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In the crystal structure of the title cocrystal, 2C12H6N2O2·C2H6N4O2, the diamino­glyoxime mol­ecules are located on inversion centres, while the 1,10-phenanthroline-5,6-dione mol­ecules are located in general positions. Both mol­ecules are connected through inter­molecular N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806049397/bh2052sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806049397/bh2052Isup2.hkl
Contains datablock I

CCDC reference: 629427

Key indicators

  • Single-crystal X-ray study
  • T = 220 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.048
  • wR factor = 0.136
  • Data-to-parameter ratio = 11.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT432_ALERT_2_B Short Inter X...Y Contact O3 .. C1 .. 2.78 Ang.
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C12 ... 1.53 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O3 .. C12 .. 2.93 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
0 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 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: IPDS Program Package (Stoe & Cie, 1998); cell refinement: IPDS Program Package; data reduction: IPDS Program Package; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL.

Bis(1,10-phenanthroline-5,6-dione) diaminoglyoxime top
Crystal data top
2C12H6N2O2·C2H6N4O2Z = 1
Mr = 538.48F(000) = 278
Triclinic, P1Dx = 1.528 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1513 (8) ÅCell parameters from 2741 reflections
b = 9.3637 (14) Åθ = 3.5–28°
c = 9.6271 (12) ŵ = 0.11 mm1
α = 78.712 (16)°T = 220 K
β = 81.427 (15)°Block, red
γ = 68.269 (15)°0.30 × 0.15 × 0.15 mm
V = 585.18 (13) Å3
Data collection top
Stoe IPDS-1
diffractometer
1395 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.040
Graphite monochromatorθmax = 25.0°, θmin = 3.2°
φ scansh = 88
3472 measured reflectionsk = 1111
1991 independent reflectionsl = 1111
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.0876P)2]
where P = (Fo2 + 2Fc2)/3
1991 reflections(Δ/σ)max < 0.001
181 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.20 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.0596 (2)0.39276 (18)0.77530 (17)0.0469 (5)
O20.1168 (3)0.1953 (2)0.58301 (16)0.0538 (5)
N10.2401 (3)0.0160 (2)1.14428 (18)0.0369 (5)
N20.4397 (3)0.2012 (2)0.95105 (18)0.0349 (4)
C10.0466 (3)0.2604 (2)0.8161 (2)0.0330 (5)
C20.0791 (3)0.1982 (2)0.9673 (2)0.0296 (5)
C30.0183 (4)0.2898 (3)1.0729 (3)0.0414 (6)
H30.10580.39281.04910.050*
C40.0155 (4)0.2272 (3)1.2118 (3)0.0484 (6)
H40.04830.28661.28510.058*
C50.1447 (4)0.0757 (3)1.2424 (2)0.0464 (6)
H50.16710.03431.33810.056*
C60.2083 (3)0.0460 (2)1.0079 (2)0.0274 (5)
C70.3172 (3)0.0578 (2)0.9010 (2)0.0277 (5)
C80.5392 (4)0.2962 (3)0.8578 (3)0.0451 (6)
H80.62410.39700.89250.054*
C90.5255 (4)0.2559 (3)0.7116 (3)0.0464 (6)
H90.60110.32650.64920.056*
C100.3983 (4)0.1099 (3)0.6613 (2)0.0406 (6)
H100.38320.07940.56340.049*
C110.2917 (3)0.0071 (2)0.7566 (2)0.0303 (5)
C120.1518 (3)0.1506 (2)0.7064 (2)0.0343 (5)
O30.4122 (3)0.3105 (2)0.75937 (17)0.0543 (5)
H1O10.49650.25580.81650.081*
N30.5422 (3)0.3635 (2)0.65360 (19)0.0427 (5)
H1N30.17130.46670.61030.064*
H2N30.18550.58760.48070.064*
N40.2380 (3)0.5176 (2)0.55172 (19)0.0421 (5)
C130.4401 (3)0.4660 (2)0.5576 (2)0.0315 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0374 (9)0.0316 (9)0.0574 (10)0.0008 (7)0.0109 (7)0.0086 (7)
O20.0679 (13)0.0519 (10)0.0327 (9)0.0121 (9)0.0220 (8)0.0091 (7)
N10.0401 (11)0.0429 (11)0.0288 (9)0.0176 (9)0.0101 (7)0.0031 (8)
N20.0303 (10)0.0268 (9)0.0419 (10)0.0042 (8)0.0099 (8)0.0013 (7)
C10.0247 (11)0.0285 (11)0.0425 (12)0.0076 (9)0.0101 (9)0.0044 (9)
C20.0252 (10)0.0291 (10)0.0351 (11)0.0106 (9)0.0041 (8)0.0026 (8)
C30.0317 (12)0.0372 (12)0.0566 (14)0.0114 (10)0.0000 (10)0.0146 (10)
C40.0464 (15)0.0648 (17)0.0454 (13)0.0279 (14)0.0075 (11)0.0262 (12)
C50.0529 (15)0.0677 (17)0.0284 (11)0.0320 (14)0.0037 (10)0.0083 (11)
C60.0252 (10)0.0300 (10)0.0282 (10)0.0113 (9)0.0082 (8)0.0008 (8)
C70.0225 (10)0.0260 (10)0.0335 (10)0.0079 (8)0.0077 (8)0.0007 (8)
C80.0341 (13)0.0302 (12)0.0644 (15)0.0017 (10)0.0099 (11)0.0070 (11)
C90.0360 (13)0.0452 (14)0.0594 (15)0.0088 (11)0.0012 (11)0.0243 (11)
C100.0400 (13)0.0500 (14)0.0355 (11)0.0180 (12)0.0033 (9)0.0103 (10)
C110.0293 (11)0.0313 (11)0.0308 (10)0.0114 (9)0.0072 (8)0.0007 (8)
C120.0342 (12)0.0350 (12)0.0319 (11)0.0124 (10)0.0118 (9)0.0065 (9)
O30.0429 (10)0.0670 (12)0.0475 (9)0.0269 (9)0.0218 (8)0.0324 (8)
N30.0425 (11)0.0449 (11)0.0385 (10)0.0198 (10)0.0149 (8)0.0161 (8)
N40.0357 (11)0.0432 (11)0.0370 (10)0.0085 (9)0.0091 (8)0.0113 (8)
C130.0347 (11)0.0265 (10)0.0318 (10)0.0086 (9)0.0108 (8)0.0004 (8)
Geometric parameters (Å, º) top
O1—C11.212 (3)C7—C111.395 (3)
O2—C121.211 (2)C8—C91.393 (3)
N1—C51.336 (3)C8—H80.9400
N1—C61.343 (2)C9—C101.372 (3)
N2—C81.326 (3)C9—H90.9400
N2—C71.343 (3)C10—C111.394 (3)
C1—C21.476 (3)C10—H100.9400
C1—C121.534 (3)C11—C121.478 (3)
C2—C31.394 (3)O3—N31.417 (3)
C2—C61.397 (3)O3—H1O10.8300
C3—C41.370 (3)N3—C131.283 (3)
C3—H30.9400N4—C131.350 (3)
C4—C51.379 (4)N4—H1N30.8701
C4—H40.9400N4—H2N30.8701
C5—H50.9400C13—C13i1.487 (4)
C6—C71.484 (3)
C5—N1—C6117.1 (2)N2—C8—C9124.0 (2)
C8—N2—C7117.77 (18)N2—C8—H8118.0
O1—C1—C2123.2 (2)C9—C8—H8118.0
O1—C1—C12118.90 (19)C10—C9—C8117.9 (2)
C2—C1—C12117.86 (17)C10—C9—H9121.0
C3—C2—C6118.37 (19)C8—C9—H9121.0
C3—C2—C1120.82 (19)C9—C10—C11119.4 (2)
C6—C2—C1120.81 (18)C9—C10—H10120.3
C4—C3—C2118.9 (2)C11—C10—H10120.3
C4—C3—H3120.5C10—C11—C7118.33 (19)
C2—C3—H3120.5C10—C11—C12120.93 (18)
C3—C4—C5118.8 (2)C7—C11—C12120.73 (18)
C3—C4—H4120.6O2—C12—C11122.6 (2)
C5—C4—H4120.6O2—C12—C1119.19 (18)
N1—C5—C4124.0 (2)C11—C12—C1118.25 (17)
N1—C5—H5118.0N3—O3—H1O198.7
C4—C5—H5118.0C13—N3—O3110.48 (19)
N1—C6—C2122.77 (19)C13—N4—H1N3117.3
N1—C6—C7115.99 (17)C13—N4—H2N3118.4
C2—C6—C7121.23 (17)H1N3—N4—H2N3123.3
N2—C7—C11122.50 (18)N3—C13—N4126.7 (2)
N2—C7—C6116.53 (17)N3—C13—C13i115.5 (2)
C11—C7—C6120.97 (17)N4—C13—C13i117.8 (2)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H1O1···N2ii0.832.272.984 (2)144
O3—H1O1···N1ii0.832.343.043 (3)143
N4—H1N3···O10.872.323.166 (3)166
N4—H2N3···O2iii0.872.423.149 (3)142
Symmetry codes: (ii) x+1, y, z+2; (iii) x, y+1, z+1.
 

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