Syntheses and crystal structure of 4-[(pyridin-3-yl)diazen­yl]morpholine and 1-[(pyridin-3-yl)diazen­yl]-1,2,3,4-tetra­hydro­quinoline

The title triazene derivatives were synthesized using a diazo­nium inter­mediate that was obtained from 3-amino­pyridine and isoamyl nitrite.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.038
• wR factor = 0.104
• Data-to-parameter ratio = 19.4

Structure: II

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.034
• wR factor = 0.094
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Datablock: ss069



Alert level G
PLAT398_ALERT_2_G Deviating  C-O-C   Angle From 120 for O1       .      109.6 Degree
PLAT480_ALERT_4_G Long H...A H-Bond Reported H2A      ..N4       .       2.67 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H2B      ..N4       .       2.68 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H7       ..N3       .       2.70 Ang.
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          6 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: ss080_2021ncs0191



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         14 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          5 Note

Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         13 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 9.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: Authors Seynabou Sokhna, Insa Seck, Samba Fama Ndoye and Lalla A\"icha Ba intervened in the synthesis and purification of molecules. The authors Marc Presse and Erwan Le Gall recorded the H and C NMR spectra and interpreted them. Authors Ibrahima El Hadj Thiam, Simon Coles and James Orton recorded the XRD and resolved the structures The authors Issa Samb, Matar Seck coordinated the work and participated with Mohamed Gaye in writing and correcting the article

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

For both structures, data collection: CrysAlis PRO (Rigaku OD, 2020); cell refinement: CrysAlis PRO (Rigaku OD, 2020); data reduction: CrysAlis PRO (Rigaku OD, 2020); program(s) used to solve structure: olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

4-[(Pyridin-3-yl)diazenyl]morpholine (I)

Crystal data

C9H12N4O	F(000) = 408
Mr = 192.23	Dx = 1.342 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
a = 5.6889 (3) Å	Cell parameters from 10944 reflections
b = 8.3058 (4) Å	θ = 2.0–36.0°
c = 20.3063 (8) Å	µ = 0.09 mm^−1
β = 97.370 (4)°	T = 100 K
V = 951.56 (8) Å^3	(cut) irregular block, colourless
Z = 4	0.26 × 0.16 × 0.14 mm

Data collection

Rigaku FRE+ equipped with VHF Varimax confocal mirrors and an AFC12 goniometer and HyPix 6000 detector diffractometer	2280 reflections with I > 2σ(I)
Detector resolution: 10 pixels mm^-1	Rint = 0.032
profile data from ω–scans	θmax = 28.7°, θmin = 2.0°
Absorption correction: analytical (CrysAlisPro; Rigaku OD, 2020)	h = −7→7
Tmin = 0.187, Tmax = 1.000	k = −11→11
47217 measured reflections	l = −27→27
2464 independent reflections

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.0504P)^2 + 0.3578P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2464 reflections	Δρmax = 0.39 e Å^−3
127 parameters	Δρmin = −0.20 e Å^−3
0 restraints

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C2	0.62623 (19)	0.79887 (13)	0.51038 (5)	0.0239 (2)
H2A	0.569056	0.840631	0.465513	0.029*
H2B	0.731480	0.881059	0.533953	0.029*
C1	0.41701 (18)	0.76924 (14)	0.54796 (5)	0.0245 (2)
H1A	0.334523	0.872026	0.554175	0.029*
H1B	0.303268	0.695170	0.522423	0.029*
C4	0.65470 (18)	0.55810 (12)	0.61131 (5)	0.0220 (2)
H4A	0.561459	0.464763	0.592211	0.026*
H4B	0.724736	0.530281	0.657060	0.026*
C3	0.84953 (18)	0.59792 (14)	0.56928 (5)	0.0240 (2)
H3A	0.953897	0.681815	0.591964	0.029*
H3B	0.946831	0.500602	0.564925	0.029*
C5	0.25737 (17)	0.66881 (12)	0.75890 (5)	0.0195 (2)
C6	0.05135 (18)	0.76118 (13)	0.75068 (5)	0.0224 (2)
H6	0.000875	0.814030	0.709820	0.027*
C7	−0.07817 (18)	0.77375 (13)	0.80398 (5)	0.0248 (2)
H7	−0.220732	0.834549	0.800057	0.030*
C8	0.00371 (19)	0.69618 (14)	0.86306 (5)	0.0258 (2)
H8	−0.086330	0.706044	0.899152	0.031*
N1	0.50202 (15)	0.69888 (11)	0.61229 (4)	0.02041 (19)
N2	0.36372 (14)	0.72537 (10)	0.65955 (4)	0.01964 (18)
N3	0.40585 (14)	0.63392 (10)	0.70942 (4)	0.01969 (18)
O1	0.75628 (13)	0.65370 (9)	0.50469 (3)	0.02197 (17)
N4	0.20195 (17)	0.60850 (12)	0.87196 (4)	0.0274 (2)
C9	0.32349 (18)	0.59528 (13)	0.82007 (5)	0.0239 (2)
H9	0.463560	0.531802	0.825257	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0285 (5)	0.0252 (5)	0.0193 (4)	0.0003 (4)	0.0080 (4)	0.0021 (4)
C1	0.0244 (5)	0.0300 (5)	0.0202 (4)	0.0050 (4)	0.0068 (4)	0.0045 (4)
C4	0.0239 (5)	0.0249 (5)	0.0182 (4)	0.0031 (4)	0.0070 (3)	0.0021 (4)
C3	0.0213 (4)	0.0339 (5)	0.0175 (4)	0.0037 (4)	0.0051 (3)	0.0012 (4)
C5	0.0211 (4)	0.0214 (4)	0.0169 (4)	−0.0034 (3)	0.0054 (3)	−0.0031 (3)
C6	0.0250 (5)	0.0250 (5)	0.0174 (4)	0.0003 (4)	0.0038 (4)	−0.0003 (4)
C7	0.0237 (5)	0.0264 (5)	0.0254 (5)	0.0014 (4)	0.0075 (4)	−0.0040 (4)
C8	0.0306 (5)	0.0286 (5)	0.0206 (5)	−0.0037 (4)	0.0126 (4)	−0.0036 (4)
N1	0.0214 (4)	0.0245 (4)	0.0167 (4)	0.0018 (3)	0.0074 (3)	0.0006 (3)
N2	0.0195 (4)	0.0225 (4)	0.0176 (4)	−0.0012 (3)	0.0048 (3)	−0.0005 (3)
N3	0.0200 (4)	0.0220 (4)	0.0175 (4)	0.0002 (3)	0.0037 (3)	−0.0005 (3)
O1	0.0243 (4)	0.0279 (4)	0.0147 (3)	0.0010 (3)	0.0064 (3)	−0.0008 (3)
N4	0.0344 (5)	0.0304 (5)	0.0185 (4)	0.0003 (4)	0.0073 (3)	0.0015 (3)
C9	0.0253 (5)	0.0265 (5)	0.0203 (5)	0.0017 (4)	0.0048 (4)	0.0000 (4)

Geometric parameters (Å, º)

C2—H2A	0.9900	C5—C6	1.3928 (14)
C2—H2B	0.9900	C5—N3	1.4230 (12)
C2—C1	1.5142 (14)	C5—C9	1.3918 (14)
C2—O1	1.4271 (12)	C6—H6	0.9500
C1—H1A	0.9900	C6—C7	1.3891 (13)
C1—H1B	0.9900	C7—H7	0.9500
C1—N1	1.4559 (12)	C7—C8	1.3886 (15)
C4—H4A	0.9900	C8—H8	0.9500
C4—H4B	0.9900	C8—N4	1.3351 (15)
C4—C3	1.5195 (13)	N1—N2	1.3350 (11)
C4—N1	1.4583 (13)	N2—N3	1.2640 (12)
C3—H3A	0.9900	N4—C9	1.3370 (13)
C3—H3B	0.9900	C9—H9	0.9500
C3—O1	1.4275 (12)
H2A—C2—H2B	108.1	O1—C3—H3B	109.2
C1—C2—H2A	109.5	C6—C5—N3	126.45 (9)
C1—C2—H2B	109.5	C9—C5—C6	118.40 (9)
O1—C2—H2A	109.5	C9—C5—N3	115.07 (9)
O1—C2—H2B	109.5	C5—C6—H6	121.0
O1—C2—C1	110.65 (8)	C7—C6—C5	118.06 (9)
C2—C1—H1A	109.9	C7—C6—H6	121.0
C2—C1—H1B	109.9	C6—C7—H7	120.5
H1A—C1—H1B	108.3	C8—C7—C6	119.05 (10)
N1—C1—C2	108.99 (8)	C8—C7—H7	120.5
N1—C1—H1A	109.9	C7—C8—H8	118.2
N1—C1—H1B	109.9	N4—C8—C7	123.64 (9)
H4A—C4—H4B	108.4	N4—C8—H8	118.2
C3—C4—H4A	110.1	C1—N1—C4	116.08 (8)
C3—C4—H4B	110.1	N2—N1—C1	114.85 (8)
N1—C4—H4A	110.1	N2—N1—C4	123.29 (8)
N1—C4—H4B	110.1	N3—N2—N1	114.09 (8)
N1—C4—C3	108.17 (8)	N2—N3—C5	112.00 (8)
C4—C3—H3A	109.2	C2—O1—C3	109.59 (7)
C4—C3—H3B	109.2	C8—N4—C9	116.83 (9)
H3A—C3—H3B	107.9	C5—C9—H9	118.0
O1—C3—C4	112.02 (8)	N4—C9—C5	124.01 (10)
O1—C3—H3A	109.2	N4—C9—H9	118.0
C2—C1—N1—C4	−51.60 (12)	C6—C7—C8—N4	−0.19 (17)
C2—C1—N1—N2	154.23 (9)	C7—C8—N4—C9	−0.74 (17)
C1—C2—O1—C3	−62.24 (10)	C8—N4—C9—C5	1.07 (16)
C1—N1—N2—N3	163.81 (9)	N1—C4—C3—O1	−54.11 (11)
C4—C3—O1—C2	61.98 (11)	N1—N2—N3—C5	178.85 (8)
C4—N1—N2—N3	11.73 (13)	N3—C5—C6—C7	176.15 (9)
C3—C4—N1—C1	50.22 (11)	N3—C5—C9—N4	−177.49 (10)
C3—C4—N1—N2	−158.00 (9)	O1—C2—C1—N1	55.81 (11)
C5—C6—C7—C8	0.81 (16)	C9—C5—C6—C7	−0.52 (15)
C6—C5—N3—N2	15.17 (14)	C9—C5—N3—N2	−168.06 (9)
C6—C5—C9—N4	−0.45 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···N4^i	0.99	2.67	3.5465 (14)	148
C2—H2B···N4^ii	0.99	2.68	3.5607 (14)	149
C3—H3A···N2^iii	0.99	2.57	3.4149 (13)	143
C7—H7···N3^iv	0.95	2.70	3.5168 (14)	145

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+1, y+1/2, −z+3/2; (iii) x+1, y, z; (iv) −x, y+1/2, −z+3/2.

1-[(Pyridin-3-yl)diazenyl]-1,2,3,4-tetrahydroquinoline (II)

Crystal data

C14H14N4	F(000) = 504
Mr = 238.29	Dx = 1.341 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
a = 15.4187 (2) Å	Cell parameters from 7895 reflections
b = 4.8130 (1) Å	θ = 2.0–36.0°
c = 15.9993 (3) Å	µ = 0.66 mm^−1
β = 96.115 (2)°	T = 100 K
V = 1180.56 (4) Å^3	(cut) irregular block, colourless
Z = 4	0.24 × 0.13 × 0.05 mm

Data collection

Rigaku FRE+ equipped with VHF Varimax confocal mirrors and an AFC12 goniometer and HyPix 6000 detector diffractometer	2010 reflections with I > 2σ(I)
Detector resolution: 10 pixels mm^-1	Rint = 0.023
profile data from ω–scans	θmax = 68.2°, θmin = 5.8°
Absorption correction: analytical (CrysAlisPro; Rigaku OD, 2020)	h = −18→17
Tmin = 0.187, Tmax = 1.000	k = −5→5
12295 measured reflections	l = −19→19
2142 independent reflections

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.0501P)^2 + 0.4022P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
2142 reflections	Δρmax = 0.22 e Å^−3
163 parameters	Δρmin = −0.19 e Å^−3
0 restraints

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.33530 (7)	0.4875 (2)	0.29703 (7)	0.0231 (3)
H1	0.279699	0.515484	0.266503	0.028*
C2	0.40405 (7)	0.6536 (2)	0.27811 (7)	0.0233 (3)
H2	0.394906	0.793635	0.236253	0.028*
C3	0.48588 (7)	0.6140 (2)	0.32051 (7)	0.0220 (3)
H3	0.533766	0.726560	0.308860	0.026*
C4	0.49636 (7)	0.4040 (2)	0.38099 (7)	0.0190 (3)
C5	0.42285 (7)	0.2529 (2)	0.39706 (7)	0.0222 (3)
H5	0.429669	0.115020	0.439742	0.027*
C6	0.72221 (7)	0.1768 (2)	0.51239 (7)	0.0207 (3)
H6A	0.709233	−0.014174	0.491712	0.025*
H6B	0.677731	0.229166	0.549830	0.025*
C7	0.81190 (7)	0.1837 (2)	0.56141 (7)	0.0226 (3)
H7A	0.815446	0.040449	0.606052	0.027*
H7B	0.821715	0.367432	0.588596	0.027*
C8	0.88195 (7)	0.1301 (2)	0.50322 (7)	0.0206 (3)
H8A	0.940339	0.144430	0.535296	0.025*
H8B	0.875328	−0.060116	0.479846	0.025*
C9	0.87424 (7)	0.3391 (2)	0.43253 (7)	0.0183 (3)
C10	0.79318 (7)	0.4562 (2)	0.40429 (7)	0.0181 (2)
C11	0.78684 (7)	0.6578 (2)	0.34059 (7)	0.0203 (3)
H11	0.732038	0.740036	0.322463	0.024*
C12	0.86059 (7)	0.7368 (2)	0.30415 (7)	0.0219 (3)
H12	0.856037	0.871900	0.260628	0.026*
C13	0.94119 (7)	0.6197 (2)	0.33081 (7)	0.0223 (3)
H13	0.991636	0.673085	0.305469	0.027*
C14	0.94718 (7)	0.4242 (2)	0.39480 (7)	0.0210 (3)
H14	1.002478	0.346140	0.413404	0.025*
N1	0.34340 (6)	0.2893 (2)	0.35634 (6)	0.0251 (2)
N2	0.57576 (6)	0.32558 (19)	0.42816 (6)	0.0196 (2)
N3	0.64124 (6)	0.43689 (19)	0.39911 (6)	0.0189 (2)
N4	0.71783 (6)	0.36903 (19)	0.44088 (6)	0.0187 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0221 (5)	0.0212 (6)	0.0257 (6)	0.0030 (5)	0.0019 (4)	−0.0037 (5)
C2	0.0265 (6)	0.0207 (6)	0.0233 (6)	0.0034 (5)	0.0050 (5)	0.0010 (5)
C3	0.0227 (5)	0.0193 (6)	0.0248 (6)	−0.0010 (4)	0.0066 (4)	−0.0001 (5)
C4	0.0207 (5)	0.0174 (5)	0.0194 (5)	0.0011 (4)	0.0048 (4)	−0.0039 (4)
C5	0.0232 (6)	0.0188 (6)	0.0252 (6)	0.0005 (5)	0.0048 (4)	0.0007 (5)
C6	0.0235 (6)	0.0191 (6)	0.0200 (5)	−0.0015 (4)	0.0052 (4)	0.0030 (4)
C7	0.0257 (6)	0.0220 (6)	0.0198 (5)	−0.0017 (5)	0.0016 (4)	0.0039 (5)
C8	0.0224 (5)	0.0157 (6)	0.0235 (6)	−0.0009 (4)	0.0012 (4)	0.0017 (4)
C9	0.0228 (5)	0.0129 (5)	0.0193 (5)	−0.0013 (4)	0.0023 (4)	−0.0028 (4)
C10	0.0209 (5)	0.0155 (5)	0.0180 (5)	−0.0033 (4)	0.0035 (4)	−0.0029 (4)
C11	0.0222 (5)	0.0178 (6)	0.0206 (5)	−0.0004 (4)	0.0008 (4)	0.0001 (4)
C12	0.0282 (6)	0.0190 (6)	0.0188 (6)	−0.0034 (5)	0.0033 (4)	0.0018 (4)
C13	0.0235 (6)	0.0210 (6)	0.0234 (6)	−0.0033 (5)	0.0076 (4)	−0.0013 (5)
C14	0.0210 (5)	0.0175 (6)	0.0250 (6)	0.0010 (4)	0.0041 (4)	−0.0021 (4)
N1	0.0225 (5)	0.0215 (5)	0.0314 (6)	−0.0004 (4)	0.0031 (4)	0.0000 (4)
N2	0.0204 (5)	0.0177 (5)	0.0213 (5)	−0.0014 (4)	0.0052 (4)	−0.0014 (4)
N3	0.0199 (5)	0.0171 (5)	0.0199 (5)	−0.0007 (4)	0.0033 (4)	−0.0020 (4)
N4	0.0192 (5)	0.0181 (5)	0.0188 (5)	−0.0011 (4)	0.0022 (4)	0.0021 (4)

Geometric parameters (Å, º)

C1—H1	0.9500	C7—C8	1.5212 (15)
C1—C2	1.3865 (16)	C8—H8A	0.9900
C1—N1	1.3422 (16)	C8—H8B	0.9900
C2—H2	0.9500	C8—C9	1.5090 (15)
C2—C3	1.3807 (16)	C9—C10	1.4013 (15)
C3—H3	0.9500	C9—C14	1.3934 (15)
C3—C4	1.3967 (16)	C10—C11	1.4030 (15)
C4—C5	1.3935 (16)	C10—N4	1.4189 (13)
C4—N2	1.4192 (14)	C11—H11	0.9500
C5—H5	0.9500	C11—C12	1.3851 (16)
C5—N1	1.3363 (15)	C12—H12	0.9500
C6—H6A	0.9900	C12—C13	1.3895 (16)
C6—H6B	0.9900	C13—H13	0.9500
C6—C7	1.5159 (15)	C13—C14	1.3864 (16)
C6—N4	1.4674 (14)	C14—H14	0.9500
C7—H7A	0.9900	N2—N3	1.2737 (13)
C7—H7B	0.9900	N3—N4	1.3341 (12)
C2—C1—H1	118.4	H8A—C8—H8B	108.2
N1—C1—H1	118.4	C9—C8—C7	109.95 (9)
N1—C1—C2	123.27 (10)	C9—C8—H8A	109.7
C1—C2—H2	120.2	C9—C8—H8B	109.7
C3—C2—C1	119.54 (11)	C10—C9—C8	120.41 (10)
C3—C2—H2	120.2	C14—C9—C8	121.19 (10)
C2—C3—H3	120.9	C14—C9—C10	118.39 (10)
C2—C3—C4	118.19 (10)	C9—C10—C11	120.21 (10)
C4—C3—H3	120.9	C9—C10—N4	119.30 (10)
C3—C4—N2	126.19 (10)	C11—C10—N4	120.49 (10)
C5—C4—C3	117.99 (10)	C10—C11—H11	120.0
C5—C4—N2	115.82 (10)	C12—C11—C10	119.91 (10)
C4—C5—H5	117.9	C12—C11—H11	120.0
N1—C5—C4	124.27 (11)	C11—C12—H12	119.8
N1—C5—H5	117.9	C11—C12—C13	120.47 (10)
H6A—C6—H6B	108.1	C13—C12—H12	119.8
C7—C6—H6A	109.5	C12—C13—H13	120.4
C7—C6—H6B	109.5	C14—C13—C12	119.27 (10)
N4—C6—H6A	109.5	C14—C13—H13	120.4
N4—C6—H6B	109.5	C9—C14—H14	119.1
N4—C6—C7	110.68 (9)	C13—C14—C9	121.74 (10)
C6—C7—H7A	109.6	C13—C14—H14	119.1
C6—C7—H7B	109.6	C5—N1—C1	116.69 (10)
C6—C7—C8	110.35 (9)	N3—N2—C4	111.49 (9)
H7A—C7—H7B	108.1	N2—N3—N4	114.08 (9)
C8—C7—H7A	109.6	C10—N4—C6	122.45 (9)
C8—C7—H7B	109.6	N3—N4—C6	120.64 (9)
C7—C8—H8A	109.7	N3—N4—C10	116.17 (9)
C7—C8—H8B	109.7
C1—C2—C3—C4	0.55 (17)	C9—C10—C11—C12	1.46 (16)
C2—C1—N1—C5	−1.03 (17)	C9—C10—N4—C6	5.22 (15)
C2—C3—C4—C5	−2.17 (16)	C9—C10—N4—N3	−164.91 (9)
C2—C3—C4—N2	177.24 (10)	C10—C9—C14—C13	0.03 (16)
C3—C4—C5—N1	2.38 (17)	C10—C11—C12—C13	−0.64 (17)
C3—C4—N2—N3	−11.45 (15)	C11—C10—N4—C6	−174.70 (10)
C4—C5—N1—C1	−0.77 (17)	C11—C10—N4—N3	15.17 (15)
C4—N2—N3—N4	−179.67 (8)	C11—C12—C13—C14	−0.47 (17)
C5—C4—N2—N3	167.97 (10)	C12—C13—C14—C9	0.78 (17)
C6—C7—C8—C9	56.49 (12)	C14—C9—C10—C11	−1.15 (16)
C7—C6—N4—C10	23.41 (14)	C14—C9—C10—N4	178.93 (9)
C7—C6—N4—N3	−166.89 (9)	N1—C1—C2—C3	1.13 (18)
C7—C8—C9—C10	−28.76 (14)	N2—C4—C5—N1	−177.08 (10)
C7—C8—C9—C14	150.10 (10)	N2—N3—N4—C6	1.30 (14)
C8—C9—C10—C11	177.73 (10)	N2—N3—N4—C10	171.63 (9)
C8—C9—C10—N4	−2.19 (15)	N4—C6—C7—C8	−53.93 (12)
C8—C9—C14—C13	−178.84 (10)	N4—C10—C11—C12	−178.62 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N3^i	0.95	2.58	3.3890 (14)	143

Symmetry code: (i) −x+3/2, y+1/2, −z+1/2.