Supplementary Material (ESI) for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2006


data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177
_publ_contact_author_name        'Steve Davies'
_publ_contact_author_address     
;Chemistry Research Laboratory
Mansfield Road
Oxford
OX1 3TA
;
_publ_contact_author_email       steve.davies@chem.ox.ac.uk
_publ_contact_author_phone       ' 01865 275 646'
_publ_contact_author_fax         ' 01865 275 633'
loop_
_publ_author_name
_publ_author_address
S.D.Bull
;Chemistry Research Laboratory
Mansfield Road
Oxford
OX1 3TA
;
S.G.Davies
;Chemistry Research Laboratory
Mansfield Road
Oxford
OX1 3TA
;
G.A.Christopher
;Chemistry Research Laboratory
Mansfield Road
Oxford
OX1 3TA
;
D.B.Kruchinin
;Chemistry Research Laboratory
Mansfield Road
Oxford
OX1 3TA
;
M.-S.Key
;Chemistry Research Laboratory
Mansfield Road
Oxford
OX1 3TA
;
;
P.M.Roberts
;
;Chemistry Research Laboratory
Mansfield Road
Oxford
OX1 3TA
;
E.D.Savory
;Chemistry Research Laboratory
Mansfield Road
Oxford
OX1 3TA
;
A.D.Smith
;Chemistry Research Laboratory
Mansfield Road
Oxford
OX1 3TA
;
J.E.Thomson
;Chemistry Research Laboratory
Mansfield Road
Oxford
OX1 3TA
;

_publ_section_title              
;
SuperQuat 5,5-Dimethyl-4-iso-propyl-oxazolidin-2-one
as a Mimic of Evans 4-tert-Butyl-oxazolidin-2-one
;

_publ_requested_category         CO # choose from: FI FM FO CI CM CO AD
_publ_requested_coeditor_name    'Dr Andrew Smith'

data_CRYSTALS_cif
_database_code_depnum_ccdc_archive 'CCDC 280122'
_audit_creation_date             02-09-12
_audit_creation_method           CRYSTALS_ver_12-03-99

#==============================================================================
# 4. TEXT
_publ_section_abstract           #Text of the abstract
;
?
;
_publ_section_comment            #Text of the paper
;
?
;
_publ_section_acknowledgements   # Acknowledgments
;
?
;
_publ_section_figure_captions    #Captions to figures
;
?
;
_publ_section_exptl_refinement   
# see also _refine_ls_hydrogen for refinement keywords.
;
H atoms placed geometrically after each cycle
;
_publ_section_exptl_prep         
;
?
;
#==========================================================================

_chemical_name_systematic        # IUPAC name, in full
?

_chemical_melting_point          'not measured'

# choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse'
_refine_ls_matrix_type           full

# choose from 'heavy, direct, difmap, geom'
_atom_sites_solution_primary     direct

# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

# choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed'
_refine_ls_hydrogen_treatment    constr

#****************************************************************************
# General computing
#=============================================================
_computing_structure_refinement  
;
CRYSTALS (Watkin et al 2001)
;
_computing_publication_material  
;
CRYSTALS (Watkin et al 2001)
;
_computing_molecular_graphics    
;
CAMERON (Watkin et al 1996)
;
#=============================================================

_cell_length_a                   6.9391(2)
_cell_angle_alpha                90
_cell_length_b                   8.0963(3)
_cell_angle_beta                 101.182(3)
_cell_length_c                   15.5077(5)
_cell_angle_gamma                90
_cell_volume                     854.70(5)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_int_tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z

# 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
'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
'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

_cell_formula_units_Z            2
_chemical_formula_sum            'C17 H27 N1 O3'
_chemical_formula_moiety         'C17 H27 N1 O3'
_chemical_compound_source        ?
_chemical_formula_weight         293.41

_cell_measurement_reflns_used    2283
_cell_measurement_theta_min      5
_cell_measurement_theta_max      30
_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    1.140
_exptl_crystal_density_meas      'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             320.000
_exptl_absorpt_coefficient_mu    0.077
# Sheldrick geometric definitions 0.98 0.98

_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  0.98
_exptl_absorpt_correction_T_max  0.98

_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            3902
_reflns_number_total             2627
_diffrn_reflns_av_R_equivalents  0.08
# Number of reflections with Friedels Law is 2627
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 2504

_diffrn_reflns_theta_min         5.178
_diffrn_reflns_theta_max         30.050
_diffrn_measured_fraction_theta_max 0.985

_diffrn_reflns_theta_full        28.322
_diffrn_measured_fraction_theta_full 0.988

_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              21

_refine_diff_density_min         -0.24
_refine_diff_density_max         0.31

_refine_ls_number_reflns         2155
_refine_ls_number_parameters     190

#_refine_ls_R_factor_ref 0.0511
_refine_ls_wR_factor_ref         0.0612
_refine_ls_goodness_of_fit_ref   0.9657

#_reflns_number_all 2627
_refine_ls_R_factor_all          0.0612
_refine_ls_wR_factor_all         0.0674

# 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                2155
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_gt          0.0612

_refine_ls_shift/su_max          0.000073
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method= Tukey and Prince
W = [weight] * [1-(deltaF/6*sigmaF)^2]^2

3.40 2.03 2.88
;
_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., 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
O1 O -0.05703(19) -0.2224(2) -0.04676(8) 0.0357 1.0000 Uani .
C2 C -0.2024(3) -0.2162(3) -0.11820(11) 0.0314 1.0000 Uani .
N3 N -0.1190(2) -0.1761(2) -0.1904(1) 0.0290 1.0000 Uani .
C4 C 0.0869(3) -0.1212(2) -0.16091(11) 0.0283 1.0000 Uani .
C5 C 0.1363(2) -0.2184(3) -0.07350(12) 0.0315 1.0000 Uani .
C6 C 0.1920(3) -0.3966(3) -0.08986(16) 0.0418 1.0000 Uani .
C7 C 0.2778(3) -0.1445(3) 0.00315(13) 0.0408 1.0000 Uani .
C8 C 0.1039(3) 0.0679(3) -0.15365(14) 0.0380 1.0000 Uani .
C9 C 0.3165(4) 0.1203(3) -0.1518(2) 0.0550 1.0000 Uani .
C10 C -0.0316(5) 0.1582(3) -0.2281(2) 0.0611 1.0000 Uani .
C11 C -0.1970(3) -0.2059(2) -0.27939(11) 0.0320 1.0000 Uani .
O12 O -0.0937(2) -0.1783(3) -0.33260(9) 0.0475 1.0000 Uani .
C13 C -0.3989(3) -0.2830(2) -0.30468(12) 0.0299 1.0000 Uani .
C14 C -0.4982(3) -0.2326(3) -0.39787(12) 0.0340 1.0000 Uani .
C15 C -0.6988(3) -0.3173(3) -0.42192(14) 0.0422 1.0000 Uani .
C16 C -0.6991(3) -0.4967(3) -0.39647(15) 0.0449 1.0000 Uani .
C17 C -0.8792(5) -0.5933(5) -0.4377(2) 0.0687 1.0000 Uani .
C18 C -0.5501(4) -0.5638(3) -0.34107(16) 0.0477 1.0000 Uani .
C19 C -0.3699(3) -0.4713(3) -0.29752(16) 0.0415 1.0000 Uani .
C20 C -0.5256(4) -0.0452(3) -0.40647(17) 0.0516 1.0000 Uani .
O21 O -0.3715(2) -0.2399(3) -0.11496(9) 0.0435 1.0000 Uani .
H41 H 0.1781 -0.1474 -0.2013 0.0393 1.0000 Uiso .
H61 H 0.3212 -0.4010 -0.1081 0.0562 1.0000 Uiso .
H62 H 0.0883 -0.4459 -0.1379 0.0562 1.0000 Uiso .
H63 H 0.1969 -0.4638 -0.0350 0.0562 1.0000 Uiso .
H71 H 0.4109 -0.1400 -0.0098 0.0546 1.0000 Uiso .
H72 H 0.2794 -0.2196 0.0564 0.0546 1.0000 Uiso .
H73 H 0.2322 -0.0334 0.0175 0.0546 1.0000 Uiso .
H81 H 0.0567 0.1031 -0.0983 0.0484 1.0000 Uiso .
H91 H 0.3342 0.2411 -0.1467 0.0731 1.0000 Uiso .
H92 H 0.3600 0.0805 -0.2072 0.0731 1.0000 Uiso .
H93 H 0.4075 0.0652 -0.1001 0.0731 1.0000 Uiso .
H101 H -0.0163 0.2774 -0.2233 0.0727 1.0000 Uiso .
H102 H 0.0095 0.1213 -0.2868 0.0727 1.0000 Uiso .
H103 H -0.1705 0.1231 -0.2328 0.0727 1.0000 Uiso .
H131 H -0.4900 -0.2456 -0.2641 0.0402 1.0000 Uiso .
H141 H -0.4111 -0.2668 -0.4391 0.0458 1.0000 Uiso .
H151 H -0.7452 -0.3074 -0.4880 0.0535 1.0000 Uiso .
H152 H -0.7943 -0.2545 -0.3929 0.0535 1.0000 Uiso .
H171 H -0.8681 -0.7114 -0.4168 0.0909 1.0000 Uiso .
H172 H -0.8958 -0.5919 -0.5031 0.0909 1.0000 Uiso .
H173 H -0.9996 -0.5433 -0.4207 0.0909 1.0000 Uiso .
H181 H -0.5604 -0.6840 -0.3252 0.0616 1.0000 Uiso .
H191 H -0.2587 -0.5019 -0.3272 0.0565 1.0000 Uiso .
H192 H -0.3345 -0.5035 -0.2339 0.0565 1.0000 Uiso .
H201 H -0.5872 -0.0145 -0.4677 0.0703 1.0000 Uiso .
H202 H -0.6090 -0.0052 -0.3648 0.0703 1.0000 Uiso .
H203 H -0.3925 0.0109 -0.3907 0.0703 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
O1 0.0285(6) 0.0483(8) 0.0315(6) 0.0047(6) 0.0091(4) 0.0028(6)
C2 0.0287(7) 0.0353(8) 0.0320(7) -0.0000(7) 0.0108(6) 0.0042(7)
N3 0.0255(6) 0.0329(7) 0.0301(6) -0.0015(5) 0.0088(5) -0.0023(5)
C4 0.0281(7) 0.0272(7) 0.0311(7) -0.0027(6) 0.0091(6) -0.0012(6)
C5 0.0256(7) 0.0342(8) 0.0361(8) 0.0019(7) 0.0098(6) 0.0014(7)
C6 0.0362(9) 0.0290(9) 0.0619(13) 0.0065(9) 0.0137(8) 0.0048(8)
C7 0.0319(9) 0.0545(12) 0.0347(9) -0.0004(9) 0.0031(7) 0.0021(8)
C8 0.043(1) 0.0262(8) 0.044(1) -0.0027(7) 0.0042(8) -0.0027(7)
C9 0.0518(13) 0.0389(11) 0.0711(16) 0.0018(11) 0.0039(11) -0.015(1)
C10 0.0689(17) 0.0325(11) 0.0720(17) 0.0127(11) -0.0110(13) -0.0026(11)
C11 0.0338(8) 0.0337(9) 0.0297(7) -0.0019(7) 0.0091(6) -0.0012(7)
O12 0.0397(8) 0.0729(13) 0.0329(6) -0.0061(7) 0.0141(5) -0.0141(7)
C13 0.0268(8) 0.0300(8) 0.0328(8) 0.0008(7) 0.0054(6) 0.0002(6)
C14 0.0350(8) 0.0342(9) 0.0323(8) 0.0005(7) 0.0053(6) 0.0026(7)
C15 0.0323(9) 0.0549(13) 0.0373(9) -0.0031(9) 0.0011(7) 0.0043(8)
C16 0.041(1) 0.0556(14) 0.039(1) -0.0078(9) 0.0084(8) -0.0155(9)
C17 0.0558(15) 0.096(3) 0.0525(13) -0.0182(15) 0.0073(11) -0.0380(16)
C18 0.0570(13) 0.035(1) 0.0488(11) -0.0023(9) 0.006(1) -0.012(1)
C19 0.040(1) 0.0285(8) 0.0522(11) 0.0045(9) 0.0002(8) 0.0018(8)
C20 0.0675(15) 0.0361(11) 0.0499(12) 0.007(1) 0.0075(11) 0.0080(11)
O21 0.0283(6) 0.0657(11) 0.0398(7) 0.0035(7) 0.0150(5) -0.0004(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
O1 . C2 . 1.347(2) yes
O1 . C5 . 1.479(2) yes
C2 . N3 . 1.394(2) yes
C2 . O21 . 1.200(2) yes
N3 . C4 . 1.481(2) yes
N3 . C11 . 1.403(2) yes
C4 . C5 . 1.547(2) yes
C4 . C8 . 1.538(3) yes
C4 . H41 . 0.995 no
C5 . C6 . 1.528(3) yes
C5 . C7 . 1.511(3) yes
C6 . H61 . 0.992 no
C6 . H62 . 1.011 no
C6 . H63 . 1.004 no
C7 . H71 . 0.984 no
C7 . H72 . 1.024 no
C7 . H73 . 0.993 no
C8 . C9 . 1.530(3) yes
C8 . C10 . 1.527(3) yes
C8 . H81 . 1.016 no
C9 . H91 . 0.987 no
C9 . H92 . 1.016 no
C9 . H93 . 1.022 no
C10 . H101 . 0.972 no
C10 . H102 . 1.048 no
C10 . H103 . 0.994 no
C11 . O12 . 1.214(2) yes
C11 . C13 . 1.515(2) yes
C13 . C14 . 1.531(2) yes
C13 . C19 . 1.539(3) yes
C13 . H131 . 1.020 no
C14 . C15 . 1.532(3) yes
C14 . C20 . 1.531(3) yes
C14 . H141 . 1.001 no
C15 . C16 . 1.506(4) yes
C15 . H151 . 1.015 no
C15 . H152 . 1.007 no
C16 . C17 . 1.507(3) yes
C16 . C18 . 1.325(4) yes
C17 . H171 . 1.007 no
C17 . H172 . 0.999 no
C17 . H173 . 1.009 no
C18 . C19 . 1.501(3) yes
C18 . H181 . 1.010 no
C19 . H191 . 1.003 no
C19 . H192 . 1.004 no
C20 . H201 . 0.994 no
C20 . H202 . 1.001 no
C20 . H203 . 1.015 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 . O1 . C5 . 110.10(13) yes
O1 . C2 . N3 . 107.92(15) yes
O1 . C2 . O21 . 122.82(16) yes
N3 . C2 . O21 . 129.25(17) yes
C2 . N3 . C4 . 110.37(14) yes
C2 . N3 . C11 . 127.51(15) yes
C4 . N3 . C11 . 121.34(14) yes
N3 . C4 . C5 . 98.87(13) yes
N3 . C4 . C8 . 112.16(16) yes
C5 . C4 . C8 . 116.19(16) yes
N3 . C4 . H41 . 115.792 no
C5 . C4 . H41 . 112.477 no
C8 . C4 . H41 . 102.065 no
O1 . C5 . C4 . 101.40(13) yes
O1 . C5 . C6 . 107.34(16) yes
C4 . C5 . C6 . 110.81(16) yes
O1 . C5 . C7 . 105.92(15) yes
C4 . C5 . C7 . 119.19(18) yes
C6 . C5 . C7 . 110.99(17) yes
C5 . C6 . H61 . 110.645 no
C5 . C6 . H62 . 109.161 no
H61 . C6 . H62 . 109.191 no
C5 . C6 . H63 . 109.804 no
H61 . C6 . H63 . 109.766 no
H62 . C6 . H63 . 108.231 no
C5 . C7 . H71 . 110.282 no
C5 . C7 . H72 . 107.662 no
H71 . C7 . H72 . 108.842 no
C5 . C7 . H73 . 110.412 no
H71 . C7 . H73 . 111.412 no
H72 . C7 . H73 . 108.117 no
C4 . C8 . C9 . 109.71(19) yes
C4 . C8 . C10 . 113.20(18) yes
C9 . C8 . C10 . 109.4(2) yes
C4 . C8 . H81 . 107.941 no
C9 . C8 . H81 . 111.992 no
C10 . C8 . H81 . 104.596 no
C8 . C9 . H91 . 112.371 no
C8 . C9 . H92 . 109.885 no
H91 . C9 . H92 . 109.262 no
C8 . C9 . H93 . 109.859 no
H91 . C9 . H93 . 108.740 no
H92 . C9 . H93 . 106.545 no
C8 . C10 . H101 . 112.029 no
C8 . C10 . H102 . 106.773 no
H101 . C10 . H102 . 107.793 no
C8 . C10 . H103 . 111.380 no
H101 . C10 . H103 . 112.304 no
H102 . C10 . H103 . 106.160 no
N3 . C11 . O12 . 118.13(17) yes
N3 . C11 . C13 . 119.13(14) yes
O12 . C11 . C13 . 122.56(16) yes
C11 . C13 . C14 . 111.04(15) yes
C11 . C13 . C19 . 106.75(16) yes
C14 . C13 . C19 . 111.16(16) yes
C11 . C13 . H131 . 111.749 no
C14 . C13 . H131 . 106.482 no
C19 . C13 . H131 . 109.716 no
C13 . C14 . C15 . 109.39(16) yes
C13 . C14 . C20 . 111.84(17) yes
C15 . C14 . C20 . 109.3(2) yes
C13 . C14 . H141 . 108.199 no
C15 . C14 . H141 . 110.707 no
C20 . C14 . H141 . 107.374 no
C14 . C15 . C16 . 114.54(18) yes
C14 . C15 . H151 . 107.788 no
C16 . C15 . H151 . 108.899 no
C14 . C15 . H152 . 108.113 no
C16 . C15 . H152 . 109.618 no
H151 . C15 . H152 . 107.663 no
C15 . C16 . C17 . 115.6(3) yes
C15 . C16 . C18 . 121.7(2) yes
C17 . C16 . C18 . 122.7(3) yes
C16 . C17 . H171 . 110.504 no
C16 . C17 . H172 . 110.330 no
H171 . C17 . H172 . 108.953 no
C16 . C17 . H173 . 109.977 no
H171 . C17 . H173 . 108.200 no
H172 . C17 . H173 . 108.825 no
C16 . C18 . C19 . 124.4(2) yes
C16 . C18 . H181 . 118.015 no
C19 . C18 . H181 . 117.587 no
C13 . C19 . C18 . 112.07(18) yes
C13 . C19 . H191 . 108.265 no
C18 . C19 . H191 . 108.537 no
C13 . C19 . H192 . 109.383 no
C18 . C19 . H192 . 109.644 no
H191 . C19 . H192 . 108.882 no
C14 . C20 . H201 . 110.739 no
C14 . C20 . H202 . 109.981 no
H201 . C20 . H202 . 109.876 no
C14 . C20 . H203 . 109.310 no
H201 . C20 . H203 . 108.726 no
H202 . C20 . H203 . 108.155 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

# Attachment 'CCDC280123.cif'

data_CRYSTALS_cif_2
_database_code_depnum_ccdc_archive 'CCDC 280123'

_audit_creation_date             04-18-08
_audit_creation_method           CRYSTALS_ver_12-03-99

#==============================================================================
# 4. TEXT

_publ_section_abstract           #Text of the abstract
;
?
;

_publ_section_comment            #Text of the paper
;
?
;

_publ_section_acknowledgements   # Acknowledgments
;
?
;

_publ_section_figure_captions    #Captions to figures
;
?
;

_publ_section_exptl_refinement   
# see also _refine_ls_hydrogen for refinement keywords.
;
H atoms placed geometrically after each cycle
;

_publ_section_exptl_prep         
;
?
;

#==========================================================================

_chemical_name_systematic        # IUPAC name, in full
?

_chemical_melting_point          ?

# choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse'
_refine_ls_matrix_type           full

# choose from 'heavy, direct, difmap, geom'
_atom_sites_solution_primary     direct

# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

# choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed'
_refine_ls_hydrogen_treatment    constr

#****************************************************************************
# General computing
#=============================================================
_computing_structure_refinement  
;
CRYSTALS (Watkin et al 2001)
;
_computing_publication_material  
;
CRYSTALS (Watkin et al 2001)
;
_computing_molecular_graphics    
;
CAMERON (Watkin et al 1996)
;
#=============================================================

_cell_length_a                   7.2402(1)
_cell_angle_alpha                90
_cell_length_b                   11.8197(2)
_cell_angle_beta                 90
_cell_length_c                   18.4670(5)
_cell_angle_gamma                90
_cell_volume                     1580.35(5)

_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            'C17 H25 N1 O3'
_chemical_formula_moiety         'C17 H25 N1 O3'
_chemical_compound_source        ?
_chemical_formula_weight         291.39

_cell_measurement_reflns_used    1967
_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    1.225
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             632.000
_exptl_absorpt_coefficient_mu    0.083
# Sheldrick geometric definitions 0.98 0.98

_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  0.98
_exptl_absorpt_correction_T_max  0.98

_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            3546
_reflns_number_total             2050
_diffrn_reflns_av_R_equivalents  0.01
# Number of reflections with Friedels Law is 2050
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 1805

_diffrn_reflns_theta_min         5.238
_diffrn_reflns_theta_max         27.469
_diffrn_measured_fraction_theta_max 0.987

_diffrn_reflns_theta_full        27.125
_diffrn_measured_fraction_theta_full 0.990

_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_reflns_limit_h_min              0
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              23

_refine_diff_density_min         -0.14
_refine_diff_density_max         0.17

_refine_ls_number_reflns         1759
_refine_ls_number_parameters     191

#_refine_ls_R_factor_ref 0.0318
_refine_ls_wR_factor_ref         0.0396
_refine_ls_goodness_of_fit_ref   1.0818

#_reflns_number_all 2050
_refine_ls_R_factor_all          0.0387
_refine_ls_wR_factor_all         0.0446

# 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                1759
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_gt          0.0396

_refine_ls_shift/su_max          0.000228
_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

1.03 0.424 0.677
;
_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

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

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
N1 N -0.86687(19) -0.22039(11) -0.12508(7) 0.0244 1.0000 Uani .
C2 C -0.8292(2) -0.30722(13) -0.18064(8) 0.0260 1.0000 Uani .
C3 C -0.8400(3) -0.41438(14) -0.13348(9) 0.0319 1.0000 Uani .
O4 O -0.7812(2) -0.3723(1) -0.06179(6) 0.0335 1.0000 Uani .
C5 C -0.8193(2) -0.26109(14) -0.05617(8) 0.0276 1.0000 Uani .
O6 O -0.8087(2) -0.2108(1) -0.00001(6) 0.0356 1.0000 Uani .
C7 C -0.7114(3) -0.51064(16) -0.1539(1) 0.0434 1.0000 Uani .
C8 C -1.0383(3) -0.45503(16) -0.12651(11) 0.0422 1.0000 Uani .
C9 C -0.6459(2) -0.28499(15) -0.22085(9) 0.0324 1.0000 Uani .
C10 C -0.6676(3) -0.19457(16) -0.2795(1) 0.0387 1.0000 Uani .
C11 C -0.4852(3) -0.2547(2) -0.17072(11) 0.0482 1.0000 Uani .
C12 C -0.9617(2) -0.12007(12) -0.14176(8) 0.0242 1.0000 Uani .
C13 C -0.9700(2) -0.02962(13) -0.08469(8) 0.0229 1.0000 Uani .
C14 C -0.7748(2) 0.02573(14) -0.07046(9) 0.0299 1.0000 Uani .
C15 C -0.8392(3) 0.13139(15) -0.02858(9) 0.0349 1.0000 Uani .
C16 C -0.9585(3) 0.17526(14) -0.09164(9) 0.0322 1.0000 Uani .
C17 C -1.0930(2) 0.07330(13) -0.10448(9) 0.0262 1.0000 Uani .
C18 C -1.2690(2) 0.08012(15) -0.05965(11) 0.0357 1.0000 Uani .
C19 C -0.8197(3) 0.16976(16) -0.1525(1) 0.0366 1.0000 Uani .
C20 C -0.7126(2) 0.07981(16) -0.1409(1) 0.0354 1.0000 Uani .
O21 O -1.02730(19) -0.1103(1) -0.20204(6) 0.0344 1.0000 Uani .
H21 H -0.9166 -0.3072 -0.2231 0.0304 1.0000 Uiso .
H71 H -0.7253 -0.5756 -0.1203 0.0517 1.0000 Uiso .
H72 H -0.7343 -0.5352 -0.2048 0.0517 1.0000 Uiso .
H73 H -0.5775 -0.4827 -0.1508 0.0517 1.0000 Uiso .
H81 H -1.0446 -0.5256 -0.0953 0.0503 1.0000 Uiso .
H82 H -1.0917 -0.4732 -0.1750 0.0503 1.0000 Uiso .
H83 H -1.1168 -0.3952 -0.1027 0.0503 1.0000 Uiso .
H91 H -0.6115 -0.3604 -0.2432 0.0393 1.0000 Uiso .
H101 H -0.5479 -0.1826 -0.3052 0.0456 1.0000 Uiso .
H102 H -0.7635 -0.2197 -0.3157 0.0456 1.0000 Uiso .
H103 H -0.7089 -0.1219 -0.2570 0.0456 1.0000 Uiso .
H111 H -0.3698 -0.2418 -0.1990 0.0562 1.0000 Uiso .
H112 H -0.4641 -0.3151 -0.1338 0.0562 1.0000 Uiso .
H113 H -0.5163 -0.1816 -0.1439 0.0562 1.0000 Uiso .
H131 H -1.0204 -0.0720 -0.0411 0.0264 1.0000 Uiso .
H141 H -0.6796 -0.0261 -0.0484 0.0353 1.0000 Uiso .
H151 H -0.9081 0.1133 0.0167 0.0425 1.0000 Uiso .
H152 H -0.7330 0.1838 -0.0159 0.0425 1.0000 Uiso .
H161 H -1.0271 0.2501 -0.0844 0.0373 1.0000 Uiso .
H171 H -1.1398 0.0686 -0.1564 0.0319 1.0000 Uiso .
H181 H -1.3445 0.1475 -0.0742 0.0429 1.0000 Uiso .
H182 H -1.3449 0.0101 -0.0653 0.0429 1.0000 Uiso .
H183 H -1.2352 0.0887 -0.0067 0.0429 1.0000 Uiso .
H191 H -0.8082 0.2240 -0.1947 0.0427 1.0000 Uiso .
H201 H -0.6121 0.0513 -0.1749 0.0418 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
N1 0.0311(6) 0.0230(6) 0.0192(6) -0.0034(5) -0.0009(5) 0.0034(5)
C2 0.0319(8) 0.0242(7) 0.0219(7) -0.0043(6) -0.0008(6) 0.0040(6)
C3 0.0440(9) 0.0267(7) 0.0250(7) -0.0026(7) -0.0035(7) 0.0041(7)
O4 0.0511(7) 0.0251(5) 0.0243(5) 0.0001(5) -0.0051(5) 0.0081(6)
C5 0.0336(8) 0.0264(7) 0.0229(7) 0.0012(6) -0.0010(6) 0.0036(6)
O6 0.0516(8) 0.0333(6) 0.0221(5) -0.0021(5) -0.0043(5) 0.0041(6)
C7 0.0656(13) 0.0283(8) 0.0363(9) -0.0043(7) -0.0046(9) 0.0142(9)
C8 0.0529(11) 0.0326(9) 0.0412(9) -0.0038(8) 0.0021(9) -0.0096(9)
C9 0.0348(8) 0.0350(8) 0.0272(7) -0.0053(7) 0.0035(7) 0.0046(7)
C10 0.046(1) 0.0395(9) 0.0308(8) -0.0001(7) 0.0080(8) -0.0044(8)
C11 0.0304(9) 0.0726(14) 0.042(1) -0.003(1) 0.0018(8) 0.003(1)
C12 0.0236(6) 0.0236(7) 0.0255(7) -0.0002(6) 0.0008(6) -0.0009(6)
C13 0.0234(6) 0.0218(7) 0.0236(6) -0.0006(6) 0.0006(6) 0.0007(6)
C14 0.0271(7) 0.0302(8) 0.0325(8) -0.0043(7) -0.0043(6) -0.0033(6)
C15 0.0412(9) 0.0302(8) 0.0333(8) -0.0060(7) -0.0045(8) -0.0058(7)
C16 0.0389(8) 0.0226(7) 0.0351(8) -0.0003(6) -0.0004(8) -0.0018(7)
C17 0.0280(7) 0.0211(7) 0.0294(8) 0.0002(6) -0.0004(6) 0.0006(6)
C18 0.0305(8) 0.0316(8) 0.0450(9) 0.0032(8) 0.0064(8) 0.0062(7)
C19 0.0389(9) 0.0334(8) 0.0376(9) 0.0031(7) 0.0005(8) -0.0126(8)
C20 0.0276(8) 0.0391(9) 0.0395(9) -0.0031(8) 0.0034(7) -0.0099(7)
O21 0.0433(7) 0.0342(6) 0.0257(5) -0.0034(5) -0.0094(5) 0.0077(6)
_refine_ls_extinction_coef       889.9(1004)
_refine_ls_extinction_method     'Larson 1970 Crystallographic Computing eq 22'
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
N1 . C2 . 1.4766(18) yes
N1 . C5 . 1.4034(19) yes
N1 . C12 . 1.405(2) yes
C2 . C3 . 1.539(2) yes
C2 . C9 . 1.543(2) yes
C2 . H21 . 1.007 no
C3 . O4 . 1.477(2) yes
C3 . C7 . 1.517(3) yes
C3 . C8 . 1.519(3) yes
O4 . C5 . 1.348(2) yes
C5 . O6 . 1.1977(19) yes
C7 . H71 . 0.992 no
C7 . H72 . 0.998 no
C7 . H73 . 1.026 no
C8 . H81 . 1.014 no
C8 . H82 . 1.000 no
C8 . H83 . 1.008 no
C9 . C10 . 1.530(2) yes
C9 . C11 . 1.530(3) yes
C9 . H91 . 1.013 no
C10 . H101 . 0.999 no
C10 . H102 . 1.009 no
C10 . H103 . 0.999 no
C11 . H111 . 0.997 no
C11 . H112 . 0.999 no
C11 . H113 . 1.021 no
C12 . C13 . 1.502(2) yes
C12 . O21 . 1.2155(19) yes
C13 . C14 . 1.580(2) yes
C13 . C17 . 1.551(2) yes
C13 . H131 . 1.017 no
C14 . C15 . 1.541(2) yes
C14 . C20 . 1.518(2) yes
C14 . H141 . 1.009 no
C15 . C16 . 1.540(3) yes
C15 . H151 . 0.998 no
C15 . H152 . 1.015 no
C16 . C17 . 1.568(2) yes
C16 . C19 . 1.509(3) yes
C16 . H161 . 1.023 no
C17 . C18 . 1.521(2) yes
C17 . H171 . 1.019 no
C18 . H181 . 1.003 no
C18 . H182 . 0.999 no
C18 . H183 . 1.013 no
C19 . C20 . 1.333(3) yes
C19 . H191 . 1.013 no
C20 . H201 . 1.018 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 . N1 . C5 . 110.28(12) yes
C2 . N1 . C12 . 121.65(12) yes
C5 . N1 . C12 . 127.46(13) yes
N1 . C2 . C3 . 99.75(12) yes
N1 . C2 . C9 . 112.02(13) yes
C3 . C2 . C9 . 117.13(14) yes
N1 . C2 . H21 . 115.107 no
C3 . C2 . H21 . 114.114 no
C9 . C2 . H21 . 99.550 no
C2 . C3 . O4 . 102.46(12) yes
C2 . C3 . C7 . 116.46(15) yes
O4 . C3 . C7 . 107.32(14) yes
C2 . C3 . C8 . 110.87(15) yes
O4 . C3 . C8 . 107.63(15) yes
C7 . C3 . C8 . 111.31(16) yes
C3 . O4 . C5 . 109.77(12) yes
N1 . C5 . O4 . 108.35(13) yes
N1 . C5 . O6 . 129.12(14) yes
O4 . C5 . O6 . 122.52(14) yes
C3 . C7 . H71 . 111.319 no
C3 . C7 . H72 . 110.485 no
H71 . C7 . H72 . 110.298 no
C3 . C7 . H73 . 108.964 no
H71 . C7 . H73 . 108.063 no
H72 . C7 . H73 . 107.596 no
C3 . C8 . H81 . 110.549 no
C3 . C8 . H82 . 110.950 no
H81 . C8 . H82 . 108.353 no
C3 . C8 . H83 . 110.360 no
H81 . C8 . H83 . 107.687 no
H82 . C8 . H83 . 108.851 no
C2 . C9 . C10 . 111.79(14) yes
C2 . C9 . C11 . 113.75(13) yes
C10 . C9 . C11 . 110.06(16) yes
C2 . C9 . H91 . 104.939 no
C10 . C9 . H91 . 110.572 no
C11 . C9 . H91 . 105.401 no
C9 . C10 . H101 . 110.288 no
C9 . C10 . H102 . 109.581 no
H101 . C10 . H102 . 108.851 no
C9 . C10 . H103 . 109.666 no
H101 . C10 . H103 . 109.610 no
H102 . C10 . H103 . 108.818 no
C9 . C11 . H111 . 110.898 no
C9 . C11 . H112 . 111.229 no
H111 . C11 . H112 . 109.773 no
C9 . C11 . H113 . 108.919 no
H111 . C11 . H113 . 108.027 no
H112 . C11 . H113 . 107.887 no
N1 . C12 . C13 . 117.80(12) yes
N1 . C12 . O21 . 118.15(14) yes
C13 . C12 . O21 . 124.01(14) yes
C12 . C13 . C14 . 112.06(13) yes
C12 . C13 . C17 . 114.57(12) yes
C14 . C13 . C17 . 103.18(12) yes
C12 . C13 . H131 . 102.696 no
C14 . C13 . H131 . 113.170 no
C17 . C13 . H131 . 111.537 no
C13 . C14 . C15 . 98.54(13) yes
C13 . C14 . C20 . 107.32(13) yes
C15 . C14 . C20 . 100.29(13) yes
C13 . C14 . H141 . 115.282 no
C15 . C14 . H141 . 119.799 no
C20 . C14 . H141 . 113.508 no
C14 . C15 . C16 . 93.61(13) yes
C14 . C15 . H151 . 113.478 no
C16 . C15 . H151 . 115.219 no
C14 . C15 . H152 . 112.400 no
C16 . C15 . H152 . 113.227 no
H151 . C15 . H152 . 108.439 no
C15 . C16 . C17 . 101.78(13) yes
C15 . C16 . C19 . 100.09(15) yes
C17 . C16 . C19 . 105.55(14) yes
C15 . C16 . H161 . 117.712 no
C17 . C16 . H161 . 112.487 no
C19 . C16 . H161 . 117.230 no
C13 . C17 . C16 . 102.15(12) yes
C13 . C17 . C18 . 113.21(13) yes
C16 . C17 . C18 . 113.41(14) yes
C13 . C17 . H171 . 111.678 no
C16 . C17 . H171 . 113.017 no
C18 . C17 . H171 . 103.722 no
C17 . C18 . H181 . 110.620 no
C17 . C18 . H182 . 111.099 no
H181 . C18 . H182 . 109.286 no
C17 . C18 . H183 . 109.143 no
H181 . C18 . H183 . 108.136 no
H182 . C18 . H183 . 108.482 no
C16 . C19 . C20 . 107.58(15) yes
C16 . C19 . H191 . 126.896 no
C20 . C19 . H191 . 125.520 no
C14 . C20 . C19 . 107.50(16) yes
C14 . C20 . H201 . 126.964 no
C19 . C20 . H201 . 125.467 no

# Attachment 'CCDC280124.cif'

data_CRYSTALS_cif_3
_database_code_depnum_ccdc_archive 'CCDC 280124'

_audit_creation_date             05-07-05
_audit_creation_method           CRYSTALS_ver_12.50

_oxford_structure_analysis_title '7051521 pr75'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   6.51670(10)
_cell_length_b                   7.9303(2)
_cell_length_c                   15.8324(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.8893(9)
_cell_angle_gamma                90
_cell_volume                     817.17(3)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z

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 C 4.2.6.8 and 6.1.1.4'
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 C 4.2.6.8 and 6.1.1.4'
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 C 4.2.6.8 and 6.1.1.4'
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 C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            2

# Given Formula = C17 H23 N1 O3
# Dc = 1.18 Fooo = 312.00 Mu = 0.80 M = 289.37
# Found Formula = C17 H23 N1 O3
# Dc = 1.18 FOOO = 312.00 Mu = 0.80 M = 289.37

_chemical_formula_sum            'C17 H23 N1 O3'
_chemical_formula_moiety         'C17 H23 N1 O3'
_chemical_compound_source        ?
_chemical_formula_weight         289.37

_cell_measurement_reflns_used    1930
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    190

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.20

_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.080

# Sheldrick geometric approximatio 0.98 0.98
# No experimental values of Tmin/max available
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       \w

_computing_data_collection       'COLLECT (Nonius BV, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  ?
_diffrn_standards_interval_count ?
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      190
_diffrn_reflns_number            3540
_reflns_number_total             1991
_diffrn_reflns_av_R_equivalents  0.009
# Number of reflections with Friedels Law is 1991
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 1874

_diffrn_reflns_theta_min         5.142
_diffrn_reflns_theta_max         27.497
_diffrn_measured_fraction_theta_max 0.986

_diffrn_reflns_theta_full        26.672
_diffrn_measured_fraction_theta_full 0.986

_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_reflns_limit_h_min              -8
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              20

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.11
_refine_diff_density_max         0.15

_refine_ls_number_reflns         1805
_refine_ls_number_restraints     1
_refine_ls_number_parameters     190

#_refine_ls_R_factor_ref 0.0308
_refine_ls_wR_factor_ref         0.0328
_refine_ls_goodness_of_fit_ref   1.1366

#_reflns_number_all 1990
_refine_ls_R_factor_all          0.0348
_refine_ls_wR_factor_all         0.0384

# 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                1805
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_gt          0.0328

_refine_ls_shift/su_max          0.000333

# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration unk

_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
0.484 0.164 0.976E-01
;

_publ_section_abstract           # Text of the abstract
; ?
;
_publ_section_comment            # Text of the paper
; ?
;
_publ_section_acknowledgements   # Acknowledgments
; ?
;
_publ_section_figure_captions    # Captions to figures
; ?
;

_publ_section_exptl_refinement   # Some potentially useful phrases are:
;
Because the data were collected with molybdenum radiation, there were no
measurable anomalous differences, as a consequence of which it was
admissible to merge Freidel pairs of reflections.

All hydrogen atoms were found in difference density syntheses.

Hydrogen atoms were placed geometrically after each cycle.

Hydrogen atoms were seen in a difference density synthesis. Those
attached to carbon atoms were repositioned geometrically.

Hydrogen were initially refined with soft restraints on the
bonds to regularise their geometry (bond lengths to accepted values,
angles either set by symmetry or to accepted values, and
U[iso] dependent upon the adjacent bonded atom),
after which they were refined with riding constraints only.
;

_publ_section_exptl_prep         
; ?
;

# End of 'script/refcif.dat'

# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C.,
Polidori, G. & Camalli, M. (1994) J. Appl. Cryst. (27), 435-435

Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Nonius BV, COLLECT Software, (1997-2001)

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Watkin D.J. (1994),
Acta Cryst, A50, 411-437

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

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint

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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.51232(18) -0.01064(17) 0.80249(8) 0.0286 1.0000 Uani . . . . . .
C2 C 0.7186(2) -0.07461(19) 0.82944(9) 0.0262 1.0000 Uani . . . . . .
C3 C 0.6886(2) -0.2630(2) 0.80839(10) 0.0297 1.0000 Uani . . . . . .
O4 O 0.46733(16) -0.28591(15) 0.82326(7) 0.0352 1.0000 Uani . . . . . .
C5 C 0.3684(2) -0.1401(2) 0.80996(10) 0.0337 1.0000 Uani . . . . . .
O6 O 0.18396(17) -0.12893(19) 0.80757(10) 0.0506 1.0000 Uani . . . . . .
C7 C 0.7169(3) -0.2983(2) 0.71551(11) 0.0407 1.0000 Uani . . . . . .
C8 C 0.8065(3) -0.3889(2) 0.86350(12) 0.0387 1.0000 Uani . . . . . .
C9 C 0.7795(3) -0.0296(2) 0.92204(10) 0.0333 1.0000 Uani . . . . . .
C10 C 0.8378(3) 0.1568(2) 0.93022(11) 0.0441 1.0000 Uani . . . . . .
C11 C 0.6162(3) -0.0717(3) 0.98435(11) 0.0484 1.0000 Uani . . . . . .
C12 C 0.4844(2) 0.1428(2) 0.76014(10) 0.0297 1.0000 Uani . . . . . .
C13 C 0.2717(2) 0.1841(2) 0.72120(10) 0.0329 1.0000 Uani . . . . . .
C14 C 0.2453(2) 0.0942(2) 0.63614(10) 0.0329 1.0000 Uani . . . . . .
C15 C 0.4022(3) 0.0917(3) 0.58013(12) 0.0476 1.0000 Uani . . . . . .
C16 C 0.3750(3) 0.0108(4) 0.50233(12) 0.0625 1.0000 Uani . . . . . .
C17 C 0.1924(4) -0.0672(3) 0.48002(13) 0.0613 1.0000 Uani . . . . . .
C18 C 0.0348(4) -0.0644(3) 0.53453(14) 0.0605 1.0000 Uani . . . . . .
C19 C 0.0606(3) 0.0164(3) 0.61216(12) 0.0473 1.0000 Uani . . . . . .
C20 C 0.2458(3) 0.3751(2) 0.71140(14) 0.0494 1.0000 Uani . . . . . .
O21 O 0.63171(17) 0.23442(16) 0.75171(8) 0.0389 1.0000 Uani . . . . . .
H21 H 0.8231 -0.0248 0.7919 0.0321 1.0000 Uiso R . . . . .
H71 H 0.6954 -0.4220 0.7027 0.0499 1.0000 Uiso R . . . . .
H72 H 0.8569 -0.2650 0.6989 0.0499 1.0000 Uiso R . . . . .
H73 H 0.6115 -0.2327 0.6795 0.0499 1.0000 Uiso R . . . . .
H81 H 0.7738 -0.5065 0.8440 0.0460 1.0000 Uiso R . . . . .
H82 H 0.7674 -0.3770 0.9240 0.0460 1.0000 Uiso R . . . . .
H83 H 0.9580 -0.3692 0.8610 0.0460 1.0000 Uiso R . . . . .
H91 H 0.9048 -0.0980 0.9390 0.0397 1.0000 Uiso R . . . . .
H101 H 0.8786 0.1859 0.9896 0.0547 1.0000 Uiso R . . . . .
H102 H 0.9584 0.1814 0.8935 0.0547 1.0000 Uiso R . . . . .
H103 H 0.7198 0.2294 0.9094 0.0547 1.0000 Uiso R . . . . .
H111 H 0.6629 -0.0395 1.0432 0.0604 1.0000 Uiso R . . . . .
H112 H 0.5815 -0.1947 0.9826 0.0604 1.0000 Uiso R . . . . .
H113 H 0.4850 -0.0061 0.9687 0.0604 1.0000 Uiso R . . . . .
H131 H 0.1649 0.1402 0.7600 0.0409 1.0000 Uiso R . . . . .
H151 H 0.5353 0.1504 0.5962 0.0574 1.0000 Uiso R . . . . .
H161 H 0.4967 0.0052 0.4636 0.0751 1.0000 Uiso R . . . . .
H171 H 0.1677 -0.1254 0.4236 0.0755 1.0000 Uiso R . . . . .
H181 H -0.1016 -0.1197 0.5182 0.0704 1.0000 Uiso R . . . . .
H191 H -0.0543 0.0191 0.6527 0.0587 1.0000 Uiso R . . . . .
H201 H 0.1054 0.4029 0.6859 0.0615 1.0000 Uiso R . . . . .
H202 H 0.2645 0.4329 0.7675 0.0615 1.0000 Uiso R . . . . .
H203 H 0.3514 0.4203 0.6728 0.0615 1.0000 Uiso R . . . . .
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
N1 0.0208(5) 0.0286(6) 0.0364(6) 0.0025(5) -0.0001(5) -0.0014(5)
C2 0.0214(6) 0.0253(6) 0.0319(7) 0.0004(6) -0.0002(5) -0.0012(5)
C3 0.0260(6) 0.0249(7) 0.0385(8) -0.0016(6) 0.0033(6) -0.0031(6)
O4 0.0273(5) 0.0290(6) 0.0496(6) 0.0014(5) 0.0035(4) -0.0062(5)
C5 0.0260(7) 0.0337(8) 0.0416(8) 0.0031(7) 0.0023(6) -0.0042(7)
O6 0.0228(5) 0.0503(8) 0.0788(9) 0.0118(7) 0.0044(5) -0.0040(6)
C7 0.0440(8) 0.0348(9) 0.0436(9) -0.0091(8) 0.0060(7) -0.0040(8)
C8 0.0374(8) 0.0257(8) 0.0528(10) 0.0041(7) 0.0009(7) 0.0014(6)
C9 0.0373(8) 0.0293(8) 0.0325(7) 0.0014(6) -0.0057(6) 0.0004(6)
C10 0.0572(11) 0.0339(9) 0.0397(9) -0.0052(8) -0.0129(8) -0.0092(8)
C11 0.0661(12) 0.0450(10) 0.0346(8) -0.0010(8) 0.0091(8) -0.0033(10)
C12 0.0289(7) 0.0276(7) 0.0320(7) -0.0003(6) -0.0035(5) 0.0002(6)
C13 0.0288(7) 0.0324(8) 0.0371(8) -0.0011(6) -0.0032(6) 0.0038(6)
C14 0.0329(7) 0.0302(8) 0.0350(7) 0.0031(7) -0.0054(6) 0.0014(6)
C15 0.0368(9) 0.0649(13) 0.0407(9) -0.0029(9) -0.0032(7) -0.0011(9)
C16 0.0570(12) 0.0891(19) 0.0411(10) -0.0104(12) 0.0006(8) 0.0106(13)
C17 0.0743(14) 0.0646(14) 0.0432(10) -0.0124(11) -0.0157(10) 0.0026(12)
C18 0.0626(13) 0.0632(14) 0.0535(11) -0.0022(11) -0.0177(10) -0.0203(12)
C19 0.0419(9) 0.0549(12) 0.0443(9) 0.0038(9) -0.0067(7) -0.0152(9)
C20 0.0479(10) 0.0348(9) 0.0634(12) -0.0064(9) -0.0169(9) 0.0102(8)
O21 0.0351(6) 0.0329(6) 0.0477(7) 0.0078(5) -0.0081(5) -0.0071(5)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          2.106(3)
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
N1 . C2 . 1.4795(18) yes
N1 . C5 . 1.399(2) yes
N1 . C12 . 1.397(2) yes
C2 . C3 . 1.541(2) yes
C2 . C9 . 1.541(2) yes
C2 . H21 . 1.007 no
C3 . O4 . 1.4836(17) yes
C3 . C7 . 1.517(2) yes
C3 . C8 . 1.510(2) yes
O4 . C5 . 1.336(2) yes
C5 . O6 . 1.2041(19) yes
C7 . H71 . 1.010 no
C7 . H72 . 0.998 no
C7 . H73 . 1.014 no
C8 . H81 . 1.002 no
C8 . H82 . 1.008 no
C8 . H83 . 1.002 no
C9 . C10 . 1.530(2) yes
C9 . C11 . 1.524(3) yes
C9 . H91 . 1.005 no
C10 . H101 . 0.991 no
C10 . H102 . 1.020 no
C10 . H103 . 1.003 no
C11 . H111 . 0.999 no
C11 . H112 . 1.002 no
C11 . H113 . 1.020 no
C12 . C13 . 1.524(2) yes
C12 . O21 . 1.2167(19) yes
C13 . C14 . 1.526(2) yes
C13 . C20 . 1.531(2) yes
C13 . H131 . 1.013 no
C14 . C15 . 1.387(2) yes
C14 . C19 . 1.388(2) yes
C15 . C16 . 1.392(3) yes
C15 . H151 . 1.006 no
C16 . C17 . 1.371(3) yes
C16 . H161 . 1.028 no
C17 . C18 . 1.374(3) yes
C17 . H171 . 1.011 no
C18 . C19 . 1.389(3) yes
C18 . H181 . 1.013 no
C19 . H191 . 1.011 no
C20 . H201 . 1.006 no
C20 . H202 . 1.002 no
C20 . H203 . 1.009 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 . N1 . C5 . 109.10(13) yes
C2 . N1 . C12 . 122.11(12) yes
C5 . N1 . C12 . 127.44(12) yes
N1 . C2 . C3 . 99.57(11) yes
N1 . C2 . C9 . 112.43(12) yes
C3 . C2 . C9 . 117.00(12) yes
N1 . C2 . H21 . 109.095 no
C3 . C2 . H21 . 109.579 no
C9 . C2 . H21 . 108.733 no
C2 . C3 . O4 . 101.43(11) yes
C2 . C3 . C7 . 111.58(13) yes
O4 . C3 . C7 . 107.34(12) yes
C2 . C3 . C8 . 117.41(13) yes
O4 . C3 . C8 . 107.32(12) yes
C7 . C3 . C8 . 110.79(14) yes
C3 . O4 . C5 . 109.52(11) yes
N1 . C5 . O4 . 109.18(12) yes
N1 . C5 . O6 . 128.01(17) yes
O4 . C5 . O6 . 122.78(16) yes
C3 . C7 . H71 . 110.529 no
C3 . C7 . H72 . 111.391 no
H71 . C7 . H72 . 108.875 no
C3 . C7 . H73 . 109.791 no
H71 . C7 . H73 . 107.593 no
H72 . C7 . H73 . 108.561 no
C3 . C8 . H81 . 110.097 no
C3 . C8 . H82 . 109.980 no
H81 . C8 . H82 . 108.624 no
C3 . C8 . H83 . 110.361 no
H81 . C8 . H83 . 109.120 no
H82 . C8 . H83 . 108.618 no
C2 . C9 . C10 . 110.81(13) yes
C2 . C9 . C11 . 114.21(14) yes
C10 . C9 . C11 . 109.59(16) yes
C2 . C9 . H91 . 107.207 no
C10 . C9 . H91 . 107.694 no
C11 . C9 . H91 . 107.036 no
C9 . C10 . H101 . 111.065 no
C9 . C10 . H102 . 109.390 no
H101 . C10 . H102 . 108.591 no
C9 . C10 . H103 . 110.118 no
H101 . C10 . H103 . 109.979 no
H102 . C10 . H103 . 107.616 no
C9 . C11 . H111 . 110.969 no
C9 . C11 . H112 . 111.075 no
H111 . C11 . H112 . 109.405 no
C9 . C11 . H113 . 109.616 no
H111 . C11 . H113 . 107.937 no
H112 . C11 . H113 . 107.732 no
N1 . C12 . C13 . 118.38(13) yes
N1 . C12 . O21 . 119.24(13) yes
C13 . C12 . O21 . 122.27(14) yes
C12 . C13 . C14 . 108.44(13) yes
C12 . C13 . C20 . 110.31(14) yes
C14 . C13 . C20 . 111.46(15) yes
C12 . C13 . H131 . 108.661 no
C14 . C13 . H131 . 108.923 no
C20 . C13 . H131 . 108.995 no
C13 . C14 . C15 . 121.12(15) yes
C13 . C14 . C19 . 120.44(15) yes
C15 . C14 . C19 . 118.42(16) yes
C14 . C15 . C16 . 120.44(18) yes
C14 . C15 . H151 . 119.090 no
C16 . C15 . H151 . 120.462 no
C15 . C16 . C17 . 120.4(2) yes
C15 . C16 . H161 . 118.637 no
C17 . C16 . H161 . 120.872 no
C16 . C17 . C18 . 119.80(19) yes
C16 . C17 . H171 . 122.048 no
C18 . C17 . H171 . 118.138 no
C17 . C18 . C19 . 120.14(19) yes
C17 . C18 . H181 . 120.397 no
C19 . C18 . H181 . 119.461 no
C18 . C19 . C14 . 120.79(19) yes
C18 . C19 . H191 . 120.727 no
C14 . C19 . H191 . 118.484 no
C13 . C20 . H201 . 110.528 no
C13 . C20 . H202 . 110.769 no
H201 . C20 . H202 . 108.872 no
C13 . C20 . H203 . 109.718 no
H201 . C20 . H203 . 108.305 no
H202 . C20 . H203 . 108.588 no