Diethyl [benzyl-amino-(1,3-diphenyl-1H-pyrazol-4--yl)meth-yl]phospho-nate.

In the title compound, C(27)H(30)N(3)O(3)P, the pyrazole ring is essentially planar [maximum deviation = 0.002 (2) Å] and it forms dihedral angles of 9.3 (1) and 40.2 (1)°, respectively, with the phenyl rings attached to the N and C atoms. In the crystal, pairs of centrosymmetrically related mol-ecules are linked into dimers by N-H⋯O hydrogen bonds.

Related literature

For the bioactivities of pyrazole derivatives, see: Sullivan et al. (2006 ▶); Patel et al. (2010 ▶); Siu et al. (2008 ▶).

Experimental

Crystal data

C27H30N3O3P

M = 475.51

Monoclinic,

a = 10.9534 (4) Å

b = 9.3777 (3) Å

c = 25.0690 (8) Å

β = 101.233 (2)°

V = 2525.70 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 293 K

0.2 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur-S diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.980, T max = 0.990

28506 measured reflections

6292 independent reflections

4220 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.124

S = 1.03

6292 reflections

403 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811032776/ci5195sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032776/ci5195Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811032776/ci5195Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C27H30N3O3P	F(000) = 1008
Mr = 475.51	Dx = 1.251 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8725 reflections
a = 10.9534 (4) Å	θ = 2.8–29.1°
b = 9.3777 (3) Å	µ = 0.14 mm−1
c = 25.0690 (8) Å	T = 293 K
β = 101.233 (2)°	Block, colourless
V = 2525.70 (15) Å3	0.2 × 0.2 × 0.2 mm
Z = 4

Oxford Diffraction Xcalibur-S diffractometer	6292 independent reflections
Radiation source: fine-focus sealed tube	4220 reflections with I > 2σ(I)
graphite	Rint = 0.031
Detector resolution: 15.9948 pixels mm-1	θmax = 28.4°, θmin = 2.3°
ω scans	h = −13→14
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −12→12
Tmin = 0.980, Tmax = 0.990	l = −33→31
28506 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0515P)2 + 0.7236P] where P = (Fo2 + 2Fc2)/3
6292 reflections	(Δ/σ)max = 0.001
403 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

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.

	x	y	z	Uiso*/Ueq
H8B	0.4103 (19)	0.338 (2)	0.1155 (8)	0.066 (6)*
H8A	0.549 (2)	0.373 (2)	0.1466 (8)	0.061 (6)*
H7	0.4879 (18)	0.455 (2)	0.0558 (9)	0.057 (6)*
H17	0.892 (3)	0.223 (3)	−0.0967 (12)	0.098 (9)*
H4	0.6887 (17)	0.4658 (19)	0.0136 (8)	0.046 (5)*
H29B	0.375 (2)	0.800 (3)	0.1338 (10)	0.080 (7)*
H22	0.768 (2)	0.755 (2)	0.1823 (9)	0.073 (7)*
H29A	0.497 (2)	0.891 (2)	0.1420 (9)	0.069 (7)*
H19	1.200 (3)	0.240 (3)	0.0216 (10)	0.095 (9)*
H20	1.085 (2)	0.343 (3)	0.0812 (10)	0.078 (7)*
H14	0.572 (2)	0.522 (3)	0.2261 (10)	0.085 (8)*
H16	0.779 (2)	0.327 (3)	−0.0394 (9)	0.077 (7)*
H10	0.244 (2)	0.501 (3)	0.1297 (10)	0.071 (7)*
H11	0.156 (3)	0.632 (3)	0.1919 (11)	0.103 (10)*
H26	0.930 (2)	0.371 (3)	0.2181 (9)	0.079 (7)*
H18	1.105 (3)	0.180 (3)	−0.0676 (11)	0.096 (8)*
H6	0.5905 (15)	0.6388 (17)	0.1330 (7)	0.036 (4)*
H30A	0.321 (3)	1.032 (3)	0.1460 (13)	0.110 (10)*
H30B	0.252 (3)	0.988 (3)	0.0857 (12)	0.111 (10)*
H27B	0.715 (2)	1.005 (3)	0.0291 (10)	0.087 (8)*
H27A	0.584 (3)	1.038 (3)	0.0488 (11)	0.102 (9)*
H13	0.494 (3)	0.653 (3)	0.2873 (13)	0.113 (11)*
H30C	0.379 (4)	1.079 (5)	0.0955 (17)	0.168 (18)*
H12	0.282 (3)	0.710 (4)	0.2731 (15)	0.146 (13)*
P	0.55474 (4)	0.75862 (4)	0.054083 (18)	0.03871 (13)
O1	0.66355 (11)	0.86067 (11)	0.08051 (5)	0.0448 (3)
N7	0.47930 (14)	0.50807 (15)	0.08404 (6)	0.0428 (3)
N3	0.85342 (13)	0.41796 (14)	0.06060 (6)	0.0420 (3)
O3	0.43152 (11)	0.82882 (13)	0.06482 (5)	0.0491 (3)
N2	0.90518 (14)	0.44221 (15)	0.11333 (6)	0.0451 (4)
O2	0.54283 (13)	0.73175 (13)	−0.00419 (5)	0.0526 (3)
C6	0.58773 (16)	0.60281 (16)	0.09730 (7)	0.0376 (4)
C5	0.71061 (16)	0.53605 (16)	0.09294 (7)	0.0392 (4)
C1	0.81900 (16)	0.51432 (17)	0.13319 (7)	0.0427 (4)
C4	0.73742 (17)	0.47270 (17)	0.04735 (8)	0.0426 (4)
C15	0.92211 (17)	0.34705 (17)	0.02579 (7)	0.0436 (4)
C21	0.84419 (17)	0.5557 (2)	0.19091 (8)	0.0478 (4)
C8	0.4667 (2)	0.41576 (19)	0.12999 (9)	0.0541 (5)
C9	0.4121 (2)	0.49577 (19)	0.17170 (8)	0.0512 (5)
C20	1.0464 (2)	0.3187 (2)	0.04401 (10)	0.0602 (5)
C29	0.4167 (2)	0.8764 (2)	0.11825 (10)	0.0604 (5)
C27	0.6709 (2)	1.0066 (2)	0.06104 (10)	0.0580 (5)
C26	0.9060 (2)	0.4626 (3)	0.23015 (9)	0.0628 (6)
C16	0.8658 (2)	0.3111 (3)	−0.02600 (9)	0.0652 (6)
C14	0.4848 (3)	0.5419 (3)	0.21966 (9)	0.0682 (6)
C23	0.8325 (3)	0.7229 (3)	0.26239 (12)	0.0854 (8)
H23	0.8065	0.8106	0.2734	0.102*
C22	0.8087 (2)	0.6875 (3)	0.20769 (10)	0.0657 (6)
C10	0.2871 (3)	0.5309 (3)	0.16212 (11)	0.0697 (6)
C18	1.0589 (2)	0.2218 (3)	−0.04303 (12)	0.0723 (7)
C17	0.9346 (2)	0.2490 (3)	−0.06048 (11)	0.0760 (7)
C12	0.3125 (4)	0.6572 (4)	0.24570 (13)	0.0964 (10)
C11	0.2376 (3)	0.6101 (3)	0.19938 (15)	0.0875 (9)
C24	0.8937 (3)	0.6297 (4)	0.30026 (11)	0.0899 (9)
H24	0.9102	0.6545	0.3369	0.108*
C19	1.1140 (2)	0.2559 (3)	0.00886 (12)	0.0724 (7)
C28	0.7401 (3)	1.0934 (3)	0.10496 (12)	0.1023 (10)
H28C	0.7453	1.1896	0.0925	0.153*
H28B	0.8225	1.0552	0.1161	0.153*
H28A	0.6982	1.0925	0.1352	0.153*
C30	0.3365 (3)	1.0064 (3)	0.11075 (16)	0.0873 (9)
C13	0.4355 (4)	0.6236 (3)	0.25610 (12)	0.0949 (9)
C25	0.9306 (3)	0.5004 (4)	0.28426 (10)	0.0862 (8)
H25	0.9726	0.4372	0.3101	0.103*

	U11	U22	U33	U12	U13	U23
P	0.0444 (3)	0.0310 (2)	0.0393 (2)	0.00695 (17)	0.00468 (18)	−0.00017 (16)
O1	0.0494 (7)	0.0322 (5)	0.0508 (7)	0.0011 (5)	0.0044 (6)	0.0044 (5)
N7	0.0512 (9)	0.0361 (7)	0.0410 (8)	−0.0005 (6)	0.0088 (7)	−0.0030 (6)
N3	0.0411 (8)	0.0384 (7)	0.0450 (8)	0.0053 (6)	0.0044 (6)	0.0006 (6)
O3	0.0474 (8)	0.0431 (6)	0.0550 (8)	0.0123 (5)	0.0056 (6)	−0.0009 (5)
N2	0.0442 (9)	0.0438 (8)	0.0440 (9)	0.0033 (6)	0.0004 (7)	0.0002 (6)
O2	0.0710 (9)	0.0441 (7)	0.0408 (7)	0.0096 (6)	0.0065 (6)	−0.0016 (5)
C6	0.0439 (10)	0.0321 (7)	0.0357 (9)	0.0042 (6)	0.0048 (7)	−0.0011 (6)
C5	0.0424 (10)	0.0317 (7)	0.0418 (9)	0.0036 (6)	0.0037 (7)	0.0025 (6)
C1	0.0443 (10)	0.0348 (8)	0.0469 (10)	−0.0003 (7)	0.0040 (8)	−0.0002 (7)
C4	0.0426 (10)	0.0398 (8)	0.0427 (10)	0.0076 (7)	0.0017 (8)	0.0021 (7)
C15	0.0429 (10)	0.0368 (8)	0.0523 (11)	0.0032 (7)	0.0121 (8)	0.0028 (7)
C21	0.0404 (10)	0.0528 (10)	0.0485 (11)	−0.0056 (8)	0.0040 (8)	−0.0055 (8)
C8	0.0726 (15)	0.0342 (9)	0.0572 (12)	−0.0024 (9)	0.0168 (11)	0.0030 (8)
C9	0.0660 (13)	0.0407 (9)	0.0493 (11)	−0.0048 (8)	0.0173 (10)	0.0080 (8)
C20	0.0493 (13)	0.0622 (12)	0.0670 (15)	0.0113 (10)	0.0058 (11)	0.0011 (10)
C29	0.0654 (15)	0.0579 (12)	0.0633 (14)	0.0136 (11)	0.0261 (12)	0.0002 (10)
C27	0.0689 (15)	0.0381 (9)	0.0672 (14)	−0.0022 (9)	0.0138 (12)	0.0137 (9)
C26	0.0624 (14)	0.0729 (15)	0.0489 (13)	0.0015 (11)	0.0004 (10)	0.0021 (10)
C16	0.0445 (13)	0.0882 (16)	0.0628 (14)	0.0068 (11)	0.0101 (10)	−0.0175 (12)
C14	0.0804 (18)	0.0683 (14)	0.0539 (14)	0.0128 (12)	0.0081 (12)	0.0023 (10)
C23	0.0794 (18)	0.0889 (18)	0.087 (2)	−0.0169 (14)	0.0155 (15)	−0.0439 (16)
C22	0.0662 (15)	0.0578 (12)	0.0681 (15)	−0.0067 (11)	0.0014 (11)	−0.0192 (11)
C10	0.0709 (17)	0.0727 (15)	0.0675 (16)	−0.0130 (12)	0.0184 (13)	0.0042 (12)
C18	0.0666 (16)	0.0752 (15)	0.0825 (18)	0.0156 (12)	0.0326 (14)	−0.0035 (12)
C17	0.0630 (16)	0.0997 (19)	0.0689 (16)	0.0079 (13)	0.0214 (13)	−0.0199 (14)
C12	0.138 (3)	0.095 (2)	0.0654 (19)	0.030 (2)	0.044 (2)	0.0089 (15)
C11	0.079 (2)	0.0930 (19)	0.103 (2)	0.0139 (16)	0.0481 (19)	0.0228 (17)
C24	0.089 (2)	0.128 (3)	0.0521 (15)	−0.0296 (18)	0.0126 (14)	−0.0301 (16)
C19	0.0474 (14)	0.0824 (16)	0.0898 (19)	0.0193 (12)	0.0191 (13)	0.0060 (13)
C28	0.155 (3)	0.0493 (13)	0.099 (2)	−0.0336 (16)	0.0141 (19)	−0.0041 (13)
C30	0.085 (2)	0.0713 (17)	0.109 (2)	0.0256 (15)	0.028 (2)	−0.0209 (16)
C13	0.130 (3)	0.094 (2)	0.0570 (17)	0.0257 (19)	0.0100 (17)	−0.0089 (14)
C25	0.0901 (19)	0.114 (2)	0.0484 (14)	−0.0115 (16)	−0.0018 (13)	0.0037 (14)

P—O2	1.4629 (13)	C27—H27B	1.02 (3)
P—O1	1.5708 (12)	C27—H27A	0.98 (3)
P—O3	1.5713 (13)	C26—C25	1.377 (3)
P—C6	1.8129 (16)	C26—H26	0.97 (3)
O1—C27	1.460 (2)	C16—C17	1.381 (3)
N7—C6	1.468 (2)	C16—H16	0.96 (2)
N7—C8	1.469 (2)	C14—C13	1.381 (4)
N7—H7	0.89 (2)	C14—H14	0.95 (3)
N3—C4	1.350 (2)	C23—C24	1.366 (4)
N3—N2	1.352 (2)	C23—C22	1.385 (3)
N3—C15	1.423 (2)	C23—H23	0.93
O3—C29	1.451 (2)	C22—H22	0.94 (2)
N2—C1	1.334 (2)	C10—C11	1.384 (4)
C6—C5	1.508 (2)	C10—H10	0.90 (2)
C6—H6	0.952 (17)	C18—C19	1.361 (4)
C5—C4	1.370 (2)	C18—C17	1.370 (4)
C5—C1	1.415 (2)	C18—H18	0.95 (3)
C1—C21	1.472 (3)	C17—H17	0.97 (3)
C4—H4	0.911 (18)	C12—C11	1.359 (5)
C15—C16	1.367 (3)	C12—C13	1.359 (5)
C15—C20	1.375 (3)	C12—H12	0.96 (4)
C21—C22	1.385 (3)	C11—H11	0.90 (3)
C21—C26	1.389 (3)	C24—C25	1.363 (4)
C8—C9	1.502 (3)	C24—H24	0.93
C8—H8B	0.98 (2)	C19—H19	0.94 (3)
C8—H8A	1.00 (2)	C28—H28C	0.96
C9—C14	1.376 (3)	C28—H28B	0.96
C9—C10	1.384 (3)	C28—H28A	0.96
C20—C19	1.387 (3)	C30—H30A	0.96 (3)
C20—H20	0.97 (2)	C30—H30B	1.03 (3)
C29—C30	1.493 (3)	C30—H30C	0.94 (5)
C29—H29B	0.97 (3)	C13—H13	0.95 (3)
C29—H29A	0.97 (2)	C25—H25	0.93
C27—C28	1.458 (3)
O2—P—O1	116.02 (8)	C28—C27—H27A	113.5 (17)
O2—P—O3	109.31 (7)	O1—C27—H27A	105.6 (17)
O1—P—O3	106.20 (7)	H27B—C27—H27A	110 (2)
O2—P—C6	115.25 (7)	C25—C26—C21	120.7 (2)
O1—P—C6	101.10 (7)	C25—C26—H26	121.6 (14)
O3—P—C6	108.25 (8)	C21—C26—H26	117.7 (14)
C27—O1—P	121.11 (13)	C15—C16—C17	119.9 (2)
C6—N7—C8	111.99 (15)	C15—C16—H16	122.0 (14)
C6—N7—H7	108.4 (13)	C17—C16—H16	118.1 (14)
C8—N7—H7	109.5 (13)	C9—C14—C13	121.2 (3)
C4—N3—N2	111.81 (14)	C9—C14—H14	118.3 (15)
C4—N3—C15	127.68 (15)	C13—C14—H14	120.3 (15)
N2—N3—C15	120.46 (14)	C24—C23—C22	120.5 (3)
C29—O3—P	122.76 (13)	C24—C23—H23	119.8
C1—N2—N3	104.94 (14)	C22—C23—H23	119.8
N7—C6—C5	115.25 (13)	C23—C22—C21	120.3 (2)
N7—C6—P	107.10 (11)	C23—C22—H22	118.7 (14)
C5—C6—P	111.61 (12)	C21—C22—H22	121.0 (14)
N7—C6—H6	107.7 (10)	C9—C10—C11	121.0 (3)
C5—C6—H6	110.5 (10)	C9—C10—H10	114.4 (16)
P—C6—H6	104.0 (10)	C11—C10—H10	124.5 (16)
C4—C5—C1	104.24 (15)	C19—C18—C17	119.3 (2)
C4—C5—C6	125.46 (15)	C19—C18—H18	121.5 (16)
C1—C5—C6	130.17 (15)	C17—C18—H18	119.2 (16)
N2—C1—C5	111.30 (15)	C18—C17—C16	120.5 (3)
N2—C1—C21	119.35 (16)	C18—C17—H17	121.1 (17)
C5—C1—C21	129.32 (16)	C16—C17—H17	118.3 (17)
N3—C4—C5	107.71 (16)	C11—C12—C13	120.0 (3)
N3—C4—H4	123.6 (12)	C11—C12—H12	123 (2)
C5—C4—H4	128.7 (12)	C13—C12—H12	117 (2)
C16—C15—C20	120.14 (19)	C12—C11—C10	120.0 (3)
C16—C15—N3	120.21 (17)	C12—C11—H11	120.9 (19)
C20—C15—N3	119.61 (17)	C10—C11—H11	119.0 (19)
C22—C21—C26	118.2 (2)	C25—C24—C23	119.9 (2)
C22—C21—C1	121.60 (18)	C25—C24—H24	120.1
C26—C21—C1	120.17 (18)	C23—C24—H24	120.1
N7—C8—C9	111.25 (15)	C18—C19—C20	121.0 (2)
N7—C8—H8B	107.3 (12)	C18—C19—H19	120.9 (16)
C9—C8—H8B	108.7 (12)	C20—C19—H19	118.1 (16)
N7—C8—H8A	110.5 (12)	C27—C28—H28C	109.5
C9—C8—H8A	111.1 (12)	C27—C28—H28B	109.5
H8B—C8—H8A	107.8 (17)	H28C—C28—H28B	109.5
C14—C9—C10	117.5 (2)	C27—C28—H28A	109.5
C14—C9—C8	121.6 (2)	H28C—C28—H28A	109.5
C10—C9—C8	120.8 (2)	H28B—C28—H28A	109.5
C15—C20—C19	119.1 (2)	C29—C30—H30A	106.8 (19)
C15—C20—H20	119.4 (14)	C29—C30—H30B	112.3 (17)
C19—C20—H20	121.5 (14)	H30A—C30—H30B	108 (2)
O3—C29—C30	107.7 (2)	C29—C30—H30C	109 (3)
O3—C29—H29B	106.8 (14)	H30A—C30—H30C	112 (3)
C30—C29—H29B	109.8 (15)	H30B—C30—H30C	109 (3)
O3—C29—H29A	111.0 (13)	C12—C13—C14	120.2 (3)
C30—C29—H29A	113.8 (14)	C12—C13—H13	125.0 (19)
H29B—C29—H29A	108 (2)	C14—C13—H13	115 (2)
C28—C27—O1	108.98 (18)	C24—C25—C26	120.4 (3)
C28—C27—H27B	110.2 (14)	C24—C25—H25	119.8
O1—C27—H27B	108.5 (14)	C26—C25—H25	119.8

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O2i	0.89 (2)	2.16 (2)	2.9891 (19)	155 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7⋯O2i	0.89 (2)	2.16 (2)	2.9891 (19)	155 (2)

Symmetry code: (i) .