Crystal structure and Hirshfeld surface analysis of N-{2-[(E)-(4-methyl­benzyl­idene)amino]­phen­yl}-2-(5-methyl-1-H-pyrazol-3-yl)acetamide hemihydrate

The asymmetric unit of the title compound contains two independent organic mol­ecules which differ primarily in the dihedral angle between the aromatic rings, viz. 7.79 (7) and 29.89 (7)°. In the crystal, the components are linked by O_water—H...N, N—H...O_water and N—H...N hydrogen bonds, forming chains along the [100] direction. The chains are linked by C—H...O and C—H...N hydrogen bonds, forming layers parallel to the ab plane. Finally, the layers are linked by C—H...π inter­actions, forming a three-dimensional structure.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.046
• wR factor = 0.122
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

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Datablock: I


Alert level C
PLAT041_ALERT_1_C Calc. and Reported SumFormula    Strings  Differ     Please Check
PLAT222_ALERT_3_C Non-Solv.  Resd 1  H   Uiso(max)/Uiso(min) Range        4.4 Ratio
PLAT222_ALERT_3_C Non-Solv.  Resd 2  H   Uiso(max)/Uiso(min) Range        4.3 Ratio
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         21 Report

Alert level G
PLAT013_ALERT_1_G N.O.K.   _shelx_hkl_checksum Found in CIF ......     Please Check
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)      0.003 Degree
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        252 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         11 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
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   7 ALERT level G = General information/check it is not something unexpected

   5 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
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Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/1 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2018/1 (Sheldrick, 2015b), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

N-{2-[(E)-(4-Methylbenzylidene)amino]phenyl}-2-(5-methyl-1-H-pyrazol-3-yl)acetamide hemihydrate

Crystal data

C20H20N4O·0.5H2O	Z = 4
Mr = 341.41	F(000) = 724
Triclinic, P1	Dx = 1.250 Mg m^−3
a = 11.546 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.564 (3) Å	Cell parameters from 5130 reflections
c = 13.172 (3) Å	θ = 2.2–28.2°
α = 101.991 (3)°	µ = 0.08 mm^−1
β = 97.535 (3)°	T = 100 K
γ = 99.847 (3)°	Rod, colourless
V = 1813.8 (7) Å^3	0.21 × 0.13 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer	8663 independent reflections
Radiation source: fine-focus sealed tube	5888 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 8.3333 pixels mm^-1	θmax = 28.2°, θmin = 1.6°
ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −16→16
Tmin = 0.88, Tmax = 0.99	l = −17→17
17171 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: difference Fourier map
wR(F^2) = 0.122	All H-atom parameters refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0564P)^2] where P = (Fo^2 + 2Fc^2)/3
8663 reflections	(Δ/σ)max < 0.001
628 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

Experimental. The diffraction data were collected in three sets of 363 frames (0.5° width in ω) at φ = 0, 120 and 240°. A scan time of 60 sec/frame was used.

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. 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 > 2sigma(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
O1	−0.24038 (9)	0.13666 (9)	0.04235 (8)	0.0313 (3)
N1	0.27104 (11)	0.26740 (10)	0.11862 (10)	0.0240 (3)
H1	0.3426 (15)	0.3173 (14)	0.1367 (13)	0.040 (5)*
N2	0.16821 (10)	0.29967 (10)	0.08749 (9)	0.0238 (3)
N3	−0.09799 (11)	0.19107 (10)	0.19035 (9)	0.0213 (3)
H3A	−0.0190 (13)	0.2168 (12)	0.2155 (12)	0.023 (4)*
N4	0.02622 (10)	0.22466 (10)	0.38113 (9)	0.0233 (3)
C1	0.35478 (14)	0.10461 (14)	0.14763 (14)	0.0284 (3)
H1A	0.3326 (16)	0.0229 (16)	0.1186 (15)	0.051 (5)*
H1B	0.3722 (16)	0.1144 (15)	0.2238 (16)	0.051 (5)*
H1C	0.4241 (17)	0.1349 (15)	0.1255 (15)	0.052 (6)*
C2	0.25432 (12)	0.15807 (11)	0.11593 (11)	0.0222 (3)
C3	0.13432 (13)	0.11639 (12)	0.08140 (11)	0.0236 (3)
H3	0.0949 (14)	0.0375 (13)	0.0687 (13)	0.036 (5)*
C4	0.08456 (12)	0.20676 (11)	0.06429 (11)	0.0205 (3)
C5	−0.04210 (13)	0.20825 (13)	0.02199 (11)	0.0229 (3)
H5A	−0.0458 (12)	0.2852 (13)	0.0168 (12)	0.026 (4)*
H5B	−0.0678 (13)	0.1591 (12)	−0.0510 (13)	0.027 (4)*
C6	−0.13684 (12)	0.17440 (11)	0.08508 (11)	0.0213 (3)
C7	−0.16340 (12)	0.16660 (11)	0.26803 (11)	0.0204 (3)
C8	−0.28614 (13)	0.12593 (12)	0.24842 (13)	0.0257 (3)
H8	−0.3322 (13)	0.1159 (12)	0.1777 (12)	0.026 (4)*
C9	−0.34209 (15)	0.09808 (15)	0.32871 (14)	0.0366 (4)
H9	−0.4304 (15)	0.0704 (13)	0.3126 (13)	0.038 (5)*
C10	−0.27788 (15)	0.11076 (17)	0.42750 (15)	0.0452 (5)
H10	−0.3172 (17)	0.0920 (15)	0.4852 (16)	0.055 (6)*
C11	−0.15655 (15)	0.15421 (15)	0.44915 (14)	0.0375 (4)
H11	−0.1124 (15)	0.1630 (14)	0.5198 (15)	0.047 (5)*
C12	−0.09769 (12)	0.18343 (11)	0.37043 (11)	0.0226 (3)
C13	0.09606 (13)	0.24843 (13)	0.46912 (12)	0.0265 (3)
H13	0.0668 (15)	0.2413 (14)	0.5348 (14)	0.047 (5)*
C14	0.22509 (13)	0.28361 (12)	0.47815 (11)	0.0246 (3)
C15	0.27780 (13)	0.29677 (12)	0.39088 (12)	0.0262 (3)
H15	0.2243 (13)	0.2821 (12)	0.3225 (12)	0.027 (4)*
C16	0.39990 (14)	0.32762 (14)	0.40179 (13)	0.0312 (4)
H16	0.4323 (14)	0.3411 (13)	0.3410 (13)	0.035 (5)*
C17	0.47409 (13)	0.34649 (13)	0.49918 (12)	0.0297 (4)
C18	0.42097 (15)	0.33447 (15)	0.58584 (13)	0.0354 (4)
H18	0.4721 (15)	0.3483 (13)	0.6554 (14)	0.040 (5)*
C19	0.29838 (14)	0.30374 (15)	0.57594 (13)	0.0350 (4)
H19	0.2595 (15)	0.2958 (14)	0.6390 (14)	0.048 (5)*
C20	0.60729 (15)	0.37970 (19)	0.50972 (17)	0.0432 (5)
H20A	0.642 (2)	0.319 (2)	0.469 (2)	0.101 (9)*
H20B	0.6300 (18)	0.4481 (18)	0.4833 (17)	0.072 (7)*
H20C	0.647 (2)	0.3942 (19)	0.583 (2)	0.087 (8)*
O2	0.52850 (9)	0.56026 (9)	0.82428 (9)	0.0319 (3)
N5	0.03382 (10)	0.52348 (10)	0.81415 (10)	0.0228 (3)
H5	−0.0253 (16)	0.5056 (14)	0.8528 (14)	0.045 (5)*
N6	0.15011 (10)	0.55805 (9)	0.86144 (9)	0.0210 (3)
N7	0.36667 (11)	0.43953 (10)	0.84380 (9)	0.0218 (3)
H7	0.2865 (15)	0.4290 (13)	0.8401 (13)	0.037 (5)*
N8	0.21561 (10)	0.25089 (10)	0.83158 (9)	0.0234 (3)
C21	−0.10166 (15)	0.48113 (16)	0.64252 (16)	0.0361 (4)
H21A	−0.163 (2)	0.4882 (19)	0.6879 (19)	0.086 (8)*
H21B	−0.1168 (17)	0.4019 (18)	0.6063 (16)	0.065 (6)*
H21C	−0.1135 (15)	0.5315 (15)	0.5943 (15)	0.052 (5)*
C22	0.01855 (13)	0.51647 (11)	0.70978 (12)	0.0245 (3)
C23	0.13064 (13)	0.54799 (12)	0.68677 (12)	0.0255 (3)
H23	0.1522 (13)	0.5523 (12)	0.6183 (13)	0.030 (4)*
C24	0.20896 (12)	0.57328 (11)	0.78264 (11)	0.0209 (3)
C25	0.34089 (13)	0.61544 (12)	0.80340 (13)	0.0236 (3)
H25A	0.3667 (13)	0.6811 (12)	0.8659 (12)	0.027 (4)*
H25B	0.3656 (13)	0.6432 (12)	0.7431 (13)	0.031 (4)*
C26	0.42068 (12)	0.53575 (12)	0.82503 (11)	0.0228 (3)
C27	0.41856 (12)	0.35211 (11)	0.86889 (11)	0.0213 (3)
C28	0.54056 (13)	0.36037 (13)	0.89766 (12)	0.0270 (3)
H28	0.5982 (15)	0.4314 (15)	0.8988 (13)	0.044 (5)*
C29	0.58176 (14)	0.27065 (13)	0.92452 (12)	0.0295 (4)
H29	0.6701 (15)	0.2783 (13)	0.9482 (13)	0.040 (5)*
C30	0.50266 (14)	0.17427 (14)	0.92401 (12)	0.0301 (4)
H30	0.5291 (14)	0.1144 (13)	0.9446 (13)	0.032 (4)*
C31	0.38173 (14)	0.16498 (13)	0.89364 (12)	0.0272 (3)
H31	0.3233 (13)	0.0982 (12)	0.8945 (11)	0.022 (4)*
C32	0.33787 (12)	0.25261 (12)	0.86328 (11)	0.0229 (3)
C33	0.14467 (13)	0.15882 (12)	0.78537 (12)	0.0245 (3)
H33	0.1751 (14)	0.0909 (13)	0.7694 (12)	0.033 (4)*
C34	0.01636 (13)	0.14971 (12)	0.75516 (11)	0.0234 (3)
C35	−0.05642 (14)	0.04580 (13)	0.70870 (13)	0.0303 (4)
H35	−0.0215 (14)	−0.0207 (14)	0.6920 (13)	0.037 (5)*
C36	−0.17876 (14)	0.03414 (13)	0.68350 (13)	0.0324 (4)
H36	−0.2277 (15)	−0.0379 (14)	0.6534 (13)	0.040 (5)*
C37	−0.23271 (13)	0.12516 (12)	0.70395 (12)	0.0269 (3)
C38	−0.15965 (14)	0.22914 (13)	0.74951 (12)	0.0263 (3)
H38	−0.1943 (13)	0.2927 (12)	0.7645 (12)	0.026 (4)*
C39	−0.03736 (13)	0.24180 (12)	0.77441 (12)	0.0246 (3)
H39	0.0132 (12)	0.3148 (12)	0.8089 (11)	0.020 (4)*
C40	−0.36608 (15)	0.11183 (16)	0.67982 (15)	0.0358 (4)
H40A	−0.4014 (16)	0.1124 (14)	0.7448 (15)	0.049 (5)*
H40B	−0.3951 (17)	0.1743 (17)	0.6509 (15)	0.060 (6)*
H40C	−0.4044 (15)	0.0410 (15)	0.6284 (14)	0.045 (5)*
O3	0.15336 (9)	0.51707 (9)	0.07448 (9)	0.0266 (2)
H3B	0.1689 (17)	0.4475 (17)	0.0720 (16)	0.060 (6)*
H3C	0.1580 (19)	0.5294 (18)	0.0125 (19)	0.075 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0194 (6)	0.0403 (6)	0.0291 (6)	0.0035 (5)	−0.0040 (4)	0.0042 (5)
N1	0.0183 (6)	0.0269 (7)	0.0278 (7)	0.0042 (5)	0.0049 (5)	0.0087 (5)
N2	0.0210 (6)	0.0262 (7)	0.0258 (7)	0.0054 (5)	0.0061 (5)	0.0083 (5)
N3	0.0147 (6)	0.0251 (6)	0.0221 (6)	0.0014 (5)	0.0006 (5)	0.0051 (5)
N4	0.0198 (6)	0.0263 (6)	0.0218 (6)	0.0023 (5)	0.0017 (5)	0.0046 (5)
C1	0.0214 (8)	0.0325 (9)	0.0330 (9)	0.0088 (7)	0.0041 (7)	0.0089 (7)
C2	0.0226 (8)	0.0239 (7)	0.0215 (7)	0.0060 (6)	0.0061 (6)	0.0059 (6)
C3	0.0229 (8)	0.0215 (8)	0.0261 (8)	0.0042 (6)	0.0028 (6)	0.0060 (6)
C4	0.0216 (7)	0.0229 (7)	0.0173 (7)	0.0041 (6)	0.0047 (6)	0.0047 (6)
C5	0.0245 (8)	0.0233 (8)	0.0202 (8)	0.0061 (6)	0.0011 (6)	0.0045 (6)
C6	0.0195 (7)	0.0200 (7)	0.0239 (7)	0.0073 (6)	0.0010 (6)	0.0035 (6)
C7	0.0191 (7)	0.0173 (7)	0.0249 (7)	0.0027 (5)	0.0047 (6)	0.0052 (6)
C8	0.0202 (8)	0.0253 (8)	0.0304 (9)	0.0028 (6)	0.0017 (6)	0.0068 (6)
C9	0.0198 (8)	0.0471 (10)	0.0421 (10)	−0.0010 (7)	0.0073 (7)	0.0142 (8)
C10	0.0302 (10)	0.0678 (13)	0.0387 (11)	−0.0023 (9)	0.0134 (8)	0.0201 (9)
C11	0.0300 (9)	0.0530 (11)	0.0283 (9)	0.0009 (8)	0.0054 (7)	0.0127 (8)
C12	0.0185 (7)	0.0235 (7)	0.0252 (8)	0.0030 (6)	0.0046 (6)	0.0049 (6)
C13	0.0256 (8)	0.0314 (8)	0.0210 (8)	0.0019 (6)	0.0036 (6)	0.0062 (6)
C14	0.0236 (8)	0.0261 (8)	0.0214 (7)	0.0027 (6)	0.0013 (6)	0.0032 (6)
C15	0.0219 (8)	0.0316 (8)	0.0209 (8)	0.0015 (6)	0.0003 (6)	0.0026 (6)
C16	0.0265 (9)	0.0382 (9)	0.0261 (8)	0.0015 (7)	0.0061 (7)	0.0045 (7)
C17	0.0211 (8)	0.0305 (8)	0.0325 (9)	0.0031 (6)	0.0000 (6)	0.0009 (7)
C18	0.0273 (9)	0.0488 (10)	0.0250 (9)	0.0033 (8)	−0.0044 (7)	0.0069 (7)
C19	0.0281 (9)	0.0509 (11)	0.0227 (8)	0.0005 (8)	0.0020 (7)	0.0086 (7)
C20	0.0216 (9)	0.0559 (13)	0.0444 (12)	0.0013 (8)	−0.0009 (8)	0.0038 (10)
O2	0.0173 (5)	0.0331 (6)	0.0444 (7)	0.0004 (4)	0.0059 (5)	0.0104 (5)
N5	0.0167 (6)	0.0225 (6)	0.0303 (7)	0.0045 (5)	0.0051 (5)	0.0081 (5)
N6	0.0179 (6)	0.0208 (6)	0.0243 (6)	0.0033 (5)	0.0036 (5)	0.0058 (5)
N7	0.0159 (6)	0.0232 (6)	0.0264 (7)	0.0031 (5)	0.0035 (5)	0.0067 (5)
N8	0.0232 (6)	0.0250 (6)	0.0223 (6)	0.0029 (5)	0.0049 (5)	0.0070 (5)
C21	0.0273 (9)	0.0372 (10)	0.0410 (10)	0.0015 (8)	−0.0063 (8)	0.0148 (8)
C22	0.0232 (8)	0.0210 (7)	0.0274 (8)	0.0022 (6)	−0.0007 (6)	0.0067 (6)
C23	0.0265 (8)	0.0258 (8)	0.0238 (8)	0.0033 (6)	0.0041 (6)	0.0069 (6)
C24	0.0220 (7)	0.0171 (7)	0.0251 (8)	0.0047 (6)	0.0058 (6)	0.0067 (6)
C25	0.0199 (8)	0.0230 (8)	0.0271 (8)	0.0002 (6)	0.0055 (6)	0.0067 (6)
C26	0.0190 (7)	0.0250 (7)	0.0210 (7)	0.0006 (6)	0.0025 (6)	0.0018 (6)
C27	0.0218 (7)	0.0254 (7)	0.0169 (7)	0.0061 (6)	0.0032 (6)	0.0044 (6)
C28	0.0230 (8)	0.0341 (9)	0.0231 (8)	0.0066 (7)	0.0031 (6)	0.0049 (6)
C29	0.0256 (8)	0.0413 (9)	0.0231 (8)	0.0133 (7)	0.0035 (7)	0.0061 (7)
C30	0.0357 (9)	0.0352 (9)	0.0244 (8)	0.0190 (8)	0.0059 (7)	0.0081 (7)
C31	0.0335 (9)	0.0268 (8)	0.0225 (8)	0.0081 (7)	0.0066 (7)	0.0056 (6)
C32	0.0234 (8)	0.0265 (8)	0.0194 (7)	0.0078 (6)	0.0052 (6)	0.0035 (6)
C33	0.0271 (8)	0.0221 (8)	0.0262 (8)	0.0056 (6)	0.0081 (6)	0.0071 (6)
C34	0.0264 (8)	0.0217 (7)	0.0228 (8)	0.0023 (6)	0.0074 (6)	0.0071 (6)
C35	0.0287 (9)	0.0219 (8)	0.0394 (9)	0.0023 (7)	0.0104 (7)	0.0049 (7)
C36	0.0302 (9)	0.0244 (8)	0.0378 (10)	−0.0046 (7)	0.0090 (7)	0.0033 (7)
C37	0.0246 (8)	0.0305 (8)	0.0257 (8)	−0.0014 (6)	0.0084 (6)	0.0101 (6)
C38	0.0286 (8)	0.0245 (8)	0.0275 (8)	0.0054 (7)	0.0061 (6)	0.0094 (6)
C39	0.0274 (8)	0.0211 (7)	0.0242 (8)	0.0011 (6)	0.0033 (6)	0.0068 (6)
C40	0.0256 (9)	0.0435 (11)	0.0355 (10)	0.0003 (8)	0.0096 (7)	0.0061 (8)
O3	0.0263 (6)	0.0266 (6)	0.0310 (6)	0.0078 (5)	0.0085 (5)	0.0116 (5)

Geometric parameters (Å, º)

O1—C6	1.2205 (16)	N5—C22	1.3453 (19)
N1—C2	1.3464 (18)	N5—N6	1.3596 (16)
N1—N2	1.3595 (16)	N5—H5	0.928 (18)
N1—H1	0.918 (17)	N6—C24	1.3410 (17)
N2—C4	1.3333 (17)	N7—C26	1.3484 (18)
N3—C6	1.3608 (18)	N7—C27	1.4137 (18)
N3—C7	1.4021 (18)	N7—H7	0.906 (17)
N3—H3A	0.907 (15)	N8—C33	1.2775 (18)
N4—C13	1.2695 (19)	N8—C32	1.4137 (18)
N4—C12	1.4136 (18)	C21—C22	1.487 (2)
C1—C2	1.492 (2)	C21—H21A	0.99 (3)
C1—H1A	0.993 (19)	C21—H21B	0.99 (2)
C1—H1B	0.974 (19)	C21—H21C	1.00 (2)
C1—H1C	0.935 (19)	C22—C23	1.379 (2)
C2—C3	1.374 (2)	C23—C24	1.396 (2)
C3—C4	1.4019 (19)	C23—H23	0.976 (16)
C3—H3	0.987 (16)	C24—C25	1.493 (2)
C4—C5	1.4999 (19)	C25—C26	1.516 (2)
C5—C6	1.515 (2)	C25—H25A	1.008 (16)
C5—H5A	0.991 (15)	C25—H25B	0.987 (16)
C5—H5B	1.004 (16)	C27—C28	1.390 (2)
C7—C8	1.3920 (19)	C27—C32	1.408 (2)
C7—C12	1.4134 (19)	C28—C29	1.388 (2)
C8—C9	1.383 (2)	C28—H28	1.014 (18)
C8—H8	0.982 (15)	C29—C30	1.385 (2)
C9—C10	1.374 (2)	C29—H29	1.009 (17)
C9—H9	0.998 (16)	C30—C31	1.379 (2)
C10—C11	1.382 (2)	C30—H30	0.935 (16)
C10—H10	0.98 (2)	C31—C32	1.396 (2)
C11—C12	1.389 (2)	C31—H31	0.986 (14)
C11—H11	0.976 (18)	C33—C34	1.461 (2)
C13—C14	1.461 (2)	C33—H33	0.971 (16)
C13—H13	0.984 (18)	C34—C35	1.394 (2)
C14—C19	1.395 (2)	C34—C39	1.397 (2)
C14—C15	1.395 (2)	C35—C36	1.383 (2)
C15—C16	1.377 (2)	C35—H35	0.985 (16)
C15—H15	0.986 (15)	C36—C37	1.388 (2)
C16—C17	1.397 (2)	C36—H36	0.955 (17)
C16—H16	0.960 (17)	C37—C38	1.394 (2)
C17—C18	1.388 (2)	C37—C40	1.504 (2)
C17—C20	1.503 (2)	C38—C39	1.381 (2)
C18—C19	1.383 (2)	C38—H38	0.949 (15)
C18—H18	0.987 (17)	C39—H39	0.981 (14)
C19—H19	1.009 (18)	C40—H40A	0.994 (19)
C20—H20A	1.02 (3)	C40—H40B	1.03 (2)
C20—H20B	1.00 (2)	C40—H40C	0.992 (18)
C20—H20C	0.98 (3)	O3—H3B	0.92 (2)
O2—C26	1.2322 (17)	O3—H3C	0.87 (2)
C2—N1—N2	112.77 (12)	C22—N5—H5	126.5 (11)
C2—N1—H1	126.3 (10)	N6—N5—H5	120.8 (11)
N2—N1—H1	120.9 (10)	C24—N6—N5	104.31 (11)
C4—N2—N1	104.56 (11)	C26—N7—C27	128.61 (12)
C6—N3—C7	128.49 (12)	C26—N7—H7	116.3 (10)
C6—N3—H3A	118.4 (9)	C27—N7—H7	115.1 (10)
C7—N3—H3A	113.0 (9)	C33—N8—C32	119.62 (13)
C13—N4—C12	122.39 (13)	C22—C21—H21A	109.1 (13)
C2—C1—H1A	110.3 (10)	C22—C21—H21B	110.9 (11)
C2—C1—H1B	111.5 (11)	H21A—C21—H21B	105.8 (18)
H1A—C1—H1B	105.2 (15)	C22—C21—H21C	111.2 (10)
C2—C1—H1C	110.8 (11)	H21A—C21—H21C	105.3 (16)
H1A—C1—H1C	110.7 (15)	H21B—C21—H21C	114.0 (16)
H1B—C1—H1C	108.1 (15)	N5—C22—C23	106.25 (13)
N1—C2—C3	105.96 (12)	N5—C22—C21	121.78 (14)
N1—C2—C1	121.99 (13)	C23—C22—C21	131.97 (15)
C3—C2—C1	132.05 (14)	C22—C23—C24	105.66 (13)
C2—C3—C4	105.94 (13)	C22—C23—H23	128.0 (9)
C2—C3—H3	125.1 (9)	C24—C23—H23	126.3 (9)
C4—C3—H3	128.9 (9)	N6—C24—C23	111.07 (13)
N2—C4—C3	110.77 (12)	N6—C24—C25	120.87 (13)
N2—C4—C5	120.30 (12)	C23—C24—C25	128.03 (13)
C3—C4—C5	128.88 (13)	C24—C25—C26	118.03 (12)
C4—C5—C6	117.61 (12)	C24—C25—H25A	111.9 (8)
C4—C5—H5A	107.9 (8)	C26—C25—H25A	104.5 (8)
C6—C5—H5A	106.3 (8)	C24—C25—H25B	109.9 (9)
C4—C5—H5B	110.6 (8)	C26—C25—H25B	106.3 (9)
C6—C5—H5B	106.5 (8)	H25A—C25—H25B	105.3 (12)
H5A—C5—H5B	107.4 (12)	O2—C26—N7	123.63 (14)
O1—C6—N3	123.85 (13)	O2—C26—C25	120.04 (13)
O1—C6—C5	120.84 (13)	N7—C26—C25	116.33 (12)
N3—C6—C5	115.30 (12)	C28—C27—C32	120.48 (13)
C8—C7—N3	123.57 (13)	C28—C27—N7	123.96 (13)
C8—C7—C12	119.98 (13)	C32—C27—N7	115.56 (12)
N3—C7—C12	116.44 (12)	C29—C28—C27	119.24 (15)
C9—C8—C7	119.49 (15)	C29—C28—H28	120.9 (10)
C9—C8—H8	120.4 (9)	C27—C28—H28	119.9 (10)
C7—C8—H8	120.1 (9)	C30—C29—C28	120.68 (15)
C10—C9—C8	120.69 (15)	C30—C29—H29	120.4 (9)
C10—C9—H9	121.6 (10)	C28—C29—H29	118.8 (9)
C8—C9—H9	117.7 (10)	C31—C30—C29	120.25 (15)
C9—C10—C11	120.54 (16)	C31—C30—H30	118.3 (10)
C9—C10—H10	121.1 (11)	C29—C30—H30	121.5 (10)
C11—C10—H10	118.3 (11)	C30—C31—C32	120.37 (15)
C10—C11—C12	120.21 (16)	C30—C31—H31	121.9 (8)
C10—C11—H11	119.5 (10)	C32—C31—H31	117.7 (8)
C12—C11—H11	120.3 (11)	C31—C32—C27	118.86 (13)
C11—C12—C7	119.00 (13)	C31—C32—N8	124.36 (13)
C11—C12—N4	125.82 (14)	C27—C32—N8	116.71 (12)
C7—C12—N4	115.11 (12)	N8—C33—C34	122.69 (14)
N4—C13—C14	121.94 (14)	N8—C33—H33	120.2 (9)
N4—C13—H13	121.9 (10)	C34—C33—H33	117.1 (9)
C14—C13—H13	116.1 (10)	C35—C34—C39	118.27 (14)
C19—C14—C15	118.66 (14)	C35—C34—C33	119.59 (13)
C19—C14—C13	119.64 (14)	C39—C34—C33	122.11 (13)
C15—C14—C13	121.70 (13)	C36—C35—C34	120.77 (15)
C16—C15—C14	120.17 (14)	C36—C35—H35	118.7 (9)
C16—C15—H15	122.5 (9)	C34—C35—H35	120.5 (9)
C14—C15—H15	117.3 (9)	C35—C36—C37	121.15 (15)
C15—C16—C17	121.55 (15)	C35—C36—H36	119.8 (10)
C15—C16—H16	117.6 (10)	C37—C36—H36	119.0 (10)
C17—C16—H16	120.7 (10)	C36—C37—C38	117.97 (14)
C18—C17—C16	117.97 (14)	C36—C37—C40	121.10 (14)
C18—C17—C20	121.12 (15)	C38—C37—C40	120.91 (15)
C16—C17—C20	120.91 (15)	C39—C38—C37	121.34 (15)
C19—C18—C17	121.03 (15)	C39—C38—H38	119.0 (9)
C19—C18—H18	120.0 (10)	C37—C38—H38	119.7 (9)
C17—C18—H18	119.0 (10)	C38—C39—C34	120.47 (14)
C18—C19—C14	120.62 (15)	C38—C39—H39	120.9 (8)
C18—C19—H19	121.2 (10)	C34—C39—H39	118.6 (8)
C14—C19—H19	118.2 (10)	C37—C40—H40A	110.8 (10)
C17—C20—H20A	112.0 (14)	C37—C40—H40B	114.9 (11)
C17—C20—H20B	111.1 (12)	H40A—C40—H40B	104.2 (15)
H20A—C20—H20B	108.0 (19)	C37—C40—H40C	112.1 (10)
C17—C20—H20C	111.5 (14)	H40A—C40—H40C	107.4 (14)
H20A—C20—H20C	105.7 (19)	H40B—C40—H40C	106.9 (15)
H20B—C20—H20C	108.4 (18)	H3B—O3—H3C	106.3 (19)
C22—N5—N6	112.71 (12)
C2—N1—N2—C4	−0.19 (15)	C22—N5—N6—C24	0.17 (15)
N2—N1—C2—C3	−0.09 (16)	N6—N5—C22—C23	0.04 (16)
N2—N1—C2—C1	−179.53 (13)	N6—N5—C22—C21	−179.52 (13)
N1—C2—C3—C4	0.31 (16)	N5—C22—C23—C24	−0.23 (16)
C1—C2—C3—C4	179.67 (15)	C21—C22—C23—C24	179.27 (16)
N1—N2—C4—C3	0.39 (15)	N5—N6—C24—C23	−0.32 (15)
N1—N2—C4—C5	−177.40 (12)	N5—N6—C24—C25	177.99 (12)
C2—C3—C4—N2	−0.45 (17)	C22—C23—C24—N6	0.35 (16)
C2—C3—C4—C5	177.10 (13)	C22—C23—C24—C25	−177.80 (14)
N2—C4—C5—C6	−120.07 (14)	N6—C24—C25—C26	75.24 (18)
C3—C4—C5—C6	62.6 (2)	C23—C24—C25—C26	−106.77 (17)
C7—N3—C6—O1	2.3 (2)	C27—N7—C26—O2	2.3 (2)
C7—N3—C6—C5	−178.85 (12)	C27—N7—C26—C25	−178.09 (13)
C4—C5—C6—O1	−154.35 (13)	C24—C25—C26—O2	167.33 (13)
C4—C5—C6—N3	26.74 (18)	C24—C25—C26—N7	−12.3 (2)
C6—N3—C7—C8	−4.5 (2)	C26—N7—C27—C28	12.5 (2)
C6—N3—C7—C12	174.38 (13)	C26—N7—C27—C32	−167.60 (13)
N3—C7—C8—C9	176.28 (14)	C32—C27—C28—C29	−2.3 (2)
C12—C7—C8—C9	−2.6 (2)	N7—C27—C28—C29	177.62 (13)
C7—C8—C9—C10	0.4 (3)	C27—C28—C29—C30	−0.8 (2)
C8—C9—C10—C11	1.6 (3)	C28—C29—C30—C31	2.0 (2)
C9—C10—C11—C12	−1.3 (3)	C29—C30—C31—C32	−0.1 (2)
C10—C11—C12—C7	−0.9 (3)	C30—C31—C32—C27	−2.9 (2)
C10—C11—C12—N4	−177.53 (16)	C30—C31—C32—N8	−179.62 (13)
C8—C7—C12—C11	2.8 (2)	C28—C27—C32—C31	4.1 (2)
N3—C7—C12—C11	−176.12 (13)	N7—C27—C32—C31	−175.82 (12)
C8—C7—C12—N4	179.83 (12)	C28—C27—C32—N8	−178.92 (12)
N3—C7—C12—N4	0.90 (18)	N7—C27—C32—N8	1.15 (18)
C13—N4—C12—C11	−6.3 (2)	C33—N8—C32—C31	−30.9 (2)
C13—N4—C12—C7	176.92 (13)	C33—N8—C32—C27	152.35 (13)
C12—N4—C13—C14	175.65 (13)	C32—N8—C33—C34	176.83 (12)
N4—C13—C14—C19	−177.01 (15)	N8—C33—C34—C35	−177.46 (14)
N4—C13—C14—C15	2.4 (2)	N8—C33—C34—C39	0.4 (2)
C19—C14—C15—C16	0.8 (2)	C39—C34—C35—C36	−0.7 (2)
C13—C14—C15—C16	−178.54 (14)	C33—C34—C35—C36	177.20 (14)
C14—C15—C16—C17	0.0 (2)	C34—C35—C36—C37	−0.2 (2)
C15—C16—C17—C18	−0.7 (2)	C35—C36—C37—C38	0.8 (2)
C15—C16—C17—C20	179.76 (16)	C35—C36—C37—C40	−177.95 (15)
C16—C17—C18—C19	0.6 (3)	C36—C37—C38—C39	−0.4 (2)
C20—C17—C18—C19	−179.91 (17)	C40—C37—C38—C39	178.34 (14)
C17—C18—C19—C14	0.3 (3)	C37—C38—C39—C34	−0.6 (2)
C15—C14—C19—C18	−1.0 (2)	C35—C34—C39—C38	1.1 (2)
C13—C14—C19—C18	178.41 (15)	C33—C34—C39—C38	−176.75 (13)

Hydrogen-bond geometry (Å, º)

Cg1, Cg3 and Cg6 are the centroids of the N1/N2/C2–C4, C14–C19 and C34–C39 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.92 (2)	1.88 (2)	2.7863 (18)	169 (2)
O3—H3B···N2	0.92 (2)	1.91 (2)	2.8047 (19)	165 (2)
O3—H3C···N6^ii	0.87 (2)	2.09 (2)	2.9530 (18)	174 (2)
N5—H5···O3^iii	0.93 (2)	1.878 (19)	2.8014 (18)	173 (2)
N7—H7···N6	0.91 (2)	2.447 (17)	3.1314 (19)	132.6 (13)
C1—H1A···O1^iv	0.99 (2)	2.56 (2)	3.436 (2)	146.9 (15)
C8—H8···O1	0.98 (2)	2.228 (15)	2.858 (2)	120.8 (12)
C28—H28···O2	1.01 (2)	2.265 (18)	2.890 (2)	118.5 (13)
C35—H35···N4^v	0.99 (2)	2.532 (18)	3.451 (2)	155.2 (13)
N3—H3A···Cg1	0.91 (2)	2.999 (15)	3.6216 (17)	127.4 (12)
C5—H5B···Cg6^ii	1.00 (2)	2.820 (16)	3.7171 (18)	149.0 (12)
C11—H11···Cg6	0.98 (2)	2.837 (19)	3.713 (2)	149.8 (14)
C15—H15···Cg1	0.99 (2)	2.913 (15)	3.7979 (19)	149.8 (12)
C20—H20B···Cg3^i	1.00 (2)	2.88 (2)	3.772 (3)	148.9 (16)

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