Crystal structure of N-(di­phenyl­phosphor­yl)-2-meth­oxy­benzamide

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.

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

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Computing details

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

Crystal data

C20H18NO3P	Dx = 1.322 Mg m^−3
Mr = 351.32	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 5505 reflections
a = 8.317 (2) Å	θ = 3.2–30.6°
b = 12.657 (2) Å	µ = 0.17 mm^−1
c = 16.763 (3) Å	T = 294 K
V = 1764.6 (6) Å^3	Block, colourless
Z = 4	0.5 × 0.4 × 0.3 mm
F(000) = 736

Data collection

Rigaku Oxford Diffraction Xcalibur, Sapphire3 diffractometer	5691 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	4247 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 16.1827 pixels mm^-1	θmax = 32.2°, θmin = 3.2°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2018)	k = −17→16
Tmin = 0.986, Tmax = 1.000	l = −23→24
18281 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.043	w = 1/[σ^2(Fo^2) + (0.0551P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.113	(Δ/σ)max = 0.001
S = 1.11	Δρmax = 0.23 e Å^−3
5691 reflections	Δρmin = −0.32 e Å^−3
227 parameters	Absolute structure: Flack x determined using 1430 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: 0.01 (4)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
P1	0.75683 (6)	0.34774 (4)	0.68054 (3)	0.03788 (14)
O1	0.8432 (2)	0.33778 (15)	0.75665 (10)	0.0522 (4)
O2	0.8579 (2)	0.57607 (14)	0.70208 (11)	0.0601 (5)
O3	0.8588 (2)	0.48946 (15)	0.46564 (10)	0.0574 (5)
N1	0.8291 (2)	0.43972 (14)	0.61711 (11)	0.0420 (4)
H1	0.839131	0.420776	0.568098	0.050*
C1	0.7720 (3)	0.23277 (18)	0.61801 (14)	0.0454 (5)
C2	0.6930 (4)	0.2254 (2)	0.54479 (17)	0.0585 (7)
H2	0.624578	0.279355	0.528470	0.070*
C3	0.7160 (4)	0.1383 (3)	0.4964 (2)	0.0768 (10)
H3	0.665554	0.134563	0.447009	0.092*
C4	0.8138 (5)	0.0571 (3)	0.5216 (2)	0.0815 (11)
H4	0.827802	−0.001937	0.489292	0.098*
C5	0.8912 (5)	0.0626 (3)	0.5942 (2)	0.0802 (10)
H5	0.956231	0.007064	0.610905	0.096*
C6	0.8722 (3)	0.1509 (2)	0.64224 (18)	0.0591 (6)
H6	0.926469	0.155311	0.690643	0.071*
C7	0.5462 (3)	0.37685 (18)	0.69283 (13)	0.0410 (5)
C8	0.4455 (3)	0.2966 (2)	0.72018 (16)	0.0528 (6)
H8	0.486311	0.229064	0.728194	0.063*
C9	0.2844 (3)	0.3171 (3)	0.73552 (18)	0.0653 (8)
H9	0.217061	0.262777	0.752171	0.078*
C10	0.2247 (3)	0.4165 (3)	0.72626 (17)	0.0669 (8)
H10	0.117415	0.430192	0.738074	0.080*
C11	0.3223 (3)	0.4969 (3)	0.6995 (2)	0.0706 (9)
H11	0.280930	0.564645	0.692976	0.085*
C12	0.4832 (3)	0.4765 (2)	0.68216 (19)	0.0553 (6)
H12	0.548597	0.530641	0.663257	0.066*
C13	0.8734 (3)	0.54108 (18)	0.63499 (14)	0.0405 (5)
C14	0.9427 (3)	0.60615 (19)	0.56888 (14)	0.0417 (5)
C15	1.0164 (3)	0.7003 (2)	0.59123 (18)	0.0557 (6)
H15	1.020894	0.718620	0.644915	0.067*
C16	1.0828 (4)	0.7669 (3)	0.5352 (3)	0.0769 (10)
H16	1.130614	0.830077	0.550753	0.092*
C17	1.0775 (4)	0.7386 (3)	0.4553 (2)	0.0814 (10)
H17	1.124742	0.782560	0.417536	0.098*
C18	1.0042 (4)	0.6472 (3)	0.43069 (19)	0.0662 (7)
H18	0.999839	0.630235	0.376750	0.079*
C19	0.9367 (3)	0.58040 (19)	0.48673 (15)	0.0460 (5)
C20	0.8551 (5)	0.4599 (3)	0.38290 (17)	0.0768 (9)
H20A	0.800672	0.513521	0.352765	0.115*
H20B	0.799139	0.393959	0.377171	0.115*
H20C	0.963101	0.452306	0.363487	0.115*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0406 (3)	0.0420 (3)	0.0310 (2)	−0.0018 (2)	0.0008 (2)	0.0024 (2)
O1	0.0519 (8)	0.0658 (11)	0.0389 (8)	0.0029 (8)	−0.0059 (7)	0.0059 (8)
O2	0.0794 (12)	0.0568 (11)	0.0442 (10)	−0.0133 (9)	0.0112 (9)	−0.0149 (8)
O3	0.0811 (12)	0.0574 (11)	0.0335 (9)	−0.0146 (9)	0.0021 (9)	0.0008 (8)
N1	0.0548 (11)	0.0402 (9)	0.0311 (9)	−0.0092 (8)	0.0059 (8)	−0.0012 (7)
C1	0.0509 (12)	0.0405 (11)	0.0446 (12)	−0.0045 (9)	0.0086 (10)	0.0009 (9)
C2	0.0654 (16)	0.0594 (16)	0.0508 (15)	−0.0080 (12)	0.0012 (12)	−0.0084 (12)
C3	0.089 (2)	0.083 (2)	0.0590 (18)	−0.0218 (19)	0.0111 (16)	−0.0255 (16)
C4	0.097 (3)	0.0608 (19)	0.086 (3)	−0.0094 (17)	0.035 (2)	−0.0242 (18)
C5	0.092 (2)	0.0549 (17)	0.094 (3)	0.0149 (16)	0.027 (2)	−0.0013 (17)
C6	0.0638 (15)	0.0519 (14)	0.0616 (16)	0.0086 (13)	0.0087 (13)	0.0025 (13)
C7	0.0408 (10)	0.0489 (12)	0.0331 (11)	−0.0032 (8)	−0.0014 (8)	−0.0044 (9)
C8	0.0548 (13)	0.0565 (15)	0.0469 (14)	−0.0089 (12)	0.0052 (11)	0.0011 (11)
C9	0.0491 (14)	0.095 (2)	0.0517 (15)	−0.0219 (14)	0.0053 (11)	−0.0048 (14)
C10	0.0392 (13)	0.104 (2)	0.0573 (17)	0.0016 (15)	−0.0015 (11)	−0.0209 (16)
C11	0.0511 (15)	0.076 (2)	0.085 (2)	0.0148 (14)	−0.0076 (15)	−0.0170 (17)
C12	0.0454 (12)	0.0560 (14)	0.0646 (16)	−0.0004 (10)	−0.0037 (12)	0.0033 (13)
C13	0.0398 (10)	0.0424 (12)	0.0391 (11)	−0.0023 (9)	0.0021 (9)	−0.0032 (9)
C14	0.0362 (10)	0.0422 (11)	0.0466 (13)	−0.0018 (9)	0.0011 (9)	0.0036 (10)
C15	0.0512 (13)	0.0511 (14)	0.0648 (17)	−0.0109 (11)	0.0025 (12)	−0.0049 (12)
C16	0.0706 (19)	0.0583 (18)	0.102 (3)	−0.0270 (15)	0.0064 (18)	0.0094 (17)
C17	0.084 (2)	0.078 (2)	0.083 (3)	−0.0257 (18)	0.0138 (19)	0.0254 (19)
C18	0.0763 (18)	0.0690 (18)	0.0532 (15)	−0.0094 (16)	0.0102 (14)	0.0132 (14)
C19	0.0463 (12)	0.0458 (13)	0.0460 (13)	−0.0034 (10)	0.0053 (10)	0.0063 (10)
C20	0.107 (3)	0.086 (2)	0.0374 (14)	−0.012 (2)	0.0033 (16)	−0.0083 (14)

Geometric parameters (Å, º)

P1—O1	1.4695 (17)	C8—C9	1.389 (4)
P1—N1	1.6871 (19)	C9—H9	0.9300
P1—C1	1.798 (2)	C9—C10	1.361 (5)
P1—C7	1.802 (2)	C10—H10	0.9300
O2—C13	1.215 (3)	C10—C11	1.377 (5)
O3—C19	1.368 (3)	C11—H11	0.9300
O3—C20	1.437 (3)	C11—C12	1.394 (4)
N1—H1	0.8600	C12—H12	0.9300
N1—C13	1.368 (3)	C13—C14	1.496 (3)
C1—C2	1.396 (4)	C14—C15	1.392 (3)
C1—C6	1.391 (4)	C14—C19	1.416 (3)
C2—H2	0.9300	C15—H15	0.9300
C2—C3	1.382 (4)	C15—C16	1.377 (4)
C3—H3	0.9300	C16—H16	0.9300
C3—C4	1.377 (5)	C16—C17	1.388 (5)
C4—H4	0.9300	C17—H17	0.9300
C4—C5	1.378 (6)	C17—C18	1.371 (5)
C5—H5	0.9300	C18—H18	0.9300
C5—C6	1.387 (4)	C18—C19	1.382 (4)
C6—H6	0.9300	C20—H20A	0.9600
C7—C8	1.394 (3)	C20—H20B	0.9600
C7—C12	1.378 (3)	C20—H20C	0.9600
C8—H8	0.9300
O1—P1—N1	115.61 (10)	C9—C10—H10	119.8
O1—P1—C1	113.72 (11)	C9—C10—C11	120.3 (2)
O1—P1—C7	113.17 (10)	C11—C10—H10	119.8
N1—P1—C1	99.56 (10)	C10—C11—H11	120.1
N1—P1—C7	106.09 (11)	C10—C11—C12	119.8 (3)
C1—P1—C7	107.49 (11)	C12—C11—H11	120.1
C19—O3—C20	118.6 (2)	C7—C12—C11	120.5 (3)
P1—N1—H1	116.4	C7—C12—H12	119.7
C13—N1—P1	127.23 (16)	C11—C12—H12	119.7
C13—N1—H1	116.4	O2—C13—N1	121.0 (2)
C2—C1—P1	122.3 (2)	O2—C13—C14	121.7 (2)
C6—C1—P1	118.4 (2)	N1—C13—C14	117.24 (19)
C6—C1—C2	119.3 (2)	C15—C14—C13	116.2 (2)
C1—C2—H2	119.9	C15—C14—C19	118.3 (2)
C3—C2—C1	120.3 (3)	C19—C14—C13	125.4 (2)
C3—C2—H2	119.9	C14—C15—H15	119.4
C2—C3—H3	120.1	C16—C15—C14	121.1 (3)
C4—C3—C2	119.9 (3)	C16—C15—H15	119.4
C4—C3—H3	120.1	C15—C16—H16	120.4
C3—C4—H4	119.7	C15—C16—C17	119.2 (3)
C3—C4—C5	120.6 (3)	C17—C16—H16	120.4
C5—C4—H4	119.7	C16—C17—H17	119.2
C4—C5—H5	120.0	C18—C17—C16	121.5 (3)
C4—C5—C6	120.0 (3)	C18—C17—H17	119.2
C6—C5—H5	120.0	C17—C18—H18	120.3
C1—C6—H6	120.0	C17—C18—C19	119.5 (3)
C5—C6—C1	119.9 (3)	C19—C18—H18	120.3
C5—C6—H6	120.0	O3—C19—C14	117.5 (2)
C8—C7—P1	118.24 (19)	O3—C19—C18	122.1 (2)
C12—C7—P1	122.82 (18)	C18—C19—C14	120.4 (2)
C12—C7—C8	118.8 (2)	O3—C20—H20A	109.5
C7—C8—H8	119.8	O3—C20—H20B	109.5
C9—C8—C7	120.3 (3)	O3—C20—H20C	109.5
C9—C8—H8	119.8	H20A—C20—H20B	109.5
C8—C9—H9	119.9	H20A—C20—H20C	109.5
C10—C9—C8	120.2 (3)	H20B—C20—H20C	109.5
C10—C9—H9	119.9
P1—N1—C13—O2	−2.7 (3)	C3—C4—C5—C6	−0.6 (5)
P1—N1—C13—C14	176.74 (16)	C4—C5—C6—C1	1.5 (5)
P1—C1—C2—C3	176.0 (2)	C6—C1—C2—C3	−0.9 (4)
P1—C1—C6—C5	−177.8 (2)	C7—P1—N1—C13	80.8 (2)
P1—C7—C8—C9	175.8 (2)	C7—P1—C1—C2	51.3 (2)
P1—C7—C12—C11	−174.1 (2)	C7—P1—C1—C6	−131.8 (2)
O1—P1—N1—C13	−45.5 (2)	C7—C8—C9—C10	−2.0 (4)
O1—P1—C1—C2	177.4 (2)	C8—C7—C12—C11	0.9 (4)
O1—P1—C1—C6	−5.7 (2)	C8—C9—C10—C11	1.8 (4)
O1—P1—C7—C8	−72.7 (2)	C9—C10—C11—C12	−0.3 (5)
O1—P1—C7—C12	102.2 (2)	C10—C11—C12—C7	−1.0 (5)
O2—C13—C14—C15	12.0 (3)	C12—C7—C8—C9	0.6 (4)
O2—C13—C14—C19	−166.9 (2)	C13—C14—C15—C16	−179.3 (2)
N1—P1—C1—C2	−59.0 (2)	C13—C14—C19—O3	1.2 (4)
N1—P1—C1—C6	117.90 (19)	C13—C14—C19—C18	179.5 (2)
N1—P1—C7—C8	159.47 (19)	C14—C15—C16—C17	−0.8 (5)
N1—P1—C7—C12	−25.6 (2)	C15—C14—C19—O3	−177.7 (2)
N1—C13—C14—C15	−167.5 (2)	C15—C14—C19—C18	0.6 (4)
N1—C13—C14—C19	13.6 (3)	C15—C16—C17—C18	1.7 (6)
C1—P1—N1—C13	−167.8 (2)	C16—C17—C18—C19	−1.4 (5)
C1—P1—C7—C8	53.7 (2)	C17—C18—C19—O3	178.4 (3)
C1—P1—C7—C12	−131.3 (2)	C17—C18—C19—C14	0.2 (4)
C1—C2—C3—C4	1.8 (5)	C19—C14—C15—C16	−0.3 (4)
C2—C1—C6—C5	−0.7 (4)	C20—O3—C19—C14	−178.1 (3)
C2—C3—C4—C5	−1.0 (5)	C20—O3—C19—C18	3.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.86	1.93	2.628 (2)	137
C18—H18···Cg^i	0.93	2.99	3.864 (3)	158

Symmetry code: (i) −x+3/2, −y+1, z−1/2.