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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520613033167/bi5010sup1.cif
Contains datablocks Form1, Form2, Chlorobenzene_Hemisolvate, Bromobenzene_Hemisolvate, Toluene_Hemisolvate, Toluene_Monosolvate, o_Xylene_Monosolvate, p_Xylene_Sesquisolvate, Monohydrate, Theobromine_AA

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S2052520613033167/bi5010Form1sup2.rtv
Contains datablock Form1

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S2052520613033167/bi5010Form2sup3.rtv
Contains datablock Form2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520613033167/bi5010Chlorobenzene_Hemisolvatesup4.hkl
Contains datablock Chlorobenzene_Hemisolvate

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S2052520613033167/bi5010Bromobenzene_Hemisolvatesup5.rtv
Contains datablock Bromobenzene_Hemisolvate

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S2052520613033167/bi5010Toluene_Hemisolvatesup6.rtv
Contains datablock Toluene_Hemisolvate

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520613033167/bi5010Toluene_Monosolvatesup7.hkl
Contains datablock Toluene_Monosolvate

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520613033167/bi5010o_Xylene_Monosolvatesup8.hkl
Contains datablock o_Xylene_Monosolvate

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520613033167/bi5010p_Xylene_Sesquisolvatesup9.hkl
Contains datablock p_Xylene_Sesquisolvate

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520613033167/bi5010Monohydratesup10.hkl
Contains datablock Monohydrate

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S2052520613033167/bi5010Theobromine_AAsup11.rtv
Contains datablock Theobromine_AA

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520613033167/bi5010sup12.pdf
DSC, TGA, SS-NMR, Rietveld difference plots

txt

Text file https://doi.org/10.1107/S2052520613033167/bi5010sup13.txt
DFT-D minimised structures (unit cell constrained)

txt

Text file https://doi.org/10.1107/S2052520613033167/bi5010sup14.txt
DFT-D minimised structures (unit cell free)

CCDC references: 907851; 907852; 907853; 907855; 907856; 907857; 907858; 907859; 975719; 975720

Experimental top

Refinement top

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

Results and discussion top

Computing details top

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 top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
(Form1) top
Crystal data top
C8H10N4O2·C7H7NO2γ = 93.5278 (9)°
Mr = 331.33V = 1567.35 (7) Å3
Triclinic, P1Z = 4
a = 8.4853 (2) ÅF(000) = 696
b = 13.4240 (3) ÅDx = 1.404 Mg m3
c = 14.8856 (4) ÅSynchrotron radiation, λ = 1.033787 Å
α = 111.7249 (16)°T = 293 K
β = 92.8464 (15)°white
Data collection top
Diamond Light Source beamline I11
diffractometer
Data collection mode: transmission
Radiation source: synchrotronScan method: continuous
Si(111) monochromator2θmin = 3.000°, 2θmax = 40.000°, 2θstep = 0.004°
Specimen mounting: glass capillary
Refinement top
Rp = 0.014310 parameters
Rwp = 0.019224 restraints
Rexp = 0.0100 constraints
RBragg = 0.003
χ2 = 3.587
9251 data pointsBackground function: Chebyshev polynomial
Profile function: pseudo-VoigtPreferred orientation correction: spherical harmonics
Crystal data top
C8H10N4O2·C7H7NO2β = 92.8464 (15)°
Mr = 331.33γ = 93.5278 (9)°
Triclinic, P1V = 1567.35 (7) Å3
a = 8.4853 (2) ÅZ = 4
b = 13.4240 (3) ÅSynchrotron radiation, λ = 1.033787 Å
c = 14.8856 (4) ÅT = 293 K
α = 111.7249 (16)°
Data collection top
Diamond Light Source beamline I11
diffractometer
Scan method: continuous
Specimen mounting: glass capillary2θmin = 3.000°, 2θmax = 40.000°, 2θstep = 0.004°
Data collection mode: transmission
Refinement top
Rp = 0.014χ2 = 3.587
Rwp = 0.0199251 data points
Rexp = 0.010310 parameters
RBragg = 0.003224 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.6670 (5)0.2757 (3)0.8500 (3)0.069
C20.5384 (5)0.3460 (4)0.8572 (5)0.069
C30.8129 (5)0.3035 (3)0.8231 (5)0.069
C40.6467 (5)0.1789 (3)0.8680 (4)0.069
O50.5913 (6)0.4391 (4)0.8481 (6)0.069
O60.4019 (8)0.3256 (7)0.8779 (6)0.069
C70.9404 (5)0.2385 (3)0.8138 (5)0.069
H80.825 (3)0.3700 (14)0.8128 (13)0.082
C90.7730 (5)0.1143 (3)0.8562 (5)0.069
N100.5137 (5)0.1447 (3)0.8967 (5)0.069
H110.513 (3)0.4828 (14)0.8425 (15)0.082
C120.9139 (6)0.1391 (3)0.8248 (5)0.069
H131.042 (3)0.2598 (13)0.7985 (16)0.082
H140.755 (2)0.0511 (14)0.8687 (14)0.082
H150.427 (3)0.1855 (14)0.8997 (15)0.082
H160.505 (3)0.0764 (14)0.9022 (14)0.082
H171.000 (3)0.0982 (14)0.8253 (13)0.082
C180.1523 (6)0.5198 (3)0.6438 (3)0.069
C190.2851 (6)0.4499 (4)0.6316 (5)0.069
C200.0001 (5)0.4852 (3)0.6610 (5)0.069
C210.1753 (5)0.6223 (3)0.6391 (4)0.069
O220.2360 (7)0.3542 (4)0.6340 (5)0.069
O230.4245 (8)0.4699 (6)0.6134 (7)0.069
C240.1305 (5)0.5468 (3)0.6701 (6)0.069
H250.014 (3)0.4158 (14)0.6637 (12)0.082
C260.0476 (5)0.6857 (3)0.6554 (5)0.069
N270.3154 (5)0.6630 (3)0.6223 (5)0.069
H280.320 (3)0.3109 (14)0.6288 (14)0.082
C290.0995 (5)0.6504 (3)0.6734 (6)0.069
H300.236 (3)0.5213 (14)0.6805 (14)0.082
H310.065 (3)0.7520 (15)0.6490 (14)0.082
H320.401 (3)0.6206 (14)0.6167 (14)0.082
H330.326 (3)0.7334 (14)0.6227 (14)0.082
H340.183 (2)0.6954 (15)0.6830 (15)0.082
C350.1660 (5)0.6970 (3)0.9007 (3)0.069
C360.3225 (5)0.6747 (3)0.8849 (4)0.069
C370.1097 (5)0.7955 (3)0.9039 (5)0.069
N380.0891 (5)0.6065 (3)0.9093 (4)0.069
N390.4342 (5)0.7452 (3)0.8737 (5)0.069
N400.3462 (7)0.5751 (4)0.8828 (6)0.069
N410.2344 (5)0.8650 (3)0.8922 (5)0.069
O420.0292 (8)0.8213 (6)0.9147 (9)0.069
C430.2025 (5)0.5362 (3)0.8978 (5)0.069
C440.0786 (5)0.5895 (4)0.9290 (3)0.069
C450.3911 (6)0.8428 (3)0.8753 (6)0.069
C460.5944 (6)0.7162 (3)0.8621 (3)0.069
C470.2030 (6)0.9771 (3)0.9085 (3)0.069
H480.183 (2)0.4666 (15)0.9004 (14)0.082
H490.099 (3)0.6421 (13)0.9900 (13)0.082
H500.150 (2)0.5926 (14)0.8775 (14)0.082
H510.097 (3)0.5204 (15)0.9309 (14)0.082
O520.4893 (9)0.9138 (6)0.8732 (8)0.069
H530.625 (3)0.6967 (14)0.9151 (14)0.082
H540.594 (3)0.6570 (15)0.8023 (15)0.082
H550.664 (3)0.7737 (13)0.8621 (14)0.082
H560.234 (2)0.9929 (14)0.8551 (15)0.082
H570.093 (3)0.9830 (16)0.9157 (13)0.082
H580.262 (2)1.0249 (15)0.9654 (14)0.082
C590.6614 (5)0.1021 (3)0.5992 (3)0.069
C600.5097 (5)0.1278 (3)0.6213 (4)0.069
C610.7217 (6)0.0082 (3)0.6030 (5)0.069
N620.7340 (5)0.1826 (3)0.5757 (4)0.069
N630.4029 (5)0.0600 (3)0.6450 (5)0.069
N640.4870 (7)0.2247 (4)0.6143 (5)0.069
N650.6067 (5)0.0555 (3)0.6278 (5)0.069
O660.8583 (8)0.0177 (6)0.5894 (8)0.069
C670.6274 (5)0.2555 (3)0.5861 (4)0.069
C680.8975 (5)0.1872 (3)0.5491 (3)0.069
C690.4528 (5)0.0340 (3)0.6502 (5)0.069
C700.2399 (5)0.0844 (3)0.6643 (3)0.069
C710.6560 (6)0.1575 (3)0.6308 (3)0.069
H720.648 (2)0.3208 (14)0.5755 (15)0.082
H730.970 (3)0.2047 (14)0.6040 (14)0.082
H740.917 (3)0.1200 (13)0.5032 (15)0.082
H750.910 (3)0.2407 (14)0.5223 (14)0.082
O760.3591 (10)0.1046 (6)0.6601 (8)0.069
H770.243 (2)0.1449 (15)0.7225 (15)0.082
H780.192 (3)0.0968 (15)0.6112 (15)0.082
H790.183 (3)0.0257 (15)0.6704 (14)0.082
H800.598 (3)0.2175 (14)0.5809 (14)0.082
H810.766 (3)0.1584 (16)0.6218 (15)0.082
H820.636 (2)0.1595 (14)0.6918 (14)0.082
Geometric parameters (Å, º) top
C1—C21.469 (7)N38—C441.488 (6)
C1—C31.392 (7)N39—C451.375 (7)
C1—C41.422 (7)N39—C461.438 (7)
C2—O51.357 (9)N40—C431.358 (8)
C2—O61.253 (9)N41—C451.395 (7)
C3—C71.412 (6)N41—C471.476 (6)
C3—H80.96 (2)C43—H480.95 (2)
C4—C91.397 (7)C44—H490.95 (2)
C4—N101.341 (7)C44—H500.96 (2)
O5—H110.93 (2)C44—H510.94 (2)
C7—C121.410 (8)C45—O521.237 (10)
C7—H130.95 (2)C46—H530.95 (2)
C9—C121.371 (8)C46—H540.95 (2)
C9—H140.94 (2)C46—H550.94 (2)
N10—H150.94 (2)C47—H560.94 (2)
N10—H160.95 (2)C47—H570.95 (2)
C12—H170.94 (2)C47—H580.95 (2)
C18—C191.486 (7)C59—C601.377 (7)
C18—C201.414 (7)C59—C611.409 (7)
C18—C211.405 (7)C59—N621.374 (7)
C19—O221.341 (8)C60—N631.393 (8)
C19—O231.261 (9)C60—N641.367 (8)
C20—C241.405 (6)C61—N651.410 (8)
C20—H250.95 (2)C61—O661.236 (8)
C21—C261.394 (6)N62—C671.346 (7)
C21—N271.351 (7)N62—C681.465 (6)
O22—H280.94 (2)N63—C691.383 (8)
C24—C291.382 (7)N63—C701.459 (6)
C24—H300.98 (2)N64—C671.372 (8)
C26—C291.383 (7)N65—C691.385 (7)
C26—H310.93 (2)N65—C711.472 (7)
N27—H320.94 (2)C67—H720.95 (2)
N27—H330.94 (2)C68—H730.95 (2)
C29—H340.94 (2)C68—H740.94 (2)
C35—C361.392 (6)C68—H750.94 (2)
C35—C371.419 (7)C69—O761.254 (10)
C35—N381.395 (7)C70—H770.94 (2)
C36—N391.358 (7)C70—H780.95 (2)
C36—N401.354 (8)C70—H790.94 (2)
C37—N411.428 (7)C71—H800.95 (2)
C37—O421.250 (9)C71—H810.95 (2)
N38—C431.361 (7)C71—H820.94 (2)
C2—C1—C3119.0 (5)C45—N41—C47114.2 (4)
C2—C1—C4122.3 (4)N38—C43—N40113.5 (5)
C3—C1—C4118.8 (4)N38—C43—H48123 (1)
C1—C2—O5111.3 (5)N40—C43—H48123 (1)
C1—C2—O6123.4 (6)N38—C44—H49110 (1)
O5—C2—O6125.1 (6)N38—C44—H50111 (1)
C1—C3—C7121.6 (5)N38—C44—H51109 (1)
C1—C3—H8117 (1)H49—C44—H50111 (2)
C7—C3—H8121 (1)H49—C44—H51109 (2)
C1—C4—C9118.8 (5)H50—C44—H51107 (2)
C1—C4—N10124.5 (4)N39—C45—N41117.2 (5)
C9—C4—N10116.7 (5)N39—C45—O52122.1 (6)
C2—O5—H11116 (1)N41—C45—O52120.2 (6)
C3—C7—C12118.5 (5)N39—C46—H53107 (1)
C3—C7—H13121 (1)N39—C46—H54107 (2)
C12—C7—H13120 (1)N39—C46—H55112 (1)
C4—C9—C12122.3 (5)H53—C46—H54111 (2)
C4—C9—H14116 (1)H53—C46—H55109 (2)
C12—C9—H14121 (1)H54—C46—H55110 (2)
C4—N10—H15116 (1)N41—C47—H56109 (1)
C4—N10—H16120 (1)N41—C47—H57108 (1)
H15—N10—H16123 (2)N41—C47—H58110 (1)
C7—C12—C9119.5 (4)H56—C47—H57111 (2)
C7—C12—H17119 (1)H56—C47—H58109 (2)
C9—C12—H17119 (1)H57—C47—H58110 (2)
C19—C18—C20120.8 (4)C60—C59—C61122.5 (5)
C19—C18—C21120.8 (4)C60—C59—N62108.0 (4)
C20—C18—C21118.4 (4)C61—C59—N62129.5 (5)
C18—C19—O22111.1 (4)C59—C60—N63122.1 (5)
C18—C19—O23127.1 (7)C59—C60—N64109.2 (5)
O22—C19—O23121.6 (6)N63—C60—N64128.7 (5)
C18—C20—C24123.1 (5)C59—C61—N65111.7 (4)
C18—C20—H25118 (1)C59—C61—O66126.5 (7)
C24—C20—H25119 (1)N65—C61—O66121.7 (7)
C18—C21—C26117.9 (5)C59—N62—C67106.1 (4)
C18—C21—N27123.2 (4)C59—N62—C68125.5 (4)
C26—C21—N27118.8 (5)C67—N62—C68128.4 (5)
C19—O22—H28111 (1)C60—N63—C69118.9 (4)
C20—C24—C29116.4 (4)C60—N63—C70122.4 (5)
C20—C24—H30122 (1)C69—N63—C70118.7 (5)
C29—C24—H30121 (1)C60—N64—C67104.9 (5)
C21—C26—C29122.4 (5)C61—N65—C69128.1 (5)
C21—C26—H31116 (1)C61—N65—C71116.2 (4)
C29—C26—H31121 (1)C69—N65—C71115.7 (5)
C21—N27—H32117 (1)N62—C67—N64111.8 (5)
C21—N27—H33120 (1)N62—C67—H72124 (1)
H32—N27—H33123 (2)N64—C67—H72125 (1)
C24—C29—C26121.2 (4)N62—C68—H73111 (1)
C24—C29—H34119 (1)N62—C68—H74109 (1)
C26—C29—H34120 (1)N62—C68—H75108 (1)
C36—C35—C37122.0 (5)H73—C68—H74109 (2)
C36—C35—N38106.5 (4)H73—C68—H75109 (2)
C37—C35—N38131.4 (4)H74—C68—H75110 (2)
C35—C36—N39123.4 (5)N63—C69—N65116.5 (5)
C35—C36—N40110.9 (5)N63—C69—O76122.4 (6)
N39—C36—N40125.6 (5)N65—C69—O76120.2 (6)
C35—C37—N41110.9 (4)N63—C70—H77108 (1)
C35—C37—O42126.5 (6)N63—C70—H78109 (1)
N41—C37—O42122.5 (6)N63—C70—H79110 (1)
C35—N38—C43104.9 (4)H77—C70—H78112 (2)
C35—N38—C44128.3 (4)H77—C70—H79110 (2)
C43—N38—C44126.8 (5)H78—C70—H79108 (2)
C36—N39—C45118.9 (4)N65—C71—H80111 (1)
C36—N39—C46119.1 (4)N65—C71—H81107 (1)
C45—N39—C46122.0 (5)N65—C71—H82108 (1)
C36—N40—C43104.2 (5)H80—C71—H81110 (2)
C37—N41—C45127.4 (5)H80—C71—H82109 (2)
C37—N41—C47118.1 (4)H81—C71—H82111 (2)
(Form2) top
Crystal data top
C8H10N4O2·C7H7NO2Z = 4
Mr = 331.33F(000) = 696
Orthorhombic, Pna21Dx = 1.363 Mg m3
a = 14.53798 (14) ÅSynchrotron radiation, λ = 1.033787 Å
b = 11.07930 (8) ÅT = 293 K
c = 10.02456 (7) Åwhite
V = 1614.66 (2) Å3
Data collection top
Diamond Light Source beamline I11
diffractometer
Data collection mode: transmission
Radiation source: synchrotronScan method: continuous
Si(111) monochromator2θmin = 3.000°, 2θmax = 40.000°, 2θstep = 0.004°
Specimen mounting: glass capillary
Refinement top
Rp = 0.010158 parameters
Rwp = 0.013112 restraints
Rexp = 0.0100 constraints
RBragg = 0.002
χ2 = 1.680
9251 data pointsBackground function: Chebyshev polynomial
Profile function: pseudo-VoigtPreferred orientation correction: spherical harmonics
Crystal data top
C8H10N4O2·C7H7NO2c = 10.02456 (7) Å
Mr = 331.33V = 1614.66 (2) Å3
Orthorhombic, Pna21Z = 4
a = 14.53798 (14) ÅSynchrotron radiation, λ = 1.033787 Å
b = 11.07930 (8) ÅT = 293 K
Data collection top
Diamond Light Source beamline I11
diffractometer
Scan method: continuous
Specimen mounting: glass capillary2θmin = 3.000°, 2θmax = 40.000°, 2θstep = 0.004°
Data collection mode: transmission
Refinement top
Rp = 0.010χ2 = 1.680
Rwp = 0.0139251 data points
Rexp = 0.010158 parameters
RBragg = 0.002112 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2841 (2)0.2263 (3)0.5133 (3)0.059
C20.3110 (2)0.2754 (5)0.6469 (3)0.059
C30.1898 (2)0.2239 (4)0.4785 (3)0.059
C40.3527 (2)0.1864 (4)0.4217 (3)0.059
O50.2381 (2)0.3110 (4)0.7185 (3)0.059
O60.3906 (3)0.2718 (4)0.6899 (4)0.059
C70.1592 (2)0.1840 (4)0.3551 (3)0.059
H80.1445 (10)0.2506 (13)0.5421 (14)0.070
C90.32135 (19)0.1454 (4)0.2956 (3)0.059
N100.44572 (17)0.1795 (4)0.4493 (3)0.059
H110.2569 (10)0.3344 (15)0.8048 (14)0.070
C120.22692 (19)0.1452 (4)0.2652 (3)0.059
H130.0934 (11)0.1819 (14)0.3363 (13)0.070
H140.3694 (10)0.1213 (12)0.2336 (13)0.070
H150.4676 (9)0.2084 (13)0.5341 (14)0.070
H160.4873 (10)0.1555 (13)0.3833 (16)0.070
H170.2072 (9)0.1175 (12)0.1823 (15)0.070
C180.6797 (2)0.5386 (3)0.6642 (3)0.059
C190.7432 (2)0.5845 (4)0.5770 (3)0.059
C200.7042 (2)0.4917 (4)0.7925 (3)0.059
N210.5956 (2)0.5507 (3)0.6018 (3)0.059
N220.8347 (2)0.5891 (4)0.6037 (3)0.059
N230.7005 (2)0.6228 (4)0.4640 (3)0.059
N240.7998 (2)0.4983 (4)0.8138 (3)0.059
O250.6488 (3)0.4511 (4)0.8730 (4)0.059
C260.6100 (2)0.6022 (4)0.4826 (3)0.059
C270.5071 (2)0.5109 (2)0.6513 (3)0.059
C280.8668 (2)0.5442 (4)0.7256 (3)0.059
C290.90036 (19)0.6416 (2)0.5107 (3)0.059
C300.83876 (18)0.4453 (3)0.9355 (3)0.059
H310.5595 (10)0.6179 (12)0.4201 (13)0.070
H320.5006 (9)0.5361 (13)0.7451 (13)0.070
H330.5031 (8)0.4208 (14)0.6458 (15)0.070
H340.4607 (9)0.5465 (14)0.5945 (16)0.070
O350.9496 (3)0.5420 (4)0.7520 (4)0.059
H360.9103 (10)0.7259 (13)0.5299 (13)0.070
H370.8760 (10)0.6343 (12)0.4222 (13)0.070
H380.9583 (10)0.5979 (12)0.5190 (13)0.070
H390.8947 (10)0.3996 (12)0.9134 (13)0.070
H400.7890 (10)0.3956 (11)0.9710 (13)0.070
H410.8572 (10)0.5079 (11)0.9987 (12)0.070
Geometric parameters (Å, º) top
C1—C21.498 (5)C19—N231.360 (5)
C1—C31.416 (4)C20—N241.408 (4)
C1—C41.426 (4)C20—O251.225 (5)
C2—O51.340 (5)N21—C261.340 (5)
C2—O61.236 (5)N21—C271.449 (4)
C3—C71.387 (5)N22—C281.399 (5)
C3—H80.962 (15)N22—C291.455 (4)
C4—C91.418 (5)N23—C261.349 (4)
C4—N101.382 (4)N24—C281.411 (5)
O5—H110.944 (15)N24—C301.467 (4)
C7—C121.402 (4)C26—H310.990 (14)
C7—H130.976 (16)C27—H320.985 (15)
C9—C121.406 (4)C27—H331.001 (15)
C9—H140.972 (14)C27—H340.967 (14)
N10—H150.962 (15)C28—O351.233 (5)
N10—H160.935 (15)C29—H360.965 (15)
C12—H170.931 (14)C29—H370.959 (13)
C18—C191.369 (4)C29—H380.976 (15)
C18—C201.432 (5)C30—H390.983 (14)
C18—N211.380 (4)C30—H400.976 (14)
C19—N221.358 (4)C30—H410.976 (14)
C2—C1—C3118.7 (3)C18—N21—C26107.9 (3)
C2—C1—C4120.4 (3)C18—N21—C27127.0 (3)
C3—C1—C4120.9 (3)C26—N21—C27125.0 (3)
C1—C2—O5112.3 (3)C19—N22—C28119.0 (3)
C1—C2—O6123.0 (4)C19—N22—C29122.1 (3)
O5—C2—O6124.3 (4)C28—N22—C29118.9 (3)
C1—C3—C7122.4 (3)C19—N23—C26106.1 (3)
C1—C3—H8119.6 (9)C20—N24—C28127.2 (3)
C7—C3—H8118.0 (9)C20—N24—C30119.1 (3)
C1—C4—C9116.6 (3)C28—N24—C30113.5 (3)
C1—C4—N10124.9 (3)N21—C26—N23110.3 (3)
C9—C4—N10118.4 (3)N21—C26—H31121.9 (9)
C2—O5—H11110.0 (9)N23—C26—H31127.7 (9)
C3—C7—C12116.5 (3)N21—C27—H32109.0 (8)
C3—C7—H13119.6 (9)N21—C27—H33109.6 (8)
C12—C7—H13123.8 (9)N21—C27—H34107.0 (9)
C4—C9—C12120.5 (3)H32—C27—H33109.3 (12)
C4—C9—H14115.3 (9)H32—C27—H34112.3 (12)
C12—C9—H14124.2 (9)H33—C27—H34109.5 (12)
C4—N10—H15118.8 (8)N22—C28—N24116.4 (3)
C4—N10—H16120.5 (10)N22—C28—O35121.3 (3)
H15—N10—H16120.4 (12)N24—C28—O35122.2 (4)
C7—C12—C9123.1 (3)N22—C29—H36110.9 (8)
C7—C12—H17117.3 (9)N22—C29—H37108.5 (9)
C9—C12—H17119.6 (9)N22—C29—H38108.2 (8)
C19—C18—C20122.8 (3)H36—C29—H37108.7 (11)
C19—C18—N21105.8 (3)H36—C29—H38109.6 (12)
C20—C18—N21131.5 (3)H37—C29—H38110.9 (17)
C18—C19—N22123.3 (3)N24—C30—H39109.8 (8)
C18—C19—N23109.9 (3)N24—C30—H40104.1 (8)
N22—C19—N23126.9 (3)N24—C30—H41111.2 (7)
C18—C20—N24111.2 (3)H39—C30—H40113.7 (12)
C18—C20—O25124.2 (3)H39—C30—H41106.6 (12)
N24—C20—O25124.6 (3)H40—C30—H41111.6 (11)
(Chlorobenzene_Hemisolvate) top
Crystal data top
2(C8H10N4O2)·2(C7H7NO2)·C6H5ClZ = 2
Mr = 775.22F(000) = 812
Triclinic, P1Dx = 1.421 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.4390 (2) ÅCell parameters from 12124 reflections
b = 13.1409 (2) Åθ = 1.0–30.0°
c = 13.2251 (3) ŵ = 0.17 mm1
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) Å3
Data collection top
Nonius Kappa CCD
diffractometer
4748 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.048
Thin slice ω and φ scansθmax = 30.1°, θmin = 3.7°
Absorption correction: multi-scan
SORTAV (Blessing, 1995)
h = 1617
Tmin = 0.828, Tmax = 0.994k = 1818
27836 measured reflectionsl = 1818
10352 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 0.89 w = 1/[σ2(Fo2) + (0.0496P)2]
where P = (Fo2 + 2Fc2)/3
10352 reflections(Δ/σ)max = 0.002
502 parametersΔρmax = 0.42 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
2(C8H10N4O2)·2(C7H7NO2)·C6H5Clγ = 63.557 (1)°
Mr = 775.22V = 1812.17 (6) Å3
Triclinic, P1Z = 2
a = 12.4390 (2) ÅMo Kα radiation
b = 13.1409 (2) ŵ = 0.17 mm1
c = 13.2251 (3) ÅT = 180 K
α = 69.439 (1)°0.42 × 0.14 × 0.12 mm
β = 80.418 (1)°
Data collection top
Nonius Kappa CCD
diffractometer
10352 independent reflections
Absorption correction: multi-scan
SORTAV (Blessing, 1995)
4748 reflections with I > 2σ(I)
Tmin = 0.828, Tmax = 0.994Rint = 0.048
27836 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.111H-atom parameters constrained
S = 0.89Δρmax = 0.42 e Å3
10352 reflectionsΔρmin = 0.36 e Å3
502 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.05856 (13)0.26720 (14)0.47104 (12)0.0340 (4)
N10.03862 (12)0.31111 (13)0.67600 (11)0.0481 (4)
H1A0.03110.32510.73780.058*
H1B0.06720.35110.61870.058*
O10.09519 (11)0.34170 (11)0.46407 (9)0.0517 (3)
C20.01479 (13)0.20238 (13)0.57175 (11)0.0292 (3)
O20.05422 (9)0.23839 (10)0.38596 (8)0.0404 (3)
H2X0.07680.28050.33060.048*
C30.00631 (13)0.22802 (14)0.66916 (12)0.0333 (4)
C40.03931 (14)0.16447 (14)0.76147 (12)0.0395 (4)
H40.04530.17960.82780.047*
C50.07513 (14)0.08137 (15)0.75768 (12)0.0414 (4)
H50.10630.04070.82120.050*
C60.06677 (14)0.05530 (14)0.66250 (12)0.0386 (4)
H60.09180.00250.66030.046*
C70.02140 (13)0.11530 (13)0.57195 (12)0.0312 (4)
H70.01420.09720.50700.037*
N30.90546 (10)0.67323 (10)0.05176 (9)0.0278 (3)
N40.83064 (10)0.58144 (11)0.11398 (9)0.0300 (3)
N50.79021 (11)0.50395 (11)0.11642 (10)0.0308 (3)
O50.73102 (9)0.46567 (9)0.12726 (8)0.0389 (3)
N60.87828 (10)0.62644 (11)0.20549 (9)0.0298 (3)
O60.93270 (9)0.69263 (9)0.10470 (8)0.0380 (3)
C150.78551 (13)0.52418 (13)0.07088 (12)0.0290 (3)
C160.89221 (13)0.65236 (13)0.05771 (12)0.0296 (3)
C170.86640 (12)0.61811 (13)0.09937 (11)0.0267 (3)
C180.81257 (12)0.54405 (13)0.04138 (12)0.0281 (3)
C190.83084 (13)0.55550 (13)0.21122 (12)0.0330 (4)
H190.82640.54280.27650.040*
C200.96061 (14)0.75379 (14)0.11715 (12)0.0366 (4)
H20A0.98880.77960.06980.055*
H20B0.90120.82390.16710.055*
H20C1.02870.71170.15830.055*
C210.73675 (15)0.41922 (14)0.09563 (13)0.0421 (4)
H21A0.74410.39690.16060.063*
H21B0.65170.45650.07640.063*
H21C0.77870.34740.03600.063*
C220.81061 (14)0.56799 (15)0.23019 (12)0.0420 (4)
H22A0.77060.64730.23990.063*
H22B0.88800.52320.26710.063*
H22C0.76000.52450.26080.063*
N70.67731 (11)0.06460 (11)0.31045 (9)0.0306 (3)
O70.82743 (9)0.16438 (10)0.12662 (8)0.0395 (3)
N80.75884 (11)0.02257 (11)0.14650 (9)0.0314 (3)
O80.68043 (9)0.10998 (9)0.15906 (8)0.0394 (3)
N90.75448 (11)0.13598 (11)0.36638 (9)0.0302 (3)
N100.68058 (11)0.00206 (11)0.45944 (9)0.0328 (3)
C230.78169 (13)0.09781 (14)0.18454 (12)0.0303 (4)
C240.70333 (13)0.05440 (13)0.20303 (12)0.0310 (4)
C250.70006 (12)0.00371 (13)0.35485 (11)0.0278 (3)
C260.74627 (13)0.08365 (13)0.29520 (11)0.0287 (3)
C270.71532 (13)0.08391 (13)0.46198 (12)0.0335 (4)
H270.71240.10320.52550.040*
C280.62802 (14)0.15003 (14)0.37628 (13)0.0396 (4)
H28A0.58870.16660.32940.059*
H28B0.56930.11610.42810.059*
H28C0.69310.22460.41540.059*
C290.79840 (14)0.22855 (14)0.34087 (13)0.0394 (4)
H29A0.77860.26190.40060.059*
H29B0.76040.29230.27480.059*
H29C0.88570.19350.33010.059*
C300.79694 (15)0.02269 (16)0.03485 (12)0.0427 (4)
H30A0.82920.05910.03160.064*
H30B0.85920.05300.01180.064*
H30C0.72790.07430.01310.064*
N20.36368 (12)0.08127 (12)0.06600 (11)0.0454 (4)
H2A0.36130.07280.00340.054*
H2B0.33430.04340.12430.054*
O30.32649 (10)0.04094 (10)0.28059 (9)0.0455 (3)
O40.38481 (9)0.13365 (9)0.35784 (8)0.0412 (3)
H4X0.35920.09500.41360.049*
C80.37163 (13)0.10893 (14)0.27311 (12)0.0324 (4)
C90.41799 (12)0.16998 (13)0.17074 (12)0.0299 (3)
C100.41228 (13)0.15231 (14)0.07260 (12)0.0325 (4)
C110.45885 (13)0.21234 (14)0.02146 (13)0.0404 (4)
H110.45560.20220.08840.048*
C120.50910 (14)0.28569 (15)0.01769 (14)0.0450 (4)
H120.54040.32500.08200.054*
C130.51459 (14)0.30287 (15)0.07916 (13)0.0425 (4)
H130.54940.35340.08130.051*
C140.46910 (13)0.24588 (13)0.17087 (13)0.0345 (4)
H140.47220.25800.23680.041*
Cl10.41515 (5)0.74908 (5)0.31917 (5)0.07674 (19)
C310.40109 (15)0.61564 (16)0.35184 (14)0.0447 (4)
C320.29997 (16)0.60650 (17)0.40470 (14)0.0494 (5)
H320.23880.67230.42460.059*
C330.28707 (19)0.5008 (2)0.42921 (15)0.0599 (5)
H330.21780.49310.46730.072*
C340.3756 (2)0.40686 (18)0.39783 (16)0.0624 (6)
H340.36680.33470.41280.075*
C350.47619 (18)0.41811 (18)0.34500 (17)0.0657 (6)
H350.53750.35260.32480.079*
C360.49009 (16)0.52213 (18)0.32062 (16)0.0571 (5)
H360.55960.52950.28300.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0388 (9)0.0389 (10)0.0270 (9)0.0189 (8)0.0010 (7)0.0106 (7)
N10.0720 (10)0.0620 (10)0.0296 (8)0.0413 (9)0.0077 (7)0.0223 (7)
O10.0821 (9)0.0652 (9)0.0347 (7)0.0550 (8)0.0111 (6)0.0194 (6)
C20.0313 (8)0.0345 (9)0.0221 (8)0.0141 (8)0.0020 (6)0.0099 (7)
O20.0600 (7)0.0571 (8)0.0200 (6)0.0406 (7)0.0078 (5)0.0125 (5)
C30.0357 (9)0.0353 (10)0.0267 (9)0.0127 (8)0.0020 (7)0.0096 (7)
C40.0451 (10)0.0452 (11)0.0225 (9)0.0133 (9)0.0018 (7)0.0126 (8)
C50.0502 (10)0.0416 (11)0.0241 (9)0.0191 (9)0.0074 (7)0.0044 (8)
C60.0494 (10)0.0348 (10)0.0296 (9)0.0201 (9)0.0016 (8)0.0056 (8)
C70.0362 (9)0.0339 (9)0.0234 (8)0.0145 (8)0.0005 (7)0.0094 (7)
N30.0342 (7)0.0328 (7)0.0213 (7)0.0202 (6)0.0032 (5)0.0075 (6)
N40.0366 (7)0.0359 (8)0.0185 (7)0.0178 (7)0.0032 (5)0.0077 (6)
N50.0368 (7)0.0312 (7)0.0278 (7)0.0181 (6)0.0008 (6)0.0086 (6)
O50.0496 (7)0.0379 (7)0.0293 (6)0.0259 (6)0.0071 (5)0.0042 (5)
N60.0349 (7)0.0368 (8)0.0220 (7)0.0192 (6)0.0028 (5)0.0099 (6)
O60.0465 (7)0.0474 (7)0.0311 (6)0.0255 (6)0.0021 (5)0.0180 (5)
C150.0296 (8)0.0251 (8)0.0266 (9)0.0105 (7)0.0016 (7)0.0036 (7)
C160.0304 (8)0.0304 (9)0.0261 (9)0.0112 (7)0.0020 (7)0.0099 (7)
C170.0269 (8)0.0293 (9)0.0223 (8)0.0120 (7)0.0008 (6)0.0065 (7)
C180.0308 (8)0.0273 (9)0.0268 (8)0.0130 (7)0.0002 (7)0.0082 (7)
C190.0363 (9)0.0376 (10)0.0272 (9)0.0165 (8)0.0007 (7)0.0118 (7)
C200.0442 (10)0.0424 (10)0.0303 (9)0.0283 (9)0.0057 (7)0.0085 (8)
C210.0549 (11)0.0398 (11)0.0427 (10)0.0304 (9)0.0024 (8)0.0127 (8)
C220.0506 (10)0.0583 (12)0.0237 (9)0.0296 (10)0.0075 (7)0.0151 (8)
N70.0393 (7)0.0343 (8)0.0228 (7)0.0217 (7)0.0035 (6)0.0076 (6)
O70.0477 (7)0.0461 (7)0.0280 (6)0.0289 (6)0.0041 (5)0.0051 (5)
N80.0392 (7)0.0386 (8)0.0188 (7)0.0196 (7)0.0045 (5)0.0097 (6)
O80.0526 (7)0.0446 (7)0.0301 (6)0.0255 (6)0.0001 (5)0.0157 (5)
N90.0385 (7)0.0323 (8)0.0231 (7)0.0191 (6)0.0001 (5)0.0067 (6)
N100.0413 (8)0.0382 (8)0.0233 (7)0.0215 (7)0.0038 (6)0.0101 (6)
C230.0308 (8)0.0351 (9)0.0235 (8)0.0153 (8)0.0008 (7)0.0052 (7)
C240.0327 (9)0.0333 (9)0.0265 (9)0.0129 (8)0.0013 (7)0.0096 (7)
C250.0300 (8)0.0323 (9)0.0220 (8)0.0140 (7)0.0004 (6)0.0088 (7)
C260.0339 (8)0.0305 (9)0.0218 (8)0.0142 (7)0.0014 (6)0.0068 (7)
C270.0399 (9)0.0398 (10)0.0238 (9)0.0197 (8)0.0013 (7)0.0101 (7)
C280.0501 (10)0.0405 (10)0.0345 (9)0.0288 (9)0.0062 (8)0.0091 (8)
C290.0522 (10)0.0409 (10)0.0344 (9)0.0294 (9)0.0009 (8)0.0090 (8)
C300.0527 (11)0.0552 (12)0.0243 (9)0.0274 (10)0.0081 (8)0.0145 (8)
N20.0595 (9)0.0576 (10)0.0308 (8)0.0322 (8)0.0029 (7)0.0185 (7)
O30.0652 (8)0.0526 (8)0.0354 (7)0.0407 (7)0.0075 (6)0.0153 (6)
O40.0597 (7)0.0509 (8)0.0243 (6)0.0349 (6)0.0071 (5)0.0123 (5)
C80.0375 (9)0.0348 (10)0.0270 (9)0.0159 (8)0.0023 (7)0.0123 (7)
C90.0282 (8)0.0300 (9)0.0280 (9)0.0103 (7)0.0006 (7)0.0080 (7)
C100.0293 (8)0.0334 (9)0.0296 (9)0.0081 (8)0.0006 (7)0.0105 (7)
C110.0401 (10)0.0429 (11)0.0264 (9)0.0103 (9)0.0037 (7)0.0090 (8)
C120.0452 (10)0.0430 (11)0.0343 (10)0.0177 (9)0.0079 (8)0.0026 (8)
C130.0457 (10)0.0409 (11)0.0408 (11)0.0233 (9)0.0055 (8)0.0087 (8)
C140.0352 (9)0.0341 (10)0.0314 (9)0.0128 (8)0.0003 (7)0.0094 (7)
Cl10.0974 (4)0.0732 (4)0.0916 (4)0.0591 (4)0.0174 (3)0.0395 (3)
C310.0485 (11)0.0506 (12)0.0474 (11)0.0279 (10)0.0038 (9)0.0218 (9)
C320.0471 (11)0.0653 (13)0.0471 (11)0.0274 (10)0.0079 (9)0.0291 (10)
C330.0716 (14)0.0754 (16)0.0461 (12)0.0464 (13)0.0047 (10)0.0161 (11)
C340.0897 (16)0.0453 (13)0.0563 (13)0.0385 (13)0.0197 (12)0.0015 (10)
C350.0540 (13)0.0550 (14)0.0879 (17)0.0106 (11)0.0176 (12)0.0309 (12)
C360.0396 (11)0.0681 (14)0.0788 (15)0.0244 (11)0.0072 (10)0.0412 (12)
Geometric parameters (Å, º) top
C1—O11.2225 (16)N8—C301.4733 (18)
C1—O21.3229 (17)O8—C241.2213 (16)
C1—C21.473 (2)N9—C271.3372 (18)
N1—C31.3544 (18)N9—C261.3852 (17)
N1—H1A0.8800N9—C291.4610 (17)
N1—H1B0.8800N10—C271.3374 (17)
C2—C71.4029 (19)N10—C251.3582 (17)
C2—C31.4185 (19)C23—C261.427 (2)
O2—H2X0.8400C25—C261.3642 (19)
C3—C41.409 (2)C27—H270.9500
C4—C51.369 (2)C28—H28A0.9800
C4—H40.9500C28—H28B0.9800
C5—C61.393 (2)C28—H28C0.9800
C5—H50.9500C29—H29A0.9800
C6—C71.372 (2)C29—H29B0.9800
C6—H60.9500C29—H29C0.9800
C7—H70.9500C30—H30A0.9800
N3—C161.3712 (18)C30—H30B0.9800
N3—C171.3759 (17)C30—H30C0.9800
N3—C201.4648 (17)N2—C101.3499 (18)
N4—C161.4027 (17)N2—H2A0.8800
N4—C151.4107 (18)N2—H2B0.8800
N4—C221.4753 (18)O3—C81.2204 (16)
N5—C191.3356 (18)O4—C81.3237 (17)
N5—C181.3892 (18)O4—H4X0.8400
N5—C211.4632 (17)C8—C91.483 (2)
O5—C151.2247 (16)C9—C141.4019 (19)
N6—C191.3331 (17)C9—C101.414 (2)
N6—C171.3568 (17)C10—C111.408 (2)
O6—C161.2217 (16)C11—C121.380 (2)
C15—C181.423 (2)C11—H110.9500
C17—C181.3670 (19)C12—C131.393 (2)
C19—H190.9500C12—H120.9500
C20—H20A0.9800C13—C141.365 (2)
C20—H20B0.9800C13—H130.9500
C20—H20C0.9800C14—H140.9500
C21—H21A0.9800Cl1—C311.7344 (17)
C21—H21B0.9800C31—C321.367 (2)
C21—H21C0.9800C31—C361.378 (2)
C22—H22A0.9800C32—C331.388 (2)
C22—H22B0.9800C32—H320.9500
C22—H22C0.9800C33—C341.380 (3)
N7—C251.3720 (17)C33—H330.9500
N7—C241.3757 (18)C34—C351.370 (3)
N7—C281.4640 (17)C34—H340.9500
O7—C231.2261 (16)C35—C361.373 (2)
N8—C231.3995 (18)C35—H350.9500
N8—C241.4064 (18)C36—H360.9500
O1—C1—O2121.74 (14)C27—N10—C25103.32 (11)
O1—C1—C2124.50 (14)O7—C23—N8121.73 (13)
O2—C1—C2113.75 (13)O7—C23—C26127.22 (14)
C3—N1—H1A120.0N8—C23—C26111.04 (12)
C3—N1—H1B120.0O8—C24—N7121.87 (13)
H1A—N1—H1B120.0O8—C24—N8121.59 (13)
C7—C2—C3118.92 (13)N7—C24—N8116.55 (12)
C7—C2—C1120.06 (13)N10—C25—C26111.92 (12)
C3—C2—C1121.01 (13)N10—C25—N7126.10 (12)
C1—O2—H2X109.5C26—C25—N7121.98 (13)
N1—C3—C4119.51 (14)C25—C26—N9105.20 (12)
N1—C3—C2122.79 (14)C25—C26—C23123.25 (13)
C4—C3—C2117.69 (13)N9—C26—C23131.46 (13)
C5—C4—C3121.45 (14)N9—C27—N10113.43 (13)
C5—C4—H4119.3N9—C27—H27123.3
C3—C4—H4119.3N10—C27—H27123.3
C4—C5—C6121.27 (15)N7—C28—H28A109.5
C4—C5—H5119.4N7—C28—H28B109.5
C6—C5—H5119.4H28A—C28—H28B109.5
C7—C6—C5118.19 (14)N7—C28—H28C109.5
C7—C6—H6120.9H28A—C28—H28C109.5
C5—C6—H6120.9H28B—C28—H28C109.5
C6—C7—C2122.47 (14)N9—C29—H29A109.5
C6—C7—H7118.8N9—C29—H29B109.5
C2—C7—H7118.8H29A—C29—H29B109.5
C16—N3—C17119.46 (11)N9—C29—H29C109.5
C16—N3—C20120.07 (11)H29A—C29—H29C109.5
C17—N3—C20120.47 (12)H29B—C29—H29C109.5
C16—N4—C15126.96 (12)N8—C30—H30A109.5
C16—N4—C22115.38 (11)N8—C30—H30B109.5
C15—N4—C22117.66 (11)H30A—C30—H30B109.5
C19—N5—C18106.10 (11)N8—C30—H30C109.5
C19—N5—C21126.73 (12)H30A—C30—H30C109.5
C18—N5—C21127.13 (12)H30B—C30—H30C109.5
C19—N6—C17103.41 (11)C10—N2—H2A120.0
O5—C15—N4121.59 (13)C10—N2—H2B120.0
O5—C15—C18127.10 (13)H2A—N2—H2B120.0
N4—C15—C18111.31 (12)C8—O4—H4X109.5
O6—C16—N3121.88 (13)O3—C8—O4122.17 (14)
O6—C16—N4121.21 (13)O3—C8—C9124.15 (13)
N3—C16—N4116.91 (12)O4—C8—C9113.67 (12)
N6—C17—C18111.98 (12)C14—C9—C10119.24 (13)
N6—C17—N3125.81 (12)C14—C9—C8119.73 (13)
C18—C17—N3122.19 (13)C10—C9—C8121.03 (13)
C17—C18—N5104.89 (12)N2—C10—C11119.32 (14)
C17—C18—C15122.86 (13)N2—C10—C9122.63 (14)
N5—C18—C15132.19 (13)C11—C10—C9118.05 (14)
N6—C19—N5113.62 (13)C12—C11—C10120.87 (15)
N6—C19—H19123.2C12—C11—H11119.6
N5—C19—H19123.2C10—C11—H11119.6
N3—C20—H20A109.5C11—C12—C13120.91 (15)
N3—C20—H20B109.5C11—C12—H12119.5
H20A—C20—H20B109.5C13—C12—H12119.5
N3—C20—H20C109.5C14—C13—C12118.88 (15)
H20A—C20—H20C109.5C14—C13—H13120.6
H20B—C20—H20C109.5C12—C13—H13120.6
N5—C21—H21A109.5C13—C14—C9122.04 (15)
N5—C21—H21B109.5C13—C14—H14119.0
H21A—C21—H21B109.5C9—C14—H14119.0
N5—C21—H21C109.5C32—C31—C36121.13 (16)
H21A—C21—H21C109.5C32—C31—Cl1119.42 (14)
H21B—C21—H21C109.5C36—C31—Cl1119.41 (14)
N4—C22—H22A109.5C31—C32—C33119.73 (18)
N4—C22—H22B109.5C31—C32—H32120.1
H22A—C22—H22B109.5C33—C32—H32120.1
N4—C22—H22C109.5C34—C33—C32119.49 (18)
H22A—C22—H22C109.5C34—C33—H33120.3
H22B—C22—H22C109.5C32—C33—H33120.3
C25—N7—C24119.58 (12)C35—C34—C33119.70 (18)
C25—N7—C28120.93 (12)C35—C34—H34120.1
C24—N7—C28119.48 (12)C33—C34—H34120.1
C23—N8—C24127.33 (12)C34—C35—C36121.31 (19)
C23—N8—C30117.13 (12)C34—C35—H35119.3
C24—N8—C30115.54 (12)C36—C35—H35119.3
C27—N9—C26106.11 (11)C35—C36—C31118.62 (17)
C27—N9—C29127.60 (12)C35—C36—H36120.7
C26—N9—C29126.29 (12)C31—C36—H36120.7
(Bromobenzene_Hemisolvate) top
Crystal data top
2(C8H10N4O2)·2(C7H7NO2)·C6H5BrV = 1876.3 (8) Å3
Mr = 819.67Z = 2
Triclinic, P1F(000) = 848
a = 12.569 (3) ÅDx = 1.451 Mg m3
b = 13.409 (3) ÅCu Kα radiation, λ = 1.5418 Å
c = 13.269 (3) ÅT = 293 K
α = 68.991 (4)°white
β = 80.215 (5)°flat sheet, 14 × 10 mm
γ = 64.007 (4)°
Data collection top
Panalytical X'pert Powder
diffractometer
Data collection mode: reflection
Radiation source: sealed X-ray tubeScan method: continuous
None monochromator2θmin = 5.005°, 2θmax = 49.992°, 2θstep = 0.017°
Specimen mounting: glass slide
Refinement top
Rp = 0.046323 parameters
Rwp = 0.059255 restraints
Rexp = 0.0400 constraints
RBragg = 0.016
χ2 = 2.161
2693 data pointsBackground function: Chebyshev polynomial
Profile function: pseudo-VoigtPreferred orientation correction: spherical harmonics
Crystal data top
2(C8H10N4O2)·2(C7H7NO2)·C6H5Brβ = 80.215 (5)°
Mr = 819.67γ = 64.007 (4)°
Triclinic, P1V = 1876.3 (8) Å3
a = 12.569 (3) ÅZ = 2
b = 13.409 (3) ÅCu Kα radiation, λ = 1.5418 Å
c = 13.269 (3) ÅT = 293 K
α = 68.991 (4)°flat sheet, 14 × 10 mm
Data collection top
Panalytical X'pert Powder
diffractometer
Scan method: continuous
Specimen mounting: glass slide2θmin = 5.005°, 2θmax = 49.992°, 2θstep = 0.017°
Data collection mode: reflection
Refinement top
Rp = 0.046χ2 = 2.161
Rwp = 0.0592693 data points
Rexp = 0.040323 parameters
RBragg = 0.016255 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4019 (7)0.6024 (6)0.3553 (8)0.027
C20.3028 (7)0.5886 (6)0.4165 (7)0.027
C30.4891 (7)0.5221 (6)0.3112 (7)0.027
Br40.4195 (5)0.7470 (5)0.3209 (5)0.027
C50.2910 (7)0.4834 (5)0.4376 (7)0.027
H60.246 (3)0.648 (3)0.441 (3)0.032
C70.4817 (7)0.4195 (5)0.3297 (7)0.027
H80.549 (3)0.538 (3)0.267 (3)0.032
C90.3890 (7)0.3930 (6)0.3965 (8)0.027
H100.228 (3)0.470 (3)0.482 (3)0.032
H110.539 (3)0.368 (3)0.297 (2)0.032
H120.392 (3)0.315 (2)0.410 (2)0.032
C130.4179 (7)0.1773 (6)0.1736 (6)0.027
C140.3708 (8)0.1145 (6)0.2730 (6)0.027
C150.4621 (8)0.2567 (6)0.1728 (6)0.027
C160.4171 (7)0.1576 (6)0.0746 (5)0.027
O170.3814 (12)0.1260 (7)0.3652 (7)0.027
O180.3287 (11)0.0424 (9)0.2753 (11)0.027
C190.5025 (9)0.3192 (6)0.0774 (5)0.027
H200.462 (3)0.267 (3)0.242 (3)0.032
C210.4639 (7)0.2243 (6)0.0234 (5)0.027
N220.3677 (7)0.0804 (5)0.0760 (5)0.027
H230.357 (3)0.071 (3)0.420 (3)0.032
C240.5059 (8)0.2995 (5)0.0188 (6)0.027
H250.524 (3)0.379 (3)0.078 (3)0.032
H260.454 (3)0.226 (3)0.092 (2)0.032
H270.344 (3)0.038 (3)0.146 (3)0.032
H280.373 (3)0.056 (3)0.012 (3)0.032
H290.522 (3)0.349 (3)0.085 (2)0.032
C300.0154 (6)0.2085 (6)0.5688 (5)0.027
C310.0651 (8)0.2638 (6)0.4715 (6)0.027
C320.0228 (8)0.1240 (6)0.5721 (5)0.027
C330.0083 (8)0.2337 (6)0.6625 (5)0.027
O340.0524 (9)0.2392 (7)0.3903 (7)0.027
O350.0943 (14)0.3467 (9)0.4537 (12)0.027
C360.0638 (9)0.0626 (6)0.6624 (6)0.027
H370.024 (3)0.113 (2)0.509 (3)0.032
C380.0354 (8)0.1739 (6)0.7574 (6)0.027
N390.0439 (8)0.3116 (6)0.6711 (5)0.027
H400.063 (3)0.295 (3)0.330 (3)0.032
C410.0690 (8)0.0870 (6)0.7593 (5)0.027
H420.087 (3)0.005 (3)0.658 (3)0.032
H430.037 (3)0.193 (3)0.821 (3)0.032
H440.082 (3)0.349 (3)0.608 (3)0.032
H450.047 (3)0.313 (3)0.743 (3)0.032
H460.092 (3)0.044 (3)0.827 (3)0.032
C470.7519 (7)0.0901 (5)0.2878 (6)0.027
C480.7031 (8)0.0108 (6)0.3469 (6)0.027
C490.7831 (7)0.1059 (6)0.1762 (6)0.027
N500.7608 (8)0.1415 (6)0.3608 (6)0.027
N510.6773 (7)0.0594 (6)0.3067 (5)0.027
N520.6895 (9)0.0082 (7)0.4510 (7)0.027
N530.7540 (7)0.0347 (6)0.1336 (6)0.027
O540.8299 (12)0.1732 (10)0.1196 (11)0.027
C550.7232 (8)0.0891 (6)0.4537 (6)0.027
C560.8045 (6)0.2353 (5)0.3486 (5)0.027
C570.6974 (8)0.0449 (6)0.1972 (6)0.027
C580.6285 (6)0.1474 (5)0.3786 (6)0.027
C590.7916 (5)0.0407 (5)0.0174 (5)0.027
H600.716 (3)0.111 (3)0.516 (2)0.032
H610.804 (2)0.283 (3)0.273 (2)0.032
H620.884 (3)0.202 (3)0.378 (3)0.032
H630.753 (3)0.281 (3)0.392 (2)0.032
O640.6688 (13)0.1027 (9)0.1590 (9)0.027
H650.547 (3)0.114 (3)0.374 (3)0.032
H660.644 (3)0.168 (3)0.451 (2)0.032
H670.660 (3)0.215 (3)0.357 (3)0.032
H680.861 (3)0.031 (3)0.020 (3)0.032
H690.811 (3)0.107 (3)0.017 (3)0.032
H700.730 (3)0.051 (3)0.025 (3)0.032
C710.8168 (6)0.5375 (5)0.0383 (6)0.027
C720.8710 (7)0.6153 (6)0.0957 (5)0.027
C730.7953 (7)0.5165 (6)0.0767 (6)0.027
N740.7959 (7)0.4969 (6)0.1172 (6)0.027
N750.9034 (7)0.6787 (6)0.0502 (6)0.027
N760.8842 (9)0.6209 (8)0.2007 (7)0.027
N770.8311 (7)0.5839 (6)0.1223 (6)0.027
O780.7515 (11)0.4492 (9)0.1345 (11)0.027
C790.8354 (7)0.5542 (6)0.2122 (6)0.027
C800.7470 (6)0.4080 (5)0.1077 (5)0.027
C810.8877 (7)0.6623 (6)0.0615 (6)0.027
C820.9637 (6)0.7585 (5)0.1163 (5)0.027
C830.8127 (6)0.5685 (5)0.2394 (6)0.027
H840.835 (3)0.544 (3)0.282 (3)0.032
H850.754 (3)0.355 (3)0.036 (3)0.032
H860.668 (3)0.446 (3)0.124 (3)0.032
H870.786 (3)0.366 (3)0.161 (3)0.032
O880.9281 (12)0.7118 (10)0.1022 (9)0.027
H891.046 (3)0.723 (3)0.100 (3)0.032
H900.960 (3)0.772 (3)0.195 (3)0.032
H910.930 (3)0.832 (3)0.098 (2)0.032
H920.741 (3)0.628 (3)0.251 (2)0.032
H930.811 (3)0.494 (3)0.275 (3)0.032
H940.874 (3)0.573 (2)0.268 (2)0.032
Geometric parameters (Å, º) top
C1—C21.413 (12)C47—N501.418 (13)
C1—C31.379 (11)C48—N511.400 (14)
C1—Br41.930 (11)C48—N521.353 (12)
C2—C51.406 (11)C49—N531.459 (14)
C2—H60.93 (4)C49—O541.246 (17)
C3—C71.351 (11)N50—C551.308 (10)
C3—H80.92 (4)N50—C561.528 (12)
C5—C91.491 (10)N51—C571.388 (10)
C5—H100.95 (3)N51—C581.518 (11)
C7—C91.433 (11)N52—C551.340 (16)
C7—H110.93 (3)N53—C571.474 (12)
C9—H120.99 (3)N53—C591.518 (9)
C13—C141.475 (10)C55—H600.95 (4)
C13—C151.396 (14)C56—H610.98 (3)
C13—C161.432 (11)C56—H620.98 (4)
C14—O171.321 (14)C56—H630.96 (3)
C14—O181.279 (19)C57—O641.256 (19)
C15—C191.400 (10)C58—H650.93 (3)
C15—H200.97 (4)C58—H660.93 (3)
C16—C211.484 (10)C58—H670.95 (4)
C16—N221.415 (14)C59—H680.96 (3)
O17—H230.95 (4)C59—H690.96 (4)
C19—C241.383 (11)C59—H700.97 (4)
C19—H250.95 (5)C71—C721.417 (11)
C21—C241.349 (14)C71—C731.448 (10)
C21—H260.94 (4)C71—N741.446 (13)
N22—H270.98 (3)C72—N751.417 (14)
N22—H280.99 (4)C72—N761.354 (12)
C24—H290.95 (3)C73—N771.492 (14)
C30—C311.433 (10)C73—O781.225 (15)
C30—C321.396 (13)N74—C791.361 (10)
C30—C331.379 (11)N74—C801.524 (12)
C31—O341.286 (15)N75—C811.410 (10)
C31—O351.253 (18)N75—C821.516 (11)
C32—C361.354 (10)N76—C791.346 (16)
C32—H370.90 (4)N77—C811.455 (12)
C33—C381.400 (10)N77—C831.483 (10)
C33—N391.349 (14)C79—H840.99 (4)
O34—H400.92 (3)C80—H850.95 (3)
C36—C411.421 (11)C80—H860.92 (3)
C36—H420.95 (5)C80—H870.99 (4)
C38—C411.394 (14)C81—O881.277 (19)
C38—H430.96 (4)C82—H890.96 (3)
N39—H440.98 (3)C82—H901.00 (4)
N39—H450.96 (4)C82—H910.99 (3)
C41—H460.95 (3)C83—H920.94 (3)
C47—C481.391 (12)C83—H930.95 (3)
C47—C491.428 (10)C83—H940.94 (4)
C2—C1—C3125.9 (8)C47—N50—C55105.2 (8)
C2—C1—Br4119.9 (6)C47—N50—C56133.2 (6)
C3—C1—Br4114.2 (7)C55—N50—C56121.6 (8)
C1—C2—C5118.4 (7)C48—N51—C57117.1 (8)
C1—C2—H6121 (3)C48—N51—C58122.0 (7)
C5—C2—H6120 (3)C57—N51—C58120.9 (9)
C1—C3—C7117.8 (8)C48—N52—C55105.6 (8)
C1—C3—H8122 (2)C49—N53—C57124.3 (7)
C7—C3—H8120 (2)C49—N53—C59116.2 (7)
C2—C5—C9116.0 (7)C57—N53—C59119.5 (8)
C2—C5—H10120 (2)N50—C55—N52114.2 (9)
C9—C5—H10124 (2)N50—C55—H60122 (2)
C3—C7—C9121.1 (7)N52—C55—H60124 (2)
C3—C7—H11117 (3)N50—C56—H61111 (3)
C9—C7—H11122 (3)N50—C56—H62112 (2)
C5—C9—C7120.5 (7)N50—C56—H63106 (2)
C5—C9—H12123 (2)H61—C56—H62109 (3)
C7—C9—H12117 (2)H61—C56—H63111 (2)
C14—C13—C15121.9 (8)H62—C56—H63106 (3)
C14—C13—C16119.2 (9)N51—C57—N53118.2 (9)
C15—C13—C16118.9 (7)N51—C57—O64117.8 (9)
C13—C14—O17118 (1)N53—C57—O64123.9 (9)
C13—C14—O18123 (1)N51—C58—H65110 (2)
O17—C14—O18118 (1)N51—C58—H66112 (3)
C13—C15—C19121.5 (8)N51—C58—H67111 (2)
C13—C15—H20116 (2)H65—C58—H66106 (3)
C19—C15—H20122 (2)H65—C58—H67109 (4)
C13—C16—C21117.0 (9)H66—C58—H67110 (3)
C13—C16—N22118.2 (7)N53—C59—H68107 (2)
C21—C16—N22124.8 (8)N53—C59—H69109 (2)
C14—O17—H23106 (3)N53—C59—H70113 (2)
C15—C19—C24120.7 (9)H68—C59—H69110 (3)
C15—C19—H25120 (2)H68—C59—H70111 (3)
C24—C19—H25120 (2)H69—C59—H70107 (3)
C16—C21—C24121.2 (8)C72—C71—C73118.8 (8)
C16—C21—H26122 (3)C72—C71—N74105.9 (6)
C24—C21—H26117 (2)C73—C71—N74135.3 (8)
C16—N22—H27117 (3)C71—C72—N75125.1 (7)
C16—N22—H28122 (3)C71—C72—N76109.1 (9)
H27—N22—H28120 (4)N75—C72—N76125.8 (8)
C19—C24—C21120.5 (8)C71—C73—N77114.8 (7)
C19—C24—H29120 (3)C71—C73—O78125 (1)
C21—C24—H29119 (3)N77—C73—O78121 (1)
C31—C30—C32120.5 (8)C71—N74—C79104.5 (8)
C31—C30—C33121.1 (9)C71—N74—C80132.5 (6)
C32—C30—C33118.3 (7)C79—N74—C80123.0 (8)
C30—C31—O34112.1 (10)C72—N75—C81120.1 (8)
C30—C31—O35127.7 (10)C72—N75—C82122.1 (6)
O34—C31—O35118.3 (10)C81—N75—C82117.6 (9)
C30—C32—C36124.1 (8)C72—N76—C79107.3 (8)
C30—C32—H37119 (3)C73—N77—C81125.1 (7)
C36—C32—H37118 (3)C73—N77—C83119.0 (7)
C30—C33—C38119.6 (9)C81—N77—C83115.8 (8)
C30—C33—N39124.5 (7)N74—C79—N76113.1 (8)
C38—C33—N39115.9 (8)N74—C79—H84124 (2)
C31—O34—H40106 (3)N76—C79—H84122 (2)
C32—C36—C41117.5 (9)N74—C80—H85111 (3)
C32—C36—H42119 (2)N74—C80—H86110 (3)
C41—C36—H42123 (2)N74—C80—H87111 (2)
C33—C38—C41120.8 (8)H85—C80—H86107 (3)
C33—C38—H43117 (2)H85—C80—H87112 (3)
C41—C38—H43122 (2)H86—C80—H87107 (3)
C33—N39—H44118 (3)N75—C81—N77115.9 (9)
C33—N39—H45118 (2)N75—C81—O88118.8 (9)
H44—N39—H45123 (4)N77—C81—O88125.2 (8)
C36—C41—C38119.6 (7)N75—C82—H89111 (2)
C36—C41—H46122 (3)N75—C82—H90111 (2)
C38—C41—H46118 (3)N75—C82—H91110 (2)
C48—C47—C49121.4 (9)H89—C82—H90106 (3)
C48—C47—N50106.0 (7)H89—C82—H91106 (3)
C49—C47—N50132.6 (8)H90—C82—H91114 (2)
C47—C48—N51125.8 (7)N77—C83—H92110 (2)
C47—C48—N52108.9 (9)N77—C83—H93108 (2)
N51—C48—N52125.2 (8)N77—C83—H94112 (2)
C47—C49—N53112.9 (8)H92—C83—H93110 (3)
C47—C49—O54124.6 (12)H92—C83—H94108 (3)
N53—C49—O54122.5 (10)H93—C83—H94109 (3)
(Toluene_Hemisolvate) top
Crystal data top
2(C8H10N4O2)·2(C7H7NO2)·C7H8V = 1873 (2) Å3
Mr = 754.80Z = 2
Triclinic, P1F(000) = 796
a = 12.475 (9) ÅDx = 1.338 (2) Mg m3
b = 13.488 (9) ÅCu Kα radiation, λ = 1.5418 Å
c = 13.316 (9) ÅT = 293 K
α = 68.318 (11)°white
β = 79.948 (16)°flat sheet, 14 × 10 mm
γ = 64.124 (11)°
Data collection top
Panalytical X'pert Powder
diffractometer
Data collection mode: reflection
Radiation source: sealed X-ray tubeScan method: continuous
None monochromator2θmin = 5.000°, 2θmax = 39.969°, 2θstep = 0.017°
Specimen mounting: glass slide
Refinement top
Rp = 0.050337 parameters
Rwp = 0.067264 restraints
Rexp = 0.0600 constraints
RBragg = 0.007
χ2 = 1.219
2058 data pointsBackground function: Chebyshev polynomial
Profile function: pseudo-voigtPreferred orientation correction: spherical harmonics
Crystal data top
2(C8H10N4O2)·2(C7H7NO2)·C7H8β = 79.948 (16)°
Mr = 754.80γ = 64.124 (11)°
Triclinic, P1V = 1873 (2) Å3
a = 12.475 (9) ÅZ = 2
b = 13.488 (9) ÅCu Kα radiation, λ = 1.5418 Å
c = 13.316 (9) ÅT = 293 K
α = 68.318 (11)°flat sheet, 14 × 10 mm
Data collection top
Panalytical X'pert Powder
diffractometer
Scan method: continuous
Specimen mounting: glass slide2θmin = 5.000°, 2θmax = 39.969°, 2θstep = 0.017°
Data collection mode: reflection
Refinement top
Rp = 0.050χ2 = 1.219
Rwp = 0.0672058 data points
Rexp = 0.060337 parameters
RBragg = 0.007264 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.421 (3)0.647 (3)0.3337 (19)0.051
C20.311 (2)0.651 (2)0.3831 (17)0.051
C30.493 (3)0.545 (3)0.3158 (17)0.051
C40.463 (3)0.753 (2)0.298 (2)0.051
C50.283 (3)0.561 (3)0.409 (2)0.051
H60.255 (9)0.715 (9)0.399 (9)0.061
C70.468 (3)0.455 (3)0.341 (2)0.051
H80.562 (10)0.540 (9)0.285 (9)0.061
H90.549 (9)0.723 (8)0.312 (9)0.061
H100.451 (9)0.793 (8)0.224 (9)0.061
H110.420 (9)0.810 (7)0.333 (9)0.061
C120.359 (3)0.458 (3)0.390 (2)0.051
H130.210 (9)0.568 (8)0.440 (10)0.061
H140.527 (10)0.389 (7)0.325 (9)0.061
H150.333 (9)0.392 (7)0.413 (9)0.061
C160.4113 (17)0.156 (2)0.185 (3)0.051
C170.370 (3)0.089 (3)0.287 (3)0.051
C180.463 (2)0.241 (2)0.190 (3)0.051
C190.409 (3)0.151 (3)0.082 (3)0.051
O200.392 (4)0.128 (3)0.368 (3)0.051
O210.323 (4)0.009 (4)0.304 (5)0.051
C220.509 (3)0.314 (3)0.100 (3)0.051
H230.466 (10)0.245 (8)0.261 (9)0.061
C240.461 (2)0.235 (3)0.010 (3)0.051
N250.358 (3)0.074 (3)0.070 (3)0.051
H260.372 (11)0.093 (11)0.442 (11)0.061
C270.507 (3)0.307 (3)0.003 (3)0.051
H280.541 (10)0.366 (9)0.113 (10)0.061
H290.463 (9)0.236 (8)0.083 (9)0.061
H300.328 (10)0.028 (8)0.135 (9)0.061
H310.356 (10)0.066 (10)0.001 (11)0.061
H320.537 (11)0.352 (8)0.067 (9)0.061
C330.003 (2)0.198 (2)0.589 (3)0.051
C340.070 (3)0.265 (3)0.500 (3)0.051
C350.033 (2)0.111 (3)0.585 (3)0.051
C360.029 (2)0.220 (3)0.686 (3)0.051
O370.098 (4)0.238 (3)0.408 (3)0.051
O380.101 (4)0.349 (4)0.497 (5)0.051
C390.090 (3)0.047 (3)0.660 (3)0.051
H400.015 (10)0.093 (8)0.523 (9)0.061
C410.091 (3)0.156 (3)0.765 (3)0.051
N420.005 (3)0.300 (3)0.711 (3)0.051
H430.139 (8)0.284 (8)0.358 (9)0.061
C440.122 (3)0.073 (3)0.755 (3)0.051
H450.110 (9)0.010 (8)0.647 (8)0.061
H460.112 (10)0.175 (9)0.830 (9)0.061
H470.036 (9)0.342 (8)0.658 (9)0.061
H480.031 (9)0.310 (8)0.780 (9)0.061
H490.164 (9)0.035 (7)0.812 (9)0.061
C500.739 (2)0.090 (3)0.303 (2)0.051
C510.682 (2)0.012 (3)0.363 (3)0.051
C520.785 (3)0.107 (3)0.189 (3)0.051
N530.740 (3)0.142 (3)0.375 (3)0.051
N540.663 (3)0.064 (3)0.319 (3)0.051
N550.651 (3)0.022 (3)0.468 (3)0.051
N560.766 (3)0.037 (3)0.146 (3)0.051
O570.842 (4)0.170 (4)0.122 (5)0.051
C580.686 (3)0.098 (3)0.477 (3)0.051
C590.788 (3)0.228 (3)0.342 (3)0.051
C600.707 (3)0.047 (3)0.204 (3)0.051
C610.595 (3)0.159 (3)0.386 (3)0.051
C620.812 (3)0.067 (3)0.026 (2)0.051
H630.674 (9)0.118 (7)0.544 (8)0.061
H640.754 (10)0.282 (9)0.275 (8)0.061
H650.872 (9)0.193 (9)0.336 (8)0.061
H660.766 (9)0.266 (8)0.394 (9)0.061
O670.688 (4)0.100 (4)0.154 (4)0.051
H680.507 (10)0.121 (8)0.374 (10)0.061
H690.604 (11)0.183 (7)0.463 (8)0.061
H700.629 (10)0.232 (8)0.367 (10)0.061
H710.853 (9)0.000 (9)0.003 (10)0.061
H720.865 (12)0.104 (11)0.021 (10)0.061
H730.746 (9)0.125 (10)0.023 (9)0.061
C740.8143 (15)0.5288 (16)0.029 (3)0.051
C750.8756 (19)0.607 (2)0.089 (3)0.051
C760.794 (3)0.513 (3)0.085 (3)0.051
N770.793 (3)0.490 (3)0.108 (3)0.051
N780.913 (3)0.663 (2)0.035 (3)0.051
N790.888 (3)0.618 (3)0.200 (3)0.051
N800.838 (3)0.576 (3)0.128 (3)0.051
O810.746 (4)0.456 (4)0.140 (5)0.051
C820.840 (3)0.548 (3)0.203 (3)0.051
C830.733 (3)0.416 (2)0.111 (3)0.051
C840.894 (3)0.648 (3)0.075 (3)0.051
C850.974 (3)0.739 (3)0.082 (2)0.051
C860.830 (3)0.560 (3)0.235 (3)0.051
H870.838 (9)0.539 (8)0.268 (9)0.061
H880.772 (9)0.339 (8)0.070 (9)0.061
H890.655 (10)0.445 (9)0.084 (9)0.061
H900.729 (10)0.421 (7)0.185 (8)0.061
O910.930 (4)0.702 (4)0.112 (4)0.051
H921.046 (9)0.705 (7)0.045 (8)0.061
H930.988 (9)0.746 (7)0.155 (10)0.061
H940.928 (9)0.812 (7)0.072 (8)0.061
H950.780 (9)0.630 (8)0.248 (8)0.061
H960.803 (9)0.504 (10)0.267 (9)0.061
H970.908 (10)0.534 (8)0.260 (8)0.061
Geometric parameters (Å, º) top
C1—C21.40 (4)C50—C521.50 (4)
C1—C31.35 (4)C50—N531.39 (6)
C1—C41.62 (5)C51—N541.47 (6)
C2—C51.31 (5)C51—N551.43 (6)
C2—H60.92 (12)C52—N561.39 (6)
C3—C71.30 (5)C52—O571.33 (6)
C3—H80.88 (12)N53—C581.44 (5)
C4—H90.99 (12)N53—C591.43 (6)
C4—H100.93 (11)N54—C601.51 (5)
C4—H110.96 (12)N54—C611.73 (5)
C5—C121.38 (4)N55—C581.32 (7)
C5—H130.92 (12)N56—C601.51 (5)
C7—C121.39 (4)N56—C621.57 (4)
C7—H140.95 (10)C58—H630.99 (13)
C12—H151.00 (12)C59—H640.94 (9)
C16—C171.47 (4)C59—H650.94 (11)
C16—C181.55 (5)C59—H660.94 (13)
C16—C191.41 (5)C60—O671.25 (8)
C17—O201.47 (7)C61—H681.00 (12)
C17—O211.38 (7)C61—H690.96 (11)
C18—C221.45 (4)C61—H701.00 (13)
C18—H230.98 (14)C62—H710.96 (12)
C19—C241.58 (5)C62—H720.97 (18)
C19—N251.51 (6)C62—H730.98 (9)
O20—H260.96 (13)C74—C751.49 (4)
C22—C271.41 (5)C74—C761.45 (5)
C22—H281.01 (16)C74—N771.44 (6)
C24—C271.38 (6)C75—N781.47 (6)
C24—H290.96 (13)C75—N791.41 (6)
N25—H300.98 (11)C76—N801.49 (6)
N25—H310.99 (17)C76—O811.16 (6)
C27—H320.97 (11)N77—C821.40 (5)
C33—C341.56 (5)N77—C831.50 (6)
C33—C351.45 (6)N78—C841.39 (5)
C33—C361.39 (5)N78—C851.43 (5)
C34—O371.35 (6)N79—C821.33 (7)
C34—O381.33 (8)N80—C841.37 (5)
C35—C391.39 (5)N80—C861.34 (5)
C35—H400.90 (13)C82—H870.93 (13)
C36—C411.44 (5)C83—H880.92 (8)
C36—N421.39 (6)C83—H890.93 (11)
O37—H430.97 (14)C83—H900.97 (12)
C39—C441.38 (5)C84—O911.26 (8)
C39—H450.98 (14)C85—H920.95 (12)
C41—C441.39 (6)C85—H930.92 (14)
C41—H460.96 (13)C85—H940.95 (10)
N42—H470.96 (12)C86—H950.94 (11)
N42—H480.96 (13)C86—H960.90 (14)
C44—H490.96 (11)C86—H970.95 (13)
C50—C511.43 (5)
C2—C1—C3115 (3)C50—C52—N56111 (3)
C2—C1—C4125 (3)C50—C52—O57135 (5)
C3—C1—C4120 (3)N56—C52—O57114 (4)
C1—C2—C5121 (3)C50—N53—C58110 (3)
C1—C2—H6123 (9)C50—N53—C59120 (3)
C5—C2—H6116 (9)C58—N53—C59130 (4)
C1—C3—C7126 (3)C51—N54—C60111 (3)
C1—C3—H8117 (9)C51—N54—C61126 (3)
C7—C3—H8117 (9)C60—N54—C61122 (4)
C1—C4—H9111 (6)C51—N55—C58109 (3)
C1—C4—H10109 (9)C52—N56—C60126 (3)
C1—C4—H11114 (7)C52—N56—C62106 (3)
H9—C4—H10108 (10)C60—N56—C62128 (4)
H9—C4—H11108 (11)N53—C58—N55108 (4)
H10—C4—H11106 (9)N53—C58—H63129 (8)
C2—C5—C12123 (3)N55—C58—H63123 (7)
C2—C5—H13117 (8)N53—C59—H64107 (10)
C12—C5—H13120 (8)N53—C59—H65111 (8)
C3—C7—C12120 (3)N53—C59—H66108 (7)
C3—C7—H14117 (8)H64—C59—H65110 (10)
C12—C7—H14123 (8)H64—C59—H66109 (9)
C5—C12—C7116 (3)H65—C59—H66110 (11)
C5—C12—H15119 (6)N54—C60—N56122 (4)
C7—C12—H15126 (6)N54—C60—O67118 (4)
C17—C16—C18119 (3)N56—C60—O67120 (4)
C17—C16—C19126 (3)N54—C61—H68112 (6)
C18—C16—C19116 (3)N54—C61—H69110 (9)
C16—C17—O20103 (3)N54—C61—H70115 (8)
C16—C17—O21130 (4)H68—C61—H69105 (10)
O20—C17—O21128 (4)H68—C61—H70108 (12)
C16—C18—C22128 (3)H69—C61—H70106 (9)
C16—C18—H23117 (7)N56—C62—H71113 (7)
C22—C18—H23115 (8)N56—C62—H72106 (8)
C16—C19—C24113 (3)N56—C62—H73111 (7)
C16—C19—N25119 (3)H71—C62—H72110 (11)
C24—C19—N25128 (3)H71—C62—H73110 (12)
C17—O20—H26117 (12)H72—C62—H73106 (10)
C18—C22—C27116 (4)C75—C74—C76116 (4)
C18—C22—H28121 (7)C75—C74—N77105 (3)
C27—C22—H28123 (7)C76—C74—N77139 (3)
C19—C24—C27130 (3)C74—C75—N78121 (3)
C19—C24—H29118 (9)C74—C75—N79111 (4)
C27—C24—H29112 (8)N78—C75—N79128 (3)
C19—N25—H30118 (9)C74—C76—N80117 (3)
C19—N25—H31122 (9)C74—C76—O81123 (5)
H30—N25—H31120 (13)N80—C76—O81121 (5)
C22—C27—C24118 (3)C74—N77—C82102 (4)
C22—C27—H32122 (10)C74—N77—C83137 (3)
C24—C27—H32119 (10)C82—N77—C83120 (4)
C34—C33—C35128 (3)C75—N78—C84123 (3)
C34—C33—C36120 (3)C75—N78—C85127 (3)
C35—C33—C36112 (3)C84—N78—C85110 (4)
C33—C34—O37116 (4)C75—N79—C82102 (3)
C33—C34—O38131 (4)C76—N80—C84129 (3)
O37—C34—O38113 (4)C76—N80—C86121 (3)
C33—C35—C39131 (4)C84—N80—C86110 (4)
C33—C35—H40116 (9)N77—C82—N79120 (4)
C39—C35—H40113 (9)N77—C82—H87121 (9)
C33—C36—C41117 (4)N79—C82—H87119 (8)
C33—C36—N42123 (3)N77—C83—H88111 (9)
C41—C36—N42119 (3)N77—C83—H89109 (10)
C34—O37—H43113 (8)N77—C83—H90110 (8)
C35—C39—C44115 (4)H88—C83—H89109 (9)
C35—C39—H45123 (7)H88—C83—H90109 (10)
C44—C39—H45122 (7)H89—C83—H90108 (11)
C36—C41—C44127 (4)N78—C84—N80114 (4)
C36—C41—H46114 (9)N78—C84—O91117 (4)
C44—C41—H46118 (8)N80—C84—O91129 (4)
C36—N42—H47119 (9)N78—C85—H92108 (6)
C36—N42—H48118 (9)N78—C85—H93108 (9)
H47—N42—H48123 (12)N78—C85—H94109 (7)
C39—C44—C41117 (3)H92—C85—H93112 (9)
C39—C44—H49122 (9)H92—C85—H94107 (10)
C41—C44—H49121 (9)H93—C85—H94113 (8)
C51—C50—C52126 (4)N80—C86—H95111 (6)
C51—C50—N53104 (3)N80—C86—H96107 (10)
C52—C50—N53130 (3)N80—C86—H97109 (7)
C50—C51—N54124 (3)H95—C86—H96112 (11)
C50—C51—N55109 (4)H95—C86—H97110 (12)
N54—C51—N55127 (3)H96—C86—H97109 (10)
(Toluene_Monosolvate) top
Crystal data top
C8H10N4O2·C7H7NO2·C7H8Z = 4
Mr = 423.47F(000) = 896
Triclinic, P1Dx = 1.314 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.7113 (3) ÅCell parameters from 14929 reflections
b = 13.5803 (6) Åθ = 1.0–22.5°
c = 23.579 (2) ŵ = 0.09 mm1
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) Å3
Data collection top
Nonius Kappa CCD
diffractometer
3560 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.082
Thin slice ω and φ scansθmax = 22.4°, θmin = 3.5°
Absorption correction: multi-scan
SORTAV (Blessing, 1995)
h = 77
Tmin = 0.740, Tmax = 1.000k = 1414
11209 measured reflectionsl = 2425
5163 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.133Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.360H-atom parameters constrained
S = 1.36 w = 1/[σ2(Fo2) + (0.2P)2]
where P = (Fo2 + 2Fc2)/3
5163 reflections(Δ/σ)max < 0.001
543 parametersΔρmax = 0.89 e Å3
0 restraintsΔρmin = 0.44 e Å3
Crystal data top
C8H10N4O2·C7H7NO2·C7H8γ = 86.065 (2)°
Mr = 423.47V = 2140.7 (2) Å3
Triclinic, P1Z = 4
a = 6.7113 (3) ÅMo Kα radiation
b = 13.5803 (6) ŵ = 0.09 mm1
c = 23.579 (2) ÅT = 180 K
α = 87.100 (2)°0.46 × 0.12 × 0.05 mm
β = 88.572 (2)°
Data collection top
Nonius Kappa CCD
diffractometer
5163 independent reflections
Absorption correction: multi-scan
SORTAV (Blessing, 1995)
3560 reflections with I > 2σ(I)
Tmin = 0.740, Tmax = 1.000Rint = 0.082
11209 measured reflectionsθmax = 22.4°
Refinement top
R[F2 > 2σ(F2)] = 0.1330 restraints
wR(F2) = 0.360H-atom parameters constrained
S = 1.36Δρmax = 0.89 e Å3
5163 reflectionsΔρmin = 0.44 e Å3
543 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.7785 (9)0.5952 (5)0.0439 (3)0.0402 (16)
N10.8047 (8)0.6757 (4)0.1607 (2)0.0448 (14)
H1A0.79950.61140.15480.054*
H1B0.81080.70150.19570.054*
O10.7746 (7)0.5311 (3)0.07865 (19)0.0492 (12)
C20.7936 (8)0.7014 (4)0.0590 (2)0.0359 (16)
O20.7678 (6)0.5743 (3)0.01134 (19)0.0497 (12)
H2X0.75010.51400.01730.060*
C30.8031 (9)0.7356 (5)0.1155 (3)0.0400 (16)
C40.8135 (9)0.8384 (5)0.1278 (3)0.0443 (17)
H40.82260.86290.16620.053*
C50.8106 (10)0.9027 (5)0.0848 (3)0.0541 (19)
H50.81660.97160.09340.065*
C60.7990 (10)0.8670 (5)0.0283 (3)0.0485 (17)
H60.79630.91150.00160.058*
C70.7916 (9)0.7692 (4)0.0160 (3)0.0387 (16)
H70.78500.74570.02260.046*
N20.3084 (7)0.8156 (4)0.6573 (2)0.0486 (15)
H2A0.28970.88020.65220.058*
H2B0.31600.78830.69190.058*
O30.2801 (6)0.9282 (3)0.48698 (18)0.0419 (11)
H3X0.25580.98960.48250.050*
O40.2654 (6)0.9657 (3)0.57836 (19)0.0475 (12)
C80.2840 (8)0.9031 (5)0.5415 (3)0.0358 (16)
C90.3151 (8)0.7964 (4)0.5554 (3)0.0299 (14)
C100.3254 (8)0.7589 (5)0.6124 (3)0.0371 (16)
C110.3521 (8)0.6541 (5)0.6214 (3)0.0434 (17)
H110.35960.62660.65920.052*
C120.3670 (9)0.5926 (5)0.5779 (3)0.0479 (18)
H120.38520.52330.58570.057*
C130.3560 (9)0.6299 (5)0.5213 (3)0.0448 (17)
H130.36450.58660.49080.054*
C140.3327 (8)0.7299 (4)0.5111 (3)0.0363 (15)
H140.32810.75560.47290.044*
N30.6942 (7)0.3458 (4)0.1368 (2)0.0420 (14)
N40.7069 (7)0.2260 (4)0.0075 (2)0.0423 (14)
N50.7132 (8)0.3809 (4)0.0342 (2)0.0439 (14)
O50.6905 (7)0.0543 (3)0.0979 (2)0.0536 (13)
O60.6786 (7)0.2933 (3)0.22845 (19)0.0533 (13)
C150.6908 (9)0.1432 (5)0.1070 (3)0.0450 (17)
N3'0.6797 (8)0.1759 (4)0.1625 (2)0.0436 (14)
C170.6855 (9)0.2732 (5)0.1785 (3)0.0430 (17)
C180.7025 (9)0.3182 (5)0.0804 (3)0.0401 (16)
C190.7001 (9)0.2230 (5)0.0661 (3)0.0382 (16)
C200.7144 (9)0.3210 (5)0.0092 (3)0.0474 (18)
H200.72010.34380.04790.057*
C210.6978 (11)0.4485 (5)0.1487 (3)0.0558 (19)
H21A0.67540.45630.18950.084*
H21B0.59230.48690.12760.084*
H21C0.82800.47230.13720.084*
C220.7073 (11)0.1430 (5)0.0292 (3)0.0547 (19)
H22A0.70650.16760.06900.082*
H22B0.58820.10650.02090.082*
H22C0.82730.09910.02260.082*
C230.6684 (13)0.1018 (5)0.2102 (3)0.064 (2)
H23A0.78620.10360.23380.097*
H23B0.66420.03590.19540.097*
H23C0.54740.11680.23310.097*
N60.1936 (7)0.1640 (4)0.3669 (2)0.0341 (12)
N70.1638 (7)0.2806 (4)0.4964 (2)0.0337 (13)
O70.1279 (6)0.4552 (3)0.40698 (18)0.0454 (12)
N80.2044 (6)0.1257 (4)0.4684 (2)0.0340 (13)
O80.1799 (6)0.2184 (3)0.27458 (19)0.0491 (12)
C240.1442 (8)0.3665 (5)0.3970 (3)0.0355 (15)
N6'0.1459 (7)0.3340 (4)0.3412 (2)0.0385 (13)
C260.1732 (9)0.2367 (5)0.3254 (3)0.0365 (15)
C270.1867 (8)0.1899 (4)0.4227 (3)0.0313 (15)
C280.1632 (8)0.2854 (4)0.4380 (2)0.0282 (14)
C290.1870 (8)0.1845 (5)0.5122 (3)0.0368 (16)
H290.19080.16050.55070.044*
C300.1200 (11)0.4102 (5)0.2951 (3)0.058 (2)
H30A0.01270.39370.27050.087*
H30B0.24470.41330.27270.087*
H30C0.08520.47440.31120.087*
C310.2204 (10)0.0611 (4)0.3534 (3)0.0472 (17)
H31A0.21470.05580.31210.071*
H31B0.11400.02450.37200.071*
H31C0.35040.03330.36680.071*
C320.1435 (10)0.3626 (5)0.5340 (3)0.0453 (17)
H32A0.16840.33800.57310.068*
H32B0.00800.39410.53160.068*
H32C0.24050.41090.52240.068*
C330.313 (2)0.8982 (9)0.2111 (5)0.137 (5)
H33A0.41350.86310.23550.205*
H33B0.22880.94410.23360.205*
H33C0.38000.93520.18030.205*
C340.1895 (10)0.8272 (5)0.1872 (2)0.074 (2)
C350.2497 (11)0.7274 (5)0.1855 (3)0.117 (4)
H350.37450.70320.20060.140*
C360.1272 (16)0.6628 (4)0.1617 (3)0.115 (4)
H360.16830.59460.16050.137*
C370.0555 (15)0.6981 (7)0.1395 (3)0.149 (6)
H370.13920.65400.12320.178*
C380.1157 (9)0.7979 (7)0.1412 (3)0.128 (5)
H380.24060.82200.12600.154*
C390.0068 (10)0.8625 (4)0.1650 (3)0.074 (2)
H390.03440.93070.16620.089*
C400.816 (2)0.8656 (10)0.3187 (5)0.140 (5)
H40A0.78830.90550.35180.210*
H40B0.77970.90510.28410.210*
H40C0.95840.84440.31690.210*
C410.7054 (14)0.7838 (5)0.3233 (3)0.110 (4)
C420.5219 (15)0.7911 (7)0.3520 (3)0.094 (3)
H420.47820.85060.36930.113*
C430.4026 (11)0.7112 (10)0.3553 (3)0.160 (7)
H430.27720.71620.37490.192*
C440.4666 (16)0.6241 (8)0.3299 (4)0.160 (7)
H440.38500.56950.33220.192*
C450.6500 (18)0.6168 (5)0.3012 (4)0.120 (4)
H450.69380.55730.28380.145*
C460.7694 (12)0.6967 (6)0.2979 (3)0.100 (3)
H460.89480.69180.27820.120*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.050 (4)0.043 (4)0.026 (4)0.000 (3)0.001 (3)0.007 (4)
N10.070 (4)0.032 (3)0.033 (3)0.002 (2)0.001 (3)0.009 (3)
O10.074 (3)0.036 (3)0.038 (3)0.005 (2)0.001 (2)0.002 (2)
C20.037 (3)0.041 (4)0.029 (4)0.002 (3)0.008 (3)0.011 (3)
O20.071 (3)0.038 (3)0.041 (3)0.004 (2)0.001 (2)0.000 (2)
C30.040 (4)0.033 (4)0.046 (5)0.004 (3)0.003 (3)0.003 (3)
C40.048 (4)0.042 (5)0.042 (4)0.002 (3)0.001 (3)0.007 (4)
C50.061 (4)0.038 (4)0.062 (5)0.000 (3)0.000 (4)0.000 (4)
C60.069 (4)0.042 (5)0.035 (4)0.005 (3)0.003 (3)0.001 (3)
C70.055 (4)0.030 (4)0.032 (4)0.001 (3)0.001 (3)0.005 (3)
N20.061 (4)0.052 (4)0.032 (3)0.004 (3)0.006 (3)0.003 (3)
O30.059 (3)0.028 (2)0.038 (3)0.0016 (19)0.0012 (19)0.002 (2)
O40.073 (3)0.034 (3)0.035 (3)0.001 (2)0.000 (2)0.001 (2)
C80.031 (3)0.042 (4)0.033 (4)0.000 (3)0.000 (3)0.003 (4)
C90.027 (3)0.024 (3)0.039 (4)0.004 (2)0.002 (2)0.003 (3)
C100.034 (3)0.042 (4)0.035 (4)0.005 (3)0.001 (3)0.005 (3)
C110.034 (4)0.041 (4)0.054 (5)0.003 (3)0.002 (3)0.013 (4)
C120.049 (4)0.035 (4)0.060 (5)0.000 (3)0.001 (3)0.000 (4)
C130.059 (4)0.031 (4)0.045 (5)0.001 (3)0.001 (3)0.005 (3)
C140.036 (3)0.037 (4)0.035 (4)0.001 (3)0.002 (3)0.002 (3)
N30.051 (3)0.042 (4)0.032 (3)0.004 (2)0.000 (2)0.001 (3)
N40.052 (3)0.039 (4)0.034 (3)0.004 (2)0.003 (2)0.005 (3)
N50.058 (3)0.040 (3)0.032 (3)0.003 (2)0.003 (2)0.009 (3)
O50.082 (3)0.031 (3)0.048 (3)0.004 (2)0.004 (2)0.001 (2)
O60.075 (3)0.053 (3)0.032 (3)0.009 (2)0.001 (2)0.004 (2)
C150.045 (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)
C170.050 (4)0.058 (5)0.021 (4)0.001 (3)0.001 (3)0.003 (4)
C180.045 (4)0.038 (4)0.036 (4)0.001 (3)0.005 (3)0.003 (3)
C190.052 (4)0.034 (4)0.027 (4)0.000 (3)0.004 (3)0.005 (3)
C200.061 (4)0.044 (5)0.035 (4)0.005 (3)0.003 (3)0.008 (4)
C210.086 (5)0.037 (4)0.046 (5)0.005 (3)0.012 (4)0.009 (4)
C220.081 (5)0.048 (5)0.035 (4)0.002 (4)0.008 (3)0.016 (4)
C230.109 (6)0.036 (4)0.047 (5)0.009 (4)0.005 (4)0.012 (4)
N60.044 (3)0.033 (3)0.025 (3)0.002 (2)0.001 (2)0.000 (3)
N70.040 (3)0.032 (3)0.029 (3)0.000 (2)0.006 (2)0.003 (2)
O70.060 (3)0.029 (3)0.047 (3)0.0012 (19)0.000 (2)0.004 (2)
N80.036 (3)0.032 (3)0.035 (3)0.005 (2)0.005 (2)0.003 (3)
O80.067 (3)0.045 (3)0.036 (3)0.004 (2)0.001 (2)0.004 (2)
C240.034 (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)
C260.045 (4)0.032 (4)0.034 (4)0.010 (3)0.002 (3)0.009 (3)
C270.024 (3)0.031 (4)0.038 (4)0.001 (2)0.002 (2)0.001 (3)
C280.032 (3)0.025 (4)0.028 (4)0.003 (2)0.000 (2)0.008 (3)
C290.034 (3)0.045 (5)0.030 (4)0.003 (3)0.001 (3)0.007 (3)
C300.083 (5)0.042 (4)0.046 (5)0.001 (4)0.005 (4)0.011 (4)
C310.072 (4)0.031 (4)0.040 (4)0.003 (3)0.000 (3)0.012 (3)
C320.060 (4)0.041 (4)0.037 (4)0.006 (3)0.003 (3)0.014 (3)
C330.184 (13)0.125 (11)0.110 (10)0.070 (9)0.039 (9)0.014 (8)
C340.107 (7)0.070 (6)0.042 (5)0.013 (5)0.002 (4)0.004 (4)
C350.191 (12)0.084 (9)0.063 (7)0.041 (8)0.030 (7)0.025 (6)
C360.231 (15)0.056 (7)0.057 (7)0.015 (8)0.031 (8)0.023 (6)
C370.213 (17)0.195 (18)0.045 (7)0.085 (13)0.005 (8)0.011 (9)
C380.223 (14)0.091 (9)0.067 (8)0.025 (9)0.059 (8)0.011 (7)
C390.112 (7)0.064 (6)0.046 (5)0.006 (5)0.015 (5)0.015 (4)
C400.228 (15)0.125 (11)0.076 (8)0.056 (10)0.035 (8)0.016 (7)
C410.195 (13)0.069 (8)0.065 (7)0.013 (8)0.023 (8)0.009 (6)
C420.132 (9)0.105 (9)0.039 (6)0.026 (7)0.002 (5)0.017 (6)
C430.26 (2)0.150 (14)0.066 (9)0.030 (15)0.079 (10)0.007 (10)
C440.212 (19)0.175 (18)0.097 (11)0.049 (13)0.086 (12)0.046 (11)
C450.162 (12)0.098 (10)0.101 (10)0.003 (9)0.026 (9)0.006 (7)
C460.178 (11)0.068 (7)0.054 (6)0.018 (7)0.006 (6)0.025 (5)
Geometric parameters (Å, º) top
C1—O11.227 (7)C23—H23B0.9800
C1—O21.320 (7)C23—H23C0.9800
C1—C21.477 (9)N6—C261.358 (8)
N1—C31.373 (8)N6—C271.377 (8)
N1—H1A0.8800N6—C311.448 (8)
N1—H1B0.8800N7—C291.338 (8)
C2—C31.390 (9)N7—C281.378 (7)
C2—C71.403 (8)N7—C321.454 (7)
O2—H2X0.8400O7—C241.235 (7)
C3—C41.416 (9)N8—C291.333 (8)
C4—C51.371 (9)N8—C271.355 (7)
C4—H40.9500O8—C261.235 (7)
C5—C61.397 (10)C24—N6'1.408 (8)
C5—H50.9500C24—C281.429 (9)
C6—C71.349 (9)N6'—C261.389 (8)
C6—H60.9500N6'—C301.468 (8)
C7—H70.9500C27—C281.360 (8)
N2—C101.340 (8)C29—H290.9500
N2—H2A0.8800C30—H30A0.9800
N2—H2B0.8800C30—H30B0.9800
O3—C81.314 (7)C30—H30C0.9800
O3—H3X0.8400C31—H31A0.9800
O4—C81.244 (7)C31—H31B0.9800
C8—C91.471 (8)C31—H31C0.9800
C9—C141.411 (8)C32—H32A0.9800
C9—C101.414 (9)C32—H32B0.9800
C10—C111.428 (9)C32—H32C0.9800
C11—C121.353 (9)C33—C341.458 (11)
C11—H110.9500C33—H33A0.9800
C12—C131.405 (9)C33—H33B0.9800
C12—H120.9500C33—H33C0.9800
C13—C141.365 (9)C34—C351.3900
C13—H130.9500C34—C391.3900
C14—H140.9500C35—C361.3900
N3—C171.361 (8)C35—H350.9500
N3—C181.398 (8)C36—C371.3900
N3—C211.439 (8)C36—H360.9500
N4—C201.333 (8)C37—C381.3900
N4—C191.380 (8)C37—H370.9500
N4—C221.456 (8)C38—C391.3900
N5—C201.337 (8)C38—H380.9500
N5—C181.352 (8)C39—H390.9500
O5—C151.237 (8)C40—C411.375 (13)
O6—C171.221 (7)C40—H40A0.9800
C15—N3'1.400 (9)C40—H40B0.9800
C15—C191.418 (9)C40—H40C0.9800
N3'—C171.396 (8)C41—C421.3900
N3'—C231.475 (8)C41—C461.3900
C18—C191.354 (9)C42—C431.3900
C20—H200.9500C42—H420.9500
C21—H21A0.9800C43—C441.3900
C21—H21B0.9800C43—H430.9500
C21—H21C0.9800C44—C451.3900
C22—H22A0.9800C44—H440.9500
C22—H22B0.9800C45—C461.3900
C22—H22C0.9800C45—H450.9500
C23—H23A0.9800C46—H460.9500
O1—C1—O2122.0 (6)H23B—C23—H23C109.5
O1—C1—C2124.3 (6)C26—N6—C27118.6 (5)
O2—C1—C2113.8 (6)C26—N6—C31121.1 (5)
C3—N1—H1A120.0C27—N6—C31120.2 (5)
C3—N1—H1B120.0C29—N7—C28106.0 (5)
H1A—N1—H1B120.0C29—N7—C32126.5 (5)
C3—C2—C7119.3 (6)C28—N7—C32127.4 (5)
C3—C2—C1120.8 (6)C29—N8—C27103.2 (5)
C7—C2—C1119.8 (6)O7—C24—N6'122.0 (5)
C1—O2—H2X109.5O7—C24—C28126.5 (6)
N1—C3—C2124.0 (6)N6'—C24—C28111.5 (5)
N1—C3—C4117.4 (6)C26—N6'—C24126.4 (5)
C2—C3—C4118.6 (6)C26—N6'—C30116.6 (5)
C5—C4—C3120.6 (6)C24—N6'—C30117.0 (5)
C5—C4—H4119.7O8—C26—N6121.7 (6)
C3—C4—H4119.7O8—C26—N6'119.9 (6)
C4—C5—C6119.9 (7)N6—C26—N6'118.3 (5)
C4—C5—H5120.0N8—C27—C28111.9 (5)
C6—C5—H5120.0N8—C27—N6125.2 (5)
C7—C6—C5120.0 (7)C28—C27—N6122.8 (5)
C7—C6—H6120.0C27—C28—N7105.4 (5)
C5—C6—H6120.0C27—C28—C24122.2 (5)
C6—C7—C2121.5 (6)N7—C28—C24132.4 (5)
C6—C7—H7119.3N8—C29—N7113.4 (5)
C2—C7—H7119.3N8—C29—H29123.3
C10—N2—H2A120.0N7—C29—H29123.3
C10—N2—H2B120.0N6'—C30—H30A109.5
H2A—N2—H2B120.0N6'—C30—H30B109.5
C8—O3—H3X109.5H30A—C30—H30B109.5
O4—C8—O3121.9 (6)N6'—C30—H30C109.5
O4—C8—C9123.0 (6)H30A—C30—H30C109.5
O3—C8—C9115.1 (6)H30B—C30—H30C109.5
C14—C9—C10119.2 (5)N6—C31—H31A109.5
C14—C9—C8119.5 (5)N6—C31—H31B109.5
C10—C9—C8121.2 (6)H31A—C31—H31B109.5
N2—C10—C9123.8 (6)N6—C31—H31C109.5
N2—C10—C11119.3 (6)H31A—C31—H31C109.5
C9—C10—C11116.9 (6)H31B—C31—H31C109.5
C12—C11—C10122.2 (6)N7—C32—H32A109.5
C12—C11—H11118.9N7—C32—H32B109.5
C10—C11—H11118.9H32A—C32—H32B109.5
C11—C12—C13120.9 (6)N7—C32—H32C109.5
C11—C12—H12119.6H32A—C32—H32C109.5
C13—C12—H12119.6H32B—C32—H32C109.5
C14—C13—C12118.5 (6)C34—C33—H33A109.5
C14—C13—H13120.8C34—C33—H33B109.5
C12—C13—H13120.8H33A—C33—H33B109.5
C13—C14—C9122.3 (6)C34—C33—H33C109.5
C13—C14—H14118.8H33A—C33—H33C109.5
C9—C14—H14118.8H33B—C33—H33C109.5
C17—N3—C18118.0 (6)C35—C34—C39120.0
C17—N3—C21122.5 (5)C35—C34—C33122.2 (8)
C18—N3—C21119.6 (5)C39—C34—C33117.8 (8)
C20—N4—C19106.1 (5)C34—C35—C36120.0
C20—N4—C22126.4 (6)C34—C35—H35120.0
C19—N4—C22127.5 (6)C36—C35—H35120.0
C20—N5—C18103.3 (5)C37—C36—C35120.0
O5—C15—N3'121.1 (6)C37—C36—H36120.0
O5—C15—C19127.2 (6)C35—C36—H36120.0
N3'—C15—C19111.7 (6)C36—C37—C38120.0
C17—N3'—C15126.7 (6)C36—C37—H37120.0
C17—N3'—C23114.7 (5)C38—C37—H37120.0
C15—N3'—C23118.6 (6)C37—C38—C39120.0
O6—C17—N3120.6 (6)C37—C38—H38120.0
O6—C17—N3'121.3 (6)C39—C38—H38120.0
N3—C17—N3'118.1 (6)C38—C39—C34120.0
N5—C18—C19112.0 (6)C38—C39—H39120.0
N5—C18—N3125.3 (6)C34—C39—H39120.0
C19—C18—N3122.7 (6)C41—C40—H40A109.5
C18—C19—N4105.4 (5)C41—C40—H40B109.5
C18—C19—C15122.7 (6)H40A—C40—H40B109.5
N4—C19—C15131.8 (6)C41—C40—H40C109.5
N4—C20—N5113.2 (6)H40A—C40—H40C109.5
N4—C20—H20123.4H40B—C40—H40C109.5
N5—C20—H20123.4C40—C41—C42118.5 (9)
N3—C21—H21A109.5C40—C41—C46121.4 (9)
N3—C21—H21B109.5C42—C41—C46120.0
H21A—C21—H21B109.5C43—C42—C41120.0
N3—C21—H21C109.5C43—C42—H42120.0
H21A—C21—H21C109.5C41—C42—H42120.0
H21B—C21—H21C109.5C42—C43—C44120.0
N4—C22—H22A109.5C42—C43—H43120.0
N4—C22—H22B109.5C44—C43—H43120.0
H22A—C22—H22B109.5C45—C44—C43120.0
N4—C22—H22C109.5C45—C44—H44120.0
H22A—C22—H22C109.5C43—C44—H44120.0
H22B—C22—H22C109.5C46—C45—C44120.0
N3'—C23—H23A109.5C46—C45—H45120.0
N3'—C23—H23B109.5C44—C45—H45120.0
H23A—C23—H23B109.5C45—C46—C41120.0
N3'—C23—H23C109.5C45—C46—H46120.0
H23A—C23—H23C109.5C41—C46—H46120.0
(o_Xylene_Monosolvate) top
Crystal data top
C8H10N4O2·C7H7NO2·C8H10F(000) = 928
Mr = 437.50Dx = 1.322 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7864 reflections
a = 13.8492 (3) Åθ = 1.0–27.5°
b = 6.7890 (2) ŵ = 0.09 mm1
c = 23.3960 (7) ÅT = 180 K
β = 92.260 (1)°Block, colourless
V = 2198.0 (1) Å30.46 × 0.16 × 0.10 mm
Z = 4
Data collection top
Nonius Kappa CCD
diffractometer
2651 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.036
Thin slice ω and φ scansθmax = 27.5°, θmin = 3.7°
Absorption correction: multi-scan
SORTAV (Blessing, 1995)
h = 1717
Tmin = 0.851, Tmax = 0.998k = 88
13598 measured reflectionsl = 2930
4909 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.127Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.436H-atom parameters constrained
S = 1.55 w = 1/[σ2(Fo2) + (0.2P)2]
where P = (Fo2 + 2Fc2)/3
4909 reflections(Δ/σ)max = 0.006
236 parametersΔρmax = 1.35 e Å3
0 restraintsΔρmin = 0.60 e Å3
Crystal data top
C8H10N4O2·C7H7NO2·C8H10V = 2198.0 (1) Å3
Mr = 437.50Z = 4
Monoclinic, P21/nMo Kα radiation
a = 13.8492 (3) ŵ = 0.09 mm1
b = 6.7890 (2) ÅT = 180 K
c = 23.3960 (7) Å0.46 × 0.16 × 0.10 mm
β = 92.260 (1)°
Data collection top
Nonius Kappa CCD
diffractometer
4909 independent reflections
Absorption correction: multi-scan
SORTAV (Blessing, 1995)
2651 reflections with I > 2σ(I)
Tmin = 0.851, Tmax = 0.998Rint = 0.036
13598 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.1270 restraints
wR(F2) = 0.436H-atom parameters constrained
S = 1.55Δρmax = 1.35 e Å3
4909 reflectionsΔρmin = 0.60 e Å3
236 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
N10.3272 (3)0.6954 (5)0.34054 (18)0.0467 (11)
H1A0.39000.71230.34530.056*
H1B0.30060.68790.30580.056*
O10.4735 (2)0.7418 (5)0.41844 (15)0.0489 (10)
C10.4142 (3)0.7227 (6)0.4558 (2)0.0349 (11)
O20.4387 (2)0.7300 (5)0.51045 (14)0.0442 (9)
H20.49870.74710.51450.053*
C20.3108 (3)0.6923 (5)0.44366 (19)0.0321 (11)
C30.2712 (4)0.6810 (6)0.3869 (2)0.0364 (11)
C40.1705 (3)0.6574 (6)0.3774 (2)0.0436 (13)
H40.14340.65060.33950.052*
C50.1109 (4)0.6441 (7)0.4240 (3)0.0502 (14)
H50.04320.62930.41750.060*
C60.1483 (4)0.6521 (7)0.4787 (3)0.0529 (14)
H60.10700.63870.50990.064*
C70.2473 (4)0.6799 (6)0.4889 (2)0.0439 (12)
H70.27230.69060.52720.053*
N20.8332 (3)0.8461 (5)0.65791 (16)0.0377 (10)
O30.9510 (2)0.8618 (5)0.59208 (15)0.0490 (10)
N30.6668 (3)0.8107 (5)0.63186 (16)0.0346 (9)
N40.6323 (3)0.8025 (5)0.52947 (17)0.0385 (10)
O50.7177 (2)0.8200 (5)0.72532 (14)0.0463 (9)
N50.7836 (3)0.8341 (5)0.50178 (17)0.0432 (11)
C80.8650 (3)0.8513 (6)0.6022 (2)0.0351 (11)
C90.7372 (3)0.8244 (6)0.6743 (2)0.0367 (11)
C100.6919 (3)0.8171 (6)0.5762 (2)0.0358 (11)
C110.7861 (3)0.8347 (6)0.56058 (19)0.0340 (11)
C120.6912 (4)0.8160 (7)0.4860 (2)0.0437 (12)
H120.66890.81290.44710.052*
C130.5668 (4)0.7872 (8)0.6456 (2)0.0504 (14)
H13A0.55890.81990.68590.076*
H13B0.54690.65050.63860.076*
H13C0.52660.87530.62150.076*
C140.8653 (4)0.8506 (7)0.4647 (2)0.0526 (14)
H14A0.84160.86400.42490.079*
H14B0.90550.73230.46870.079*
H14C0.90380.96670.47570.079*
C150.9038 (4)0.8675 (9)0.7054 (2)0.0556 (14)
H15A0.96870.87850.69050.083*
H15B0.90100.75190.73040.083*
H15C0.88930.98620.72730.083*
C160.2575 (4)0.4880 (9)0.6600 (3)0.1219 (13)*
C170.2648 (4)0.2998 (9)0.6831 (3)0.1219 (13)*
C180.1820 (5)0.2006 (7)0.6987 (3)0.1219 (13)*
H180.18700.07190.71450.146*
C190.0921 (4)0.2896 (9)0.6911 (3)0.1219 (13)*
H190.03550.22180.70180.146*
C200.0848 (4)0.4779 (9)0.6680 (3)0.1219 (13)*
H200.02330.53880.66280.146*
C210.1676 (5)0.5771 (7)0.6524 (3)0.1219 (13)*
H210.16260.70580.63660.146*
C220.3526 (6)0.5551 (15)0.6435 (4)0.1219 (13)*
H22A0.40070.52330.67390.183*
H22B0.35110.69790.63740.183*
H22C0.36980.48910.60810.183*
C230.3540 (7)0.1898 (13)0.6868 (5)0.1219 (13)*
H23A0.40340.26660.70810.183*
H23B0.37570.16310.64820.183*
H23C0.34350.06490.70660.183*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.053 (3)0.058 (3)0.028 (2)0.003 (2)0.005 (2)0.0047 (18)
O10.0424 (19)0.070 (2)0.035 (2)0.0049 (17)0.0026 (16)0.0015 (16)
C10.044 (3)0.031 (2)0.029 (3)0.0041 (19)0.003 (2)0.0022 (18)
O20.0418 (19)0.056 (2)0.034 (2)0.0010 (15)0.0066 (15)0.0041 (15)
C20.040 (3)0.027 (2)0.030 (3)0.0001 (18)0.000 (2)0.0028 (17)
C30.048 (3)0.027 (2)0.035 (3)0.0040 (19)0.001 (2)0.0015 (18)
C40.048 (3)0.040 (3)0.042 (3)0.005 (2)0.008 (2)0.002 (2)
C50.033 (3)0.051 (3)0.066 (4)0.003 (2)0.008 (3)0.007 (3)
C60.051 (3)0.058 (3)0.051 (4)0.002 (2)0.016 (3)0.002 (3)
C70.054 (3)0.043 (3)0.035 (3)0.002 (2)0.004 (2)0.006 (2)
N20.040 (2)0.040 (2)0.032 (2)0.0013 (16)0.0068 (17)0.0034 (16)
O30.038 (2)0.059 (2)0.051 (2)0.0039 (15)0.0006 (16)0.0035 (16)
N30.037 (2)0.036 (2)0.030 (2)0.0034 (15)0.0011 (17)0.0023 (15)
N40.042 (2)0.037 (2)0.035 (2)0.0081 (16)0.0084 (19)0.0017 (16)
O50.051 (2)0.060 (2)0.028 (2)0.0029 (15)0.0024 (16)0.0025 (15)
N50.053 (3)0.044 (2)0.033 (2)0.0059 (18)0.0002 (19)0.0021 (17)
C80.035 (3)0.035 (2)0.035 (3)0.0037 (18)0.002 (2)0.0023 (19)
C90.044 (3)0.034 (2)0.033 (3)0.0039 (19)0.004 (2)0.0039 (18)
C100.044 (3)0.026 (2)0.037 (3)0.0054 (18)0.005 (2)0.0033 (18)
C110.044 (3)0.031 (2)0.027 (2)0.0016 (18)0.001 (2)0.0006 (17)
C120.050 (3)0.051 (3)0.029 (3)0.005 (2)0.012 (2)0.002 (2)
C130.046 (3)0.060 (3)0.046 (3)0.004 (2)0.003 (2)0.012 (2)
C140.066 (4)0.058 (3)0.035 (3)0.006 (2)0.016 (3)0.002 (2)
C150.040 (3)0.086 (4)0.041 (3)0.004 (3)0.005 (2)0.004 (3)
Geometric parameters (Å, º) top
N1—C31.361 (6)C8—C111.439 (7)
N1—H1A0.8800C10—C111.374 (6)
N1—H1B0.8800C12—H120.9500
O1—C11.230 (6)C13—H13A0.9800
C1—O21.311 (6)C13—H13B0.9800
C1—C21.463 (7)C13—H13C0.9800
O2—H20.8400C14—H14A0.9800
C2—C71.405 (6)C14—H14B0.9800
C2—C31.420 (7)C14—H14C0.9800
C3—C41.412 (7)C15—H15A0.9800
C4—C51.396 (7)C15—H15B0.9800
C4—H40.9500C15—H15C0.9800
C5—C61.362 (8)C16—C171.3900
C5—H50.9500C16—C211.3900
C6—C71.395 (7)C16—C221.459 (9)
C6—H60.9500C17—C181.3900
C7—H70.9500C17—C231.444 (10)
N2—C81.394 (6)C18—C191.3900
N2—C91.405 (6)C18—H180.9500
N2—C151.459 (6)C19—C201.3900
O3—C81.225 (5)C19—H190.9500
N3—C91.367 (6)C20—C211.3900
N3—C101.361 (6)C20—H200.9500
N3—C131.443 (6)C21—H210.9500
N4—C121.331 (6)C22—H22A0.9800
N4—C101.348 (6)C22—H22B0.9800
O5—C91.234 (5)C22—H22C0.9800
N5—C121.322 (6)C23—H23A0.9800
N5—C111.375 (6)C23—H23B0.9800
N5—C141.457 (6)C23—H23C0.9800
C3—N1—H1A120.0N4—C12—H12123.0
C3—N1—H1B120.0N3—C13—H13A109.5
H1A—N1—H1B120.0N3—C13—H13B109.5
O1—C1—O2122.3 (4)H13A—C13—H13B109.5
O1—C1—C2123.6 (4)N3—C13—H13C109.5
O2—C1—C2114.1 (4)H13A—C13—H13C109.5
C1—O2—H2109.5H13B—C13—H13C109.5
C7—C2—C3118.1 (4)N5—C14—H14A109.5
C7—C2—C1119.9 (4)N5—C14—H14B109.5
C3—C2—C1121.9 (4)H14A—C14—H14B109.5
N1—C3—C2122.0 (4)N5—C14—H14C109.5
N1—C3—C4118.3 (5)H14A—C14—H14C109.5
C2—C3—C4119.7 (4)H14B—C14—H14C109.5
C5—C4—C3119.7 (5)N2—C15—H15A109.5
C5—C4—H4120.1N2—C15—H15B109.5
C3—C4—H4120.1H15A—C15—H15B109.5
C6—C5—C4121.1 (5)N2—C15—H15C109.5
C6—C5—H5119.5H15A—C15—H15C109.5
C4—C5—H5119.5H15B—C15—H15C109.5
C5—C6—C7120.1 (5)C17—C16—C21120.0
C5—C6—H6120.0C17—C16—C22109.7 (6)
C7—C6—H6120.0C21—C16—C22130.1 (6)
C6—C7—C2121.3 (5)C16—C17—C18120.0
C6—C7—H7119.4C16—C17—C23123.2 (6)
C2—C7—H7119.4C18—C17—C23116.5 (6)
C8—N2—C9126.6 (4)C17—C18—C19120.0
C8—N2—C15118.9 (4)C17—C18—H18120.0
C9—N2—C15114.5 (4)C19—C18—H18120.0
C9—N3—C10119.4 (4)C20—C19—C18120.0
C9—N3—C13120.6 (4)C20—C19—H19120.0
C10—N3—C13120.0 (4)C18—C19—H19120.0
C12—N4—C10104.0 (4)C21—C20—C19120.0
C12—N5—C11105.4 (4)C21—C20—H20120.0
C12—N5—C14127.4 (5)C19—C20—H20120.0
C11—N5—C14127.3 (4)C20—C21—C16120.0
O3—C8—N2121.8 (4)C20—C21—H21120.0
O3—C8—C11126.4 (4)C16—C21—H21120.0
N2—C8—C11111.7 (4)C16—C22—H22A109.5
O5—C9—N3121.6 (4)C16—C22—H22B109.5
O5—C9—N2120.8 (4)H22A—C22—H22B109.5
N3—C9—N2117.6 (4)C16—C22—H22C109.5
N4—C10—N3127.1 (4)H22A—C22—H22C109.5
N4—C10—C11110.3 (4)H22B—C22—H22C109.5
N3—C10—C11122.6 (5)C17—C23—H23A109.5
C10—C11—N5106.3 (4)C17—C23—H23B109.5
C10—C11—C8122.1 (4)H23A—C23—H23B109.5
N5—C11—C8131.7 (4)C17—C23—H23C109.5
N5—C12—N4114.1 (4)H23A—C23—H23C109.5
N5—C12—H12123.0H23B—C23—H23C109.5
(p_Xylene_Sesquisolvate) top
Crystal data top
C8H10N4O2·C7H7NO2·1.5(C8H10)Z = 2
Mr = 490.58F(000) = 522
Triclinic, P1Dx = 1.261 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.8474 (8) ÅCell parameters from 22396 reflections
b = 13.431 (2) Åθ = 1.0–22.5°
c = 14.440 (3) ŵ = 0.09 mm1
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) Å3
Data collection top
Nonius Kappa CCD
diffractometer
1845 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.112
Thin slice ω and φ scansθmax = 22.6°, θmin = 3.6°
Absorption correction: multi-scan
SORTAV (Blessing, 1995)
h = 77
Tmin = 0.562, Tmax = 0.998k = 1314
8643 measured reflectionsl = 1515
3298 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.086Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.226H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.129P)2]
where P = (Fo2 + 2Fc2)/3
3298 reflections(Δ/σ)max = 0.002
331 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C8H10N4O2·C7H7NO2·1.5(C8H10)γ = 88.687 (8)°
Mr = 490.58V = 1291.7 (4) Å3
Triclinic, P1Z = 2
a = 6.8474 (8) ÅMo Kα radiation
b = 13.431 (2) ŵ = 0.09 mm1
c = 14.440 (3) ÅT = 180 K
α = 77.009 (3)°0.46 × 0.02 × 0.02 mm
β = 86.596 (4)°
Data collection top
Nonius Kappa CCD
diffractometer
3298 independent reflections
Absorption correction: multi-scan
SORTAV (Blessing, 1995)
1845 reflections with I > 2σ(I)
Tmin = 0.562, Tmax = 0.998Rint = 0.112
8643 measured reflectionsθmax = 22.6°
Refinement top
R[F2 > 2σ(F2)] = 0.0860 restraints
wR(F2) = 0.226H-atom parameters constrained
S = 0.97Δρmax = 0.32 e Å3
3298 reflectionsΔρmin = 0.26 e Å3
331 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
O10.2407 (5)0.0021 (3)0.5809 (3)0.0705 (10)
H1X0.24610.02880.53350.085*
O20.2518 (5)0.1397 (3)0.4663 (3)0.0726 (10)
N10.2464 (6)0.3204 (3)0.5189 (3)0.0705 (12)
H1A0.25110.29120.47010.085*
H1B0.24730.38750.50950.085*
C10.2443 (6)0.0986 (4)0.5517 (4)0.0566 (13)
C20.2356 (6)0.1554 (4)0.6277 (3)0.0503 (12)
C30.2376 (6)0.2624 (4)0.6085 (4)0.0541 (13)
C40.2296 (6)0.3111 (4)0.6870 (4)0.0647 (14)
H40.23150.38360.67540.078*
C50.2192 (7)0.2549 (4)0.7788 (4)0.0667 (14)
H50.21350.28860.83010.080*
C60.2170 (7)0.1487 (5)0.7974 (4)0.0705 (15)
H60.21000.10970.86110.085*
C70.2252 (6)0.1010 (4)0.7221 (4)0.0614 (14)
H70.22370.02850.73500.074*
O30.7153 (5)0.2840 (3)0.8026 (3)0.0689 (10)
O40.7532 (5)0.4547 (3)0.4893 (2)0.0680 (10)
N20.7332 (5)0.3672 (3)0.6449 (3)0.0563 (11)
N30.7497 (5)0.2819 (3)0.5183 (3)0.0546 (10)
N40.7438 (5)0.0960 (3)0.5681 (3)0.0568 (11)
N50.7233 (5)0.0865 (3)0.7260 (3)0.0558 (11)
C80.7253 (6)0.2783 (4)0.7184 (4)0.0549 (13)
C90.7464 (6)0.3713 (4)0.5463 (4)0.0549 (13)
C100.7420 (6)0.1904 (4)0.5866 (4)0.0515 (12)
C110.7289 (6)0.1887 (3)0.6820 (4)0.0496 (12)
C120.7340 (7)0.0356 (4)0.6557 (4)0.0627 (14)
H120.73440.03690.66710.075*
C130.7627 (8)0.2817 (4)0.4169 (4)0.0738 (16)
H13A0.85650.33340.38350.111*
H13B0.63380.29740.39090.111*
H13C0.80670.21420.40850.111*
C140.7106 (8)0.0424 (4)0.8275 (4)0.0700 (15)
H14A0.69530.03180.83830.105*
H14B0.59750.07180.85710.105*
H14C0.83020.05730.85560.105*
C150.7303 (9)0.4671 (4)0.6714 (4)0.0811 (17)
H15A0.72140.45660.74090.122*
H15B0.61700.50720.64500.122*
H15C0.85070.50390.64580.122*
C160.1509 (9)0.8531 (5)0.9595 (5)0.097 (2)
H16A0.12270.80811.02210.145*
H16B0.04180.85140.91890.145*
H16C0.16820.92310.96670.145*
C170.3353 (8)0.8172 (4)0.9143 (4)0.0686 (15)
C180.4894 (8)0.7760 (4)0.9671 (4)0.0723 (16)
H180.48110.77081.03390.087*
C190.6566 (9)0.7418 (4)0.9250 (4)0.0752 (16)
H190.76050.71300.96350.090*
C200.6757 (8)0.7488 (4)0.8267 (4)0.0740 (16)
C210.8562 (9)0.7106 (6)0.7795 (5)0.103 (2)
H21A0.84620.72790.71030.155*
H21B0.86720.63630.80160.155*
H21C0.97240.74280.79590.155*
C220.5226 (9)0.7911 (4)0.7730 (4)0.0743 (16)
H220.53310.79780.70600.089*
C230.3535 (9)0.8240 (4)0.8149 (4)0.0739 (16)
H230.24850.85140.77650.089*
C240.3206 (11)0.4878 (6)1.1461 (6)0.121 (3)
H24A0.38440.42131.15650.182*
H24B0.41600.54241.12450.182*
H24C0.26890.49601.20570.182*
C250.1551 (9)0.4935 (5)1.0714 (5)0.0855 (18)
C260.0179 (11)0.5455 (5)1.0751 (5)0.0907 (19)
H260.03270.57741.12660.109*
C270.1673 (10)0.5514 (5)1.0061 (5)0.0876 (19)
H270.28250.58731.01150.105*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.099 (3)0.041 (2)0.073 (3)0.0054 (17)0.0044 (18)0.0147 (18)
O20.104 (3)0.050 (2)0.062 (3)0.0036 (18)0.0001 (19)0.010 (2)
N10.097 (3)0.043 (3)0.069 (3)0.004 (2)0.002 (2)0.006 (2)
C10.062 (3)0.040 (4)0.068 (4)0.007 (2)0.001 (2)0.013 (3)
C20.050 (3)0.039 (3)0.062 (4)0.004 (2)0.001 (2)0.012 (3)
C30.047 (3)0.046 (3)0.066 (4)0.003 (2)0.004 (2)0.004 (3)
C40.060 (3)0.057 (4)0.086 (4)0.001 (2)0.003 (3)0.034 (4)
C50.075 (3)0.063 (4)0.063 (4)0.003 (3)0.001 (3)0.017 (3)
C60.083 (4)0.065 (4)0.062 (4)0.003 (3)0.003 (3)0.012 (3)
C70.066 (3)0.048 (3)0.069 (4)0.002 (2)0.007 (2)0.010 (3)
O30.090 (2)0.061 (2)0.055 (3)0.0094 (17)0.0006 (18)0.0120 (19)
O40.097 (3)0.038 (2)0.064 (2)0.0074 (17)0.0054 (17)0.0008 (19)
N20.067 (2)0.041 (3)0.062 (3)0.0044 (18)0.0021 (19)0.014 (2)
N30.067 (3)0.042 (3)0.056 (3)0.0053 (18)0.0022 (18)0.015 (2)
N40.068 (3)0.037 (3)0.067 (3)0.0067 (18)0.0044 (19)0.013 (2)
N50.066 (3)0.041 (3)0.058 (3)0.0083 (18)0.0038 (18)0.007 (2)
C80.051 (3)0.050 (4)0.060 (4)0.008 (2)0.002 (2)0.003 (3)
C90.055 (3)0.045 (4)0.064 (4)0.005 (2)0.001 (2)0.012 (3)
C100.047 (3)0.044 (3)0.063 (4)0.005 (2)0.001 (2)0.009 (3)
C110.047 (3)0.036 (3)0.065 (4)0.004 (2)0.004 (2)0.008 (3)
C120.066 (3)0.042 (3)0.078 (4)0.004 (2)0.006 (3)0.009 (3)
C130.111 (4)0.063 (4)0.051 (4)0.010 (3)0.007 (3)0.020 (3)
C140.093 (4)0.049 (3)0.064 (4)0.010 (3)0.005 (3)0.002 (3)
C150.126 (5)0.054 (4)0.068 (4)0.007 (3)0.009 (3)0.021 (3)
C160.093 (4)0.091 (5)0.106 (5)0.006 (3)0.003 (4)0.022 (4)
C170.075 (4)0.058 (4)0.070 (4)0.015 (3)0.005 (3)0.008 (3)
C180.078 (4)0.073 (4)0.061 (4)0.019 (3)0.006 (3)0.003 (3)
C190.084 (4)0.063 (4)0.069 (4)0.019 (3)0.014 (3)0.010 (3)
C200.084 (4)0.060 (4)0.072 (4)0.017 (3)0.007 (3)0.000 (3)
C210.094 (5)0.100 (6)0.112 (6)0.000 (4)0.011 (4)0.018 (4)
C220.103 (5)0.056 (4)0.063 (4)0.020 (3)0.010 (3)0.007 (3)
C230.090 (4)0.050 (4)0.077 (4)0.020 (3)0.026 (3)0.003 (3)
C240.124 (6)0.094 (6)0.145 (7)0.019 (4)0.017 (5)0.028 (5)
C250.103 (5)0.051 (4)0.100 (5)0.009 (3)0.020 (4)0.005 (4)
C260.112 (5)0.066 (4)0.099 (5)0.007 (4)0.036 (4)0.021 (4)
C270.091 (5)0.062 (4)0.108 (6)0.021 (3)0.020 (4)0.009 (4)
Geometric parameters (Å, º) top
O1—C11.323 (6)C13—H13C0.9800
O1—H1X0.8400C14—H14A0.9800
O2—C11.231 (6)C14—H14B0.9800
N1—C31.350 (6)C14—H14C0.9800
N1—H1A0.8800C15—H15A0.9800
N1—H1B0.8800C15—H15B0.9800
C1—C21.469 (7)C15—H15C0.9800
C2—C71.392 (6)C16—C171.506 (8)
C2—C31.401 (6)C16—H16A0.9800
C3—C41.429 (7)C16—H16B0.9800
C4—C51.368 (7)C16—H16C0.9800
C4—H40.9500C17—C181.371 (7)
C5—C61.390 (7)C17—C231.416 (8)
C5—H50.9500C18—C191.381 (7)
C6—C71.379 (7)C18—H180.9500
C6—H60.9500C19—C201.400 (8)
C7—H70.9500C19—H190.9500
O3—C81.233 (6)C20—C221.376 (7)
O4—C91.232 (5)C20—C211.512 (8)
N2—C81.407 (6)C21—H21A0.9800
N2—C91.411 (6)C21—H21B0.9800
N2—C151.474 (6)C21—H21C0.9800
N3—C91.349 (6)C22—C231.384 (8)
N3—C101.391 (6)C22—H220.9500
N3—C131.462 (6)C23—H230.9500
N4—C121.339 (6)C24—C251.508 (9)
N4—C101.353 (6)C24—H24A0.9800
N5—C121.344 (6)C24—H24B0.9800
N5—C111.377 (6)C24—H24C0.9800
N5—C141.450 (6)C25—C27i1.392 (9)
C8—C111.418 (7)C25—C261.399 (8)
C10—C111.369 (6)C26—C271.376 (8)
C12—H120.9500C26—H260.9500
C13—H13A0.9800C27—C25i1.392 (9)
C13—H13B0.9800C27—H270.9500
C1—O1—H1X109.5N5—C14—H14B109.5
C3—N1—H1A120.0H14A—C14—H14B109.5
C3—N1—H1B120.0N5—C14—H14C109.5
H1A—N1—H1B120.0H14A—C14—H14C109.5
O2—C1—O1121.0 (5)H14B—C14—H14C109.5
O2—C1—C2123.7 (5)N2—C15—H15A109.5
O1—C1—C2115.2 (5)N2—C15—H15B109.5
C7—C2—C3118.9 (5)H15A—C15—H15B109.5
C7—C2—C1118.9 (5)N2—C15—H15C109.5
C3—C2—C1122.2 (5)H15A—C15—H15C109.5
N1—C3—C2122.4 (5)H15B—C15—H15C109.5
N1—C3—C4119.2 (5)C17—C16—H16A109.5
C2—C3—C4118.4 (5)C17—C16—H16B109.5
C5—C4—C3120.9 (5)H16A—C16—H16B109.5
C5—C4—H4119.5C17—C16—H16C109.5
C3—C4—H4119.5H16A—C16—H16C109.5
C4—C5—C6120.5 (5)H16B—C16—H16C109.5
C4—C5—H5119.8C18—C17—C23117.7 (5)
C6—C5—H5119.8C18—C17—C16121.9 (6)
C7—C6—C5119.0 (5)C23—C17—C16120.4 (5)
C7—C6—H6120.5C17—C18—C19121.3 (5)
C5—C6—H6120.5C17—C18—H18119.3
C6—C7—C2122.3 (5)C19—C18—H18119.3
C6—C7—H7118.8C18—C19—C20121.2 (5)
C2—C7—H7118.8C18—C19—H19119.4
C8—N2—C9126.4 (4)C20—C19—H19119.4
C8—N2—C15118.3 (4)C22—C20—C19117.9 (6)
C9—N2—C15115.4 (4)C22—C20—C21120.1 (6)
C9—N3—C10119.5 (4)C19—C20—C21122.0 (6)
C9—N3—C13119.9 (4)C20—C21—H21A109.5
C10—N3—C13120.6 (4)C20—C21—H21B109.5
C12—N4—C10102.2 (4)H21A—C21—H21B109.5
C12—N5—C11106.0 (4)C20—C21—H21C109.5
C12—N5—C14126.8 (4)H21A—C21—H21C109.5
C11—N5—C14127.3 (4)H21B—C21—H21C109.5
O3—C8—N2120.8 (5)C20—C22—C23121.2 (6)
O3—C8—C11127.5 (5)C20—C22—H22119.4
N2—C8—C11111.7 (5)C23—C22—H22119.4
O4—C9—N3122.6 (5)C22—C23—C17120.7 (5)
O4—C9—N2119.7 (5)C22—C23—H23119.7
N3—C9—N2117.7 (4)C17—C23—H23119.7
N4—C10—C11113.0 (4)C25—C24—H24A109.5
N4—C10—N3125.3 (5)C25—C24—H24B109.5
C11—C10—N3121.6 (5)H24A—C24—H24B109.5
C10—C11—N5104.7 (4)C25—C24—H24C109.5
C10—C11—C8123.1 (5)H24A—C24—H24C109.5
N5—C11—C8132.1 (5)H24B—C24—H24C109.5
N4—C12—N5114.1 (5)C27i—C25—C26116.2 (6)
N4—C12—H12123.0C27i—C25—C24121.8 (6)
N5—C12—H12123.0C26—C25—C24122.0 (7)
N3—C13—H13A109.5C27—C26—C25121.7 (6)
N3—C13—H13B109.5C27—C26—H26119.2
H13A—C13—H13B109.5C25—C26—H26119.2
N3—C13—H13C109.5C26—C27—C25i122.1 (6)
H13A—C13—H13C109.5C26—C27—H27118.9
H13B—C13—H13C109.5C25i—C27—H27118.9
N5—C14—H14A109.5
Symmetry code: (i) x, y+1, z+2.
(Monohydrate) top
Crystal data top
C8H10N4O2·C7H7NO2·H2OF(000) = 1472
Mr = 349.35Dx = 1.440 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 18126 reflections
a = 10.2641 (2) Åθ = 1.0–27.1°
b = 26.9469 (7) ŵ = 0.11 mm1
c = 11.9845 (3) ÅT = 180 K
β = 103.547 (2)°Block, colourless
V = 3222.52 (13) Å30.32 × 0.12 × 0.10 mm
Z = 8
Data collection top
Nonius Kappa CCD
diffractometer
3701 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.053
Thin slice ω and φ scansθmax = 27.1°, θmin = 3.6°
Absorption correction: multi-scan
SORTAV (Blessing, 1995)
h = 1313
Tmin = 0.877, Tmax = 0.994k = 3434
18826 measured reflectionsl = 1415
7046 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163H atoms treated by a mixture of independent and constrained refinement
S = 0.96 w = 1/[σ2(Fo2) + (0.083P)2]
where P = (Fo2 + 2Fc2)/3
7046 reflections(Δ/σ)max = 0.001
469 parametersΔρmax = 0.32 e Å3
6 restraintsΔρmin = 0.34 e Å3
Crystal data top
C8H10N4O2·C7H7NO2·H2OV = 3222.52 (13) Å3
Mr = 349.35Z = 8
Monoclinic, P21/cMo Kα radiation
a = 10.2641 (2) ŵ = 0.11 mm1
b = 26.9469 (7) ÅT = 180 K
c = 11.9845 (3) Å0.32 × 0.12 × 0.10 mm
β = 103.547 (2)°
Data collection top
Nonius Kappa CCD
diffractometer
7046 independent reflections
Absorption correction: multi-scan
SORTAV (Blessing, 1995)
3701 reflections with I > 2σ(I)
Tmin = 0.877, Tmax = 0.994Rint = 0.053
18826 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0566 restraints
wR(F2) = 0.163H atoms treated by a mixture of independent and constrained refinement
S = 0.96Δρmax = 0.32 e Å3
7046 reflectionsΔρmin = 0.34 e Å3
469 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
N20.7698 (2)0.11684 (8)0.56077 (16)0.0335 (5)
N30.79013 (19)0.20275 (8)0.60224 (17)0.0361 (5)
O30.65429 (18)0.15286 (8)0.67935 (15)0.0509 (5)
N40.99363 (19)0.16092 (8)0.40382 (17)0.0356 (5)
O40.92381 (18)0.25417 (7)0.52473 (16)0.0490 (5)
N50.90393 (19)0.08753 (8)0.43110 (16)0.0343 (5)
C80.8796 (2)0.21211 (10)0.5332 (2)0.0341 (6)
C90.9111 (2)0.16884 (10)0.47873 (19)0.0316 (6)
C100.8587 (2)0.12326 (9)0.49244 (19)0.0303 (6)
C110.7334 (3)0.15690 (11)0.6184 (2)0.0382 (6)
C120.9856 (3)0.11239 (10)0.3790 (2)0.0388 (6)
H121.03330.09710.32920.047*
C130.7143 (3)0.06802 (10)0.5739 (2)0.0438 (7)
H13A0.69640.05050.50030.066*
H13B0.63070.07180.59910.066*
H13C0.77870.04890.63130.066*
C140.7469 (3)0.24439 (12)0.6636 (2)0.0521 (8)
H14A0.75710.23550.74450.078*
H14B0.65270.25200.62920.078*
H14C0.80210.27360.65820.078*
C151.0761 (3)0.19725 (11)0.3628 (2)0.0480 (7)
H15A1.10950.18300.29970.072*
H15B1.15210.20650.42560.072*
H15C1.02250.22680.33560.072*
C10.5006 (2)0.19424 (10)0.3836 (2)0.0336 (6)
N10.6345 (2)0.13733 (8)0.23640 (17)0.0415 (6)
H1A0.65010.16940.24560.050*
H1B0.67530.11990.19270.050*
O10.42287 (16)0.21415 (7)0.44619 (15)0.0469 (5)
H1X0.43980.24460.45520.056*
C20.4787 (2)0.14057 (9)0.3609 (2)0.0321 (6)
O20.58178 (17)0.21937 (7)0.34845 (16)0.0479 (5)
C30.5472 (2)0.11481 (10)0.2899 (2)0.0343 (6)
C40.5227 (3)0.06348 (10)0.2733 (2)0.0410 (7)
H40.56780.04540.22560.049*
C50.4351 (3)0.03935 (11)0.3247 (2)0.0473 (7)
H50.42100.00470.31280.057*
C60.3662 (3)0.06472 (10)0.3943 (2)0.0473 (7)
H60.30470.04780.42910.057*
C70.3889 (3)0.11467 (10)0.4116 (2)0.0404 (7)
H70.34250.13220.45930.049*
N70.28462 (19)0.16013 (7)1.07163 (15)0.0307 (5)
N80.23375 (18)0.07438 (8)1.05519 (16)0.0328 (5)
O80.12952 (17)0.12623 (7)1.15614 (15)0.0442 (5)
N90.49279 (19)0.11223 (8)0.90411 (16)0.0334 (5)
O90.33692 (17)0.02074 (6)0.95356 (15)0.0414 (5)
N100.45111 (19)0.18681 (8)0.96878 (16)0.0328 (5)
C230.3253 (2)0.06300 (9)0.98755 (19)0.0302 (6)
C240.3967 (2)0.10563 (9)0.96707 (19)0.0286 (5)
C250.3755 (2)0.15199 (9)1.00521 (19)0.0287 (5)
C260.2111 (2)0.12083 (10)1.0980 (2)0.0340 (6)
C270.5204 (2)0.16079 (10)0.9076 (2)0.0384 (6)
H270.58310.17530.87020.046*
C280.2631 (3)0.20962 (10)1.1138 (2)0.0419 (7)
H28A0.16840.21871.08700.063*
H28B0.31870.23371.08480.063*
H28C0.28770.20971.19790.063*
C290.1527 (3)0.03415 (11)1.0850 (2)0.0448 (7)
H29A0.05750.04251.05890.067*
H29B0.17510.02951.16840.067*
H29C0.17110.00341.04760.067*
C300.5485 (3)0.07380 (10)0.8426 (2)0.0466 (7)
H30A0.62370.08760.81510.070*
H30B0.47910.06220.77710.070*
H30C0.58010.04590.89450.070*
N60.0428 (2)0.08593 (9)0.82817 (17)0.0453 (6)
H6A0.08250.10370.87220.054*
H6B0.06230.05430.81670.054*
O60.15779 (17)0.00931 (7)0.60934 (14)0.0496 (5)
H6X0.14470.02150.60400.059*
O70.01721 (18)0.00256 (7)0.72414 (15)0.0474 (5)
C160.0924 (2)0.02812 (10)0.6820 (2)0.0359 (6)
C170.1171 (2)0.08127 (10)0.7069 (2)0.0336 (6)
C180.0486 (2)0.10739 (10)0.7781 (2)0.0334 (6)
C190.0782 (3)0.15828 (10)0.7979 (2)0.0378 (6)
H190.03220.17670.84440.045*
C200.1710 (3)0.18138 (10)0.7520 (2)0.0424 (7)
H200.18970.21550.76770.051*
C210.2395 (3)0.15584 (10)0.6821 (2)0.0422 (7)
H210.30420.17230.65030.051*
C220.2116 (2)0.10634 (10)0.6598 (2)0.0378 (6)
H220.25720.08880.61160.045*
O1W0.8371 (2)0.35517 (9)0.4826 (2)0.0694 (6)
H11W0.876 (3)0.3218 (7)0.509 (2)0.083*
H12W0.843 (3)0.3729 (10)0.5596 (19)0.083*
O2W0.1984 (2)0.06684 (8)0.87423 (19)0.0680 (6)
H21W0.253 (2)0.0341 (9)0.913 (2)0.082*
H22W0.118 (2)0.0482 (10)0.814 (2)0.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0393 (12)0.0279 (13)0.0354 (11)0.0009 (10)0.0132 (10)0.0011 (9)
N30.0388 (11)0.0320 (13)0.0406 (12)0.0043 (10)0.0151 (10)0.0038 (10)
O30.0579 (11)0.0509 (14)0.0539 (11)0.0015 (10)0.0336 (10)0.0018 (10)
N40.0384 (11)0.0297 (13)0.0417 (12)0.0042 (10)0.0153 (10)0.0037 (10)
O40.0537 (11)0.0291 (12)0.0711 (13)0.0040 (9)0.0284 (10)0.0080 (10)
N50.0378 (11)0.0316 (13)0.0352 (11)0.0001 (10)0.0118 (10)0.0018 (10)
C80.0335 (13)0.0264 (16)0.0425 (15)0.0022 (12)0.0092 (12)0.0002 (12)
C90.0315 (13)0.0304 (15)0.0348 (13)0.0005 (11)0.0117 (11)0.0018 (11)
C100.0329 (13)0.0264 (14)0.0315 (13)0.0021 (11)0.0072 (11)0.0017 (11)
C110.0396 (14)0.0374 (17)0.0366 (14)0.0080 (13)0.0066 (13)0.0067 (12)
C120.0417 (15)0.0339 (16)0.0432 (15)0.0006 (13)0.0148 (13)0.0085 (13)
C130.0536 (16)0.0307 (16)0.0506 (16)0.0069 (14)0.0190 (13)0.0046 (13)
C140.0550 (17)0.046 (2)0.0606 (18)0.0061 (15)0.0233 (15)0.0154 (15)
C150.0491 (16)0.0411 (18)0.0627 (18)0.0086 (14)0.0310 (14)0.0039 (14)
C10.0353 (13)0.0282 (15)0.0373 (14)0.0037 (12)0.0085 (12)0.0002 (11)
N10.0469 (13)0.0327 (13)0.0488 (13)0.0006 (11)0.0190 (11)0.0008 (10)
O10.0538 (11)0.0266 (11)0.0684 (12)0.0028 (9)0.0308 (10)0.0077 (9)
C20.0317 (13)0.0265 (14)0.0370 (14)0.0014 (11)0.0059 (11)0.0020 (11)
O20.0513 (11)0.0312 (11)0.0688 (12)0.0077 (10)0.0295 (9)0.0008 (9)
C30.0361 (14)0.0313 (15)0.0337 (14)0.0025 (12)0.0047 (12)0.0030 (11)
C40.0495 (16)0.0317 (17)0.0417 (15)0.0026 (13)0.0106 (13)0.0032 (12)
C50.0617 (18)0.0265 (16)0.0561 (17)0.0060 (14)0.0184 (15)0.0058 (13)
C60.0549 (17)0.0310 (17)0.0614 (18)0.0059 (14)0.0244 (15)0.0017 (14)
C70.0445 (15)0.0276 (16)0.0531 (16)0.0015 (13)0.0194 (13)0.0007 (12)
N70.0360 (11)0.0236 (12)0.0360 (11)0.0007 (10)0.0153 (9)0.0014 (9)
N80.0325 (11)0.0280 (12)0.0394 (12)0.0045 (10)0.0117 (9)0.0006 (9)
O80.0453 (10)0.0447 (13)0.0514 (11)0.0004 (9)0.0290 (9)0.0012 (9)
N90.0366 (11)0.0247 (12)0.0427 (12)0.0037 (10)0.0171 (10)0.0024 (9)
O90.0502 (11)0.0227 (10)0.0557 (11)0.0041 (9)0.0216 (9)0.0038 (8)
N100.0335 (11)0.0264 (12)0.0417 (12)0.0026 (10)0.0152 (10)0.0034 (9)
C230.0325 (13)0.0276 (15)0.0305 (13)0.0009 (11)0.0073 (11)0.0014 (11)
C240.0314 (12)0.0253 (14)0.0307 (12)0.0016 (11)0.0107 (11)0.0015 (10)
C250.0289 (12)0.0246 (14)0.0332 (13)0.0004 (11)0.0081 (11)0.0031 (11)
C260.0319 (13)0.0382 (17)0.0326 (14)0.0008 (12)0.0085 (12)0.0012 (12)
C270.0377 (14)0.0302 (16)0.0498 (16)0.0006 (13)0.0152 (12)0.0085 (13)
C280.0514 (15)0.0282 (16)0.0504 (16)0.0061 (13)0.0209 (13)0.0038 (12)
C290.0449 (15)0.0376 (18)0.0559 (17)0.0124 (13)0.0202 (13)0.0000 (13)
C300.0584 (17)0.0344 (17)0.0588 (17)0.0098 (14)0.0372 (14)0.0034 (13)
N60.0542 (14)0.0351 (14)0.0511 (13)0.0060 (12)0.0215 (11)0.0062 (11)
O60.0657 (12)0.0275 (11)0.0644 (12)0.0004 (10)0.0335 (10)0.0047 (9)
O70.0543 (11)0.0325 (12)0.0604 (12)0.0064 (10)0.0238 (10)0.0021 (10)
C160.0402 (14)0.0285 (15)0.0392 (14)0.0025 (13)0.0098 (12)0.0003 (12)
C170.0386 (14)0.0264 (15)0.0333 (13)0.0008 (12)0.0031 (12)0.0034 (11)
C180.0361 (13)0.0306 (15)0.0313 (13)0.0001 (12)0.0039 (11)0.0035 (11)
C190.0476 (15)0.0271 (15)0.0367 (14)0.0049 (13)0.0063 (12)0.0016 (12)
C200.0577 (17)0.0255 (15)0.0423 (15)0.0007 (14)0.0084 (14)0.0020 (12)
C210.0535 (16)0.0319 (17)0.0441 (15)0.0042 (14)0.0174 (13)0.0043 (13)
C220.0446 (15)0.0304 (16)0.0390 (14)0.0023 (13)0.0109 (12)0.0035 (12)
O1W0.0700 (14)0.0482 (15)0.0979 (17)0.0035 (12)0.0354 (13)0.0062 (13)
O2W0.0757 (15)0.0530 (16)0.0779 (15)0.0095 (13)0.0231 (12)0.0057 (12)
Geometric parameters (Å, º) top
N2—C101.372 (3)N7—C281.461 (3)
N2—C111.379 (3)N8—C261.393 (3)
N2—C131.457 (3)N8—C231.411 (3)
N3—C81.395 (3)N8—C291.461 (3)
N3—C111.398 (3)O8—C261.217 (3)
N3—C141.466 (3)N9—C271.337 (3)
O3—C111.218 (3)N9—C241.387 (3)
N4—C121.339 (3)N9—C301.463 (3)
N4—C91.387 (3)O9—C231.225 (3)
N4—C151.453 (3)N10—C271.334 (3)
O4—C81.234 (3)N10—C251.353 (3)
N5—C121.336 (3)C23—C241.414 (3)
N5—C101.358 (3)C24—C251.365 (3)
C8—C91.411 (3)C27—H270.9500
C9—C101.366 (3)C28—H28A0.9800
C12—H120.9500C28—H28B0.9800
C13—H13A0.9800C28—H28C0.9800
C13—H13B0.9800C29—H29A0.9800
C13—H13C0.9800C29—H29B0.9800
C14—H14A0.9800C29—H29C0.9800
C14—H14B0.9800C30—H30A0.9800
C14—H14C0.9800C30—H30B0.9800
C15—H15A0.9800C30—H30C0.9800
C15—H15B0.9800N6—C181.356 (3)
C15—H15C0.9800N6—H6A0.8800
C1—O21.223 (3)N6—H6B0.8800
C1—O11.329 (3)O6—C161.319 (3)
C1—C21.479 (3)O6—H6X0.8400
N1—C31.360 (3)O7—C161.227 (3)
N1—H1A0.8800C16—C171.473 (3)
N1—H1B0.8800C17—C221.405 (3)
O1—H1X0.8400C17—C181.413 (3)
C2—C71.404 (3)C18—C191.413 (4)
C2—C31.407 (3)C19—C201.358 (3)
C3—C41.411 (4)C19—H190.9500
C4—C51.368 (4)C20—C211.394 (4)
C4—H40.9500C20—H200.9500
C5—C61.392 (4)C21—C221.377 (4)
C5—H50.9500C21—H210.9500
C6—C71.374 (4)C22—H220.9500
C6—H60.9500O1W—H11W1.005 (17)
C7—H70.9500O1W—H12W1.028 (17)
N7—C251.379 (3)O2W—H21W1.090 (17)
N7—C261.380 (3)O2W—H22W1.087 (17)
C10—N2—C11119.7 (2)C25—N7—C28121.5 (2)
C10—N2—C13120.7 (2)C26—N7—C28119.1 (2)
C11—N2—C13119.6 (2)C26—N8—C23126.7 (2)
C8—N3—C11126.5 (2)C26—N8—C29115.0 (2)
C8—N3—C14118.5 (2)C23—N8—C29118.2 (2)
C11—N3—C14115.0 (2)C27—N9—C24106.4 (2)
C12—N4—C9106.2 (2)C27—N9—C30127.1 (2)
C12—N4—C15126.4 (2)C24—N9—C30126.5 (2)
C9—N4—C15127.4 (2)C27—N10—C25103.5 (2)
C12—N5—C10103.2 (2)O9—C23—N8121.5 (2)
O4—C8—N3121.4 (2)O9—C23—C24127.1 (2)
O4—C8—C9126.3 (2)N8—C23—C24111.4 (2)
N3—C8—C9112.3 (2)C25—C24—N9104.7 (2)
C10—C9—N4104.9 (2)C25—C24—C23123.8 (2)
C10—C9—C8123.2 (2)N9—C24—C23131.5 (2)
N4—C9—C8131.9 (2)N10—C25—C24112.2 (2)
N5—C10—C9112.2 (2)N10—C25—N7126.4 (2)
N5—C10—N2126.4 (2)C24—C25—N7121.4 (2)
C9—C10—N2121.4 (2)O8—C26—N7121.7 (2)
O3—C11—N2121.8 (3)O8—C26—N8121.0 (2)
O3—C11—N3121.3 (3)N7—C26—N8117.2 (2)
N2—C11—N3116.9 (2)N10—C27—N9113.2 (2)
N5—C12—N4113.5 (2)N10—C27—H27123.4
N5—C12—H12123.3N9—C27—H27123.4
N4—C12—H12123.3N7—C28—H28A109.5
N2—C13—H13A109.5N7—C28—H28B109.5
N2—C13—H13B109.5H28A—C28—H28B109.5
H13A—C13—H13B109.5N7—C28—H28C109.5
N2—C13—H13C109.5H28A—C28—H28C109.5
H13A—C13—H13C109.5H28B—C28—H28C109.5
H13B—C13—H13C109.5N8—C29—H29A109.5
N3—C14—H14A109.5N8—C29—H29B109.5
N3—C14—H14B109.5H29A—C29—H29B109.5
H14A—C14—H14B109.5N8—C29—H29C109.5
N3—C14—H14C109.5H29A—C29—H29C109.5
H14A—C14—H14C109.5H29B—C29—H29C109.5
H14B—C14—H14C109.5N9—C30—H30A109.5
N4—C15—H15A109.5N9—C30—H30B109.5
N4—C15—H15B109.5H30A—C30—H30B109.5
H15A—C15—H15B109.5N9—C30—H30C109.5
N4—C15—H15C109.5H30A—C30—H30C109.5
H15A—C15—H15C109.5H30B—C30—H30C109.5
H15B—C15—H15C109.5C18—N6—H6A120.0
O2—C1—O1121.2 (2)C18—N6—H6B120.0
O2—C1—C2124.4 (2)H6A—N6—H6B120.0
O1—C1—C2114.4 (2)C16—O6—H6X109.5
C3—N1—H1A120.0O7—C16—O6121.5 (2)
C3—N1—H1B120.0O7—C16—C17123.9 (2)
H1A—N1—H1B120.0O6—C16—C17114.7 (2)
C1—O1—H1X109.5C22—C17—C18119.4 (2)
C7—C2—C3119.3 (2)C22—C17—C16119.2 (2)
C7—C2—C1119.5 (2)C18—C17—C16121.4 (2)
C3—C2—C1121.2 (2)N6—C18—C19118.9 (2)
N1—C3—C2122.8 (2)N6—C18—C17123.2 (2)
N1—C3—C4119.1 (2)C19—C18—C17117.9 (2)
C2—C3—C4118.1 (2)C20—C19—C18121.3 (3)
C5—C4—C3121.1 (3)C20—C19—H19119.3
C5—C4—H4119.5C18—C19—H19119.3
C3—C4—H4119.5C19—C20—C21121.2 (3)
C4—C5—C6121.1 (3)C19—C20—H20119.4
C4—C5—H5119.5C21—C20—H20119.4
C6—C5—H5119.5C22—C21—C20118.9 (3)
C7—C6—C5118.7 (3)C22—C21—H21120.5
C7—C6—H6120.7C20—C21—H21120.5
C5—C6—H6120.7C21—C22—C17121.3 (3)
C6—C7—C2121.8 (3)C21—C22—H22119.4
C6—C7—H7119.1C17—C22—H22119.4
C2—C7—H7119.1H11W—O1W—H12W101.5 (18)
C25—N7—C26119.4 (2)H21W—O2W—H22W98.4 (17)
(Theobromine_AA) top
Crystal data top
C7H8N4O2·C7H7NO2Z = 4
Mr = 317.31F(000) = 664
Monoclinic, P21/cDx = 1.437 (1) Mg m3
a = 6.5769 (10) ÅCu Kα radiation, λ = 1.5418 Å
b = 21.905 (3) ÅT = 293 K
c = 11.0496 (16) Åwhite
β = 112.912 (6)°flat sheet, 14 × 10 mm
V = 1466.3 (4) Å3
Data collection top
Panalytical X'pert Powder
diffractometer
Data collection mode: reflection
Radiation source: sealed X-ray tubeScan method: continuous
None monochromator2θmin = 4.993°, 2θmax = 60.004°, 2θstep = 0.033°
Specimen mounting: glass slide
Refinement top
Rp = 0.035166 parameters
Rwp = 0.040103 restraints
Rexp = 0.0110 constraints
RBragg = 0.023
χ2 = 13.853
1668 data pointsBackground function: Chebyshev polynomial
Profile function: pseudo-VoigtPreferred orientation correction: spherical harmonics
Crystal data top
C7H8N4O2·C7H7NO2β = 112.912 (6)°
Mr = 317.31V = 1466.3 (4) Å3
Monoclinic, P21/cZ = 4
a = 6.5769 (10) ÅCu Kα radiation, λ = 1.5418 Å
b = 21.905 (3) ÅT = 293 K
c = 11.0496 (16) Åflat sheet, 14 × 10 mm
Data collection top
Panalytical X'pert Powder
diffractometer
Scan method: continuous
Specimen mounting: glass slide2θmin = 4.993°, 2θmax = 60.004°, 2θstep = 0.033°
Data collection mode: reflection
Refinement top
Rp = 0.035χ2 = 13.853
Rwp = 0.0401668 data points
Rexp = 0.011166 parameters
RBragg = 0.023103 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.6170 (7)0.3272 (3)0.3697 (5)0.051
C20.4000 (9)0.3560 (3)0.3364 (6)0.051
C30.6527 (9)0.2854 (3)0.2811 (5)0.051
C40.7957 (8)0.3411 (3)0.4939 (5)0.051
O50.2473 (10)0.3385 (3)0.2187 (8)0.051
O60.3623 (15)0.3964 (4)0.4067 (9)0.051
C70.8560 (9)0.2592 (3)0.3074 (5)0.051
H80.516 (4)0.2745 (12)0.189 (2)0.061
N90.7635 (9)0.3817 (3)0.5830 (5)0.051
C101.0068 (9)0.3124 (3)0.5186 (6)0.051
H110.099 (4)0.3577 (12)0.200 (2)0.061
C121.0319 (9)0.2714 (3)0.4303 (6)0.051
H130.878 (4)0.2288 (12)0.235 (2)0.061
H140.610 (4)0.3993 (10)0.560 (2)0.061
H150.881 (4)0.3887 (11)0.674 (3)0.061
H161.149 (4)0.3224 (10)0.609 (3)0.061
H171.195 (4)0.2509 (11)0.453 (2)0.061
C180.5522 (8)0.4630 (3)0.1725 (6)0.051
N190.7221 (8)0.4898 (3)0.2858 (6)0.051
C200.6570 (8)0.4192 (3)0.1190 (6)0.051
C210.3198 (9)0.4773 (3)0.1070 (6)0.051
C220.9160 (8)0.4633 (3)0.2889 (7)0.051
C230.6921 (7)0.5393 (2)0.3747 (5)0.051
N240.5388 (8)0.3851 (3)0.0004 (6)0.051
N250.8811 (11)0.4184 (4)0.1974 (8)0.051
O260.2208 (14)0.5190 (5)0.1423 (10)0.051
N270.2135 (9)0.4406 (3)0.0069 (6)0.051
H281.084 (4)0.4777 (13)0.353 (2)0.061
H290.746 (3)0.5235 (13)0.479 (3)0.061
H300.514 (4)0.5525 (11)0.340 (2)0.061
H310.786 (4)0.5807 (11)0.372 (3)0.061
C320.3019 (9)0.3960 (3)0.0624 (6)0.051
C330.6574 (7)0.3404 (2)0.0580 (5)0.051
H340.047 (4)0.4511 (10)0.064 (3)0.061
O350.1750 (17)0.3691 (4)0.1635 (10)0.051
H360.821 (4)0.3287 (11)0.016 (2)0.061
H370.681 (4)0.3586 (11)0.145 (2)0.061
H380.562 (4)0.2987 (11)0.087 (3)0.061
Geometric parameters (Å, º) top
C1—C21.471 (8)N19—C221.390 (9)
C1—C31.425 (9)N19—C231.527 (9)
C1—C41.450 (6)C20—N241.449 (8)
C2—O51.353 (8)C20—N251.389 (8)
C2—O61.264 (13)C21—O261.268 (13)
C3—C71.378 (8)C21—N271.426 (9)
C3—H81.09 (2)C22—N251.364 (11)
C4—N91.403 (9)C22—H281.10 (2)
C4—C101.449 (8)C23—H291.12 (3)
O5—H111.00 (3)C23—H301.12 (2)
C7—C121.425 (7)C23—H311.10 (3)
C7—H131.09 (3)N24—C321.457 (8)
N9—H141.02 (3)N24—C331.537 (9)
N9—H151.01 (2)N27—C321.396 (10)
C10—C121.383 (10)N27—H341.05 (2)
C10—H161.09 (2)C32—O351.251 (10)
C12—H171.10 (3)C33—H361.10 (2)
C18—N191.439 (7)C33—H371.11 (3)
C18—C201.437 (10)C33—H381.08 (2)
C18—C211.448 (7)
C2—C1—C3120.5 (4)C18—C20—N24123.0 (5)
C2—C1—C4119.8 (5)C18—C20—N25108.3 (6)
C3—C1—C4119.7 (5)N24—C20—N25128.6 (7)
C1—C2—O5113.8 (6)C18—C21—O26124.8 (6)
C1—C2—O6123.4 (5)C18—C21—N27112.3 (6)
O5—C2—O6122.7 (7)O26—C21—N27122.9 (6)
C1—C3—C7121.9 (4)N19—C22—N25113.3 (5)
C1—C3—H8119 (2)N19—C22—H28125 (2)
C7—C3—H8119 (2)N25—C22—H28121 (2)
C1—C4—N9120.6 (5)N19—C23—H29112 (2)
C1—C4—C10116.8 (5)N19—C23—H30110 (1)
N9—C4—C10122.5 (4)N19—C23—H31111 (2)
C2—O5—H11111 (2)H29—C23—H30108 (2)
C3—C7—C12118.9 (6)H29—C23—H31109 (2)
C3—C7—H13119 (2)H30—C23—H31108 (2)
C12—C7—H13121 (1)C20—N24—C32116.1 (6)
C4—N9—H14117 (1)C20—N24—C33121.8 (4)
C4—N9—H15122 (2)C32—N24—C33122.1 (5)
H14—N9—H15120 (2)C20—N25—C22106.5 (7)
C4—C10—C12121.2 (5)C21—N27—C32129.6 (5)
C4—C10—H16120 (2)C21—N27—H34116 (2)
C12—C10—H16119 (2)C32—N27—H34114 (2)
C7—C12—C10121.3 (5)N24—C32—N27117.4 (5)
C7—C12—H17120 (1)N24—C32—O35124.3 (8)
C10—C12—H17119 (1)N27—C32—O35118.4 (7)
N19—C18—C20107.3 (5)N24—C33—H36110 (2)
N19—C18—C21131.1 (6)N24—C33—H37113 (1)
C20—C18—C21121.4 (5)N24—C33—H38109 (2)
C18—N19—C22104.2 (6)H36—C33—H37108 (2)
C18—N19—C23126.8 (5)H36—C33—H38108 (2)
C22—N19—C23129.0 (4)H37—C33—H38108 (2)

Experimental details

(Form1)(Form2)(Chlorobenzene_Hemisolvate)(Bromobenzene_Hemisolvate)
Crystal data
Chemical formulaC8H10N4O2·C7H7NO2C8H10N4O2·C7H7NO22(C8H10N4O2)·2(C7H7NO2)·C6H5Cl2(C8H10N4O2)·2(C7H7NO2)·C6H5Br
Mr331.33331.33775.22819.67
Crystal system, space groupTriclinic, P1Orthorhombic, Pna21Triclinic, P1Triclinic, P1
Temperature (K)293293180293
a, b, c (Å)8.4853 (2), 13.4240 (3), 14.8856 (4)14.53798 (14), 11.07930 (8), 10.02456 (7)12.4390 (2), 13.1409 (2), 13.2251 (3)12.569 (3), 13.409 (3), 13.269 (3)
α, β, γ (°)111.7249 (16), 92.8464 (15), 93.5278 (9)90, 90, 9069.439 (1), 80.418 (1), 63.557 (1)68.991 (4), 80.215 (5), 64.007 (4)
V3)1567.35 (7)1614.66 (2)1812.17 (6)1876.3 (8)
Z4422
Radiation typeSynchrotron, λ = 1.033787 ÅSynchrotron, λ = 1.033787 ÅMo KαCu Kα, λ = 1.5418 Å
µ (mm1)??0.17
Specimen shape, size (mm)Cylinder, ? × ? × ?Cylinder, ? × ? × ?0.42 × 0.14 × 0.12Flat sheet, 14 × 10
Data collection
DiffractometerDiamond Light Source beamline I11
diffractometer
Diamond Light Source beamline I11
diffractometer
Nonius Kappa CCD
diffractometer
Panalytical X'pert Powder
diffractometer
Specimen mountingGlass capillaryGlass capillaryGlass slide
Data collection modeTransmissionTransmissionReflection
Data collection methodContinuousContinuousThin slice ω and φ scansContinuous
Absorption correctionMulti-scan
SORTAV (Blessing, 1995)
Tmin, Tmax0.828, 0.994
No. of measured, independent and
observed reflections
27836, 10352, 4748
Rint0.048
θ values (°)2θmin = 3.000 2θmax = 40.000 2θstep = 0.0042θmin = 3.000 2θmax = 40.000 2θstep = 0.004θmax = 30.1, θmin = 3.72θmin = 5.005 2θmax = 49.992 2θstep = 0.017
Distance from source to specimen (mm)0.705
Refinement
R factors and goodness of fitRp = 0.014, Rwp = 0.019, Rexp = 0.010, RBragg = 0.003, χ2 = 3.587Rp = 0.010, Rwp = 0.013, Rexp = 0.010, RBragg = 0.002, χ2 = 1.680R[F2 > 2σ(F2)] = 0.044, wR(F2) = 0.111, S = 0.89Rp = 0.046, Rwp = 0.059, Rexp = 0.040, RBragg = 0.016, χ2 = 2.161
No. of reflections/data points92519251103522693
No. of parameters310158502323
No. of restraints2241120255
H-atom treatment??H-atom parameters constrained?
Δρmax, Δρmin (e Å3)0.42, 0.36


(Toluene_Hemisolvate)(Toluene_Monosolvate)(o_Xylene_Monosolvate)(p_Xylene_Sesquisolvate)
Crystal data
Chemical formula2(C8H10N4O2)·2(C7H7NO2)·C7H8C8H10N4O2·C7H7NO2·C7H8C8H10N4O2·C7H7NO2·C8H10C8H10N4O2·C7H7NO2·1.5(C8H10)
Mr754.80423.47437.50490.58
Crystal system, space groupTriclinic, P1Triclinic, P1Monoclinic, P21/nTriclinic, P1
Temperature (K)293180180180
a, b, c (Å)12.475 (9), 13.488 (9), 13.316 (9)6.7113 (3), 13.5803 (6), 23.579 (2)13.8492 (3), 6.7890 (2), 23.3960 (7)6.8474 (8), 13.431 (2), 14.440 (3)
α, β, γ (°)68.318 (11), 79.948 (16), 64.124 (11)87.100 (2), 88.572 (2), 86.065 (2)90, 92.260 (1), 9077.009 (3), 86.596 (4), 88.687 (8)
V3)1873 (2)2140.7 (2)2198.0 (1)1291.7 (4)
Z2442
Radiation typeCu Kα, λ = 1.5418 ÅMo KαMo KαMo Kα
µ (mm1)0.090.090.09
Specimen shape, size (mm)Flat sheet, 14 × 100.46 × 0.12 × 0.050.46 × 0.16 × 0.100.46 × 0.02 × 0.02
Data collection
DiffractometerPanalytical X'pert Powder
diffractometer
Nonius Kappa CCD
diffractometer
Nonius Kappa CCD
diffractometer
Nonius Kappa CCD
diffractometer
Specimen mountingGlass slide
Data collection modeReflection
Data collection methodContinuousThin slice ω and φ scansThin slice ω and φ scansThin slice ω and φ scans
Absorption correctionMulti-scan
SORTAV (Blessing, 1995)
Multi-scan
SORTAV (Blessing, 1995)
Multi-scan
SORTAV (Blessing, 1995)
Tmin, Tmax0.740, 1.0000.851, 0.9980.562, 0.998
No. of measured, independent and
observed reflections
11209, 5163, 3560 13598, 4909, 2651 8643, 3298, 1845
Rint0.0820.0360.112
θ values (°)2θmin = 5.000 2θmax = 39.969 2θstep = 0.017θmax = 22.4, θmin = 3.5θmax = 27.5, θmin = 3.7θmax = 22.6, θmin = 3.6
Distance from source to specimen (mm)0.5360.6490.541
Refinement
R factors and goodness of fitRp = 0.050, Rwp = 0.067, Rexp = 0.060, RBragg = 0.007, χ2 = 1.219R[F2 > 2σ(F2)] = 0.133, wR(F2) = 0.360, S = 1.36R[F2 > 2σ(F2)] = 0.127, wR(F2) = 0.436, S = 1.55R[F2 > 2σ(F2)] = 0.086, wR(F2) = 0.226, S = 0.97
No. of reflections/data points2058516349093298
No. of parameters337543236331
No. of restraints264000
H-atom treatment?H-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.89, 0.441.35, 0.600.32, 0.26


(Monohydrate)(Theobromine_AA)
Crystal data
Chemical formulaC8H10N4O2·C7H7NO2·H2OC7H8N4O2·C7H7NO2
Mr349.35317.31
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/c
Temperature (K)180293
a, b, c (Å)10.2641 (2), 26.9469 (7), 11.9845 (3)6.5769 (10), 21.905 (3), 11.0496 (16)
α, β, γ (°)90, 103.547 (2), 9090, 112.912 (6), 90
V3)3222.52 (13)1466.3 (4)
Z84
Radiation typeMo KαCu Kα, λ = 1.5418 Å
µ (mm1)0.11
Specimen shape, size (mm)0.32 × 0.12 × 0.10Flat sheet, 14 × 10
Data collection
DiffractometerNonius Kappa CCD
diffractometer
Panalytical X'pert Powder
diffractometer
Specimen mountingGlass slide
Data collection modeReflection
Data collection methodThin slice ω and φ scansContinuous
Absorption correctionMulti-scan
SORTAV (Blessing, 1995)
Tmin, Tmax0.877, 0.994
No. of measured, independent and
observed reflections
18826, 7046, 3701
Rint0.053
θ values (°)θmax = 27.1, θmin = 3.62θmin = 4.993 2θmax = 60.004 2θstep = 0.033
Distance from source to specimen (mm)0.641
Refinement
R factors and goodness of fitR[F2 > 2σ(F2)] = 0.056, wR(F2) = 0.163, S = 0.96Rp = 0.035, Rwp = 0.040, Rexp = 0.011, RBragg = 0.023, χ2 = 13.853
No. of reflections/data points70461668
No. of parameters469166
No. of restraints6103
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement?
Δρmax, Δρmin (e Å3)0.32, 0.34

Computer programs: X'Pert Data Collector (Panalytical, 2010), Collect (Nonius, 1998), DASH 3.3 (David et al., 2006) and DICVOL 06 (Boultif & Louer, 2004), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997), TOPAS Academic (Coelho, 2007), SIR92 (Altomare et al., 1994), TOPAS Academic, SHELXL97 (Sheldrick, 2008), SHELXL97.

 

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