Crystal structure of caesium dimethyl-N-benzoyl­amido­phosphate monohydrate

The crystal structure of the caesium salt of dimethyl-N-benzoyl­amido­phosphate is reported and discussed.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.033
• wR factor = 0.076
• Data-to-parameter ratio = 24.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         O4 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        Cs1 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         P1 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.078 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          3 Note
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          2 Info
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          3 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        3.4 Low
PLAT967_ALERT_5_G Note: Two-Theta Cutoff Value in Embedded .res ..       60.0 Degree
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

---

Computing details

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT2014/4 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2019/2 (Sheldrick, 2015b); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

Aqua[dimethyl (N-benzoylamido-κO)phosphonato-κO]caesium

Crystal data

[Cs(C9H11NO4P)(H2O)]	F(000) = 736
Mr = 379.08	Dx = 1.874 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.3676 (4) Å	Cell parameters from 3272 reflections
b = 6.8089 (2) Å	θ = 3.6–28.2°
c = 13.7336 (3) Å	µ = 2.88 mm^−1
β = 90.549 (2)°	T = 294 K
V = 1343.46 (6) Å^3	Block, colourless
Z = 4	0.5 × 0.3 × 0.2 mm

Data collection

Xcalibur, Sapphire3 diffractometer	3169 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm^-1	Rint = 0.032
ω scans	θmax = 30.0°, θmin = 3.3°
Absorption correction: multi-scan (CrysAlisPro; Agilent, 2014)	h = −19→20
Tmin = 0.505, Tmax = 1.000	k = −9→9
13393 measured reflections	l = −18→19
3918 independent reflections

Refinement

Refinement on F^2	Primary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.076	w = 1/[σ^2(Fo^2) + (0.0307P)^2 + 0.4727P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
3918 reflections	Δρmax = 0.52 e Å^−3
162 parameters	Δρmin = −0.79 e Å^−3
3 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cs1	0.48526 (2)	0.71528 (3)	0.62552 (2)	0.04947 (8)
O5	0.4180 (2)	0.7620 (5)	0.8390 (2)	0.0816 (9)
H5A	0.371 (2)	0.806 (8)	0.869 (3)	0.122*
H5B	0.4702 (17)	0.723 (7)	0.863 (3)	0.122*
P1	0.66854 (5)	0.81111 (12)	0.39433 (6)	0.04547 (18)
O1	0.67121 (16)	0.4475 (4)	0.50718 (17)	0.0667 (7)
O2	0.57605 (15)	0.8484 (4)	0.43493 (16)	0.0618 (6)
O3	0.65141 (15)	0.6826 (4)	0.29932 (16)	0.0597 (6)
O4	0.70550 (16)	1.0147 (4)	0.3582 (2)	0.0768 (8)
N1	0.75168 (18)	0.7207 (4)	0.45799 (19)	0.0499 (6)
C1	0.74267 (19)	0.5511 (5)	0.50430 (18)	0.0438 (6)
C2	0.82889 (19)	0.4816 (4)	0.55712 (17)	0.0415 (6)
C3	0.8379 (3)	0.2855 (5)	0.5831 (2)	0.0534 (7)
H3	0.789853	0.198137	0.569188	0.064*
C4	0.9172 (3)	0.2191 (6)	0.6290 (3)	0.0668 (10)
H4	0.922916	0.087133	0.645488	0.080*
C5	0.9879 (2)	0.3473 (7)	0.6507 (3)	0.0682 (10)
H5	1.041536	0.302436	0.682000	0.082*
C6	0.9797 (2)	0.5411 (7)	0.6262 (2)	0.0607 (9)
H6	1.027423	0.628199	0.641683	0.073*
C7	0.90089 (19)	0.6085 (5)	0.5786 (2)	0.0477 (7)
H7	0.896380	0.740050	0.561044	0.057*
C8	0.7258 (3)	0.6063 (7)	0.2424 (3)	0.0770 (11)
H8A	0.772305	0.550223	0.284658	0.116*
H8B	0.752921	0.710446	0.205037	0.116*
H8C	0.702224	0.506856	0.199145	0.116*
C9	0.7984 (2)	1.0682 (6)	0.3429 (3)	0.0672 (9)
H9A	0.815023	1.038514	0.276950	0.101*
H9B	0.838067	0.996211	0.386767	0.101*
H9C	0.805753	1.206393	0.354371	0.101*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cs1	0.05209 (12)	0.05443 (14)	0.04190 (11)	0.00312 (8)	0.00059 (8)	0.00041 (8)
O5	0.0608 (16)	0.129 (3)	0.0550 (15)	0.0128 (17)	0.0018 (13)	−0.0145 (15)
P1	0.0379 (4)	0.0511 (5)	0.0475 (4)	0.0007 (3)	0.0042 (3)	0.0067 (3)
O1	0.0604 (13)	0.0699 (17)	0.0694 (14)	−0.0275 (12)	−0.0167 (11)	0.0249 (12)
O2	0.0450 (11)	0.0797 (17)	0.0608 (13)	0.0057 (11)	0.0116 (10)	−0.0051 (12)
O3	0.0486 (12)	0.0814 (18)	0.0492 (12)	0.0121 (11)	0.0043 (10)	−0.0048 (11)
O4	0.0550 (13)	0.0640 (17)	0.111 (2)	−0.0022 (12)	−0.0041 (13)	0.0376 (15)
N1	0.0432 (13)	0.0525 (16)	0.0539 (14)	−0.0066 (11)	−0.0026 (11)	0.0116 (11)
C1	0.0461 (14)	0.0500 (17)	0.0353 (13)	−0.0080 (13)	0.0028 (11)	0.0029 (12)
C2	0.0455 (14)	0.0512 (17)	0.0279 (11)	−0.0044 (12)	0.0034 (10)	0.0001 (11)
C3	0.065 (2)	0.0528 (19)	0.0425 (15)	−0.0022 (15)	0.0017 (14)	0.0034 (13)
C4	0.079 (3)	0.063 (2)	0.058 (2)	0.0165 (19)	0.0020 (18)	0.0101 (17)
C5	0.057 (2)	0.096 (3)	0.0516 (18)	0.018 (2)	−0.0009 (15)	0.0060 (19)
C6	0.0455 (17)	0.087 (3)	0.0495 (17)	−0.0040 (16)	−0.0013 (13)	−0.0041 (16)
C7	0.0470 (15)	0.0526 (19)	0.0434 (14)	−0.0034 (14)	0.0025 (12)	−0.0033 (12)
C8	0.067 (2)	0.089 (3)	0.076 (2)	−0.001 (2)	0.0257 (19)	−0.020 (2)
C9	0.072 (2)	0.059 (2)	0.072 (2)	−0.0156 (18)	0.0157 (17)	0.0108 (17)

Geometric parameters (Å, º)

Cs1—O1^i	3.086 (2)	C1—C2	1.506 (4)
Cs1—O1	3.631 (3)	C2—C3	1.388 (4)
Cs1—O2^ii	3.206 (3)	C2—C7	1.377 (4)
Cs1—O2	3.072 (2)	C3—H3	0.9300
Cs1—O3^iii	3.431 (2)	C3—C4	1.374 (5)
Cs1—O3^i	3.507 (3)	C4—H4	0.9300
Cs1—O4^ii	3.310 (2)	C4—C5	1.369 (6)
Cs1—O5	3.112 (3)	C5—H5	0.9300
Cs1—O5^iv	3.418 (4)	C5—C6	1.367 (6)
O5—H5A	0.853 (10)	C6—H6	0.9300
O5—H5B	0.856 (10)	C6—C7	1.379 (4)
P1—O2	1.468 (2)	C7—H7	0.9300
P1—O3	1.588 (2)	C8—H8A	0.9600
P1—O4	1.567 (3)	C8—H8B	0.9600
P1—N1	1.597 (3)	C8—H8C	0.9600
O1—C1	1.247 (3)	C9—H9A	0.9600
O3—C8	1.428 (4)	C9—H9B	0.9600
O4—C9	1.402 (4)	C9—H9C	0.9600
N1—C1	1.325 (4)
O1^i—Cs1—O5^iv	93.03 (7)	C1—O1—Cs1^i	141.26 (18)
O1^i—Cs1—O5	111.22 (7)	C1—O1—Cs1	109.9 (2)
O1^i—Cs1—O1	95.18 (5)	Cs1—O2—Cs1^ii	112.10 (7)
O1^i—Cs1—O2^ii	89.03 (6)	P1—O2—Cs1	131.74 (14)
O1^i—Cs1—O3^iii	169.01 (6)	P1—O2—Cs1^ii	108.03 (13)
O1^i—Cs1—O3^i	59.31 (5)	Cs1^vi—O3—Cs1^i	88.49 (5)
O1^i—Cs1—O4^ii	68.92 (7)	P1—O3—Cs1^i	105.47 (10)
O2^ii—Cs1—O5^iv	169.77 (6)	P1—O3—Cs1^vi	124.13 (11)
O2—Cs1—O5	155.59 (8)	C8—O3—Cs1^i	107.7 (2)
O2—Cs1—O5^iv	102.27 (6)	C8—O3—Cs1^vi	102.3 (2)
O2^ii—Cs1—O1	123.43 (5)	C8—O3—P1	122.6 (2)
O2—Cs1—O1	56.40 (6)	P1—O4—Cs1^ii	100.77 (10)
O2—Cs1—O1^i	85.16 (6)	C9—O4—Cs1^ii	131.0 (2)
O2—Cs1—O2^ii	67.90 (7)	C9—O4—P1	127.1 (2)
O2—Cs1—O3^iii	103.57 (6)	C1—N1—P1	121.5 (2)
O2^ii—Cs1—O3^iii	100.36 (6)	O1—C1—N1	126.3 (3)
O2—Cs1—O3^i	136.23 (6)	O1—C1—C2	118.8 (3)
O2^ii—Cs1—O3^i	129.70 (5)	N1—C1—C2	114.9 (2)
O2—Cs1—O4^ii	104.60 (6)	C3—C2—C1	120.0 (3)
O2^ii—Cs1—O4^ii	43.69 (6)	C7—C2—C1	121.3 (3)
O3^i—Cs1—O1	99.23 (5)	C7—C2—C3	118.7 (3)
O3^iii—Cs1—O1	84.44 (5)	C2—C3—H3	119.7
O3^iii—Cs1—O3^i	109.86 (5)	C4—C3—C2	120.6 (3)
O4^ii—Cs1—O5^iv	145.89 (7)	C4—C3—H3	119.7
O4^ii—Cs1—O1	157.27 (6)	C3—C4—H4	120.0
O4^ii—Cs1—O3^iii	114.31 (7)	C5—C4—C3	120.0 (4)
O4^ii—Cs1—O3^i	86.73 (6)	C5—C4—H4	120.0
O5—Cs1—O5^iv	95.01 (7)	C4—C5—H5	120.0
O5^iv—Cs1—O1	46.41 (6)	C6—C5—C4	119.9 (3)
O5—Cs1—O1	135.19 (7)	C6—C5—H5	120.0
O5—Cs1—O2^ii	93.57 (7)	C5—C6—H6	119.8
O5^iv—Cs1—O3^iii	78.73 (7)	C5—C6—C7	120.4 (3)
O5—Cs1—O3^i	67.78 (8)	C7—C6—H6	119.8
O5—Cs1—O3^iii	62.88 (7)	C2—C7—C6	120.3 (3)
O5^iv—Cs1—O3^i	59.24 (6)	C2—C7—H7	119.9
O5—Cs1—O4^ii	67.35 (7)	C6—C7—H7	119.9
Cs1—O5—Cs1^v	95.57 (9)	O3—C8—H8A	109.5
Cs1—O5—H5A	138 (3)	O3—C8—H8B	109.5
Cs1^v—O5—H5A	86 (4)	O3—C8—H8C	109.5
Cs1^v—O5—H5B	82 (4)	H8A—C8—H8B	109.5
Cs1—O5—H5B	93 (3)	H8A—C8—H8C	109.5
H5A—O5—H5B	129 (3)	H8B—C8—H8C	109.5
O2—P1—O3	105.88 (13)	O4—C9—H9A	109.5
O2—P1—O4	106.13 (15)	O4—C9—H9B	109.5
O2—P1—N1	122.26 (14)	O4—C9—H9C	109.5
O3—P1—N1	110.27 (14)	H9A—C9—H9B	109.5
O4—P1—O3	106.15 (15)	H9A—C9—H9C	109.5
O4—P1—N1	105.09 (13)	H9B—C9—H9C	109.5
Cs1^i—O1—Cs1	84.82 (5)
Cs1—O1—C1—N1	−62.6 (3)	O4—P1—O3—Cs1^i	−165.17 (10)
Cs1^i—O1—C1—N1	44.7 (5)	O4—P1—O3—Cs1^vi	−66.28 (16)
Cs1—O1—C1—C2	117.8 (2)	O4—P1—O3—C8	71.3 (3)
Cs1^i—O1—C1—C2	−135.0 (3)	O4—P1—N1—C1	176.7 (2)
P1—N1—C1—O1	−2.4 (5)	N1—P1—O2—Cs1	−13.3 (3)
P1—N1—C1—C2	177.2 (2)	N1—P1—O2—Cs1^ii	131.82 (14)
O1—C1—C2—C3	18.9 (4)	N1—P1—O3—Cs1^vi	−179.60 (12)
O1—C1—C2—C7	−162.7 (3)	N1—P1—O3—Cs1^i	81.52 (12)
O2—P1—O3—Cs1^i	−52.64 (14)	N1—P1—O3—C8	−42.0 (3)
O2—P1—O3—Cs1^vi	46.24 (18)	N1—P1—O4—Cs1^ii	−141.69 (12)
O2—P1—O3—C8	−176.2 (3)	N1—P1—O4—C9	27.5 (4)
O2—P1—O4—Cs1^ii	−10.89 (15)	N1—C1—C2—C3	−160.8 (3)
O2—P1—O4—C9	158.3 (3)	N1—C1—C2—C7	17.7 (4)
O2—P1—N1—C1	56.0 (3)	C1—C2—C3—C4	178.3 (3)
O3—P1—O2—Cs1	113.94 (18)	C1—C2—C7—C6	−179.3 (2)
O3—P1—O2—Cs1^ii	−100.92 (13)	C2—C3—C4—C5	0.7 (5)
O3—P1—O4—Cs1^ii	101.47 (12)	C3—C2—C7—C6	−0.8 (4)
O3—P1—O4—C9	−89.4 (3)	C3—C4—C5—C6	−0.2 (5)
O3—P1—N1—C1	−69.3 (3)	C4—C5—C6—C7	−0.8 (5)
O4—P1—O2—Cs1^ii	11.62 (16)	C5—C6—C7—C2	1.3 (5)
O4—P1—O2—Cs1	−133.52 (18)	C7—C2—C3—C4	−0.2 (4)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1; (iii) x, −y+3/2, z+1/2; (iv) −x+1, y−1/2, −z+3/2; (v) −x+1, y+1/2, −z+3/2; (vi) x, −y+3/2, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O1^v	0.85 (1)	2.05 (3)	2.785 (3)	143 (4)
O5—H5B···O2^iii	0.86 (1)	1.87 (1)	2.721 (4)	170 (4)

Symmetry codes: (iii) x, −y+3/2, z+1/2; (v) −x+1, y+1/2, −z+3/2.