Dicyclo­hexyl­aminium N-(tert-butoxy­carbon­yl)-l-threoninate: a monoclinic structure with Z′ = 4

Bryndal, I.; Lis, T.

doi:10.1107/S1600536807007489

Buy article online - an online subscription or single-article purchase is required to access this article.

Dicyclohexylaminium N-(tert-butoxycarbonyl)-L-threoninate: a monoclinic structure with Z′ = 4

I. Bryndal and T. Lis

The crystal structure of the title compound {systematic name: dicyclohexylaminium (2S,3R)-2-[(tert-butoxycarbonyl)amino]-3-hydroxybutanoate}, C₁₂H₂₄N⁺·C₉H₁₆NO₅⁻, contains Boc-L-threoninate anions and dicyclohexylaminium cations. A network of O—H

O and N—H

O hydrogen bonds leads to chains of ions running along the b axis.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807007489/hb2273sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807007489/hb2273Isup2.hkl Contains datablock I

CCDC reference: 640339

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.005 Å
R factor = 0.072
wR factor = 0.162
Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.70 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.59 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.05 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.22 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.30 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.91 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           30.00
           From the CIF: _reflns_number_total              14315
           Count of symmetry unique reflns        14389
           Completeness (_total/calc)             99.49%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C21    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C22    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C23    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C24    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C31    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C32    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C33    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C34    = .          R

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

   8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 1998) and DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL97.

Dicyclohexylaminium (2S,3R)-2-[(tert-butoxycarbonyl)amino]-3-hydroxybutanoate] top

Crystal data top

C₁₂H₂₄N⁺·C₉H₁₆NO₅⁻	F(000) = 1760
M_r = 400.55	D_x = 1.134 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 31986 reflections
a = 19.789 (5) Å	θ = 4.4–30.0°
b = 10.389 (3) Å	µ = 0.08 mm⁻¹
c = 23.081 (6) Å	T = 100 K
β = 98.62 (3)°	Block, colourless
V = 4692 (2) Å³	0.40 × 0.28 × 0.26 mm
Z = 8

Data collection top

Xcalibur PX κ-geometry diffractometer with CCD Onyx camera	12331 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.058
Graphite monochromator	θ_max = 30.0°, θ_min = 4.4°
ω and φ scans	h = −27→27
77687 measured reflections	k = −14→12
14315 independent reflections	l = −32→32

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)] = 0.072	Hydrogen site location: difference Fourier map
wR(F²) = 0.162	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0728P)² + 1.0518P] where P = (F_o² + 2F_c²)/3
14315 reflections	(Δ/σ)_max < 0.001
1029 parameters	Δρ_max = 0.40 e Å⁻³
1 restraint	Δρ_min = −0.25 e Å⁻³

Special details top

Experimental. (CrysAlis RED; Oxford Diffraction, 2003)

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
N11	0.36141 (11)	0.4058 (2)	0.49861 (9)	0.0184 (4)
H11A	0.3926	0.4716	0.4992	0.022*
H11B	0.3858	0.3300	0.5025	0.022*
C101	0.31777 (14)	0.4053 (3)	0.43911 (11)	0.0198 (5)
H101	0.2883	0.4840	0.4354	0.024*
C102	0.27190 (16)	0.2867 (3)	0.43074 (13)	0.0268 (6)
H10A	0.2403	0.2867	0.4602	0.032*
H10B	0.3002	0.2078	0.4364	0.032*
C103	0.23069 (17)	0.2875 (3)	0.36883 (14)	0.0338 (7)
H10C	0.2027	0.2082	0.3630	0.041*
H10D	0.1992	0.3621	0.3648	0.041*
C104	0.27677 (18)	0.2950 (4)	0.32191 (14)	0.0361 (8)
H10E	0.3052	0.2163	0.3232	0.043*
H10F	0.2485	0.3000	0.2828	0.043*
C105	0.32246 (18)	0.4119 (4)	0.33139 (14)	0.0390 (8)
H10G	0.2941	0.4908	0.3267	0.047*
H10H	0.3535	0.4135	0.3015	0.047*
C106	0.36495 (16)	0.4104 (4)	0.39274 (12)	0.0321 (7)
H10I	0.3955	0.3344	0.3968	0.039*
H10J	0.3937	0.4887	0.3984	0.039*
C107	0.32613 (14)	0.4202 (3)	0.55186 (12)	0.0196 (5)
H107	0.2977	0.3420	0.5556	0.024*
C108	0.28004 (15)	0.5388 (3)	0.54673 (13)	0.0241 (6)
H10K	0.2423	0.5271	0.5138	0.029*
H10L	0.3067	0.6153	0.5382	0.029*
C109	0.25026 (16)	0.5611 (3)	0.60348 (14)	0.0303 (7)
H10M	0.2223	0.6404	0.5997	0.036*
H10N	0.2201	0.4881	0.6100	0.036*
C110	0.30702 (16)	0.5738 (3)	0.65601 (14)	0.0315 (7)
H11C	0.3353	0.6503	0.6509	0.038*
H11D	0.2866	0.5855	0.6923	0.038*
C111	0.35166 (16)	0.4534 (3)	0.66136 (13)	0.0283 (6)
H11E	0.3239	0.3782	0.6697	0.034*
H11F	0.3891	0.4638	0.6946	0.034*
C112	0.38197 (15)	0.4288 (3)	0.60531 (12)	0.0254 (6)
H11G	0.4082	0.3474	0.6093	0.030*
H11H	0.4139	0.4994	0.5995	0.030*
N12	0.36205 (11)	0.4084 (2)	0.00198 (10)	0.0191 (4)
H12A	0.3932	0.4745	0.0032	0.023*
H12B	0.3865	0.3328	0.0058	0.023*
C201	0.32569 (14)	0.4214 (3)	0.05464 (12)	0.0212 (5)
H201	0.2978	0.3421	0.0579	0.025*
C202	0.27862 (15)	0.5378 (3)	0.04955 (13)	0.0267 (6)
H20A	0.2420	0.5263	0.0157	0.032*
H20B	0.3049	0.6158	0.0425	0.032*
C203	0.24673 (16)	0.5554 (4)	0.10530 (15)	0.0343 (7)
H20C	0.2168	0.4810	0.1102	0.041*
H20D	0.2181	0.6340	0.1018	0.041*
C204	0.30176 (17)	0.5667 (4)	0.15906 (15)	0.0356 (8)
H20E	0.3292	0.6453	0.1557	0.043*
H20F	0.2798	0.5747	0.1947	0.043*
C205	0.34837 (18)	0.4501 (4)	0.16477 (14)	0.0367 (8)
H20G	0.3219	0.3726	0.1723	0.044*
H20H	0.3851	0.4621	0.1985	0.044*
C206	0.38021 (16)	0.4304 (3)	0.10858 (13)	0.0297 (7)
H20I	0.4112	0.5032	0.1038	0.036*
H20J	0.4077	0.3505	0.1122	0.036*
C207	0.31966 (14)	0.4089 (3)	−0.05772 (12)	0.0221 (5)
H207	0.2920	0.4898	−0.0620	0.026*
C208	0.27090 (15)	0.2946 (3)	−0.06564 (14)	0.0287 (6)
H20K	0.2394	0.2983	−0.0362	0.034*
H20L	0.2971	0.2132	−0.0599	0.034*
C209	0.23011 (17)	0.2986 (4)	−0.12742 (15)	0.0370 (8)
H20M	0.1995	0.2228	−0.1333	0.044*
H20N	0.2013	0.3769	−0.1317	0.044*
C210	0.2772 (2)	0.2990 (4)	−0.17411 (15)	0.0433 (9)
H21E	0.3033	0.2173	−0.1721	0.052*
H21F	0.2495	0.3048	−0.2134	0.052*
C211	0.3268 (2)	0.4120 (4)	−0.16526 (14)	0.0433 (9)
H21I	0.3010	0.4937	−0.1712	0.052*
H21J	0.3585	0.4076	−0.1946	0.052*
C212	0.36785 (17)	0.4095 (4)	−0.10364 (13)	0.0336 (7)
H21K	0.3979	0.4860	−0.0979	0.040*
H21L	0.3971	0.3317	−0.0989	0.040*
N13	0.13160 (12)	0.9354 (2)	0.50931 (10)	0.0211 (5)
H13A	0.1096	0.8577	0.5108	0.025*
H13B	0.0984	0.9974	0.5008	0.025*
C301	0.16975 (15)	0.9630 (3)	0.56951 (12)	0.0223 (5)
H301	0.2013	0.8893	0.5811	0.027*
C302	0.11929 (16)	0.9693 (4)	0.61212 (13)	0.0339 (7)
H30A	0.0933	0.8876	0.6107	0.041*
H30B	0.0864	1.0400	0.6008	0.041*
C303	0.15591 (18)	0.9922 (4)	0.67494 (15)	0.0415 (9)
H30C	0.1217	1.0010	0.7019	0.050*
H30D	0.1855	0.9176	0.6879	0.050*
C304	0.1991 (2)	1.1141 (4)	0.67696 (18)	0.0512 (11)
H30E	0.1688	1.1895	0.6680	0.061*
H30F	0.2247	1.1253	0.7169	0.061*
C305	0.2492 (2)	1.1072 (4)	0.63309 (17)	0.0479 (10)
H30G	0.2819	1.0362	0.6442	0.057*
H30H	0.2755	1.1886	0.6345	0.057*
C306	0.2129 (2)	1.0853 (3)	0.57062 (15)	0.0379 (8)
H30I	0.2470	1.0761	0.5436	0.046*
H30J	0.1833	1.1599	0.5577	0.046*
C307	0.17209 (14)	0.9300 (3)	0.45922 (12)	0.0221 (6)
H307	0.1946	1.0151	0.4555	0.026*
C308	0.22695 (15)	0.8252 (3)	0.47002 (14)	0.0279 (6)
H30K	0.2056	0.7430	0.4792	0.033*
H30L	0.2610	0.8492	0.5042	0.033*
C309	0.26293 (16)	0.8072 (4)	0.41617 (15)	0.0341 (7)
H30M	0.2880	0.8868	0.4093	0.041*
H30N	0.2965	0.7362	0.4236	0.041*
C310	0.21201 (17)	0.7765 (4)	0.36221 (15)	0.0351 (7)
H31A	0.1893	0.6934	0.3678	0.042*
H31B	0.2362	0.7682	0.3278	0.042*
C311	0.15854 (17)	0.8825 (4)	0.35107 (14)	0.0353 (7)
H31C	0.1809	0.9636	0.3419	0.042*
H31D	0.1246	0.8592	0.3167	0.042*
C312	0.12203 (15)	0.9036 (3)	0.40373 (13)	0.0278 (6)
H31E	0.0947	0.8263	0.4097	0.033*
H31F	0.0903	0.9773	0.3959	0.033*
N14	0.13667 (11)	0.9546 (2)	0.00704 (10)	0.0195 (5)
H14A	0.1089	1.0258	0.0007	0.023*
H14B	0.1087	0.8835	0.0041	0.023*
C401	0.17288 (15)	0.9613 (3)	0.06853 (13)	0.0248 (6)
H401	0.2034	0.8845	0.0759	0.030*
C402	0.11987 (16)	0.9551 (3)	0.10985 (13)	0.0278 (6)
H40A	0.0936	0.8739	0.1032	0.033*
H40B	0.0875	1.0277	0.1016	0.033*
C403	0.15414 (19)	0.9614 (4)	0.17359 (15)	0.0377 (8)
H40C	0.1187	0.9602	0.1996	0.045*
H40D	0.1835	0.8848	0.1827	0.045*
C404	0.1971 (2)	1.0822 (4)	0.18538 (18)	0.0546 (11)
H40E	0.2208	1.0815	0.2263	0.066*
H40F	0.1674	1.1591	0.1800	0.066*
C405	0.2498 (2)	1.0878 (5)	0.14308 (18)	0.0613 (13)
H40G	0.2820	1.0150	0.1514	0.074*
H40H	0.2763	1.1686	0.1499	0.074*
C406	0.2167 (2)	1.0819 (4)	0.07832 (17)	0.0473 (10)
H40I	0.1881	1.1592	0.0683	0.057*
H40J	0.2527	1.0801	0.0528	0.057*
C407	0.17926 (14)	0.9478 (3)	−0.04200 (13)	0.0227 (6)
H407	0.2109	1.0233	−0.0390	0.027*
C408	0.22132 (15)	0.8245 (3)	−0.03674 (14)	0.0281 (6)
H40K	0.1911	0.7505	−0.0321	0.034*
H40L	0.2563	0.8293	−0.0013	0.034*
C409	0.25660 (17)	0.8027 (3)	−0.09067 (16)	0.0357 (7)
H40M	0.2916	0.8702	−0.0922	0.043*
H40N	0.2800	0.7183	−0.0873	0.043*
C410	0.20592 (19)	0.8062 (4)	−0.14646 (16)	0.0381 (8)
H41A	0.1723	0.7358	−0.1460	0.046*
H41B	0.2301	0.7930	−0.1806	0.046*
C411	0.1691 (2)	0.9349 (4)	−0.15213 (16)	0.0430 (9)
H41C	0.1363	0.9368	−0.1890	0.052*
H41D	0.2027	1.0050	−0.1536	0.052*
C412	0.13081 (17)	0.9557 (4)	−0.09972 (14)	0.0361 (8)
H41E	0.1085	1.0412	−0.1031	0.043*
H41F	0.0947	0.8896	−0.1003	0.043*
N1	0.55521 (12)	0.4173 (2)	0.55244 (9)	0.0189 (4)
H1	0.5325	0.3445	0.5465	0.023*
O11	0.54405 (10)	0.71790 (19)	0.48010 (9)	0.0237 (4)
O21	0.45754 (10)	0.59982 (19)	0.50193 (10)	0.0246 (4)
O31	0.60544 (11)	0.3098 (2)	0.45357 (9)	0.0262 (4)
H31	0.5906	0.2496	0.4724	0.039*
O41	0.61516 (11)	0.5502 (2)	0.61958 (9)	0.0267 (4)
O51	0.55830 (10)	0.37244 (19)	0.64618 (8)	0.0226 (4)
C11	0.51943 (14)	0.6136 (3)	0.49521 (12)	0.0189 (5)
C21	0.56677 (14)	0.4961 (2)	0.50323 (11)	0.0176 (5)
H21	0.6151	0.5274	0.5105	0.021*
C31	0.55758 (14)	0.4130 (3)	0.44739 (11)	0.0202 (5)
H31X	0.5103	0.3766	0.4410	0.024*
C41	0.5685 (2)	0.4896 (3)	0.39390 (14)	0.0402 (8)
H41X	0.5648	0.4324	0.3598	0.060*
H41Y	0.6141	0.5288	0.4005	0.060*
H41Z	0.5338	0.5573	0.3867	0.060*
C51	0.57917 (14)	0.4556 (3)	0.60695 (12)	0.0194 (5)
C61	0.57801 (15)	0.3934 (3)	0.70907 (12)	0.0239 (6)
C71	0.5539 (2)	0.5251 (3)	0.72664 (14)	0.0354 (8)
H71X	0.5051	0.5351	0.7118	0.053*
H71Y	0.5799	0.5924	0.7100	0.053*
H71Z	0.5612	0.5324	0.7695	0.053*
C81	0.53892 (18)	0.2868 (3)	0.73469 (13)	0.0316 (7)
H81X	0.5539	0.2031	0.7217	0.047*
H81Y	0.4898	0.2973	0.7213	0.047*
H81Z	0.5478	0.2912	0.7776	0.047*
C91	0.65397 (17)	0.3739 (4)	0.72606 (16)	0.0400 (8)
H91X	0.6786	0.4398	0.7071	0.060*
H91Y	0.6666	0.2884	0.7134	0.060*
H91Z	0.6660	0.3810	0.7687	0.060*
N2	0.55594 (12)	0.4201 (2)	0.05375 (9)	0.0187 (4)
H2	0.5327	0.3479	0.0476	0.022*
O12	0.54330 (10)	0.71927 (19)	−0.02085 (9)	0.0227 (4)
O22	0.45810 (10)	0.6018 (2)	0.00451 (9)	0.0244 (4)
O32	0.60885 (11)	0.3140 (2)	−0.04350 (10)	0.0278 (5)
H32	0.5919	0.2499	−0.0288	0.042*
O42	0.61612 (12)	0.5511 (2)	0.12148 (9)	0.0283 (5)
O52	0.56048 (11)	0.3714 (2)	0.14719 (8)	0.0239 (4)
C12	0.51941 (14)	0.6159 (3)	−0.00395 (12)	0.0187 (5)
C22	0.56773 (14)	0.4996 (2)	0.00473 (11)	0.0170 (5)
H22	0.6158	0.5323	0.0125	0.020*
C32	0.56015 (16)	0.4154 (3)	−0.05109 (12)	0.0228 (6)
H32X	0.5132	0.3776	−0.0579	0.027*
C42	0.5715 (2)	0.4910 (4)	−0.10446 (15)	0.0441 (9)
H42X	0.5697	0.4328	−0.1381	0.066*
H42Y	0.6164	0.5327	−0.0972	0.066*
H42Z	0.5359	0.5566	−0.1129	0.066*
C52	0.58053 (14)	0.4569 (3)	0.10843 (12)	0.0200 (5)
C62	0.57641 (16)	0.3944 (3)	0.21021 (12)	0.0242 (6)
C72	0.53883 (18)	0.2853 (3)	0.23491 (14)	0.0324 (7)
H72X	0.5545	0.2029	0.2211	0.049*
H72Y	0.4896	0.2944	0.2218	0.049*
H72Z	0.5480	0.2879	0.2778	0.049*
C82	0.65293 (17)	0.3813 (4)	0.23002 (15)	0.0380 (8)
H82X	0.6768	0.4531	0.2143	0.057*
H82Y	0.6690	0.2998	0.2156	0.057*
H82Z	0.6624	0.3826	0.2729	0.057*
C92	0.5493 (2)	0.5247 (3)	0.22559 (14)	0.0362 (8)
H92X	0.5013	0.5328	0.2079	0.054*
H92Y	0.5762	0.5929	0.2105	0.054*
H92Z	0.5530	0.5325	0.2683	0.054*
N3	−0.04306 (12)	0.8725 (2)	0.44286 (10)	0.0213 (5)
H3	−0.0211	0.8074	0.4614	0.026*
O13	−0.07657 (12)	1.1979 (2)	0.47317 (10)	0.0335 (5)
O23	0.02658 (11)	1.1082 (2)	0.48457 (10)	0.0290 (5)
O33	−0.10715 (11)	0.8049 (2)	0.54166 (10)	0.0279 (5)
H33	−0.0847	0.7408	0.5331	0.042*
O43	−0.03115 (11)	0.7882 (2)	0.35397 (9)	0.0278 (4)
O53	−0.07089 (11)	0.9925 (2)	0.36351 (9)	0.0261 (4)
C13	−0.03806 (15)	1.1022 (3)	0.47759 (12)	0.0227 (6)
C23	−0.07233 (14)	0.9694 (3)	0.47776 (12)	0.0208 (5)
H23	−0.1219	0.9793	0.4618	0.025*
C33	−0.06651 (14)	0.9184 (3)	0.54088 (12)	0.0205 (5)
H33X	−0.0177	0.8961	0.5551	0.025*
C43	−0.09015 (17)	1.0155 (3)	0.58260 (13)	0.0267 (6)
H43X	−0.0884	0.9764	0.6214	0.040*
H43Y	−0.1372	1.0418	0.5679	0.040*
H43Z	−0.0602	1.0911	0.5854	0.040*
C53	−0.04773 (15)	0.8769 (3)	0.38389 (12)	0.0230 (6)
C63	−0.07864 (16)	1.0242 (3)	0.30058 (12)	0.0269 (6)
C73	−0.00963 (17)	1.0182 (4)	0.27844 (14)	0.0352 (7)
H73X	0.0049	0.9282	0.2769	0.053*
H73Y	0.0244	1.0665	0.3051	0.053*
H73Z	−0.0140	1.0558	0.2391	0.053*
C83	−0.13141 (18)	0.9373 (4)	0.26622 (14)	0.0392 (8)
H83X	−0.1730	0.9372	0.2845	0.059*
H83Y	−0.1133	0.8496	0.2660	0.059*
H83Z	−0.1421	0.9688	0.2259	0.059*
C93	−0.10387 (19)	1.1620 (4)	0.30022 (16)	0.0383 (8)
H93X	−0.0709	1.2144	0.3260	0.057*
H93Y	−0.1483	1.1644	0.3142	0.057*
H93Z	−0.1087	1.1962	0.2602	0.057*
N4	−0.05188 (13)	0.9884 (2)	−0.06243 (10)	0.0223 (5)
H4	−0.0374	0.9083	−0.0588	0.027*
O14	−0.03822 (10)	1.27286 (19)	0.02319 (9)	0.0237 (4)
O24	0.04663 (10)	1.1545 (2)	−0.00190 (10)	0.0273 (5)
O34	−0.11735 (10)	0.8713 (2)	0.02455 (10)	0.0274 (5)
H34	−0.0991	0.8003	0.0189	0.041*
O44	−0.08469 (11)	1.1541 (2)	−0.12469 (9)	0.0277 (5)
O54	−0.04419 (11)	0.9649 (2)	−0.15663 (9)	0.0270 (4)
C14	−0.01516 (14)	1.1712 (3)	0.00406 (12)	0.0195 (5)
C24	−0.06553 (14)	1.0607 (2)	−0.01163 (12)	0.0187 (5)
H24	−0.1124	1.0984	−0.0209	0.022*
C34	−0.06548 (15)	0.9656 (3)	0.04013 (12)	0.0211 (5)
H34X	−0.0201	0.9216	0.0479	0.025*
C44	−0.07905 (18)	1.0316 (3)	0.09535 (13)	0.0295 (7)
H44X	−0.0763	0.9686	0.1272	0.044*
H44Y	−0.1248	1.0700	0.0888	0.044*
H44Z	−0.0449	1.0993	0.1059	0.044*
C54	−0.06178 (15)	1.0461 (3)	−0.11517 (13)	0.0232 (6)
C64	−0.05461 (19)	1.0037 (4)	−0.21862 (13)	0.0371 (8)
C74	−0.1296 (2)	1.0286 (5)	−0.23993 (16)	0.0511 (11)
H74X	−0.1442	1.1055	−0.2206	0.077*
H74Y	−0.1566	0.9544	−0.2306	0.077*
H74Z	−0.1366	1.0421	−0.2824	0.077*
C84	−0.0301 (3)	0.8838 (5)	−0.24781 (17)	0.0570 (12)
H84X	−0.0567	0.8090	−0.2385	0.086*
H84Y	0.0184	0.8693	−0.2333	0.086*
H84Z	−0.0363	0.8963	−0.2904	0.086*
C94	−0.0094 (2)	1.1198 (4)	−0.22717 (18)	0.0526 (11)
H94X	0.0378	1.1016	−0.2096	0.079*
H94Y	−0.0260	1.1955	−0.2083	0.079*
H94Z	−0.0111	1.1366	−0.2691	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N11	0.0185 (10)	0.0181 (10)	0.0182 (11)	0.0002 (9)	0.0018 (8)	−0.0005 (9)
C101	0.0194 (12)	0.0235 (13)	0.0157 (12)	−0.0006 (11)	−0.0002 (10)	−0.0020 (10)
C102	0.0251 (14)	0.0247 (14)	0.0278 (15)	−0.0025 (12)	−0.0048 (12)	−0.0003 (12)
C103	0.0314 (16)	0.0319 (16)	0.0339 (17)	−0.0022 (14)	−0.0094 (13)	−0.0062 (14)
C104	0.0378 (18)	0.0425 (19)	0.0234 (15)	0.0124 (15)	−0.0100 (13)	−0.0117 (14)
C105	0.0348 (17)	0.063 (2)	0.0181 (14)	−0.0006 (17)	−0.0009 (13)	0.0026 (15)
C106	0.0274 (15)	0.053 (2)	0.0160 (13)	−0.0034 (15)	0.0036 (11)	−0.0001 (14)
C107	0.0218 (13)	0.0185 (12)	0.0185 (12)	−0.0008 (10)	0.0031 (10)	−0.0005 (10)
C108	0.0223 (13)	0.0254 (13)	0.0247 (14)	0.0047 (11)	0.0033 (11)	0.0011 (12)
C109	0.0245 (14)	0.0376 (17)	0.0295 (16)	0.0079 (13)	0.0060 (12)	−0.0036 (13)
C110	0.0307 (16)	0.0371 (17)	0.0274 (15)	−0.0026 (14)	0.0068 (13)	−0.0139 (13)
C111	0.0292 (15)	0.0363 (16)	0.0187 (13)	0.0020 (13)	0.0010 (11)	−0.0033 (12)
C112	0.0226 (14)	0.0323 (15)	0.0206 (13)	0.0039 (12)	0.0008 (11)	−0.0012 (12)
N12	0.0197 (11)	0.0164 (10)	0.0212 (11)	0.0009 (9)	0.0026 (9)	0.0006 (9)
C201	0.0203 (13)	0.0201 (12)	0.0240 (13)	−0.0005 (11)	0.0059 (11)	0.0001 (11)
C202	0.0214 (14)	0.0286 (14)	0.0290 (15)	0.0050 (12)	0.0007 (11)	−0.0046 (13)
C203	0.0221 (15)	0.0434 (18)	0.0376 (18)	0.0041 (14)	0.0047 (13)	−0.0129 (15)
C204	0.0313 (17)	0.046 (2)	0.0308 (17)	−0.0016 (15)	0.0086 (13)	−0.0145 (15)
C205	0.0347 (18)	0.052 (2)	0.0246 (15)	0.0013 (16)	0.0077 (13)	−0.0037 (15)
C206	0.0284 (15)	0.0417 (18)	0.0189 (14)	0.0108 (13)	0.0028 (11)	0.0008 (12)
C207	0.0230 (13)	0.0227 (12)	0.0185 (13)	0.0029 (11)	−0.0036 (10)	−0.0006 (11)
C208	0.0203 (14)	0.0278 (15)	0.0358 (17)	0.0000 (12)	−0.0031 (12)	−0.0060 (13)
C209	0.0284 (16)	0.0365 (18)	0.0408 (19)	0.0047 (14)	−0.0119 (14)	−0.0104 (15)
C210	0.047 (2)	0.045 (2)	0.0308 (18)	0.0216 (17)	−0.0171 (15)	−0.0134 (16)
C211	0.048 (2)	0.060 (2)	0.0197 (15)	0.0090 (19)	−0.0031 (14)	−0.0011 (16)
C212	0.0296 (16)	0.053 (2)	0.0175 (14)	−0.0047 (15)	0.0022 (12)	−0.0027 (14)
N13	0.0206 (11)	0.0184 (11)	0.0229 (12)	−0.0020 (9)	−0.0016 (9)	0.0027 (9)
C301	0.0239 (13)	0.0196 (12)	0.0210 (13)	−0.0036 (11)	−0.0043 (11)	0.0023 (11)
C302	0.0269 (15)	0.050 (2)	0.0227 (14)	0.0023 (15)	−0.0045 (12)	−0.0048 (14)
C303	0.0323 (17)	0.067 (3)	0.0234 (15)	−0.0036 (18)	−0.0016 (13)	−0.0117 (16)
C304	0.061 (3)	0.045 (2)	0.040 (2)	0.011 (2)	−0.0175 (19)	−0.0198 (18)
C305	0.059 (2)	0.0378 (19)	0.039 (2)	−0.0246 (18)	−0.0173 (18)	0.0043 (16)
C306	0.047 (2)	0.0285 (16)	0.0332 (17)	−0.0166 (15)	−0.0119 (15)	0.0041 (14)
C307	0.0233 (13)	0.0229 (13)	0.0203 (13)	−0.0021 (11)	0.0043 (11)	0.0032 (11)
C308	0.0241 (14)	0.0281 (15)	0.0308 (16)	−0.0003 (12)	0.0019 (12)	0.0024 (12)
C309	0.0242 (15)	0.0388 (18)	0.0402 (18)	−0.0015 (14)	0.0084 (13)	−0.0002 (15)
C310	0.0312 (17)	0.0402 (18)	0.0364 (18)	−0.0079 (15)	0.0134 (14)	−0.0065 (15)
C311	0.0325 (17)	0.050 (2)	0.0241 (15)	−0.0010 (15)	0.0051 (13)	0.0024 (15)
C312	0.0199 (13)	0.0385 (17)	0.0244 (14)	0.0005 (13)	0.0015 (11)	0.0015 (13)
N14	0.0174 (11)	0.0159 (10)	0.0246 (12)	−0.0001 (9)	0.0010 (9)	0.0024 (9)
C401	0.0227 (14)	0.0212 (13)	0.0287 (15)	−0.0010 (11)	−0.0024 (11)	0.0041 (12)
C402	0.0296 (15)	0.0258 (14)	0.0275 (15)	−0.0025 (12)	0.0027 (12)	−0.0008 (12)
C403	0.043 (2)	0.0411 (19)	0.0270 (16)	−0.0002 (17)	−0.0003 (14)	0.0003 (15)
C404	0.073 (3)	0.048 (2)	0.036 (2)	−0.014 (2)	−0.014 (2)	−0.0087 (18)
C405	0.062 (3)	0.073 (3)	0.042 (2)	−0.039 (3)	−0.015 (2)	0.004 (2)
C406	0.049 (2)	0.046 (2)	0.042 (2)	−0.0244 (18)	−0.0089 (17)	0.0074 (17)
C407	0.0205 (13)	0.0179 (12)	0.0311 (15)	0.0002 (10)	0.0081 (11)	0.0030 (11)
C408	0.0231 (14)	0.0220 (13)	0.0383 (17)	0.0029 (11)	0.0016 (12)	0.0004 (12)
C409	0.0293 (16)	0.0330 (17)	0.047 (2)	0.0059 (14)	0.0129 (15)	−0.0037 (15)
C410	0.0399 (19)	0.0421 (19)	0.0361 (18)	−0.0085 (16)	0.0181 (15)	−0.0044 (15)
C411	0.042 (2)	0.061 (2)	0.0301 (17)	0.0109 (18)	0.0174 (15)	0.0127 (17)
C412	0.0326 (17)	0.049 (2)	0.0280 (16)	0.0096 (16)	0.0089 (13)	0.0108 (15)
N1	0.0251 (11)	0.0174 (10)	0.0141 (10)	−0.0036 (9)	0.0023 (9)	0.0011 (8)
O11	0.0234 (10)	0.0168 (9)	0.0303 (11)	−0.0013 (8)	0.0016 (8)	0.0066 (8)
O21	0.0217 (10)	0.0176 (9)	0.0351 (12)	0.0003 (8)	0.0060 (8)	0.0014 (8)
O31	0.0284 (11)	0.0214 (10)	0.0308 (11)	0.0040 (8)	0.0108 (9)	0.0004 (8)
O41	0.0348 (11)	0.0244 (10)	0.0197 (10)	−0.0106 (9)	0.0004 (8)	−0.0020 (8)
O51	0.0305 (11)	0.0229 (9)	0.0138 (9)	−0.0063 (8)	0.0013 (8)	0.0026 (8)
C11	0.0224 (13)	0.0163 (11)	0.0166 (12)	−0.0023 (10)	−0.0013 (10)	0.0012 (10)
C21	0.0206 (12)	0.0161 (11)	0.0158 (12)	−0.0019 (10)	0.0023 (10)	0.0019 (9)
C31	0.0256 (13)	0.0207 (12)	0.0146 (12)	0.0016 (11)	0.0042 (10)	−0.0003 (10)
C41	0.073 (3)	0.0297 (16)	0.0204 (15)	0.0016 (17)	0.0136 (16)	0.0006 (13)
C51	0.0233 (13)	0.0185 (12)	0.0166 (12)	0.0027 (11)	0.0035 (10)	0.0023 (10)
C61	0.0310 (15)	0.0271 (14)	0.0132 (12)	−0.0022 (12)	0.0020 (11)	0.0026 (10)
C71	0.054 (2)	0.0307 (16)	0.0229 (15)	0.0018 (15)	0.0104 (14)	−0.0006 (13)
C81	0.0444 (19)	0.0327 (16)	0.0188 (13)	−0.0021 (15)	0.0079 (13)	0.0075 (12)
C91	0.0324 (18)	0.053 (2)	0.0325 (17)	−0.0004 (16)	−0.0016 (14)	0.0142 (16)
N2	0.0232 (11)	0.0153 (10)	0.0165 (11)	−0.0043 (9)	−0.0008 (9)	0.0016 (8)
O12	0.0217 (10)	0.0175 (9)	0.0283 (11)	−0.0030 (8)	0.0019 (8)	0.0061 (8)
O22	0.0218 (10)	0.0191 (9)	0.0333 (11)	−0.0007 (8)	0.0069 (8)	0.0002 (8)
O32	0.0272 (11)	0.0224 (10)	0.0369 (12)	0.0034 (9)	0.0153 (9)	−0.0012 (9)
O42	0.0399 (12)	0.0239 (10)	0.0206 (10)	−0.0113 (9)	0.0030 (9)	−0.0026 (8)
O52	0.0346 (11)	0.0241 (10)	0.0122 (8)	−0.0072 (9)	0.0010 (8)	0.0018 (8)
C12	0.0220 (13)	0.0157 (11)	0.0178 (12)	0.0013 (10)	0.0006 (10)	0.0005 (10)
C22	0.0193 (12)	0.0152 (11)	0.0162 (12)	0.0004 (10)	0.0022 (10)	0.0003 (9)
C32	0.0309 (15)	0.0186 (12)	0.0187 (13)	0.0025 (12)	0.0031 (11)	−0.0010 (11)
C42	0.080 (3)	0.0337 (17)	0.0213 (15)	0.0068 (19)	0.0165 (17)	0.0018 (13)
C52	0.0243 (13)	0.0172 (11)	0.0189 (12)	−0.0017 (11)	0.0039 (10)	0.0006 (10)
C62	0.0347 (16)	0.0251 (14)	0.0125 (12)	−0.0001 (12)	0.0028 (11)	0.0003 (10)
C72	0.0433 (19)	0.0325 (16)	0.0226 (14)	−0.0010 (15)	0.0092 (13)	0.0077 (13)
C82	0.0366 (18)	0.047 (2)	0.0275 (16)	−0.0014 (16)	−0.0049 (14)	0.0079 (15)
C92	0.058 (2)	0.0300 (16)	0.0226 (15)	0.0072 (16)	0.0124 (15)	0.0000 (13)
N3	0.0274 (12)	0.0191 (10)	0.0175 (11)	0.0025 (10)	0.0040 (9)	0.0005 (9)
O13	0.0437 (14)	0.0202 (10)	0.0378 (13)	0.0075 (10)	0.0101 (11)	0.0039 (9)
O23	0.0257 (11)	0.0243 (10)	0.0346 (12)	−0.0010 (9)	−0.0033 (9)	0.0036 (9)
O33	0.0269 (11)	0.0219 (10)	0.0372 (12)	−0.0018 (9)	0.0125 (9)	−0.0027 (9)
O43	0.0314 (11)	0.0267 (10)	0.0253 (10)	0.0000 (9)	0.0043 (9)	−0.0068 (9)
O53	0.0322 (11)	0.0265 (10)	0.0189 (10)	0.0022 (9)	0.0020 (8)	0.0053 (8)
C13	0.0303 (15)	0.0222 (13)	0.0153 (12)	0.0010 (12)	0.0029 (11)	−0.0001 (11)
C23	0.0205 (13)	0.0216 (13)	0.0201 (13)	0.0028 (11)	0.0023 (10)	−0.0027 (11)
C33	0.0202 (12)	0.0217 (12)	0.0193 (12)	−0.0008 (11)	0.0024 (10)	0.0010 (10)
C43	0.0354 (16)	0.0235 (14)	0.0223 (14)	0.0020 (12)	0.0076 (12)	−0.0005 (11)
C53	0.0245 (14)	0.0219 (13)	0.0217 (13)	−0.0060 (11)	0.0004 (11)	−0.0016 (11)
C63	0.0291 (15)	0.0344 (16)	0.0161 (13)	−0.0021 (13)	−0.0003 (11)	0.0043 (12)
C73	0.0331 (17)	0.047 (2)	0.0261 (15)	−0.0009 (15)	0.0075 (13)	0.0060 (14)
C83	0.0337 (17)	0.058 (2)	0.0235 (15)	−0.0134 (16)	−0.0048 (13)	−0.0010 (15)
C93	0.043 (2)	0.0396 (18)	0.0327 (17)	0.0032 (16)	0.0059 (15)	0.0109 (15)
N4	0.0315 (13)	0.0161 (10)	0.0189 (11)	0.0019 (9)	0.0031 (10)	−0.0014 (9)
O14	0.0259 (10)	0.0180 (9)	0.0274 (11)	−0.0017 (8)	0.0046 (8)	−0.0031 (8)
O24	0.0219 (10)	0.0195 (9)	0.0407 (13)	0.0052 (8)	0.0055 (9)	0.0053 (9)
O34	0.0230 (10)	0.0202 (9)	0.0408 (12)	−0.0038 (8)	0.0105 (9)	−0.0031 (9)
O44	0.0307 (11)	0.0231 (10)	0.0286 (11)	0.0044 (9)	0.0024 (9)	0.0039 (9)
O54	0.0356 (12)	0.0267 (10)	0.0185 (9)	0.0068 (9)	0.0031 (8)	0.0017 (8)
C14	0.0229 (14)	0.0156 (11)	0.0186 (12)	0.0003 (10)	−0.0014 (10)	0.0028 (10)
C24	0.0202 (12)	0.0155 (11)	0.0208 (13)	0.0010 (10)	0.0042 (10)	−0.0030 (10)
C34	0.0237 (13)	0.0189 (12)	0.0214 (13)	−0.0040 (11)	0.0058 (11)	−0.0006 (11)
C44	0.0414 (18)	0.0246 (14)	0.0248 (14)	0.0000 (13)	0.0127 (13)	0.0027 (12)
C54	0.0226 (13)	0.0227 (13)	0.0250 (14)	−0.0026 (11)	0.0062 (11)	−0.0013 (11)
C64	0.048 (2)	0.048 (2)	0.0149 (13)	0.0187 (17)	0.0061 (13)	0.0024 (13)
C74	0.050 (2)	0.070 (3)	0.0283 (18)	0.022 (2)	−0.0100 (16)	−0.0106 (19)
C84	0.076 (3)	0.067 (3)	0.0274 (18)	0.035 (3)	0.0053 (18)	−0.0031 (19)
C94	0.061 (3)	0.060 (3)	0.044 (2)	0.016 (2)	0.027 (2)	0.024 (2)

Geometric parameters (Å, º) top

N11—C101	1.509 (3)	C407—C408	1.523 (4)
N11—C107	1.509 (3)	C407—H407	1.0000
N11—H11A	0.9200	C408—C409	1.533 (5)
N11—H11B	0.9200	C408—H40K	0.9900
C101—C106	1.523 (4)	C408—H40L	0.9900
C101—C102	1.526 (4)	C409—C410	1.510 (5)
C101—H101	1.0000	C409—H40M	0.9900
C102—C103	1.535 (4)	C409—H40N	0.9900
C102—H10A	0.9900	C410—C411	1.518 (5)
C102—H10B	0.9900	C410—H41A	0.9900
C103—C104	1.519 (5)	C410—H41B	0.9900
C103—H10C	0.9900	C411—C412	1.536 (4)
C103—H10D	0.9900	C411—H41C	0.9900
C104—C105	1.510 (5)	C411—H41D	0.9900
C104—H10E	0.9900	C412—H41E	0.9900
C104—H10F	0.9900	C412—H41F	0.9900
C105—C106	1.535 (4)	N1—C51	1.337 (3)
C105—H10G	0.9900	N1—C21	1.446 (3)
C105—H10H	0.9900	N1—H1	0.8800
C106—H10I	0.9900	O11—C11	1.259 (3)
C106—H10J	0.9900	O21—C11	1.265 (3)
C107—C108	1.527 (4)	O31—C31	1.423 (3)
C107—C112	1.531 (4)	O31—H31	0.8400
C107—H107	1.0000	O41—C51	1.223 (3)
C108—C109	1.532 (4)	O51—C51	1.360 (3)
C108—H10K	0.9900	O51—C61	1.462 (3)
C108—H10L	0.9900	C11—C21	1.533 (4)
C109—C110	1.530 (4)	C21—C31	1.539 (4)
C109—H10M	0.9900	C21—H21	1.0000
C109—H10N	0.9900	C31—C41	1.512 (4)
C110—C111	1.525 (5)	C31—H31X	1.0000
C110—H11C	0.9900	C41—H41X	0.9800
C110—H11D	0.9900	C41—H41Y	0.9800
C111—C112	1.527 (4)	C41—H41Z	0.9800
C111—H11E	0.9900	C61—C91	1.509 (5)
C111—H11F	0.9900	C61—C81	1.521 (4)
C112—H11G	0.9900	C61—C71	1.523 (4)
C112—H11H	0.9900	C71—H71X	0.9800
N12—C207	1.502 (3)	C71—H71Y	0.9800
N12—C201	1.508 (3)	C71—H71Z	0.9800
N12—H12A	0.9200	C81—H81X	0.9800
N12—H12B	0.9200	C81—H81Y	0.9800
C201—C202	1.520 (4)	C81—H81Z	0.9800
C201—C206	1.523 (4)	C91—H91X	0.9800
C201—H201	1.0000	C91—H91Y	0.9800
C202—C203	1.527 (4)	C91—H91Z	0.9800
C202—H20A	0.9900	N2—C52	1.339 (3)
C202—H20B	0.9900	N2—C22	1.448 (3)
C203—C204	1.528 (5)	N2—H2	0.8800
C203—H20C	0.9900	O12—C12	1.259 (3)
C203—H20D	0.9900	O22—C12	1.266 (3)
C204—C205	1.516 (5)	O32—C32	1.421 (3)
C204—H20E	0.9900	O32—H32	0.8400
C204—H20F	0.9900	O42—C52	1.216 (3)
C205—C206	1.538 (4)	O52—C52	1.361 (3)
C205—H20G	0.9900	O52—C62	1.461 (3)
C205—H20H	0.9900	C12—C22	1.535 (4)
C206—H20I	0.9900	C22—C32	1.546 (4)
C206—H20J	0.9900	C22—H22	1.0000
C207—C208	1.524 (4)	C32—C42	1.506 (4)
C207—C212	1.528 (4)	C32—H32X	1.0000
C207—H207	1.0000	C42—H42X	0.9800
C208—C209	1.530 (4)	C42—H42Y	0.9800
C208—H20K	0.9900	C42—H42Z	0.9800
C208—H20L	0.9900	C62—C72	1.513 (4)
C209—C210	1.527 (5)	C62—C92	1.517 (4)
C209—H20M	0.9900	C62—C82	1.521 (5)
C209—H20N	0.9900	C72—H72X	0.9800
C210—C211	1.524 (6)	C72—H72Y	0.9800
C210—H21E	0.9900	C72—H72Z	0.9800
C210—H21F	0.9900	C82—H82X	0.9800
C211—C212	1.528 (4)	C82—H82Y	0.9800
C211—H21I	0.9900	C82—H82Z	0.9800
C211—H21J	0.9900	C92—H92X	0.9800
C212—H21K	0.9900	C92—H92Y	0.9800
C212—H21L	0.9900	C92—H92Z	0.9800
N13—C307	1.503 (4)	N3—C53	1.351 (4)
N13—C301	1.506 (4)	N3—C23	1.462 (3)
N13—H13A	0.9200	N3—H3	0.8800
N13—H13B	0.9200	O13—C13	1.248 (4)
C301—C302	1.504 (4)	O23—C13	1.266 (4)
C301—C306	1.529 (4)	O33—C33	1.430 (3)
C301—H301	1.0000	O33—H33	0.8400
C302—C303	1.539 (4)	O43—C53	1.225 (4)
C302—H30A	0.9900	O53—C53	1.345 (4)
C302—H30B	0.9900	O53—C63	1.475 (3)
C303—C304	1.524 (6)	C13—C23	1.538 (4)
C303—H30C	0.9900	C23—C33	1.538 (4)
C303—H30D	0.9900	C23—H23	1.0000
C304—C305	1.521 (6)	C33—C43	1.516 (4)
C304—H30E	0.9900	C33—H33X	1.0000
C304—H30F	0.9900	C43—H43X	0.9800
C305—C306	1.529 (5)	C43—H43Y	0.9800
C305—H30G	0.9900	C43—H43Z	0.9800
C305—H30H	0.9900	C63—C83	1.512 (4)
C306—H30I	0.9900	C63—C93	1.515 (5)
C306—H30J	0.9900	C63—C73	1.530 (4)
C307—C312	1.522 (4)	C73—H73X	0.9800
C307—C308	1.531 (4)	C73—H73Y	0.9800
C307—H307	1.0000	C73—H73Z	0.9800
C308—C309	1.534 (4)	C83—H83X	0.9800
C308—H30K	0.9900	C83—H83Y	0.9800
C308—H30L	0.9900	C83—H83Z	0.9800
C309—C310	1.514 (5)	C93—H93X	0.9800
C309—H30M	0.9900	C93—H93Y	0.9800
C309—H30N	0.9900	C93—H93Z	0.9800
C310—C311	1.522 (5)	N4—C54	1.345 (4)
C310—H31A	0.9900	N4—C24	1.451 (3)
C310—H31B	0.9900	N4—H4	0.8800
C311—C312	1.520 (4)	O14—C14	1.257 (3)
C311—H31C	0.9900	O24—C14	1.263 (3)
C311—H31D	0.9900	O34—C34	1.425 (3)
C312—H31E	0.9900	O34—H34	0.8400
C312—H31F	0.9900	O44—C54	1.218 (4)
N14—C401	1.493 (4)	O54—C54	1.359 (3)
N14—C407	1.511 (4)	O54—C64	1.471 (4)
N14—H14A	0.9200	C14—C24	1.528 (4)
N14—H14B	0.9200	C24—C34	1.550 (4)
C401—C402	1.521 (4)	C24—H24	1.0000
C401—C406	1.521 (5)	C34—C44	1.507 (4)
C401—H401	1.0000	C34—H34X	1.0000
C402—C403	1.526 (4)	C44—H44X	0.9800
C402—H40A	0.9900	C44—H44Y	0.9800
C402—H40B	0.9900	C44—H44Z	0.9800
C403—C404	1.517 (6)	C64—C74	1.514 (5)
C403—H40C	0.9900	C64—C84	1.529 (5)
C403—H40D	0.9900	C64—C94	1.532 (6)
C404—C405	1.532 (7)	C74—H74X	0.9800
C404—H40E	0.9900	C74—H74Y	0.9800
C404—H40F	0.9900	C74—H74Z	0.9800
C405—C406	1.540 (5)	C84—H84X	0.9800
C405—H40G	0.9900	C84—H84Y	0.9800
C405—H40H	0.9900	C84—H84Z	0.9800
C406—H40I	0.9900	C94—H94X	0.9800
C406—H40J	0.9900	C94—H94Y	0.9800
C407—C412	1.523 (4)	C94—H94Z	0.9800

C101—N11—C107	118.0 (2)	C405—C404—H40F	109.8
C101—N11—H11A	107.8	H40E—C404—H40F	108.2
C107—N11—H11A	107.8	C404—C405—C406	112.7 (4)
C101—N11—H11B	107.8	C404—C405—H40G	109.1
C107—N11—H11B	107.8	C406—C405—H40G	109.1
H11A—N11—H11B	107.1	C404—C405—H40H	109.1
N11—C101—C106	108.2 (2)	C406—C405—H40H	109.1
N11—C101—C102	111.5 (2)	H40G—C405—H40H	107.8
C106—C101—C102	110.8 (2)	C401—C406—C405	109.1 (3)
N11—C101—H101	108.8	C401—C406—H40I	109.9
C106—C101—H101	108.8	C405—C406—H40I	109.9
C102—C101—H101	108.8	C401—C406—H40J	109.9
C101—C102—C103	109.7 (3)	C405—C406—H40J	109.9
C101—C102—H10A	109.7	H40I—C406—H40J	108.3
C103—C102—H10A	109.7	N14—C407—C412	107.7 (2)
C101—C102—H10B	109.7	N14—C407—C408	109.8 (2)
C103—C102—H10B	109.7	C412—C407—C408	112.3 (3)
H10A—C102—H10B	108.2	N14—C407—H407	109.0
C104—C103—C102	111.8 (3)	C412—C407—H407	109.0
C104—C103—H10C	109.2	C408—C407—H407	109.0
C102—C103—H10C	109.2	C407—C408—C409	111.7 (3)
C104—C103—H10D	109.2	C407—C408—H40K	109.3
C102—C103—H10D	109.2	C409—C408—H40K	109.3
H10C—C103—H10D	107.9	C407—C408—H40L	109.3
C105—C104—C103	110.4 (3)	C409—C408—H40L	109.3
C105—C104—H10E	109.6	H40K—C408—H40L	107.9
C103—C104—H10E	109.6	C410—C409—C408	111.3 (3)
C105—C104—H10F	109.6	C410—C409—H40M	109.4
C103—C104—H10F	109.6	C408—C409—H40M	109.4
H10E—C104—H10F	108.1	C410—C409—H40N	109.4
C104—C105—C106	111.0 (3)	C408—C409—H40N	109.4
C104—C105—H10G	109.4	H40M—C409—H40N	108.0
C106—C105—H10G	109.4	C409—C410—C411	110.1 (3)
C104—C105—H10H	109.4	C409—C410—H41A	109.6
C106—C105—H10H	109.4	C411—C410—H41A	109.6
H10G—C105—H10H	108.0	C409—C410—H41B	109.6
C101—C106—C105	109.9 (3)	C411—C410—H41B	109.6
C101—C106—H10I	109.7	H41A—C410—H41B	108.2
C105—C106—H10I	109.7	C410—C411—C412	110.1 (3)
C101—C106—H10J	109.7	C410—C411—H41C	109.6
C105—C106—H10J	109.7	C412—C411—H41C	109.6
H10I—C106—H10J	108.2	C410—C411—H41D	109.6
N11—C107—C108	111.2 (2)	C412—C411—H41D	109.6
N11—C107—C112	107.2 (2)	H41C—C411—H41D	108.2
C108—C107—C112	111.5 (2)	C407—C412—C411	111.2 (3)
N11—C107—H107	109.0	C407—C412—H41E	109.4
C108—C107—H107	109.0	C411—C412—H41E	109.4
C112—C107—H107	109.0	C407—C412—H41F	109.4
C107—C108—C109	110.9 (2)	C411—C412—H41F	109.4
C107—C108—H10K	109.5	H41E—C412—H41F	108.0
C109—C108—H10K	109.5	C51—N1—C21	119.7 (2)
C107—C108—H10L	109.5	C51—N1—H1	120.1
C109—C108—H10L	109.5	C21—N1—H1	120.1
H10K—C108—H10L	108.0	C31—O31—H31	109.5
C110—C109—C108	111.1 (2)	C51—O51—C61	120.3 (2)
C110—C109—H10M	109.4	O11—C11—O21	123.6 (3)
C108—C109—H10M	109.4	O11—C11—C21	117.7 (2)
C110—C109—H10N	109.4	O21—C11—C21	118.7 (2)
C108—C109—H10N	109.4	N1—C21—C11	112.3 (2)
H10M—C109—H10N	108.0	N1—C21—C31	109.1 (2)
C111—C110—C109	109.9 (3)	C11—C21—C31	110.6 (2)
C111—C110—H11C	109.7	N1—C21—H21	108.2
C109—C110—H11C	109.7	C11—C21—H21	108.2
C111—C110—H11D	109.7	C31—C21—H21	108.2
C109—C110—H11D	109.7	O31—C31—C41	107.7 (2)
H11C—C110—H11D	108.2	O31—C31—C21	110.2 (2)
C110—C111—C112	111.4 (3)	C41—C31—C21	112.0 (2)
C110—C111—H11E	109.3	O31—C31—H31X	109.0
C112—C111—H11E	109.3	C41—C31—H31X	109.0
C110—C111—H11F	109.3	C21—C31—H31X	109.0
C112—C111—H11F	109.3	C31—C41—H41X	109.5
H11E—C111—H11F	108.0	C31—C41—H41Y	109.5
C111—C112—C107	111.4 (2)	H41X—C41—H41Y	109.5
C111—C112—H11G	109.3	C31—C41—H41Z	109.5
C107—C112—H11G	109.3	H41X—C41—H41Z	109.5
C111—C112—H11H	109.3	H41Y—C41—H41Z	109.5
C107—C112—H11H	109.3	O41—C51—N1	125.1 (3)
H11G—C112—H11H	108.0	O41—C51—O51	125.2 (2)
C207—N12—C201	118.1 (2)	N1—C51—O51	109.7 (2)
C207—N12—H12A	107.8	O51—C61—C91	110.2 (3)
C201—N12—H12A	107.8	O51—C61—C81	101.6 (2)
C207—N12—H12B	107.8	C91—C61—C81	110.2 (3)
C201—N12—H12B	107.8	O51—C61—C71	110.5 (2)
H12A—N12—H12B	107.1	C91—C61—C71	113.0 (3)
N12—C201—C202	111.7 (2)	C81—C61—C71	110.7 (3)
N12—C201—C206	107.4 (2)	C61—C71—H71X	109.5
C202—C201—C206	111.4 (2)	C61—C71—H71Y	109.5
N12—C201—H201	108.8	H71X—C71—H71Y	109.5
C202—C201—H201	108.8	C61—C71—H71Z	109.5
C206—C201—H201	108.8	H71X—C71—H71Z	109.5
C201—C202—C203	110.9 (3)	H71Y—C71—H71Z	109.5
C201—C202—H20A	109.5	C61—C81—H81X	109.5
C203—C202—H20A	109.5	C61—C81—H81Y	109.5
C201—C202—H20B	109.5	H81X—C81—H81Y	109.5
C203—C202—H20B	109.5	C61—C81—H81Z	109.5
H20A—C202—H20B	108.1	H81X—C81—H81Z	109.5
C202—C203—C204	111.1 (3)	H81Y—C81—H81Z	109.5
C202—C203—H20C	109.4	C61—C91—H91X	109.5
C204—C203—H20C	109.4	C61—C91—H91Y	109.5
C202—C203—H20D	109.4	H91X—C91—H91Y	109.5
C204—C203—H20D	109.4	C61—C91—H91Z	109.5
H20C—C203—H20D	108.0	H91X—C91—H91Z	109.5
C205—C204—C203	111.1 (3)	H91Y—C91—H91Z	109.5
C205—C204—H20E	109.4	C52—N2—C22	119.7 (2)
C203—C204—H20E	109.4	C52—N2—H2	120.1
C205—C204—H20F	109.4	C22—N2—H2	120.1
C203—C204—H20F	109.4	C32—O32—H32	109.5
H20E—C204—H20F	108.0	C52—O52—C62	120.4 (2)
C204—C205—C206	110.7 (3)	O12—C12—O22	124.0 (2)
C204—C205—H20G	109.5	O12—C12—C22	117.2 (2)
C206—C205—H20G	109.5	O22—C12—C22	118.8 (2)
C204—C205—H20H	109.5	N2—C22—C12	112.4 (2)
C206—C205—H20H	109.5	N2—C22—C32	108.8 (2)
H20G—C205—H20H	108.1	C12—C22—C32	110.9 (2)
C201—C206—C205	111.6 (3)	N2—C22—H22	108.2
C201—C206—H20I	109.3	C12—C22—H22	108.2
C205—C206—H20I	109.3	C32—C22—H22	108.2
C201—C206—H20J	109.3	O32—C32—C42	107.8 (3)
C205—C206—H20J	109.3	O32—C32—C22	109.7 (2)
H20I—C206—H20J	108.0	C42—C32—C22	112.3 (3)
N12—C207—C208	111.3 (2)	O32—C32—H32X	109.0
N12—C207—C212	108.4 (2)	C42—C32—H32X	109.0
C208—C207—C212	111.7 (3)	C22—C32—H32X	109.0
N12—C207—H207	108.4	C32—C42—H42X	109.5
C208—C207—H207	108.4	C32—C42—H42Y	109.5
C212—C207—H207	108.4	H42X—C42—H42Y	109.5
C207—C208—C209	109.1 (3)	C32—C42—H42Z	109.5
C207—C208—H20K	109.9	H42X—C42—H42Z	109.5
C209—C208—H20K	109.9	H42Y—C42—H42Z	109.5
C207—C208—H20L	109.9	O42—C52—N2	125.3 (3)
C209—C208—H20L	109.9	O42—C52—O52	125.2 (3)
H20K—C208—H20L	108.3	N2—C52—O52	109.4 (2)
C210—C209—C208	111.4 (3)	O52—C62—C72	102.0 (2)
C210—C209—H20M	109.3	O52—C62—C92	110.4 (2)
C208—C209—H20M	109.3	C72—C62—C92	111.7 (3)
C210—C209—H20N	109.3	O52—C62—C82	109.9 (2)
C208—C209—H20N	109.3	C72—C62—C82	110.1 (3)
H20M—C209—H20N	108.0	C92—C62—C82	112.3 (3)
C211—C210—C209	110.9 (3)	C62—C72—H72X	109.5
C211—C210—H21E	109.5	C62—C72—H72Y	109.5
C209—C210—H21E	109.5	H72X—C72—H72Y	109.5
C211—C210—H21F	109.5	C62—C72—H72Z	109.5
C209—C210—H21F	109.5	H72X—C72—H72Z	109.5
H21E—C210—H21F	108.1	H72Y—C72—H72Z	109.5
C210—C211—C212	110.7 (3)	C62—C82—H82X	109.5
C210—C211—H21I	109.5	C62—C82—H82Y	109.5
C212—C211—H21I	109.5	H82X—C82—H82Y	109.5
C210—C211—H21J	109.5	C62—C82—H82Z	109.5
C212—C211—H21J	109.5	H82X—C82—H82Z	109.5
H21I—C211—H21J	108.1	H82Y—C82—H82Z	109.5
C211—C212—C207	110.2 (3)	C62—C92—H92X	109.5
C211—C212—H21K	109.6	C62—C92—H92Y	109.5
C207—C212—H21K	109.6	H92X—C92—H92Y	109.5
C211—C212—H21L	109.6	C62—C92—H92Z	109.5
C207—C212—H21L	109.6	H92X—C92—H92Z	109.5
H21K—C212—H21L	108.1	H92Y—C92—H92Z	109.5
C307—N13—C301	117.7 (2)	C53—N3—C23	124.0 (2)
C307—N13—H13A	107.9	C53—N3—H3	118.0
C301—N13—H13A	107.9	C23—N3—H3	118.0
C307—N13—H13B	107.9	C33—O33—H33	109.5
C301—N13—H13B	107.9	C53—O53—C63	121.6 (2)
H13A—N13—H13B	107.2	O13—C13—O23	124.3 (3)
C302—C301—N13	108.7 (2)	O13—C13—C23	116.8 (2)
C302—C301—C306	112.2 (3)	O23—C13—C23	118.8 (2)
N13—C301—C306	112.1 (2)	N3—C23—C13	113.9 (2)
C302—C301—H301	107.9	N3—C23—C33	107.8 (2)
N13—C301—H301	107.9	C13—C23—C33	109.9 (2)
C306—C301—H301	107.9	N3—C23—H23	108.4
C301—C302—C303	110.9 (3)	C13—C23—H23	108.4
C301—C302—H30A	109.4	C33—C23—H23	108.4
C303—C302—H30A	109.4	O33—C33—C43	108.3 (2)
C301—C302—H30B	109.4	O33—C33—C23	109.5 (2)
C303—C302—H30B	109.4	C43—C33—C23	112.7 (2)
H30A—C302—H30B	108.0	O33—C33—H33X	108.8
C304—C303—C302	109.9 (3)	C43—C33—H33X	108.8
C304—C303—H30C	109.7	C23—C33—H33X	108.8
C302—C303—H30C	109.7	C33—C43—H43X	109.5
C304—C303—H30D	109.7	C33—C43—H43Y	109.5
C302—C303—H30D	109.7	H43X—C43—H43Y	109.5
H30C—C303—H30D	108.2	C33—C43—H43Z	109.5
C305—C304—C303	111.1 (3)	H43X—C43—H43Z	109.5
C305—C304—H30E	109.4	H43Y—C43—H43Z	109.5
C303—C304—H30E	109.4	O43—C53—O53	125.5 (3)
C305—C304—H30F	109.4	O43—C53—N3	124.0 (3)
C303—C304—H30F	109.4	O53—C53—N3	110.5 (2)
H30E—C304—H30F	108.0	O53—C63—C83	110.2 (3)
C304—C305—C306	112.0 (3)	O53—C63—C93	101.7 (3)
C304—C305—H30G	109.2	C83—C63—C93	111.1 (3)
C306—C305—H30G	109.2	O53—C63—C73	110.7 (2)
C304—C305—H30H	109.2	C83—C63—C73	112.4 (3)
C306—C305—H30H	109.2	C93—C63—C73	110.3 (3)
H30G—C305—H30H	107.9	C63—C73—H73X	109.5
C305—C306—C301	108.8 (3)	C63—C73—H73Y	109.5
C305—C306—H30I	109.9	H73X—C73—H73Y	109.5
C301—C306—H30I	109.9	C63—C73—H73Z	109.5
C305—C306—H30J	109.9	H73X—C73—H73Z	109.5
C301—C306—H30J	109.9	H73Y—C73—H73Z	109.5
H30I—C306—H30J	108.3	C63—C83—H83X	109.5
N13—C307—C312	107.4 (2)	C63—C83—H83Y	109.5
N13—C307—C308	110.4 (2)	H83X—C83—H83Y	109.5
C312—C307—C308	111.4 (2)	C63—C83—H83Z	109.5
N13—C307—H307	109.2	H83X—C83—H83Z	109.5
C312—C307—H307	109.2	H83Y—C83—H83Z	109.5
C308—C307—H307	109.2	C63—C93—H93X	109.5
C307—C308—C309	111.0 (3)	C63—C93—H93Y	109.5
C307—C308—H30K	109.4	H93X—C93—H93Y	109.5
C309—C308—H30K	109.4	C63—C93—H93Z	109.5
C307—C308—H30L	109.4	H93X—C93—H93Z	109.5
C309—C308—H30L	109.4	H93Y—C93—H93Z	109.5
H30K—C308—H30L	108.0	C54—N4—C24	118.8 (2)
C310—C309—C308	111.1 (3)	C54—N4—H4	120.6
C310—C309—H30M	109.4	C24—N4—H4	120.6
C308—C309—H30M	109.4	C34—O34—H34	109.5
C310—C309—H30N	109.4	C54—O54—C64	120.1 (2)
C308—C309—H30N	109.4	O14—C14—O24	124.2 (3)
H30M—C309—H30N	108.0	O14—C14—C24	117.2 (2)
C309—C310—C311	110.3 (3)	O24—C14—C24	118.6 (2)
C309—C310—H31A	109.6	N4—C24—C14	112.7 (2)
C311—C310—H31A	109.6	N4—C24—C34	108.3 (2)
C309—C310—H31B	109.6	C14—C24—C34	111.8 (2)
C311—C310—H31B	109.6	N4—C24—H24	107.9
H31A—C310—H31B	108.1	C14—C24—H24	107.9
C312—C311—C310	111.8 (3)	C34—C24—H24	107.9
C312—C311—H31C	109.3	O34—C34—C44	108.3 (2)
C310—C311—H31C	109.3	O34—C34—C24	109.0 (2)
C312—C311—H31D	109.3	C44—C34—C24	112.5 (2)
C310—C311—H31D	109.3	O34—C34—H34X	109.0
H31C—C311—H31D	107.9	C44—C34—H34X	109.0
C311—C312—C307	111.8 (2)	C24—C34—H34X	109.0
C311—C312—H31E	109.3	C34—C44—H44X	109.5
C307—C312—H31E	109.3	C34—C44—H44Y	109.5
C311—C312—H31F	109.3	H44X—C44—H44Y	109.5
C307—C312—H31F	109.3	C34—C44—H44Z	109.5
H31E—C312—H31F	107.9	H44X—C44—H44Z	109.5
C401—N14—C407	118.2 (2)	H44Y—C44—H44Z	109.5
C401—N14—H14A	107.8	O44—C54—N4	125.0 (3)
C407—N14—H14A	107.8	O44—C54—O54	124.9 (3)
C401—N14—H14B	107.8	N4—C54—O54	110.1 (2)
C407—N14—H14B	107.8	O54—C64—C74	110.5 (3)
H14A—N14—H14B	107.1	O54—C64—C84	101.4 (3)
N14—C401—C402	108.4 (2)	C74—C64—C84	110.9 (3)
N14—C401—C406	111.2 (3)	O54—C64—C94	110.0 (3)
C402—C401—C406	111.9 (3)	C74—C64—C94	112.7 (3)
N14—C401—H401	108.4	C84—C64—C94	110.8 (3)
C402—C401—H401	108.4	C64—C74—H74X	109.5
C406—C401—H401	108.4	C64—C74—H74Y	109.5
C401—C402—C403	110.7 (3)	H74X—C74—H74Y	109.5
C401—C402—H40A	109.5	C64—C74—H74Z	109.5
C403—C402—H40A	109.5	H74X—C74—H74Z	109.5
C401—C402—H40B	109.5	H74Y—C74—H74Z	109.5
C403—C402—H40B	109.5	C64—C84—H84X	109.5
H40A—C402—H40B	108.1	C64—C84—H84Y	109.5
C404—C403—C402	111.4 (3)	H84X—C84—H84Y	109.5
C404—C403—H40C	109.3	C64—C84—H84Z	109.5
C402—C403—H40C	109.3	H84X—C84—H84Z	109.5
C404—C403—H40D	109.3	H84Y—C84—H84Z	109.5
C402—C403—H40D	109.3	C64—C94—H94X	109.5
H40C—C403—H40D	108.0	C64—C94—H94Y	109.5
C403—C404—C405	109.5 (3)	H94X—C94—H94Y	109.5
C403—C404—H40E	109.8	C64—C94—H94Z	109.5
C405—C404—H40E	109.8	H94X—C94—H94Z	109.5
C403—C404—H40F	109.8	H94Y—C94—H94Z	109.5

C107—N11—C101—C106	171.5 (2)	C407—C408—C409—C410	−54.1 (4)
C107—N11—C101—C102	−66.5 (3)	C408—C409—C410—C411	58.6 (4)
N11—C101—C102—C103	−177.7 (2)	C409—C410—C411—C412	−59.9 (4)
C106—C101—C102—C103	−57.2 (3)	N14—C407—C412—C411	−173.9 (3)
C101—C102—C103—C104	56.2 (4)	C408—C407—C412—C411	−52.8 (4)
C102—C103—C104—C105	−56.2 (4)	C410—C411—C412—C407	57.0 (4)
C103—C104—C105—C106	56.8 (4)	C51—N1—C21—C11	−76.5 (3)
N11—C101—C106—C105	−179.3 (3)	C51—N1—C21—C31	160.4 (2)
C102—C101—C106—C105	58.3 (4)	O11—C11—C21—N1	141.6 (2)
C104—C105—C106—C101	−58.0 (4)	O21—C11—C21—N1	−41.0 (3)
C101—N11—C107—C108	−53.3 (3)	O11—C11—C21—C31	−96.2 (3)
C101—N11—C107—C112	−175.4 (2)	O21—C11—C21—C31	81.2 (3)
N11—C107—C108—C109	−174.1 (2)	N1—C21—C31—O31	−60.5 (3)
C112—C107—C108—C109	−54.5 (3)	C11—C21—C31—O31	175.5 (2)
C107—C108—C109—C110	56.6 (3)	N1—C21—C31—C41	179.6 (3)
C108—C109—C110—C111	−57.6 (4)	C11—C21—C31—C41	55.6 (3)
C109—C110—C111—C112	57.1 (3)	C21—N1—C51—O41	−5.3 (4)
C110—C111—C112—C107	−55.6 (3)	C21—N1—C51—O51	175.6 (2)
N11—C107—C112—C111	175.9 (2)	C61—O51—C51—O41	0.8 (4)
C108—C107—C112—C111	54.0 (3)	C61—O51—C51—N1	180.0 (2)
C207—N12—C201—C202	−52.5 (3)	C51—O51—C61—C91	−67.8 (3)
C207—N12—C201—C206	−174.9 (2)	C51—O51—C61—C81	175.3 (2)
N12—C201—C202—C203	−175.5 (2)	C51—O51—C61—C71	57.8 (3)
C206—C201—C202—C203	−55.4 (3)	C52—N2—C22—C12	−78.6 (3)
C201—C202—C203—C204	56.3 (4)	C52—N2—C22—C32	158.3 (2)
C202—C203—C204—C205	−57.0 (4)	O12—C12—C22—N2	144.2 (2)
C203—C204—C205—C206	55.8 (4)	O22—C12—C22—N2	−37.8 (3)
N12—C201—C206—C205	177.4 (3)	O12—C12—C22—C32	−93.9 (3)
C202—C201—C206—C205	54.8 (4)	O22—C12—C22—C32	84.1 (3)
C204—C205—C206—C201	−55.0 (4)	N2—C22—C32—O32	−60.3 (3)
C201—N12—C207—C208	−62.9 (3)	C12—C22—C32—O32	175.7 (2)
C201—N12—C207—C212	173.9 (2)	N2—C22—C32—C42	179.9 (3)
N12—C207—C208—C209	−179.0 (2)	C12—C22—C32—C42	55.9 (3)
C212—C207—C208—C209	−57.6 (3)	C22—N2—C52—O42	−4.0 (4)
C207—C208—C209—C210	57.0 (4)	C22—N2—C52—O52	177.0 (2)
C208—C209—C210—C211	−57.1 (4)	C62—O52—C52—O42	5.5 (4)
C209—C210—C211—C212	56.1 (4)	C62—O52—C52—N2	−175.5 (2)
C210—C211—C212—C207	−56.2 (4)	C52—O52—C62—C72	174.4 (2)
N12—C207—C212—C211	−179.2 (3)	C52—O52—C62—C92	55.6 (3)
C208—C207—C212—C211	57.8 (4)	C52—O52—C62—C82	−68.9 (3)
C307—N13—C301—C302	177.7 (3)	C53—N3—C23—C13	−67.1 (3)
C307—N13—C301—C306	53.2 (3)	C53—N3—C23—C33	170.7 (3)
N13—C301—C302—C303	177.8 (3)	O13—C13—C23—N3	138.2 (3)
C306—C301—C302—C303	−57.7 (4)	O23—C13—C23—N3	−45.0 (4)
C301—C302—C303—C304	56.1 (4)	O13—C13—C23—C33	−100.7 (3)
C302—C303—C304—C305	−55.7 (4)	O23—C13—C23—C33	76.1 (3)
C303—C304—C305—C306	57.2 (4)	N3—C23—C33—O33	−64.0 (3)
C304—C305—C306—C301	−56.2 (4)	C13—C23—C33—O33	171.3 (2)
C302—C301—C306—C305	56.8 (4)	N3—C23—C33—C43	175.4 (2)
N13—C301—C306—C305	179.4 (3)	C13—C23—C33—C43	50.8 (3)
C301—N13—C307—C312	−178.9 (2)	C63—O53—C53—O43	−0.1 (4)
C301—N13—C307—C308	59.5 (3)	C63—O53—C53—N3	178.0 (2)
N13—C307—C308—C309	173.1 (2)	C23—N3—C53—O43	−170.2 (3)
C312—C307—C308—C309	53.9 (3)	C23—N3—C53—O53	11.7 (4)
C307—C308—C309—C310	−56.4 (4)	C53—O53—C63—C83	63.4 (4)
C308—C309—C310—C311	57.4 (4)	C53—O53—C63—C93	−178.7 (3)
C309—C310—C311—C312	−56.6 (4)	C53—O53—C63—C73	−61.5 (4)
C310—C311—C312—C307	54.7 (4)	C54—N4—C24—C14	−67.8 (3)
N13—C307—C312—C311	−174.1 (3)	C54—N4—C24—C34	167.9 (2)
C308—C307—C312—C311	−53.2 (3)	O14—C14—C24—N4	144.0 (2)
C407—N14—C401—C402	−174.9 (2)	O24—C14—C24—N4	−37.2 (3)
C407—N14—C401—C406	61.6 (4)	O14—C14—C24—C34	−93.7 (3)
N14—C401—C402—C403	179.9 (3)	O24—C14—C24—C34	85.1 (3)
C406—C401—C402—C403	−57.0 (4)	N4—C24—C34—O34	−60.1 (3)
C401—C402—C403—C404	57.1 (4)	C14—C24—C34—O34	175.1 (2)
C402—C403—C404—C405	−56.2 (4)	N4—C24—C34—C44	179.8 (2)
C403—C404—C405—C406	56.4 (5)	C14—C24—C34—C44	55.0 (3)
N14—C401—C406—C405	177.0 (3)	C24—N4—C54—O44	−3.7 (4)
C402—C401—C406—C405	55.6 (4)	C24—N4—C54—O54	178.0 (2)
C404—C405—C406—C401	−55.8 (5)	C64—O54—C54—O44	−2.2 (4)
C401—N14—C407—C412	−174.3 (3)	C64—O54—C54—N4	176.2 (3)
C401—N14—C407—C408	63.1 (3)	C54—O54—C64—C74	−60.8 (4)
N14—C407—C408—C409	171.0 (2)	C54—O54—C64—C84	−178.4 (3)
C412—C407—C408—C409	51.1 (3)	C54—O54—C64—C94	64.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11B···O11ⁱ	0.92	1.81	2.697 (3)	161
N11—H11A···O21	0.92	1.85	2.765 (3)	178
N12—H12A···O22	0.92	1.84	2.761 (3)	177
N12—H12B···O12ⁱⁱ	0.92	1.82	2.704 (3)	162
N13—H13A···O13ⁱⁱⁱ	0.92	1.84	2.751 (3)	169
N13—H13B···O23	0.92	1.82	2.741 (3)	175
N14—H14A···O24	0.92	1.81	2.724 (3)	170
N14—H14B···O14^iv	0.92	1.84	2.728 (3)	160
N1—H1···O11ⁱ	0.88	2.03	2.876 (3)	161
O31—H31···O21ⁱ	0.84	1.96	2.784 (3)	166
N2—H2···O12ⁱⁱ	0.88	2.04	2.888 (3)	162
O32—H32···O22ⁱⁱ	0.84	1.96	2.789 (3)	172
N3—H3···O23ⁱⁱⁱ	0.88	2.43	3.207 (3)	148
N3—H3···O13ⁱⁱⁱ	0.88	2.54	3.358 (4)	156
O33—H33···O23ⁱⁱⁱ	0.84	1.88	2.715 (3)	174
N4—H4···O14^iv	0.88	2.13	2.921 (3)	150
O34—H34···O24^iv	0.84	1.91	2.743 (3)	171
C208—H20K···O34^iv	0.99	2.58	3.411 (4)	141
C210—H21E···O42ⁱⁱ	0.99	2.52	3.434 (4)	154
C402—H40A···O44^iv	0.99	2.35	3.233 (4)	148
C412—H41F···O14^iv	0.99	2.55	3.325 (4)	136

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

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page