Crystal structures of N-(pyridin-2-ylmeth­yl)pyrazine-2-carboxamide (monoclinic polymorph) and N-(pyridin-4-ylmeth­yl)pyrazine-2-carboxamide

The title molecules, HL1 and HL2, differ in their conformation with the pyridine ring being inclined to the pyrazine ring by 61.34 (6) and 84.33 (12)°, respectively. The crystal packing is also slightly different, with molecules of HL1 linked by pairs of N—H...N hydrogen bonds, forming inversion dimers, while for HL2 molecules are linked by N—H...N and C—H...N hydrogen bonds, forming chains along [010].

Key indicators

Structure: HL1

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.032
• wR factor = 0.088
• Data-to-parameter ratio = 13.1

Structure: HL2

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.054
• wR factor = 0.127
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Datablock: HL1



Alert level A
PLAT015_ALERT_5_A No _shelx_hkl_file record in SHELXL20xy CIF ...      Please Do !

Alert level C
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          7 Why ?
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          6 Note

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         15 Note

   1 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
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check




Datablock: HL2



Alert level A
PLAT015_ALERT_5_A No _shelx_hkl_file record in SHELXL20xy CIF ...      Please Do !

Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      6.415 Check

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT910_ALERT_3_G Missing # of FCF Reflections Below Th(Min) .....          1 Why ?

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

---

Computing details

Data collection: EXPOSE in IPDSI (Stoe & Cie, 1997) for HL1; STADI4 (Stoe & Cie, 1997) for HL2. Cell refinement: CELL in IPDSI (Stoe & Cie, 1997) for HL1; STADI4 (Stoe & Cie, 1997) for HL2. Data reduction: INTEGRATE in IPDSI (Stoe & Cie, 1997) for HL1; X-RED (Stoe & Cie, 1997) for HL2. For both compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

(HL1) N-(Pyridin-2-ylmethyl)pyrazine-2-carboxamide

Crystal data

C11H10N4O	F(000) = 448
Mr = 214.23	Dx = 1.395 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 4.1527 (4) Å	Cell parameters from 6532 reflections
b = 20.4629 (18) Å	θ = 2.0–25.9°
c = 12.0106 (11) Å	µ = 0.10 mm^−1
β = 91.461 (11)°	T = 153 K
V = 1020.28 (16) Å^3	Block, colourless
Z = 4	0.50 × 0.40 × 0.35 mm

Data collection

Stoe IPDS 1 diffractometer	1548 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
Plane graphite monochromator	θmax = 25.9°, θmin = 2.0°
φ rotation scans	h = −5→5
7822 measured reflections	k = −25→25
1958 independent reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: mixed
wR(F^2) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0539P)^2 + 0.0704P] where P = (Fo^2 + 2Fc^2)/3
1958 reflections	(Δ/σ)max < 0.001
149 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

Experimental. Spectrosopic data for HL1: ¹H NMR (400 MHz, DMSO-d6; code Hh/NH, Hl/C3, Hn/C1, Hm/C2, Hb/C11, Hd/C9, He/C8, Hc/C10, Hg/C6): 9.50 (t, 1H, Jhg = 6.0, Hh); 9.23 (d, 1H, Jlm = 1.5, Hl); 8.91 (d, 1H, Jnm = 2.5, Hn); 8.78 (dd, 1H, Jmn = 2.5, Jml = 1.5, Hm); 8.53 (ddd, 1H, Jbc = 4.8, Jbd = 1.8, Jbe = 0.8, Hb); 7.76 (td, 1H, Jdc = 7.7, Jdb = 1.8, Hd); 7.35 (d, 1H, Jed = 7.9, He); 7.28 (dd, 1H, Jcd = 7.7, Jcb = 4.8, Hc); 4.64 (d, 2H, Jgh = 6.0, He). ¹³C NMR (400 MHz, DMSO-d6): 163.9, 158.6, 149.7, 148.6, 145.5, 144.4, 144.3, 137.6, 123.1, 121.9, 45.0. IR (KBr pellet, cm^-1): 3248 (m), 3066 (w), 3018 (w), 2949 (w), 1669 (versus), 1593 (m), 1570 (m), 1517 (versus), 1478 (m), 1462 (s), 1440 (s), 1423 (s), 1389 (s), 1350 (m), 1320 (m), 1287 (s), 1250 (m), 1221 (m), 1168 (s), 1148 (m), 1103 (m), 1055 (m), 1021 (s), 1000 (m), 975 (m), 870 (m), 840 (w), 776 (m), 753 (s), 707 (m), 634 (m), 611 (m), 528 (m), 444 (m).

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.

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

	x	y	z	Uiso*/Ueq
N1	0.7345 (3)	0.30055 (5)	0.42625 (8)	0.0260 (2)
N2	0.7780 (3)	0.16917 (5)	0.49125 (9)	0.0343 (3)
N3	0.4290 (2)	0.38859 (5)	0.55546 (8)	0.0224 (2)
H3N	0.514 (4)	0.3982 (7)	0.4892 (13)	0.037 (4)*
N4	0.5222 (3)	0.53951 (5)	0.66045 (8)	0.0293 (3)
O1	0.3074 (2)	0.30857 (4)	0.67870 (7)	0.0344 (2)
C1	0.6100 (3)	0.27903 (5)	0.52119 (9)	0.0215 (3)
C2	0.6318 (3)	0.21416 (6)	0.55317 (10)	0.0287 (3)
H2	0.5401	0.2011	0.6213	0.034*
C3	0.9010 (3)	0.19099 (6)	0.39702 (10)	0.0305 (3)
H3	1.0071	0.1609	0.3501	0.037*
C4	0.8800 (3)	0.25567 (6)	0.36486 (10)	0.0290 (3)
H4	0.9724	0.2686	0.2967	0.035*
C5	0.4355 (3)	0.32697 (6)	0.59277 (9)	0.0229 (3)
C6	0.2435 (3)	0.43932 (6)	0.60984 (10)	0.0263 (3)
H6A	0.0627	0.4186	0.6488	0.032*
H6B	0.1503	0.4688	0.5522	0.032*
C7	0.4391 (3)	0.47934 (5)	0.69249 (9)	0.0219 (3)
C8	0.5266 (3)	0.45428 (6)	0.79615 (10)	0.0271 (3)
H8	0.4640	0.4113	0.8163	0.033*
C9	0.7051 (3)	0.49220 (6)	0.86977 (10)	0.0312 (3)
H9	0.7682	0.4757	0.9410	0.037*
C10	0.7906 (4)	0.55455 (6)	0.83801 (11)	0.0350 (3)
H10	0.9115	0.5822	0.8870	0.042*
C11	0.6957 (4)	0.57556 (6)	0.73353 (11)	0.0376 (3)
H11	0.7569	0.6183	0.7117	0.045*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0305 (6)	0.0246 (5)	0.0231 (5)	−0.0011 (4)	0.0045 (4)	−0.0005 (4)
N2	0.0434 (7)	0.0239 (5)	0.0356 (6)	0.0046 (5)	0.0043 (5)	−0.0006 (4)
N3	0.0263 (5)	0.0207 (5)	0.0201 (5)	0.0007 (4)	0.0020 (4)	−0.0008 (4)
N4	0.0412 (7)	0.0219 (5)	0.0249 (5)	0.0016 (4)	0.0022 (4)	0.0007 (4)
O1	0.0454 (6)	0.0295 (5)	0.0288 (5)	0.0000 (4)	0.0154 (4)	0.0036 (4)
C1	0.0219 (6)	0.0217 (6)	0.0208 (5)	−0.0024 (5)	−0.0014 (4)	−0.0008 (4)
C2	0.0369 (8)	0.0247 (6)	0.0246 (6)	0.0006 (5)	0.0032 (5)	0.0016 (5)
C3	0.0327 (7)	0.0275 (6)	0.0313 (7)	0.0029 (5)	0.0039 (5)	−0.0067 (5)
C4	0.0321 (7)	0.0305 (6)	0.0246 (6)	−0.0012 (5)	0.0056 (5)	−0.0028 (5)
C5	0.0233 (6)	0.0242 (6)	0.0211 (6)	−0.0021 (5)	−0.0003 (5)	−0.0001 (4)
C6	0.0244 (7)	0.0248 (6)	0.0296 (6)	0.0062 (5)	−0.0010 (5)	−0.0021 (5)
C7	0.0210 (6)	0.0213 (6)	0.0235 (6)	0.0055 (5)	0.0057 (4)	−0.0011 (4)
C8	0.0275 (7)	0.0258 (6)	0.0281 (6)	0.0005 (5)	0.0024 (5)	0.0046 (5)
C9	0.0333 (7)	0.0374 (7)	0.0228 (6)	0.0044 (6)	−0.0001 (5)	0.0010 (5)
C10	0.0420 (8)	0.0310 (7)	0.0317 (7)	−0.0002 (6)	−0.0034 (6)	−0.0093 (5)
C11	0.0554 (9)	0.0207 (6)	0.0366 (7)	−0.0046 (6)	−0.0022 (6)	−0.0006 (5)

Geometric parameters (Å, º)

N1—C4	1.3323 (16)	C3—H3	0.9500
N1—C1	1.3386 (15)	C4—H4	0.9500
N2—C3	1.3307 (17)	C6—C7	1.5082 (16)
N2—C2	1.3387 (16)	C6—H6A	0.9900
N3—C5	1.3382 (15)	C6—H6B	0.9900
N3—C6	1.4570 (15)	C7—C8	1.3865 (17)
N3—H3N	0.901 (16)	C8—C9	1.3784 (18)
N4—C7	1.3379 (15)	C8—H8	0.9500
N4—C11	1.3422 (17)	C9—C10	1.3806 (18)
O1—C5	1.2319 (14)	C9—H9	0.9500
C1—C2	1.3842 (16)	C10—C11	1.3745 (19)
C1—C5	1.5028 (16)	C10—H10	0.9500
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.3808 (18)
C4—N1—C1	115.80 (10)	N3—C6—C7	113.57 (9)
C3—N2—C2	115.53 (11)	N3—C6—H6A	108.9
C5—N3—C6	121.84 (10)	C7—C6—H6A	108.9
C5—N3—H3N	119.7 (9)	N3—C6—H6B	108.9
C6—N3—H3N	117.7 (9)	C7—C6—H6B	108.9
C7—N4—C11	117.12 (10)	H6A—C6—H6B	107.7
N1—C1—C2	121.86 (11)	N4—C7—C8	122.34 (11)
N1—C1—C5	118.36 (10)	N4—C7—C6	116.69 (10)
C2—C1—C5	119.76 (10)	C8—C7—C6	120.97 (11)
N2—C2—C1	122.19 (11)	C9—C8—C7	119.49 (11)
N2—C2—H2	118.9	C9—C8—H8	120.3
C1—C2—H2	118.9	C7—C8—H8	120.3
N2—C3—C4	122.47 (11)	C8—C9—C10	118.73 (11)
N2—C3—H3	118.8	C8—C9—H9	120.6
C4—C3—H3	118.8	C10—C9—H9	120.6
N1—C4—C3	122.14 (11)	C11—C10—C9	118.14 (12)
N1—C4—H4	118.9	C11—C10—H10	120.9
C3—C4—H4	118.9	C9—C10—H10	120.9
O1—C5—N3	124.27 (11)	N4—C11—C10	124.17 (12)
O1—C5—C1	120.30 (10)	N4—C11—H11	117.9
N3—C5—C1	115.43 (10)	C10—C11—H11	117.9
C4—N1—C1—C2	0.03 (17)	C2—C1—C5—N3	179.54 (11)
C4—N1—C1—C5	−178.51 (11)	C5—N3—C6—C7	95.48 (13)
C3—N2—C2—C1	0.06 (19)	C11—N4—C7—C8	−0.18 (18)
N1—C1—C2—N2	−0.1 (2)	C11—N4—C7—C6	179.86 (11)
C5—C1—C2—N2	178.43 (11)	N3—C6—C7—N4	104.41 (12)
C2—N2—C3—C4	0.03 (19)	N3—C6—C7—C8	−75.55 (14)
C1—N1—C4—C3	0.05 (18)	N4—C7—C8—C9	0.12 (18)
N2—C3—C4—N1	−0.1 (2)	C6—C7—C8—C9	−179.92 (11)
C6—N3—C5—O1	−5.16 (19)	C7—C8—C9—C10	0.33 (19)
C6—N3—C5—C1	174.05 (10)	C8—C9—C10—C11	−0.7 (2)
N1—C1—C5—O1	177.36 (11)	C7—N4—C11—C10	−0.2 (2)
C2—C1—C5—O1	−1.21 (18)	C9—C10—C11—N4	0.6 (2)
N1—C1—C5—N3	−1.88 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···N1	0.901 (16)	2.332 (15)	2.7136 (15)	105.4 (11)
N3—H3N···N4^i	0.901 (16)	2.206 (16)	2.9929 (14)	145.6 (13)
C3—H3···O1^ii	0.95	2.51	3.1544 (15)	125
C4—H4···O1^ii	0.95	2.56	3.1748 (15)	123
C10—H10···N2^iii	0.95	2.62	3.5678 (17)	174

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

(HL2) N-(Pyridin-4-ylmethyl)pyrazine-2-carboxamide

Crystal data

C11H10N4O	F(000) = 448
Mr = 214.23	Dx = 1.371 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.8564 (14) Å	Cell parameters from 20 reflections
b = 11.1841 (11) Å	θ = 10.4–17.6°
c = 6.9122 (10) Å	µ = 0.09 mm^−1
β = 104.356 (14)°	T = 293 K
V = 1037.7 (2) Å^3	Block, colourless
Z = 4	0.38 × 0.30 × 0.19 mm

Data collection

Stoe AED2 four-circle diffractometer	Rint = 0.032
Radiation source: fine-focus sealed tube	θmax = 25.5°, θmin = 2.4°
Plane graphite monochromator	h = −16→16
2θ/ω scans	k = −13→0
4132 measured reflections	l = −8→8
1937 independent reflections	2 standard reflections every 60 min
1198 reflections with I > 2σ(I)	intensity decay: 2%

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.054	w = 1/[σ^2(Fo^2) + (0.0426P)^2 + 0.1904P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.127	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.17 e Å^−3
1937 reflections	Δρmin = −0.16 e Å^−3
150 parameters	Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.014 (2)

Special details

Experimental. Spectroscopic data for HL2: ¹H NMR (400 MHz, DMSO-d6; code Hh/NH, Hl/C3, Hn/C1, Hm/C2, Hb/C11, Hd/C9, Ha/C11/, He/C8, Hg/C6): 9.63 (t, 1H, Jhg = 6.3, Hh); 9.21 (d, 1H, Jlm = 1.5, Hl); 8.90 (d, 1H, Jnm = 2.5, Hn); 8.77 (dd, 1H, Jmn = 2.5, Jml = 1.5, Hm); 8.49 (dd, 2H, Jba = 4.4, Jbe = 1.6, Hb = Hd); 7.31 (dd, 2H, Jab = 4.4, Jad = 1.6, Ha = He); 4.54 (d, 2H, Jgh = 6.3, Hg). ¹³C NMR (400 MHz, DMSO-d6): 164.2, 150.4, 149.0, 148.5, 145.4, 144.5, 144.3, 123.0, 42.4. IR (KBr pellet, cm^-1): 3366 (versus), 3089 (s), 3050 (m), 3031 (s), 2967 (m), 2935 (s), 1966 (w), 1924 (w), 1834 (w), 1674 (versus), 1634 (s), 1602 (versus), 1585 (s), 1564 (s) 1526 (versus), 1467 (versus), 1429 (versus), 1415 (versus), 1399 (versus), 1359 (s), 1329 (s), 1288 (versus), 1240 (m), 1216 (versus), 1167 (s), 1155 (s), 1059 (versus), 1025 (versus), 1020 (versus), 993 (s), 981 (s), 968 (s), 887 (m), 870 (s), 842 (s), 832 (s), 804 (versus), 775 (s), 731 (m), 652 (versus), 608 (s), 517 (s), 479 (m), 445 (versus), 411 (m).

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.

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

	x	y	z	Uiso*/Ueq
O1	0.32038 (14)	0.28041 (15)	0.2248 (3)	0.0618 (6)
N1	0.52051 (15)	0.08089 (17)	0.2297 (3)	0.0456 (6)
N2	0.61838 (17)	0.29856 (19)	0.2153 (3)	0.0530 (6)
N3	0.32823 (16)	0.0787 (2)	0.2548 (3)	0.0495 (6)
H3N	0.367 (2)	0.022 (2)	0.251 (4)	0.057 (9)*
N4	0.04496 (18)	−0.1046 (2)	−0.2659 (4)	0.0677 (7)
C1	0.47371 (18)	0.1855 (2)	0.2255 (3)	0.0389 (6)
C2	0.5226 (2)	0.2927 (2)	0.2174 (4)	0.0477 (7)
H2	0.4870	0.3635	0.2132	0.057*
C3	0.6641 (2)	0.1935 (2)	0.2189 (4)	0.0531 (7)
H3	0.7309	0.1925	0.2166	0.064*
C4	0.61612 (19)	0.0861 (2)	0.2258 (4)	0.0510 (7)
H4	0.6515	0.0153	0.2279	0.061*
C5	0.36661 (19)	0.1863 (2)	0.2342 (4)	0.0442 (6)
C6	0.22661 (19)	0.0590 (2)	0.2660 (4)	0.0548 (7)
H6A	0.1972	0.1350	0.2877	0.066*
H6B	0.2267	0.0080	0.3795	0.066*
C7	0.16399 (17)	0.0020 (2)	0.0798 (4)	0.0431 (6)
C8	0.1571 (2)	0.0498 (2)	−0.1071 (4)	0.0534 (7)
H8	0.1922	0.1187	−0.1216	0.064*
C9	0.0979 (2)	−0.0052 (3)	−0.2711 (5)	0.0652 (8)
H9	0.0943	0.0291	−0.3953	0.078*
C10	0.0528 (2)	−0.1497 (2)	−0.0853 (5)	0.0627 (8)
H10	0.0171	−0.2188	−0.0752	0.075*
C11	0.11055 (19)	−0.1010 (2)	0.0887 (4)	0.0517 (7)
H11	0.1134	−0.1374	0.2110	0.062*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0615 (13)	0.0417 (11)	0.0868 (15)	0.0116 (10)	0.0272 (11)	−0.0013 (10)
N1	0.0459 (13)	0.0334 (12)	0.0586 (14)	0.0012 (10)	0.0149 (10)	−0.0024 (10)
N2	0.0553 (15)	0.0427 (14)	0.0610 (15)	−0.0100 (11)	0.0144 (11)	−0.0006 (11)
N3	0.0421 (14)	0.0421 (14)	0.0663 (16)	−0.0008 (11)	0.0170 (11)	−0.0043 (11)
N4	0.0590 (16)	0.0684 (18)	0.0749 (19)	0.0011 (13)	0.0148 (14)	−0.0111 (15)
C1	0.0441 (14)	0.0323 (13)	0.0399 (14)	−0.0006 (11)	0.0101 (11)	−0.0028 (11)
C2	0.0560 (18)	0.0325 (15)	0.0531 (17)	0.0008 (12)	0.0109 (13)	−0.0023 (12)
C3	0.0488 (17)	0.0505 (16)	0.0607 (17)	−0.0050 (14)	0.0149 (13)	0.0007 (14)
C4	0.0496 (16)	0.0406 (15)	0.0646 (18)	0.0044 (13)	0.0174 (13)	−0.0019 (13)
C5	0.0501 (16)	0.0376 (14)	0.0447 (15)	0.0009 (13)	0.0117 (12)	−0.0045 (12)
C6	0.0471 (16)	0.0585 (18)	0.0625 (19)	−0.0012 (13)	0.0206 (14)	−0.0040 (14)
C7	0.0321 (13)	0.0416 (14)	0.0582 (18)	0.0048 (11)	0.0162 (12)	0.0016 (12)
C8	0.0442 (15)	0.0551 (17)	0.0646 (19)	−0.0022 (13)	0.0204 (14)	0.0059 (15)
C9	0.0589 (19)	0.084 (2)	0.056 (2)	0.0091 (17)	0.0214 (16)	0.0066 (17)
C10	0.0530 (18)	0.0444 (16)	0.092 (3)	−0.0008 (14)	0.0204 (17)	−0.0063 (17)
C11	0.0457 (15)	0.0439 (15)	0.0674 (19)	0.0043 (13)	0.0179 (13)	0.0087 (14)

Geometric parameters (Å, º)

O1—C5	1.225 (3)	C3—H3	0.9300
N1—C4	1.333 (3)	C4—H4	0.9300
N1—C1	1.334 (3)	C6—C7	1.504 (3)
N2—C3	1.332 (3)	C6—H6A	0.9700
N2—C2	1.333 (3)	C6—H6B	0.9700
N3—C5	1.338 (3)	C7—C11	1.379 (3)
N3—C6	1.446 (3)	C7—C8	1.379 (4)
N3—H3N	0.83 (3)	C8—C9	1.369 (4)
N4—C10	1.325 (4)	C8—H8	0.9300
N4—C9	1.337 (4)	C9—H9	0.9300
C1—C2	1.385 (3)	C10—C11	1.381 (4)
C1—C5	1.500 (3)	C10—H10	0.9300
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.379 (3)
C4—N1—C1	116.2 (2)	N3—C6—C7	112.4 (2)
C3—N2—C2	115.2 (2)	N3—C6—H6A	109.1
C5—N3—C6	124.1 (2)	C7—C6—H6A	109.1
C5—N3—H3N	113.8 (19)	N3—C6—H6B	109.1
C6—N3—H3N	121.9 (19)	C7—C6—H6B	109.1
C10—N4—C9	115.1 (3)	H6A—C6—H6B	107.9
N1—C1—C2	121.3 (2)	C11—C7—C8	116.9 (3)
N1—C1—C5	119.0 (2)	C11—C7—C6	121.2 (2)
C2—C1—C5	119.6 (2)	C8—C7—C6	121.9 (2)
N2—C2—C1	122.8 (2)	C9—C8—C7	119.3 (3)
N2—C2—H2	118.6	C9—C8—H8	120.3
C1—C2—H2	118.6	C7—C8—H8	120.3
N2—C3—C4	122.5 (3)	N4—C9—C8	124.8 (3)
N2—C3—H3	118.7	N4—C9—H9	117.6
C4—C3—H3	118.7	C8—C9—H9	117.6
N1—C4—C3	121.9 (2)	N4—C10—C11	124.4 (3)
N1—C4—H4	119.0	N4—C10—H10	117.8
C3—C4—H4	119.0	C11—C10—H10	117.8
O1—C5—N3	124.2 (2)	C7—C11—C10	119.5 (3)
O1—C5—C1	120.9 (2)	C7—C11—H11	120.3
N3—C5—C1	114.9 (2)	C10—C11—H11	120.3
C4—N1—C1—C2	0.1 (3)	C2—C1—C5—N3	−175.8 (2)
C4—N1—C1—C5	−178.6 (2)	C5—N3—C6—C7	108.0 (3)
C3—N2—C2—C1	0.9 (4)	N3—C6—C7—C11	126.7 (3)
N1—C1—C2—N2	−0.7 (4)	N3—C6—C7—C8	−53.3 (3)
C5—C1—C2—N2	178.0 (2)	C11—C7—C8—C9	0.8 (4)
C2—N2—C3—C4	−0.5 (4)	C6—C7—C8—C9	−179.2 (2)
C1—N1—C4—C3	0.3 (4)	C10—N4—C9—C8	0.0 (4)
N2—C3—C4—N1	−0.1 (4)	C7—C8—C9—N4	−0.3 (4)
C6—N3—C5—O1	0.9 (4)	C9—N4—C10—C11	−0.1 (4)
C6—N3—C5—C1	−179.9 (2)	C8—C7—C11—C10	−0.9 (4)
N1—C1—C5—O1	−177.8 (2)	C6—C7—C11—C10	179.1 (2)
C2—C1—C5—O1	3.4 (4)	N4—C10—C11—C7	0.6 (4)
N1—C1—C5—N3	2.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···N1	0.83 (3)	2.27 (3)	2.713 (3)	114 (2)
N3—H3N···N2^i	0.83 (3)	2.52 (3)	3.214 (3)	142 (2)
C2—H2···N1^ii	0.93	2.47	3.315 (3)	151
C8—H8···O1^iii	0.93	2.55	3.373 (3)	148

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