2-(1-Naphth­yl)isoindoline-1,3-dione

The asymmetric unit of the title compound, C₁₈H₁₁NO₂, comprises three independent mol­ecules, which differ in the dihedral angle between the phthalimide unit and the naphthalene ring system. In the asymmetric unit, two mol­ecules lie on either side of the phthalimide plane of the third mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.012 Å
• R factor = 0.059
• wR factor = 0.185
• Data-to-parameter ratio = 6.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry .....         95 PerFi
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C53    -   C54     ..       7.89 su
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         12

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       6.73
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.23
PLAT113_ALERT_2_C ADDSYM Suggests Possible Pseudo/New Spacegroup .       Pnma
PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ...    4055.00 Ang-3
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT213_ALERT_2_C Atom C37     has ADP max/min Ratio .............       3.40 prola
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C37
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C48
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C51
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C54
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C38
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C49
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C50
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.41

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           25.02
           From the CIF: _reflns_number_total               3660
           Count of symmetry unique reflns         3661
           Completeness (_total/calc)             99.97%
           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

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  13 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

2-(1-Naphthyl)isoindoline-1,3-dione

Crystal data

C18H11NO2	F(000) = 1704
Mr = 273.28	Dx = 1.343 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2464 reflections
a = 16.029 (13) Å	θ = 2.5–20.2°
b = 8.709 (7) Å	µ = 0.09 mm^−1
c = 29.04 (2) Å	T = 294 K
V = 4055 (6) Å^3	Plate, colourless
Z = 12	0.26 × 0.24 × 0.12 mm

Data collection

Bruker SMART 1000 CCD diffractometer	3660 independent reflections
Radiation source: fine-focus sealed tube	1981 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.087
φ and ω scans	θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −19→19
Tmin = 0.977, Tmax = 0.990	k = −7→10
19648 measured reflections	l = −34→28

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.185	H-atom parameters constrained
S = 1.15	w = 1/[σ^2(Fo^2) + (0.0822P)^2 + 0.621P] where P = (Fo^2 + 2Fc^2)/3
3660 reflections	(Δ/σ)max = 0.004
544 parameters	Δρmax = 0.50 e Å^−3
7 restraints	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.

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.0721 (4)	0.6127 (9)	0.0711 (3)	0.077 (2)
O2	0.1807 (4)	0.2751 (8)	0.1750 (3)	0.074 (2)
O3	0.1951 (3)	0.2727 (7)	0.3871 (2)	0.0655 (18)
O4	0.0900 (3)	0.6222 (8)	0.4902 (2)	0.0704 (19)
O5	0.3318 (3)	−0.0368 (6)	0.3015 (3)	0.098 (2)
O6	0.0967 (3)	0.2553 (5)	0.2848 (3)	0.0756 (17)
N1	0.1482 (4)	0.4558 (8)	0.1196 (3)	0.0555 (19)
N2	0.1627 (4)	0.4611 (7)	0.4407 (2)	0.0466 (17)
N3	0.2023 (3)	0.0764 (6)	0.2929 (3)	0.076 (3)
C1	0.0756 (5)	0.5064 (12)	0.0980 (4)	0.059 (3)
C2	0.0058 (4)	0.4085 (9)	0.1145 (3)	0.0432 (19)
C3	−0.0778 (5)	0.4090 (11)	0.1044 (3)	0.062 (3)
H3	−0.0993	0.4740	0.0819	0.075*
C4	−0.1291 (6)	0.3103 (13)	0.1284 (4)	0.074 (3)
H4	−0.1858	0.3074	0.1217	0.089*
C5	−0.0981 (6)	0.2181 (12)	0.1615 (4)	0.070 (3)
H5	−0.1345	0.1546	0.1776	0.084*
C6	−0.0138 (5)	0.2145 (10)	0.1724 (3)	0.063 (3)
H6	0.0068	0.1510	0.1955	0.076*
C7	0.0385 (5)	0.3107 (10)	0.1471 (3)	0.052 (2)
C8	0.1303 (5)	0.3369 (10)	0.1515 (3)	0.049 (2)
C9	0.2286 (5)	0.5320 (10)	0.1159 (3)	0.051 (2)
C10	0.2572 (5)	0.6094 (11)	0.1541 (3)	0.060 (2)
H10	0.2264	0.6118	0.1813	0.072*
C11	0.3350 (6)	0.6851 (11)	0.1507 (4)	0.068 (3)
H11	0.3560	0.7379	0.1760	0.082*
C12	0.3795 (6)	0.6818 (12)	0.1110 (4)	0.071 (3)
H12	0.4305	0.7323	0.1092	0.085*
C13	0.3487 (4)	0.6027 (10)	0.0730 (3)	0.052 (2)
C14	0.3936 (6)	0.6023 (12)	0.0302 (5)	0.074 (3)
H14	0.4423	0.6597	0.0276	0.089*
C15	0.3657 (6)	0.5184 (12)	−0.0071 (4)	0.079 (3)
H15	0.3962	0.5135	−0.0343	0.095*
C16	0.2920 (6)	0.4434 (11)	−0.0024 (4)	0.071 (3)
H16	0.2720	0.3896	−0.0278	0.086*
C17	0.2448 (5)	0.4408 (10)	0.0367 (3)	0.055 (2)
H17	0.1955	0.3850	0.0382	0.066*
C18	0.2726 (4)	0.5230 (11)	0.0737 (3)	0.050 (2)
C19	0.1435 (5)	0.3400 (10)	0.4104 (3)	0.057 (2)
C20	0.0523 (4)	0.3164 (9)	0.4144 (3)	0.045 (2)
C21	0.0012 (5)	0.2159 (11)	0.3921 (3)	0.062 (3)
H21	0.0222	0.1474	0.3705	0.075*
C22	−0.0836 (5)	0.2187 (11)	0.4029 (4)	0.068 (3)
H22	−0.1199	0.1529	0.3876	0.082*
C23	−0.1147 (5)	0.3192 (11)	0.4363 (4)	0.063 (3)
H23	−0.1714	0.3188	0.4432	0.076*
C24	−0.0620 (5)	0.4192 (11)	0.4594 (3)	0.061 (3)
H24	−0.0819	0.4858	0.4819	0.074*
C25	0.0227 (4)	0.4154 (10)	0.4472 (3)	0.050 (2)
C26	0.0909 (5)	0.5143 (11)	0.4633 (3)	0.047 (2)
C27	0.2440 (4)	0.5343 (10)	0.4426 (3)	0.049 (2)
C28	0.2735 (5)	0.6094 (9)	0.4060 (3)	0.057 (2)
H28	0.2414	0.6127	0.3793	0.068*
C29	0.3516 (5)	0.6841 (11)	0.4062 (4)	0.066 (3)
H29	0.3715	0.7331	0.3800	0.079*
C30	0.3975 (5)	0.6826 (11)	0.4460 (4)	0.066 (3)
H30	0.4489	0.7321	0.4468	0.079*
C31	0.3680 (4)	0.6069 (9)	0.4863 (3)	0.053 (2)
C32	0.4138 (5)	0.5996 (11)	0.5288 (4)	0.066 (3)
H32	0.4652	0.6487	0.5308	0.079*
C33	0.3854 (6)	0.5263 (13)	0.5645 (5)	0.085 (3)
H33	0.4166	0.5292	0.5915	0.102*
C34	0.3079 (6)	0.4403 (13)	0.5646 (4)	0.077 (3)
H34	0.2900	0.3846	0.5901	0.093*
C35	0.2634 (5)	0.4469 (11)	0.5250 (3)	0.060 (2)
H35	0.2128	0.3948	0.5239	0.073*
C36	0.2894 (4)	0.5291 (9)	0.4846 (3)	0.0399 (19)
C37	0.2883 (4)	0.0762 (9)	0.2912 (5)	0.100 (5)
C38	0.3138 (3)	0.2372 (7)	0.2855 (4)	0.0515 (19)
C39	0.3921 (4)	0.3026 (8)	0.2839 (4)	0.067 (2)
H39	0.4399	0.2421	0.2849	0.081*
C40	0.3975 (5)	0.4586 (8)	0.2808 (4)	0.067 (2)
H40	0.4499	0.5044	0.2796	0.080*
C41	0.3277 (5)	0.5495 (8)	0.2794 (4)	0.064 (2)
H41	0.3333	0.6558	0.2790	0.077*
C42	0.2480 (4)	0.4837 (7)	0.2786 (3)	0.0570 (19)
H42	0.2002	0.5436	0.2758	0.068*
C43	0.2435 (4)	0.3257 (6)	0.2819 (4)	0.0470 (17)
C44	0.1696 (4)	0.2228 (7)	0.2851 (4)	0.060 (2)
C45	0.1510 (2)	−0.0561 (4)	0.30707 (17)	0.060 (2)
C46	0.1406 (3)	−0.0913 (6)	0.35339 (15)	0.069 (3)
H46	0.1676	−0.0334	0.3758	0.083*
C47	0.0897 (3)	−0.2133 (7)	0.36628 (15)	0.068 (3)
H47	0.0828	−0.2369	0.3973	0.082*
C48	0.0493 (3)	−0.3000 (5)	0.3329 (2)	0.083 (3)
H48	0.0153	−0.3816	0.3415	0.100*
C49	0.05972 (17)	−0.2647 (3)	0.28653 (18)	0.0514 (18)
C50	0.11054 (17)	−0.1427 (3)	0.27364 (14)	0.0429 (18)
C51	0.1210 (3)	−0.1075 (6)	0.22732 (15)	0.076 (3)
H51	0.1550	−0.0259	0.2187	0.091*
C52	0.0805 (4)	−0.1941 (7)	0.19389 (15)	0.076 (3)
H52	0.0875	−0.1705	0.1629	0.091*
C53	0.0297 (3)	−0.3161 (7)	0.2068 (2)	0.093 (3)
H53	0.0027	−0.3741	0.1844	0.112*
C54	0.0193 (2)	−0.3514 (4)	0.2531 (2)	0.094 (4)
H54	−0.0147	−0.4329	0.2617	0.113*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.049 (4)	0.095 (5)	0.088 (5)	0.003 (3)	0.004 (3)	0.037 (5)
O2	0.038 (3)	0.081 (5)	0.101 (5)	0.008 (3)	−0.003 (3)	0.023 (4)
O3	0.037 (3)	0.073 (4)	0.086 (5)	0.008 (3)	0.002 (3)	−0.024 (4)
O4	0.056 (4)	0.074 (4)	0.081 (5)	−0.006 (3)	0.013 (3)	−0.026 (4)
O5	0.055 (3)	0.061 (3)	0.177 (7)	0.011 (3)	0.013 (4)	0.014 (4)
O6	0.027 (3)	0.060 (3)	0.140 (5)	0.007 (2)	0.004 (4)	0.009 (5)
N1	0.036 (4)	0.064 (5)	0.067 (5)	−0.005 (3)	−0.002 (3)	0.016 (4)
N2	0.032 (3)	0.050 (4)	0.057 (5)	0.003 (3)	0.001 (3)	−0.008 (4)
N3	0.024 (3)	0.039 (3)	0.166 (9)	−0.006 (2)	0.005 (4)	0.010 (4)
C1	0.042 (5)	0.060 (6)	0.076 (7)	0.004 (4)	−0.006 (5)	0.001 (6)
C2	0.036 (4)	0.049 (5)	0.045 (5)	−0.005 (4)	0.005 (4)	−0.003 (4)
C3	0.048 (5)	0.075 (7)	0.064 (6)	−0.001 (5)	−0.009 (4)	−0.002 (5)
C4	0.041 (5)	0.084 (8)	0.096 (8)	−0.017 (5)	0.000 (6)	−0.011 (7)
C5	0.048 (5)	0.071 (7)	0.090 (9)	−0.009 (5)	0.005 (5)	0.004 (6)
C6	0.046 (5)	0.060 (6)	0.085 (7)	−0.005 (4)	0.009 (5)	0.006 (5)
C7	0.036 (4)	0.054 (5)	0.066 (6)	−0.004 (4)	0.007 (4)	−0.006 (5)
C8	0.037 (4)	0.052 (5)	0.058 (6)	0.005 (4)	0.008 (5)	−0.004 (5)
C9	0.035 (4)	0.059 (5)	0.061 (6)	−0.007 (4)	−0.011 (4)	0.011 (5)
C10	0.052 (5)	0.076 (7)	0.051 (6)	−0.002 (4)	0.002 (5)	−0.011 (5)
C11	0.061 (6)	0.077 (7)	0.068 (7)	−0.014 (5)	−0.021 (6)	−0.007 (5)
C12	0.041 (5)	0.082 (7)	0.090 (8)	−0.011 (5)	−0.005 (6)	0.031 (6)
C13	0.028 (4)	0.052 (5)	0.075 (6)	−0.001 (4)	−0.008 (5)	0.002 (5)
C14	0.042 (5)	0.060 (7)	0.121 (10)	0.003 (4)	0.024 (6)	0.026 (7)
C15	0.065 (7)	0.076 (7)	0.096 (9)	0.001 (6)	0.032 (6)	0.006 (7)
C16	0.065 (6)	0.071 (7)	0.078 (8)	0.007 (5)	0.010 (6)	−0.020 (6)
C17	0.045 (5)	0.055 (5)	0.066 (6)	0.002 (4)	0.003 (5)	0.001 (5)
C18	0.028 (4)	0.056 (6)	0.065 (6)	0.000 (4)	0.000 (4)	0.005 (5)
C19	0.035 (4)	0.057 (6)	0.077 (7)	0.000 (4)	−0.007 (5)	−0.005 (5)
C20	0.026 (4)	0.047 (5)	0.063 (6)	0.004 (4)	−0.004 (4)	0.004 (5)
C21	0.042 (5)	0.071 (6)	0.074 (7)	0.002 (4)	−0.002 (5)	−0.012 (5)
C22	0.038 (5)	0.071 (7)	0.096 (8)	−0.014 (4)	−0.008 (5)	−0.002 (6)
C23	0.031 (4)	0.066 (6)	0.094 (7)	−0.006 (4)	0.006 (5)	0.002 (6)
C24	0.040 (5)	0.073 (7)	0.071 (7)	0.000 (4)	0.006 (4)	0.007 (6)
C25	0.023 (4)	0.059 (5)	0.067 (6)	0.003 (4)	−0.004 (4)	0.013 (5)
C26	0.041 (5)	0.054 (6)	0.047 (5)	0.001 (4)	−0.006 (4)	0.003 (5)
C27	0.025 (4)	0.058 (5)	0.063 (6)	0.006 (4)	0.008 (4)	−0.004 (5)
C28	0.041 (5)	0.059 (6)	0.070 (7)	−0.007 (4)	0.014 (5)	−0.013 (5)
C29	0.053 (5)	0.068 (6)	0.076 (7)	−0.008 (5)	0.021 (5)	0.000 (5)
C30	0.039 (5)	0.061 (6)	0.097 (8)	−0.012 (4)	0.020 (6)	−0.007 (6)
C31	0.031 (4)	0.051 (5)	0.078 (7)	0.000 (4)	−0.005 (5)	−0.024 (5)
C32	0.044 (5)	0.057 (6)	0.096 (8)	0.004 (4)	−0.016 (6)	−0.014 (6)
C33	0.071 (7)	0.077 (8)	0.109 (10)	0.004 (6)	−0.038 (7)	0.009 (7)
C34	0.065 (6)	0.093 (8)	0.074 (7)	0.003 (5)	−0.020 (6)	−0.012 (6)
C35	0.038 (4)	0.072 (6)	0.071 (7)	0.002 (4)	−0.003 (5)	−0.004 (5)
C36	0.030 (4)	0.037 (4)	0.053 (5)	0.002 (3)	0.004 (4)	−0.006 (4)
C37	0.024 (4)	0.045 (4)	0.229 (15)	0.010 (3)	0.010 (6)	0.013 (7)
C38	0.021 (3)	0.046 (3)	0.088 (6)	0.001 (3)	0.006 (4)	0.001 (5)
C39	0.039 (4)	0.063 (4)	0.099 (6)	−0.002 (3)	0.012 (6)	0.007 (7)
C40	0.052 (5)	0.063 (5)	0.085 (6)	−0.023 (4)	0.016 (6)	−0.006 (7)
C41	0.060 (5)	0.046 (4)	0.085 (6)	−0.015 (4)	0.007 (6)	0.002 (6)
C42	0.048 (4)	0.050 (4)	0.074 (5)	0.002 (3)	0.010 (5)	−0.003 (5)
C43	0.036 (4)	0.034 (3)	0.071 (5)	−0.006 (3)	0.008 (5)	−0.016 (5)
C44	0.032 (4)	0.044 (4)	0.103 (7)	0.003 (3)	0.007 (5)	0.000 (6)
C45	0.035 (4)	0.057 (5)	0.088 (7)	0.008 (4)	0.008 (4)	0.007 (5)
C46	0.070 (6)	0.050 (5)	0.087 (8)	0.006 (5)	0.021 (5)	0.018 (5)
C47	0.072 (6)	0.074 (7)	0.059 (7)	0.017 (5)	0.016 (5)	0.019 (5)
C48	0.058 (6)	0.066 (6)	0.125 (10)	0.016 (5)	0.026 (6)	0.015 (7)
C49	0.033 (4)	0.040 (4)	0.081 (6)	0.003 (3)	0.003 (5)	−0.002 (5)
C50	0.027 (4)	0.033 (3)	0.069 (6)	0.000 (3)	0.005 (4)	0.000 (4)
C51	0.053 (5)	0.079 (7)	0.096 (8)	0.018 (5)	0.012 (6)	0.003 (6)
C52	0.090 (8)	0.070 (7)	0.067 (7)	−0.003 (6)	−0.014 (6)	−0.012 (6)
C53	0.105 (9)	0.074 (8)	0.102 (9)	0.023 (7)	0.001 (7)	−0.014 (6)
C54	0.045 (5)	0.052 (5)	0.186 (13)	0.015 (4)	−0.022 (7)	−0.037 (7)

Geometric parameters (Å, º)

O1—C1	1.213 (11)	C23—H23	0.9300
O2—C8	1.186 (10)	C24—C25	1.403 (11)
O3—C19	1.220 (10)	C24—H24	0.9300
O4—C26	1.222 (10)	C25—C26	1.468 (11)
O5—C37	1.243 (9)	C27—C28	1.335 (11)
O6—C44	1.202 (7)	C27—C36	1.422 (11)
N1—C1	1.395 (10)	C28—C29	1.411 (11)
N1—C8	1.417 (11)	C28—H28	0.9300
N1—C9	1.454 (10)	C29—C30	1.370 (13)
N2—C26	1.403 (10)	C29—H29	0.9300
N2—C19	1.408 (11)	C30—C31	1.423 (13)
N2—C27	1.452 (10)	C30—H30	0.9300
N3—C37	1.380 (9)	C31—C36	1.431 (10)
N3—C44	1.397 (9)	C31—C32	1.437 (14)
N3—C45	1.475 (6)	C32—C33	1.299 (14)
C1—C2	1.486 (12)	C32—H32	0.9300
C2—C3	1.372 (11)	C33—C34	1.451 (14)
C2—C7	1.376 (11)	C33—H33	0.9300
C3—C4	1.378 (13)	C34—C35	1.356 (12)
C3—H3	0.9300	C34—H34	0.9300
C4—C5	1.346 (14)	C35—C36	1.436 (12)
C4—H4	0.9300	C35—H35	0.9300
C5—C6	1.388 (13)	C37—C38	1.471 (10)
C5—H5	0.9300	C38—C43	1.369 (8)
C6—C7	1.395 (12)	C38—C39	1.378 (9)
C6—H6	0.9300	C39—C40	1.364 (9)
C7—C8	1.496 (11)	C39—H39	0.9300
C9—C10	1.378 (11)	C40—C41	1.372 (10)
C9—C18	1.415 (12)	C40—H40	0.9300
C10—C11	1.415 (12)	C41—C42	1.401 (9)
C10—H10	0.9300	C41—H41	0.9300
C11—C12	1.354 (14)	C42—C43	1.381 (8)
C11—H11	0.9300	C42—H42	0.9300
C12—C13	1.391 (13)	C43—C44	1.488 (8)
C12—H12	0.9300	C45—C46	1.3900
C13—C18	1.404 (11)	C45—C50	1.3900
C13—C14	1.435 (14)	C46—C47	1.3900
C14—C15	1.382 (15)	C46—H46	0.9300
C14—H14	0.9300	C47—C48	1.3900
C15—C16	1.357 (13)	C47—H47	0.9300
C15—H15	0.9300	C48—C49	1.3900
C16—C17	1.365 (12)	C48—H48	0.9300
C16—H16	0.9300	C49—C50	1.3900
C17—C18	1.366 (12)	C49—C54	1.3900
C17—H17	0.9300	C50—C51	1.3900
C19—C20	1.480 (10)	C51—C52	1.3900
C20—C21	1.362 (11)	C51—H51	0.9300
C20—C25	1.371 (11)	C52—C53	1.3900
C21—C22	1.395 (11)	C52—H52	0.9300
C21—H21	0.9300	C53—C54	1.3900
C22—C23	1.399 (13)	C53—H53	0.9300
C22—H22	0.9300	C54—H54	0.9300
C23—C24	1.386 (13)
C1—N1—C8	110.9 (7)	N2—C26—C25	105.5 (7)
C1—N1—C9	124.2 (7)	C28—C27—C36	121.2 (8)
C8—N1—C9	124.2 (7)	C28—C27—N2	120.2 (8)
C26—N2—C19	111.1 (7)	C36—C27—N2	118.5 (7)
C26—N2—C27	125.0 (7)	C27—C28—C29	122.4 (9)
C19—N2—C27	123.3 (6)	C27—C28—H28	118.8
C37—N3—C44	111.7 (6)	C29—C28—H28	118.8
C37—N3—C45	124.5 (6)	C30—C29—C28	118.5 (9)
C44—N3—C45	123.4 (5)	C30—C29—H29	120.8
O1—C1—N1	124.7 (8)	C28—C29—H29	120.8
O1—C1—C2	127.7 (8)	C29—C30—C31	121.3 (8)
N1—C1—C2	107.5 (8)	C29—C30—H30	119.4
C3—C2—C7	121.4 (7)	C31—C30—H30	119.4
C3—C2—C1	131.6 (8)	C30—C31—C36	118.9 (8)
C7—C2—C1	106.9 (7)	C30—C31—C32	123.8 (8)
C2—C3—C4	118.1 (9)	C36—C31—C32	117.3 (9)
C2—C3—H3	120.9	C33—C32—C31	121.9 (9)
C4—C3—H3	120.9	C33—C32—H32	119.0
C5—C4—C3	120.9 (9)	C31—C32—H32	119.0
C5—C4—H4	119.6	C32—C33—C34	123.7 (10)
C3—C4—H4	119.6	C32—C33—H33	118.1
C4—C5—C6	122.3 (10)	C34—C33—H33	118.1
C4—C5—H5	118.8	C35—C34—C33	115.2 (10)
C6—C5—H5	118.8	C35—C34—H34	122.4
C5—C6—C7	116.8 (9)	C33—C34—H34	122.4
C5—C6—H6	121.6	C34—C35—C36	124.2 (8)
C7—C6—H6	121.6	C34—C35—H35	117.9
C2—C7—C6	120.3 (7)	C36—C35—H35	117.9
C2—C7—C8	109.9 (7)	C27—C36—C31	117.7 (8)
C6—C7—C8	129.6 (9)	C27—C36—C35	124.6 (7)
O2—C8—N1	124.7 (7)	C31—C36—C35	117.6 (8)
O2—C8—C7	130.6 (8)	O5—C37—N3	123.6 (7)
N1—C8—C7	104.7 (7)	O5—C37—C38	128.8 (7)
C10—C9—C18	124.0 (8)	N3—C37—C38	106.3 (6)
C10—C9—N1	117.2 (8)	C43—C38—C39	120.9 (6)
C18—C9—N1	118.8 (7)	C43—C38—C37	108.4 (5)
C9—C10—C11	117.6 (9)	C39—C38—C37	130.6 (6)
C9—C10—H10	121.2	C40—C39—C38	118.1 (6)
C11—C10—H10	121.2	C40—C39—H39	120.9
C12—C11—C10	121.0 (9)	C38—C39—H39	120.9
C12—C11—H11	119.5	C39—C40—C41	121.7 (6)
C10—C11—H11	119.5	C39—C40—H40	119.2
C11—C12—C13	119.9 (8)	C41—C40—H40	119.2
C11—C12—H12	120.0	C40—C41—C42	120.5 (6)
C13—C12—H12	120.0	C40—C41—H41	119.7
C12—C13—C18	122.7 (9)	C42—C41—H41	119.7
C12—C13—C14	120.7 (9)	C43—C42—C41	117.0 (6)
C18—C13—C14	116.5 (9)	C43—C42—H42	121.5
C15—C14—C13	121.2 (9)	C41—C42—H42	121.5
C15—C14—H14	119.4	C38—C43—C42	121.6 (6)
C13—C14—H14	119.4	C38—C43—C44	108.1 (5)
C16—C15—C14	117.3 (10)	C42—C43—C44	130.2 (6)
C16—C15—H15	121.4	O6—C44—N3	125.5 (6)
C14—C15—H15	121.4	O6—C44—C43	129.1 (6)
C15—C16—C17	125.0 (10)	N3—C44—C43	105.2 (5)
C15—C16—H16	117.5	C46—C45—C50	120.0
C17—C16—H16	117.5	C46—C45—N3	120.6 (4)
C16—C17—C18	117.8 (8)	C50—C45—N3	119.3 (4)
C16—C17—H17	121.1	C45—C46—C47	120.0
C18—C17—H17	121.1	C45—C46—H46	120.0
C17—C18—C13	122.1 (9)	C47—C46—H46	120.0
C17—C18—C9	123.2 (7)	C48—C47—C46	120.0
C13—C18—C9	114.7 (8)	C48—C47—H47	120.0
O3—C19—N2	124.0 (7)	C46—C47—H47	120.0
O3—C19—C20	130.3 (8)	C47—C48—C49	120.0
N2—C19—C20	105.7 (7)	C47—C48—H48	120.0
C21—C20—C25	121.8 (7)	C49—C48—H48	120.0
C21—C20—C19	130.2 (8)	C48—C49—C50	120.0
C25—C20—C19	108.0 (7)	C48—C49—C54	120.0
C20—C21—C22	117.9 (9)	C50—C49—C54	120.0
C20—C21—H21	121.1	C51—C50—C49	120.0
C22—C21—H21	121.1	C51—C50—C45	120.0
C21—C22—C23	121.0 (8)	C49—C50—C45	120.0
C21—C22—H22	119.5	C50—C51—C52	120.0
C23—C22—H22	119.5	C50—C51—H51	120.0
C24—C23—C22	120.7 (8)	C52—C51—H51	120.0
C24—C23—H23	119.6	C53—C52—C51	120.0
C22—C23—H23	119.6	C53—C52—H52	120.0
C23—C24—C25	117.0 (9)	C51—C52—H52	120.0
C23—C24—H24	121.5	C52—C53—C54	120.0
C25—C24—H24	121.5	C52—C53—H53	120.0
C20—C25—C24	121.6 (8)	C54—C53—H53	120.0
C20—C25—C26	109.5 (7)	C53—C54—C49	120.0
C24—C25—C26	128.8 (9)	C53—C54—H54	120.0
O4—C26—N2	124.2 (7)	C49—C54—H54	120.0
O4—C26—C25	130.3 (8)
C8—N1—C1—O1	175.8 (10)	C24—C25—C26—N2	179.7 (8)
C9—N1—C1—O1	5.5 (15)	C26—N2—C27—C28	−107.5 (10)
C8—N1—C1—C2	−3.5 (10)	C19—N2—C27—C28	62.9 (11)
C9—N1—C1—C2	−173.8 (8)	C26—N2—C27—C36	70.0 (10)
O1—C1—C2—C3	0.7 (17)	C19—N2—C27—C36	−119.6 (9)
N1—C1—C2—C3	180.0 (8)	C36—C27—C28—C29	1.7 (13)
O1—C1—C2—C7	−175.8 (10)	N2—C27—C28—C29	179.2 (7)
N1—C1—C2—C7	3.5 (9)	C27—C28—C29—C30	−1.9 (13)
C7—C2—C3—C4	1.3 (13)	C28—C29—C30—C31	0.5 (14)
C1—C2—C3—C4	−174.8 (9)	C29—C30—C31—C36	0.9 (13)
C2—C3—C4—C5	1.1 (14)	C29—C30—C31—C32	179.1 (9)
C3—C4—C5—C6	−1.5 (16)	C30—C31—C32—C33	−178.5 (9)
C4—C5—C6—C7	−0.6 (15)	C36—C31—C32—C33	−0.3 (13)
C3—C2—C7—C6	−3.4 (13)	C31—C32—C33—C34	2.8 (17)
C1—C2—C7—C6	173.5 (8)	C32—C33—C34—C35	−3.1 (15)
C3—C2—C7—C8	−179.1 (7)	C33—C34—C35—C36	1.1 (14)
C1—C2—C7—C8	−2.2 (9)	C28—C27—C36—C31	−0.2 (11)
C5—C6—C7—C2	2.9 (13)	N2—C27—C36—C31	−177.7 (7)
C5—C6—C7—C8	177.7 (9)	C28—C27—C36—C35	−177.9 (8)
C1—N1—C8—O2	−178.8 (9)	N2—C27—C36—C35	4.6 (11)
C9—N1—C8—O2	−8.6 (14)	C30—C31—C36—C27	−1.1 (11)
C1—N1—C8—C7	2.2 (9)	C32—C31—C36—C27	−179.4 (7)
C9—N1—C8—C7	172.4 (7)	C30—C31—C36—C35	176.7 (7)
C2—C7—C8—O2	−178.8 (9)	C32—C31—C36—C35	−1.5 (10)
C6—C7—C8—O2	6.0 (16)	C34—C35—C36—C27	178.7 (9)
C2—C7—C8—N1	0.1 (9)	C34—C35—C36—C31	1.0 (12)
C6—C7—C8—N1	−175.1 (9)	C44—N3—C37—O5	172.6 (12)
C1—N1—C9—C10	108.2 (10)	C45—N3—C37—O5	0 (2)
C8—N1—C9—C10	−60.8 (11)	C44—N3—C37—C38	4.8 (15)
C1—N1—C9—C18	−71.8 (11)	C45—N3—C37—C38	−167.9 (9)
C8—N1—C9—C18	119.2 (9)	O5—C37—C38—C43	−169.6 (14)
C18—C9—C10—C11	0.5 (14)	N3—C37—C38—C43	−2.7 (15)
N1—C9—C10—C11	−179.5 (8)	O5—C37—C38—C39	10 (2)
C9—C10—C11—C12	0.3 (14)	N3—C37—C38—C39	176.7 (12)
C10—C11—C12—C13	−0.2 (14)	C43—C38—C39—C40	2.9 (18)
C11—C12—C13—C18	−0.6 (14)	C37—C38—C39—C40	−176.4 (13)
C11—C12—C13—C14	177.8 (9)	C38—C39—C40—C41	0 (2)
C12—C13—C14—C15	177.0 (9)	C39—C40—C41—C42	−3.6 (19)
C18—C13—C14—C15	−4.5 (13)	C40—C41—C42—C43	3.7 (17)
C13—C14—C15—C16	3.5 (14)	C39—C38—C43—C42	−2.7 (18)
C14—C15—C16—C17	−2.1 (15)	C37—C38—C43—C42	176.7 (11)
C15—C16—C17—C18	1.7 (14)	C39—C38—C43—C44	−179.7 (12)
C16—C17—C18—C13	−2.8 (13)	C37—C38—C43—C44	−0.3 (13)
C16—C17—C18—C9	178.7 (9)	C41—C42—C43—C38	−0.7 (17)
C12—C13—C18—C17	−177.4 (8)	C41—C42—C43—C44	175.6 (11)
C14—C13—C18—C17	4.1 (12)	C37—N3—C44—O6	−179.8 (14)
C12—C13—C18—C9	1.3 (12)	C45—N3—C44—O6	−7.0 (18)
C14—C13—C18—C9	−177.2 (8)	C37—N3—C44—C43	−4.9 (14)
C10—C9—C18—C17	177.4 (9)	C45—N3—C44—C43	167.9 (8)
N1—C9—C18—C17	−2.6 (12)	C38—C43—C44—O6	177.7 (14)
C10—C9—C18—C13	−1.2 (13)	C42—C43—C44—O6	1 (2)
N1—C9—C18—C13	178.7 (7)	C38—C43—C44—N3	3.1 (12)
C26—N2—C19—O3	−179.1 (9)	C42—C43—C44—N3	−173.6 (11)
C27—N2—C19—O3	9.4 (14)	C37—N3—C45—C46	79.1 (11)
C26—N2—C19—C20	0.3 (9)	C44—N3—C45—C46	−92.7 (9)
C27—N2—C19—C20	−171.3 (7)	C37—N3—C45—C50	−103.0 (11)
O3—C19—C20—C21	−1.9 (17)	C44—N3—C45—C50	85.1 (10)
N2—C19—C20—C21	178.8 (9)	C50—C45—C46—C47	0.0
O3—C19—C20—C25	176.5 (10)	N3—C45—C46—C47	177.8 (4)
N2—C19—C20—C25	−2.8 (9)	C45—C46—C47—C48	0.0
C25—C20—C21—C22	1.7 (14)	C46—C47—C48—C49	0.0
C19—C20—C21—C22	179.9 (9)	C47—C48—C49—C50	0.0
C20—C21—C22—C23	−1.6 (15)	C47—C48—C49—C54	180.0
C21—C22—C23—C24	0.4 (16)	C48—C49—C50—C51	180.0
C22—C23—C24—C25	0.6 (14)	C54—C49—C50—C51	0.0
C21—C20—C25—C24	−0.6 (13)	C48—C49—C50—C45	0.0
C19—C20—C25—C24	−179.2 (8)	C54—C49—C50—C45	180.0
C21—C20—C25—C26	−177.2 (8)	C46—C45—C50—C51	180.0
C19—C20—C25—C26	4.2 (9)	N3—C45—C50—C51	2.2 (4)
C23—C24—C25—C20	−0.6 (13)	C46—C45—C50—C49	0.0
C23—C24—C25—C26	175.3 (9)	N3—C45—C50—C49	−177.8 (4)
C19—N2—C26—O4	−177.3 (8)	C49—C50—C51—C52	0.0
C27—N2—C26—O4	−5.9 (13)	C45—C50—C51—C52	180.0
C19—N2—C26—C25	2.2 (9)	C50—C51—C52—C53	0.0
C27—N2—C26—C25	173.6 (7)	C51—C52—C53—C54	0.0
C20—C25—C26—O4	175.4 (9)	C52—C53—C54—C49	0.0
C24—C25—C26—O4	−0.9 (16)	C48—C49—C54—C53	180.0
C20—C25—C26—N2	−4.0 (9)	C50—C49—C54—C53	0.0