5-(2-Hydroxy­phen­yl)-4-(4-methoxy­phen­yl)-3-(4-methyl­phen­yl)-4H-1,2,4-triazole

In the title compound, C₂₂H₁₉N₃O₂, there are two independent mol­ecules in the asymmetric unit. Intra­molecular O—H...N hydrogen bonds are observed in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.129
• Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C24    -   C25     ..       7.01 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C31    -   C32     ..       7.35 su

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N3     -   C1      ..       5.25 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N4     -   N5      ..       6.78 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C34

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

5-(2-Hydroxyphenyl)-4-(4-methoxyphenyl)-3-(4-methylphenyl)-4H-1,2,4-triazole

Crystal data

C22H19N3O2	Z = 4
Mr = 357.40	F(000) = 752
Triclinic, P1	Dx = 1.285 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5954 (4) Å	Cell parameters from 3025 reflections
b = 12.4637 (5) Å	θ = 2.3–25.3°
c = 15.8750 (6) Å	µ = 0.08 mm^−1
α = 90.9566 (6)°	T = 298 K
β = 103.2093 (6)°	Block, colourless
γ = 90.4278 (6)°	0.18 × 0.16 × 0.11 mm
V = 1847.95 (13) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	8963 independent reflections
Radiation source: fine-focus sealed tube	4446 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.985, Tmax = 0.991	k = −16→16
22546 measured reflections	l = −20→21

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.129	w = 1/[σ^2(Fo^2) + (0.0672P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max = 0.019
8963 reflections	Δρmax = 0.20 e Å^−3
500 parameters	Δρmin = −0.12 e Å^−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997a), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0081 (12)

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
C1	0.24942 (14)	1.01507 (11)	0.49980 (9)	0.0562 (3)
C2	0.10930 (14)	0.87280 (11)	0.47266 (9)	0.0564 (4)
C3	0.02160 (14)	0.78044 (11)	0.43379 (9)	0.0588 (4)
C4	−0.01245 (17)	0.70181 (13)	0.48799 (10)	0.0686 (4)
C5	−0.09376 (19)	0.61227 (13)	0.45341 (13)	0.0818 (5)
H5	−0.1156	0.5605	0.4901	0.098*
C6	−0.14188 (19)	0.59956 (14)	0.36592 (14)	0.0857 (5)
H6	−0.1936	0.5382	0.3433	0.103*
C7	−0.11408 (18)	0.67720 (14)	0.31116 (12)	0.0808 (5)
H7	−0.1496	0.6696	0.2517	0.097*
C8	−0.03340 (16)	0.76601 (13)	0.34493 (10)	0.0701 (4)
H8	−0.0149	0.8180	0.3075	0.084*
C9	0.34288 (14)	1.10637 (11)	0.49094 (9)	0.0555 (3)
C10	0.42773 (16)	1.10746 (12)	0.43117 (10)	0.0634 (4)
H10	0.4250	1.0492	0.3934	0.076*
C11	0.51598 (16)	1.19357 (12)	0.42689 (10)	0.0680 (4)
H11	0.5714	1.1924	0.3859	0.082*
C12	0.52475 (15)	1.28183 (12)	0.48172 (10)	0.0655 (4)
C13	0.44224 (17)	1.27926 (13)	0.54290 (10)	0.0706 (4)
H13	0.4471	1.3368	0.5815	0.085*
C14	0.35334 (16)	1.19362 (12)	0.54785 (9)	0.0650 (4)
H14	0.2996	1.1941	0.5898	0.078*
C15	0.61729 (18)	1.37738 (13)	0.47302 (12)	0.0877 (5)
H15A	0.7098	1.3533	0.4678	0.132*
H15B	0.6277	1.4233	0.5233	0.132*
H15C	0.5733	1.4164	0.4224	0.132*
C16	0.17266 (14)	0.95902 (10)	0.34289 (8)	0.0527 (3)
C17	0.25054 (15)	0.89442 (11)	0.30036 (9)	0.0591 (4)
H17	0.3103	0.8426	0.3305	0.071*
C18	0.24011 (15)	0.90631 (11)	0.21283 (9)	0.0619 (4)
H18	0.2919	0.8619	0.1839	0.074*
C19	0.15301 (16)	0.98390 (12)	0.16841 (9)	0.0613 (4)
C20	0.07391 (17)	1.04825 (12)	0.21219 (9)	0.0705 (4)
H20	0.0138	1.1001	0.1823	0.085*
C21	0.08364 (16)	1.03603 (11)	0.29886 (9)	0.0641 (4)
H21	0.0306	1.0794	0.3278	0.077*
C22	0.20854 (19)	0.93831 (14)	0.03339 (10)	0.0820 (5)
H22A	0.3092	0.9410	0.0595	0.123*
H22B	0.1922	0.9647	−0.0245	0.123*
H22C	0.1744	0.8655	0.0318	0.123*
C23	0.29425 (19)	0.53207 (14)	0.88987 (11)	0.0805 (5)
C24	0.46717 (19)	0.51286 (12)	0.82096 (11)	0.0750 (5)
C25	0.57951 (19)	0.52689 (13)	0.77400 (10)	0.0742 (5)
C26	0.6467 (2)	0.43526 (15)	0.74909 (12)	0.0911 (6)
C27	0.7551 (3)	0.4467 (2)	0.70579 (13)	0.1096 (7)
H27	0.7995	0.3858	0.6903	0.132*
C28	0.7983 (2)	0.5443 (2)	0.68527 (12)	0.1006 (6)
H28	0.8715	0.5500	0.6559	0.121*
C29	0.7341 (2)	0.63527 (16)	0.70789 (12)	0.0911 (5)
H29	0.7633	0.7025	0.6935	0.109*
C30	0.6272 (2)	0.62657 (14)	0.75155 (11)	0.0820 (5)
H30	0.5850	0.6887	0.7668	0.098*
C31	0.18659 (19)	0.58328 (13)	0.92926 (11)	0.0782 (5)
C32	0.1918 (2)	0.57627 (16)	1.01618 (13)	0.0980 (6)
H32	0.2622	0.5349	1.0505	0.118*
C33	0.0949 (2)	0.62928 (17)	1.05370 (13)	0.1009 (6)
H33	0.1022	0.6229	1.1128	0.121*
C34	−0.0111 (2)	0.69076 (15)	1.00679 (14)	0.0896 (5)
C35	−0.0212 (2)	0.69422 (17)	0.91951 (14)	0.1001 (6)
H35	−0.0955	0.7322	0.8853	0.120*
C36	0.0754 (2)	0.64311 (17)	0.88078 (13)	0.0962 (6)
H36	0.0662	0.6486	0.8214	0.115*
C37	−0.1104 (2)	0.75419 (17)	1.04873 (16)	0.1185 (7)
H37A	−0.1329	0.8206	1.0191	0.178*
H37B	−0.0648	0.7690	1.1082	0.178*
H37C	−0.1969	0.7136	1.0457	0.178*
C38	0.38954 (15)	0.70377 (11)	0.84731 (9)	0.0579 (4)
C39	0.46871 (16)	0.75577 (11)	0.92031 (9)	0.0638 (4)
H39	0.5164	0.7165	0.9673	0.077*
C40	0.47669 (16)	0.86524 (11)	0.92317 (9)	0.0640 (4)
H40	0.5298	0.9005	0.9723	0.077*
C41	0.40582 (15)	0.92418 (10)	0.85303 (9)	0.0554 (3)
C42	0.32699 (15)	0.87201 (11)	0.78019 (9)	0.0601 (4)
H42	0.2799	0.9110	0.7329	0.072*
C43	0.31854 (15)	0.76107 (11)	0.77817 (9)	0.0619 (4)
H43	0.2644	0.7253	0.7296	0.074*
C44	0.3460 (2)	1.09826 (13)	0.79523 (12)	0.0996 (6)
H44A	0.3799	1.0830	0.7440	0.149*
H44B	0.3637	1.1725	0.8115	0.149*
H44C	0.2450	1.0834	0.7841	0.149*
H1	0.074 (2)	0.7768 (13)	0.5875 (14)	0.134 (9)*
H2	0.545 (2)	0.3377 (19)	0.8002 (15)	0.146 (11)*
N1	0.22230 (13)	0.98581 (10)	0.57369 (7)	0.0630 (3)
N2	0.13441 (13)	0.89634 (10)	0.55629 (7)	0.0636 (3)
N3	0.18100 (12)	0.94645 (9)	0.43397 (7)	0.0540 (3)
N4	0.3256 (2)	0.42997 (12)	0.89016 (12)	0.1030 (5)
N5	0.4330 (2)	0.41817 (12)	0.84640 (12)	0.0988 (5)
N6	0.37982 (14)	0.58820 (9)	0.84669 (8)	0.0686 (3)
O1	0.02918 (15)	0.70856 (11)	0.57578 (8)	0.0918 (4)
O2	0.13424 (13)	1.00302 (9)	0.08275 (6)	0.0852 (3)
O3	0.6088 (2)	0.33499 (12)	0.76654 (12)	0.1232 (5)
O4	0.41904 (12)	1.03287 (8)	0.86360 (6)	0.0756 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0584 (8)	0.0628 (9)	0.0483 (8)	0.0149 (7)	0.0131 (6)	0.0062 (7)
C2	0.0571 (8)	0.0643 (9)	0.0499 (8)	0.0127 (7)	0.0156 (7)	0.0112 (7)
C3	0.0576 (8)	0.0634 (9)	0.0572 (9)	0.0104 (7)	0.0162 (7)	0.0097 (7)
C4	0.0689 (10)	0.0706 (10)	0.0672 (11)	0.0103 (8)	0.0162 (8)	0.0151 (8)
C5	0.0856 (12)	0.0671 (11)	0.0949 (14)	0.0051 (9)	0.0241 (10)	0.0197 (9)
C6	0.0857 (12)	0.0693 (11)	0.1033 (15)	0.0000 (9)	0.0244 (11)	0.0013 (10)
C7	0.0829 (11)	0.0840 (12)	0.0742 (11)	−0.0073 (10)	0.0161 (9)	−0.0050 (9)
C8	0.0715 (10)	0.0761 (11)	0.0637 (10)	−0.0011 (8)	0.0175 (8)	0.0045 (8)
C9	0.0561 (8)	0.0605 (9)	0.0500 (8)	0.0106 (7)	0.0116 (6)	0.0057 (7)
C10	0.0709 (10)	0.0610 (9)	0.0612 (9)	0.0087 (8)	0.0210 (8)	0.0010 (7)
C11	0.0697 (10)	0.0714 (10)	0.0671 (10)	0.0052 (8)	0.0242 (8)	0.0044 (8)
C12	0.0585 (9)	0.0676 (10)	0.0675 (10)	0.0068 (7)	0.0081 (7)	0.0061 (8)
C13	0.0709 (10)	0.0710 (10)	0.0671 (10)	0.0019 (8)	0.0110 (8)	−0.0100 (8)
C14	0.0674 (9)	0.0742 (10)	0.0541 (9)	0.0079 (8)	0.0150 (7)	0.0003 (7)
C15	0.0832 (12)	0.0814 (12)	0.0986 (14)	−0.0102 (10)	0.0213 (10)	−0.0009 (10)
C16	0.0598 (8)	0.0568 (8)	0.0430 (7)	0.0063 (7)	0.0138 (6)	0.0081 (6)
C17	0.0649 (9)	0.0601 (9)	0.0541 (9)	0.0144 (7)	0.0164 (7)	0.0097 (6)
C18	0.0691 (9)	0.0630 (9)	0.0572 (9)	0.0079 (7)	0.0218 (7)	−0.0011 (7)
C19	0.0707 (9)	0.0698 (9)	0.0446 (8)	0.0007 (8)	0.0153 (7)	0.0061 (7)
C20	0.0838 (11)	0.0742 (10)	0.0542 (9)	0.0266 (8)	0.0156 (8)	0.0162 (7)
C21	0.0744 (10)	0.0675 (9)	0.0538 (9)	0.0207 (7)	0.0203 (7)	0.0077 (7)
C22	0.0925 (12)	0.1028 (13)	0.0560 (9)	−0.0119 (10)	0.0286 (9)	−0.0072 (9)
C23	0.0813 (12)	0.0698 (12)	0.0798 (12)	−0.0184 (10)	−0.0035 (9)	0.0108 (9)
C24	0.0865 (12)	0.0490 (9)	0.0749 (11)	−0.0022 (9)	−0.0115 (9)	−0.0012 (8)
C25	0.0852 (12)	0.0638 (10)	0.0623 (10)	0.0077 (9)	−0.0067 (9)	−0.0028 (8)
C26	0.1171 (16)	0.0672 (12)	0.0734 (12)	0.0170 (11)	−0.0100 (11)	−0.0110 (9)
C27	0.133 (2)	0.1104 (18)	0.0781 (14)	0.0440 (15)	0.0080 (13)	−0.0147 (12)
C28	0.1072 (15)	0.1196 (17)	0.0692 (12)	0.0331 (14)	0.0075 (10)	−0.0028 (12)
C29	0.0855 (13)	0.1013 (15)	0.0843 (13)	0.0118 (11)	0.0139 (10)	0.0046 (10)
C30	0.0852 (12)	0.0713 (11)	0.0842 (12)	0.0123 (9)	0.0081 (10)	−0.0012 (9)
C31	0.0758 (11)	0.0784 (11)	0.0712 (11)	−0.0267 (9)	−0.0027 (9)	0.0169 (9)
C32	0.0965 (14)	0.1036 (15)	0.0817 (14)	−0.0090 (12)	−0.0062 (11)	0.0215 (11)
C33	0.1054 (16)	0.1171 (16)	0.0737 (13)	−0.0190 (13)	0.0069 (12)	0.0160 (11)
C34	0.0783 (12)	0.0928 (13)	0.0945 (15)	−0.0293 (10)	0.0125 (11)	0.0207 (11)
C35	0.0744 (12)	0.1236 (16)	0.0971 (16)	−0.0086 (11)	0.0065 (11)	0.0392 (12)
C36	0.0820 (13)	0.1240 (16)	0.0771 (12)	−0.0110 (12)	0.0052 (10)	0.0278 (11)
C37	0.1041 (16)	0.1251 (18)	0.1351 (19)	−0.0251 (14)	0.0452 (14)	0.0176 (14)
C38	0.0642 (9)	0.0509 (8)	0.0539 (8)	−0.0059 (7)	0.0038 (7)	0.0025 (6)
C39	0.0754 (10)	0.0597 (9)	0.0494 (8)	−0.0019 (7)	−0.0002 (7)	0.0080 (7)
C40	0.0775 (10)	0.0603 (9)	0.0474 (8)	−0.0047 (7)	0.0008 (7)	−0.0019 (7)
C41	0.0641 (9)	0.0504 (8)	0.0512 (8)	0.0009 (6)	0.0123 (7)	−0.0005 (6)
C42	0.0688 (9)	0.0591 (9)	0.0489 (8)	0.0059 (7)	0.0055 (7)	0.0062 (7)
C43	0.0715 (9)	0.0602 (9)	0.0481 (8)	−0.0035 (7)	0.0019 (7)	−0.0026 (7)
C44	0.1221 (15)	0.0607 (10)	0.1027 (14)	0.0085 (10)	−0.0034 (12)	0.0199 (10)
N1	0.0691 (8)	0.0720 (8)	0.0492 (7)	0.0060 (7)	0.0157 (6)	0.0066 (6)
N2	0.0679 (8)	0.0733 (8)	0.0513 (7)	0.0052 (6)	0.0166 (6)	0.0075 (6)
N3	0.0592 (7)	0.0593 (7)	0.0443 (6)	0.0072 (5)	0.0131 (5)	0.0062 (5)
N4	0.1086 (13)	0.0628 (10)	0.1271 (14)	−0.0195 (9)	0.0046 (11)	0.0183 (9)
N5	0.1062 (13)	0.0609 (10)	0.1202 (14)	−0.0076 (9)	0.0067 (10)	0.0078 (8)
N6	0.0785 (9)	0.0548 (8)	0.0646 (8)	−0.0099 (7)	0.0000 (7)	0.0047 (6)
O1	0.1101 (10)	0.0946 (10)	0.0698 (8)	−0.0079 (8)	0.0174 (7)	0.0251 (7)
O2	0.1053 (9)	0.1071 (9)	0.0466 (6)	0.0216 (7)	0.0233 (6)	0.0119 (6)
O3	0.1670 (16)	0.0674 (9)	0.1274 (13)	0.0193 (9)	0.0181 (12)	−0.0135 (8)
O4	0.0964 (8)	0.0530 (6)	0.0697 (7)	0.0030 (5)	0.0031 (6)	0.0009 (5)

Geometric parameters (Å, º)

C1—N1	1.3150 (17)	C23—C31	1.469 (3)
C1—N3	1.3794 (17)	C24—N5	1.317 (2)
C1—C9	1.4720 (19)	C24—N6	1.381 (2)
C2—N2	1.3216 (17)	C24—C25	1.455 (2)
C2—N3	1.3770 (17)	C25—C30	1.400 (2)
C2—C3	1.462 (2)	C25—C26	1.410 (2)
C3—C8	1.397 (2)	C26—O3	1.350 (2)
C3—C4	1.400 (2)	C26—C27	1.379 (3)
C4—O1	1.3602 (18)	C27—C28	1.351 (3)
C4—C5	1.388 (2)	C27—H27	0.9300
C5—C6	1.366 (2)	C28—C29	1.375 (3)
C5—H5	0.9300	C28—H28	0.9300
C6—C7	1.376 (2)	C29—C30	1.367 (2)
C6—H6	0.9300	C29—H29	0.9300
C7—C8	1.375 (2)	C30—H30	0.9300
C7—H7	0.9300	C31—C32	1.374 (2)
C8—H8	0.9300	C31—C36	1.394 (2)
C9—C10	1.3845 (19)	C32—C33	1.380 (3)
C9—C14	1.3903 (19)	C32—H32	0.9300
C10—C11	1.374 (2)	C33—C34	1.364 (3)
C10—H10	0.9300	C33—H33	0.9300
C11—C12	1.381 (2)	C34—C35	1.368 (3)
C11—H11	0.9300	C34—C37	1.503 (3)
C12—C13	1.387 (2)	C35—C36	1.378 (3)
C12—C15	1.507 (2)	C35—H35	0.9300
C13—C14	1.376 (2)	C36—H36	0.9300
C13—H13	0.9300	C37—H37A	0.9600
C14—H14	0.9300	C37—H37B	0.9600
C15—H15A	0.9600	C37—H37C	0.9600
C15—H15B	0.9600	C38—C43	1.3677 (18)
C15—H15C	0.9600	C38—C39	1.3803 (18)
C16—C17	1.3725 (18)	C38—N6	1.4424 (17)
C16—C21	1.3788 (18)	C39—C40	1.3653 (18)
C16—N3	1.4411 (16)	C39—H39	0.9300
C17—C18	1.3808 (18)	C40—C41	1.3895 (19)
C17—H17	0.9300	C40—H40	0.9300
C18—C19	1.3771 (18)	C41—O4	1.3637 (15)
C18—H18	0.9300	C41—C42	1.3783 (19)
C19—O2	1.3558 (16)	C42—C43	1.3840 (18)
C19—C20	1.391 (2)	C42—H42	0.9300
C20—C21	1.3688 (19)	C43—H43	0.9300
C20—H20	0.9300	C44—O4	1.4227 (18)
C21—H21	0.9300	C44—H44A	0.9600
C22—O2	1.4197 (19)	C44—H44B	0.9600
C22—H22A	0.9600	C44—H44C	0.9600
C22—H22B	0.9600	N1—N2	1.3784 (16)
C22—H22C	0.9600	N4—N5	1.376 (2)
C23—N4	1.310 (2)	O1—H1	0.946 (15)
C23—N6	1.378 (2)	O3—H2	0.902 (16)
N1—C1—N3	110.07 (13)	C30—C25—C24	124.30 (15)
N1—C1—C9	123.94 (13)	C26—C25—C24	118.92 (17)
N3—C1—C9	125.97 (12)	O3—C26—C27	118.0 (2)
N2—C2—N3	108.44 (12)	O3—C26—C25	122.1 (2)
N2—C2—C3	122.49 (13)	C27—C26—C25	119.9 (2)
N3—C2—C3	129.05 (12)	C28—C27—C26	121.6 (2)
C8—C3—C4	117.13 (15)	C28—C27—H27	119.2
C8—C3—C2	123.97 (13)	C26—C27—H27	119.2
C4—C3—C2	118.89 (14)	C27—C28—C29	119.9 (2)
O1—C4—C5	116.47 (15)	C27—C28—H28	120.0
O1—C4—C3	122.98 (15)	C29—C28—H28	120.0
C5—C4—C3	120.54 (16)	C30—C29—C28	119.8 (2)
C6—C5—C4	120.49 (16)	C30—C29—H29	120.1
C6—C5—H5	119.8	C28—C29—H29	120.1
C4—C5—H5	119.8	C29—C30—C25	121.92 (17)
C5—C6—C7	120.28 (17)	C29—C30—H30	119.0
C5—C6—H6	119.9	C25—C30—H30	119.0
C7—C6—H6	119.9	C32—C31—C36	116.5 (2)
C8—C7—C6	119.53 (17)	C32—C31—C23	121.66 (17)
C8—C7—H7	120.2	C36—C31—C23	121.81 (17)
C6—C7—H7	120.2	C31—C32—C33	121.44 (19)
C7—C8—C3	121.97 (15)	C31—C32—H32	119.3
C7—C8—H8	119.0	C33—C32—H32	119.3
C3—C8—H8	119.0	C34—C33—C32	122.1 (2)
C10—C9—C14	117.76 (14)	C34—C33—H33	119.0
C10—C9—C1	123.03 (13)	C32—C33—H33	119.0
C14—C9—C1	119.12 (13)	C33—C34—C35	116.9 (2)
C11—C10—C9	120.83 (14)	C33—C34—C37	121.9 (2)
C11—C10—H10	119.6	C35—C34—C37	121.2 (2)
C9—C10—H10	119.6	C34—C35—C36	122.02 (19)
C10—C11—C12	121.92 (14)	C34—C35—H35	119.0
C10—C11—H11	119.0	C36—C35—H35	119.0
C12—C11—H11	119.0	C35—C36—C31	120.98 (18)
C11—C12—C13	117.06 (15)	C35—C36—H36	119.5
C11—C12—C15	120.86 (15)	C31—C36—H36	119.5
C13—C12—C15	122.06 (15)	C34—C37—H37A	109.5
C14—C13—C12	121.62 (15)	C34—C37—H37B	109.5
C14—C13—H13	119.2	H37A—C37—H37B	109.5
C12—C13—H13	119.2	C34—C37—H37C	109.5
C13—C14—C9	120.77 (14)	H37A—C37—H37C	109.5
C13—C14—H14	119.6	H37B—C37—H37C	109.5
C9—C14—H14	119.6	C43—C38—C39	120.50 (13)
C12—C15—H15A	109.5	C43—C38—N6	120.88 (12)
C12—C15—H15B	109.5	C39—C38—N6	118.59 (12)
H15A—C15—H15B	109.5	C40—C39—C38	119.64 (13)
C12—C15—H15C	109.5	C40—C39—H39	120.2
H15A—C15—H15C	109.5	C38—C39—H39	120.2
H15B—C15—H15C	109.5	C39—C40—C41	120.31 (13)
C17—C16—C21	120.52 (12)	C39—C40—H40	119.8
C17—C16—N3	120.56 (11)	C41—C40—H40	119.8
C21—C16—N3	118.92 (12)	O4—C41—C42	124.78 (12)
C16—C17—C18	120.00 (12)	O4—C41—C40	115.30 (12)
C16—C17—H17	120.0	C42—C41—C40	119.91 (13)
C18—C17—H17	120.0	C41—C42—C43	119.36 (13)
C19—C18—C17	120.01 (13)	C41—C42—H42	120.3
C19—C18—H18	120.0	C43—C42—H42	120.3
C17—C18—H18	120.0	C38—C43—C42	120.27 (13)
O2—C19—C18	125.29 (13)	C38—C43—H43	119.9
O2—C19—C20	115.33 (13)	C42—C43—H43	119.9
C18—C19—C20	119.37 (13)	O4—C44—H44A	109.5
C21—C20—C19	120.60 (13)	O4—C44—H44B	109.5
C21—C20—H20	119.7	H44A—C44—H44B	109.5
C19—C20—H20	119.7	O4—C44—H44C	109.5
C20—C21—C16	119.50 (13)	H44A—C44—H44C	109.5
C20—C21—H21	120.2	H44B—C44—H44C	109.5
C16—C21—H21	120.2	C1—N1—N2	106.92 (12)
O2—C22—H22A	109.5	C2—N2—N1	109.10 (11)
O2—C22—H22B	109.5	C2—N3—C1	105.47 (11)
H22A—C22—H22B	109.5	C2—N3—C16	127.81 (11)
O2—C22—H22C	109.5	C1—N3—C16	126.28 (11)
H22A—C22—H22C	109.5	C23—N4—N5	107.31 (15)
H22B—C22—H22C	109.5	C24—N5—N4	109.20 (16)
N4—C23—N6	109.71 (18)	C23—N6—C24	105.69 (14)
N4—C23—C31	127.09 (18)	C23—N6—C38	123.51 (14)
N6—C23—C31	123.20 (15)	C24—N6—C38	129.62 (14)
N5—C24—N6	108.08 (18)	C4—O1—H1	104.7 (13)
N5—C24—C25	122.23 (17)	C19—O2—C22	118.44 (12)
N6—C24—C25	129.69 (14)	C26—O3—H2	110.0 (16)
C30—C25—C26	116.78 (19)	C41—O4—C44	118.30 (12)
N2—C2—C3—C8	165.26 (13)	C36—C31—C32—C33	−2.4 (3)
N3—C2—C3—C8	−16.6 (2)	C23—C31—C32—C33	176.47 (17)
N2—C2—C3—C4	−13.6 (2)	C31—C32—C33—C34	0.3 (3)
N3—C2—C3—C4	164.59 (13)	C32—C33—C34—C35	2.6 (3)
C8—C3—C4—O1	−177.14 (13)	C32—C33—C34—C37	−175.91 (18)
C2—C3—C4—O1	1.8 (2)	C33—C34—C35—C36	−3.4 (3)
C8—C3—C4—C5	2.0 (2)	C37—C34—C35—C36	175.08 (18)
C2—C3—C4—C5	−179.10 (13)	C34—C35—C36—C31	1.4 (3)
O1—C4—C5—C6	179.12 (15)	C32—C31—C36—C35	1.6 (3)
C3—C4—C5—C6	0.0 (2)	C23—C31—C36—C35	−177.30 (17)
C4—C5—C6—C7	−2.1 (3)	C43—C38—C39—C40	−0.4 (2)
C5—C6—C7—C8	2.2 (3)	N6—C38—C39—C40	−178.47 (14)
C6—C7—C8—C3	−0.2 (2)	C38—C39—C40—C41	−0.1 (2)
C4—C3—C8—C7	−1.9 (2)	C39—C40—C41—O4	178.84 (13)
C2—C3—C8—C7	179.24 (14)	C39—C40—C41—C42	0.0 (2)
N1—C1—C9—C10	146.37 (14)	O4—C41—C42—C43	−178.18 (13)
N3—C1—C9—C10	−31.8 (2)	C40—C41—C42—C43	0.5 (2)
N1—C1—C9—C14	−30.0 (2)	C39—C38—C43—C42	0.9 (2)
N3—C1—C9—C14	151.76 (13)	N6—C38—C43—C42	178.98 (13)
C14—C9—C10—C11	−1.9 (2)	C41—C42—C43—C38	−1.0 (2)
C1—C9—C10—C11	−178.33 (13)	N3—C1—N1—N2	−0.02 (14)
C9—C10—C11—C12	0.4 (2)	C9—C1—N1—N2	−178.46 (11)
C10—C11—C12—C13	1.2 (2)	N3—C2—N2—N1	0.23 (14)
C10—C11—C12—C15	−177.19 (13)	C3—C2—N2—N1	178.75 (11)
C11—C12—C13—C14	−1.2 (2)	C1—N1—N2—C2	−0.13 (15)
C15—C12—C13—C14	177.12 (14)	N2—C2—N3—C1	−0.23 (14)
C12—C13—C14—C9	−0.3 (2)	C3—C2—N3—C1	−178.62 (12)
C10—C9—C14—C13	1.8 (2)	N2—C2—N3—C16	−172.88 (12)
C1—C9—C14—C13	178.42 (12)	C3—C2—N3—C16	8.7 (2)
C21—C16—C17—C18	0.0 (2)	N1—C1—N3—C2	0.15 (14)
N3—C16—C17—C18	179.13 (12)	C9—C1—N3—C2	178.56 (12)
C16—C17—C18—C19	0.8 (2)	N1—C1—N3—C16	172.95 (12)
C17—C18—C19—O2	180.00 (13)	C9—C1—N3—C16	−8.6 (2)
C17—C18—C19—C20	−1.3 (2)	C17—C16—N3—C2	−81.62 (17)
O2—C19—C20—C21	179.76 (14)	C21—C16—N3—C2	97.50 (17)
C18—C19—C20—C21	0.9 (2)	C17—C16—N3—C1	107.18 (16)
C19—C20—C21—C16	−0.1 (2)	C21—C16—N3—C1	−73.70 (17)
C17—C16—C21—C20	−0.4 (2)	N6—C23—N4—N5	−0.2 (2)
N3—C16—C21—C20	−179.51 (13)	C31—C23—N4—N5	−179.59 (16)
N5—C24—C25—C30	−174.79 (15)	N6—C24—N5—N4	−1.08 (19)
N6—C24—C25—C30	5.3 (3)	C25—C24—N5—N4	179.00 (15)
N5—C24—C25—C26	4.9 (2)	C23—N4—N5—C24	0.8 (2)
N6—C24—C25—C26	−174.97 (15)	N4—C23—N6—C24	−0.47 (18)
C30—C25—C26—O3	−179.43 (15)	C31—C23—N6—C24	178.98 (14)
C24—C25—C26—O3	0.8 (2)	N4—C23—N6—C38	−169.13 (13)
C30—C25—C26—C27	0.8 (2)	C31—C23—N6—C38	10.3 (2)
C24—C25—C26—C27	−178.91 (16)	N5—C24—N6—C23	0.95 (17)
O3—C26—C27—C28	179.42 (17)	C25—C24—N6—C23	−179.14 (16)
C25—C26—C27—C28	−0.8 (3)	N5—C24—N6—C38	168.67 (13)
C26—C27—C28—C29	0.2 (3)	C25—C24—N6—C38	−11.4 (3)
C27—C28—C29—C30	0.4 (3)	C43—C38—N6—C23	−101.90 (17)
C28—C29—C30—C25	−0.4 (3)	C39—C38—N6—C23	76.19 (19)
C26—C25—C30—C29	−0.2 (2)	C43—C38—N6—C24	92.32 (19)
C24—C25—C30—C29	179.49 (16)	C39—C38—N6—C24	−89.59 (19)
N4—C23—C31—C32	58.6 (2)	C18—C19—O2—C22	0.5 (2)
N6—C23—C31—C32	−120.79 (18)	C20—C19—O2—C22	−178.26 (14)
N4—C23—C31—C36	−122.6 (2)	C42—C41—O4—C44	0.4 (2)
N6—C23—C31—C36	58.0 (2)	C40—C41—O4—C44	−178.31 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.95 (2)	1.72 (2)	2.5932 (18)	153 (2)
O3—H2···N5	0.90 (2)	1.75 (2)	2.547 (3)	147 (2)