# Supplementary Material (ESI) for Organic and Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2010

data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Yves Genisson'
'Nathalie Andrieu-Abadie'
'Stephanie Ballereau'
'Sonia Ladeira'
'Karine Maaliki'
'Yahya Salma'

_publ_contact_author_name        'Yves Genisson'
_publ_contact_author_email       GENISSON@CHIMIE.UPS-TLSE.FR

_publ_section_title              
;
Flexible and enantioselective access to jaspine B and
biologically active chain-modified analogues thereof.
;

# Attachment 'Gnisson-X-ray-9-20.CIF'

data_9
_database_code_depnum_ccdc_archive 'CCDC 769812'
#TrackingRef 'Gnisson-X-ray-9-20.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H23 N O5'
_chemical_formula_weight         357.39
_chemical_absolute_configuration syn

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.4011(2)
_cell_length_b                   21.6780(6)
_cell_length_c                   11.5033(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.832(2)
_cell_angle_gamma                90.00
_cell_volume                     1843.35(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9934
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      29.92

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9466
_exptl_absorpt_correction_T_max  0.9817
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            31473
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         5.17
_diffrn_reflns_theta_max         30.51
_reflns_number_total             10457
_reflns_number_gt                8163
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0537P)^2^+0.2020P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.5(6)
_refine_ls_number_reflns         10457
_refine_ls_number_parameters     477
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1130
_refine_ls_wR_factor_gt          0.1015
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.81109(17) 0.79950(6) 0.62713(12) 0.0493(3) Uani 1 1 d . . .
O2 O 0.5935(2) 0.46097(7) 0.84919(13) 0.0598(4) Uani 1 1 d . . .
O3 O 0.32108(17) 0.47431(6) 0.75998(13) 0.0515(3) Uani 1 1 d . . .
O4 O 0.4122(2) 0.46038(5) 0.46849(14) 0.0540(3) Uani 1 1 d . . .
H4A H 0.497(3) 0.4493(11) 0.426(2) 0.065 Uiso 1 1 d . . .
O5 O 0.31318(19) 0.62113(5) 0.41539(12) 0.0517(3) Uani 1 1 d . . .
N1 N 0.55234(17) 0.52176(7) 0.68663(14) 0.0433(3) Uani 1 1 d . . .
C1 C 0.8708(3) 0.82637(10) 0.5219(2) 0.0563(5) Uani 1 1 d . . .
H1A H 0.7907 0.8132 0.4561 0.084 Uiso 1 1 calc R . .
H1B H 0.9947 0.8129 0.5092 0.084 Uiso 1 1 calc R . .
H1C H 0.8679 0.8714 0.5282 0.084 Uiso 1 1 calc R . .
C2 C 0.7987(2) 0.73637(8) 0.63151(15) 0.0394(4) Uani 1 1 d . . .
C3 C 0.8503(2) 0.69691(8) 0.54466(16) 0.0415(4) Uani 1 1 d . . .
H3 H 0.8989 0.7129 0.4759 0.050 Uiso 1 1 calc R . .
C4 C 0.8302(2) 0.63337(8) 0.55923(16) 0.0428(4) Uani 1 1 d . . .
H4 H 0.8648 0.6064 0.4992 0.051 Uiso 1 1 calc R . .
C5 C 0.7614(2) 0.60868(8) 0.65861(16) 0.0401(4) Uani 1 1 d . . .
C6 C 0.7118(2) 0.64936(9) 0.74513(17) 0.0458(4) Uani 1 1 d . . .
H6 H 0.6645 0.6334 0.8143 0.055 Uiso 1 1 calc R . .
C7 C 0.7297(2) 0.71239(9) 0.73271(17) 0.0463(4) Uani 1 1 d . . .
H7 H 0.6952 0.7393 0.7929 0.056 Uiso 1 1 calc R . .
C8 C 0.7399(2) 0.53965(9) 0.6724(2) 0.0481(4) Uani 1 1 d . . .
H8A H 0.7848 0.5187 0.6030 0.058 Uiso 1 1 calc R . .
H8B H 0.8148 0.5257 0.7411 0.058 Uiso 1 1 calc R . .
C9 C 0.5004(2) 0.48438(7) 0.77106(16) 0.0427(4) Uani 1 1 d . . .
C10 C 0.2433(2) 0.50967(8) 0.66430(18) 0.0462(4) Uani 1 1 d . . .
H10A H 0.1558 0.5402 0.6923 0.055 Uiso 1 1 calc R . .
H10B H 0.1796 0.4823 0.6069 0.055 Uiso 1 1 calc R . .
C11 C 0.40168(19) 0.54243(7) 0.60925(15) 0.0362(3) Uani 1 1 d . . .
H11 H 0.3870 0.5881 0.6165 0.043 Uiso 1 1 calc R . .
C12 C 0.4253(2) 0.52567(7) 0.48269(16) 0.0390(3) Uani 1 1 d . . .
H12 H 0.5483 0.5392 0.4609 0.047 Uiso 1 1 calc R . .
C13 C 0.2858(3) 0.55664(7) 0.40222(17) 0.0442(4) Uani 1 1 d . . .
H13A H 0.3016 0.5441 0.3206 0.053 Uiso 1 1 calc R . .
H13B H 0.1622 0.5452 0.4235 0.053 Uiso 1 1 calc R . .
C14 C 0.2178(2) 0.65732(7) 0.33186(15) 0.0377(3) Uani 1 1 d . . .
H14A H 0.0861 0.6514 0.3381 0.045 Uiso 1 1 calc R . .
H14B H 0.2501 0.6449 0.2527 0.045 Uiso 1 1 calc R . .
C15 C 0.26648(18) 0.72417(7) 0.35267(14) 0.0324(3) Uani 1 1 d . . .
C16 C 0.3444(2) 0.74367(7) 0.45875(15) 0.0383(3) Uani 1 1 d . . .
H16 H 0.3659 0.7150 0.5203 0.046 Uiso 1 1 calc R . .
C17 C 0.3909(2) 0.80538(8) 0.47446(17) 0.0452(4) Uani 1 1 d . . .
H17 H 0.4439 0.8186 0.5471 0.054 Uiso 1 1 calc R . .
C18 C 0.3610(3) 0.84749(8) 0.3860(2) 0.0532(5) Uani 1 1 d . . .
H18 H 0.3928 0.8896 0.3974 0.064 Uiso 1 1 calc R . .
C19 C 0.2843(3) 0.82800(9) 0.28033(19) 0.0537(5) Uani 1 1 d . . .
H19 H 0.2640 0.8568 0.2188 0.064 Uiso 1 1 calc R . .
C20 C 0.2366(2) 0.76634(8) 0.26366(16) 0.0427(4) Uani 1 1 d . . .
H20 H 0.1834 0.7533 0.1909 0.051 Uiso 1 1 calc R . .
O6 O 0.7463(2) 0.10036(6) 0.10910(12) 0.0536(3) Uani 1 1 d . . .
O7 O 0.7136(3) 0.45131(10) 0.3468(2) 0.1083(8) Uani 1 1 d . . .
O8 O 0.9953(2) 0.45726(7) 0.28754(16) 0.0695(4) Uani 1 1 d . . .
O9 O 0.8959(2) 0.46593(6) 0.00328(14) 0.0617(4) Uani 1 1 d . . .
H9 H 0.802(3) 0.4703(13) -0.042(3) 0.074 Uiso 1 1 d . . .
O10 O 1.1126(2) 0.32222(6) -0.06421(13) 0.0607(4) Uani 1 1 d . . .
N2 N 0.8115(2) 0.38899(7) 0.20274(14) 0.0450(3) Uani 1 1 d . . .
C21 C 0.6809(3) 0.06923(10) 0.0075(2) 0.0626(5) Uani 1 1 d . . .
H21A H 0.7349 0.0874 -0.0607 0.094 Uiso 1 1 calc R . .
H21B H 0.5490 0.0732 -0.0004 0.094 Uiso 1 1 calc R . .
H21C H 0.7136 0.0255 0.0132 0.094 Uiso 1 1 calc R . .
C22 C 0.7178(2) 0.16250(8) 0.11670(15) 0.0398(3) Uani 1 1 d . . .
C23 C 0.7905(2) 0.19109(8) 0.21679(16) 0.0427(4) Uani 1 1 d . . .
H23 H 0.8572 0.1675 0.2737 0.051 Uiso 1 1 calc R . .
C24 C 0.7667(2) 0.25312(8) 0.23388(17) 0.0428(4) Uani 1 1 d . . .
H24 H 0.8156 0.2719 0.3031 0.051 Uiso 1 1 calc R . .
C25 C 0.6716(2) 0.28898(8) 0.15093(17) 0.0412(4) Uani 1 1 d . . .
C26 C 0.6019(2) 0.26022(9) 0.05145(18) 0.0486(4) Uani 1 1 d . . .
H26 H 0.5377 0.2842 -0.0061 0.058 Uiso 1 1 calc R . .
C27 C 0.6225(2) 0.19740(9) 0.03284(16) 0.0468(4) Uani 1 1 d . . .
H27 H 0.5724 0.1786 -0.0360 0.056 Uiso 1 1 calc R . .
C28 C 0.6429(2) 0.35708(9) 0.1716(2) 0.0522(5) Uani 1 1 d . . .
H28A H 0.5866 0.3759 0.1003 0.063 Uiso 1 1 calc R . .
H28B H 0.5584 0.3624 0.2350 0.063 Uiso 1 1 calc R . .
C29 C 0.8284(3) 0.43341(9) 0.2837(2) 0.0605(5) Uani 1 1 d . . .
C30 C 1.1012(3) 0.42726(9) 0.20428(18) 0.0513(4) Uani 1 1 d . . .
H30A H 1.2010 0.4036 0.2437 0.062 Uiso 1 1 calc R . .
H30B H 1.1536 0.4578 0.1516 0.062 Uiso 1 1 calc R . .
C31 C 0.9710(2) 0.38361(7) 0.13546(15) 0.0370(3) Uani 1 1 d . . .
H31 H 1.0183 0.3404 0.1402 0.044 Uiso 1 1 calc R . .
C32 C 0.9347(3) 0.40171(7) 0.00855(16) 0.0441(4) Uani 1 1 d . . .
H32 H 0.8259 0.3786 -0.0228 0.053 Uiso 1 1 calc R . .
C33 C 1.0909(3) 0.38709(9) -0.06563(19) 0.0555(5) Uani 1 1 d . . .
H33A H 1.0654 0.4018 -0.1462 0.067 Uiso 1 1 calc R . .
H33B H 1.2024 0.4075 -0.0339 0.067 Uiso 1 1 calc R . .
C34 C 1.2076(2) 0.29908(9) -0.15727(16) 0.0444(4) Uani 1 1 d . . .
H34A H 1.3323 0.3157 -0.1535 0.053 Uiso 1 1 calc R . .
H34B H 1.1473 0.3122 -0.2319 0.053 Uiso 1 1 calc R . .
C35 C 1.2131(2) 0.22955(9) -0.15100(15) 0.0399(4) Uani 1 1 d . . .
C36 C 1.3011(2) 0.19718(10) -0.23661(16) 0.0497(4) Uani 1 1 d . . .
H36 H 1.3591 0.2190 -0.2959 0.060 Uiso 1 1 calc R . .
C37 C 1.3041(3) 0.13323(11) -0.2352(2) 0.0609(6) Uani 1 1 d . . .
H37 H 1.3635 0.1115 -0.2939 0.073 Uiso 1 1 calc R . .
C38 C 1.2218(3) 0.10109(11) -0.1495(2) 0.0609(6) Uani 1 1 d . . .
H38 H 1.2246 0.0573 -0.1490 0.073 Uiso 1 1 calc R . .
C39 C 1.1351(3) 0.13271(10) -0.0642(2) 0.0538(5) Uani 1 1 d . . .
H39 H 1.0781 0.1105 -0.0049 0.065 Uiso 1 1 calc R . .
C40 C 1.1308(2) 0.19686(9) -0.06461(17) 0.0447(4) Uani 1 1 d . . .
H40 H 1.0713 0.2183 -0.0055 0.054 Uiso 1 1 calc 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
O1 0.0535(7) 0.0453(6) 0.0488(8) -0.0039(6) 0.0014(6) 0.0008(5)
O2 0.0761(9) 0.0500(7) 0.0529(9) 0.0126(7) -0.0023(7) 0.0102(7)
O3 0.0513(7) 0.0461(7) 0.0582(9) 0.0099(6) 0.0138(6) -0.0071(5)
O4 0.0680(8) 0.0254(5) 0.0696(10) 0.0008(6) 0.0120(7) 0.0056(5)
O5 0.0727(8) 0.0268(5) 0.0530(8) -0.0005(5) -0.0229(7) 0.0030(5)
N1 0.0318(6) 0.0448(7) 0.0531(9) 0.0134(7) -0.0003(6) -0.0021(5)
C1 0.0576(11) 0.0510(10) 0.0604(14) 0.0076(10) 0.0044(9) -0.0019(8)
C2 0.0313(7) 0.0480(9) 0.0385(9) -0.0028(7) -0.0025(6) -0.0012(6)
C3 0.0409(8) 0.0504(9) 0.0334(9) 0.0004(7) 0.0034(7) -0.0064(7)
C4 0.0386(8) 0.0481(9) 0.0417(10) -0.0048(8) 0.0032(7) -0.0044(7)
C5 0.0260(6) 0.0498(9) 0.0443(10) 0.0034(7) -0.0016(6) -0.0025(6)
C6 0.0355(7) 0.0609(11) 0.0414(10) 0.0064(8) 0.0061(7) -0.0048(7)
C7 0.0400(8) 0.0594(11) 0.0398(10) -0.0071(8) 0.0054(7) 0.0018(7)
C8 0.0317(7) 0.0486(9) 0.0636(13) 0.0105(9) -0.0015(7) 0.0017(7)
C9 0.0534(9) 0.0316(7) 0.0433(10) 0.0017(7) 0.0063(8) 0.0030(6)
C10 0.0367(8) 0.0504(10) 0.0520(11) -0.0006(8) 0.0070(7) -0.0083(7)
C11 0.0293(6) 0.0327(7) 0.0465(10) 0.0033(6) -0.0003(6) -0.0005(5)
C12 0.0416(8) 0.0277(7) 0.0481(10) 0.0021(6) 0.0055(7) 0.0010(6)
C13 0.0582(10) 0.0287(7) 0.0449(10) -0.0037(7) -0.0056(8) 0.0000(6)
C14 0.0451(8) 0.0343(7) 0.0330(8) -0.0008(6) -0.0067(6) 0.0033(6)
C15 0.0308(6) 0.0320(6) 0.0343(8) 0.0004(6) 0.0005(6) 0.0030(5)
C16 0.0443(8) 0.0376(8) 0.0327(8) 0.0004(6) -0.0023(6) 0.0006(6)
C17 0.0493(9) 0.0420(8) 0.0436(10) -0.0065(7) -0.0048(7) -0.0061(7)
C18 0.0604(11) 0.0368(8) 0.0615(13) 0.0009(8) -0.0069(9) -0.0113(8)
C19 0.0672(11) 0.0389(8) 0.0537(12) 0.0163(8) -0.0117(9) -0.0055(8)
C20 0.0477(8) 0.0421(8) 0.0371(9) 0.0033(7) -0.0099(7) -0.0016(7)
O6 0.0694(8) 0.0432(7) 0.0476(8) 0.0034(6) -0.0042(6) -0.0023(6)
O7 0.1266(17) 0.0810(13) 0.1237(19) -0.0418(12) 0.0692(15) 0.0035(12)
O8 0.0884(11) 0.0529(8) 0.0677(11) -0.0233(7) 0.0080(8) -0.0146(7)
O9 0.0876(10) 0.0352(6) 0.0608(10) 0.0037(6) -0.0125(8) 0.0077(7)
O10 0.0972(11) 0.0429(7) 0.0449(8) 0.0022(6) 0.0320(7) -0.0004(7)
N2 0.0480(7) 0.0381(7) 0.0498(9) -0.0036(6) 0.0104(7) -0.0010(6)
C21 0.0845(15) 0.0513(11) 0.0517(13) -0.0035(10) -0.0006(11) -0.0074(10)
C22 0.0390(7) 0.0420(8) 0.0384(9) 0.0066(7) 0.0028(6) -0.0061(7)
C23 0.0407(8) 0.0457(9) 0.0411(10) 0.0099(7) -0.0047(7) -0.0040(6)
C24 0.0368(7) 0.0480(9) 0.0430(10) 0.0033(7) -0.0022(7) -0.0080(6)
C25 0.0299(7) 0.0423(8) 0.0517(10) 0.0081(7) 0.0036(7) -0.0028(6)
C26 0.0422(8) 0.0525(10) 0.0503(11) 0.0161(8) -0.0074(8) -0.0018(7)
C27 0.0488(9) 0.0536(10) 0.0371(10) 0.0060(8) -0.0056(7) -0.0069(8)
C28 0.0376(8) 0.0464(9) 0.0729(14) 0.0066(9) 0.0063(8) 0.0053(7)
C29 0.0838(15) 0.0411(9) 0.0581(14) -0.0049(9) 0.0175(11) 0.0078(10)
C30 0.0589(10) 0.0479(10) 0.0466(11) -0.0004(8) -0.0035(8) -0.0116(8)
C31 0.0411(7) 0.0308(6) 0.0393(9) -0.0008(6) 0.0039(6) -0.0027(6)
C32 0.0603(10) 0.0319(7) 0.0395(10) 0.0008(7) -0.0017(8) -0.0036(7)
C33 0.0803(13) 0.0401(9) 0.0474(12) 0.0051(8) 0.0166(10) -0.0106(9)
C34 0.0423(8) 0.0575(10) 0.0341(9) 0.0054(8) 0.0088(7) -0.0005(7)
C35 0.0319(7) 0.0559(10) 0.0317(9) 0.0002(7) 0.0014(6) 0.0039(7)
C36 0.0374(8) 0.0785(13) 0.0333(9) -0.0040(9) 0.0019(7) 0.0080(8)
C37 0.0529(10) 0.0775(14) 0.0515(12) -0.0230(11) -0.0049(9) 0.0217(10)
C38 0.0564(11) 0.0558(12) 0.0687(15) -0.0123(11) -0.0143(10) 0.0086(9)
C39 0.0522(10) 0.0532(10) 0.0555(12) 0.0034(9) -0.0016(9) -0.0007(8)
C40 0.0404(8) 0.0519(10) 0.0423(10) -0.0005(8) 0.0059(7) 0.0037(7)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.373(2) . ?
O1 C1 1.433(3) . ?
O2 C9 1.216(2) . ?
O3 C9 1.345(2) . ?
O3 C10 1.438(2) . ?
O4 C12 1.4275(18) . ?
O5 C14 1.4035(19) . ?
O5 C13 1.4197(19) . ?
N1 C9 1.336(2) . ?
N1 C8 1.458(2) . ?
N1 C11 1.462(2) . ?
C2 C3 1.383(3) . ?
C2 C7 1.395(3) . ?
C3 C4 1.396(2) . ?
C4 C5 1.382(3) . ?
C5 C6 1.393(3) . ?
C5 C8 1.514(3) . ?
C6 C7 1.381(3) . ?
C10 C11 1.534(2) . ?
C11 C12 1.519(3) . ?
C12 C13 1.510(2) . ?
C14 C15 1.509(2) . ?
C15 C20 1.382(2) . ?
C15 C16 1.390(2) . ?
C16 C17 1.391(2) . ?
C17 C18 1.377(3) . ?
C18 C19 1.382(3) . ?
C19 C20 1.393(2) . ?
O6 C22 1.367(2) . ?
O6 C21 1.414(2) . ?
O7 C29 1.209(3) . ?
O8 C29 1.338(3) . ?
O8 C30 1.424(3) . ?
O9 C32 1.422(2) . ?
O10 C34 1.402(2) . ?
O10 C33 1.415(2) . ?
N2 C29 1.341(3) . ?
N2 C31 1.448(2) . ?
N2 C28 1.456(2) . ?
C22 C27 1.390(2) . ?
C22 C23 1.392(3) . ?
C23 C24 1.372(2) . ?
C24 C25 1.394(2) . ?
C25 C26 1.381(3) . ?
C25 C28 1.512(3) . ?
C26 C27 1.388(3) . ?
C30 C31 1.541(2) . ?
C31 C32 1.523(2) . ?
C32 C33 1.504(3) . ?
C34 C35 1.510(3) . ?
C35 C40 1.386(3) . ?
C35 C36 1.396(3) . ?
C36 C37 1.386(3) . ?
C37 C38 1.373(4) . ?
C38 C39 1.382(3) . ?
C39 C40 1.391(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 117.40(15) . . ?
C9 O3 C10 109.99(13) . . ?
C14 O5 C13 114.40(12) . . ?
C9 N1 C8 123.57(15) . . ?
C9 N1 C11 112.96(13) . . ?
C8 N1 C11 123.47(14) . . ?
O1 C2 C3 124.66(17) . . ?
O1 C2 C7 115.46(16) . . ?
C3 C2 C7 119.87(17) . . ?
C2 C3 C4 119.24(17) . . ?
C5 C4 C3 121.80(17) . . ?
C4 C5 C6 117.84(17) . . ?
C4 C5 C8 120.93(17) . . ?
C6 C5 C8 121.23(17) . . ?
C7 C6 C5 121.50(18) . . ?
C6 C7 C2 119.74(17) . . ?
N1 C8 C5 112.33(13) . . ?
O2 C9 N1 128.12(17) . . ?
O2 C9 O3 121.52(17) . . ?
N1 C9 O3 110.36(15) . . ?
O3 C10 C11 106.11(13) . . ?
N1 C11 C12 112.93(13) . . ?
N1 C11 C10 100.50(13) . . ?
C12 C11 C10 114.30(13) . . ?
O4 C12 C13 109.27(14) . . ?
O4 C12 C11 109.66(14) . . ?
C13 C12 C11 111.93(13) . . ?
O5 C13 C12 106.41(13) . . ?
O5 C14 C15 108.68(12) . . ?
C20 C15 C16 119.59(14) . . ?
C20 C15 C14 119.29(14) . . ?
C16 C15 C14 121.10(14) . . ?
C15 C16 C17 119.72(15) . . ?
C18 C17 C16 120.79(17) . . ?
C17 C18 C19 119.43(16) . . ?
C18 C19 C20 120.31(17) . . ?
C15 C20 C19 120.15(16) . . ?
C22 O6 C21 118.39(15) . . ?
C29 O8 C30 109.81(15) . . ?
C34 O10 C33 114.04(15) . . ?
C29 N2 C31 112.25(16) . . ?
C29 N2 C28 124.14(18) . . ?
C31 N2 C28 122.81(15) . . ?
O6 C22 C27 124.51(16) . . ?
O6 C22 C23 115.90(15) . . ?
C27 C22 C23 119.59(16) . . ?
C24 C23 C22 120.51(16) . . ?
C23 C24 C25 120.85(17) . . ?
C26 C25 C24 118.09(16) . . ?
C26 C25 C28 121.44(17) . . ?
C24 C25 C28 120.45(17) . . ?
C25 C26 C27 122.10(16) . . ?
C26 C27 C22 118.86(17) . . ?
N2 C28 C25 112.16(14) . . ?
O7 C29 O8 122.1(2) . . ?
O7 C29 N2 127.1(2) . . ?
O8 C29 N2 110.78(18) . . ?
O8 C30 C31 105.97(15) . . ?
N2 C31 C32 112.44(14) . . ?
N2 C31 C30 100.46(14) . . ?
C32 C31 C30 114.24(14) . . ?
O9 C32 C33 109.95(15) . . ?
O9 C32 C31 108.59(14) . . ?
C33 C32 C31 112.66(16) . . ?
O10 C33 C32 107.02(15) . . ?
O10 C34 C35 109.52(14) . . ?
C40 C35 C36 119.05(18) . . ?
C40 C35 C34 122.21(16) . . ?
C36 C35 C34 118.73(17) . . ?
C37 C36 C35 120.1(2) . . ?
C38 C37 C36 120.6(2) . . ?
C37 C38 C39 119.7(2) . . ?
C38 C39 C40 120.3(2) . . ?
C35 C40 C39 120.21(19) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        30.51
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.033

#===END

data_20
_database_code_depnum_ccdc_archive 'CCDC 769813'
#TrackingRef 'Gnisson-X-ray-9-20.CIF'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C15 H17 N O4'
_chemical_formula_sum            'C15 H17 N O4'
_chemical_formula_weight         275.3
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration syn

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

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

_cell_length_a                   4.5326(2)
_cell_length_b                   25.9051(12)
_cell_length_c                   6.2404(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.523(3)
_cell_angle_gamma                90
_cell_volume                     686.23(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    1851
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      22.95
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.994

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.046
_diffrn_reflns_number            7458
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         29.09
_diffrn_reflns_theta_full        26.3
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.917
_reflns_number_total             1727
_reflns_number_gt                1310
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0503P)^2^+0.1843P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1727
_refine_ls_number_parameters     182
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.1006
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.06
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.048

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.5493(6) 0.28527(9) 0.4438(4) 0.0347(6) Uani 1 1 d . . .
O4 O 0.8929(6) 0.34684(9) 0.8723(4) 0.0340(6) Uani 1 1 d . . .
O1 O 0.1297(7) 0.01424(9) 0.8189(5) 0.0439(7) Uani 1 1 d . . .
N1 N 0.7624(7) 0.23231(10) 0.7374(5) 0.0304(7) Uani 1 1 d . . .
O2 O 0.8436(8) 0.21937(10) 0.3965(5) 0.0487(8) Uani 1 1 d . . .
C8 C 0.9225(9) 0.18671(13) 0.8602(6) 0.0339(8) Uani 1 1 d . . .
H8A H 1.0347 0.196 1.0186 0.041 Uiso 1 1 calc R . .
H8B H 1.0771 0.1755 0.795 0.041 Uiso 1 1 calc R . .
C5 C 0.7048(8) 0.14231(12) 0.8533(6) 0.0284(7) Uani 1 1 d . . .
C13 C 0.5931(9) 0.35825(13) 0.7030(6) 0.0319(8) Uani 1 1 d . . .
H13 H 0.4633 0.3765 0.7754 0.038 Uiso 1 1 calc R . .
C2 C 0.3236(9) 0.05656(14) 0.8437(6) 0.0341(8) Uani 1 1 d . . .
C7 C 0.5121(10) 0.07667(13) 1.0505(6) 0.0358(9) Uani 1 1 d . . .
H7 H 0.5134 0.0619 1.1866 0.043 Uiso 1 1 calc R . .
C9 C 0.7301(10) 0.24228(13) 0.5181(6) 0.0331(8) Uani 1 1 d . . .
C10 C 0.4480(9) 0.30523(13) 0.6219(6) 0.0309(8) Uani 1 1 d . . .
H10 H 0.218 0.3057 0.5764 0.037 Uiso 1 1 calc R . .
C4 C 0.5078(9) 0.12174(14) 0.6459(6) 0.0340(8) Uani 1 1 d . . .
H4 H 0.5028 0.1367 0.5093 0.041 Uiso 1 1 calc R . .
C14 C 0.6382(11) 0.39207(14) 0.5225(6) 0.0410(9) Uani 1 1 d . . .
H14 H 0.7909 0.3825 0.4622 0.049 Uiso 1 1 calc R . .
C6 C 0.7018(9) 0.11954(14) 1.0546(6) 0.0335(8) Uani 1 1 d . . .
H6 H 0.8285 0.1331 1.1946 0.04 Uiso 1 1 calc R . .
C11 C 0.6037(8) 0.26973(12) 0.8311(5) 0.0274(7) Uani 1 1 d . . .
H11 H 0.4494 0.2538 0.888 0.033 Uiso 1 1 calc R . .
C3 C 0.3200(10) 0.07936(13) 0.6409(6) 0.0361(8) Uani 1 1 d . . .
H3 H 0.1905 0.066 0.5012 0.043 Uiso 1 1 calc R . .
C12 C 0.8299(10) 0.30598(13) 1.0067(6) 0.0349(9) Uani 1 1 d . . .
H12A H 0.7331 0.3195 1.1113 0.042 Uiso 1 1 calc R . .
H12B H 1.0226 0.2881 1.0943 0.042 Uiso 1 1 calc R . .
C1 C 0.1625(13) -0.01405(16) 1.0222(8) 0.0535(12) Uani 1 1 d . . .
H1A H 0.3809 -0.0218 1.1015 0.08 Uiso 1 1 calc R . .
H1B H 0.0449 -0.0456 0.9826 0.08 Uiso 1 1 calc R . .
H1C H 0.0838 0.0063 1.1192 0.08 Uiso 1 1 calc R . .
C15 C 0.4768(12) 0.43432(17) 0.4435(8) 0.0560(12) Uani 1 1 d . . .
H15A H 0.3222 0.445 0.5001 0.067 Uiso 1 1 calc R . .
H15B H 0.5169 0.4536 0.331 0.067 Uiso 1 1 calc 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
O3 0.0472(18) 0.0329(13) 0.0210(11) 0.0003(9) 0.0084(12) -0.0016(11)
O4 0.0386(16) 0.0328(13) 0.0289(12) -0.0019(10) 0.0098(12) -0.0063(11)
O1 0.055(2) 0.0339(14) 0.0410(15) 0.0019(12) 0.0148(15) -0.0131(12)
N1 0.0375(19) 0.0288(15) 0.0268(14) 0.0019(11) 0.0136(15) 0.0007(12)
O2 0.078(2) 0.0407(15) 0.0405(14) -0.0064(12) 0.0371(16) -0.0040(14)
C8 0.032(2) 0.0338(18) 0.0348(19) 0.0021(15) 0.0098(18) -0.0001(15)
C5 0.027(2) 0.0287(17) 0.0303(18) -0.0002(13) 0.0111(17) 0.0043(13)
C13 0.036(2) 0.0319(19) 0.0293(17) 0.0002(14) 0.0132(18) 0.0003(14)
C2 0.038(2) 0.0303(18) 0.0342(19) 0.0011(15) 0.0128(18) 0.0004(15)
C7 0.046(3) 0.0361(19) 0.0269(17) 0.0035(14) 0.0153(18) 0.0008(16)
C9 0.044(2) 0.0303(18) 0.0268(17) -0.0030(14) 0.0147(18) -0.0078(15)
C10 0.029(2) 0.0324(17) 0.0313(18) 0.0040(14) 0.0103(18) 0.0018(14)
C4 0.043(2) 0.0336(18) 0.0263(18) 0.0025(15) 0.0128(18) 0.0026(15)
C14 0.053(3) 0.037(2) 0.0350(19) 0.0001(16) 0.018(2) -0.0047(18)
C6 0.039(2) 0.0334(18) 0.0282(18) -0.0022(14) 0.0115(18) 0.0014(15)
C11 0.029(2) 0.0296(17) 0.0266(16) 0.0003(13) 0.0137(16) -0.0008(13)
C3 0.043(2) 0.0343(19) 0.0276(17) -0.0025(15) 0.0074(18) -0.0040(16)
C12 0.050(3) 0.0349(18) 0.0224(16) -0.0023(14) 0.0152(18) -0.0022(16)
C1 0.068(3) 0.045(2) 0.047(2) 0.0085(19) 0.020(3) -0.014(2)
C15 0.066(4) 0.045(2) 0.052(3) 0.010(2) 0.014(3) -0.001(2)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C9 1.364(4) . ?
O3 C10 1.439(4) . ?
O4 C13 1.430(5) . ?
O4 C12 1.440(4) . ?
O1 C2 1.379(4) . ?
O1 C1 1.427(5) . ?
N1 C9 1.349(4) . ?
N1 C11 1.447(4) . ?
N1 C8 1.456(4) . ?
O2 C9 1.211(4) . ?
C8 C5 1.506(5) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C5 C6 1.392(4) . ?
C5 C4 1.395(5) . ?
C13 C14 1.496(5) . ?
C13 C10 1.530(5) . ?
C13 H13 0.98 . ?
C2 C7 1.376(5) . ?
C2 C3 1.392(5) . ?
C7 C6 1.399(5) . ?
C7 H7 0.93 . ?
C10 C11 1.550(5) . ?
C10 H10 0.98 . ?
C4 C3 1.383(5) . ?
C4 H4 0.93 . ?
C14 C15 1.313(6) . ?
C14 H14 0.93 . ?
C6 H6 0.93 . ?
C11 C12 1.532(5) . ?
C11 H11 0.98 . ?
C3 H3 0.93 . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C1 H1A 0.96 . ?
C1 H1B 0.96 . ?
C1 H1C 0.96 . ?
C15 H15A 0.93 . ?
C15 H15B 0.93 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O3 C10 110.3(2) . . ?
C13 O4 C12 104.6(3) . . ?
C2 O1 C1 116.4(3) . . ?
C9 N1 C11 112.9(3) . . ?
C9 N1 C8 123.1(3) . . ?
C11 N1 C8 123.9(2) . . ?
N1 C8 C5 113.8(3) . . ?
N1 C8 H8A 108.8 . . ?
C5 C8 H8A 108.8 . . ?
N1 C8 H8B 108.8 . . ?
C5 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C6 C5 C4 118.0(3) . . ?
C6 C5 C8 120.7(3) . . ?
C4 C5 C8 121.2(3) . . ?
O4 C13 C14 109.4(3) . . ?
O4 C13 C10 104.2(3) . . ?
C14 C13 C10 115.7(3) . . ?
O4 C13 H13 109.1 . . ?
C14 C13 H13 109.1 . . ?
C10 C13 H13 109.1 . . ?
C7 C2 O1 124.6(3) . . ?
C7 C2 C3 119.9(3) . . ?
O1 C2 C3 115.6(3) . . ?
C2 C7 C6 119.5(3) . . ?
C2 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
O2 C9 N1 128.5(3) . . ?
O2 C9 O3 121.6(3) . . ?
N1 C9 O3 109.9(3) . . ?
O3 C10 C13 111.2(3) . . ?
O3 C10 C11 105.2(2) . . ?
C13 C10 C11 103.8(3) . . ?
O3 C10 H10 112.1 . . ?
C13 C10 H10 112.1 . . ?
C11 C10 H10 112.1 . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C15 C14 C13 124.4(4) . . ?
C15 C14 H14 117.8 . . ?
C13 C14 H14 117.8 . . ?
C5 C6 C7 121.3(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
N1 C11 C12 113.4(3) . . ?
N1 C11 C10 101.6(2) . . ?
C12 C11 C10 103.4(3) . . ?
N1 C11 H11 112.5 . . ?
C12 C11 H11 112.5 . . ?
C10 C11 H11 112.5 . . ?
C4 C3 C2 120.4(4) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
O4 C12 C11 104.7(3) . . ?
O4 C12 H12A 110.8 . . ?
C11 C12 H12A 110.8 . . ?
O4 C12 H12B 110.8 . . ?
C11 C12 H12B 110.8 . . ?
H12A C12 H12B 108.9 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C14 C15 H15A 120 . . ?
C14 C15 H15B 120 . . ?
H15A C15 H15B 120 . . ?

#===END