9-Amino-5,7-di­bromo-1,2,3,4-tetra­hydro­acridine hemihydrate

The asymmetric unit of the title compound, C₁₃H₁₂Br₂N₂·0.5H₂O, includes two mol­ecules of 5,7-di­bromo-1,2,3,4-tetra­hydro­acridin-9-amine and one water mol­ecule. In the crystal, C—H...O, N—H...N, N—H...O and O—H...N hydrogen bonds connect the mol­ecules, forming a two-dimensional network parallel to (010). The two-dimensional sheets are further assembled into a three-dimensional structure through C—H...π and π–π stacking inter­actions [centroid–centroid distance = 3.719 (2) Å].

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.039
• wR factor = 0.080
• Data-to-parameter ratio = 19.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor       O1     --  H2O    ...     Please Check

Alert level C
PLAT041_ALERT_1_C Calc. and Reported SumFormula    Strings  Differ     Please Check
PLAT420_ALERT_2_C D-H Without Acceptor       N2     --  H2NB   ...     Please Check
PLAT420_ALERT_2_C D-H Without Acceptor       N4     --  H4NA   ...     Please Check
PLAT434_ALERT_2_C Short Inter HL..HL Contact Br1    ..  Br1     ..       3.33 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.916 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min)           8 Note

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          3 Note
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT045_ALERT_1_G Calculated and Reported Z Differ by a Factor ...       0.50 Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.009 Degree
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          3 Report
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          4 Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         38 Note
PLAT960_ALERT_3_G Number of Intensities with I  <   - 2*sig(I) ...          4 Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Note

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   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

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

9-Amino-5,7-dibromo-1,2,3,4-tetrahydroacridine hemihydrate

Crystal data

C13H12Br2N2·0.5H2O	Z = 4
Mr = 365.05	F(000) = 716
Triclinic, P1	Dx = 1.860 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.404 (2) Å	Cell parameters from 9584 reflections
b = 11.163 (2) Å	θ = 3.5–28.3°
c = 13.263 (3) Å	µ = 6.20 mm^−1
α = 80.607 (9)°	T = 296 K
β = 75.713 (9)°	Block, yellow
γ = 76.407 (9)°	0.16 × 0.13 × 0.12 mm
V = 1303.3 (5) Å^3

Data collection

Bruker APEXII CCD diffractometer	4883 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.055
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	θmax = 28.4°, θmin = 3.1°
Tmin = 0.409, Tmax = 0.746	h = −12→12
66562 measured reflections	k = −14→14
6486 independent reflections	l = −17→17

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)] = 0.039	w = 1/[σ^2(Fo^2) + (0.0191P)^2 + 2.4473P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.080	(Δ/σ)max = 0.001
S = 1.09	Δρmax = 0.63 e Å^−3
6486 reflections	Δρmin = −0.83 e Å^−3
335 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
3 restraints	Extinction coefficient: 0.0038 (3)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs 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.

The amino and water H atoms were located in a difference Fourier map and refined with U_iso(H) = 1.2U_eq(N) or 1.5U_eq(O). DFIX instructions were used to keep the H atoms of the water molecule in place. The C-bound H atoms were included in calculated positions and treated as riding atoms, with C—H = 0.93–0.97 Å, and with U_iso(H) = 1.2U_eq(C).

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

	x	y	z	Uiso*/Ueq
Br1	0.91349 (5)	0.88067 (3)	0.02649 (4)	0.0546 (2)
Br2	0.87277 (6)	0.44474 (4)	0.29818 (3)	0.0539 (1)
Br3	0.37866 (5)	0.47644 (3)	0.40689 (3)	0.0495 (1)
Br4	0.41617 (4)	0.08140 (4)	0.72633 (3)	0.0426 (1)
N1	0.7550 (3)	0.3730 (2)	0.1241 (2)	0.0273 (8)
N2	0.7120 (5)	0.5786 (3)	−0.1647 (3)	0.0515 (13)
C1	0.8727 (4)	0.7188 (3)	0.0515 (3)	0.0330 (10)
C2	0.8871 (4)	0.6491 (3)	0.1476 (3)	0.0339 (10)
C3	0.8504 (4)	0.5353 (3)	0.1682 (2)	0.0310 (10)
C4	0.7960 (3)	0.4850 (3)	0.0972 (2)	0.0251 (8)
C5	0.7853 (3)	0.5580 (3)	0.0001 (2)	0.0262 (9)
C6	0.8266 (4)	0.6763 (3)	−0.0213 (3)	0.0332 (10)
C7	0.7288 (4)	0.5106 (3)	−0.0721 (2)	0.0321 (10)
C8	0.6920 (4)	0.3941 (3)	−0.0450 (2)	0.0307 (9)
C9	0.7041 (3)	0.3311 (3)	0.0539 (2)	0.0280 (9)
C10	0.6592 (4)	0.2070 (3)	0.0881 (3)	0.0362 (11)
C11	0.5783 (5)	0.1696 (4)	0.0163 (3)	0.0508 (14)
C12	0.6505 (5)	0.1991 (4)	−0.0964 (3)	0.0559 (16)
C13	0.6399 (5)	0.3390 (4)	−0.1225 (3)	0.0462 (11)
N3	0.6966 (3)	−0.0310 (2)	0.56636 (19)	0.0277 (8)
N4	0.8774 (4)	0.1289 (3)	0.2676 (2)	0.0424 (10)
O1	0.7290 (4)	0.8667 (3)	0.7765 (2)	0.0711 (11)
C14	0.4807 (4)	0.3162 (3)	0.4538 (3)	0.0324 (10)
C15	0.4262 (4)	0.2654 (3)	0.5559 (3)	0.0339 (10)
C16	0.4985 (3)	0.1505 (3)	0.5898 (2)	0.0287 (9)
C17	0.6288 (3)	0.0828 (3)	0.5277 (2)	0.0258 (9)
C18	0.6816 (3)	0.1404 (3)	0.4257 (2)	0.0261 (9)
C19	0.6036 (4)	0.2572 (3)	0.3890 (2)	0.0308 (9)
C20	0.8175 (4)	0.0774 (3)	0.3640 (2)	0.0283 (9)
C21	0.8858 (4)	−0.0400 (3)	0.4041 (2)	0.0292 (9)
C22	0.8187 (4)	−0.0896 (3)	0.5043 (2)	0.0277 (9)
C23	0.8851 (4)	−0.2184 (3)	0.5482 (3)	0.0394 (11)
C24	0.9843 (5)	−0.2968 (4)	0.4651 (3)	0.0537 (14)
C25	1.0988 (5)	−0.2286 (4)	0.3966 (4)	0.0584 (14)
C26	1.0254 (4)	−0.1100 (3)	0.3383 (3)	0.0424 (11)
H2NA	0.727 (5)	0.651 (4)	−0.175 (4)	0.0620*
H2	0.92100	0.68000	0.19630	0.0410*
H2NB	0.678 (5)	0.552 (4)	−0.205 (4)	0.0620*
H6	0.82160	0.72350	−0.08540	0.0400*
H10A	0.59490	0.20900	0.15750	0.0440*
H10B	0.74860	0.14390	0.09290	0.0440*
H11A	0.57990	0.08130	0.03100	0.0600*
H11B	0.47450	0.21320	0.02960	0.0600*
H12A	0.60080	0.16990	−0.14080	0.0670*
H12B	0.75490	0.15690	−0.10960	0.0670*
H13A	0.70040	0.35560	−0.19190	0.0560*
H13B	0.53680	0.37890	−0.12350	0.0560*
H4NA	0.959 (5)	0.099 (4)	0.242 (3)	0.0510*
H4NB	0.842 (5)	0.205 (4)	0.242 (3)	0.0510*
H15	0.34330	0.30870	0.59940	0.0410*
H19	0.63590	0.29330	0.32140	0.0370*
H23A	0.94320	−0.21190	0.59750	0.0470*
H23B	0.80430	−0.25950	0.58630	0.0470*
H24A	1.03420	−0.37400	0.49790	0.0640*
H24B	0.92370	−0.31650	0.42290	0.0640*
H25A	1.16580	−0.28180	0.34630	0.0700*
H25B	1.15790	−0.20790	0.43920	0.0700*
H26A	1.09710	−0.05630	0.31330	0.0510*
H26B	1.00010	−0.13110	0.27770	0.0510*
H1O	0.701 (6)	0.889 (5)	0.722 (2)	0.1070*
H2O	0.667 (5)	0.909 (5)	0.818 (3)	0.1070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0611 (3)	0.0270 (2)	0.0741 (3)	−0.0200 (2)	−0.0034 (2)	−0.0024 (2)
Br2	0.0882 (3)	0.0448 (2)	0.0405 (2)	−0.0242 (2)	−0.0337 (2)	0.0079 (2)
Br3	0.0652 (3)	0.0303 (2)	0.0496 (2)	0.0111 (2)	−0.0265 (2)	−0.0035 (2)
Br4	0.0434 (2)	0.0474 (2)	0.0309 (2)	−0.0080 (2)	−0.0006 (2)	−0.0004 (2)
N1	0.0327 (14)	0.0211 (12)	0.0274 (13)	−0.0059 (11)	−0.0067 (11)	−0.0002 (10)
N2	0.081 (3)	0.0457 (19)	0.0334 (17)	−0.0193 (19)	−0.0248 (17)	0.0077 (15)
C1	0.0310 (17)	0.0193 (14)	0.045 (2)	−0.0060 (13)	−0.0005 (14)	−0.0038 (13)
C2	0.0378 (19)	0.0269 (16)	0.0405 (19)	−0.0100 (14)	−0.0090 (15)	−0.0080 (14)
C3	0.0349 (18)	0.0290 (16)	0.0280 (16)	−0.0039 (13)	−0.0076 (13)	−0.0027 (13)
C4	0.0244 (15)	0.0219 (14)	0.0261 (15)	−0.0025 (12)	−0.0025 (12)	−0.0026 (12)
C5	0.0258 (15)	0.0220 (14)	0.0282 (16)	−0.0050 (12)	−0.0026 (12)	−0.0004 (12)
C6	0.0347 (18)	0.0255 (15)	0.0348 (18)	−0.0048 (13)	−0.0049 (14)	0.0033 (13)
C7	0.0354 (18)	0.0337 (17)	0.0247 (16)	−0.0049 (14)	−0.0052 (13)	−0.0017 (13)
C8	0.0331 (17)	0.0322 (16)	0.0269 (16)	−0.0057 (13)	−0.0051 (13)	−0.0069 (13)
C9	0.0275 (16)	0.0221 (14)	0.0320 (16)	−0.0033 (12)	−0.0034 (13)	−0.0031 (12)
C10	0.043 (2)	0.0265 (16)	0.0412 (19)	−0.0116 (14)	−0.0091 (16)	−0.0034 (14)
C11	0.057 (2)	0.042 (2)	0.061 (3)	−0.0202 (19)	−0.016 (2)	−0.0080 (19)
C12	0.074 (3)	0.051 (2)	0.055 (3)	−0.022 (2)	−0.018 (2)	−0.021 (2)
C13	0.057 (2)	0.052 (2)	0.0362 (19)	−0.0154 (19)	−0.0149 (18)	−0.0098 (17)
N3	0.0324 (14)	0.0243 (12)	0.0256 (13)	−0.0038 (11)	−0.0084 (11)	0.0002 (10)
N4	0.0477 (19)	0.0361 (17)	0.0309 (16)	−0.0018 (15)	0.0032 (14)	0.0040 (13)
O1	0.082 (2)	0.070 (2)	0.0372 (16)	0.0135 (18)	−0.0083 (16)	0.0128 (15)
C14	0.0416 (19)	0.0229 (15)	0.0349 (17)	−0.0018 (13)	−0.0174 (15)	−0.0027 (13)
C15	0.0334 (18)	0.0319 (17)	0.0353 (18)	0.0010 (14)	−0.0099 (14)	−0.0083 (14)
C16	0.0297 (16)	0.0312 (16)	0.0259 (15)	−0.0074 (13)	−0.0063 (13)	−0.0034 (13)
C17	0.0282 (16)	0.0248 (14)	0.0278 (15)	−0.0057 (12)	−0.0114 (13)	−0.0037 (12)
C18	0.0313 (16)	0.0226 (14)	0.0266 (15)	−0.0060 (12)	−0.0105 (13)	−0.0016 (12)
C19	0.0393 (18)	0.0253 (15)	0.0286 (16)	−0.0055 (13)	−0.0123 (14)	0.0005 (13)
C20	0.0341 (17)	0.0261 (15)	0.0265 (15)	−0.0076 (13)	−0.0077 (13)	−0.0040 (12)
C21	0.0305 (16)	0.0273 (15)	0.0299 (16)	−0.0022 (13)	−0.0083 (13)	−0.0061 (13)
C22	0.0323 (17)	0.0230 (14)	0.0307 (16)	−0.0033 (12)	−0.0141 (13)	−0.0033 (12)
C23	0.046 (2)	0.0288 (17)	0.0392 (19)	0.0028 (15)	−0.0147 (16)	0.0017 (15)
C24	0.064 (3)	0.035 (2)	0.056 (2)	0.0098 (19)	−0.020 (2)	−0.0065 (18)
C25	0.050 (2)	0.051 (2)	0.063 (3)	0.012 (2)	−0.010 (2)	−0.011 (2)
C26	0.040 (2)	0.0388 (19)	0.042 (2)	0.0014 (16)	−0.0038 (16)	−0.0082 (16)

Geometric parameters (Å, º)

Br1—C1	1.895 (3)	C12—H12B	0.9700
Br2—C3	1.884 (3)	C12—H12A	0.9700
Br3—C14	1.906 (3)	C13—H13B	0.9700
Br4—C16	1.899 (3)	C13—H13A	0.9700
N1—C4	1.361 (4)	N4—H4NB	0.88 (4)
N1—C9	1.335 (4)	N4—H4NA	0.78 (5)
N2—C7	1.358 (5)	C14—C15	1.401 (5)
C1—C2	1.400 (5)	C14—C19	1.358 (5)
C1—C6	1.341 (5)	C15—C16	1.365 (5)
C2—C3	1.362 (5)	C16—C17	1.422 (4)
N2—H2NA	0.84 (5)	C17—C18	1.423 (4)
N2—H2NB	0.81 (5)	C18—C20	1.431 (4)
C3—C4	1.417 (4)	C18—C19	1.412 (5)
C4—C5	1.420 (4)	C20—C21	1.399 (5)
C5—C7	1.424 (4)	C21—C26	1.507 (5)
C5—C6	1.428 (5)	C21—C22	1.408 (4)
C7—C8	1.392 (5)	C22—C23	1.510 (5)
C8—C13	1.507 (5)	C23—C24	1.508 (6)
C8—C9	1.401 (4)	C24—C25	1.497 (7)
C9—C10	1.510 (5)	C25—C26	1.525 (6)
C10—C11	1.515 (6)	O1—H1O	0.81 (4)
C11—C12	1.499 (6)	O1—H2O	0.81 (5)
C12—C13	1.528 (6)	C15—H15	0.9300
C2—H2	0.9300	C19—H19	0.9300
N3—C17	1.361 (4)	C23—H23A	0.9700
N3—C22	1.334 (4)	C23—H23B	0.9700
N4—C20	1.356 (4)	C24—H24B	0.9700
C6—H6	0.9300	C24—H24A	0.9700
C10—H10A	0.9700	C25—H25A	0.9700
C10—H10B	0.9700	C25—H25B	0.9700
C11—H11A	0.9700	C26—H26B	0.9700
C11—H11B	0.9700	C26—H26A	0.9700
C4—N1—C9	117.2 (2)	H4NA—N4—H4NB	117 (4)
Br1—C1—C2	118.4 (3)	C20—N4—H4NA	117 (3)
Br1—C1—C6	119.4 (3)	C20—N4—H4NB	123 (3)
C2—C1—C6	122.2 (3)	Br3—C14—C19	119.5 (3)
C1—C2—C3	118.7 (3)	Br3—C14—C15	117.7 (3)
H2NA—N2—H2NB	122 (5)	C15—C14—C19	122.7 (3)
C7—N2—H2NA	118 (4)	C14—C15—C16	118.0 (3)
C7—N2—H2NB	120 (3)	Br4—C16—C15	116.8 (2)
Br2—C3—C2	117.1 (3)	Br4—C16—C17	120.2 (2)
Br2—C3—C4	120.1 (2)	C15—C16—C17	123.0 (3)
C2—C3—C4	122.9 (3)	N3—C17—C18	123.3 (3)
N1—C4—C5	123.3 (3)	N3—C17—C16	120.2 (2)
N1—C4—C3	120.1 (3)	C16—C17—C18	116.6 (3)
C3—C4—C5	116.6 (3)	C17—C18—C19	120.5 (3)
C4—C5—C6	120.0 (3)	C17—C18—C20	117.6 (3)
C4—C5—C7	117.8 (3)	C19—C18—C20	121.9 (3)
C6—C5—C7	122.2 (3)	C14—C19—C18	119.2 (3)
C1—C6—C5	119.6 (3)	C18—C20—C21	118.6 (3)
C5—C7—C8	118.3 (3)	N4—C20—C21	120.5 (3)
N2—C7—C8	121.6 (3)	N4—C20—C18	120.8 (3)
N2—C7—C5	120.1 (3)	C20—C21—C22	118.3 (3)
C7—C8—C9	119.1 (3)	C20—C21—C26	119.4 (3)
C7—C8—C13	119.3 (3)	C22—C21—C26	122.3 (3)
C9—C8—C13	121.7 (3)	C21—C22—C23	119.8 (3)
C8—C9—C10	120.8 (3)	N3—C22—C21	124.8 (3)
N1—C9—C8	124.3 (3)	N3—C22—C23	115.4 (3)
N1—C9—C10	114.9 (3)	C22—C23—C24	113.1 (3)
C9—C10—C11	114.7 (3)	C23—C24—C25	110.1 (4)
C10—C11—C12	111.0 (4)	C24—C25—C26	111.5 (4)
C11—C12—C13	110.0 (3)	C21—C26—C25	113.7 (3)
C8—C13—C12	112.5 (3)	H1O—O1—H2O	104 (5)
C1—C2—H2	121.00	C14—C15—H15	121.00
C3—C2—H2	121.00	C16—C15—H15	121.00
C17—N3—C22	117.3 (2)	C18—C19—H19	120.00
C5—C6—H6	120.00	C14—C19—H19	120.00
C1—C6—H6	120.00	C22—C23—H23A	109.00
C9—C10—H10A	109.00	C22—C23—H23B	109.00
C9—C10—H10B	109.00	C24—C23—H23B	109.00
C11—C10—H10B	109.00	H23A—C23—H23B	108.00
H10A—C10—H10B	108.00	C24—C23—H23A	109.00
C11—C10—H10A	109.00	C23—C24—H24B	110.00
C10—C11—H11B	109.00	C25—C24—H24A	110.00
C12—C11—H11A	109.00	C25—C24—H24B	110.00
C12—C11—H11B	109.00	H24A—C24—H24B	108.00
H11A—C11—H11B	108.00	C23—C24—H24A	110.00
C10—C11—H11A	109.00	C24—C25—H25B	109.00
C11—C12—H12B	110.00	C26—C25—H25A	109.00
C13—C12—H12A	110.00	C24—C25—H25A	109.00
C11—C12—H12A	110.00	H25A—C25—H25B	108.00
H12A—C12—H12B	108.00	C26—C25—H25B	109.00
C13—C12—H12B	110.00	C21—C26—H26A	109.00
C8—C13—H13A	109.00	C21—C26—H26B	109.00
C8—C13—H13B	109.00	C25—C26—H26B	109.00
C12—C13—H13B	109.00	H26A—C26—H26B	108.00
H13A—C13—H13B	108.00	C25—C26—H26A	109.00
C12—C13—H13A	109.00
C9—N1—C4—C3	179.7 (3)	C22—N3—C17—C16	−179.8 (3)
C4—N1—C9—C8	0.7 (5)	C17—N3—C22—C21	3.0 (5)
C4—N1—C9—C10	−179.6 (3)	C17—N3—C22—C23	−176.8 (3)
C9—N1—C4—C5	0.8 (4)	C22—N3—C17—C18	0.2 (5)
Br1—C1—C2—C3	176.6 (3)	Br3—C14—C15—C16	179.8 (3)
Br1—C1—C6—C5	−175.5 (3)	Br3—C14—C19—C18	177.8 (3)
C2—C1—C6—C5	2.3 (6)	C15—C14—C19—C18	−0.8 (6)
C6—C1—C2—C3	−1.2 (6)	C19—C14—C15—C16	−1.6 (6)
C1—C2—C3—Br2	179.7 (3)	C14—C15—C16—Br4	−177.3 (3)
C1—C2—C3—C4	−1.0 (6)	C14—C15—C16—C17	2.3 (5)
Br2—C3—C4—N1	2.2 (4)	Br4—C16—C17—N3	−1.1 (4)
Br2—C3—C4—C5	−178.8 (2)	Br4—C16—C17—C18	178.9 (2)
C2—C3—C4—C5	1.9 (5)	C15—C16—C17—C18	−0.6 (5)
C2—C3—C4—N1	−177.1 (3)	C15—C16—C17—N3	179.4 (3)
N1—C4—C5—C7	−0.1 (5)	N3—C17—C18—C20	−3.6 (5)
N1—C4—C5—C6	178.2 (3)	N3—C17—C18—C19	178.1 (3)
C3—C4—C5—C6	−0.8 (4)	C16—C17—C18—C19	−1.9 (4)
C3—C4—C5—C7	−179.1 (3)	C16—C17—C18—C20	176.4 (3)
C4—C5—C6—C1	−1.3 (5)	C17—C18—C19—C14	2.6 (5)
C4—C5—C7—C8	−2.1 (5)	C17—C18—C20—C21	3.9 (5)
C6—C5—C7—N2	−0.3 (5)	C19—C18—C20—N4	0.7 (5)
C6—C5—C7—C8	179.7 (3)	C19—C18—C20—C21	−177.8 (3)
C7—C5—C6—C1	177.0 (3)	C20—C18—C19—C14	−175.7 (3)
C4—C5—C7—N2	178.0 (3)	C17—C18—C20—N4	−177.6 (3)
C5—C7—C8—C9	3.4 (5)	C18—C20—C21—C22	−1.1 (5)
N2—C7—C8—C9	−176.6 (4)	N4—C20—C21—C22	−179.7 (3)
N2—C7—C8—C13	3.3 (6)	N4—C20—C21—C26	−1.1 (5)
C5—C7—C8—C13	−176.7 (3)	C18—C20—C21—C26	177.4 (3)
C7—C8—C9—C10	177.4 (3)	C20—C21—C22—C23	177.2 (3)
C13—C8—C9—N1	177.3 (3)	C26—C21—C22—N3	179.0 (3)
C7—C8—C13—C12	162.3 (4)	C20—C21—C26—C25	172.6 (3)
C9—C8—C13—C12	−17.8 (5)	C22—C21—C26—C25	−8.9 (5)
C13—C8—C9—C10	−2.4 (5)	C26—C21—C22—C23	−1.3 (5)
C7—C8—C9—N1	−2.9 (5)	C20—C21—C22—N3	−2.5 (5)
N1—C9—C10—C11	170.5 (3)	N3—C22—C23—C24	159.5 (3)
C8—C9—C10—C11	−9.8 (5)	C21—C22—C23—C24	−20.3 (5)
C9—C10—C11—C12	42.3 (5)	C22—C23—C24—C25	51.8 (5)
C10—C11—C12—C13	−62.7 (5)	C23—C24—C25—C26	−62.6 (5)
C11—C12—C13—C8	49.9 (5)	C24—C25—C26—C21	40.6 (5)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the N3/C1/C18/C20–C22 pyridine ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2NA···O1^i	0.84 (5)	2.39 (4)	3.215 (5)	168 (5)
O1—H1O···N3^ii	0.81 (4)	2.12 (3)	2.895 (4)	161 (5)
N4—H4NB···N1	0.88 (4)	2.36 (4)	3.207 (4)	161 (4)
C6—H6···O1^i	0.93	2.42	3.315 (5)	162
C25—H25B···Cg1^iii	0.97	2.95	3.820 (5)	151

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