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In the crystal structure of the title compound, C10H10N3+·NO3·H2O, (I), the asymmetric unit contains two crystallographically independent but similar subunits. The protonated C10H10N3+ cation adopts the normal transtrans configuration and approximately planar geometry. Multiple hydrogen-bonding interactions expand the structure, resulting in a two-dimensional layered architecture, which is further stabilized by aromatic π–π stacking interactions between the protonated cations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804004015/lh6172sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804004015/lh6172Isup2.hkl
Contains datablock I

CCDC reference: 236105

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.068
  • wR factor = 0.182
  • Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT242_ALERT_2_A Check Low U(eq) as Compared to Neighbors .... N8
Author Response: The atom N8 belongs to a nitrate anion. The larger than normal displacement ellipsoids for the O atoms (O4, O5 and O6) suggest that this anion may be partially disordered (a similar situation may also occur for the nitrate anion containing N7). In the present refinement a disorder model of the nitrate anion was not used. It should also be noted that the highest density peak, of 0.73e/\%A^3^ in the final difference Fourier is approximately 1.36 \%A from N8.


Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C14 - C15 .. 8.61 su PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... N7
Author Response: The atom N8 belongs to a nitrate anion. The larger than normal displacement ellipsoids for the O atoms (O4, O5 and O6) suggest that this anion may be partially disordered (a similar situation may also occur for the nitrate anion containing N7). In the present refinement a disorder model of the nitrate anion was not used. It should also be noted that the highest density peak, of 0.73e/\%A^3^ in the final difference Fourier is approximately 1.36 \%A from N8.


Alert level C DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.732 Test value = 0.600 DIFMX02_ALERT_1_C The minimum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.73 e/A   3 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT432_ALERT_2_C Short Inter X...Y Contact O4 .. C15 .. 2.95 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: SHELXL97.

(2-Pyridinio-2'-pyridyl)amine nitrate hydrate top
Crystal data top
C10H12N4O4Z = 4
Mr = 252.24F(000) = 528
Triclinic, P1Dx = 1.433 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.795 (2) ÅCell parameters from 845 reflections
b = 9.734 (3) Åθ = 2.3–25.0°
c = 17.164 (5) ŵ = 0.11 mm1
α = 95.982 (6)°T = 293 K
β = 102.332 (6)°Block, colorless
γ = 110.480 (5)°0.30 × 0.20 × 0.20 mm
V = 1168.9 (6) Å3
Data collection top
BRUKER SMART 1000
diffractometer
2266 reflections with I > 2σ(I)
ω scansRint = 0.018
Absorption correction: multi-scan
[SAINT (Bruker 1998) and SADABS (Sheldrick, 1998)]
θmax = 25.0°
Tmin = 0.967, Tmax = 0.978h = 96
4852 measured reflectionsk = 1011
4088 independent reflectionsl = 2019
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.068 w = 1/[σ2(Fo2) + (0.0606P)2 + 0.642P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.182(Δ/σ)max < 0.001
S = 1.10Δρmax = 0.73 e Å3
4088 reflectionsΔρmin = 0.45 e Å3
328 parameters
Special details top

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

Refinement. Full-MATRIX

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.4234 (5)0.7232 (4)0.1797 (2)0.1012 (12)
O20.5142 (4)0.9570 (3)0.1957 (2)0.0934 (11)
O30.6887 (5)0.8491 (5)0.1603 (2)0.1119 (13)
O40.3006 (7)0.3156 (5)0.3487 (3)0.166 (2)
O50.3951 (4)0.1399 (4)0.3268 (2)0.0846 (9)
O60.1037 (5)0.1059 (4)0.2904 (3)0.1204 (15)
N10.8552 (4)0.6273 (3)1.05874 (17)0.0490 (8)
H10.92560.70171.09790.059*
N20.6526 (4)0.5560 (3)0.92712 (17)0.0497 (8)
H20.63510.46440.92940.060*
N30.7338 (4)0.3693 (3)1.01641 (18)0.0544 (8)
N40.7763 (4)0.4024 (3)0.43517 (16)0.0455 (7)
H40.79380.34350.39950.055*
N50.7179 (4)0.4306 (4)0.56278 (18)0.0577 (8)
H50.73100.52150.56050.069*
N60.7849 (4)0.6410 (3)0.4740 (2)0.0609 (9)
N70.5448 (5)0.8439 (4)0.17742 (18)0.0565 (8)
N80.2665 (6)0.1826 (4)0.3265 (2)0.0663 (9)
C10.7652 (5)0.6628 (4)0.9918 (2)0.0428 (8)
C20.7893 (5)0.8104 (4)0.9876 (2)0.0512 (9)
H2A0.86620.88681.03180.061*
C30.7012 (6)0.8424 (5)0.9193 (3)0.0635 (11)
H3A0.71720.94100.91690.076*
C40.5864 (6)0.7290 (5)0.8525 (3)0.0658 (11)
H4A0.52620.75080.80530.079*
C50.5646 (6)0.5876 (5)0.8578 (2)0.0610 (11)
H5A0.48890.51050.81370.073*
C60.8503 (5)0.4890 (4)1.0734 (2)0.0438 (8)
C70.9653 (5)0.4803 (5)1.1449 (2)0.0588 (10)
H7A1.04760.56601.18270.071*
C80.9537 (6)0.3406 (5)1.1580 (3)0.0653 (11)
H8A1.02860.33081.20540.078*
C90.8313 (7)0.2156 (5)1.1010 (3)0.0695 (12)
H9A0.82040.12041.10930.083*
C100.7263 (6)0.2354 (4)1.0316 (3)0.0647 (11)
H10A0.64470.15100.99270.078*
C110.7365 (4)0.3464 (4)0.5016 (2)0.0439 (9)
C120.7182 (5)0.1998 (4)0.5069 (2)0.0578 (10)
H12A0.73080.13990.46440.069*
C130.6827 (6)0.1452 (5)0.5727 (3)0.0723 (13)
H13A0.67250.04800.57600.087*
C140.6615 (6)0.2315 (6)0.6348 (3)0.0772 (14)
H14A0.63600.19270.68020.093*
C150.6771 (6)0.3730 (6)0.6308 (2)0.0752 (14)
H15A0.66100.43140.67290.090*
C160.7924 (5)0.5405 (4)0.4173 (2)0.0463 (9)
C170.8179 (5)0.5694 (5)0.3418 (2)0.0619 (11)
H17A0.82220.49710.30320.074*
C180.8365 (6)0.7099 (6)0.3267 (3)0.0807 (15)
H18A0.85360.73420.27720.097*
C190.8296 (6)0.8139 (6)0.3857 (4)0.0909 (17)
H19A0.84260.90910.37660.109*
C200.8036 (6)0.7754 (5)0.4567 (4)0.0812 (14)
H20A0.79830.84620.49590.097*
O1W0.1092 (4)0.8689 (3)0.17904 (16)0.0676 (8)
H1WA0.07990.92300.21590.101*
H1WB0.23050.88340.18330.101*
O2W0.8092 (4)0.1897 (3)0.32182 (17)0.0761 (9)
H2WA0.91660.18590.31260.114*
H2WB0.69880.13290.28490.114*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.107 (3)0.063 (2)0.111 (3)0.006 (2)0.039 (2)0.0044 (18)
O20.079 (2)0.057 (2)0.135 (3)0.0331 (17)0.011 (2)0.0049 (18)
O30.100 (3)0.164 (4)0.131 (3)0.085 (3)0.072 (2)0.067 (3)
O40.176 (5)0.113 (4)0.195 (5)0.062 (3)0.049 (4)0.047 (3)
O50.072 (2)0.087 (2)0.099 (2)0.0426 (19)0.0114 (18)0.0162 (18)
O60.060 (2)0.100 (3)0.180 (4)0.027 (2)0.021 (2)0.025 (3)
N10.0561 (19)0.0378 (17)0.0493 (18)0.0166 (14)0.0102 (15)0.0059 (13)
N20.0535 (19)0.0460 (18)0.0503 (18)0.0209 (15)0.0129 (15)0.0087 (15)
N30.065 (2)0.0389 (18)0.061 (2)0.0212 (15)0.0193 (17)0.0092 (15)
N40.0487 (18)0.0434 (17)0.0411 (16)0.0152 (14)0.0104 (14)0.0063 (13)
N50.0495 (19)0.065 (2)0.055 (2)0.0215 (16)0.0112 (16)0.0057 (17)
N60.054 (2)0.0414 (19)0.087 (2)0.0207 (15)0.0142 (18)0.0104 (17)
N70.062 (2)0.059 (2)0.0506 (19)0.0256 (19)0.0146 (17)0.0092 (16)
N80.075 (3)0.052 (2)0.073 (2)0.028 (2)0.023 (2)0.0054 (18)
C10.043 (2)0.045 (2)0.043 (2)0.0168 (16)0.0153 (17)0.0095 (17)
C20.057 (2)0.042 (2)0.058 (2)0.0181 (18)0.0195 (19)0.0135 (18)
C30.076 (3)0.056 (3)0.078 (3)0.035 (2)0.033 (2)0.031 (2)
C40.079 (3)0.079 (3)0.061 (3)0.046 (3)0.026 (2)0.034 (2)
C50.060 (3)0.077 (3)0.045 (2)0.030 (2)0.0075 (19)0.007 (2)
C60.044 (2)0.043 (2)0.052 (2)0.0190 (17)0.0203 (18)0.0160 (17)
C70.054 (2)0.063 (3)0.063 (3)0.023 (2)0.016 (2)0.021 (2)
C80.070 (3)0.078 (3)0.070 (3)0.041 (3)0.030 (2)0.041 (3)
C90.087 (3)0.057 (3)0.096 (3)0.043 (3)0.050 (3)0.038 (3)
C100.086 (3)0.042 (2)0.076 (3)0.028 (2)0.033 (3)0.015 (2)
C110.0327 (19)0.051 (2)0.040 (2)0.0119 (16)0.0020 (16)0.0050 (17)
C120.052 (2)0.051 (2)0.062 (3)0.0135 (18)0.009 (2)0.0157 (19)
C130.061 (3)0.073 (3)0.078 (3)0.018 (2)0.014 (2)0.029 (3)
C140.058 (3)0.097 (4)0.075 (3)0.022 (3)0.014 (2)0.044 (3)
C150.050 (3)0.125 (4)0.047 (3)0.034 (3)0.013 (2)0.002 (3)
C160.035 (2)0.046 (2)0.054 (2)0.0144 (16)0.0045 (17)0.0132 (18)
C170.051 (2)0.063 (3)0.064 (3)0.013 (2)0.007 (2)0.024 (2)
C180.050 (3)0.092 (4)0.092 (4)0.014 (3)0.007 (2)0.051 (3)
C190.059 (3)0.056 (3)0.155 (5)0.020 (2)0.014 (3)0.046 (4)
C200.067 (3)0.056 (3)0.121 (4)0.028 (2)0.020 (3)0.015 (3)
O1W0.0533 (16)0.0633 (18)0.0747 (18)0.0179 (13)0.0089 (14)0.0028 (14)
O2W0.0599 (18)0.082 (2)0.0789 (19)0.0285 (15)0.0166 (15)0.0142 (16)
Geometric parameters (Å, º) top
O1—N71.235 (4)C5—H5A0.9300
O2—N71.229 (4)C6—C71.386 (5)
O3—N71.205 (4)C7—C81.376 (5)
O4—N81.227 (5)C7—H7A0.9300
O5—N81.212 (4)C8—C91.374 (6)
O6—N81.207 (4)C8—H8A0.9300
N1—C11.357 (4)C9—C101.366 (6)
N1—C61.384 (4)C9—H9A0.9300
N1—H10.8600C10—H10A0.9300
N2—C11.337 (4)C11—C121.398 (5)
N2—C51.363 (4)C12—C131.337 (5)
N2—H20.8600C12—H12A0.9300
N3—C61.335 (4)C13—C141.363 (6)
N3—C101.339 (5)C13—H13A0.9300
N4—C111.362 (4)C14—C151.350 (6)
N4—C161.380 (4)C14—H14A0.9300
N4—H40.8600C15—H15A0.9300
N5—C111.328 (4)C16—C171.394 (5)
N5—C151.396 (5)C17—C181.382 (6)
N5—H50.8600C17—H17A0.9300
N6—C161.331 (5)C18—C191.379 (7)
N6—C201.337 (5)C18—H18A0.9300
C1—C21.393 (5)C19—C201.347 (7)
C2—C31.351 (5)C19—H19A0.9300
C2—H2A0.9300C20—H20A0.9300
C3—C41.393 (6)O1W—H1WA0.8977
C3—H3A0.9300O1W—H1WB0.8916
C4—C51.342 (5)O2W—H2WA0.8964
C4—H4A0.9300O2W—H2WB0.8992
C1—N1—C6129.6 (3)C9—C8—C7120.0 (4)
C1—N1—H1115.2C9—C8—H8A120.0
C6—N1—H1115.2C7—C8—H8A120.0
C1—N2—C5122.1 (3)C10—C9—C8118.0 (4)
C1—N2—H2119.0C10—C9—H9A121.0
C5—N2—H2119.0C8—C9—H9A121.0
C6—N3—C10117.1 (3)N3—C10—C9123.9 (4)
C11—N4—C16128.9 (3)N3—C10—H10A118.1
C11—N4—H4115.5C9—C10—H10A118.1
C16—N4—H4115.5N5—C11—N4120.7 (3)
C11—N5—C15120.6 (4)N5—C11—C12119.1 (3)
C11—N5—H5119.7N4—C11—C12120.2 (3)
C15—N5—H5119.7C13—C12—C11120.5 (4)
C16—N6—C20117.5 (4)C13—C12—H12A119.7
O3—N7—O2122.3 (4)C11—C12—H12A119.7
O3—N7—O1120.7 (4)C12—C13—C14120.2 (5)
O2—N7—O1117.0 (4)C12—C13—H13A119.9
O6—N8—O5122.3 (4)C14—C13—H13A119.9
O6—N8—O4115.8 (4)C15—C14—C13120.4 (4)
O5—N8—O4120.3 (4)C15—C14—H14A119.8
N2—C1—N1120.3 (3)C13—C14—H14A119.8
N2—C1—C2118.2 (3)C14—C15—N5119.3 (4)
N1—C1—C2121.5 (3)C14—C15—H15A120.3
C3—C2—C1120.0 (4)N5—C15—H15A120.3
C3—C2—H2A120.0N6—C16—N4117.8 (3)
C1—C2—H2A120.0N6—C16—C17123.1 (4)
C2—C3—C4120.5 (4)N4—C16—C17119.0 (3)
C2—C3—H3A119.7C18—C17—C16117.3 (4)
C4—C3—H3A119.7C18—C17—H17A121.4
C5—C4—C3118.5 (4)C16—C17—H17A121.4
C5—C4—H4A120.7C19—C18—C17119.5 (5)
C3—C4—H4A120.7C19—C18—H18A120.3
C4—C5—N2120.6 (4)C17—C18—H18A120.3
C4—C5—H5A119.7C20—C19—C18119.0 (5)
N2—C5—H5A119.7C20—C19—H19A120.5
N3—C6—N1117.3 (3)C18—C19—H19A120.5
N3—C6—C7123.1 (3)N6—C20—C19123.7 (5)
N1—C6—C7119.6 (3)N6—C20—H20A118.2
C8—C7—C6117.8 (4)C19—C20—H20A118.2
C8—C7—H7A121.1H1WA—O1W—H1WB119.6
C6—C7—H7A121.1H2WA—O2W—H2WB117.8
C5—N2—C1—N1177.8 (3)C15—N5—C11—N4180.0 (3)
C5—N2—C1—C21.1 (5)C15—N5—C11—C121.2 (5)
C6—N1—C1—N20.3 (5)C16—N4—C11—N54.0 (5)
C6—N1—C1—C2179.2 (3)C16—N4—C11—C12177.3 (3)
N2—C1—C2—C30.5 (5)N5—C11—C12—C130.1 (5)
N1—C1—C2—C3178.5 (3)N4—C11—C12—C13178.7 (3)
C1—C2—C3—C40.3 (6)C11—C12—C13—C140.9 (6)
C2—C3—C4—C50.4 (6)C12—C13—C14—C150.4 (7)
C3—C4—C5—N20.2 (6)C13—C14—C15—N50.8 (6)
C1—N2—C5—C41.0 (5)C11—N5—C15—C141.6 (5)
C10—N3—C6—N1178.5 (3)C20—N6—C16—N4179.0 (3)
C10—N3—C6—C72.0 (5)C20—N6—C16—C170.2 (5)
C1—N1—C6—N34.0 (5)C11—N4—C16—N66.4 (5)
C1—N1—C6—C7175.5 (3)C11—N4—C16—C17174.4 (3)
N3—C6—C7—C81.8 (5)N6—C16—C17—C180.2 (5)
N1—C6—C7—C8178.8 (3)N4—C16—C17—C18179.0 (3)
C6—C7—C8—C90.2 (6)C16—C17—C18—C190.1 (6)
C7—C8—C9—C101.0 (6)C17—C18—C19—C200.4 (7)
C6—N3—C10—C90.7 (6)C16—N6—C20—C190.1 (6)
C8—C9—C10—N30.8 (6)C18—C19—C20—N60.4 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1wi0.861.922.775 (5)173
N2—H2···N30.861.992.650 (5)132
N2—H2···O1ii0.862.322.910 (4)126
N4—H4···O2w0.861.952.808 (4)173
N5—H5···N60.862.002.651 (5)131
N5—H5···O4ii0.862.222.827 (5)127
O1w—H1wa···O6iii0.902.012.857 (4)157
O1w—H1wb···O20.892.032.908 (5)169
O2w—H2wa···O6iv0.901.962.823 (4)161
O2w—H2wb···O2v0.902.032.883 (4)157
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y+1, z+1; (iii) x, y+1, z; (iv) x+1, y, z; (v) x, y1, z.
 

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