 (15)
C9—H14	0.972 (14)	C27—H34	0.967 (14)
N10—H15	0.962 (15)	C28—O35	1.233 (5)
N10—H16	0.935 (15)	C29—H36	0.965 (15)
C12—H17	0.931 (14)	C29—H37	0.959 (13)
C18—C19	1.369 (4)	C29—H38	0.976 (15)
C18—C20	1.432 (5)	C30—H39	0.983 (14)
C18—N21	1.380 (4)	C30—H40	0.976 (14)
C19—N22	1.358 (4)	C30—H41	0.976 (14)
C2—C1—C3	118.7 (3)	C18—N21—C26	107.9 (3)
C2—C1—C4	120.4 (3)	C18—N21—C27	127.0 (3)
C3—C1—C4	120.9 (3)	C26—N21—C27	125.0 (3)
C1—C2—O5	112.3 (3)	C19—N22—C28	119.0 (3)
C1—C2—O6	123.0 (4)	C19—N22—C29	122.1 (3)
O5—C2—O6	124.3 (4)	C28—N22—C29	118.9 (3)
C1—C3—C7	122.4 (3)	C19—N23—C26	106.1 (3)
C1—C3—H8	119.6 (9)	C20—N24—C28	127.2 (3)
C7—C3—H8	118.0 (9)	C20—N24—C30	119.1 (3)
C1—C4—C9	116.6 (3)	C28—N24—C30	113.5 (3)
C1—C4—N10	124.9 (3)	N21—C26—N23	110.3 (3)
C9—C4—N10	118.4 (3)	N21—C26—H31	121.9 (9)
C2—O5—H11	110.0 (9)	N23—C26—H31	127.7 (9)
C3—C7—C12	116.5 (3)	N21—C27—H32	109.0 (8)
C3—C7—H13	119.6 (9)	N21—C27—H33	109.6 (8)
C12—C7—H13	123.8 (9)	N21—C27—H34	107.0 (9)
C4—C9—C12	120.5 (3)	H32—C27—H33	109.3 (12)
C4—C9—H14	115.3 (9)	H32—C27—H34	112.3 (12)
C12—C9—H14	124.2 (9)	H33—C27—H34	109.5 (12)
C4—N10—H15	118.8 (8)	N22—C28—N24	116.4 (3)
C4—N10—H16	120.5 (10)	N22—C28—O35	121.3 (3)
H15—N10—H16	120.4 (12)	N24—C28—O35	122.2 (4)
C7—C12—C9	123.1 (3)	N22—C29—H36	110.9 (8)
C7—C12—H17	117.3 (9)	N22—C29—H37	108.5 (9)
C9—C12—H17	119.6 (9)	N22—C29—H38	108.2 (8)
C19—C18—C20	122.8 (3)	H36—C29—H37	108.7 (11)
C19—C18—N21	105.8 (3)	H36—C29—H38	109.6 (12)
C20—C18—N21	131.5 (3)	H37—C29—H38	110.9 (17)
C18—C19—N22	123.3 (3)	N24—C30—H39	109.8 (8)
C18—C19—N23	109.9 (3)	N24—C30—H40	104.1 (8)
N22—C19—N23	126.9 (3)	N24—C30—H41	111.2 (7)
C18—C20—N24	111.2 (3)	H39—C30—H40	113.7 (12)
C18—C20—O25	124.2 (3)	H39—C30—H41	106.6 (12)
N24—C20—O25	124.6 (3)	H40—C30—H41	111.6 (11)

(Chlorobenzene_Hemisolvate)

Crystal data

2(C8H10N4O2)·2(C7H7NO2)·C6H5Cl	Z = 2
Mr = 775.22	F(000) = 812
Triclinic, P1	Dx = 1.421 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 12.4390 (2) Å	Cell parameters from 12124 reflections
b = 13.1409 (2) Å	θ = 1.0–30.0°
c = 13.2251 (3) Å	µ = 0.17 mm^−1
α = 69.439 (1)°	T = 180 K
β = 80.418 (1)°	Block, colourless
γ = 63.557 (1)°	0.42 × 0.14 × 0.12 mm
V = 1812.17 (6) Å^3

Data collection

Nonius Kappa CCD diffractometer	4748 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.048
Thin slice ω and φ scans	θmax = 30.1°, θmin = 3.7°
Absorption correction: multi-scan SORTAV (Blessing, 1995)	h = −16→17
Tmin = 0.828, Tmax = 0.994	k = −18→18
27836 measured reflections	l = −18→18
10352 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H-atom parameters constrained
S = 0.89	w = 1/[σ^2(Fo^2) + (0.0496P)^2] where P = (Fo^2 + 2Fc^2)/3
10352 reflections	(Δ/σ)max = 0.002
502 parameters	Δρmax = 0.42 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−3

Special details

Experimental. The –COOH hydrogen atoms were located and their positions were refined satisfactorily.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.05856 (13)	0.26720 (14)	0.47104 (12)	0.0340 (4)
N1	0.03862 (12)	0.31111 (13)	0.67600 (11)	0.0481 (4)
H1A	0.0311	0.3251	0.7378	0.058*
H1B	0.0672	0.3511	0.6187	0.058*
O1	0.09519 (11)	0.34170 (11)	0.46407 (9)	0.0517 (3)
C2	0.01479 (13)	0.20238 (13)	0.57175 (11)	0.0292 (3)
O2	0.05422 (9)	0.23839 (10)	0.38596 (8)	0.0404 (3)
H2X	0.0768	0.2805	0.3306	0.048*
C3	0.00631 (13)	0.22802 (14)	0.66916 (12)	0.0333 (4)
C4	−0.03931 (14)	0.16447 (14)	0.76147 (12)	0.0395 (4)
H4	−0.0453	0.1796	0.8278	0.047*
C5	−0.07513 (14)	0.08137 (15)	0.75768 (12)	0.0414 (4)
H5	−0.1063	0.0407	0.8212	0.050*
C6	−0.06677 (14)	0.05530 (14)	0.66250 (12)	0.0386 (4)
H6	−0.0918	−0.0025	0.6603	0.046*
C7	−0.02140 (13)	0.11530 (13)	0.57195 (12)	0.0312 (4)
H7	−0.0142	0.0972	0.5070	0.037*
N3	0.90546 (10)	0.67323 (10)	−0.05176 (9)	0.0278 (3)
N4	0.83064 (10)	0.58144 (11)	0.11398 (9)	0.0300 (3)
N5	0.79021 (11)	0.50395 (11)	−0.11642 (10)	0.0308 (3)
O5	0.73102 (9)	0.46567 (9)	0.12726 (8)	0.0389 (3)
N6	0.87828 (10)	0.62644 (11)	−0.20549 (9)	0.0298 (3)
O6	0.93270 (9)	0.69263 (9)	0.10470 (8)	0.0380 (3)
C15	0.78551 (13)	0.52418 (13)	0.07088 (12)	0.0290 (3)
C16	0.89221 (13)	0.65236 (13)	0.05771 (12)	0.0296 (3)
C17	0.86640 (12)	0.61811 (13)	−0.09937 (11)	0.0267 (3)
C18	0.81257 (12)	0.54405 (13)	−0.04138 (12)	0.0281 (3)
C19	0.83084 (13)	0.55550 (13)	−0.21122 (12)	0.0330 (4)
H19	0.8264	0.5428	−0.2765	0.040*
C20	0.96061 (14)	0.75379 (14)	−0.11715 (12)	0.0366 (4)
H20A	0.9888	0.7796	−0.0698	0.055*
H20B	0.9012	0.8239	−0.1671	0.055*
H20C	1.0287	0.7117	−0.1583	0.055*
C21	0.73675 (15)	0.41922 (14)	−0.09563 (13)	0.0421 (4)
H21A	0.7441	0.3969	−0.1606	0.063*
H21B	0.6517	0.4565	−0.0764	0.063*
H21C	0.7787	0.3474	−0.0360	0.063*
C22	0.81061 (14)	0.56799 (15)	0.23019 (12)	0.0420 (4)
H22A	0.7706	0.6473	0.2399	0.063*
H22B	0.8880	0.5232	0.2671	0.063*
H22C	0.7600	0.5245	0.2608	0.063*
N7	0.67731 (11)	−0.06460 (11)	0.31045 (9)	0.0306 (3)
O7	0.82743 (9)	0.16438 (10)	0.12662 (8)	0.0395 (3)
N8	0.75884 (11)	0.02257 (11)	0.14650 (9)	0.0314 (3)
O8	0.68043 (9)	−0.10998 (9)	0.15906 (8)	0.0394 (3)
N9	0.75448 (11)	0.13598 (11)	0.36638 (9)	0.0302 (3)
N10	0.68058 (11)	0.00206 (11)	0.45944 (9)	0.0328 (3)
C23	0.78169 (13)	0.09781 (14)	0.18454 (12)	0.0303 (4)
C24	0.70333 (13)	−0.05440 (13)	0.20303 (12)	0.0310 (4)
C25	0.70006 (12)	0.00371 (13)	0.35485 (11)	0.0278 (3)
C26	0.74627 (13)	0.08365 (13)	0.29520 (11)	0.0287 (3)
C27	0.71532 (13)	0.08391 (13)	0.46198 (12)	0.0335 (4)
H27	0.7124	0.1032	0.5255	0.040*
C28	0.62802 (14)	−0.15003 (14)	0.37628 (13)	0.0396 (4)
H28A	0.5887	−0.1666	0.3294	0.059*
H28B	0.5693	−0.1161	0.4281	0.059*
H28C	0.6931	−0.2246	0.4154	0.059*
C29	0.79840 (14)	0.22855 (14)	0.34087 (13)	0.0394 (4)
H29A	0.7786	0.2619	0.4006	0.059*
H29B	0.7604	0.2923	0.2748	0.059*
H29C	0.8857	0.1935	0.3301	0.059*
C30	0.79694 (15)	0.02269 (16)	0.03485 (12)	0.0427 (4)
H30A	0.8292	−0.0591	0.0316	0.064*
H30B	0.8592	0.0530	0.0118	0.064*
H30C	0.7279	0.0743	−0.0131	0.064*
N2	0.36368 (12)	0.08127 (12)	0.06600 (11)	0.0454 (4)
H2A	0.3613	0.0728	0.0034	0.054*
H2B	0.3343	0.0434	0.1243	0.054*
O3	0.32649 (10)	0.04094 (10)	0.28059 (9)	0.0455 (3)
O4	0.38481 (9)	0.13365 (9)	0.35784 (8)	0.0412 (3)
H4X	0.3592	0.0950	0.4136	0.049*
C8	0.37163 (13)	0.10893 (14)	0.27311 (12)	0.0324 (4)
C9	0.41799 (12)	0.16998 (13)	0.17074 (12)	0.0299 (3)
C10	0.41228 (13)	0.15231 (14)	0.07260 (12)	0.0325 (4)
C11	0.45885 (13)	0.21234 (14)	−0.02146 (13)	0.0404 (4)
H11	0.4556	0.2022	−0.0884	0.048*
C12	0.50910 (14)	0.28569 (15)	−0.01769 (14)	0.0450 (4)
H12	0.5404	0.3250	−0.0820	0.054*
C13	0.51459 (14)	0.30287 (15)	0.07916 (13)	0.0425 (4)
H13	0.5494	0.3534	0.0813	0.051*
C14	0.46910 (13)	0.24588 (13)	0.17087 (13)	0.0345 (4)
H14	0.4722	0.2580	0.2368	0.041*
Cl1	0.41515 (5)	0.74908 (5)	0.31917 (5)	0.07674 (19)
C31	0.40109 (15)	0.61564 (16)	0.35184 (14)	0.0447 (4)
C32	0.29997 (16)	0.60650 (17)	0.40470 (14)	0.0494 (5)
H32	0.2388	0.6723	0.4246	0.059*
C33	0.28707 (19)	0.5008 (2)	0.42921 (15)	0.0599 (5)
H33	0.2178	0.4931	0.4673	0.072*
C34	0.3756 (2)	0.40686 (18)	0.39783 (16)	0.0624 (6)
H34	0.3668	0.3347	0.4128	0.075*
C35	0.47619 (18)	0.41811 (18)	0.34500 (17)	0.0657 (6)
H35	0.5375	0.3526	0.3248	0.079*
C36	0.49009 (16)	0.52213 (18)	0.32062 (16)	0.0571 (5)
H36	0.5596	0.5295	0.2830	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0388 (9)	0.0389 (10)	0.0270 (9)	−0.0189 (8)	0.0010 (7)	−0.0106 (7)
N1	0.0720 (10)	0.0620 (10)	0.0296 (8)	−0.0413 (9)	0.0077 (7)	−0.0223 (7)
O1	0.0821 (9)	0.0652 (9)	0.0347 (7)	−0.0550 (8)	0.0111 (6)	−0.0194 (6)
C2	0.0313 (8)	0.0345 (9)	0.0221 (8)	−0.0141 (8)	0.0020 (6)	−0.0099 (7)
O2	0.0600 (7)	0.0571 (8)	0.0200 (6)	−0.0406 (7)	0.0078 (5)	−0.0125 (5)
C3	0.0357 (9)	0.0353 (10)	0.0267 (9)	−0.0127 (8)	−0.0020 (7)	−0.0096 (7)
C4	0.0451 (10)	0.0452 (11)	0.0225 (9)	−0.0133 (9)	0.0018 (7)	−0.0126 (8)
C5	0.0502 (10)	0.0416 (11)	0.0241 (9)	−0.0191 (9)	0.0074 (7)	−0.0044 (8)
C6	0.0494 (10)	0.0348 (10)	0.0296 (9)	−0.0201 (9)	0.0016 (8)	−0.0056 (8)
C7	0.0362 (9)	0.0339 (9)	0.0234 (8)	−0.0145 (8)	0.0005 (7)	−0.0094 (7)
N3	0.0342 (7)	0.0328 (7)	0.0213 (7)	−0.0202 (6)	0.0032 (5)	−0.0075 (6)
N4	0.0366 (7)	0.0359 (8)	0.0185 (7)	−0.0178 (7)	0.0032 (5)	−0.0077 (6)
N5	0.0368 (7)	0.0312 (7)	0.0278 (7)	−0.0181 (6)	0.0008 (6)	−0.0086 (6)
O5	0.0496 (7)	0.0379 (7)	0.0293 (6)	−0.0259 (6)	0.0071 (5)	−0.0042 (5)
N6	0.0349 (7)	0.0368 (8)	0.0220 (7)	−0.0192 (6)	0.0028 (5)	−0.0099 (6)
O6	0.0465 (7)	0.0474 (7)	0.0311 (6)	−0.0255 (6)	0.0021 (5)	−0.0180 (5)
C15	0.0296 (8)	0.0251 (8)	0.0266 (9)	−0.0105 (7)	0.0016 (7)	−0.0036 (7)
C16	0.0304 (8)	0.0304 (9)	0.0261 (9)	−0.0112 (7)	0.0020 (7)	−0.0099 (7)
C17	0.0269 (8)	0.0293 (9)	0.0223 (8)	−0.0120 (7)	0.0008 (6)	−0.0065 (7)
C18	0.0308 (8)	0.0273 (9)	0.0268 (8)	−0.0130 (7)	0.0002 (7)	−0.0082 (7)
C19	0.0363 (9)	0.0376 (10)	0.0272 (9)	−0.0165 (8)	0.0007 (7)	−0.0118 (7)
C20	0.0442 (10)	0.0424 (10)	0.0303 (9)	−0.0283 (9)	0.0057 (7)	−0.0085 (8)
C21	0.0549 (11)	0.0398 (11)	0.0427 (10)	−0.0304 (9)	0.0024 (8)	−0.0127 (8)
C22	0.0506 (10)	0.0583 (12)	0.0237 (9)	−0.0296 (10)	0.0075 (7)	−0.0151 (8)
N7	0.0393 (7)	0.0343 (8)	0.0228 (7)	−0.0217 (7)	0.0035 (6)	−0.0076 (6)
O7	0.0477 (7)	0.0461 (7)	0.0280 (6)	−0.0289 (6)	0.0041 (5)	−0.0051 (5)
N8	0.0392 (7)	0.0386 (8)	0.0188 (7)	−0.0196 (7)	0.0045 (5)	−0.0097 (6)
O8	0.0526 (7)	0.0446 (7)	0.0301 (6)	−0.0255 (6)	−0.0001 (5)	−0.0157 (5)
N9	0.0385 (7)	0.0323 (8)	0.0231 (7)	−0.0191 (6)	−0.0001 (5)	−0.0067 (6)
N10	0.0413 (8)	0.0382 (8)	0.0233 (7)	−0.0215 (7)	0.0038 (6)	−0.0101 (6)
C23	0.0308 (8)	0.0351 (9)	0.0235 (8)	−0.0153 (8)	−0.0008 (7)	−0.0052 (7)
C24	0.0327 (9)	0.0333 (9)	0.0265 (9)	−0.0129 (8)	−0.0013 (7)	−0.0096 (7)
C25	0.0300 (8)	0.0323 (9)	0.0220 (8)	−0.0140 (7)	0.0004 (6)	−0.0088 (7)
C26	0.0339 (8)	0.0305 (9)	0.0218 (8)	−0.0142 (7)	−0.0014 (6)	−0.0068 (7)
C27	0.0399 (9)	0.0398 (10)	0.0238 (9)	−0.0197 (8)	0.0013 (7)	−0.0101 (7)
C28	0.0501 (10)	0.0405 (10)	0.0345 (9)	−0.0288 (9)	0.0062 (8)	−0.0091 (8)
C29	0.0522 (10)	0.0409 (10)	0.0344 (9)	−0.0294 (9)	−0.0009 (8)	−0.0090 (8)
C30	0.0527 (11)	0.0552 (12)	0.0243 (9)	−0.0274 (10)	0.0081 (8)	−0.0145 (8)
N2	0.0595 (9)	0.0576 (10)	0.0308 (8)	−0.0322 (8)	0.0029 (7)	−0.0185 (7)
O3	0.0652 (8)	0.0526 (8)	0.0354 (7)	−0.0407 (7)	0.0075 (6)	−0.0153 (6)
O4	0.0597 (7)	0.0509 (8)	0.0243 (6)	−0.0349 (6)	0.0071 (5)	−0.0123 (5)
C8	0.0375 (9)	0.0348 (10)	0.0270 (9)	−0.0159 (8)	0.0023 (7)	−0.0123 (7)
C9	0.0282 (8)	0.0300 (9)	0.0280 (9)	−0.0103 (7)	0.0006 (7)	−0.0080 (7)
C10	0.0293 (8)	0.0334 (9)	0.0296 (9)	−0.0081 (8)	−0.0006 (7)	−0.0105 (7)
C11	0.0401 (10)	0.0429 (11)	0.0264 (9)	−0.0103 (9)	0.0037 (7)	−0.0090 (8)
C12	0.0452 (10)	0.0430 (11)	0.0343 (10)	−0.0177 (9)	0.0079 (8)	−0.0026 (8)
C13	0.0457 (10)	0.0409 (11)	0.0408 (11)	−0.0233 (9)	0.0055 (8)	−0.0087 (8)
C14	0.0352 (9)	0.0341 (10)	0.0314 (9)	−0.0128 (8)	0.0003 (7)	−0.0094 (7)
Cl1	0.0974 (4)	0.0732 (4)	0.0916 (4)	−0.0591 (4)	0.0174 (3)	−0.0395 (3)
C31	0.0485 (11)	0.0506 (12)	0.0474 (11)	−0.0279 (10)	0.0038 (9)	−0.0218 (9)
C32	0.0471 (11)	0.0653 (13)	0.0471 (11)	−0.0274 (10)	0.0079 (9)	−0.0291 (10)
C33	0.0716 (14)	0.0754 (16)	0.0461 (12)	−0.0464 (13)	0.0047 (10)	−0.0161 (11)
C34	0.0897 (16)	0.0453 (13)	0.0563 (13)	−0.0385 (13)	−0.0197 (12)	0.0015 (10)
C35	0.0540 (13)	0.0550 (14)	0.0879 (17)	−0.0106 (11)	−0.0176 (12)	−0.0309 (12)
C36	0.0396 (11)	0.0681 (14)	0.0788 (15)	−0.0244 (11)	0.0072 (10)	−0.0412 (12)

Geometric parameters (Å, º)

C1—O1	1.2225 (16)	N8—C30	1.4733 (18)
C1—O2	1.3229 (17)	O8—C24	1.2213 (16)
C1—C2	1.473 (2)	N9—C27	1.3372 (18)
N1—C3	1.3544 (18)	N9—C26	1.3852 (17)
N1—H1A	0.8800	N9—C29	1.4610 (17)
N1—H1B	0.8800	N10—C27	1.3374 (17)
C2—C7	1.4029 (19)	N10—C25	1.3582 (17)
C2—C3	1.4185 (19)	C23—C26	1.427 (2)
O2—H2X	0.8400	C25—C26	1.3642 (19)
C3—C4	1.409 (2)	C27—H27	0.9500
C4—C5	1.369 (2)	C28—H28A	0.9800
C4—H4	0.9500	C28—H28B	0.9800
C5—C6	1.393 (2)	C28—H28C	0.9800
C5—H5	0.9500	C29—H29A	0.9800
C6—C7	1.372 (2)	C29—H29B	0.9800
C6—H6	0.9500	C29—H29C	0.9800
C7—H7	0.9500	C30—H30A	0.9800
N3—C16	1.3712 (18)	C30—H30B	0.9800
N3—C17	1.3759 (17)	C30—H30C	0.9800
N3—C20	1.4648 (17)	N2—C10	1.3499 (18)
N4—C16	1.4027 (17)	N2—H2A	0.8800
N4—C15	1.4107 (18)	N2—H2B	0.8800
N4—C22	1.4753 (18)	O3—C8	1.2204 (16)
N5—C19	1.3356 (18)	O4—C8	1.3237 (17)
N5—C18	1.3892 (18)	O4—H4X	0.8400
N5—C21	1.4632 (17)	C8—C9	1.483 (2)
O5—C15	1.2247 (16)	C9—C14	1.4019 (19)
N6—C19	1.3331 (17)	C9—C10	1.414 (2)
N6—C17	1.3568 (17)	C10—C11	1.408 (2)
O6—C16	1.2217 (16)	C11—C12	1.380 (2)
C15—C18	1.423 (2)	C11—H11	0.9500
C17—C18	1.3670 (19)	C12—C13	1.393 (2)
C19—H19	0.9500	C12—H12	0.9500
C20—H20A	0.9800	C13—C14	1.365 (2)
C20—H20B	0.9800	C13—H13	0.9500
C20—H20C	0.9800	C14—H14	0.9500
C21—H21A	0.9800	Cl1—C31	1.7344 (17)
C21—H21B	0.9800	C31—C32	1.367 (2)
C21—H21C	0.9800	C31—C36	1.378 (2)
C22—H22A	0.9800	C32—C33	1.388 (2)
C22—H22B	0.9800	C32—H32	0.9500
C22—H22C	0.9800	C33—C34	1.380 (3)
N7—C25	1.3720 (17)	C33—H33	0.9500
N7—C24	1.3757 (18)	C34—C35	1.370 (3)
N7—C28	1.4640 (17)	C34—H34	0.9500
O7—C23	1.2261 (16)	C35—C36	1.373 (2)
N8—C23	1.3995 (18)	C35—H35	0.9500
N8—C24	1.4064 (18)	C36—H36	0.9500
O1—C1—O2	121.74 (14)	C27—N10—C25	103.32 (11)
O1—C1—C2	124.50 (14)	O7—C23—N8	121.73 (13)
O2—C1—C2	113.75 (13)	O7—C23—C26	127.22 (14)
C3—N1—H1A	120.0	N8—C23—C26	111.04 (12)
C3—N1—H1B	120.0	O8—C24—N7	121.87 (13)
H1A—N1—H1B	120.0	O8—C24—N8	121.59 (13)
C7—C2—C3	118.92 (13)	N7—C24—N8	116.55 (12)
C7—C2—C1	120.06 (13)	N10—C25—C26	111.92 (12)
C3—C2—C1	121.01 (13)	N10—C25—N7	126.10 (12)
C1—O2—H2X	109.5	C26—C25—N7	121.98 (13)
N1—C3—C4	119.51 (14)	C25—C26—N9	105.20 (12)
N1—C3—C2	122.79 (14)	C25—C26—C23	123.25 (13)
C4—C3—C2	117.69 (13)	N9—C26—C23	131.46 (13)
C5—C4—C3	121.45 (14)	N9—C27—N10	113.43 (13)
C5—C4—H4	119.3	N9—C27—H27	123.3
C3—C4—H4	119.3	N10—C27—H27	123.3
C4—C5—C6	121.27 (15)	N7—C28—H28A	109.5
C4—C5—H5	119.4	N7—C28—H28B	109.5
C6—C5—H5	119.4	H28A—C28—H28B	109.5
C7—C6—C5	118.19 (14)	N7—C28—H28C	109.5
C7—C6—H6	120.9	H28A—C28—H28C	109.5
C5—C6—H6	120.9	H28B—C28—H28C	109.5
C6—C7—C2	122.47 (14)	N9—C29—H29A	109.5
C6—C7—H7	118.8	N9—C29—H29B	109.5
C2—C7—H7	118.8	H29A—C29—H29B	109.5
C16—N3—C17	119.46 (11)	N9—C29—H29C	109.5
C16—N3—C20	120.07 (11)	H29A—C29—H29C	109.5
C17—N3—C20	120.47 (12)	H29B—C29—H29C	109.5
C16—N4—C15	126.96 (12)	N8—C30—H30A	109.5
C16—N4—C22	115.38 (11)	N8—C30—H30B	109.5
C15—N4—C22	117.66 (11)	H30A—C30—H30B	109.5
C19—N5—C18	106.10 (11)	N8—C30—H30C	109.5
C19—N5—C21	126.73 (12)	H30A—C30—H30C	109.5
C18—N5—C21	127.13 (12)	H30B—C30—H30C	109.5
C19—N6—C17	103.41 (11)	C10—N2—H2A	120.0
O5—C15—N4	121.59 (13)	C10—N2—H2B	120.0
O5—C15—C18	127.10 (13)	H2A—N2—H2B	120.0
N4—C15—C18	111.31 (12)	C8—O4—H4X	109.5
O6—C16—N3	121.88 (13)	O3—C8—O4	122.17 (14)
O6—C16—N4	121.21 (13)	O3—C8—C9	124.15 (13)
N3—C16—N4	116.91 (12)	O4—C8—C9	113.67 (12)
N6—C17—C18	111.98 (12)	C14—C9—C10	119.24 (13)
N6—C17—N3	125.81 (12)	C14—C9—C8	119.73 (13)
C18—C17—N3	122.19 (13)	C10—C9—C8	121.03 (13)
C17—C18—N5	104.89 (12)	N2—C10—C11	119.32 (14)
C17—C18—C15	122.86 (13)	N2—C10—C9	122.63 (14)
N5—C18—C15	132.19 (13)	C11—C10—C9	118.05 (14)
N6—C19—N5	113.62 (13)	C12—C11—C10	120.87 (15)
N6—C19—H19	123.2	C12—C11—H11	119.6
N5—C19—H19	123.2	C10—C11—H11	119.6
N3—C20—H20A	109.5	C11—C12—C13	120.91 (15)
N3—C20—H20B	109.5	C11—C12—H12	119.5
H20A—C20—H20B	109.5	C13—C12—H12	119.5
N3—C20—H20C	109.5	C14—C13—C12	118.88 (15)
H20A—C20—H20C	109.5	C14—C13—H13	120.6
H20B—C20—H20C	109.5	C12—C13—H13	120.6
N5—C21—H21A	109.5	C13—C14—C9	122.04 (15)
N5—C21—H21B	109.5	C13—C14—H14	119.0
H21A—C21—H21B	109.5	C9—C14—H14	119.0
N5—C21—H21C	109.5	C32—C31—C36	121.13 (16)
H21A—C21—H21C	109.5	C32—C31—Cl1	119.42 (14)
H21B—C21—H21C	109.5	C36—C31—Cl1	119.41 (14)
N4—C22—H22A	109.5	C31—C32—C33	119.73 (18)
N4—C22—H22B	109.5	C31—C32—H32	120.1
H22A—C22—H22B	109.5	C33—C32—H32	120.1
N4—C22—H22C	109.5	C34—C33—C32	119.49 (18)
H22A—C22—H22C	109.5	C34—C33—H33	120.3
H22B—C22—H22C	109.5	C32—C33—H33	120.3
C25—N7—C24	119.58 (12)	C35—C34—C33	119.70 (18)
C25—N7—C28	120.93 (12)	C35—C34—H34	120.1
C24—N7—C28	119.48 (12)	C33—C34—H34	120.1
C23—N8—C24	127.33 (12)	C34—C35—C36	121.31 (19)
C23—N8—C30	117.13 (12)	C34—C35—H35	119.3
C24—N8—C30	115.54 (12)	C36—C35—H35	119.3
C27—N9—C26	106.11 (11)	C35—C36—C31	118.62 (17)
C27—N9—C29	127.60 (12)	C35—C36—H36	120.7
C26—N9—C29	126.29 (12)	C31—C36—H36	120.7

(Bromobenzene_Hemisolvate)

Crystal data

2(C8H10N4O2)·2(C7H7NO2)·C6H5Br	V = 1876.3 (8) Å^3
Mr = 819.67	Z = 2
Triclinic, P1	F(000) = 848
a = 12.569 (3) Å	Dx = 1.451 Mg m^−3
b = 13.409 (3) Å	Cu Kα radiation, λ = 1.5418 Å
c = 13.269 (3) Å	T = 293 K
α = 68.991 (4)°	white
β = 80.215 (5)°	flat sheet, 14 × 10 mm
γ = 64.007 (4)°

Data collection

Panalytical X'pert Powder diffractometer	Data collection mode: reflection
Radiation source: sealed X-ray tube	Scan method: continuous
None monochromator	2θmin = 5.005°, 2θmax = 49.992°, 2θstep = 0.017°
Specimen mounting: glass slide

Refinement

Rp = 0.046	323 parameters
Rwp = 0.059	255 restraints
Rexp = 0.040	0 constraints
RBragg = 0.016
χ^2 = 2.161
2693 data points	Background function: Chebyshev polynomial
Profile function: pseudo-Voigt	Preferred orientation correction: spherical harmonics

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.4019 (7)	0.6024 (6)	0.3553 (8)	0.027
C2	0.3028 (7)	0.5886 (6)	0.4165 (7)	0.027
C3	0.4891 (7)	0.5221 (6)	0.3112 (7)	0.027
Br4	0.4195 (5)	0.7470 (5)	0.3209 (5)	0.027
C5	0.2910 (7)	0.4834 (5)	0.4376 (7)	0.027
H6	0.246 (3)	0.648 (3)	0.441 (3)	0.032
C7	0.4817 (7)	0.4195 (5)	0.3297 (7)	0.027
H8	0.549 (3)	0.538 (3)	0.267 (3)	0.032
C9	0.3890 (7)	0.3930 (6)	0.3965 (8)	0.027
H10	0.228 (3)	0.470 (3)	0.482 (3)	0.032
H11	0.539 (3)	0.368 (3)	0.297 (2)	0.032
H12	0.392 (3)	0.315 (2)	0.410 (2)	0.032
C13	0.4179 (7)	0.1773 (6)	0.1736 (6)	0.027
C14	0.3708 (8)	0.1145 (6)	0.2730 (6)	0.027
C15	0.4621 (8)	0.2567 (6)	0.1728 (6)	0.027
C16	0.4171 (7)	0.1576 (6)	0.0746 (5)	0.027
O17	0.3814 (12)	0.1260 (7)	0.3652 (7)	0.027
O18	0.3287 (11)	0.0424 (9)	0.2753 (11)	0.027
C19	0.5025 (9)	0.3192 (6)	0.0774 (5)	0.027
H20	0.462 (3)	0.267 (3)	0.242 (3)	0.032
C21	0.4639 (7)	0.2243 (6)	−0.0234 (5)	0.027
N22	0.3677 (7)	0.0804 (5)	0.0760 (5)	0.027
H23	0.357 (3)	0.071 (3)	0.420 (3)	0.032
C24	0.5059 (8)	0.2995 (5)	−0.0188 (6)	0.027
H25	0.524 (3)	0.379 (3)	0.078 (3)	0.032
H26	0.454 (3)	0.226 (3)	−0.092 (2)	0.032
H27	0.344 (3)	0.038 (3)	0.146 (3)	0.032
H28	0.373 (3)	0.056 (3)	0.012 (3)	0.032
H29	0.522 (3)	0.349 (3)	−0.085 (2)	0.032
C30	0.0154 (6)	0.2085 (6)	0.5688 (5)	0.027
C31	0.0651 (8)	0.2638 (6)	0.4715 (6)	0.027
C32	−0.0228 (8)	0.1240 (6)	0.5721 (5)	0.027
C33	0.0083 (8)	0.2337 (6)	0.6625 (5)	0.027
O34	0.0524 (9)	0.2392 (7)	0.3903 (7)	0.027
O35	0.0943 (14)	0.3467 (9)	0.4537 (12)	0.027
C36	−0.0638 (9)	0.0626 (6)	0.6624 (6)	0.027
H37	−0.024 (3)	0.113 (2)	0.509 (3)	0.032
C38	−0.0354 (8)	0.1739 (6)	0.7574 (6)	0.027
N39	0.0439 (8)	0.3116 (6)	0.6711 (5)	0.027
H40	0.063 (3)	0.295 (3)	0.330 (3)	0.032
C41	−0.0690 (8)	0.0870 (6)	0.7593 (5)	0.027
H42	−0.087 (3)	0.005 (3)	0.658 (3)	0.032
H43	−0.037 (3)	0.193 (3)	0.821 (3)	0.032
H44	0.082 (3)	0.349 (3)	0.608 (3)	0.032
H45	0.047 (3)	0.313 (3)	0.743 (3)	0.032
H46	−0.092 (3)	0.044 (3)	0.827 (3)	0.032
C47	0.7519 (7)	0.0901 (5)	0.2878 (6)	0.027
C48	0.7031 (8)	0.0108 (6)	0.3469 (6)	0.027
C49	0.7831 (7)	0.1059 (6)	0.1762 (6)	0.027
N50	0.7608 (8)	0.1415 (6)	0.3608 (6)	0.027
N51	0.6773 (7)	−0.0594 (6)	0.3067 (5)	0.027
N52	0.6895 (9)	0.0082 (7)	0.4510 (7)	0.027
N53	0.7540 (7)	0.0347 (6)	0.1336 (6)	0.027
O54	0.8299 (12)	0.1732 (10)	0.1196 (11)	0.027
C55	0.7232 (8)	0.0891 (6)	0.4537 (6)	0.027
C56	0.8045 (6)	0.2353 (5)	0.3486 (5)	0.027
C57	0.6974 (8)	−0.0449 (6)	0.1972 (6)	0.027
C58	0.6285 (6)	−0.1474 (5)	0.3786 (6)	0.027
C59	0.7916 (5)	0.0407 (5)	0.0174 (5)	0.027
H60	0.716 (3)	0.111 (3)	0.516 (2)	0.032
H61	0.804 (2)	0.283 (3)	0.273 (2)	0.032
H62	0.884 (3)	0.202 (3)	0.378 (3)	0.032
H63	0.753 (3)	0.281 (3)	0.392 (2)	0.032
O64	0.6688 (13)	−0.1027 (9)	0.1590 (9)	0.027
H65	0.547 (3)	−0.114 (3)	0.374 (3)	0.032
H66	0.644 (3)	−0.168 (3)	0.451 (2)	0.032
H67	0.660 (3)	−0.215 (3)	0.357 (3)	0.032
H68	0.861 (3)	−0.031 (3)	0.020 (3)	0.032
H69	0.811 (3)	0.107 (3)	−0.017 (3)	0.032
H70	0.730 (3)	0.051 (3)	−0.025 (3)	0.032
C71	0.8168 (6)	0.5375 (5)	−0.0383 (6)	0.027
C72	0.8710 (7)	0.6153 (6)	−0.0957 (5)	0.027
C73	0.7953 (7)	0.5165 (6)	0.0767 (6)	0.027
N74	0.7959 (7)	0.4969 (6)	−0.1172 (6)	0.027
N75	0.9034 (7)	0.6787 (6)	−0.0502 (6)	0.027
N76	0.8842 (9)	0.6209 (8)	−0.2007 (7)	0.027
N77	0.8311 (7)	0.5839 (6)	0.1223 (6)	0.027
O78	0.7515 (11)	0.4492 (9)	0.1345 (11)	0.027
C79	0.8354 (7)	0.5542 (6)	−0.2122 (6)	0.027
C80	0.7470 (6)	0.4080 (5)	−0.1077 (5)	0.027
C81	0.8877 (7)	0.6623 (6)	0.0615 (6)	0.027
C82	0.9637 (6)	0.7585 (5)	−0.1163 (5)	0.027
C83	0.8127 (6)	0.5685 (5)	0.2394 (6)	0.027
H84	0.835 (3)	0.544 (3)	−0.282 (3)	0.032
H85	0.754 (3)	0.355 (3)	−0.036 (3)	0.032
H86	0.668 (3)	0.446 (3)	−0.124 (3)	0.032
H87	0.786 (3)	0.366 (3)	−0.161 (3)	0.032
O88	0.9281 (12)	0.7118 (10)	0.1022 (9)	0.027
H89	1.046 (3)	0.723 (3)	−0.100 (3)	0.032
H90	0.960 (3)	0.772 (3)	−0.195 (3)	0.032
H91	0.930 (3)	0.832 (3)	−0.098 (2)	0.032
H92	0.741 (3)	0.628 (3)	0.251 (2)	0.032
H93	0.811 (3)	0.494 (3)	0.275 (3)	0.032
H94	0.874 (3)	0.573 (2)	0.268 (2)	0.032

Geometric parameters (Å, º)

C1—C2	1.413 (12)	C47—N50	1.418 (13)
C1—C3	1.379 (11)	C48—N51	1.400 (14)
C1—Br4	1.930 (11)	C48—N52	1.353 (12)
C2—C5	1.406 (11)	C49—N53	1.459 (14)
C2—H6	0.93 (4)	C49—O54	1.246 (17)
C3—C7	1.351 (11)	N50—C55	1.308 (10)
C3—H8	0.92 (4)	N50—C56	1.528 (12)
C5—C9	1.491 (10)	N51—C57	1.388 (10)
C5—H10	0.95 (3)	N51—C58	1.518 (11)
C7—C9	1.433 (11)	N52—C55	1.340 (16)
C7—H11	0.93 (3)	N53—C57	1.474 (12)
C9—H12	0.99 (3)	N53—C59	1.518 (9)
C13—C14	1.475 (10)	C55—H60	0.95 (4)
C13—C15	1.396 (14)	C56—H61	0.98 (3)
C13—C16	1.432 (11)	C56—H62	0.98 (4)
C14—O17	1.321 (14)	C56—H63	0.96 (3)
C14—O18	1.279 (19)	C57—O64	1.256 (19)
C15—C19	1.400 (10)	C58—H65	0.93 (3)
C15—H20	0.97 (4)	C58—H66	0.93 (3)
C16—C21	1.484 (10)	C58—H67	0.95 (4)
C16—N22	1.415 (14)	C59—H68	0.96 (3)
O17—H23	0.95 (4)	C59—H69	0.96 (4)
C19—C24	1.383 (11)	C59—H70	0.97 (4)
C19—H25	0.95 (5)	C71—C72	1.417 (11)
C21—C24	1.349 (14)	C71—C73	1.448 (10)
C21—H26	0.94 (4)	C71—N74	1.446 (13)
N22—H27	0.98 (3)	C72—N75	1.417 (14)
N22—H28	0.99 (4)	C72—N76	1.354 (12)
C24—H29	0.95 (3)	C73—N77	1.492 (14)
C30—C31	1.433 (10)	C73—O78	1.225 (15)
C30—C32	1.396 (13)	N74—C79	1.361 (10)
C30—C33	1.379 (11)	N74—C80	1.524 (12)
C31—O34	1.286 (15)	N75—C81	1.410 (10)
C31—O35	1.253 (18)	N75—C82	1.516 (11)
C32—C36	1.354 (10)	N76—C79	1.346 (16)
C32—H37	0.90 (4)	N77—C81	1.455 (12)
C33—C38	1.400 (10)	N77—C83	1.483 (10)
C33—N39	1.349 (14)	C79—H84	0.99 (4)
O34—H40	0.92 (3)	C80—H85	0.95 (3)
C36—C41	1.421 (11)	C80—H86	0.92 (3)
C36—H42	0.95 (5)	C80—H87	0.99 (4)
C38—C41	1.394 (14)	C81—O88	1.277 (19)
C38—H43	0.96 (4)	C82—H89	0.96 (3)
N39—H44	0.98 (3)	C82—H90	1.00 (4)
N39—H45	0.96 (4)	C82—H91	0.99 (3)
C41—H46	0.95 (3)	C83—H92	0.94 (3)
C47—C48	1.391 (12)	C83—H93	0.95 (3)
C47—C49	1.428 (10)	C83—H94	0.94 (4)
C2—C1—C3	125.9 (8)	C47—N50—C55	105.2 (8)
C2—C1—Br4	119.9 (6)	C47—N50—C56	133.2 (6)
C3—C1—Br4	114.2 (7)	C55—N50—C56	121.6 (8)
C1—C2—C5	118.4 (7)	C48—N51—C57	117.1 (8)
C1—C2—H6	121 (3)	C48—N51—C58	122.0 (7)
C5—C2—H6	120 (3)	C57—N51—C58	120.9 (9)
C1—C3—C7	117.8 (8)	C48—N52—C55	105.6 (8)
C1—C3—H8	122 (2)	C49—N53—C57	124.3 (7)
C7—C3—H8	120 (2)	C49—N53—C59	116.2 (7)
C2—C5—C9	116.0 (7)	C57—N53—C59	119.5 (8)
C2—C5—H10	120 (2)	N50—C55—N52	114.2 (9)
C9—C5—H10	124 (2)	N50—C55—H60	122 (2)
C3—C7—C9	121.1 (7)	N52—C55—H60	124 (2)
C3—C7—H11	117 (3)	N50—C56—H61	111 (3)
C9—C7—H11	122 (3)	N50—C56—H62	112 (2)
C5—C9—C7	120.5 (7)	N50—C56—H63	106 (2)
C5—C9—H12	123 (2)	H61—C56—H62	109 (3)
C7—C9—H12	117 (2)	H61—C56—H63	111 (2)
C14—C13—C15	121.9 (8)	H62—C56—H63	106 (3)
C14—C13—C16	119.2 (9)	N51—C57—N53	118.2 (9)
C15—C13—C16	118.9 (7)	N51—C57—O64	117.8 (9)
C13—C14—O17	118 (1)	N53—C57—O64	123.9 (9)
C13—C14—O18	123 (1)	N51—C58—H65	110 (2)
O17—C14—O18	118 (1)	N51—C58—H66	112 (3)
C13—C15—C19	121.5 (8)	N51—C58—H67	111 (2)
C13—C15—H20	116 (2)	H65—C58—H66	106 (3)
C19—C15—H20	122 (2)	H65—C58—H67	109 (4)
C13—C16—C21	117.0 (9)	H66—C58—H67	110 (3)
C13—C16—N22	118.2 (7)	N53—C59—H68	107 (2)
C21—C16—N22	124.8 (8)	N53—C59—H69	109 (2)
C14—O17—H23	106 (3)	N53—C59—H70	113 (2)
C15—C19—C24	120.7 (9)	H68—C59—H69	110 (3)
C15—C19—H25	120 (2)	H68—C59—H70	111 (3)
C24—C19—H25	120 (2)	H69—C59—H70	107 (3)
C16—C21—C24	121.2 (8)	C72—C71—C73	118.8 (8)
C16—C21—H26	122 (3)	C72—C71—N74	105.9 (6)
C24—C21—H26	117 (2)	C73—C71—N74	135.3 (8)
C16—N22—H27	117 (3)	C71—C72—N75	125.1 (7)
C16—N22—H28	122 (3)	C71—C72—N76	109.1 (9)
H27—N22—H28	120 (4)	N75—C72—N76	125.8 (8)
C19—C24—C21	120.5 (8)	C71—C73—N77	114.8 (7)
C19—C24—H29	120 (3)	C71—C73—O78	125 (1)
C21—C24—H29	119 (3)	N77—C73—O78	121 (1)
C31—C30—C32	120.5 (8)	C71—N74—C79	104.5 (8)
C31—C30—C33	121.1 (9)	C71—N74—C80	132.5 (6)
C32—C30—C33	118.3 (7)	C79—N74—C80	123.0 (8)
C30—C31—O34	112.1 (10)	C72—N75—C81	120.1 (8)
C30—C31—O35	127.7 (10)	C72—N75—C82	122.1 (6)
O34—C31—O35	118.3 (10)	C81—N75—C82	117.6 (9)
C30—C32—C36	124.1 (8)	C72—N76—C79	107.3 (8)
C30—C32—H37	119 (3)	C73—N77—C81	125.1 (7)
C36—C32—H37	118 (3)	C73—N77—C83	119.0 (7)
C30—C33—C38	119.6 (9)	C81—N77—C83	115.8 (8)
C30—C33—N39	124.5 (7)	N74—C79—N76	113.1 (8)
C38—C33—N39	115.9 (8)	N74—C79—H84	124 (2)
C31—O34—H40	106 (3)	N76—C79—H84	122 (2)
C32—C36—C41	117.5 (9)	N74—C80—H85	111 (3)
C32—C36—H42	119 (2)	N74—C80—H86	110 (3)
C41—C36—H42	123 (2)	N74—C80—H87	111 (2)
C33—C38—C41	120.8 (8)	H85—C80—H86	107 (3)
C33—C38—H43	117 (2)	H85—C80—H87	112 (3)
C41—C38—H43	122 (2)	H86—C80—H87	107 (3)
C33—N39—H44	118 (3)	N75—C81—N77	115.9 (9)
C33—N39—H45	118 (2)	N75—C81—O88	118.8 (9)
H44—N39—H45	123 (4)	N77—C81—O88	125.2 (8)
C36—C41—C38	119.6 (7)	N75—C82—H89	111 (2)
C36—C41—H46	122 (3)	N75—C82—H90	111 (2)
C38—C41—H46	118 (3)	N75—C82—H91	110 (2)
C48—C47—C49	121.4 (9)	H89—C82—H90	106 (3)
C48—C47—N50	106.0 (7)	H89—C82—H91	106 (3)
C49—C47—N50	132.6 (8)	H90—C82—H91	114 (2)
C47—C48—N51	125.8 (7)	N77—C83—H92	110 (2)
C47—C48—N52	108.9 (9)	N77—C83—H93	108 (2)
N51—C48—N52	125.2 (8)	N77—C83—H94	112 (2)
C47—C49—N53	112.9 (8)	H92—C83—H93	110 (3)
C47—C49—O54	124.6 (12)	H92—C83—H94	108 (3)
N53—C49—O54	122.5 (10)	H93—C83—H94	109 (3)

(Toluene_Hemisolvate)

Crystal data

2(C8H10N4O2)·2(C7H7NO2)·C7H8	V = 1873 (2) Å^3
Mr = 754.80	Z = 2
Triclinic, P1	F(000) = 796
a = 12.475 (9) Å	Dx = 1.338 (2) Mg m^−3
b = 13.488 (9) Å	Cu Kα radiation, λ = 1.5418 Å
c = 13.316 (9) Å	T = 293 K
α = 68.318 (11)°	white
β = 79.948 (16)°	flat sheet, 14 × 10 mm
γ = 64.124 (11)°

Data collection

Panalytical X'pert Powder diffractometer	Data collection mode: reflection
Radiation source: sealed X-ray tube	Scan method: continuous
None monochromator	2θmin = 5.000°, 2θmax = 39.969°, 2θstep = 0.017°
Specimen mounting: glass slide

Refinement

Rp = 0.050	337 parameters
Rwp = 0.067	264 restraints
Rexp = 0.060	0 constraints
RBragg = 0.007
χ^2 = 1.219
2058 data points	Background function: Chebyshev polynomial
Profile function: pseudo-voigt	Preferred orientation correction: spherical harmonics

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.421 (3)	0.647 (3)	0.3337 (19)	0.051
C2	0.311 (2)	0.651 (2)	0.3831 (17)	0.051
C3	0.493 (3)	0.545 (3)	0.3158 (17)	0.051
C4	0.463 (3)	0.753 (2)	0.298 (2)	0.051
C5	0.283 (3)	0.561 (3)	0.409 (2)	0.051
H6	0.255 (9)	0.715 (9)	0.399 (9)	0.061
C7	0.468 (3)	0.455 (3)	0.341 (2)	0.051
H8	0.562 (10)	0.540 (9)	0.285 (9)	0.061
H9	0.549 (9)	0.723 (8)	0.312 (9)	0.061
H10	0.451 (9)	0.793 (8)	0.224 (9)	0.061
H11	0.420 (9)	0.810 (7)	0.333 (9)	0.061
C12	0.359 (3)	0.458 (3)	0.390 (2)	0.051
H13	0.210 (9)	0.568 (8)	0.440 (10)	0.061
H14	0.527 (10)	0.389 (7)	0.325 (9)	0.061
H15	0.333 (9)	0.392 (7)	0.413 (9)	0.061
C16	0.4113 (17)	0.156 (2)	0.185 (3)	0.051
C17	0.370 (3)	0.089 (3)	0.287 (3)	0.051
C18	0.463 (2)	0.241 (2)	0.190 (3)	0.051
C19	0.409 (3)	0.151 (3)	0.082 (3)	0.051
O20	0.392 (4)	0.128 (3)	0.368 (3)	0.051
O21	0.323 (4)	0.009 (4)	0.304 (5)	0.051
C22	0.509 (3)	0.314 (3)	0.100 (3)	0.051
H23	0.466 (10)	0.245 (8)	0.261 (9)	0.061
C24	0.461 (2)	0.235 (3)	−0.010 (3)	0.051
N25	0.358 (3)	0.074 (3)	0.070 (3)	0.051
H26	0.372 (11)	0.093 (11)	0.442 (11)	0.061
C27	0.507 (3)	0.307 (3)	−0.003 (3)	0.051
H28	0.541 (10)	0.366 (9)	0.113 (10)	0.061
H29	0.463 (9)	0.236 (8)	−0.083 (9)	0.061
H30	0.328 (10)	0.028 (8)	0.135 (9)	0.061
H31	0.356 (10)	0.066 (10)	−0.001 (11)	0.061
H32	0.537 (11)	0.352 (8)	−0.067 (9)	0.061
C33	0.003 (2)	0.198 (2)	0.589 (3)	0.051
C34	0.070 (3)	0.265 (3)	0.500 (3)	0.051
C35	−0.033 (2)	0.111 (3)	0.585 (3)	0.051
C36	−0.029 (2)	0.220 (3)	0.686 (3)	0.051
O37	0.098 (4)	0.238 (3)	0.408 (3)	0.051
O38	0.101 (4)	0.349 (4)	0.497 (5)	0.051
C39	−0.090 (3)	0.047 (3)	0.660 (3)	0.051
H40	−0.015 (10)	0.093 (8)	0.523 (9)	0.061
C41	−0.091 (3)	0.156 (3)	0.765 (3)	0.051
N42	−0.005 (3)	0.300 (3)	0.711 (3)	0.051
H43	0.139 (8)	0.284 (8)	0.358 (9)	0.061
C44	−0.122 (3)	0.073 (3)	0.755 (3)	0.051
H45	−0.110 (9)	−0.010 (8)	0.647 (8)	0.061
H46	−0.112 (10)	0.175 (9)	0.830 (9)	0.061
H47	0.036 (9)	0.342 (8)	0.658 (9)	0.061
H48	−0.031 (9)	0.310 (8)	0.780 (9)	0.061
H49	−0.164 (9)	0.035 (7)	0.812 (9)	0.061
C50	0.739 (2)	0.090 (3)	0.303 (2)	0.051
C51	0.682 (2)	0.012 (3)	0.363 (3)	0.051
C52	0.785 (3)	0.107 (3)	0.189 (3)	0.051
N53	0.740 (3)	0.142 (3)	0.375 (3)	0.051
N54	0.663 (3)	−0.064 (3)	0.319 (3)	0.051
N55	0.651 (3)	0.022 (3)	0.468 (3)	0.051
N56	0.766 (3)	0.037 (3)	0.146 (3)	0.051
O57	0.842 (4)	0.170 (4)	0.122 (5)	0.051
C58	0.686 (3)	0.098 (3)	0.477 (3)	0.051
C59	0.788 (3)	0.228 (3)	0.342 (3)	0.051
C60	0.707 (3)	−0.047 (3)	0.204 (3)	0.051
C61	0.595 (3)	−0.159 (3)	0.386 (3)	0.051
C62	0.812 (3)	0.067 (3)	0.026 (2)	0.051
H63	0.674 (9)	0.118 (7)	0.544 (8)	0.061
H64	0.754 (10)	0.282 (9)	0.275 (8)	0.061
H65	0.872 (9)	0.193 (9)	0.336 (8)	0.061
H66	0.766 (9)	0.266 (8)	0.394 (9)	0.061
O67	0.688 (4)	−0.100 (4)	0.154 (4)	0.051
H68	0.507 (10)	−0.121 (8)	0.374 (10)	0.061
H69	0.604 (11)	−0.183 (7)	0.463 (8)	0.061
H70	0.629 (10)	−0.232 (8)	0.367 (10)	0.061
H71	0.853 (9)	−0.000 (9)	0.003 (10)	0.061
H72	0.865 (12)	0.104 (11)	0.021 (10)	0.061
H73	0.746 (9)	0.125 (10)	−0.023 (9)	0.061
C74	0.8143 (15)	0.5288 (16)	−0.029 (3)	0.051
C75	0.8756 (19)	0.607 (2)	−0.089 (3)	0.051
C76	0.794 (3)	0.513 (3)	0.085 (3)	0.051
N77	0.793 (3)	0.490 (3)	−0.108 (3)	0.051
N78	0.913 (3)	0.663 (2)	−0.035 (3)	0.051
N79	0.888 (3)	0.618 (3)	−0.200 (3)	0.051
N80	0.838 (3)	0.576 (3)	0.128 (3)	0.051
O81	0.746 (4)	0.456 (4)	0.140 (5)	0.051
C82	0.840 (3)	0.548 (3)	−0.203 (3)	0.051
C83	0.733 (3)	0.416 (2)	−0.111 (3)	0.051
C84	0.894 (3)	0.648 (3)	0.075 (3)	0.051
C85	0.974 (3)	0.739 (3)	−0.082 (2)	0.051
C86	0.830 (3)	0.560 (3)	0.235 (3)	0.051
H87	0.838 (9)	0.539 (8)	−0.268 (9)	0.061
H88	0.772 (9)	0.339 (8)	−0.070 (9)	0.061
H89	0.655 (10)	0.445 (9)	−0.084 (9)	0.061
H90	0.729 (10)	0.421 (7)	−0.185 (8)	0.061
O91	0.930 (4)	0.702 (4)	0.112 (4)	0.051
H92	1.046 (9)	0.705 (7)	−0.045 (8)	0.061
H93	0.988 (9)	0.746 (7)	−0.155 (10)	0.061
H94	0.928 (9)	0.812 (7)	−0.072 (8)	0.061
H95	0.780 (9)	0.630 (8)	0.248 (8)	0.061
H96	0.803 (9)	0.504 (10)	0.267 (9)	0.061
H97	0.908 (10)	0.534 (8)	0.260 (8)	0.061

Geometric parameters (Å, º)

C1—C2	1.40 (4)	C50—C52	1.50 (4)
C1—C3	1.35 (4)	C50—N53	1.39 (6)
C1—C4	1.62 (5)	C51—N54	1.47 (6)
C2—C5	1.31 (5)	C51—N55	1.43 (6)
C2—H6	0.92 (12)	C52—N56	1.39 (6)
C3—C7	1.30 (5)	C52—O57	1.33 (6)
C3—H8	0.88 (12)	N53—C58	1.44 (5)
C4—H9	0.99 (12)	N53—C59	1.43 (6)
C4—H10	0.93 (11)	N54—C60	1.51 (5)
C4—H11	0.96 (12)	N54—C61	1.73 (5)
C5—C12	1.38 (4)	N55—C58	1.32 (7)
C5—H13	0.92 (12)	N56—C60	1.51 (5)
C7—C12	1.39 (4)	N56—C62	1.57 (4)
C7—H14	0.95 (10)	C58—H63	0.99 (13)
C12—H15	1.00 (12)	C59—H64	0.94 (9)
C16—C17	1.47 (4)	C59—H65	0.94 (11)
C16—C18	1.55 (5)	C59—H66	0.94 (13)
C16—C19	1.41 (5)	C60—O67	1.25 (8)
C17—O20	1.47 (7)	C61—H68	1.00 (12)
C17—O21	1.38 (7)	C61—H69	0.96 (11)
C18—C22	1.45 (4)	C61—H70	1.00 (13)
C18—H23	0.98 (14)	C62—H71	0.96 (12)
C19—C24	1.58 (5)	C62—H72	0.97 (18)
C19—N25	1.51 (6)	C62—H73	0.98 (9)
O20—H26	0.96 (13)	C74—C75	1.49 (4)
C22—C27	1.41 (5)	C74—C76	1.45 (5)
C22—H28	1.01 (16)	C74—N77	1.44 (6)
C24—C27	1.38 (6)	C75—N78	1.47 (6)
C24—H29	0.96 (13)	C75—N79	1.41 (6)
N25—H30	0.98 (11)	C76—N80	1.49 (6)
N25—H31	0.99 (17)	C76—O81	1.16 (6)
C27—H32	0.97 (11)	N77—C82	1.40 (5)
C33—C34	1.56 (5)	N77—C83	1.50 (6)
C33—C35	1.45 (6)	N78—C84	1.39 (5)
C33—C36	1.39 (5)	N78—C85	1.43 (5)
C34—O37	1.35 (6)	N79—C82	1.33 (7)
C34—O38	1.33 (8)	N80—C84	1.37 (5)
C35—C39	1.39 (5)	N80—C86	1.34 (5)
C35—H40	0.90 (13)	C82—H87	0.93 (13)
C36—C41	1.44 (5)	C83—H88	0.92 (8)
C36—N42	1.39 (6)	C83—H89	0.93 (11)
O37—H43	0.97 (14)	C83—H90	0.97 (12)
C39—C44	1.38 (5)	C84—O91	1.26 (8)
C39—H45	0.98 (14)	C85—H92	0.95 (12)
C41—C44	1.39 (6)	C85—H93	0.92 (14)
C41—H46	0.96 (13)	C85—H94	0.95 (10)
N42—H47	0.96 (12)	C86—H95	0.94 (11)
N42—H48	0.96 (13)	C86—H96	0.90 (14)
C44—H49	0.96 (11)	C86—H97	0.95 (13)
C50—C51	1.43 (5)
C2—C1—C3	115 (3)	C50—C52—N56	111 (3)
C2—C1—C4	125 (3)	C50—C52—O57	135 (5)
C3—C1—C4	120 (3)	N56—C52—O57	114 (4)
C1—C2—C5	121 (3)	C50—N53—C58	110 (3)
C1—C2—H6	123 (9)	C50—N53—C59	120 (3)
C5—C2—H6	116 (9)	C58—N53—C59	130 (4)
C1—C3—C7	126 (3)	C51—N54—C60	111 (3)
C1—C3—H8	117 (9)	C51—N54—C61	126 (3)
C7—C3—H8	117 (9)	C60—N54—C61	122 (4)
C1—C4—H9	111 (6)	C51—N55—C58	109 (3)
C1—C4—H10	109 (9)	C52—N56—C60	126 (3)
C1—C4—H11	114 (7)	C52—N56—C62	106 (3)
H9—C4—H10	108 (10)	C60—N56—C62	128 (4)
H9—C4—H11	108 (11)	N53—C58—N55	108 (4)
H10—C4—H11	106 (9)	N53—C58—H63	129 (8)
C2—C5—C12	123 (3)	N55—C58—H63	123 (7)
C2—C5—H13	117 (8)	N53—C59—H64	107 (10)
C12—C5—H13	120 (8)	N53—C59—H65	111 (8)
C3—C7—C12	120 (3)	N53—C59—H66	108 (7)
C3—C7—H14	117 (8)	H64—C59—H65	110 (10)
C12—C7—H14	123 (8)	H64—C59—H66	109 (9)
C5—C12—C7	116 (3)	H65—C59—H66	110 (11)
C5—C12—H15	119 (6)	N54—C60—N56	122 (4)
C7—C12—H15	126 (6)	N54—C60—O67	118 (4)
C17—C16—C18	119 (3)	N56—C60—O67	120 (4)
C17—C16—C19	126 (3)	N54—C61—H68	112 (6)
C18—C16—C19	116 (3)	N54—C61—H69	110 (9)
C16—C17—O20	103 (3)	N54—C61—H70	115 (8)
C16—C17—O21	130 (4)	H68—C61—H69	105 (10)
O20—C17—O21	128 (4)	H68—C61—H70	108 (12)
C16—C18—C22	128 (3)	H69—C61—H70	106 (9)
C16—C18—H23	117 (7)	N56—C62—H71	113 (7)
C22—C18—H23	115 (8)	N56—C62—H72	106 (8)
C16—C19—C24	113 (3)	N56—C62—H73	111 (7)
C16—C19—N25	119 (3)	H71—C62—H72	110 (11)
C24—C19—N25	128 (3)	H71—C62—H73	110 (12)
C17—O20—H26	117 (12)	H72—C62—H73	106 (10)
C18—C22—C27	116 (4)	C75—C74—C76	116 (4)
C18—C22—H28	121 (7)	C75—C74—N77	105 (3)
C27—C22—H28	123 (7)	C76—C74—N77	139 (3)
C19—C24—C27	130 (3)	C74—C75—N78	121 (3)
C19—C24—H29	118 (9)	C74—C75—N79	111 (4)
C27—C24—H29	112 (8)	N78—C75—N79	128 (3)
C19—N25—H30	118 (9)	C74—C76—N80	117 (3)
C19—N25—H31	122 (9)	C74—C76—O81	123 (5)
H30—N25—H31	120 (13)	N80—C76—O81	121 (5)
C22—C27—C24	118 (3)	C74—N77—C82	102 (4)
C22—C27—H32	122 (10)	C74—N77—C83	137 (3)
C24—C27—H32	119 (10)	C82—N77—C83	120 (4)
C34—C33—C35	128 (3)	C75—N78—C84	123 (3)
C34—C33—C36	120 (3)	C75—N78—C85	127 (3)
C35—C33—C36	112 (3)	C84—N78—C85	110 (4)
C33—C34—O37	116 (4)	C75—N79—C82	102 (3)
C33—C34—O38	131 (4)	C76—N80—C84	129 (3)
O37—C34—O38	113 (4)	C76—N80—C86	121 (3)
C33—C35—C39	131 (4)	C84—N80—C86	110 (4)
C33—C35—H40	116 (9)	N77—C82—N79	120 (4)
C39—C35—H40	113 (9)	N77—C82—H87	121 (9)
C33—C36—C41	117 (4)	N79—C82—H87	119 (8)
C33—C36—N42	123 (3)	N77—C83—H88	111 (9)
C41—C36—N42	119 (3)	N77—C83—H89	109 (10)
C34—O37—H43	113 (8)	N77—C83—H90	110 (8)
C35—C39—C44	115 (4)	H88—C83—H89	109 (9)
C35—C39—H45	123 (7)	H88—C83—H90	109 (10)
C44—C39—H45	122 (7)	H89—C83—H90	108 (11)
C36—C41—C44	127 (4)	N78—C84—N80	114 (4)
C36—C41—H46	114 (9)	N78—C84—O91	117 (4)
C44—C41—H46	118 (8)	N80—C84—O91	129 (4)
C36—N42—H47	119 (9)	N78—C85—H92	108 (6)
C36—N42—H48	118 (9)	N78—C85—H93	108 (9)
H47—N42—H48	123 (12)	N78—C85—H94	109 (7)
C39—C44—C41	117 (3)	H92—C85—H93	112 (9)
C39—C44—H49	122 (9)	H92—C85—H94	107 (10)
C41—C44—H49	121 (9)	H93—C85—H94	113 (8)
C51—C50—C52	126 (4)	N80—C86—H95	111 (6)
C51—C50—N53	104 (3)	N80—C86—H96	107 (10)
C52—C50—N53	130 (3)	N80—C86—H97	109 (7)
C50—C51—N54	124 (3)	H95—C86—H96	112 (11)
C50—C51—N55	109 (4)	H95—C86—H97	110 (12)
N54—C51—N55	127 (3)	H96—C86—H97	109 (10)

(Toluene_Monosolvate)

Crystal data

C8H10N4O2·C7H7NO2·C7H8	Z = 4
Mr = 423.47	F(000) = 896
Triclinic, P1	Dx = 1.314 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.7113 (3) Å	Cell parameters from 14929 reflections
b = 13.5803 (6) Å	θ = 1.0–22.5°
c = 23.579 (2) Å	µ = 0.09 mm^−1
α = 87.100 (2)°	T = 180 K
β = 88.572 (2)°	Block, colourless
γ = 86.065 (2)°	0.46 × 0.12 × 0.05 mm
V = 2140.7 (2) Å^3

Data collection

Nonius Kappa CCD diffractometer	3560 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.082
Thin slice ω and φ scans	θmax = 22.4°, θmin = 3.5°
Absorption correction: multi-scan SORTAV (Blessing, 1995)	h = −7→7
Tmin = 0.740, Tmax = 1.000	k = −14→14
11209 measured reflections	l = −24→25
5163 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)] = 0.133	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.360	H-atom parameters constrained
S = 1.36	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
5163 reflections	(Δ/σ)max < 0.001
543 parameters	Δρmax = 0.89 e Å^−3
0 restraints	Δρmin = −0.44 e Å^−3

Special details

Experimental. Poorly diffracting crystals —> relatively poor data. The –COOH hydrogen atoms were NOT located but placed in reasonable positions consistent with the C—O distances and the O—H···N hydrogen bonds.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.7785 (9)	0.5952 (5)	−0.0439 (3)	0.0402 (16)
N1	0.8047 (8)	0.6757 (4)	−0.1607 (2)	0.0448 (14)
H1A	0.7995	0.6114	−0.1548	0.054*
H1B	0.8108	0.7015	−0.1957	0.054*
O1	0.7746 (7)	0.5311 (3)	−0.07865 (19)	0.0492 (12)
C2	0.7936 (8)	0.7014 (4)	−0.0590 (2)	0.0359 (16)
O2	0.7678 (6)	0.5743 (3)	0.01134 (19)	0.0497 (12)
H2X	0.7501	0.5140	0.0173	0.060*
C3	0.8031 (9)	0.7356 (5)	−0.1155 (3)	0.0400 (16)
C4	0.8135 (9)	0.8384 (5)	−0.1278 (3)	0.0443 (17)
H4	0.8226	0.8629	−0.1662	0.053*
C5	0.8106 (10)	0.9027 (5)	−0.0848 (3)	0.0541 (19)
H5	0.8166	0.9716	−0.0934	0.065*
C6	0.7990 (10)	0.8670 (5)	−0.0283 (3)	0.0485 (17)
H6	0.7963	0.9115	0.0016	0.058*
C7	0.7916 (9)	0.7692 (4)	−0.0160 (3)	0.0387 (16)
H7	0.7850	0.7457	0.0226	0.046*
N2	0.3084 (7)	0.8156 (4)	0.6573 (2)	0.0486 (15)
H2A	0.2897	0.8802	0.6522	0.058*
H2B	0.3160	0.7883	0.6919	0.058*
O3	0.2801 (6)	0.9282 (3)	0.48698 (18)	0.0419 (11)
H3X	0.2558	0.9896	0.4825	0.050*
O4	0.2654 (6)	0.9657 (3)	0.57836 (19)	0.0475 (12)
C8	0.2840 (8)	0.9031 (5)	0.5415 (3)	0.0358 (16)
C9	0.3151 (8)	0.7964 (4)	0.5554 (3)	0.0299 (14)
C10	0.3254 (8)	0.7589 (5)	0.6124 (3)	0.0371 (16)
C11	0.3521 (8)	0.6541 (5)	0.6214 (3)	0.0434 (17)
H11	0.3596	0.6266	0.6592	0.052*
C12	0.3670 (9)	0.5926 (5)	0.5779 (3)	0.0479 (18)
H12	0.3852	0.5233	0.5857	0.057*
C13	0.3560 (9)	0.6299 (5)	0.5213 (3)	0.0448 (17)
H13	0.3645	0.5866	0.4908	0.054*
C14	0.3327 (8)	0.7299 (4)	0.5111 (3)	0.0363 (15)
H14	0.3281	0.7556	0.4729	0.044*
N3	0.6942 (7)	0.3458 (4)	0.1368 (2)	0.0420 (14)
N4	0.7069 (7)	0.2260 (4)	0.0075 (2)	0.0423 (14)
N5	0.7132 (8)	0.3809 (4)	0.0342 (2)	0.0439 (14)
O5	0.6905 (7)	0.0543 (3)	0.0979 (2)	0.0536 (13)
O6	0.6786 (7)	0.2933 (3)	0.22845 (19)	0.0533 (13)
C15	0.6908 (9)	0.1432 (5)	0.1070 (3)	0.0450 (17)
N3'	0.6797 (8)	0.1759 (4)	0.1625 (2)	0.0436 (14)
C17	0.6855 (9)	0.2732 (5)	0.1785 (3)	0.0430 (17)
C18	0.7025 (9)	0.3182 (5)	0.0804 (3)	0.0401 (16)
C19	0.7001 (9)	0.2230 (5)	0.0661 (3)	0.0382 (16)
C20	0.7144 (9)	0.3210 (5)	−0.0092 (3)	0.0474 (18)
H20	0.7201	0.3438	−0.0479	0.057*
C21	0.6978 (11)	0.4485 (5)	0.1487 (3)	0.0558 (19)
H21A	0.6754	0.4563	0.1895	0.084*
H21B	0.5923	0.4869	0.1276	0.084*
H21C	0.8280	0.4723	0.1372	0.084*
C22	0.7073 (11)	0.1430 (5)	−0.0292 (3)	0.0547 (19)
H22A	0.7065	0.1676	−0.0690	0.082*
H22B	0.5882	0.1065	−0.0209	0.082*
H22C	0.8273	0.0991	−0.0226	0.082*
C23	0.6684 (13)	0.1018 (5)	0.2102 (3)	0.064 (2)
H23A	0.7862	0.1036	0.2338	0.097*
H23B	0.6642	0.0359	0.1954	0.097*
H23C	0.5474	0.1168	0.2331	0.097*
N6	0.1936 (7)	0.1640 (4)	0.3669 (2)	0.0341 (12)
N7	0.1638 (7)	0.2806 (4)	0.4964 (2)	0.0337 (13)
O7	0.1279 (6)	0.4552 (3)	0.40698 (18)	0.0454 (12)
N8	0.2044 (6)	0.1257 (4)	0.4684 (2)	0.0340 (13)
O8	0.1799 (6)	0.2184 (3)	0.27458 (19)	0.0491 (12)
C24	0.1442 (8)	0.3665 (5)	0.3970 (3)	0.0355 (15)
N6'	0.1459 (7)	0.3340 (4)	0.3412 (2)	0.0385 (13)
C26	0.1732 (9)	0.2367 (5)	0.3254 (3)	0.0365 (15)
C27	0.1867 (8)	0.1899 (4)	0.4227 (3)	0.0313 (15)
C28	0.1632 (8)	0.2854 (4)	0.4380 (2)	0.0282 (14)
C29	0.1870 (8)	0.1845 (5)	0.5122 (3)	0.0368 (16)
H29	0.1908	0.1605	0.5507	0.044*
C30	0.1200 (11)	0.4102 (5)	0.2951 (3)	0.058 (2)
H30A	0.0127	0.3937	0.2705	0.087*
H30B	0.2447	0.4133	0.2727	0.087*
H30C	0.0852	0.4744	0.3112	0.087*
C31	0.2204 (10)	0.0611 (4)	0.3534 (3)	0.0472 (17)
H31A	0.2147	0.0558	0.3121	0.071*
H31B	0.1140	0.0245	0.3720	0.071*
H31C	0.3504	0.0333	0.3668	0.071*
C32	0.1435 (10)	0.3626 (5)	0.5340 (3)	0.0453 (17)
H32A	0.1684	0.3380	0.5731	0.068*
H32B	0.0080	0.3941	0.5316	0.068*
H32C	0.2405	0.4109	0.5224	0.068*
C33	0.313 (2)	0.8982 (9)	0.2111 (5)	0.137 (5)
H33A	0.4135	0.8631	0.2355	0.205*
H33B	0.2288	0.9441	0.2336	0.205*
H33C	0.3800	0.9352	0.1803	0.205*
C34	0.1895 (10)	0.8272 (5)	0.1872 (2)	0.074 (2)
C35	0.2497 (11)	0.7274 (5)	0.1855 (3)	0.117 (4)
H35	0.3745	0.7032	0.2006	0.140*
C36	0.1272 (16)	0.6628 (4)	0.1617 (3)	0.115 (4)
H36	0.1683	0.5946	0.1605	0.137*
C37	−0.0555 (15)	0.6981 (7)	0.1395 (3)	0.149 (6)
H37	−0.1392	0.6540	0.1232	0.178*
C38	−0.1157 (9)	0.7979 (7)	0.1412 (3)	0.128 (5)
H38	−0.2406	0.8220	0.1260	0.154*
C39	0.0068 (10)	0.8625 (4)	0.1650 (3)	0.074 (2)
H39	−0.0344	0.9307	0.1662	0.089*
C40	0.816 (2)	0.8656 (10)	0.3187 (5)	0.140 (5)
H40A	0.7883	0.9055	0.3518	0.210*
H40B	0.7797	0.9051	0.2841	0.210*
H40C	0.9584	0.8444	0.3169	0.210*
C41	0.7054 (14)	0.7838 (5)	0.3233 (3)	0.110 (4)
C42	0.5219 (15)	0.7911 (7)	0.3520 (3)	0.094 (3)
H42	0.4782	0.8506	0.3693	0.113*
C43	0.4026 (11)	0.7112 (10)	0.3553 (3)	0.160 (7)
H43	0.2772	0.7162	0.3749	0.192*
C44	0.4666 (16)	0.6241 (8)	0.3299 (4)	0.160 (7)
H44	0.3850	0.5695	0.3322	0.192*
C45	0.6500 (18)	0.6168 (5)	0.3012 (4)	0.120 (4)
H45	0.6938	0.5573	0.2838	0.145*
C46	0.7694 (12)	0.6967 (6)	0.2979 (3)	0.100 (3)
H46	0.8948	0.6918	0.2782	0.120*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.050 (4)	0.043 (4)	0.026 (4)	0.000 (3)	−0.001 (3)	0.007 (4)
N1	0.070 (4)	0.032 (3)	0.033 (3)	−0.002 (2)	−0.001 (3)	−0.009 (3)
O1	0.074 (3)	0.036 (3)	0.038 (3)	−0.005 (2)	−0.001 (2)	−0.002 (2)
C2	0.037 (3)	0.041 (4)	0.029 (4)	0.002 (3)	−0.008 (3)	0.011 (3)
O2	0.071 (3)	0.038 (3)	0.041 (3)	−0.004 (2)	−0.001 (2)	0.000 (2)
C3	0.040 (4)	0.033 (4)	0.046 (5)	0.004 (3)	0.003 (3)	−0.003 (3)
C4	0.048 (4)	0.042 (5)	0.042 (4)	−0.002 (3)	−0.001 (3)	0.007 (4)
C5	0.061 (4)	0.038 (4)	0.062 (5)	0.000 (3)	0.000 (4)	0.000 (4)
C6	0.069 (4)	0.042 (5)	0.035 (4)	−0.005 (3)	−0.003 (3)	−0.001 (3)
C7	0.055 (4)	0.030 (4)	0.032 (4)	−0.001 (3)	−0.001 (3)	−0.005 (3)
N2	0.061 (4)	0.052 (4)	0.032 (3)	−0.004 (3)	−0.006 (3)	0.003 (3)
O3	0.059 (3)	0.028 (2)	0.038 (3)	−0.0016 (19)	0.0012 (19)	0.002 (2)
O4	0.073 (3)	0.034 (3)	0.035 (3)	−0.001 (2)	0.000 (2)	−0.001 (2)
C8	0.031 (3)	0.042 (4)	0.033 (4)	0.000 (3)	0.000 (3)	0.003 (4)
C9	0.027 (3)	0.024 (3)	0.039 (4)	−0.004 (2)	−0.002 (2)	0.003 (3)
C10	0.034 (3)	0.042 (4)	0.035 (4)	−0.005 (3)	−0.001 (3)	0.005 (3)
C11	0.034 (4)	0.041 (4)	0.054 (5)	−0.003 (3)	−0.002 (3)	0.013 (4)
C12	0.049 (4)	0.035 (4)	0.060 (5)	0.000 (3)	−0.001 (3)	0.000 (4)
C13	0.059 (4)	0.031 (4)	0.045 (5)	−0.001 (3)	0.001 (3)	−0.005 (3)
C14	0.036 (3)	0.037 (4)	0.035 (4)	−0.001 (3)	−0.002 (3)	0.002 (3)
N3	0.051 (3)	0.042 (4)	0.032 (3)	−0.004 (2)	0.000 (2)	0.001 (3)
N4	0.052 (3)	0.039 (4)	0.034 (3)	0.004 (2)	0.003 (2)	0.005 (3)
N5	0.058 (3)	0.040 (3)	0.032 (3)	0.003 (2)	0.003 (2)	0.009 (3)
O5	0.082 (3)	0.031 (3)	0.048 (3)	−0.004 (2)	0.004 (2)	−0.001 (2)
O6	0.075 (3)	0.053 (3)	0.032 (3)	−0.009 (2)	0.001 (2)	0.004 (2)
C15	0.045 (4)	0.042 (5)	0.048 (5)	−0.007 (3)	−0.004 (3)	0.006 (4)
N3'	0.058 (3)	0.035 (3)	0.037 (3)	−0.006 (2)	0.001 (2)	0.004 (3)
C17	0.050 (4)	0.058 (5)	0.021 (4)	−0.001 (3)	−0.001 (3)	0.003 (4)
C18	0.045 (4)	0.038 (4)	0.036 (4)	−0.001 (3)	0.005 (3)	0.003 (3)
C19	0.052 (4)	0.034 (4)	0.027 (4)	0.000 (3)	0.004 (3)	0.005 (3)
C20	0.061 (4)	0.044 (5)	0.035 (4)	0.005 (3)	0.003 (3)	0.008 (4)
C21	0.086 (5)	0.037 (4)	0.046 (5)	−0.005 (3)	−0.012 (4)	−0.009 (4)
C22	0.081 (5)	0.048 (5)	0.035 (4)	0.002 (4)	0.008 (3)	−0.016 (4)
C23	0.109 (6)	0.036 (4)	0.047 (5)	−0.009 (4)	0.005 (4)	0.012 (4)
N6	0.044 (3)	0.033 (3)	0.025 (3)	−0.002 (2)	−0.001 (2)	0.000 (3)
N7	0.040 (3)	0.032 (3)	0.029 (3)	0.000 (2)	−0.006 (2)	−0.003 (2)
O7	0.060 (3)	0.029 (3)	0.047 (3)	0.0012 (19)	0.000 (2)	−0.004 (2)
N8	0.036 (3)	0.032 (3)	0.035 (3)	−0.005 (2)	−0.005 (2)	0.003 (3)
O8	0.067 (3)	0.045 (3)	0.036 (3)	−0.004 (2)	0.001 (2)	−0.004 (2)
C24	0.034 (3)	0.036 (4)	0.037 (4)	−0.006 (3)	−0.002 (3)	0.001 (3)
N6'	0.048 (3)	0.035 (3)	0.032 (3)	−0.002 (2)	−0.001 (2)	0.008 (3)
C26	0.045 (4)	0.032 (4)	0.034 (4)	−0.010 (3)	0.002 (3)	−0.009 (3)
C27	0.024 (3)	0.031 (4)	0.038 (4)	0.001 (2)	0.002 (2)	0.001 (3)
C28	0.032 (3)	0.025 (4)	0.028 (4)	−0.003 (2)	0.000 (2)	−0.008 (3)
C29	0.034 (3)	0.045 (5)	0.030 (4)	−0.003 (3)	−0.001 (3)	0.007 (3)
C30	0.083 (5)	0.042 (4)	0.046 (5)	0.001 (4)	−0.005 (4)	0.011 (4)
C31	0.072 (4)	0.031 (4)	0.040 (4)	−0.003 (3)	0.000 (3)	−0.012 (3)
C32	0.060 (4)	0.041 (4)	0.037 (4)	−0.006 (3)	−0.003 (3)	−0.014 (3)
C33	0.184 (13)	0.125 (11)	0.110 (10)	−0.070 (9)	−0.039 (9)	0.014 (8)
C34	0.107 (7)	0.070 (6)	0.042 (5)	0.013 (5)	0.002 (4)	−0.004 (4)
C35	0.191 (12)	0.084 (9)	0.063 (7)	0.041 (8)	0.030 (7)	0.025 (6)
C36	0.231 (15)	0.056 (7)	0.057 (7)	−0.015 (8)	0.031 (8)	−0.023 (6)
C37	0.213 (17)	0.195 (18)	0.045 (7)	−0.085 (13)	0.005 (8)	0.011 (9)
C38	0.223 (14)	0.091 (9)	0.067 (8)	−0.025 (9)	0.059 (8)	0.011 (7)
C39	0.112 (7)	0.064 (6)	0.046 (5)	−0.006 (5)	0.015 (5)	−0.015 (4)
C40	0.228 (15)	0.125 (11)	0.076 (8)	−0.056 (10)	−0.035 (8)	−0.016 (7)
C41	0.195 (13)	0.069 (8)	0.065 (7)	−0.013 (8)	−0.023 (8)	0.009 (6)
C42	0.132 (9)	0.105 (9)	0.039 (6)	0.026 (7)	−0.002 (5)	0.017 (6)
C43	0.26 (2)	0.150 (14)	0.066 (9)	0.030 (15)	−0.079 (10)	0.007 (10)
C44	0.212 (19)	0.175 (18)	0.097 (11)	−0.049 (13)	−0.086 (12)	0.046 (11)
C45	0.162 (12)	0.098 (10)	0.101 (10)	−0.003 (9)	−0.026 (9)	0.006 (7)
C46	0.178 (11)	0.068 (7)	0.054 (6)	0.018 (7)	−0.006 (6)	−0.025 (5)

Geometric parameters (Å, º)

C1—O1	1.227 (7)	C23—H23B	0.9800
C1—O2	1.320 (7)	C23—H23C	0.9800
C1—C2	1.477 (9)	N6—C26	1.358 (8)
N1—C3	1.373 (8)	N6—C27	1.377 (8)
N1—H1A	0.8800	N6—C31	1.448 (8)
N1—H1B	0.8800	N7—C29	1.338 (8)
C2—C3	1.390 (9)	N7—C28	1.378 (7)
C2—C7	1.403 (8)	N7—C32	1.454 (7)
O2—H2X	0.8400	O7—C24	1.235 (7)
C3—C4	1.416 (9)	N8—C29	1.333 (8)
C4—C5	1.371 (9)	N8—C27	1.355 (7)
C4—H4	0.9500	O8—C26	1.235 (7)
C5—C6	1.397 (10)	C24—N6'	1.408 (8)
C5—H5	0.9500	C24—C28	1.429 (9)
C6—C7	1.349 (9)	N6'—C26	1.389 (8)
C6—H6	0.9500	N6'—C30	1.468 (8)
C7—H7	0.9500	C27—C28	1.360 (8)
N2—C10	1.340 (8)	C29—H29	0.9500
N2—H2A	0.8800	C30—H30A	0.9800
N2—H2B	0.8800	C30—H30B	0.9800
O3—C8	1.314 (7)	C30—H30C	0.9800
O3—H3X	0.8400	C31—H31A	0.9800
O4—C8	1.244 (7)	C31—H31B	0.9800
C8—C9	1.471 (8)	C31—H31C	0.9800
C9—C14	1.411 (8)	C32—H32A	0.9800
C9—C10	1.414 (9)	C32—H32B	0.9800
C10—C11	1.428 (9)	C32—H32C	0.9800
C11—C12	1.353 (9)	C33—C34	1.458 (11)
C11—H11	0.9500	C33—H33A	0.9800
C12—C13	1.405 (9)	C33—H33B	0.9800
C12—H12	0.9500	C33—H33C	0.9800
C13—C14	1.365 (9)	C34—C35	1.3900
C13—H13	0.9500	C34—C39	1.3900
C14—H14	0.9500	C35—C36	1.3900
N3—C17	1.361 (8)	C35—H35	0.9500
N3—C18	1.398 (8)	C36—C37	1.3900
N3—C21	1.439 (8)	C36—H36	0.9500
N4—C20	1.333 (8)	C37—C38	1.3900
N4—C19	1.380 (8)	C37—H37	0.9500
N4—C22	1.456 (8)	C38—C39	1.3900
N5—C20	1.337 (8)	C38—H38	0.9500
N5—C18	1.352 (8)	C39—H39	0.9500
O5—C15	1.237 (8)	C40—C41	1.375 (13)
O6—C17	1.221 (7)	C40—H40A	0.9800
C15—N3'	1.400 (9)	C40—H40B	0.9800
C15—C19	1.418 (9)	C40—H40C	0.9800
N3'—C17	1.396 (8)	C41—C42	1.3900
N3'—C23	1.475 (8)	C41—C46	1.3900
C18—C19	1.354 (9)	C42—C43	1.3900
C20—H20	0.9500	C42—H42	0.9500
C21—H21A	0.9800	C43—C44	1.3900
C21—H21B	0.9800	C43—H43	0.9500
C21—H21C	0.9800	C44—C45	1.3900
C22—H22A	0.9800	C44—H44	0.9500
C22—H22B	0.9800	C45—C46	1.3900
C22—H22C	0.9800	C45—H45	0.9500
C23—H23A	0.9800	C46—H46	0.9500
O1—C1—O2	122.0 (6)	H23B—C23—H23C	109.5
O1—C1—C2	124.3 (6)	C26—N6—C27	118.6 (5)
O2—C1—C2	113.8 (6)	C26—N6—C31	121.1 (5)
C3—N1—H1A	120.0	C27—N6—C31	120.2 (5)
C3—N1—H1B	120.0	C29—N7—C28	106.0 (5)
H1A—N1—H1B	120.0	C29—N7—C32	126.5 (5)
C3—C2—C7	119.3 (6)	C28—N7—C32	127.4 (5)
C3—C2—C1	120.8 (6)	C29—N8—C27	103.2 (5)
C7—C2—C1	119.8 (6)	O7—C24—N6'	122.0 (5)
C1—O2—H2X	109.5	O7—C24—C28	126.5 (6)
N1—C3—C2	124.0 (6)	N6'—C24—C28	111.5 (5)
N1—C3—C4	117.4 (6)	C26—N6'—C24	126.4 (5)
C2—C3—C4	118.6 (6)	C26—N6'—C30	116.6 (5)
C5—C4—C3	120.6 (6)	C24—N6'—C30	117.0 (5)
C5—C4—H4	119.7	O8—C26—N6	121.7 (6)
C3—C4—H4	119.7	O8—C26—N6'	119.9 (6)
C4—C5—C6	119.9 (7)	N6—C26—N6'	118.3 (5)
C4—C5—H5	120.0	N8—C27—C28	111.9 (5)
C6—C5—H5	120.0	N8—C27—N6	125.2 (5)
C7—C6—C5	120.0 (7)	C28—C27—N6	122.8 (5)
C7—C6—H6	120.0	C27—C28—N7	105.4 (5)
C5—C6—H6	120.0	C27—C28—C24	122.2 (5)
C6—C7—C2	121.5 (6)	N7—C28—C24	132.4 (5)
C6—C7—H7	119.3	N8—C29—N7	113.4 (5)
C2—C7—H7	119.3	N8—C29—H29	123.3
C10—N2—H2A	120.0	N7—C29—H29	123.3
C10—N2—H2B	120.0	N6'—C30—H30A	109.5
H2A—N2—H2B	120.0	N6'—C30—H30B	109.5
C8—O3—H3X	109.5	H30A—C30—H30B	109.5
O4—C8—O3	121.9 (6)	N6'—C30—H30C	109.5
O4—C8—C9	123.0 (6)	H30A—C30—H30C	109.5
O3—C8—C9	115.1 (6)	H30B—C30—H30C	109.5
C14—C9—C10	119.2 (5)	N6—C31—H31A	109.5
C14—C9—C8	119.5 (5)	N6—C31—H31B	109.5
C10—C9—C8	121.2 (6)	H31A—C31—H31B	109.5
N2—C10—C9	123.8 (6)	N6—C31—H31C	109.5
N2—C10—C11	119.3 (6)	H31A—C31—H31C	109.5
C9—C10—C11	116.9 (6)	H31B—C31—H31C	109.5
C12—C11—C10	122.2 (6)	N7—C32—H32A	109.5
C12—C11—H11	118.9	N7—C32—H32B	109.5
C10—C11—H11	118.9	H32A—C32—H32B	109.5
C11—C12—C13	120.9 (6)	N7—C32—H32C	109.5
C11—C12—H12	119.6	H32A—C32—H32C	109.5
C13—C12—H12	119.6	H32B—C32—H32C	109.5
C14—C13—C12	118.5 (6)	C34—C33—H33A	109.5
C14—C13—H13	120.8	C34—C33—H33B	109.5
C12—C13—H13	120.8	H33A—C33—H33B	109.5
C13—C14—C9	122.3 (6)	C34—C33—H33C	109.5
C13—C14—H14	118.8	H33A—C33—H33C	109.5
C9—C14—H14	118.8	H33B—C33—H33C	109.5
C17—N3—C18	118.0 (6)	C35—C34—C39	120.0
C17—N3—C21	122.5 (5)	C35—C34—C33	122.2 (8)
C18—N3—C21	119.6 (5)	C39—C34—C33	117.8 (8)
C20—N4—C19	106.1 (5)	C34—C35—C36	120.0
C20—N4—C22	126.4 (6)	C34—C35—H35	120.0
C19—N4—C22	127.5 (6)	C36—C35—H35	120.0
C20—N5—C18	103.3 (5)	C37—C36—C35	120.0
O5—C15—N3'	121.1 (6)	C37—C36—H36	120.0
O5—C15—C19	127.2 (6)	C35—C36—H36	120.0
N3'—C15—C19	111.7 (6)	C36—C37—C38	120.0
C17—N3'—C15	126.7 (6)	C36—C37—H37	120.0
C17—N3'—C23	114.7 (5)	C38—C37—H37	120.0
C15—N3'—C23	118.6 (6)	C37—C38—C39	120.0
O6—C17—N3	120.6 (6)	C37—C38—H38	120.0
O6—C17—N3'	121.3 (6)	C39—C38—H38	120.0
N3—C17—N3'	118.1 (6)	C38—C39—C34	120.0
N5—C18—C19	112.0 (6)	C38—C39—H39	120.0
N5—C18—N3	125.3 (6)	C34—C39—H39	120.0
C19—C18—N3	122.7 (6)	C41—C40—H40A	109.5
C18—C19—N4	105.4 (5)	C41—C40—H40B	109.5
C18—C19—C15	122.7 (6)	H40A—C40—H40B	109.5
N4—C19—C15	131.8 (6)	C41—C40—H40C	109.5
N4—C20—N5	113.2 (6)	H40A—C40—H40C	109.5
N4—C20—H20	123.4	H40B—C40—H40C	109.5
N5—C20—H20	123.4	C40—C41—C42	118.5 (9)
N3—C21—H21A	109.5	C40—C41—C46	121.4 (9)
N3—C21—H21B	109.5	C42—C41—C46	120.0
H21A—C21—H21B	109.5	C43—C42—C41	120.0
N3—C21—H21C	109.5	C43—C42—H42	120.0
H21A—C21—H21C	109.5	C41—C42—H42	120.0
H21B—C21—H21C	109.5	C42—C43—C44	120.0
N4—C22—H22A	109.5	C42—C43—H43	120.0
N4—C22—H22B	109.5	C44—C43—H43	120.0
H22A—C22—H22B	109.5	C45—C44—C43	120.0
N4—C22—H22C	109.5	C45—C44—H44	120.0
H22A—C22—H22C	109.5	C43—C44—H44	120.0
H22B—C22—H22C	109.5	C46—C45—C44	120.0
N3'—C23—H23A	109.5	C46—C45—H45	120.0
N3'—C23—H23B	109.5	C44—C45—H45	120.0
H23A—C23—H23B	109.5	C45—C46—C41	120.0
N3'—C23—H23C	109.5	C45—C46—H46	120.0
H23A—C23—H23C	109.5	C41—C46—H46	120.0

(o_Xylene_Monosolvate)

Crystal data

C8H10N4O2·C7H7NO2·C8H10	F(000) = 928
Mr = 437.50	Dx = 1.322 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7864 reflections
a = 13.8492 (3) Å	θ = 1.0–27.5°
b = 6.7890 (2) Å	µ = 0.09 mm^−1
c = 23.3960 (7) Å	T = 180 K
β = 92.260 (1)°	Block, colourless
V = 2198.0 (1) Å^3	0.46 × 0.16 × 0.10 mm
Z = 4

Data collection

Nonius Kappa CCD diffractometer	2651 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
Thin slice ω and φ scans	θmax = 27.5°, θmin = 3.7°
Absorption correction: multi-scan SORTAV (Blessing, 1995)	h = −17→17
Tmin = 0.851, Tmax = 0.998	k = −8→8
13598 measured reflections	l = −29→30
4909 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)] = 0.127	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.436	H-atom parameters constrained
S = 1.55	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
4909 reflections	(Δ/σ)max = 0.006
236 parameters	Δρmax = 1.35 e Å^−3
0 restraints	Δρmin = −0.60 e Å^−3

Special details

Experimental. The o-xylene solvate molecule is poorly resolved, modelled with geometric constraints and a common isotropic displacement parameter for its C atoms.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.3272 (3)	0.6954 (5)	0.34054 (18)	0.0467 (11)
H1A	0.3900	0.7123	0.3453	0.056*
H1B	0.3006	0.6879	0.3058	0.056*
O1	0.4735 (2)	0.7418 (5)	0.41844 (15)	0.0489 (10)
C1	0.4142 (3)	0.7227 (6)	0.4558 (2)	0.0349 (11)
O2	0.4387 (2)	0.7300 (5)	0.51045 (14)	0.0442 (9)
H2	0.4987	0.7471	0.5145	0.053*
C2	0.3108 (3)	0.6923 (5)	0.44366 (19)	0.0321 (11)
C3	0.2712 (4)	0.6810 (6)	0.3869 (2)	0.0364 (11)
C4	0.1705 (3)	0.6574 (6)	0.3774 (2)	0.0436 (13)
H4	0.1434	0.6506	0.3395	0.052*
C5	0.1109 (4)	0.6441 (7)	0.4240 (3)	0.0502 (14)
H5	0.0432	0.6293	0.4175	0.060*
C6	0.1483 (4)	0.6521 (7)	0.4787 (3)	0.0529 (14)
H6	0.1070	0.6387	0.5099	0.064*
C7	0.2473 (4)	0.6799 (6)	0.4889 (2)	0.0439 (12)
H7	0.2723	0.6906	0.5272	0.053*
N2	0.8332 (3)	0.8461 (5)	0.65791 (16)	0.0377 (10)
O3	0.9510 (2)	0.8618 (5)	0.59208 (15)	0.0490 (10)
N3	0.6668 (3)	0.8107 (5)	0.63186 (16)	0.0346 (9)
N4	0.6323 (3)	0.8025 (5)	0.52947 (17)	0.0385 (10)
O5	0.7177 (2)	0.8200 (5)	0.72532 (14)	0.0463 (9)
N5	0.7836 (3)	0.8341 (5)	0.50178 (17)	0.0432 (11)
C8	0.8650 (3)	0.8513 (6)	0.6022 (2)	0.0351 (11)
C9	0.7372 (3)	0.8244 (6)	0.6743 (2)	0.0367 (11)
C10	0.6919 (3)	0.8171 (6)	0.5762 (2)	0.0358 (11)
C11	0.7861 (3)	0.8347 (6)	0.56058 (19)	0.0340 (11)
C12	0.6912 (4)	0.8160 (7)	0.4860 (2)	0.0437 (12)
H12	0.6689	0.8129	0.4471	0.052*
C13	0.5668 (4)	0.7872 (8)	0.6456 (2)	0.0504 (14)
H13A	0.5589	0.8199	0.6859	0.076*
H13B	0.5469	0.6505	0.6386	0.076*
H13C	0.5266	0.8753	0.6215	0.076*
C14	0.8653 (4)	0.8506 (7)	0.4647 (2)	0.0526 (14)
H14A	0.8416	0.8640	0.4249	0.079*
H14B	0.9055	0.7323	0.4687	0.079*
H14C	0.9038	0.9667	0.4757	0.079*
C15	0.9038 (4)	0.8675 (9)	0.7054 (2)	0.0556 (14)
H15A	0.9687	0.8785	0.6905	0.083*
H15B	0.9010	0.7519	0.7304	0.083*
H15C	0.8893	0.9862	0.7273	0.083*
C16	0.2575 (4)	0.4880 (9)	0.6600 (3)	0.1219 (13)*
C17	0.2648 (4)	0.2998 (9)	0.6831 (3)	0.1219 (13)*
C18	0.1820 (5)	0.2006 (7)	0.6987 (3)	0.1219 (13)*
H18	0.1870	0.0719	0.7145	0.146*
C19	0.0921 (4)	0.2896 (9)	0.6911 (3)	0.1219 (13)*
H19	0.0355	0.2218	0.7018	0.146*
C20	0.0848 (4)	0.4779 (9)	0.6680 (3)	0.1219 (13)*
H20	0.0233	0.5388	0.6628	0.146*
C21	0.1676 (5)	0.5771 (7)	0.6524 (3)	0.1219 (13)*
H21	0.1626	0.7058	0.6366	0.146*
C22	0.3526 (6)	0.5551 (15)	0.6435 (4)	0.1219 (13)*
H22A	0.4007	0.5233	0.6739	0.183*
H22B	0.3511	0.6979	0.6374	0.183*
H22C	0.3698	0.4891	0.6081	0.183*
C23	0.3540 (7)	0.1898 (13)	0.6868 (5)	0.1219 (13)*
H23A	0.4034	0.2666	0.7081	0.183*
H23B	0.3757	0.1631	0.6482	0.183*
H23C	0.3435	0.0649	0.7066	0.183*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.053 (3)	0.058 (3)	0.028 (2)	0.003 (2)	−0.005 (2)	−0.0047 (18)
O1	0.0424 (19)	0.070 (2)	0.035 (2)	0.0049 (17)	0.0026 (16)	−0.0015 (16)
C1	0.044 (3)	0.031 (2)	0.029 (3)	0.0041 (19)	−0.003 (2)	0.0022 (18)
O2	0.0418 (19)	0.056 (2)	0.034 (2)	−0.0010 (15)	−0.0066 (15)	0.0041 (15)
C2	0.040 (3)	0.027 (2)	0.030 (3)	−0.0001 (18)	0.000 (2)	0.0028 (17)
C3	0.048 (3)	0.027 (2)	0.035 (3)	0.0040 (19)	0.001 (2)	0.0015 (18)
C4	0.048 (3)	0.040 (3)	0.042 (3)	0.005 (2)	−0.008 (2)	−0.002 (2)
C5	0.033 (3)	0.051 (3)	0.066 (4)	−0.003 (2)	−0.008 (3)	−0.007 (3)
C6	0.051 (3)	0.058 (3)	0.051 (4)	0.002 (2)	0.016 (3)	0.002 (3)
C7	0.054 (3)	0.043 (3)	0.035 (3)	0.002 (2)	0.004 (2)	−0.006 (2)
N2	0.040 (2)	0.040 (2)	0.032 (2)	0.0013 (16)	−0.0068 (17)	−0.0034 (16)
O3	0.038 (2)	0.059 (2)	0.051 (2)	−0.0039 (15)	−0.0006 (16)	0.0035 (16)
N3	0.037 (2)	0.036 (2)	0.030 (2)	−0.0034 (15)	−0.0011 (17)	0.0023 (15)
N4	0.042 (2)	0.037 (2)	0.035 (2)	0.0081 (16)	−0.0084 (19)	−0.0017 (16)
O5	0.051 (2)	0.060 (2)	0.028 (2)	−0.0029 (15)	−0.0024 (16)	0.0025 (15)
N5	0.053 (3)	0.044 (2)	0.033 (2)	0.0059 (18)	0.0002 (19)	−0.0021 (17)
C8	0.035 (3)	0.035 (2)	0.035 (3)	0.0037 (18)	−0.002 (2)	0.0023 (19)
C9	0.044 (3)	0.034 (2)	0.033 (3)	−0.0039 (19)	−0.004 (2)	0.0039 (18)
C10	0.044 (3)	0.026 (2)	0.037 (3)	0.0054 (18)	−0.005 (2)	−0.0033 (18)
C11	0.044 (3)	0.031 (2)	0.027 (2)	0.0016 (18)	0.001 (2)	0.0006 (17)
C12	0.050 (3)	0.051 (3)	0.029 (3)	0.005 (2)	−0.012 (2)	−0.002 (2)
C13	0.046 (3)	0.060 (3)	0.046 (3)	0.004 (2)	0.003 (2)	0.012 (2)
C14	0.066 (4)	0.058 (3)	0.035 (3)	0.006 (2)	0.016 (3)	0.002 (2)
C15	0.040 (3)	0.086 (4)	0.041 (3)	−0.004 (3)	−0.005 (2)	−0.004 (3)

Geometric parameters (Å, º)

N1—C3	1.361 (6)	C8—C11	1.439 (7)
N1—H1A	0.8800	C10—C11	1.374 (6)
N1—H1B	0.8800	C12—H12	0.9500
O1—C1	1.230 (6)	C13—H13A	0.9800
C1—O2	1.311 (6)	C13—H13B	0.9800
C1—C2	1.463 (7)	C13—H13C	0.9800
O2—H2	0.8400	C14—H14A	0.9800
C2—C7	1.405 (6)	C14—H14B	0.9800
C2—C3	1.420 (7)	C14—H14C	0.9800
C3—C4	1.412 (7)	C15—H15A	0.9800
C4—C5	1.396 (7)	C15—H15B	0.9800
C4—H4	0.9500	C15—H15C	0.9800
C5—C6	1.362 (8)	C16—C17	1.3900
C5—H5	0.9500	C16—C21	1.3900
C6—C7	1.395 (7)	C16—C22	1.459 (9)
C6—H6	0.9500	C17—C18	1.3900
C7—H7	0.9500	C17—C23	1.444 (10)
N2—C8	1.394 (6)	C18—C19	1.3900
N2—C9	1.405 (6)	C18—H18	0.9500
N2—C15	1.459 (6)	C19—C20	1.3900
O3—C8	1.225 (5)	C19—H19	0.9500
N3—C9	1.367 (6)	C20—C21	1.3900
N3—C10	1.361 (6)	C20—H20	0.9500
N3—C13	1.443 (6)	C21—H21	0.9500
N4—C12	1.331 (6)	C22—H22A	0.9800
N4—C10	1.348 (6)	C22—H22B	0.9800
O5—C9	1.234 (5)	C22—H22C	0.9800
N5—C12	1.322 (6)	C23—H23A	0.9800
N5—C11	1.375 (6)	C23—H23B	0.9800
N5—C14	1.457 (6)	C23—H23C	0.9800
C3—N1—H1A	120.0	N4—C12—H12	123.0
C3—N1—H1B	120.0	N3—C13—H13A	109.5
H1A—N1—H1B	120.0	N3—C13—H13B	109.5
O1—C1—O2	122.3 (4)	H13A—C13—H13B	109.5
O1—C1—C2	123.6 (4)	N3—C13—H13C	109.5
O2—C1—C2	114.1 (4)	H13A—C13—H13C	109.5
C1—O2—H2	109.5	H13B—C13—H13C	109.5
C7—C2—C3	118.1 (4)	N5—C14—H14A	109.5
C7—C2—C1	119.9 (4)	N5—C14—H14B	109.5
C3—C2—C1	121.9 (4)	H14A—C14—H14B	109.5
N1—C3—C2	122.0 (4)	N5—C14—H14C	109.5
N1—C3—C4	118.3 (5)	H14A—C14—H14C	109.5
C2—C3—C4	119.7 (4)	H14B—C14—H14C	109.5
C5—C4—C3	119.7 (5)	N2—C15—H15A	109.5
C5—C4—H4	120.1	N2—C15—H15B	109.5
C3—C4—H4	120.1	H15A—C15—H15B	109.5
C6—C5—C4	121.1 (5)	N2—C15—H15C	109.5
C6—C5—H5	119.5	H15A—C15—H15C	109.5
C4—C5—H5	119.5	H15B—C15—H15C	109.5
C5—C6—C7	120.1 (5)	C17—C16—C21	120.0
C5—C6—H6	120.0	C17—C16—C22	109.7 (6)
C7—C6—H6	120.0	C21—C16—C22	130.1 (6)
C6—C7—C2	121.3 (5)	C16—C17—C18	120.0
C6—C7—H7	119.4	C16—C17—C23	123.2 (6)
C2—C7—H7	119.4	C18—C17—C23	116.5 (6)
C8—N2—C9	126.6 (4)	C17—C18—C19	120.0
C8—N2—C15	118.9 (4)	C17—C18—H18	120.0
C9—N2—C15	114.5 (4)	C19—C18—H18	120.0
C9—N3—C10	119.4 (4)	C20—C19—C18	120.0
C9—N3—C13	120.6 (4)	C20—C19—H19	120.0
C10—N3—C13	120.0 (4)	C18—C19—H19	120.0
C12—N4—C10	104.0 (4)	C21—C20—C19	120.0
C12—N5—C11	105.4 (4)	C21—C20—H20	120.0
C12—N5—C14	127.4 (5)	C19—C20—H20	120.0
C11—N5—C14	127.3 (4)	C20—C21—C16	120.0
O3—C8—N2	121.8 (4)	C20—C21—H21	120.0
O3—C8—C11	126.4 (4)	C16—C21—H21	120.0
N2—C8—C11	111.7 (4)	C16—C22—H22A	109.5
O5—C9—N3	121.6 (4)	C16—C22—H22B	109.5
O5—C9—N2	120.8 (4)	H22A—C22—H22B	109.5
N3—C9—N2	117.6 (4)	C16—C22—H22C	109.5
N4—C10—N3	127.1 (4)	H22A—C22—H22C	109.5
N4—C10—C11	110.3 (4)	H22B—C22—H22C	109.5
N3—C10—C11	122.6 (5)	C17—C23—H23A	109.5
C10—C11—N5	106.3 (4)	C17—C23—H23B	109.5
C10—C11—C8	122.1 (4)	H23A—C23—H23B	109.5
N5—C11—C8	131.7 (4)	C17—C23—H23C	109.5
N5—C12—N4	114.1 (4)	H23A—C23—H23C	109.5
N5—C12—H12	123.0	H23B—C23—H23C	109.5

(p_Xylene_Sesquisolvate)

Crystal data

C8H10N4O2·C7H7NO2·1.5(C8H10)	Z = 2
Mr = 490.58	F(000) = 522
Triclinic, P1	Dx = 1.261 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8474 (8) Å	Cell parameters from 22396 reflections
b = 13.431 (2) Å	θ = 1.0–22.5°
c = 14.440 (3) Å	µ = 0.09 mm^−1
α = 77.009 (3)°	T = 180 K
β = 86.596 (4)°	Block, colourless
γ = 88.687 (8)°	0.46 × 0.02 × 0.02 mm
V = 1291.7 (4) Å^3

Data collection

Nonius Kappa CCD diffractometer	1845 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.112
Thin slice ω and φ scans	θmax = 22.6°, θmin = 3.6°
Absorption correction: multi-scan SORTAV (Blessing, 1995)	h = −7→7
Tmin = 0.562, Tmax = 0.998	k = −13→14
8643 measured reflections	l = −15→15
3298 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)] = 0.086	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.226	H-atom parameters constrained
S = 0.97	w = 1/[σ^2(Fo^2) + (0.129P)^2] where P = (Fo^2 + 2Fc^2)/3
3298 reflections	(Δ/σ)max = 0.002
331 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

Experimental. Poor crystal —> poor data (theta(max)=22.5deg). The –COOH hydrogen atom was NOT located but placed in the most reasonable position.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.2407 (5)	−0.0021 (3)	0.5809 (3)	0.0705 (10)
H1X	0.2461	−0.0288	0.5335	0.085*
O2	0.2518 (5)	0.1397 (3)	0.4663 (3)	0.0726 (10)
N1	0.2464 (6)	0.3204 (3)	0.5189 (3)	0.0705 (12)
H1A	0.2511	0.2912	0.4701	0.085*
H1B	0.2473	0.3875	0.5095	0.085*
C1	0.2443 (6)	0.0986 (4)	0.5517 (4)	0.0566 (13)
C2	0.2356 (6)	0.1554 (4)	0.6277 (3)	0.0503 (12)
C3	0.2376 (6)	0.2624 (4)	0.6085 (4)	0.0541 (13)
C4	0.2296 (6)	0.3111 (4)	0.6870 (4)	0.0647 (14)
H4	0.2315	0.3836	0.6754	0.078*
C5	0.2192 (7)	0.2549 (4)	0.7788 (4)	0.0667 (14)
H5	0.2135	0.2886	0.8301	0.080*
C6	0.2170 (7)	0.1487 (5)	0.7974 (4)	0.0705 (15)
H6	0.2100	0.1097	0.8611	0.085*
C7	0.2252 (6)	0.1010 (4)	0.7221 (4)	0.0614 (14)
H7	0.2237	0.0285	0.7350	0.074*
O3	0.7153 (5)	0.2840 (3)	0.8026 (3)	0.0689 (10)
O4	0.7532 (5)	0.4547 (3)	0.4893 (2)	0.0680 (10)
N2	0.7332 (5)	0.3672 (3)	0.6449 (3)	0.0563 (11)
N3	0.7497 (5)	0.2819 (3)	0.5183 (3)	0.0546 (10)
N4	0.7438 (5)	0.0960 (3)	0.5681 (3)	0.0568 (11)
N5	0.7233 (5)	0.0865 (3)	0.7260 (3)	0.0558 (11)
C8	0.7253 (6)	0.2783 (4)	0.7184 (4)	0.0549 (13)
C9	0.7464 (6)	0.3713 (4)	0.5463 (4)	0.0549 (13)
C10	0.7420 (6)	0.1904 (4)	0.5866 (4)	0.0515 (12)
C11	0.7289 (6)	0.1887 (3)	0.6820 (4)	0.0496 (12)
C12	0.7340 (7)	0.0356 (4)	0.6557 (4)	0.0627 (14)
H12	0.7344	−0.0369	0.6671	0.075*
C13	0.7627 (8)	0.2817 (4)	0.4169 (4)	0.0738 (16)
H13A	0.8565	0.3334	0.3835	0.111*
H13B	0.6338	0.2974	0.3909	0.111*
H13C	0.8067	0.2142	0.4085	0.111*
C14	0.7106 (8)	0.0424 (4)	0.8275 (4)	0.0700 (15)
H14A	0.6953	−0.0318	0.8383	0.105*
H14B	0.5975	0.0718	0.8571	0.105*
H14C	0.8302	0.0573	0.8556	0.105*
C15	0.7303 (9)	0.4671 (4)	0.6714 (4)	0.0811 (17)
H15A	0.7214	0.4566	0.7409	0.122*
H15B	0.6170	0.5072	0.6450	0.122*
H15C	0.8507	0.5039	0.6458	0.122*
C16	0.1509 (9)	0.8531 (5)	0.9595 (5)	0.097 (2)
H16A	0.1227	0.8081	1.0221	0.145*
H16B	0.0418	0.8514	0.9189	0.145*
H16C	0.1682	0.9231	0.9667	0.145*
C17	0.3353 (8)	0.8172 (4)	0.9143 (4)	0.0686 (15)
C18	0.4894 (8)	0.7760 (4)	0.9671 (4)	0.0723 (16)
H18	0.4811	0.7708	1.0339	0.087*
C19	0.6566 (9)	0.7418 (4)	0.9250 (4)	0.0752 (16)
H19	0.7605	0.7130	0.9635	0.090*
C20	0.6757 (8)	0.7488 (4)	0.8267 (4)	0.0740 (16)
C21	0.8562 (9)	0.7106 (6)	0.7795 (5)	0.103 (2)
H21A	0.8462	0.7279	0.7103	0.155*
H21B	0.8672	0.6363	0.8016	0.155*
H21C	0.9724	0.7428	0.7959	0.155*
C22	0.5226 (9)	0.7911 (4)	0.7730 (4)	0.0743 (16)
H22	0.5331	0.7978	0.7060	0.089*
C23	0.3535 (9)	0.8240 (4)	0.8149 (4)	0.0739 (16)
H23	0.2485	0.8514	0.7765	0.089*
C24	−0.3206 (11)	0.4878 (6)	1.1461 (6)	0.121 (3)
H24A	−0.3844	0.4213	1.1565	0.182*
H24B	−0.4160	0.5424	1.1245	0.182*
H24C	−0.2689	0.4960	1.2057	0.182*
C25	−0.1551 (9)	0.4935 (5)	1.0714 (5)	0.0855 (18)
C26	0.0179 (11)	0.5455 (5)	1.0751 (5)	0.0907 (19)
H26	0.0327	0.5774	1.1266	0.109*
C27	0.1673 (10)	0.5514 (5)	1.0061 (5)	0.0876 (19)
H27	0.2825	0.5873	1.0115	0.105*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.099 (3)	0.041 (2)	0.073 (3)	−0.0054 (17)	−0.0044 (18)	−0.0147 (18)
O2	0.104 (3)	0.050 (2)	0.062 (3)	−0.0036 (18)	0.0001 (19)	−0.010 (2)
N1	0.097 (3)	0.043 (3)	0.069 (3)	−0.004 (2)	−0.002 (2)	−0.006 (2)
C1	0.062 (3)	0.040 (4)	0.068 (4)	−0.007 (2)	−0.001 (2)	−0.013 (3)
C2	0.050 (3)	0.039 (3)	0.062 (4)	−0.004 (2)	−0.001 (2)	−0.012 (3)
C3	0.047 (3)	0.046 (3)	0.066 (4)	−0.003 (2)	−0.004 (2)	−0.004 (3)
C4	0.060 (3)	0.057 (4)	0.086 (4)	0.001 (2)	−0.003 (3)	−0.034 (4)
C5	0.075 (3)	0.063 (4)	0.063 (4)	−0.003 (3)	0.001 (3)	−0.017 (3)
C6	0.083 (4)	0.065 (4)	0.062 (4)	−0.003 (3)	0.003 (3)	−0.012 (3)
C7	0.066 (3)	0.048 (3)	0.069 (4)	−0.002 (2)	−0.007 (2)	−0.010 (3)
O3	0.090 (2)	0.061 (2)	0.055 (3)	−0.0094 (17)	−0.0006 (18)	−0.0120 (19)
O4	0.097 (3)	0.038 (2)	0.064 (2)	−0.0074 (17)	−0.0054 (17)	−0.0008 (19)
N2	0.067 (2)	0.041 (3)	0.062 (3)	−0.0044 (18)	−0.0021 (19)	−0.014 (2)
N3	0.067 (3)	0.042 (3)	0.056 (3)	−0.0053 (18)	−0.0022 (18)	−0.015 (2)
N4	0.068 (3)	0.037 (3)	0.067 (3)	−0.0067 (18)	−0.0044 (19)	−0.013 (2)
N5	0.066 (3)	0.041 (3)	0.058 (3)	−0.0083 (18)	−0.0038 (18)	−0.007 (2)
C8	0.051 (3)	0.050 (4)	0.060 (4)	−0.008 (2)	−0.002 (2)	−0.003 (3)
C9	0.055 (3)	0.045 (4)	0.064 (4)	−0.005 (2)	−0.001 (2)	−0.012 (3)
C10	0.047 (3)	0.044 (3)	0.063 (4)	−0.005 (2)	−0.001 (2)	−0.009 (3)
C11	0.047 (3)	0.036 (3)	0.065 (4)	−0.004 (2)	−0.004 (2)	−0.008 (3)
C12	0.066 (3)	0.042 (3)	0.078 (4)	−0.004 (2)	−0.006 (3)	−0.009 (3)
C13	0.111 (4)	0.063 (4)	0.051 (4)	−0.010 (3)	−0.007 (3)	−0.020 (3)
C14	0.093 (4)	0.049 (3)	0.064 (4)	−0.010 (3)	−0.005 (3)	−0.002 (3)
C15	0.126 (5)	0.054 (4)	0.068 (4)	−0.007 (3)	−0.009 (3)	−0.021 (3)
C16	0.093 (4)	0.091 (5)	0.106 (5)	−0.006 (3)	−0.003 (4)	−0.022 (4)
C17	0.075 (4)	0.058 (4)	0.070 (4)	−0.015 (3)	−0.005 (3)	−0.008 (3)
C18	0.078 (4)	0.073 (4)	0.061 (4)	−0.019 (3)	−0.006 (3)	−0.003 (3)
C19	0.084 (4)	0.063 (4)	0.069 (4)	−0.019 (3)	−0.014 (3)	0.010 (3)
C20	0.084 (4)	0.060 (4)	0.072 (4)	−0.017 (3)	−0.007 (3)	0.000 (3)
C21	0.094 (5)	0.100 (6)	0.112 (6)	0.000 (4)	0.011 (4)	−0.018 (4)
C22	0.103 (5)	0.056 (4)	0.063 (4)	−0.020 (3)	−0.010 (3)	−0.007 (3)
C23	0.090 (4)	0.050 (4)	0.077 (4)	−0.020 (3)	−0.026 (3)	0.003 (3)
C24	0.124 (6)	0.094 (6)	0.145 (7)	−0.019 (4)	0.017 (5)	−0.028 (5)
C25	0.103 (5)	0.051 (4)	0.100 (5)	−0.009 (3)	−0.020 (4)	−0.005 (4)
C26	0.112 (5)	0.066 (4)	0.099 (5)	−0.007 (4)	−0.036 (4)	−0.021 (4)
C27	0.091 (5)	0.062 (4)	0.108 (6)	−0.021 (3)	−0.020 (4)	−0.009 (4)

Geometric parameters (Å, º)

O1—C1	1.323 (6)	C13—H13C	0.9800
O1—H1X	0.8400	C14—H14A	0.9800
O2—C1	1.231 (6)	C14—H14B	0.9800
N1—C3	1.350 (6)	C14—H14C	0.9800
N1—H1A	0.8800	C15—H15A	0.9800
N1—H1B	0.8800	C15—H15B	0.9800
C1—C2	1.469 (7)	C15—H15C	0.9800
C2—C7	1.392 (6)	C16—C17	1.506 (8)
C2—C3	1.401 (6)	C16—H16A	0.9800
C3—C4	1.429 (7)	C16—H16B	0.9800
C4—C5	1.368 (7)	C16—H16C	0.9800
C4—H4	0.9500	C17—C18	1.371 (7)
C5—C6	1.390 (7)	C17—C23	1.416 (8)
C5—H5	0.9500	C18—C19	1.381 (7)
C6—C7	1.379 (7)	C18—H18	0.9500
C6—H6	0.9500	C19—C20	1.400 (8)
C7—H7	0.9500	C19—H19	0.9500
O3—C8	1.233 (6)	C20—C22	1.376 (7)
O4—C9	1.232 (5)	C20—C21	1.512 (8)
N2—C8	1.407 (6)	C21—H21A	0.9800
N2—C9	1.411 (6)	C21—H21B	0.9800
N2—C15	1.474 (6)	C21—H21C	0.9800
N3—C9	1.349 (6)	C22—C23	1.384 (8)
N3—C10	1.391 (6)	C22—H22	0.9500
N3—C13	1.462 (6)	C23—H23	0.9500
N4—C12	1.339 (6)	C24—C25	1.508 (9)
N4—C10	1.353 (6)	C24—H24A	0.9800
N5—C12	1.344 (6)	C24—H24B	0.9800
N5—C11	1.377 (6)	C24—H24C	0.9800
N5—C14	1.450 (6)	C25—C27^i	1.392 (9)
C8—C11	1.418 (7)	C25—C26	1.399 (8)
C10—C11	1.369 (6)	C26—C27	1.376 (8)
C12—H12	0.9500	C26—H26	0.9500
C13—H13A	0.9800	C27—C25^i	1.392 (9)
C13—H13B	0.9800	C27—H27	0.9500
C1—O1—H1X	109.5	N5—C14—H14B	109.5
C3—N1—H1A	120.0	H14A—C14—H14B	109.5
C3—N1—H1B	120.0	N5—C14—H14C	109.5
H1A—N1—H1B	120.0	H14A—C14—H14C	109.5
O2—C1—O1	121.0 (5)	H14B—C14—H14C	109.5
O2—C1—C2	123.7 (5)	N2—C15—H15A	109.5
O1—C1—C2	115.2 (5)	N2—C15—H15B	109.5
C7—C2—C3	118.9 (5)	H15A—C15—H15B	109.5
C7—C2—C1	118.9 (5)	N2—C15—H15C	109.5
C3—C2—C1	122.2 (5)	H15A—C15—H15C	109.5
N1—C3—C2	122.4 (5)	H15B—C15—H15C	109.5
N1—C3—C4	119.2 (5)	C17—C16—H16A	109.5
C2—C3—C4	118.4 (5)	C17—C16—H16B	109.5
C5—C4—C3	120.9 (5)	H16A—C16—H16B	109.5
C5—C4—H4	119.5	C17—C16—H16C	109.5
C3—C4—H4	119.5	H16A—C16—H16C	109.5
C4—C5—C6	120.5 (5)	H16B—C16—H16C	109.5
C4—C5—H5	119.8	C18—C17—C23	117.7 (5)
C6—C5—H5	119.8	C18—C17—C16	121.9 (6)
C7—C6—C5	119.0 (5)	C23—C17—C16	120.4 (5)
C7—C6—H6	120.5	C17—C18—C19	121.3 (5)
C5—C6—H6	120.5	C17—C18—H18	119.3
C6—C7—C2	122.3 (5)	C19—C18—H18	119.3
C6—C7—H7	118.8	C18—C19—C20	121.2 (5)
C2—C7—H7	118.8	C18—C19—H19	119.4
C8—N2—C9	126.4 (4)	C20—C19—H19	119.4
C8—N2—C15	118.3 (4)	C22—C20—C19	117.9 (6)
C9—N2—C15	115.4 (4)	C22—C20—C21	120.1 (6)
C9—N3—C10	119.5 (4)	C19—C20—C21	122.0 (6)
C9—N3—C13	119.9 (4)	C20—C21—H21A	109.5
C10—N3—C13	120.6 (4)	C20—C21—H21B	109.5
C12—N4—C10	102.2 (4)	H21A—C21—H21B	109.5
C12—N5—C11	106.0 (4)	C20—C21—H21C	109.5
C12—N5—C14	126.8 (4)	H21A—C21—H21C	109.5
C11—N5—C14	127.3 (4)	H21B—C21—H21C	109.5
O3—C8—N2	120.8 (5)	C20—C22—C23	121.2 (6)
O3—C8—C11	127.5 (5)	C20—C22—H22	119.4
N2—C8—C11	111.7 (5)	C23—C22—H22	119.4
O4—C9—N3	122.6 (5)	C22—C23—C17	120.7 (5)
O4—C9—N2	119.7 (5)	C22—C23—H23	119.7
N3—C9—N2	117.7 (4)	C17—C23—H23	119.7
N4—C10—C11	113.0 (4)	C25—C24—H24A	109.5
N4—C10—N3	125.3 (5)	C25—C24—H24B	109.5
C11—C10—N3	121.6 (5)	H24A—C24—H24B	109.5
C10—C11—N5	104.7 (4)	C25—C24—H24C	109.5
C10—C11—C8	123.1 (5)	H24A—C24—H24C	109.5
N5—C11—C8	132.1 (5)	H24B—C24—H24C	109.5
N4—C12—N5	114.1 (5)	C27^i—C25—C26	116.2 (6)
N4—C12—H12	123.0	C27^i—C25—C24	121.8 (6)
N5—C12—H12	123.0	C26—C25—C24	122.0 (7)
N3—C13—H13A	109.5	C27—C26—C25	121.7 (6)
N3—C13—H13B	109.5	C27—C26—H26	119.2
H13A—C13—H13B	109.5	C25—C26—H26	119.2
N3—C13—H13C	109.5	C26—C27—C25^i	122.1 (6)
H13A—C13—H13C	109.5	C26—C27—H27	118.9
H13B—C13—H13C	109.5	C25^i—C27—H27	118.9
N5—C14—H14A	109.5

Symmetry code: (i) −x, −y+1, −z+2.

(Monohydrate)

Crystal data

C8H10N4O2·C7H7NO2·H2O	F(000) = 1472
Mr = 349.35	Dx = 1.440 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 18126 reflections
a = 10.2641 (2) Å	θ = 1.0–27.1°
b = 26.9469 (7) Å	µ = 0.11 mm^−1
c = 11.9845 (3) Å	T = 180 K
β = 103.547 (2)°	Block, colourless
V = 3222.52 (13) Å^3	0.32 × 0.12 × 0.10 mm
Z = 8

Data collection

Nonius Kappa CCD diffractometer	3701 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.053
Thin slice ω and φ scans	θmax = 27.1°, θmin = 3.6°
Absorption correction: multi-scan SORTAV (Blessing, 1995)	h = −13→13
Tmin = 0.877, Tmax = 0.994	k = −34→34
18826 measured reflections	l = −14→15
7046 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ^2(Fo^2) + (0.083P)^2] where P = (Fo^2 + 2Fc^2)/3
7046 reflections	(Δ/σ)max = 0.001
469 parameters	Δρmax = 0.32 e Å^−3
6 restraints	Δρmin = −0.34 e Å^−3

Special details

Experimental. The hydrogen atoms of water oxygen atom O2W were NOT located but were placed in reasonable positions.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N2	0.7698 (2)	0.11684 (8)	0.56077 (16)	0.0335 (5)
N3	0.79013 (19)	0.20275 (8)	0.60224 (17)	0.0361 (5)
O3	0.65429 (18)	0.15286 (8)	0.67935 (15)	0.0509 (5)
N4	0.99363 (19)	0.16092 (8)	0.40382 (17)	0.0356 (5)
O4	0.92381 (18)	0.25417 (7)	0.52473 (16)	0.0490 (5)
N5	0.90393 (19)	0.08753 (8)	0.43110 (16)	0.0343 (5)
C8	0.8796 (2)	0.21211 (10)	0.5332 (2)	0.0341 (6)
C9	0.9111 (2)	0.16884 (10)	0.47873 (19)	0.0316 (6)
C10	0.8587 (2)	0.12326 (9)	0.49244 (19)	0.0303 (6)
C11	0.7334 (3)	0.15690 (11)	0.6184 (2)	0.0382 (6)
C12	0.9856 (3)	0.11239 (10)	0.3790 (2)	0.0388 (6)
H12	1.0333	0.0971	0.3292	0.047*
C13	0.7143 (3)	0.06802 (10)	0.5739 (2)	0.0438 (7)
H13A	0.6964	0.0505	0.5003	0.066*
H13B	0.6307	0.0718	0.5991	0.066*
H13C	0.7787	0.0489	0.6313	0.066*
C14	0.7469 (3)	0.24439 (12)	0.6636 (2)	0.0521 (8)
H14A	0.7571	0.2355	0.7445	0.078*
H14B	0.6527	0.2520	0.6292	0.078*
H14C	0.8021	0.2736	0.6582	0.078*
C15	1.0761 (3)	0.19725 (11)	0.3628 (2)	0.0480 (7)
H15A	1.1095	0.1830	0.2997	0.072*
H15B	1.1521	0.2065	0.4256	0.072*
H15C	1.0225	0.2268	0.3356	0.072*
C1	0.5006 (2)	0.19424 (10)	0.3836 (2)	0.0336 (6)
N1	0.6345 (2)	0.13733 (8)	0.23640 (17)	0.0415 (6)
H1A	0.6501	0.1694	0.2456	0.050*
H1B	0.6753	0.1199	0.1927	0.050*
O1	0.42287 (16)	0.21415 (7)	0.44619 (15)	0.0469 (5)
H1X	0.4398	0.2446	0.4552	0.056*
C2	0.4787 (2)	0.14057 (9)	0.3609 (2)	0.0321 (6)
O2	0.58178 (17)	0.21937 (7)	0.34845 (16)	0.0479 (5)
C3	0.5472 (2)	0.11481 (10)	0.2899 (2)	0.0343 (6)
C4	0.5227 (3)	0.06348 (10)	0.2733 (2)	0.0410 (7)
H4	0.5678	0.0454	0.2256	0.049*
C5	0.4351 (3)	0.03935 (11)	0.3247 (2)	0.0473 (7)
H5	0.4210	0.0047	0.3128	0.057*
C6	0.3662 (3)	0.06472 (10)	0.3943 (2)	0.0473 (7)
H6	0.3047	0.0478	0.4291	0.057*
C7	0.3889 (3)	0.11467 (10)	0.4116 (2)	0.0404 (7)
H7	0.3425	0.1322	0.4593	0.049*
N7	0.28462 (19)	0.16013 (7)	1.07163 (15)	0.0307 (5)
N8	0.23375 (18)	0.07438 (8)	1.05519 (16)	0.0328 (5)
O8	0.12952 (17)	0.12623 (7)	1.15614 (15)	0.0442 (5)
N9	0.49279 (19)	0.11223 (8)	0.90411 (16)	0.0334 (5)
O9	0.33692 (17)	0.02074 (6)	0.95356 (15)	0.0414 (5)
N10	0.45111 (19)	0.18681 (8)	0.96878 (16)	0.0328 (5)
C23	0.3253 (2)	0.06300 (9)	0.98755 (19)	0.0302 (6)
C24	0.3967 (2)	0.10563 (9)	0.96707 (19)	0.0286 (5)
C25	0.3755 (2)	0.15199 (9)	1.00521 (19)	0.0287 (5)
C26	0.2111 (2)	0.12083 (10)	1.0980 (2)	0.0340 (6)
C27	0.5204 (2)	0.16079 (10)	0.9076 (2)	0.0384 (6)
H27	0.5831	0.1753	0.8702	0.046*
C28	0.2631 (3)	0.20962 (10)	1.1138 (2)	0.0419 (7)
H28A	0.1684	0.2187	1.0870	0.063*
H28B	0.3187	0.2337	1.0848	0.063*
H28C	0.2877	0.2097	1.1979	0.063*
C29	0.1527 (3)	0.03415 (11)	1.0850 (2)	0.0448 (7)
H29A	0.0575	0.0425	1.0589	0.067*
H29B	0.1751	0.0295	1.1684	0.067*
H29C	0.1711	0.0034	1.0476	0.067*
C30	0.5485 (3)	0.07380 (10)	0.8426 (2)	0.0466 (7)
H30A	0.6237	0.0876	0.8151	0.070*
H30B	0.4791	0.0622	0.7771	0.070*
H30C	0.5801	0.0459	0.8945	0.070*
N6	−0.0428 (2)	0.08593 (9)	0.82817 (17)	0.0453 (6)
H6A	−0.0825	0.1037	0.8722	0.054*
H6B	−0.0623	0.0543	0.8167	0.054*
O6	0.15779 (17)	0.00931 (7)	0.60934 (14)	0.0496 (5)
H6X	0.1447	−0.0215	0.6040	0.059*
O7	0.01721 (18)	0.00256 (7)	0.72414 (15)	0.0474 (5)
C16	0.0924 (2)	0.02812 (10)	0.6820 (2)	0.0359 (6)
C17	0.1171 (2)	0.08127 (10)	0.7069 (2)	0.0336 (6)
C18	0.0486 (2)	0.10739 (10)	0.7781 (2)	0.0334 (6)
C19	0.0782 (3)	0.15828 (10)	0.7979 (2)	0.0378 (6)
H19	0.0322	0.1767	0.8444	0.045*
C20	0.1710 (3)	0.18138 (10)	0.7520 (2)	0.0424 (7)
H20	0.1897	0.2155	0.7677	0.051*
C21	0.2395 (3)	0.15584 (10)	0.6821 (2)	0.0422 (7)
H21	0.3042	0.1723	0.6503	0.051*
C22	0.2116 (2)	0.10634 (10)	0.6598 (2)	0.0378 (6)
H22	0.2572	0.0888	0.6116	0.045*
O1W	0.8371 (2)	0.35517 (9)	0.4826 (2)	0.0694 (6)
H11W	0.876 (3)	0.3218 (7)	0.509 (2)	0.083*
H12W	0.843 (3)	0.3729 (10)	0.5596 (19)	0.083*
O2W	0.1984 (2)	−0.06684 (8)	0.87423 (19)	0.0680 (6)
H21W	0.253 (2)	−0.0341 (9)	0.913 (2)	0.082*
H22W	0.118 (2)	−0.0482 (10)	0.814 (2)	0.082*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N2	0.0393 (12)	0.0279 (13)	0.0354 (11)	−0.0009 (10)	0.0132 (10)	0.0011 (9)
N3	0.0388 (11)	0.0320 (13)	0.0406 (12)	0.0043 (10)	0.0151 (10)	−0.0038 (10)
O3	0.0579 (11)	0.0509 (14)	0.0539 (11)	0.0015 (10)	0.0336 (10)	0.0018 (10)
N4	0.0384 (11)	0.0297 (13)	0.0417 (12)	−0.0042 (10)	0.0153 (10)	−0.0037 (10)
O4	0.0537 (11)	0.0291 (12)	0.0711 (13)	−0.0040 (9)	0.0284 (10)	−0.0080 (10)
N5	0.0378 (11)	0.0316 (13)	0.0352 (11)	0.0001 (10)	0.0118 (10)	−0.0018 (10)
C8	0.0335 (13)	0.0264 (16)	0.0425 (15)	0.0022 (12)	0.0092 (12)	−0.0002 (12)
C9	0.0315 (13)	0.0304 (15)	0.0348 (13)	0.0005 (11)	0.0117 (11)	0.0018 (11)
C10	0.0329 (13)	0.0264 (14)	0.0315 (13)	0.0021 (11)	0.0072 (11)	0.0017 (11)
C11	0.0396 (14)	0.0374 (17)	0.0366 (14)	0.0080 (13)	0.0066 (13)	0.0067 (12)
C12	0.0417 (15)	0.0339 (16)	0.0432 (15)	0.0006 (13)	0.0148 (13)	−0.0085 (13)
C13	0.0536 (16)	0.0307 (16)	0.0506 (16)	−0.0069 (14)	0.0190 (13)	0.0046 (13)
C14	0.0550 (17)	0.046 (2)	0.0606 (18)	0.0061 (15)	0.0233 (15)	−0.0154 (15)
C15	0.0491 (16)	0.0411 (18)	0.0627 (18)	−0.0086 (14)	0.0310 (14)	−0.0039 (14)
C1	0.0353 (13)	0.0282 (15)	0.0373 (14)	0.0037 (12)	0.0085 (12)	0.0002 (11)
N1	0.0469 (13)	0.0327 (13)	0.0488 (13)	−0.0006 (11)	0.0190 (11)	0.0008 (10)
O1	0.0538 (11)	0.0266 (11)	0.0684 (12)	−0.0028 (9)	0.0308 (10)	−0.0077 (9)
C2	0.0317 (13)	0.0265 (14)	0.0370 (14)	0.0014 (11)	0.0059 (11)	0.0020 (11)
O2	0.0513 (11)	0.0312 (11)	0.0688 (12)	−0.0077 (10)	0.0295 (9)	−0.0008 (9)
C3	0.0361 (14)	0.0313 (15)	0.0337 (14)	0.0025 (12)	0.0047 (12)	0.0030 (11)
C4	0.0495 (16)	0.0317 (17)	0.0417 (15)	0.0026 (13)	0.0106 (13)	−0.0032 (12)
C5	0.0617 (18)	0.0265 (16)	0.0561 (17)	−0.0060 (14)	0.0184 (15)	−0.0058 (13)
C6	0.0549 (17)	0.0310 (17)	0.0614 (18)	−0.0059 (14)	0.0244 (15)	−0.0017 (14)
C7	0.0445 (15)	0.0276 (16)	0.0531 (16)	0.0015 (13)	0.0194 (13)	0.0007 (12)
N7	0.0360 (11)	0.0236 (12)	0.0360 (11)	−0.0007 (10)	0.0153 (9)	−0.0014 (9)
N8	0.0325 (11)	0.0280 (12)	0.0394 (12)	−0.0045 (10)	0.0117 (9)	0.0006 (9)
O8	0.0453 (10)	0.0447 (13)	0.0514 (11)	−0.0004 (9)	0.0290 (9)	−0.0012 (9)
N9	0.0366 (11)	0.0247 (12)	0.0427 (12)	0.0037 (10)	0.0171 (10)	0.0024 (9)
O9	0.0502 (11)	0.0227 (10)	0.0557 (11)	−0.0041 (9)	0.0216 (9)	−0.0038 (8)
N10	0.0335 (11)	0.0264 (12)	0.0417 (12)	−0.0026 (10)	0.0152 (10)	0.0034 (9)
C23	0.0325 (13)	0.0276 (15)	0.0305 (13)	0.0009 (11)	0.0073 (11)	0.0014 (11)
C24	0.0314 (12)	0.0253 (14)	0.0307 (12)	0.0016 (11)	0.0107 (11)	0.0015 (10)
C25	0.0289 (12)	0.0246 (14)	0.0332 (13)	0.0004 (11)	0.0081 (11)	0.0031 (11)
C26	0.0319 (13)	0.0382 (17)	0.0326 (14)	0.0008 (12)	0.0085 (12)	0.0012 (12)
C27	0.0377 (14)	0.0302 (16)	0.0498 (16)	0.0006 (13)	0.0152 (12)	0.0085 (13)
C28	0.0514 (15)	0.0282 (16)	0.0504 (16)	0.0061 (13)	0.0209 (13)	−0.0038 (12)
C29	0.0449 (15)	0.0376 (18)	0.0559 (17)	−0.0124 (13)	0.0202 (13)	0.0000 (13)
C30	0.0584 (17)	0.0344 (17)	0.0588 (17)	0.0098 (14)	0.0372 (14)	0.0034 (13)
N6	0.0542 (14)	0.0351 (14)	0.0511 (13)	−0.0060 (12)	0.0215 (11)	−0.0062 (11)
O6	0.0657 (12)	0.0275 (11)	0.0644 (12)	−0.0004 (10)	0.0335 (10)	−0.0047 (9)
O7	0.0543 (11)	0.0325 (12)	0.0604 (12)	−0.0064 (10)	0.0238 (10)	−0.0021 (10)
C16	0.0402 (14)	0.0285 (15)	0.0392 (14)	0.0025 (13)	0.0098 (12)	−0.0003 (12)
C17	0.0386 (14)	0.0264 (15)	0.0333 (13)	−0.0008 (12)	0.0031 (12)	0.0034 (11)
C18	0.0361 (13)	0.0306 (15)	0.0313 (13)	−0.0001 (12)	0.0039 (11)	0.0035 (11)
C19	0.0476 (15)	0.0271 (15)	0.0367 (14)	0.0049 (13)	0.0063 (12)	0.0016 (12)
C20	0.0577 (17)	0.0255 (15)	0.0423 (15)	−0.0007 (14)	0.0084 (14)	0.0020 (12)
C21	0.0535 (16)	0.0319 (17)	0.0441 (15)	−0.0042 (14)	0.0174 (13)	0.0043 (13)
C22	0.0446 (15)	0.0304 (16)	0.0390 (14)	−0.0023 (13)	0.0109 (12)	0.0035 (12)
O1W	0.0700 (14)	0.0482 (15)	0.0979 (17)	0.0035 (12)	0.0354 (13)	0.0062 (13)
O2W	0.0757 (15)	0.0530 (16)	0.0779 (15)	−0.0095 (13)	0.0231 (12)	−0.0057 (12)

Geometric parameters (Å, º)

N2—C10	1.372 (3)	N7—C28	1.461 (3)
N2—C11	1.379 (3)	N8—C26	1.393 (3)
N2—C13	1.457 (3)	N8—C23	1.411 (3)
N3—C8	1.395 (3)	N8—C29	1.461 (3)
N3—C11	1.398 (3)	O8—C26	1.217 (3)
N3—C14	1.466 (3)	N9—C27	1.337 (3)
O3—C11	1.218 (3)	N9—C24	1.387 (3)
N4—C12	1.339 (3)	N9—C30	1.463 (3)
N4—C9	1.387 (3)	O9—C23	1.225 (3)
N4—C15	1.453 (3)	N10—C27	1.334 (3)
O4—C8	1.234 (3)	N10—C25	1.353 (3)
N5—C12	1.336 (3)	C23—C24	1.414 (3)
N5—C10	1.358 (3)	C24—C25	1.365 (3)
C8—C9	1.411 (3)	C27—H27	0.9500
C9—C10	1.366 (3)	C28—H28A	0.9800
C12—H12	0.9500	C28—H28B	0.9800
C13—H13A	0.9800	C28—H28C	0.9800
C13—H13B	0.9800	C29—H29A	0.9800
C13—H13C	0.9800	C29—H29B	0.9800
C14—H14A	0.9800	C29—H29C	0.9800
C14—H14B	0.9800	C30—H30A	0.9800
C14—H14C	0.9800	C30—H30B	0.9800
C15—H15A	0.9800	C30—H30C	0.9800
C15—H15B	0.9800	N6—C18	1.356 (3)
C15—H15C	0.9800	N6—H6A	0.8800
C1—O2	1.223 (3)	N6—H6B	0.8800
C1—O1	1.329 (3)	O6—C16	1.319 (3)
C1—C2	1.479 (3)	O6—H6X	0.8400
N1—C3	1.360 (3)	O7—C16	1.227 (3)
N1—H1A	0.8800	C16—C17	1.473 (3)
N1—H1B	0.8800	C17—C22	1.405 (3)
O1—H1X	0.8400	C17—C18	1.413 (3)
C2—C7	1.404 (3)	C18—C19	1.413 (4)
C2—C3	1.407 (3)	C19—C20	1.358 (3)
C3—C4	1.411 (4)	C19—H19	0.9500
C4—C5	1.368 (4)	C20—C21	1.394 (4)
C4—H4	0.9500	C20—H20	0.9500
C5—C6	1.392 (4)	C21—C22	1.377 (4)
C5—H5	0.9500	C21—H21	0.9500
C6—C7	1.374 (4)	C22—H22	0.9500
C6—H6	0.9500	O1W—H11W	1.005 (17)
C7—H7	0.9500	O1W—H12W	1.028 (17)
N7—C25	1.379 (3)	O2W—H21W	1.090 (17)
N7—C26	1.380 (3)	O2W—H22W	1.087 (17)
C10—N2—C11	119.7 (2)	C25—N7—C28	121.5 (2)
C10—N2—C13	120.7 (2)	C26—N7—C28	119.1 (2)
C11—N2—C13	119.6 (2)	C26—N8—C23	126.7 (2)
C8—N3—C11	126.5 (2)	C26—N8—C29	115.0 (2)
C8—N3—C14	118.5 (2)	C23—N8—C29	118.2 (2)
C11—N3—C14	115.0 (2)	C27—N9—C24	106.4 (2)
C12—N4—C9	106.2 (2)	C27—N9—C30	127.1 (2)
C12—N4—C15	126.4 (2)	C24—N9—C30	126.5 (2)
C9—N4—C15	127.4 (2)	C27—N10—C25	103.5 (2)
C12—N5—C10	103.2 (2)	O9—C23—N8	121.5 (2)
O4—C8—N3	121.4 (2)	O9—C23—C24	127.1 (2)
O4—C8—C9	126.3 (2)	N8—C23—C24	111.4 (2)
N3—C8—C9	112.3 (2)	C25—C24—N9	104.7 (2)
C10—C9—N4	104.9 (2)	C25—C24—C23	123.8 (2)
C10—C9—C8	123.2 (2)	N9—C24—C23	131.5 (2)
N4—C9—C8	131.9 (2)	N10—C25—C24	112.2 (2)
N5—C10—C9	112.2 (2)	N10—C25—N7	126.4 (2)
N5—C10—N2	126.4 (2)	C24—C25—N7	121.4 (2)
C9—C10—N2	121.4 (2)	O8—C26—N7	121.7 (2)
O3—C11—N2	121.8 (3)	O8—C26—N8	121.0 (2)
O3—C11—N3	121.3 (3)	N7—C26—N8	117.2 (2)
N2—C11—N3	116.9 (2)	N10—C27—N9	113.2 (2)
N5—C12—N4	113.5 (2)	N10—C27—H27	123.4
N5—C12—H12	123.3	N9—C27—H27	123.4
N4—C12—H12	123.3	N7—C28—H28A	109.5
N2—C13—H13A	109.5	N7—C28—H28B	109.5
N2—C13—H13B	109.5	H28A—C28—H28B	109.5
H13A—C13—H13B	109.5	N7—C28—H28C	109.5
N2—C13—H13C	109.5	H28A—C28—H28C	109.5
H13A—C13—H13C	109.5	H28B—C28—H28C	109.5
H13B—C13—H13C	109.5	N8—C29—H29A	109.5
N3—C14—H14A	109.5	N8—C29—H29B	109.5
N3—C14—H14B	109.5	H29A—C29—H29B	109.5
H14A—C14—H14B	109.5	N8—C29—H29C	109.5
N3—C14—H14C	109.5	H29A—C29—H29C	109.5
H14A—C14—H14C	109.5	H29B—C29—H29C	109.5
H14B—C14—H14C	109.5	N9—C30—H30A	109.5
N4—C15—H15A	109.5	N9—C30—H30B	109.5
N4—C15—H15B	109.5	H30A—C30—H30B	109.5
H15A—C15—H15B	109.5	N9—C30—H30C	109.5
N4—C15—H15C	109.5	H30A—C30—H30C	109.5
H15A—C15—H15C	109.5	H30B—C30—H30C	109.5
H15B—C15—H15C	109.5	C18—N6—H6A	120.0
O2—C1—O1	121.2 (2)	C18—N6—H6B	120.0
O2—C1—C2	124.4 (2)	H6A—N6—H6B	120.0
O1—C1—C2	114.4 (2)	C16—O6—H6X	109.5
C3—N1—H1A	120.0	O7—C16—O6	121.5 (2)
C3—N1—H1B	120.0	O7—C16—C17	123.9 (2)
H1A—N1—H1B	120.0	O6—C16—C17	114.7 (2)
C1—O1—H1X	109.5	C22—C17—C18	119.4 (2)
C7—C2—C3	119.3 (2)	C22—C17—C16	119.2 (2)
C7—C2—C1	119.5 (2)	C18—C17—C16	121.4 (2)
C3—C2—C1	121.2 (2)	N6—C18—C19	118.9 (2)
N1—C3—C2	122.8 (2)	N6—C18—C17	123.2 (2)
N1—C3—C4	119.1 (2)	C19—C18—C17	117.9 (2)
C2—C3—C4	118.1 (2)	C20—C19—C18	121.3 (3)
C5—C4—C3	121.1 (3)	C20—C19—H19	119.3
C5—C4—H4	119.5	C18—C19—H19	119.3
C3—C4—H4	119.5	C19—C20—C21	121.2 (3)
C4—C5—C6	121.1 (3)	C19—C20—H20	119.4
C4—C5—H5	119.5	C21—C20—H20	119.4
C6—C5—H5	119.5	C22—C21—C20	118.9 (3)
C7—C6—C5	118.7 (3)	C22—C21—H21	120.5
C7—C6—H6	120.7	C20—C21—H21	120.5
C5—C6—H6	120.7	C21—C22—C17	121.3 (3)
C6—C7—C2	121.8 (3)	C21—C22—H22	119.4
C6—C7—H7	119.1	C17—C22—H22	119.4
C2—C7—H7	119.1	H11W—O1W—H12W	101.5 (18)
C25—N7—C26	119.4 (2)	H21W—O2W—H22W	98.4 (17)

(Theobromine_AA)

Crystal data

C7H8N4O2·C7H7NO2	Z = 4
Mr = 317.31	F(000) = 664
Monoclinic, P21/c	Dx = 1.437 (1) Mg m^−3
a = 6.5769 (10) Å	Cu Kα radiation, λ = 1.5418 Å
b = 21.905 (3) Å	T = 293 K
c = 11.0496 (16) Å	white
β = 112.912 (6)°	flat sheet, 14 × 10 mm
V = 1466.3 (4) Å^3

Data collection

Panalytical X'pert Powder diffractometer	Data collection mode: reflection
Radiation source: sealed X-ray tube	Scan method: continuous
None monochromator	2θmin = 4.993°, 2θmax = 60.004°, 2θstep = 0.033°
Specimen mounting: glass slide

Refinement

Rp = 0.035	166 parameters
Rwp = 0.040	103 restraints
Rexp = 0.011	0 constraints
RBragg = 0.023
χ^2 = 13.853
1668 data points	Background function: Chebyshev polynomial
Profile function: pseudo-Voigt	Preferred orientation correction: spherical harmonics

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.6170 (7)	0.3272 (3)	0.3697 (5)	0.051
C2	0.4000 (9)	0.3560 (3)	0.3364 (6)	0.051
C3	0.6527 (9)	0.2854 (3)	0.2811 (5)	0.051
C4	0.7957 (8)	0.3411 (3)	0.4939 (5)	0.051
O5	0.2473 (10)	0.3385 (3)	0.2187 (8)	0.051
O6	0.3623 (15)	0.3964 (4)	0.4067 (9)	0.051
C7	0.8560 (9)	0.2592 (3)	0.3074 (5)	0.051
H8	0.516 (4)	0.2745 (12)	0.189 (2)	0.061
N9	0.7635 (9)	0.3817 (3)	0.5830 (5)	0.051
C10	1.0068 (9)	0.3124 (3)	0.5186 (6)	0.051
H11	0.099 (4)	0.3577 (12)	0.200 (2)	0.061
C12	1.0319 (9)	0.2714 (3)	0.4303 (6)	0.051
H13	0.878 (4)	0.2288 (12)	0.235 (2)	0.061
H14	0.610 (4)	0.3993 (10)	0.560 (2)	0.061
H15	0.881 (4)	0.3887 (11)	0.674 (3)	0.061
H16	1.149 (4)	0.3224 (10)	0.609 (3)	0.061
H17	1.195 (4)	0.2509 (11)	0.453 (2)	0.061
C18	0.5522 (8)	0.4630 (3)	0.1725 (6)	0.051
N19	0.7221 (8)	0.4898 (3)	0.2858 (6)	0.051
C20	0.6570 (8)	0.4192 (3)	0.1190 (6)	0.051
C21	0.3198 (9)	0.4773 (3)	0.1070 (6)	0.051
C22	0.9160 (8)	0.4633 (3)	0.2889 (7)	0.051
C23	0.6921 (7)	0.5393 (2)	0.3747 (5)	0.051
N24	0.5388 (8)	0.3851 (3)	−0.0004 (6)	0.051
N25	0.8811 (11)	0.4184 (4)	0.1974 (8)	0.051
O26	0.2208 (14)	0.5190 (5)	0.1423 (10)	0.051
N27	0.2135 (9)	0.4406 (3)	−0.0069 (6)	0.051
H28	1.084 (4)	0.4777 (13)	0.353 (2)	0.061
H29	0.746 (3)	0.5235 (13)	0.479 (3)	0.061
H30	0.514 (4)	0.5525 (11)	0.340 (2)	0.061
H31	0.786 (4)	0.5807 (11)	0.372 (3)	0.061
C32	0.3019 (9)	0.3960 (3)	−0.0624 (6)	0.051
C33	0.6574 (7)	0.3404 (2)	−0.0580 (5)	0.051
H34	0.047 (4)	0.4511 (10)	−0.064 (3)	0.061
O35	0.1750 (17)	0.3691 (4)	−0.1635 (10)	0.051
H36	0.821 (4)	0.3287 (11)	0.016 (2)	0.061
H37	0.681 (4)	0.3586 (11)	−0.145 (2)	0.061
H38	0.562 (4)	0.2987 (11)	−0.087 (3)	0.061

Geometric parameters (Å, º)

C1—C2	1.471 (8)	N19—C22	1.390 (9)
C1—C3	1.425 (9)	N19—C23	1.527 (9)
C1—C4	1.450 (6)	C20—N24	1.449 (8)
C2—O5	1.353 (8)	C20—N25	1.389 (8)
C2—O6	1.264 (13)	C21—O26	1.268 (13)
C3—C7	1.378 (8)	C21—N27	1.426 (9)
C3—H8	1.09 (2)	C22—N25	1.364 (11)
C4—N9	1.403 (9)	C22—H28	1.10 (2)
C4—C10	1.449 (8)	C23—H29	1.12 (3)
O5—H11	1.00 (3)	C23—H30	1.12 (2)
C7—C12	1.425 (7)	C23—H31	1.10 (3)
C7—H13	1.09 (3)	N24—C32	1.457 (8)
N9—H14	1.02 (3)	N24—C33	1.537 (9)
N9—H15	1.01 (2)	N27—C32	1.396 (10)
C10—C12	1.383 (10)	N27—H34	1.05 (2)
C10—H16	1.09 (2)	C32—O35	1.251 (10)
C12—H17	1.10 (3)	C33—H36	1.10 (2)
C18—N19	1.439 (7)	C33—H37	1.11 (3)
C18—C20	1.437 (10)	C33—H38	1.08 (2)
C18—C21	1.448 (7)
C2—C1—C3	120.5 (4)	C18—C20—N24	123.0 (5)
C2—C1—C4	119.8 (5)	C18—C20—N25	108.3 (6)
C3—C1—C4	119.7 (5)	N24—C20—N25	128.6 (7)
C1—C2—O5	113.8 (6)	C18—C21—O26	124.8 (6)
C1—C2—O6	123.4 (5)	C18—C21—N27	112.3 (6)
O5—C2—O6	122.7 (7)	O26—C21—N27	122.9 (6)
C1—C3—C7	121.9 (4)	N19—C22—N25	113.3 (5)
C1—C3—H8	119 (2)	N19—C22—H28	125 (2)
C7—C3—H8	119 (2)	N25—C22—H28	121 (2)
C1—C4—N9	120.6 (5)	N19—C23—H29	112 (2)
C1—C4—C10	116.8 (5)	N19—C23—H30	110 (1)
N9—C4—C10	122.5 (4)	N19—C23—H31	111 (2)
C2—O5—H11	111 (2)	H29—C23—H30	108 (2)
C3—C7—C12	118.9 (6)	H29—C23—H31	109 (2)
C3—C7—H13	119 (2)	H30—C23—H31	108 (2)
C12—C7—H13	121 (1)	C20—N24—C32	116.1 (6)
C4—N9—H14	117 (1)	C20—N24—C33	121.8 (4)
C4—N9—H15	122 (2)	C32—N24—C33	122.1 (5)
H14—N9—H15	120 (2)	C20—N25—C22	106.5 (7)
C4—C10—C12	121.2 (5)	C21—N27—C32	129.6 (5)
C4—C10—H16	120 (2)	C21—N27—H34	116 (2)
C12—C10—H16	119 (2)	C32—N27—H34	114 (2)
C7—C12—C10	121.3 (5)	N24—C32—N27	117.4 (5)
C7—C12—H17	120 (1)	N24—C32—O35	124.3 (8)
C10—C12—H17	119 (1)	N27—C32—O35	118.4 (7)
N19—C18—C20	107.3 (5)	N24—C33—H36	110 (2)
N19—C18—C21	131.1 (6)	N24—C33—H37	113 (1)
C20—C18—C21	121.4 (5)	N24—C33—H38	109 (2)
C18—N19—C22	104.2 (6)	H36—C33—H37	108 (2)
C18—N19—C23	126.8 (5)	H36—C33—H38	108 (2)
C22—N19—C23	129.0 (4)	H37—C33—H38	108 (2)