metal-organic papers
m74
Sommer and Rheingold [CuI(C6H18N6P4)] doi:10.1107/S1600536805040791 Acta Cryst.(2006). E62, m74–m76 Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
A copper(I) coordination polymer containing an
adamantane P–N cage ligand
Roger D. Sommera* and Arnold L. Rheingoldb
a
DePaul University, Department of Chemistry, 1036 W. Belden Ave., Chicago, IL 60614-3251, USA, andbDepartment of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
Correspondence e-mail: rsommer@condor.depaul.edu
Key indicators
Single-crystal X-ray study
T= 100 K
Mean(C–N) = 0.003 A˚
Rfactor = 0.027
wRfactor = 0.069
Data-to-parameter ratio = 21.3
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2006 International Union of Crystallography
Printed in Great Britain – all rights reserved
The tetradentate non-chelating ligand 2,4,6,8,9,10-hexa-methyl-2,4,6,8,9,10-hexaaza-1,3,5,7-tetraphosphaadamantane, P4(NCH3)6, reacts with one equivalent of cuprous iodide to
yield the title coordination polymer, catena -poly[[iodo-copper(I)]- -2,4,6,8,9,10-hexamethyl-2,4,6,8,9,10-hexaaza-1,3,5,7-tetraphosphaadamantane-2
P1:P3], [CuI(C6H18N6P4)]n.
The polymer is linked through P—Cu coordination at two vertices of the cage. The CuI ions have a trigonal–planar geometry, coordinated by P atoms from two different ligands and the iodide. This structure represents the first crystal-lographically characterized coordination compound of this cage ligand.
Comment
Spectroscopic studies have shown that the cage compound P4(NCH3)6can coordinate up to four Lewis acids [Ni(CO)3, or
BH3], one at each P vertex (Reiss & Van Wazer, 1967, 1968).
Crystallographic studies of chalcogenide derivatives P4(NCH3)6Xn(X= O or S,n= 1–4) have also been reported
(Casabiancaet al., 1978; Cottonet al., 1982, 1983). To date, no crystallographic characterization has been carried out on the coordination complexes of P4(NCH3)6. We have found this
ligand to be effective at coordinating soft metal ions and here report the crystal structure of the coordination polymer [P4(NCH3)6CuI]n, (I). The Cu—P bond lengths are consistent
with other known structures of CuI with P—N ligands at 2.2434 (8) and 2.2390 (8) A˚ for Cu1—P1 and Cu1—P4i, respectively [symmetry code: (i) 2 x, y + 1
2, z + 1 2]. IR
spectroscopy of solid (I) as a KBr pellet indicated a shift in
(P—N) from 825 cm1 for the uncomplexed ligand to 853 cm1, with shoulders at 871 and 880 cm1, for the complexed ligand. This shift is consistent with previous studies of the chalcogenide derivatives of the ligand (Casabianca et al., 1977).
It is interesting to compare this structure with the CuI complex formed by hexamethylphosphorus triamide, the
monomeric analog of P4(NCH3)6. The HMPT complex of Cu I
forms a cube-shaped Cu4I4 core with the P ligands bound
peripherally to the four Cu vertices (Arkhireevaet al., 1990) The crystallographic cone angle for the cage ligand is esti-mated to be 140, roughly 10 larger than that of HMPT
(Mueller & Mingos, 1995).
The internal structure of the cage shows minor distortions to the P—N bond lengths typical of this family of compounds (Cottonet al., 1978, 1982, 1983). The bonds lengths for P atoms bonded to Cu (P1 and P4) are consistently shorter than those for non-coordinated P atoms. The geometry around the N atoms in the cage is roughly planar. The sum of angles around N atoms ranges from 356 to 346. The least planar N atoms are
at positions where this distortion relieves crowding between methyl groups of neighboring cages. The P P distances within the cage range from 2.975 to 3.037 A˚ .
Experimental
Manipulations were carried out using standard Schlenck techniques. The title compound was prepared by cannula addition of cuprous iodide (0.050 g) in freshly distilled acetonitrile (20 ml) to a similarly prepared solution of P4(NCH3)6 (0.105 g). Some precipitation
occurred immediately. The reaction flask was sealed under nitrogen and refrigerated at 277 K. Crystal formation was observed after two days. The white blocks are air stable over a period of one week.
Crystal data
[CuI(C6H18N6P4)]
Mr= 488.58
Monoclinic,P21=c
a= 8.4321 (5) A˚
b= 11.6068 (7) A˚
c= 16.2351 (10) A˚
= 94.863 (1)
V= 1583.20 (17) A˚3
Z= 4
Dx= 2.05 Mg m
3
MoKradiation Cell parameters from 6312
reflections
= 2.4–27.5
= 3.73 mm1
T= 100 (2) K Block, colorless 0.190.160.14 mm
Data collection
Bruker SMART CCD area-detector diffractometer
’and!scans
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)
Tmin= 0.474,Tmax= 0.594
9801 measured reflections
3605 independent reflections 3234 reflections withI> 2(I)
Rint= 0.022 max= 27.5
h=10!8
k=14!15
l=21!20
Refinement
Refinement onF2 R[F2> 2(F2)] = 0.027
wR(F2) = 0.069
S= 1.03 3605 reflections 169 parameters
H-atom parameters constrained
w= 1/[2
(Fo2) + (0.0262P)2
+ 1.8652P]
whereP= (Fo2+ 2Fc2)/3
(/)max= 0.001
max= 1.23 e A˚
3
min=0.71 e A˚
3
metal-organic papers
Acta Cryst.(2006). E62, m74–m76 Sommer and Rheingold [CuI(C
[image:2.610.89.223.72.277.2]6H18N6P4)]
m75
Figure 3
[image:2.610.310.566.73.206.2]View along thebaxis of P4(NCH3)6CuIn. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.
Figure 2
Displacement ellipsoid plot of [P4(NCH3)6CuI]n(n= 3). Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.
Figure 1
[image:2.610.315.565.255.537.2]H atoms were placed at appropriate positions (C—H = 0.98 A˚ ) and refined withUiso(H) = 1.2Ueq(C). The largest peak of residual
elec-tron density is 1.02 A˚ from C4. The position of atoms C2 and C4 in a relatively open region of space in the crystal structure allows greater vibrational motion, resulting in elongated displacement ellipsoids for these atoms. Modeling of C4 as a disordered methyl group with refined occupancy gave no improvement in structure refinement.
Data collection:SMART(Bruker, 2001); cell refinement:SAINT
(Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97(Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics:
ORTEP-3(Farrugia, 1997) andPOV-Ray(Persistence of Vision Pty. Ltd, 2004); software used to prepare material for publication:WinGX
(Farrugia, 1999).
RDS would like to thank Dr Bruce Noll for useful discussions.
References
Arkhireeva, T. M., Bulychev, B. M., Sizov, A. I., Sokolova, T. A., Belsky, V. K. & Soloveichik, G. L. (1990).Inorg. Chim. Acta,169, 109–118.
Bruker (2001).SMARTandSAINT. Bruker AXS Inc., Madison Wisconsin, USA.
Casabianca, F., Cotton, F. A., Riess, J. G., Rice, C. E. & Stults, B. R. (1978).
Inorg. Chem.17, 3521–3525.
Casabianca, F., Pinkerton, A. A. & Riess, J. G. (1977).Inorg. Chem.16, 864– 867.
Cotton, F. A., Riess, J. G., Rice, C. E. & Stults, B. R. (1978).Inorg. Chem.17, 3232–3236.
Cotton, F. A., Riess, J. G., Rice, C. E. & Stults, B. R. (1982).Inorg. Chem.21, 3123–3126.
Cotton, F. A., Riess, J. G. & Stults, B. R. (1983).Inorg. Chem.22, 133–136. Farrugia, L. J. (1997).J. Appl. Cryst.30, 565.
Farrugia, L. J. (1999).J. Appl. Cryst.32, 837–838.
Mueller, T. E. & Mingos, D. M. P. (1995).Transition Met. Chem.20, 533–539. Persistence of Vision Pty. Ltd (2004). POV-Ray. Version 3.6. http://
www.povray.org/download/.
Reiss, J. G. & Van Wazer, J. R. (1967).J. Organomet. Chem.8, 347–353. Reiss, J. G. & Van Wazer, J. R. (1968).Bull. Chem. Soc. Fr.8, 3087–3094. Sheldrick, G. M. (1996).SADABS. University of Gottingen, Germany. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of
Go¨ttingen, Germany.
metal-organic papers
m76
Sommer and Rheingold [CuI(Csupporting information
sup-1
Acta Cryst. (2006). E62, m74–m76supporting information
Acta Cryst. (2006). E62, m74–m76 [doi:10.1107/S1600536805040791]
A copper(I) coordination polymer containing an adamantane P
–
N cage ligand
Roger D. Sommer and Arnold L. Rheingold
S1. Comment
Spectroscopic studies have shown that the cage compound P4(NCH3)6 can coordinate up to four Lewis acids [Ni(CO)3, or
BH3], one at each P vertex (Riess or Reiss & Van Wazer, 1967, 1968). Crystallographic studies of chalcogenide
derivatives P4(NCH3)6Xn (X = O or S, n = 1–4) have also been reported (Casabianca et al., 1978; Cotton et al., 1982,
1983). To date, no crystallographic characterization has been carried out on the coordiation complexes of P4(NCH3)6. We
have found this ligand to be effective at coordinating soft metal ions and here report the crystal structure of the
coordination polymer [P4(NCH3)6CuI]n, (I). The Cu—P bond lengths are consistent with other known structures of CuI
with P—N ligands at 2.2434 (8) and 2.2390 (8) Å for Cu1—P1 and Cu1—P4i, respectively. IR spectroscopy of solid (I)
as a KBr pellet indicated a shift in νP—N from 825 cm−1 for the uncomplexed ligand to 853 cm−1 with shoulders at 871
and 880 cm−1 for the complexed ligand. This shift is consistent with previous studies of the chalcogenide derivatives of
the ligand. (Casabianca et al., 1977)
It is interesting to compare this structure with the CuI complex formed by hexamethylphosphorustriamide (HMPT), the
monomeric analog of P4(NCH3)6. The HMPT complex of CuI forms a cube-shaped Cu4I4 core with the P ligands bound
peripherally to the four Cu vertices (Arkhireeva et al., 1990) The crystallographic cone angle for the cage ligand is
estimated to be 140°, roughly 10° larger than that of HMPT (Mueller & Mingos, 1995).
The internal structure of the cage shows minor distortions to the P—N bond lengths typical of this family of compounds
(Cotton et al., 1978, 1982, 1983). The P—N bonds lengths for P bonded to Cu (P1 and P4) are consistently shorter than
those for non-coordinated P atoms. The geometry around the N atoms in the cage is roughly planar. The sum of angles
around N atoms ranges from 356 to 346°. The least planar N atoms are at positions where this distortion relieves
crowding between methyl groups of neighboring cages. The P—P distances within the cage range from 2.975 to 3.037 Å.
S2. Experimental
Manipulations were carried out using standard Schlenck technique. The title compound was prepared by cannula addition
of cuprous iodide (0.050 g) in freshly distilled acetonitrile (20 ml) to a similarly prepared solution of P4(NCH3)6 (0.105
g). Some precipitation occurred immediately. The reaction flask was sealed under nitrogen and refrigerated at 277 K.
Crystal formation was observed after two days. The white blocks are air stable over a period of one week.
S3. Refinement
Hydrogen atoms were placed at appropriate positions (C—H = 0.98 Å) and refined with a riding isotropic displacement
parameter 1.2 times that of the parent atom. The largest peak of residual electron density is 1.02 Å from C4. The position
of atoms C2 and C4 in a relatively open region of space in the crystal allows greater vibrational motion resulting in
elongated thermal ellipsoids for these atoms. Modeling of C4 as a disordered methyl group using a refined free variable
supporting information
[image:5.610.149.460.74.523.2]sup-2
Acta Cryst. (2006). E62, m74–m76Figure 1
Displacement ellipsoid plot of monomer unit. Displacement ellipsoids are drawn at the 50% probability level. H atoms
supporting information
[image:6.610.128.484.69.255.2]sup-3
Acta Cryst. (2006). E62, m74–m76Figure 2
Displacement ellipsoid plot of [P4(NCH3)6CuI]n (n = 3). Displacement ellipsoids are drawn at the 50% probability level.
supporting information
[image:7.610.132.485.67.468.2]sup-4
Acta Cryst. (2006). E62, m74–m76Figure 3
View along the b axis of P4(NCH3)6CuIn. Displacment ellipsoids are drawn at the 50% probability level. H atoms have
been omitted for clarity.
catena-poly[[iodocopper(I)]-µ-2,4,6,8,9,10-hexamethyl-2,4,6,8,9,10-hexaaza-
1,3,5,7-tetraphosphaadamantane-κ2P1:P3]
Crystal data [CuI(C6H18N6P4)]
Mr = 488.58
Monoclinic, P21/c
a = 8.4321 (5) Å b = 11.6068 (7) Å c = 16.2351 (10) Å β = 94.863 (1)° V = 1583.20 (17) Å3
Z = 4
F(000) = 952 Dx = 2.05 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 6312 reflections θ = 2.4–27.5°
µ = 3.73 mm−1
supporting information
sup-5
Acta Cryst. (2006). E62, m74–m76Data collection
Bruker SMART CCD area-detector diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
φ and ω scans
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
Tmin = 0.474, Tmax = 0.594
9801 measured reflections 3605 independent reflections 3234 reflections with I > 2σ(I) Rint = 0.022
θmax = 27.5°, θmin = 2.2°
h = −10→8 k = −14→15 l = −21→20
Refinement Refinement on F2
Least-squares matrix: full R[F2 > 2σ(F2)] = 0.027
wR(F2) = 0.069
S = 1.03 3602 reflections 169 parameters
0 restraints
H-atom parameters constrained w = 1/[σ2(F
o2) + (0.0262P)2 + 1.8652P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 1.23 e Å−3
Δρmin = −0.71 e Å−3
Special details
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.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
I1 0.72936 (2) 0.579312 (15) 0.069568 (12) 0.02046 (6)
Cu1 0.87384 (4) 0.71572 (3) 0.17027 (2) 0.01346 (8)
P1 1.04422 (8) 0.63047 (6) 0.26493 (4) 0.01229 (14)
P2 1.18719 (9) 0.62129 (6) 0.43828 (5) 0.01779 (15)
P3 1.39471 (8) 0.58751 (6) 0.29620 (5) 0.01705 (15)
P4 1.16248 (8) 0.40671 (6) 0.33530 (4) 0.01180 (14)
N1 1.0492 (3) 0.67457 (19) 0.36375 (14) 0.0160 (5)
N2 1.3636 (3) 0.63634 (19) 0.39244 (15) 0.0181 (5)
N3 1.2322 (3) 0.64358 (19) 0.23728 (14) 0.0156 (5)
N4 1.3376 (3) 0.44569 (19) 0.30059 (15) 0.0158 (5)
N5 1.1578 (3) 0.47475 (19) 0.42786 (14) 0.0151 (5)
N6 1.0262 (2) 0.48477 (18) 0.27578 (13) 0.0120 (4)
C1 0.9770 (4) 0.7866 (2) 0.38322 (18) 0.0205 (6)
H1A 1.0461 0.8494 0.3675 0.031*
H1B 0.9649 0.7909 0.4426 0.031*
H1C 0.8724 0.7938 0.3524 0.031*
C2 1.4423 (4) 0.7485 (3) 0.4131 (2) 0.0286 (7)
H2A 1.5502 0.7479 0.395 0.043*
H2B 1.4477 0.7608 0.473 0.043*
H2C 1.3809 0.8109 0.385 0.043*
C3 1.2445 (4) 0.6293 (3) 0.14700 (18) 0.0231 (6)
H3A 1.2028 0.5535 0.1295 0.035*
supporting information
sup-6
Acta Cryst. (2006). E62, m74–m76H3C 1.1824 0.6896 0.1169 0.035*
C4 1.4647 (4) 0.3604 (3) 0.3021 (3) 0.0486 (11)
H4A 1.5276 0.3634 0.3557 0.073*
H4B 1.5334 0.377 0.2579 0.073*
H4C 1.4183 0.2834 0.2939 0.073*
C5 1.2448 (4) 0.4127 (2) 0.49809 (18) 0.0216 (6)
H5A 1.234 0.3294 0.4894 0.032*
H5B 1.1999 0.4339 0.5497 0.032*
H5C 1.3576 0.434 0.5014 0.032*
C6 0.8605 (3) 0.4478 (2) 0.28647 (18) 0.0154 (5)
H6A 0.8445 0.3689 0.2659 0.023*
H6B 0.7857 0.4996 0.2553 0.023*
H6C 0.8419 0.4506 0.3452 0.023*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
I1 0.02546 (11) 0.01183 (10) 0.02227 (11) −0.00239 (7) −0.00864 (7) −0.00094 (7)
Cu1 0.01347 (16) 0.00879 (16) 0.01740 (17) 0.00064 (12) −0.00299 (12) 0.00017 (12)
P1 0.0122 (3) 0.0086 (3) 0.0155 (3) 0.0002 (2) −0.0019 (2) −0.0004 (2)
P2 0.0240 (4) 0.0112 (3) 0.0168 (4) 0.0015 (3) −0.0061 (3) −0.0028 (3)
P3 0.0119 (3) 0.0109 (3) 0.0277 (4) −0.0014 (2) −0.0024 (3) 0.0019 (3)
P4 0.0115 (3) 0.0088 (3) 0.0146 (3) −0.0001 (2) −0.0019 (2) −0.0005 (2)
N1 0.0195 (12) 0.0114 (11) 0.0165 (12) 0.0032 (9) −0.0024 (9) −0.0027 (9)
N2 0.0172 (11) 0.0102 (11) 0.0250 (13) −0.0022 (9) −0.0091 (9) −0.0009 (9)
N3 0.0136 (11) 0.0141 (11) 0.0184 (12) 0.0000 (8) −0.0016 (9) 0.0010 (9)
N4 0.0124 (11) 0.0084 (10) 0.0263 (13) 0.0000 (8) 0.0007 (9) 0.0008 (9)
N5 0.0205 (12) 0.0115 (11) 0.0127 (11) 0.0011 (9) −0.0032 (9) −0.0001 (8)
N6 0.0105 (10) 0.0089 (10) 0.0161 (11) −0.0003 (8) −0.0015 (8) 0.0002 (8)
C1 0.0289 (16) 0.0109 (13) 0.0219 (15) 0.0061 (11) 0.0029 (12) −0.0008 (11)
C2 0.0264 (17) 0.0123 (14) 0.044 (2) −0.0054 (12) −0.0125 (14) −0.0048 (13)
C3 0.0217 (15) 0.0255 (16) 0.0225 (15) 0.0013 (12) 0.0042 (12) 0.0030 (12)
C4 0.0276 (19) 0.0192 (18) 0.102 (4) 0.0005 (14) 0.025 (2) −0.0033 (19)
C5 0.0313 (16) 0.0172 (14) 0.0150 (14) 0.0008 (12) −0.0059 (12) 0.0015 (11)
C6 0.0122 (12) 0.0122 (13) 0.0217 (14) −0.0007 (10) 0.0009 (10) −0.0007 (10)
Geometric parameters (Å, º)
I1—Cu1 2.5151 (4) N5—C5 1.488 (3)
Cu1—P4i 2.2387 (7) N6—C6 1.486 (3)
Cu1—P1 2.2430 (7) C1—H1A 0.98
P1—N1 1.681 (2) C1—H1B 0.98
P1—N3 1.691 (2) C1—H1C 0.98
P1—N6 1.708 (2) C2—H2A 0.98
P2—N1 1.721 (2) C2—H2B 0.98
P2—N5 1.725 (2) C2—H2C 0.98
P2—N2 1.728 (3) C3—H3A 0.98
supporting information
sup-7
Acta Cryst. (2006). E62, m74–m76P3—N4 1.718 (2) C3—H3C 0.98
P3—N3 1.730 (2) C4—H4A 0.98
P4—N4 1.686 (2) C4—H4B 0.98
P4—N6 1.699 (2) C4—H4C 0.98
P4—N5 1.701 (2) C5—H5A 0.98
P4—Cu1ii 2.2387 (7) C5—H5B 0.98
N1—C1 1.481 (3) C5—H5C 0.98
N2—C2 1.487 (3) C6—H6A 0.98
N3—C3 1.487 (4) C6—H6B 0.98
N4—C4 1.458 (4) C6—H6C 0.98
P4i—Cu1—P1 122.82 (3) P4—N6—P1 121.66 (13)
P4i—Cu1—I1 122.69 (2) N1—C1—H1A 109.5
P1—Cu1—I1 114.49 (2) N1—C1—H1B 109.5
N1—P1—N3 106.14 (12) H1A—C1—H1B 109.5
N1—P1—N6 101.44 (11) N1—C1—H1C 109.5
N3—P1—N6 102.12 (11) H1A—C1—H1C 109.5
N1—P1—Cu1 118.83 (8) H1B—C1—H1C 109.5
N3—P1—Cu1 109.81 (8) N2—C2—H2A 109.5
N6—P1—Cu1 116.74 (8) N2—C2—H2B 109.5
N1—P2—N5 101.67 (11) H2A—C2—H2B 109.5
N1—P2—N2 102.50 (12) N2—C2—H2C 109.5
N5—P2—N2 100.33 (11) H2A—C2—H2C 109.5
N2—P3—N4 102.43 (12) H2B—C2—H2C 109.5
N2—P3—N3 101.87 (11) N3—C3—H3A 109.5
N4—P3—N3 99.89 (11) N3—C3—H3B 109.5
N4—P4—N6 103.64 (11) H3A—C3—H3B 109.5
N4—P4—N5 104.91 (12) N3—C3—H3C 109.5
N6—P4—N5 100.93 (11) H3A—C3—H3C 109.5
N4—P4—Cu1ii 111.89 (8) H3B—C3—H3C 109.5
N6—P4—Cu1ii 114.93 (8) N4—C4—H4A 109.5
N5—P4—Cu1ii 118.82 (8) N4—C4—H4B 109.5
C1—N1—P1 119.58 (18) H4A—C4—H4B 109.5
C1—N1—P2 115.53 (18) N4—C4—H4C 109.5
P1—N1—P2 121.47 (14) H4A—C4—H4C 109.5
C2—N2—P3 113.5 (2) H4B—C4—H4C 109.5
C2—N2—P2 112.0 (2) N5—C5—H5A 109.5
P3—N2—P2 124.52 (13) N5—C5—H5B 109.5
C3—N3—P1 113.37 (18) H5A—C5—H5B 109.5
C3—N3—P3 112.63 (18) N5—C5—H5C 109.5
P1—N3—P3 122.39 (14) H5A—C5—H5C 109.5
C4—N4—P4 118.4 (2) H5B—C5—H5C 109.5
C4—N4—P3 116.3 (2) N6—C6—H6A 109.5
P4—N4—P3 121.83 (13) N6—C6—H6B 109.5
C5—N5—P4 113.91 (18) H6A—C6—H6B 109.5
C5—N5—P2 110.15 (17) N6—C6—H6C 109.5
supporting information
sup-8
Acta Cryst. (2006). E62, m74–m76C6—N6—P4 112.14 (17) H6B—C6—H6C 109.5
C6—N6—P1 112.98 (16)