data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Steve Davies'
_publ_contact_author_email       STEVE.DAVIES@CHEM.OX.AC.UK

_publ_section_title              
;
Double diastereoselective conjugate addition of
homochiral lithium amides to homochiral a,b-unsaturated esters
containing cis- and trans-dioxolane units
;
loop_
_publ_author_name
'Steve Davies'
'Matthew J. Durbin'
'Euan C. Goddard'
'Peter M. Kelly'
'Wataru Kurosawa'
'James A. Lee'
;
R.L.Nicholson
;
'Paul D. Price'
'Paul M. Roberts'
'Angela J. Russell'
'Philip M. Scott'
'Andrew D. Smith'

# Attachment 'CCDC_668996'

data_CRYSTALS_cif
_database_code_depnum_ccdc_archive 'CCDC 668996'
#=============================================================

_cell_length_a                   11.5712(2)
_cell_angle_alpha                90
_cell_length_b                   13.9737(2)
_cell_angle_beta                 90
_cell_length_c                   17.0380(2)
_cell_angle_gamma                90
_cell_volume                     2754.92(7)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_int_tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2

# choose from: rm (reference molecule of
# known chirality), ad (anomolous
# dispersion - ie. Flack param), rmad
# (both rm and ad), syn (known from
# synthetic pathway), unk (unknown)
# or . (not applicable).

_chemical_absolute_configuration unk

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 International_Tables_Vol_IV_Table_2.2B
'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 International_Tables_Vol_IV_Table_2.2B
'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 International_Tables_Vol_IV_Table_2.2B
'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 International_Tables_Vol_IV_Table_2.2B

_cell_formula_units_Z            4
_chemical_formula_sum            'C29 H39 N1 O4'
_chemical_formula_moiety         'C29 H39 N1 O4'
_chemical_compound_source        ?
_chemical_formula_weight         465.63

_cell_measurement_reflns_used    3420
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    190

_exptl_crystal_description       ' block '
_exptl_crystal_colour            ' colourless '
_exptl_crystal_size_min          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.20

_exptl_crystal_density_diffrn    1.123
_exptl_crystal_density_meas      'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             1008.000
_exptl_absorpt_coefficient_mu    0.074
# Sheldrick geometric definitions 0.99 0.99

_diffrn_measurement_device_type  
;
Enraf Nonius Kappa CCD
;
_diffrn_radiation_monochromator  graphite
_computing_data_collection       
;
COLLECT (Nonius BV, 1997)
;
_computing_data_reduction        
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_computing_cell_refinement       
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_computing_structure_solution    
;
SIR92 (Altomare et al, 1994)
;
_diffrn_measurement_method       \w
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_T_max  0.99

_diffrn_standards_interval_time  0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0.00

_diffrn_ambient_temperature      190
_diffrn_reflns_number            6213
_reflns_number_total             3491
_diffrn_reflns_av_R_equivalents  0.01
# Number of reflections with Friedels Law is 3491
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 3154

_diffrn_reflns_theta_min         5.164
_diffrn_reflns_theta_max         27.475
_diffrn_measured_fraction_theta_max 0.987

_diffrn_reflns_theta_full        27.269
_diffrn_measured_fraction_theta_full 0.989

_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_reflns_limit_h_min              0
_reflns_limit_h_max              15
_reflns_limit_k_min              0
_reflns_limit_k_max              18
_reflns_limit_l_min              0
_reflns_limit_l_max              22

_refine_diff_density_min         -0.13
_refine_diff_density_max         0.16

_refine_ls_number_reflns         2932
_refine_ls_number_parameters     307

#_refine_ls_R_factor_ref 0.0321
_refine_ls_wR_factor_ref         0.0396
_refine_ls_goodness_of_fit_ref   1.0881

#_reflns_number_all 3491
_refine_ls_R_factor_all          0.0408
_refine_ls_wR_factor_all         0.0465

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>3.00u(I)
_reflns_number_gt                2932
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_gt          0.0396

_refine_ls_shift/su_max          0.000495
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method = Prince modified Chebychev polynomial, (Watkin, 1994)
W = [weight] * [1-(deltaF/6*sigmaF)^2]^2

1.12 0.464 0.724
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073

## -------------------REFERENCES ----------------------##
## Insert your own references - in alphabetic order
_publ_section_references         
;

Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C.,
Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution
of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435

COLLECT Software, Nonius BV 1997-2001)

Otwinowski, Z. & Minor, W. (1996), Processing of X-ray
Diffraction Data Collected in Oscillation Mode. Methods Enzymol.
276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press.

Watkin D.J. (1994),
Acta Cryst, A50, 411-437
Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper
R.I. (2001) CRYSTALS
Issue 11. Chemical Crystallography Laboratory, OXFORD, UK.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical
Crystallography Laboratory, OXFORD, UK.
;

# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_attached_hydrogens
# Replace trailing . with the number of unfound
# hydrogen atoms attaced to relavent atom
C1 C 1.09766(12) 0.0932(1) 0.91670(8) 0.0252 1.0000 Uani .
C2 C 1.14396(12) 0.1925(1) 0.93940(8) 0.0247 1.0000 Uani .
C3 C 1.26054(13) 0.19177(12) 0.98505(8) 0.0296 1.0000 Uani .
O4 O 1.3205(1) 0.27345(9) 0.95443(8) 0.0419 1.0000 Uani .
C5 C 1.24926(15) 0.31994(12) 0.89691(9) 0.0352 1.0000 Uani .
O6 O 1.1711(1) 0.24751(8) 0.87155(6) 0.0327 1.0000 Uani .
C7 C 1.18797(18) 0.40381(12) 0.93411(11) 0.0444 1.0000 Uani .
C8 C 1.3231(2) 0.34897(18) 0.82821(13) 0.0609 1.0000 Uani .
C9 C 1.33546(14) 0.10585(13) 0.9734(1) 0.0365 1.0000 Uani .
C10 C 1.37194(19) 0.05109(18) 1.03126(15) 0.0594 1.0000 Uani .
N11 N 1.0099(1) 0.09077(9) 0.85424(7) 0.0272 1.0000 Uani .
C12 C 1.05493(13) 0.10235(12) 0.77305(8) 0.0309 1.0000 Uani .
C13 C 1.15647(14) 0.03683(12) 0.75731(9) 0.0318 1.0000 Uani .
C14 C 1.25594(15) 0.07247(14) 0.7219(1) 0.0397 1.0000 Uani .
C15 C 1.34795(16) 0.01132(17) 0.70446(12) 0.0506 1.0000 Uani .
C16 C 1.34161(18) -0.08455(17) 0.72289(12) 0.0539 1.0000 Uani .
C17 C 1.2428(2) -0.12030(15) 0.75848(12) 0.0537 1.0000 Uani .
C18 C 1.15056(17) -0.06006(13) 0.7745(1) 0.0435 1.0000 Uani .
C19 C 0.96016(16) 0.08029(17) 0.7129(1) 0.0479 1.0000 Uani .
C20 C 0.90962(12) 0.15226(11) 0.86862(9) 0.0294 1.0000 Uani .
C21 C 0.79404(12) 0.10196(12) 0.85836(8) 0.0284 1.0000 Uani .
C22 C 0.78337(14) 0.00366(12) 0.8683(1) 0.0352 1.0000 Uani .
C23 C 0.67582(16) -0.04040(13) 0.86397(11) 0.0415 1.0000 Uani .
C24 C 0.57776(15) 0.01278(16) 0.84940(12) 0.0449 1.0000 Uani .
C25 C 0.58748(15) 0.11052(16) 0.83857(12) 0.0465 1.0000 Uani .
C26 C 0.69480(14) 0.15474(13) 0.8434(1) 0.0358 1.0000 Uani .
C27 C 1.05004(14) 0.04752(12) 0.99213(9) 0.0311 1.0000 Uani .
C28 C 1.03597(15) -0.05989(12) 0.9875(1) 0.0349 1.0000 Uani .
O29 O 0.9404(1) -0.08694(8) 1.02607(7) 0.0376 1.0000 Uani .
C30 C 0.90812(19) -0.18900(13) 1.03524(13) 0.0493 1.0000 Uani .
C31 C 0.8954(3) -0.23723(16) 0.95627(17) 0.0748 1.0000 Uani .
C32 C 0.7924(2) -0.18209(17) 1.07587(19) 0.0720 1.0000 Uani .
C33 C 0.9965(2) -0.23841(17) 1.08626(19) 0.0748 1.0000 Uani .
O34 O 1.10308(14) -0.1134(1) 0.95646(9) 0.0579 1.0000 Uani .
H11 H 1.1633 0.0554 0.8928 0.0316 1.0000 Uiso .
H21 H 1.0789 0.2193 0.9724 0.0319 1.0000 Uiso .
H31 H 1.2427 0.1924 1.0428 0.0355 1.0000 Uiso .
H71 H 1.1374 0.4368 0.8942 0.0557 1.0000 Uiso .
H72 H 1.2449 0.4515 0.9551 0.0557 1.0000 Uiso .
H73 H 1.1370 0.3819 0.9787 0.0557 1.0000 Uiso .
H81 H 1.2745 0.3820 0.7871 0.0765 1.0000 Uiso .
H82 H 1.3860 0.3939 0.8449 0.0765 1.0000 Uiso .
H83 H 1.3597 0.2910 0.8032 0.0765 1.0000 Uiso .
H91 H 1.3579 0.0875 0.9183 0.0481 1.0000 Uiso .
H101 H 1.3517 0.0681 1.0876 0.0708 1.0000 Uiso .
H102 H 1.4232 -0.0054 1.0217 0.0708 1.0000 Uiso .
H121 H 1.0833 0.1708 0.7676 0.0386 1.0000 Uiso .
H141 H 1.2612 0.1427 0.7092 0.0511 1.0000 Uiso .
H151 H 1.4197 0.0381 0.6781 0.0639 1.0000 Uiso .
H161 H 1.4082 -0.1287 0.7109 0.0661 1.0000 Uiso .
H171 H 1.2388 -0.1903 0.7718 0.0639 1.0000 Uiso .
H181 H 1.0770 -0.0869 0.7991 0.0542 1.0000 Uiso .
H191 H 0.9887 0.0883 0.6580 0.0578 1.0000 Uiso .
H192 H 0.9324 0.0122 0.7198 0.0578 1.0000 Uiso .
H193 H 0.8917 0.1240 0.7211 0.0578 1.0000 Uiso .
H201 H 0.9135 0.1778 0.9235 0.0386 1.0000 Uiso .
H202 H 0.9115 0.2077 0.8309 0.0386 1.0000 Uiso .
H221 H 0.8538 -0.0367 0.8788 0.0448 1.0000 Uiso .
H231 H 0.6704 -0.1110 0.8720 0.0507 1.0000 Uiso .
H241 H 0.5006 -0.0212 0.8455 0.0539 1.0000 Uiso .
H251 H 0.5168 0.1502 0.8264 0.0587 1.0000 Uiso .
H261 H 0.7008 0.2264 0.8356 0.0445 1.0000 Uiso .
H271 H 1.1047 0.0633 1.0369 0.0398 1.0000 Uiso .
H272 H 0.9729 0.0768 1.0043 0.0398 1.0000 Uiso .
H311 H 0.8750 -0.3060 0.9600 0.0949 1.0000 Uiso .
H312 H 0.9726 -0.2331 0.9252 0.0949 1.0000 Uiso .
H313 H 0.8361 -0.2037 0.9220 0.0949 1.0000 Uiso .
H321 H 0.7616 -0.2476 1.0869 0.0914 1.0000 Uiso .
H322 H 0.8032 -0.1480 1.1283 0.0914 1.0000 Uiso .
H323 H 0.7370 -0.1452 1.0437 0.0914 1.0000 Uiso .
H331 H 0.9740 -0.3078 1.0927 0.0869 1.0000 Uiso .
H332 H 0.9987 -0.2076 1.1391 0.0869 1.0000 Uiso .
H333 H 1.0739 -0.2347 1.0611 0.0869 1.0000 Uiso .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0230(6) 0.0281(7) 0.0246(6) -0.0026(5) 0.0020(5) -0.0002(6)
C2 0.0220(6) 0.0289(7) 0.0233(6) -0.0010(5) -0.0002(5) -0.0006(6)
C3 0.0257(7) 0.0364(8) 0.0268(6) -0.0007(6) -0.0033(6) -0.0029(6)
O4 0.0318(6) 0.0369(6) 0.0570(7) 0.0099(5) -0.0152(6) -0.0099(5)
C5 0.0347(8) 0.0360(8) 0.0350(7) 0.0043(6) -0.0059(7) -0.0100(7)
O6 0.0352(6) 0.0360(6) 0.0269(5) 0.0027(4) -0.0036(4) -0.0103(5)
C7 0.054(1) 0.0299(8) 0.049(1) 0.0045(7) -0.0107(9) -0.0023(8)
C8 0.0646(13) 0.0650(13) 0.0533(11) 0.007(1) 0.0129(11) -0.0273(12)
C9 0.0248(7) 0.0401(8) 0.0444(8) 0.0041(7) -0.0037(7) -0.0005(7)
C10 0.0461(11) 0.0578(13) 0.0743(14) 0.0224(11) -0.014(1) 0.005(1)
N11 0.0207(5) 0.0338(6) 0.0272(6) -0.0060(5) 0.0010(5) -0.0001(5)
C12 0.0279(7) 0.0389(8) 0.0258(7) -0.0052(6) 0.0003(6) -0.0025(7)
C13 0.0309(7) 0.0389(8) 0.0256(6) -0.0094(6) 0.0017(6) -0.0021(7)
C14 0.0327(8) 0.052(1) 0.0347(8) -0.0114(7) 0.0036(7) -0.0096(8)
C15 0.0303(8) 0.0722(14) 0.049(1) -0.020(1) 0.0065(8) -0.0063(9)
C16 0.043(1) 0.0670(13) 0.0515(11) -0.021(1) 0.0025(9) 0.015(1)
C17 0.0694(14) 0.046(1) 0.046(1) -0.0113(8) 0.009(1) 0.013(1)
C18 0.050(1) 0.0415(9) 0.0392(8) -0.0101(7) 0.0139(8) -0.0015(8)
C19 0.0381(9) 0.0746(13) 0.0310(8) -0.0127(8) -0.0054(7) -0.001(1)
C20 0.0218(6) 0.0312(7) 0.0352(7) -0.0047(6) 0.0002(6) -0.0009(6)
C21 0.0241(6) 0.0373(7) 0.0239(6) -0.0039(6) 0.0008(5) -0.0020(6)
C22 0.0280(7) 0.0354(8) 0.0421(8) -0.0023(7) -0.0026(7) -0.0019(7)
C23 0.0375(8) 0.0412(9) 0.0459(9) -0.0028(8) -0.0004(8) -0.0105(8)
C24 0.0277(8) 0.0599(12) 0.0470(9) -0.0025(9) -0.0013(7) -0.0133(8)
C25 0.0237(8) 0.0645(12) 0.051(1) 0.0096(9) -0.0036(7) 0.0014(8)
C26 0.0279(7) 0.0413(8) 0.0383(8) 0.0035(7) -0.0015(7) -0.0003(7)
C27 0.0332(7) 0.0301(7) 0.0301(7) -0.0005(6) 0.0069(6) -0.0021(7)
C28 0.0362(8) 0.0321(8) 0.0364(8) 0.0044(6) 0.0044(7) 0.0034(7)
O29 0.0380(6) 0.0268(5) 0.0479(6) 0.0070(5) 0.0060(5) -0.0008(5)
C30 0.052(1) 0.0255(8) 0.0707(12) 0.0128(8) 0.000(1) -0.0048(8)
C31 0.104(2) 0.033(1) 0.0876(17) -0.0037(11) -0.0087(17) -0.0116(13)
C32 0.0590(13) 0.0477(12) 0.109(2) 0.0181(13) 0.0177(15) -0.0149(11)
C33 0.0744(16) 0.0458(12) 0.104(2) 0.0356(13) -0.0096(16) -0.0007(12)
O34 0.0636(9) 0.0350(6) 0.075(1) 0.0037(7) 0.0284(8) 0.0121(7)
_refine_ls_extinction_method     None
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.536(2) yes
C1 . N11 . 1.4710(18) yes
C1 . C27 . 1.537(2) yes
C1 . H11 . 1.011 no
C2 . C3 . 1.5571(19) yes
C2 . O6 . 1.4233(17) yes
C2 . H21 . 1.011 no
C3 . O4 . 1.434(2) yes
C3 . C9 . 1.494(2) yes
C3 . H31 . 1.006 no
O4 . C5 . 1.436(2) yes
C5 . O6 . 1.4241(19) yes
C5 . C7 . 1.509(3) yes
C5 . C8 . 1.505(3) yes
C7 . H71 . 1.009 no
C7 . H72 . 1.002 no
C7 . H73 . 1.010 no
C8 . H81 . 1.011 no
C8 . H82 . 1.003 no
C8 . H83 . 1.009 no
C9 . C10 . 1.317(3) yes
C9 . H91 . 1.008 no
C10 . H101 . 1.016 no
C10 . H102 . 1.001 no
N11 . C12 . 1.4868(18) yes
N11 . C20 . 1.4649(19) yes
C12 . C13 . 1.514(2) yes
C12 . C19 . 1.532(2) yes
C12 . H121 . 1.016 no
C13 . C14 . 1.391(2) yes
C13 . C18 . 1.387(3) yes
C14 . C15 . 1.397(3) yes
C14 . H141 . 1.007 no
C15 . C16 . 1.378(3) yes
C15 . H151 . 1.015 no
C16 . C17 . 1.387(3) yes
C16 . H161 . 1.008 no
C17 . C18 . 1.387(3) yes
C17 . H171 . 1.005 no
C18 . H181 . 1.020 no
C19 . H191 . 0.999 no
C19 . H192 . 1.011 no
C19 . H193 . 1.011 no
C20 . C21 . 1.521(2) yes
C20 . H201 . 1.002 no
C20 . H202 . 1.007 no
C21 . C22 . 1.389(2) yes
C21 . C26 . 1.388(2) yes
C22 . C23 . 1.390(2) yes
C22 . H221 . 1.007 no
C23 . C24 . 1.379(3) yes
C23 . H231 . 0.998 no
C24 . C25 . 1.383(3) yes
C24 . H241 . 1.014 no
C25 . C26 . 1.390(2) yes
C25 . H251 . 1.009 no
C26 . H261 . 1.013 no
C27 . C28 . 1.512(2) yes
C27 . H271 . 1.015 no
C27 . H272 . 1.003 no
C28 . O29 . 1.341(2) yes
C28 . O34 . 1.200(2) yes
O29 . C30 . 1.482(2) yes
C30 . C31 . 1.512(4) yes
C30 . C32 . 1.511(3) yes
C30 . C33 . 1.509(3) yes
C31 . H311 . 0.992 no
C31 . H312 . 1.040 no
C31 . H313 . 1.016 no
C32 . H321 . 0.999 no
C32 . H322 . 1.021 no
C32 . H323 . 0.988 no
C33 . H331 . 1.010 no
C33 . H332 . 0.999 no
C33 . H333 . 0.994 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . N11 . 116.35(12) yes
C2 . C1 . C27 . 106.84(11) yes
N11 . C1 . C27 . 110.35(12) yes
C2 . C1 . H11 . 108.196 no
N11 . C1 . H11 . 102.382 no
C27 . C1 . H11 . 112.845 no
C1 . C2 . C3 . 114.96(12) yes
C1 . C2 . O6 . 111.11(11) yes
C3 . C2 . O6 . 102.58(11) yes
C1 . C2 . H21 . 102.422 no
C3 . C2 . H21 . 111.689 no
O6 . C2 . H21 . 114.542 no
C2 . C3 . O4 . 103.42(11) yes
C2 . C3 . C9 . 116.21(13) yes
O4 . C3 . C9 . 108.10(12) yes
C2 . C3 . H31 . 108.122 no
O4 . C3 . H31 . 116.618 no
C9 . C3 . H31 . 104.851 no
C3 . O4 . C5 . 109.32(11) yes
O4 . C5 . O6 . 104.47(13) yes
O4 . C5 . C7 . 109.53(14) yes
O6 . C5 . C7 . 112.40(14) yes
O4 . C5 . C8 . 109.08(16) yes
O6 . C5 . C8 . 108.42(14) yes
C7 . C5 . C8 . 112.59(16) yes
C2 . O6 . C5 . 106.12(11) yes
C5 . C7 . H71 . 110.118 no
C5 . C7 . H72 . 110.898 no
H71 . C7 . H72 . 108.535 no
C5 . C7 . H73 . 110.777 no
H71 . C7 . H73 . 107.945 no
H72 . C7 . H73 . 108.482 no
C5 . C8 . H81 . 110.270 no
C5 . C8 . H82 . 111.113 no
H81 . C8 . H82 . 108.369 no
C5 . C8 . H83 . 110.561 no
H81 . C8 . H83 . 107.896 no
H82 . C8 . H83 . 108.537 no
C3 . C9 . C10 . 123.62(19) yes
C3 . C9 . H91 . 118.501 no
C10 . C9 . H91 . 117.862 no
C9 . C10 . H101 . 119.773 no
C9 . C10 . H102 . 121.750 no
H101 . C10 . H102 . 118.390 no
C1 . N11 . C12 . 115.40(11) yes
C1 . N11 . C20 . 114.34(11) yes
C12 . N11 . C20 . 111.67(12) yes
N11 . C12 . C13 . 111.77(13) yes
N11 . C12 . C19 . 110.46(13) yes
C13 . C12 . C19 . 108.39(13) yes
N11 . C12 . H121 . 107.539 no
C13 . C12 . H121 . 107.632 no
C19 . C12 . H121 . 111.040 no
C12 . C13 . C14 . 120.16(15) yes
C12 . C13 . C18 . 120.98(16) yes
C14 . C13 . C18 . 118.80(17) yes
C13 . C14 . C15 . 120.25(18) yes
C13 . C14 . H141 . 119.519 no
C15 . C14 . H141 . 120.228 no
C14 . C15 . C16 . 120.35(18) yes
C14 . C15 . H151 . 119.451 no
C16 . C15 . H151 . 120.195 no
C15 . C16 . C17 . 119.58(18) yes
C15 . C16 . H161 . 120.562 no
C17 . C16 . H161 . 119.856 no
C16 . C17 . C18 . 120.14(19) yes
C16 . C17 . H171 . 119.180 no
C18 . C17 . H171 . 120.677 no
C13 . C18 . C17 . 120.85(18) yes
C13 . C18 . H181 . 119.164 no
C17 . C18 . H181 . 119.988 no
C12 . C19 . H191 . 111.527 no
C12 . C19 . H192 . 109.816 no
H191 . C19 . H192 . 108.626 no
C12 . C19 . H193 . 110.355 no
H191 . C19 . H193 . 108.695 no
H192 . C19 . H193 . 107.724 no
N11 . C20 . C21 . 113.99(12) yes
N11 . C20 . H201 . 109.254 no
C21 . C20 . H201 . 108.136 no
N11 . C20 . H202 . 109.083 no
C21 . C20 . H202 . 107.523 no
H201 . C20 . H202 . 108.727 no
C20 . C21 . C22 . 121.40(14) yes
C20 . C21 . C26 . 120.20(14) yes
C22 . C21 . C26 . 118.29(15) yes
C21 . C22 . C23 . 120.72(16) yes
C21 . C22 . H221 . 120.198 no
C23 . C22 . H221 . 119.077 no
C22 . C23 . C24 . 120.49(16) yes
C22 . C23 . H231 . 119.144 no
C24 . C23 . H231 . 120.364 no
C23 . C24 . C25 . 119.30(16) yes
C23 . C24 . H241 . 118.946 no
C25 . C24 . H241 . 121.735 no
C24 . C25 . C26 . 120.26(17) yes
C24 . C25 . H251 . 120.295 no
C26 . C25 . H251 . 119.438 no
C21 . C26 . C25 . 120.93(17) yes
C21 . C26 . H261 . 119.511 no
C25 . C26 . H261 . 119.561 no
C1 . C27 . C28 . 114.03(13) yes
C1 . C27 . H271 . 108.326 no
C28 . C27 . H271 . 108.825 no
C1 . C27 . H272 . 108.825 no
C28 . C27 . H272 . 108.644 no
H271 . C27 . H272 . 108.031 no
C27 . C28 . O29 . 110.05(14) yes
C27 . C28 . O34 . 124.86(16) yes
O29 . C28 . O34 . 125.02(16) yes
C28 . O29 . C30 . 122.04(14) yes
O29 . C30 . C31 . 111.07(17) yes
O29 . C30 . C32 . 102.12(16) yes
C31 . C30 . C32 . 110.5(2) yes
O29 . C30 . C33 . 109.28(17) yes
C31 . C30 . C33 . 112.0(2) yes
C32 . C30 . C33 . 111.5(2) yes
C30 . C31 . H311 . 113.469 no
C30 . C31 . H312 . 110.164 no
H311 . C31 . H312 . 106.951 no
C30 . C31 . H313 . 111.849 no
H311 . C31 . H313 . 108.819 no
H312 . C31 . H313 . 105.146 no
C30 . C32 . H321 . 110.088 no
C30 . C32 . H322 . 108.833 no
H321 . C32 . H322 . 107.889 no
C30 . C32 . H323 . 110.709 no
H321 . C32 . H323 . 110.492 no
H322 . C32 . H323 . 108.758 no
C30 . C33 . H331 . 109.098 no
C30 . C33 . H332 . 109.815 no
H331 . C33 . H332 . 108.810 no
C30 . C33 . H333 . 109.806 no
H331 . C33 . H333 . 109.202 no
H332 . C33 . H333 . 110.085 no

# Replace trailing . with the number of unfound
# hydrogen atoms attaced to relavent atom
# Replace trailing . with the number of unfound
# hydrogen atoms attaced to relavent atom
# Replace trailing . with the number of unfound
# hydrogen atoms attaced to relavent atom