







Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808027347/ym2072sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808027347/ym2072Isup2.hkl |
CCDC reference: 702430
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.042
- wR factor = 0.105
- Data-to-parameter ratio = 15.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT417_ALERT_2_C Short Inter D-H..H-D H10O .. H11C .. 2.11 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact N5 .. C7 .. 2.98 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact C2 .. C6 .. 3.11 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact C5 .. C18 .. 3.13 Ang. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Labels .......... 5 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C5 H8 N3 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 4 H2 O
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
An aqueous solution of CrCl3 (24 mg, 0.15 mmol), pyridine-2,6-diamine (32 mg, 0.3 mmol) and 4-Hydroxypyridine-2,6-dicarboxylic acid (54 mg, 0.3 mmol) was added to each other in a 1:2:2 molar ratio, and the reaction mixture was heated at about 50°C for 4 h. Violet crystals of the title compound were obtained from the solution after two weeks at room temperature.
The hydrogen atoms of NH2 and OH groups and also H atoms of water molecule were found in difference Fourier synthesis. The hydrogen atoms of the H(C) atom positions were calculated. All Hydrogen atoms were refined in isotropic approximation in riding model with the Uiso(H) parameters equal to 1.2 Ueq(Xi), where U(Xi) the equivalent thermal parameters of the carbon or nitrogen or oxygen atom to which corresponding H atom is bonded.
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
(C5H8N3)[Cr(C7H3NO5)2]·2H2O | F(000) = 1148 |
Mr = 560.38 | Dx = 1.718 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 1320 reflections |
a = 6.9590 (4) Å | θ = 3–28° |
b = 20.9904 (12) Å | µ = 0.61 mm−1 |
c = 14.8951 (8) Å | T = 100 K |
β = 95.3030 (13)° | Needle, black |
V = 2166.4 (2) Å3 | 0.32 × 0.08 × 0.07 mm |
Z = 4 |
Bruker APEXII CCD area-detector' diffractometer | 5229 independent reflections |
Radiation source: fine-focus sealed tube | 3694 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.078 |
ω scans | θmax = 28.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −9→9 |
Tmin = 0.829, Tmax = 0.959 | k = −27→27 |
24511 measured reflections | l = −19→19 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: mixed |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0468P)2 + 0.9675P] where P = (Fo2 + 2Fc2)/3 |
5229 reflections | (Δ/σ)max = 0.002 |
336 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.57 e Å−3 |
(C5H8N3)[Cr(C7H3NO5)2]·2H2O | V = 2166.4 (2) Å3 |
Mr = 560.38 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.9590 (4) Å | µ = 0.61 mm−1 |
b = 20.9904 (12) Å | T = 100 K |
c = 14.8951 (8) Å | 0.32 × 0.08 × 0.07 mm |
β = 95.3030 (13)° |
Bruker APEXII CCD area-detector' diffractometer | 5229 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 3694 reflections with I > 2σ(I) |
Tmin = 0.829, Tmax = 0.959 | Rint = 0.078 |
24511 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.47 e Å−3 |
5229 reflections | Δρmin = −0.57 e Å−3 |
336 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cr1 | 0.46263 (6) | 1.098248 (19) | 0.20578 (3) | 0.00992 (10) | |
O1 | 0.3226 (2) | 1.01686 (8) | 0.17083 (11) | 0.0124 (4) | |
O2 | 0.1871 (3) | 0.95887 (8) | 0.05618 (11) | 0.0141 (4) | |
O3 | 0.5836 (2) | 1.18207 (8) | 0.18501 (11) | 0.0127 (4) | |
O4 | 0.6584 (3) | 1.25241 (8) | 0.08081 (12) | 0.0154 (4) | |
O5 | 0.3766 (3) | 1.11140 (8) | −0.20081 (11) | 0.0166 (4) | |
H5O | 0.4037 | 1.1423 | −0.2284 | 0.020* | |
O6 | 0.7149 (2) | 1.05418 (8) | 0.23449 (11) | 0.0138 (4) | |
O7 | 0.9177 (3) | 1.01550 (9) | 0.34882 (12) | 0.0192 (4) | |
O8 | 0.2157 (2) | 1.14101 (8) | 0.23077 (11) | 0.0135 (4) | |
O9 | 0.0389 (3) | 1.17639 (9) | 0.33928 (12) | 0.0174 (4) | |
O10 | 0.5003 (3) | 1.09070 (9) | 0.61131 (11) | 0.0190 (4) | |
H10O | 0.6029 | 1.0846 | 0.6388 | 0.023* | |
O11 | 0.1788 (3) | 0.93417 (8) | 0.28815 (12) | 0.0159 (4) | |
H11D | 0.0901 | 0.9544 | 0.3071 | 0.019* | |
H11C | 0.2300 | 0.9525 | 0.2480 | 0.046 (11)* | |
O12 | 0.4442 (3) | 1.21870 (8) | −0.27326 (12) | 0.0170 (4) | |
H12A | 0.4497 | 1.2508 | −0.2418 | 0.020* | |
H12B | 0.3656 | 1.2273 | −0.3160 | 0.020* | |
N1 | 0.4410 (3) | 1.10250 (10) | 0.07265 (13) | 0.0106 (4) | |
N2 | 0.4719 (3) | 1.09238 (9) | 0.33828 (13) | 0.0105 (4) | |
N3 | −0.0320 (3) | 1.16527 (10) | −0.07279 (13) | 0.0117 (4) | |
H3NA | −0.0906 | 1.1294 | −0.0859 | 0.014* | |
N4 | −0.0433 (3) | 1.19284 (11) | −0.22368 (14) | 0.0178 (5) | |
H4NB | −0.0924 | 1.1563 | −0.2413 | 0.021* | |
H4NA | −0.0025 | 1.2175 | −0.2648 | 0.032 (9)* | |
N5 | −0.0454 (3) | 1.13054 (10) | 0.07407 (14) | 0.0135 (4) | |
H5NB | 0.0119 | 1.1350 | 0.1281 | 0.016* | |
H5NA | −0.0986 | 1.0961 | 0.0506 | 0.016* | |
C1 | 0.3476 (3) | 1.05598 (11) | 0.02427 (16) | 0.0101 (5) | |
C2 | 0.3233 (4) | 1.05809 (12) | −0.06822 (16) | 0.0117 (5) | |
H2A | 0.2573 | 1.0250 | −0.1019 | 0.014* | |
C3 | 0.3993 (3) | 1.11092 (11) | −0.11176 (16) | 0.0108 (5) | |
C4 | 0.4932 (3) | 1.15980 (12) | −0.05965 (16) | 0.0110 (5) | |
H4A | 0.5443 | 1.1959 | −0.0876 | 0.013* | |
C5 | 0.5088 (3) | 1.15376 (11) | 0.03232 (16) | 0.0108 (5) | |
C6 | 0.2781 (3) | 1.00555 (11) | 0.08605 (16) | 0.0105 (5) | |
C7 | 0.5931 (3) | 1.20100 (12) | 0.10225 (16) | 0.0111 (5) | |
C8 | 0.6272 (4) | 1.06604 (12) | 0.38294 (16) | 0.0123 (5) | |
C9 | 0.6455 (4) | 1.06333 (12) | 0.47589 (16) | 0.0122 (5) | |
H9A | 0.7555 | 1.0444 | 0.5078 | 0.015* | |
C10 | 0.4959 (4) | 1.08960 (11) | 0.52222 (16) | 0.0137 (5) | |
C11 | 0.3335 (4) | 1.11654 (12) | 0.47336 (17) | 0.0137 (5) | |
H11A | 0.2305 | 1.1339 | 0.5032 | 0.016* | |
C12 | 0.3287 (4) | 1.11698 (11) | 0.38087 (16) | 0.0117 (5) | |
C13 | 0.7689 (4) | 1.04231 (12) | 0.31917 (16) | 0.0128 (5) | |
C14 | 0.1782 (4) | 1.14746 (11) | 0.31450 (16) | 0.0118 (5) | |
C15 | 0.0192 (4) | 1.20629 (12) | −0.13776 (17) | 0.0132 (5) | |
C16 | 0.1308 (4) | 1.25899 (12) | −0.11129 (17) | 0.0149 (5) | |
H16A | 0.1713 | 1.2879 | −0.1549 | 0.018* | |
C17 | 0.1819 (4) | 1.26871 (12) | −0.02048 (17) | 0.0138 (5) | |
H17A | 0.2600 | 1.3044 | −0.0023 | 0.017* | |
C18 | 0.1230 (4) | 1.22815 (12) | 0.04490 (17) | 0.0135 (5) | |
H18A | 0.1551 | 1.2368 | 0.1071 | 0.016* | |
C19 | 0.0162 (4) | 1.17463 (12) | 0.01759 (16) | 0.0122 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cr1 | 0.0125 (2) | 0.0104 (2) | 0.00680 (19) | 0.00029 (16) | 0.00056 (14) | −0.00067 (15) |
O1 | 0.0170 (9) | 0.0115 (9) | 0.0083 (9) | −0.0017 (7) | 0.0000 (7) | 0.0004 (6) |
O2 | 0.0167 (9) | 0.0123 (9) | 0.0131 (9) | −0.0027 (7) | 0.0006 (7) | −0.0010 (7) |
O3 | 0.0161 (9) | 0.0135 (9) | 0.0084 (9) | −0.0023 (7) | 0.0003 (7) | −0.0013 (7) |
O4 | 0.0189 (10) | 0.0120 (9) | 0.0149 (10) | −0.0027 (8) | −0.0011 (7) | 0.0010 (7) |
O5 | 0.0284 (11) | 0.0143 (10) | 0.0068 (9) | −0.0023 (8) | 0.0011 (7) | 0.0021 (7) |
O6 | 0.0143 (9) | 0.0156 (9) | 0.0114 (9) | 0.0019 (7) | 0.0014 (7) | −0.0015 (7) |
O7 | 0.0170 (10) | 0.0241 (11) | 0.0161 (10) | 0.0082 (8) | −0.0007 (7) | −0.0006 (8) |
O8 | 0.0135 (9) | 0.0175 (9) | 0.0092 (9) | 0.0023 (7) | −0.0002 (7) | −0.0007 (7) |
O9 | 0.0177 (10) | 0.0214 (10) | 0.0134 (10) | 0.0071 (8) | 0.0029 (7) | −0.0001 (7) |
O10 | 0.0214 (10) | 0.0279 (11) | 0.0073 (9) | 0.0029 (8) | −0.0010 (7) | −0.0002 (7) |
O11 | 0.0169 (10) | 0.0181 (10) | 0.0136 (9) | 0.0020 (8) | 0.0052 (7) | 0.0022 (7) |
O12 | 0.0230 (10) | 0.0145 (9) | 0.0128 (9) | −0.0013 (8) | −0.0018 (7) | 0.0020 (7) |
N1 | 0.0102 (10) | 0.0101 (10) | 0.0117 (10) | 0.0019 (8) | 0.0014 (8) | −0.0019 (8) |
N2 | 0.0125 (10) | 0.0100 (10) | 0.0088 (10) | 0.0002 (8) | 0.0003 (8) | −0.0009 (8) |
N3 | 0.0133 (11) | 0.0102 (10) | 0.0118 (11) | −0.0008 (8) | 0.0018 (8) | 0.0010 (8) |
N4 | 0.0215 (12) | 0.0190 (12) | 0.0125 (11) | −0.0055 (10) | −0.0010 (9) | 0.0041 (9) |
N5 | 0.0147 (11) | 0.0158 (11) | 0.0097 (10) | −0.0018 (9) | −0.0007 (8) | −0.0002 (8) |
C1 | 0.0092 (12) | 0.0094 (12) | 0.0118 (12) | 0.0024 (9) | 0.0024 (9) | −0.0006 (9) |
C2 | 0.0116 (12) | 0.0098 (12) | 0.0132 (13) | 0.0025 (9) | −0.0008 (9) | −0.0012 (9) |
C3 | 0.0117 (12) | 0.0140 (13) | 0.0066 (11) | 0.0042 (10) | 0.0001 (9) | −0.0002 (9) |
C4 | 0.0102 (12) | 0.0115 (12) | 0.0114 (12) | 0.0030 (9) | 0.0018 (9) | 0.0018 (9) |
C5 | 0.0081 (12) | 0.0110 (12) | 0.0134 (13) | 0.0015 (9) | 0.0017 (9) | −0.0007 (9) |
C6 | 0.0103 (12) | 0.0116 (12) | 0.0099 (12) | 0.0025 (10) | 0.0030 (9) | 0.0002 (9) |
C7 | 0.0088 (12) | 0.0133 (12) | 0.0113 (12) | 0.0031 (10) | 0.0011 (9) | −0.0018 (9) |
C8 | 0.0129 (13) | 0.0105 (12) | 0.0134 (13) | −0.0018 (10) | −0.0002 (10) | −0.0004 (9) |
C9 | 0.0140 (13) | 0.0112 (12) | 0.0110 (12) | 0.0022 (10) | −0.0014 (9) | 0.0005 (9) |
C10 | 0.0201 (13) | 0.0110 (12) | 0.0098 (12) | −0.0014 (10) | 0.0008 (10) | 0.0015 (9) |
C11 | 0.0160 (13) | 0.0123 (12) | 0.0132 (13) | −0.0016 (10) | 0.0037 (10) | −0.0013 (9) |
C12 | 0.0122 (12) | 0.0100 (12) | 0.0124 (12) | −0.0020 (9) | −0.0011 (9) | −0.0021 (9) |
C13 | 0.0154 (13) | 0.0117 (12) | 0.0113 (12) | −0.0009 (10) | 0.0011 (10) | −0.0017 (9) |
C14 | 0.0145 (13) | 0.0109 (12) | 0.0098 (12) | −0.0008 (10) | 0.0005 (9) | 0.0003 (9) |
C15 | 0.0130 (13) | 0.0143 (13) | 0.0123 (13) | 0.0050 (10) | 0.0016 (10) | 0.0030 (9) |
C16 | 0.0150 (13) | 0.0125 (13) | 0.0173 (14) | 0.0019 (10) | 0.0030 (10) | 0.0039 (10) |
C17 | 0.0111 (12) | 0.0088 (12) | 0.0214 (14) | 0.0015 (10) | 0.0010 (10) | −0.0017 (10) |
C18 | 0.0120 (13) | 0.0130 (13) | 0.0154 (13) | 0.0014 (10) | 0.0000 (10) | −0.0025 (10) |
C19 | 0.0090 (12) | 0.0152 (13) | 0.0123 (13) | 0.0034 (10) | −0.0001 (9) | −0.0002 (9) |
Cr1—N2 | 1.973 (2) | N4—C15 | 1.343 (3) |
Cr1—N1 | 1.977 (2) | N4—H4NB | 0.8700 |
Cr1—O3 | 1.9872 (17) | N4—H4NA | 0.8700 |
Cr1—O6 | 1.9957 (18) | N5—C19 | 1.347 (3) |
Cr1—O8 | 2.0036 (17) | N5—H5NB | 0.8700 |
Cr1—O1 | 2.0111 (17) | N5—H5NA | 0.8701 |
O1—C6 | 1.294 (3) | C1—C2 | 1.373 (3) |
O2—C6 | 1.227 (3) | C1—C6 | 1.511 (3) |
O3—C7 | 1.303 (3) | C2—C3 | 1.412 (3) |
O4—C7 | 1.225 (3) | C2—H2A | 0.9500 |
O5—C3 | 1.321 (3) | C3—C4 | 1.410 (3) |
O5—H5O | 0.7999 | C4—C5 | 1.370 (3) |
O6—C13 | 1.306 (3) | C4—H4A | 0.9500 |
O7—C13 | 1.225 (3) | C5—C7 | 1.516 (3) |
O8—C14 | 1.305 (3) | C8—C9 | 1.380 (3) |
O9—C14 | 1.229 (3) | C8—C13 | 1.515 (3) |
O10—C10 | 1.325 (3) | C9—C10 | 1.413 (3) |
O10—H10O | 0.8000 | C9—H9A | 0.9500 |
O11—H11D | 0.8199 | C10—C11 | 1.405 (4) |
O11—H11C | 0.8201 | C11—C12 | 1.375 (3) |
O12—H12A | 0.8198 | C11—H11A | 0.9500 |
O12—H12B | 0.8201 | C12—C14 | 1.514 (3) |
N1—C5 | 1.339 (3) | C15—C16 | 1.388 (4) |
N1—C1 | 1.345 (3) | C16—C17 | 1.382 (4) |
N2—C12 | 1.334 (3) | C16—H16A | 0.9500 |
N2—C8 | 1.335 (3) | C17—C18 | 1.384 (4) |
N3—C15 | 1.367 (3) | C17—H17A | 0.9500 |
N3—C19 | 1.371 (3) | C18—C19 | 1.387 (3) |
N3—H3NA | 0.8701 | C18—H18A | 0.9500 |
N2—Cr1—N1 | 177.33 (9) | C5—C4—H4A | 120.9 |
N2—Cr1—O3 | 103.64 (8) | C3—C4—H4A | 120.9 |
N1—Cr1—O3 | 78.35 (8) | N1—C5—C4 | 121.6 (2) |
N2—Cr1—O6 | 79.04 (8) | N1—C5—C7 | 110.3 (2) |
N1—Cr1—O6 | 102.70 (8) | C4—C5—C7 | 128.0 (2) |
O3—Cr1—O6 | 93.82 (7) | O2—C6—O1 | 124.7 (2) |
N2—Cr1—O8 | 77.96 (8) | O2—C6—C1 | 121.4 (2) |
N1—Cr1—O8 | 100.31 (8) | O1—C6—C1 | 113.9 (2) |
O3—Cr1—O8 | 90.88 (7) | O4—C7—O3 | 124.6 (2) |
O6—Cr1—O8 | 156.99 (7) | O4—C7—C5 | 121.8 (2) |
N2—Cr1—O1 | 100.15 (8) | O3—C7—C5 | 113.6 (2) |
N1—Cr1—O1 | 77.79 (8) | N2—C8—C9 | 120.8 (2) |
O3—Cr1—O1 | 156.06 (7) | N2—C8—C13 | 111.6 (2) |
O6—Cr1—O1 | 93.28 (7) | C9—C8—C13 | 127.6 (2) |
O8—Cr1—O1 | 91.46 (7) | C8—C9—C10 | 118.0 (2) |
C6—O1—Cr1 | 118.37 (15) | C8—C9—H9A | 121.0 |
C7—O3—Cr1 | 118.46 (15) | C10—C9—H9A | 121.0 |
C3—O5—H5O | 120.7 | O10—C10—C11 | 117.1 (2) |
C13—O6—Cr1 | 117.65 (15) | O10—C10—C9 | 123.1 (2) |
C14—O8—Cr1 | 118.36 (15) | C11—C10—C9 | 119.8 (2) |
C10—O10—H10O | 116.5 | C12—C11—C10 | 117.7 (2) |
H11D—O11—H11C | 113.6 | C12—C11—H11A | 121.1 |
H12A—O12—H12B | 104.7 | C10—C11—H11A | 121.1 |
C5—N1—C1 | 121.1 (2) | N2—C12—C11 | 121.6 (2) |
C5—N1—Cr1 | 119.27 (16) | N2—C12—C14 | 110.8 (2) |
C1—N1—Cr1 | 119.54 (16) | C11—C12—C14 | 127.5 (2) |
C12—N2—C8 | 121.9 (2) | O7—C13—O6 | 126.4 (2) |
C12—N2—Cr1 | 119.67 (17) | O7—C13—C8 | 120.2 (2) |
C8—N2—Cr1 | 118.33 (16) | O6—C13—C8 | 113.4 (2) |
C15—N3—C19 | 123.3 (2) | O9—C14—O8 | 124.9 (2) |
C15—N3—H3NA | 122.3 | O9—C14—C12 | 122.0 (2) |
C19—N3—H3NA | 114.3 | O8—C14—C12 | 113.1 (2) |
C15—N4—H4NB | 123.8 | N4—C15—N3 | 117.4 (2) |
C15—N4—H4NA | 116.6 | N4—C15—C16 | 124.2 (2) |
H4NB—N4—H4NA | 117.1 | N3—C15—C16 | 118.5 (2) |
C19—N5—H5NB | 111.0 | C17—C16—C15 | 118.9 (2) |
C19—N5—H5NA | 117.8 | C17—C16—H16A | 120.6 |
H5NB—N5—H5NA | 127.1 | C15—C16—H16A | 120.6 |
N1—C1—C2 | 121.5 (2) | C16—C17—C18 | 122.1 (2) |
N1—C1—C6 | 110.4 (2) | C16—C17—H17A | 118.9 |
C2—C1—C6 | 128.1 (2) | C18—C17—H17A | 118.9 |
C1—C2—C3 | 118.0 (2) | C17—C18—C19 | 118.5 (2) |
C1—C2—H2A | 121.0 | C17—C18—H18A | 120.7 |
C3—C2—H2A | 121.0 | C19—C18—H18A | 120.7 |
O5—C3—C4 | 123.6 (2) | N5—C19—N3 | 116.8 (2) |
O5—C3—C2 | 116.9 (2) | N5—C19—C18 | 124.5 (2) |
C4—C3—C2 | 119.5 (2) | N3—C19—C18 | 118.7 (2) |
C5—C4—C3 | 118.2 (2) | ||
N2—Cr1—O1—C6 | 175.80 (17) | C3—C4—C5—C7 | −176.5 (2) |
N1—Cr1—O1—C6 | −2.46 (16) | Cr1—O1—C6—O2 | −177.36 (19) |
O3—Cr1—O1—C6 | 2.3 (3) | Cr1—O1—C6—C1 | 2.3 (3) |
O6—Cr1—O1—C6 | −104.75 (17) | N1—C1—C6—O2 | 179.2 (2) |
O8—Cr1—O1—C6 | 97.77 (17) | C2—C1—C6—O2 | −0.1 (4) |
N2—Cr1—O3—C7 | −177.73 (16) | N1—C1—C6—O1 | −0.5 (3) |
N1—Cr1—O3—C7 | 0.44 (17) | C2—C1—C6—O1 | −179.8 (2) |
O6—Cr1—O3—C7 | 102.64 (17) | Cr1—O3—C7—O4 | 177.52 (19) |
O8—Cr1—O3—C7 | −99.91 (17) | Cr1—O3—C7—C5 | −0.6 (3) |
O1—Cr1—O3—C7 | −4.3 (3) | N1—C5—C7—O4 | −177.7 (2) |
N2—Cr1—O6—C13 | −0.10 (17) | C4—C5—C7—O4 | 0.4 (4) |
N1—Cr1—O6—C13 | −178.02 (17) | N1—C5—C7—O3 | 0.5 (3) |
O3—Cr1—O6—C13 | 103.07 (17) | C4—C5—C7—O3 | 178.6 (2) |
O8—Cr1—O6—C13 | 1.7 (3) | C12—N2—C8—C9 | −0.1 (4) |
O1—Cr1—O6—C13 | −99.81 (17) | Cr1—N2—C8—C9 | 176.98 (18) |
N2—Cr1—O8—C14 | 2.31 (17) | C12—N2—C8—C13 | −179.5 (2) |
N1—Cr1—O8—C14 | −179.77 (17) | Cr1—N2—C8—C13 | −2.4 (3) |
O3—Cr1—O8—C14 | −101.46 (17) | N2—C8—C9—C10 | −0.4 (4) |
O6—Cr1—O8—C14 | 0.5 (3) | C13—C8—C9—C10 | 178.9 (2) |
O1—Cr1—O8—C14 | 102.37 (17) | C8—C9—C10—O10 | −178.7 (2) |
O3—Cr1—N1—C5 | −0.11 (17) | C8—C9—C10—C11 | 0.9 (4) |
O6—Cr1—N1—C5 | −91.45 (18) | O10—C10—C11—C12 | 178.6 (2) |
O8—Cr1—N1—C5 | 88.65 (18) | C9—C10—C11—C12 | −1.0 (4) |
O1—Cr1—N1—C5 | 177.91 (19) | C8—N2—C12—C11 | 0.0 (4) |
O3—Cr1—N1—C1 | −175.84 (19) | Cr1—N2—C12—C11 | −176.99 (18) |
O6—Cr1—N1—C1 | 92.83 (18) | C8—N2—C12—C14 | 176.2 (2) |
O8—Cr1—N1—C1 | −87.08 (18) | Cr1—N2—C12—C14 | −0.8 (3) |
O1—Cr1—N1—C1 | 2.18 (17) | C10—C11—C12—N2 | 0.5 (4) |
O3—Cr1—N2—C12 | 87.31 (19) | C10—C11—C12—C14 | −175.0 (2) |
O6—Cr1—N2—C12 | 178.62 (19) | Cr1—O6—C13—O7 | 179.5 (2) |
O8—Cr1—N2—C12 | −0.64 (18) | Cr1—O6—C13—C8 | −1.1 (3) |
O1—Cr1—N2—C12 | −89.97 (19) | N2—C8—C13—O7 | −178.4 (2) |
O3—Cr1—N2—C8 | −89.81 (18) | C9—C8—C13—O7 | 2.3 (4) |
O6—Cr1—N2—C8 | 1.50 (18) | N2—C8—C13—O6 | 2.2 (3) |
O8—Cr1—N2—C8 | −177.77 (19) | C9—C8—C13—O6 | −177.1 (2) |
O1—Cr1—N2—C8 | 92.91 (18) | Cr1—O8—C14—O9 | 174.9 (2) |
C5—N1—C1—C2 | 2.1 (3) | Cr1—O8—C14—C12 | −3.3 (3) |
Cr1—N1—C1—C2 | 177.73 (18) | N2—C12—C14—O9 | −175.7 (2) |
C5—N1—C1—C6 | −177.3 (2) | C11—C12—C14—O9 | 0.2 (4) |
Cr1—N1—C1—C6 | −1.6 (3) | N2—C12—C14—O8 | 2.6 (3) |
N1—C1—C2—C3 | −0.1 (3) | C11—C12—C14—O8 | 178.5 (2) |
C6—C1—C2—C3 | 179.1 (2) | C19—N3—C15—N4 | −177.6 (2) |
C1—C2—C3—O5 | 179.0 (2) | C19—N3—C15—C16 | 2.1 (4) |
C1—C2—C3—C4 | −1.2 (3) | N4—C15—C16—C17 | 178.2 (2) |
O5—C3—C4—C5 | −179.6 (2) | N3—C15—C16—C17 | −1.5 (4) |
C2—C3—C4—C5 | 0.6 (3) | C15—C16—C17—C18 | −1.0 (4) |
C1—N1—C5—C4 | −2.7 (3) | C16—C17—C18—C19 | 2.8 (4) |
Cr1—N1—C5—C4 | −178.40 (18) | C15—N3—C19—N5 | 179.4 (2) |
C1—N1—C5—C7 | 175.5 (2) | C15—N3—C19—C18 | −0.3 (4) |
Cr1—N1—C5—C7 | −0.2 (3) | C17—C18—C19—N5 | 178.2 (2) |
C3—C4—C5—N1 | 1.4 (4) | C17—C18—C19—N3 | −2.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3NA···O2i | 0.87 | 2.03 | 2.840 (3) | 154 |
N4—H4NB···O11i | 0.87 | 2.09 | 2.958 (3) | 173 |
N4—H4NA···O3ii | 0.87 | 2.33 | 3.122 (3) | 151 |
N5—H5NB···O8 | 0.87 | 1.99 | 2.831 (3) | 162 |
N5—H5NA···O2i | 0.87 | 2.01 | 2.812 (3) | 152 |
O5—H5O···O12 | 0.80 | 1.77 | 2.560 (2) | 169 |
O10—H10O···O11iii | 0.80 | 1.83 | 2.624 (3) | 173 |
O11—H11C···O1 | 0.82 | 1.92 | 2.719 (2) | 163 |
O11—H11D···O7iv | 0.82 | 1.90 | 2.709 (3) | 169 |
O12—H12A···O9v | 0.82 | 2.01 | 2.809 (3) | 165 |
O12—H12B···O4ii | 0.82 | 2.05 | 2.872 (3) | 177 |
C16—H16A···O3ii | 0.95 | 2.49 | 3.265 (3) | 139 |
C18—H18A···O12vi | 0.95 | 2.59 | 3.279 (3) | 130 |
Symmetry codes: (i) −x, −y+2, −z; (ii) x−1/2, −y+5/2, z−1/2; (iii) −x+1, −y+2, −z+1; (iv) x−1, y, z; (v) x+1/2, −y+5/2, z−1/2; (vi) x−1/2, −y+5/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | (C5H8N3)[Cr(C7H3NO5)2]·2H2O |
Mr | 560.38 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 6.9590 (4), 20.9904 (12), 14.8951 (8) |
β (°) | 95.3030 (13) |
V (Å3) | 2166.4 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.61 |
Crystal size (mm) | 0.32 × 0.08 × 0.07 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector' diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.829, 0.959 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 24511, 5229, 3694 |
Rint | 0.078 |
(sin θ/λ)max (Å−1) | 0.661 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.104, 1.02 |
No. of reflections | 5229 |
No. of parameters | 336 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.47, −0.57 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3NA···O2i | 0.87 | 2.03 | 2.840 (3) | 154 |
N4—H4NB···O11i | 0.87 | 2.09 | 2.958 (3) | 173 |
N4—H4NA···O3ii | 0.87 | 2.33 | 3.122 (3) | 151 |
N5—H5NB···O8 | 0.87 | 1.99 | 2.831 (3) | 162 |
N5—H5NA···O2i | 0.87 | 2.01 | 2.812 (3) | 152 |
O5—H5O···O12 | 0.80 | 1.77 | 2.560 (2) | 169 |
O10—H10O···O11iii | 0.80 | 1.83 | 2.624 (3) | 173 |
O11—H11C···O1 | 0.82 | 1.92 | 2.719 (2) | 163 |
O11—H11D···O7iv | 0.82 | 1.90 | 2.709 (3) | 169 |
O12—H12A···O9v | 0.82 | 2.01 | 2.809 (3) | 165 |
O12—H12B···O4ii | 0.82 | 2.05 | 2.872 (3) | 177 |
C16—H16A···O3ii | 0.95 | 2.49 | 3.265 (3) | 139 |
C18—H18A···O12vi | 0.95 | 2.59 | 3.279 (3) | 130 |
Symmetry codes: (i) −x, −y+2, −z; (ii) x−1/2, −y+5/2, z−1/2; (iii) −x+1, −y+2, −z+1; (iv) x−1, y, z; (v) x+1/2, −y+5/2, z−1/2; (vi) x−1/2, −y+5/2, z+1/2. |
The molecular structure of the title compound is shown in Fig. 1. Hydrogen bond geometries are given in Table 1. According to the crystal structure, the title compound is composed of an anionic complex, [Cr(hypydc)2]-, protonated diamino-2,6-pyridinium as a counter ion, (pydaH)+, and two uncoordinated water molecules. This compound crystallizes in the monoclinic system, space group P21/n with four molecules in the unit cell.
The CrIII atom is six-coordinated by two 4-hydroxypyridine-2,6-dicarboxylate, (hypydc)2-, groups which act as tridentate ligand through one pyridine N atom and two carboxylate O atoms. N1 and N2 atoms of two (hypydc)2- fragments occupy the axial position, while O1, O3, O6 and O8 atoms form the equatorial plane. The N1—Cr1—N2 angle [177.33 (9)°] deviates slightly from linearity. Therefore, the coordination geometry around CrIII can be described as distorted octahedral. The bond angles O6—Cr1—O1, O3—Cr1—O6, O3—Cr1—O8 and O1—Cr1—O8 (93.28 (7)°, 93.82 (7)°, 90.88 (7)° and 91.46 (7)°, respectively), and the O1—Cr1—O6—C13 and O8—Cr1—O1—C6 torsion angles (-99.81 (17)° and (97.77 (17)°, respectively) show that these two (hypydc)2- groups are almost perpendicular. Furthermore, the bond angles O1—Cr1—O3 [156.06 (7)°] and O6—Cr1—O8 [156.99 (7)°] indicate that four carboxylate groups of the two dianions are in a flattened tetrahedral arrangement around the CrIII atom.
In the crystal structure of (pydaH)[Cr(hypydc)2].2H2O, the spaces between to layers of [Cr(hypydc)2]- anions are filled with (pydaH)+ cations and water molecules. There are also π-π stacking interactions between the aromatic ring of the coordinated (hypydc)2– anion and the aromatic ring of the (pydaH)+ cation with distances of 3.3353 (14) Å for Cg1···Cg2. There are also C—O···π stacking interactions between C6–O2 and Cg1 with O···π distance of 3.166 (2) Å (1 - x, 2 - y, -z) [Cg1 and Cg2 are the centroid for (N1/C1—C5) and (N3/C15—C19) rings, respectively] (Fig. 2).
Intermolecular O—H···O, N—H···O and C—H···O hydrogen bonding with D···A ranging from 2.560 (2) to 3.279 (3) Å, ionpairing, π–π and C—O···π stacking interactions seem to be effective in the stabilization of the crystal structure, resulting in the formation of an interesting supramolecular structure (Fig. 3).