Download citation
Download citation
link to html
The title compound, C12H16ClN2OP·2H2O, is a bicyclic phosphon­amide, containing carbon and phosphorus asymmetric centers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803025546/ac6070sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803025546/ac6070Isup2.hkl
Contains datablock I

CCDC reference: 234891

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.044
  • wR factor = 0.128
  • Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C9 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C10
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 2 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, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(1R*,3aS*)-1-(chloromethyl)-1λ5-phospha-2,6a-diazaperhydropentalene 1-oxide dihydrate top
Crystal data top
C12H16ClN2OP·2H2OF(000) = 1296
Mr = 306.72Dx = 1.342 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 486 reflections
a = 10.8756 (4) Åθ = 2.4–22.0°
b = 8.9390 (3) ŵ = 0.36 mm1
c = 31.227 (1) ÅT = 273 K
V = 3035.79 (18) Å3Block, colorless
Z = 80.34 × 0.26 × 0.24 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2976 independent reflections
Radiation source: fine-focus sealed tube2444 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
φ and ω scansθmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1013
Tmin = 0.887, Tmax = 0.918k = 811
15965 measured reflectionsl = 3835
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0646P)2 + 1.4344P]
where P = (Fo2 + 2Fc2)/3
2976 reflections(Δ/σ)max = 0.002
189 parametersΔρmax = 0.33 e Å3
4 restraintsΔρmin = 0.28 e Å3
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
Cl11.19910 (7)0.00584 (10)0.64832 (2)0.0731 (3)
O10.97200 (15)0.26161 (19)0.57157 (5)0.0519 (4)
O20.67640 (19)0.0936 (2)0.46773 (7)0.0652 (5)
O30.29161 (19)0.1757 (2)0.49073 (7)0.0657 (5)
P10.99187 (5)0.12667 (6)0.598076 (17)0.03787 (19)
N10.91500 (16)0.12069 (19)0.64414 (6)0.0412 (4)
N20.94271 (18)0.0338 (2)0.58118 (6)0.0485 (5)
C10.8521 (2)0.2117 (3)0.71420 (8)0.0564 (6)
H10.80830.12380.71870.068*
C20.8532 (3)0.3221 (4)0.74541 (9)0.0709 (8)
H20.80880.30770.77050.085*
C30.9181 (3)0.4517 (4)0.74008 (9)0.0685 (8)
H30.91940.52430.76140.082*
C40.9811 (3)0.4717 (3)0.70257 (10)0.0657 (7)
H41.02590.55930.69860.079*
C50.9800 (2)0.3660 (3)0.67059 (9)0.0545 (6)
H51.02190.38380.64510.065*
C60.91611 (19)0.2323 (2)0.67620 (7)0.0426 (5)
C70.8610 (2)0.0276 (3)0.65240 (8)0.0503 (6)
H7A0.78020.01730.66530.060*
H7B0.91290.08450.67170.060*
C80.8515 (2)0.1057 (3)0.60953 (9)0.0522 (6)
H80.76890.08990.59780.063*
C90.8830 (4)0.2704 (3)0.60711 (14)0.0944 (12)
H9A0.90410.30770.63530.113*
H9B0.81280.32650.59660.113*
C100.9858 (4)0.2884 (4)0.57845 (15)0.0994 (13)
H10A0.96970.36940.55850.119*
H10B1.05930.31280.59460.119*
C111.0043 (3)0.1453 (3)0.55445 (11)0.0694 (8)
H11A1.09100.12260.55140.083*
H11B0.96710.15030.52630.083*
C121.1565 (2)0.1191 (3)0.60684 (7)0.0467 (5)
H12A1.19650.08850.58050.056*
H12B1.18580.21860.61390.056*
H210.611 (2)0.132 (4)0.4597 (11)0.092 (12)*
H220.708 (3)0.161 (3)0.4829 (9)0.073 (10)*
H240.306 (3)0.090 (2)0.4992 (11)0.088 (11)*
H230.341 (3)0.184 (4)0.4696 (9)0.098 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0582 (4)0.0971 (6)0.0640 (4)0.0226 (4)0.0065 (3)0.0190 (4)
O10.0524 (9)0.0501 (9)0.0530 (9)0.0007 (7)0.0026 (7)0.0136 (7)
O20.0639 (12)0.0507 (11)0.0809 (14)0.0047 (10)0.0094 (10)0.0056 (10)
O30.0677 (13)0.0602 (12)0.0692 (12)0.0087 (10)0.0159 (10)0.0113 (10)
P10.0340 (3)0.0395 (3)0.0401 (3)0.0007 (2)0.0002 (2)0.0037 (2)
N10.0382 (9)0.0391 (9)0.0463 (10)0.0035 (7)0.0062 (8)0.0001 (8)
N20.0463 (10)0.0483 (11)0.0507 (11)0.0059 (8)0.0062 (9)0.0048 (9)
C10.0614 (15)0.0583 (15)0.0496 (13)0.0010 (12)0.0066 (11)0.0001 (11)
C20.086 (2)0.0816 (19)0.0455 (14)0.0023 (17)0.0100 (13)0.0077 (14)
C30.0742 (19)0.0744 (19)0.0568 (17)0.0060 (15)0.0074 (14)0.0210 (14)
C40.0626 (17)0.0598 (16)0.0746 (19)0.0071 (13)0.0052 (14)0.0139 (14)
C50.0514 (14)0.0543 (15)0.0577 (14)0.0060 (11)0.0046 (11)0.0078 (11)
C60.0353 (10)0.0469 (12)0.0456 (12)0.0063 (9)0.0036 (9)0.0005 (9)
C70.0465 (13)0.0469 (13)0.0574 (14)0.0081 (10)0.0077 (10)0.0065 (11)
C80.0414 (12)0.0446 (13)0.0704 (15)0.0078 (10)0.0111 (11)0.0046 (11)
C90.118 (3)0.0449 (16)0.120 (3)0.0012 (18)0.049 (2)0.0023 (17)
C100.097 (3)0.0541 (19)0.147 (4)0.0163 (17)0.037 (2)0.010 (2)
C110.0635 (17)0.0648 (18)0.0800 (19)0.0098 (13)0.0217 (14)0.0263 (15)
C120.0385 (11)0.0511 (13)0.0507 (12)0.0007 (10)0.0009 (9)0.0036 (10)
Geometric parameters (Å, º) top
Cl1—C121.772 (2)C4—C51.375 (4)
O1—P11.4787 (16)C4—H40.9300
O2—H210.833 (18)C5—C61.393 (3)
O2—H220.842 (18)C5—H50.9300
O3—H240.828 (18)C7—C81.513 (3)
O3—H230.851 (18)C7—H7A0.9700
P1—N21.619 (2)C7—H7B0.9700
P1—N11.6646 (18)C8—C91.514 (4)
P1—C121.813 (2)C8—H80.9800
N1—C61.413 (3)C9—C101.441 (5)
N1—C71.473 (3)C9—H9A0.9700
N2—C111.462 (3)C9—H9B0.9700
N2—C81.477 (3)C10—C111.496 (5)
C1—C21.387 (4)C10—H10A0.9700
C1—C61.388 (3)C10—H10B0.9700
C1—H10.9300C11—H11A0.9700
C2—C31.366 (4)C11—H11B0.9700
C2—H20.9300C12—H12A0.9700
C3—C41.369 (4)C12—H12B0.9700
C3—H30.9300
H21—O2—H22103 (3)C8—C7—H7A110.4
H24—O3—H23102 (3)N1—C7—H7B110.4
O1—P1—N2119.46 (10)C8—C7—H7B110.4
O1—P1—N1115.88 (10)H7A—C7—H7B108.6
N2—P1—N195.02 (9)N2—C8—C7106.50 (18)
O1—P1—C12105.03 (10)N2—C8—C9104.0 (2)
N2—P1—C12110.02 (11)C7—C8—C9118.5 (3)
N1—P1—C12111.37 (10)N2—C8—H8109.1
C6—N1—C7120.97 (18)C7—C8—H8109.1
C6—N1—P1125.82 (14)C9—C8—H8109.1
C7—N1—P1112.37 (14)C10—C9—C8108.4 (3)
C11—N2—C8110.67 (19)C10—C9—H9A110.0
C11—N2—P1129.70 (17)C8—C9—H9A110.0
C8—N2—P1114.32 (15)C10—C9—H9B110.0
C2—C1—C6120.1 (2)C8—C9—H9B110.0
C2—C1—H1119.9H9A—C9—H9B108.4
C6—C1—H1119.9C9—C10—C11108.6 (3)
C3—C2—C1121.5 (3)C9—C10—H10A110.0
C3—C2—H2119.3C11—C10—H10A110.0
C1—C2—H2119.3C9—C10—H10B110.0
C2—C3—C4118.3 (3)C11—C10—H10B110.0
C2—C3—H3120.8H10A—C10—H10B108.3
C4—C3—H3120.8N2—C11—C10103.6 (2)
C3—C4—C5121.8 (3)N2—C11—H11A111.0
C3—C4—H4119.1C10—C11—H11A111.0
C5—C4—H4119.1N2—C11—H11B111.0
C4—C5—C6120.2 (2)C10—C11—H11B111.0
C4—C5—H5119.9H11A—C11—H11B109.0
C6—C5—H5119.9Cl1—C12—P1113.08 (12)
C1—C6—C5118.1 (2)Cl1—C12—H12A109.0
C1—C6—N1120.5 (2)P1—C12—H12A109.0
C5—C6—N1121.4 (2)Cl1—C12—H12B109.0
N1—C7—C8106.69 (19)P1—C12—H12B109.0
N1—C7—H7A110.4H12A—C12—H12B107.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H23···O1i0.85 (2)1.98 (2)2.819 (3)168 (4)
O3—H24···O2ii0.83 (2)1.95 (2)2.757 (3)166 (3)
O2—H22···O3iii0.84 (2)1.91 (2)2.740 (3)171 (3)
O2—H21···O1i0.83 (2)2.03 (2)2.850 (3)167 (4)
Symmetry codes: (i) x1/2, y+1/2, z+1; (ii) x+1, y, z+1; (iii) x+1/2, y+1/2, z+1.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds