N-(4-Methyl­pyridin-2-yl)-5H-dibenzo[d,f][1,3]diazepine-6-carboxamide toluene hemisolvate

Hodorowicz, M.; Stadnicka, K.; Trzewik, B.; Zaleska, B.

doi:10.1107/S1600536807042687

N-(4-Methylpyridin-2-yl)-5H-dibenzo[d,f][1,3]diazepine-6-carboxamide toluene hemisolvate

M. Hodorowicz, K. Stadnicka, B. Trzewik and B. Zaleska

The title compound, C₂₀H₁₆N₄O·0.5C₇H₈, crystallizes with half a toluene molecule (disordered about a centre of inversion); the seven-membered diazepine ring adopts a twist-boat conformation. The structure features two intramolecular (N—H

O and N—H

N) and one intermolecular hydrogen bond. Additional intermolecular π–π interactions (3.556–3.651 Å) give rise to a three-dimensional network in the crystal structure.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042687/ng2316sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042687/ng2316Isup2.hkl Contains datablock I

CCDC reference: 663806

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
Disorder in solvent or counterion
R factor = 0.052
wR factor = 0.148
Data-to-parameter ratio = 30.0

checkCIF/PLATON results

No syntax errors found



Alert level A
REFLT03_ALERT_3_A  Reflection count > 15% excess reflns - sys abs data present?
           From the CIF: _diffrn_reflns_theta_max           27.43
           From the CIF: _diffrn_reflns_theta_full          27.43
           From the CIF: _reflns_number_total               8631
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         4400
           Completeness (_total/calc)            196.16%

Author Response: Refinement with redundant (i.e. not merged/unique) data set: data set combined of two independent measurements; refinement with BASF parameter as the scale factor for second data set.


Alert level B
PLAT021_ALERT_1_B Ratio Unique / Expected Reflections too High ...       1.96

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        C54
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C51
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C52
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.15
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   8 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
   2 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Benzodiazepines are one of the most important substances in medicinal chemistry, representing the prototypical 'privileged structure' (Evans et al. 1988). Compounds based on the diazepine skeleton are psychotherapeutic agents widely used for the treatment of anxiety and neurosis (Sternbach, 1978). The crystal structure analysis of N-(4-methylpyridin-2-yl)-5H-dibenzo[d,f][1,3] diazepine-6-carboxamide was performed to find out the influence of methyl substituent on molecular geometry and packing properties. The molecular structure of the title compound is shown in Fig. 1. The symmetrically independent part of the unit cell is composed of title compound molecule and disordered toluene molecule. The core of the diazepine molecule is composed of a seven-membered ring to which a pyridin-2-ylamino carbonyl substituent is attached and two benzene rings are fused. The puckering parameters of the seven-membered ring (atoms in N3, C2,···,C31 sequence): q2 = 0.5752, q3 = 0.0819, QT = 0.5810, φ2 = -6.33, φ3 = 10.46, θ2 = 81.89°, indicate a twisted-boat conformation with a pseudo-mirror plane (C_s) through the N3 atom and the centre of C41—C46 bond. From the chemical point of view there is also a pseudo 2-fold axis (C₂) bisecting the diazepine ring through C2 and the center of C36–C46 bond. The bond lengths and valence angles are typical and comparable with the values reported in the literature (Allen et al. 1987). Two N atoms are involved in hydrogen bonds: two intra- and one intermolecular (Table 1). The intermolecular N3—H3···O1 [-x, 1 - y, 1 - z] interaction is relatively weak due to simultaneous donor participation in intramolecular interaction (bifurcated hydrogen bond). In addition, there are two types of π–π interactions, which assist in the stabilization of the three-dimensional-packing. The benzene ring C31···C36 is strictly parallel to another one in position [1 - x, 1 - y, 1 - z], with interplanar spacing of 3.556 Å, the ring-centroid separation of 3.883 Å and with ring offset of 1.560 Å. The pyridine ring is nearly parallel to another benzene ring C41···C46 of the molecule at [1 - x, - y, 1 - z]. The interplanar spacing is 3.651 Å, the corresponding ring-centroid separation is 3.790 Å, resulting in the offset of 1.017 Å. The π–π interaction are illustrated in Fig. 2. As it can be seen in Fig. 2, the solvent accessible cavities at 0, 1/2, 1 are filled with disordered toluene molecules which stabilized three-dimensional structure (total potential solvent area of 195.7 Å³ makes 20.3% of unit cell volume).

Related literature top

For literature on the medicinal and psychotherapeutic uses of similar compounds, see Evans et al. (1988); Sternbach (1978). For comparativ bond distances, see Allen et al. (1987).

Experimental top

Recrystallization from toluene afforded crystals suitable for X-ray measurements.

Structure description top

For literature on the medicinal and psychotherapeutic uses of similar compounds, see Evans et al. (1988); Sternbach (1978). For comparativ bond distances, see Allen et al. (1987).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

	Fig. 1. ORTEP-3 (Farrugia, 1997) drawing of the title compound with labels. Displacement ellipsoids of non-H atoms drawn at 30% probability level.
	Fig. 2. ORTEP-3 (Farrugia, 1997) drawing of the crystal packing viewed along [010] with marked π–π interactions (dashed bonds). Hydrogen atoms are omitted.

N-(4-Methylpyridin-2-yl)-5H-dibenzo[d,f][1,3]diazepine-6- carboxamide toluene hemisolvate top

Crystal data top

C₂₀H₁₆N₄O·0.5C₇H₈	Z = 2
M_r = 374.44	F(000) = 394
Triclinic, P1	D_x = 1.291 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9323 (2) Å	Cell parameters from 2469 reflections
b = 9.6863 (2) Å	θ = 1.0–27.5°
c = 12.1478 (3) Å	µ = 0.08 mm⁻¹
α = 77.050 (1)°	T = 293 K
β = 87.529 (1)°	Prism, orange
γ = 70.191 (1)°	0.29 × 0.21 × 0.15 mm
V = 963.08 (4) Å³

Data collection top

Nonius KappaCCD diffractometer	8631 independent reflections
Radiation source: fine-focus sealed tube	5192 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	R_int = 0.000
Detector resolution: 9 pixels mm^-1	θ_max = 27.4°, θ_min = 2.4°
φ and ω scans to fill asymmetric unit	h = −11→11
Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997)	k = −12→12
T_min = 0.977, T_max = 0.988	l = 0→15
17061 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)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.148	w = 1/[σ²(F_o²) + (0.0656P)² + 0.0957P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.01
8631 reflections	Δρ_max = 0.18 e Å⁻³
288 parameters	Δρ_min = −0.18 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: 0.014 (3)

Crystal data top

C₂₀H₁₆N₄O·0.5C₇H₈	γ = 70.191 (1)°
M_r = 374.44	V = 963.08 (4) Å³
Triclinic, P1	Z = 2
a = 8.9323 (2) Å	Mo Kα radiation
b = 9.6863 (2) Å	µ = 0.08 mm⁻¹
c = 12.1478 (3) Å	T = 293 K
α = 77.050 (1)°	0.29 × 0.21 × 0.15 mm
β = 87.529 (1)°

Data collection top

Nonius KappaCCD diffractometer	8631 independent reflections
Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997)	5192 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.988	R_int = 0.000
17061 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.18 e Å⁻³
8631 reflections	Δρ_min = −0.18 e Å⁻³
288 parameters

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 with redundant (i.e. not merged/unique) data set: data set combined of two independent measurements; refinement with BASF parameter as the scale factor for second data set. 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.17801 (13)	0.23113 (12)	0.51837 (9)	0.0458 (3)
O1	0.07918 (10)	0.32376 (9)	0.56173 (8)	0.0611 (2)
C2	0.27718 (12)	0.28173 (12)	0.42283 (9)	0.0430 (3)
N3	0.23275 (11)	0.43460 (10)	0.38922 (9)	0.0505 (3)
H3	0.1546 (16)	0.4821 (14)	0.4286 (10)	0.058 (4)*
C31	0.34450 (12)	0.51109 (11)	0.36175 (9)	0.0435 (3)
C32	0.32397 (14)	0.63436 (12)	0.40814 (10)	0.0534 (3)
H32	0.2384	0.6645	0.4540	0.064*
C33	0.42946 (16)	0.71276 (13)	0.38688 (11)	0.0605 (3)
H33	0.4140	0.7963	0.4174	0.073*
C34	0.55721 (15)	0.66709 (14)	0.32055 (12)	0.0603 (3)
H34	0.6297	0.7184	0.3071	0.072*
C35	0.57746 (14)	0.54485 (13)	0.27409 (10)	0.0521 (3)
H35	0.6645	0.5149	0.2294	0.062*
C36	0.47134 (12)	0.46415 (11)	0.29185 (9)	0.0427 (2)
C46	0.49668 (12)	0.33809 (12)	0.23420 (9)	0.0430 (2)
C45	0.56872 (14)	0.34457 (14)	0.13001 (10)	0.0560 (3)
H45	0.5935	0.4302	0.0970	0.067*
C44	0.60463 (17)	0.22908 (16)	0.07395 (12)	0.0687 (4)
H44	0.6513	0.2380	0.0040	0.082*
C43	0.57127 (17)	0.10084 (17)	0.12164 (12)	0.0702 (4)
H43	0.5972	0.0214	0.0852	0.084*
C42	0.49880 (14)	0.09106 (14)	0.22422 (11)	0.0565 (3)
H42	0.4765	0.0039	0.2565	0.068*
C41	0.45811 (12)	0.20788 (12)	0.28090 (9)	0.0428 (2)
N4	0.38063 (10)	0.17891 (10)	0.38303 (8)	0.0450 (2)
N2	0.20866 (12)	0.08255 (11)	0.54501 (9)	0.0513 (3)
H2	0.2779 (16)	0.0327 (15)	0.5026 (12)	0.069 (4)*
C21	0.12759 (13)	−0.00035 (12)	0.61882 (9)	0.0458 (3)
C22	0.03000 (14)	0.05641 (14)	0.70102 (10)	0.0531 (3)
H22	0.0155	0.1528	0.7103	0.064*
C23	−0.04599 (15)	−0.03245 (15)	0.76942 (10)	0.0577 (3)
C24	−0.01902 (16)	−0.17409 (15)	0.75086 (11)	0.0645 (4)
H24	−0.0679	−0.2374	0.7946	0.077*
C25	0.08051 (16)	−0.22065 (14)	0.66741 (12)	0.0624 (3)
H25	0.0970	−0.3166	0.6565	0.075*
N26	0.15561 (12)	−0.13681 (10)	0.60055 (8)	0.0539 (3)
C27	−0.1531 (2)	0.0259 (2)	0.86000 (13)	0.0853 (5)
H27A	−0.1950	−0.0498	0.8997	0.102*
H27B	−0.2393	0.1146	0.8260	0.102*
H27C	−0.0933	0.0502	0.9121	0.102*
C50	0.0601 (10)	0.3448 (10)	−0.1225 (8)	0.141 (4)	0.50
H50A	0.0559	0.4006	−0.1991	0.169*	0.50
H50B	−0.0135	0.2908	−0.1153	0.169*	0.50
H50C	0.1659	0.2749	−0.1032	0.169*	0.50
C51	0.0177 (5)	0.4482 (4)	−0.0469 (2)	0.0800 (9)	0.50
C52	0.1356 (3)	0.4569 (3)	0.0196 (3)	0.0699 (17)	0.50
H52	0.2411	0.3975	0.0150	0.084*	0.50
C53	0.0958 (5)	0.5544 (4)	0.0928 (2)	0.0986 (13)	0.50
H53	0.1747	0.5603	0.1373	0.118*	0.50
C54	−0.0619 (6)	0.6433 (4)	0.0996 (3)	0.118 (4)	0.50
H54	−0.0886	0.7085	0.1486	0.142*	0.50
C55	−0.1799 (3)	0.6345 (4)	0.0332 (4)	0.1057 (14)	0.50
H55	−0.2854	0.6940	0.0377	0.127*	0.50
C56	−0.1400 (4)	0.5370 (5)	−0.0401 (3)	0.099 (3)	0.50
H56	−0.2189	0.5312	−0.0845	0.119*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0459 (6)	0.0426 (6)	0.0505 (6)	−0.0172 (5)	0.0101 (5)	−0.0112 (5)
O1	0.0620 (5)	0.0468 (5)	0.0748 (6)	−0.0191 (4)	0.0306 (5)	−0.0182 (4)
C2	0.0421 (5)	0.0398 (6)	0.0486 (6)	−0.0160 (4)	0.0072 (5)	−0.0103 (5)
N3	0.0454 (5)	0.0385 (5)	0.0656 (6)	−0.0132 (4)	0.0204 (5)	−0.0124 (4)
C31	0.0451 (6)	0.0366 (5)	0.0464 (6)	−0.0134 (4)	0.0077 (5)	−0.0062 (4)
C32	0.0592 (7)	0.0416 (6)	0.0570 (7)	−0.0142 (5)	0.0147 (6)	−0.0128 (5)
C33	0.0734 (8)	0.0438 (7)	0.0698 (8)	−0.0238 (6)	0.0090 (7)	−0.0187 (6)
C34	0.0628 (7)	0.0495 (7)	0.0760 (9)	−0.0293 (6)	0.0082 (7)	−0.0139 (6)
C35	0.0500 (6)	0.0488 (7)	0.0588 (7)	−0.0208 (5)	0.0128 (5)	−0.0101 (5)
C36	0.0435 (5)	0.0381 (6)	0.0446 (6)	−0.0137 (4)	0.0060 (5)	−0.0063 (4)
C46	0.0387 (5)	0.0444 (6)	0.0449 (6)	−0.0130 (4)	0.0064 (5)	−0.0104 (5)
C45	0.0584 (7)	0.0615 (7)	0.0519 (7)	−0.0253 (6)	0.0156 (6)	−0.0150 (6)
C44	0.0777 (9)	0.0797 (10)	0.0563 (8)	−0.0304 (7)	0.0272 (7)	−0.0292 (7)
C43	0.0783 (9)	0.0711 (9)	0.0721 (9)	−0.0259 (7)	0.0227 (8)	−0.0404 (7)
C42	0.0594 (7)	0.0505 (7)	0.0644 (8)	−0.0199 (6)	0.0138 (6)	−0.0221 (6)
C41	0.0389 (5)	0.0421 (6)	0.0459 (6)	−0.0114 (4)	0.0058 (5)	−0.0112 (4)
N4	0.0454 (5)	0.0399 (5)	0.0496 (5)	−0.0148 (4)	0.0107 (4)	−0.0110 (4)
N2	0.0558 (6)	0.0414 (5)	0.0557 (6)	−0.0171 (4)	0.0203 (5)	−0.0110 (4)
C21	0.0452 (6)	0.0430 (6)	0.0466 (6)	−0.0160 (5)	0.0030 (5)	−0.0033 (5)
C22	0.0604 (7)	0.0534 (7)	0.0495 (6)	−0.0248 (6)	0.0104 (6)	−0.0121 (5)
C23	0.0575 (7)	0.0733 (9)	0.0446 (6)	−0.0305 (6)	0.0065 (6)	−0.0053 (6)
C24	0.0656 (8)	0.0658 (9)	0.0628 (8)	−0.0354 (7)	0.0029 (7)	0.0049 (6)
C25	0.0651 (8)	0.0464 (7)	0.0745 (9)	−0.0238 (6)	0.0006 (7)	−0.0026 (6)
N26	0.0550 (6)	0.0419 (5)	0.0615 (6)	−0.0163 (4)	0.0049 (5)	−0.0058 (4)
C27	0.0911 (11)	0.1162 (13)	0.0609 (9)	−0.0534 (10)	0.0294 (8)	−0.0204 (9)
C50	0.189 (11)	0.164 (8)	0.103 (4)	−0.106 (7)	0.024 (5)	−0.027 (5)
C51	0.104 (3)	0.076 (2)	0.0657 (19)	−0.055 (2)	0.010 (2)	0.0105 (16)
C52	0.049 (3)	0.080 (4)	0.076 (2)	−0.037 (3)	−0.010 (2)	0.018 (2)
C53	0.100 (3)	0.114 (4)	0.089 (3)	−0.062 (3)	−0.022 (2)	0.008 (2)
C54	0.157 (9)	0.081 (4)	0.114 (6)	−0.049 (5)	0.037 (5)	−0.010 (4)
C55	0.081 (3)	0.105 (3)	0.117 (4)	−0.037 (2)	0.014 (3)	0.011 (3)
C56	0.096 (6)	0.114 (7)	0.084 (3)	−0.054 (5)	−0.007 (3)	0.015 (3)

Geometric parameters (Å, º) top

C1—O1	1.223 (1)	N2—H2	0.87 (1)
C1—N2	1.335 (1)	C21—N26	1.327 (1)
C1—C2	1.524 (2)	C21—C22	1.380 (2)
C2—N4	1.278 (1)	C22—C23	1.385 (2)
C2—N3	1.364 (1)	C22—H22	0.9300
N3—C31	1.421 (1)	C23—C24	1.379 (2)
N3—H3	0.88 (1)	C23—C27	1.506 (2)
C31—C32	1.386 (2)	C24—C25	1.370 (2)
C31—C36	1.397 (1)	C24—H24	0.9300
C32—C33	1.381 (2)	C25—N26	1.340 (2)
C32—H32	0.9300	C25—H25	0.9300
C33—C34	1.373 (2)	C27—H27A	0.9600
C33—H33	0.9300	C27—H27B	0.9600
C34—C35	1.378 (2)	C27—H27C	0.9600
C34—H34	0.9300	C50—C51	1.455 (8)
C35—C36	1.402 (2)	C50—H50A	0.9600
C35—H35	0.9300	C50—H50B	0.9600
C36—C46	1.488 (2)	C50—H50C	0.9600
C46—C45	1.393 (2)	C51—C52	1.3900
C46—C41	1.410 (2)	C51—C56	1.3900
C45—C44	1.377 (2)	C52—C53	1.3900
C45—H45	0.9300	C52—H52	0.9300
C44—C43	1.372 (2)	C53—C54	1.3900
C44—H44	0.9300	C53—H53	0.9300
C43—C42	1.378 (2)	C54—C55	1.3900
C43—H43	0.9300	C54—H54	0.9300
C42—C41	1.391 (1)	C55—C56	1.3900
C42—H42	0.9300	C55—H55	0.9300
C41—N4	1.414 (1)	C56—H56	0.9300
N2—C21	1.410 (1)

O1—C1—N2	126.0 (1)	C2—N4—C41	123.5 (1)
O1—C1—C2	120.4 (1)	C1—N2—C21	128.8 (1)
N2—C1—C2	113.7 (1)	C1—N2—H2	114.6 (9)
N4—C2—N3	130.1 (1)	C21—N2—H2	115.8 (9)
N4—C2—C1	117.1 (1)	N26—C21—C22	124.3 (1)
N3—C2—C1	112.7 (1)	N26—C21—N2	112.9 (1)
C2—N3—C31	122.7 (1)	C22—C21—N2	122.8 (1)
C2—N3—H3	113.0 (8)	C21—C22—C23	118.9 (1)
C31—N3—H3	111.5 (8)	C21—C22—H22	120.5
C32—C31—C36	120.8 (1)	C23—C22—H22	120.5
C32—C31—N3	117.3 (1)	C24—C23—C22	117.4 (1)
C36—C31—N3	121.9 (1)	C24—C23—C27	122.3 (1)
C33—C32—C31	120.6 (1)	C22—C23—C27	120.3 (1)
C33—C32—H32	119.7	C25—C24—C23	119.4 (1)
C31—C32—H32	119.7	C25—C24—H24	120.3
C34—C33—C32	119.8 (1)	C23—C24—H24	120.3
C34—C33—H33	120.1	N26—C25—C24	124.2 (1)
C32—C33—H33	120.1	N26—C25—H25	117.9
C33—C34—C35	119.6 (1)	C24—C25—H25	117.9
C33—C34—H34	120.2	C21—N26—C25	115.7 (1)
C35—C34—H34	120.2	C23—C27—H27A	109.5
C34—C35—C36	122.3 (1)	C23—C27—H27B	109.5
C34—C35—H35	118.9	H27A—C27—H27B	109.5
C36—C35—H35	118.9	C23—C27—H27C	109.5
C31—C36—C35	116.8 (1)	H27A—C27—H27C	109.5
C31—C36—C46	124.0 (1)	H27B—C27—H27C	109.5
C35—C36—C46	119.1 (1)	C52—C51—C56	120.0
C45—C46—C41	117.3 (1)	C52—C51—C50	119.7 (5)
C45—C46—C36	118.8 (1)	C56—C51—C50	120.3 (5)
C41—C46—C36	123.9 (1)	C51—C52—C53	120.0
C44—C45—C46	122.5 (1)	C51—C52—H52	120.0
C44—C45—H45	118.7	C53—C52—H52	120.0
C46—C45—H45	118.7	C52—C53—C54	120.0
C43—C44—C45	119.8 (1)	C52—C53—H53	120.0
C43—C44—H44	120.1	C54—C53—H53	120.0
C45—C44—H44	120.1	C55—C54—C53	120.0
C44—C43—C42	119.2 (1)	C55—C54—H54	120.0
C44—C43—H43	120.4	C53—C54—H54	120.0
C42—C43—H43	120.4	C56—C55—C54	120.0
C43—C42—C41	121.9 (1)	C56—C55—H55	120.0
C43—C42—H42	119.1	C54—C55—H55	120.0
C41—C42—H42	119.1	C55—C56—C51	120.0
C42—C41—C46	119.2 (1)	C55—C56—H56	120.0
C42—C41—N4	113.7 (1)	C51—C56—H56	120.0
C46—C41—N4	127.1 (1)

O1—C1—C2—N4	178.5 (1)	C45—C46—C41—C42	2.6 (2)
N2—C1—C2—N4	−2.8 (2)	C36—C46—C41—C42	−174.7 (1)
O1—C1—C2—N3	−4.9 (2)	C45—C46—C41—N4	−177.9 (1)
N2—C1—C2—N3	173.7 (1)	C36—C46—C41—N4	4.9 (2)
N4—C2—N3—C31	−44.4 (2)	N3—C2—N4—C41	−9.1 (2)
C1—C2—N3—C31	139.6 (1)	C1—C2—N4—C41	166.7 (1)
C2—N3—C31—C32	−132.8 (1)	C42—C41—N4—C2	−149.2 (1)
C2—N3—C31—C36	46.6 (2)	C46—C41—N4—C2	31.2 (2)
C36—C31—C32—C33	−0.5 (2)	O1—C1—N2—C21	6.7 (2)
N3—C31—C32—C33	178.9 (1)	C2—C1—N2—C21	−171.9 (1)
C31—C32—C33—C34	−0.9 (2)	C1—N2—C21—N26	160.4 (1)
C32—C33—C34—C35	1.1 (2)	C1—N2—C21—C22	−19.7 (2)
C33—C34—C35—C36	0.1 (2)	N26—C21—C22—C23	−0.5 (2)
C32—C31—C36—C35	1.7 (2)	N2—C21—C22—C23	179.6 (1)
N3—C31—C36—C35	−177.7 (1)	C21—C22—C23—C24	0.0 (2)
C32—C31—C36—C46	−176.7 (1)	C21—C22—C23—C27	179.9 (1)
N3—C31—C36—C46	3.9 (2)	C22—C23—C24—C25	0.3 (2)
C34—C35—C36—C31	−1.5 (2)	C27—C23—C24—C25	−179.7 (1)
C34—C35—C36—C46	177.0 (1)	C23—C24—C25—N26	−0.1 (2)
C31—C36—C46—C45	148.6 (1)	C22—C21—N26—C25	0.7 (2)
C35—C36—C46—C45	−29.8 (2)	N2—C21—N26—C25	−179.4 (1)
C31—C36—C46—C41	−34.2 (2)	C24—C25—N26—C21	−0.4 (2)
C35—C36—C46—C41	147.5 (1)	C56—C51—C52—C53	0.0
C41—C46—C45—C44	−1.1 (2)	C50—C51—C52—C53	−179.4 (5)
C36—C46—C45—C44	176.3 (1)	C51—C52—C53—C54	0.0
C46—C45—C44—C43	−0.9 (2)	C52—C53—C54—C55	0.0
C45—C44—C43—C42	1.4 (2)	C53—C54—C55—C56	0.0
C44—C43—C42—C41	0.1 (2)	C54—C55—C56—C51	0.0
C43—C42—C41—C46	−2.2 (2)	C52—C51—C56—C55	0.0
C43—C42—C41—N4	178.2 (1)	C50—C51—C56—C55	179.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.88 (1)	2.22 (1)	2.677 (1)	112 (1)
N3—H3···O1ⁱ	0.88 (1)	2.31 (1)	3.108 (1)	151 (1)
N2—H2···N4	0.87 (1)	2.19 (1)	2.644 (1)	112 (1)

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₆N₄O·0.5C₇H₈
M_r	374.44
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.9323 (2), 9.6863 (2), 12.1478 (3)
α, β, γ (°)	77.050 (1), 87.529 (1), 70.191 (1)
V (Å³)	963.08 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.29 × 0.21 × 0.15

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	Multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.977, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	17061, 8631, 5192
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.148, 1.02
No. of reflections	8631
No. of parameters	288
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.18

Computer programs: COLLECT (Nonius, 2000), SCALEPACK (Otwinowski & Minor, 1997), SCALEPACK and DENZO (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997).