Crystal structures and Hirshfeld surface analyses of two new tetra­kis-substituted pyrazines and a degredation product

The crystal structures of two new tetra­kis-substituted pyrazine compounds, 1,1′,1′′,1′′′-(pyrazine-2,3,5,6-tetra­yl)tetra­kis­(N,N-di­methyl­methanamine) and N,N′,N′′,N′′′-[pyrazine-2,3,5,6tetra­yltetra­kis­(methyl­ene)]tetra­kis­(N-methyl­aniline), and a degredation product, N,N′-[(6-phenyl-6,7-di­hydro-5H-pyrrolo­[3,4-b]pyrazine-2,3-di­yl)bis­(methyl­ene)]bis­(N-methyl­aniline), are described and have been analysed by Hirshfeld surface analysis.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.060
• wR factor = 0.154
• Data-to-parameter ratio = 17.3

Structure: II

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.049
• wR factor = 0.108
• Data-to-parameter ratio = 14.2

Structure: III

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.035
• wR factor = 0.079
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT242_ALERT_2_C Low    MainMol Ueq as Compared to Neighbors of         N2 Check
PLAT242_ALERT_2_C Low    MainMol Ueq as Compared to Neighbors of         N3 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.770 Check
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

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

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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




Datablock: II


Alert level C
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........  C<I>G</I> Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.892 Check
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT012_ALERT_1_G N.O.K.   _shelx_res_checksum Found in CIF ......     Please Check
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check

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

   4 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
   1 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




Datablock: III



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full value Low .      0.939 Why?

Author Response: With the STOE IPDS I, one-circle diffractometer, for the triclinic system often only 93% of the Ewald sphere is accessible.

Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections (too) Low ..        38% Check
PLAT911_ALERT_3_B Missing FCF Refl Between Thmin & STh/L=    0.600        255 Report

Alert level C
GOODF01_ALERT_2_C  The least squares goodness of fit parameter lies
            outside the range 0.80 <> 2.00
            Goodness of fit given =      0.682
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C18      --C19      .        6.0 s.u.
PLAT410_ALERT_2_C Short Intra H...H Contact  H21A     ..H23      .       1.98 Ang.
                                                      x,y,z  =      1_555 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     25.883 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.912 Check
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.013 Degree
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 Reflection(s) Below Theta(Min).          1 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          2 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check

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

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

---

Computing details

Data collection: STADI4 (Stoe & Cie, 1997) for (I), (II); EXPOSE in IPDS-I (Stoe & Cie, 2004) for (III). Cell refinement: STADI4 (Stoe & Cie, 1997) for (I), (II); CELL in IPDS-I (Stoe & Cie, 2004) for (III). Data reduction: X-RED (Stoe & Cie, 1997) for (I), (II); INTEGRATE in IPDS-I (Stoe & Cie, 2004) for (III). For all structures, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: SHELXL2018/3 (Sheldrick, 2015), PLATON (Spek, 2020) and publCIF (Westrip, 2010).

1,1',1'',1'''-(Pyrazine-2,3,5,6-tetrayl)tetrakis(N,N-dimethylmethanamine) (I)

Crystal data

C16H32N6	F(000) = 340
Mr = 308.47	Dx = 1.045 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.7577 (14) Å	Cell parameters from 22 reflections
b = 10.348 (2) Å	θ = 12.6–18.1°
c = 9.9118 (16) Å	µ = 0.07 mm^−1
β = 101.663 (15)°	T = 293 K
V = 980.2 (3) Å^3	Block, colourless
Z = 2	0.53 × 0.53 × 0.26 mm

Data collection

Stoe–Siemens AED2, 4-circle diffractometer	Rint = 0.055
Radiation source: fine-focus sealed tube	θmax = 25.5°, θmin = 2.7°
Plane graphite monochromator	h = −11→11
ω/\2q scans	k = 0→12
3347 measured reflections	l = −11→11
1818 independent reflections	2 standard reflections every 60 min
1111 reflections with I > 2σ(I)	intensity decay: 1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.060	H-atom parameters constrained
wR(F^2) = 0.154	w = 1/[σ^2(Fo^2) + (0.0488P)^2 + 0.2847P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
1818 reflections	Δρmax = 0.15 e Å^−3
105 parameters	Δρmin = −0.12 e Å^−3
0 restraints	Extinction correction: (SHELXL2018/3; Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.043 (7)

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
N1	0.07379 (18)	0.10665 (19)	0.46684 (19)	0.0504 (5)
N2	0.2065 (2)	−0.0663 (2)	0.2414 (2)	0.0657 (7)
N3	0.1836 (2)	0.1754 (2)	0.8033 (2)	0.0699 (7)
C1	0.0393 (2)	0.0085 (2)	0.3779 (2)	0.0465 (6)
C2	0.0345 (2)	0.0981 (2)	0.5885 (2)	0.0476 (6)
C3	0.0864 (3)	0.0171 (3)	0.2426 (2)	0.0576 (7)
H3A	0.009971	−0.008061	0.168567	0.069*
H3B	0.111131	0.105746	0.226663	0.069*
C4	0.2207 (4)	−0.0957 (4)	0.1004 (3)	0.1046 (12)
H4A	0.234545	−0.016958	0.053752	0.157*
H4B	0.137243	−0.137698	0.052395	0.157*
H4C	0.299513	−0.151713	0.102710	0.157*
C5	0.3335 (3)	−0.0092 (4)	0.3188 (3)	0.0979 (12)
H5C	0.409862	−0.068297	0.321975	0.147*
H5B	0.322027	0.009064	0.410892	0.147*
H5A	0.352858	0.069624	0.275133	0.147*
C6	0.0739 (3)	0.2095 (2)	0.6863 (3)	0.0615 (7)
H6A	0.105348	0.281127	0.637289	0.074*
H6B	−0.008203	0.237656	0.719505	0.074*
C7	0.3174 (3)	0.1604 (4)	0.7623 (4)	0.1168 (15)
H7A	0.346508	0.242054	0.731787	0.175*
H7B	0.308288	0.098709	0.688686	0.175*
H7C	0.386012	0.130348	0.839465	0.175*
C8	0.1949 (4)	0.2720 (3)	0.9118 (3)	0.1000 (12)
H8A	0.107852	0.277166	0.942547	0.150*
H8B	0.215925	0.354560	0.876707	0.150*
H8C	0.268255	0.248005	0.987590	0.150*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0471 (11)	0.0513 (12)	0.0535 (12)	0.0003 (9)	0.0121 (9)	0.0005 (10)
N2	0.0654 (14)	0.0752 (16)	0.0629 (14)	0.0117 (12)	0.0279 (11)	0.0066 (12)
N3	0.0630 (14)	0.0758 (16)	0.0663 (14)	−0.0068 (12)	0.0021 (11)	−0.0189 (12)
C1	0.0433 (12)	0.0490 (14)	0.0465 (13)	0.0037 (11)	0.0076 (10)	0.0006 (12)
C2	0.0420 (12)	0.0478 (14)	0.0522 (14)	0.0030 (11)	0.0076 (10)	−0.0032 (11)
C3	0.0597 (15)	0.0629 (17)	0.0520 (14)	0.0059 (13)	0.0152 (12)	0.0041 (12)
C4	0.130 (3)	0.117 (3)	0.081 (2)	0.032 (2)	0.056 (2)	0.002 (2)
C5	0.0565 (17)	0.145 (3)	0.096 (2)	0.001 (2)	0.0259 (17)	0.019 (2)
C6	0.0660 (17)	0.0529 (15)	0.0666 (16)	−0.0012 (13)	0.0157 (13)	−0.0089 (13)
C7	0.060 (2)	0.154 (4)	0.131 (3)	−0.008 (2)	0.0089 (19)	−0.058 (3)
C8	0.105 (3)	0.111 (3)	0.078 (2)	−0.022 (2)	0.0064 (19)	−0.037 (2)

Geometric parameters (Å, º)

N1—C2	1.340 (3)	C4—H4B	0.9600
N1—C1	1.342 (3)	C4—H4C	0.9600
N2—C5	1.446 (4)	C5—H5C	0.9600
N2—C3	1.457 (3)	C5—H5B	0.9600
N2—C4	1.463 (3)	C5—H5A	0.9600
N3—C7	1.452 (4)	C6—H6A	0.9700
N3—C6	1.454 (3)	C6—H6B	0.9700
N3—C8	1.456 (3)	C7—H7A	0.9600
C1—C2^i	1.394 (3)	C7—H7B	0.9600
C1—C3	1.506 (3)	C7—H7C	0.9600
C2—C6	1.505 (3)	C8—H8A	0.9600
C3—H3A	0.9700	C8—H8B	0.9600
C3—H3B	0.9700	C8—H8C	0.9600
C4—H4A	0.9600
C2—N1—C1	117.5 (2)	N2—C5—H5C	109.5
C5—N2—C3	111.0 (2)	N2—C5—H5B	109.5
C5—N2—C4	110.8 (2)	H5C—C5—H5B	109.5
C3—N2—C4	111.3 (2)	N2—C5—H5A	109.5
C7—N3—C6	111.2 (2)	H5C—C5—H5A	109.5
C7—N3—C8	110.0 (2)	H5B—C5—H5A	109.5
C6—N3—C8	110.9 (2)	N3—C6—C2	112.3 (2)
N1—C1—C2^i	121.0 (2)	N3—C6—H6A	109.1
N1—C1—C3	117.3 (2)	C2—C6—H6A	109.1
C2^i—C1—C3	121.7 (2)	N3—C6—H6B	109.1
N1—C2—C1^i	121.5 (2)	C2—C6—H6B	109.1
N1—C2—C6	116.5 (2)	H6A—C6—H6B	107.9
C1^i—C2—C6	121.9 (2)	N3—C7—H7A	109.5
N2—C3—C1	111.3 (2)	N3—C7—H7B	109.5
N2—C3—H3A	109.4	H7A—C7—H7B	109.5
C1—C3—H3A	109.4	N3—C7—H7C	109.5
N2—C3—H3B	109.4	H7A—C7—H7C	109.5
C1—C3—H3B	109.4	H7B—C7—H7C	109.5
H3A—C3—H3B	108.0	N3—C8—H8A	109.5
N2—C4—H4A	109.5	N3—C8—H8B	109.5
N2—C4—H4B	109.5	H8A—C8—H8B	109.5
H4A—C4—H4B	109.5	N3—C8—H8C	109.5
N2—C4—H4C	109.5	H8A—C8—H8C	109.5
H4A—C4—H4C	109.5	H8B—C8—H8C	109.5
H4B—C4—H4C	109.5
C2—N1—C1—C2^i	−0.1 (3)	N1—C1—C3—N2	103.4 (2)
C2—N1—C1—C3	−178.68 (19)	C2^i—C1—C3—N2	−75.2 (3)
C1—N1—C2—C1^i	0.1 (3)	C7—N3—C6—C2	71.6 (3)
C1—N1—C2—C6	−179.79 (19)	C8—N3—C6—C2	−165.7 (2)
C5—N2—C3—C1	−77.0 (3)	N1—C2—C6—N3	−108.7 (2)
C4—N2—C3—C1	159.1 (2)	C1^i—C2—C6—N3	71.4 (3)

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···N3^i	0.97	2.62	3.261 (4)	124

Symmetry code: (i) −x, −y, −z+1.

N,N',N'',N'''-[Pyrazine-2,3,5,6\ tetrayltetrakis(methylene)]tetrakis(N-methylaniline) (II)

Crystal data

C36H40N6	Z = 1
Mr = 556.74	F(000) = 298
Triclinic, P1	Dx = 1.251 Mg m^−3
a = 8.6753 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9160 (11) Å	Cell parameters from 28 reflections
c = 10.0631 (10) Å	θ = 12.5–17.6°
α = 85.774 (10)°	µ = 0.08 mm^−1
β = 73.468 (11)°	T = 293 K
γ = 82.467 (11)°	Block, pale-greenish-yellow
V = 739.21 (15) Å^3	0.38 × 0.30 × 0.27 mm

Data collection

Stoe–Siemens AED2, 4-circle diffractometer	Rint = 0.031
Radiation source: fine-focus sealed tube	θmax = 25.5°, θmin = 2.1°
Plane graphite monochromator	h = −9→10
ω/\2q scans	k = −10→10
5354 measured reflections	l = −12→12
2741 independent reflections	2 standard reflections every 60 min
1913 reflections with I > 2σ(I)	intensity decay: 1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.0254P)^2 + 0.254P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
2741 reflections	Δρmax = 0.13 e Å^−3
193 parameters	Δρmin = −0.14 e Å^−3
0 restraints	Extinction correction: (SHELXL2018/3; Sheldrick 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.026 (3)

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
N1	0.46201 (19)	0.59971 (18)	0.89913 (16)	0.0393 (4)
N2	0.5739 (2)	0.31235 (19)	0.66461 (17)	0.0454 (4)
N3	0.2493 (2)	0.85914 (19)	0.95305 (17)	0.0481 (5)
C1	0.5585 (2)	0.4702 (2)	0.86471 (19)	0.0366 (5)
C2	0.4027 (2)	0.6301 (2)	1.0334 (2)	0.0378 (5)
C3	0.6246 (2)	0.4442 (2)	0.7110 (2)	0.0437 (5)
H3A	0.590818	0.533444	0.660508	0.052*
H3B	0.741879	0.433034	0.687257	0.052*
C4	0.4248 (3)	0.3268 (2)	0.63526 (19)	0.0429 (5)
C5	0.3070 (3)	0.4493 (3)	0.6795 (2)	0.0502 (6)
H5	0.328637	0.524582	0.728604	0.060*
C6	0.1604 (3)	0.4603 (3)	0.6515 (2)	0.0619 (7)
H6	0.083983	0.542794	0.682224	0.074*
C7	0.1237 (3)	0.3508 (3)	0.5785 (3)	0.0674 (7)
H7	0.024139	0.359185	0.559288	0.081*
C8	0.2367 (3)	0.2306 (3)	0.5354 (3)	0.0661 (7)
H8	0.212966	0.155880	0.486985	0.079*
C9	0.3863 (3)	0.2167 (2)	0.5618 (2)	0.0549 (6)
H9	0.461601	0.133665	0.530481	0.066*
C10	0.7008 (3)	0.2013 (3)	0.5894 (3)	0.0645 (7)
H10A	0.799406	0.208832	0.612583	0.097*
H10B	0.717471	0.220396	0.491434	0.097*
H10C	0.669345	0.101522	0.614401	0.097*
C11	0.2938 (3)	0.7782 (2)	1.0686 (2)	0.0488 (6)
H11A	0.195686	0.756971	1.138934	0.059*
H11B	0.348395	0.843600	1.108603	0.059*
C12	0.1177 (2)	0.8292 (2)	0.9122 (2)	0.0431 (5)
C13	0.0121 (3)	0.7258 (3)	0.9845 (2)	0.0586 (6)
H13	0.032849	0.671020	1.061037	0.070*
C14	−0.1220 (3)	0.7040 (3)	0.9440 (3)	0.0697 (7)
H14	−0.191144	0.635993	0.994996	0.084*
C15	−0.1562 (3)	0.7802 (3)	0.8302 (3)	0.0690 (7)
H15	−0.247073	0.765006	0.803564	0.083*
C16	−0.0517 (3)	0.8795 (3)	0.7571 (3)	0.0643 (7)
H16	−0.072129	0.931190	0.679059	0.077*
C17	0.0822 (3)	0.9052 (2)	0.7956 (2)	0.0516 (6)
H17	0.149960	0.973716	0.743706	0.062*
C18	0.3667 (3)	0.9499 (3)	0.8637 (3)	0.0633 (7)
H18A	0.407036	0.906772	0.774033	0.095*
H18B	0.454775	0.952213	0.903352	0.095*
H18C	0.316286	1.051147	0.854497	0.095*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0443 (10)	0.0408 (10)	0.0350 (9)	−0.0041 (8)	−0.0144 (7)	−0.0032 (7)
N2	0.0498 (11)	0.0481 (10)	0.0390 (10)	0.0057 (8)	−0.0163 (8)	−0.0112 (8)
N3	0.0541 (11)	0.0469 (11)	0.0455 (10)	0.0000 (9)	−0.0210 (9)	0.0016 (8)
C1	0.0371 (11)	0.0405 (11)	0.0347 (11)	−0.0066 (9)	−0.0126 (9)	−0.0044 (9)
C2	0.0400 (11)	0.0397 (11)	0.0366 (11)	−0.0044 (9)	−0.0147 (9)	−0.0040 (9)
C3	0.0454 (12)	0.0489 (12)	0.0360 (11)	−0.0029 (10)	−0.0106 (9)	−0.0039 (9)
C4	0.0523 (13)	0.0451 (12)	0.0314 (11)	−0.0027 (10)	−0.0142 (9)	0.0021 (9)
C5	0.0551 (14)	0.0576 (14)	0.0379 (12)	0.0042 (11)	−0.0159 (10)	−0.0098 (10)
C6	0.0490 (14)	0.0793 (18)	0.0521 (14)	0.0084 (13)	−0.0120 (11)	−0.0046 (13)
C7	0.0535 (15)	0.090 (2)	0.0637 (16)	−0.0169 (14)	−0.0239 (13)	0.0119 (15)
C8	0.0831 (19)	0.0582 (16)	0.0719 (17)	−0.0206 (14)	−0.0412 (15)	0.0038 (13)
C9	0.0747 (16)	0.0424 (13)	0.0524 (14)	−0.0010 (11)	−0.0275 (12)	−0.0030 (10)
C10	0.0631 (16)	0.0667 (16)	0.0613 (15)	0.0207 (13)	−0.0210 (12)	−0.0223 (13)
C11	0.0574 (14)	0.0506 (13)	0.0406 (12)	0.0052 (10)	−0.0210 (10)	−0.0074 (10)
C12	0.0464 (12)	0.0381 (11)	0.0429 (12)	0.0086 (9)	−0.0140 (10)	−0.0078 (9)
C13	0.0673 (16)	0.0563 (15)	0.0519 (14)	−0.0083 (12)	−0.0173 (12)	0.0048 (11)
C14	0.0597 (16)	0.0732 (18)	0.0723 (18)	−0.0179 (13)	−0.0071 (14)	−0.0057 (14)
C15	0.0550 (15)	0.0744 (18)	0.083 (2)	0.0020 (14)	−0.0280 (14)	−0.0203 (15)
C16	0.0704 (17)	0.0633 (16)	0.0654 (16)	0.0085 (13)	−0.0356 (14)	−0.0040 (13)
C17	0.0555 (14)	0.0492 (13)	0.0509 (13)	−0.0012 (11)	−0.0196 (11)	0.0026 (10)
C18	0.0677 (16)	0.0617 (15)	0.0676 (16)	−0.0143 (13)	−0.0287 (13)	0.0036 (13)

Geometric parameters (Å, º)

N1—C2	1.336 (2)	C8—H8	0.9300
N1—C1	1.339 (2)	C9—H9	0.9300
N2—C4	1.395 (3)	C10—H10A	0.9600
N2—C10	1.454 (3)	C10—H10B	0.9600
N2—C3	1.459 (3)	C10—H10C	0.9600
N3—C12	1.382 (3)	C11—H11A	0.9700
N3—C11	1.442 (2)	C11—H11B	0.9700
N3—C18	1.445 (3)	C12—C13	1.400 (3)
C1—C2^i	1.395 (3)	C12—C17	1.401 (3)
C1—C3	1.512 (3)	C13—C14	1.378 (3)
C2—C11	1.521 (3)	C13—H13	0.9300
C3—H3A	0.9700	C14—C15	1.374 (4)
C3—H3B	0.9700	C14—H14	0.9300
C4—C9	1.398 (3)	C15—C16	1.371 (4)
C4—C5	1.398 (3)	C15—H15	0.9300
C5—C6	1.369 (3)	C16—C17	1.375 (3)
C5—H5	0.9300	C16—H16	0.9300
C6—C7	1.384 (3)	C17—H17	0.9300
C6—H6	0.9300	C18—H18A	0.9600
C7—C8	1.359 (4)	C18—H18B	0.9600
C7—H7	0.9300	C18—H18C	0.9600
C8—C9	1.386 (3)
C2—N1—C1	118.46 (16)	C7—C8—C9	121.7 (2)
C4—N2—C10	117.64 (17)	C7—C8—H8	119.2
C4—N2—C3	118.71 (16)	C9—C8—H8	119.2
C10—N2—C3	117.17 (18)	C8—C9—C4	120.4 (2)
C12—N3—C11	122.00 (18)	C8—C9—H9	119.8
C12—N3—C18	120.07 (17)	C4—C9—H9	119.8
C11—N3—C18	116.70 (18)	N3—C12—C13	122.77 (19)
N1—C1—C2^i	120.79 (16)	N3—C12—C17	120.5 (2)
N1—C1—C3	115.85 (16)	C13—C12—C17	116.7 (2)
C2^i—C1—C3	123.33 (17)	C14—C13—C12	121.0 (2)
N1—C2—C1^i	120.74 (17)	C14—C13—H13	119.5
N1—C2—C11	117.03 (17)	C12—C13—H13	119.5
C1^i—C2—C11	122.23 (17)	C15—C14—C13	121.6 (2)
N2—C3—C1	114.84 (17)	C15—C14—H14	119.2
N2—C3—H3A	108.6	C13—C14—H14	119.2
C1—C3—H3A	108.6	C16—C15—C14	117.7 (2)
N2—C3—H3B	108.6	C16—C15—H15	121.1
C1—C3—H3B	108.6	C14—C15—H15	121.1
H3A—C3—H3B	107.5	C15—C16—C17	122.1 (2)
N3—C11—C2	115.02 (17)	C15—C16—H16	119.0
N3—C11—H11A	108.5	C17—C16—H16	119.0
C2—C11—H11A	108.5	C16—C17—C12	120.8 (2)
N3—C11—H11B	108.5	C16—C17—H17	119.6
C2—C11—H11B	108.5	C12—C17—H17	119.6
H11A—C11—H11B	107.5	N3—C18—H18A	109.5
N2—C4—C9	120.81 (19)	N3—C18—H18B	109.5
N2—C4—C5	121.91 (19)	H18A—C18—H18B	109.5
C9—C4—C5	117.3 (2)	N3—C18—H18C	109.5
C6—C5—C4	121.1 (2)	H18A—C18—H18C	109.5
C6—C5—H5	119.5	H18B—C18—H18C	109.5
C4—C5—H5	119.5	N2—C10—H10A	109.5
C5—C6—C7	121.2 (2)	N2—C10—H10B	109.5
C5—C6—H6	119.4	H10A—C10—H10B	109.5
C7—C6—H6	119.4	N2—C10—H10C	109.5
C8—C7—C6	118.4 (2)	H10A—C10—H10C	109.5
C8—C7—H7	120.8	H10B—C10—H10C	109.5
C6—C7—H7	120.8
C2—N1—C1—C2^i	−0.5 (3)	C4—C5—C6—C7	−0.1 (4)
C2—N1—C1—C3	−178.66 (17)	C5—C6—C7—C8	0.4 (4)
C1—N1—C2—C1^i	0.5 (3)	C6—C7—C8—C9	−0.6 (4)
C1—N1—C2—C11	179.92 (17)	C7—C8—C9—C4	0.5 (4)
C4—N2—C3—C1	83.8 (2)	N2—C4—C9—C8	178.8 (2)
C10—N2—C3—C1	−125.0 (2)	C5—C4—C9—C8	−0.2 (3)
N1—C1—C3—N2	−117.34 (19)	C11—N3—C12—C13	4.2 (3)
C2^i—C1—C3—N2	64.5 (2)	C18—N3—C12—C13	171.1 (2)
C12—N3—C11—C2	86.2 (2)	C11—N3—C12—C17	−177.13 (19)
C18—N3—C11—C2	−81.1 (2)	C18—N3—C12—C17	−10.2 (3)
N1—C2—C11—N3	8.2 (3)	N3—C12—C13—C14	177.1 (2)
C1^i—C2—C11—N3	−172.42 (18)	C17—C12—C13—C14	−1.7 (3)
C10—N2—C4—C9	14.5 (3)	C12—C13—C14—C15	1.2 (4)
C3—N2—C4—C9	165.50 (19)	C13—C14—C15—C16	0.1 (4)
C10—N2—C4—C5	−166.6 (2)	C14—C15—C16—C17	−0.8 (4)
C3—N2—C4—C5	−15.6 (3)	C15—C16—C17—C12	0.3 (4)
N2—C4—C5—C6	−178.9 (2)	N3—C12—C17—C16	−177.8 (2)
C9—C4—C5—C6	0.0 (3)	C13—C12—C17—C16	1.0 (3)

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º)

Cg2 and Cg3 are the centroids of rings C4–C9 and C12–C17, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N1	0.93	2.50	3.331 (3)	149
C6—H6···Cg3	0.93	2.99	3.804 (3)	147
C3—H3A···Cg2^ii	0.97	2.83	3.561 (2)	133

Symmetry code: (ii) −x+1, −y+1, −z+1.

N,N'-[(6-Phenyl-6,7-dihydro-5H-pyrrolo[3,4-\ b]pyrazine-2,3-diyl)bis(methylene)]bis(N-methylaniline) (III)

Crystal data

C28H29N5	Z = 2
Mr = 435.56	F(000) = 464
Triclinic, P1	Dx = 1.247 Mg m^−3
a = 8.686 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.7731 (11) Å	Cell parameters from 5000 reflections
c = 14.3948 (16) Å	θ = 1.7–26.1°
α = 85.915 (13)°	µ = 0.08 mm^−1
β = 75.349 (13)°	T = 293 K
γ = 78.891 (13)°	Hexagonal plate, pale yellow
V = 1159.8 (2) Å^3	0.45 × 0.35 × 0.10 mm

Data collection

Stoe IPDS 1 diffractometer	1518 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.051
Plane graphite monochromator	θmax = 25.3°, θmin = 2.1°
φ rotation scans	h = −10→10
8653 measured reflections	k = −11→11
3953 independent reflections	l = −17→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.079	w = 1/[σ^2(Fo^2) + (0.0308P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.68	(Δ/σ)max < 0.001
3953 reflections	Δρmax = 0.12 e Å^−3
301 parameters	Δρmin = −0.12 e Å^−3
0 restraints	Extinction correction: (SHELXL2018/3; Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0154 (11)

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
N1	0.4060 (2)	0.8786 (2)	0.20916 (11)	0.0559 (5)
N2	0.2666 (2)	0.9790 (2)	0.05437 (12)	0.0596 (6)
N3	0.5915 (2)	0.6863 (2)	−0.00687 (11)	0.0641 (6)
N4	−0.0765 (2)	1.1354 (2)	0.19845 (12)	0.0567 (5)
N5	0.2256 (2)	0.9508 (2)	0.39598 (12)	0.0607 (6)
C1	0.2797 (3)	0.9865 (2)	0.21849 (14)	0.0536 (6)
C2	0.4566 (2)	0.8223 (2)	0.12258 (14)	0.0510 (6)
C3	0.3862 (3)	0.8699 (3)	0.04787 (13)	0.0522 (6)
C4	0.2133 (2)	1.0385 (2)	0.14142 (15)	0.0550 (6)
C5	0.5911 (3)	0.7029 (2)	0.09341 (13)	0.0611 (7)
H5A	0.692953	0.724226	0.098842	0.073*
H5B	0.570113	0.619743	0.131738	0.073*
C6	0.4643 (2)	0.7825 (2)	−0.03875 (13)	0.0577 (7)
H6A	0.388274	0.733319	−0.055210	0.069*
H6B	0.508592	0.838726	−0.093682	0.069*
C7	0.6870 (3)	0.5773 (3)	−0.06142 (15)	0.0559 (6)
C8	0.8004 (3)	0.4812 (3)	−0.02614 (15)	0.0620 (7)
H8	0.810894	0.489435	0.035832	0.074*
C9	0.8976 (3)	0.3735 (3)	−0.08282 (17)	0.0725 (8)
H9	0.972506	0.309893	−0.058215	0.087*
C10	0.8853 (3)	0.3590 (3)	−0.17452 (19)	0.0773 (8)
H10	0.951563	0.286567	−0.212066	0.093*
C11	0.7738 (3)	0.4528 (3)	−0.21026 (16)	0.0764 (8)
H11	0.764776	0.443527	−0.272410	0.092*
C12	0.6751 (3)	0.5608 (3)	−0.15511 (15)	0.0665 (7)
H12	0.599899	0.623164	−0.180367	0.080*
C13	0.2210 (3)	1.0516 (2)	0.31746 (14)	0.0602 (7)
H13A	0.287658	1.119063	0.321236	0.072*
H13B	0.110758	1.101454	0.324780	0.072*
C14	0.1121 (3)	0.8654 (3)	0.42226 (14)	0.0560 (6)
C15	−0.0211 (3)	0.8838 (3)	0.38231 (15)	0.0629 (7)
H15	−0.032502	0.953551	0.335842	0.076*
C16	−0.1360 (3)	0.8000 (3)	0.41067 (19)	0.0781 (8)
H16	−0.224404	0.814656	0.383465	0.094*
C17	−0.1225 (4)	0.6956 (3)	0.4781 (2)	0.0906 (9)
H17	−0.199630	0.638472	0.496365	0.109*
C18	0.0080 (5)	0.6771 (3)	0.51850 (19)	0.0919 (10)
H18	0.017561	0.607346	0.565218	0.110*
C19	0.1240 (3)	0.7587 (3)	0.49158 (17)	0.0713 (8)
H19	0.211426	0.743206	0.519603	0.086*
C20	0.3718 (3)	0.9195 (3)	0.43102 (17)	0.0861 (9)
H20A	0.435685	0.990627	0.408568	0.129*
H20B	0.433210	0.830763	0.407665	0.129*
H20C	0.343173	0.916359	0.499973	0.129*
C21	0.0812 (3)	1.1664 (2)	0.14886 (15)	0.0651 (7)
H21A	0.106550	1.237790	0.183089	0.078*
H21B	0.077662	1.202914	0.084840	0.078*
C22	−0.1951 (3)	1.2457 (3)	0.24527 (14)	0.0534 (6)
C23	−0.1678 (3)	1.3796 (3)	0.24765 (15)	0.0688 (7)
H23	−0.069134	1.402028	0.213889	0.083*
C24	−0.2859 (4)	1.4813 (3)	0.29992 (19)	0.0860 (9)
H24	−0.264807	1.570861	0.301192	0.103*
C25	−0.4332 (4)	1.4517 (4)	0.34971 (19)	0.0920 (11)
H25	−0.511567	1.519698	0.385288	0.110*
C26	−0.4620 (3)	1.3199 (4)	0.34573 (18)	0.0911 (10)
H26	−0.562113	1.299000	0.378099	0.109*
C27	−0.3461 (3)	1.2173 (3)	0.29485 (16)	0.0719 (8)
H27	−0.368766	1.128393	0.293559	0.086*
C28	−0.1287 (3)	1.0303 (3)	0.15362 (17)	0.0805 (8)
H28A	−0.200292	0.983359	0.201593	0.121*
H28B	−0.036112	0.963950	0.123096	0.121*
H28C	−0.184352	1.073996	0.106462	0.121*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0524 (11)	0.0660 (15)	0.0465 (11)	−0.0088 (11)	−0.0077 (9)	−0.0042 (9)
N2	0.0533 (12)	0.0728 (15)	0.0465 (11)	−0.0058 (11)	−0.0064 (9)	0.0024 (10)
N3	0.0620 (12)	0.0785 (16)	0.0446 (11)	0.0103 (12)	−0.0146 (9)	−0.0111 (10)
N4	0.0522 (12)	0.0551 (14)	0.0605 (11)	−0.0069 (11)	−0.0106 (10)	−0.0064 (10)
N5	0.0562 (13)	0.0813 (17)	0.0459 (11)	−0.0163 (12)	−0.0104 (10)	−0.0081 (10)
C1	0.0503 (14)	0.0603 (18)	0.0468 (13)	−0.0137 (13)	−0.0020 (11)	−0.0047 (11)
C2	0.0461 (13)	0.0629 (17)	0.0413 (13)	−0.0085 (13)	−0.0070 (11)	−0.0013 (12)
C3	0.0469 (13)	0.0650 (17)	0.0419 (13)	−0.0106 (13)	−0.0056 (11)	0.0000 (12)
C4	0.0498 (14)	0.0601 (17)	0.0505 (14)	−0.0082 (13)	−0.0063 (12)	0.0022 (12)
C5	0.0567 (14)	0.0749 (19)	0.0467 (13)	−0.0009 (14)	−0.0100 (11)	−0.0089 (12)
C6	0.0524 (14)	0.0736 (18)	0.0449 (12)	−0.0084 (13)	−0.0094 (11)	−0.0039 (12)
C7	0.0486 (14)	0.0627 (18)	0.0532 (14)	−0.0095 (14)	−0.0052 (11)	−0.0076 (12)
C8	0.0555 (14)	0.0709 (19)	0.0563 (14)	−0.0066 (15)	−0.0098 (12)	−0.0068 (13)
C9	0.0645 (17)	0.069 (2)	0.0777 (18)	−0.0034 (15)	−0.0112 (14)	−0.0085 (15)
C10	0.0739 (19)	0.074 (2)	0.0766 (18)	−0.0108 (17)	0.0001 (15)	−0.0247 (15)
C11	0.0800 (19)	0.088 (2)	0.0597 (15)	−0.0135 (18)	−0.0103 (14)	−0.0186 (15)
C12	0.0623 (16)	0.080 (2)	0.0562 (15)	−0.0069 (15)	−0.0135 (12)	−0.0119 (13)
C13	0.0618 (16)	0.0653 (18)	0.0513 (13)	−0.0143 (13)	−0.0053 (11)	−0.0109 (13)
C14	0.0589 (16)	0.0647 (19)	0.0397 (13)	−0.0072 (15)	−0.0032 (12)	−0.0143 (12)
C15	0.0598 (16)	0.074 (2)	0.0540 (14)	−0.0175 (15)	−0.0057 (13)	−0.0109 (13)
C16	0.070 (2)	0.085 (2)	0.0761 (18)	−0.0172 (18)	−0.0039 (15)	−0.0237 (17)
C17	0.092 (2)	0.079 (3)	0.092 (2)	−0.039 (2)	0.0180 (18)	−0.0243 (19)
C18	0.127 (3)	0.069 (2)	0.0706 (19)	−0.018 (2)	−0.006 (2)	−0.0067 (15)
C19	0.086 (2)	0.064 (2)	0.0615 (16)	−0.0086 (17)	−0.0154 (14)	−0.0066 (14)
C20	0.0670 (17)	0.122 (3)	0.0789 (17)	−0.0167 (17)	−0.0316 (14)	−0.0145 (16)
C21	0.0603 (16)	0.0617 (19)	0.0639 (14)	−0.0040 (14)	−0.0043 (12)	0.0023 (13)
C22	0.0536 (16)	0.0608 (19)	0.0442 (12)	−0.0012 (14)	−0.0162 (11)	0.0003 (12)
C23	0.0726 (17)	0.061 (2)	0.0673 (16)	−0.0041 (17)	−0.0117 (13)	−0.0061 (14)
C24	0.100 (2)	0.065 (2)	0.0893 (19)	0.0040 (19)	−0.0269 (18)	−0.0202 (16)
C25	0.081 (2)	0.110 (3)	0.0742 (19)	0.019 (2)	−0.0162 (17)	−0.0368 (19)
C26	0.0629 (18)	0.121 (3)	0.0784 (19)	0.003 (2)	−0.0059 (14)	−0.0256 (19)
C27	0.0598 (16)	0.080 (2)	0.0711 (15)	−0.0083 (16)	−0.0100 (14)	−0.0066 (14)
C28	0.0687 (17)	0.086 (2)	0.0927 (18)	−0.0024 (16)	−0.0318 (15)	−0.0313 (16)

Geometric parameters (Å, º)

N1—C2	1.333 (2)	C12—H12	0.9300
N1—C1	1.354 (2)	C13—H13A	0.9700
N2—C3	1.328 (2)	C13—H13B	0.9700
N2—C4	1.352 (2)	C14—C15	1.394 (3)
N3—C7	1.374 (2)	C14—C19	1.398 (3)
N3—C6	1.453 (2)	C15—C16	1.376 (3)
N3—C5	1.463 (2)	C15—H15	0.9300
N4—C22	1.415 (3)	C16—C17	1.367 (4)
N4—C28	1.449 (3)	C16—H16	0.9300
N4—C21	1.453 (3)	C17—C18	1.376 (4)
N5—C14	1.376 (3)	C17—H17	0.9300
N5—C13	1.449 (3)	C18—C19	1.367 (4)
N5—C20	1.454 (3)	C18—H18	0.9300
C1—C4	1.397 (3)	C19—H19	0.9300
C1—C13	1.527 (3)	C20—H20A	0.9600
C2—C3	1.377 (2)	C20—H20B	0.9600
C2—C5	1.483 (3)	C20—H20C	0.9600
C3—C6	1.498 (3)	C21—H21A	0.9700
C4—C21	1.515 (3)	C21—H21B	0.9700
C5—H5A	0.9700	C22—C23	1.378 (3)
C5—H5B	0.9700	C22—C27	1.395 (3)
C6—H6A	0.9700	C23—C24	1.390 (3)
C6—H6B	0.9700	C23—H23	0.9300
C7—C8	1.392 (3)	C24—C25	1.373 (4)
C7—C12	1.401 (3)	C24—H24	0.9300
C8—C9	1.385 (3)	C25—C26	1.366 (4)
C8—H8	0.9300	C25—H25	0.9300
C9—C10	1.370 (3)	C26—C27	1.378 (3)
C9—H9	0.9300	C26—H26	0.9300
C10—C11	1.373 (3)	C27—H27	0.9300
C10—H10	0.9300	C28—H28A	0.9600
C11—C12	1.380 (3)	C28—H28B	0.9600
C11—H11	0.9300	C28—H28C	0.9600
C2—N1—C1	114.96 (16)	C1—C13—H13B	108.9
C3—N2—C4	115.23 (17)	H13A—C13—H13B	107.7
C7—N3—C6	122.57 (16)	N5—C14—C15	121.3 (2)
C7—N3—C5	123.11 (17)	N5—C14—C19	121.3 (2)
C6—N3—C5	113.64 (16)	C15—C14—C19	117.3 (3)
C22—N4—C28	118.35 (19)	C16—C15—C14	120.9 (3)
C22—N4—C21	117.9 (2)	C16—C15—H15	119.5
C28—N4—C21	114.48 (18)	C14—C15—H15	119.5
C14—N5—C13	120.75 (19)	C17—C16—C15	121.1 (3)
C14—N5—C20	119.8 (2)	C17—C16—H16	119.4
C13—N5—C20	117.9 (2)	C15—C16—H16	119.4
N1—C1—C4	122.07 (18)	C16—C17—C18	118.5 (3)
N1—C1—C13	115.34 (18)	C16—C17—H17	120.8
C4—C1—C13	122.5 (2)	C18—C17—H17	120.8
N1—C2—C3	122.80 (19)	C19—C18—C17	121.6 (3)
N1—C2—C5	125.96 (18)	C19—C18—H18	119.2
C3—C2—C5	111.24 (18)	C17—C18—H18	119.2
N2—C3—C2	123.17 (19)	C18—C19—C14	120.6 (3)
N2—C3—C6	126.31 (18)	C18—C19—H19	119.7
C2—C3—C6	110.52 (19)	C14—C19—H19	119.7
N2—C4—C1	121.65 (19)	N5—C20—H20A	109.5
N2—C4—C21	115.81 (19)	N5—C20—H20B	109.5
C1—C4—C21	122.52 (19)	H20A—C20—H20B	109.5
N3—C5—C2	102.26 (16)	N5—C20—H20C	109.5
N3—C5—H5A	111.3	H20A—C20—H20C	109.5
C2—C5—H5A	111.3	H20B—C20—H20C	109.5
N3—C5—H5B	111.3	N4—C21—C4	112.0 (2)
C2—C5—H5B	111.3	N4—C21—H21A	109.2
H5A—C5—H5B	109.2	C4—C21—H21A	109.2
N3—C6—C3	102.22 (16)	N4—C21—H21B	109.2
N3—C6—H6A	111.3	C4—C21—H21B	109.2
C3—C6—H6A	111.3	H21A—C21—H21B	107.9
N3—C6—H6B	111.3	C23—C22—C27	117.8 (2)
C3—C6—H6B	111.3	C23—C22—N4	123.5 (2)
H6A—C6—H6B	109.2	C27—C22—N4	118.7 (3)
N3—C7—C8	121.19 (19)	C22—C23—C24	120.7 (3)
N3—C7—C12	120.9 (2)	C22—C23—H23	119.6
C8—C7—C12	117.9 (2)	C24—C23—H23	119.6
C9—C8—C7	120.4 (2)	C25—C24—C23	121.0 (3)
C9—C8—H8	119.8	C25—C24—H24	119.5
C7—C8—H8	119.8	C23—C24—H24	119.5
C10—C9—C8	121.2 (2)	C26—C25—C24	118.4 (3)
C10—C9—H9	119.4	C26—C25—H25	120.8
C8—C9—H9	119.4	C24—C25—H25	120.8
C9—C10—C11	119.1 (2)	C25—C26—C27	121.5 (3)
C9—C10—H10	120.4	C25—C26—H26	119.3
C11—C10—H10	120.4	C27—C26—H26	119.3
C10—C11—C12	120.8 (2)	C26—C27—C22	120.6 (3)
C10—C11—H11	119.6	C26—C27—H27	119.7
C12—C11—H11	119.6	C22—C27—H27	119.7
C11—C12—C7	120.6 (2)	N4—C28—H28A	109.5
C11—C12—H12	119.7	N4—C28—H28B	109.5
C7—C12—H12	119.7	H28A—C28—H28B	109.5
N5—C13—C1	113.53 (19)	N4—C28—H28C	109.5
N5—C13—H13A	108.9	H28A—C28—H28C	109.5
C1—C13—H13A	108.9	H28B—C28—H28C	109.5
N5—C13—H13B	108.9
C2—N1—C1—C4	−2.9 (3)	N3—C7—C12—C11	178.6 (2)
C2—N1—C1—C13	−180.0 (2)	C8—C7—C12—C11	−0.4 (3)
C1—N1—C2—C3	0.0 (3)	C14—N5—C13—C1	−75.0 (2)
C1—N1—C2—C5	−179.5 (2)	C20—N5—C13—C1	91.0 (3)
C4—N2—C3—C2	−2.3 (3)	N1—C1—C13—N5	−37.6 (3)
C4—N2—C3—C6	178.1 (2)	C4—C1—C13—N5	145.3 (2)
N1—C2—C3—N2	2.8 (3)	C13—N5—C14—C15	−7.6 (3)
C5—C2—C3—N2	−177.7 (2)	C20—N5—C14—C15	−173.29 (19)
N1—C2—C3—C6	−177.6 (2)	C13—N5—C14—C19	173.80 (19)
C5—C2—C3—C6	2.0 (3)	C20—N5—C14—C19	8.1 (3)
C3—N2—C4—C1	−0.6 (3)	N5—C14—C15—C16	−178.5 (2)
C3—N2—C4—C21	177.8 (2)	C19—C14—C15—C16	0.2 (3)
N1—C1—C4—N2	3.4 (3)	C14—C15—C16—C17	−0.6 (4)
C13—C1—C4—N2	−179.8 (2)	C15—C16—C17—C18	0.9 (4)
N1—C1—C4—C21	−174.9 (2)	C16—C17—C18—C19	−1.0 (4)
C13—C1—C4—C21	2.0 (3)	C17—C18—C19—C14	0.7 (4)
C7—N3—C5—C2	−173.1 (2)	N5—C14—C19—C18	178.4 (2)
C6—N3—C5—C2	−2.3 (2)	C15—C14—C19—C18	−0.3 (3)
N1—C2—C5—N3	179.7 (2)	C22—N4—C21—C4	154.45 (18)
C3—C2—C5—N3	0.1 (2)	C28—N4—C21—C4	−59.3 (2)
C7—N3—C6—C3	174.2 (2)	N2—C4—C21—N4	103.8 (2)
C5—N3—C6—C3	3.3 (2)	C1—C4—C21—N4	−77.8 (3)
N2—C3—C6—N3	176.5 (2)	C28—N4—C22—C23	−146.2 (2)
C2—C3—C6—N3	−3.2 (2)	C21—N4—C22—C23	−1.2 (3)
C6—N3—C7—C8	−175.5 (2)	C28—N4—C22—C27	36.3 (3)
C5—N3—C7—C8	−5.5 (3)	C21—N4—C22—C27	−178.72 (19)
C6—N3—C7—C12	5.6 (3)	C27—C22—C23—C24	1.6 (3)
C5—N3—C7—C12	175.6 (2)	N4—C22—C23—C24	−175.92 (19)
N3—C7—C8—C9	−178.8 (2)	C22—C23—C24—C25	−0.6 (4)
C12—C7—C8—C9	0.1 (3)	C23—C24—C25—C26	−0.8 (4)
C7—C8—C9—C10	0.2 (4)	C24—C25—C26—C27	1.3 (4)
C8—C9—C10—C11	−0.3 (4)	C25—C26—C27—C22	−0.3 (4)
C9—C10—C11—C12	0.1 (4)	C23—C22—C27—C26	−1.2 (3)
C10—C11—C12—C7	0.3 (4)	N4—C22—C27—C26	176.5 (2)

Hydrogen-bond geometry (Å, º)

Cg2 and Cg3 are the centroids of rings N1/N2/C1–C4 and C7–C12, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···N4	0.93	2.61	3.542 (3)	175
C28—H28B···N2	0.96	2.59	3.323 (3)	133
C6—H6B···Cg2^i	0.97	2.82	3.601 (2)	138
C23—H23···Cg3^i	0.93	2.97	3.881 (3)	168

Symmetry code: (i) −x+1, −y+2, −z.