(E)-N′-[3-Meth­oxy-2-(2-nitro­benz­yloxy)benzyl­idene]­isonicotino­hydrazide

The title compound, C₂₁H₁₈N₄O₅, crystallizes with two mol­ecules in the asymmetric unit. The conformations of these non-planar mol­ecules are simlilar. Intra- and inter­molecular N—H...(O,N) hydrogen-bond systems and inter­molecular C—H...O and C—H...N hydrogen bonds help to consolidate the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.057
• wR factor = 0.129
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         40 Perc.
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.51 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N8     -   C42     ..       5.54 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C23
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N8
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      46.00 A   3 

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

   0 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
   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

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); 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.

(E)—N'-[3-Methoxy-2-(2-nitrobenzyloxy)benzylidene]isonicotinohydrazide

Crystal data

C21H18N4O5	F(000) = 1696
Mr = 406.39	Dx = 1.308 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2481 reflections
a = 7.8965 (17) Å	θ = 2.6–20.5°
b = 26.120 (6) Å	µ = 0.10 mm^−1
c = 20.139 (4) Å	T = 294 K
β = 96.355 (4)°	Block, yellow
V = 4128.3 (15) Å^3	0.24 × 0.20 × 0.12 mm
Z = 8

Data collection

Bruker SMART APEX CCD area-detector diffractometer	8411 independent reflections
Radiation source: fine-focus sealed tube	3364 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.082
φ and ω scans	θmax = 26.4°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→9
Tmin = 0.958, Tmax = 0.989	k = −31→32
23178 measured reflections	l = −24→25

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)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.129	w = 1/[σ^2(Fo^2) + (0.0359P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
8411 reflections	Δρmax = 0.30 e Å^−3
544 parameters	Δρmin = −0.22 e Å^−3
24 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: 0.0021 (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 > 2σ(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	0.8196 (3)	0.26942 (8)	0.68413 (10)	0.0652 (7)
O2	0.4569 (2)	0.08248 (7)	0.83831 (9)	0.0456 (5)
O3	0.6133 (3)	0.01480 (8)	0.92288 (10)	0.0585 (6)
O4	0.4972 (3)	0.01273 (11)	0.66114 (12)	0.0980 (9)
O5	0.3024 (3)	−0.02557 (11)	0.59894 (12)	0.0951 (9)
O6	0.3025 (3)	0.16367 (8)	0.67614 (10)	0.0632 (6)
O7	0.0182 (2)	0.35273 (7)	0.84421 (9)	0.0477 (5)
O8	0.2060 (3)	0.41903 (8)	0.92201 (10)	0.0621 (6)
O9	0.0665 (3)	0.41170 (11)	0.66125 (13)	0.1022 (10)
O10	−0.1148 (3)	0.45626 (13)	0.60247 (14)	0.1195 (11)
N1	0.3406 (5)	0.33658 (14)	0.52378 (19)	0.1019 (12)
N2	0.5915 (3)	0.23158 (9)	0.72212 (12)	0.0534 (7)
H2A	0.4824	0.2287	0.7189	0.064*
N3	0.6925 (3)	0.20473 (9)	0.77072 (12)	0.0473 (6)
N4	0.3493 (4)	0.00037 (11)	0.64806 (14)	0.0617 (8)
N5	−0.2345 (4)	0.10120 (12)	0.54225 (16)	0.0798 (9)
N6	0.0928 (3)	0.19941 (9)	0.72860 (12)	0.0517 (7)
H6	−0.0148	0.2018	0.7314	0.062*
N7	0.2071 (3)	0.22571 (9)	0.77310 (12)	0.0499 (7)
N8	−0.0769 (4)	0.42702 (13)	0.64876 (15)	0.0689 (9)
C1	0.6138 (5)	0.30784 (13)	0.57236 (18)	0.0745 (11)
H1	0.7299	0.3056	0.5687	0.089*
C2	0.5068 (7)	0.33169 (16)	0.5232 (2)	0.0958 (14)
H2	0.5551	0.3453	0.4870	0.115*
C3	0.2779 (5)	0.31736 (16)	0.5765 (2)	0.0983 (14)
H3	0.1615	0.3206	0.5788	0.118*
C4	0.3741 (4)	0.29266 (13)	0.62858 (19)	0.0759 (11)
H4	0.3225	0.2797	0.6644	0.091*
C5	0.5476 (4)	0.28745 (11)	0.62678 (16)	0.0528 (8)
C6	0.6651 (4)	0.26206 (12)	0.68013 (15)	0.0496 (8)
C7	0.6118 (4)	0.17208 (11)	0.80196 (14)	0.0462 (8)
H7	0.4942	0.1696	0.7925	0.055*
C8	0.6995 (3)	0.13841 (12)	0.85235 (14)	0.0416 (8)
C9	0.8610 (4)	0.14947 (12)	0.88455 (15)	0.0546 (9)
H9	0.9156	0.1797	0.8751	0.066*
C10	0.9391 (4)	0.11561 (13)	0.93027 (15)	0.0609 (9)
H10	1.0463	0.1234	0.9518	0.073*
C11	0.8615 (4)	0.07040 (13)	0.94472 (14)	0.0534 (9)
H11	0.9166	0.0477	0.9755	0.064*
C12	0.7009 (4)	0.05865 (12)	0.91332 (14)	0.0450 (8)
C13	0.6207 (3)	0.09302 (12)	0.86820 (13)	0.0413 (8)
C14	0.6950 (4)	−0.02331 (12)	0.96693 (15)	0.0667 (10)
H14A	0.7984	−0.0343	0.9504	0.100*
H14B	0.6201	−0.0521	0.9691	0.100*
H14C	0.7209	−0.0090	1.0108	0.100*
C15	0.4550 (3)	0.05656 (11)	0.77545 (14)	0.0460 (8)
H15A	0.5251	0.0260	0.7807	0.055*
H15B	0.5005	0.0787	0.7431	0.055*
C16	0.2734 (3)	0.04227 (10)	0.75147 (14)	0.0409 (7)
C17	0.1437 (4)	0.05492 (12)	0.78937 (16)	0.0555 (9)
H17	0.1699	0.0730	0.8290	0.067*
C18	−0.0235 (4)	0.04148 (14)	0.77001 (19)	0.0696 (11)
H18	−0.1077	0.0503	0.7968	0.084*
C19	−0.0666 (4)	0.01508 (13)	0.7115 (2)	0.0688 (10)
H19	−0.1796	0.0062	0.6987	0.083*
C20	0.0573 (4)	0.00197 (12)	0.67223 (16)	0.0592 (9)
H20	0.0299	−0.0160	0.6326	0.071*
C21	0.2240 (4)	0.01588 (11)	0.69246 (15)	0.0445 (8)
C22	0.0467 (4)	0.13301 (14)	0.57063 (17)	0.0739 (11)
H22	0.1539	0.1388	0.5571	0.089*
C23	−0.0804 (5)	0.11098 (16)	0.52733 (19)	0.0939 (14)
H23	−0.0550	0.1025	0.4847	0.113*
C24	−0.2660 (4)	0.11431 (13)	0.60323 (19)	0.0687 (10)
H24	−0.3747	0.1085	0.6153	0.082*
C25	−0.1466 (4)	0.13609 (12)	0.64982 (16)	0.0581 (9)
H25	−0.1750	0.1439	0.6923	0.070*
C26	0.0133 (4)	0.14626 (11)	0.63362 (15)	0.0452 (8)
C27	0.1504 (4)	0.17012 (12)	0.68097 (15)	0.0463 (8)
C28	0.1385 (4)	0.25801 (11)	0.80937 (14)	0.0481 (8)
H28	0.0204	0.2609	0.8054	0.058*
C29	0.2415 (4)	0.29047 (12)	0.85686 (14)	0.0457 (8)
C30	0.4017 (4)	0.27567 (13)	0.88693 (16)	0.0647 (10)
H30	0.4443	0.2435	0.8782	0.078*
C31	0.4963 (4)	0.30842 (14)	0.92915 (16)	0.0699 (10)
H31	0.6027	0.2982	0.9491	0.084*
C32	0.4354 (4)	0.35669 (14)	0.94247 (15)	0.0606 (9)
H32	0.5017	0.3787	0.9709	0.073*
C33	0.2768 (4)	0.37230 (12)	0.91384 (14)	0.0477 (8)
C34	0.1802 (3)	0.33820 (12)	0.87151 (14)	0.0428 (8)
C35	0.2993 (4)	0.45431 (12)	0.96661 (16)	0.0777 (11)
H35A	0.3141	0.4401	1.0108	0.117*
H35B	0.2375	0.4859	0.9671	0.117*
H35C	0.4089	0.4606	0.9518	0.117*
C36	0.0182 (3)	0.37367 (12)	0.77848 (14)	0.0471 (8)
H36A	0.0634	0.3488	0.7494	0.056*
H36B	0.0897	0.4039	0.7801	0.056*
C37	−0.1621 (3)	0.38743 (11)	0.75175 (15)	0.0449 (8)
C38	−0.2952 (4)	0.37516 (12)	0.78811 (16)	0.0598 (9)
H38	−0.2724	0.3581	0.8286	0.072*
C39	−0.4618 (4)	0.38780 (14)	0.7653 (2)	0.0733 (11)
H39	−0.5492	0.3789	0.7905	0.088*
C40	−0.4993 (4)	0.41337 (14)	0.7060 (2)	0.0742 (11)
H40	−0.6114	0.4219	0.6911	0.089*
C41	−0.3706 (4)	0.42625 (13)	0.66902 (17)	0.0641 (10)
H41	−0.3942	0.4439	0.6289	0.077*
C42	−0.2062 (4)	0.41291 (12)	0.69159 (15)	0.0489 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0407 (14)	0.0704 (16)	0.0831 (17)	−0.0013 (13)	0.0008 (11)	0.0140 (13)
O2	0.0336 (11)	0.0631 (14)	0.0390 (12)	0.0021 (10)	−0.0011 (9)	−0.0039 (10)
O3	0.0527 (13)	0.0606 (16)	0.0588 (14)	−0.0021 (13)	−0.0092 (11)	0.0111 (12)
O4	0.0555 (16)	0.151 (3)	0.0899 (19)	−0.0252 (18)	0.0166 (14)	−0.0500 (18)
O5	0.095 (2)	0.132 (2)	0.0575 (17)	−0.0245 (18)	0.0048 (14)	−0.0382 (17)
O6	0.0373 (13)	0.0826 (17)	0.0693 (16)	0.0029 (12)	0.0044 (11)	−0.0181 (12)
O7	0.0367 (12)	0.0613 (14)	0.0443 (13)	0.0034 (11)	0.0014 (9)	−0.0014 (11)
O8	0.0652 (15)	0.0536 (15)	0.0656 (15)	−0.0006 (13)	−0.0014 (11)	−0.0156 (12)
O9	0.0584 (17)	0.152 (3)	0.099 (2)	0.0232 (18)	0.0219 (15)	0.0517 (18)
O10	0.108 (2)	0.182 (3)	0.0694 (19)	0.028 (2)	0.0108 (16)	0.052 (2)
N1	0.112 (3)	0.097 (3)	0.090 (3)	0.017 (3)	−0.017 (2)	0.026 (2)
N2	0.0320 (14)	0.0602 (19)	0.0655 (18)	0.0048 (14)	−0.0059 (13)	0.0169 (15)
N3	0.0380 (15)	0.0523 (17)	0.0499 (17)	0.0072 (14)	−0.0033 (13)	0.0059 (14)
N4	0.063 (2)	0.076 (2)	0.0455 (18)	−0.0074 (18)	0.0019 (16)	−0.0075 (16)
N5	0.060 (2)	0.111 (3)	0.065 (2)	0.001 (2)	−0.0092 (17)	−0.0292 (19)
N6	0.0316 (14)	0.0642 (19)	0.0573 (17)	−0.0011 (14)	−0.0037 (12)	−0.0198 (15)
N7	0.0392 (15)	0.0564 (18)	0.0507 (17)	0.0003 (14)	−0.0102 (13)	−0.0117 (14)
N8	0.061 (2)	0.096 (3)	0.0481 (19)	0.006 (2)	−0.0026 (17)	0.0111 (17)
C1	0.078 (3)	0.079 (3)	0.067 (3)	0.010 (2)	0.011 (2)	0.011 (2)
C2	0.120 (4)	0.097 (3)	0.070 (3)	0.012 (3)	0.004 (3)	0.025 (2)
C3	0.071 (3)	0.107 (4)	0.111 (4)	0.019 (3)	−0.017 (3)	0.030 (3)
C4	0.061 (2)	0.074 (3)	0.090 (3)	0.009 (2)	−0.006 (2)	0.028 (2)
C5	0.052 (2)	0.047 (2)	0.058 (2)	0.0048 (18)	−0.0045 (17)	0.0041 (17)
C6	0.044 (2)	0.046 (2)	0.058 (2)	0.0018 (18)	0.0026 (17)	−0.0025 (17)
C7	0.0366 (18)	0.052 (2)	0.049 (2)	0.0060 (17)	0.0021 (15)	−0.0050 (17)
C8	0.0376 (18)	0.047 (2)	0.0392 (18)	0.0034 (16)	−0.0015 (14)	−0.0030 (15)
C9	0.046 (2)	0.060 (2)	0.055 (2)	−0.0060 (18)	−0.0076 (16)	0.0019 (18)
C10	0.047 (2)	0.074 (3)	0.057 (2)	−0.008 (2)	−0.0144 (17)	0.003 (2)
C11	0.048 (2)	0.063 (2)	0.046 (2)	−0.0010 (19)	−0.0107 (16)	0.0058 (17)
C12	0.0414 (19)	0.054 (2)	0.0389 (19)	−0.0067 (18)	0.0002 (15)	0.0001 (17)
C13	0.0314 (17)	0.058 (2)	0.0328 (18)	0.0039 (16)	−0.0024 (14)	−0.0048 (16)
C14	0.071 (2)	0.067 (2)	0.059 (2)	0.002 (2)	−0.0060 (18)	0.0106 (19)
C15	0.0396 (18)	0.054 (2)	0.0439 (19)	−0.0003 (16)	0.0016 (14)	−0.0052 (16)
C16	0.0327 (17)	0.0433 (19)	0.0453 (19)	0.0009 (15)	−0.0029 (14)	0.0056 (16)
C17	0.0326 (18)	0.070 (2)	0.063 (2)	0.0037 (18)	0.0013 (16)	−0.0074 (18)
C18	0.036 (2)	0.087 (3)	0.086 (3)	0.003 (2)	0.0094 (18)	−0.008 (2)
C19	0.038 (2)	0.070 (3)	0.095 (3)	−0.0010 (19)	−0.007 (2)	−0.005 (2)
C20	0.054 (2)	0.062 (2)	0.058 (2)	−0.006 (2)	−0.0106 (18)	−0.0007 (18)
C21	0.0412 (19)	0.049 (2)	0.043 (2)	−0.0022 (17)	0.0011 (16)	0.0035 (16)
C22	0.044 (2)	0.113 (3)	0.065 (3)	0.001 (2)	0.0076 (19)	−0.027 (2)
C23	0.066 (3)	0.149 (4)	0.065 (3)	0.006 (3)	0.000 (2)	−0.046 (3)
C24	0.053 (2)	0.082 (3)	0.069 (3)	−0.010 (2)	−0.003 (2)	−0.013 (2)
C25	0.051 (2)	0.072 (2)	0.050 (2)	−0.0081 (19)	0.0005 (17)	−0.0119 (18)
C26	0.0387 (19)	0.048 (2)	0.047 (2)	0.0052 (16)	−0.0041 (15)	−0.0069 (16)
C27	0.0389 (19)	0.050 (2)	0.048 (2)	0.0048 (17)	−0.0017 (16)	−0.0019 (16)
C28	0.0416 (19)	0.051 (2)	0.050 (2)	0.0030 (17)	−0.0011 (16)	−0.0012 (17)
C29	0.0406 (18)	0.052 (2)	0.0424 (19)	0.0032 (17)	−0.0054 (14)	−0.0047 (16)
C30	0.058 (2)	0.062 (2)	0.068 (2)	0.013 (2)	−0.0178 (18)	−0.013 (2)
C31	0.050 (2)	0.081 (3)	0.072 (3)	0.012 (2)	−0.0223 (18)	−0.014 (2)
C32	0.056 (2)	0.068 (3)	0.053 (2)	−0.005 (2)	−0.0152 (17)	−0.0141 (19)
C33	0.050 (2)	0.051 (2)	0.040 (2)	−0.0005 (19)	−0.0014 (16)	−0.0046 (17)
C34	0.0321 (17)	0.058 (2)	0.0375 (18)	0.0023 (17)	0.0000 (14)	0.0005 (16)
C35	0.097 (3)	0.062 (2)	0.073 (3)	−0.016 (2)	0.003 (2)	−0.023 (2)
C36	0.0378 (18)	0.054 (2)	0.049 (2)	0.0032 (16)	0.0041 (15)	0.0020 (17)
C37	0.0337 (17)	0.046 (2)	0.054 (2)	0.0026 (16)	0.0034 (15)	−0.0062 (16)
C38	0.041 (2)	0.071 (2)	0.066 (2)	0.0020 (19)	0.0008 (17)	0.0058 (19)
C39	0.036 (2)	0.095 (3)	0.090 (3)	−0.004 (2)	0.0105 (19)	0.002 (2)
C40	0.039 (2)	0.094 (3)	0.085 (3)	0.009 (2)	−0.010 (2)	−0.001 (2)
C41	0.053 (2)	0.074 (3)	0.061 (2)	0.011 (2)	−0.0109 (19)	0.001 (2)
C42	0.044 (2)	0.056 (2)	0.047 (2)	0.0006 (17)	0.0025 (17)	−0.0006 (17)

Geometric parameters (Å, º)

O1—C6	1.229 (3)	C14—H14C	0.9600
O2—C13	1.392 (3)	C15—C16	1.509 (3)
O2—C15	1.434 (3)	C15—H15A	0.9700
O3—C12	1.363 (3)	C15—H15B	0.9700
O3—C14	1.438 (3)	C16—C17	1.383 (4)
O4—N4	1.212 (3)	C16—C21	1.392 (4)
O5—N4	1.222 (3)	C17—C18	1.380 (4)
O6—C27	1.227 (3)	C17—H17	0.9300
O7—C34	1.389 (3)	C18—C19	1.375 (4)
O7—C36	1.432 (3)	C18—H18	0.9300
O8—C33	1.360 (3)	C19—C20	1.368 (4)
O8—C35	1.433 (3)	C19—H19	0.9300
O9—N8	1.201 (3)	C20—C21	1.383 (4)
O10—N8	1.217 (3)	C20—H20	0.9300
N1—C3	1.319 (5)	C22—C26	1.368 (4)
N1—C2	1.320 (5)	C22—C23	1.380 (4)
N2—C6	1.340 (4)	C22—H22	0.9300
N2—N3	1.383 (3)	C23—H23	0.9300
N2—H2A	0.8600	C24—C25	1.377 (4)
N3—C7	1.272 (3)	C24—H24	0.9300
N4—C21	1.462 (4)	C25—C26	1.365 (4)
N5—C23	1.310 (4)	C25—H25	0.9300
N5—C24	1.325 (4)	C26—C27	1.497 (4)
N6—C27	1.345 (3)	C28—C29	1.457 (4)
N6—N7	1.382 (3)	C28—H28	0.9300
N6—H6	0.8600	C29—C34	1.381 (4)
N7—C28	1.275 (3)	C29—C30	1.395 (4)
N8—C42	1.455 (4)	C30—C31	1.368 (4)
C1—C5	1.373 (4)	C30—H30	0.9300
C1—C2	1.377 (5)	C31—C32	1.386 (4)
C1—H1	0.9300	C31—H31	0.9300
C2—H2	0.9300	C32—C33	1.381 (4)
C3—C4	1.385 (5)	C32—H32	0.9300
C3—H3	0.9300	C33—C34	1.399 (4)
C4—C5	1.381 (4)	C35—H35A	0.9600
C4—H4	0.9300	C35—H35B	0.9600
C5—C6	1.494 (4)	C35—H35C	0.9600
C7—C8	1.458 (4)	C36—C37	1.508 (4)
C7—H7	0.9300	C36—H36A	0.9700
C8—C13	1.392 (4)	C36—H36B	0.9700
C8—C9	1.395 (4)	C37—C38	1.384 (4)
C9—C10	1.373 (4)	C37—C42	1.392 (4)
C9—H9	0.9300	C38—C39	1.384 (4)
C10—C11	1.377 (4)	C38—H38	0.9300
C10—H10	0.9300	C39—C40	1.372 (4)
C11—C12	1.387 (4)	C39—H39	0.9300
C11—H11	0.9300	C40—C41	1.367 (4)
C12—C13	1.380 (4)	C40—H40	0.9300
C14—H14A	0.9600	C41—C42	1.372 (4)
C14—H14B	0.9600	C41—H41	0.9300
C13—O2—C15	113.17 (19)	C17—C18—H18	119.7
C12—O3—C14	118.0 (2)	C20—C19—C18	119.7 (3)
C34—O7—C36	112.1 (2)	C20—C19—H19	120.1
C33—O8—C35	117.6 (2)	C18—C19—H19	120.1
C3—N1—C2	115.6 (4)	C19—C20—C21	118.8 (3)
C6—N2—N3	119.4 (2)	C19—C20—H20	120.6
C6—N2—H2A	120.3	C21—C20—H20	120.6
N3—N2—H2A	120.3	C20—C21—C16	123.3 (3)
C7—N3—N2	114.1 (2)	C20—C21—N4	115.7 (3)
O4—N4—O5	121.5 (3)	C16—C21—N4	121.0 (3)
O4—N4—C21	119.6 (3)	C26—C22—C23	119.3 (3)
O5—N4—C21	118.9 (3)	C26—C22—H22	120.3
C23—N5—C24	115.9 (3)	C23—C22—H22	120.3
C27—N6—N7	119.8 (2)	N5—C23—C22	124.4 (3)
C27—N6—H6	120.1	N5—C23—H23	117.8
N7—N6—H6	120.1	C22—C23—H23	117.8
C28—N7—N6	114.3 (2)	N5—C24—C25	123.7 (3)
O9—N8—O10	121.1 (3)	N5—C24—H24	118.2
O9—N8—C42	119.9 (3)	C25—C24—H24	118.2
O10—N8—C42	118.9 (3)	C26—C25—C24	119.9 (3)
C5—C1—C2	119.5 (4)	C26—C25—H25	120.0
C5—C1—H1	120.3	C24—C25—H25	120.0
C2—C1—H1	120.3	C25—C26—C22	116.8 (3)
N1—C2—C1	124.7 (4)	C25—C26—C27	123.5 (3)
N1—C2—H2	117.7	C22—C26—C27	119.7 (3)
C1—C2—H2	117.7	O6—C27—N6	123.1 (3)
N1—C3—C4	124.3 (4)	O6—C27—C26	122.5 (3)
N1—C3—H3	117.8	N6—C27—C26	114.4 (3)
C4—C3—H3	117.8	N7—C28—C29	121.3 (3)
C5—C4—C3	119.3 (4)	N7—C28—H28	119.4
C5—C4—H4	120.4	C29—C28—H28	119.4
C3—C4—H4	120.4	C34—C29—C30	118.6 (3)
C1—C5—C4	116.7 (3)	C34—C29—C28	118.8 (3)
C1—C5—C6	119.0 (3)	C30—C29—C28	122.5 (3)
C4—C5—C6	124.3 (3)	C31—C30—C29	120.2 (3)
O1—C6—N2	123.2 (3)	C31—C30—H30	119.9
O1—C6—C5	120.7 (3)	C29—C30—H30	119.9
N2—C6—C5	116.1 (3)	C30—C31—C32	120.8 (3)
N3—C7—C8	121.6 (3)	C30—C31—H31	119.6
N3—C7—H7	119.2	C32—C31—H31	119.6
C8—C7—H7	119.2	C33—C32—C31	120.4 (3)
C13—C8—C9	118.6 (3)	C33—C32—H32	119.8
C13—C8—C7	118.9 (3)	C31—C32—H32	119.8
C9—C8—C7	122.5 (3)	O8—C33—C32	125.5 (3)
C10—C9—C8	119.9 (3)	O8—C33—C34	116.2 (3)
C10—C9—H9	120.1	C32—C33—C34	118.3 (3)
C8—C9—H9	120.1	C29—C34—O7	119.4 (3)
C9—C10—C11	121.1 (3)	C29—C34—C33	121.7 (3)
C9—C10—H10	119.4	O7—C34—C33	118.9 (3)
C11—C10—H10	119.4	O8—C35—H35A	109.5
C10—C11—C12	120.0 (3)	O8—C35—H35B	109.5
C10—C11—H11	120.0	H35A—C35—H35B	109.5
C12—C11—H11	120.0	O8—C35—H35C	109.5
O3—C12—C13	115.9 (3)	H35A—C35—H35C	109.5
O3—C12—C11	125.0 (3)	H35B—C35—H35C	109.5
C13—C12—C11	119.1 (3)	O7—C36—C37	108.9 (2)
C12—C13—O2	119.5 (3)	O7—C36—H36A	109.9
C12—C13—C8	121.4 (3)	C37—C36—H36A	109.9
O2—C13—C8	119.1 (3)	O7—C36—H36B	109.9
O3—C14—H14A	109.5	C37—C36—H36B	109.9
O3—C14—H14B	109.5	H36A—C36—H36B	108.3
H14A—C14—H14B	109.5	C38—C37—C42	116.1 (3)
O3—C14—H14C	109.5	C38—C37—C36	119.9 (3)
H14A—C14—H14C	109.5	C42—C37—C36	124.0 (3)
H14B—C14—H14C	109.5	C37—C38—C39	121.3 (3)
O2—C15—C16	108.4 (2)	C37—C38—H38	119.4
O2—C15—H15A	110.0	C39—C38—H38	119.4
C16—C15—H15A	110.0	C40—C39—C38	120.7 (3)
O2—C15—H15B	110.0	C40—C39—H39	119.7
C16—C15—H15B	110.0	C38—C39—H39	119.7
H15A—C15—H15B	108.4	C41—C40—C39	119.5 (3)
C17—C16—C21	115.8 (3)	C41—C40—H40	120.3
C17—C16—C15	120.0 (3)	C39—C40—H40	120.3
C21—C16—C15	124.2 (3)	C40—C41—C42	119.3 (3)
C18—C17—C16	121.8 (3)	C40—C41—H41	120.3
C18—C17—H17	119.1	C42—C41—H41	120.3
C16—C17—H17	119.1	C41—C42—C37	123.1 (3)
C19—C18—C17	120.5 (3)	C41—C42—N8	116.1 (3)
C19—C18—H18	119.7	C37—C42—N8	120.8 (3)
C6—N2—N3—C7	−171.3 (3)	O5—N4—C21—C16	175.4 (3)
C27—N6—N7—C28	170.0 (3)	C24—N5—C23—C22	0.6 (6)
C3—N1—C2—C1	1.0 (7)	C26—C22—C23—N5	−0.4 (6)
C5—C1—C2—N1	−0.4 (7)	C23—N5—C24—C25	−1.1 (6)
C2—N1—C3—C4	−1.0 (7)	N5—C24—C25—C26	1.4 (5)
N1—C3—C4—C5	0.4 (6)	C24—C25—C26—C22	−1.1 (5)
C2—C1—C5—C4	−0.3 (5)	C24—C25—C26—C27	179.6 (3)
C2—C1—C5—C6	−179.4 (3)	C23—C22—C26—C25	0.6 (5)
C3—C4—C5—C1	0.3 (5)	C23—C22—C26—C27	179.9 (3)
C3—C4—C5—C6	179.4 (3)	N7—N6—C27—O6	2.9 (5)
N3—N2—C6—O1	−3.3 (5)	N7—N6—C27—C26	−176.5 (2)
N3—N2—C6—C5	176.8 (2)	C25—C26—C27—O6	154.6 (3)
C1—C5—C6—O1	17.1 (5)	C22—C26—C27—O6	−24.7 (5)
C4—C5—C6—O1	−162.0 (3)	C25—C26—C27—N6	−26.0 (4)
C1—C5—C6—N2	−163.0 (3)	C22—C26—C27—N6	154.8 (3)
C4—C5—C6—N2	17.9 (5)	N6—N7—C28—C29	−177.4 (2)
N2—N3—C7—C8	176.6 (2)	N7—C28—C29—C34	150.3 (3)
N3—C7—C8—C13	−158.1 (3)	N7—C28—C29—C30	−28.1 (5)
N3—C7—C8—C9	20.7 (4)	C34—C29—C30—C31	−1.1 (5)
C13—C8—C9—C10	0.6 (4)	C28—C29—C30—C31	177.4 (3)
C7—C8—C9—C10	−178.2 (3)	C29—C30—C31—C32	−0.3 (5)
C8—C9—C10—C11	0.6 (5)	C30—C31—C32—C33	0.8 (5)
C9—C10—C11—C12	−0.6 (5)	C35—O8—C33—C32	−3.3 (4)
C14—O3—C12—C13	177.0 (3)	C35—O8—C33—C34	178.2 (3)
C14—O3—C12—C11	−2.4 (4)	C31—C32—C33—O8	−178.3 (3)
C10—C11—C12—O3	178.9 (3)	C31—C32—C33—C34	0.1 (5)
C10—C11—C12—C13	−0.6 (4)	C30—C29—C34—O7	−177.4 (3)
O3—C12—C13—O2	2.9 (4)	C28—C29—C34—O7	4.2 (4)
C11—C12—C13—O2	−177.6 (2)	C30—C29—C34—C33	2.0 (4)
O3—C12—C13—C8	−177.7 (2)	C28—C29—C34—C33	−176.5 (3)
C11—C12—C13—C8	1.8 (4)	C36—O7—C34—C29	−84.8 (3)
C15—O2—C13—C12	−92.8 (3)	C36—O7—C34—C33	95.8 (3)
C15—O2—C13—C8	87.8 (3)	O8—C33—C34—C29	177.1 (3)
C9—C8—C13—C12	−1.8 (4)	C32—C33—C34—C29	−1.6 (4)
C7—C8—C13—C12	177.1 (3)	O8—C33—C34—O7	−3.6 (4)
C9—C8—C13—O2	177.6 (2)	C32—C33—C34—O7	177.8 (3)
C7—C8—C13—O2	−3.6 (4)	C34—O7—C36—C37	178.8 (2)
C13—O2—C15—C16	174.1 (2)	O7—C36—C37—C38	−5.2 (4)
O2—C15—C16—C17	0.2 (4)	O7—C36—C37—C42	174.0 (3)
O2—C15—C16—C21	−179.0 (2)	C42—C37—C38—C39	−0.1 (5)
C21—C16—C17—C18	0.8 (5)	C36—C37—C38—C39	179.2 (3)
C15—C16—C17—C18	−178.4 (3)	C37—C38—C39—C40	−0.6 (5)
C16—C17—C18—C19	−0.4 (5)	C38—C39—C40—C41	0.3 (6)
C17—C18—C19—C20	0.1 (5)	C39—C40—C41—C42	0.6 (5)
C18—C19—C20—C21	−0.2 (5)	C40—C41—C42—C37	−1.3 (5)
C19—C20—C21—C16	0.7 (5)	C40—C41—C42—N8	178.8 (3)
C19—C20—C21—N4	179.8 (3)	C38—C37—C42—C41	1.0 (5)
C17—C16—C21—C20	−1.0 (4)	C36—C37—C42—C41	−178.2 (3)
C15—C16—C21—C20	178.2 (3)	C38—C37—C42—N8	−179.1 (3)
C17—C16—C21—N4	180.0 (3)	C36—C37—C42—N8	1.7 (5)
C15—C16—C21—N4	−0.8 (4)	O9—N8—C42—C41	−171.6 (3)
O4—N4—C21—C20	177.4 (3)	O10—N8—C42—C41	11.8 (5)
O5—N4—C21—C20	−3.8 (4)	O9—N8—C42—C37	8.4 (5)
O4—N4—C21—C16	−3.5 (4)	O10—N8—C42—C37	−168.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O6	0.86	2.32	2.957 (3)	131
N2—H2A···N7	0.86	2.54	3.314 (3)	150
N6—H6···O1^i	0.86	2.34	2.894 (3)	123
N6—H6···N3^i	0.86	2.53	3.365 (3)	165
C25—H25···N3^i	0.93	2.55	3.382 (4)	150
C40—H40···O9^i	0.93	2.56	3.448 (4)	159
C32—H32···N5^ii	0.93	2.45	3.299 (4)	151
C14—H14C···O10^ii	0.96	2.54	3.445 (4)	157

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