6-Methyl-N-(2-methyl­phen­yl)-3-phenyl-1,6-dihydro-1,2,4,5-tetra­zine-1-carbox­amide. Corrigendum

Xu, F.; Hu, W.

doi:10.1107/S160053680903013X

addenda and errata

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page e15

https://doi.org/10.1107/S160053680903013X

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6-Methyl-N-(2-methylphenyl)-3-phenyl-1,6-dihydro-1,2,4,5-tetrazine-1-carboxamide. Corrigendum

Feng Xu ^a and Weixiao Hu ^a ^*

^aCollege of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310032, People's Republic of China
^*Correspondence e-mail: huyang@mail.hz.zj.cn

(Received 1 July 2009; accepted 29 July 2009; online 9 January 2010)

The formula of the title compound in the paper by Xu & Hu [Acta Cryst. (2008 ), E64, o1432] is corrected.

In the paper by Xu & Hu [Acta Cryst. (2008 ), E64, o1432], the chemical formula is corrected and the structure has been rerefined to include a missing H atom. The Crystal data, Data collection and Refinement sections are updated together with the hydrogen-bond data.

2. Experimental

2.1.1. Crystal data

C₁₇H₁₇N₅O
M_r = 307.36
Monoclinic, P 2₁ /c
a = 13.941 (6) Å
b = 5.675 (2) Å
c = 20.614 (8) Å
β = 102.055 (6)°
V = 1594.8 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.12 × 0.10 × 0.06 mm

2.1.2. Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.990, T_max = 0.995
7095 measured reflections
3280 independent reflections
1899 reflections with I > 2σ(I)
R_int = 0.087

2.1.3. Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.170
S = 0.91
3280 reflections
215 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Oⁱ	0.93	2.56	3.385 (3)	148
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053680903013X/lx9060sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680903013X/lx9060Isup2.hkl

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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).

6-Methyl-N-(2-methylphenyl)-3-phenyl-1,6-dihydro-1,2,4,5-tetrazine-1-carboxamide top

Crystal data top

C₁₇H₁₇N₅O	F(000) = 644
M_r = 307.36	D_x = 1.276 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 378–380 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.941 (6) Å	Cell parameters from 742 reflections
b = 5.675 (2) Å	θ = 3.2–24.8°
c = 20.614 (8) Å	µ = 0.08 mm⁻¹
β = 102.055 (6)°	T = 293 K
V = 1594.8 (11) Å³	Prism, red
Z = 4	0.12 × 0.10 × 0.06 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3280 independent reflections
Radiation source: fine-focus sealed tube	1899 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.087
Detector resolution: 10.0 pixels mm^-1	θ_max = 26.5°, θ_min = 1.5°
φ and ω scans	h = −17→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −6→7
T_min = 0.990, T_max = 0.995	l = −25→25
7095 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)] = 0.064	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.170	w = 1/[σ²(F_o²) + (0.0932P)²] where P = (F_o² + 2F_c²)/3
S = 0.91	(Δ/σ)_max < 0.001
3280 reflections	Δρ_max = 0.54 e Å⁻³
215 parameters	Δρ_min = −0.31 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.021 (4)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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 > 2sigma(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
O	0.79549 (13)	0.2358 (3)	0.73526 (8)	0.0685 (5)
N1	0.82379 (14)	0.4541 (3)	0.64939 (9)	0.0552 (5)
N2	0.79315 (13)	0.5181 (3)	0.58485 (9)	0.0522 (5)
N3	0.88534 (17)	0.8632 (4)	0.61618 (12)	0.0685 (6)
N4	0.91853 (17)	0.7948 (4)	0.67409 (12)	0.0724 (6)
N5	0.68918 (15)	0.2115 (4)	0.63448 (10)	0.0598 (6)
H5N	0.6759 (17)	0.282 (4)	0.5967 (12)	0.054 (6)*
C1	0.91906 (18)	0.5354 (4)	0.68427 (11)	0.0587 (6)
C2	0.83633 (17)	0.7032 (4)	0.56768 (11)	0.0526 (6)
C3	0.82173 (17)	0.7755 (4)	0.49788 (12)	0.0542 (6)
C4	0.77371 (19)	0.6256 (5)	0.44798 (12)	0.0644 (7)
H4	0.7490	0.4824	0.4592	0.077*
C5	0.7624 (2)	0.6873 (6)	0.38197 (14)	0.0813 (9)
H5	0.7307	0.5853	0.3491	0.098*
C6	0.7975 (2)	0.8971 (6)	0.36496 (16)	0.0825 (9)
H6	0.7889	0.9392	0.3205	0.099*
C7	0.8452 (3)	1.0452 (6)	0.41287 (18)	0.0876 (10)
H7	0.8701	1.1870	0.4009	0.105*
C8	0.8571 (2)	0.9862 (5)	0.47985 (15)	0.0788 (8)
H8	0.8889	1.0897	0.5123	0.095*
C9	0.76906 (18)	0.2904 (4)	0.67787 (11)	0.0535 (6)
C10	0.61865 (18)	0.0506 (4)	0.64801 (11)	0.0559 (6)
C11	0.6437 (2)	−0.1223 (5)	0.69669 (13)	0.0724 (8)
H11	0.7077	−0.1329	0.7210	0.087*
C12	0.5740 (3)	−0.2762 (6)	0.70856 (15)	0.0883 (10)
H12	0.5905	−0.3910	0.7412	0.106*
C13	0.4807 (3)	−0.2619 (6)	0.67292 (18)	0.0928 (11)
H13	0.4330	−0.3646	0.6817	0.111*
C14	0.4564 (2)	−0.0944 (6)	0.62345 (16)	0.0817 (9)
H14	0.3926	−0.0891	0.5987	0.098*
C15	0.52429 (19)	0.0652 (4)	0.60974 (12)	0.0601 (7)
C16	1.00241 (18)	0.4238 (5)	0.65920 (13)	0.0658 (7)
H16A	1.0013	0.2564	0.6656	0.099*
H16B	1.0636	0.4865	0.6832	0.099*
H16C	0.9955	0.4575	0.6128	0.099*
C17	0.4969 (3)	0.2482 (6)	0.55605 (17)	0.0790 (8)
H17A	0.431 (3)	0.232 (5)	0.5290 (16)	0.102 (10)*
H17B	0.543 (2)	0.223 (5)	0.5212 (15)	0.092 (9)*
H17C	0.511 (3)	0.408 (7)	0.5726 (16)	0.107 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O	0.0755 (12)	0.0808 (13)	0.0475 (10)	−0.0050 (9)	0.0090 (8)	0.0014 (7)
N1	0.0491 (11)	0.0653 (12)	0.0486 (10)	−0.0056 (10)	0.0039 (8)	0.0001 (8)
N2	0.0469 (11)	0.0556 (11)	0.0529 (11)	−0.0018 (9)	0.0077 (8)	0.0026 (8)
N3	0.0682 (14)	0.0511 (12)	0.0823 (15)	−0.0009 (10)	0.0067 (12)	−0.0101 (10)
N4	0.0740 (15)	0.0636 (14)	0.0742 (15)	−0.0012 (11)	0.0030 (12)	−0.0181 (11)
N5	0.0537 (12)	0.0737 (14)	0.0501 (12)	−0.0109 (10)	0.0064 (10)	0.0102 (9)
C1	0.0521 (15)	0.0578 (14)	0.0616 (14)	−0.0068 (12)	0.0015 (11)	−0.0095 (10)
C2	0.0488 (13)	0.0424 (12)	0.0658 (14)	0.0002 (11)	0.0098 (11)	−0.0017 (9)
C3	0.0427 (13)	0.0485 (13)	0.0722 (15)	0.0022 (10)	0.0137 (11)	0.0085 (10)
C4	0.0610 (16)	0.0681 (16)	0.0637 (15)	−0.0068 (13)	0.0123 (12)	0.0116 (11)
C5	0.0763 (19)	0.101 (2)	0.0649 (16)	−0.0060 (17)	0.0117 (14)	0.0133 (14)
C6	0.0736 (19)	0.095 (2)	0.0832 (19)	0.0109 (18)	0.0271 (16)	0.0321 (17)
C7	0.094 (2)	0.0653 (19)	0.115 (3)	−0.0012 (17)	0.047 (2)	0.0308 (17)
C8	0.084 (2)	0.0583 (17)	0.098 (2)	−0.0070 (15)	0.0271 (16)	0.0097 (14)
C9	0.0520 (14)	0.0604 (14)	0.0484 (13)	0.0014 (11)	0.0111 (11)	−0.0033 (10)
C10	0.0597 (15)	0.0570 (14)	0.0548 (13)	−0.0092 (12)	0.0210 (11)	−0.0027 (10)
C11	0.0846 (19)	0.0703 (17)	0.0646 (15)	−0.0100 (15)	0.0209 (14)	0.0082 (12)
C12	0.119 (3)	0.080 (2)	0.0732 (18)	−0.028 (2)	0.035 (2)	0.0027 (14)
C13	0.106 (3)	0.089 (2)	0.097 (2)	−0.042 (2)	0.053 (2)	−0.0174 (18)
C14	0.0644 (18)	0.090 (2)	0.096 (2)	−0.0193 (16)	0.0277 (16)	−0.0261 (17)
C15	0.0571 (16)	0.0621 (15)	0.0645 (14)	−0.0049 (12)	0.0205 (12)	−0.0115 (11)
C16	0.0513 (15)	0.0635 (16)	0.0779 (16)	−0.0031 (12)	0.0029 (12)	0.0007 (11)
C17	0.064 (2)	0.078 (2)	0.087 (2)	0.0031 (17)	−0.0032 (17)	−0.0037 (16)

Geometric parameters (Å, º) top

O—C9	1.204 (3)	C7—C8	1.397 (4)
N1—N2	1.359 (3)	C7—H7	0.9300
N1—C9	1.406 (3)	C8—H8	0.9300
N1—C1	1.447 (3)	C10—C15	1.388 (4)
N2—C2	1.296 (3)	C10—C11	1.395 (4)
N3—N4	1.249 (3)	C11—C12	1.366 (4)
N3—C2	1.416 (3)	C11—H11	0.9300
N4—C1	1.487 (3)	C12—C13	1.356 (5)
N5—C9	1.351 (3)	C12—H12	0.9300
N5—C10	1.412 (3)	C13—C14	1.383 (5)
N5—H5N	0.86 (2)	C13—H13	0.9300
C1—C16	1.506 (3)	C14—C15	1.381 (4)
C2—C3	1.469 (3)	C14—H14	0.9300
C3—C8	1.374 (4)	C15—C17	1.508 (4)
C3—C4	1.394 (4)	C16—H16A	0.9600
C4—C5	1.382 (4)	C16—H16B	0.9600
C4—H4	0.9300	C16—H16C	0.9600
C5—C6	1.361 (4)	C17—H17A	0.98 (4)
C5—H5	0.9300	C17—H17B	1.07 (3)
C6—C7	1.360 (5)	C17—H17C	0.97 (4)
C6—H6	0.9300

N2—N1—C9	119.9 (2)	O—C9—N5	127.3 (2)
N2—N1—C1	118.0 (2)	O—C9—N1	119.9 (2)
C9—N1—C1	121.7 (2)	N5—C9—N1	112.8 (2)
C2—N2—N1	114.5 (2)	C15—C10—C11	121.1 (2)
N4—N3—C2	120.2 (2)	C15—C10—N5	117.7 (2)
N3—N4—C1	115.6 (2)	C11—C10—N5	121.1 (2)
C9—N5—C10	126.5 (2)	C12—C11—C10	119.9 (3)
C9—N5—H5N	115.8 (16)	C12—C11—H11	120.1
C10—N5—H5N	117.0 (16)	C10—C11—H11	120.1
N1—C1—N4	105.6 (2)	C13—C12—C11	120.2 (3)
N1—C1—C16	112.9 (2)	C13—C12—H12	119.9
N4—C1—C16	110.4 (2)	C11—C12—H12	119.9
N2—C2—N3	120.7 (2)	C12—C13—C14	120.0 (3)
N2—C2—C3	121.1 (2)	C12—C13—H13	120.0
N3—C2—C3	117.4 (2)	C14—C13—H13	120.0
C8—C3—C4	118.4 (2)	C15—C14—C13	122.0 (3)
C8—C3—C2	121.6 (2)	C15—C14—H14	119.0
C4—C3—C2	120.0 (2)	C13—C14—H14	119.0
C5—C4—C3	120.7 (2)	C14—C15—C10	116.9 (2)
C5—C4—H4	119.7	C14—C15—C17	121.5 (3)
C3—C4—H4	119.7	C10—C15—C17	121.5 (2)
C6—C5—C4	120.2 (3)	C1—C16—H16A	109.5
C6—C5—H5	119.9	C1—C16—H16B	109.5
C4—C5—H5	119.9	H16A—C16—H16B	109.5
C7—C6—C5	120.1 (3)	C1—C16—H16C	109.5
C7—C6—H6	120.0	H16A—C16—H16C	109.5
C5—C6—H6	120.0	H16B—C16—H16C	109.5
C6—C7—C8	120.6 (3)	C15—C17—H17A	114.5 (19)
C6—C7—H7	119.7	C15—C17—H17B	107.6 (16)
C8—C7—H7	119.7	H17A—C17—H17B	104 (2)
C3—C8—C7	120.1 (3)	C15—C17—H17C	112.6 (19)
C3—C8—H8	120.0	H17A—C17—H17C	113 (3)
C7—C8—H8	120.0	H17B—C17—H17C	105 (3)

C9—N1—N2—C2	166.3 (2)	C4—C3—C8—C7	−0.5 (4)
C1—N1—N2—C2	−21.5 (3)	C2—C3—C8—C7	177.5 (3)
C2—N3—N4—C1	10.6 (3)	C6—C7—C8—C3	1.0 (5)
N2—N1—C1—N4	52.3 (3)	C10—N5—C9—O	1.3 (4)
C9—N1—C1—N4	−135.5 (2)	C10—N5—C9—N1	−178.6 (2)
N2—N1—C1—C16	−68.4 (3)	N2—N1—C9—O	−179.1 (2)
C9—N1—C1—C16	103.7 (2)	C1—N1—C9—O	8.9 (3)
N3—N4—C1—N1	−45.4 (3)	N2—N1—C9—N5	0.8 (3)
N3—N4—C1—C16	77.0 (3)	C1—N1—C9—N5	−171.2 (2)
N1—N2—C2—N3	−19.4 (3)	C9—N5—C10—C15	152.7 (2)
N1—N2—C2—C3	171.32 (19)	C9—N5—C10—C11	−29.4 (4)
N4—N3—C2—N2	25.8 (3)	C15—C10—C11—C12	−2.0 (4)
N4—N3—C2—C3	−164.6 (2)	N5—C10—C11—C12	−179.8 (2)
N2—C2—C3—C8	171.8 (2)	C10—C11—C12—C13	0.3 (4)
N3—C2—C3—C8	2.2 (3)	C11—C12—C13—C14	1.4 (5)
N2—C2—C3—C4	−10.2 (4)	C12—C13—C14—C15	−1.6 (5)
N3—C2—C3—C4	−179.8 (2)	C13—C14—C15—C10	0.0 (4)
C8—C3—C4—C5	0.3 (4)	C13—C14—C15—C17	−179.5 (3)
C2—C3—C4—C5	−177.7 (2)	C11—C10—C15—C14	1.8 (3)
C3—C4—C5—C6	−0.5 (4)	N5—C10—C15—C14	179.7 (2)
C4—C5—C6—C7	1.0 (5)	C11—C10—C15—C17	−178.7 (3)
C5—C6—C7—C8	−1.2 (5)	N5—C10—C15—C17	−0.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Oⁱ	0.93	2.56	3.385 (3)	148

Symmetry code: (i) x, −y+3/2, z−1/2.

References

Xu, F. & Hu, W. (2008). Acta Cryst. E64, o1432. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar

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