Orthorhombic and monoclinic polymorphs of 1,3,5-tri­phenyl­per­hydro-1,3,5-triazine-2,4,6-trione at 120 K: chains and sheets formed by C—H⋯π(arene) hydrogen bonds

Mariyatra, M.B.; Panchanatheswaran, K.; Low, J.N.; Glidewell, C.

doi:10.1107/S0108270104017342

organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 60| Part 9| September 2004| Pages o682-o685

doi:10.1107/S0108270104017342

Orthorhombic and monoclinic polymorphs of 1,3,5-triphenylperhydro-1,3,5-triazine-2,4,6-trione at 120 K: chains and sheets formed by C—H⋯π(arene) hydrogen bonds

M. Baby Mariyatra,^a Krishnaswamy Panchanatheswaran,^a John N. Low ^b ‡ and Christopher Glidewell ^c ^*

^aDepartment of Chemistry, Bharathidasan University, Tiruchirappalli, Tamil Nadu 620 024, India, ^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and ^cSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
^*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 13 July 2004; accepted 15 July 2004; online 21 August 2004)

The title compound, C₂₁H₁₅N₃O₃, crystallizes in two polymorphic forms. In the orthorhombic polymorph, (I), in space group Fdd2 with Z′ = 1, the molecules lie in general positions, while in the monoclinic polymorph, (II), in space group C2/c with Z′ = $[{1 \over 2}]$ , the molecules lie across twofold rotation axes. In each polymorph, the molecules are linked by a single C—H⋯π(arene) hydrogen bond, forming chains in polymorph (I) and sheets in (II).

Comment

We report here the molecular and supramolecular structures at 120 K of two polymorphic forms of 1,3,5-triphenyl-1,3,5-perhydrotriazine-2,4,6-trione, the cyclic trimer of phenyl isocyanate, PhNCO. The orthorhombic polymorph, (I) (Fig. 1), crystallizes in space group Fdd2 with Z′ = 1, and the monoclinic polymorph, (II) (Fig. 2), crystallizes in space group C2/c, with Z′ = $[{1 \over 2}]$ . The molecules in (II) lie across twofold rotation axes, with the reference molecule lying across the axis along ( $[{1 \over 2}]$ , y, $[{1 \over 4}]$ ). The structure of (II) was reported from ambient-temperature data some years ago (Usanmaz, 1979 ) and it is clear from the cell dimensions and space group that this earlier structure was of the same phase as (II), thus suggesting that the monoclinic phase does not undergo any temperature-dependent change, at least within the range 120–300 K.

The bond lengths and angles in (I) and (II) (Tables 1 and 3) are very similar, and the distances show evidence of strong bond fixation. Within the heterocyclic rings, the internal bond angles at the N atoms are consistently some 10° larger than the internal angles at the C atoms. In polymorph (II), the heterocyclic ring is slightly puckered. The ring-puckering parameters (Cremer & Pople, 1975 ) for the atom sequence N1—C2—N3—C4—N3ⁱ—C2ⁱ [symmetry code: (i) 1 − x, y, $[{1 \over 2}]$ − z] of θ = 90.0 (7)° and φ = 270.0 (6)° indicate a twist-boat ring conformation (Boeyens, 1978 ), although the puckering amplitude Q is fairly small, at 0.104 (2) Å. The conformations defined by the phenyl rings (Figs. 1 and 2, and Tables 1 and 3) are very similar.

In the crystal structure of (I), there are no C—H⋯O or C—H⋯N hydrogen bonds and no aromatic π–π stacking interactions. However, the molecules are linked into chains by a single C—H⋯π(arene) interaction (Table 2). Aromatic atom C14 in the molecule at (x, y, z) acts as hydrogen-bond donor to phenyl ring C31–C36 in the molecule at ( $[{5 \over 4}]$ − x, y − $[{1 \over 4}]$ , $[{3 \over 4}]$ + z), while atom C14 at ( $[{5 \over 4}]$ − x, y − $[{1 \over 4}]$ , $[{3 \over 4}]$ + z) in turn acts as donor to the C31–C36 ring at (x, y − $[{1 \over 2}]$ , $[{3 \over 2}]$ + z), so producing a chain running parallel to the [0 $[\overline 1]$ 3] direction and generated by the d-glide plane at x = $[{5 \over 8}]$ (Fig. 3). There are no direction-specific interactions between adjacent chains.

The original report (Usanmaz, 1979) on the monoclinic phase, (II), did not identify any direction-specific interactions between the molecules. However, the intermolecular interactions present in (II) are, in fact, very similar to those in orthorhombic phase (I). While C—H⋯O and C—H⋯N hydrogen bonds and aromatic π–π stacking interactions are all absent, the molecules are linked by a single C—H⋯π(arene) hydrogen bond (Table 4), but now forming sheets as opposed to the simple chain in (I). The ring containing atom C11, which lies across a twofold rotation axis, acts as a double acceptor of C—H⋯π(arene) hydrogen bonds, one on each face. This ring in the reference molecule accepts such hydrogen bonds from atoms C33 at (x − $[{1 \over 2}]$ , $[{1 \over 2}]$ + y, z − 1) and ( $[{3 \over 2}]$ − x, $[{1 \over 2}]$ + y, $[{3 \over 2}]$ − z), while atoms C33 at (x, y, z) and (1 − x, y, $[{1 \over 2}]$ − z) in the reference molecule act as donors to the ring faces at ( $[{3 \over 2}]$ − x, y − $[{1 \over 2}]$ , $[{3 \over 2}]$ − z) and (x − $[{1 \over 2}]$ , y − $[{1 \over 2}]$ , z − 1), respectively. Thus, with the reference molecule lying across the axis along ( $[{1 \over 2}]$ , y, $[{1 \over 4}]$ ), the donor and acceptor molecules lie across the axes (0, y, $[-{3 \over 4}]$ ) and (1, y, $[{5 \over 4}]$ ), so that each molecule is linked to four others, forming a ( $[\overline 2]$ 01) sheet (Fig. 4).

We have not investigated the relative thermodynamic stability of the two polymorphs. Their densities are almost identical, so that no useful deductions concerning stability (Burger & Ramberger, 1979 ) can be made here.

Figure 1
The molecule in the orthorhombic polymorph, (I

), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.

Figure 2
The molecule in the monoclinic polymorph, (II

), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. [Symmetry code: (i) 1 −x, y, $[{1 \over 2}]$ − z.]

Figure 3
Part of the crystal structure of polymorph (I

), showing a hydrogen-bonded chain running along the [0 $[\overline 1]$ 3] direction. For the sake of clarity, H atoms not involved in the motif shown have been omitted. Cg3 is the centroid of ring C31–C36. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions ( $[{5 \over 4}]$ − x, y − $[{1 \over 4}]$ , $[{3 \over 4}]$ + z) and ( $[{5 \over 4}]$ − x, $[{1 \over 4}]$ + y, z − $[{3 \over 4}]$ ), respectively.

Figure 4
A stereoview of part of the crystal structure of polymorph (II

), showing a hydrogen-bonded ( $[\overline 2]$ 01) sheet. For the sake of clarity, H atoms not involved in the motif shown have been omitted.

Experimental

The orthorhombic polymorph, (I), was obtained as an adventitious product from the attempted preparation of the heterocumulene Ph₃P=C=C=O via reaction of Ph₃P=CHCOOCH₂CH₃ with n-butyllithium and excess phenyl isocyanate (m.p. 544–545 K). The monoclinic polymorph, (II), was obtained from a methanol solution containing (I) and uranyl nitrate hexahydrate [m.p. > 550 K; literature m.p. for (II): 553–555 K (Usanmaz, 1979)]. However, similar crystallization from a methanol solution containing mercury(II) chloride gave polymorph (I) rather than polymorph (II).

Polymorph (I)

Crystal data

C₂₁H₁₅N₃O₃
M_r = 357.36
Orthorhombic, Fdd2
a = 23.3764 (8) Å
b = 37.1079 (12) Å
c = 7.7091 (2) Å
V = 6687.3 (4) Å³
Z = 16
D_x = 1.420 Mg m⁻³
Mo Kα radiation
Cell parameters from 2065 reflections
θ = 3.2–27.6°
μ = 0.10 mm⁻¹
T = 120 (2) K
Block, yellow
0.50 × 0.24 × 0.10 mm

Data collection

Nonius KappaCCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.966, T_max = 0.990
22 356 measured reflections
2065 independent reflections
1859 reflections with I > 2σ(I)
R_int = 0.045
θ_max = 27.6°
h = −30 → 29
k = −48 → 48
l = −9 → 10

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.082
S = 1.08
2065 reflections
244 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0501P)² + 2.7798P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.001
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Selected geometric parameters (Å, °) for orthorhombic polymorph (I)

N1—C2	1.389 (3)
C2—N3	1.388 (2)
N3—C4	1.395 (2)
C4—N5	1.395 (3)
N5—C6	1.394 (2)
C6—N1	1.389 (2)
N1—C11	1.448 (2)
N3—C31	1.448 (3)
N5—C51	1.452 (2)
C2—O2	1.208 (2)
C4—O4	1.204 (2)
C6—O6	1.210 (2)

C6—N1—C2	125.11 (16)
C2—N3—C4	124.97 (17)
C4—N5—C6	124.38 (16)
N1—C2—N3	115.05 (16)
N3—C4—N5	115.01 (16)
N5—C6—N1	115.19 (17)

C2—N1—C11—C12	103.9 (2)
C4—N3—C31—C32	−101.5 (2)
C6—N5—C51—C52	−119.9 (2)

Table 2
Hydrogen-bonding geometry (Å, °) for orthorhombic polymorph (I)

Cg3 is the centroid of ring C31–C36.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯Cg3ⁱ	0.95	2.71	3.541 (2)	146
Symmetry code: (i) $[{\script{5\over 4}}-x,y-{\script{1\over 4}},{\script{3\over 4}}+z]$ .

Polymorph (II)

Crystal data

C₂₁H₁₅N₃O₃
M_r = 357.36
Monoclinic, C2/c
a = 15.6526 (3) Å
b = 13.6819 (3) Å
c = 9.6454 (2) Å
β = 126.035 (2)°
V = 1670.39 (7) Å³
Z = 4
D_x = 1.421 Mg m⁻³
Mo Kα radiation
Cell parameters from 1927 reflections
θ = 3.2–27.5°
μ = 0.10 mm⁻¹
T = 120 (2) K
Block, yellow
0.50 × 0.40 × 0.12 mm

Data collection

Nonius KappaCCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) T_min = 0.945, T_max = 0.988
13 735 measured reflections
1927 independent reflections
1620 reflections with I > 2σ(I)
R_int = 0.031
θ_max = 27.5°
h = −20 → 20
k = −17 → 17
l = −11 → 12

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.124
S = 1.17
1927 reflections
126 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.073P)² + 0.412P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.43 e Å⁻³
Extinction correction: SHELXL97 (Sheldrick, 1997 )
Extinction coefficient: 0.034 (3)

Table 3
Selected geometric parameters (Å, °) for monoclinic polymorph (II)

N1—C2	1.3940 (13)
C2—N3	1.3949 (16)
N3—C4	1.3914 (13)
N1—C11	1.455 (2)
N3—C31	1.4516 (14)
C2—O2	1.2035 (14)
C4—O4	1.204 (2)

C2ⁱ—N1—C2	124.59 (14)
C2—N3—C4	124.80 (10)
N1—C2—N3	114.92 (10)
N3—C4—N3ⁱ	114.86 (14)

C2—N1—C11—C12	69.56 (8)
C4—N3—C31—C32	−100.07 (12)
Symmetry code: (i) $[1-x,y,{\script{1\over 2}}-z]$ .

Table 4
Hydrogen-bonding geometry (Å, °) for monoclinic polymorph (II)

Cg2 is the centroid of ring C11–C14/C13ⁱ/C12ⁱ.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C33—H33⋯Cg2ⁱⁱ	0.95	2.95	3.678 (2)	134
Symmetry codes: (i) $[1-x,y,{\script{1\over 2}}-z]$ ; (ii) $[{\script{1\over 2}}+x,y-{\script{1\over 2}},1+z]$ .

For polymorph (I), the space group Fdd2 was uniquely assigned from the systematic absences. For polymorph (II), the systematic absences permitted C2/c or Cc as possible space groups; C2/c was selected and confirmed by the systematic absences. All H atoms were located from difference maps and then treated as riding atoms, with C—H distances of 0.95 Å and U_iso(H) = 1.2U_eq(C). In the absence of significant anomalous scattering, the Flack (1983 ) parameter for (I) was indeterminate (Flack & Bernardinelli, 1999 , 2000 ). Accordingly, the Friedel-equivalent reflections were merged prior to the final refinements. It was thus not possible to establish the correct orientation of the structure of (I) relative to the polar-axis direction (Jones, 1986 ).

For both polymorphs, data collection: COLLECT (Nonius, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003 ) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I, II. DOI: 10.1107/S0108270104017342/sk1750sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270104017342/sk1750Isup2.hkl

Structure factors: contains datablock II. DOI: 10.1107/S0108270104017342/sk1750IIsup3.hkl

Comment top

We report here the molecular and supramolecular structures at 120 K of two polymorphic forms of 1,3,5-triphenyl-1,3,5-perhydrotriazine-2,4,6-trione, the cyclic trimer of phenyl isocyanate, PhNCO. The orthorhombic polymorph, (I) (Fig. 1), crystallizes in space group Fdd2 with Z' = 1, and the monoclinic polymorph, (II) (Fig. 2), crystallizes in space group C2/c, with Z' = 1/2. The molecules in (II) lie across twofold rotation axes, with the reference molecule lying across the axis along (1/2, y, 1/4). The structure of (II) was reported from ambient-temperature data some years ago (Usanmaz, 1979), and it is clear from the cell dimensions and space group that this earlier structure was of the same phase as (II), thus suggesting that the monoclinic phase does not undergo any temperature-dependent change, at least within the range 120–300 K. \sch

The bond lengths and angles in (I) and (II) (Tables 1 and 3) are very similar, and the distances show evidence of strong bond fixation. Within the heterocyclic rings, the internal bond angles at N are consistently some 10° larger than the internal angles at C. In polymorph (II), the heterocyclic ring is slightly puckered. The ring-puckering parameters (Cremer & Pople, 1975) for the atom sequence N1/C2—C4/N3ⁱ/C2ⁱ [symmetry code: (i) 1 − x, y, 1/2 − z] of θ = 90.0 (7)° and ϕ = 270.0 (6)° indicate a twist-boat ring conformation (Boeyens, 1978), although the puckering amplitude Q is fairly small, at 0.104 (2) Å. The conformations defined by the phenyl rings (Figs. 1 and 2, and Tables 1 and 3) are very similar.

In the crystal structure of (I), there are no C—H···O or C—H···N hydrogen bonds and no aromatic π–π stacking interactions. However, the molecules are linked into chains by a single C—H···π(arene) interaction (Table 2). The aromatic atom C14 in the molecule at (x, y, z) acts as hydrogen-bond donor to the phenyl ring C31—C36 in the molecule at (5/4 − x, y − 1/4, 3/4 + z), while atom C14 at (5/4 − x, y − 1/4, 3/4 + z) in turn acts as donor to the C31—C36 ring at (x, y − 1/2, 3/2 + z), so producing a chain running parallel to the [013] direction and generated by the d-glide plane at x = 5/8 (Fig. 3). There are no direction-specific interactions between adjacent chains.

The original report (Usanmaz, 1979) on the monoclinic phase, (II), did not identify any direction-specific interactions between the molecules. However, the intermolecular interactions present in (II) are, in fact, very similar to those in the orthorhombic phase, (I). While C—H···O and C—H···N hydrogen bonds and aromatic π–π stacking interactions are all absent, the molecules are linked by a single C—H···π(arene) hydrogen bond (Table 4), but now forming sheets as opposed to the simple chain in (I). The ring containing atom C11, which lies across a twofold rotation axis, acts as a double acceptor of C—H···π(arene) hydrogen bonds, one on each face. This ring in the reference molecule accepts such hydrogen bonds from atoms C33 at (x − 1/2, 1/2 + y, z − 1) and (3/2 − x, 1/2 + y, 3/2 − z), while the atoms C33 at (x, y, z) and (1 − x, y, 1/2 − z) in the reference molecule act as donors to the ring faces at (3/2 − x, y − 1/2, 3/2 − z) and (x − 1/2, y − 1/2, z − 1), respectively. Thus, with the reference molecule lying across the axis along (1/2, y, 1/4), the donor and acceptor molecules lie across across the axes (0, y, −3/4) and (1, y, 5/4), so that each molecule is linked to four others forming a (201) sheet (Fig. 4).

Table 2. Hydrogen-bond parameters (Å, °) for polymorph (I). Cg3 is the centroid of ring C31—C36.

Table 4. Hydrogen-bond parameters (Å, °) for polymorph (II). Cg2 is the centroid of ring C11—C14/C13ⁱ/C12ⁱ [symmetry code:(i) 1 − x, y, 1/2 − z].

Experimental top

The orthorhombic polymorph, (I), was obtained as an adventitious product from the attempted preparation of the heterocumulene Ph₃P═C═C═O via reaction of Ph₃P═CHCOOCH₂CH₃ with n-butyllithium and excess of phenyl isocyanate (m. p. 544–545 K). The monoclinic polymorph, (II), was obtained from a methanolic solution containing (I) and uranyl nitrate hexahydrate [m. p. > 550 K; literature m. p. for (II): 553–555 K (Usanmaz, 1979)]. However, similar crystallization from a methanolic solution containing mercury(II) chloride gave polymorph (I), rather than polymorph (II).

Computing details top

For both compounds, data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and COLLECT (Otwinowski & Minor, 1997); data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top

	Fig. 1. The molecule in the orthorhombic polymorph, (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The molecule in the monoclinic polymorph, (II), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. The atoms marked with the suffix 'a' are at the symmetry position (1 − x, y, 1/2 − z).
	Fig. 3. Part of the crystal structure of polymorph (I), showing a hydrogen-bonded chain running along the [013] direction. For the sake of clarity, H atoms not involved in the motif shown have been omitted. Cg3 is the centroid of ring C31—C36. The atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (5/4 − x, y − 1/4, 3/4 + z) and (5/4 − x, 1/4 + y, z − 3/4), respectively.
	Fig. 4. A stereoview of part of the crystal structure of polymorph (II), showing a hydrogen-bonded (201) sheet. For the sake of clarity, H atoms not involved in the motif shown have been omitted.

(I) 1,3,5-triphenylperhydro-1,3,5-triazine-2,4,6-trione, orthorhombic polymorph top

Crystal data top

C₂₁H₁₅N₃O₃	F(000) = 2976
M_r = 357.36	D_x = 1.420 Mg m⁻³
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 2065 reflections
a = 23.3764 (8) Å	θ = 3.2–27.6°
b = 37.1079 (12) Å	µ = 0.10 mm⁻¹
c = 7.7091 (2) Å	T = 120 K
V = 6687.3 (4) Å³	Block, yellow
Z = 16	0.5 × 0.24 × 0.1 mm

Data collection top

Nonius KappaCCD area-detector diffractometer	2065 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1859 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.6°, θ_min = 3.2°
ϕ and ω scans	h = −30→29
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −48→48
T_min = 0.966, T_max = 0.990	l = −9→10
22356 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0501P)² + 2.7798P] where P = (F_o² + 2F_c²)/3
2065 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.17 e Å⁻³
1 restraint	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₁H₁₅N₃O₃	V = 6687.3 (4) Å³
M_r = 357.36	Z = 16
Orthorhombic, Fdd2	Mo Kα radiation
a = 23.3764 (8) Å	µ = 0.10 mm⁻¹
b = 37.1079 (12) Å	T = 120 K
c = 7.7091 (2) Å	0.5 × 0.24 × 0.1 mm

Data collection top

Nonius KappaCCD area-detector diffractometer	2065 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1859 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.990	R_int = 0.045
22356 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	1 restraint
wR(F²) = 0.082	H-atom parameters constrained
S = 1.08	Δρ_max = 0.17 e Å⁻³
2065 reflections	Δρ_min = −0.24 e Å⁻³
244 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O2	0.59934 (6)	0.46727 (4)	0.6011 (2)	0.0259 (3)
O4	0.67073 (6)	0.58096 (4)	0.5631 (2)	0.0241 (3)
O6	0.73397 (6)	0.50498 (4)	0.9884 (2)	0.0251 (3)
N1	0.66767 (7)	0.48505 (4)	0.7945 (2)	0.0182 (3)
N3	0.63468 (7)	0.52415 (4)	0.5780 (2)	0.0191 (4)
N5	0.70165 (7)	0.54461 (4)	0.7836 (2)	0.0180 (3)
C2	0.63165 (8)	0.49025 (5)	0.6535 (3)	0.0194 (4)
C4	0.66991 (8)	0.55213 (5)	0.6347 (3)	0.0184 (4)
C6	0.70397 (8)	0.51096 (5)	0.8638 (3)	0.0185 (4)
C11	0.66554 (8)	0.44999 (5)	0.8767 (3)	0.0187 (4)
C12	0.70869 (9)	0.42549 (5)	0.8476 (3)	0.0229 (4)
C13	0.70482 (9)	0.39154 (5)	0.9220 (3)	0.0251 (4)
C14	0.65788 (9)	0.38223 (5)	1.0203 (3)	0.0242 (4)
C15	0.61465 (9)	0.40724 (5)	1.0501 (3)	0.0249 (4)
C16	0.61874 (8)	0.44142 (5)	0.9796 (3)	0.0224 (4)
C31	0.59919 (8)	0.53105 (5)	0.4277 (3)	0.0181 (4)
C32	0.54180 (9)	0.53877 (5)	0.4513 (3)	0.0219 (4)
C33	0.50794 (8)	0.54602 (6)	0.3077 (3)	0.0237 (4)
C34	0.53164 (9)	0.54582 (5)	0.1436 (3)	0.0233 (4)
C35	0.58931 (10)	0.53800 (5)	0.1218 (3)	0.0251 (4)
C36	0.62337 (9)	0.53040 (5)	0.2642 (3)	0.0227 (4)
C51	0.73447 (8)	0.57402 (5)	0.8579 (3)	0.0186 (4)
C52	0.70574 (9)	0.60461 (5)	0.9137 (3)	0.0231 (4)
C53	0.73669 (9)	0.63366 (6)	0.9758 (3)	0.0263 (5)
C54	0.79557 (9)	0.63153 (6)	0.9865 (3)	0.0251 (5)
C55	0.82382 (9)	0.60053 (6)	0.9361 (3)	0.0251 (4)
C56	0.79332 (8)	0.57165 (5)	0.8687 (3)	0.0214 (4)
H12	0.7407	0.4317	0.7777	0.027*
H13	0.7348	0.3746	0.9050	0.030*
H14	0.6550	0.3587	1.0679	0.029*
H15	0.5824	0.4009	1.1186	0.030*
H16	0.5898	0.4588	1.0013	0.027*
H32	0.5258	0.5391	0.5645	0.026*
H33	0.4684	0.5511	0.3222	0.028*
H34	0.5085	0.5510	0.0456	0.028*
H35	0.6055	0.5379	0.0087	0.030*
H36	0.6627	0.5248	0.2496	0.027*
H52	0.6652	0.6056	0.9094	0.028*
H53	0.7175	0.6550	1.0109	0.032*
H54	0.8168	0.6515	1.0288	0.030*
H55	0.8642	0.5990	0.9476	0.030*
H56	0.8126	0.5506	0.8305	0.026*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0284 (8)	0.0189 (7)	0.0305 (8)	−0.0030 (6)	−0.0088 (6)	0.0015 (6)
O4	0.0260 (7)	0.0194 (7)	0.0270 (8)	−0.0024 (6)	−0.0035 (6)	0.0052 (6)
O6	0.0253 (8)	0.0241 (7)	0.0259 (8)	−0.0015 (6)	−0.0067 (6)	0.0030 (6)
N1	0.0187 (8)	0.0156 (8)	0.0203 (8)	0.0001 (6)	−0.0011 (7)	0.0020 (6)
N3	0.0190 (8)	0.0171 (8)	0.0211 (9)	−0.0009 (6)	−0.0041 (6)	0.0017 (6)
N5	0.0178 (8)	0.0168 (7)	0.0195 (8)	−0.0012 (6)	−0.0012 (7)	0.0005 (6)
C2	0.0181 (9)	0.0192 (9)	0.0210 (10)	0.0017 (8)	−0.0007 (8)	0.0004 (8)
C4	0.0156 (9)	0.0194 (9)	0.0203 (10)	−0.0002 (7)	0.0003 (8)	−0.0012 (8)
C6	0.0180 (9)	0.0176 (9)	0.0199 (9)	−0.0001 (7)	0.0019 (8)	0.0014 (8)
C11	0.0207 (9)	0.0156 (9)	0.0198 (10)	−0.0011 (7)	−0.0019 (8)	0.0012 (7)
C12	0.0221 (10)	0.0231 (10)	0.0235 (10)	0.0005 (8)	0.0016 (8)	0.0007 (8)
C13	0.0290 (11)	0.0197 (10)	0.0266 (10)	0.0051 (8)	0.0003 (9)	−0.0002 (8)
C14	0.0327 (11)	0.0183 (10)	0.0216 (10)	−0.0040 (8)	−0.0041 (9)	0.0026 (8)
C15	0.0236 (10)	0.0254 (10)	0.0257 (11)	−0.0045 (8)	0.0008 (9)	0.0026 (9)
C16	0.0186 (9)	0.0215 (10)	0.0272 (10)	0.0005 (8)	0.0005 (8)	0.0009 (8)
C31	0.0186 (9)	0.0139 (9)	0.0219 (10)	−0.0007 (7)	−0.0041 (8)	0.0007 (7)
C32	0.0225 (10)	0.0205 (9)	0.0227 (10)	−0.0006 (8)	0.0012 (8)	0.0009 (8)
C33	0.0176 (10)	0.0228 (10)	0.0308 (11)	−0.0005 (8)	−0.0023 (9)	0.0045 (8)
C34	0.0237 (10)	0.0217 (10)	0.0243 (11)	−0.0011 (8)	−0.0065 (8)	0.0021 (8)
C35	0.0302 (11)	0.0248 (10)	0.0204 (10)	−0.0002 (8)	0.0000 (9)	0.0004 (8)
C36	0.0202 (10)	0.0222 (10)	0.0256 (11)	0.0030 (8)	0.0017 (8)	−0.0013 (8)
C51	0.0207 (10)	0.0167 (9)	0.0184 (9)	−0.0049 (7)	−0.0017 (8)	0.0011 (7)
C52	0.0180 (9)	0.0234 (10)	0.0278 (11)	0.0002 (8)	−0.0010 (9)	0.0007 (8)
C53	0.0301 (11)	0.0193 (10)	0.0295 (11)	0.0006 (8)	−0.0005 (9)	−0.0028 (9)
C54	0.0294 (11)	0.0223 (10)	0.0235 (11)	−0.0072 (9)	−0.0016 (9)	−0.0016 (8)
C55	0.0201 (10)	0.0295 (11)	0.0256 (10)	−0.0043 (8)	−0.0017 (9)	0.0009 (9)
C56	0.0196 (10)	0.0224 (10)	0.0222 (10)	−0.0005 (8)	0.0009 (8)	0.0004 (8)

Geometric parameters (Å, º) top

N1—C2	1.389 (3)	C31—C36	1.382 (3)
C2—N3	1.388 (2)	C31—C32	1.384 (3)
N3—C4	1.395 (2)	C32—C33	1.387 (3)
C4—N5	1.395 (3)	C32—H32	0.95
N5—C6	1.394 (2)	C33—C34	1.381 (3)
C6—N1	1.389 (2)	C33—H33	0.95
N1—C11	1.448 (2)	C34—C35	1.389 (3)
N3—C31	1.448 (3)	C34—H34	0.95
N5—C51	1.452 (2)	C35—C36	1.385 (3)
C2—O2	1.208 (2)	C35—H35	0.95
C4—O4	1.204 (2)	C36—H36	0.95
C6—O6	1.210 (2)	C51—C56	1.381 (3)
C11—C12	1.376 (3)	C51—C52	1.387 (3)
C11—C16	1.388 (3)	C52—C53	1.384 (3)
C12—C13	1.387 (3)	C52—H52	0.95
C12—H12	0.95	C53—C54	1.381 (3)
C13—C14	1.378 (3)	C53—H53	0.95
C13—H13	0.95	C54—C55	1.382 (3)
C14—C15	1.391 (3)	C54—H54	0.95
C14—H14	0.95	C55—C56	1.388 (3)
C15—C16	1.383 (3)	C55—H55	0.95
C15—H15	0.95	C56—H56	0.95
C16—H16	0.95

C2—N1—C11	116.52 (15)	C34—C33—C32	120.06 (18)
C6—N1—C11	118.35 (16)	C34—C33—H33	120.0
C12—C11—C16	121.28 (17)	C32—C33—H33	120.0
C12—C11—N1	119.82 (18)	C33—C34—C35	120.1 (2)
C16—C11—N1	118.88 (17)	C33—C34—H34	119.9
C11—C12—C13	119.01 (19)	C35—C34—H34	119.9
C11—C12—H12	120.5	C36—C35—C34	120.3 (2)
C13—C12—H12	120.5	C36—C35—H35	119.9
C14—C13—C12	120.5 (2)	C34—C35—H35	119.9
C14—C13—H13	119.8	C31—C36—C35	118.96 (18)
C12—C13—H13	119.8	C31—C36—H36	120.5
C13—C14—C15	120.13 (19)	C35—C36—H36	120.5
C13—C14—H14	119.9	O4—C4—N5	123.12 (17)
C15—C14—H14	119.9	O4—C4—N3	121.80 (18)
C16—C15—C14	119.8 (2)	C6—N5—C51	118.56 (16)
C16—C15—H15	120.1	C4—N5—C51	117.07 (15)
C14—C15—H15	120.1	C56—C51—C52	121.06 (18)
C15—C16—C11	119.29 (18)	C56—C51—N5	120.14 (17)
C15—C16—H16	120.4	C52—C51—N5	118.79 (17)
C11—C16—H16	120.4	C53—C52—C51	119.44 (19)
O2—C2—N3	122.08 (18)	C53—C52—H52	120.3
O2—C2—N1	122.87 (18)	C51—C52—H52	120.3
C6—N1—C2	125.11 (16)	C54—C53—C52	119.82 (19)
C2—N3—C4	124.97 (17)	C54—C53—H53	120.1
C4—N5—C6	124.38 (16)	C52—C53—H53	120.1
N1—C2—N3	115.05 (16)	C53—C54—C55	120.46 (19)
N3—C4—N5	115.01 (16)	C53—C54—H54	119.8
N5—C6—N1	115.19 (17)	C55—C54—H54	119.8
C2—N3—C31	117.82 (15)	C54—C55—C56	120.16 (19)
C4—N3—C31	117.20 (15)	C54—C55—H55	119.9
C36—C31—C32	121.37 (18)	C56—C55—H55	119.9
C36—C31—N3	119.51 (17)	C51—C56—C55	119.00 (19)
C32—C31—N3	119.11 (18)	C51—C56—H56	120.5
C31—C32—C33	119.22 (19)	C55—C56—H56	120.5
C31—C32—H32	120.4	O6—C6—N1	122.17 (17)
C33—C32—H32	120.4	O6—C6—N5	122.60 (17)

C2—N1—C11—C12	103.9 (2)	N3—C31—C36—C35	−178.28 (18)
C6—N1—C11—C12	−77.6 (2)	C34—C35—C36—C31	−0.6 (3)
C2—N1—C11—C16	−74.1 (2)	C2—N3—C4—O4	179.75 (19)
C6—N1—C11—C16	104.3 (2)	C31—N3—C4—O4	0.5 (3)
C16—C11—C12—C13	0.5 (3)	C2—N3—C4—N5	−3.1 (3)
N1—C11—C12—C13	−177.51 (18)	C31—N3—C4—N5	177.72 (16)
C11—C12—C13—C14	1.4 (3)	O4—C4—N5—C6	−176.37 (19)
C12—C13—C14—C15	−1.9 (3)	N3—C4—N5—C6	6.5 (3)
C13—C14—C15—C16	0.5 (3)	O4—C4—N5—C51	3.3 (3)
C14—C15—C16—C11	1.4 (3)	N3—C4—N5—C51	−173.89 (17)
C12—C11—C16—C15	−1.9 (3)	C6—N5—C51—C56	61.5 (2)
N1—C11—C16—C15	176.14 (19)	C4—N5—C51—C56	−118.2 (2)
C6—N1—C2—O2	−177.5 (2)	C6—N5—C51—C52	−119.9 (2)
C11—N1—C2—O2	0.9 (3)	C4—N5—C51—C52	60.5 (2)
C6—N1—C2—N3	1.5 (3)	C56—C51—C52—C53	2.2 (3)
C11—N1—C2—N3	179.90 (17)	N5—C51—C52—C53	−176.41 (19)
O2—C2—N3—C4	178.34 (19)	C51—C52—C53—C54	−2.0 (3)
N1—C2—N3—C4	−0.7 (3)	C52—C53—C54—C55	−0.2 (4)
O2—C2—N3—C31	−2.4 (3)	C53—C54—C55—C56	2.2 (3)
N1—C2—N3—C31	178.54 (16)	C52—C51—C56—C55	−0.2 (3)
C2—N3—C31—C36	−101.8 (2)	N5—C51—C56—C55	178.4 (2)
C4—N3—C31—C36	77.5 (2)	C54—C55—C56—C51	−1.9 (3)
C2—N3—C31—C32	79.2 (2)	C2—N1—C6—O6	179.14 (18)
C4—N3—C31—C32	−101.5 (2)	C11—N1—C6—O6	0.8 (3)
C36—C31—C32—C33	−0.1 (3)	C2—N1—C6—N5	1.5 (3)
N3—C31—C32—C33	178.87 (18)	C11—N1—C6—N5	−176.87 (16)
C31—C32—C33—C34	−0.6 (3)	C4—N5—C6—O6	176.58 (18)
C32—C33—C34—C35	0.6 (3)	C51—N5—C6—O6	−3.0 (3)
C33—C34—C35—C36	−0.1 (3)	C4—N5—C6—N1	−5.8 (3)
C32—C31—C36—C35	0.6 (3)	C51—N5—C6—N1	174.62 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Cg3ⁱ	0.95	2.71	3.541 (2)	146

Symmetry code: (i) −x+5/4, y−1/4, z+3/4.

(II) 1,3,5-triphenylperhydro-1,3,5-triazine-2,4,6-trione, monoclinic polymorph top

Crystal data top

C₂₁H₁₅N₃O₃	F(000) = 744
M_r = 357.36	D_x = 1.421 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1927 reflections
a = 15.6526 (3) Å	θ = 3.2–27.5°
b = 13.6819 (3) Å	µ = 0.10 mm⁻¹
c = 9.6454 (2) Å	T = 120 K
β = 126.035 (2)°	Block, yellow
V = 1670.39 (7) Å³	0.50 × 0.40 × 0.12 mm
Z = 4

Data collection top

Nonius KappaCCD area-detector diffractometer	1927 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1620 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
ϕ and ω scans	h = −20→20
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −17→17
T_min = 0.945, T_max = 0.988	l = −11→12
13735 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.124	w = 1/[σ²(F_o²) + (0.073P)² + 0.412P] where P = (F_o² + 2F_c²)/3
S = 1.17	(Δ/σ)_max < 0.001
1927 reflections	Δρ_max = 0.60 e Å⁻³
126 parameters	Δρ_min = −0.43 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.034 (3)

Crystal data top

C₂₁H₁₅N₃O₃	V = 1670.39 (7) Å³
M_r = 357.36	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 15.6526 (3) Å	µ = 0.10 mm⁻¹
b = 13.6819 (3) Å	T = 120 K
c = 9.6454 (2) Å	0.50 × 0.40 × 0.12 mm
β = 126.035 (2)°

Data collection top

Nonius KappaCCD area-detector diffractometer	1927 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1620 reflections with I > 2σ(I)
T_min = 0.945, T_max = 0.988	R_int = 0.031
13735 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.17	Δρ_max = 0.60 e Å⁻³
1927 reflections	Δρ_min = −0.43 e Å⁻³
126 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O2	0.66010 (7)	0.63216 (7)	0.51159 (11)	0.0261 (3)
O4	0.5000	0.34468 (9)	0.2500	0.0267 (3)
N1	0.5000	0.63634 (10)	0.2500	0.0182 (3)
N3	0.58646 (7)	0.48741 (7)	0.37623 (12)	0.0179 (3)
C2	0.58763 (9)	0.58898 (9)	0.38977 (14)	0.0182 (3)
C4	0.5000	0.43267 (12)	0.2500	0.0184 (4)
C11	0.5000	0.74266 (12)	0.2500	0.0191 (4)
C12	0.56906 (10)	0.79229 (9)	0.22977 (16)	0.0237 (3)
C13	0.56885 (10)	0.89359 (10)	0.23030 (18)	0.0280 (3)
C14	0.5000	0.94402 (14)	0.2500	0.0284 (4)
C31	0.68035 (9)	0.43351 (8)	0.50611 (15)	0.0178 (3)
C32	0.70066 (10)	0.41796 (9)	0.66448 (16)	0.0222 (3)
C33	0.78925 (11)	0.36537 (10)	0.78823 (17)	0.0263 (3)
C34	0.85598 (10)	0.32776 (10)	0.75138 (16)	0.0255 (3)
C35	0.83488 (10)	0.34338 (9)	0.59244 (17)	0.0241 (3)
C36	0.74678 (10)	0.39654 (9)	0.46805 (16)	0.0212 (3)
H12	0.6160	0.7574	0.2157	0.028*
H13	0.6161	0.9285	0.2171	0.034*
H14	0.5000	1.0135	0.2500	0.034*
H32	0.6541	0.4432	0.6884	0.027*
H33	0.8042	0.3551	0.8979	0.032*
H24	0.9164	0.2911	0.8356	0.031*
H35	0.8811	0.3175	0.5682	0.029*
H36	0.7322	0.4074	0.3588	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0234 (5)	0.0184 (5)	0.0238 (5)	−0.0009 (4)	0.0068 (4)	−0.0022 (3)
O4	0.0202 (7)	0.0154 (7)	0.0338 (7)	0.000	0.0099 (6)	0.000
N1	0.0178 (7)	0.0135 (7)	0.0200 (7)	0.000	0.0093 (6)	0.000
N3	0.0168 (5)	0.0139 (5)	0.0202 (5)	0.0007 (4)	0.0094 (5)	0.0003 (4)
C2	0.0191 (6)	0.0165 (6)	0.0200 (6)	−0.0001 (4)	0.0120 (5)	−0.0002 (4)
C4	0.0170 (8)	0.0166 (8)	0.0224 (8)	0.000	0.0120 (7)	0.000
C11	0.0182 (8)	0.0143 (8)	0.0178 (8)	0.000	0.0067 (7)	0.000
C12	0.0220 (6)	0.0203 (7)	0.0266 (6)	0.0008 (5)	0.0131 (5)	0.0006 (5)
C13	0.0238 (7)	0.0206 (7)	0.0328 (7)	−0.0034 (5)	0.0129 (6)	0.0031 (5)
C14	0.0229 (9)	0.0134 (8)	0.0314 (10)	0.000	0.0063 (8)	0.000
C31	0.0166 (6)	0.0124 (6)	0.0199 (6)	−0.0020 (4)	0.0082 (5)	0.0002 (4)
C32	0.0233 (6)	0.0206 (6)	0.0239 (6)	−0.0013 (5)	0.0146 (5)	−0.0008 (5)
C33	0.0293 (7)	0.0247 (7)	0.0197 (6)	−0.0015 (5)	0.0115 (6)	0.0013 (5)
C34	0.0197 (6)	0.0193 (7)	0.0242 (7)	0.0006 (5)	0.0057 (5)	0.0021 (5)
C35	0.0196 (6)	0.0206 (7)	0.0307 (7)	0.0009 (5)	0.0140 (6)	−0.0006 (5)
C36	0.0219 (6)	0.0190 (6)	0.0227 (6)	−0.0007 (5)	0.0131 (5)	0.0008 (5)

Geometric parameters (Å, º) top

N1—C2	1.3940 (13)	C14—H14	0.95
C2—N3	1.3949 (16)	C31—C32	1.3815 (18)
N3—C4	1.3914 (13)	C31—C36	1.3859 (17)
N1—C11	1.455 (2)	C32—C33	1.3850 (18)
N3—C31	1.4516 (14)	C32—H32	0.95
C2—O2	1.2035 (14)	C33—C34	1.3851 (19)
C4—O4	1.204 (2)	C33—H33	0.95
C11—C12	1.3841 (15)	C34—C35	1.3818 (19)
C12—C13	1.3860 (18)	C34—H24	0.95
C12—H12	0.95	C35—C36	1.3869 (17)
C13—C14	1.3836 (17)	C35—H35	0.95
C13—H13	0.95	C36—H36	0.95

C2ⁱ—N1—C2	124.59 (14)	C32—C31—C36	121.08 (11)
C2—N3—C4	124.80 (10)	C32—C31—N3	119.34 (10)
N1—C2—N3	114.92 (10)	C36—C31—N3	119.56 (10)
N3—C4—N3ⁱ	114.86 (14)	C31—C32—C33	119.69 (12)
C2—N1—C11	117.70 (7)	C31—C32—H32	120.2
C12—C11—C12ⁱ	121.24 (16)	C33—C32—H32	120.2
C12—C11—N1	119.38 (8)	C32—C33—C34	119.72 (12)
C11—C12—C13	119.10 (12)	C32—C33—H33	120.1
C11—C12—H12	120.4	C34—C33—H33	120.1
C13—C12—H12	120.4	C35—C34—C33	120.20 (12)
C14—C13—C12	120.19 (12)	C35—C34—H24	119.9
C14—C13—H13	119.9	C33—C34—H24	119.9
C12—C13—H13	119.9	C34—C35—C36	120.53 (12)
C13ⁱ—C14—C13	120.18 (17)	C34—C35—H35	119.7
C13—C14—H14	119.9	C36—C35—H35	119.7
O2—C2—N1	122.83 (12)	C31—C36—C35	118.77 (11)
O2—C2—N3	122.24 (11)	C31—C36—H36	120.6
C4—N3—C31	116.84 (10)	C35—C36—H36	120.6
C2—N3—C31	118.32 (9)	O4—C4—N3	122.57 (7)

C2ⁱ—N1—C11—C12	−110.44 (8)	C4—N3—C31—C36	78.41 (12)
C2—N1—C11—C12	69.56 (8)	C2—N3—C31—C36	−103.88 (13)
C12ⁱ—C11—C12—C13	0.15 (8)	C36—C31—C32—C33	0.59 (19)
N1—C11—C12—C13	−179.85 (8)	N3—C31—C32—C33	179.05 (10)
C11—C12—C13—C14	−0.31 (16)	C31—C32—C33—C34	−0.83 (19)
C2ⁱ—N1—C2—O2	−176.93 (12)	C32—C33—C34—C35	0.61 (19)
C11—N1—C2—O2	3.07 (12)	C33—C34—C35—C36	−0.2 (2)
C11—N1—C2—N3	−175.41 (6)	C32—C31—C36—C35	−0.13 (18)
O2—C2—N3—C4	171.57 (9)	N3—C31—C36—C35	−178.59 (10)
N1—C2—N3—C4	−9.94 (14)	C34—C35—C36—C31	−0.09 (19)
O2—C2—N3—C31	−5.94 (16)	C2—N3—C4—O4	−174.67 (7)
N1—C2—N3—C31	172.55 (8)	C31—N3—C4—O4	2.87 (10)
C4—N3—C31—C32	−100.07 (12)	C31—N3—C4—N3ⁱ	−177.13 (10)
C2—N3—C31—C32	77.63 (14)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C33—H33···Cg2ⁱⁱ	0.95	2.95	3.678 (2)	134

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

Experimental details

	(I)	(II)
Crystal data
Chemical formula	C₂₁H₁₅N₃O₃	C₂₁H₁₅N₃O₃
M_r	357.36	357.36
Crystal system, space group	Orthorhombic, Fdd2	Monoclinic, C2/c
Temperature (K)	120	120
a, b, c (Å)	23.3764 (8), 37.1079 (12), 7.7091 (2)	15.6526 (3), 13.6819 (3), 9.6454 (2)
α, β, γ (°)	90, 90, 90	90, 126.035 (2), 90
V (Å³)	6687.3 (4)	1670.39 (7)
Z	16	4
Radiation type	Mo Kα	Mo Kα
µ (mm⁻¹)	0.10	0.10
Crystal size (mm)	0.5 × 0.24 × 0.1	0.50 × 0.40 × 0.12

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.966, 0.990	0.945, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	22356, 2065, 1859	13735, 1927, 1620
R_int	0.045	0.031
(sin θ/λ)_max (Å⁻¹)	0.651	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.082, 1.08	0.050, 0.124, 1.17
No. of reflections	2065	1927
No. of parameters	244	126
No. of restraints	1	0
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.24	0.60, −0.43

Computer programs: COLLECT (Nonius, 1998), DENZO and COLLECT (Otwinowski & Minor, 1997), DENZO and COLLECT, OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997), OSCAIL and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Selected geometric parameters (Å, º) for (I) top

N1—C2	1.389 (3)	N1—C11	1.448 (2)
C2—N3	1.388 (2)	N3—C31	1.448 (3)
N3—C4	1.395 (2)	N5—C51	1.452 (2)
C4—N5	1.395 (3)	C2—O2	1.208 (2)
N5—C6	1.394 (2)	C4—O4	1.204 (2)
C6—N1	1.389 (2)	C6—O6	1.210 (2)

C6—N1—C2	125.11 (16)	N1—C2—N3	115.05 (16)
C2—N3—C4	124.97 (17)	N3—C4—N5	115.01 (16)
C4—N5—C6	124.38 (16)	N5—C6—N1	115.19 (17)

C2—N1—C11—C12	103.9 (2)	C6—N5—C51—C52	−119.9 (2)
C4—N3—C31—C32	−101.5 (2)

Hydrogen-bond geometry (Å, º) for (I) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Cg3ⁱ	0.95	2.71	3.541 (2)	146

Symmetry code: (i) −x+5/4, y−1/4, z+3/4.

Selected geometric parameters (Å, º) for (II) top

N1—C2	1.3940 (13)	N3—C31	1.4516 (14)
C2—N3	1.3949 (16)	C2—O2	1.2035 (14)
N3—C4	1.3914 (13)	C4—O4	1.204 (2)
N1—C11	1.455 (2)

C2ⁱ—N1—C2	124.59 (14)	N1—C2—N3	114.92 (10)
C2—N3—C4	124.80 (10)	N3—C4—N3ⁱ	114.86 (14)

C2—N1—C11—C12	69.56 (8)	C4—N3—C31—C32	−100.07 (12)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) for (II) top

D—H···A	D—H	H···A	D···A	D—H···A
C33—H33···Cg2ⁱⁱ	0.95	2.95	3.678 (2)	134

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

Footnotes

‡Postal address: Department of Electrical Engineering and Physics, University of Dundee, Dundee DD1 4HN, Scotland.

Acknowledgements

The X-ray data were collected at the EPSRC X-ray Crystallographic Service, University of Southampton, England; the authors thank the staff for all their help and advice. JNL thanks NCR Self-Service, Dundee, for grants which have provided computing facilities for this work.

References

Boeyens, J. C. A. (1978). J. Cryst. Mol. Struct. 8, 317–320. CrossRef Web of Science Google Scholar
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Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1353–1359. Google Scholar
Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada. Google Scholar
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ISSN: 2053-2296

Volume 60| Part 9| September 2004| Pages o682-o685

doi:10.1107/S0108270104017342

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Orthorhombic and monoclinic polymorphs of 1,3,5-tri­phenyl­per­hydro-1,3,5-triazine-2,4,6-trione at 120 K: chains and sheets formed by C—H⋯π(arene) hydrogen bonds

Comment

Experimental

Polymorph (I)

Crystal data

Data collection

Refinement

Polymorph (II)

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

Orthorhombic and monoclinic polymorphs of 1,3,5-triphenylperhydro-1,3,5-triazine-2,4,6-trione at 120 K: chains and sheets formed by C—H⋯π(arene) hydrogen bonds