1,2-Dibenzoyl­hydrazine–dimethyl­formamide (3/1)

He, Q.-P.; Li, H.-G.; Wang, G.-B.; Fu, F.-L.; Liu, M.-S.

doi:10.1107/S1600536809016778

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1267

doi:10.1107/S1600536809016778

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1,2-Dibenzoylhydrazine–dimethylformamide (3/1)

Qing-Peng He,^a ^* Hong-Gang Li,^b Guang-Bo Wang,^c Feng-Lian Fu ^c and Ming-Shi Liu ^d

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China, ^bClinical Medicine Department, Weifang Medical University, Weifang, Shangdong, 261042, People's Republic of China, ^cShandong Wuxun High School, Guanxian, Shandong 252500, People's Republic of China, and ^dPetroChina Jinxi Branch Company (Bihai), 125001, People's Republic of China
^*Correspondence e-mail: heqp2008@163.com

(Received 5 April 2009; accepted 5 May 2009; online 14 May 2009)

The title compound, 3C₁₄H₁₂N₂O₂·C₃H₇NO, was synthesized by reaction of benzoyl chloride with hydrazine hydrate under microwave irradition. The asymmetric unit comprises three 1,2-dibenzoylhydrazine molecules and one dimethylformamide molecule. The 1,2-dibenzoylhydrazine molecules are linked by pairs of N—H⋯O hydrogen bonds into chains propagating along [010].

Related literature

For background literature concerning microwave-assisted synthesis, see: Galema (1997 ). For the unsolvated crystal structure of 1,2-dibenzoylhydrazine, see: Shanmuga Sundara Raj et al. (2000 ).

Experimental

Crystal data

3C₁₄H₁₂N₂O₂·C₃H₇NO
M_r = 793.86
Triclinic, $[P \overline 1]$
a = 10.7666 (12) Å
b = 11.4615 (13) Å
c = 18.100 (2) Å
α = 100.127 (2)°
β = 96.084 (2)°
γ = 108.382 (3)°
V = 2055.2 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.50 × 0.32 × 0.27 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.957, T_max = 0.977
6846 measured reflections
4163 independent reflections
2487 reflections with I > 2σ(I)
R_int = 0.075
θ_max = 20.8°

Refinement

R[F² > 2σ(F²)] = 0.120
wR(F²) = 0.359
S = 1.14
4163 reflections
534 parameters
H-atom parameters constrained
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5ⁱ	0.86	2.04	2.846 (9)	156
N6—H6⋯O2ⁱⁱ	0.86	2.01	2.826 (9)	157
N2—H2⋯O3	0.86	2.00	2.800 (9)	155
N3—H3⋯O6	0.86	1.96	2.778 (10)	158
N4—H4⋯O1	0.86	1.92	2.743 (9)	160
N5—H5⋯O4	0.86	1.97	2.774 (9)	155
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809016778/bi2365sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809016778/bi2365Isup2.hkl

checkCIF report

Comment top

In recent years, high-speed synthesis using microwave radiation has attracted considerable attention, and some important reviews in the study of microwave-assisted organic synthesis have been published (Galema, 1997). We describe in this paper a user-friendly microwave irradiation protocol for the synthesis of the title compound, and its crystal structure.

In the crystal structure, the asymmetric unit comprises three 1,2-dibenzoylhydrazine molecules and one dimethylformamide solvent molecule. The bond lengths and angles are normal and comparable to those in the unsolvated crystal structure of 1,2-dibenzoylhydrazine (Shanmuga Sundara Raj et al., 2000). Molecules are linked by N—H···O hydrogen bonds between the amide H and carbonyl O atoms, forming ten-membered rings, into chains propagating along [010]. the dimethylformamide molecules lie between these chains.

Related literature top

For background literature concerning microwave-assisted synthesis, see: Galema (1997). For the unsolvated crystal structure of 1,2-dibenzoylhydrazine, see: Shanmuga Sundara Raj et al. (2000).

Experimental top

Benzoyl chloride (0.5 mmol) and hydrazine hydrate (0.5 mmol) were mixed in a 50 ml flask. After microwave irradiation for 5 min at 275 W, then cooling to room temperature, the resulting mixture was washed with 10 ml water to yield a white product. The crude product was recrystallised from ethanol to afford the title compound as a crystalline solid. Elemental analysis calculated for C₄₅H₄₃N₇O₇: C 68.08, H 5.46, N 12.35%; found: C 68.24, H 5.68, N 12.28%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The content of asymmetric unit of the title compound showing the atomic numbering scheme and 30% probability displacement ellipsoids.The solvent molecular is omitted for clarity.

1,2-Dibenzoylhydrazine–dimethylformamide (3/1) top

Crystal data top

3C₁₄H₁₂N₂O₂·C₃H₇NO	Z = 2
M_r = 793.86	F(000) = 836
Triclinic, P1	D_x = 1.283 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.7666 (12) Å	Cell parameters from 1452 reflections
b = 11.4615 (13) Å	θ = 2.3–21.0°
c = 18.100 (2) Å	µ = 0.09 mm⁻¹
α = 100.127 (2)°	T = 298 K
β = 96.084 (2)°	Needle, colourless
γ = 108.382 (3)°	0.50 × 0.32 × 0.27 mm
V = 2055.2 (4) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	4163 independent reflections
Radiation source: fine-focus sealed tube	2487 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.075
ϕ and ω scans	θ_max = 20.8°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.957, T_max = 0.977	k = −11→11
6846 measured reflections	l = −10→18

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)] = 0.120	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.359	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
4163 reflections	(Δ/σ)_max = 0.001
534 parameters	Δρ_max = 0.66 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

3C₁₄H₁₂N₂O₂·C₃H₇NO	γ = 108.382 (3)°
M_r = 793.86	V = 2055.2 (4) Å³
Triclinic, P1	Z = 2
a = 10.7666 (12) Å	Mo Kα radiation
b = 11.4615 (13) Å	µ = 0.09 mm⁻¹
c = 18.100 (2) Å	T = 298 K
α = 100.127 (2)°	0.50 × 0.32 × 0.27 mm
β = 96.084 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	4163 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2487 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.977	R_int = 0.075
6846 measured reflections	θ_max = 20.8°

Refinement top

R[F² > 2σ(F²)] = 0.120	0 restraints
wR(F²) = 0.359	H-atom parameters constrained
S = 1.14	Δρ_max = 0.66 e Å⁻³
4163 reflections	Δρ_min = −0.52 e Å⁻³
534 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 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
N1	0.1213 (7)	0.7581 (6)	0.2502 (4)	0.0367 (18)
H1	0.0827	0.8132	0.2585	0.044*
N2	0.1953 (7)	0.7353 (7)	0.3099 (4)	0.0373 (19)
H2	0.1642	0.6671	0.3257	0.045*
N3	0.1123 (6)	0.3584 (6)	0.2436 (4)	0.0377 (19)
H3	0.0958	0.2827	0.2184	0.045*
N4	0.2312 (6)	0.4518 (6)	0.2435 (4)	0.0364 (18)
H4	0.2316	0.5089	0.2184	0.044*
N5	0.1935 (7)	0.1264 (6)	0.3108 (4)	0.0368 (18)
H5	0.2342	0.2062	0.3268	0.044*
N6	0.2322 (7)	0.0597 (6)	0.2525 (4)	0.0354 (18)
H6	0.2766	0.0117	0.2619	0.042*
N7	0.380 (3)	0.619 (2)	0.8906 (19)	0.200 (10)
O1	0.1675 (7)	0.6159 (6)	0.1659 (3)	0.0541 (18)
O2	0.3604 (6)	0.9179 (6)	0.3238 (3)	0.0472 (17)
O3	0.0421 (6)	0.4918 (6)	0.3186 (4)	0.0495 (17)
O4	0.3487 (5)	0.3746 (6)	0.3198 (3)	0.0460 (16)
O5	0.0327 (6)	−0.0487 (6)	0.3225 (3)	0.0491 (17)
O6	0.1339 (7)	0.1356 (6)	0.1664 (3)	0.0550 (18)
O7	0.5384 (19)	0.6803 (19)	1.0039 (13)	0.241 (8)
C1	0.1106 (9)	0.6927 (8)	0.1791 (5)	0.036 (2)
C2	0.0228 (9)	0.7136 (8)	0.1180 (5)	0.040 (2)
C3	0.0276 (11)	0.6610 (10)	0.0446 (6)	0.062 (3)
H3A	0.0873	0.6187	0.0359	0.074*
C4	−0.0520 (15)	0.6694 (11)	−0.0146 (6)	0.077 (4)
H4A	−0.0452	0.6346	−0.0638	0.093*
C5	−0.1417 (14)	0.7274 (14)	−0.0044 (7)	0.082 (4)
H5A	−0.1977	0.7307	−0.0462	0.099*
C6	−0.1506 (11)	0.7816 (12)	0.0676 (8)	0.080 (4)
H6A	−0.2132	0.8208	0.0753	0.095*
C7	−0.0630 (10)	0.7770 (10)	0.1300 (6)	0.059 (3)
H7	−0.0642	0.8173	0.1791	0.071*
C8	0.3152 (9)	0.8189 (8)	0.3433 (4)	0.032 (2)
C9	0.3875 (8)	0.7849 (8)	0.4068 (4)	0.034 (2)
C10	0.3335 (9)	0.6761 (9)	0.4323 (5)	0.042 (2)
H10	0.2486	0.6210	0.4099	0.050*
C11	0.4055 (10)	0.6491 (11)	0.4910 (5)	0.058 (3)
H11	0.3709	0.5739	0.5066	0.070*
C12	0.5278 (11)	0.7334 (12)	0.5261 (6)	0.069 (3)
H12	0.5746	0.7186	0.5676	0.083*
C13	0.5791 (11)	0.8381 (12)	0.4996 (7)	0.079 (4)
H13	0.6642	0.8930	0.5217	0.095*
C14	0.5094 (9)	0.8667 (10)	0.4404 (5)	0.059 (3)
H14	0.5459	0.9409	0.4242	0.071*
C15	0.0250 (8)	0.3862 (9)	0.2823 (5)	0.034 (2)
C16	−0.1008 (8)	0.2810 (8)	0.2787 (5)	0.037 (2)
C17	−0.1390 (9)	0.1684 (10)	0.2308 (6)	0.061 (3)
H17	−0.0848	0.1536	0.1962	0.073*
C18	−0.2547 (12)	0.0737 (11)	0.2306 (8)	0.088 (4)
H18	−0.2788	−0.0021	0.1949	0.106*
C19	−0.3312 (12)	0.0886 (12)	0.2797 (7)	0.079 (4)
H19	−0.4076	0.0225	0.2805	0.094*
C20	−0.2992 (11)	0.2016 (14)	0.3301 (7)	0.096 (5)
H20	−0.3558	0.2150	0.3635	0.115*
C21	−0.1791 (10)	0.2973 (11)	0.3306 (6)	0.072 (3)
H21	−0.1532	0.3726	0.3669	0.086*
C22	0.3466 (8)	0.4540 (8)	0.2825 (5)	0.028 (2)
C23	0.4680 (8)	0.5553 (8)	0.2778 (5)	0.035 (2)
C24	0.5759 (9)	0.5837 (11)	0.3321 (6)	0.060 (3)
H24	0.5733	0.5376	0.3697	0.073*
C25	0.6887 (10)	0.6805 (12)	0.3313 (7)	0.075 (3)
H25	0.7604	0.7021	0.3706	0.091*
C26	0.7002 (11)	0.7455 (12)	0.2764 (8)	0.078 (4)
H26	0.7796	0.8080	0.2755	0.093*
C27	0.5919 (13)	0.7169 (12)	0.2219 (8)	0.090 (4)
H27	0.5964	0.7615	0.1834	0.108*
C28	0.4764 (10)	0.6236 (11)	0.2228 (6)	0.064 (3)
H28	0.4027	0.6064	0.1856	0.077*
C29	0.0926 (8)	0.0672 (9)	0.3427 (5)	0.034 (2)
C30	0.0563 (8)	0.1458 (8)	0.4058 (4)	0.031 (2)
C31	0.1238 (9)	0.2727 (9)	0.4328 (5)	0.043 (2)
H31	0.1956	0.3129	0.4112	0.052*
C32	0.0865 (10)	0.3404 (11)	0.4910 (6)	0.060 (3)
H32	0.1310	0.4268	0.5074	0.072*
C33	−0.0139 (11)	0.2833 (13)	0.5246 (6)	0.069 (3)
H33	−0.0357	0.3295	0.5656	0.082*
C34	−0.0833 (14)	0.1591 (14)	0.4992 (7)	0.090 (4)
H34	−0.1546	0.1204	0.5217	0.108*
C35	−0.0472 (10)	0.0886 (10)	0.4387 (6)	0.063 (3)
H35	−0.0943	0.0029	0.4212	0.076*
C36	0.2001 (9)	0.0699 (8)	0.1802 (5)	0.036 (2)
C37	0.2514 (9)	0.0059 (8)	0.1209 (5)	0.040 (2)
C38	0.3468 (10)	−0.0487 (10)	0.1344 (6)	0.060 (3)
H38	0.3815	−0.0460	0.1842	0.072*
C39	0.3899 (14)	−0.1055 (13)	0.0763 (9)	0.097 (4)
H39	0.4526	−0.1435	0.0861	0.116*
C40	0.342 (2)	−0.1079 (14)	0.0027 (10)	0.109 (5)
H40	0.3763	−0.1423	−0.0373	0.131*
C41	0.2433 (19)	−0.0595 (15)	−0.0117 (7)	0.103 (5)
H41	0.2061	−0.0657	−0.0617	0.123*
C42	0.2011 (12)	−0.0039 (10)	0.0458 (6)	0.065 (3)
H42	0.1351	0.0300	0.0352	0.079*
C43	0.410 (3)	0.596 (3)	0.962 (2)	0.211 (14)
H43	0.3533	0.5326	0.9804	0.253*
C44	0.486 (3)	0.704 (2)	0.8626 (15)	0.210 (11)
H44A	0.4908	0.7890	0.8813	0.315*
H44B	0.4685	0.6839	0.8079	0.315*
H44C	0.5690	0.6944	0.8802	0.315*
C45	0.252 (3)	0.556 (2)	0.8505 (16)	0.214 (12)
H45A	0.2029	0.4992	0.8783	0.321*
H45B	0.2558	0.5102	0.8015	0.321*
H45C	0.2096	0.6168	0.8438	0.321*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.046 (4)	0.032 (4)	0.037 (5)	0.022 (4)	−0.004 (3)	0.012 (4)
N2	0.047 (5)	0.030 (4)	0.035 (4)	0.014 (4)	−0.007 (4)	0.015 (3)
N3	0.032 (4)	0.018 (4)	0.053 (5)	−0.001 (4)	0.006 (4)	0.001 (3)
N4	0.028 (4)	0.024 (4)	0.055 (5)	0.003 (4)	0.005 (4)	0.017 (3)
N5	0.055 (5)	0.021 (4)	0.036 (4)	0.013 (4)	0.014 (4)	0.009 (3)
N6	0.055 (5)	0.029 (4)	0.032 (4)	0.021 (4)	0.017 (4)	0.012 (3)
N7	0.137 (19)	0.131 (18)	0.30 (3)	0.011 (15)	0.05 (2)	0.01 (2)
O1	0.076 (5)	0.049 (4)	0.050 (4)	0.038 (4)	0.008 (3)	0.016 (3)
O2	0.046 (4)	0.033 (4)	0.058 (4)	0.007 (3)	−0.005 (3)	0.021 (3)
O3	0.048 (4)	0.026 (4)	0.068 (4)	0.006 (3)	0.014 (3)	0.004 (3)
O4	0.038 (4)	0.038 (4)	0.060 (4)	0.006 (3)	0.001 (3)	0.025 (3)
O5	0.051 (4)	0.028 (4)	0.062 (4)	0.006 (3)	0.020 (3)	0.003 (3)
O6	0.086 (5)	0.049 (4)	0.043 (4)	0.043 (4)	0.005 (3)	0.011 (3)
O7	0.176 (15)	0.178 (17)	0.33 (2)	0.041 (14)	0.001 (15)	0.025 (16)
C1	0.048 (6)	0.021 (5)	0.038 (6)	0.006 (5)	0.002 (4)	0.011 (4)
C2	0.048 (6)	0.022 (5)	0.049 (6)	0.012 (5)	−0.008 (5)	0.016 (5)
C3	0.088 (8)	0.046 (7)	0.044 (7)	0.028 (6)	−0.015 (6)	−0.005 (5)
C4	0.113 (10)	0.069 (9)	0.042 (7)	0.032 (8)	−0.014 (7)	0.002 (6)
C5	0.089 (9)	0.095 (10)	0.057 (9)	0.025 (8)	−0.014 (7)	0.031 (7)
C6	0.065 (8)	0.096 (10)	0.103 (11)	0.051 (7)	0.012 (7)	0.044 (8)
C7	0.059 (7)	0.069 (8)	0.053 (6)	0.028 (6)	−0.002 (5)	0.018 (5)
C8	0.047 (6)	0.019 (5)	0.033 (5)	0.016 (5)	0.005 (5)	0.006 (4)
C9	0.037 (6)	0.034 (6)	0.033 (5)	0.017 (5)	−0.001 (4)	0.004 (4)
C10	0.040 (5)	0.046 (6)	0.035 (5)	0.012 (5)	−0.004 (4)	0.013 (5)
C11	0.054 (7)	0.068 (7)	0.055 (6)	0.016 (6)	−0.004 (5)	0.037 (6)
C12	0.066 (8)	0.083 (9)	0.062 (7)	0.026 (7)	−0.009 (6)	0.036 (7)
C13	0.068 (8)	0.068 (9)	0.087 (9)	0.014 (7)	−0.037 (7)	0.024 (7)
C14	0.046 (6)	0.052 (7)	0.064 (7)	0.004 (6)	−0.013 (6)	0.009 (6)
C15	0.029 (5)	0.026 (6)	0.045 (5)	0.006 (5)	−0.003 (4)	0.010 (5)
C16	0.026 (5)	0.037 (6)	0.039 (5)	0.002 (5)	−0.001 (4)	0.008 (5)
C17	0.031 (6)	0.045 (7)	0.084 (8)	−0.012 (5)	0.002 (5)	0.012 (6)
C18	0.069 (8)	0.056 (8)	0.100 (10)	−0.033 (7)	0.014 (8)	0.018 (7)
C19	0.056 (8)	0.068 (9)	0.079 (9)	−0.021 (7)	−0.003 (7)	0.019 (7)
C20	0.061 (8)	0.103 (12)	0.093 (9)	−0.022 (8)	0.033 (7)	0.021 (9)
C21	0.046 (7)	0.077 (9)	0.066 (7)	−0.004 (6)	0.008 (6)	−0.001 (6)
C22	0.026 (5)	0.023 (5)	0.036 (5)	0.008 (4)	0.004 (4)	0.010 (4)
C23	0.026 (5)	0.033 (5)	0.045 (5)	0.008 (4)	0.010 (5)	0.011 (5)
C24	0.034 (6)	0.075 (8)	0.065 (7)	0.005 (6)	0.006 (5)	0.027 (6)
C25	0.049 (7)	0.068 (8)	0.081 (8)	−0.013 (6)	0.003 (6)	0.010 (7)
C26	0.050 (8)	0.067 (9)	0.097 (9)	−0.005 (6)	0.018 (7)	0.013 (8)
C27	0.070 (9)	0.083 (10)	0.104 (10)	−0.006 (8)	0.012 (8)	0.053 (8)
C28	0.041 (6)	0.074 (8)	0.079 (7)	0.005 (6)	0.009 (5)	0.046 (7)
C29	0.038 (5)	0.029 (6)	0.039 (5)	0.015 (5)	0.007 (4)	0.010 (5)
C30	0.039 (5)	0.030 (6)	0.026 (5)	0.013 (4)	0.006 (4)	0.009 (4)
C31	0.045 (6)	0.042 (7)	0.040 (5)	0.015 (5)	0.010 (4)	0.001 (5)
C32	0.061 (7)	0.057 (7)	0.058 (7)	0.023 (6)	0.014 (6)	−0.004 (6)
C33	0.076 (8)	0.072 (9)	0.057 (7)	0.031 (7)	0.025 (6)	−0.009 (6)
C34	0.109 (10)	0.088 (11)	0.098 (9)	0.045 (9)	0.073 (8)	0.031 (8)
C35	0.067 (7)	0.054 (7)	0.070 (7)	0.015 (6)	0.040 (6)	0.012 (6)
C36	0.053 (6)	0.021 (5)	0.038 (6)	0.011 (5)	0.014 (5)	0.013 (4)
C37	0.045 (6)	0.035 (6)	0.038 (6)	0.007 (5)	0.013 (4)	0.008 (4)
C38	0.063 (7)	0.076 (8)	0.052 (6)	0.038 (6)	0.022 (5)	0.010 (6)
C39	0.116 (11)	0.104 (11)	0.093 (11)	0.063 (9)	0.048 (9)	0.017 (9)
C40	0.160 (15)	0.077 (11)	0.089 (13)	0.028 (11)	0.070 (11)	0.008 (9)
C41	0.165 (15)	0.091 (11)	0.060 (9)	0.050 (11)	0.024 (9)	0.022 (8)
C42	0.115 (9)	0.050 (7)	0.045 (7)	0.039 (7)	0.028 (7)	0.016 (5)
C43	0.16 (3)	0.13 (2)	0.31 (4)	0.020 (19)	0.04 (3)	0.00 (3)
C44	0.17 (2)	0.14 (2)	0.29 (3)	0.017 (17)	0.06 (2)	0.00 (2)
C45	0.15 (2)	0.14 (2)	0.30 (3)	0.001 (17)	0.02 (2)	0.01 (2)

Geometric parameters (Å, º) top

N1—C1	1.344 (10)	C17—C18	1.369 (14)
N1—N2	1.385 (9)	C17—H17	0.930
N1—H1	0.860	C18—C19	1.298 (16)
N2—C8	1.342 (10)	C18—H18	0.930
N2—H2	0.860	C19—C20	1.366 (17)
N3—C15	1.313 (10)	C19—H19	0.930
N3—N4	1.385 (9)	C20—C21	1.405 (15)
N3—H3	0.860	C20—H20	0.930
N4—C22	1.353 (10)	C21—H21	0.930
N4—H4	0.860	C22—C23	1.472 (12)
N5—C29	1.333 (10)	C23—C24	1.352 (12)
N5—N6	1.372 (9)	C23—C28	1.363 (12)
N5—H5	0.860	C24—C25	1.366 (14)
N6—C36	1.352 (10)	C24—H24	0.930
N6—H6	0.860	C25—C26	1.337 (16)
N7—C43	1.38 (3)	C25—H25	0.930
N7—C45	1.39 (3)	C26—C27	1.357 (15)
N7—C44	1.45 (3)	C26—H26	0.930
O1—C1	1.226 (10)	C27—C28	1.365 (15)
O2—C8	1.215 (9)	C27—H27	0.930
O3—C15	1.219 (10)	C28—H28	0.930
O4—C22	1.229 (9)	C29—C30	1.492 (11)
O5—C29	1.247 (10)	C30—C35	1.357 (12)
O6—C36	1.227 (10)	C30—C31	1.375 (11)
O7—C43	1.45 (3)	C31—C32	1.369 (13)
C1—C2	1.480 (12)	C31—H31	0.930
C2—C7	1.356 (13)	C32—C33	1.341 (14)
C2—C3	1.372 (13)	C32—H32	0.930
C3—C4	1.337 (14)	C33—C34	1.350 (16)
C3—H3A	0.930	C33—H33	0.930
C4—C5	1.345 (16)	C34—C35	1.408 (15)
C4—H4A	0.930	C34—H34	0.930
C5—C6	1.368 (16)	C35—H35	0.930
C5—H5A	0.930	C36—C37	1.450 (12)
C6—C7	1.412 (15)	C37—C42	1.381 (13)
C6—H6A	0.930	C37—C38	1.383 (13)
C7—H7	0.930	C38—C39	1.340 (15)
C8—C9	1.497 (12)	C38—H38	0.930
C9—C14	1.351 (12)	C39—C40	1.369 (19)
C9—C10	1.380 (12)	C39—H39	0.930
C10—C11	1.386 (12)	C40—C41	1.37 (2)
C10—H10	0.930	C40—H40	0.930
C11—C12	1.369 (14)	C41—C42	1.321 (18)
C11—H11	0.930	C41—H41	0.930
C12—C13	1.347 (15)	C42—H42	0.930
C12—H12	0.930	C43—H43	0.930
C13—C14	1.389 (14)	C44—H44A	0.960
C13—H13	0.930	C44—H44B	0.960
C14—H14	0.930	C44—H44C	0.960
C15—C16	1.488 (12)	C45—H45A	0.960
C16—C17	1.335 (13)	C45—H45B	0.960
C16—C21	1.354 (12)	C45—H45C	0.960

C1—N1—N2	118.9 (7)	C16—C21—C20	120.7 (11)
C1—N1—H1	120.5	C16—C21—H21	119.7
N2—N1—H1	120.5	C20—C21—H21	119.7
C8—N2—N1	120.5 (7)	O4—C22—N4	121.0 (7)
C8—N2—H2	119.7	O4—C22—C23	122.2 (7)
N1—N2—H2	119.7	N4—C22—C23	116.8 (8)
C15—N3—N4	119.7 (6)	C24—C23—C28	118.5 (9)
C15—N3—H3	120.1	C24—C23—C22	117.9 (8)
N4—N3—H3	120.1	C28—C23—C22	123.6 (8)
C22—N4—N3	120.8 (7)	C23—C24—C25	119.5 (10)
C22—N4—H4	119.6	C23—C24—H24	120.2
N3—N4—H4	119.6	C25—C24—H24	120.2
C29—N5—N6	119.9 (7)	C26—C25—C24	122.7 (11)
C29—N5—H5	120.1	C26—C25—H25	118.6
N6—N5—H5	120.1	C24—C25—H25	118.6
C36—N6—N5	119.5 (7)	C25—C26—C27	117.6 (11)
C36—N6—H6	120.2	C25—C26—H26	121.2
N5—N6—H6	120.2	C27—C26—H26	121.2
C43—N7—C45	118 (3)	C26—C27—C28	120.9 (12)
C43—N7—C44	118 (3)	C26—C27—H27	119.6
C45—N7—C44	125 (3)	C28—C27—H27	119.6
O1—C1—N1	121.5 (8)	C23—C28—C27	120.7 (10)
O1—C1—C2	121.5 (8)	C23—C28—H28	119.7
N1—C1—C2	117.0 (8)	C27—C28—H28	119.7
C7—C2—C3	118.9 (8)	O5—C29—N5	122.2 (7)
C7—C2—C1	124.6 (9)	O5—C29—C30	120.9 (8)
C3—C2—C1	116.4 (9)	N5—C29—C30	116.9 (8)
C4—C3—C2	121.2 (11)	C35—C30—C31	118.7 (8)
C4—C3—H3A	119.4	C35—C30—C29	118.3 (8)
C2—C3—H3A	119.4	C31—C30—C29	123.0 (8)
C3—C4—C5	121.2 (11)	C32—C31—C30	120.7 (9)
C3—C4—H4A	119.4	C32—C31—H31	119.6
C5—C4—H4A	119.4	C30—C31—H31	119.6
C4—C5—C6	119.9 (11)	C33—C32—C31	120.5 (10)
C4—C5—H5A	120.0	C33—C32—H32	119.7
C6—C5—H5A	120.0	C31—C32—H32	119.7
C5—C6—C7	118.9 (11)	C32—C33—C34	120.4 (10)
C5—C6—H6A	120.5	C32—C33—H33	119.8
C7—C6—H6A	120.5	C34—C33—H33	119.8
C2—C7—C6	119.7 (10)	C33—C34—C35	119.6 (10)
C2—C7—H7	120.2	C33—C34—H34	120.2
C6—C7—H7	120.2	C35—C34—H34	120.2
O2—C8—N2	121.4 (7)	C30—C35—C34	120.0 (10)
O2—C8—C9	122.3 (8)	C30—C35—H35	120.0
N2—C8—C9	116.3 (8)	C34—C35—H35	120.0
C14—C9—C10	120.1 (8)	O6—C36—N6	120.5 (8)
C14—C9—C8	117.3 (9)	O6—C36—C37	121.5 (8)
C10—C9—C8	122.6 (8)	N6—C36—C37	118.0 (9)
C9—C10—C11	120.1 (8)	C42—C37—C38	117.1 (9)
C9—C10—H10	120.0	C42—C37—C36	118.7 (9)
C11—C10—H10	120.0	C38—C37—C36	124.2 (9)
C12—C11—C10	119.8 (10)	C39—C38—C37	120.6 (11)
C12—C11—H11	120.1	C39—C38—H38	119.7
C10—C11—H11	120.1	C37—C38—H38	119.7
C13—C12—C11	119.0 (9)	C38—C39—C40	120.4 (13)
C13—C12—H12	120.5	C38—C39—H39	119.8
C11—C12—H12	120.5	C40—C39—H39	119.8
C12—C13—C14	122.2 (10)	C41—C40—C39	119.7 (13)
C12—C13—H13	118.9	C41—C40—H40	120.2
C14—C13—H13	118.9	C39—C40—H40	120.2
C9—C14—C13	118.8 (10)	C42—C41—C40	119.5 (13)
C9—C14—H14	120.6	C42—C41—H41	120.3
C13—C14—H14	120.6	C40—C41—H41	120.3
O3—C15—N3	123.3 (7)	C41—C42—C37	122.6 (12)
O3—C15—C16	120.3 (8)	C41—C42—H42	118.7
N3—C15—C16	116.4 (8)	C37—C42—H42	118.7
C17—C16—C21	117.0 (9)	N7—C43—O7	113 (4)
C17—C16—C15	124.9 (8)	N7—C43—H43	123.4
C21—C16—C15	118.0 (8)	O7—C43—H43	123.4
C16—C17—C18	122.8 (11)	N7—C44—H44A	109.5
C16—C17—H17	118.6	N7—C44—H44B	109.5
C18—C17—H17	118.6	H44A—C44—H44B	109.5
C19—C18—C17	120.7 (12)	N7—C44—H44C	109.5
C19—C18—H18	119.6	H44A—C44—H44C	109.5
C17—C18—H18	119.6	H44B—C44—H44C	109.5
C18—C19—C20	119.9 (11)	N7—C45—H45A	109.5
C18—C19—H19	120.1	N7—C45—H45B	109.5
C20—C19—H19	120.1	H45A—C45—H45B	109.5
C19—C20—C21	118.8 (12)	N7—C45—H45C	109.5
C19—C20—H20	120.6	H45A—C45—H45C	109.5
C21—C20—H20	120.6	H45B—C45—H45C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5ⁱ	0.86	2.04	2.846 (9)	156
N6—H6···O2ⁱⁱ	0.86	2.01	2.826 (9)	157
N2—H2···O3	0.86	2.00	2.800 (9)	155
N3—H3···O6	0.86	1.96	2.778 (10)	158
N4—H4···O1	0.86	1.92	2.743 (9)	160
N5—H5···O4	0.86	1.97	2.774 (9)	155

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

Experimental details

Crystal data
Chemical formula	3C₁₄H₁₂N₂O₂·C₃H₇NO
M_r	793.86
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	10.7666 (12), 11.4615 (13), 18.100 (2)
α, β, γ (°)	100.127 (2), 96.084 (2), 108.382 (3)
V (Å³)	2055.2 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.32 × 0.27

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.957, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	6846, 4163, 2487
R_int	0.075
θ_max (°)	20.8
(sin θ/λ)_max (Å⁻¹)	0.500

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.120, 0.359, 1.14
No. of reflections	4163
No. of parameters	534
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.52

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5ⁱ	0.86	2.04	2.846 (9)	155.9
N6—H6···O2ⁱⁱ	0.86	2.01	2.826 (9)	157.4
N2—H2···O3	0.86	2.00	2.800 (9)	155.1
N3—H3···O6	0.86	1.96	2.778 (10)	157.5
N4—H4···O1	0.86	1.92	2.743 (9)	159.6
N5—H5···O4	0.86	1.97	2.774 (9)	155.2

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

Acknowledgements

This project was supported by the Foundation of Liaocheng University (grant No. X071013).

References

Galema, S. A. (1997). Chem. Soc. Rev. 26, 233–238. CrossRef CAS Web of Science Google Scholar
Shanmuga Sundara Raj, S., Yamin, B. M., Boshaala, A. M. A., Tarafder, M. T. H., Crouse, K. A. & Fun, H.-K. (2000). Acta Cryst. C56, 1011–1012. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Systems, Inc., Madison, Wisconsin, USA. Google Scholar