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In the title compound, C13H14N4O·C7H9N3O, a phenyl­carbonohydrazide mol­ecule cocrystallizes with a phenyl­semicarbazide mol­ecule. In the crystal structure, extensive hydrogen-bonding and π–π stacking inter­actions stabilize the structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680601172X/sj2034sup1.cif
Contains datablocks I, d

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680601172X/sj2034Isup2.hkl
Contains datablock I

CCDC reference: 608493

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.054
  • wR factor = 0.105
  • Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C18 - C19 .. 8.80 su PLAT230_ALERT_2_B Hirshfeld Test Diff for O1 - C7 .. 8.35 su
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.836 0.994 Tmin(prime) and Tmax expected: 0.972 0.994 RR(prime) = 0.860 Please check that your absorption correction is appropriate. PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 40 Perc. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.86 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - C14 .. 5.53 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C17 - C18 .. 6.40 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C19 - C20 .. 5.57 su PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1A ... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A .. O1 .. 2.61 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C13 H14 N4 O PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C7 H9 N3 O
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 12 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 3 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: TEXSAN (Molecular Structure Corporation, 1998); cell refinement: TEXSAN; data reduction: TEXSAN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1993); software used to prepare material for publication: SHELXL97.

Diphenylcarbonohydrazide phenylsemicarbazide top
Crystal data top
C13H14N4O·C7H9N3OF(000) = 832
Mr = 393.45Dx = 1.308 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4516 reflections
a = 14.0097 (9) Åθ = 1.7–27.5°
b = 5.8841 (3) ŵ = 0.09 mm1
c = 24.3124 (19) ÅT = 293 K
β = 94.273 (3)°Plate, colorless
V = 1998.6 (2) Å30.32 × 0.17 × 0.07 mm
Z = 4
Data collection top
Rigaku Weissenberg IP
diffractometer
4516 independent reflections
Radiation source: fine-focus sealed tube1815 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.059
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
(TEXSAN; Molecular Structure Corporation, 1998)
h = 018
Tmin = 0.836, Tmax = 0.994k = 07
18299 measured reflectionsl = 3131
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0229P)2]
where P = (Fo2 + 2Fc2)/3
4516 reflections(Δ/σ)max < 0.001
262 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.38 e Å3
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. 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
O10.18231 (12)0.2251 (3)0.20019 (6)0.0491 (5)
O20.02616 (11)0.3820 (3)0.06953 (6)0.0430 (4)
N10.25927 (14)0.3167 (4)0.15896 (8)0.0487 (6)
H1A0.21700.40930.14450.058*
N20.23432 (15)0.1370 (4)0.19223 (8)0.0546 (6)
H2B0.24410.14920.22750.065*
N30.17038 (14)0.0558 (4)0.11627 (7)0.0540 (6)
H3B0.14480.17460.10080.065*
H3C0.18010.06320.09690.065*
N40.03660 (14)0.7262 (4)0.04818 (8)0.0453 (5)
H4B0.02580.70650.01410.054*
N50.08227 (14)0.9266 (4)0.06360 (7)0.0441 (5)
H5B0.05561.01930.08740.053*
N60.02065 (13)0.6122 (4)0.13819 (7)0.0449 (5)
H6B0.03680.74780.14690.054*
N70.00711 (15)0.4499 (4)0.18007 (7)0.0468 (5)
H7A0.04370.45020.20230.056*
C10.35766 (18)0.3401 (5)0.14989 (10)0.0471 (7)
C20.3871 (2)0.5431 (5)0.12705 (11)0.0594 (8)
H2A0.34350.66060.11980.071*
C30.4823 (2)0.5686 (7)0.11514 (13)0.0765 (9)
H3A0.50210.70320.09950.092*
C40.5471 (2)0.3960 (8)0.12639 (14)0.0894 (12)
H4A0.61050.41260.11820.107*
C50.5172 (3)0.2002 (7)0.14975 (15)0.0846 (11)
H5A0.56120.08470.15800.102*
C60.4227 (2)0.1691 (5)0.16151 (11)0.0637 (8)
H6A0.40360.03380.17710.076*
C70.19515 (16)0.0561 (5)0.17061 (10)0.0425 (6)
C80.17498 (18)0.9673 (5)0.03769 (9)0.0424 (6)
C90.19680 (19)1.1785 (5)0.01570 (10)0.0523 (7)
H9A0.15001.29090.01670.063*
C100.2873 (2)1.2247 (5)0.00769 (11)0.0637 (8)
H10A0.30141.36840.02200.076*
C110.3570 (2)1.0599 (6)0.01004 (11)0.0666 (9)
H11A0.41821.09170.02560.080*
C120.3353 (2)0.8472 (6)0.01088 (12)0.0652 (8)
H12A0.38170.73390.00900.078*
C130.24452 (19)0.8014 (5)0.03467 (10)0.0544 (7)
H13A0.23030.65740.04870.065*
C140.00948 (16)0.5653 (5)0.08491 (9)0.0372 (6)
C150.07927 (17)0.2860 (4)0.18473 (9)0.0415 (6)
C160.17139 (18)0.3116 (5)0.16065 (9)0.0510 (7)
H16A0.18710.43880.13910.061*
C170.2402 (2)0.1477 (6)0.16860 (11)0.0616 (8)
H17A0.30170.16550.15190.074*
C180.2191 (2)0.0396 (6)0.20058 (11)0.0628 (8)
H18A0.26570.14840.20570.075*
C190.1278 (2)0.0647 (5)0.22503 (10)0.0601 (8)
H19A0.11340.19030.24730.072*
C200.05692 (18)0.0940 (5)0.21697 (9)0.0485 (7)
H20A0.00490.07280.23290.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0537 (11)0.0459 (11)0.0466 (10)0.0027 (9)0.0041 (8)0.0089 (9)
O20.0526 (10)0.0346 (10)0.0414 (9)0.0103 (9)0.0012 (8)0.0026 (8)
N10.0479 (14)0.0430 (13)0.0535 (12)0.0022 (11)0.0074 (10)0.0053 (12)
N20.0748 (16)0.0472 (15)0.0403 (11)0.0122 (13)0.0044 (11)0.0016 (12)
N30.0734 (15)0.0443 (14)0.0415 (11)0.0126 (12)0.0148 (11)0.0016 (11)
N40.0578 (14)0.0424 (13)0.0362 (10)0.0141 (12)0.0072 (10)0.0036 (11)
N50.0540 (13)0.0331 (12)0.0431 (11)0.0072 (11)0.0093 (10)0.0078 (10)
N60.0632 (14)0.0361 (12)0.0362 (10)0.0034 (11)0.0075 (10)0.0006 (11)
N70.0557 (13)0.0481 (13)0.0359 (10)0.0018 (12)0.0028 (9)0.0061 (11)
C10.0483 (17)0.0428 (16)0.0485 (14)0.0034 (14)0.0071 (13)0.0146 (14)
C20.0559 (18)0.0549 (19)0.0674 (18)0.0034 (16)0.0042 (15)0.0094 (17)
C30.067 (2)0.080 (2)0.084 (2)0.021 (2)0.0164 (17)0.017 (2)
C40.051 (2)0.116 (4)0.103 (3)0.006 (3)0.0108 (19)0.045 (3)
C50.060 (2)0.077 (3)0.113 (3)0.014 (2)0.014 (2)0.031 (2)
C60.063 (2)0.0509 (18)0.0745 (19)0.0062 (17)0.0135 (16)0.0181 (17)
C70.0348 (14)0.0464 (16)0.0452 (14)0.0039 (13)0.0037 (11)0.0060 (15)
C80.0479 (16)0.0420 (15)0.0375 (13)0.0030 (14)0.0035 (12)0.0014 (13)
C90.0640 (19)0.0377 (16)0.0533 (15)0.0025 (15)0.0068 (14)0.0009 (14)
C100.076 (2)0.0501 (18)0.0630 (17)0.0170 (18)0.0093 (16)0.0003 (16)
C110.0558 (18)0.077 (2)0.0655 (18)0.0127 (19)0.0083 (15)0.0038 (19)
C120.0509 (18)0.069 (2)0.0755 (19)0.0061 (17)0.0003 (15)0.0006 (18)
C130.0587 (17)0.0436 (17)0.0605 (16)0.0020 (15)0.0015 (14)0.0061 (15)
C140.0358 (14)0.0373 (15)0.0383 (13)0.0031 (12)0.0027 (10)0.0000 (13)
C150.0465 (15)0.0449 (16)0.0340 (12)0.0026 (14)0.0079 (11)0.0030 (13)
C160.0506 (16)0.0552 (18)0.0475 (14)0.0031 (15)0.0050 (12)0.0048 (14)
C170.0543 (18)0.071 (2)0.0594 (17)0.0020 (17)0.0032 (14)0.0014 (18)
C180.0545 (19)0.071 (2)0.0642 (18)0.0106 (17)0.0124 (15)0.0109 (18)
C190.084 (2)0.0461 (17)0.0528 (16)0.0039 (18)0.0200 (15)0.0063 (15)
C200.0535 (17)0.0505 (17)0.0424 (13)0.0009 (16)0.0095 (12)0.0019 (15)
Geometric parameters (Å, º) top
O1—C71.248 (3)C4—H4A0.9300
O2—C141.257 (3)C5—C61.387 (4)
N1—N21.391 (3)C5—H5A0.9300
N1—C11.419 (3)C6—H6A0.9300
N1—H1A0.8600C8—C131.377 (3)
N2—C71.351 (3)C8—C91.378 (3)
N2—H2B0.8600C9—C101.378 (4)
N3—C71.341 (3)C9—H9A0.9300
N3—H3B0.8600C10—C111.374 (4)
N3—H3C0.8600C10—H10A0.9300
N4—C141.337 (3)C11—C121.376 (4)
N4—N51.406 (3)C11—H11A0.9300
N4—H4B0.8600C12—C131.383 (4)
N5—C81.421 (3)C12—H12A0.9300
N5—H5B0.8600C13—H13A0.9300
N6—C141.345 (3)C15—C161.385 (3)
N6—N71.398 (3)C15—C201.397 (3)
N6—H6B0.8600C16—C171.388 (4)
N7—C151.408 (3)C16—H16A0.9300
N7—H7A0.8600C17—C181.369 (4)
C1—C61.372 (4)C17—H17A0.9300
C1—C21.392 (4)C18—C191.378 (4)
C2—C31.394 (4)C18—H18A0.9300
C2—H2A0.9300C19—C201.388 (4)
C3—C41.376 (5)C19—H19A0.9300
C3—H3A0.9300C20—H20A0.9300
C4—C51.364 (5)
N2—N1—C1116.9 (2)N3—C7—N2116.7 (2)
N2—N1—H1A121.5C13—C8—C9118.9 (2)
C1—N1—H1A121.5C13—C8—N5121.6 (2)
C7—N2—N1121.67 (19)C9—C8—N5119.6 (2)
C7—N2—H2B119.2C10—C9—C8120.6 (3)
N1—N2—H2B119.2C10—C9—H9A119.7
C7—N3—H3B120.0C8—C9—H9A119.7
C7—N3—H3C120.0C11—C10—C9120.5 (3)
H3B—N3—H3C120.0C11—C10—H10A119.8
C14—N4—N5121.88 (19)C9—C10—H10A119.8
C14—N4—H4B119.1C10—C11—C12119.3 (3)
N5—N4—H4B119.1C10—C11—H11A120.3
N4—N5—C8116.27 (19)C12—C11—H11A120.3
N4—N5—H5B121.9C11—C12—C13120.1 (3)
C8—N5—H5B121.9C11—C12—H12A119.9
C14—N6—N7122.8 (2)C13—C12—H12A119.9
C14—N6—H6B118.6C8—C13—C12120.6 (3)
N7—N6—H6B118.6C8—C13—H13A119.7
N6—N7—C15117.85 (18)C12—C13—H13A119.7
N6—N7—H7A121.1O2—C14—N4120.5 (2)
C15—N7—H7A121.1O2—C14—N6122.7 (2)
C6—C1—C2120.0 (3)N4—C14—N6116.8 (2)
C6—C1—N1122.3 (3)C16—C15—C20119.2 (3)
C2—C1—N1117.7 (2)C16—C15—N7122.9 (2)
C1—C2—C3119.4 (3)C20—C15—N7117.8 (2)
C1—C2—H2A120.3C15—C16—C17120.1 (3)
C3—C2—H2A120.3C15—C16—H16A120.0
C4—C3—C2120.4 (3)C17—C16—H16A120.0
C4—C3—H3A119.8C18—C17—C16121.0 (3)
C2—C3—H3A119.8C18—C17—H17A119.5
C5—C4—C3119.2 (3)C16—C17—H17A119.5
C5—C4—H4A120.4C17—C18—C19119.1 (3)
C3—C4—H4A120.4C17—C18—H18A120.5
C4—C5—C6121.7 (3)C19—C18—H18A120.5
C4—C5—H5A119.2C18—C19—C20121.2 (3)
C6—C5—H5A119.2C18—C19—H19A119.4
C1—C6—C5119.3 (3)C20—C19—H19A119.4
C1—C6—H6A120.3C19—C20—C15119.4 (2)
C5—C6—H6A120.3C19—C20—H20A120.3
O1—C7—N3122.1 (2)C15—C20—H20A120.3
O1—C7—N2121.2 (2)
C1—N1—N2—C7101.7 (3)C9—C10—C11—C120.5 (5)
C14—N4—N5—C8120.5 (2)C10—C11—C12—C130.9 (5)
C14—N6—N7—C1575.9 (3)C9—C8—C13—C121.2 (4)
N2—N1—C1—C615.2 (3)N5—C8—C13—C12177.8 (2)
N2—N1—C1—C2166.5 (2)C11—C12—C13—C80.0 (4)
C6—C1—C2—C31.3 (4)N5—N4—C14—O2175.83 (19)
N1—C1—C2—C3177.1 (2)N5—N4—C14—N65.4 (3)
C1—C2—C3—C40.7 (4)N7—N6—C14—O29.8 (3)
C2—C3—C4—C50.5 (5)N7—N6—C14—N4171.5 (2)
C3—C4—C5—C61.2 (5)N6—N7—C15—C1617.6 (3)
C2—C1—C6—C50.7 (4)N6—N7—C15—C20164.9 (2)
N1—C1—C6—C5177.6 (2)C20—C15—C16—C170.1 (4)
C4—C5—C6—C10.6 (5)N7—C15—C16—C17177.5 (2)
N1—N2—C7—O1172.4 (2)C15—C16—C17—C180.7 (4)
N1—N2—C7—N38.1 (4)C16—C17—C18—C190.1 (4)
N4—N5—C8—C1348.5 (3)C17—C18—C19—C201.1 (4)
N4—N5—C8—C9132.5 (2)C18—C19—C20—C151.8 (4)
C13—C8—C9—C101.6 (4)C16—C15—C20—C191.2 (4)
N5—C8—C9—C10177.5 (2)N7—C15—C20—C19176.4 (2)
C8—C9—C10—C110.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3B···O20.862.152.952 (2)154
N7—H7A···O10.862.352.973 (3)129
N1—H1A···O1i0.862.613.098 (3)117
N2—H2B···O1ii0.862.112.899 (2)153
N4—H4B···O2iii0.862.102.946 (2)168
N5—H5B···O2iv0.862.483.079 (3)128
Symmetry codes: (i) x, y1, z; (ii) x+1/2, y1/2, z+1/2; (iii) x, y+1, z; (iv) x, y+1, z.
 

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