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In the title compound, C18H22NO3P, the mol­ecules are linked by two N—H...N hydrogen bonds to form sheets built from R{_2^2}(8) rings.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805018003/hg6202sup1.cif
Contains datablocks sgwan, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805018003/hg6202Isup2.hkl
Contains datablock I

CCDC reference: 277279

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.045
  • wR factor = 0.121
  • Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C15 - C16 .. 5.23 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97; molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL.

2-benzylamino-4-phenyl-5,5-dimethyl-1,3,2-dioxaphosphorinane-2-oxide top
Crystal data top
C18H22NO3PZ = 2
Mr = 331.34F(000) = 352
Triclinic, P1Dx = 1.280 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.1916 (10) ÅCell parameters from 4140 reflections
b = 9.9676 (11) Åθ = 2.4–28.2°
c = 10.0055 (11) ŵ = 0.17 mm1
α = 86.049 (2)°T = 292 K
β = 72.405 (2)°Block, colourless
γ = 79.700 (2)°0.40 × 0.30 × 0.20 mm
V = 859.61 (16) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
3313 independent reflections
Radiation source: fine-focus sealed tube3056 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
φ and ω scansθmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 119
Tmin = 0.934, Tmax = 0.966k = 1212
5225 measured reflectionsl = 129
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.121 w = 1/[σ2(Fo2) + (0.0585P)2 + 0.2466P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
3313 reflectionsΔρmax = 0.23 e Å3
210 parametersΔρmin = 0.40 e Å3
Primary atom site location: structure-invariant direct methods
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
xyzUiso*/Ueq
C10.7514 (2)0.76324 (18)1.12149 (18)0.0447 (4)
C20.8227 (3)0.8756 (2)1.1123 (2)0.0532 (5)
H20.76820.96231.10370.064*
C30.9736 (3)0.8611 (3)1.1157 (2)0.0681 (6)
H31.01970.93791.11070.082*
C41.0560 (3)0.7335 (3)1.1264 (3)0.0760 (7)
H41.15830.72341.12700.091*
C50.9858 (3)0.6209 (3)1.1363 (3)0.0782 (7)
H51.04060.53431.14440.094*
C60.8346 (3)0.6359 (2)1.1343 (3)0.0634 (6)
H60.78800.55911.14170.076*
C70.5850 (2)0.78199 (19)1.1211 (2)0.0488 (4)
H7A0.51990.77941.21740.059*
H7B0.55840.87201.08300.059*
C80.5651 (2)0.87176 (19)0.6900 (2)0.0450 (4)
H8A0.51280.96320.67750.054*
H8B0.53920.81130.63180.054*
C90.73971 (19)0.87015 (17)0.64041 (18)0.0406 (4)
C100.7832 (2)0.97418 (19)0.7202 (2)0.0521 (5)
H10A0.74840.95470.81900.078*
H10B0.73501.06410.70120.078*
H10C0.89350.96930.69060.078*
C110.7829 (3)0.9061 (2)0.4838 (2)0.0639 (6)
H11A0.72640.99400.46960.096*
H11B0.75750.83870.43440.096*
H11C0.89200.90820.44900.096*
C120.81955 (18)0.72366 (16)0.66185 (17)0.0363 (4)
H120.79060.66220.60550.044*
C130.99396 (19)0.70126 (16)0.62436 (18)0.0394 (4)
C141.0826 (2)0.6551 (2)0.4926 (2)0.0532 (5)
H141.03450.63940.42690.064*
C151.2432 (3)0.6319 (2)0.4579 (3)0.0714 (7)
H151.30240.60210.36870.086*
C161.3144 (2)0.6532 (2)0.5550 (3)0.0732 (7)
H161.42180.63690.53180.088*
C171.2279 (2)0.6981 (2)0.6859 (3)0.0644 (6)
H171.27690.71240.75130.077*
C181.0681 (2)0.7225 (2)0.7214 (2)0.0488 (4)
H181.01000.75320.81050.059*
N10.54762 (17)0.68160 (15)1.04174 (16)0.0455 (4)
H10.50300.61701.08870.055*
O10.76194 (12)0.68402 (11)0.80907 (12)0.0384 (3)
O20.52944 (15)0.57087 (13)0.82421 (13)0.0486 (3)
O30.50851 (13)0.83011 (12)0.83543 (13)0.0450 (3)
P10.58277 (5)0.68198 (4)0.87492 (4)0.03679 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0584 (11)0.0456 (9)0.0320 (8)0.0138 (8)0.0132 (8)0.0010 (7)
C20.0702 (13)0.0508 (11)0.0441 (10)0.0211 (9)0.0194 (9)0.0038 (8)
C30.0800 (15)0.0878 (17)0.0527 (13)0.0441 (13)0.0289 (11)0.0109 (11)
C40.0668 (14)0.113 (2)0.0601 (14)0.0211 (14)0.0342 (12)0.0073 (13)
C50.0839 (18)0.0763 (16)0.0839 (18)0.0012 (13)0.0479 (15)0.0020 (13)
C60.0775 (15)0.0499 (11)0.0726 (15)0.0136 (10)0.0360 (12)0.0035 (10)
C70.0559 (11)0.0460 (10)0.0419 (10)0.0123 (8)0.0069 (8)0.0068 (8)
C80.0404 (9)0.0458 (9)0.0505 (10)0.0078 (7)0.0179 (8)0.0095 (8)
C90.0383 (9)0.0426 (9)0.0420 (9)0.0107 (7)0.0128 (7)0.0078 (7)
C100.0478 (10)0.0405 (9)0.0692 (13)0.0138 (8)0.0157 (9)0.0012 (8)
C110.0640 (13)0.0750 (14)0.0496 (12)0.0133 (11)0.0166 (10)0.0232 (10)
C120.0367 (8)0.0406 (8)0.0327 (8)0.0115 (6)0.0096 (6)0.0012 (6)
C130.0359 (8)0.0384 (8)0.0416 (9)0.0092 (6)0.0069 (7)0.0009 (7)
C140.0511 (11)0.0529 (11)0.0508 (11)0.0147 (8)0.0027 (9)0.0087 (8)
C150.0549 (12)0.0584 (13)0.0790 (16)0.0131 (10)0.0182 (11)0.0182 (11)
C160.0352 (10)0.0623 (13)0.113 (2)0.0088 (9)0.0074 (12)0.0062 (13)
C170.0430 (11)0.0690 (13)0.0861 (17)0.0134 (9)0.0253 (11)0.0051 (12)
C180.0399 (9)0.0568 (11)0.0511 (11)0.0100 (8)0.0146 (8)0.0002 (8)
N10.0499 (8)0.0464 (8)0.0414 (8)0.0222 (7)0.0077 (7)0.0028 (6)
O10.0337 (6)0.0423 (6)0.0377 (6)0.0083 (5)0.0091 (5)0.0083 (5)
O20.0543 (7)0.0505 (7)0.0466 (7)0.0233 (6)0.0161 (6)0.0044 (5)
O30.0349 (6)0.0452 (7)0.0504 (7)0.0060 (5)0.0077 (5)0.0065 (5)
P10.0340 (2)0.0385 (3)0.0385 (3)0.01216 (17)0.00916 (18)0.00383 (17)
Geometric parameters (Å, º) top
C1—C61.380 (3)C10—H10C0.9600
C1—C21.380 (3)C11—H11A0.9600
C1—C71.509 (3)C11—H11B0.9600
C2—C31.379 (3)C11—H11C0.9600
C2—H20.9300C12—O11.4592 (19)
C3—C41.375 (4)C12—C131.510 (2)
C3—H30.9300C12—H120.9800
C4—C51.375 (4)C13—C141.384 (3)
C4—H40.9300C13—C181.390 (3)
C5—C61.376 (3)C14—C151.390 (3)
C5—H50.9300C14—H140.9300
C6—H60.9300C15—C161.371 (4)
C7—N11.465 (2)C15—H150.9300
C7—H7A0.9700C16—C171.368 (4)
C7—H7B0.9700C16—H160.9300
C8—O31.448 (2)C17—C181.383 (3)
C8—C91.528 (2)C17—H170.9300
C8—H8A0.9700C18—H180.9300
C8—H8B0.9700N1—P11.6013 (15)
C9—C101.525 (2)N1—H10.8600
C9—C111.529 (3)O1—P11.5814 (11)
C9—C121.544 (2)O2—P11.4650 (13)
C10—H10A0.9600O3—P11.5888 (12)
C10—H10B0.9600
C6—C1—C2118.44 (19)C9—C11—H11A109.5
C6—C1—C7121.68 (17)C9—C11—H11B109.5
C2—C1—C7119.86 (17)H11A—C11—H11B109.5
C3—C2—C1120.9 (2)C9—C11—H11C109.5
C3—C2—H2119.6H11A—C11—H11C109.5
C1—C2—H2119.6H11B—C11—H11C109.5
C4—C3—C2120.1 (2)O1—C12—C13106.99 (13)
C4—C3—H3119.9O1—C12—C9108.87 (12)
C2—C3—H3119.9C13—C12—C9116.19 (13)
C3—C4—C5119.4 (2)O1—C12—H12108.2
C3—C4—H4120.3C13—C12—H12108.2
C5—C4—H4120.3C9—C12—H12108.2
C4—C5—C6120.3 (2)C14—C13—C18118.95 (17)
C4—C5—H5119.9C14—C13—C12119.84 (16)
C6—C5—H5119.9C18—C13—C12121.19 (15)
C5—C6—C1120.9 (2)C13—C14—C15120.3 (2)
C5—C6—H6119.6C13—C14—H14119.9
C1—C6—H6119.6C15—C14—H14119.9
N1—C7—C1115.78 (15)C16—C15—C14120.0 (2)
N1—C7—H7A108.3C16—C15—H15120.0
C1—C7—H7A108.3C14—C15—H15120.0
N1—C7—H7B108.3C17—C16—C15120.3 (2)
C1—C7—H7B108.3C17—C16—H16119.9
H7A—C7—H7B107.4C15—C16—H16119.9
O3—C8—C9113.17 (13)C16—C17—C18120.3 (2)
O3—C8—H8A108.9C16—C17—H17119.8
C9—C8—H8A108.9C18—C17—H17119.8
O3—C8—H8B108.9C17—C18—C13120.20 (19)
C9—C8—H8B108.9C17—C18—H18119.9
H8A—C8—H8B107.8C13—C18—H18119.9
C10—C9—C8110.51 (15)C7—N1—P1125.52 (12)
C10—C9—C11110.23 (16)C7—N1—H1117.2
C8—C9—C11106.93 (15)P1—N1—H1117.2
C10—C9—C12111.93 (14)C12—O1—P1118.75 (10)
C8—C9—C12107.71 (13)C8—O3—P1115.72 (10)
C11—C9—C12109.37 (15)O2—P1—O1113.64 (7)
C9—C10—H10A109.5O2—P1—O3114.16 (7)
C9—C10—H10B109.5O1—P1—O3102.17 (6)
H10A—C10—H10B109.5O2—P1—N1113.76 (7)
C9—C10—H10C109.5O1—P1—N1106.91 (7)
H10A—C10—H10C109.5O3—P1—N1105.16 (8)
H10B—C10—H10C109.5
C6—C1—C2—C30.1 (3)C9—C12—C13—C1887.3 (2)
C7—C1—C2—C3178.52 (18)C18—C13—C14—C150.7 (3)
C1—C2—C3—C40.9 (3)C12—C13—C14—C15178.92 (17)
C2—C3—C4—C51.2 (4)C13—C14—C15—C160.9 (3)
C3—C4—C5—C60.5 (4)C14—C15—C16—C170.5 (4)
C4—C5—C6—C10.4 (4)C15—C16—C17—C180.0 (4)
C2—C1—C6—C50.7 (3)C16—C17—C18—C130.1 (3)
C7—C1—C6—C5179.1 (2)C14—C13—C18—C170.3 (3)
C6—C1—C7—N140.8 (2)C12—C13—C18—C17178.42 (17)
C2—C1—C7—N1140.81 (17)C1—C7—N1—P179.0 (2)
O3—C8—C9—C1064.02 (19)C13—C12—O1—P1173.84 (10)
O3—C8—C9—C11176.00 (15)C9—C12—O1—P159.86 (15)
O3—C8—C9—C1258.54 (18)C9—C8—O3—P158.46 (17)
C10—C9—C12—O164.84 (17)C12—O1—P1—O271.01 (12)
C8—C9—C12—O156.84 (16)C12—O1—P1—O352.46 (12)
C11—C9—C12—O1172.70 (14)C12—O1—P1—N1162.65 (11)
C10—C9—C12—C1355.97 (19)C8—O3—P1—O273.55 (13)
C8—C9—C12—C13177.65 (14)C8—O3—P1—O149.56 (12)
C11—C9—C12—C1366.49 (19)C8—O3—P1—N1161.07 (12)
O1—C12—C13—C14143.66 (16)C7—N1—P1—O2178.65 (14)
C9—C12—C13—C1494.52 (19)C7—N1—P1—O155.08 (16)
O1—C12—C13—C1834.5 (2)C7—N1—P1—O353.02 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.862.042.8690 (19)161
Symmetry code: (i) x+1, y+1, z+2.
 

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