The title compound, C
19H
16NO
4P, was obtained by the reaction of diphenylphosphine oxide and 4-nitrobenzaldehyde. Molecules are linked into chains, running along the
b axis, by O—H
O and C—H
O intermolecular hydrogen bonds.
Supporting information
CCDC reference: 636219
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.042
- wR factor = 0.128
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact O3 .. N1 .. 2.85 Ang.
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.72 mm
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.74 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for O4 - N1 .. 5.59 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C10
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C12
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C13
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C8 -C13 1.36 Ang.
PLAT430_ALERT_2_C Short Inter D...A Contact O3 .. O3 .. 2.90 Ang.
PLAT430_ALERT_2_C Short Inter D...A Contact O4 .. O4 .. 2.89 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
11 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
11 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
(Diphenylphosphoryl)(4-nitrophenyl)methanol
top
Crystal data top
C19H16NO4P | F(000) = 736 |
Mr = 353.30 | Dx = 1.417 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4573 reflections |
a = 11.449 (3) Å | θ = 2.4–28.2° |
b = 6.1417 (15) Å | µ = 0.19 mm−1 |
c = 23.624 (6) Å | T = 298 K |
β = 94.409 (5)° | Plate, colourless |
V = 1656.2 (7) Å3 | 0.72 × 0.27 × 0.20 mm |
Z = 4 | |
Data collection top
Bruker APEX area-detector diffractometer | 3236 independent reflections |
Radiation source: fine-focus sealed tube | 2800 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 26.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −11→14 |
Tmin = 0.875, Tmax = 0.963 | k = −7→7 |
8522 measured reflections | l = −23→29 |
Refinement top
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0846P)2 + 0.3649P] where P = (Fo2 + 2Fc2)/3 |
3236 reflections | (Δ/σ)max = 0.001 |
226 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
P1 | 0.54209 (4) | 0.01463 (7) | 0.191756 (18) | 0.03708 (16) | |
O2 | 0.72213 (10) | 0.1251 (2) | 0.25261 (5) | 0.0423 (3) | |
H2A | 0.7808 | 0.1983 | 0.2611 | 0.064* | |
O1 | 0.57975 (11) | −0.2168 (2) | 0.19343 (5) | 0.0470 (3) | |
C1 | 0.66566 (14) | 0.2040 (3) | 0.20149 (7) | 0.0369 (4) | |
H1B | 0.6358 | 0.3509 | 0.2078 | 0.044* | |
N1 | 0.96475 (16) | 0.2451 (3) | 0.02073 (7) | 0.0535 (4) | |
C2 | 0.74280 (14) | 0.2096 (3) | 0.15313 (7) | 0.0369 (4) | |
C3 | 0.82106 (16) | 0.0433 (3) | 0.14530 (8) | 0.0434 (4) | |
H3A | 0.8236 | −0.0769 | 0.1693 | 0.052* | |
C8 | 0.46256 (14) | 0.0782 (3) | 0.12548 (8) | 0.0426 (4) | |
O4 | 0.92624 (16) | 0.3266 (3) | −0.02382 (6) | 0.0695 (4) | |
O3 | 1.06368 (14) | 0.1752 (3) | 0.02947 (6) | 0.0661 (4) | |
C6 | 0.80997 (18) | 0.3970 (3) | 0.07307 (8) | 0.0506 (5) | |
H6A | 0.8059 | 0.5143 | 0.0481 | 0.061* | |
C7 | 0.73895 (16) | 0.3869 (3) | 0.11712 (8) | 0.0474 (4) | |
H7A | 0.6876 | 0.5008 | 0.1228 | 0.057* | |
C4 | 0.89517 (16) | 0.0540 (3) | 0.10241 (8) | 0.0459 (4) | |
H4A | 0.9496 | −0.0556 | 0.0977 | 0.055* | |
C14 | 0.45469 (14) | 0.0823 (3) | 0.24917 (8) | 0.0427 (4) | |
C5 | 0.88694 (16) | 0.2302 (3) | 0.06671 (7) | 0.0434 (4) | |
C15 | 0.4414 (2) | −0.0722 (4) | 0.28999 (10) | 0.0629 (6) | |
H15A | 0.4748 | −0.2092 | 0.2867 | 0.076* | |
C19 | 0.4049 (2) | 0.2855 (4) | 0.25517 (10) | 0.0639 (6) | |
H19A | 0.4146 | 0.3929 | 0.2282 | 0.077* | |
C18 | 0.3413 (2) | 0.3295 (5) | 0.30073 (11) | 0.0745 (7) | |
H18A | 0.3064 | 0.4651 | 0.3041 | 0.089* | |
C17 | 0.3294 (2) | 0.1747 (5) | 0.34085 (10) | 0.0749 (7) | |
H17A | 0.2872 | 0.2055 | 0.3720 | 0.090* | |
C13 | 0.4239 (3) | 0.2807 (4) | 0.10951 (11) | 0.0895 (10) | |
H13A | 0.4401 | 0.3983 | 0.1336 | 0.107* | |
C9 | 0.4396 (2) | −0.0901 (4) | 0.08827 (10) | 0.0731 (7) | |
H9A | 0.4651 | −0.2298 | 0.0981 | 0.088* | |
C16 | 0.3788 (2) | −0.0252 (5) | 0.33597 (11) | 0.0811 (8) | |
H16A | 0.3702 | −0.1303 | 0.3637 | 0.097* | |
C11 | 0.3392 (2) | 0.1442 (5) | 0.02213 (10) | 0.0776 (7) | |
H11A | 0.2963 | 0.1663 | −0.0124 | 0.093* | |
C12 | 0.3615 (3) | 0.3131 (5) | 0.05830 (11) | 0.1014 (11) | |
H12A | 0.3343 | 0.4516 | 0.0483 | 0.122* | |
C10 | 0.3794 (3) | −0.0550 (5) | 0.03645 (12) | 0.0908 (9) | |
H10A | 0.3664 | −0.1701 | 0.0112 | 0.109* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0299 (3) | 0.0363 (3) | 0.0445 (3) | 0.00144 (16) | −0.00065 (17) | −0.00121 (17) |
O2 | 0.0369 (6) | 0.0495 (7) | 0.0398 (6) | −0.0070 (5) | −0.0025 (5) | 0.0025 (5) |
O1 | 0.0392 (7) | 0.0387 (6) | 0.0618 (8) | 0.0022 (5) | −0.0055 (5) | −0.0026 (5) |
C1 | 0.0344 (8) | 0.0367 (8) | 0.0393 (8) | −0.0010 (6) | 0.0013 (6) | −0.0018 (6) |
N1 | 0.0627 (11) | 0.0509 (9) | 0.0488 (9) | −0.0114 (8) | 0.0165 (8) | −0.0064 (7) |
C2 | 0.0336 (8) | 0.0384 (8) | 0.0383 (8) | −0.0024 (6) | −0.0007 (6) | −0.0020 (6) |
C3 | 0.0446 (10) | 0.0401 (8) | 0.0460 (9) | 0.0038 (7) | 0.0068 (7) | 0.0062 (7) |
C8 | 0.0301 (8) | 0.0507 (10) | 0.0464 (9) | 0.0019 (7) | −0.0016 (7) | −0.0043 (7) |
O4 | 0.0949 (12) | 0.0740 (10) | 0.0411 (8) | −0.0109 (9) | 0.0153 (7) | 0.0058 (7) |
O3 | 0.0557 (9) | 0.0734 (10) | 0.0721 (10) | −0.0051 (8) | 0.0245 (7) | −0.0092 (8) |
C6 | 0.0600 (12) | 0.0468 (10) | 0.0451 (10) | 0.0037 (9) | 0.0050 (8) | 0.0104 (8) |
C7 | 0.0490 (10) | 0.0434 (9) | 0.0501 (10) | 0.0093 (8) | 0.0059 (8) | 0.0046 (8) |
C4 | 0.0454 (10) | 0.0451 (9) | 0.0481 (10) | 0.0064 (8) | 0.0086 (8) | 0.0005 (8) |
C14 | 0.0293 (8) | 0.0519 (10) | 0.0466 (9) | −0.0011 (7) | 0.0017 (7) | −0.0005 (8) |
C5 | 0.0450 (10) | 0.0481 (9) | 0.0375 (8) | −0.0058 (8) | 0.0067 (7) | −0.0021 (7) |
C15 | 0.0573 (13) | 0.0726 (14) | 0.0594 (12) | 0.0065 (11) | 0.0085 (10) | 0.0136 (11) |
C19 | 0.0603 (13) | 0.0618 (13) | 0.0723 (14) | 0.0109 (10) | 0.0223 (10) | 0.0035 (11) |
C18 | 0.0613 (14) | 0.0851 (17) | 0.0795 (16) | 0.0137 (12) | 0.0211 (12) | −0.0102 (14) |
C17 | 0.0520 (13) | 0.118 (2) | 0.0567 (13) | 0.0025 (13) | 0.0148 (10) | −0.0095 (14) |
C13 | 0.129 (2) | 0.0663 (15) | 0.0662 (14) | 0.0418 (16) | −0.0377 (15) | −0.0164 (12) |
C9 | 0.0922 (17) | 0.0563 (13) | 0.0665 (14) | −0.0010 (12) | −0.0206 (13) | −0.0084 (10) |
C16 | 0.0723 (17) | 0.117 (2) | 0.0559 (13) | 0.0064 (15) | 0.0149 (12) | 0.0215 (14) |
C11 | 0.0684 (15) | 0.0986 (19) | 0.0613 (14) | 0.0091 (14) | −0.0247 (11) | −0.0021 (13) |
C12 | 0.134 (3) | 0.0882 (19) | 0.0740 (17) | 0.0531 (19) | −0.0420 (17) | −0.0096 (14) |
C10 | 0.116 (2) | 0.0816 (18) | 0.0688 (16) | −0.0099 (17) | −0.0339 (16) | −0.0169 (13) |
Geometric parameters (Å, º) top
P1—O1 | 1.4848 (13) | C4—H4A | 0.93 |
P1—C8 | 1.7927 (18) | C14—C15 | 1.370 (3) |
P1—C14 | 1.7950 (18) | C14—C19 | 1.384 (3) |
P1—C1 | 1.8324 (17) | C15—C16 | 1.377 (3) |
O2—C1 | 1.4110 (19) | C15—H15A | 0.93 |
O2—H2A | 0.82 | C19—C18 | 1.372 (3) |
C1—C2 | 1.497 (2) | C19—H19A | 0.93 |
C1—H1B | 0.98 | C18—C17 | 1.357 (4) |
N1—O3 | 1.214 (2) | C18—H18A | 0.93 |
N1—O4 | 1.217 (2) | C17—C16 | 1.360 (4) |
N1—C5 | 1.460 (2) | C17—H17A | 0.93 |
C2—C7 | 1.380 (2) | C13—C12 | 1.372 (3) |
C2—C3 | 1.381 (2) | C13—H13A | 0.93 |
C3—C4 | 1.372 (2) | C9—C10 | 1.375 (3) |
C3—H3A | 0.93 | C9—H9A | 0.93 |
C8—C13 | 1.364 (3) | C16—H16A | 0.93 |
C8—C9 | 1.369 (3) | C11—C10 | 1.341 (4) |
C6—C5 | 1.367 (3) | C11—C12 | 1.355 (4) |
C6—C7 | 1.370 (3) | C11—H11A | 0.93 |
C6—H6A | 0.93 | C12—H12A | 0.93 |
C7—H7A | 0.93 | C10—H10A | 0.93 |
C4—C5 | 1.371 (3) | | |
| | | |
O1—P1—C8 | 111.01 (8) | C15—C14—P1 | 118.05 (16) |
O1—P1—C14 | 112.27 (8) | C19—C14—P1 | 122.97 (15) |
C8—P1—C14 | 109.53 (8) | C6—C5—C4 | 122.57 (16) |
O1—P1—C1 | 112.61 (7) | C6—C5—N1 | 118.07 (16) |
C8—P1—C1 | 107.87 (8) | C4—C5—N1 | 119.35 (16) |
C14—P1—C1 | 103.18 (8) | C14—C15—C16 | 120.2 (2) |
C1—O2—H2A | 109.5 | C14—C15—H15A | 119.9 |
O2—C1—C2 | 113.74 (13) | C16—C15—H15A | 119.9 |
O2—C1—P1 | 100.82 (10) | C18—C19—C14 | 120.4 (2) |
C2—C1—P1 | 114.44 (11) | C18—C19—H19A | 119.8 |
O2—C1—H1B | 109.2 | C14—C19—H19A | 119.8 |
C2—C1—H1B | 109.2 | C17—C18—C19 | 119.9 (2) |
P1—C1—H1B | 109.2 | C17—C18—H18A | 120.1 |
O3—N1—O4 | 124.31 (17) | C19—C18—H18A | 120.1 |
O3—N1—C5 | 117.79 (16) | C18—C17—C16 | 120.6 (2) |
O4—N1—C5 | 117.90 (18) | C18—C17—H17A | 119.7 |
C7—C2—C3 | 119.43 (16) | C16—C17—H17A | 119.7 |
C7—C2—C1 | 119.71 (15) | C8—C13—C12 | 120.8 (2) |
C3—C2—C1 | 120.82 (15) | C8—C13—H13A | 119.6 |
C4—C3—C2 | 120.54 (16) | C12—C13—H13A | 119.6 |
C4—C3—H3A | 119.7 | C8—C9—C10 | 120.8 (2) |
C2—C3—H3A | 119.7 | C8—C9—H9A | 119.6 |
C13—C8—C9 | 117.95 (19) | C10—C9—H9A | 119.6 |
C13—C8—P1 | 124.92 (15) | C17—C16—C15 | 120.0 (2) |
C9—C8—P1 | 117.13 (16) | C17—C16—H16A | 120.0 |
C5—C6—C7 | 118.35 (16) | C15—C16—H16A | 120.0 |
C5—C6—H6A | 120.8 | C10—C11—C12 | 119.6 (2) |
C7—C6—H6A | 120.8 | C10—C11—H11A | 120.2 |
C6—C7—C2 | 120.72 (16) | C12—C11—H11A | 120.2 |
C6—C7—H7A | 119.6 | C11—C12—C13 | 120.3 (3) |
C2—C7—H7A | 119.6 | C11—C12—H12A | 119.8 |
C5—C4—C3 | 118.35 (16) | C13—C12—H12A | 119.8 |
C5—C4—H4A | 120.8 | C11—C10—C9 | 120.4 (2) |
C3—C4—H4A | 120.8 | C11—C10—H10A | 119.8 |
C15—C14—C19 | 118.92 (19) | C9—C10—H10A | 119.8 |
| | | |
O1—P1—C1—O2 | −53.69 (12) | C8—P1—C14—C19 | −53.15 (19) |
C8—P1—C1—O2 | −176.54 (10) | C1—P1—C14—C19 | 61.53 (18) |
C14—P1—C1—O2 | 67.59 (11) | C7—C6—C5—C4 | 0.3 (3) |
O1—P1—C1—C2 | 68.80 (13) | C7—C6—C5—N1 | −178.21 (17) |
C8—P1—C1—C2 | −54.05 (14) | C3—C4—C5—C6 | 1.6 (3) |
C14—P1—C1—C2 | −169.92 (12) | C3—C4—C5—N1 | −179.93 (16) |
O2—C1—C2—C7 | −137.88 (16) | O3—N1—C5—C6 | 143.53 (19) |
P1—C1—C2—C7 | 106.95 (16) | O4—N1—C5—C6 | −36.5 (2) |
O2—C1—C2—C3 | 39.7 (2) | O3—N1—C5—C4 | −35.0 (2) |
P1—C1—C2—C3 | −75.50 (18) | O4—N1—C5—C4 | 144.94 (18) |
C7—C2—C3—C4 | 0.5 (3) | C19—C14—C15—C16 | 0.4 (3) |
C1—C2—C3—C4 | −177.09 (15) | P1—C14—C15—C16 | 177.59 (19) |
O1—P1—C8—C13 | −175.0 (2) | C15—C14—C19—C18 | −1.3 (3) |
C14—P1—C8—C13 | 60.4 (2) | P1—C14—C19—C18 | −178.36 (19) |
C1—P1—C8—C13 | −51.2 (2) | C14—C19—C18—C17 | 1.6 (4) |
O1—P1—C8—C9 | 4.7 (2) | C19—C18—C17—C16 | −0.9 (4) |
C14—P1—C8—C9 | −119.80 (18) | C9—C8—C13—C12 | 1.6 (4) |
C1—P1—C8—C9 | 128.57 (18) | P1—C8—C13—C12 | −178.6 (3) |
C5—C6—C7—C2 | −1.9 (3) | C13—C8—C9—C10 | 0.0 (4) |
C3—C2—C7—C6 | 1.5 (3) | P1—C8—C9—C10 | −179.8 (2) |
C1—C2—C7—C6 | 179.06 (16) | C18—C17—C16—C15 | −0.1 (4) |
C2—C3—C4—C5 | −1.9 (3) | C14—C15—C16—C17 | 0.3 (4) |
O1—P1—C14—C15 | 5.97 (18) | C10—C11—C12—C13 | −0.6 (5) |
C8—P1—C14—C15 | 129.77 (17) | C8—C13—C12—C11 | −1.3 (5) |
C1—P1—C14—C15 | −115.55 (16) | C12—C11—C10—C9 | 2.1 (5) |
O1—P1—C14—C19 | −176.95 (16) | C8—C9—C10—C11 | −1.8 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O1i | 0.82 | 1.93 | 2.696 (2) | 156 |
C1—H1B···O2i | 0.98 | 2.47 | 3.050 (2) | 117 |
Symmetry code: (i) −x+3/2, y+1/2, −z+1/2. |