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The title compound, C24H22N2OP2, is an asymmetrically substituted hydrazine derivative bearing a phosphoryl and a phosphanyl substituent. The PNNP backbone has a torsion angle of −131.01 (8)°. In the crystal, mol­ecules form centrosymmetric dimers by inter­molecular N—H...O hydrogen bonds, which are further linked into a three-dimensional network by weak C—H...O and C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314618017844/rz4028sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314618017844/rz4028Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314618017844/rz4028Isup3.cml
Supplementary material

CCDC reference: 1885876

Key indicators

  • Single-crystal X-ray study
  • T = 200 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.031
  • wR factor = 0.075
  • Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT420_ALERT_2_C D-H Without Acceptor N1 --H1 . Please Check PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 3.151 Check
Alert level G PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note) 0.004 Degree PLAT180_ALERT_4_G Check Cell Rounding: # of Values Ending with 0 = 3 Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 14 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 4 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: X-AREA (Stoe & Cie, 2012); cell refinement: X-AREA (Stoe & Cie, 2012); data reduction: X-AREA (Stoe & Cie, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

1-Diphenylphosphanyl-2-(diphenylphosphoryl)hydrazine top
Crystal data top
C24H22N2OP2Z = 2
Mr = 416.37F(000) = 436
Triclinic, P1Dx = 1.308 Mg m3
a = 8.4464 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.4163 (5) ÅCell parameters from 7632 reflections
c = 13.4880 (6) Åθ = 2.1–29.7°
α = 71.550 (4)°µ = 0.22 mm1
β = 76.477 (4)°T = 200 K
γ = 71.750 (4)°Prism, colourless
V = 1057.04 (9) Å30.43 × 0.20 × 0.16 mm
Data collection top
Stoe IPDS II
diffractometer
3786 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.034
Graphite monochromatorθmax = 28.0°, θmin = 2.1°
ω scansh = 1110
18510 measured reflectionsk = 1313
5106 independent reflectionsl = 1717
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.075 w = 1/[σ2(Fo2) + (0.0467P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.89(Δ/σ)max = 0.001
5106 reflectionsΔρmax = 0.38 e Å3
270 parametersΔρmin = 0.22 e Å3
Special details top

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

Refinement. The N-bound hydrogen atoms H1 and H2B could be found from the difference Fourier map and were refined freely. All other H atoms were placed in idealized positions with d(C—H) = 0.95 Å and refined using a riding model with Uiso(H) fixed at 1.2 Ueq(C).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.48544 (17)0.69757 (13)0.19890 (10)0.0229 (3)
C20.5326 (2)0.64375 (15)0.29896 (11)0.0315 (3)
H2A0.62990.56760.31100.038*
C30.4392 (2)0.70007 (17)0.38115 (12)0.0396 (4)
H3A0.47250.66300.44940.048*
C40.2977 (2)0.81011 (17)0.36409 (13)0.0416 (4)
H4A0.23260.84810.42080.050*
C50.2506 (2)0.86493 (18)0.26515 (14)0.0439 (4)
H5A0.15340.94130.25360.053*
C60.34393 (19)0.80947 (15)0.18232 (12)0.0328 (3)
H6A0.31110.84810.11400.039*
C70.80465 (17)0.66634 (13)0.05663 (10)0.0229 (3)
C80.93398 (19)0.59595 (15)0.11728 (11)0.0302 (3)
H8A0.92100.51850.17620.036*
C91.08141 (19)0.63851 (17)0.09194 (12)0.0347 (3)
H9A1.16960.59000.13340.042*
C101.10071 (19)0.75072 (17)0.00700 (12)0.0344 (3)
H10A1.20140.78050.00940.041*
C110.9744 (2)0.82020 (17)0.05451 (12)0.0382 (4)
H11A0.98880.89700.11360.046*
C120.82649 (19)0.77819 (15)0.03034 (11)0.0319 (3)
H12A0.74000.82580.07320.038*
C130.61345 (17)0.11965 (13)0.30235 (10)0.0246 (3)
C140.6910 (2)0.02742 (16)0.38775 (12)0.0351 (3)
H14A0.67790.05650.44990.042*
C150.7867 (2)0.10579 (17)0.38350 (13)0.0429 (4)
H15A0.83780.16790.44280.052*
C160.8082 (2)0.14876 (16)0.29358 (14)0.0414 (4)
H16A0.87560.23980.29020.050*
C170.7314 (2)0.05915 (15)0.20848 (12)0.0365 (3)
H17A0.74510.08910.14670.044*
C180.63471 (19)0.07405 (14)0.21248 (11)0.0287 (3)
H18A0.58230.13490.15340.034*
C190.28166 (18)0.29918 (14)0.33548 (10)0.0261 (3)
C200.2203 (2)0.19537 (16)0.32568 (12)0.0354 (3)
H20A0.29670.11670.30420.042*
C210.0494 (2)0.20513 (18)0.34677 (14)0.0419 (4)
H21A0.00930.13370.33900.050*
C220.0634 (2)0.31765 (17)0.37906 (12)0.0377 (4)
H22A0.18080.32400.39360.045*
C230.0042 (2)0.42118 (16)0.39012 (12)0.0384 (4)
H23A0.08110.49870.41280.046*
C240.1660 (2)0.41228 (15)0.36827 (12)0.0339 (3)
H24A0.20520.48440.37570.041*
N10.65219 (16)0.45605 (12)0.14559 (9)0.0252 (2)
N20.50757 (15)0.40184 (11)0.18533 (9)0.0259 (2)
O10.50978 (12)0.68341 (10)0.00130 (7)0.0275 (2)
P10.60334 (4)0.62701 (3)0.09005 (3)0.02070 (8)
P20.50410 (5)0.29827 (4)0.31182 (3)0.02479 (9)
H10.732 (2)0.4119 (19)0.1144 (15)0.044 (5)*
H2B0.482 (2)0.3803 (18)0.1384 (14)0.036 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0239 (7)0.0243 (6)0.0238 (6)0.0102 (5)0.0020 (5)0.0081 (5)
C20.0354 (8)0.0317 (7)0.0270 (7)0.0057 (6)0.0070 (6)0.0082 (5)
C30.0557 (11)0.0402 (8)0.0244 (7)0.0137 (8)0.0051 (7)0.0098 (6)
C40.0500 (10)0.0414 (8)0.0338 (8)0.0118 (7)0.0067 (7)0.0200 (7)
C50.0395 (10)0.0407 (9)0.0474 (9)0.0040 (7)0.0058 (8)0.0210 (7)
C60.0328 (8)0.0334 (7)0.0328 (7)0.0032 (6)0.0082 (6)0.0123 (6)
C70.0221 (7)0.0266 (6)0.0212 (6)0.0075 (5)0.0023 (5)0.0075 (5)
C80.0279 (8)0.0342 (7)0.0258 (6)0.0087 (6)0.0059 (6)0.0022 (5)
C90.0244 (8)0.0465 (9)0.0335 (7)0.0072 (7)0.0087 (6)0.0097 (6)
C100.0252 (8)0.0479 (9)0.0358 (8)0.0172 (7)0.0020 (6)0.0159 (7)
C110.0368 (9)0.0422 (8)0.0333 (8)0.0204 (7)0.0036 (7)0.0021 (6)
C120.0288 (8)0.0362 (7)0.0286 (7)0.0112 (6)0.0088 (6)0.0000 (6)
C130.0242 (7)0.0254 (6)0.0246 (6)0.0102 (5)0.0031 (5)0.0036 (5)
C140.0407 (9)0.0359 (7)0.0277 (7)0.0094 (7)0.0106 (6)0.0038 (6)
C150.0464 (10)0.0344 (8)0.0391 (9)0.0046 (7)0.0149 (7)0.0029 (6)
C160.0439 (10)0.0265 (7)0.0462 (9)0.0045 (7)0.0028 (7)0.0065 (6)
C170.0447 (10)0.0316 (7)0.0334 (8)0.0114 (7)0.0008 (7)0.0122 (6)
C180.0328 (8)0.0293 (7)0.0237 (6)0.0099 (6)0.0041 (6)0.0046 (5)
C190.0291 (7)0.0288 (6)0.0193 (6)0.0092 (6)0.0026 (5)0.0039 (5)
C200.0316 (8)0.0380 (8)0.0405 (8)0.0126 (6)0.0012 (7)0.0167 (7)
C210.0352 (9)0.0490 (9)0.0476 (9)0.0188 (7)0.0009 (7)0.0171 (8)
C220.0266 (8)0.0475 (9)0.0308 (7)0.0078 (7)0.0032 (6)0.0016 (6)
C230.0347 (9)0.0360 (8)0.0339 (8)0.0006 (7)0.0035 (7)0.0058 (6)
C240.0383 (9)0.0288 (7)0.0324 (7)0.0066 (6)0.0052 (6)0.0073 (6)
N10.0251 (6)0.0233 (5)0.0266 (6)0.0070 (5)0.0006 (5)0.0080 (4)
N20.0336 (7)0.0259 (5)0.0226 (5)0.0143 (5)0.0060 (5)0.0045 (4)
O10.0285 (5)0.0326 (5)0.0238 (5)0.0090 (4)0.0077 (4)0.0070 (4)
P10.02160 (18)0.02251 (16)0.01936 (15)0.00718 (13)0.00382 (12)0.00538 (12)
P20.0297 (2)0.02590 (17)0.02158 (16)0.01021 (14)0.00453 (14)0.00654 (13)
Geometric parameters (Å, º) top
C1—C61.3874 (19)C14—C151.381 (2)
C1—C21.3883 (18)C14—H14A0.9500
C1—P11.7967 (13)C15—C161.376 (2)
C2—C31.382 (2)C15—H15A0.9500
C2—H2A0.9500C16—C171.378 (2)
C3—C41.378 (2)C16—H16A0.9500
C3—H3A0.9500C17—C181.383 (2)
C4—C51.374 (2)C17—H17A0.9500
C4—H4A0.9500C18—H18A0.9500
C5—C61.384 (2)C19—C201.389 (2)
C5—H5A0.9500C19—C241.395 (2)
C6—H6A0.9500C19—P21.8283 (15)
C7—C121.3914 (19)C20—C211.382 (2)
C7—C81.3916 (19)C20—H20A0.9500
C7—P11.7953 (14)C21—C221.379 (2)
C8—C91.384 (2)C21—H21A0.9500
C8—H8A0.9500C22—C231.382 (2)
C9—C101.375 (2)C22—H22A0.9500
C9—H9A0.9500C23—C241.378 (2)
C10—C111.379 (2)C23—H23A0.9500
C10—H10A0.9500C24—H24A0.9500
C11—C121.386 (2)N1—N21.4256 (16)
C11—H11A0.9500N1—P11.6561 (11)
C12—H12A0.9500N1—H10.80 (2)
C13—C181.3915 (18)N2—P21.7049 (12)
C13—C141.3918 (19)N2—H2B0.828 (18)
C13—P21.8304 (14)O1—P11.4813 (9)
C6—C1—C2119.11 (13)C14—C15—H15A119.9
C6—C1—P1119.08 (10)C15—C16—C17119.71 (15)
C2—C1—P1121.82 (10)C15—C16—H16A120.1
C3—C2—C1120.48 (14)C17—C16—H16A120.1
C3—C2—H2A119.8C16—C17—C18120.43 (14)
C1—C2—H2A119.8C16—C17—H17A119.8
C4—C3—C2119.92 (14)C18—C17—H17A119.8
C4—C3—H3A120.0C17—C18—C13120.55 (13)
C2—C3—H3A120.0C17—C18—H18A119.7
C5—C4—C3120.08 (14)C13—C18—H18A119.7
C5—C4—H4A120.0C20—C19—C24118.04 (14)
C3—C4—H4A120.0C20—C19—P2125.26 (11)
C4—C5—C6120.32 (15)C24—C19—P2116.68 (11)
C4—C5—H5A119.8C21—C20—C19120.75 (14)
C6—C5—H5A119.8C21—C20—H20A119.6
C5—C6—C1120.08 (14)C19—C20—H20A119.6
C5—C6—H6A120.0C22—C21—C20120.52 (15)
C1—C6—H6A120.0C22—C21—H21A119.7
C12—C7—C8119.27 (13)C20—C21—H21A119.7
C12—C7—P1117.66 (10)C21—C22—C23119.42 (15)
C8—C7—P1122.95 (10)C21—C22—H22A120.3
C9—C8—C7120.12 (13)C23—C22—H22A120.3
C9—C8—H8A119.9C24—C23—C22120.17 (14)
C7—C8—H8A119.9C24—C23—H23A119.9
C10—C9—C8120.22 (14)C22—C23—H23A119.9
C10—C9—H9A119.9C23—C24—C19121.09 (14)
C8—C9—H9A119.9C23—C24—H24A119.5
C9—C10—C11120.22 (14)C19—C24—H24A119.5
C9—C10—H10A119.9N2—N1—P1112.75 (9)
C11—C10—H10A119.9N2—N1—H1117.6 (14)
C10—C11—C12120.14 (14)P1—N1—H1114.7 (14)
C10—C11—H11A119.9N1—N2—P2114.25 (9)
C12—C11—H11A119.9N1—N2—H2B110.2 (12)
C11—C12—C7120.01 (13)P2—N2—H2B121.8 (12)
C11—C12—H12A120.0O1—P1—N1119.35 (6)
C7—C12—H12A120.0O1—P1—C7111.77 (6)
C18—C13—C14118.22 (13)N1—P1—C7102.73 (6)
C18—C13—P2124.11 (10)O1—P1—C1110.99 (6)
C14—C13—P2117.48 (10)N1—P1—C1102.73 (6)
C15—C14—C13120.97 (14)C7—P1—C1108.36 (6)
C15—C14—H14A119.5N2—P2—C1996.79 (6)
C13—C14—H14A119.5N2—P2—C13106.30 (6)
C16—C15—C14120.11 (14)C19—P2—C13103.11 (6)
C16—C15—H15A119.9
C6—C1—C2—C30.5 (2)C22—C23—C24—C190.4 (2)
P1—C1—C2—C3179.87 (12)C20—C19—C24—C230.1 (2)
C1—C2—C3—C40.3 (2)P2—C19—C24—C23178.73 (11)
C2—C3—C4—C50.8 (3)P1—N1—N2—P2131.01 (8)
C3—C4—C5—C60.5 (3)N2—N1—P1—O159.52 (11)
C4—C5—C6—C10.3 (3)N2—N1—P1—C7176.20 (9)
C2—C1—C6—C50.8 (2)N2—N1—P1—C163.73 (10)
P1—C1—C6—C5179.58 (13)C12—C7—P1—O121.64 (13)
C12—C7—C8—C91.0 (2)C8—C7—P1—O1162.43 (11)
P1—C7—C8—C9174.91 (11)C12—C7—P1—N1150.79 (11)
C7—C8—C9—C100.2 (2)C8—C7—P1—N133.28 (13)
C8—C9—C10—C111.0 (2)C12—C7—P1—C1100.97 (11)
C9—C10—C11—C120.7 (2)C8—C7—P1—C174.96 (12)
C10—C11—C12—C70.5 (2)C6—C1—P1—O111.40 (13)
C8—C7—C12—C111.3 (2)C2—C1—P1—O1169.00 (11)
P1—C7—C12—C11174.78 (12)C6—C1—P1—N1140.06 (11)
C18—C13—C14—C150.1 (2)C2—C1—P1—N140.34 (13)
P2—C13—C14—C15175.06 (13)C6—C1—P1—C7111.69 (12)
C13—C14—C15—C160.7 (3)C2—C1—P1—C767.91 (13)
C14—C15—C16—C171.1 (3)N1—N2—P2—C19165.14 (9)
C15—C16—C17—C180.7 (3)N1—N2—P2—C1389.02 (10)
C16—C17—C18—C130.0 (2)C20—C19—P2—N297.04 (13)
C14—C13—C18—C170.4 (2)C24—C19—P2—N284.50 (11)
P2—C13—C18—C17174.35 (12)C20—C19—P2—C1311.50 (14)
C24—C19—C20—C210.7 (2)C24—C19—P2—C13166.97 (10)
P2—C19—C20—C21179.15 (12)C18—C13—P2—N221.59 (14)
C19—C20—C21—C220.7 (2)C14—C13—P2—N2153.23 (11)
C20—C21—C22—C230.1 (2)C18—C13—P2—C1979.63 (13)
C21—C22—C23—C240.5 (2)C14—C13—P2—C19105.55 (12)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C19–C24 and C7–C12 phenyl rings, respectively.
D—H···AD—HH···AD···AD—H···A
N2—H2B···O1i0.828 (18)2.132 (18)2.9357 (14)163.6 (17)
C10—H10A···O1ii0.952.503.2854 (19)140
C15—H15A···Cg1iii0.952.703.6125 (17)162
C17—H17A···Cg2iv0.952.913.7171 (18)144
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z; (iii) x+1, y, z+1; (iv) x, y1, z.
 

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