Diethyl (1-benzyl-4-phenyl-3-tri­fluoro­methyl-1H-pyrrol-2-yl)phospho­nate

In the title compound, C₂₂H₂₃F₃NO₃P, the dihedral angles between the pyrrole ring and the benzyl and phenyl rings are 81.38 (7) and 46.21 (8)°, respectively. The ethyl phosphate groups present with P—O—C—C torsion angles of −178.47 (10) and 106.72 (16)°, and an intra­molecular C—H...O hydrogen bond occurs. In the extended structure, mol­ecules are linked by C—H...O and C—H...F hydrogen bonds to generate [001] chains.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.031
• wR factor = 0.079
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Non-Solvent Resd 1   C   Ueq(max)/Ueq(min) Range        4.1 Ratio
PLAT222_ALERT_3_C Non-Solvent Resd 1   H Uiso(max)/Uiso(min) Range        4.6 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     --  C3      ..        5.3 s.u.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      3.628 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min)           6 Note
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          9 Report

Alert level G
PLAT395_ALERT_2_G Deviating  X-O-Y  Angle from 120 Deg for  O2          119.5 Degree
PLAT395_ALERT_2_G Deviating  X-O-Y  Angle from 120 Deg for  O3          119.6 Degree
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          9 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 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
   6 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis CCD (Oxford Diffraction, 2008); data reduction: CrysAlis CCD (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).

Diethyl (1-benzyl-4-phenyl-3-trifluoromethyl-1H-pyrrol-2-yl)phosphonate

Crystal data

C22H23F3NO3P	F(000) = 912
Mr = 437.38	Dx = 1.335 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.7056 (3) Å	Cell parameters from 14420 reflections
b = 10.6494 (2) Å	θ = 3.0–26.0°
c = 14.9163 (3) Å	µ = 0.17 mm^−1
β = 91.744 (2)°	T = 150 K
V = 2176.12 (8) Å^3	Irregular, colourless
Z = 4	0.27 × 0.20 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur diffractometer	3251 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Detector resolution: 1024 x 1024 with blocks 2 x 2 pixels mm^-1	θmax = 26.0°, θmin = 3.0°
ω scan	h = −16→16
14420 measured reflections	k = −13→13
4254 independent reflections	l = −12→18

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.079	w = 1/[σ^2(Fo^2) + (0.0481P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max < 0.001
4254 reflections	Δρmax = 0.32 e Å^−3
271 parameters	Δρmin = −0.31 e Å^−3

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.

Refinement. All H atoms were found in a difference map but set to idealized positions and treated as riding atoms with C_Ar—H = 0.93 Å and U_iso(H) = 1.2U_eq(C) for C—H, with C—H₃ = 0.96 Å and U_iso(H) = 1.5U_eq(C) and with C—H₂ = 0.97 and U_iso(H) = 1.2U_eq(C).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.26227 (8)	0.28475 (10)	0.23073 (7)	0.0171 (2)
O1	0.25503 (8)	0.18705 (9)	−0.02572 (6)	0.0291 (3)
O2	0.24039 (8)	0.04337 (9)	0.11152 (6)	0.0278 (2)
O3	0.39528 (7)	0.13043 (9)	0.08712 (6)	0.0263 (2)
P1	0.28542 (3)	0.16327 (3)	0.06738 (2)	0.02047 (10)
F1	0.27999 (7)	0.45000 (8)	−0.02257 (5)	0.0319 (2)
F2	0.18429 (7)	0.58775 (8)	0.02989 (5)	0.0386 (3)
F3	0.12551 (7)	0.41436 (9)	−0.02136 (6)	0.0409 (3)
C1	0.47105 (11)	0.21634 (16)	0.05827 (10)	0.0327 (4)
H1A	0.4640	0.2972	0.0873	0.039*
H1B	0.4656	0.2287	−0.0061	0.039*
C2	0.56792 (12)	0.1603 (2)	0.08338 (12)	0.0469 (5)
H2A	0.6189	0.2155	0.0650	0.070*
H2B	0.5744	0.0806	0.0541	0.070*
H2C	0.5727	0.1486	0.1472	0.070*
C3	0.13611 (13)	0.01934 (17)	0.10071 (12)	0.0457 (5)
H3A	0.1034	0.0943	0.0783	0.055*
H3B	0.1096	−0.0014	0.1584	0.055*
C4	0.11827 (18)	−0.0846 (2)	0.03792 (16)	0.0701 (7)
H4A	0.0493	−0.0993	0.0312	0.105*
H4B	0.1497	−0.1591	0.0607	0.105*
H4C	0.1441	−0.0637	−0.0193	0.105*
C5	0.25575 (10)	0.29234 (12)	0.13827 (8)	0.0172 (3)
C6	0.21315 (10)	0.40874 (12)	0.11826 (8)	0.0170 (3)
C7	0.19250 (9)	0.47038 (13)	0.20012 (8)	0.0173 (3)
C8	0.22526 (10)	0.39073 (13)	0.26700 (9)	0.0188 (3)
H8	0.2225	0.4071	0.3281	0.023*
C9	0.20027 (11)	0.46319 (13)	0.02681 (9)	0.0242 (3)
C10	0.13887 (10)	0.58735 (13)	0.21848 (9)	0.0200 (3)
C11	0.05005 (11)	0.61462 (14)	0.17435 (10)	0.0267 (3)
H11	0.0274	0.5630	0.1279	0.032*
C12	−0.00447 (12)	0.71717 (15)	0.19877 (12)	0.0363 (4)
H12	−0.0633	0.7345	0.1686	0.044*
C13	0.02780 (14)	0.79382 (17)	0.26762 (12)	0.0437 (5)
H13	−0.0096	0.8622	0.2846	0.052*
C14	0.11546 (14)	0.76936 (16)	0.31135 (12)	0.0433 (5)
H14	0.1376	0.8219	0.3574	0.052*
C15	0.17114 (12)	0.66642 (15)	0.28696 (10)	0.0310 (4)
H15	0.2304	0.6505	0.3168	0.037*
C16	0.30577 (10)	0.18449 (13)	0.28608 (9)	0.0196 (3)
H16A	0.2948	0.1048	0.2559	0.023*
H16B	0.2726	0.1813	0.3426	0.023*
C17	0.41387 (10)	0.19995 (13)	0.30541 (8)	0.0197 (3)
C18	0.46153 (11)	0.31409 (14)	0.29963 (9)	0.0251 (3)
H18	0.4272	0.3847	0.2800	0.030*
C19	0.56011 (12)	0.32431 (15)	0.32285 (10)	0.0315 (4)
H19	0.5913	0.4016	0.3187	0.038*
C20	0.61174 (12)	0.22048 (17)	0.35194 (10)	0.0339 (4)
H20	0.6778	0.2273	0.3673	0.041*
C21	0.56512 (12)	0.10625 (16)	0.35826 (11)	0.0343 (4)
H21	0.5998	0.0360	0.3781	0.041*
C22	0.46686 (11)	0.09576 (14)	0.33519 (10)	0.0271 (3)
H22	0.4360	0.0184	0.3396	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0182 (6)	0.0208 (6)	0.0122 (5)	0.0017 (5)	−0.0011 (4)	0.0016 (5)
O1	0.0432 (7)	0.0281 (6)	0.0156 (5)	0.0017 (5)	−0.0035 (4)	−0.0029 (4)
O2	0.0356 (6)	0.0217 (5)	0.0259 (5)	−0.0050 (5)	−0.0030 (5)	0.0010 (4)
O3	0.0274 (6)	0.0254 (6)	0.0262 (5)	0.0054 (4)	0.0026 (4)	−0.0006 (4)
P1	0.0273 (2)	0.01945 (19)	0.01456 (18)	0.00111 (16)	−0.00119 (14)	−0.00163 (14)
F1	0.0448 (6)	0.0329 (5)	0.0183 (4)	−0.0001 (4)	0.0085 (4)	0.0028 (4)
F2	0.0683 (7)	0.0245 (5)	0.0230 (4)	0.0135 (5)	0.0022 (4)	0.0064 (4)
F3	0.0426 (6)	0.0514 (6)	0.0273 (5)	−0.0019 (5)	−0.0215 (4)	0.0024 (4)
C1	0.0307 (9)	0.0403 (10)	0.0272 (8)	−0.0023 (7)	0.0034 (7)	0.0030 (7)
C2	0.0302 (10)	0.0725 (14)	0.0380 (10)	0.0048 (9)	0.0000 (8)	0.0055 (9)
C3	0.0437 (11)	0.0435 (11)	0.0497 (11)	−0.0130 (9)	−0.0002 (9)	0.0068 (9)
C4	0.0680 (16)	0.0592 (14)	0.0819 (16)	−0.0233 (12)	−0.0168 (13)	−0.0115 (12)
C5	0.0163 (7)	0.0221 (7)	0.0130 (6)	−0.0012 (6)	−0.0021 (5)	0.0003 (5)
C6	0.0155 (7)	0.0196 (7)	0.0158 (6)	−0.0017 (6)	−0.0030 (5)	0.0005 (5)
C7	0.0134 (7)	0.0208 (7)	0.0177 (7)	−0.0010 (6)	−0.0007 (5)	−0.0009 (5)
C8	0.0188 (7)	0.0240 (7)	0.0135 (6)	0.0013 (6)	0.0003 (5)	−0.0024 (5)
C9	0.0326 (9)	0.0226 (8)	0.0172 (7)	0.0032 (7)	−0.0041 (6)	−0.0004 (6)
C10	0.0197 (7)	0.0210 (7)	0.0196 (7)	0.0003 (6)	0.0026 (6)	0.0016 (6)
C11	0.0237 (8)	0.0243 (8)	0.0320 (8)	0.0024 (6)	−0.0024 (6)	−0.0007 (6)
C12	0.0261 (9)	0.0325 (9)	0.0502 (10)	0.0097 (7)	−0.0015 (8)	0.0004 (8)
C13	0.0434 (11)	0.0346 (10)	0.0537 (11)	0.0163 (8)	0.0094 (9)	−0.0074 (8)
C14	0.0542 (12)	0.0363 (10)	0.0393 (10)	0.0084 (9)	−0.0005 (9)	−0.0182 (8)
C15	0.0321 (9)	0.0328 (9)	0.0278 (8)	0.0052 (7)	−0.0044 (7)	−0.0072 (7)
C16	0.0250 (8)	0.0195 (7)	0.0141 (6)	0.0021 (6)	−0.0018 (6)	0.0033 (5)
C17	0.0241 (8)	0.0239 (8)	0.0110 (6)	0.0037 (6)	0.0000 (5)	−0.0019 (5)
C18	0.0268 (8)	0.0247 (8)	0.0235 (7)	0.0026 (6)	−0.0030 (6)	0.0034 (6)
C19	0.0290 (9)	0.0350 (9)	0.0303 (8)	−0.0061 (7)	−0.0024 (7)	0.0000 (7)
C20	0.0222 (8)	0.0503 (11)	0.0290 (9)	0.0055 (8)	−0.0042 (7)	−0.0063 (7)
C21	0.0298 (9)	0.0367 (10)	0.0359 (9)	0.0140 (8)	−0.0064 (7)	−0.0003 (8)
C22	0.0301 (9)	0.0220 (8)	0.0290 (8)	0.0055 (7)	−0.0025 (7)	−0.0008 (6)

Geometric parameters (Å, º)

N1—C8	1.3567 (17)	C7—C10	1.4763 (19)
N1—C5	1.3817 (16)	C8—H8	0.9300
N1—C16	1.4654 (16)	C10—C15	1.386 (2)
O1—P1	1.4598 (10)	C10—C11	1.3966 (19)
O2—C3	1.456 (2)	C11—C12	1.379 (2)
O2—P1	1.5715 (10)	C11—H11	0.9300
O3—C1	1.4586 (18)	C12—C13	1.374 (2)
O3—P1	1.5650 (10)	C12—H12	0.9300
P1—C5	1.7886 (14)	C13—C14	1.374 (2)
F1—C9	1.3436 (17)	C13—H13	0.9300
F2—C9	1.3455 (16)	C14—C15	1.390 (2)
F3—C9	1.3385 (16)	C14—H14	0.9300
C1—C2	1.493 (2)	C15—H15	0.9300
C1—H1A	0.9700	C16—C17	1.5097 (19)
C1—H1B	0.9700	C16—H16A	0.9700
C2—H2A	0.9600	C16—H16B	0.9700
C2—H2B	0.9600	C17—C18	1.384 (2)
C2—H2C	0.9600	C17—C22	1.392 (2)
C3—C4	1.466 (3)	C18—C19	1.389 (2)
C3—H3A	0.9700	C18—H18	0.9300
C3—H3B	0.9700	C19—C20	1.376 (2)
C4—H4A	0.9600	C19—H19	0.9300
C4—H4B	0.9600	C20—C21	1.379 (2)
C4—H4C	0.9600	C20—H20	0.9300
C5—C6	1.3987 (18)	C21—C22	1.384 (2)
C6—C7	1.4223 (18)	C21—H21	0.9300
C6—C9	1.4877 (18)	C22—H22	0.9300
C7—C8	1.3745 (18)
C8—N1—C5	109.62 (11)	F3—C9—F2	106.18 (11)
C8—N1—C16	122.15 (10)	F1—C9—F2	104.94 (11)
C5—N1—C16	128.16 (11)	F3—C9—C6	114.09 (12)
C3—O2—P1	119.54 (10)	F1—C9—C6	112.71 (11)
C1—O3—P1	119.59 (9)	F2—C9—C6	111.58 (11)
O1—P1—O3	117.57 (6)	C15—C10—C11	118.37 (13)
O1—P1—O2	115.80 (6)	C15—C10—C7	120.00 (12)
O3—P1—O2	97.32 (6)	C11—C10—C7	121.31 (12)
O1—P1—C5	111.45 (6)	C12—C11—C10	120.79 (14)
O3—P1—C5	107.17 (6)	C12—C11—H11	119.6
O2—P1—C5	106.11 (6)	C10—C11—H11	119.6
O3—C1—C2	108.10 (13)	C13—C12—C11	120.21 (15)
O3—C1—H1A	110.1	C13—C12—H12	119.9
C2—C1—H1A	110.1	C11—C12—H12	119.9
O3—C1—H1B	110.1	C12—C13—C14	119.93 (16)
C2—C1—H1B	110.1	C12—C13—H13	120.0
H1A—C1—H1B	108.4	C14—C13—H13	120.0
C1—C2—H2A	109.5	C13—C14—C15	120.26 (16)
C1—C2—H2B	109.5	C13—C14—H14	119.9
H2A—C2—H2B	109.5	C15—C14—H14	119.9
C1—C2—H2C	109.5	C10—C15—C14	120.43 (15)
H2A—C2—H2C	109.5	C10—C15—H15	119.8
H2B—C2—H2C	109.5	C14—C15—H15	119.8
O2—C3—C4	110.34 (16)	N1—C16—C17	114.09 (11)
O2—C3—H3A	109.6	N1—C16—H16A	108.7
C4—C3—H3A	109.6	C17—C16—H16A	108.7
O2—C3—H3B	109.6	N1—C16—H16B	108.7
C4—C3—H3B	109.6	C17—C16—H16B	108.7
H3A—C3—H3B	108.1	H16A—C16—H16B	107.6
C3—C4—H4A	109.5	C18—C17—C22	118.52 (14)
C3—C4—H4B	109.5	C18—C17—C16	123.11 (12)
H4A—C4—H4B	109.5	C22—C17—C16	118.27 (13)
C3—C4—H4C	109.5	C17—C18—C19	120.72 (14)
H4A—C4—H4C	109.5	C17—C18—H18	119.6
H4B—C4—H4C	109.5	C19—C18—H18	119.6
N1—C5—C6	106.19 (11)	C20—C19—C18	120.18 (15)
N1—C5—P1	122.43 (10)	C20—C19—H19	119.9
C6—C5—P1	130.99 (10)	C18—C19—H19	119.9
C5—C6—C7	108.57 (11)	C19—C20—C21	119.72 (15)
C5—C6—C9	125.33 (12)	C19—C20—H20	120.1
C7—C6—C9	125.88 (12)	C21—C20—H20	120.1
C8—C7—C6	105.62 (11)	C20—C21—C22	120.24 (15)
C8—C7—C10	122.65 (12)	C20—C21—H21	119.9
C6—C7—C10	131.45 (12)	C22—C21—H21	119.9
N1—C8—C7	109.98 (11)	C21—C22—C17	120.62 (15)
N1—C8—H8	125.0	C21—C22—H22	119.7
C7—C8—H8	125.0	C17—C22—H22	119.7
F3—C9—F1	106.69 (11)
C1—O3—P1—O1	55.83 (12)	C5—C6—C9—F3	77.75 (18)
C1—O3—P1—O2	−179.97 (10)	C7—C6—C9—F3	−108.26 (15)
C1—O3—P1—C5	−70.55 (11)	C5—C6—C9—F1	−44.13 (18)
C3—O2—P1—O1	−46.40 (13)	C7—C6—C9—F1	129.86 (14)
C3—O2—P1—O3	−171.88 (11)	C5—C6—C9—F2	−161.91 (13)
C3—O2—P1—C5	77.82 (12)	C7—C6—C9—F2	12.1 (2)
P1—O3—C1—C2	−178.47 (11)	C8—C7—C10—C15	44.5 (2)
P1—O2—C3—C4	106.72 (16)	C6—C7—C10—C15	−142.47 (15)
C8—N1—C5—C6	0.25 (14)	C8—C7—C10—C11	−128.81 (15)
C16—N1—C5—C6	−176.76 (13)	C6—C7—C10—C11	44.2 (2)
C8—N1—C5—P1	−173.24 (10)	C15—C10—C11—C12	−0.5 (2)
C16—N1—C5—P1	9.75 (19)	C7—C10—C11—C12	173.01 (14)
O1—P1—C5—N1	169.14 (10)	C10—C11—C12—C13	−0.4 (2)
O3—P1—C5—N1	−60.93 (12)	C11—C12—C13—C14	1.0 (3)
O2—P1—C5—N1	42.25 (12)	C12—C13—C14—C15	−0.8 (3)
O1—P1—C5—C6	−2.57 (15)	C11—C10—C15—C14	0.7 (2)
O3—P1—C5—C6	127.36 (13)	C7—C10—C15—C14	−172.85 (14)
O2—P1—C5—C6	−129.45 (13)	C13—C14—C15—C10	−0.1 (3)
N1—C5—C6—C7	−1.00 (15)	C8—N1—C16—C17	−89.45 (15)
P1—C5—C6—C7	171.72 (11)	C5—N1—C16—C17	87.23 (16)
N1—C5—C6—C9	173.87 (12)	N1—C16—C17—C18	21.10 (18)
P1—C5—C6—C9	−13.4 (2)	N1—C16—C17—C22	−162.55 (12)
C5—C6—C7—C8	1.35 (15)	C22—C17—C18—C19	0.1 (2)
C9—C6—C7—C8	−173.48 (13)	C16—C17—C18—C19	176.48 (12)
C5—C6—C7—C10	−172.52 (13)	C17—C18—C19—C20	0.1 (2)
C9—C6—C7—C10	12.7 (2)	C18—C19—C20—C21	−0.2 (2)
C5—N1—C8—C7	0.62 (15)	C19—C20—C21—C22	0.2 (2)
C16—N1—C8—C7	177.85 (12)	C20—C21—C22—C17	0.0 (2)
C6—C7—C8—N1	−1.20 (15)	C18—C17—C22—C21	−0.2 (2)
C10—C7—C8—N1	173.34 (12)	C16—C17—C22—C21	−176.68 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O2	0.97	2.35	3.1144 (16)	135
C8—H8···O1^i	0.93	2.43	3.2148 (16)	142
C16—H16B···O1^i	0.97	2.43	3.2178 (17)	138
C16—H16B···F1^i	0.97	2.45	3.2224 (15)	136

Symmetry code: (i) x, −y+1/2, z+1/2.