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A combined experimental and theoretical study of one oxaphosphinane derivative was made on the basis of a topological analysis of its electron density distributions. The electron density was determined from a high-resolution X-ray diffraction data set measured with synchrotron radiation at 100 K, whereas theoretical calculations were performed using density functional theory (DFT) methods at the B3LYP\6-311++G(3df,3pd) level of approximation. The charge-density distribution and analysis of topological properties revealed that the P—O bond is of the transit closed-shell type. The crystal structure possesses one intra- and several intermolecular hydrogen bonds. They were characterized quantitatively by topological properties using Bader's Atoms in Molecules theory. All hydrogen bonds were classified as weak. Further analysis of the experimental electron density by the source function allowed the intramolecular hydrogen bond to be characterized as an isolated hydrogen bond, in contrast to the resonance-assisted hydrogen bond in related molecules, such as chromone derivatives.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052519213027267/gw5021sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519213027267/gw5021Isup2.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052519213027267/gw5021sup3.pdf
Additional tables

CCDC reference: 964654

Experimental top

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1.

Results and discussion top

Computing details top

Data collection: MarCCD (Paulmann & Morgenroth, 2006); cell refinement: EVAL 15 (Schreurs, 2010); data reduction: EVAL 15 (Schreurs, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: Volkov et al., (2006); molecular graphics: Volkov et al., (2006); software used to prepare material for publication: Volkov et al., (2006).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
3-(1-amino-ethylidene)-2-methoxy-2-oxo-2,3-dihydro-2λ5-benzo[e][1,2] oxaphosphinin-4-one top
Crystal data top
C11H12NO4PZ = 4
Mr = 253.19F(000) = 528
Orthorhombic, P212121Dx = 1.413 Mg m3
Hall symbol: P 2ac 2abSynchrotron radiation, λ = 0.60000 Å
a = 9.2532 (10) ŵ = 0.23 mm1
b = 10.1555 (16) ÅT = 100 K
c = 12.6610 (12) ÅBlock, colourless
V = 1189.8 (3) Å30.45 × 0.3 × 0.18 mm
Data collection top
Huber
diffractometer
Rint = 0.035
Radiation source: synchrotronθmax = 48.6°, θmin = 2.2°
ϕ scanh = 2321
98994 measured reflectionsk = 1725
17584 independent reflectionsl = 2929
16534 reflections with I > 2σ(I)
Refinement top
Refinement on F534 parameters
Least-squares matrix: full0 restraints
R[F2 > 2σ(F2)] = 0.015 w1 = 1/[s2(Fo)]
wR(F2) = 0.017(Δ/σ)max < 0.001
S = 1.37Δρmax = 0.13 e Å3
14864 reflectionsΔρmin = 0.30 e Å3
Crystal data top
C11H12NO4PV = 1189.8 (3) Å3
Mr = 253.19Z = 4
Orthorhombic, P212121Synchrotron radiation, λ = 0.60000 Å
a = 9.2532 (10) ŵ = 0.23 mm1
b = 10.1555 (16) ÅT = 100 K
c = 12.6610 (12) Å0.45 × 0.3 × 0.18 mm
Data collection top
Huber
diffractometer
16534 reflections with I > 2σ(I)
98994 measured reflectionsRint = 0.035
17584 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.015534 parameters
wR(F2) = 0.0170 restraints
S = 1.37Δρmax = 0.13 e Å3
14864 reflectionsΔρmin = 0.30 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P(2)0.661925 (5)0.482849 (4)0.074523 (4)0.014
O(1)0.79064 (2)0.589242 (19)0.07178 (2)0.018
O(4)0.94685 (3)0.24666 (3)0.20485 (2)0.021
O(21)0.53019 (3)0.55035 (3)0.11139 (2)0.021
O(22)0.65057 (3)0.43039 (2)0.042492 (16)0.019
N(1)0.68818 (3)0.17020 (2)0.264657 (19)0.020
C(3)0.73085 (2)0.350744 (18)0.147879 (15)0.015
C(4)0.88637 (2)0.334200 (19)0.151694 (15)0.015
C(5)1.12308 (2)0.38966 (2)0.066650 (18)0.018
C(6)1.21239 (3)0.47156 (3)0.00743 (2)0.022
C(7)1.16036 (3)0.59292 (3)0.02899 (2)0.023
C(8)1.01866 (3)0.63147 (2)0.00725 (2)0.021
C(9)0.93004 (2)0.546727 (18)0.050172 (16)0.016
C(10)0.97952 (2)0.425563 (18)0.088410 (14)0.015
C(23)0.60537 (4)0.51966 (3)0.12529 (2)0.025
C(31)0.63736 (2)0.26343 (2)0.201981 (16)0.017
C(311)0.47572 (3)0.26942 (3)0.19046 (2)0.025
H(1)0.7964740.162790.2718450.035
H(2)0.6144060.1177740.3055780.040
H(5)1.1616080.2959290.0961510.036
H(6)1.3222380.4416580.0097890.043
H(7)1.227330.6595940.0743730.044
H(8)0.9738040.7238380.0346550.038
H(23A)0.5866910.4603660.1927510.046
H(23B)0.6915860.5864170.1378210.043
H(23C)0.5093780.5678890.101340.045
H(31A)0.4223510.1915690.230150.046
H(31B)0.4515240.2605520.109020.041
H(31C)0.4323930.3627260.2102440.042
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P(2)0.017529 (15)0.011967 (15)0.012494 (15)0.001408 (12)0.000818 (12)0.000247 (11)
O(1)0.02055 (6)0.01086 (5)0.02307 (7)0.00051 (5)0.00017 (6)0.00030 (5)
O(4)0.02124 (7)0.01938 (7)0.02338 (9)0.00517 (6)0.00429 (7)0.00844 (7)
O(21)0.02100 (7)0.02011 (7)0.02270 (8)0.00577 (6)0.00369 (7)0.00002 (7)
O(22)0.02992 (9)0.01515 (6)0.01176 (5)0.00107 (6)0.00087 (6)0.00053 (4)
N(1)0.02209 (7)0.01893 (7)0.01913 (7)0.00005 (6)0.00286 (6)0.00668 (6)
C(3)0.01831 (6)0.01347 (5)0.01276 (5)0.00047 (5)0.00122 (5)0.00145 (4)
C(4)0.01857 (6)0.01286 (5)0.01443 (6)0.00179 (5)0.00243 (5)0.00152 (4)
C(5)0.01772 (6)0.01542 (6)0.02166 (7)0.00023 (5)0.00226 (5)0.00093 (5)
C(6)0.01860 (7)0.01981 (8)0.02660 (9)0.00359 (6)0.00263 (6)0.00174 (7)
C(7)0.02188 (7)0.01935 (7)0.02827 (10)0.00631 (7)0.00154 (7)0.00454 (7)
C(8)0.02301 (8)0.01417 (6)0.02590 (9)0.00413 (6)0.00030 (6)0.00427 (6)
C(9)0.01930 (6)0.01118 (5)0.01810 (6)0.00129 (5)0.00008 (5)0.00044 (4)
C(10)0.01797 (6)0.01196 (5)0.01555 (6)0.00007 (4)0.00149 (4)0.00017 (4)
C(23)0.03553 (11)0.02295 (9)0.01653 (7)0.00569 (9)0.00431 (8)0.00664 (7)
C(31)0.01919 (6)0.01649 (6)0.01408 (6)0.00068 (5)0.00135 (5)0.00236 (5)
C(311)0.01989 (7)0.02841 (11)0.02535 (10)0.00272 (8)0.00058 (7)0.00854 (8)
H(1)0.0285400.0387720.0387180.0022350.0013990.013738
H(2)0.0357690.0436270.0395040.0048270.0072420.019888
H(5)0.0330450.0280720.0483540.0079330.0057580.010379
H(6)0.0261940.0459770.0574090.0028870.0120010.008524
H(7)0.0377820.0387730.0545650.0114590.0095850.015414
H(8)0.0415330.0221230.0508950.0004550.0006430.011577
H(23A)0.0648120.0484470.0255510.0065880.0109560.000789
H(23B)0.0403220.0428420.0446460.0132300.0056970.017506
H(23C)0.0390600.0525880.0423630.0116500.0022890.013691
H(31A)0.0370720.0477050.0517920.0090610.0063550.022578
H(31B)0.0370870.0589370.0258160.0036260.0015350.001158
H(31C)0.0351100.0382140.0524260.0066070.0034910.004192
Geometric parameters (Å, º) top
P(2)—O(1)1.6085 (2)C(6)—C(7)1.4012 (4)
P(2)—O(21)1.4743 (2)C(6)—H(6)1.0830
P(2)—O(22)1.5779 (2)C(7)—C(8)1.3959 (4)
P(2)—C(3)1.7519 (2)C(7)—H(7)1.0829
O(1)—C(9)1.3874 (3)C(8)—C(9)1.3934 (3)
O(4)—C(4)1.2476 (3)C(8)—H(8)1.0828
N(1)—C(31)1.3218 (3)C(9)—C(10)1.3993 (3)
N(1)—H(1)1.0090C(23)—H(23A)1.0593
N(1)—H(2)1.0089C(23)—H(23B)1.0589
C(3)—C(4)1.4497 (3)C(23)—H(23C)1.0586
C(3)—C(31)1.4155 (3)C(31)—C(311)1.5040 (3)
C(4)—C(10)1.4986 (3)C(311)—H(31A)1.0589
C(5)—C(6)1.3918 (3)C(311)—H(31B)1.0590
C(5)—C(10)1.4048 (3)C(311)—H(31C)1.0590
C(5)—H(5)1.0829
O(1)—P(2)—O(21)107.861 (14)C(6)—C(7)—H(7)121.87
O(1)—P(2)—O(22)104.823 (13)C(8)—C(7)—H(7)117.83
O(1)—P(2)—C(3)104.851 (11)C(7)—C(8)—C(9)118.85 (2)
O(21)—P(2)—O(22)113.525 (16)C(7)—C(8)—H(8)122.67
O(21)—P(2)—C(3)119.290 (13)C(9)—C(8)—H(8)118.47
O(22)—P(2)—C(3)105.276 (10)O(1)—C(9)—C(8)117.24 (2)
P(2)—O(1)—C(9)118.922 (15)O(1)—C(9)—C(10)120.639 (19)
C(31)—N(1)—H(1)117.44C(8)—C(9)—C(10)122.08 (2)
C(31)—N(1)—H(2)116.46C(4)—C(10)—C(5)119.209 (18)
H(1)—N(1)—H(2)125.89C(4)—C(10)—C(9)122.768 (18)
P(2)—C(3)—C(4)117.891 (14)C(5)—C(10)—C(9)118.022 (19)
P(2)—C(3)—C(31)120.916 (16)H(23A)—C(23)—H(23B)111.47
C(4)—C(3)—C(31)121.193 (17)H(23A)—C(23)—H(23C)110.92
O(4)—C(4)—C(3)123.08 (2)H(23B)—C(23)—H(23C)112.27
O(4)—C(4)—C(10)118.14 (2)N(1)—C(31)—C(3)121.45 (2)
C(3)—C(4)—C(10)118.775 (17)N(1)—C(31)—C(311)116.16 (2)
C(6)—C(5)—C(10)120.80 (2)C(3)—C(31)—C(311)122.38 (2)
C(6)—C(5)—H(5)121.04C(31)—C(311)—H(31A)112.81
C(10)—C(5)—H(5)118.15C(31)—C(311)—H(31B)107.53
C(5)—C(6)—C(7)119.93 (2)C(31)—C(311)—H(31C)112.94
C(5)—C(6)—H(6)119.88H(31A)—C(311)—H(31B)107.45
C(7)—C(6)—H(6)120.19H(31A)—C(311)—H(31C)112.29
C(6)—C(7)—C(8)120.30 (2)H(31B)—C(311)—H(31C)103.08

Experimental details

Crystal data
Chemical formulaC11H12NO4P
Mr253.19
Crystal system, space groupOrthorhombic, P212121
Temperature (K)100
a, b, c (Å)9.2532 (10), 10.1555 (16), 12.6610 (12)
V3)1189.8 (3)
Z4
Radiation typeSynchrotron, λ = 0.60000 Å
µ (mm1)0.23
Crystal size (mm)0.45 × 0.3 × 0.18
Data collection
DiffractometerHuber
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
98994, 17584, 16534
Rint0.035
(sin θ/λ)max1)1.250
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.015, 0.017, 1.37
No. of reflections14864
No. of parameters534
Δρmax, Δρmin (e Å3)0.13, 0.30

Computer programs: MarCCD (Paulmann & Morgenroth, 2006), EVAL 15 (Schreurs, 2010), SHELXS97 (Sheldrick, 2008), Volkov et al., (2006).

Selected geometric parameters (Å, º) top
P(2)—O(1)1.6085 (2)C(6)—C(7)1.4012 (4)
P(2)—O(21)1.4743 (2)C(6)—H(6)1.0830
P(2)—O(22)1.5779 (2)C(7)—C(8)1.3959 (4)
P(2)—C(3)1.7519 (2)C(7)—H(7)1.0829
O(1)—C(9)1.3874 (3)C(8)—C(9)1.3934 (3)
O(4)—C(4)1.2476 (3)C(8)—H(8)1.0828
N(1)—C(31)1.3218 (3)C(9)—C(10)1.3993 (3)
N(1)—H(1)1.0090C(23)—H(23A)1.0593
N(1)—H(2)1.0089C(23)—H(23B)1.0589
C(3)—C(4)1.4497 (3)C(23)—H(23C)1.0586
C(3)—C(31)1.4155 (3)C(31)—C(311)1.5040 (3)
C(4)—C(10)1.4986 (3)C(311)—H(31A)1.0589
C(5)—C(6)1.3918 (3)C(311)—H(31B)1.0590
C(5)—C(10)1.4048 (3)C(311)—H(31C)1.0590
C(5)—H(5)1.0829
O(1)—P(2)—O(21)107.861 (14)C(6)—C(7)—H(7)121.87
O(1)—P(2)—O(22)104.823 (13)C(8)—C(7)—H(7)117.83
O(1)—P(2)—C(3)104.851 (11)C(7)—C(8)—C(9)118.85 (2)
O(21)—P(2)—O(22)113.525 (16)C(7)—C(8)—H(8)122.67
O(21)—P(2)—C(3)119.290 (13)C(9)—C(8)—H(8)118.47
O(22)—P(2)—C(3)105.276 (10)O(1)—C(9)—C(8)117.24 (2)
P(2)—O(1)—C(9)118.922 (15)O(1)—C(9)—C(10)120.639 (19)
C(31)—N(1)—H(1)117.44C(8)—C(9)—C(10)122.08 (2)
C(31)—N(1)—H(2)116.46C(4)—C(10)—C(5)119.209 (18)
H(1)—N(1)—H(2)125.89C(4)—C(10)—C(9)122.768 (18)
P(2)—C(3)—C(4)117.891 (14)C(5)—C(10)—C(9)118.022 (19)
P(2)—C(3)—C(31)120.916 (16)H(23A)—C(23)—H(23B)111.47
C(4)—C(3)—C(31)121.193 (17)H(23A)—C(23)—H(23C)110.92
O(4)—C(4)—C(3)123.08 (2)H(23B)—C(23)—H(23C)112.27
O(4)—C(4)—C(10)118.14 (2)N(1)—C(31)—C(3)121.45 (2)
C(3)—C(4)—C(10)118.775 (17)N(1)—C(31)—C(311)116.16 (2)
C(6)—C(5)—C(10)120.80 (2)C(3)—C(31)—C(311)122.38 (2)
C(6)—C(5)—H(5)121.04C(31)—C(311)—H(31A)112.81
C(10)—C(5)—H(5)118.15C(31)—C(311)—H(31B)107.53
C(5)—C(6)—C(7)119.93 (2)C(31)—C(311)—H(31C)112.94
C(5)—C(6)—H(6)119.88H(31A)—C(311)—H(31B)107.45
C(7)—C(6)—H(6)120.19H(31A)—C(311)—H(31C)112.29
C(6)—C(7)—C(8)120.30 (2)H(31B)—C(311)—H(31C)103.08
 

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