Crystal structure of (2E)-2-meth­oxy­imino-2-{2-[(2-methyl­phen­oxy)meth­yl]phen­yl}-N′-(4-nitro­benzyl­idene)ethano­hydrazide

The title compound crystallizes with the two mol­ecules in the asymmetric unit (Z′ = 2) oriented almost perpendicular to each other [dihedral angle between the central core of each mol­ecule = 77.95 (3)°]. The two mol­ecules exhibit similar conformations with an extended structure and are linked by bifurcated hydrogen bonds into a ribbon along the a-axis direction.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.094
• Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2A    --  N1A     ..        5.2 su
PLAT480_ALERT_4_C Long H...A H-Bond Reported H17B   ..  N4A     ..       2.68 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5BA   ..  O2A     ..       2.63 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .         59 Ang3
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.728 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Th(Min) ...          5 Report
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         19 Report

Alert level G
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         10 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         70 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis 2007); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(2E)-2-Methoxyimino-2-{2-[(2-methylphenoxy)methyl]phenyl}-N'-(4-nitrobenzylidene)ethanohydrazide

Crystal data

C24H22N4O5	F(000) = 1872
Mr = 446.45	Dx = 1.327 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.6821 (4) Å	Cell parameters from 9882 reflections
b = 23.2151 (12) Å	θ = 2.4–28.2°
c = 25.1943 (15) Å	µ = 0.10 mm^−1
β = 95.803 (2)°	T = 120 K
V = 4470.1 (4) Å^3	Needle, colourless
Z = 8	0.45 × 0.21 × 0.14 mm

Data collection

Bruker APEXII diffractometer	8755 reflections with I > 2σ(I)
ω scans	Rint = 0.031
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	θmax = 28.3°, θmin = 2.4°
Tmin = 0.692, Tmax = 0.746	h = −10→10
34631 measured reflections	k = −30→30
11046 independent reflections	l = −33→33

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.0372P)^2 + 1.7501P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
11046 reflections	Δρmax = 0.35 e Å^−3
607 parameters	Δρmin = −0.22 e Å^−3

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.

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

	x	y	z	Uiso*/Ueq
O1A	−0.26253 (16)	0.40731 (5)	0.53333 (5)	0.0423 (3)
O2A	−0.02317 (16)	0.36271 (4)	0.51986 (4)	0.0405 (3)
O3A	0.09946 (11)	0.75766 (4)	0.62417 (3)	0.01910 (18)
O4A	0.63124 (11)	0.82755 (4)	0.69184 (3)	0.01848 (18)
O5A	0.58188 (11)	0.87760 (4)	0.52350 (3)	0.02218 (19)
N1A	−0.10267 (18)	0.40448 (5)	0.53527 (4)	0.0303 (3)
N2A	0.21581 (12)	0.64878 (4)	0.61833 (4)	0.01462 (19)
N3A	0.32523 (13)	0.69387 (4)	0.63413 (4)	0.01431 (19)
H3A	0.437 (2)	0.6869 (7)	0.6411 (6)	0.030 (4)*
N4A	0.52650 (13)	0.78002 (4)	0.67838 (4)	0.0158 (2)
C1A	0.18827 (16)	0.55055 (5)	0.59120 (4)	0.0175 (2)
C2A	0.27370 (18)	0.50151 (6)	0.57471 (5)	0.0233 (3)
H2AA	0.3977	0.5014	0.5757	0.028*
C3A	0.17973 (19)	0.45306 (6)	0.55686 (5)	0.0251 (3)
H3AA	0.2375	0.4198	0.5455	0.030*
C4A	0.00012 (19)	0.45453 (5)	0.55613 (5)	0.0231 (3)
C5A	−0.08892 (18)	0.50194 (6)	0.57312 (5)	0.0245 (3)
H5AA	−0.2127	0.5014	0.5728	0.029*
C6A	0.00629 (17)	0.55002 (5)	0.59056 (5)	0.0210 (3)
H6AA	−0.0525	0.5830	0.6022	0.025*
C7A	0.29202 (15)	0.60136 (5)	0.60856 (4)	0.0167 (2)
H7AA	0.4161	0.5992	0.6126	0.020*
C8A	0.25467 (15)	0.74729 (5)	0.63586 (4)	0.0141 (2)
C9A	0.38222 (15)	0.79508 (5)	0.65171 (4)	0.0141 (2)
C10A	0.78988 (17)	0.80896 (6)	0.72185 (6)	0.0283 (3)
H10A	0.8557	0.8426	0.7362	0.042*
H10B	0.8608	0.7872	0.6986	0.042*
H10C	0.7615	0.7843	0.7513	0.042*
C11A	0.32872 (15)	0.85461 (5)	0.63561 (5)	0.0161 (2)
C12A	0.18674 (16)	0.87956 (6)	0.65749 (5)	0.0227 (3)
H12A	0.1305	0.8593	0.6837	0.027*
C13A	0.12772 (17)	0.93369 (6)	0.64103 (6)	0.0287 (3)
H13A	0.0335	0.9511	0.6568	0.034*
C14A	0.20638 (18)	0.96246 (6)	0.60155 (6)	0.0285 (3)
H14A	0.1623	0.9987	0.5890	0.034*
C15A	0.34927 (18)	0.93837 (5)	0.58034 (5)	0.0234 (3)
H15A	0.4031	0.9586	0.5536	0.028*
C16A	0.41512 (16)	0.88485 (5)	0.59776 (5)	0.0172 (2)
C17A	0.58044 (16)	0.86198 (5)	0.57803 (4)	0.0179 (2)
H17A	0.6839	0.8785	0.5994	0.022*
H17B	0.5849	0.8195	0.5818	0.022*
C18A	0.73512 (16)	0.86995 (5)	0.50045 (5)	0.0180 (2)
C19A	0.89187 (17)	0.85147 (6)	0.52730 (5)	0.0221 (3)
H19A	0.8994	0.8430	0.5644	0.027*
C20A	1.03816 (17)	0.84545 (6)	0.49918 (6)	0.0262 (3)
H20A	1.1461	0.8330	0.5173	0.031*
C21A	1.02759 (18)	0.85741 (6)	0.44521 (6)	0.0273 (3)
H21A	1.1279	0.8536	0.4263	0.033*
C22A	0.86849 (18)	0.87511 (5)	0.41876 (5)	0.0232 (3)
H22A	0.8613	0.8827	0.3816	0.028*
C23A	0.72052 (17)	0.88192 (5)	0.44540 (5)	0.0191 (2)
C24A	0.54785 (18)	0.89964 (6)	0.41707 (5)	0.0238 (3)
H24A	0.5586	0.9032	0.3788	0.036*
H24B	0.5127	0.9368	0.4310	0.036*
H24C	0.4594	0.8705	0.4229	0.036*
O1B	0.38132 (18)	0.77311 (5)	0.32876 (4)	0.0468 (3)
O2B	0.15770 (17)	0.74670 (6)	0.36820 (5)	0.0509 (3)
O3B	0.62240 (11)	0.63511 (4)	0.68689 (3)	0.01902 (18)
O4B	1.16718 (11)	0.66162 (4)	0.77511 (3)	0.01737 (17)
O5B	1.15483 (11)	0.48146 (4)	0.72363 (3)	0.01938 (18)
N1B	0.31493 (19)	0.75518 (5)	0.36773 (4)	0.0308 (3)
N2B	0.70567 (12)	0.68705 (4)	0.59787 (4)	0.01368 (19)
N3B	0.82799 (13)	0.67735 (4)	0.64094 (4)	0.01422 (19)
H3B	0.939 (2)	0.6897 (6)	0.6404 (6)	0.023 (4)*
N4B	1.04705 (12)	0.67334 (4)	0.73131 (4)	0.01504 (19)
C1B	0.64769 (15)	0.71712 (5)	0.50724 (4)	0.0149 (2)
C2B	0.71807 (17)	0.73457 (5)	0.46063 (5)	0.0211 (3)
H2BA	0.8413	0.7375	0.4603	0.025*
C3B	0.60910 (19)	0.74755 (5)	0.41500 (5)	0.0237 (3)
H3BA	0.6562	0.7596	0.3834	0.028*
C4B	0.43094 (18)	0.74257 (5)	0.41647 (5)	0.0213 (3)
C5B	0.35669 (17)	0.72551 (6)	0.46181 (5)	0.0224 (3)
H5BA	0.2333	0.7226	0.4618	0.027*
C6B	0.46675 (16)	0.71285 (5)	0.50711 (5)	0.0189 (2)
H6BA	0.4184	0.7011	0.5386	0.023*
C7B	0.76688 (15)	0.70484 (5)	0.55520 (4)	0.0151 (2)
H7BA	0.8894	0.7101	0.5547	0.018*
C8B	0.77310 (15)	0.65102 (5)	0.68428 (4)	0.0135 (2)
C9B	0.91295 (14)	0.64002 (5)	0.72976 (4)	0.0135 (2)
C10B	1.30753 (16)	0.70259 (6)	0.77600 (5)	0.0228 (3)
H10D	1.3809	0.6998	0.8101	0.034*
H10E	1.2591	0.7416	0.7719	0.034*
H10F	1.3784	0.6944	0.7467	0.034*
C11B	0.87970 (14)	0.59275 (5)	0.76739 (4)	0.0136 (2)
C12B	0.73387 (15)	0.59676 (5)	0.79640 (5)	0.0168 (2)
H12B	0.6619	0.6301	0.7932	0.020*
C13B	0.69440 (16)	0.55214 (6)	0.82974 (5)	0.0193 (2)
H13B	0.5972	0.5553	0.8501	0.023*
C14B	0.79674 (16)	0.50289 (5)	0.83340 (5)	0.0197 (2)
H14B	0.7677	0.4719	0.8556	0.024*
C15B	0.94123 (16)	0.49860 (5)	0.80488 (5)	0.0174 (2)
H15B	1.0106	0.4646	0.8076	0.021*
C16B	0.98577 (15)	0.54373 (5)	0.77224 (4)	0.0141 (2)
C17B	1.15104 (15)	0.53835 (5)	0.74491 (5)	0.0157 (2)
H17C	1.1514	0.5671	0.7159	0.019*
H17D	1.2549	0.5450	0.7708	0.019*
C18B	1.30751 (16)	0.46297 (5)	0.70551 (4)	0.0173 (2)
C19B	1.45797 (16)	0.49618 (6)	0.70528 (5)	0.0202 (2)
H19B	1.4604	0.5345	0.7186	0.024*
C20B	1.60527 (17)	0.47275 (6)	0.68534 (5)	0.0262 (3)
H20B	1.7091	0.4950	0.6856	0.031*
C21B	1.60113 (19)	0.41739 (7)	0.66519 (6)	0.0316 (3)
H21B	1.7010	0.4017	0.6511	0.038*
C22B	1.44928 (19)	0.38478 (6)	0.66570 (5)	0.0285 (3)
H22B	1.4473	0.3467	0.6519	0.034*
C23B	1.30058 (17)	0.40636 (5)	0.68578 (5)	0.0208 (3)
C24B	1.13482 (19)	0.37187 (6)	0.68574 (6)	0.0277 (3)
H24D	1.1497	0.3346	0.6685	0.042*
H24E	1.0381	0.3929	0.6661	0.042*
H24F	1.1086	0.3656	0.7226	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0443 (7)	0.0344 (6)	0.0491 (7)	−0.0186 (5)	0.0097 (5)	−0.0134 (5)
O2A	0.0595 (8)	0.0217 (5)	0.0416 (6)	−0.0068 (5)	0.0120 (5)	−0.0129 (4)
O3A	0.0119 (4)	0.0179 (4)	0.0267 (4)	−0.0008 (3)	−0.0017 (3)	0.0026 (3)
O4A	0.0147 (4)	0.0185 (4)	0.0211 (4)	−0.0050 (3)	−0.0039 (3)	−0.0009 (3)
O5A	0.0194 (4)	0.0303 (5)	0.0167 (4)	0.0004 (4)	0.0012 (3)	0.0059 (3)
N1A	0.0474 (8)	0.0215 (6)	0.0227 (6)	−0.0116 (5)	0.0074 (5)	−0.0043 (4)
N2A	0.0138 (5)	0.0159 (5)	0.0140 (4)	−0.0033 (4)	0.0002 (4)	0.0004 (4)
N3A	0.0093 (5)	0.0158 (5)	0.0175 (5)	−0.0017 (4)	−0.0002 (4)	−0.0010 (4)
N4A	0.0142 (5)	0.0171 (5)	0.0159 (5)	−0.0045 (4)	0.0009 (4)	−0.0011 (4)
C1A	0.0214 (6)	0.0169 (6)	0.0135 (5)	−0.0003 (5)	−0.0017 (4)	−0.0002 (4)
C2A	0.0242 (7)	0.0221 (6)	0.0224 (6)	0.0044 (5)	−0.0038 (5)	−0.0023 (5)
C3A	0.0362 (8)	0.0179 (6)	0.0201 (6)	0.0056 (6)	−0.0029 (5)	−0.0028 (5)
C4A	0.0376 (8)	0.0172 (6)	0.0142 (5)	−0.0070 (5)	0.0016 (5)	−0.0011 (4)
C5A	0.0258 (7)	0.0245 (7)	0.0239 (6)	−0.0065 (5)	0.0052 (5)	−0.0043 (5)
C6A	0.0229 (6)	0.0183 (6)	0.0223 (6)	−0.0023 (5)	0.0044 (5)	−0.0046 (5)
C7A	0.0138 (5)	0.0193 (6)	0.0165 (5)	0.0013 (5)	−0.0006 (4)	−0.0006 (4)
C8A	0.0121 (5)	0.0171 (5)	0.0129 (5)	−0.0018 (4)	0.0012 (4)	0.0019 (4)
C9A	0.0126 (5)	0.0161 (5)	0.0138 (5)	−0.0014 (4)	0.0020 (4)	−0.0002 (4)
C10A	0.0185 (6)	0.0311 (7)	0.0325 (7)	−0.0036 (6)	−0.0113 (5)	0.0013 (6)
C11A	0.0135 (5)	0.0148 (5)	0.0192 (5)	−0.0006 (4)	−0.0032 (4)	−0.0028 (4)
C12A	0.0148 (6)	0.0224 (6)	0.0305 (7)	−0.0012 (5)	0.0016 (5)	−0.0049 (5)
C13A	0.0166 (6)	0.0222 (7)	0.0463 (8)	0.0031 (5)	−0.0014 (6)	−0.0099 (6)
C14A	0.0257 (7)	0.0147 (6)	0.0425 (8)	0.0040 (5)	−0.0097 (6)	−0.0027 (5)
C15A	0.0279 (7)	0.0153 (6)	0.0255 (6)	−0.0016 (5)	−0.0047 (5)	0.0006 (5)
C16A	0.0193 (6)	0.0144 (5)	0.0168 (5)	−0.0024 (5)	−0.0033 (4)	−0.0025 (4)
C17A	0.0225 (6)	0.0152 (5)	0.0159 (5)	−0.0013 (5)	0.0015 (4)	0.0016 (4)
C18A	0.0186 (6)	0.0159 (6)	0.0192 (6)	−0.0037 (5)	0.0012 (4)	0.0006 (4)
C19A	0.0227 (6)	0.0229 (6)	0.0199 (6)	−0.0030 (5)	−0.0024 (5)	0.0005 (5)
C20A	0.0181 (6)	0.0276 (7)	0.0319 (7)	−0.0028 (5)	−0.0028 (5)	−0.0036 (5)
C21A	0.0228 (7)	0.0281 (7)	0.0323 (7)	−0.0045 (6)	0.0087 (5)	−0.0040 (6)
C22A	0.0299 (7)	0.0203 (6)	0.0202 (6)	−0.0053 (5)	0.0058 (5)	0.0008 (5)
C23A	0.0235 (6)	0.0138 (5)	0.0197 (6)	−0.0043 (5)	0.0009 (5)	0.0019 (4)
C24A	0.0285 (7)	0.0242 (6)	0.0178 (6)	−0.0007 (5)	−0.0018 (5)	0.0050 (5)
O1B	0.0826 (9)	0.0361 (6)	0.0180 (5)	−0.0131 (6)	−0.0128 (5)	0.0090 (4)
O2B	0.0429 (7)	0.0751 (9)	0.0307 (6)	0.0191 (7)	−0.0162 (5)	−0.0011 (6)
O3B	0.0124 (4)	0.0228 (4)	0.0212 (4)	−0.0031 (3)	−0.0016 (3)	0.0059 (3)
O4B	0.0134 (4)	0.0196 (4)	0.0177 (4)	−0.0032 (3)	−0.0056 (3)	0.0028 (3)
O5B	0.0167 (4)	0.0159 (4)	0.0262 (4)	0.0012 (3)	0.0048 (3)	−0.0049 (3)
N1B	0.0534 (8)	0.0185 (5)	0.0175 (5)	0.0063 (5)	−0.0112 (5)	−0.0022 (4)
N2B	0.0113 (4)	0.0140 (5)	0.0149 (4)	0.0010 (4)	−0.0026 (3)	−0.0001 (3)
N3B	0.0088 (4)	0.0176 (5)	0.0157 (5)	−0.0002 (4)	−0.0018 (3)	0.0005 (4)
N4B	0.0127 (5)	0.0172 (5)	0.0144 (4)	0.0015 (4)	−0.0029 (4)	−0.0001 (4)
C1B	0.0189 (6)	0.0112 (5)	0.0145 (5)	−0.0018 (4)	0.0009 (4)	−0.0015 (4)
C2B	0.0243 (6)	0.0217 (6)	0.0178 (6)	−0.0082 (5)	0.0044 (5)	−0.0026 (5)
C3B	0.0396 (8)	0.0178 (6)	0.0139 (5)	−0.0088 (6)	0.0035 (5)	−0.0009 (4)
C4B	0.0362 (7)	0.0121 (5)	0.0137 (5)	0.0020 (5)	−0.0064 (5)	−0.0013 (4)
C5B	0.0201 (6)	0.0247 (6)	0.0214 (6)	0.0033 (5)	−0.0029 (5)	−0.0007 (5)
C6B	0.0184 (6)	0.0223 (6)	0.0159 (5)	0.0005 (5)	0.0013 (4)	0.0030 (4)
C7B	0.0119 (5)	0.0162 (5)	0.0172 (5)	−0.0018 (4)	0.0017 (4)	−0.0022 (4)
C8B	0.0122 (5)	0.0112 (5)	0.0167 (5)	0.0020 (4)	−0.0009 (4)	−0.0010 (4)
C9B	0.0116 (5)	0.0131 (5)	0.0155 (5)	0.0022 (4)	0.0001 (4)	−0.0012 (4)
C10B	0.0177 (6)	0.0265 (7)	0.0229 (6)	−0.0095 (5)	−0.0049 (5)	0.0022 (5)
C11B	0.0126 (5)	0.0150 (5)	0.0124 (5)	−0.0012 (4)	−0.0024 (4)	−0.0009 (4)
C12B	0.0134 (5)	0.0178 (6)	0.0187 (5)	0.0016 (5)	−0.0009 (4)	−0.0021 (4)
C13B	0.0139 (6)	0.0258 (6)	0.0186 (6)	−0.0029 (5)	0.0027 (4)	−0.0006 (5)
C14B	0.0186 (6)	0.0212 (6)	0.0191 (6)	−0.0049 (5)	0.0002 (5)	0.0045 (5)
C15B	0.0167 (6)	0.0154 (5)	0.0193 (6)	0.0011 (5)	−0.0014 (4)	0.0012 (4)
C16B	0.0132 (5)	0.0156 (5)	0.0127 (5)	−0.0006 (4)	−0.0018 (4)	−0.0016 (4)
C17B	0.0157 (5)	0.0136 (5)	0.0177 (5)	0.0014 (4)	0.0012 (4)	−0.0012 (4)
C18B	0.0180 (6)	0.0190 (6)	0.0145 (5)	0.0053 (5)	−0.0002 (4)	0.0004 (4)
C19B	0.0188 (6)	0.0234 (6)	0.0179 (6)	0.0019 (5)	0.0001 (5)	−0.0018 (5)
C20B	0.0164 (6)	0.0392 (8)	0.0226 (6)	0.0023 (6)	0.0002 (5)	−0.0034 (5)
C21B	0.0223 (7)	0.0431 (9)	0.0296 (7)	0.0138 (6)	0.0040 (5)	−0.0054 (6)
C22B	0.0320 (7)	0.0250 (7)	0.0279 (7)	0.0123 (6)	−0.0003 (6)	−0.0060 (5)
C23B	0.0245 (6)	0.0189 (6)	0.0183 (6)	0.0051 (5)	−0.0014 (5)	0.0000 (4)
C24B	0.0335 (8)	0.0172 (6)	0.0325 (7)	−0.0005 (6)	0.0029 (6)	−0.0032 (5)

Geometric parameters (Å, º)

O1A—N1A	1.2258 (17)	O1B—N1B	1.2242 (17)
O2A—N1A	1.2296 (16)	O2B—N1B	1.2250 (18)
O3A—C8A	1.2228 (14)	O3B—C8B	1.2233 (14)
O4A—N4A	1.3873 (13)	O4B—N4B	1.3918 (12)
O4A—C10A	1.4341 (15)	O4B—C10B	1.4361 (14)
O5A—C18A	1.3758 (15)	O5B—C18B	1.3700 (14)
O5A—C17A	1.4222 (14)	O5B—C17B	1.4266 (14)
N1A—C4A	1.4716 (17)	N1B—C4B	1.4719 (16)
N2A—C7A	1.2823 (15)	N2B—C7B	1.2844 (15)
N2A—N3A	1.3759 (14)	N2B—N3B	1.3803 (13)
N3A—C8A	1.3560 (15)	N3B—C8B	1.3552 (15)
N3A—H3A	0.871 (17)	N3B—H3B	0.901 (16)
N4A—C9A	1.2853 (15)	N4B—C9B	1.2856 (15)
C1A—C6A	1.3965 (17)	C1B—C6B	1.3932 (17)
C1A—C2A	1.3982 (17)	C1B—C2B	1.4013 (16)
C1A—C7A	1.4654 (17)	C1B—C7B	1.4683 (16)
C2A—C3A	1.3865 (19)	C2B—C3B	1.3852 (18)
C2A—H2AA	0.9500	C2B—H2BA	0.9500
C3A—C4A	1.378 (2)	C3B—C4B	1.378 (2)
C3A—H3AA	0.9500	C3B—H3BA	0.9500
C4A—C5A	1.3864 (19)	C4B—C5B	1.3852 (18)
C5A—C6A	1.3815 (18)	C5B—C6B	1.3816 (17)
C5A—H5AA	0.9500	C5B—H5BA	0.9500
C6A—H6AA	0.9500	C6B—H6BA	0.9500
C7A—H7AA	0.9500	C7B—H7BA	0.9500
C8A—C9A	1.5072 (16)	C8B—C9B	1.5110 (15)
C9A—C11A	1.4864 (16)	C9B—C11B	1.4892 (16)
C10A—H10A	0.9800	C10B—H10D	0.9800
C10A—H10B	0.9800	C10B—H10E	0.9800
C10A—H10C	0.9800	C10B—H10F	0.9800
C11A—C12A	1.3965 (17)	C11B—C16B	1.3979 (16)
C11A—C16A	1.4039 (17)	C11B—C12B	1.4012 (16)
C12A—C13A	1.3851 (19)	C12B—C13B	1.3865 (17)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—C14A	1.386 (2)	C13B—C14B	1.3854 (18)
C13A—H13A	0.9500	C13B—H13B	0.9500
C14A—C15A	1.386 (2)	C14B—C15B	1.3855 (17)
C14A—H14A	0.9500	C14B—H14B	0.9500
C15A—C16A	1.3954 (17)	C15B—C16B	1.3956 (16)
C15A—H15A	0.9500	C15B—H15B	0.9500
C16A—C17A	1.5065 (17)	C16B—C17B	1.5094 (16)
C17A—H17A	0.9900	C17B—H17C	0.9900
C17A—H17B	0.9900	C17B—H17D	0.9900
C18A—C19A	1.3881 (18)	C18B—C19B	1.3899 (18)
C18A—C23A	1.4076 (16)	C18B—C23B	1.4040 (17)
C19A—C20A	1.3947 (19)	C19B—C20B	1.3941 (18)
C19A—H19A	0.9500	C19B—H19B	0.9500
C20A—C21A	1.382 (2)	C20B—C21B	1.381 (2)
C20A—H20A	0.9500	C20B—H20B	0.9500
C21A—C22A	1.394 (2)	C21B—C22B	1.392 (2)
C21A—H21A	0.9500	C21B—H21B	0.9500
C22A—C23A	1.3863 (18)	C22B—C23B	1.3888 (18)
C22A—H22A	0.9500	C22B—H22B	0.9500
C23A—C24A	1.4989 (18)	C23B—C24B	1.5040 (19)
C24A—H24A	0.9800	C24B—H24D	0.9800
C24A—H24B	0.9800	C24B—H24E	0.9800
C24A—H24C	0.9800	C24B—H24F	0.9800
N4A—O4A—C10A	109.30 (9)	N4B—O4B—C10B	108.64 (8)
C18A—O5A—C17A	117.74 (9)	C18B—O5B—C17B	117.78 (9)
O1A—N1A—O2A	123.86 (12)	O1B—N1B—O2B	123.61 (12)
O1A—N1A—C4A	118.11 (12)	O1B—N1B—C4B	118.07 (13)
O2A—N1A—C4A	118.01 (13)	O2B—N1B—C4B	118.32 (12)
C7A—N2A—N3A	115.55 (10)	C7B—N2B—N3B	115.65 (10)
C8A—N3A—N2A	118.07 (10)	C8B—N3B—N2B	117.68 (10)
C8A—N3A—H3A	123.4 (11)	C8B—N3B—H3B	121.9 (9)
N2A—N3A—H3A	118.4 (11)	N2B—N3B—H3B	120.4 (9)
C9A—N4A—O4A	111.07 (9)	C9B—N4B—O4B	111.82 (9)
C6A—C1A—C2A	119.26 (11)	C6B—C1B—C2B	119.21 (11)
C6A—C1A—C7A	121.62 (11)	C6B—C1B—C7B	121.81 (10)
C2A—C1A—C7A	119.12 (11)	C2B—C1B—C7B	118.97 (11)
C3A—C2A—C1A	120.81 (12)	C3B—C2B—C1B	120.43 (12)
C3A—C2A—H2AA	119.6	C3B—C2B—H2BA	119.8
C1A—C2A—H2AA	119.6	C1B—C2B—H2BA	119.8
C4A—C3A—C2A	118.16 (12)	C4B—C3B—C2B	118.56 (11)
C4A—C3A—H3AA	120.9	C4B—C3B—H3BA	120.7
C2A—C3A—H3AA	120.9	C2B—C3B—H3BA	120.7
C3A—C4A—C5A	122.68 (12)	C3B—C4B—C5B	122.63 (11)
C3A—C4A—N1A	119.05 (12)	C3B—C4B—N1B	118.70 (12)
C5A—C4A—N1A	118.26 (13)	C5B—C4B—N1B	118.67 (12)
C6A—C5A—C4A	118.54 (13)	C6B—C5B—C4B	118.26 (12)
C6A—C5A—H5AA	120.7	C6B—C5B—H5BA	120.9
C4A—C5A—H5AA	120.7	C4B—C5B—H5BA	120.9
C5A—C6A—C1A	120.53 (12)	C5B—C6B—C1B	120.92 (11)
C5A—C6A—H6AA	119.7	C5B—C6B—H6BA	119.5
C1A—C6A—H6AA	119.7	C1B—C6B—H6BA	119.5
N2A—C7A—C1A	120.21 (11)	N2B—C7B—C1B	120.04 (10)
N2A—C7A—H7AA	119.9	N2B—C7B—H7BA	120.0
C1A—C7A—H7AA	119.9	C1B—C7B—H7BA	120.0
O3A—C8A—N3A	123.75 (11)	O3B—C8B—N3B	123.56 (10)
O3A—C8A—C9A	120.72 (10)	O3B—C8B—C9B	120.83 (10)
N3A—C8A—C9A	115.50 (10)	N3B—C8B—C9B	115.58 (10)
N4A—C9A—C11A	126.56 (10)	N4B—C9B—C11B	127.77 (10)
N4A—C9A—C8A	116.19 (10)	N4B—C9B—C8B	115.32 (10)
C11A—C9A—C8A	117.24 (10)	C11B—C9B—C8B	116.91 (10)
O4A—C10A—H10A	109.5	O4B—C10B—H10D	109.5
O4A—C10A—H10B	109.5	O4B—C10B—H10E	109.5
H10A—C10A—H10B	109.5	H10D—C10B—H10E	109.5
O4A—C10A—H10C	109.5	O4B—C10B—H10F	109.5
H10A—C10A—H10C	109.5	H10D—C10B—H10F	109.5
H10B—C10A—H10C	109.5	H10E—C10B—H10F	109.5
C12A—C11A—C16A	120.16 (11)	C16B—C11B—C12B	119.89 (10)
C12A—C11A—C9A	118.91 (11)	C16B—C11B—C9B	121.31 (10)
C16A—C11A—C9A	120.90 (10)	C12B—C11B—C9B	118.74 (10)
C13A—C12A—C11A	120.22 (12)	C13B—C12B—C11B	120.11 (11)
C13A—C12A—H12A	119.9	C13B—C12B—H12B	119.9
C11A—C12A—H12A	119.9	C11B—C12B—H12B	119.9
C12A—C13A—C14A	119.90 (13)	C14B—C13B—C12B	119.98 (11)
C12A—C13A—H13A	120.0	C14B—C13B—H13B	120.0
C14A—C13A—H13A	120.0	C12B—C13B—H13B	120.0
C13A—C14A—C15A	120.12 (12)	C15B—C14B—C13B	120.25 (11)
C13A—C14A—H14A	119.9	C15B—C14B—H14B	119.9
C15A—C14A—H14A	119.9	C13B—C14B—H14B	119.9
C14A—C15A—C16A	120.92 (12)	C14B—C15B—C16B	120.58 (11)
C14A—C15A—H15A	119.5	C14B—C15B—H15B	119.7
C16A—C15A—H15A	119.5	C16B—C15B—H15B	119.7
C15A—C16A—C11A	118.54 (11)	C15B—C16B—C11B	119.15 (11)
C15A—C16A—C17A	120.06 (11)	C15B—C16B—C17B	118.32 (10)
C11A—C16A—C17A	121.34 (10)	C11B—C16B—C17B	122.50 (10)
O5A—C17A—C16A	108.55 (10)	O5B—C17B—C16B	107.34 (9)
O5A—C17A—H17A	110.0	O5B—C17B—H17C	110.2
C16A—C17A—H17A	110.0	C16B—C17B—H17C	110.2
O5A—C17A—H17B	110.0	O5B—C17B—H17D	110.2
C16A—C17A—H17B	110.0	C16B—C17B—H17D	110.2
H17A—C17A—H17B	108.4	H17C—C17B—H17D	108.5
O5A—C18A—C19A	124.84 (11)	O5B—C18B—C19B	124.60 (11)
O5A—C18A—C23A	113.83 (11)	O5B—C18B—C23B	114.10 (11)
C19A—C18A—C23A	121.32 (11)	C19B—C18B—C23B	121.30 (11)
C18A—C19A—C20A	119.16 (12)	C18B—C19B—C20B	119.39 (12)
C18A—C19A—H19A	120.4	C18B—C19B—H19B	120.3
C20A—C19A—H19A	120.4	C20B—C19B—H19B	120.3
C21A—C20A—C19A	120.62 (13)	C21B—C20B—C19B	120.41 (13)
C21A—C20A—H20A	119.7	C21B—C20B—H20B	119.8
C19A—C20A—H20A	119.7	C19B—C20B—H20B	119.8
C20A—C21A—C22A	119.41 (12)	C20B—C21B—C22B	119.40 (12)
C20A—C21A—H21A	120.3	C20B—C21B—H21B	120.3
C22A—C21A—H21A	120.3	C22B—C21B—H21B	120.3
C23A—C22A—C21A	121.64 (12)	C23B—C22B—C21B	121.88 (13)
C23A—C22A—H22A	119.2	C23B—C22B—H22B	119.1
C21A—C22A—H22A	119.2	C21B—C22B—H22B	119.1
C22A—C23A—C18A	117.83 (12)	C22B—C23B—C18B	117.61 (12)
C22A—C23A—C24A	122.02 (11)	C22B—C23B—C24B	122.36 (12)
C18A—C23A—C24A	120.12 (11)	C18B—C23B—C24B	120.02 (11)
C23A—C24A—H24A	109.5	C23B—C24B—H24D	109.5
C23A—C24A—H24B	109.5	C23B—C24B—H24E	109.5
H24A—C24A—H24B	109.5	H24D—C24B—H24E	109.5
C23A—C24A—H24C	109.5	C23B—C24B—H24F	109.5
H24A—C24A—H24C	109.5	H24D—C24B—H24F	109.5
H24B—C24A—H24C	109.5	H24E—C24B—H24F	109.5
C7A—N2A—N3A—C8A	168.52 (10)	C7B—N2B—N3B—C8B	−170.95 (10)
C10A—O4A—N4A—C9A	179.55 (10)	C10B—O4B—N4B—C9B	−176.53 (10)
C6A—C1A—C2A—C3A	1.25 (18)	C6B—C1B—C2B—C3B	0.15 (18)
C7A—C1A—C2A—C3A	−178.53 (11)	C7B—C1B—C2B—C3B	−178.76 (11)
C1A—C2A—C3A—C4A	−0.35 (19)	C1B—C2B—C3B—C4B	−0.39 (18)
C2A—C3A—C4A—C5A	−0.91 (19)	C2B—C3B—C4B—C5B	0.46 (19)
C2A—C3A—C4A—N1A	177.51 (11)	C2B—C3B—C4B—N1B	−178.76 (11)
O1A—N1A—C4A—C3A	−177.67 (12)	O1B—N1B—C4B—C3B	−4.50 (17)
O2A—N1A—C4A—C3A	0.95 (18)	O2B—N1B—C4B—C3B	174.85 (13)
O1A—N1A—C4A—C5A	0.82 (18)	O1B—N1B—C4B—C5B	176.25 (12)
O2A—N1A—C4A—C5A	179.44 (12)	O2B—N1B—C4B—C5B	−4.41 (18)
C3A—C4A—C5A—C6A	1.21 (19)	C3B—C4B—C5B—C6B	−0.27 (19)
N1A—C4A—C5A—C6A	−177.22 (11)	N1B—C4B—C5B—C6B	178.95 (11)
C4A—C5A—C6A—C1A	−0.26 (19)	C4B—C5B—C6B—C1B	0.01 (19)
C2A—C1A—C6A—C5A	−0.93 (18)	C2B—C1B—C6B—C5B	0.05 (18)
C7A—C1A—C6A—C5A	178.84 (11)	C7B—C1B—C6B—C5B	178.92 (11)
N3A—N2A—C7A—C1A	−179.72 (9)	N3B—N2B—C7B—C1B	−179.29 (10)
C6A—C1A—C7A—N2A	−7.33 (17)	C6B—C1B—C7B—N2B	3.31 (17)
C2A—C1A—C7A—N2A	172.45 (11)	C2B—C1B—C7B—N2B	−177.82 (11)
N2A—N3A—C8A—O3A	0.00 (16)	N2B—N3B—C8B—O3B	0.70 (17)
N2A—N3A—C8A—C9A	−178.06 (9)	N2B—N3B—C8B—C9B	178.48 (9)
O4A—N4A—C9A—C11A	0.81 (16)	O4B—N4B—C9B—C11B	−1.30 (16)
O4A—N4A—C9A—C8A	−178.51 (9)	O4B—N4B—C9B—C8B	178.23 (9)
O3A—C8A—C9A—N4A	159.45 (11)	O3B—C8B—C9B—N4B	−158.18 (11)
N3A—C8A—C9A—N4A	−22.43 (14)	N3B—C8B—C9B—N4B	23.97 (14)
O3A—C8A—C9A—C11A	−19.94 (15)	O3B—C8B—C9B—C11B	21.41 (15)
N3A—C8A—C9A—C11A	158.18 (10)	N3B—C8B—C9B—C11B	−156.45 (10)
N4A—C9A—C11A—C12A	−113.93 (14)	N4B—C9B—C11B—C16B	−64.63 (16)
C8A—C9A—C11A—C12A	65.38 (14)	C8B—C9B—C11B—C16B	115.84 (12)
N4A—C9A—C11A—C16A	68.15 (16)	N4B—C9B—C11B—C12B	118.44 (13)
C8A—C9A—C11A—C16A	−112.54 (12)	C8B—C9B—C11B—C12B	−61.09 (14)
C16A—C11A—C12A—C13A	1.55 (18)	C16B—C11B—C12B—C13B	−0.20 (17)
C9A—C11A—C12A—C13A	−176.39 (11)	C9B—C11B—C12B—C13B	176.77 (10)
C11A—C12A—C13A—C14A	2.0 (2)	C11B—C12B—C13B—C14B	−1.59 (18)
C12A—C13A—C14A—C15A	−3.1 (2)	C12B—C13B—C14B—C15B	1.63 (18)
C13A—C14A—C15A—C16A	0.6 (2)	C13B—C14B—C15B—C16B	0.12 (18)
C14A—C15A—C16A—C11A	2.83 (18)	C14B—C15B—C16B—C11B	−1.89 (17)
C14A—C15A—C16A—C17A	−174.24 (12)	C14B—C15B—C16B—C17B	176.07 (11)
C12A—C11A—C16A—C15A	−3.91 (17)	C12B—C11B—C16B—C15B	1.92 (16)
C9A—C11A—C16A—C15A	173.99 (11)	C9B—C11B—C16B—C15B	−174.98 (10)
C12A—C11A—C16A—C17A	173.11 (11)	C12B—C11B—C16B—C17B	−175.95 (10)
C9A—C11A—C16A—C17A	−8.98 (17)	C9B—C11B—C16B—C17B	7.15 (16)
C18A—O5A—C17A—C16A	168.60 (10)	C18B—O5B—C17B—C16B	−168.30 (9)
C15A—C16A—C17A—O5A	−37.34 (15)	C15B—C16B—C17B—O5B	44.51 (13)
C11A—C16A—C17A—O5A	145.68 (11)	C11B—C16B—C17B—O5B	−137.60 (10)
C17A—O5A—C18A—C19A	−4.23 (17)	C17B—O5B—C18B—C19B	−1.51 (16)
C17A—O5A—C18A—C23A	174.92 (10)	C17B—O5B—C18B—C23B	179.35 (10)
O5A—C18A—C19A—C20A	179.98 (12)	O5B—C18B—C19B—C20B	−179.43 (11)
C23A—C18A—C19A—C20A	0.89 (19)	C23B—C18B—C19B—C20B	−0.35 (18)
C18A—C19A—C20A—C21A	−0.3 (2)	C18B—C19B—C20B—C21B	1.04 (19)
C19A—C20A—C21A—C22A	−0.6 (2)	C19B—C20B—C21B—C22B	−1.0 (2)
C20A—C21A—C22A—C23A	1.0 (2)	C20B—C21B—C22B—C23B	0.2 (2)
C21A—C22A—C23A—C18A	−0.43 (19)	C21B—C22B—C23B—C18B	0.44 (19)
C21A—C22A—C23A—C24A	−178.58 (12)	C21B—C22B—C23B—C24B	179.00 (13)
O5A—C18A—C23A—C22A	−179.71 (11)	O5B—C18B—C23B—C22B	178.79 (11)
C19A—C18A—C23A—C22A	−0.52 (18)	C19B—C18B—C23B—C22B	−0.38 (18)
O5A—C18A—C23A—C24A	−1.52 (16)	O5B—C18B—C23B—C24B	0.20 (16)
C19A—C18A—C23A—C24A	177.66 (12)	C19B—C18B—C23B—C24B	−178.97 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3A···O3B	0.871 (17)	2.117 (17)	2.8679 (13)	144.0 (14)
N3A—H3A···N2B	0.871 (17)	2.432 (16)	3.1530 (14)	140.5 (13)
C7A—H7AA···O3B	0.95	2.47	3.1523 (14)	129
C10A—H10C···O1B^i	0.98	2.46	3.3159 (18)	145
C17A—H17B···N4A	0.99	2.68	3.2243 (15)	115
N3B—H3B···O3A^ii	0.901 (16)	2.068 (16)	2.8605 (13)	146.1 (13)
N3B—H3B···N2A^ii	0.901 (16)	2.444 (15)	3.1598 (14)	136.6 (12)
C5B—H5BA···O2A^iii	0.95	2.63	3.3484 (18)	133
C7B—H7BA···O3A^ii	0.95	2.51	3.1864 (14)	128
C17B—H17C···N4B	0.99	2.63	3.2436 (15)	120

Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) x+1, y, z; (iii) −x, −y+1, −z+1.