Diisopropyl 2-[(4-nitro­benzo­yl)amino]­propane­dioate

The title compound, C₁₆H₂₀N₂O₇, crystallizes in the space group C2 with two mol­ecules in the asymmetric unit. The crystal packing shows O...π inter­actions between the two mol­ecules.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.013 Å
• R factor = 0.081
• wR factor = 0.276
• Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C14      --C15      .        7.1 s.u.
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O12      --C26      .        8.2 s.u.
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C26      --C27      .       11.0 s.u.
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C26      --C28      .        9.3 s.u.
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C30      --C31      .       12.7 s.u.
PLAT242_ALERT_2_B Low    'MainMol' Ueq as Compared to Neighbors of        C30 Check
PLAT340_ALERT_3_B Low Bond Precision on  C-C Bonds ...............    0.01262 Ang.

Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.600
           From the CIF: _refine_ls_abs_structure_Flack_su    1.000
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections (too) Low ..        46% Check
PLAT084_ALERT_3_C High wR2 Value (i.e. > 0.25) ...................       0.28 Report
PLAT220_ALERT_2_C NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range        3.4 Ratio
PLAT220_ALERT_2_C NonSolvent   Resd 2  C   Ueq(max)/Ueq(min) Range        3.6 Ratio
PLAT234_ALERT_4_C Large Hirshfeld Difference C14      --C16      .       0.17 Ang.
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         N1 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C10 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C13 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C14 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C25 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C26 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C29 Check
PLAT334_ALERT_2_C Small <C-C> Benzene Dist.   C1       -C6       .       1.37 Ang.
PLAT334_ALERT_2_C Small <C-C> Benzene Dist.   C17      -C22      .       1.37 Ang.
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C26      - C27      .       1.43 Ang.
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C30      - C32      .       1.43 Ang.
PLAT907_ALERT_2_C Flack x > 0.5, Structure Needs to be Inverted? .       0.60 Check

Alert level G
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          6 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      1.000 Report
PLAT128_ALERT_4_G Alternate Setting for Input Space Group  C2              I2 Note
PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records          1 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records          1 Report
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          2 Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         52 Note
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         32 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        3.9 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info
PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by          2 Check

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  22 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
   9 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2014/4 (Sheldrick, 2015a); program(s) used to refine structure: 4SHELXL2018/43 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Diisopropyl 2-[(4-nitrobenzoyl)amino]propanedioate

Crystal data

C16H20N2O7	F(000) = 1488
Mr = 352.34	Dx = 1.325 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 38.408 (10) Å	Cell parameters from 2123 reflections
b = 5.1523 (13) Å	θ = 2.3–19.0°
c = 19.752 (5) Å	µ = 0.11 mm^−1
β = 115.341 (4)°	T = 296 K
V = 3532.7 (15) Å^3	Needle, colourless
Z = 8	0.50 × 0.08 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer	3977 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.062
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θmax = 28.4°, θmin = 2.0°
Tmin = 0.534, Tmax = 0.745	h = −50→50
18724 measured reflections	k = −6→6
8693 independent reflections	l = −26→26

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.081	w = 1/[σ^2(Fo^2) + (0.1417P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.276	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.49 e Å^−3
8693 reflections	Δρmin = −0.34 e Å^−3
459 parameters	Absolute structure: Flack x determined using 1214 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
52 restraints	Absolute structure parameter: 0.6 (10)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
O1	0.88102 (19)	0.2244 (16)	0.6329 (5)	0.118 (2)
O2	0.90133 (17)	0.5358 (18)	0.7072 (4)	0.128 (3)
O3	0.71544 (12)	0.9400 (9)	0.6084 (3)	0.0712 (13)
O4	0.67465 (15)	0.5799 (14)	0.6930 (3)	0.0944 (19)
O5	0.61676 (14)	0.7265 (11)	0.6190 (3)	0.0753 (14)
O6	0.63941 (14)	0.2095 (10)	0.4886 (3)	0.0837 (16)
O7	0.59253 (12)	0.4686 (11)	0.4841 (3)	0.0795 (15)
N1	0.87565 (19)	0.4161 (17)	0.6630 (4)	0.0811 (18)
N2	0.69438 (14)	0.5333 (10)	0.5764 (3)	0.0555 (13)
H2N2	0.700003	0.375915	0.570495	0.067*
C1	0.83549 (19)	0.4910 (16)	0.6442 (4)	0.0641 (18)
C2	0.8060 (2)	0.3469 (16)	0.5940 (4)	0.0681 (18)
H2	0.810805	0.206553	0.569638	0.082*
C3	0.76912 (18)	0.4137 (14)	0.5804 (3)	0.0577 (16)
H3	0.748686	0.313843	0.547615	0.069*
C4	0.76178 (16)	0.6251 (12)	0.6142 (3)	0.0500 (14)
C5	0.79215 (18)	0.7752 (13)	0.6635 (4)	0.0599 (16)
H5	0.787483	0.920965	0.686133	0.072*
C6	0.82960 (18)	0.7034 (15)	0.6783 (4)	0.0682 (19)
H6	0.850388	0.800012	0.711361	0.082*
C7	0.72186 (18)	0.7100 (13)	0.6000 (3)	0.0551 (15)
C8	0.65570 (17)	0.5975 (12)	0.5606 (4)	0.0555 (15)
H8	0.649966	0.764484	0.534248	0.067*
C9	0.65032 (19)	0.6329 (14)	0.6321 (4)	0.0604 (16)
C10	0.6067 (3)	0.7816 (19)	0.6811 (4)	0.086 (3)
H10	0.622571	0.675836	0.724629	0.103*
C11	0.6145 (3)	1.065 (2)	0.6998 (6)	0.122 (4)
H11A	0.641204	1.100776	0.713532	0.182*
H11B	0.608425	1.107266	0.740821	0.182*
H11C	0.598852	1.167367	0.656892	0.182*
C12	0.5657 (3)	0.712 (2)	0.6551 (7)	0.120 (4)
H12A	0.550242	0.819530	0.613445	0.181*
H12B	0.558195	0.736768	0.695147	0.181*
H12C	0.562101	0.532895	0.639884	0.181*
C13	0.62848 (17)	0.3987 (13)	0.5080 (3)	0.0539 (15)
C14	0.5632 (2)	0.3031 (18)	0.4300 (5)	0.089 (3)
H14	0.574593	0.184705	0.406273	0.107*
C15	0.5350 (4)	0.490 (3)	0.3721 (8)	0.156 (5)
H15A	0.518994	0.570858	0.392476	0.235*
H15B	0.519074	0.395818	0.327625	0.235*
H15C	0.549129	0.621206	0.359918	0.235*
C16	0.5450 (4)	0.157 (4)	0.4700 (9)	0.172 (6)
H16A	0.564320	0.061675	0.510334	0.258*
H16B	0.526439	0.038554	0.436017	0.258*
H16C	0.532346	0.275346	0.489680	0.258*
O8	0.80326 (17)	0.2861 (12)	0.7820 (3)	0.0891 (17)
O9	0.81622 (17)	0.6196 (13)	0.8529 (4)	0.0951 (18)
O10	0.66470 (15)	−0.0673 (10)	0.8979 (3)	0.0747 (13)
O11	0.65449 (17)	0.6482 (13)	1.0333 (3)	0.0934 (18)
O12	0.60149 (14)	0.4539 (13)	1.0243 (3)	0.0924 (18)
O13	0.58449 (16)	0.4185 (15)	0.8261 (3)	0.103 (2)
O14	0.56464 (13)	0.1570 (11)	0.8898 (3)	0.0754 (14)
N3	0.79752 (15)	0.4276 (13)	0.8251 (3)	0.0664 (15)
N4	0.65984 (14)	0.3465 (11)	0.9276 (3)	0.0595 (14)
H4N4	0.668115	0.503086	0.930582	0.071*
C17	0.76625 (18)	0.3554 (13)	0.8470 (4)	0.0572 (16)
C18	0.7437 (2)	0.1486 (14)	0.8140 (4)	0.0645 (17)
H18	0.747804	0.051632	0.778358	0.077*
C19	0.71472 (18)	0.0839 (13)	0.8336 (4)	0.0585 (16)
H19	0.699443	−0.060793	0.812472	0.070*
C20	0.70813 (17)	0.2356 (12)	0.8855 (3)	0.0507 (14)
C21	0.73146 (18)	0.4425 (14)	0.9176 (4)	0.0594 (16)
H21	0.727253	0.542696	0.952543	0.071*
C22	0.76095 (19)	0.5053 (15)	0.8993 (4)	0.0639 (17)
H22	0.776969	0.645826	0.921640	0.077*
C23	0.67578 (17)	0.1561 (13)	0.9041 (3)	0.0532 (15)
C24	0.62899 (17)	0.2893 (13)	0.9479 (4)	0.0575 (16)
H24	0.632877	0.115292	0.969983	0.069*
C25	0.63007 (19)	0.4888 (14)	1.0067 (4)	0.0604 (16)
C26	0.5982 (3)	0.642 (2)	1.0786 (5)	0.101 (3)
H26	0.618275	0.775429	1.092635	0.121*
C27	0.6031 (4)	0.483 (4)	1.1412 (8)	0.166 (5)
H27A	0.583457	0.351385	1.125663	0.249*
H27B	0.601108	0.587697	1.179561	0.249*
H27C	0.627983	0.401613	1.160547	0.249*
C28	0.5600 (4)	0.757 (3)	1.0432 (9)	0.163 (5)
H28A	0.541281	0.622836	1.019716	0.245*
H28B	0.559144	0.880016	1.006063	0.245*
H28C	0.554309	0.842906	1.080354	0.245*
C29	0.5902 (2)	0.2985 (14)	0.8801 (4)	0.0601 (16)
C30	0.5250 (2)	0.1611 (18)	0.8325 (4)	0.080 (2)
H30	0.522370	0.300077	0.796814	0.096*
C31	0.5161 (5)	−0.083 (4)	0.7929 (10)	0.184 (6)
H31A	0.515314	−0.218117	0.825734	0.277*
H31B	0.535656	−0.122663	0.776323	0.277*
H31C	0.491564	−0.071294	0.750378	0.277*
C32	0.5000 (3)	0.216 (5)	0.8673 (8)	0.185 (8)
H32A	0.473706	0.210829	0.830379	0.277*
H32B	0.505665	0.386042	0.889470	0.277*
H32C	0.503806	0.089532	0.905427	0.277*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.083 (4)	0.128 (6)	0.150 (6)	0.017 (4)	0.058 (4)	−0.019 (5)
O2	0.050 (3)	0.177 (8)	0.134 (6)	0.000 (4)	0.019 (4)	−0.021 (6)
O3	0.059 (3)	0.056 (3)	0.094 (3)	0.000 (2)	0.029 (2)	−0.010 (3)
O4	0.073 (3)	0.142 (6)	0.064 (3)	0.034 (4)	0.025 (3)	0.015 (3)
O5	0.063 (3)	0.101 (4)	0.063 (3)	0.023 (3)	0.028 (2)	0.000 (3)
O6	0.063 (3)	0.064 (3)	0.103 (4)	0.005 (2)	0.015 (3)	−0.014 (3)
O7	0.041 (2)	0.100 (4)	0.090 (3)	−0.005 (3)	0.021 (2)	−0.031 (3)
N1	0.058 (4)	0.105 (6)	0.087 (4)	0.008 (4)	0.038 (4)	0.009 (4)
N2	0.045 (3)	0.047 (3)	0.074 (3)	−0.002 (2)	0.024 (3)	−0.001 (2)
C1	0.054 (4)	0.084 (5)	0.065 (4)	0.007 (4)	0.036 (3)	0.011 (4)
C2	0.064 (4)	0.075 (4)	0.072 (4)	−0.001 (4)	0.036 (4)	−0.008 (4)
C3	0.051 (3)	0.067 (4)	0.054 (3)	−0.007 (3)	0.021 (3)	−0.009 (3)
C4	0.050 (3)	0.053 (3)	0.047 (3)	−0.001 (3)	0.021 (3)	0.006 (3)
C5	0.056 (4)	0.056 (4)	0.065 (4)	−0.005 (3)	0.023 (3)	−0.012 (3)
C6	0.044 (4)	0.080 (5)	0.073 (4)	−0.014 (3)	0.018 (3)	−0.011 (4)
C7	0.055 (4)	0.057 (4)	0.049 (3)	−0.003 (3)	0.019 (3)	0.000 (3)
C8	0.053 (4)	0.051 (4)	0.063 (4)	0.004 (3)	0.025 (3)	0.002 (3)
C9	0.054 (4)	0.066 (4)	0.057 (4)	0.004 (3)	0.020 (3)	0.000 (3)
C10	0.083 (6)	0.116 (7)	0.067 (5)	0.034 (5)	0.039 (4)	−0.001 (5)
C11	0.136 (9)	0.121 (9)	0.097 (7)	0.020 (7)	0.039 (7)	−0.030 (7)
C12	0.096 (7)	0.151 (10)	0.145 (9)	0.020 (7)	0.081 (7)	0.011 (8)
C13	0.050 (4)	0.053 (4)	0.053 (3)	0.002 (3)	0.017 (3)	−0.002 (3)
C14	0.047 (4)	0.104 (6)	0.107 (6)	0.010 (4)	0.023 (4)	−0.036 (5)
C15	0.154 (5)	0.156 (5)	0.153 (5)	−0.004 (3)	0.060 (3)	0.004 (3)
C16	0.171 (6)	0.172 (6)	0.171 (6)	−0.009 (3)	0.071 (3)	0.002 (3)
O8	0.101 (4)	0.101 (4)	0.094 (4)	−0.011 (3)	0.070 (3)	−0.013 (3)
O9	0.094 (4)	0.094 (4)	0.120 (5)	−0.019 (4)	0.068 (4)	−0.005 (4)
O10	0.088 (3)	0.056 (3)	0.095 (3)	−0.010 (3)	0.054 (3)	−0.003 (3)
O11	0.102 (4)	0.113 (4)	0.090 (4)	−0.045 (4)	0.064 (3)	−0.032 (3)
O12	0.076 (3)	0.124 (5)	0.098 (4)	−0.021 (3)	0.057 (3)	−0.046 (4)
O13	0.082 (4)	0.141 (6)	0.083 (4)	−0.008 (4)	0.034 (3)	0.038 (4)
O14	0.060 (3)	0.092 (4)	0.072 (3)	−0.013 (3)	0.026 (3)	0.006 (3)
N3	0.057 (3)	0.071 (4)	0.077 (4)	−0.004 (3)	0.034 (3)	0.007 (3)
N4	0.055 (3)	0.052 (3)	0.081 (4)	0.000 (2)	0.038 (3)	0.003 (3)
C17	0.051 (3)	0.064 (4)	0.059 (4)	0.003 (3)	0.026 (3)	0.012 (3)
C18	0.072 (4)	0.064 (4)	0.065 (4)	−0.001 (4)	0.036 (3)	−0.009 (3)
C19	0.058 (4)	0.056 (4)	0.066 (4)	0.000 (3)	0.031 (3)	−0.010 (3)
C20	0.046 (3)	0.050 (3)	0.057 (3)	0.005 (3)	0.023 (3)	0.006 (3)
C21	0.058 (4)	0.064 (4)	0.062 (4)	−0.004 (3)	0.031 (3)	−0.008 (3)
C22	0.059 (4)	0.069 (4)	0.064 (4)	−0.008 (3)	0.026 (3)	−0.008 (3)
C23	0.055 (4)	0.052 (4)	0.057 (4)	0.000 (3)	0.029 (3)	0.002 (3)
C24	0.055 (4)	0.062 (4)	0.071 (4)	0.004 (3)	0.041 (3)	0.006 (3)
C25	0.057 (4)	0.068 (4)	0.061 (4)	−0.008 (4)	0.029 (3)	0.002 (3)
C26	0.101 (3)	0.104 (3)	0.101 (3)	−0.0013 (14)	0.0461 (17)	−0.0033 (14)
C27	0.169 (5)	0.166 (5)	0.162 (5)	0.011 (3)	0.070 (3)	−0.003 (3)
C28	0.164 (5)	0.164 (5)	0.162 (5)	0.009 (3)	0.071 (3)	−0.002 (3)
C29	0.067 (4)	0.067 (4)	0.058 (4)	0.006 (3)	0.038 (3)	0.007 (3)
C30	0.066 (5)	0.088 (5)	0.074 (5)	−0.007 (4)	0.020 (4)	−0.009 (4)
C31	0.182 (6)	0.182 (7)	0.185 (7)	0.003 (3)	0.075 (4)	−0.005 (3)
C32	0.087 (7)	0.32 (2)	0.153 (11)	0.015 (11)	0.056 (8)	−0.026 (15)

Geometric parameters (Å, º)

O1—N1	1.216 (10)	O8—N3	1.210 (7)
O2—N1	1.174 (9)	O9—N3	1.207 (8)
O3—C7	1.236 (8)	O10—C23	1.215 (8)
O4—C9	1.197 (7)	O11—C25	1.186 (8)
O5—C9	1.294 (8)	O12—C25	1.297 (8)
O5—C10	1.463 (9)	O12—C26	1.491 (11)
O6—C13	1.188 (8)	O13—C29	1.170 (8)
O7—C13	1.304 (8)	O14—C29	1.299 (8)
O7—C14	1.452 (9)	O14—C30	1.459 (9)
N1—C1	1.475 (9)	N3—C17	1.488 (8)
N2—C7	1.318 (8)	N4—C23	1.340 (8)
N2—C8	1.420 (7)	N4—C24	1.434 (7)
N2—H2N2	0.8600	N4—H4N4	0.8600
C1—C6	1.354 (10)	C17—C18	1.353 (10)
C1—C2	1.363 (10)	C17—C22	1.373 (9)
C2—C3	1.368 (9)	C18—C19	1.367 (9)
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.368 (9)	C19—C20	1.395 (8)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.391 (8)	C20—C21	1.362 (9)
C4—C7	1.501 (9)	C20—C23	1.496 (8)
C5—C6	1.389 (9)	C21—C22	1.367 (9)
C5—H5	0.9300	C21—H21	0.9300
C6—H6	0.9300	C22—H22	0.9300
C8—C13	1.514 (9)	C24—C29	1.520 (9)
C8—C9	1.525 (9)	C24—C25	1.538 (10)
C8—H8	0.9800	C24—H24	0.9800
C10—C12	1.475 (13)	C26—C27	1.430 (17)
C10—C11	1.504 (15)	C26—C28	1.454 (16)
C10—H10	0.9800	C26—H26	0.9800
C11—H11A	0.9600	C27—H27A	0.9600
C11—H11B	0.9600	C27—H27B	0.9600
C11—H11C	0.9600	C27—H27C	0.9600
C12—H12A	0.9600	C28—H28A	0.9600
C12—H12B	0.9600	C28—H28B	0.9600
C12—H12C	0.9600	C28—H28C	0.9600
C14—C16	1.465 (16)	C30—C32	1.427 (13)
C14—C15	1.534 (17)	C30—C31	1.44 (2)
C14—H14	0.9800	C30—H30	0.9800
C15—H15A	0.9600	C31—H31A	0.9600
C15—H15B	0.9600	C31—H31B	0.9600
C15—H15C	0.9600	C31—H31C	0.9600
C16—H16A	0.9600	C32—H32A	0.9600
C16—H16B	0.9600	C32—H32B	0.9600
C16—H16C	0.9600	C32—H32C	0.9600
C9—O5—C10	120.1 (5)	C25—O12—C26	116.4 (7)
C13—O7—C14	118.2 (6)	C29—O14—C30	118.8 (6)
O2—N1—O1	121.8 (8)	O9—N3—O8	124.2 (6)
O2—N1—C1	120.3 (8)	O9—N3—C17	118.0 (6)
O1—N1—C1	117.9 (8)	O8—N3—C17	117.8 (6)
C7—N2—C8	121.4 (5)	C23—N4—C24	120.1 (6)
C7—N2—H2N2	119.3	C23—N4—H4N4	120.0
C8—N2—H2N2	119.3	C24—N4—H4N4	120.0
C6—C1—C2	122.6 (6)	C18—C17—C22	122.4 (6)
C6—C1—N1	117.7 (7)	C18—C17—N3	119.1 (6)
C2—C1—N1	119.6 (7)	C22—C17—N3	118.5 (6)
C1—C2—C3	118.3 (7)	C17—C18—C19	119.1 (6)
C1—C2—H2	120.8	C17—C18—H18	120.5
C3—C2—H2	120.8	C19—C18—H18	120.5
C2—C3—C4	121.1 (6)	C18—C19—C20	119.8 (6)
C2—C3—H3	119.4	C18—C19—H19	120.1
C4—C3—H3	119.4	C20—C19—H19	120.1
C3—C4—C5	119.9 (6)	C21—C20—C19	119.3 (6)
C3—C4—C7	123.2 (6)	C21—C20—C23	123.4 (5)
C5—C4—C7	116.9 (6)	C19—C20—C23	117.3 (6)
C6—C5—C4	118.8 (6)	C20—C21—C22	121.1 (6)
C6—C5—H5	120.6	C20—C21—H21	119.4
C4—C5—H5	120.6	C22—C21—H21	119.4
C1—C6—C5	119.2 (6)	C21—C22—C17	118.2 (6)
C1—C6—H6	120.4	C21—C22—H22	120.9
C5—C6—H6	120.4	C17—C22—H22	120.9
O3—C7—N2	122.3 (6)	O10—C23—N4	122.4 (6)
O3—C7—C4	120.0 (6)	O10—C23—C20	121.8 (6)
N2—C7—C4	117.7 (6)	N4—C23—C20	115.8 (6)
N2—C8—C13	110.1 (5)	N4—C24—C29	111.4 (5)
N2—C8—C9	111.6 (5)	N4—C24—C25	108.4 (5)
C13—C8—C9	112.9 (5)	C29—C24—C25	110.1 (5)
N2—C8—H8	107.3	N4—C24—H24	109.0
C13—C8—H8	107.3	C29—C24—H24	109.0
C9—C8—H8	107.3	C25—C24—H24	109.0
O4—C9—O5	124.7 (6)	O11—C25—O12	125.2 (7)
O4—C9—C8	123.2 (6)	O11—C25—C24	123.9 (6)
O5—C9—C8	112.1 (5)	O12—C25—C24	110.9 (6)
O5—C10—C12	106.7 (7)	C27—C26—C28	112.4 (11)
O5—C10—C11	107.3 (8)	C27—C26—O12	103.2 (10)
C12—C10—C11	113.2 (9)	C28—C26—O12	107.3 (9)
O5—C10—H10	109.9	C27—C26—H26	111.2
C12—C10—H10	109.9	C28—C26—H26	111.2
C11—C10—H10	109.9	O12—C26—H26	111.2
C10—C11—H11A	109.5	C26—C27—H27A	109.5
C10—C11—H11B	109.5	C26—C27—H27B	109.5
H11A—C11—H11B	109.5	H27A—C27—H27B	109.5
C10—C11—H11C	109.5	C26—C27—H27C	109.5
H11A—C11—H11C	109.5	H27A—C27—H27C	109.5
H11B—C11—H11C	109.5	H27B—C27—H27C	109.5
C10—C12—H12A	109.5	C26—C28—H28A	109.5
C10—C12—H12B	109.5	C26—C28—H28B	109.5
H12A—C12—H12B	109.5	H28A—C28—H28B	109.5
C10—C12—H12C	109.5	C26—C28—H28C	109.5
H12A—C12—H12C	109.5	H28A—C28—H28C	109.5
H12B—C12—H12C	109.5	H28B—C28—H28C	109.5
O6—C13—O7	125.1 (6)	O13—C29—O14	124.9 (7)
O6—C13—C8	122.7 (6)	O13—C29—C24	123.3 (7)
O7—C13—C8	112.0 (6)	O14—C29—C24	111.8 (5)
O7—C14—C16	107.7 (9)	C32—C30—C31	112.6 (13)
O7—C14—C15	104.9 (9)	C32—C30—O14	108.9 (8)
C16—C14—C15	112.2 (9)	C31—C30—O14	109.4 (9)
O7—C14—H14	110.6	C32—C30—H30	108.6
C16—C14—H14	110.6	C31—C30—H30	108.6
C15—C14—H14	110.6	O14—C30—H30	108.6
C14—C15—H15A	109.5	C30—C31—H31A	109.5
C14—C15—H15B	109.5	C30—C31—H31B	109.5
H15A—C15—H15B	109.5	H31A—C31—H31B	109.5
C14—C15—H15C	109.5	C30—C31—H31C	109.5
H15A—C15—H15C	109.5	H31A—C31—H31C	109.5
H15B—C15—H15C	109.5	H31B—C31—H31C	109.5
C14—C16—H16A	109.5	C30—C32—H32A	109.5
C14—C16—H16B	109.5	C30—C32—H32B	109.5
H16A—C16—H16B	109.5	H32A—C32—H32B	109.5
C14—C16—H16C	109.5	C30—C32—H32C	109.5
H16A—C16—H16C	109.5	H32A—C32—H32C	109.5
H16B—C16—H16C	109.5	H32B—C32—H32C	109.5