Crystal structure and Hirshfeld surface analysis of 2-{[(E)-(3-cyclo­butyl-1H-1,2,4-triazol-5-yl)imino]­meth­yl}phenol

2-{[(E)-(3-Cyclo­butyl-1H-1,2,4-triazol-5-yl)imino]­meth­yl}phenol was synthesized by an eco-friendly microwave-assisted method that is highly selective and efficient. In the crystal, mol­ecules are linked by N—H...N and C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.058
• wR factor = 0.153
• Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack parameter is too small
           From the CIF: _refine_ls_abs_structure_Flack   -1.000
           From the CIF: _refine_ls_abs_structure_Flack_su    2.000
PLAT234_ALERT_4_C Large Hirshfeld Difference C10      --C11      .       0.16 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C11      --C12      .       0.16 Ang.
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C11 Check
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C12 Check
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C38 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C10 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00789 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C13 H14 N4 O
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.922 Check
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          1 Check

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          6 Report
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      2.000 Report
PLAT063_ALERT_4_G Crystal Size Possibly too Large for Beam Size ..       0.76 mm
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as      mixed Check
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2 Note
              C13 H14 N4 O
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          3 Note
              C13 H14 N4 O
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         23 Note
PLAT916_ALERT_2_G Hooft y and Flack x Parameter Values Differ by .       0.22 Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
  11 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

   2 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
   3 ALERT type 3 Indicator that the structure quality may be low
   9 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT2017/1 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017/1 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: WinGX (Farrugia, 2012).

2-{[(E)-(3-Cyclobutyl-1H-1,2,4-triazol-5-yl)imino]methyl}phenol

Crystal data

C13H14N4O	F(000) = 768
Mr = 242.28	Dx = 1.244 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 5.2717 (3) Å	Cell parameters from 17085 reflections
b = 24.9066 (14) Å	θ = 1.4–27.4°
c = 14.8628 (7) Å	µ = 0.08 mm^−1
β = 96.214 (4)°	T = 296 K
V = 1940.02 (18) Å^3	Stick, yellow
Z = 6	0.76 × 0.52 × 0.30 mm

Data collection

Stoe IPDS 2 diffractometer	8333 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	5374 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm^-1	Rint = 0.096
rotation method scans	θmax = 26.9°, θmin = 1.4°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −6→6
Tmin = 0.938, Tmax = 0.980	k = −31→31
15228 measured reflections	l = −18→18

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.058	w = 1/[σ^2(Fo^2) + (0.084P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.153	(Δ/σ)max < 0.001
S = 0.94	Δρmax = 0.16 e Å^−3
8333 reflections	Δρmin = −0.19 e Å^−3
493 parameters	Absolute structure: Refined as an inversion twin
1 restraint	Absolute structure parameter: −1 (2)

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.

Refinement. Refined as a two-component inversion twin.

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

	x	y	z	Uiso*/Ueq
N11	−0.7970 (7)	−0.44524 (14)	−0.4433 (2)	0.0699 (9)
H11	−0.897406	−0.472528	−0.444919	0.084*
N6	−1.0215 (7)	−0.54788 (13)	−0.4431 (2)	0.0652 (9)
N5	−0.8325 (6)	−0.56917 (14)	−0.5739 (2)	0.0616 (8)
N9	−0.3235 (7)	−0.36402 (14)	−0.3466 (2)	0.0699 (9)
N12	−0.6141 (7)	−0.37213 (14)	−0.4855 (2)	0.0698 (9)
O2	−0.4440 (6)	−0.51862 (14)	−0.6305 (2)	0.0792 (8)
H2	−0.548954	−0.525821	−0.595446	0.119*
N10	−0.6221 (8)	−0.43214 (14)	−0.3725 (2)	0.0709 (9)
N7	−1.1902 (7)	−0.57344 (14)	−0.3961 (2)	0.0667 (9)
H7D	−1.247216	−0.560968	−0.348178	0.088 (16)*
O1	−0.7626 (7)	−0.65935 (15)	−0.2019 (2)	0.0900 (10)
H1	−0.871881	−0.635799	−0.204508	0.135*
N8	−1.1368 (7)	−0.62721 (14)	−0.5071 (2)	0.0645 (8)
N3	−1.5053 (9)	−0.49514 (16)	−0.2114 (2)	0.0809 (11)
H3D	−1.563359	−0.470387	−0.248339	0.077 (14)*
N1	−1.1418 (7)	−0.60443 (14)	−0.1485 (2)	0.0673 (9)
C21	−0.9973 (8)	−0.58229 (16)	−0.5094 (3)	0.0597 (9)
N4	−1.4393 (8)	−0.54232 (16)	−0.0881 (2)	0.0779 (10)
N2	−1.3418 (8)	−0.53404 (15)	−0.2310 (2)	0.0756 (10)
C20	−0.8486 (8)	−0.59720 (17)	−0.6470 (3)	0.0615 (9)
H20	−0.967147	−0.624910	−0.654904	0.074*
C35	−0.7894 (9)	−0.40930 (16)	−0.5098 (3)	0.0654 (10)
C34	−0.5166 (9)	−0.38873 (16)	−0.4011 (3)	0.0630 (10)
O3	−0.0219 (9)	−0.35762 (17)	−0.1976 (3)	0.1155 (15)
H3	−0.124553	−0.371866	−0.235635	0.173*
C8	−1.3077 (9)	−0.56122 (17)	−0.1547 (3)	0.0673 (10)
C7	−1.1444 (9)	−0.63770 (19)	−0.0833 (3)	0.0709 (11)
H7	−1.257747	−0.631869	−0.040517	0.085*
C32	−0.0082 (8)	−0.29555 (16)	−0.3204 (3)	0.0637 (10)
C22	−1.2564 (8)	−0.62051 (16)	−0.4337 (3)	0.0633 (10)
C33	−0.2150 (9)	−0.32178 (18)	−0.3745 (3)	0.0674 (11)
H33	−0.271873	−0.307826	−0.431097	0.081*
C19	−0.6849 (8)	−0.58627 (17)	−0.7172 (3)	0.0607 (9)
C31	0.1081 (9)	−0.2502 (2)	−0.3523 (3)	0.0764 (12)
H31	0.048601	−0.236737	−0.409058	0.092*
C23	−1.4205 (9)	−0.66013 (18)	−0.3935 (3)	0.0721 (12)
H23	−1.533394	−0.642112	−0.354781	0.087*
C1	−0.7985 (8)	−0.69374 (19)	−0.1338 (3)	0.0713 (11)
C6	−0.9800 (8)	−0.68365 (18)	−0.0732 (3)	0.0646 (10)
C9	−1.5652 (11)	−0.5004 (2)	−0.1259 (3)	0.0799 (13)
C15	−0.3418 (9)	−0.5393 (2)	−0.7774 (3)	0.0825 (13)
H15	−0.211309	−0.513991	−0.770918	0.099*
C14	−0.4932 (7)	−0.54795 (18)	−0.7067 (3)	0.0634 (10)
C16	−0.3863 (11)	−0.5680 (3)	−0.8555 (3)	0.0887 (15)
H16	−0.285384	−0.561698	−0.901974	0.106*
C30	0.3059 (10)	−0.2248 (2)	−0.3032 (4)	0.0835 (13)
H30	0.377953	−0.194138	−0.325682	0.100*
C24	−1.2859 (11)	−0.7076 (2)	−0.3438 (4)	0.0945 (16)
H24A	−1.275498	−0.704915	−0.278389	0.113*
H24B	−1.120686	−0.715851	−0.363368	0.113*
C5	−1.0037 (10)	−0.7208 (2)	−0.0045 (3)	0.0838 (13)
H5	−1.123504	−0.714929	0.036028	0.101*
C27	0.0858 (9)	−0.3150 (2)	−0.2347 (3)	0.0773 (13)
C36	−0.9562 (9)	−0.41109 (19)	−0.5962 (3)	0.0741 (11)
H36	−1.079123	−0.440553	−0.595341	0.089*
C18	−0.7251 (9)	−0.6154 (2)	−0.7978 (3)	0.0758 (12)
H18	−0.852386	−0.641378	−0.805055	0.091*
C2	−0.6502 (10)	−0.7394 (2)	−0.1235 (4)	0.0910 (15)
H2A	−0.529395	−0.745790	−0.163398	0.109*
C4	−0.8513 (11)	−0.7665 (2)	0.0046 (4)	0.0957 (16)
H4	−0.867080	−0.790781	0.051120	0.115*
C26	−1.5682 (9)	−0.7009 (2)	−0.4542 (4)	0.0835 (14)
H26A	−1.749634	−0.693456	−0.464529	0.100*
H26B	−1.497645	−0.706884	−0.510986	0.100*
C3	−0.6767 (12)	−0.7752 (3)	−0.0564 (4)	0.0997 (17)
H3A	−0.575938	−0.805905	−0.051536	0.120*
C10	−1.7219 (14)	−0.4618 (2)	−0.0811 (4)	0.106 (2)
H10	−1.841507	−0.443208	−0.125701	0.127*
C28	0.2882 (11)	−0.2889 (3)	−0.1857 (4)	0.0950 (16)
H28	0.350184	−0.301504	−0.128671	0.114*
C17	−0.5736 (11)	−0.6054 (3)	−0.8673 (3)	0.0888 (15)
H17	−0.600936	−0.624342	−0.921459	0.107*
C29	0.3970 (10)	−0.2450 (2)	−0.2204 (4)	0.0878 (14)
H29	0.535293	−0.228508	−0.187238	0.105*
C39	−1.0923 (12)	−0.3597 (3)	−0.6292 (4)	0.0994 (17)
H39A	−1.271579	−0.358844	−0.619836	0.119*
H39B	−1.006271	−0.327158	−0.606644	0.119*
C25	−1.5013 (11)	−0.7440 (2)	−0.3854 (4)	0.0948 (16)
H25A	−1.442921	−0.777109	−0.410537	0.114*
H25B	−1.632828	−0.750774	−0.345929	0.114*
C37	−0.8362 (12)	−0.4113 (3)	−0.6856 (3)	0.1036 (18)
H37A	−0.667032	−0.395503	−0.681379	0.124*
H37B	−0.839005	−0.446067	−0.715000	0.124*
C38	−1.0446 (15)	−0.3741 (3)	−0.7240 (4)	0.121 (2)
H38A	−1.186802	−0.392224	−0.758146	0.145*
H38B	−0.984828	−0.344306	−0.758075	0.145*
C11	−1.5830 (19)	−0.4224 (4)	−0.0169 (8)	0.167 (4)
H11A	−1.414523	−0.434387	0.007721	0.200*
H11B	−1.576586	−0.386355	−0.041158	0.200*
C12	−1.776 (2)	−0.4295 (5)	0.0446 (6)	0.177 (4)
H12A	−1.907206	−0.401994	0.038835	0.212*
H12B	−1.706473	−0.433875	0.107314	0.212*
C13	−1.8566 (14)	−0.4810 (4)	−0.0013 (5)	0.125 (2)
H13A	−2.039826	−0.484886	−0.014726	0.150*
H13B	−1.781036	−0.512679	0.028581	0.150*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.097 (2)	0.0553 (18)	0.0566 (19)	−0.0203 (18)	0.0055 (17)	−0.0031 (15)
N6	0.092 (2)	0.0555 (18)	0.0513 (17)	−0.0169 (17)	0.0211 (16)	−0.0036 (15)
N5	0.0716 (18)	0.0616 (18)	0.0541 (17)	−0.0049 (16)	0.0186 (14)	−0.0007 (15)
N9	0.096 (3)	0.059 (2)	0.0516 (17)	−0.0067 (19)	−0.0049 (17)	0.0045 (15)
N12	0.093 (2)	0.060 (2)	0.0533 (18)	−0.0144 (18)	−0.0069 (16)	0.0124 (15)
O2	0.088 (2)	0.086 (2)	0.0657 (18)	−0.0154 (17)	0.0176 (14)	−0.0036 (16)
N10	0.105 (3)	0.0541 (19)	0.0528 (18)	−0.0139 (18)	0.0040 (18)	0.0043 (15)
N7	0.097 (2)	0.0576 (19)	0.0495 (17)	−0.0128 (18)	0.0262 (17)	−0.0061 (15)
O1	0.097 (2)	0.092 (2)	0.086 (2)	0.0105 (19)	0.0338 (18)	0.0083 (19)
N8	0.078 (2)	0.0558 (19)	0.0634 (19)	−0.0051 (17)	0.0253 (16)	−0.0067 (15)
N3	0.133 (3)	0.063 (2)	0.0467 (18)	0.016 (2)	0.0101 (19)	0.0084 (16)
N1	0.089 (2)	0.063 (2)	0.0517 (18)	0.0084 (18)	0.0155 (16)	0.0017 (15)
C21	0.073 (2)	0.055 (2)	0.053 (2)	−0.0082 (19)	0.0154 (17)	−0.0015 (17)
N4	0.120 (3)	0.073 (2)	0.0427 (16)	0.028 (2)	0.0158 (17)	0.0011 (16)
N2	0.121 (3)	0.061 (2)	0.0473 (18)	0.007 (2)	0.0200 (18)	0.0027 (15)
C20	0.071 (2)	0.058 (2)	0.058 (2)	−0.0010 (19)	0.0162 (18)	−0.0006 (17)
C35	0.085 (3)	0.053 (2)	0.057 (2)	−0.010 (2)	−0.0011 (19)	0.0053 (18)
C34	0.088 (3)	0.052 (2)	0.047 (2)	−0.008 (2)	−0.0001 (18)	0.0050 (16)
O3	0.158 (4)	0.100 (3)	0.077 (2)	−0.045 (3)	−0.040 (2)	0.035 (2)
C8	0.098 (3)	0.062 (2)	0.045 (2)	0.007 (2)	0.0171 (19)	−0.0001 (17)
C7	0.087 (3)	0.076 (3)	0.051 (2)	0.008 (2)	0.0143 (19)	−0.004 (2)
C32	0.078 (2)	0.058 (2)	0.053 (2)	0.000 (2)	−0.0030 (18)	0.0000 (18)
C22	0.078 (2)	0.055 (2)	0.060 (2)	−0.008 (2)	0.0214 (19)	−0.0068 (18)
C33	0.089 (3)	0.060 (2)	0.050 (2)	−0.002 (2)	−0.0051 (19)	0.0058 (18)
C19	0.066 (2)	0.066 (2)	0.052 (2)	0.0133 (19)	0.0129 (17)	0.0042 (17)
C31	0.089 (3)	0.071 (3)	0.065 (3)	−0.010 (2)	−0.008 (2)	0.009 (2)
C23	0.083 (3)	0.065 (2)	0.075 (3)	−0.015 (2)	0.035 (2)	−0.010 (2)
C1	0.069 (2)	0.074 (3)	0.070 (3)	0.000 (2)	0.000 (2)	−0.006 (2)
C6	0.072 (2)	0.064 (2)	0.056 (2)	0.004 (2)	−0.0003 (18)	−0.0023 (18)
C9	0.121 (4)	0.075 (3)	0.044 (2)	0.019 (3)	0.008 (2)	−0.003 (2)
C15	0.078 (3)	0.098 (3)	0.074 (3)	−0.004 (3)	0.025 (2)	0.018 (3)
C14	0.065 (2)	0.074 (2)	0.052 (2)	0.007 (2)	0.0095 (17)	0.0100 (18)
C16	0.097 (3)	0.113 (4)	0.060 (3)	0.019 (3)	0.028 (2)	0.013 (3)
C30	0.088 (3)	0.075 (3)	0.085 (3)	−0.011 (3)	−0.004 (2)	0.004 (2)
C24	0.097 (3)	0.100 (4)	0.084 (3)	−0.030 (3)	−0.002 (3)	0.025 (3)
C5	0.096 (3)	0.089 (3)	0.065 (3)	0.011 (3)	0.001 (2)	0.014 (2)
C27	0.098 (3)	0.071 (3)	0.059 (3)	−0.008 (2)	−0.011 (2)	0.008 (2)
C36	0.084 (3)	0.068 (3)	0.068 (3)	−0.017 (2)	−0.005 (2)	0.003 (2)
C18	0.084 (3)	0.086 (3)	0.059 (2)	0.007 (2)	0.017 (2)	−0.007 (2)
C2	0.083 (3)	0.099 (4)	0.091 (4)	0.020 (3)	0.006 (3)	0.001 (3)
C4	0.114 (4)	0.086 (3)	0.084 (4)	0.013 (3)	−0.008 (3)	0.023 (3)
C26	0.075 (3)	0.084 (3)	0.093 (3)	−0.019 (2)	0.013 (2)	−0.003 (3)
C3	0.102 (4)	0.093 (4)	0.100 (4)	0.035 (3)	−0.008 (3)	0.000 (3)
C10	0.161 (5)	0.091 (4)	0.064 (3)	0.059 (4)	0.001 (3)	0.002 (3)
C28	0.114 (4)	0.099 (4)	0.064 (3)	−0.013 (3)	−0.027 (3)	0.006 (3)
C17	0.097 (3)	0.117 (4)	0.055 (2)	0.015 (3)	0.019 (2)	−0.004 (3)
C29	0.089 (3)	0.088 (3)	0.082 (3)	−0.016 (3)	−0.011 (3)	−0.009 (3)
C39	0.099 (4)	0.100 (4)	0.093 (4)	0.017 (3)	−0.016 (3)	−0.006 (3)
C25	0.103 (4)	0.073 (3)	0.110 (4)	−0.020 (3)	0.021 (3)	−0.009 (3)
C37	0.113 (4)	0.136 (5)	0.058 (3)	0.020 (4)	−0.006 (3)	−0.006 (3)
C38	0.142 (5)	0.139 (6)	0.077 (4)	0.015 (5)	−0.010 (3)	0.022 (4)
C11	0.174 (7)	0.119 (6)	0.216 (10)	−0.016 (6)	0.064 (7)	−0.104 (7)
C12	0.224 (10)	0.199 (10)	0.109 (6)	0.031 (9)	0.022 (6)	−0.063 (7)
C13	0.120 (5)	0.137 (6)	0.126 (6)	0.026 (4)	0.043 (4)	−0.021 (5)

Geometric parameters (Å, º)

N11—C35	1.338 (5)	C15—C16	1.361 (8)
N11—N10	1.361 (5)	C15—C14	1.403 (6)
N11—H11	0.8600	C15—H15	0.9300
N6—C21	1.322 (5)	C16—C17	1.356 (8)
N6—N7	1.349 (5)	C16—H16	0.9300
N5—C20	1.287 (5)	C30—C29	1.369 (7)
N5—C21	1.400 (5)	C30—H30	0.9300
N9—C33	1.287 (6)	C24—C25	1.530 (8)
N9—C34	1.376 (5)	C24—H24A	0.9700
N12—C35	1.330 (5)	C24—H24B	0.9700
N12—C34	1.368 (5)	C5—C4	1.391 (8)
O2—C14	1.349 (5)	C5—H5	0.9300
O2—H2	0.8200	C27—C28	1.386 (7)
N10—C34	1.308 (5)	C36—C39	1.523 (7)
N7—C22	1.330 (5)	C36—C37	1.533 (8)
N7—H7D	0.8600	C36—H36	0.9800
O1—C1	1.355 (6)	C18—C17	1.395 (7)
O1—H1	0.8200	C18—H18	0.9300
N8—C22	1.328 (5)	C2—C3	1.355 (9)
N8—C21	1.341 (5)	C2—H2A	0.9300
N3—C9	1.347 (6)	C4—C3	1.377 (8)
N3—N2	1.349 (6)	C4—H4	0.9300
N3—H3D	0.8600	C26—C25	1.498 (8)
N1—C7	1.276 (6)	C26—H26A	0.9700
N1—C8	1.383 (6)	C26—H26B	0.9700
N4—C9	1.329 (6)	C3—H3A	0.9300
N4—C8	1.353 (5)	C10—C11	1.503 (10)
N2—C8	1.316 (5)	C10—C13	1.524 (10)
C20—C19	1.451 (5)	C10—H10	0.9800
C20—H20	0.9300	C28—C29	1.361 (8)
C35—C36	1.476 (6)	C28—H28	0.9300
O3—C27	1.351 (6)	C17—H17	0.9300
O3—H3	0.8200	C29—H29	0.9300
C7—C6	1.434 (6)	C39—C38	1.502 (9)
C7—H7	0.9300	C39—H39A	0.9700
C32—C31	1.393 (6)	C39—H39B	0.9700
C32—C27	1.402 (6)	C25—H25A	0.9700
C32—C33	1.439 (6)	C25—H25B	0.9700
C22—C23	1.481 (6)	C37—C38	1.501 (9)
C33—H33	0.9300	C37—H37A	0.9700
C19—C14	1.386 (6)	C37—H37B	0.9700
C19—C18	1.396 (6)	C38—H38A	0.9700
C31—C30	1.362 (7)	C38—H38B	0.9700
C31—H31	0.9300	C11—C12	1.450 (13)
C23—C26	1.517 (7)	C11—H11A	0.9700
C23—C24	1.527 (8)	C11—H11B	0.9700
C23—H23	0.9800	C12—C13	1.493 (13)
C1—C2	1.379 (7)	C12—H12A	0.9700
C1—C6	1.406 (6)	C12—H12B	0.9700
C6—C5	1.394 (7)	C13—H13A	0.9700
C9—C10	1.472 (7)	C13—H13B	0.9700
C35—N11—N10	109.8 (3)	C4—C5—C6	121.1 (5)
C35—N11—H11	125.1	C4—C5—H5	119.4
N10—N11—H11	125.1	C6—C5—H5	119.4
C21—N6—N7	101.7 (3)	O3—C27—C28	119.2 (4)
C20—N5—C21	117.5 (3)	O3—C27—C32	121.3 (4)
C33—N9—C34	120.1 (3)	C28—C27—C32	119.5 (4)
C35—N12—C34	102.7 (3)	C35—C36—C39	118.1 (4)
C14—O2—H2	109.5	C35—C36—C37	119.4 (4)
C34—N10—N11	103.0 (3)	C39—C36—C37	87.0 (4)
C22—N7—N6	110.8 (3)	C35—C36—H36	110.1
C22—N7—H7D	124.6	C39—C36—H36	110.1
N6—N7—H7D	124.6	C37—C36—H36	110.1
C1—O1—H1	109.5	C17—C18—C19	119.8 (5)
C22—N8—C21	103.1 (3)	C17—C18—H18	120.1
C9—N3—N2	110.8 (4)	C19—C18—H18	120.1
C9—N3—H3D	124.6	C3—C2—C1	121.4 (5)
N2—N3—H3D	124.6	C3—C2—H2A	119.3
C7—N1—C8	119.8 (4)	C1—C2—H2A	119.3
N6—C21—N8	115.1 (3)	C3—C4—C5	119.0 (5)
N6—C21—N5	118.4 (3)	C3—C4—H4	120.5
N8—C21—N5	126.5 (3)	C5—C4—H4	120.5
C9—N4—C8	103.7 (4)	C25—C26—C23	90.3 (4)
C8—N2—N3	102.4 (3)	C25—C26—H26A	113.6
N5—C20—C19	121.1 (4)	C23—C26—H26A	113.6
N5—C20—H20	119.5	C25—C26—H26B	113.6
C19—C20—H20	119.5	C23—C26—H26B	113.6
N12—C35—N11	109.9 (3)	H26A—C26—H26B	110.9
N12—C35—C36	126.0 (4)	C2—C3—C4	120.7 (5)
N11—C35—C36	124.1 (4)	C2—C3—H3A	119.7
N10—C34—N12	114.6 (4)	C4—C3—H3A	119.7
N10—C34—N9	119.5 (4)	C9—C10—C11	117.0 (6)
N12—C34—N9	125.9 (4)	C9—C10—C13	118.6 (5)
C27—O3—H3	109.5	C11—C10—C13	86.9 (6)
N2—C8—N4	114.7 (4)	C9—C10—H10	110.8
N2—C8—N1	118.9 (3)	C11—C10—H10	110.8
N4—C8—N1	126.4 (4)	C13—C10—H10	110.8
N1—C7—C6	122.8 (4)	C29—C28—C27	120.6 (5)
N1—C7—H7	118.6	C29—C28—H28	119.7
C6—C7—H7	118.6	C27—C28—H28	119.7
C31—C32—C27	117.6 (4)	C16—C17—C18	119.6 (5)
C31—C32—C33	120.9 (4)	C16—C17—H17	120.2
C27—C32—C33	121.5 (4)	C18—C17—H17	120.2
N8—C22—N7	109.3 (3)	C28—C29—C30	121.0 (5)
N8—C22—C23	126.8 (4)	C28—C29—H29	119.5
N7—C22—C23	123.7 (4)	C30—C29—H29	119.5
N9—C33—C32	121.9 (4)	C38—C39—C36	88.9 (5)
N9—C33—H33	119.1	C38—C39—H39A	113.8
C32—C33—H33	119.1	C36—C39—H39A	113.8
C14—C19—C18	119.7 (4)	C38—C39—H39B	113.8
C14—C19—C20	122.0 (4)	C36—C39—H39B	113.8
C18—C19—C20	118.2 (4)	H39A—C39—H39B	111.1
C30—C31—C32	122.3 (4)	C26—C25—C24	87.8 (4)
C30—C31—H31	118.8	C26—C25—H25A	114.0
C32—C31—H31	118.8	C24—C25—H25A	114.0
C22—C23—C26	119.4 (4)	C26—C25—H25B	114.0
C22—C23—C24	116.7 (4)	C24—C25—H25B	114.0
C26—C23—C24	87.2 (4)	H25A—C25—H25B	111.2
C22—C23—H23	110.5	C38—C37—C36	88.5 (5)
C26—C23—H23	110.5	C38—C37—H37A	113.9
C24—C23—H23	110.5	C36—C37—H37A	113.9
O1—C1—C2	118.8 (5)	C38—C37—H37B	113.9
O1—C1—C6	121.7 (4)	C36—C37—H37B	113.9
C2—C1—C6	119.6 (5)	H37A—C37—H37B	111.1
C5—C6—C1	118.2 (4)	C37—C38—C39	88.9 (4)
C5—C6—C7	120.4 (4)	C37—C38—H38A	113.8
C1—C6—C7	121.4 (4)	C39—C38—H38A	113.8
N4—C9—N3	108.5 (4)	C37—C38—H38B	113.8
N4—C9—C10	126.9 (4)	C39—C38—H38B	113.8
N3—C9—C10	124.3 (4)	H38A—C38—H38B	111.1
C16—C15—C14	119.9 (5)	C12—C11—C10	89.7 (7)
C16—C15—H15	120.1	C12—C11—H11A	113.7
C14—C15—H15	120.1	C10—C11—H11A	113.7
O2—C14—C19	122.7 (4)	C12—C11—H11B	113.7
O2—C14—C15	118.2 (4)	C10—C11—H11B	113.7
C19—C14—C15	119.2 (4)	H11A—C11—H11B	110.9
C17—C16—C15	121.9 (5)	C11—C12—C13	90.0 (6)
C17—C16—H16	119.1	C11—C12—H12A	113.6
C15—C16—H16	119.1	C13—C12—H12A	113.6
C31—C30—C29	119.0 (5)	C11—C12—H12B	113.6
C31—C30—H30	120.5	C13—C12—H12B	113.6
C29—C30—H30	120.5	H12A—C12—H12B	110.9
C23—C24—C25	88.7 (4)	C12—C13—C10	87.3 (7)
C23—C24—H24A	113.9	C12—C13—H13A	114.1
C25—C24—H24A	113.9	C10—C13—H13A	114.1
C23—C24—H24B	113.9	C12—C13—H13B	114.1
C25—C24—H24B	113.9	C10—C13—H13B	114.1
H24A—C24—H24B	111.1	H13A—C13—H13B	111.3
C35—N11—N10—C34	−0.4 (5)	C20—C19—C14—O2	0.6 (6)
C21—N6—N7—C22	0.6 (5)	C18—C19—C14—C15	−0.3 (6)
N7—N6—C21—N8	−0.2 (5)	C20—C19—C14—C15	−179.9 (4)
N7—N6—C21—N5	180.0 (4)	C16—C15—C14—O2	−179.7 (5)
C22—N8—C21—N6	−0.3 (5)	C16—C15—C14—C19	0.7 (7)
C22—N8—C21—N5	179.5 (4)	C14—C15—C16—C17	−0.4 (8)
C20—N5—C21—N6	−166.4 (4)	C32—C31—C30—C29	1.2 (8)
C20—N5—C21—N8	13.8 (6)	C22—C23—C24—C25	−139.8 (4)
C9—N3—N2—C8	−0.6 (5)	C26—C23—C24—C25	−18.1 (4)
C21—N5—C20—C19	−180.0 (4)	C1—C6—C5—C4	0.4 (7)
C34—N12—C35—N11	0.7 (5)	C7—C6—C5—C4	178.0 (5)
C34—N12—C35—C36	179.8 (5)	C31—C32—C27—O3	177.7 (5)
N10—N11—C35—N12	−0.2 (5)	C33—C32—C27—O3	−3.1 (8)
N10—N11—C35—C36	−179.3 (4)	C31—C32—C27—C28	−0.3 (7)
N11—N10—C34—N12	0.9 (5)	C33—C32—C27—C28	178.9 (5)
N11—N10—C34—N9	−179.0 (4)	N12—C35—C36—C39	−47.2 (7)
C35—N12—C34—N10	−1.1 (5)	N11—C35—C36—C39	131.7 (5)
C35—N12—C34—N9	178.9 (5)	N12—C35—C36—C37	56.2 (7)
C33—N9—C34—N10	178.8 (4)	N11—C35—C36—C37	−124.8 (5)
C33—N9—C34—N12	−1.1 (7)	C14—C19—C18—C17	−0.5 (7)
N3—N2—C8—N4	0.3 (5)	C20—C19—C18—C17	179.1 (4)
N3—N2—C8—N1	−178.3 (4)	O1—C1—C2—C3	179.8 (5)
C9—N4—C8—N2	0.2 (6)	C6—C1—C2—C3	0.5 (8)
C9—N4—C8—N1	178.6 (5)	C6—C5—C4—C3	−0.8 (9)
C7—N1—C8—N2	−165.7 (4)	C22—C23—C26—C25	137.8 (5)
C7—N1—C8—N4	15.9 (7)	C24—C23—C26—C25	18.5 (4)
C8—N1—C7—C6	179.3 (4)	C1—C2—C3—C4	−0.9 (9)
C21—N8—C22—N7	0.6 (5)	C5—C4—C3—C2	1.1 (9)
C21—N8—C22—C23	−174.3 (4)	N4—C9—C10—C11	72.4 (9)
N6—N7—C22—N8	−0.8 (5)	N3—C9—C10—C11	−100.3 (8)
N6—N7—C22—C23	174.3 (4)	N4—C9—C10—C13	−29.6 (10)
C34—N9—C33—C32	−178.4 (4)	N3—C9—C10—C13	157.6 (6)
C31—C32—C33—N9	179.4 (4)	O3—C27—C28—C29	−178.4 (6)
C27—C32—C33—N9	0.2 (7)	C32—C27—C28—C29	−0.5 (9)
N5—C20—C19—C14	4.4 (6)	C15—C16—C17—C18	−0.4 (8)
N5—C20—C19—C18	−175.2 (4)	C19—C18—C17—C16	0.9 (8)
C27—C32—C31—C30	−0.1 (7)	C27—C28—C29—C30	1.6 (9)
C33—C32—C31—C30	−179.3 (5)	C31—C30—C29—C28	−1.9 (9)
N8—C22—C23—C26	−29.5 (7)	C35—C36—C39—C38	141.3 (5)
N7—C22—C23—C26	156.2 (4)	C37—C36—C39—C38	19.3 (5)
N8—C22—C23—C24	73.2 (6)	C23—C26—C25—C24	−18.5 (4)
N7—C22—C23—C24	−101.0 (5)	C23—C24—C25—C26	18.4 (4)
O1—C1—C6—C5	−179.5 (4)	C35—C36—C37—C38	−140.0 (5)
C2—C1—C6—C5	−0.2 (7)	C39—C36—C37—C38	−19.3 (5)
O1—C1—C6—C7	3.0 (6)	C36—C37—C38—C39	19.6 (5)
C2—C1—C6—C7	−177.8 (4)	C36—C39—C38—C37	−19.7 (5)
N1—C7—C6—C5	−175.3 (5)	C9—C10—C11—C12	−139.3 (7)
N1—C7—C6—C1	2.2 (7)	C13—C10—C11—C12	−18.5 (8)
C8—N4—C9—N3	−0.6 (6)	C10—C11—C12—C13	18.9 (8)
C8—N4—C9—C10	−174.3 (6)	C11—C12—C13—C10	−18.7 (8)
N2—N3—C9—N4	0.8 (6)	C9—C10—C13—C12	137.3 (7)
N2—N3—C9—C10	174.7 (5)	C11—C10—C13—C12	18.0 (7)
C18—C19—C14—O2	−179.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7D···N2	0.86	1.98	2.836 (5)	174
N11—H11···N6	0.86	1.99	2.817 (5)	161
O1—H1···N1	0.82	1.89	2.615 (5)	146
O2—H2···N5	0.82	1.90	2.619 (4)	146
O3—H3···N9	0.82	1.87	2.588 (5)	146
C10—H10···O3^i	0.98	2.52	3.411 (6)	151
N3—H3D···N10^ii	0.86	2.07	2.874 (5)	155

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