Ethyl 3-[4-(ethoxy­carbon­yl)phen­yl]-3,4-dihydro­quinazoline-6-carboxyl­ate

The crystal structure of the title compound, C₂₀H₂₀N₂O₄, contains two mol­ecules in the asymmetric unit. The crystal packing involves π–π, C—H...O and C—H...N interactions.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.045
• wR factor = 0.095
• Data-to-parameter ratio = 9.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.04 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.74 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.82 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.21 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT432_ALERT_2_C Short Inter X...Y Contact  O6     ..  C11     ..       2.99 Ang.

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           28.67
           From the CIF: _reflns_number_total               4288
           Count of symmetry unique reflns         4311
           Completeness (_total/calc)             99.47%
           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
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 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

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Computing details

Data collection: SMART and GEMINI (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT and XPREP (Siemens, 1995); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997), WinGX32 (Farrugia, 1999), POV-RAY (Cason, 2002) and WebLab ViewerPro (Molecular Simulations, 2000); software used to prepare material for publication: enCIFer (Version 1.0; Allen et al., 2004).

Ethyl 3-[4-(ethoxycarbonyl)phenyl]-3,4-dihydroquinazoline-6-carboxylate

Crystal data

C20H20N2O4	F(000) = 744
Mr = 352.38	Dx = 1.401 Mg m^−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 894 reflections
a = 19.875 (9) Å	θ = 2.9–26.1°
b = 7.393 (3) Å	µ = 0.10 mm^−1
c = 11.529 (5) Å	T = 150 K
β = 99.622 (9)°	Plate, colourless
V = 1670.2 (13) Å^3	0.50 × 0.17 × 0.11 mm
Z = 4

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	4288 independent reflections
Radiation source: sealed tube	3021 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
ω scans	θmax = 28.7°, θmin = 2.1°
Absorption correction: multi-scan (TWINABS; Siemens, 1995)	h = 0→26
Tmin = 0.863, Tmax = 0.990	k = −9→0
7366 measured reflections	l = −15→15

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.095	H-atom parameters constrained
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0478P)^2] where P = (Fo^2 + 2Fc^2)/3
4288 reflections	(Δ/σ)max < 0.001
474 parameters	Δρmax = 0.24 e Å^−3
2 restraints	Δρmin = −0.24 e Å^−3

Special details

Experimental. The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. 39 standard reflections were obtained by recollecting the first 50 CCD frames at the end of data collection. They were then used for a decay correction, giving an overall decay of 0.08%.

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
C1	0.8116 (3)	0.3052 (8)	0.8267 (5)	0.0385 (15)
H1A	0.8145	0.1854	0.7915	0.058*
H1B	0.8557	0.3359	0.8744	0.058*
H1C	0.8000	0.3954	0.7643	0.058*
C2	0.7576 (3)	0.3035 (8)	0.9033 (5)	0.0268 (14)
H2A	0.7705	0.2199	0.9704	0.032*
H2B	0.7515	0.4261	0.9344	0.032*
C3	0.6412 (3)	0.2359 (7)	0.8846 (5)	0.0226 (14)
C4	0.5779 (3)	0.1769 (7)	0.8054 (4)	0.0195 (13)
C5	0.5161 (3)	0.2081 (7)	0.8400 (4)	0.0185 (12)
H5	0.5145	0.2661	0.9131	0.022*
C6	0.4557 (3)	0.1555 (6)	0.7692 (5)	0.0187 (12)
C7	0.4582 (3)	0.0720 (7)	0.6617 (4)	0.0207 (13)
C8	0.5205 (3)	0.0397 (7)	0.6281 (4)	0.0232 (14)
H8	0.5220	−0.0191	0.5553	0.028*
C9	0.5812 (3)	0.0912 (7)	0.6982 (4)	0.0232 (14)
H9	0.6239	0.0688	0.6741	0.028*
C10	0.3899 (3)	0.1877 (7)	0.8112 (4)	0.0209 (13)
H10A	0.3866	0.1066	0.8784	0.025*
H10B	0.3882	0.3141	0.8387	0.025*
C11	0.3420 (3)	0.0668 (7)	0.6165 (4)	0.0220 (13)
H11	0.3021	0.0346	0.5629	0.026*
C12	0.2664 (3)	0.2071 (6)	0.7335 (4)	0.0197 (13)
C13	0.2540 (3)	0.2440 (7)	0.8448 (5)	0.0227 (14)
H13	0.2898	0.2309	0.9100	0.027*
C14	0.1904 (3)	0.2999 (7)	0.8636 (4)	0.0218 (13)
H14	0.1826	0.3245	0.9411	0.026*
C15	0.1379 (3)	0.3199 (7)	0.7685 (5)	0.0226 (12)
C16	0.1507 (3)	0.2877 (7)	0.6589 (5)	0.0305 (14)
H16	0.1150	0.3031	0.5938	0.037*
C17	0.2142 (3)	0.2330 (7)	0.6384 (5)	0.0269 (14)
H17	0.2221	0.2134	0.5604	0.032*
C18	0.0700 (3)	0.3787 (7)	0.7931 (5)	0.0294 (13)
C19	−0.0460 (3)	0.4234 (8)	0.7090 (5)	0.0408 (15)
H19A	−0.0459	0.4980	0.7804	0.049*
H19B	−0.0730	0.3126	0.7163	0.049*
C20	−0.0767 (3)	0.5275 (9)	0.6016 (6)	0.0561 (19)
H20A	−0.0532	0.6439	0.6004	0.084*
H20B	−0.1252	0.5487	0.6030	0.084*
H20C	−0.0717	0.4582	0.5311	0.084*
C21	0.1043 (3)	0.8063 (8)	0.6393 (5)	0.0387 (16)
H21A	0.1191	0.8862	0.5806	0.058*
H21B	0.0620	0.8531	0.6612	0.058*
H21C	0.0963	0.6846	0.6063	0.058*
C22	0.1587 (3)	0.7986 (8)	0.7464 (5)	0.0314 (15)
H22A	0.1655	0.9194	0.7836	0.038*
H22B	0.1458	0.7123	0.8046	0.038*
C23	0.2764 (3)	0.7289 (7)	0.7903 (5)	0.0260 (15)
C24	0.3367 (3)	0.6715 (7)	0.7437 (4)	0.0205 (13)
C25	0.4002 (3)	0.7046 (7)	0.8112 (4)	0.0203 (13)
H25	0.4029	0.7611	0.8859	0.024*
C26	0.4594 (3)	0.6567 (6)	0.7713 (5)	0.0184 (12)
C27	0.4555 (3)	0.5766 (6)	0.6615 (5)	0.0186 (12)
C28	0.3926 (3)	0.5407 (7)	0.5957 (4)	0.0216 (13)
H28	0.3898	0.4814	0.5219	0.026*
C29	0.3340 (3)	0.5895 (7)	0.6353 (4)	0.0205 (13)
H29	0.2910	0.5668	0.5878	0.025*
C30	0.5276 (3)	0.6881 (7)	0.8472 (4)	0.0205 (14)
H30A	0.5302	0.8146	0.8757	0.025*
H30B	0.5323	0.6074	0.9166	0.025*
C31	0.5717 (3)	0.5684 (7)	0.6762 (4)	0.0229 (14)
H31	0.6109	0.5370	0.6434	0.027*
C32	0.6498 (3)	0.7126 (7)	0.8322 (5)	0.0212 (13)
C33	0.6643 (3)	0.7538 (7)	0.9523 (5)	0.0253 (14)
H33	0.6298	0.7406	0.9997	0.030*
C34	0.7281 (3)	0.8130 (7)	1.0020 (5)	0.0290 (14)
H34	0.7371	0.8423	1.0833	0.035*
C35	0.7792 (3)	0.8306 (7)	0.9357 (5)	0.0279 (14)
C36	0.7659 (3)	0.7901 (7)	0.8172 (4)	0.0246 (13)
H36	0.8010	0.8009	0.7708	0.030*
C37	0.7013 (3)	0.7338 (7)	0.7663 (5)	0.0246 (14)
H37	0.6922	0.7092	0.6843	0.030*
C38	0.8470 (3)	0.8982 (7)	0.9930 (5)	0.0306 (13)
C39	0.9601 (3)	0.9588 (8)	0.9650 (5)	0.0378 (15)
H39A	0.9807	0.8994	1.0394	0.045*
H39B	0.9565	1.0902	0.9796	0.045*
C40	1.0028 (3)	0.9256 (9)	0.8715 (5)	0.0513 (18)
H40A	1.0075	0.7951	0.8604	0.077*
H40B	1.0480	0.9795	0.8956	0.077*
H40C	0.9808	0.9806	0.7975	0.077*
N1	0.3991 (3)	0.0228 (5)	0.5863 (3)	0.0211 (11)
N2	0.3317 (2)	0.1537 (6)	0.7157 (4)	0.0193 (10)
N3	0.5143 (3)	0.5257 (6)	0.6154 (4)	0.0250 (12)
N4	0.5837 (2)	0.6538 (6)	0.7827 (4)	0.0222 (11)
O1	0.6950 (2)	0.2430 (5)	0.8296 (3)	0.0288 (10)
O2	0.6426 (2)	0.2796 (6)	0.9850 (3)	0.0364 (11)
O3	0.0586 (2)	0.4252 (6)	0.8876 (3)	0.0550 (13)
O4	0.0230 (2)	0.3763 (6)	0.6969 (3)	0.0407 (11)
O5	0.2203 (2)	0.7395 (5)	0.7064 (3)	0.0253 (10)
O6	0.2746 (2)	0.7638 (6)	0.8913 (3)	0.0367 (12)
O7	0.8588 (2)	0.9626 (5)	1.0894 (3)	0.0409 (10)
O8	0.89337 (19)	0.8836 (5)	0.9222 (3)	0.0336 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.020 (3)	0.049 (4)	0.045 (4)	−0.009 (3)	0.000 (3)	−0.002 (3)
C2	0.020 (4)	0.029 (3)	0.029 (3)	−0.002 (3)	−0.003 (2)	−0.008 (2)
C3	0.023 (4)	0.022 (3)	0.025 (3)	−0.002 (3)	0.008 (3)	0.001 (3)
C4	0.028 (4)	0.016 (3)	0.012 (3)	0.004 (2)	−0.002 (2)	0.000 (2)
C5	0.022 (3)	0.016 (3)	0.018 (3)	0.007 (2)	0.006 (2)	0.003 (2)
C6	0.023 (3)	0.014 (3)	0.018 (3)	−0.003 (3)	0.001 (2)	0.003 (2)
C7	0.030 (4)	0.016 (3)	0.015 (3)	0.002 (3)	0.000 (3)	0.000 (2)
C8	0.038 (4)	0.019 (3)	0.013 (3)	0.007 (3)	0.007 (3)	0.004 (2)
C9	0.026 (4)	0.025 (3)	0.018 (3)	0.004 (3)	0.001 (3)	0.006 (2)
C10	0.021 (3)	0.021 (3)	0.018 (3)	−0.004 (3)	−0.002 (2)	−0.001 (2)
C11	0.030 (4)	0.017 (3)	0.017 (3)	−0.002 (3)	−0.002 (3)	−0.001 (2)
C12	0.025 (4)	0.014 (3)	0.018 (3)	0.001 (2)	−0.002 (2)	−0.002 (2)
C13	0.029 (4)	0.021 (3)	0.015 (3)	−0.004 (2)	−0.005 (3)	−0.001 (2)
C14	0.026 (4)	0.025 (3)	0.015 (3)	0.002 (2)	0.004 (2)	−0.001 (2)
C15	0.021 (3)	0.025 (3)	0.021 (3)	−0.002 (2)	0.004 (2)	−0.001 (2)
C16	0.023 (3)	0.034 (3)	0.031 (3)	−0.004 (3)	−0.006 (2)	0.005 (3)
C17	0.030 (4)	0.030 (3)	0.021 (3)	−0.002 (3)	0.006 (3)	−0.002 (2)
C18	0.027 (3)	0.035 (3)	0.025 (3)	−0.002 (2)	0.002 (3)	0.000 (3)
C19	0.023 (3)	0.059 (4)	0.041 (3)	0.003 (3)	0.006 (3)	−0.005 (3)
C20	0.042 (4)	0.059 (4)	0.068 (5)	0.012 (3)	0.009 (4)	0.021 (4)
C21	0.032 (4)	0.046 (4)	0.037 (4)	−0.001 (3)	0.002 (3)	−0.010 (3)
C22	0.024 (4)	0.035 (3)	0.034 (3)	0.000 (3)	0.005 (3)	−0.001 (3)
C23	0.033 (4)	0.023 (3)	0.022 (3)	−0.008 (3)	0.005 (3)	−0.001 (3)
C24	0.017 (3)	0.021 (3)	0.021 (3)	−0.002 (2)	−0.003 (2)	0.004 (2)
C25	0.033 (4)	0.018 (3)	0.011 (2)	0.003 (3)	0.006 (2)	0.002 (2)
C26	0.026 (4)	0.016 (3)	0.013 (3)	−0.005 (3)	0.000 (2)	0.003 (2)
C27	0.024 (4)	0.014 (3)	0.018 (3)	0.003 (3)	0.004 (3)	0.007 (2)
C28	0.029 (4)	0.020 (3)	0.016 (3)	0.002 (3)	0.005 (3)	0.001 (2)
C29	0.026 (4)	0.020 (3)	0.012 (3)	−0.002 (3)	−0.007 (2)	0.005 (2)
C30	0.031 (4)	0.021 (3)	0.009 (2)	−0.003 (3)	0.001 (2)	−0.002 (2)
C31	0.035 (4)	0.022 (3)	0.013 (3)	0.005 (3)	0.007 (3)	0.000 (2)
C32	0.019 (4)	0.021 (3)	0.020 (3)	0.005 (3)	−0.009 (3)	0.003 (2)
C33	0.024 (4)	0.030 (3)	0.021 (3)	0.004 (2)	0.001 (3)	0.001 (2)
C34	0.032 (4)	0.031 (3)	0.022 (3)	0.002 (3)	−0.004 (3)	−0.001 (2)
C35	0.029 (4)	0.028 (3)	0.027 (3)	0.004 (3)	0.005 (3)	0.003 (2)
C36	0.029 (4)	0.026 (3)	0.018 (3)	0.000 (3)	0.003 (2)	0.001 (2)
C37	0.029 (4)	0.027 (3)	0.017 (3)	0.002 (2)	0.001 (3)	0.002 (2)
C38	0.033 (4)	0.029 (3)	0.029 (3)	0.003 (3)	0.002 (3)	0.001 (2)
C39	0.026 (3)	0.041 (4)	0.044 (3)	−0.010 (3)	0.000 (3)	−0.005 (3)
C40	0.035 (4)	0.062 (4)	0.059 (4)	−0.016 (3)	0.014 (3)	−0.013 (4)
N1	0.022 (3)	0.024 (3)	0.015 (2)	−0.005 (2)	−0.002 (2)	−0.001 (2)
N2	0.017 (3)	0.023 (3)	0.017 (2)	−0.002 (2)	0.000 (2)	−0.001 (2)
N3	0.031 (4)	0.024 (3)	0.018 (2)	−0.006 (2)	−0.001 (2)	−0.004 (2)
N4	0.024 (3)	0.021 (2)	0.021 (3)	−0.001 (2)	0.003 (2)	0.000 (2)
O1	0.022 (3)	0.036 (2)	0.027 (2)	−0.0032 (18)	−0.0007 (19)	−0.0027 (18)
O2	0.022 (3)	0.068 (3)	0.018 (2)	0.003 (2)	−0.0009 (18)	−0.007 (2)
O3	0.031 (3)	0.103 (4)	0.030 (2)	0.025 (2)	0.001 (2)	−0.009 (2)
O4	0.019 (2)	0.066 (3)	0.036 (2)	0.002 (2)	0.0009 (19)	−0.004 (2)
O5	0.019 (2)	0.034 (2)	0.023 (2)	0.0006 (18)	0.0016 (18)	−0.0038 (18)
O6	0.032 (3)	0.052 (3)	0.026 (2)	0.003 (2)	0.006 (2)	−0.010 (2)
O7	0.039 (3)	0.052 (2)	0.030 (2)	−0.005 (2)	0.0012 (19)	−0.010 (2)
O8	0.022 (2)	0.047 (2)	0.030 (2)	−0.0047 (19)	0.0011 (17)	−0.0051 (18)

Geometric parameters (Å, º)

C1—C2	1.500 (7)	C21—C22	1.500 (7)
C1—H1A	0.9800	C21—H21A	0.9800
C1—H1B	0.9800	C21—H21B	0.9800
C1—H1C	0.9800	C21—H21C	0.9800
C2—O1	1.455 (6)	C22—O5	1.446 (6)
C2—H2A	0.9900	C22—H22A	0.9900
C2—H2B	0.9900	C22—H22B	0.9900
C3—O2	1.198 (6)	C23—O6	1.198 (6)
C3—O1	1.331 (7)	C23—O5	1.350 (7)
C3—C4	1.491 (8)	C23—C24	1.457 (8)
C4—C5	1.374 (7)	C24—C29	1.382 (7)
C4—C9	1.400 (7)	C24—C25	1.390 (8)
C5—C6	1.389 (8)	C25—C26	1.379 (7)
C5—H5	0.9500	C25—H25	0.9500
C6—C7	1.393 (6)	C26—C27	1.388 (6)
C6—C10	1.488 (8)	C26—C30	1.504 (8)
C7—C8	1.379 (8)	C27—C28	1.376 (8)
C7—N1	1.388 (7)	C27—N3	1.414 (7)
C8—C9	1.388 (8)	C28—C29	1.368 (7)
C8—H8	0.9500	C28—H28	0.9500
C9—H9	0.9500	C29—H29	0.9500
C10—N2	1.479 (7)	C30—N4	1.462 (7)
C10—H10A	0.9900	C30—H30A	0.9900
C10—H10B	0.9900	C30—H30B	0.9900
C11—N1	1.283 (7)	C31—N3	1.274 (7)
C11—N2	1.357 (6)	C31—N4	1.365 (6)
C11—H11	0.9500	C31—H31	0.9500
C12—C13	1.373 (7)	C32—C37	1.381 (8)
C12—C17	1.390 (7)	C32—C33	1.400 (7)
C12—N2	1.404 (7)	C32—N4	1.411 (7)
C13—C14	1.382 (8)	C33—C34	1.374 (8)
C13—H13	0.9500	C33—H33	0.9500
C14—C15	1.389 (7)	C34—C35	1.375 (7)
C14—H14	0.9500	C34—H34	0.9500
C15—C16	1.352 (7)	C35—C36	1.380 (7)
C15—C18	1.488 (7)	C35—C38	1.485 (8)
C16—C17	1.383 (7)	C36—C37	1.383 (8)
C16—H16	0.9500	C36—H36	0.9500
C17—H17	0.9500	C37—H37	0.9500
C18—O3	1.200 (6)	C38—O7	1.196 (6)
C18—O4	1.325 (6)	C38—O8	1.333 (6)
C19—O4	1.444 (7)	C39—O8	1.446 (6)
C19—C20	1.499 (7)	C39—C40	1.499 (7)
C19—H19A	0.9900	C39—H39A	0.9900
C19—H19B	0.9900	C39—H39B	0.9900
C20—H20A	0.9800	C40—H40A	0.9800
C20—H20B	0.9800	C40—H40B	0.9800
C20—H20C	0.9800	C40—H40C	0.9800
C2—C1—H1A	109.5	O5—C22—C21	106.3 (5)
C2—C1—H1B	109.5	O5—C22—H22A	110.5
H1A—C1—H1B	109.5	C21—C22—H22A	110.5
C2—C1—H1C	109.5	O5—C22—H22B	110.5
H1A—C1—H1C	109.5	C21—C22—H22B	110.5
H1B—C1—H1C	109.5	H22A—C22—H22B	108.7
O1—C2—C1	106.6 (4)	O6—C23—O5	122.0 (6)
O1—C2—H2A	110.4	O6—C23—C24	125.4 (6)
C1—C2—H2A	110.4	O5—C23—C24	112.6 (5)
O1—C2—H2B	110.4	C29—C24—C25	118.6 (5)
C1—C2—H2B	110.4	C29—C24—C23	123.5 (5)
H2A—C2—H2B	108.6	C25—C24—C23	117.9 (5)
O2—C3—O1	124.0 (6)	C26—C25—C24	120.9 (5)
O2—C3—C4	123.4 (6)	C26—C25—H25	119.5
O1—C3—C4	112.5 (5)	C24—C25—H25	119.5
C5—C4—C9	120.6 (5)	C25—C26—C27	119.5 (5)
C5—C4—C3	118.5 (5)	C25—C26—C30	120.2 (5)
C9—C4—C3	120.9 (5)	C27—C26—C30	120.3 (5)
C4—C5—C6	120.6 (5)	C28—C27—C26	119.5 (5)
C4—C5—H5	119.7	C28—C27—N3	118.3 (5)
C6—C5—H5	119.7	C26—C27—N3	122.1 (5)
C5—C6—C7	119.4 (6)	C29—C28—C27	120.7 (5)
C5—C6—C10	118.9 (5)	C29—C28—H28	119.6
C7—C6—C10	121.6 (5)	C27—C28—H28	119.6
C8—C7—N1	119.0 (5)	C28—C29—C24	120.7 (5)
C8—C7—C6	119.6 (6)	C28—C29—H29	119.6
N1—C7—C6	121.4 (6)	C24—C29—H29	119.6
C7—C8—C9	121.6 (5)	N4—C30—C26	111.6 (4)
C7—C8—H8	119.2	N4—C30—H30A	109.3
C9—C8—H8	119.2	C26—C30—H30A	109.3
C8—C9—C4	118.2 (5)	N4—C30—H30B	109.3
C8—C9—H9	120.9	C26—C30—H30B	109.3
C4—C9—H9	120.9	H30A—C30—H30B	108.0
N2—C10—C6	110.6 (4)	N3—C31—N4	128.0 (6)
N2—C10—H10A	109.5	N3—C31—H31	116.0
C6—C10—H10A	109.5	N4—C31—H31	116.0
N2—C10—H10B	109.5	C37—C32—C33	118.1 (5)
C6—C10—H10B	109.5	C37—C32—N4	122.6 (5)
H10A—C10—H10B	108.1	C33—C32—N4	119.4 (5)
N1—C11—N2	127.8 (5)	C34—C33—C32	120.3 (6)
N1—C11—H11	116.1	C34—C33—H33	119.9
N2—C11—H11	116.1	C32—C33—H33	119.9
C13—C12—C17	118.9 (6)	C33—C34—C35	121.0 (5)
C13—C12—N2	120.4 (5)	C33—C34—H34	119.5
C17—C12—N2	120.6 (5)	C35—C34—H34	119.5
C12—C13—C14	121.2 (5)	C34—C35—C36	119.5 (6)
C12—C13—H13	119.4	C34—C35—C38	118.9 (5)
C14—C13—H13	119.4	C36—C35—C38	121.5 (5)
C13—C14—C15	119.6 (5)	C35—C36—C37	119.7 (5)
C13—C14—H14	120.2	C35—C36—H36	120.2
C15—C14—H14	120.2	C37—C36—H36	120.2
C16—C15—C14	119.0 (6)	C32—C37—C36	121.4 (5)
C16—C15—C18	123.2 (5)	C32—C37—H37	119.3
C14—C15—C18	117.8 (5)	C36—C37—H37	119.3
C15—C16—C17	122.1 (5)	O7—C38—O8	123.5 (6)
C15—C16—H16	118.9	O7—C38—C35	124.8 (6)
C17—C16—H16	118.9	O8—C38—C35	111.7 (5)
C16—C17—C12	119.2 (5)	O8—C39—C40	106.8 (4)
C16—C17—H17	120.4	O8—C39—H39A	110.4
C12—C17—H17	120.4	C40—C39—H39A	110.4
O3—C18—O4	123.3 (5)	O8—C39—H39B	110.4
O3—C18—C15	124.8 (5)	C40—C39—H39B	110.4
O4—C18—C15	111.8 (5)	H39A—C39—H39B	108.6
O4—C19—C20	107.8 (5)	C39—C40—H40A	109.5
O4—C19—H19A	110.1	C39—C40—H40B	109.5
C20—C19—H19A	110.1	H40A—C40—H40B	109.5
O4—C19—H19B	110.1	C39—C40—H40C	109.5
C20—C19—H19B	110.1	H40A—C40—H40C	109.5
H19A—C19—H19B	108.5	H40B—C40—H40C	109.5
C19—C20—H20A	109.5	C11—N1—C7	117.3 (4)
C19—C20—H20B	109.5	C11—N2—C12	122.0 (5)
H20A—C20—H20B	109.5	C11—N2—C10	119.9 (5)
C19—C20—H20C	109.5	C12—N2—C10	118.1 (4)
H20A—C20—H20C	109.5	C31—N3—C27	116.6 (5)
H20B—C20—H20C	109.5	C31—N4—C32	121.2 (5)
C22—C21—H21A	109.5	C31—N4—C30	120.2 (5)
C22—C21—H21B	109.5	C32—N4—C30	118.6 (4)
H21A—C21—H21B	109.5	C3—O1—C2	114.2 (4)
C22—C21—H21C	109.5	C18—O4—C19	117.7 (4)
H21A—C21—H21C	109.5	C23—O5—C22	115.5 (4)
H21B—C21—H21C	109.5	C38—O8—C39	116.7 (4)
O2—C3—C4—C5	13.6 (8)	C25—C26—C30—N4	−171.4 (4)
O1—C3—C4—C5	−163.2 (4)	C27—C26—C30—N4	9.6 (6)
O2—C3—C4—C9	−166.2 (5)	C37—C32—C33—C34	−0.1 (8)
O1—C3—C4—C9	17.0 (7)	N4—C32—C33—C34	−179.3 (5)
C9—C4—C5—C6	−0.2 (8)	C32—C33—C34—C35	−1.0 (9)
C3—C4—C5—C6	180.0 (5)	C33—C34—C35—C36	0.8 (8)
C4—C5—C6—C7	−0.6 (7)	C33—C34—C35—C38	179.0 (5)
C4—C5—C6—C10	178.5 (4)	C34—C35—C36—C37	0.5 (8)
C5—C6—C7—C8	1.2 (7)	C38—C35—C36—C37	−177.6 (5)
C10—C6—C7—C8	−177.9 (5)	C33—C32—C37—C36	1.4 (8)
C5—C6—C7—N1	−177.8 (5)	N4—C32—C37—C36	−179.4 (5)
C10—C6—C7—N1	3.2 (7)	C35—C36—C37—C32	−1.6 (8)
N1—C7—C8—C9	177.9 (5)	C34—C35—C38—O7	−10.7 (8)
C6—C7—C8—C9	−1.0 (7)	C36—C35—C38—O7	167.5 (5)
C7—C8—C9—C4	0.3 (7)	C34—C35—C38—O8	171.2 (5)
C5—C4—C9—C8	0.3 (7)	C36—C35—C38—O8	−10.6 (7)
C3—C4—C9—C8	−179.9 (5)	N2—C11—N1—C7	−1.5 (8)
C5—C6—C10—N2	169.7 (4)	C8—C7—N1—C11	−175.0 (5)
C7—C6—C10—N2	−11.2 (6)	C6—C7—N1—C11	3.9 (7)
C17—C12—C13—C14	2.3 (8)	N1—C11—N2—C12	174.6 (5)
N2—C12—C13—C14	178.8 (5)	N1—C11—N2—C10	−8.1 (8)
C12—C13—C14—C15	−0.2 (8)	C13—C12—N2—C11	160.4 (5)
C13—C14—C15—C16	−1.4 (8)	C17—C12—N2—C11	−23.2 (7)
C13—C14—C15—C18	179.4 (5)	C13—C12—N2—C10	−17.0 (7)
C14—C15—C16—C17	0.9 (8)	C17—C12—N2—C10	159.5 (4)
C18—C15—C16—C17	−180.0 (5)	C6—C10—N2—C11	13.4 (6)
C15—C16—C17—C12	1.2 (8)	C6—C10—N2—C12	−169.2 (4)
C13—C12—C17—C16	−2.7 (8)	N4—C31—N3—C27	1.9 (8)
N2—C12—C17—C16	−179.2 (5)	C28—C27—N3—C31	176.9 (5)
C16—C15—C18—O3	−172.4 (6)	C26—C27—N3—C31	−4.8 (7)
C14—C15—C18—O3	6.8 (8)	N3—C31—N4—C32	−171.8 (5)
C16—C15—C18—O4	6.8 (8)	N3—C31—N4—C30	7.5 (8)
C14—C15—C18—O4	−174.1 (5)	C37—C32—N4—C31	18.1 (8)
O6—C23—C24—C29	163.0 (6)	C33—C32—N4—C31	−162.7 (5)
O5—C23—C24—C29	−16.9 (8)	C37—C32—N4—C30	−161.2 (5)
O6—C23—C24—C25	−18.4 (9)	C33—C32—N4—C30	18.0 (7)
O5—C23—C24—C25	161.7 (4)	C26—C30—N4—C31	−12.4 (6)
C29—C24—C25—C26	−0.1 (7)	C26—C30—N4—C32	166.9 (4)
C23—C24—C25—C26	−178.8 (5)	O2—C3—O1—C2	2.0 (8)
C24—C25—C26—C27	0.9 (7)	C4—C3—O1—C2	178.9 (4)
C24—C25—C26—C30	−178.0 (5)	C1—C2—O1—C3	−179.3 (4)
C25—C26—C27—C28	−2.2 (6)	O3—C18—O4—C19	−3.3 (9)
C30—C26—C27—C28	176.8 (5)	C15—C18—O4—C19	177.6 (4)
C25—C26—C27—N3	179.5 (5)	C20—C19—O4—C18	143.2 (5)
C30—C26—C27—N3	−1.5 (6)	O6—C23—O5—C22	1.0 (8)
C26—C27—C28—C29	2.6 (7)	C24—C23—O5—C22	−179.1 (4)
N3—C27—C28—C29	−179.0 (4)	C21—C22—O5—C23	178.2 (5)
C27—C28—C29—C24	−1.8 (8)	O7—C38—O8—C39	−3.0 (8)
C25—C24—C29—C28	0.5 (8)	C35—C38—O8—C39	175.1 (4)
C23—C24—C29—C28	179.1 (5)	C40—C39—O8—C38	179.7 (5)