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In the title compound, C20H18NO3P, the C=O and P=O groups of the carbacyl­amido­phosphate (CAPh) fragments are located in a synclinal position relative to each othe. The N—H group is involved in the formation of an intra­molecular hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205698901900762X/lh5904sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205698901900762X/lh5904Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205698901900762X/lh5904Isup3.cml
Supplementary material

CCDC reference: 1918613

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.043
  • wR factor = 0.113
  • Data-to-parameter ratio = 25.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00432 Ang. PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 3.769 Check PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min). 6 Note PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage 89 %
Alert level G PLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do ! PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 1 Report PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 181 Note PLAT961_ALERT_5_G Dataset Contains no Negative Intensities ....... Please Check PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 2 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 4 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 3 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

N-(Diphenylphosphoryl)-2-methoxybenzamide top
Crystal data top
C20H18NO3PDx = 1.322 Mg m3
Mr = 351.32Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 5505 reflections
a = 8.317 (2) Åθ = 3.2–30.6°
b = 12.657 (2) ŵ = 0.17 mm1
c = 16.763 (3) ÅT = 294 K
V = 1764.6 (6) Å3Block, colourless
Z = 40.5 × 0.4 × 0.3 mm
F(000) = 736
Data collection top
Rigaku Oxford Diffraction Xcalibur, Sapphire3
diffractometer
5691 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source4247 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
Detector resolution: 16.1827 pixels mm-1θmax = 32.2°, θmin = 3.2°
ω scansh = 1212
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2018)
k = 1716
Tmin = 0.986, Tmax = 1.000l = 2324
18281 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.043 w = 1/[σ2(Fo2) + (0.0551P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.113(Δ/σ)max = 0.001
S = 1.11Δρmax = 0.23 e Å3
5691 reflectionsΔρmin = 0.32 e Å3
227 parametersAbsolute structure: Flack x determined using 1430 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraintsAbsolute structure parameter: 0.01 (4)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P10.75683 (6)0.34774 (4)0.68054 (3)0.03788 (14)
O10.8432 (2)0.33778 (15)0.75665 (10)0.0522 (4)
O20.8579 (2)0.57607 (14)0.70208 (11)0.0601 (5)
O30.8588 (2)0.48946 (15)0.46564 (10)0.0574 (5)
N10.8291 (2)0.43972 (14)0.61711 (11)0.0420 (4)
H10.8391310.4207760.5680980.050*
C10.7720 (3)0.23277 (18)0.61801 (14)0.0454 (5)
C20.6930 (4)0.2254 (2)0.54479 (17)0.0585 (7)
H20.6245780.2793550.5284700.070*
C30.7160 (4)0.1383 (3)0.4964 (2)0.0768 (10)
H30.6655540.1345630.4470090.092*
C40.8138 (5)0.0571 (3)0.5216 (2)0.0815 (11)
H40.8278020.0019370.4892920.098*
C50.8912 (5)0.0626 (3)0.5942 (2)0.0802 (10)
H50.9562310.0070640.6109050.096*
C60.8722 (3)0.1509 (2)0.64224 (18)0.0591 (6)
H60.9264690.1553110.6906430.071*
C70.5462 (3)0.37685 (18)0.69283 (13)0.0410 (5)
C80.4455 (3)0.2966 (2)0.72018 (16)0.0528 (6)
H80.4863110.2290640.7281940.063*
C90.2844 (3)0.3171 (3)0.73552 (18)0.0653 (8)
H90.2170610.2627770.7521710.078*
C100.2247 (3)0.4165 (3)0.72626 (17)0.0669 (8)
H100.1174150.4301920.7380740.080*
C110.3223 (3)0.4969 (3)0.6995 (2)0.0706 (9)
H110.2809300.5646450.6929760.085*
C120.4832 (3)0.4765 (2)0.68216 (19)0.0553 (6)
H120.5485970.5306410.6632570.066*
C130.8734 (3)0.54108 (18)0.63499 (14)0.0405 (5)
C140.9427 (3)0.60615 (19)0.56888 (14)0.0417 (5)
C151.0164 (3)0.7003 (2)0.59123 (18)0.0557 (6)
H151.0208940.7186200.6449150.067*
C161.0828 (4)0.7669 (3)0.5352 (3)0.0769 (10)
H161.1306140.8300770.5507530.092*
C171.0775 (4)0.7386 (3)0.4553 (2)0.0814 (10)
H171.1247420.7825600.4175360.098*
C181.0042 (4)0.6472 (3)0.43069 (19)0.0662 (7)
H180.9998390.6302350.3767500.079*
C190.9367 (3)0.58040 (19)0.48673 (15)0.0460 (5)
C200.8551 (5)0.4599 (3)0.38290 (17)0.0768 (9)
H20A0.8006720.5135210.3527650.115*
H20B0.7991390.3939590.3771710.115*
H20C0.9631010.4523060.3634870.115*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0406 (3)0.0420 (3)0.0310 (2)0.0018 (2)0.0008 (2)0.0024 (2)
O10.0519 (8)0.0658 (11)0.0389 (8)0.0029 (8)0.0059 (7)0.0059 (8)
O20.0794 (12)0.0568 (11)0.0442 (10)0.0133 (9)0.0112 (9)0.0149 (8)
O30.0811 (12)0.0574 (11)0.0335 (9)0.0146 (9)0.0021 (9)0.0008 (8)
N10.0548 (11)0.0402 (9)0.0311 (9)0.0092 (8)0.0059 (8)0.0012 (7)
C10.0509 (12)0.0405 (11)0.0446 (12)0.0045 (9)0.0086 (10)0.0009 (9)
C20.0654 (16)0.0594 (16)0.0508 (15)0.0080 (12)0.0012 (12)0.0084 (12)
C30.089 (2)0.083 (2)0.0590 (18)0.0218 (19)0.0111 (16)0.0255 (16)
C40.097 (3)0.0608 (19)0.086 (3)0.0094 (17)0.035 (2)0.0242 (18)
C50.092 (2)0.0549 (17)0.094 (3)0.0149 (16)0.027 (2)0.0013 (17)
C60.0638 (15)0.0519 (14)0.0616 (16)0.0086 (13)0.0087 (13)0.0025 (13)
C70.0408 (10)0.0489 (12)0.0331 (11)0.0032 (8)0.0014 (8)0.0044 (9)
C80.0548 (13)0.0565 (15)0.0469 (14)0.0089 (12)0.0052 (11)0.0011 (11)
C90.0491 (14)0.095 (2)0.0517 (15)0.0219 (14)0.0053 (11)0.0048 (14)
C100.0392 (13)0.104 (2)0.0573 (17)0.0016 (15)0.0015 (11)0.0209 (16)
C110.0511 (15)0.076 (2)0.085 (2)0.0148 (14)0.0076 (15)0.0170 (17)
C120.0454 (12)0.0560 (14)0.0646 (16)0.0004 (10)0.0037 (12)0.0033 (13)
C130.0398 (10)0.0424 (12)0.0391 (11)0.0023 (9)0.0021 (9)0.0032 (9)
C140.0362 (10)0.0422 (11)0.0466 (13)0.0018 (9)0.0011 (9)0.0036 (10)
C150.0512 (13)0.0511 (14)0.0648 (17)0.0109 (11)0.0025 (12)0.0049 (12)
C160.0706 (19)0.0583 (18)0.102 (3)0.0270 (15)0.0064 (18)0.0094 (17)
C170.084 (2)0.078 (2)0.083 (3)0.0257 (18)0.0138 (19)0.0254 (19)
C180.0763 (18)0.0690 (18)0.0532 (15)0.0094 (16)0.0102 (14)0.0132 (14)
C190.0463 (12)0.0458 (13)0.0460 (13)0.0034 (10)0.0053 (10)0.0063 (10)
C200.107 (3)0.086 (2)0.0374 (14)0.012 (2)0.0033 (16)0.0083 (14)
Geometric parameters (Å, º) top
P1—O11.4695 (17)C8—C91.389 (4)
P1—N11.6871 (19)C9—H90.9300
P1—C11.798 (2)C9—C101.361 (5)
P1—C71.802 (2)C10—H100.9300
O2—C131.215 (3)C10—C111.377 (5)
O3—C191.368 (3)C11—H110.9300
O3—C201.437 (3)C11—C121.394 (4)
N1—H10.8600C12—H120.9300
N1—C131.368 (3)C13—C141.496 (3)
C1—C21.396 (4)C14—C151.392 (3)
C1—C61.391 (4)C14—C191.416 (3)
C2—H20.9300C15—H150.9300
C2—C31.382 (4)C15—C161.377 (4)
C3—H30.9300C16—H160.9300
C3—C41.377 (5)C16—C171.388 (5)
C4—H40.9300C17—H170.9300
C4—C51.378 (6)C17—C181.371 (5)
C5—H50.9300C18—H180.9300
C5—C61.387 (4)C18—C191.382 (4)
C6—H60.9300C20—H20A0.9600
C7—C81.394 (3)C20—H20B0.9600
C7—C121.378 (3)C20—H20C0.9600
C8—H80.9300
O1—P1—N1115.61 (10)C9—C10—H10119.8
O1—P1—C1113.72 (11)C9—C10—C11120.3 (2)
O1—P1—C7113.17 (10)C11—C10—H10119.8
N1—P1—C199.56 (10)C10—C11—H11120.1
N1—P1—C7106.09 (11)C10—C11—C12119.8 (3)
C1—P1—C7107.49 (11)C12—C11—H11120.1
C19—O3—C20118.6 (2)C7—C12—C11120.5 (3)
P1—N1—H1116.4C7—C12—H12119.7
C13—N1—P1127.23 (16)C11—C12—H12119.7
C13—N1—H1116.4O2—C13—N1121.0 (2)
C2—C1—P1122.3 (2)O2—C13—C14121.7 (2)
C6—C1—P1118.4 (2)N1—C13—C14117.24 (19)
C6—C1—C2119.3 (2)C15—C14—C13116.2 (2)
C1—C2—H2119.9C15—C14—C19118.3 (2)
C3—C2—C1120.3 (3)C19—C14—C13125.4 (2)
C3—C2—H2119.9C14—C15—H15119.4
C2—C3—H3120.1C16—C15—C14121.1 (3)
C4—C3—C2119.9 (3)C16—C15—H15119.4
C4—C3—H3120.1C15—C16—H16120.4
C3—C4—H4119.7C15—C16—C17119.2 (3)
C3—C4—C5120.6 (3)C17—C16—H16120.4
C5—C4—H4119.7C16—C17—H17119.2
C4—C5—H5120.0C18—C17—C16121.5 (3)
C4—C5—C6120.0 (3)C18—C17—H17119.2
C6—C5—H5120.0C17—C18—H18120.3
C1—C6—H6120.0C17—C18—C19119.5 (3)
C5—C6—C1119.9 (3)C19—C18—H18120.3
C5—C6—H6120.0O3—C19—C14117.5 (2)
C8—C7—P1118.24 (19)O3—C19—C18122.1 (2)
C12—C7—P1122.82 (18)C18—C19—C14120.4 (2)
C12—C7—C8118.8 (2)O3—C20—H20A109.5
C7—C8—H8119.8O3—C20—H20B109.5
C9—C8—C7120.3 (3)O3—C20—H20C109.5
C9—C8—H8119.8H20A—C20—H20B109.5
C8—C9—H9119.9H20A—C20—H20C109.5
C10—C9—C8120.2 (3)H20B—C20—H20C109.5
C10—C9—H9119.9
P1—N1—C13—O22.7 (3)C3—C4—C5—C60.6 (5)
P1—N1—C13—C14176.74 (16)C4—C5—C6—C11.5 (5)
P1—C1—C2—C3176.0 (2)C6—C1—C2—C30.9 (4)
P1—C1—C6—C5177.8 (2)C7—P1—N1—C1380.8 (2)
P1—C7—C8—C9175.8 (2)C7—P1—C1—C251.3 (2)
P1—C7—C12—C11174.1 (2)C7—P1—C1—C6131.8 (2)
O1—P1—N1—C1345.5 (2)C7—C8—C9—C102.0 (4)
O1—P1—C1—C2177.4 (2)C8—C7—C12—C110.9 (4)
O1—P1—C1—C65.7 (2)C8—C9—C10—C111.8 (4)
O1—P1—C7—C872.7 (2)C9—C10—C11—C120.3 (5)
O1—P1—C7—C12102.2 (2)C10—C11—C12—C71.0 (5)
O2—C13—C14—C1512.0 (3)C12—C7—C8—C90.6 (4)
O2—C13—C14—C19166.9 (2)C13—C14—C15—C16179.3 (2)
N1—P1—C1—C259.0 (2)C13—C14—C19—O31.2 (4)
N1—P1—C1—C6117.90 (19)C13—C14—C19—C18179.5 (2)
N1—P1—C7—C8159.47 (19)C14—C15—C16—C170.8 (5)
N1—P1—C7—C1225.6 (2)C15—C14—C19—O3177.7 (2)
N1—C13—C14—C15167.5 (2)C15—C14—C19—C180.6 (4)
N1—C13—C14—C1913.6 (3)C15—C16—C17—C181.7 (6)
C1—P1—N1—C13167.8 (2)C16—C17—C18—C191.4 (5)
C1—P1—C7—C853.7 (2)C17—C18—C19—O3178.4 (3)
C1—P1—C7—C12131.3 (2)C17—C18—C19—C140.2 (4)
C1—C2—C3—C41.8 (5)C19—C14—C15—C160.3 (4)
C2—C1—C6—C50.7 (4)C20—O3—C19—C14178.1 (3)
C2—C3—C4—C51.0 (5)C20—O3—C19—C183.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O30.861.932.628 (2)137
C18—H18···Cgi0.932.993.864 (3)158
Symmetry code: (i) x+3/2, y+1, z1/2.
 

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