Crystal structures of two bis-carbamoyl­methyl­phosphine oxide (CMPO) compounds

The crystal structures of two multidentate CMPO-containing organic ligands are described. Both compounds feature N—H...O hydrogen bonds in the solid state.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.117
• Data-to-parameter ratio = 14.8

Structure: II

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.035
• wR factor = 0.093
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         32 Report

Alert level G
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         35 Note
PLAT955_ALERT_1_G Reported (CIF) and Actual (FCF) Lmax Differ by .          1 Units
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Info

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

   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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: II


Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          1 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         18 Note
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          9 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        69% Note
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O3             118.7 Degree
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O4             121.8 Degree
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O3A            119.9 Degree
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O4A            119.1 Degree
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         12 Note
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         20 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         23 Note
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
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  14 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
   5 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

For both structures, data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013). Program(s) used to solve structure: SHELXS (Sheldrick, 2008) for (I); olex2.solve (Bourhis et al., 2015) for (II). For both structures, program(s) used to refine structure: SHELXL (Sheldrick, 2015). Molecular graphics: OLEX2 (Dolomanov et al., 2009; Bourhis et al., 2015) for (I); OLEX2 (Dolomanov et al., 2009) for (II). Software used to prepare material for publication: CrystalMaker (Palmer, 2007) for (I); OLEX2 (Dolomanov et al., 2009) for (II).

{[(3-{[2-(Diphenylphosphinoyl)ethanamido]methyl}benzyl)carbamoyl]methyl}diphenylphosphine oxide (I)

Crystal data

C36H34N2O4P2	F(000) = 1304
Mr = 620.59	Dx = 1.312 Mg m^−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
a = 13.0352 (2) Å	Cell parameters from 7639 reflections
b = 14.1348 (4) Å	θ = 4.6–71.9°
c = 17.0471 (4) Å	µ = 1.60 mm^−1
β = 90.217 (2)°	T = 173 K
V = 3140.90 (13) Å^3	Needle, colourless
Z = 4	0.38 × 0.11 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer	2543 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.050
Absorption correction: multi-scan (SADABS; Bruker, 2013)	θmax = 72.1°, θmin = 4.6°
Tmin = 0.617, Tmax = 0.754	h = −16→16
16825 measured reflections	k = −17→16
3022 independent reflections	l = −21→20

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.071P)^2 + 1.6884P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
3022 reflections	Δρmax = 0.33 e Å^−3
204 parameters	Δρmin = −0.27 e Å^−3
0 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
P1	0.61558 (3)	0.01942 (3)	0.65310 (2)	0.02456 (15)
O1	0.51178 (11)	0.16409 (10)	0.52941 (8)	0.0387 (4)
O2	0.63820 (10)	0.08953 (9)	0.71622 (8)	0.0319 (3)
N1	0.40562 (13)	0.18290 (11)	0.63349 (10)	0.0304 (4)
H1	0.3839 (17)	0.1569 (16)	0.6753 (14)	0.031 (6)*
C1	0.46922 (13)	0.13271 (13)	0.58793 (10)	0.0279 (4)
C2	0.48641 (14)	0.03112 (13)	0.61386 (10)	0.0279 (4)
H2A	0.477236	−0.012087	0.568671	0.033*
H2B	0.435750	0.013809	0.654532	0.033*
C3	0.39481 (17)	0.28492 (14)	0.62513 (12)	0.0367 (5)
H3A	0.321015	0.301452	0.625674	0.044*
H3B	0.422971	0.304441	0.573764	0.044*
C4	0.44947 (14)	0.33936 (13)	0.68985 (12)	0.0323 (4)
C5	0.44880 (15)	0.43806 (14)	0.69115 (14)	0.0388 (5)
H5	0.413150	0.472302	0.651594	0.047*
C6	0.500000	0.4858 (2)	0.750000	0.0418 (7)
H6	0.500001	0.553010	0.750000	0.050*
C7	0.500000	0.29186 (19)	0.750000	0.0337 (6)
H7	0.500000	0.224650	0.750000	0.040*
C8	0.70406 (14)	0.03028 (13)	0.57209 (10)	0.0282 (4)
C9	0.75675 (18)	0.11496 (16)	0.56285 (13)	0.0430 (5)
H9	0.745261	0.165338	0.598650	0.052*
C10	0.8259 (2)	0.12686 (19)	0.50205 (16)	0.0560 (7)
H10	0.862193	0.184740	0.496512	0.067*
C11	0.84148 (19)	0.0541 (2)	0.44976 (15)	0.0575 (7)
H11	0.888183	0.062054	0.407633	0.069*
C12	0.78956 (18)	−0.03057 (19)	0.45821 (14)	0.0495 (6)
H12	0.800717	−0.080434	0.421862	0.059*
C13	0.72129 (15)	−0.04301 (15)	0.51949 (12)	0.0355 (4)
H13	0.686365	−0.101540	0.525499	0.043*
C14	0.62569 (14)	−0.10082 (13)	0.68680 (11)	0.0278 (4)
C15	0.57441 (16)	−0.17625 (14)	0.65110 (12)	0.0342 (4)
H15	0.527354	−0.164934	0.609453	0.041*
C16	0.59268 (17)	−0.26772 (15)	0.67688 (13)	0.0407 (5)
H16	0.557730	−0.319191	0.652892	0.049*
C17	0.66130 (17)	−0.28459 (16)	0.73716 (16)	0.0472 (6)
H17	0.674521	−0.347566	0.753841	0.057*
C18	0.71074 (17)	−0.20969 (18)	0.77322 (15)	0.0481 (6)
H18	0.757181	−0.221448	0.815181	0.058*
C19	0.69321 (15)	−0.11785 (15)	0.74878 (12)	0.0359 (4)
H19	0.726984	−0.066640	0.774090	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0270 (2)	0.0245 (2)	0.0222 (2)	0.00211 (17)	0.00302 (17)	−0.00095 (16)
O1	0.0434 (8)	0.0417 (8)	0.0310 (7)	0.0046 (6)	0.0073 (6)	0.0093 (6)
O2	0.0351 (7)	0.0325 (7)	0.0281 (6)	0.0011 (6)	0.0016 (5)	−0.0055 (5)
N1	0.0345 (8)	0.0285 (8)	0.0283 (8)	0.0040 (7)	0.0030 (7)	0.0035 (6)
C1	0.0282 (9)	0.0317 (10)	0.0238 (9)	0.0006 (7)	−0.0023 (7)	0.0012 (7)
C2	0.0294 (9)	0.0291 (9)	0.0251 (8)	0.0009 (7)	0.0022 (7)	−0.0011 (7)
C3	0.0426 (11)	0.0291 (10)	0.0385 (11)	0.0092 (8)	0.0008 (9)	0.0063 (8)
C4	0.0296 (9)	0.0283 (9)	0.0392 (10)	0.0032 (7)	0.0094 (8)	0.0039 (8)
C5	0.0317 (10)	0.0297 (10)	0.0549 (13)	0.0048 (8)	0.0128 (9)	0.0078 (9)
C6	0.0384 (15)	0.0224 (13)	0.065 (2)	0.000	0.0157 (14)	0.000
C7	0.0376 (14)	0.0230 (12)	0.0406 (15)	0.000	0.0051 (12)	0.000
C8	0.0262 (8)	0.0327 (9)	0.0256 (8)	0.0033 (7)	0.0025 (7)	0.0008 (7)
C9	0.0521 (13)	0.0356 (11)	0.0415 (12)	−0.0065 (10)	0.0124 (10)	−0.0018 (9)
C10	0.0556 (14)	0.0547 (15)	0.0577 (15)	−0.0170 (12)	0.0174 (12)	0.0078 (12)
C11	0.0456 (13)	0.0782 (18)	0.0488 (14)	−0.0083 (13)	0.0236 (11)	0.0011 (13)
C12	0.0458 (13)	0.0615 (15)	0.0414 (12)	0.0029 (11)	0.0146 (10)	−0.0137 (11)
C13	0.0328 (10)	0.0391 (11)	0.0346 (10)	−0.0002 (8)	0.0049 (8)	−0.0050 (8)
C14	0.0293 (9)	0.0271 (9)	0.0269 (8)	0.0046 (7)	0.0069 (7)	0.0024 (7)
C15	0.0392 (10)	0.0327 (10)	0.0308 (9)	0.0015 (8)	0.0041 (8)	0.0007 (8)
C16	0.0451 (11)	0.0284 (10)	0.0487 (12)	−0.0008 (9)	0.0110 (10)	0.0017 (9)
C17	0.0375 (11)	0.0345 (11)	0.0698 (16)	0.0057 (9)	0.0081 (11)	0.0192 (11)
C18	0.0340 (11)	0.0506 (13)	0.0595 (14)	0.0032 (10)	−0.0052 (10)	0.0233 (12)
C19	0.0299 (9)	0.0381 (11)	0.0398 (11)	−0.0002 (8)	−0.0003 (8)	0.0062 (9)

Geometric parameters (Å, º)

P1—O2	1.4915 (13)	C8—C13	1.389 (3)
P1—C2	1.8169 (19)	C9—H9	0.9500
P1—C8	1.8091 (18)	C9—C10	1.386 (3)
P1—C14	1.7988 (18)	C10—H10	0.9500
O1—C1	1.226 (2)	C10—C11	1.377 (4)
N1—H1	0.85 (2)	C11—H11	0.9500
N1—C1	1.341 (2)	C11—C12	1.382 (4)
N1—C3	1.456 (2)	C12—H12	0.9500
C1—C2	1.519 (3)	C12—C13	1.386 (3)
C2—H2A	0.9900	C13—H13	0.9500
C2—H2B	0.9900	C14—C15	1.397 (3)
C3—H3A	0.9900	C14—C19	1.393 (3)
C3—H3B	0.9900	C15—H15	0.9500
C3—C4	1.520 (3)	C15—C16	1.386 (3)
C4—C5	1.395 (3)	C16—H16	0.9500
C4—C7	1.390 (2)	C16—C17	1.381 (3)
C5—H5	0.9500	C17—H17	0.9500
C5—C6	1.379 (3)	C17—C18	1.382 (4)
C6—H6	0.9500	C18—H18	0.9500
C7—H7	0.9500	C18—C19	1.382 (3)
C8—C9	1.389 (3)	C19—H19	0.9500
O2—P1—C2	112.68 (8)	C9—C8—P1	118.45 (15)
O2—P1—C8	111.68 (8)	C13—C8—P1	122.32 (15)
O2—P1—C14	112.54 (8)	C13—C8—C9	119.22 (18)
C8—P1—C2	107.69 (8)	C8—C9—H9	119.6
C14—P1—C2	105.68 (9)	C10—C9—C8	120.8 (2)
C14—P1—C8	106.13 (8)	C10—C9—H9	119.6
C1—N1—H1	117.7 (15)	C9—C10—H10	120.3
C1—N1—C3	121.81 (17)	C11—C10—C9	119.4 (2)
C3—N1—H1	118.5 (15)	C11—C10—H10	120.3
O1—C1—N1	124.21 (18)	C10—C11—H11	119.8
O1—C1—C2	120.80 (17)	C10—C11—C12	120.4 (2)
N1—C1—C2	114.98 (15)	C12—C11—H11	119.8
P1—C2—H2A	109.8	C11—C12—H12	119.9
P1—C2—H2B	109.8	C11—C12—C13	120.3 (2)
C1—C2—P1	109.19 (12)	C13—C12—H12	119.9
C1—C2—H2A	109.8	C8—C13—H13	120.1
C1—C2—H2B	109.8	C12—C13—C8	119.9 (2)
H2A—C2—H2B	108.3	C12—C13—H13	120.1
N1—C3—H3A	109.1	C15—C14—P1	123.20 (15)
N1—C3—H3B	109.1	C19—C14—P1	116.79 (15)
N1—C3—C4	112.67 (16)	C19—C14—C15	119.90 (18)
H3A—C3—H3B	107.8	C14—C15—H15	120.2
C4—C3—H3A	109.1	C16—C15—C14	119.5 (2)
C4—C3—H3B	109.1	C16—C15—H15	120.2
C5—C4—C3	120.98 (19)	C15—C16—H16	119.8
C7—C4—C3	120.69 (18)	C17—C16—C15	120.5 (2)
C7—C4—C5	118.3 (2)	C17—C16—H16	119.8
C4—C5—H5	120.1	C16—C17—H17	120.1
C6—C5—C4	119.8 (2)	C16—C17—C18	119.9 (2)
C6—C5—H5	120.1	C18—C17—H17	120.1
C5—C6—C5^i	121.4 (3)	C17—C18—H18	119.7
C5^i—C6—H6	119.3	C19—C18—C17	120.6 (2)
C5—C6—H6	119.3	C19—C18—H18	119.7
C4—C7—C4^i	122.2 (3)	C14—C19—H19	120.2
C4—C7—H7	118.9	C18—C19—C14	119.6 (2)
C4^i—C7—H7	118.9	C18—C19—H19	120.2

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the C14–C19 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.85 (2)	2.10 (2)	2.940 (2)	168 (2)
C3—H3A···Cg^ii	0.99	2.76	3.622 (2)	146

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

Diethyl [({2-[2-(diethoxyphosphinoyl)ethanamido]ethyl}carbamoyl)methyl]phosphonate (II)

Crystal data

C14H30N2O8P2	Dx = 1.306 Mg m^−3
Mr = 416.34	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pbca	Cell parameters from 6034 reflections
a = 8.9401 (1) Å	θ = 4.1–72.0°
b = 15.0535 (2) Å	µ = 2.23 mm^−1
c = 15.7314 (3) Å	T = 173 K
V = 2117.13 (5) Å^3	Plate, colourless
Z = 4	0.34 × 0.23 × 0.06 mm
F(000) = 888

Data collection

Bruker APEXII CCD diffractometer	1839 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.028
Absorption correction: multi-scan (SADABS; Bruker, 2013)	θmax = 72.2°, θmin = 5.6°
Tmin = 0.612, Tmax = 0.754	h = −11→10
10282 measured reflections	k = −18→12
2057 independent reflections	l = −19→16

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.093	w = 1/[σ^2(Fo^2) + (0.045P)^2 + 0.8277P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2057 reflections	Δρmax = 0.21 e Å^−3
154 parameters	Δρmin = −0.27 e Å^−3
20 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	Occ. (<1)
P1	0.49865 (8)	0.16848 (6)	0.58724 (5)	0.0291 (2)	0.7387 (19)
O2	0.3858 (2)	0.23508 (12)	0.56270 (16)	0.0402 (5)	0.7387 (19)
O3	0.6214 (2)	0.20596 (15)	0.64985 (15)	0.0364 (4)	0.7387 (19)
O4	0.43649 (17)	0.08482 (10)	0.63416 (10)	0.0361 (4)	0.7387 (19)
C2	0.5970 (5)	0.1213 (3)	0.49806 (18)	0.0255 (6)	0.7387 (19)
H2A	0.526044	0.087298	0.462353	0.031*	0.7387 (19)
H2B	0.639568	0.169666	0.462907	0.031*	0.7387 (19)
C4	0.6892 (3)	0.2924 (2)	0.6313 (3)	0.0433 (7)	0.7387 (19)
H4A	0.620650	0.340728	0.648672	0.052*	0.7387 (19)
H4B	0.708400	0.297943	0.569581	0.052*	0.7387 (19)
C5	0.8336 (4)	0.2991 (3)	0.6797 (3)	0.0521 (8)	0.7387 (19)
H5A	0.901244	0.251520	0.661636	0.078*	0.7387 (19)
H5B	0.813603	0.293490	0.740726	0.078*	0.7387 (19)
H5C	0.880239	0.356862	0.668357	0.078*	0.7387 (19)
C6	0.3339 (3)	0.09235 (16)	0.70583 (18)	0.0470 (6)	0.7387 (19)
H6A	0.250321	0.132632	0.691026	0.056*	0.7387 (19)
H6B	0.386886	0.117380	0.755628	0.056*	0.7387 (19)
C7	0.2754 (9)	0.0033 (4)	0.7266 (5)	0.0514 (10)	0.7387 (19)
H7A	0.209468	−0.016933	0.680694	0.077*	0.7387 (19)
H7B	0.218830	0.006108	0.779863	0.077*	0.7387 (19)
H7C	0.358860	−0.038321	0.732867	0.077*	0.7387 (19)
O1	0.69589 (11)	−0.01159 (7)	0.56001 (7)	0.0369 (3)
N1	0.85841 (14)	0.09068 (9)	0.51170 (9)	0.0333 (3)
C1	0.72039 (15)	0.06112 (9)	0.52745 (9)	0.0287 (3)
C3	0.98811 (16)	0.03699 (10)	0.53232 (10)	0.0348 (3)
H3A	0.974766	0.010625	0.589473	0.042*
H3B	1.078035	0.075326	0.533945	0.042*
P1A	0.5246 (3)	0.19107 (16)	0.60724 (17)	0.0291 (2)	0.2613 (19)
O2A	0.4150 (8)	0.2586 (4)	0.5806 (5)	0.0402 (5)	0.2613 (19)
O3A	0.6639 (8)	0.2236 (5)	0.6594 (5)	0.0364 (4)	0.2613 (19)
O4A	0.4656 (5)	0.1195 (3)	0.6726 (3)	0.0361 (4)	0.2613 (19)
C2A	0.5883 (17)	0.1303 (10)	0.5188 (7)	0.0255 (6)	0.2613 (19)
H2AA	0.501156	0.097716	0.495619	0.031*	0.2613 (19)
H2AB	0.618606	0.173979	0.474973	0.031*	0.2613 (19)
C4A	0.7429 (11)	0.3020 (7)	0.6334 (9)	0.0433 (7)	0.2613 (19)
H4AA	0.678295	0.354818	0.640873	0.052*	0.2613 (19)
H4AB	0.770059	0.297421	0.572537	0.052*	0.2613 (19)
C5A	0.8806 (14)	0.3114 (11)	0.6859 (11)	0.0521 (8)	0.2613 (19)
H5AA	0.953206	0.265798	0.669311	0.078*	0.2613 (19)
H5AB	0.855187	0.304251	0.746069	0.078*	0.2613 (19)
H5AC	0.924122	0.370407	0.676741	0.078*	0.2613 (19)
C6A	0.3201 (9)	0.0845 (5)	0.6622 (5)	0.0470 (6)	0.2613 (19)
H6AA	0.303480	0.070051	0.601507	0.056*	0.2613 (19)
H6AB	0.245523	0.129747	0.679118	0.056*	0.2613 (19)
C7A	0.299 (3)	0.0026 (12)	0.7147 (16)	0.0514 (10)	0.2613 (19)
H7AA	0.272633	−0.047288	0.677574	0.077*	0.2613 (19)
H7AB	0.218138	0.012506	0.755778	0.077*	0.2613 (19)
H7AC	0.391725	−0.010925	0.745083	0.077*	0.2613 (19)
H1	0.871 (2)	0.1397 (13)	0.4883 (11)	0.038 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0313 (3)	0.0177 (4)	0.0384 (4)	0.0034 (3)	0.0024 (3)	0.0043 (3)
O2	0.0366 (11)	0.0231 (11)	0.0610 (14)	0.0061 (8)	0.0015 (8)	0.0068 (9)
O3	0.0456 (14)	0.0265 (12)	0.0372 (9)	0.0008 (8)	−0.0094 (9)	0.0011 (7)
O4	0.0430 (8)	0.0243 (8)	0.0409 (9)	0.0049 (6)	0.0152 (7)	0.0033 (6)
C2	0.0263 (9)	0.0256 (12)	0.0248 (18)	0.0006 (8)	0.0027 (13)	0.0054 (13)
C4	0.052 (2)	0.0284 (12)	0.0494 (10)	0.0007 (15)	−0.0097 (18)	0.0029 (9)
C5	0.053 (3)	0.0453 (18)	0.0576 (14)	−0.0050 (17)	−0.012 (2)	0.0038 (12)
C6	0.0605 (13)	0.0392 (11)	0.0413 (14)	−0.0010 (10)	0.0244 (14)	−0.0052 (12)
C7	0.054 (3)	0.0554 (12)	0.045 (2)	−0.0040 (14)	0.0188 (16)	0.0094 (12)
O1	0.0330 (5)	0.0251 (5)	0.0526 (6)	−0.0028 (4)	−0.0023 (5)	0.0110 (5)
N1	0.0263 (6)	0.0241 (6)	0.0496 (8)	−0.0009 (5)	0.0012 (5)	0.0071 (6)
C1	0.0285 (7)	0.0231 (7)	0.0343 (7)	−0.0023 (5)	−0.0019 (5)	0.0030 (5)
C3	0.0257 (7)	0.0333 (8)	0.0453 (8)	0.0002 (6)	−0.0029 (6)	0.0010 (7)
P1A	0.0313 (3)	0.0177 (4)	0.0384 (4)	0.0034 (3)	0.0024 (3)	0.0043 (3)
O2A	0.0366 (11)	0.0231 (11)	0.0610 (14)	0.0061 (8)	0.0015 (8)	0.0068 (9)
O3A	0.0456 (14)	0.0265 (12)	0.0372 (9)	0.0008 (8)	−0.0094 (9)	0.0011 (7)
O4A	0.0430 (8)	0.0243 (8)	0.0409 (9)	0.0049 (6)	0.0152 (7)	0.0033 (6)
C2A	0.0263 (9)	0.0256 (12)	0.0248 (18)	0.0006 (8)	0.0027 (13)	0.0054 (13)
C4A	0.052 (2)	0.0284 (12)	0.0494 (10)	0.0007 (15)	−0.0097 (18)	0.0029 (9)
C5A	0.053 (3)	0.0453 (18)	0.0576 (14)	−0.0050 (17)	−0.012 (2)	0.0038 (12)
C6A	0.0605 (13)	0.0392 (11)	0.0413 (14)	−0.0010 (10)	0.0244 (14)	−0.0052 (12)
C7A	0.054 (3)	0.0554 (12)	0.045 (2)	−0.0040 (14)	0.0188 (16)	0.0094 (12)

Geometric parameters (Å, º)

P1—O2	1.474 (2)	C1—C2A	1.580 (15)
P1—O3	1.5791 (16)	C3—C3^i	1.523 (3)
P1—O4	1.5619 (15)	C3—H3A	0.9900
P1—C2	1.801 (2)	C3—H3B	0.9900
O3—C4	1.464 (3)	P1A—O2A	1.473 (7)
O4—C6	1.458 (3)	P1A—O3A	1.570 (6)
C2—H2A	0.9900	P1A—O4A	1.581 (5)
C2—H2B	0.9900	P1A—C2A	1.760 (9)
C2—C1	1.501 (5)	O3A—C4A	1.435 (10)
C4—H4A	0.9900	O4A—C6A	1.413 (9)
C4—H4B	0.9900	C2A—H2AA	0.9900
C4—C5	1.502 (4)	C2A—H2AB	0.9900
C5—H5A	0.9800	C4A—H4AA	0.9900
C5—H5B	0.9800	C4A—H4AB	0.9900
C5—H5C	0.9800	C4A—C5A	1.489 (10)
C6—H6A	0.9900	C5A—H5AA	0.9800
C6—H6B	0.9900	C5A—H5AB	0.9800
C6—C7	1.475 (6)	C5A—H5AC	0.9800
C7—H7A	0.9800	C6A—H6AA	0.9900
C7—H7B	0.9800	C6A—H6AB	0.9900
C7—H7C	0.9800	C6A—C7A	1.495 (12)
O1—C1	1.2282 (17)	C7A—H7AA	0.9800
N1—C1	1.3348 (18)	C7A—H7AB	0.9800
N1—C3	1.4502 (19)	C7A—H7AC	0.9800
N1—H1	0.832 (19)
O2—P1—O3	113.34 (11)	N1—C1—C2A	117.1 (6)
O2—P1—O4	115.38 (11)	N1—C3—C3^i	111.71 (16)
O2—P1—C2	113.46 (18)	N1—C3—H3A	109.3
O3—P1—C2	106.70 (17)	N1—C3—H3B	109.3
O4—P1—O3	103.93 (11)	C3^i—C3—H3A	109.3
O4—P1—C2	102.95 (16)	C3^i—C3—H3B	109.3
C4—O3—P1	118.74 (19)	H3A—C3—H3B	107.9
C6—O4—P1	121.77 (14)	O2A—P1A—O3A	117.5 (4)
P1—C2—H2A	109.5	O2A—P1A—O4A	115.7 (4)
P1—C2—H2B	109.5	O2A—P1A—C2A	110.4 (6)
H2A—C2—H2B	108.0	O3A—P1A—O4A	97.9 (4)
C1—C2—P1	110.9 (2)	O3A—P1A—C2A	108.6 (6)
C1—C2—H2A	109.5	O4A—P1A—C2A	105.6 (5)
C1—C2—H2B	109.5	C4A—O3A—P1A	119.8 (7)
O3—C4—H4A	110.0	C6A—O4A—P1A	119.0 (5)
O3—C4—H4B	110.0	C1—C2A—P1A	121.1 (8)
O3—C4—C5	108.4 (3)	C1—C2A—H2AA	107.1
H4A—C4—H4B	108.4	C1—C2A—H2AB	107.1
C5—C4—H4A	110.0	P1A—C2A—H2AA	107.1
C5—C4—H4B	110.0	P1A—C2A—H2AB	107.1
C4—C5—H5A	109.5	H2AA—C2A—H2AB	106.8
C4—C5—H5B	109.5	O3A—C4A—H4AA	109.9
C4—C5—H5C	109.5	O3A—C4A—H4AB	109.9
H5A—C5—H5B	109.5	O3A—C4A—C5A	109.1 (9)
H5A—C5—H5C	109.5	H4AA—C4A—H4AB	108.3
H5B—C5—H5C	109.5	C5A—C4A—H4AA	109.9
O4—C6—H6A	109.9	C5A—C4A—H4AB	109.9
O4—C6—H6B	109.9	C4A—C5A—H5AA	109.5
O4—C6—C7	108.9 (3)	C4A—C5A—H5AB	109.5
H6A—C6—H6B	108.3	C4A—C5A—H5AC	109.5
C7—C6—H6A	109.9	H5AA—C5A—H5AB	109.5
C7—C6—H6B	109.9	H5AA—C5A—H5AC	109.5
C6—C7—H7A	109.5	H5AB—C5A—H5AC	109.5
C6—C7—H7B	109.5	O4A—C6A—H6AA	109.4
C6—C7—H7C	109.5	O4A—C6A—H6AB	109.4
H7A—C7—H7B	109.5	O4A—C6A—C7A	111.1 (13)
H7A—C7—H7C	109.5	H6AA—C6A—H6AB	108.0
H7B—C7—H7C	109.5	C7A—C6A—H6AA	109.4
C1—N1—C3	120.79 (12)	C7A—C6A—H6AB	109.4
C1—N1—H1	119.9 (13)	C6A—C7A—H7AA	109.5
C3—N1—H1	119.3 (13)	C6A—C7A—H7AB	109.5
O1—C1—C2	122.4 (2)	C6A—C7A—H7AC	109.5
O1—C1—N1	122.64 (13)	H7AA—C7A—H7AB	109.5
O1—C1—C2A	119.3 (6)	H7AA—C7A—H7AC	109.5
N1—C1—C2	114.9 (2)	H7AB—C7A—H7AC	109.5
P1—O3—C4—C5	−160.9 (3)	C1—N1—C3—C3^i	77.0 (2)
P1—O4—C6—C7	170.3 (4)	C3—N1—C1—C2	−176.50 (16)
P1—C2—C1—O1	71.4 (3)	C3—N1—C1—O1	0.4 (2)
P1—C2—C1—N1	−111.8 (2)	C3—N1—C1—C2A	169.1 (4)
O2—P1—O3—C4	−45.5 (3)	P1A—O3A—C4A—C5A	−172.5 (10)
O2—P1—O4—C6	−48.7 (2)	P1A—O4A—C6A—C7A	165.3 (11)
O2—P1—C2—C1	174.3 (2)	O2A—P1A—O3A—C4A	−44.3 (11)
O3—P1—O4—C6	76.0 (2)	O2A—P1A—O4A—C6A	40.5 (6)
O3—P1—C2—C1	48.8 (3)	O2A—P1A—C2A—C1	172.8 (8)
O4—P1—O3—C4	−171.6 (2)	O3A—P1A—O4A—C6A	166.2 (6)
O4—P1—C2—C1	−60.3 (3)	O3A—P1A—C2A—C1	42.7 (11)
C2—P1—O3—C4	80.1 (3)	O4A—P1A—O3A—C4A	−168.7 (8)
C2—P1—O4—C6	−172.9 (2)	O4A—P1A—C2A—C1	−61.4 (11)
O1—C1—C2A—P1A	76.3 (10)	C2A—P1A—O3A—C4A	81.9 (10)
N1—C1—C2A—P1A	−92.8 (9)	C2A—P1A—O4A—C6A	−81.9 (7)

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^ii	0.832 (19)	2.05 (2)	2.883 (2)	175.0 (18)
N1—H1···O2A^ii	0.832 (19)	1.92 (2)	2.741 (8)	170.2 (18)

Symmetry code: (ii) x+1/2, −y+1/2, −z+1.