3-Phenyl-5-p-tolyl-4-(3,4,5-tri­methoxy­benzyl­amino)-4H-1,2,4-triazole

In the title mol­ecule, C₂₅H₂₅N₄O₃, the dihedral angles between the phenyl, p-tolyl and trimethoxybenzylamino rings and the triazole ring are 34.3 (1), 52.9 (1) and 59.5 (1)°. The crystal structure is stabilized by N—H...N and C—H...N interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
Some non-H atoms missing
• R factor = 0.070
• wR factor = 0.224
• Data-to-parameter ratio = 21.7

checkCIF/PLATON results

No syntax errors found



Alert level B
DIFMX01_ALERT_2_B  The maximum difference density is > 0.1*ZMAX*1.00
            _refine_diff_density_max given =      0.877
            Test value =      0.800
PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............       0.88 e/A   3
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N2     -   N3       =      12.00 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C1     -   C3       =      10.95 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C2     -   C9       =      12.31 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C5     -   C6       =      10.28 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C10    -   C11      =       7.60 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C12    -   C15      =       8.05 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C13    -   C14      =       9.46 su

Alert level C
CHEMW01_ALERT_1_C  The difference between the given and expected weight for
            compound is greater 1 mass unit. Check that all hydrogen
            atoms have been taken into account.
DIFMX02_ALERT_1_C  The minimum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         42 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.99
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.80 mm
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.85
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.65 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.78 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C8       =       5.05 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4     -   C5       =       6.30 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C12    -   C13      =       6.36 su
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         C5
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C3
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C12

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C25 H25 N4 O3
            Atom count from the _atom_site data:  C25 H26 N4 O3
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: Large difference may be due to a
            symmetry error - see SYMMG tests
           From the CIF: _cell_formula_units_Z    4
           From the CIF: _chemical_formula_sum  C25 H25 N4 O3
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        100.00    100.00    0.00
           H        100.00    104.00   -4.00
           N         16.00     16.00    0.00
           O         12.00     12.00    0.00

   0 ALERT level A = In general: serious problem
   9 ALERT level B = Potentially serious problem
  17 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  18 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1997) and PARST (Nardelli, 1995).

3-Phenyl-5-p-tolyl-4-(3,4,5-trimethoxybenzylamino)-4H-1,2,4-triazole

Crystal data

C25H25N4O3	F(000) = 912
Mr = 430.51	Dx = 1.233 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.2141 (9) Å	Cell parameters from 22255 reflections
b = 9.8945 (5) Å	θ = 1.8–29.3°
c = 17.8861 (12) Å	µ = 0.08 mm^−1
β = 97.336 (5)°	T = 293 K
V = 2319.4 (3) Å^3	Prismatic, colourless
Z = 4	0.80 × 0.51 × 0.23 mm

Data collection

Stoe IPDS 2 diffractometer	6461 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2717 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.000
Detector resolution: 6.67 pixels mm^-1	θmax = 29.6°, θmin = 1.8°
rotation method scans	h = −18→18
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	k = 0→13
Tmin = 0.928, Tmax = 0.982	l = 0→24
6461 measured reflections

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)] = 0.070	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.224	w = 1/[σ^2(Fo^2) + (0.1262P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.83	(Δ/σ)max < 0.001
6461 reflections	Δρmax = 0.88 e Å^−3
298 parameters	Δρmin = −0.31 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (2)

Special details

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.

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 > σ(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 (Ų)

	x	y	z	Uiso*/Ueq
O2	0.25690 (13)	0.16742 (16)	0.48652 (10)	0.0744 (5)
N4	0.62928 (15)	0.45658 (17)	0.68185 (11)	0.0607 (5)
C22	0.52370 (17)	0.2735 (2)	0.51896 (13)	0.0608 (6)
H22	0.5864	0.2493	0.5045	0.073*
N1	0.63392 (15)	0.32612 (17)	0.71356 (10)	0.0615 (5)
C18	0.42537 (17)	0.4140 (2)	0.59168 (12)	0.0591 (6)
H18	0.4218	0.4849	0.6254	0.071*
C19	0.33795 (17)	0.3437 (2)	0.56356 (12)	0.0595 (6)
O1	0.24276 (13)	0.3728 (2)	0.58098 (11)	0.0835 (6)
C2	0.6967 (2)	0.2220 (2)	0.70312 (14)	0.0677 (7)
C16	0.61322 (17)	0.4546 (2)	0.59876 (13)	0.0604 (6)
H16A	0.6717	0.4129	0.5803	0.073*
H16B	0.6078	0.5466	0.5800	0.073*
C17	0.51815 (17)	0.3777 (2)	0.56914 (12)	0.0551 (5)
C20	0.34343 (17)	0.2381 (2)	0.51345 (12)	0.0607 (6)
O3	0.43324 (16)	0.10241 (19)	0.43842 (12)	0.0876 (6)
N2	0.6684 (2)	0.1144 (2)	0.73602 (14)	0.0869 (8)
C9	0.7788 (2)	0.2302 (2)	0.65563 (15)	0.0733 (8)
C21	0.43630 (19)	0.2045 (2)	0.48992 (13)	0.0636 (6)
C14	0.7786 (2)	0.1369 (3)	0.59801 (17)	0.0802 (8)
H14	0.7306	0.0677	0.5926	0.096*
C1	0.5619 (2)	0.2733 (2)	0.75425 (13)	0.0717 (7)
C3	0.4748 (2)	0.3446 (3)	0.77930 (14)	0.0728 (7)
N3	0.5824 (2)	0.1469 (2)	0.76896 (14)	0.0860 (7)
C10	0.8525 (2)	0.3299 (3)	0.66486 (17)	0.0783 (8)
H10	0.8549	0.3901	0.7050	0.094*
C24	0.2068 (2)	0.2208 (3)	0.41775 (16)	0.0879 (9)
H24A	0.1881	0.3131	0.4252	0.132*
H24B	0.1466	0.1687	0.4019	0.132*
H24C	0.2520	0.2166	0.3798	0.132*
C8	0.4784 (2)	0.4780 (3)	0.80062 (16)	0.0865 (8)
H8	0.5377	0.5276	0.7981	0.104*
C11	0.9219 (3)	0.3394 (3)	0.6148 (2)	0.0962 (10)
H11	0.9702	0.4083	0.6200	0.115*
C13	0.8485 (3)	0.1475 (3)	0.5499 (2)	0.0937 (10)
H13	0.8470	0.0846	0.5111	0.112*
C12	0.9211 (2)	0.2451 (4)	0.55498 (19)	0.0934 (9)
C7	0.3953 (3)	0.5391 (4)	0.8257 (2)	0.1018 (10)
H7	0.3993	0.6294	0.8402	0.122*
C25	0.5190 (3)	0.0838 (4)	0.3990 (2)	0.1072 (11)
H25A	0.5337	0.1668	0.3747	0.161*
H25B	0.5044	0.0143	0.3618	0.161*
H25C	0.5770	0.0579	0.4340	0.161*
C23	0.2293 (2)	0.4968 (4)	0.6155 (2)	0.1058 (11)
H23A	0.2643	0.4957	0.6660	0.159*
H23B	0.1579	0.5123	0.6170	0.159*
H23C	0.2566	0.5677	0.5874	0.159*
C15	0.9943 (3)	0.2586 (6)	0.5039 (3)	0.1458 (17)
H15A	0.9710	0.2111	0.4581	0.219*
H15B	1.0582	0.2213	0.5260	0.219*
H15C	1.0031	0.3525	0.4929	0.219*
C6	0.3059 (3)	0.4683 (5)	0.8297 (2)	0.1191 (13)
H6	0.2496	0.5098	0.8462	0.143*
C4	0.3851 (3)	0.2734 (4)	0.7833 (2)	0.1094 (12)
H4	0.3804	0.1831	0.7687	0.131*
C5	0.3031 (3)	0.3367 (6)	0.8089 (3)	0.1358 (17)
H5	0.2439	0.2874	0.8119	0.163*
H4N	0.6789 (18)	0.498 (2)	0.7003 (13)	0.058 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0726 (10)	0.0734 (10)	0.0704 (10)	−0.0228 (8)	−0.0170 (8)	0.0003 (8)
N4	0.0663 (12)	0.0408 (8)	0.0680 (12)	−0.0070 (8)	−0.0189 (9)	0.0044 (8)
C22	0.0616 (13)	0.0562 (12)	0.0609 (13)	0.0027 (10)	−0.0071 (10)	0.0054 (10)
N1	0.0741 (12)	0.0462 (9)	0.0559 (10)	−0.0023 (9)	−0.0232 (9)	0.0039 (8)
C18	0.0633 (14)	0.0561 (12)	0.0531 (12)	−0.0043 (10)	−0.0106 (10)	0.0006 (9)
C19	0.0571 (13)	0.0660 (13)	0.0519 (12)	−0.0062 (10)	−0.0062 (10)	0.0035 (10)
O1	0.0602 (11)	0.1040 (14)	0.0845 (12)	−0.0097 (9)	0.0027 (9)	−0.0231 (11)
C2	0.0825 (16)	0.0505 (12)	0.0620 (14)	0.0007 (11)	−0.0217 (12)	−0.0002 (10)
C16	0.0605 (12)	0.0536 (11)	0.0622 (13)	−0.0038 (9)	−0.0114 (10)	0.0132 (10)
C17	0.0611 (13)	0.0494 (10)	0.0499 (11)	−0.0035 (9)	−0.0115 (9)	0.0122 (9)
C20	0.0676 (14)	0.0544 (12)	0.0544 (12)	−0.0112 (10)	−0.0141 (10)	0.0055 (10)
O3	0.0951 (14)	0.0739 (11)	0.0887 (13)	−0.0013 (10)	−0.0074 (11)	−0.0266 (10)
N2	0.122 (2)	0.0501 (11)	0.0776 (14)	−0.0038 (12)	−0.0274 (14)	0.0154 (10)
C9	0.0883 (17)	0.0445 (11)	0.0757 (16)	0.0110 (11)	−0.0331 (14)	−0.0088 (11)
C21	0.0740 (15)	0.0516 (12)	0.0601 (13)	0.0000 (10)	−0.0113 (11)	0.0003 (10)
C14	0.0867 (19)	0.0688 (15)	0.0784 (18)	0.0085 (14)	−0.0154 (15)	−0.0112 (13)
C1	0.0953 (18)	0.0580 (13)	0.0538 (13)	−0.0216 (13)	−0.0209 (12)	0.0162 (10)
C3	0.0805 (17)	0.0750 (16)	0.0576 (13)	−0.0075 (13)	−0.0120 (12)	0.0160 (12)
N3	0.1095 (19)	0.0677 (14)	0.0755 (15)	−0.0045 (13)	−0.0083 (14)	0.0185 (11)
C10	0.0756 (17)	0.0673 (15)	0.0882 (19)	0.0058 (12)	−0.0036 (15)	−0.0190 (13)
C24	0.0788 (17)	0.102 (2)	0.0744 (17)	−0.0102 (15)	−0.0242 (14)	−0.0024 (15)
C8	0.0842 (19)	0.096 (2)	0.0724 (17)	−0.0120 (16)	−0.0156 (14)	0.0001 (15)
C11	0.085 (2)	0.0848 (19)	0.114 (3)	0.0015 (15)	−0.0061 (19)	−0.0155 (18)
C13	0.096 (2)	0.0820 (19)	0.094 (2)	0.0068 (16)	−0.0239 (18)	−0.0206 (16)
C12	0.0733 (18)	0.122 (3)	0.085 (2)	0.0187 (18)	0.0107 (15)	0.0006 (18)
C7	0.086 (2)	0.117 (3)	0.098 (2)	0.005 (2)	−0.0085 (18)	−0.003 (2)
C25	0.123 (3)	0.102 (2)	0.099 (2)	0.006 (2)	0.020 (2)	−0.0332 (19)
C23	0.0744 (19)	0.126 (3)	0.115 (3)	0.0066 (18)	0.0064 (17)	−0.032 (2)
C15	0.100 (3)	0.203 (5)	0.135 (3)	−0.007 (3)	0.016 (3)	−0.004 (4)
C6	0.122 (3)	0.126 (3)	0.104 (3)	−0.008 (3)	−0.003 (2)	0.035 (2)
C4	0.124 (3)	0.092 (2)	0.110 (3)	−0.034 (2)	0.005 (2)	0.0335 (19)
C5	0.093 (3)	0.162 (4)	0.158 (4)	−0.013 (3)	0.037 (3)	0.056 (3)

Geometric parameters (Å, º)

O2—C20	1.374 (2)	C3—C8	1.372 (4)
O2—C24	1.422 (3)	C3—C4	1.388 (4)
N4—N1	1.408 (2)	C10—C11	1.364 (5)
N4—C16	1.474 (3)	C10—H10	0.9300
N4—H4N	0.81 (2)	C24—H24A	0.9600
C22—C17	1.375 (3)	C24—H24B	0.9600
C22—C21	1.384 (3)	C24—H24C	0.9600
C22—H22	0.9300	C8—C7	1.379 (5)
N1—C2	1.351 (3)	C8—H8	0.9300
N1—C1	1.373 (3)	C11—C12	1.419 (5)
C18—C17	1.386 (3)	C11—H11	0.9300
C18—C19	1.387 (3)	C13—C12	1.356 (5)
C18—H18	0.9300	C13—H13	0.9300
C19—O1	1.365 (3)	C12—C15	1.419 (5)
C19—C20	1.385 (3)	C7—C6	1.382 (5)
O1—C23	1.395 (4)	C7—H7	0.9300
C2—N2	1.295 (3)	C25—H25A	0.9600
C2—C9	1.462 (4)	C25—H25B	0.9600
C16—C17	1.506 (3)	C25—H25C	0.9600
C16—H16A	0.9700	C23—H23A	0.9600
C16—H16B	0.9700	C23—H23B	0.9600
C20—C21	1.388 (4)	C23—H23C	0.9600
O3—C21	1.365 (3)	C15—H15A	0.9600
O3—C25	1.421 (4)	C15—H15B	0.9600
N2—N3	1.382 (4)	C15—H15C	0.9600
C9—C10	1.382 (4)	C6—C5	1.353 (6)
C9—C14	1.383 (4)	C6—H6	0.9300
C14—C13	1.346 (5)	C4—C5	1.380 (6)
C14—H14	0.9300	C4—H4	0.9300
C1—N3	1.300 (3)	C5—H5	0.9300
C1—C3	1.468 (4)
C20—O2—C24	112.87 (19)	C11—C10—H10	120.2
N1—N4—C16	112.76 (16)	C9—C10—H10	120.2
N1—N4—H4N	108.0 (16)	O2—C24—H24A	109.5
C16—N4—H4N	115.1 (17)	O2—C24—H24B	109.5
C17—C22—C21	120.2 (2)	H24A—C24—H24B	109.5
C17—C22—H22	119.9	O2—C24—H24C	109.5
C21—C22—H22	119.9	H24A—C24—H24C	109.5
C2—N1—C1	105.2 (2)	H24B—C24—H24C	109.5
C2—N1—N4	129.7 (2)	C3—C8—C7	120.7 (3)
C1—N1—N4	124.4 (2)	C3—C8—H8	119.6
C17—C18—C19	119.4 (2)	C7—C8—H8	119.6
C17—C18—H18	120.3	C10—C11—C12	120.6 (3)
C19—C18—H18	120.3	C10—C11—H11	119.7
O1—C19—C20	115.64 (19)	C12—C11—H11	119.7
O1—C19—C18	124.1 (2)	C14—C13—C12	123.4 (3)
C20—C19—C18	120.2 (2)	C14—C13—H13	118.3
C19—O1—C23	117.4 (2)	C12—C13—H13	118.3
N2—C2—N1	110.2 (3)	C13—C12—C15	123.9 (4)
N2—C2—C9	126.0 (2)	C13—C12—C11	117.1 (3)
N1—C2—C9	123.5 (2)	C15—C12—C11	118.9 (4)
N4—C16—C17	111.57 (19)	C8—C7—C6	121.1 (4)
N4—C16—H16A	109.3	C8—C7—H7	119.5
C17—C16—H16A	109.3	C6—C7—H7	119.5
N4—C16—H16B	109.3	O3—C25—H25A	109.5
C17—C16—H16B	109.3	O3—C25—H25B	109.5
H16A—C16—H16B	108.0	H25A—C25—H25B	109.5
C22—C17—C18	120.5 (2)	O3—C25—H25C	109.5
C22—C17—C16	119.8 (2)	H25A—C25—H25C	109.5
C18—C17—C16	119.7 (2)	H25B—C25—H25C	109.5
O2—C20—C19	120.1 (2)	O1—C23—H23A	109.5
O2—C20—C21	120.0 (2)	O1—C23—H23B	109.5
C19—C20—C21	119.9 (2)	H23A—C23—H23B	109.5
C21—O3—C25	118.3 (2)	O1—C23—H23C	109.5
C2—N2—N3	107.7 (2)	H23A—C23—H23C	109.5
C10—C9—C14	120.0 (3)	H23B—C23—H23C	109.5
C10—C9—C2	122.3 (2)	C12—C15—H15A	109.5
C14—C9—C2	117.7 (3)	C12—C15—H15B	109.5
O3—C21—C22	124.7 (2)	H15A—C15—H15B	109.5
O3—C21—C20	115.5 (2)	C12—C15—H15C	109.5
C22—C21—C20	119.7 (2)	H15A—C15—H15C	109.5
C13—C14—C9	119.3 (3)	H15B—C15—H15C	109.5
C13—C14—H14	120.4	C5—C6—C7	117.9 (4)
C9—C14—H14	120.4	C5—C6—H6	121.1
N3—C1—N1	109.4 (3)	C7—C6—H6	121.1
N3—C1—C3	123.5 (3)	C5—C4—C3	119.8 (4)
N1—C1—C3	127.0 (2)	C5—C4—H4	120.1
C8—C3—C4	118.3 (3)	C3—C4—H4	120.1
C8—C3—C1	123.1 (3)	C6—C5—C4	122.2 (4)
C4—C3—C1	118.6 (3)	C6—C5—H5	118.9
C1—N3—N2	107.4 (2)	C4—C5—H5	118.9
C11—C10—C9	119.6 (3)
C16—N4—N1—C2	57.1 (3)	O2—C20—C21—O3	1.7 (3)
C16—N4—N1—C1	−112.4 (2)	C19—C20—C21—O3	−177.7 (2)
C17—C18—C19—O1	−178.7 (2)	O2—C20—C21—C22	−178.10 (19)
C17—C18—C19—C20	0.0 (3)	C19—C20—C21—C22	2.5 (3)
C20—C19—O1—C23	−164.5 (2)	C10—C9—C14—C13	−2.3 (4)
C18—C19—O1—C23	14.3 (4)	C2—C9—C14—C13	175.2 (2)
C1—N1—C2—N2	−1.6 (2)	C2—N1—C1—N3	1.8 (2)
N4—N1—C2—N2	−172.65 (19)	N4—N1—C1—N3	173.45 (19)
C1—N1—C2—C9	173.51 (19)	C2—N1—C1—C3	−178.9 (2)
N4—N1—C2—C9	2.5 (3)	N4—N1—C1—C3	−7.2 (3)
N1—N4—C16—C17	56.6 (3)	N3—C1—C3—C8	144.5 (3)
C21—C22—C17—C18	0.6 (3)	N1—C1—C3—C8	−34.8 (3)
C21—C22—C17—C16	−178.32 (19)	N3—C1—C3—C4	−34.1 (4)
C19—C18—C17—C22	0.4 (3)	N1—C1—C3—C4	146.7 (3)
C19—C18—C17—C16	179.33 (19)	N1—C1—N3—N2	−1.3 (3)
N4—C16—C17—C22	−125.8 (2)	C3—C1—N3—N2	179.3 (2)
N4—C16—C17—C18	55.3 (2)	C2—N2—N3—C1	0.3 (3)
C24—O2—C20—C19	92.0 (3)	C14—C9—C10—C11	3.1 (4)
C24—O2—C20—C21	−87.4 (3)	C2—C9—C10—C11	−174.4 (2)
O1—C19—C20—O2	−2.0 (3)	C4—C3—C8—C7	0.4 (4)
C18—C19—C20—O2	179.09 (19)	C1—C3—C8—C7	−178.2 (3)
O1—C19—C20—C21	177.4 (2)	C9—C10—C11—C12	−2.2 (4)
C18—C19—C20—C21	−1.5 (3)	C9—C14—C13—C12	0.7 (4)
N1—C2—N2—N3	0.8 (3)	C14—C13—C12—C15	−178.9 (4)
C9—C2—N2—N3	−174.1 (2)	C14—C13—C12—C11	0.2 (5)
N2—C2—C9—C10	−132.2 (3)	C10—C11—C12—C13	0.6 (5)
N1—C2—C9—C10	53.5 (3)	C10—C11—C12—C15	179.7 (4)
N2—C2—C9—C14	50.4 (3)	C3—C8—C7—C6	−0.4 (5)
N1—C2—C9—C14	−124.0 (2)	C8—C7—C6—C5	0.6 (6)
C25—O3—C21—C22	−14.6 (4)	C8—C3—C4—C5	−0.6 (5)
C25—O3—C21—C20	165.6 (3)	C1—C3—C4—C5	178.0 (3)
C17—C22—C21—O3	178.1 (2)	C7—C6—C5—C4	−0.9 (6)
C17—C22—C21—C20	−2.0 (3)	C3—C4—C5—C6	0.9 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4N···N2^i	0.81 (2)	2.47 (2)	3.277 (3)	176 (1)
C10—H10···N2^i	0.93	2.49	3.357 (4)	155

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