6,6′-Dimeth­oxy-2,2′-(ethane-1,2-diyldiammoniodimethyl­ene)diphenol dinitrate

Liu, Y.-F.; Xia, H.-T.; Yang, S.-P.; Wang, D.-Q.

doi:10.1107/S1600536807004047

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6,6′-Dimethoxy-2,2′-(ethane-1,2-diyldiammoniodimethylene)diphenol dinitrate

Y.-F. Liu, H.-T. Xia, S.-P. Yang and D.-Q. Wang

In the title compound, C₁₈H₂₆N₂O₄²⁺·2NO₃⁻, the ions are linked into two chains by C—H

O hydrogen bonds; these chains are linked into sheets parallel to (001). The asymmetric unit consists of one cation, two half-cations and four anions. Two of the cations have a centre of symmetry at the mid-point of the central C—C bond.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807004047/wn2103sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807004047/wn2103Isup2.hkl Contains datablock I

CCDC reference: 635371

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.012 Å
R factor = 0.099
wR factor = 0.289
Data-to-parameter ratio = 11.4

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.89

Author Response: The crystal outward appearance is a thin slice.


Alert level B
REFLT03_ALERT_3_B  Reflection count < 90% complete (theta max?)
           From the CIF: _diffrn_reflns_theta_max           25.01
           From the CIF: _diffrn_reflns_theta_full          25.01
           From the CIF: _reflns_number_total               6553
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         7384
           Completeness (_total/calc)             88.75%
PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low ....       0.89
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         37 Perc.
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         12

Alert level C
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.289
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT084_ALERT_2_C High R2 Value ..................................       0.29
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C14
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C19
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N5
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N6
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N7
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.40
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.12
PLAT432_ALERT_2_C Short Inter X...Y Contact  O12    ..  C18     ..       3.00 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H27A   ..  O7      ..       2.62 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15    ..  O2      ..       2.62 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7A    ..  O4      ..       2.62 Ang.

   1 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
  14 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
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

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.

6,6'-Dimethoxy-2,2'-(ethane-1,2-diyldiiminiodimethylene)diphenol dinitrate top

Crystal data top

C₁₈H₂₆N₂O₄²⁺·2NO₃⁻	Z = 4
M_r = 458.43	F(000) = 968.0
Triclinic, P1	D_x = 1.454 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.799 (11) Å	Cell parameters from 2155 reflections
b = 12.417 (11) Å	θ = 2.4–21.1°
c = 16.354 (15) Å	µ = 0.12 mm⁻¹
α = 109.127 (12)°	T = 298 K
β = 110.774 (12)°	Block, colourless
γ = 90.582 (13)°	0.38 × 0.19 × 0.14 mm
V = 2095 (3) Å³

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	6553 independent reflections
Radiation source: fine-focus sealed tube	2443 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.069
φ and ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→13
T_min = 0.956, T_max = 0.983	k = −14→11
9489 measured reflections	l = −15→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.099	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.289	H-atom parameters constrained
S = 0.91	w = 1/[σ²(F_o²) + (0.139P)²] where P = (F_o² + 2F_c²)/3
6553 reflections	(Δ/σ)_max < 0.001
577 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.5189 (6)	0.7388 (5)	0.5943 (4)	0.0489 (17)
H1A	0.5164	0.6623	0.5811	0.059*
H1B	0.4636	0.7628	0.6201	0.059*
N2	0.3347 (6)	0.7228 (5)	0.3487 (4)	0.0464 (16)
H2A	0.3553	0.7983	0.3618	0.056*
H2B	0.2532	0.7053	0.3167	0.056*
N3	0.0257 (5)	0.4290 (4)	0.3887 (4)	0.0327 (13)
H3A	0.0852	0.3940	0.4176	0.039*
H3B	0.0541	0.4601	0.3560	0.039*
N4	0.1406 (5)	0.0679 (5)	0.6078 (4)	0.0392 (14)
H4A	0.1717	0.1069	0.5810	0.047*
H4B	0.2008	0.0338	0.6370	0.047*
N5	0.3349 (8)	0.4903 (6)	0.5464 (4)	0.0543 (18)
N6	0.0356 (8)	0.5768 (6)	0.2387 (5)	0.0592 (19)
N7	0.6806 (8)	0.1149 (8)	0.3150 (6)	0.077 (2)
N8	0.2673 (7)	0.9825 (6)	0.4298 (5)	0.0513 (17)
O1	0.7542 (5)	0.6163 (4)	0.6966 (3)	0.0507 (14)
H1	0.7921	0.5678	0.7142	0.076*
O2	0.8547 (5)	0.6042 (4)	0.8649 (4)	0.0568 (15)
O3	0.5301 (5)	0.8542 (5)	0.3069 (3)	0.0565 (15)
H3	0.5663	0.9099	0.3055	0.085*
O4	0.5165 (6)	0.9135 (5)	0.1594 (4)	0.0677 (17)
O5	0.0724 (5)	0.1920 (4)	0.3726 (3)	0.0434 (13)
H5	0.1156	0.1423	0.3810	0.065*
O6	0.1111 (5)	0.0074 (4)	0.2509 (3)	0.0532 (15)
O7	0.1993 (5)	0.3000 (4)	0.6228 (3)	0.0507 (14)
H7	0.2306	0.3504	0.6120	0.076*
O8	0.3653 (5)	0.4862 (4)	0.7399 (4)	0.0552 (15)
O9	0.4475 (6)	0.4982 (5)	0.5700 (5)	0.0742 (19)
O10	0.2844 (6)	0.5760 (6)	0.5482 (5)	0.081 (2)
O11	0.2713 (5)	0.3932 (5)	0.5171 (4)	0.0609 (16)
O12	0.1162 (6)	0.5673 (5)	0.3113 (4)	0.0634 (16)
O13	0.0671 (7)	0.6451 (6)	0.2085 (5)	0.084 (2)
O14	−0.0631 (7)	0.5209 (6)	0.2025 (5)	0.087 (2)
O15	0.6318 (7)	0.1918 (6)	0.2922 (6)	0.105 (3)
O16	0.7665 (7)	0.0797 (6)	0.2917 (6)	0.093 (2)
O17	0.6487 (7)	0.0780 (6)	0.3672 (5)	0.090 (2)
O18	0.2456 (5)	1.0842 (4)	0.4670 (4)	0.0560 (15)
O19	0.3568 (6)	0.9693 (5)	0.4077 (4)	0.0582 (15)
O20	0.1970 (6)	0.8976 (6)	0.4135 (5)	0.0779 (19)
C1	0.6444 (7)	0.7990 (7)	0.6616 (5)	0.056 (2)
H1C	0.7032	0.7696	0.6338	0.068*
H1D	0.6475	0.8804	0.6710	0.068*
C2	0.6817 (7)	0.7858 (7)	0.7529 (5)	0.0459 (19)
C3	0.7425 (7)	0.6979 (6)	0.7701 (5)	0.0392 (18)
C4	0.7924 (7)	0.6952 (6)	0.8593 (5)	0.0435 (19)
C5	0.7781 (7)	0.7776 (7)	0.9324 (5)	0.056 (2)
H5A	0.8114	0.7757	0.9926	0.068*
C6	0.7107 (9)	0.8660 (8)	0.9138 (6)	0.068 (3)
H6	0.6961	0.9220	0.9615	0.081*
C7	0.6670 (8)	0.8689 (8)	0.8251 (7)	0.065 (2)
H7A	0.6262	0.9295	0.8141	0.078*
C8	0.9398 (9)	0.6173 (7)	0.9565 (6)	0.071 (3)
H8A	0.9885	0.6918	0.9846	0.106*
H8B	0.9922	0.5587	0.9520	0.106*
H8C	0.8959	0.6100	0.9942	0.106*
C9	0.3974 (9)	0.6551 (7)	0.2881 (6)	0.056 (2)
H9A	0.4841	0.6648	0.3255	0.067*
H9B	0.3657	0.5741	0.2662	0.067*
C10	0.3822 (8)	0.6883 (7)	0.2067 (6)	0.050 (2)
C11	0.4547 (7)	0.7900 (6)	0.2200 (5)	0.0392 (18)
C12	0.4419 (8)	0.8137 (7)	0.1430 (5)	0.048 (2)
C13	0.3658 (9)	0.7525 (8)	0.0565 (6)	0.060 (2)
H13	0.3603	0.7743	0.0061	0.072*
C14	0.2975 (10)	0.6579 (9)	0.0452 (6)	0.076 (3)
H14	0.2436	0.6138	−0.0148	0.091*
C15	0.3029 (8)	0.6230 (7)	0.1171 (6)	0.060 (2)
H15	0.2542	0.5565	0.1062	0.072*
C16	0.5412 (10)	0.9394 (9)	0.0899 (8)	0.087 (3)
H16A	0.5559	0.8711	0.0483	0.130*
H16B	0.6123	0.9968	0.1183	0.130*
H16C	0.4723	0.9683	0.0553	0.130*
C17	0.4885 (7)	0.7646 (6)	0.5067 (5)	0.0458 (19)
H17A	0.5498	0.7410	0.4802	0.055*
H17B	0.4891	0.8469	0.5209	0.055*
C18	0.3645 (7)	0.7022 (6)	0.4371 (5)	0.047 (2)
H18A	0.3631	0.6202	0.4250	0.056*
H18B	0.3030	0.7279	0.4629	0.056*
C19	−0.0843 (7)	0.3390 (6)	0.3211 (5)	0.054 (2)
H19A	−0.1156	0.3059	0.3563	0.064*
H19B	−0.1481	0.3763	0.2892	0.064*
C20	−0.0569 (7)	0.2454 (5)	0.2506 (5)	0.0399 (18)
C21	0.0196 (7)	0.1727 (6)	0.2799 (5)	0.0392 (18)
C22	0.0374 (7)	0.0765 (5)	0.2142 (5)	0.0367 (17)
C23	−0.0183 (8)	0.0602 (7)	0.1205 (5)	0.053 (2)
H23	−0.0057	−0.0022	0.0758	0.064*
C24	−0.0918 (9)	0.1361 (6)	0.0941 (5)	0.057 (2)
H24	−0.1315	0.1240	0.0309	0.069*
C25	−0.1085 (8)	0.2298 (6)	0.1589 (5)	0.056 (2)
H25	−0.1556	0.2831	0.1397	0.067*
C26	0.1258 (9)	−0.0968 (6)	0.1876 (6)	0.072 (3)
H26A	0.0470	−0.1415	0.1475	0.108*
H26B	0.1753	−0.1401	0.2222	0.108*
H26C	0.1651	−0.0790	0.1504	0.108*
C27	0.0002 (7)	0.5221 (5)	0.4602 (5)	0.0389 (17)
H27A	−0.0787	0.5446	0.4323	0.047*
H27B	0.0624	0.5887	0.4859	0.047*
C28	0.1031 (7)	0.1516 (6)	0.6790 (5)	0.049 (2)
H28A	0.0352	0.1856	0.6476	0.059*
H28B	0.0745	0.1107	0.7110	0.059*
C29	0.2035 (7)	0.2452 (6)	0.7494 (5)	0.0440 (19)
C30	0.2449 (7)	0.3225 (6)	0.7177 (4)	0.0374 (17)
C31	0.3305 (7)	0.4161 (6)	0.7787 (5)	0.0462 (19)
C32	0.3722 (8)	0.4352 (6)	0.8719 (5)	0.052 (2)
H32	0.4281	0.5001	0.9145	0.063*
C33	0.3304 (9)	0.3563 (7)	0.9031 (5)	0.062 (2)
H33	0.3601	0.3681	0.9667	0.074*
C34	0.2479 (8)	0.2642 (6)	0.8423 (6)	0.052 (2)
H34	0.2207	0.2126	0.8640	0.063*
C35	0.4429 (9)	0.5900 (6)	0.7973 (6)	0.069 (3)
H35A	0.4196	0.6265	0.8494	0.103*
H35B	0.4365	0.6398	0.7621	0.103*
H35C	0.5259	0.5750	0.8198	0.103*
C36	0.0406 (7)	−0.0229 (6)	0.5330 (5)	0.0429 (19)
H36A	0.0755	−0.0851	0.5005	0.052*
H36B	−0.0056	−0.0540	0.5609	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.051 (4)	0.041 (4)	0.054 (4)	0.005 (3)	0.013 (3)	0.023 (3)
N2	0.063 (4)	0.039 (3)	0.051 (4)	0.013 (3)	0.029 (3)	0.025 (3)
N3	0.040 (3)	0.026 (3)	0.034 (3)	0.001 (3)	0.015 (3)	0.013 (2)
N4	0.047 (4)	0.035 (3)	0.030 (3)	−0.010 (3)	0.011 (3)	0.009 (3)
N5	0.080 (6)	0.042 (4)	0.041 (4)	−0.002 (4)	0.022 (4)	0.016 (3)
N6	0.060 (6)	0.052 (5)	0.061 (5)	0.014 (4)	0.019 (4)	0.019 (4)
N7	0.051 (6)	0.084 (7)	0.082 (6)	0.000 (5)	0.014 (5)	0.023 (5)
N8	0.069 (5)	0.040 (4)	0.058 (4)	0.016 (4)	0.029 (4)	0.027 (3)
O1	0.073 (4)	0.046 (3)	0.025 (3)	0.006 (3)	0.012 (3)	0.010 (2)
O2	0.063 (4)	0.052 (3)	0.051 (3)	0.009 (3)	0.010 (3)	0.026 (3)
O3	0.071 (4)	0.059 (3)	0.028 (3)	0.008 (3)	0.012 (3)	0.008 (2)
O4	0.093 (5)	0.058 (4)	0.063 (4)	0.004 (3)	0.044 (4)	0.019 (3)
O5	0.066 (4)	0.040 (3)	0.019 (2)	0.013 (3)	0.014 (2)	0.008 (2)
O6	0.081 (4)	0.041 (3)	0.031 (3)	0.020 (3)	0.018 (3)	0.007 (2)
O7	0.071 (4)	0.039 (3)	0.026 (3)	−0.010 (3)	0.007 (2)	0.004 (2)
O8	0.078 (4)	0.038 (3)	0.052 (3)	−0.005 (3)	0.024 (3)	0.019 (3)
O9	0.045 (4)	0.075 (4)	0.112 (5)	0.003 (3)	0.024 (4)	0.051 (4)
O10	0.078 (5)	0.059 (4)	0.116 (6)	0.018 (4)	0.036 (4)	0.045 (4)
O11	0.067 (4)	0.061 (4)	0.053 (3)	−0.012 (3)	0.023 (3)	0.018 (3)
O12	0.071 (4)	0.066 (4)	0.055 (4)	0.004 (3)	0.025 (3)	0.021 (3)
O13	0.106 (6)	0.081 (5)	0.088 (5)	0.016 (4)	0.043 (4)	0.051 (4)
O14	0.054 (4)	0.087 (5)	0.096 (5)	0.004 (4)	0.012 (4)	0.021 (4)
O15	0.094 (6)	0.064 (5)	0.129 (7)	0.014 (4)	0.012 (5)	0.033 (4)
O16	0.076 (5)	0.090 (5)	0.137 (7)	0.021 (4)	0.056 (5)	0.052 (5)
O17	0.104 (6)	0.079 (5)	0.081 (5)	0.001 (4)	0.041 (5)	0.015 (4)
O18	0.071 (4)	0.046 (3)	0.053 (3)	0.019 (3)	0.026 (3)	0.017 (3)
O19	0.067 (4)	0.058 (4)	0.067 (4)	0.019 (3)	0.041 (3)	0.027 (3)
O20	0.073 (5)	0.071 (4)	0.106 (5)	0.011 (4)	0.045 (4)	0.039 (4)
C1	0.045 (5)	0.064 (5)	0.057 (5)	−0.003 (4)	0.002 (4)	0.037 (4)
C2	0.043 (5)	0.051 (5)	0.040 (4)	0.001 (4)	0.010 (4)	0.019 (4)
C3	0.039 (4)	0.043 (4)	0.035 (4)	−0.006 (4)	0.015 (3)	0.013 (3)
C4	0.053 (5)	0.043 (4)	0.040 (4)	0.007 (4)	0.018 (4)	0.020 (4)
C5	0.051 (5)	0.065 (6)	0.035 (5)	−0.009 (4)	0.007 (4)	0.004 (4)
C6	0.082 (7)	0.068 (6)	0.049 (6)	0.011 (5)	0.036 (5)	0.003 (5)
C7	0.057 (6)	0.059 (6)	0.070 (6)	0.014 (5)	0.024 (5)	0.013 (5)
C8	0.082 (7)	0.057 (6)	0.064 (6)	0.013 (5)	0.006 (5)	0.035 (5)
C9	0.091 (7)	0.049 (5)	0.057 (5)	0.026 (5)	0.045 (5)	0.039 (4)
C10	0.062 (6)	0.048 (5)	0.056 (5)	0.024 (4)	0.031 (4)	0.030 (4)
C11	0.054 (5)	0.027 (4)	0.035 (4)	0.005 (3)	0.017 (4)	0.007 (3)
C12	0.062 (6)	0.047 (5)	0.033 (4)	0.013 (4)	0.020 (4)	0.008 (4)
C13	0.080 (7)	0.061 (6)	0.043 (5)	0.017 (5)	0.027 (5)	0.021 (4)
C14	0.083 (8)	0.096 (8)	0.040 (5)	0.030 (7)	0.013 (5)	0.024 (5)
C15	0.064 (6)	0.044 (5)	0.061 (6)	−0.005 (4)	0.023 (5)	0.007 (4)
C16	0.110 (9)	0.082 (7)	0.097 (8)	0.023 (6)	0.065 (7)	0.039 (6)
C17	0.054 (5)	0.048 (4)	0.034 (4)	0.007 (4)	0.009 (4)	0.021 (3)
C18	0.060 (5)	0.049 (5)	0.035 (4)	0.003 (4)	0.019 (4)	0.019 (4)
C19	0.042 (5)	0.047 (5)	0.048 (5)	−0.001 (4)	0.006 (4)	0.000 (4)
C20	0.051 (5)	0.021 (4)	0.033 (4)	0.000 (3)	0.009 (4)	−0.002 (3)
C21	0.047 (5)	0.041 (4)	0.025 (4)	−0.007 (4)	0.013 (3)	0.007 (3)
C22	0.058 (5)	0.023 (3)	0.028 (4)	0.004 (3)	0.021 (4)	0.002 (3)
C23	0.088 (6)	0.049 (5)	0.021 (4)	0.008 (5)	0.023 (4)	0.007 (3)
C24	0.099 (7)	0.038 (4)	0.025 (4)	0.004 (5)	0.013 (4)	0.009 (3)
C25	0.076 (6)	0.040 (5)	0.035 (5)	0.010 (4)	0.004 (4)	0.012 (4)
C26	0.105 (8)	0.035 (5)	0.066 (6)	0.027 (5)	0.033 (6)	0.005 (4)
C27	0.057 (5)	0.027 (4)	0.035 (4)	0.006 (3)	0.022 (4)	0.009 (3)
C28	0.054 (5)	0.045 (5)	0.045 (5)	−0.012 (4)	0.022 (4)	0.006 (4)
C29	0.051 (5)	0.045 (4)	0.039 (4)	−0.001 (4)	0.019 (4)	0.015 (4)
C30	0.046 (5)	0.031 (4)	0.026 (4)	0.000 (3)	0.009 (3)	0.004 (3)
C31	0.054 (5)	0.041 (4)	0.041 (5)	0.010 (4)	0.020 (4)	0.009 (4)
C32	0.071 (6)	0.032 (4)	0.035 (4)	−0.003 (4)	0.004 (4)	0.004 (3)
C33	0.090 (7)	0.049 (5)	0.030 (4)	0.002 (5)	0.014 (4)	0.003 (4)
C34	0.077 (6)	0.037 (4)	0.049 (5)	−0.001 (4)	0.030 (5)	0.017 (4)
C35	0.098 (7)	0.032 (4)	0.060 (6)	−0.017 (5)	0.021 (5)	0.007 (4)
C36	0.056 (5)	0.037 (4)	0.036 (4)	−0.006 (4)	0.021 (4)	0.010 (3)

Geometric parameters (Å, º) top

N1—C17	1.490 (9)	C8—H8C	0.9600
N1—C1	1.499 (10)	C9—C10	1.472 (10)
N1—H1A	0.9000	C9—H9A	0.9700
N1—H1B	0.9000	C9—H9B	0.9700
N2—C18	1.470 (9)	C10—C15	1.383 (11)
N2—C9	1.491 (9)	C10—C11	1.428 (10)
N2—H2A	0.9000	C11—C12	1.343 (10)
N2—H2B	0.9000	C12—C13	1.329 (11)
N3—C27	1.470 (8)	C13—C14	1.341 (13)
N3—C19	1.516 (9)	C13—H13	0.9300
N3—H3A	0.9000	C14—C15	1.362 (12)
N3—H3B	0.9000	C14—H14	0.9300
N4—C36	1.485 (9)	C15—H15	0.9300
N4—C28	1.489 (9)	C16—H16A	0.9600
N4—H4A	0.9000	C16—H16B	0.9600
N4—H4B	0.9000	C16—H16C	0.9600
N5—O10	1.222 (8)	C17—C18	1.502 (10)
N5—O9	1.238 (9)	C17—H17A	0.9700
N5—O11	1.263 (8)	C17—H17B	0.9700
N6—O14	1.189 (9)	C18—H18A	0.9700
N6—O13	1.225 (9)	C18—H18B	0.9700
N6—O12	1.274 (9)	C19—C20	1.476 (10)
N7—O15	1.214 (10)	C19—H19A	0.9700
N7—O16	1.240 (10)	C19—H19B	0.9700
N7—O17	1.249 (10)	C20—C25	1.348 (10)
N8—O19	1.227 (8)	C20—C21	1.361 (10)
N8—O20	1.230 (8)	C21—C22	1.395 (9)
N8—O18	1.282 (8)	C22—C23	1.380 (10)
O1—C3	1.347 (8)	C23—C24	1.359 (11)
O1—H1	0.8200	C23—H23	0.9300
O2—C4	1.365 (9)	C24—C25	1.363 (10)
O2—C8	1.432 (9)	C24—H24	0.9300
O3—C11	1.339 (8)	C25—H25	0.9300
O3—H3	0.8200	C26—H26A	0.9600
O4—C16	1.399 (10)	C26—H26B	0.9600
O4—C12	1.405 (9)	C26—H26C	0.9600
O5—C21	1.355 (8)	C27—C27ⁱ	1.571 (13)
O5—H5	0.8200	C27—H27A	0.9700
O6—C22	1.355 (8)	C27—H27B	0.9700
O6—C26	1.425 (8)	C28—C29	1.485 (10)
O7—C30	1.377 (8)	C28—H28A	0.9700
O7—H7	0.8200	C28—H28B	0.9700
O8—C31	1.368 (9)	C29—C34	1.355 (10)
O8—C35	1.398 (9)	C29—C30	1.388 (10)
C1—C2	1.464 (10)	C30—C31	1.367 (10)
C1—H1C	0.9700	C31—C32	1.359 (10)
C1—H1D	0.9700	C32—C33	1.400 (11)
C2—C7	1.357 (11)	C32—H32	0.9300
C2—C3	1.363 (10)	C33—C34	1.338 (11)
C3—C4	1.377 (10)	C33—H33	0.9300
C4—C5	1.361 (10)	C34—H34	0.9300
C5—C6	1.413 (12)	C35—H35A	0.9600
C5—H5A	0.9300	C35—H35B	0.9600
C6—C7	1.368 (12)	C35—H35C	0.9600
C6—H6	0.9300	C36—C36ⁱⁱ	1.444 (14)
C7—H7A	0.9300	C36—H36A	0.9700
C8—H8A	0.9600	C36—H36B	0.9700
C8—H8B	0.9600

C17—N1—C1	109.5 (6)	C15—C14—H14	118.3
C17—N1—H1A	109.8	C14—C15—C10	118.8 (8)
C1—N1—H1A	109.8	C14—C15—H15	120.6
C17—N1—H1B	109.8	C10—C15—H15	120.6
C1—N1—H1B	109.8	O4—C16—H16A	109.5
H1A—N1—H1B	108.2	O4—C16—H16B	109.5
C18—N2—C9	114.0 (6)	H16A—C16—H16B	109.5
C18—N2—H2A	108.7	O4—C16—H16C	109.5
C9—N2—H2A	108.7	H16A—C16—H16C	109.5
C18—N2—H2B	108.7	H16B—C16—H16C	109.5
C9—N2—H2B	108.7	N1—C17—C18	110.4 (6)
H2A—N2—H2B	107.6	N1—C17—H17A	109.6
C27—N3—C19	114.3 (5)	C18—C17—H17A	109.6
C27—N3—H3A	108.7	N1—C17—H17B	109.6
C19—N3—H3A	108.7	C18—C17—H17B	109.6
C27—N3—H3B	108.7	H17A—C17—H17B	108.1
C19—N3—H3B	108.7	N2—C18—C17	111.3 (6)
H3A—N3—H3B	107.6	N2—C18—H18A	109.4
C36—N4—C28	114.7 (6)	C17—C18—H18A	109.4
C36—N4—H4A	108.6	N2—C18—H18B	109.4
C28—N4—H4A	108.6	C17—C18—H18B	109.4
C36—N4—H4B	108.6	H18A—C18—H18B	108.0
C28—N4—H4B	108.6	C20—C19—N3	113.6 (6)
H4A—N4—H4B	107.6	C20—C19—H19A	108.8
O10—N5—O9	120.0 (7)	N3—C19—H19A	108.8
O10—N5—O11	119.8 (8)	C20—C19—H19B	108.8
O9—N5—O11	120.2 (7)	N3—C19—H19B	108.8
O14—N6—O13	123.0 (8)	H19A—C19—H19B	107.7
O14—N6—O12	121.3 (8)	C25—C20—C21	120.4 (6)
O13—N6—O12	115.8 (8)	C25—C20—C19	121.2 (7)
O15—N7—O16	119.8 (11)	C21—C20—C19	118.4 (7)
O15—N7—O17	119.2 (10)	O5—C21—C20	119.1 (6)
O16—N7—O17	120.9 (10)	O5—C21—C22	121.1 (6)
O19—N8—O20	119.4 (6)	C20—C21—C22	119.8 (6)
O19—N8—O18	120.1 (7)	O6—C22—C23	126.1 (6)
O20—N8—O18	120.4 (7)	O6—C22—C21	114.9 (6)
C3—O1—H1	109.5	C23—C22—C21	119.0 (7)
C4—O2—C8	115.1 (6)	C24—C23—C22	119.3 (7)
C11—O3—H3	109.5	C24—C23—H23	120.3
C16—O4—C12	124.2 (7)	C22—C23—H23	120.3
C21—O5—H5	109.5	C23—C24—C25	121.1 (7)
C22—O6—C26	117.7 (6)	C23—C24—H24	119.5
C30—O7—H7	109.5	C25—C24—H24	119.5
C31—O8—C35	120.1 (6)	C20—C25—C24	120.2 (7)
C2—C1—N1	114.5 (6)	C20—C25—H25	119.9
C2—C1—H1C	108.6	C24—C25—H25	119.9
N1—C1—H1C	108.6	O6—C26—H26A	109.5
C2—C1—H1D	108.6	O6—C26—H26B	109.5
N1—C1—H1D	108.6	H26A—C26—H26B	109.5
H1C—C1—H1D	107.6	O6—C26—H26C	109.5
C7—C2—C3	118.5 (7)	H26A—C26—H26C	109.5
C7—C2—C1	119.6 (8)	H26B—C26—H26C	109.5
C3—C2—C1	121.6 (7)	N3—C27—C27ⁱ	108.8 (6)
O1—C3—C2	116.9 (6)	N3—C27—H27A	109.9
O1—C3—C4	121.9 (7)	C27ⁱ—C27—H27A	109.9
C2—C3—C4	121.2 (7)	N3—C27—H27B	109.9
C5—C4—O2	125.4 (7)	C27ⁱ—C27—H27B	109.9
C5—C4—C3	121.0 (7)	H27A—C27—H27B	108.3
O2—C4—C3	113.6 (6)	C29—C28—N4	113.2 (6)
C4—C5—C6	117.7 (8)	C29—C28—H28A	108.9
C4—C5—H5A	121.2	N4—C28—H28A	108.9
C6—C5—H5A	121.2	C29—C28—H28B	108.9
C7—C6—C5	119.7 (8)	N4—C28—H28B	108.9
C7—C6—H6	120.1	H28A—C28—H28B	107.7
C5—C6—H6	120.1	C34—C29—C30	119.2 (7)
C2—C7—C6	121.8 (8)	C34—C29—C28	123.7 (7)
C2—C7—H7A	119.1	C30—C29—C28	116.9 (7)
C6—C7—H7A	119.1	C31—C30—O7	121.3 (6)
O2—C8—H8A	109.5	C31—C30—C29	120.8 (7)
O2—C8—H8B	109.5	O7—C30—C29	117.8 (6)
H8A—C8—H8B	109.5	C32—C31—C30	119.3 (7)
O2—C8—H8C	109.5	C32—C31—O8	124.8 (7)
H8A—C8—H8C	109.5	C30—C31—O8	115.9 (7)
H8B—C8—H8C	109.5	C31—C32—C33	119.5 (7)
C10—C9—N2	113.9 (6)	C31—C32—H32	120.3
C10—C9—H9A	108.8	C33—C32—H32	120.3
N2—C9—H9A	108.8	C34—C33—C32	120.5 (7)
C10—C9—H9B	108.8	C34—C33—H33	119.8
N2—C9—H9B	108.8	C32—C33—H33	119.8
H9A—C9—H9B	107.7	C33—C34—C29	120.8 (7)
C15—C10—C11	118.6 (7)	C33—C34—H34	119.6
C15—C10—C9	122.6 (8)	C29—C34—H34	119.6
C11—C10—C9	118.8 (7)	O8—C35—H35A	109.5
O3—C11—C12	124.7 (7)	O8—C35—H35B	109.5
O3—C11—C10	118.6 (7)	H35A—C35—H35B	109.5
C12—C11—C10	116.7 (7)	O8—C35—H35C	109.5
C13—C12—C11	125.7 (8)	H35A—C35—H35C	109.5
C13—C12—O4	119.7 (8)	H35B—C35—H35C	109.5
C11—C12—O4	114.6 (7)	C36ⁱⁱ—C36—N4	110.9 (7)
C12—C13—C14	116.9 (9)	C36ⁱⁱ—C36—H36A	109.5
C12—C13—H13	121.6	N4—C36—H36A	109.5
C14—C13—H13	121.6	C36ⁱⁱ—C36—H36B	109.5
C13—C14—C15	123.4 (9)	N4—C36—H36B	109.5
C13—C14—H14	118.3	H36A—C36—H36B	108.0

C17—N1—C1—C2	176.4 (7)	C27—N3—C19—C20	−179.3 (6)
N1—C1—C2—C7	−96.1 (9)	N3—C19—C20—C25	−115.2 (8)
N1—C1—C2—C3	90.7 (9)	N3—C19—C20—C21	66.4 (9)
C7—C2—C3—O1	179.3 (7)	C25—C20—C21—O5	178.5 (7)
C1—C2—C3—O1	−7.4 (10)	C19—C20—C21—O5	−3.1 (10)
C7—C2—C3—C4	−2.6 (12)	C25—C20—C21—C22	−5.0 (11)
C1—C2—C3—C4	170.7 (7)	C19—C20—C21—C22	173.4 (7)
C8—O2—C4—C5	−19.7 (11)	C26—O6—C22—C23	−5.2 (11)
C8—O2—C4—C3	160.4 (7)	C26—O6—C22—C21	175.5 (7)
O1—C3—C4—C5	−179.0 (7)	O5—C21—C22—O6	−0.7 (10)
C2—C3—C4—C5	2.9 (11)	C20—C21—C22—O6	−177.2 (6)
O1—C3—C4—O2	0.8 (10)	O5—C21—C22—C23	179.9 (7)
C2—C3—C4—O2	−177.2 (7)	C20—C21—C22—C23	3.4 (11)
O2—C4—C5—C6	179.9 (8)	O6—C22—C23—C24	178.8 (8)
C3—C4—C5—C6	−0.2 (12)	C21—C22—C23—C24	−1.9 (12)
C4—C5—C6—C7	−2.7 (13)	C22—C23—C24—C25	2.0 (13)
C3—C2—C7—C6	−0.4 (13)	C21—C20—C25—C24	5.0 (12)
C1—C2—C7—C6	−173.8 (8)	C19—C20—C25—C24	−173.4 (8)
C5—C6—C7—C2	3.0 (14)	C23—C24—C25—C20	−3.5 (14)
C18—N2—C9—C10	−171.4 (7)	C19—N3—C27—C27ⁱ	79.9 (9)
N2—C9—C10—C15	−103.7 (9)	C36—N4—C28—C29	−176.6 (6)
N2—C9—C10—C11	78.2 (10)	N4—C28—C29—C34	−119.2 (8)
C15—C10—C11—O3	179.0 (7)	N4—C28—C29—C30	66.8 (9)
C9—C10—C11—O3	−2.9 (10)	C34—C29—C30—C31	0.8 (11)
C15—C10—C11—C12	−1.2 (10)	C28—C29—C30—C31	175.1 (7)
C9—C10—C11—C12	176.9 (7)	C34—C29—C30—O7	179.1 (7)
O3—C11—C12—C13	−178.5 (7)	C28—C29—C30—O7	−6.6 (10)
C10—C11—C12—C13	1.7 (12)	O7—C30—C31—C32	179.6 (7)
O3—C11—C12—O4	0.8 (11)	C29—C30—C31—C32	−2.2 (11)
C10—C11—C12—O4	−179.0 (6)	O7—C30—C31—O8	1.4 (10)
C16—O4—C12—C13	−17.1 (12)	C29—C30—C31—O8	179.6 (6)
C16—O4—C12—C11	163.6 (8)	C35—O8—C31—C32	−4.6 (11)
C11—C12—C13—C14	−1.1 (13)	C35—O8—C31—C30	173.5 (7)
O4—C12—C13—C14	179.7 (7)	C30—C31—C32—C33	2.5 (12)
C12—C13—C14—C15	0.0 (13)	O8—C31—C32—C33	−179.5 (7)
C13—C14—C15—C10	0.4 (14)	C31—C32—C33—C34	−1.5 (13)
C11—C10—C15—C14	0.3 (12)	C32—C33—C34—C29	0.1 (13)
C9—C10—C15—C14	−177.8 (8)	C30—C29—C34—C33	0.2 (12)
C1—N1—C17—C18	178.3 (6)	C28—C29—C34—C33	−173.7 (8)
C9—N2—C18—C17	77.3 (8)	C28—N4—C36—C36ⁱⁱ	75.2 (9)
N1—C17—C18—N2	−177.8 (6)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C36—H36B···O5ⁱⁱ	0.97	2.56	3.477 (9)	158
C27—H27A···O7ⁱ	0.97	2.62	3.473 (9)	147
C15—H15···O2ⁱⁱⁱ	0.93	2.62	3.511 (10)	161
C7—H7A···O4^iv	0.93	2.62	3.480 (11)	155

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

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