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In the title four compounds, C13H11N·C7H4N2O6, (I), C15H15N·C7H4N2O6, (II), C16H17N·C7H4N2O6, (III), and C16H17N·C7H4N2O6, (IV), the donor and acceptor mol­ecules are stacked alternately to form one-dimensional columns. In (I), the N-methyl group of the donor is nearly eclipsed with respect to one of the nitro groups of the neighboring acceptor in a column, whereas the N-iso­propyl, N-butyl and N-iso­butyl groups are in anti positions with respect to one of the nitro groups of the neighboring acceptor in compounds (II)-(IV).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010000384X/qa0229sup1.cif
Contains datablocks dnba, I, II, III, IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010000384X/qa0229Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010000384X/qa0229IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010000384X/qa0229IIIsup4.hkl
Contains datablock III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010000384X/qa0229IVsup5.hkl
Contains datablock IV

CCDC references: 144701; 144702; 144703; 144704

Comment top

Crystals of (I) underwent photoredox reactions initiated by the excited nitro group, leading to α-oxidation of the N-alkyl groups. Complexes (III) and (IV) were less photoreactive than (I), and no reaction was observed for (II) (Ito et al., 1998).

In (I), the N-methyl group of the donor is nearly eclipsed to one of the nitro groups of the neighboring acceptor in a column, whereas the N-isopropyl, N-butyl and N-isobutyl groups are in anti positions with respect to one of the nitro groups of the neighboring acceptor in (II)-(IV).

Experimental top

Equimolar mixtures of N-alkylcarbazoles and 3,5-dinitrobenzoic acid were recrystallized from ethylacetate [for (I)], acetonitrile [for (II)–(III)] and acetone [for (IV)].

Refinement top

In compounds (I)–(IV), the 3,5-dinitrobenzoic acid molecules form a dimeric structure with cyclic hydrogen bonds. The acid proton has two possible positions with site-occupation factors of 50%. They were located from difference syntheses and refined isotropically. The O—H bond lengths are 0.73 (5)–0.88 (5) Å for (I), 0.78 (4)–0.82 (4) Å for (II), 0.64 (7)–1.01 (8) Å for (III) and 0.80 (6)–0.90 (8) Å for (IV). The other H-atom positional parameters were calculated geometrically and fixed with Uiso(H) = 1.2Ueq(parent atom).

Computing details top

For all compounds, data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: TEXSAN.

(I) top
Crystal data top
C13H11N·C7H4N2O6Z = 2
Mr = 393.36Dx = 1.446 Mg m3
Triclinic, P1Mo Kα radiation, λ = 0.71073 Å
a = 8.414 (1) ÅCell parameters from 25 reflections
b = 15.763 (2) Åθ = 14.8–15.0°
c = 6.991 (1) ŵ = 0.11 mm1
α = 91.82 (1)°T = 298 K
β = 99.91 (1)°Plate-like, orange
γ = 81.59 (1)°0.6 × 0.4 × 0.1 mm
V = 903.6 (2) Å3
Data collection top
Rigaku AFC-7R
diffractometer
θmax = 27.5°, θmin = 2.5°
θ–2θ scansh = 611
5045 measured reflectionsk = 2020
4128 independent reflectionsl = 99
2977 reflections with I > 2σ(I)3 standard reflections every 150 reflections
Rint = 0.005 intensity decay: none
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.044 w = 1/[σ2(Fo2) + (0.0715P)2 + 0.1508P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.147(Δ/σ)max = 0.001
S = 1.08Δρmax = 0.29 e Å3
4128 reflectionsΔρmin = 0.18 e Å3
270 parameters
Crystal data top
C13H11N·C7H4N2O6γ = 81.59 (1)°
Mr = 393.36V = 903.6 (2) Å3
Triclinic, P1Z = 2
a = 8.414 (1) ÅMo Kα radiation
b = 15.763 (2) ŵ = 0.11 mm1
c = 6.991 (1) ÅT = 298 K
α = 91.82 (1)°0.6 × 0.4 × 0.1 mm
β = 99.91 (1)°
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.005
5045 measured reflections3 standard reflections every 150 reflections
4128 independent reflections intensity decay: none
2977 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.044270 parameters
wR(F2) = 0.147H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.29 e Å3
4128 reflectionsΔρmin = 0.18 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.3140 (2)0.54272 (9)0.3736 (2)0.0704 (4)
O20.5349 (2)0.60566 (9)0.4766 (2)0.0710 (4)
O30.5136 (2)0.90733 (9)0.3326 (3)0.0834 (4)
O40.2827 (2)0.98623 (8)0.2436 (2)0.0822 (4)
O50.2015 (2)0.8524 (1)0.0584 (3)0.0887 (5)
O60.1918 (2)0.7173 (1)0.1029 (3)0.0908 (5)
N70.3667 (2)0.91724 (9)0.2839 (2)0.0596 (4)
N80.1284 (2)0.7826 (1)0.1113 (2)0.0635 (4)
N90.0120 (2)0.7610 (1)0.3163 (2)0.0611 (4)
C100.3879 (2)0.6073 (1)0.3959 (2)0.0541 (4)
C110.2954 (2)0.6914 (1)0.3249 (2)0.0490 (3)
C120.3735 (2)0.7634 (1)0.3352 (2)0.0493 (3)
C130.2834 (2)0.8407 (1)0.2723 (2)0.0487 (3)
C140.1193 (2)0.8496 (1)0.1991 (2)0.0507 (4)
C150.0465 (2)0.7761 (1)0.1896 (2)0.0498 (4)
C160.1307 (2)0.6974 (1)0.2502 (2)0.0506 (4)
C170.1087 (2)0.8131 (1)0.2849 (2)0.0524 (4)
C180.0977 (2)0.9014 (1)0.3100 (3)0.0688 (5)
C190.2411 (3)0.9368 (1)0.2651 (3)0.0806 (6)
C200.3892 (3)0.8878 (2)0.1986 (3)0.0795 (6)
C210.3991 (2)0.8016 (1)0.1730 (3)0.0665 (5)
C220.2587 (2)0.7628 (1)0.2161 (2)0.0512 (4)
C230.2270 (2)0.6762 (1)0.2055 (2)0.0559 (4)
C240.3221 (3)0.5983 (2)0.1466 (3)0.0809 (6)
C250.2462 (5)0.5255 (2)0.1544 (4)0.1098 (10)
C260.0810 (5)0.5293 (2)0.2188 (5)0.117 (1)
C270.0156 (3)0.6041 (2)0.2773 (4)0.0922 (7)
C280.0583 (2)0.6780 (1)0.2692 (3)0.0615 (4)
C290.1823 (2)0.7891 (2)0.3917 (3)0.0859 (7)
H10.351 (6)0.503 (3)0.424 (6)0.0696 (2)*0.50
H20.585 (6)0.557 (4)0.528 (7)0.0809 (2)*0.50
H120.48840.75930.38550.0561*
H140.05760.90470.15640.0574*
H160.07600.64780.24160.0572*
H180.00560.93690.35430.0788*
H190.23510.99870.28320.0934*
H200.48820.91510.16560.0920*
H210.50290.76650.12860.0738*
H240.43700.59380.10080.0910*
H250.30430.46990.11970.1273*
H260.03350.47630.21680.1279*
H270.13110.60520.32230.1088*
H29A0.24170.74020.40130.0986*
H29B0.19420.81310.51840.0986*
H29C0.22800.83090.30610.0986*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0756 (9)0.0456 (7)0.0824 (9)0.0108 (6)0.0118 (7)0.0115 (6)
O20.0556 (7)0.0527 (7)0.097 (1)0.0010 (6)0.0056 (7)0.0145 (7)
O30.0602 (8)0.0673 (9)0.122 (1)0.0201 (7)0.0028 (8)0.0144 (8)
O40.0793 (9)0.0466 (7)0.119 (1)0.0067 (6)0.0124 (8)0.0136 (7)
O50.0586 (8)0.0788 (10)0.114 (1)0.0117 (7)0.0080 (8)0.0024 (9)
O60.0591 (8)0.084 (1)0.124 (1)0.0210 (8)0.0084 (8)0.0036 (9)
N70.0620 (9)0.0497 (8)0.0684 (9)0.0112 (7)0.0106 (7)0.0065 (6)
N80.0502 (8)0.0675 (10)0.0681 (9)0.0030 (7)0.0021 (7)0.0017 (7)
N90.0372 (7)0.079 (1)0.0664 (9)0.0127 (7)0.0037 (6)0.0023 (7)
C100.0550 (9)0.0467 (8)0.0570 (9)0.0054 (7)0.0000 (7)0.0038 (7)
C110.0521 (8)0.0456 (8)0.0463 (8)0.0033 (6)0.0027 (6)0.0029 (6)
C120.0472 (8)0.0490 (8)0.0499 (8)0.0060 (6)0.0034 (6)0.0036 (6)
C130.0530 (8)0.0454 (8)0.0481 (8)0.0075 (6)0.0083 (6)0.0034 (6)
C140.0530 (9)0.0475 (8)0.0487 (8)0.0012 (7)0.0074 (6)0.0035 (6)
C150.0446 (8)0.0539 (9)0.0481 (8)0.0034 (7)0.0033 (6)0.0000 (6)
C160.0532 (8)0.0467 (8)0.0508 (8)0.0093 (7)0.0038 (7)0.0003 (6)
C170.0446 (8)0.0635 (10)0.0501 (8)0.0086 (7)0.0107 (6)0.0046 (7)
C180.072 (1)0.065 (1)0.069 (1)0.0006 (9)0.0174 (9)0.0016 (9)
C190.105 (2)0.067 (1)0.083 (1)0.035 (1)0.034 (1)0.015 (1)
C200.075 (1)0.097 (2)0.078 (1)0.043 (1)0.021 (1)0.020 (1)
C210.0454 (9)0.096 (1)0.061 (1)0.0208 (9)0.0100 (7)0.0121 (10)
C220.0409 (8)0.068 (1)0.0453 (8)0.0097 (7)0.0085 (6)0.0052 (7)
C230.0551 (9)0.064 (1)0.0483 (8)0.0067 (8)0.0105 (7)0.0004 (7)
C240.090 (1)0.082 (1)0.064 (1)0.010 (1)0.013 (1)0.008 (1)
C250.170 (3)0.064 (1)0.096 (2)0.002 (2)0.036 (2)0.016 (1)
C260.165 (3)0.080 (2)0.121 (2)0.050 (2)0.038 (2)0.001 (2)
C270.102 (2)0.094 (2)0.094 (2)0.052 (2)0.024 (1)0.010 (1)
C280.062 (1)0.072 (1)0.0558 (9)0.0236 (9)0.0142 (8)0.0049 (8)
C290.0434 (9)0.133 (2)0.077 (1)0.011 (1)0.0001 (9)0.004 (1)
Geometric parameters (Å, º) top
O1—C101.260 (2)C17—C221.406 (2)
O1—H10.73 (5)C18—C191.385 (3)
O2—C101.265 (2)C18—H180.970
O2—H20.88 (5)C19—C201.382 (3)
O3—N71.213 (2)C19—H190.980
O4—N71.220 (2)C20—C211.363 (3)
O5—N81.214 (2)C20—H200.982
O6—N81.222 (2)C21—C221.393 (3)
N7—C131.474 (2)C21—H210.970
N8—C151.469 (2)C22—C231.435 (3)
N9—C171.382 (2)C23—C241.395 (3)
N9—C281.379 (2)C23—C281.409 (2)
N9—C291.449 (2)C24—C251.388 (4)
C10—C111.489 (2)C24—H240.958
C11—C121.386 (2)C25—C261.379 (6)
C11—C161.385 (2)C25—H250.957
C12—C131.379 (2)C26—C271.362 (4)
C12—H120.964C26—H260.979
C13—C141.376 (2)C27—C281.394 (4)
C14—C151.381 (2)C27—H270.966
C14—H140.973C29—H29A0.972
C15—C161.376 (2)C29—H29B0.958
C16—H160.960C29—H29C0.959
C17—C181.397 (3)
C10—O1—H1120 (4)C19—C18—H18121.2
C10—O2—H2116 (3)C18—C19—C20122.2 (2)
O3—N7—O4124.5 (2)C18—C19—H19117.8
O3—N7—C13117.9 (1)C20—C19—H19120.1
O4—N7—C13117.6 (1)C19—C20—C21120.6 (2)
O5—N8—O6123.8 (2)C19—C20—H20120.1
O5—N8—C15118.2 (2)C21—C20—H20119.3
O6—N8—C15118.0 (1)C20—C21—C22119.6 (2)
C17—N9—C28108.5 (1)C20—C21—H21121.2
C17—N9—C29125.3 (2)C22—C21—H21119.2
C28—N9—C29126.2 (2)C17—C22—C21119.4 (2)
O1—C10—O2124.4 (1)C17—C22—C23107.0 (1)
O1—C10—C11117.8 (1)C21—C22—C23133.6 (1)
O2—C10—C11117.7 (2)C22—C23—C24134.7 (2)
C10—C11—C12120.2 (1)C22—C23—C28106.3 (1)
C10—C11—C16119.6 (2)C24—C23—C28119.0 (2)
C12—C11—C16120.2 (1)C23—C24—C25118.4 (2)
C11—C12—C13118.7 (1)C23—C24—H24122.2
C11—C12—H12120.4C25—C24—H24119.4
C13—C12—H12120.9C24—C25—C26121.3 (2)
N7—C13—C12118.6 (1)C24—C25—H25122.8
N7—C13—C14118.6 (1)C26—C25—H25115.9
C12—C13—C14122.9 (2)C25—C26—C27122.0 (3)
C13—C14—C15116.6 (1)C25—C26—H26117.6
C13—C14—H14121.7C27—C26—H26120.4
C15—C14—H14121.7C26—C27—C28117.6 (3)
N8—C15—C14118.4 (1)C26—C27—H27120.5
N8—C15—C16118.8 (1)C28—C27—H27121.8
C14—C15—C16122.9 (1)N9—C28—C23109.3 (2)
C11—C16—C15118.8 (2)N9—C28—C27128.9 (2)
C11—C16—H16120.6C23—C28—C27121.8 (2)
C15—C16—H16120.6N9—C29—H29A109.3
N9—C17—C18129.8 (1)N9—C29—H29B110.4
N9—C17—C22109.0 (1)N9—C29—H29C110.2
C18—C17—C22121.2 (2)H29A—C29—H29B108.6
C17—C18—C19117.0 (2)H29A—C29—H29C108.5
C17—C18—H18121.8H29B—C29—H29C109.7
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.73 (5)1.92 (5)2.648 (2)172 (5)
O2—H2···O1i0.88 (5)1.77 (5)2.648 (2)179 (5)
Symmetry code: (i) x+1, y+1, z+1.
(II) top
Crystal data top
C15H15N·C7H4N2O6Dx = 1.368 Mg m3
Mr = 421.41Mo Kα radiation, λ = 0.71073 Å
Monoclinic, P21/aCell parameters from 25 reflections
a = 8.504 (2) Åθ = 12.9–14.9°
b = 29.533 (4) ŵ = 0.10 mm1
c = 8.568 (2) ÅT = 298 K
β = 108.05 (2)°Prism, orange
V = 2045.8 (7) Å30.5 × 0.5 × 0.5 mm
Z = 4
Data collection top
Rigaku AFC-7R
diffractometer
θmax = 27.5°, θmin = 2.5°
ω scansh = 011
4990 measured reflectionsk = 038
4685 independent reflectionsl = 1111
3283 reflections with I > 2σ(I)3 standard reflections every 150 reflections
Rint = 0.011 intensity decay: none
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.041 w = 1/[σ2(Fo2) + (0.0542P)2 + 0.4038P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.122(Δ/σ)max = 0.001
S = 1.05Δρmax = 0.21 e Å3
4685 reflectionsΔρmin = 0.16 e Å3
288 parameters
Crystal data top
C15H15N·C7H4N2O6V = 2045.8 (7) Å3
Mr = 421.41Z = 4
Monoclinic, P21/aMo Kα radiation
a = 8.504 (2) ŵ = 0.10 mm1
b = 29.533 (4) ÅT = 298 K
c = 8.568 (2) Å0.5 × 0.5 × 0.5 mm
β = 108.05 (2)°
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.011
4990 measured reflections3 standard reflections every 150 reflections
4685 independent reflections intensity decay: none
3283 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.041288 parameters
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.21 e Å3
4685 reflectionsΔρmin = 0.16 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.0226 (2)0.04384 (4)0.8774 (2)0.0606 (3)
O20.1986 (2)0.00141 (4)0.8629 (2)0.0596 (3)
O30.7332 (2)0.04803 (7)0.4968 (2)0.0970 (5)
O40.7483 (2)0.10037 (6)0.3189 (2)0.1084 (6)
O50.2710 (2)0.19129 (5)0.3509 (2)0.0817 (4)
O60.0299 (2)0.16733 (5)0.4925 (2)0.0758 (4)
N70.6713 (2)0.07701 (6)0.4337 (2)0.0707 (4)
N80.1798 (2)0.16475 (5)0.4448 (2)0.0564 (4)
N90.1902 (2)0.15813 (4)0.9916 (2)0.0465 (3)
C100.1272 (2)0.03405 (5)0.8168 (2)0.0444 (3)
C110.2308 (2)0.06314 (5)0.6819 (2)0.0424 (3)
C120.3995 (2)0.05581 (5)0.6200 (2)0.0472 (3)
C130.4926 (2)0.08431 (6)0.4990 (2)0.0500 (4)
C140.4246 (2)0.12029 (5)0.4386 (2)0.0507 (4)
C150.2578 (2)0.12641 (5)0.5040 (2)0.0454 (3)
C160.1577 (2)0.09853 (5)0.6235 (2)0.0443 (3)
C170.3188 (2)0.17607 (5)0.8648 (2)0.0471 (4)
C180.3213 (2)0.21217 (6)0.7593 (2)0.0596 (4)
C190.4665 (3)0.22179 (6)0.6387 (3)0.0715 (6)
C200.6101 (3)0.19693 (8)0.6203 (3)0.0731 (6)
C210.6102 (2)0.16132 (7)0.7240 (2)0.0625 (5)
C220.4635 (2)0.15013 (6)0.8467 (2)0.0483 (4)
C230.4179 (2)0.11450 (5)0.9659 (2)0.0468 (4)
C240.5036 (2)0.07788 (6)1.0045 (2)0.0602 (4)
C250.4202 (3)0.04785 (6)1.1229 (3)0.0676 (5)
C260.2531 (3)0.05316 (6)1.2039 (2)0.0633 (5)
C270.1636 (2)0.08915 (6)1.1707 (2)0.0527 (4)
C280.2487 (2)0.11996 (5)1.0511 (2)0.0434 (3)
C290.0238 (2)0.17727 (6)1.0673 (2)0.0524 (4)
C300.0890 (2)0.16815 (6)0.9637 (2)0.0677 (5)
C310.0289 (2)0.22717 (7)1.1096 (2)0.0735 (6)
H10.080 (5)0.031 (1)0.952 (6)0.0560 (1)*0.50
H20.144 (5)0.013 (1)0.943 (5)0.0530 (1)*0.50
H120.45030.03070.65800.0528*
H140.49200.13960.35280.0566*
H160.03840.10350.66650.0491*
H180.22180.22960.77040.0669*
H190.47210.24630.56270.0785*
H200.71180.20470.53480.0838*
H210.71060.14440.71190.0694*
H240.62040.07410.94920.0671*
H250.47720.02191.14930.0762*
H260.19800.03161.28620.0685*
H270.04680.09221.22690.0583*
H290.02420.16191.17120.0560*
H30A0.19660.18071.01640.0764*
H30B0.04260.18180.85800.0764*
H30C0.09840.13600.95120.0764*
H31A0.08230.24411.00940.0825*
H31B0.07930.23901.15850.0825*
H31C0.09390.23151.18320.0825*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0483 (7)0.0612 (8)0.0639 (8)0.0032 (6)0.0051 (6)0.0221 (6)
O20.0602 (7)0.0528 (7)0.0599 (7)0.0017 (6)0.0102 (6)0.0206 (6)
O30.0576 (9)0.116 (1)0.109 (1)0.0145 (9)0.0134 (9)0.019 (1)
O40.0598 (9)0.111 (1)0.124 (1)0.0116 (9)0.0173 (9)0.036 (1)
O50.108 (1)0.0617 (8)0.0807 (9)0.0196 (8)0.0365 (9)0.0353 (7)
O60.0753 (10)0.0687 (9)0.0779 (9)0.0199 (7)0.0160 (8)0.0140 (7)
N70.0499 (9)0.074 (1)0.077 (1)0.0049 (8)0.0033 (8)0.0019 (9)
N80.083 (1)0.0422 (7)0.0457 (7)0.0028 (7)0.0228 (7)0.0050 (6)
N90.0425 (7)0.0443 (7)0.0542 (7)0.0099 (5)0.0173 (6)0.0018 (6)
C100.0481 (9)0.0409 (8)0.0435 (8)0.0037 (6)0.0130 (7)0.0051 (6)
C110.0490 (8)0.0377 (7)0.0395 (7)0.0050 (6)0.0124 (6)0.0014 (6)
C120.0507 (9)0.0432 (8)0.0473 (8)0.0015 (7)0.0148 (7)0.0017 (7)
C130.0461 (8)0.0515 (9)0.0477 (8)0.0077 (7)0.0077 (7)0.0025 (7)
C140.062 (1)0.0451 (8)0.0415 (8)0.0136 (7)0.0102 (7)0.0045 (6)
C150.0613 (10)0.0371 (7)0.0383 (7)0.0028 (7)0.0162 (7)0.0012 (6)
C160.0510 (9)0.0396 (8)0.0407 (7)0.0025 (6)0.0120 (6)0.0010 (6)
C170.0491 (9)0.0420 (8)0.0548 (9)0.0002 (7)0.0225 (7)0.0059 (7)
C180.071 (1)0.0459 (9)0.067 (1)0.0034 (8)0.0292 (10)0.0017 (8)
C190.091 (2)0.056 (1)0.071 (1)0.026 (1)0.029 (1)0.0080 (9)
C200.068 (1)0.076 (1)0.071 (1)0.031 (1)0.014 (1)0.004 (1)
C210.0446 (9)0.073 (1)0.070 (1)0.0091 (8)0.0181 (8)0.0151 (10)
C220.0427 (8)0.0509 (9)0.0560 (9)0.0007 (7)0.0221 (7)0.0100 (7)
C230.0459 (8)0.0475 (8)0.0529 (9)0.0094 (7)0.0239 (7)0.0124 (7)
C240.061 (1)0.062 (1)0.067 (1)0.0234 (9)0.0325 (9)0.0154 (9)
C250.095 (1)0.052 (1)0.070 (1)0.029 (1)0.045 (1)0.0120 (9)
C260.098 (2)0.0448 (9)0.0548 (10)0.0073 (9)0.035 (1)0.0014 (8)
C270.060 (1)0.0501 (9)0.0500 (9)0.0030 (8)0.0206 (8)0.0049 (7)
C280.0477 (8)0.0407 (7)0.0467 (8)0.0084 (6)0.0220 (7)0.0080 (6)
C290.0473 (9)0.0563 (9)0.0529 (9)0.0168 (7)0.0148 (7)0.0054 (7)
C300.052 (1)0.075 (1)0.082 (1)0.0136 (9)0.0291 (9)0.013 (1)
C310.078 (1)0.062 (1)0.086 (1)0.027 (1)0.034 (1)0.025 (1)
Geometric parameters (Å, º) top
O1—C101.251 (2)C19—C201.391 (3)
O1—H10.78 (4)C19—H190.966
O2—C101.266 (2)C20—C211.377 (3)
O2—H20.82 (4)C20—H200.972
O3—N71.216 (3)C21—C221.399 (2)
O4—N71.214 (2)C21—H210.967
O5—N81.215 (2)C22—C231.433 (2)
O6—N81.215 (2)C23—C241.400 (3)
N7—C131.463 (2)C23—C281.407 (2)
N8—C151.479 (2)C24—C251.368 (3)
N9—C171.387 (2)C24—H240.965
N9—C281.391 (2)C25—C261.384 (3)
N9—C291.474 (2)C25—H250.970
C10—C111.490 (2)C26—C271.387 (3)
C11—C121.383 (2)C26—H260.958
C11—C161.386 (2)C27—C281.394 (2)
C12—C131.379 (2)C27—H270.964
C12—H120.964C29—C301.518 (3)
C13—C141.384 (3)C29—C311.521 (3)
C14—C151.366 (2)C29—H290.971
C14—H140.966C30—H30A0.960
C15—C161.383 (2)C30—H30B0.958
C16—H160.978C30—H30C0.961
C17—C181.393 (3)C31—H31A0.976
C17—C221.417 (2)C31—H31B0.951
C18—C191.372 (3)C31—H31C0.967
C18—H180.969
C10—O1—H1122 (3)C21—C20—H20119.3
C10—O2—H2118 (3)C20—C21—C22119.1 (2)
O3—N7—O4124.1 (2)C20—C21—H21120.2
O3—N7—C13118.4 (2)C22—C21—H21120.6
O4—N7—C13117.5 (2)C17—C22—C21119.7 (2)
O5—N8—O6124.8 (2)C17—C22—C23106.6 (1)
O5—N8—C15117.3 (2)C21—C22—C23133.6 (2)
O6—N8—C15117.9 (1)C22—C23—C24133.6 (1)
C17—N9—C28108.2 (1)C22—C23—C28107.0 (1)
C17—N9—C29128.0 (1)C24—C23—C28119.3 (1)
C28—N9—C29123.6 (1)C23—C24—C25119.2 (2)
O1—C10—O2124.8 (1)C23—C24—H24120.3
O1—C10—C11118.1 (1)C25—C24—H24120.5
O2—C10—C11117.1 (1)C24—C25—C26120.9 (2)
C10—C11—C12120.1 (1)C24—C25—H25120.2
C10—C11—C16119.4 (1)C26—C25—H25118.8
C12—C11—C16120.5 (1)C25—C26—C27121.8 (2)
C11—C12—C13118.6 (2)C25—C26—H26119.1
C11—C12—H12120.7C27—C26—H26119.1
C13—C12—H12120.7C26—C27—C28117.3 (1)
N7—C13—C12118.9 (2)C26—C27—H27121.0
N7—C13—C14118.3 (1)C28—C27—H27121.7
C12—C13—C14122.7 (1)N9—C28—C23109.1 (1)
C13—C14—C15116.7 (1)N9—C28—C27129.4 (1)
C13—C14—H14121.3C23—C28—C27121.4 (1)
C15—C14—H14121.9N9—C29—C30111.6 (1)
N8—C15—C14118.7 (1)N9—C29—C31112.4 (1)
N8—C15—C16118.1 (1)N9—C29—H29107.3
C14—C15—C16123.2 (2)C30—C29—C31112.4 (2)
C11—C16—C15118.3 (1)C30—C29—H29106.9
C11—C16—H16120.4C31—C29—H29105.7
C15—C16—H16121.3C29—C30—H30A109.8
N9—C17—C18130.6 (2)C29—C30—H30B109.1
N9—C17—C22109.1 (1)C29—C30—H30C109.3
C18—C17—C22120.3 (1)H30A—C30—H30B109.6
C17—C18—C19118.4 (2)H30A—C30—H30C109.4
C17—C18—H18120.4H30B—C30—H30C109.6
C19—C18—H18121.2C29—C31—H31A109.1
C18—C19—C20122.0 (2)C29—C31—H31B111.4
C18—C19—H19120.5C29—C31—H31C110.3
C20—C19—H19117.5H31A—C31—H31B108.8
C19—C20—C21120.4 (2)H31A—C31—H31C107.5
C19—C20—H20120.4H31B—C31—H31C109.6
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.78 (4)1.86 (4)2.629 (2)174 (5)
O2—H2···O1i0.82 (4)1.81 (4)2.629 (2)178 (4)
Symmetry code: (i) x, y, z+2.
(III) top
Crystal data top
C16H17N·C7H4N2O6Z = 4
Mr = 435.44Dx = 1.344 Mg m3
Triclinic, P1Mo Kα radiation, λ = 0.71073 Å
a = 16.723 (2) ÅCell parameters from 25 reflections
b = 16.784 (3) Åθ = 11.8–14.7°
c = 8.4129 (9) ŵ = 0.10 mm1
α = 102.36 (1)°T = 298 K
β = 92.34 (1)°Prism, orange
γ = 109.91 (1)°0.6 × 0.5 × 0.2 mm
V = 2152.0 (6) Å3
Data collection top
Rigaku AFC-7R
diffractometer
θmax = 27.5°, θmin = 2.5°
θ–2θ scansh = 022
10208 measured reflectionsk = 2222
9870 independent reflectionsl = 1111
4817 reflections with I > 2σ(I)3 standard reflections every 150 reflections
Rint = 0.010 intensity decay: none
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.061 w = 1/[σ2(Fo2) + (0.050P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.192(Δ/σ)max = 0.001
S = 1.74Δρmax = 0.24 e Å3
9870 reflectionsΔρmin = 0.25 e Å3
593 parameters
Crystal data top
C16H17N·C7H4N2O6γ = 109.91 (1)°
Mr = 435.44V = 2152.0 (6) Å3
Triclinic, P1Z = 4
a = 16.723 (2) ÅMo Kα radiation
b = 16.784 (3) ŵ = 0.10 mm1
c = 8.4129 (9) ÅT = 298 K
α = 102.36 (1)°0.6 × 0.5 × 0.2 mm
β = 92.34 (1)°
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.010
10208 measured reflections3 standard reflections every 150 reflections
9870 independent reflections intensity decay: none
4817 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.061593 parameters
wR(F2) = 0.192H atoms treated by a mixture of independent and constrained refinement
S = 1.74Δρmax = 0.24 e Å3
9870 reflectionsΔρmin = 0.25 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.1139 (2)0.3069 (2)0.8584 (3)0.0751 (8)
O1*0.0704 (1)0.2143 (1)0.5645 (3)0.0705 (6)
O20.0230 (2)0.1692 (1)0.7635 (3)0.0719 (6)
O2*0.0097 (1)0.3540 (1)0.6844 (3)0.0665 (5)
O30.0840 (2)0.0625 (2)0.9435 (4)0.125 (1)
O3*0.1002 (2)0.5786 (1)0.6063 (3)0.0879 (7)
O40.1969 (2)0.0341 (2)1.1044 (4)0.123 (1)
O4*0.1979 (2)0.5499 (1)0.4060 (3)0.1023 (8)
O50.4042 (2)0.2571 (2)1.2670 (3)0.0994 (8)
O5*0.3542 (2)0.2507 (2)0.1185 (3)0.0964 (7)
O60.3728 (2)0.3626 (2)1.2126 (3)0.1074 (8)
O6*0.3153 (2)0.1498 (2)0.1733 (3)0.0997 (8)
N70.1496 (2)0.0125 (2)1.0244 (4)0.0814 (8)
N7*0.1524 (2)0.5285 (2)0.4910 (3)0.0695 (6)
N80.3570 (2)0.2854 (2)1.2035 (3)0.0746 (7)
N8*0.3070 (2)0.2259 (2)0.1906 (3)0.0692 (6)
N90.3086 (2)0.2507 (2)0.6347 (3)0.0702 (7)
N9*0.2725 (1)0.2366 (1)0.7314 (3)0.0609 (6)
C100.0895 (2)0.2252 (2)0.8477 (3)0.0571 (7)
C10*0.0521 (2)0.2969 (2)0.5896 (3)0.0540 (6)
C110.1462 (2)0.1957 (2)0.9426 (3)0.0522 (6)
C11*0.1120 (2)0.3247 (2)0.4983 (3)0.0505 (6)
C120.1219 (2)0.1080 (2)0.9414 (3)0.0556 (6)
C12*0.1029 (2)0.4123 (2)0.5331 (3)0.0515 (6)
C130.1753 (2)0.0811 (2)1.0266 (3)0.0583 (7)
C13*0.1608 (2)0.4366 (2)0.4509 (3)0.0536 (6)
C140.2533 (2)0.1369 (2)1.1121 (3)0.0581 (7)
C14*0.2269 (2)0.3776 (2)0.3358 (3)0.0550 (6)
C150.2748 (2)0.2232 (2)1.1109 (3)0.0542 (6)
C15*0.2339 (2)0.2919 (2)0.3068 (3)0.0546 (6)
C160.2228 (2)0.2540 (2)1.0285 (3)0.0559 (6)
C16*0.1785 (2)0.2632 (2)0.3839 (3)0.0541 (6)
C170.3370 (2)0.1947 (2)0.7003 (4)0.0686 (8)
C17*0.3080 (2)0.2944 (2)0.6928 (3)0.0637 (7)
C180.4137 (2)0.2124 (2)0.7987 (4)0.089 (1)
C18*0.3799 (2)0.2763 (2)0.5781 (4)0.087 (1)
C190.4264 (2)0.1463 (4)0.8528 (5)0.106 (1)
C19*0.3987 (2)0.3483 (4)0.5592 (5)0.115 (2)
C200.3643 (4)0.0633 (3)0.8107 (5)0.108 (1)
C20*0.3521 (4)0.4326 (4)0.6504 (7)0.127 (2)
C210.2882 (3)0.0435 (2)0.7125 (4)0.088 (1)
C21*0.2842 (3)0.4492 (2)0.7628 (4)0.097 (1)
C220.2742 (2)0.1114 (2)0.6555 (4)0.0659 (8)
C22*0.2596 (2)0.3792 (2)0.7852 (4)0.0673 (8)
C230.2056 (2)0.1170 (2)0.5561 (3)0.0673 (8)
C23*0.1928 (2)0.3717 (2)0.8863 (3)0.0614 (7)
C240.1276 (3)0.0583 (2)0.4748 (4)0.094 (1)
C24*0.1249 (3)0.4329 (2)0.9997 (4)0.087 (1)
C250.0752 (2)0.0857 (4)0.3898 (5)0.111 (1)
C25*0.0700 (2)0.4025 (3)1.0729 (4)0.102 (1)
C260.0980 (3)0.1716 (4)0.3830 (4)0.108 (1)
C26*0.0812 (2)0.3143 (3)1.0379 (4)0.093 (1)
C270.1752 (3)0.2338 (2)0.4602 (4)0.0814 (9)
C27*0.1475 (2)0.2521 (2)0.9265 (4)0.0700 (8)
C280.2288 (2)0.2047 (2)0.5461 (3)0.0646 (7)
C28*0.2027 (2)0.2831 (2)0.8504 (3)0.0562 (7)
C290.3612 (2)0.3412 (2)0.6392 (4)0.090 (1)
C29*0.3014 (2)0.1437 (2)0.6573 (4)0.0724 (8)
C300.3591 (2)0.4080 (2)0.7868 (3)0.0679 (8)
C30*0.3724 (2)0.0888 (2)0.7351 (4)0.0747 (9)
C310.4133 (2)0.4993 (2)0.7712 (4)0.0835 (9)
C31*0.3984 (2)0.0080 (2)0.6605 (4)0.0860 (10)
C320.4164 (2)0.5697 (2)0.9123 (4)0.104 (1)
C32*0.4633 (3)0.0640 (2)0.7417 (5)0.116 (1)
H10.092 (4)0.323 (4)0.820 (7)0.0343 (2)*0.50
H1*0.034 (3)0.196 (3)0.606 (7)0.0470 (2)*0.50
H20.007 (4)0.182 (4)0.716 (9)0.0661 (3)*0.50
H2*0.044 (5)0.330 (4)0.750 (8)0.0931 (3)*0.50
H120.06800.06600.88160.0662*
H12*0.05640.45620.61230.0589*
H140.29100.11651.17030.0675*
H14*0.26570.39700.27900.0629*
H160.24120.31651.03170.0645*
H16*0.18560.20110.35930.0616*
H180.45680.27200.82630.1002*
H18*0.41470.21670.51720.1043*
H190.48000.15720.92030.1203*
H19*0.44620.34110.48120.1297*
H200.37480.01870.85380.1320*
H20*0.36850.47980.62780.1407*
H210.24610.01490.68590.1027*
H21*0.25320.50810.82630.1150*
H240.10840.00310.47800.1099*
H24*0.11870.49461.02780.1026*
H250.02130.04410.33090.1259*
H25*0.02190.44381.14920.1232*
H260.06030.18980.32030.1279*
H26*0.04110.29611.09370.1085*
H270.19250.29550.45710.0975*
H27*0.15500.19030.90140.0827*
H29A0.34190.35630.54290.1049*
H29B0.41980.34490.63280.1049*
H29*A0.25320.12540.66590.0873*
H29*B0.32050.13500.54320.0873*
H30A0.30170.40540.79780.0772*
H30B0.38280.39780.88400.0772*
H30*A0.35610.10030.85080.0843*
H30*B0.42330.10470.72070.0843*
H31A0.38980.50910.67340.0933*
H31B0.47100.50120.75810.0933*
H31*A0.34690.02280.66530.0978*
H31*B0.41960.02020.54510.0978*
H32A0.45130.62530.89580.1152*
H32B0.44020.56081.01030.1152*
H32C0.35930.56920.92510.1152*
H32*B0.51560.05090.73580.1292*
H32*C0.44300.05280.85700.1292*
H32*A0.47720.12490.69230.1292*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.083 (2)0.072 (2)0.080 (2)0.036 (1)0.006 (1)0.028 (1)
O1*0.079 (1)0.069 (1)0.074 (1)0.042 (1)0.004 (1)0.015 (1)
O20.066 (1)0.074 (1)0.078 (2)0.028 (1)0.009 (1)0.021 (1)
O2*0.060 (1)0.070 (1)0.070 (1)0.022 (1)0.005 (1)0.022 (1)
O30.121 (2)0.067 (2)0.170 (3)0.014 (2)0.042 (2)0.034 (2)
O3*0.102 (2)0.057 (1)0.090 (2)0.018 (1)0.015 (1)0.009 (1)
O40.126 (2)0.078 (2)0.170 (3)0.043 (2)0.034 (2)0.042 (2)
O4*0.095 (2)0.076 (2)0.142 (2)0.038 (1)0.023 (2)0.036 (1)
O50.078 (2)0.112 (2)0.098 (2)0.034 (1)0.029 (1)0.010 (1)
O5*0.080 (2)0.106 (2)0.089 (2)0.031 (1)0.030 (1)0.005 (1)
O60.104 (2)0.081 (2)0.112 (2)0.005 (1)0.023 (2)0.023 (1)
O6*0.104 (2)0.070 (2)0.094 (2)0.004 (1)0.022 (1)0.007 (1)
N70.076 (2)0.064 (2)0.103 (2)0.025 (2)0.006 (2)0.023 (2)
N7*0.068 (2)0.059 (2)0.083 (2)0.022 (1)0.003 (1)0.025 (1)
N80.074 (2)0.079 (2)0.061 (2)0.019 (2)0.001 (1)0.012 (1)
N8*0.060 (2)0.075 (2)0.056 (1)0.009 (1)0.000 (1)0.009 (1)
N90.072 (2)0.058 (1)0.073 (2)0.015 (1)0.014 (1)0.015 (1)
N9*0.059 (1)0.054 (1)0.059 (1)0.010 (1)0.008 (1)0.009 (1)
C100.065 (2)0.062 (2)0.053 (2)0.030 (2)0.009 (1)0.018 (1)
C10*0.060 (2)0.060 (2)0.049 (2)0.027 (1)0.009 (1)0.016 (1)
C110.051 (2)0.064 (2)0.048 (1)0.026 (1)0.010 (1)0.016 (1)
C11*0.050 (1)0.059 (2)0.046 (1)0.021 (1)0.009 (1)0.016 (1)
C120.051 (2)0.056 (2)0.061 (2)0.020 (1)0.003 (1)0.015 (1)
C12*0.048 (1)0.060 (2)0.045 (1)0.017 (1)0.004 (1)0.014 (1)
C130.064 (2)0.052 (2)0.064 (2)0.025 (1)0.009 (1)0.017 (1)
C13*0.054 (2)0.056 (2)0.055 (2)0.020 (1)0.011 (1)0.020 (1)
C140.063 (2)0.067 (2)0.054 (2)0.033 (2)0.008 (1)0.016 (1)
C14*0.046 (1)0.070 (2)0.053 (2)0.021 (1)0.006 (1)0.023 (1)
C150.049 (2)0.064 (2)0.047 (1)0.019 (1)0.005 (1)0.010 (1)
C15*0.046 (1)0.071 (2)0.041 (1)0.014 (1)0.007 (1)0.014 (1)
C160.062 (2)0.061 (2)0.048 (1)0.023 (1)0.013 (1)0.016 (1)
C16*0.061 (2)0.060 (2)0.045 (1)0.024 (1)0.013 (1)0.016 (1)
C170.072 (2)0.070 (2)0.063 (2)0.027 (2)0.021 (2)0.010 (2)
C17*0.056 (2)0.079 (2)0.059 (2)0.023 (2)0.018 (1)0.021 (2)
C180.073 (2)0.116 (3)0.080 (2)0.039 (2)0.018 (2)0.017 (2)
C18*0.061 (2)0.131 (3)0.077 (2)0.037 (2)0.015 (2)0.036 (2)
C190.095 (3)0.147 (4)0.096 (3)0.073 (3)0.020 (2)0.021 (3)
C19*0.090 (3)0.207 (5)0.096 (3)0.089 (4)0.038 (2)0.074 (3)
C200.147 (4)0.136 (4)0.090 (3)0.104 (4)0.040 (3)0.032 (3)
C20*0.161 (5)0.191 (5)0.116 (4)0.132 (5)0.080 (4)0.091 (4)
C210.122 (3)0.071 (2)0.084 (2)0.047 (2)0.045 (2)0.016 (2)
C21*0.143 (4)0.091 (3)0.098 (3)0.070 (3)0.069 (3)0.050 (2)
C220.077 (2)0.060 (2)0.061 (2)0.029 (2)0.023 (2)0.008 (1)
C22*0.082 (2)0.068 (2)0.060 (2)0.031 (2)0.032 (2)0.022 (2)
C230.075 (2)0.060 (2)0.054 (2)0.016 (2)0.021 (2)0.001 (1)
C23*0.075 (2)0.050 (2)0.049 (2)0.008 (1)0.022 (1)0.010 (1)
C240.094 (3)0.082 (2)0.076 (2)0.006 (2)0.023 (2)0.001 (2)
C24*0.096 (3)0.073 (2)0.058 (2)0.008 (2)0.021 (2)0.004 (2)
C250.081 (3)0.147 (4)0.067 (2)0.011 (3)0.003 (2)0.005 (3)
C25*0.079 (3)0.127 (3)0.049 (2)0.018 (2)0.010 (2)0.008 (2)
C260.100 (3)0.176 (5)0.058 (2)0.066 (3)0.014 (2)0.018 (3)
C26*0.063 (2)0.150 (4)0.058 (2)0.019 (2)0.007 (2)0.038 (2)
C270.098 (3)0.100 (3)0.063 (2)0.052 (2)0.025 (2)0.024 (2)
C27*0.071 (2)0.085 (2)0.059 (2)0.026 (2)0.019 (2)0.030 (2)
C280.073 (2)0.063 (2)0.054 (2)0.021 (2)0.019 (2)0.008 (1)
C28*0.053 (2)0.060 (2)0.048 (2)0.009 (1)0.013 (1)0.015 (1)
C290.105 (3)0.065 (2)0.084 (2)0.009 (2)0.032 (2)0.019 (2)
C29*0.075 (2)0.059 (2)0.065 (2)0.007 (2)0.011 (2)0.004 (1)
C300.071 (2)0.066 (2)0.066 (2)0.021 (2)0.009 (1)0.020 (1)
C30*0.082 (2)0.059 (2)0.064 (2)0.005 (2)0.014 (2)0.007 (1)
C310.085 (2)0.066 (2)0.087 (2)0.012 (2)0.011 (2)0.017 (2)
C31*0.081 (2)0.069 (2)0.084 (2)0.004 (2)0.006 (2)0.007 (2)
C320.114 (3)0.083 (2)0.103 (3)0.025 (2)0.010 (2)0.016 (2)
C32*0.114 (3)0.084 (3)0.122 (3)0.001 (2)0.003 (3)0.030 (2)
Geometric parameters (Å, º) top
O1—C101.272 (4)C19*—C20*1.391 (7)
O1—H10.64 (7)C19*—H19*0.967
O1*—C10*1.281 (4)C20—C211.385 (7)
O1*—H1*0.86 (6)C20—H200.961
O2—C101.249 (3)C20*—C21*1.359 (7)
O2—H20.74 (8)C20*—H20*0.973
O2*—C10*1.247 (3)C21—C221.410 (5)
O2*—H2*1.01 (8)C21—H210.965
O3—N71.199 (4)C21*—C22*1.416 (6)
O3*—N7*1.221 (3)C21*—H21*0.966
O4—N71.211 (5)C22—C231.433 (5)
O4*—N7*1.214 (4)C22*—C23*1.432 (5)
O5—N81.211 (4)C23—C241.380 (4)
O5*—N8*1.207 (4)C23—C281.410 (4)
O6—N81.215 (4)C23*—C24*1.398 (4)
O6*—N8*1.211 (4)C23*—C28*1.401 (4)
N7—C131.477 (4)C24—C251.361 (7)
N7*—C13*1.463 (4)C24—H240.976
N8—C151.475 (3)C24*—C25*1.375 (7)
N8*—C15*1.482 (3)C24*—H24*0.978
N9—C171.384 (5)C25—C261.374 (8)
N9—C281.379 (4)C25—H250.965
N9—C291.465 (4)C25*—C26*1.390 (7)
N9*—C17*1.383 (5)C25*—H25*0.963
N9*—C28*1.386 (3)C26—C271.379 (5)
N9*—C29*1.448 (3)C26—H260.971
C10—C111.487 (5)C26*—C27*1.379 (4)
C10*—C11*1.489 (4)C26*—H26*0.970
C11—C121.385 (4)C27—C281.400 (6)
C11—C161.374 (3)C27—H270.983
C11*—C12*1.390 (4)C27*—C28*1.399 (5)
C11*—C16*1.391 (3)C27*—H27*0.977
C12—C131.369 (4)C29—C301.495 (4)
C12—H120.969C29—H29A0.972
C12*—C13*1.384 (4)C29—H29B0.966
C12*—H12*0.973C29*—C30*1.504 (4)
C13—C141.379 (3)C29*—H29*A0.960
C13*—C14*1.377 (3)C29*—H29*B0.964
C14—C151.370 (4)C30—C311.529 (4)
C14—H140.974C30—H30A0.955
C14*—C15*1.369 (4)C30—H30B0.967
C14*—H14*0.971C30*—C31*1.512 (4)
C15—C161.384 (4)C30*—H30*A0.960
C15*—C16*1.379 (4)C30*—H30*B0.985
C16—H160.981C31—C321.471 (4)
C16*—H16*0.981C31—H31A0.966
C17—C181.403 (5)C31—H31B0.967
C17—C221.394 (4)C31*—C32*1.472 (5)
C17*—C18*1.414 (4)C31*—H31*A0.976
C17*—C22*1.406 (4)C31*—H31*B0.974
C18—C191.361 (7)C32—H32A0.960
C18—H180.984C32—H32B0.963
C18*—C19*1.386 (8)C32—H32C0.962
C18*—H18*0.980C32*—H32*B0.975
C19—C201.386 (6)C32*—H32*C0.971
C19—H190.981C32*—H32*A0.958
C10—O1—H1121 (4)C20*—C21*—H21*120.3
C10*—O1*—H1*118 (3)C22*—C21*—H21*120.7
C10—O2—H2121 (4)C17—C22—C21118.8 (3)
C10*—O2*—H2*114 (3)C17—C22—C23106.8 (3)
O3—N7—O4123.9 (3)C21—C22—C23134.4 (3)
O3—N7—C13118.7 (3)C17*—C22*—C21*118.5 (3)
O4—N7—C13117.4 (2)C17*—C22*—C23*106.7 (3)
O3*—N7*—O4*124.3 (3)C21*—C22*—C23*134.8 (2)
O3*—N7*—C13*118.4 (3)C22—C23—C24134.8 (3)
O4*—N7*—C13*117.3 (2)C22—C23—C28107.3 (2)
O5—N8—O6124.0 (2)C24—C23—C28117.9 (3)
O5—N8—C15118.5 (3)C22*—C23*—C24*132.9 (3)
O6—N8—C15117.5 (3)C22*—C23*—C28*106.9 (2)
O5*—N8*—O6*124.1 (2)C24*—C23*—C28*120.1 (3)
O5*—N8*—C15*118.5 (3)C23—C24—C25120.1 (3)
O6*—N8*—C15*117.5 (3)C23—C24—H24121.2
C17—N9—C28109.4 (2)C25—C24—H24118.7
C17—N9—C29124.4 (2)C23*—C24*—C25*117.4 (3)
C28—N9—C29125.6 (3)C23*—C24*—H24*120.4
C17*—N9*—C28*108.3 (2)C25*—C24*—H24*122.1
C17*—N9*—C29*126.0 (2)C24—C25—C26121.4 (3)
C28*—N9*—C29*125.6 (3)C24—C25—H25119.8
O1—C10—O2125.2 (3)C26—C25—H25118.7
O1—C10—C11116.3 (2)C24*—C25*—C26*121.9 (3)
O2—C10—C11118.5 (3)C24*—C25*—H25*118.9
O1*—C10*—O2*125.5 (3)C26*—C25*—H25*119.2
O1*—C10*—C11*115.7 (2)C25—C26—C27121.7 (5)
O2*—C10*—C11*118.8 (3)C25—C26—H26120.3
C10—C11—C12119.3 (2)C27—C26—H26118.0
C10—C11—C16120.8 (3)C25*—C26*—C27*122.2 (4)
C12—C11—C16119.9 (3)C25*—C26*—H26*118.8
C10*—C11*—C12*119.4 (2)C27*—C26*—H26*119.1
C10*—C11*—C16*120.4 (2)C26—C27—C28116.4 (4)
C12*—C11*—C16*120.2 (3)C26—C27—H27122.9
C11—C12—C13118.9 (2)C28—C27—H27120.8
C11—C12—H12120.9C26*—C27*—C28*116.0 (3)
C13—C12—H12120.2C26*—C27*—H27*122.1
C11*—C12*—C13*118.6 (2)C28*—C27*—H27*121.9
C11*—C12*—H12*121.1N9—C28—C23107.7 (3)
C13*—C12*—H12*120.2N9—C28—C27129.8 (3)
N7—C13—C12118.8 (2)C23—C28—C27122.5 (3)
N7—C13—C14117.9 (3)N9*—C28*—C23*109.0 (3)
C12—C13—C14123.3 (3)N9*—C28*—C27*128.6 (2)
N7*—C13*—C12*118.5 (2)C23*—C28*—C27*122.4 (2)
N7*—C13*—C14*118.8 (3)N9—C29—C30115.5 (3)
C12*—C13*—C14*122.8 (3)N9—C29—H29A108.5
C13—C14—C15116.0 (3)N9—C29—H29B108.4
C13—C14—H14122.2C30—C29—H29A107.7
C15—C14—H14121.8C30—C29—H29B108.5
C13*—C14*—C15*116.6 (3)H29A—C29—H29B107.9
C13*—C14*—H14*120.6N9*—C29*—C30*114.4 (3)
C15*—C14*—H14*122.8N9*—C29*—H29*A107.9
N8—C15—C14117.8 (3)N9*—C29*—H29*B107.5
N8—C15—C16119.1 (3)C30*—C29*—H29*A108.5
C14—C15—C16123.1 (2)C30*—C29*—H29*B109.4
N8*—C15*—C14*118.2 (3)H29*A—C29*—H29*B109.1
N8*—C15*—C16*118.1 (3)C29—C30—C31109.8 (2)
C14*—C15*—C16*123.7 (2)C29—C30—H30A110.6
C11—C16—C15118.8 (2)C29—C30—H30B109.7
C11—C16—H16121.5C31—C30—H30A109.0
C15—C16—H16119.7C31—C30—H30B108.3
C11*—C16*—C15*118.1 (2)H30A—C30—H30B109.3
C11*—C16*—H16*120.7C29*—C30*—C31*113.2 (3)
C15*—C16*—H16*121.2C29*—C30*—H30*A110.4
N9—C17—C18129.5 (3)C29*—C30*—H30*B109.0
N9—C17—C22108.7 (3)C31*—C30*—H30*A109.1
C18—C17—C22121.8 (3)C31*—C30*—H30*B107.6
N9*—C17*—C18*128.2 (3)H30*A—C30*—H30*B107.4
N9*—C17*—C22*109.0 (3)C30—C31—C32113.9 (3)
C18*—C17*—C22*122.8 (3)C30—C31—H31A108.2
C17—C18—C19118.9 (3)C30—C31—H31B108.5
C17—C18—H18119.3C32—C31—H31A108.9
C19—C18—H18121.9C32—C31—H31B108.9
C17*—C18*—C19*115.6 (3)H31A—C31—H31B108.4
C17*—C18*—H18*122.2C30*—C31*—C32*114.6 (3)
C19*—C18*—H18*122.2C30*—C31*—H31*A107.6
C18—C19—C20120.1 (4)C30*—C31*—H31*B108.9
C18—C19—H19120.0C32*—C31*—H31*A109.0
C20—C19—H19119.9C32*—C31*—H31*B109.3
C18*—C19*—C20*122.5 (5)H31*A—C31*—H31*B107.1
C18*—C19*—H19*120.3C31—C32—H32A110.1
C20*—C19*—H19*117.1C31—C32—H32B109.5
C19—C20—C21122.5 (5)C31—C32—H32C109.5
C19—C20—H20117.7H32A—C32—H32B109.2
C21—C20—H20119.8H32A—C32—H32C109.3
C19*—C20*—C21*121.5 (6)H32B—C32—H32C109.1
C19*—C20*—H20*117.5C31*—C32*—H32*B109.9
C21*—C20*—H20*120.9C31*—C32*—H32*C110.3
C20—C21—C22118.0 (3)C31*—C32*—H32*A112.1
C20—C21—H21120.4H32*B—C32*—H32*C107.3
C22—C21—H21121.5H32*B—C32*—H32*A108.3
C20*—C21*—C22*119.0 (3)H32*C—C32*—H32*A108.7
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2*0.64 (7)2.02 (7)2.651 (4)171 (6)
O1*—H1*···O20.86 (6)1.82 (6)2.637 (4)158 (5)
O2—H2···O1*0.74 (8)1.90 (8)2.637 (4)169 (8)
O2*—H2*···O11.01 (8)1.65 (8)2.651 (4)170 (6)
(IV) top
Crystal data top
C16H17N·C7H4N2O6Dx = 1.364 Mg m3
Mr = 435.44Mo Kα radiation, λ = 0.71073 Å
Monoclinic, P21/cCell parameters from 25 reflections
a = 8.212 (2) Åθ = 12.3–14.7°
b = 31.924 (2) ŵ = 0.10 mm1
c = 8.438 (1) ÅT = 298 K
β = 106.54 (1)°Prism, orange
V = 2120.5 (6) Å30.5 × 0.4 × 0.3 mm
Z = 4
Data collection top
Rigaku AFC-7R
diffractometer
θmax = 27.5°, θmin = 2.5°
ω scansh = 1111
5184 measured reflectionsk = 041
4864 independent reflectionsl = 110
2811 reflections with I > 2σ(I)3 standard reflections every 150 reflections
Rint = 0.006 intensity decay: none
Refinement top
Refinement on F2 w = 1/[σ2(Fo2) + (0.0409P)2 + 1.8479P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.049(Δ/σ)max = 0.001
wR(F2) = 0.165Δρmax = 0.20 e Å3
S = 1.03Δρmin = 0.25 e Å3
4864 reflectionsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
298 parametersExtinction coefficient: 0.0044 (7)
H atoms treated by a mixture of independent and constrained refinement
Crystal data top
C16H17N·C7H4N2O6V = 2120.5 (6) Å3
Mr = 435.44Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.212 (2) ŵ = 0.10 mm1
b = 31.924 (2) ÅT = 298 K
c = 8.438 (1) Å0.5 × 0.4 × 0.3 mm
β = 106.54 (1)°
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.006
5184 measured reflections3 standard reflections every 150 reflections
4864 independent reflections intensity decay: none
2811 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.049298 parameters
wR(F2) = 0.165H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.20 e Å3
4864 reflectionsΔρmin = 0.25 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.6288 (3)0.45743 (7)0.0189 (3)0.0671 (6)
O20.6442 (3)0.50128 (7)0.1912 (3)0.0699 (6)
O30.9712 (4)0.4595 (1)0.7416 (3)0.1084 (10)
O41.1433 (5)0.40767 (9)0.7761 (3)0.126 (1)
O51.1618 (3)0.32148 (7)0.3129 (3)0.0873 (7)
O60.9912 (3)0.33483 (8)0.0721 (3)0.0851 (7)
N71.0354 (4)0.43026 (9)0.6898 (3)0.0793 (8)
N81.0544 (3)0.34276 (7)0.2182 (4)0.0639 (6)
N90.5426 (3)0.34977 (7)0.2175 (3)0.0560 (6)
C100.6893 (4)0.46903 (8)0.1302 (3)0.0538 (6)
C110.8202 (3)0.44159 (8)0.2400 (3)0.0509 (6)
C120.8718 (4)0.44946 (8)0.4092 (3)0.0557 (7)
C130.9849 (4)0.42230 (9)0.5103 (3)0.0565 (7)
C141.0490 (3)0.38745 (8)0.4520 (3)0.0581 (7)
C150.9941 (3)0.38056 (8)0.2846 (3)0.0532 (6)
C160.8814 (3)0.40684 (8)0.1767 (3)0.0532 (6)
C170.6518 (4)0.33008 (9)0.3521 (3)0.0581 (7)
C180.7513 (4)0.2947 (1)0.3567 (4)0.0702 (8)
C190.8561 (4)0.2825 (1)0.5092 (5)0.085 (1)
C200.8614 (4)0.3042 (1)0.6531 (4)0.089 (1)
C210.7607 (4)0.3388 (1)0.6492 (4)0.079 (1)
C220.6543 (4)0.3521 (1)0.4974 (3)0.0615 (7)
C230.5408 (4)0.3871 (1)0.4471 (3)0.0617 (7)
C240.4940 (5)0.4209 (1)0.5301 (4)0.0768 (10)
C250.3856 (5)0.4505 (1)0.4420 (5)0.085 (1)
C260.3198 (4)0.44778 (9)0.2709 (5)0.0788 (10)
C270.3625 (4)0.41464 (9)0.1836 (3)0.0649 (8)
C280.4746 (4)0.38472 (9)0.2734 (3)0.0564 (7)
C290.5275 (3)0.34156 (7)0.0433 (3)0.0547 (7)
C300.3687 (3)0.31808 (8)0.0511 (3)0.0499 (6)
C310.3676 (3)0.31583 (8)0.2309 (3)0.0665 (8)
C320.3584 (4)0.27506 (9)0.0194 (3)0.0721 (9)
H10.559 (9)0.473 (2)0.076 (8)0.0595 (2)*0.50
H20.56 (1)0.517 (3)0.130 (10)0.1044 (4)*0.50
H120.83230.47380.45480.0629*
H141.13040.36930.52490.0655*
H160.84780.40100.05970.0603*
H180.74870.27890.25940.0808*
H190.92760.25840.51780.0974*
H200.93900.29560.75810.0988*
H210.75960.35350.74980.0882*
H240.53610.42310.64800.0898*
H250.35360.47380.49820.0940*
H260.24100.46920.21110.0941*
H270.31700.41270.06470.0711*
H29A0.53030.36800.01240.0618*
H29B0.62460.32520.03730.0618*
H300.27160.33430.04520.0549*
H31A0.36790.34340.27630.0742*
H31B0.46590.30070.24070.0742*
H31C0.26680.30120.29470.0742*
H32A0.36070.27720.13390.0832*
H32B0.45290.25810.01140.0832*
H32C0.25420.26140.04080.0832*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.073 (1)0.070 (1)0.052 (1)0.016 (1)0.007 (1)0.003 (1)
O20.074 (1)0.059 (1)0.069 (1)0.015 (1)0.007 (1)0.004 (1)
O30.127 (2)0.123 (2)0.066 (2)0.028 (2)0.011 (1)0.024 (2)
O40.186 (3)0.092 (2)0.064 (2)0.042 (2)0.022 (2)0.003 (1)
O50.093 (2)0.070 (1)0.095 (2)0.031 (1)0.022 (1)0.012 (1)
O60.088 (2)0.089 (2)0.075 (2)0.017 (1)0.016 (1)0.021 (1)
N70.102 (2)0.068 (2)0.057 (2)0.002 (2)0.004 (2)0.002 (1)
N80.062 (2)0.055 (1)0.077 (2)0.005 (1)0.024 (1)0.001 (1)
N90.066 (1)0.057 (1)0.044 (1)0.007 (1)0.015 (1)0.008 (1)
C100.058 (2)0.049 (1)0.052 (2)0.001 (1)0.013 (1)0.001 (1)
C110.050 (1)0.047 (1)0.054 (2)0.004 (1)0.012 (1)0.003 (1)
C120.061 (2)0.047 (1)0.058 (2)0.003 (1)0.014 (1)0.003 (1)
C130.064 (2)0.053 (2)0.047 (1)0.006 (1)0.008 (1)0.002 (1)
C140.062 (2)0.047 (1)0.060 (2)0.002 (1)0.008 (1)0.008 (1)
C150.054 (2)0.046 (1)0.059 (2)0.004 (1)0.015 (1)0.001 (1)
C160.054 (2)0.051 (1)0.053 (1)0.004 (1)0.013 (1)0.002 (1)
C170.057 (2)0.065 (2)0.054 (2)0.013 (1)0.018 (1)0.003 (1)
C180.068 (2)0.077 (2)0.066 (2)0.004 (2)0.020 (2)0.001 (2)
C190.069 (2)0.097 (3)0.089 (3)0.007 (2)0.024 (2)0.016 (2)
C200.069 (2)0.128 (3)0.065 (2)0.007 (2)0.012 (2)0.018 (2)
C210.070 (2)0.115 (3)0.052 (2)0.020 (2)0.019 (2)0.002 (2)
C220.059 (2)0.080 (2)0.047 (2)0.020 (2)0.018 (1)0.008 (1)
C230.068 (2)0.069 (2)0.054 (2)0.025 (2)0.025 (1)0.016 (1)
C240.087 (2)0.084 (2)0.069 (2)0.028 (2)0.037 (2)0.031 (2)
C250.102 (3)0.068 (2)0.100 (3)0.021 (2)0.052 (2)0.032 (2)
C260.087 (2)0.056 (2)0.103 (3)0.011 (2)0.042 (2)0.011 (2)
C270.075 (2)0.054 (2)0.068 (2)0.014 (1)0.024 (2)0.004 (1)
C280.068 (2)0.052 (2)0.053 (2)0.017 (1)0.023 (1)0.012 (1)
C290.064 (2)0.056 (2)0.047 (1)0.010 (1)0.021 (1)0.009 (1)
C300.054 (1)0.045 (1)0.052 (1)0.001 (1)0.016 (1)0.008 (1)
C310.075 (2)0.069 (2)0.054 (2)0.003 (2)0.014 (1)0.014 (1)
C320.085 (2)0.053 (2)0.077 (2)0.015 (2)0.020 (2)0.004 (1)
Geometric parameters (Å, º) top
O1—C101.269 (3)C19—H190.959
O1—H10.80 (6)C20—C211.374 (6)
O2—C101.253 (4)C20—H200.972
O2—H20.90 (8)C21—C221.396 (4)
O3—N71.212 (4)C21—H210.972
O4—N71.212 (4)C22—C231.437 (4)
O5—N81.215 (3)C23—C241.398 (5)
O6—N81.220 (4)C23—C281.413 (4)
N7—C131.473 (4)C24—C251.364 (5)
N8—C151.474 (4)C24—H240.958
N9—C171.382 (3)C25—C261.392 (5)
N9—C281.389 (4)C25—H250.960
N9—C291.464 (4)C26—C271.390 (5)
C10—C111.488 (3)C26—H260.978
C11—C121.391 (4)C27—C281.391 (4)
C11—C161.386 (4)C27—H270.968
C12—C131.375 (4)C29—C301.519 (3)
C12—H120.965C29—H29A0.969
C13—C141.380 (4)C29—H29B0.966
C14—C151.373 (4)C30—C311.516 (4)
C14—H140.963C30—C321.509 (4)
C15—C161.382 (3)C30—H300.963
C16—H160.965C31—H31A0.961
C17—C181.388 (4)C31—H31B0.964
C17—C221.409 (4)C31—H31C0.969
C18—C191.385 (4)C32—H32A0.963
C18—H180.959C32—H32B0.964
C19—C201.388 (6)C32—H32C0.966
C10—O1—H1116 (5)C22—C21—H21119.7
C10—O2—H2120 (5)C17—C22—C21119.8 (3)
O3—N7—O4124.0 (3)C17—C22—C23106.5 (2)
O3—N7—C13118.7 (3)C21—C22—C23133.7 (3)
O4—N7—C13117.3 (3)C22—C23—C24134.3 (3)
O5—N8—O6124.7 (3)C22—C23—C28106.9 (3)
O5—N8—C15117.9 (3)C24—C23—C28118.7 (3)
O6—N8—C15117.5 (2)C23—C24—C25119.4 (3)
C17—N9—C28108.4 (2)C23—C24—H24120.5
C17—N9—C29126.4 (2)C25—C24—H24120.0
C28—N9—C29123.9 (2)C24—C25—C26121.5 (3)
O1—C10—O2124.7 (2)C24—C25—H25119.8
O1—C10—C11117.0 (2)C26—C25—H25118.7
O2—C10—C11118.3 (2)C25—C26—C27120.9 (3)
C10—C11—C12119.2 (2)C25—C26—H26119.8
C10—C11—C16120.5 (2)C27—C26—H26119.3
C12—C11—C16120.1 (2)C26—C27—C28117.5 (3)
C11—C12—C13118.5 (3)C26—C27—H27121.2
C11—C12—H12121.1C28—C27—H27121.3
C13—C12—H12120.4N9—C28—C23108.7 (2)
N7—C13—C12118.1 (3)N9—C28—C27129.4 (2)
N7—C13—C14118.8 (2)C23—C28—C27121.9 (3)
C12—C13—C14123.1 (2)N9—C29—C30115.4 (2)
C13—C14—C15116.7 (2)N9—C29—H29A108.9
C13—C14—H14121.6N9—C29—H29B108.3
C15—C14—H14121.7C30—C29—H29A108.1
N8—C15—C14118.3 (2)C30—C29—H29B107.7
N8—C15—C16118.8 (2)H29A—C29—H29B108.2
C14—C15—C16122.9 (3)C29—C30—C31107.9 (2)
C11—C16—C15118.7 (2)C29—C30—C32112.2 (2)
C11—C16—H16121.4C29—C30—H30107.9
C15—C16—H16119.9C31—C30—C32111.5 (2)
N9—C17—C18129.2 (3)C31—C30—H30107.9
N9—C17—C22109.4 (2)C32—C30—H30109.1
C18—C17—C22121.3 (2)C30—C31—H31A110.8
C17—C18—C19117.4 (3)C30—C31—H31B110.1
C17—C18—H18122.4C30—C31—H31C109.8
C19—C18—H18120.2H31A—C31—H31B109.1
C18—C19—C20121.8 (3)H31A—C31—H31C108.6
C18—C19—H19120.1H31B—C31—H31C108.4
C20—C19—H19118.0C30—C32—H32A110.2
C19—C20—C21120.8 (3)C30—C32—H32B110.2
C19—C20—H20120.3C30—C32—H32C110.2
C21—C20—H20118.9H32A—C32—H32B108.9
C20—C21—C22118.8 (3)H32A—C32—H32C108.7
C20—C21—H21121.5H32B—C32—H32C108.6
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.80 (6)1.87 (7)2.650 (3)165 (8)
O2—H2···O1i0.90 (8)1.76 (8)2.650 (3)171 (9)
Symmetry code: (i) x+1, y+1, z.

Experimental details

(I)(II)(III)(IV)
Crystal data
Chemical formulaC13H11N·C7H4N2O6C15H15N·C7H4N2O6C16H17N·C7H4N2O6C16H17N·C7H4N2O6
Mr393.36421.41435.44435.44
Crystal system, space groupTriclinic, P1Monoclinic, P21/aTriclinic, P1Monoclinic, P21/c
Temperature (K)298298298298
a, b, c (Å)8.414 (1), 15.763 (2), 6.991 (1)8.504 (2), 29.533 (4), 8.568 (2)16.723 (2), 16.784 (3), 8.4129 (9)8.212 (2), 31.924 (2), 8.438 (1)
α, β, γ (°)91.82 (1), 99.91 (1), 81.59 (1)90, 108.05 (2), 90102.36 (1), 92.34 (1), 109.91 (1)90, 106.54 (1), 90
V3)903.6 (2)2045.8 (7)2152.0 (6)2120.5 (6)
Z2444
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.110.100.100.10
Crystal size (mm)0.6 × 0.4 × 0.10.5 × 0.5 × 0.50.6 × 0.5 × 0.20.5 × 0.4 × 0.3
Data collection
DiffractometerRigaku AFC-7R
diffractometer
Rigaku AFC-7R
diffractometer
Rigaku AFC-7R
diffractometer
Rigaku AFC-7R
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
5045, 4128, 2977 4990, 4685, 3283 10208, 9870, 4817 5184, 4864, 2811
Rint0.0050.0110.0100.006
(sin θ/λ)max1)0.6500.6500.6500.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.147, 1.08 0.041, 0.122, 1.05 0.061, 0.192, 1.74 0.049, 0.165, 1.03
No. of reflections4128468598704864
No. of parameters270288593298
No. of restraints????
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.29, 0.180.21, 0.160.24, 0.250.20, 0.25

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), TEXSAN.

Selected geometric parameters (Å, º) for (I) top
O1—C101.260 (2)O5—N81.214 (2)
O2—C101.265 (2)O6—N81.222 (2)
O3—N71.213 (2)N9—C291.449 (2)
O4—N71.220 (2)
O3—N7—O4124.5 (2)O1—C10—C11117.8 (1)
O5—N8—O6123.8 (2)O2—C10—C11117.7 (2)
O1—C10—O2124.4 (1)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.73 (5)1.92 (5)2.648 (2)172 (5)
O2—H2···O1i0.88 (5)1.77 (5)2.648 (2)179 (5)
Symmetry code: (i) x+1, y+1, z+1.
Selected geometric parameters (Å, º) for (II) top
O1—C101.251 (2)O6—N81.215 (2)
O2—C101.266 (2)N9—C291.474 (2)
O3—N71.216 (3)C29—C301.518 (3)
O4—N71.214 (2)C29—C311.521 (3)
O5—N81.215 (2)
O3—N7—O4124.1 (2)O1—C10—C11118.1 (1)
O5—N8—O6124.8 (2)O2—C10—C11117.1 (1)
O1—C10—O2124.8 (1)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.78 (4)1.86 (4)2.629 (2)174 (5)
O2—H2···O1i0.82 (4)1.81 (4)2.629 (2)178 (4)
Symmetry code: (i) x, y, z+2.
Selected geometric parameters (Å, º) for (III) top
O1—C101.272 (4)O6—N81.215 (4)
O1*—C10*1.281 (4)O6*—N8*1.211 (4)
O2—C101.249 (3)N9—C291.465 (4)
O2*—C10*1.247 (3)N9*—C29*1.448 (3)
O3—N71.199 (4)C29—C301.495 (4)
O3*—N7*1.221 (3)C29*—C30*1.504 (4)
O4—N71.211 (5)C30—C311.529 (4)
O4*—N7*1.214 (4)C30*—C31*1.512 (4)
O5—N81.211 (4)C31—C321.471 (4)
O5*—N8*1.207 (4)C31*—C32*1.472 (5)
O3—N7—O4123.9 (3)O1—C10—C11116.3 (2)
O3*—N7*—O4*124.3 (3)O2—C10—C11118.5 (3)
O5—N8—O6124.0 (2)O1*—C10*—O2*125.5 (3)
O5*—N8*—O6*124.1 (2)O1*—C10*—C11*115.7 (2)
O1—C10—O2125.2 (3)O2*—C10*—C11*118.8 (3)
Hydrogen-bond geometry (Å, º) for (III) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2*0.64 (7)2.02 (7)2.651 (4)171 (6)
O1*—H1*···O20.86 (6)1.82 (6)2.637 (4)158 (5)
O2—H2···O1*0.74 (8)1.90 (8)2.637 (4)169 (8)
O2*—H2*···O11.01 (8)1.65 (8)2.651 (4)170 (6)
Selected geometric parameters (Å, º) for (IV) top
O1—C101.269 (3)O6—N81.220 (4)
O2—C101.253 (4)N9—C291.464 (4)
O3—N71.212 (4)C29—C301.519 (3)
O4—N71.212 (4)C30—C311.516 (4)
O5—N81.215 (3)C30—C321.509 (4)
O3—N7—O4124.0 (3)O1—C10—C11117.0 (2)
O5—N8—O6124.7 (3)O2—C10—C11118.3 (2)
O1—C10—O2124.7 (2)
Hydrogen-bond geometry (Å, º) for (IV) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.80 (6)1.87 (7)2.650 (3)165 (8)
O2—H2···O1i0.90 (8)1.76 (8)2.650 (3)171 (9)
Symmetry code: (i) x+1, y+1, z.
 

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