# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_(R)-3a
_database_code_depnum_ccdc_archive 'CCDC 1849794'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-09-10 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         323.38
_chemical_absolute_configuration syn

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.2977(2)
_cell_length_b                   7.4401(2)
_cell_length_c                   18.2018(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.594(2)
_cell_angle_gamma                90
_cell_volume                     851.98(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6313
_cell_measurement_theta_min      4.8642
_cell_measurement_theta_max      67.8741
_cell_measurement_temperature    173

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344

_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           'SADABS (Sheldrick 1996)'

_diffrn_ambient_temperature      173

_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_diffrn_source_type              ?

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_diffrn_measurement_device_type  'Bruker APEXII Ultra CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            9149
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_theta_min         2.430
_diffrn_reflns_theta_max         68.227
_diffrn_reflns_theta_full        68.227
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_refine_special_details          
;
;

_reflns_number_total             2815
_reflns_number_gt                2709
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0805
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_number_reflns         2815
_refine_ls_number_parameters     225
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0414P)²+0.1448P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.158
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 1085 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.15(7)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.1224(3) 0.5380(3) 0.81999(11) 0.0369(5) Uani d . . . 1 . .
C C2 0.2979(4) 0.6359(3) 0.86450(12) 0.0384(5) Uani d . . . 1 . .
H H2A 0.421 0.6616 0.8342 0.046 Uiso calc U . R 1 . .
H H2B 0.3465 0.5653 0.9082 0.046 Uiso calc U . R 1 . .
C C3 0.1869(3) 0.8090(3) 0.88671(12) 0.0387(5) Uani d . . . 1 . .
H H3 0.1627 0.8866 0.8423 0.046 Uiso calc U . R 1 . .
C C4 -0.0283(4) 0.7382(4) 0.91111(14) 0.0481(6) Uani d . . . 1 . .
H H4A -0.017 0.697 0.9628 0.058 Uiso calc U . R 1 . .
H H4B -0.1385 0.8329 0.9064 0.058 Uiso calc U . R 1 . .
C C5 -0.0822(4) 0.5806(4) 0.85899(13) 0.0428(5) Uani d . . . 1 . .
H H5A -0.1289 0.4748 0.8871 0.051 Uiso calc U . R 1 . .
H H5B -0.1973 0.6145 0.8228 0.051 Uiso calc U . R 1 . .
C C6 0.3096(4) 0.9152(3) 0.94588(13) 0.0432(6) Uani d . . . 1 . .
C C7 0.2526(3) 0.4975(3) 0.70755(11) 0.0352(5) Uani d . . . 1 . .
H H7 0.401 0.5322 0.7235 0.042 Uiso calc U . R 1 . .
C C8 0.2053(3) 0.3101(3) 0.73752(11) 0.0360(5) Uani d . . . 1 . .
H H8 0.0752 0.2602 0.7114 0.043 Uiso calc U . R 1 . .
C C9 0.2238(4) 0.5227(3) 0.62574(12) 0.0377(5) Uani d . . . 1 . .
C C10 0.0391(4) 0.5918(4) 0.59270(13) 0.0507(6) Uani d . . . 1 . .
H H10 -0.0779 0.6201 0.6218 0.061 Uiso calc U . R 1 . .
C C11 0.0239(5) 0.6201(4) 0.51721(15) 0.0626(8) Uani d . . . 1 . .
H H11 -0.1027 0.6687 0.4949 0.075 Uiso calc U . R 1 . .
C C12 0.1920(5) 0.5777(4) 0.47458(14) 0.0598(7) Uani d . . . 1 . .
H H12 0.1815 0.5979 0.423 0.072 Uiso calc U . R 1 . .
C C13 0.3743(5) 0.5064(5) 0.50652(14) 0.0586(7) Uani d . . . 1 . .
H H13 0.4896 0.4758 0.477 0.07 Uiso calc U . R 1 . .
C C14 0.3905(4) 0.4789(4) 0.58183(13) 0.0471(6) Uani d . . . 1 . .
H H14 0.5173 0.4294 0.6037 0.057 Uiso calc U . R 1 . .
C C15 0.3839(4) 0.1771(3) 0.73445(12) 0.0366(5) Uani d . . . 1 . .
C C16 0.3711(4) 0.0315(3) 0.68693(12) 0.0435(5) Uani d . . . 1 . .
H H16 0.2459 0.013 0.6568 0.052 Uiso calc U . R 1 . .
C C17 0.5406(5) -0.0875(3) 0.68320(15) 0.0514(6) Uani d . . . 1 . .
H H17 0.5318 -0.1861 0.6501 0.062 Uiso calc U . R 1 . .
C C18 0.7214(4) -0.0622(4) 0.72760(15) 0.0526(6) Uani d . . . 1 . .
H H18 0.8373 -0.1433 0.7251 0.063 Uiso calc U . R 1 . .
C C19 0.7336(4) 0.0806(4) 0.77557(15) 0.0508(6) Uani d . . . 1 . .
H H19 0.8576 0.0973 0.8065 0.061 Uiso calc U . R 1 . .
C C20 0.5670(4) 0.1993(3) 0.77892(14) 0.0441(5) Uani d . . . 1 . .
H H20 0.5773 0.2978 0.8121 0.053 Uiso calc U . R 1 . .
N N1 0.3258(4) 1.0890(3) 0.93543(12) 0.0501(5) Uani d . . . 1 . .
O O1 0.3833(4) 0.8413(3) 1.00162(11) 0.0719(6) Uani d . . . 1 . .
O O2 0.1609(2) 0.3492(2) 0.81272(8) 0.0397(4) Uani d . . . 1 . .
O O3 0.1071(2) 0.6046(2) 0.74627(8) 0.0366(3) Uani d . . . 1 . .
H H1N 0.419(5) 1.149(4) 0.9633(17) 0.055(8) Uiso d . . . 1 . .
H H2N 0.274(5) 1.132(5) 0.895(2) 0.064(9) Uiso d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O3 . 1.430(3) ?
C1 O2 . 1.433(3) ?
C1 C2 . 1.526(3) ?
C1 C5 . 1.532(3) ?
C2 C3 . 1.529(3) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C6 . 1.519(3) ?
C3 C4 . 1.538(3) ?
C3 H3 . 1.0 ?
C4 C5 . 1.537(4) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 O1 . 1.227(3) ?
C6 N1 . 1.311(3) ?
C7 O3 . 1.425(3) ?
C7 C9 . 1.503(3) ?
C7 C8 . 1.532(3) ?
C7 H7 . 1.0 ?
C8 O2 . 1.439(3) ?
C8 C15 . 1.501(3) ?
C8 H8 . 1.0 ?
C9 C10 . 1.385(3) ?
C9 C14 . 1.387(3) ?
C10 C11 . 1.389(4) ?
C10 H10 . 0.95 ?
C11 C12 . 1.377(4) ?
C11 H11 . 0.95 ?
C12 C13 . 1.370(4) ?
C12 H12 . 0.95 ?
C13 C14 . 1.385(4) ?
C13 H13 . 0.95 ?
C14 H14 . 0.95 ?
C15 C16 . 1.386(3) ?
C15 C20 . 1.388(3) ?
C16 C17 . 1.391(4) ?
C16 H16 . 0.95 ?
C17 C18 . 1.379(4) ?
C17 H17 . 0.95 ?
C18 C19 . 1.375(4) ?
C18 H18 . 0.95 ?
C19 C20 . 1.375(4) ?
C19 H19 . 0.95 ?
C20 H20 . 0.95 ?
N1 H1N . 0.88(3) ?
N1 H2N . 0.85(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 C1 O2 . . 104.95(17) ?
O3 C1 C2 . . 110.44(18) ?
O2 C1 C2 . . 113.31(18) ?
O3 C1 C5 . . 109.93(17) ?
O2 C1 C5 . . 113.25(19) ?
C2 C1 C5 . . 105.04(18) ?
C1 C2 C3 . . 102.33(18) ?
C1 C2 H2A . . 111.3 ?
C3 C2 H2A . . 111.3 ?
C1 C2 H2B . . 111.3 ?
C3 C2 H2B . . 111.3 ?
H2A C2 H2B . . 109.2 ?
C6 C3 C2 . . 113.69(18) ?
C6 C3 C4 . . 113.59(19) ?
C2 C3 C4 . . 101.98(19) ?
C6 C3 H3 . . 109.1 ?
C2 C3 H3 . . 109.1 ?
C4 C3 H3 . . 109.1 ?
C5 C4 C3 . . 104.82(18) ?
C5 C4 H4A . . 110.8 ?
C3 C4 H4A . . 110.8 ?
C5 C4 H4B . . 110.8 ?
C3 C4 H4B . . 110.8 ?
H4A C4 H4B . . 108.9 ?
C1 C5 C4 . . 106.08(19) ?
C1 C5 H5A . . 110.5 ?
C4 C5 H5A . . 110.5 ?
C1 C5 H5B . . 110.5 ?
C4 C5 H5B . . 110.5 ?
H5A C5 H5B . . 108.7 ?
O1 C6 N1 . . 122.2(2) ?
O1 C6 C3 . . 121.0(2) ?
N1 C6 C3 . . 116.8(2) ?
O3 C7 C9 . . 111.65(17) ?
O3 C7 C8 . . 101.15(16) ?
C9 C7 C8 . . 116.71(18) ?
O3 C7 H7 . . 109.0 ?
C9 C7 H7 . . 109.0 ?
C8 C7 H7 . . 109.0 ?
O2 C8 C15 . . 110.31(17) ?
O2 C8 C7 . . 101.76(17) ?
C15 C8 C7 . . 115.39(17) ?
O2 C8 H8 . . 109.7 ?
C15 C8 H8 . . 109.7 ?
C7 C8 H8 . . 109.7 ?
C10 C9 C14 . . 118.7(2) ?
C10 C9 C7 . . 122.5(2) ?
C14 C9 C7 . . 118.8(2) ?
C9 C10 C11 . . 120.3(2) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
C12 C11 C10 . . 120.2(3) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C13 C12 C11 . . 120.0(2) ?
C13 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
C12 C13 C14 . . 120.0(3) ?
C12 C13 H13 . . 120.0 ?
C14 C13 H13 . . 120.0 ?
C13 C14 C9 . . 120.8(2) ?
C13 C14 H14 . . 119.6 ?
C9 C14 H14 . . 119.6 ?
C16 C15 C20 . . 118.7(2) ?
C16 C15 C8 . . 121.0(2) ?
C20 C15 C8 . . 120.2(2) ?
C15 C16 C17 . . 120.3(2) ?
C15 C16 H16 . . 119.9 ?
C17 C16 H16 . . 119.9 ?
C18 C17 C16 . . 120.0(2) ?
C18 C17 H17 . . 120.0 ?
C16 C17 H17 . . 120.0 ?
C19 C18 C17 . . 119.9(2) ?
C19 C18 H18 . . 120.1 ?
C17 C18 H18 . . 120.1 ?
C20 C19 C18 . . 120.2(2) ?
C20 C19 H19 . . 119.9 ?
C18 C19 H19 . . 119.9 ?
C19 C20 C15 . . 120.9(2) ?
C19 C20 H20 . . 119.6 ?
C15 C20 H20 . . 119.6 ?
C6 N1 H1N . . 118.(2) ?
C6 N1 H2N . . 118.(2) ?
H1N N1 H2N . . 122.(3) ?
C1 O2 C8 . . 109.10(16) ?
C7 O3 C1 . . 104.64(16) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O3 C1 C2 C3 . . . . 81.8(2) ?
O2 C1 C2 C3 . . . . -160.81(17) ?
C5 C1 C2 C3 . . . . -36.7(2) ?
C1 C2 C3 C6 . . . . 167.22(19) ?
C1 C2 C3 C4 . . . . 44.5(2) ?
C6 C3 C4 C5 . . . . -158.4(2) ?
C2 C3 C4 C5 . . . . -35.6(2) ?
O3 C1 C5 C4 . . . . -104.3(2) ?
O2 C1 C5 C4 . . . . 138.6(2) ?
C2 C1 C5 C4 . . . . 14.5(2) ?
C3 C4 C5 C1 . . . . 13.2(3) ?
C2 C3 C6 O1 . . . . -47.9(3) ?
C4 C3 C6 O1 . . . . 68.1(3) ?
C2 C3 C6 N1 . . . . 134.4(2) ?
C4 C3 C6 N1 . . . . -109.6(3) ?
O3 C7 C8 O2 . . . . -35.68(19) ?
C9 C7 C8 O2 . . . . -157.03(17) ?
O3 C7 C8 C15 . . . . -155.11(17) ?
C9 C7 C8 C15 . . . . 83.5(2) ?
O3 C7 C9 C10 . . . . -19.7(3) ?
C8 C7 C9 C10 . . . . 96.0(3) ?
O3 C7 C9 C14 . . . . 158.8(2) ?
C8 C7 C9 C14 . . . . -85.6(3) ?
C14 C9 C10 C11 . . . . -1.4(4) ?
C7 C9 C10 C11 . . . . 177.1(3) ?
C9 C10 C11 C12 . . . . 0.7(5) ?
C10 C11 C12 C13 . . . . 0.4(5) ?
C11 C12 C13 C14 . . . . -0.8(5) ?
C12 C13 C14 C9 . . . . 0.0(4) ?
C10 C9 C14 C13 . . . . 1.1(4) ?
C7 C9 C14 C13 . . . . -177.5(2) ?
O2 C8 C15 C16 . . . . 134.6(2) ?
C7 C8 C15 C16 . . . . -110.8(2) ?
O2 C8 C15 C20 . . . . -46.1(3) ?
C7 C8 C15 C20 . . . . 68.5(3) ?
C20 C15 C16 C17 . . . . -1.2(3) ?
C8 C15 C16 C17 . . . . 178.1(2) ?
C15 C16 C17 C18 . . . . 0.8(4) ?
C16 C17 C18 C19 . . . . 0.1(4) ?
C17 C18 C19 C20 . . . . -0.6(4) ?
C18 C19 C20 C15 . . . . 0.3(4) ?
C16 C15 C20 C19 . . . . 0.6(4) ?
C8 C15 C20 C19 . . . . -178.6(2) ?
O3 C1 O2 C8 . . . . 10.0(2) ?
C2 C1 O2 C8 . . . . -110.6(2) ?
C5 C1 O2 C8 . . . . 129.92(18) ?
C15 C8 O2 C1 . . . . 138.76(18) ?
C7 C8 O2 C1 . . . . 15.8(2) ?
C9 C7 O3 C1 . . . . 167.93(18) ?
C8 C7 O3 C1 . . . . 43.10(19) ?
O2 C1 O3 C7 . . . . -34.0(2) ?
C2 C1 O3 C7 . . . . 88.4(2) ?
C5 C1 O3 C7 . . . . -156.14(18) ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_(R)-3b
_database_code_depnum_ccdc_archive 'CCDC 1849796'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-09-10 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H23 N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         337.40
_chemical_absolute_configuration syn

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.4767(4)
_cell_length_b                   6.7235(5)
_cell_length_c                   20.8609(14)
_cell_angle_alpha                90
_cell_angle_beta                 93.851(4)
_cell_angle_gamma                90
_cell_volume                     906.36(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4108
_cell_measurement_theta_min      4.2482
_cell_measurement_theta_max      68.2854
_cell_measurement_temperature    173

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360

_exptl_absorpt_coefficient_mu    0.659
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           'SADABS (Sheldrick 1996)'

_diffrn_ambient_temperature      173

_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_diffrn_source_type              ?

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_diffrn_measurement_device_type  'Bruker APEXII Ultra CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            6157
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_theta_min         2.123
_diffrn_reflns_theta_max         68.280
_diffrn_reflns_theta_full        68.280
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24

_refine_special_details          
;
;

_reflns_number_total             2627
_reflns_number_gt                2505
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.0995
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_number_reflns         2627
_refine_ls_number_parameters     226
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0480P)²+0.2719P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.133
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 784 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.26(12)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4278(4) 0.8494(4) 0.78094(14) 0.0341(6) Uani d . . . 1 . .
C C2 0.5730(4) 0.9245(5) 0.74184(14) 0.0413(7) Uani d . . . 1 . .
H H2 0.5535 0.9075 0.6966 0.05 Uiso calc U . R 1 . .
C C3 0.7467(5) 1.0242(5) 0.76754(18) 0.0476(8) Uani d . . . 1 . .
H H3 0.8434 1.0778 0.7399 0.057 Uiso calc U . R 1 . .
C C4 0.7793(5) 1.0458(5) 0.83299(18) 0.0479(8) Uani d . . . 1 . .
H H4 0.9006 1.1102 0.8508 0.057 Uiso calc U . R 1 . .
C C5 0.6350(5) 0.9734(6) 0.87266(16) 0.0476(8) Uani d . . . 1 . .
H H5 0.656 0.9901 0.9178 0.057 Uiso calc U . R 1 . .
C C6 0.4594(5) 0.8763(5) 0.84710(15) 0.0419(7) Uani d . . . 1 . .
H H6 0.3602 0.8279 0.8748 0.05 Uiso calc U . R 1 . .
C C7 0.1532(4) 0.4745(5) 0.83890(13) 0.0332(6) Uani d . . . 1 . .
C C8 0.2804(5) 0.3747(5) 0.88405(15) 0.0440(7) Uani d . . . 1 . .
H H8 0.4134 0.3314 0.8734 0.053 Uiso calc U . R 1 . .
C C9 0.2149(6) 0.3375(6) 0.94478(16) 0.0547(9) Uani d . . . 1 . .
H H9 0.3039 0.27 0.9756 0.066 Uiso calc U . R 1 . .
C C10 0.0231(6) 0.3974(6) 0.96066(15) 0.0530(9) Uani d . . . 1 . .
H H10 -0.0216 0.3708 1.0023 0.064 Uiso calc U . R 1 . .
C C11 -0.1057(5) 0.4970(5) 0.91571(15) 0.0454(8) Uani d . . . 1 . .
H H11 -0.2383 0.5404 0.9267 0.055 Uiso calc U . R 1 . .
C C12 -0.0422(5) 0.5334(5) 0.85495(13) 0.0369(6) Uani d . . . 1 . .
H H12 -0.1325 0.599 0.824 0.044 Uiso calc U . R 1 . .
C C13 0.2291(4) 0.5186(5) 0.77342(13) 0.0330(6) Uani d . . . 1 . .
H H13 0.3677 0.4562 0.7693 0.04 Uiso calc U . R 1 . .
C C14 0.2360(4) 0.7388(5) 0.75545(13) 0.0328(6) Uani d . . . 1 . .
H H14 0.111 0.8067 0.7707 0.039 Uiso calc U . R 1 . .
C C15 0.1199(4) 0.5479(5) 0.66713(13) 0.0337(6) Uani d . . . 1 . .
C C16 -0.0869(4) 0.5876(5) 0.63072(14) 0.0385(7) Uani d . . . 1 . .
H H16A -0.0664 0.6784 0.5943 0.046 Uiso calc U . R 1 . .
H H16B -0.1809 0.6537 0.6596 0.046 Uiso calc U . R 1 . .
C C17 -0.1855(4) 0.3952(5) 0.60532(14) 0.0398(7) Uani d . . . 1 . .
H H17A -0.3151 0.4265 0.5794 0.048 Uiso calc U . R 1 . .
H H17B -0.2215 0.3114 0.642 0.048 Uiso calc U . R 1 . .
C C18 -0.0414(4) 0.2797(5) 0.56419(13) 0.0373(7) Uani d . . . 1 . .
H H18A -0.0187 0.3569 0.5249 0.045 Uiso calc U . R 1 . .
H H18B -0.1073 0.152 0.5509 0.045 Uiso calc U . R 1 . .
C C19 0.1680(4) 0.2383(5) 0.60070(12) 0.0312(6) Uani d . . . 1 . .
H H19 0.1462 0.1471 0.6375 0.037 Uiso calc U . R 1 . .
C C20 0.2653(4) 0.4324(5) 0.62667(13) 0.0315(6) Uani d . . . 1 . .
H H20A 0.394 0.4014 0.6531 0.038 Uiso calc U . R 1 . .
H H20B 0.3027 0.5161 0.5902 0.038 Uiso calc U . R 1 . .
C C21 0.3131(4) 0.1386(5) 0.55585(12) 0.0310(6) Uani d . . . 1 . .
N N1 0.3732(4) -0.0449(4) 0.57087(11) 0.0373(6) Uani d . . . 1 . .
H H1A 0.4555 -0.1093 0.5462 0.045 Uiso calc U . R 1 . .
H H1B 0.3308 -0.1023 0.6055 0.045 Uiso calc U . R 1 . .
O O1 0.0836(3) 0.4437(3) 0.72474(8) 0.0343(4) Uani d . . . 1 . .
O O2 0.2196(3) 0.7318(3) 0.68697(9) 0.0373(5) Uani d . . . 1 . .
O O3 0.3672(3) 0.2262(4) 0.50815(9) 0.0407(5) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.381(4) ?
C1 C6 . 1.393(4) ?
C1 C14 . 1.514(4) ?
C2 C3 . 1.386(5) ?
C2 H2 . 0.95 ?
C3 C4 . 1.375(5) ?
C3 H3 . 0.95 ?
C4 C5 . 1.378(5) ?
C4 H4 . 0.95 ?
C5 C6 . 1.387(5) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
C7 C8 . 1.382(4) ?
C7 C12 . 1.389(4) ?
C7 C13 . 1.512(4) ?
C8 C9 . 1.385(5) ?
C8 H8 . 0.95 ?
C9 C10 . 1.368(6) ?
C9 H9 . 0.95 ?
C10 C11 . 1.385(5) ?
C10 H10 . 0.95 ?
C11 C12 . 1.381(4) ?
C11 H11 . 0.95 ?
C12 H12 . 0.95 ?
C13 O1 . 1.430(3) ?
C13 C14 . 1.529(4) ?
C13 H13 . 1.0 ?
C14 O2 . 1.426(3) ?
C14 H14 . 1.0 ?
C15 O1 . 1.424(3) ?
C15 O2 . 1.442(4) ?
C15 C16 . 1.518(4) ?
C15 C20 . 1.520(4) ?
C16 C17 . 1.522(5) ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
C17 C18 . 1.522(4) ?
C17 H17A . 0.99 ?
C17 H17B . 0.99 ?
C18 C19 . 1.536(4) ?
C18 H18A . 0.99 ?
C18 H18B . 0.99 ?
C19 C21 . 1.525(4) ?
C19 C20 . 1.532(4) ?
C19 H19 . 1.0 ?
C20 H20A . 0.99 ?
C20 H20B . 0.99 ?
C21 O3 . 1.227(3) ?
C21 N1 . 1.325(4) ?
N1 H1A . 0.88 ?
N1 H1B . 0.88 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 118.5(3) ?
C2 C1 C14 . . 123.2(3) ?
C6 C1 C14 . . 118.3(3) ?
C1 C2 C3 . . 121.0(3) ?
C1 C2 H2 . . 119.5 ?
C3 C2 H2 . . 119.5 ?
C4 C3 C2 . . 120.1(3) ?
C4 C3 H3 . . 120.0 ?
C2 C3 H3 . . 120.0 ?
C3 C4 C5 . . 119.6(3) ?
C3 C4 H4 . . 120.2 ?
C5 C4 H4 . . 120.2 ?
C4 C5 C6 . . 120.5(3) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C5 C6 C1 . . 120.3(3) ?
C5 C6 H6 . . 119.9 ?
C1 C6 H6 . . 119.9 ?
C8 C7 C12 . . 119.0(3) ?
C8 C7 C13 . . 119.7(3) ?
C12 C7 C13 . . 121.2(3) ?
C7 C8 C9 . . 120.4(3) ?
C7 C8 H8 . . 119.8 ?
C9 C8 H8 . . 119.8 ?
C10 C9 C8 . . 120.5(3) ?
C10 C9 H9 . . 119.8 ?
C8 C9 H9 . . 119.8 ?
C9 C10 C11 . . 119.6(3) ?
C9 C10 H10 . . 120.2 ?
C11 C10 H10 . . 120.2 ?
C12 C11 C10 . . 120.3(3) ?
C12 C11 H11 . . 119.8 ?
C10 C11 H11 . . 119.8 ?
C11 C12 C7 . . 120.2(3) ?
C11 C12 H12 . . 119.9 ?
C7 C12 H12 . . 119.9 ?
O1 C13 C7 . . 109.5(2) ?
O1 C13 C14 . . 101.3(2) ?
C7 C13 C14 . . 115.4(2) ?
O1 C13 H13 . . 110.1 ?
C7 C13 H13 . . 110.1 ?
C14 C13 H13 . . 110.1 ?
O2 C14 C1 . . 111.9(2) ?
O2 C14 C13 . . 102.3(2) ?
C1 C14 C13 . . 115.2(2) ?
O2 C14 H14 . . 109.1 ?
C1 C14 H14 . . 109.1 ?
C13 C14 H14 . . 109.1 ?
O1 C15 O2 . . 106.0(2) ?
O1 C15 C16 . . 108.6(2) ?
O2 C15 C16 . . 110.9(3) ?
O1 C15 C20 . . 111.1(2) ?
O2 C15 C20 . . 108.4(2) ?
C16 C15 C20 . . 111.8(2) ?
C15 C16 C17 . . 111.1(3) ?
C15 C16 H16A . . 109.4 ?
C17 C16 H16A . . 109.4 ?
C15 C16 H16B . . 109.4 ?
C17 C16 H16B . . 109.4 ?
H16A C16 H16B . . 108.0 ?
C16 C17 C18 . . 111.8(2) ?
C16 C17 H17A . . 109.3 ?
C18 C17 H17A . . 109.3 ?
C16 C17 H17B . . 109.3 ?
C18 C17 H17B . . 109.3 ?
H17A C17 H17B . . 107.9 ?
C17 C18 C19 . . 111.6(2) ?
C17 C18 H18A . . 109.3 ?
C19 C18 H18A . . 109.3 ?
C17 C18 H18B . . 109.3 ?
C19 C18 H18B . . 109.3 ?
H18A C18 H18B . . 108.0 ?
C21 C19 C20 . . 109.6(2) ?
C21 C19 C18 . . 109.6(2) ?
C20 C19 C18 . . 110.4(2) ?
C21 C19 H19 . . 109.1 ?
C20 C19 H19 . . 109.1 ?
C18 C19 H19 . . 109.1 ?
C15 C20 C19 . . 112.1(2) ?
C15 C20 H20A . . 109.2 ?
C19 C20 H20A . . 109.2 ?
C15 C20 H20B . . 109.2 ?
C19 C20 H20B . . 109.2 ?
H20A C20 H20B . . 107.9 ?
O3 C21 N1 . . 122.9(3) ?
O3 C21 C19 . . 120.5(3) ?
N1 C21 C19 . . 116.6(2) ?
C21 N1 H1A . . 120.0 ?
C21 N1 H1B . . 120.0 ?
H1A N1 H1B . . 120.0 ?
C15 O1 C13 . . 106.7(2) ?
C14 O2 C15 . . 108.5(2) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.1(5) ?
C14 C1 C2 C3 . . . . -179.8(3) ?
C1 C2 C3 C4 . . . . 1.5(5) ?
C2 C3 C4 C5 . . . . -2.1(5) ?
C3 C4 C5 C6 . . . . 1.1(5) ?
C4 C5 C6 C1 . . . . 0.5(5) ?
C2 C1 C6 C5 . . . . -1.1(5) ?
C14 C1 C6 C5 . . . . 178.8(3) ?
C12 C7 C8 C9 . . . . -1.2(5) ?
C13 C7 C8 C9 . . . . 178.4(3) ?
C7 C8 C9 C10 . . . . 0.6(6) ?
C8 C9 C10 C11 . . . . -0.4(6) ?
C9 C10 C11 C12 . . . . 0.9(6) ?
C10 C11 C12 C7 . . . . -1.5(5) ?
C8 C7 C12 C11 . . . . 1.6(5) ?
C13 C7 C12 C11 . . . . -178.0(3) ?
C8 C7 C13 O1 . . . . 126.0(3) ?
C12 C7 C13 O1 . . . . -54.4(4) ?
C8 C7 C13 C14 . . . . -120.5(3) ?
C12 C7 C13 C14 . . . . 59.1(4) ?
C2 C1 C14 O2 . . . . -3.1(4) ?
C6 C1 C14 O2 . . . . 177.1(3) ?
C2 C1 C14 C13 . . . . 113.2(3) ?
C6 C1 C14 C13 . . . . -66.7(3) ?
O1 C13 C14 O2 . . . . -36.9(2) ?
C7 C13 C14 O2 . . . . -155.1(2) ?
O1 C13 C14 C1 . . . . -158.5(2) ?
C7 C13 C14 C1 . . . . 83.3(3) ?
O1 C15 C16 C17 . . . . -68.2(3) ?
O2 C15 C16 C17 . . . . 175.8(2) ?
C20 C15 C16 C17 . . . . 54.7(3) ?
C15 C16 C17 C18 . . . . -55.2(3) ?
C16 C17 C18 C19 . . . . 55.4(3) ?
C17 C18 C19 C21 . . . . -175.1(3) ?
C17 C18 C19 C20 . . . . -54.3(3) ?
O1 C15 C20 C19 . . . . 66.6(3) ?
O2 C15 C20 C19 . . . . -177.3(2) ?
C16 C15 C20 C19 . . . . -54.9(3) ?
C21 C19 C20 C15 . . . . 175.0(2) ?
C18 C19 C20 C15 . . . . 54.1(3) ?
C20 C19 C21 O3 . . . . -58.4(3) ?
C18 C19 C21 O3 . . . . 63.0(3) ?
C20 C19 C21 N1 . . . . 122.4(3) ?
C18 C19 C21 N1 . . . . -116.2(3) ?
O2 C15 O1 C13 . . . . -23.2(3) ?
C16 C15 O1 C13 . . . . -142.4(2) ?
C20 C15 O1 C13 . . . . 94.3(3) ?
C7 C13 O1 C15 . . . . 159.4(2) ?
C14 C13 O1 C15 . . . . 37.1(3) ?
C1 C14 O2 C15 . . . . 147.8(2) ?
C13 C14 O2 C15 . . . . 23.9(3) ?
O1 C15 O2 C14 . . . . -1.8(3) ?
C16 C15 O2 C14 . . . . 115.8(2) ?
C20 C15 O2 C14 . . . . -121.2(2) ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_(S)-3a
_database_code_depnum_ccdc_archive 'CCDC 1849795'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-09-10 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         323.38
_chemical_absolute_configuration syn

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.2884(3)
_cell_length_b                   9.3902(5)
_cell_length_c                   14.9711(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.263(2)
_cell_angle_gamma                90
_cell_volume                     874.86(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7776
_cell_measurement_theta_min      5.5779
_cell_measurement_theta_max      68.1775
_cell_measurement_temperature    173

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344

_exptl_absorpt_coefficient_mu    0.662
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           'SADABS (Sheldrick 1996)'

_diffrn_ambient_temperature      173

_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_diffrn_source_type              ?

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_diffrn_measurement_device_type  'Bruker APEXII Ultra CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            8323
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_theta_min         2.983
_diffrn_reflns_theta_max         68.172
_diffrn_reflns_theta_full        68.172
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             2857
_reflns_number_gt                2790
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1005
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_number_reflns         2857
_refine_ls_number_parameters     225
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0565P)²+0.1724P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.109
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 1150 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(7)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.4442(3) 0.5084(2) 0.66340(11) 0.0406(4) Uani d . . . 1 . .
O O2 0.5745(3) 0.6876(2) 0.75799(12) 0.0463(5) Uani d . . . 1 . .
N N1 -0.0690(4) 0.7992(4) 0.43186(17) 0.0582(7) Uani d . . . 1 . .
C C8 0.6256(4) 0.5569(3) 0.80410(16) 0.0365(5) Uani d . . . 1 . .
H H8 0.5118 0.5354 0.8424 0.044 Uiso calc U . R 1 . .
O O3 0.0989(4) 0.9690(3) 0.5201(2) 0.0876(10) Uani d . . . 1 . .
C C1 0.4792(4) 0.6583(3) 0.66739(16) 0.0384(5) Uani d . . . 1 . .
C C11 1.1870(4) 0.6696(3) 0.90822(19) 0.0478(6) Uani d . . . 1 . .
H H11 1.2908 0.7396 0.8991 0.057 Uiso calc U . R 1 . .
C C9 0.8399(4) 0.5646(3) 0.86373(15) 0.0360(5) Uani d . . . 1 . .
C C10 0.9925(4) 0.6658(3) 0.85160(16) 0.0398(5) Uani d . . . 1 . .
H H10 0.9638 0.7333 0.8041 0.048 Uiso calc U . R 1 . .
C C7 0.6109(4) 0.4478(3) 0.72755(16) 0.0373(5) Uani d . . . 1 . .
H H7 0.749 0.4449 0.7018 0.045 Uiso calc U . R 1 . .
C C4 0.2389(4) 0.7328(3) 0.53890(18) 0.0460(6) Uani d . . . 1 . .
H H4 0.1866 0.6367 0.5167 0.055 Uiso calc U . R 1 . .
C C15 0.5482(4) 0.3003(3) 0.75256(17) 0.0454(6) Uani d . . . 1 . .
C C6 0.0819(4) 0.8454(3) 0.4964(2) 0.0509(7) Uani d . . . 1 . .
C C5 0.2661(4) 0.7338(3) 0.64061(18) 0.0440(6) Uani d . . . 1 . .
H H5A 0.1476 0.6819 0.6632 0.053 Uiso calc U . R 1 . .
H H5B 0.2713 0.8324 0.6642 0.053 Uiso calc U . R 1 . .
C C12 1.2313(5) 0.5737(4) 0.97720(19) 0.0581(8) Uani d . . . 1 . .
H H12 1.3642 0.5779 1.0164 0.07 Uiso calc U . R 1 . .
C C2 0.6203(4) 0.7085(3) 0.59827(18) 0.0447(6) Uani d . . . 1 . .
H H2A 0.713 0.7886 0.6228 0.054 Uiso calc U . R 1 . .
H H2B 0.7129 0.6298 0.5824 0.054 Uiso calc U . R 1 . .
C C18 0.4448(10) 0.0279(4) 0.8016(3) 0.0874(15) Uani d . . . 1 . .
H H18 0.4098 -0.0657 0.8187 0.105 Uiso calc U . R 1 . .
C C20 0.3591(5) 0.2773(4) 0.7880(2) 0.0590(8) Uani d . . . 1 . .
H H20 0.2658 0.3548 0.7951 0.071 Uiso calc U . R 1 . .
C C16 0.6814(6) 0.1862(3) 0.7414(2) 0.0608(8) Uani d . . . 1 . .
H H16 0.8102 0.2013 0.7165 0.073 Uiso calc U . R 1 . .
C C3 0.4677(5) 0.7557(5) 0.5161(2) 0.0681(10) Uani d . . . 1 . .
H H3A 0.4902 0.6984 0.4628 0.082 Uiso calc U . R 1 . .
H H3B 0.4911 0.8573 0.5029 0.082 Uiso calc U . R 1 . .
C C17 0.6283(10) 0.0504(4) 0.7663(3) 0.0825(13) Uani d . . . 1 . .
H H17 0.7209 -0.0272 0.7586 0.099 Uiso calc U . R 1 . .
C C13 1.0823(6) 0.4716(5) 0.9893(2) 0.0708(10) Uani d . . . 1 . .
H H13 1.1134 0.4034 1.0362 0.085 Uiso calc U . R 1 . .
C C14 0.8865(5) 0.4673(4) 0.9333(2) 0.0593(8) Uani d . . . 1 . .
H H14 0.7835 0.397 0.9428 0.071 Uiso calc U . R 1 . .
C C19 0.3062(7) 0.1405(5) 0.8132(3) 0.0800(13) Uani d . . . 1 . .
H H19 0.1776 0.1239 0.838 0.096 Uiso calc U . R 1 . .
H H1N -0.092(5) 0.698(4) 0.4239(19) 0.043(8) Uiso d . . . 1 . .
H H2N -0.170(8) 0.858(6) 0.406(3) 0.086(13) Uiso d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.425(3) ?
O1 C7 . 1.434(3) ?
O2 C8 . 1.422(3) ?
O2 C1 . 1.429(3) ?
N1 C6 . 1.327(4) ?
N1 H1N . 0.97(4) ?
N1 H2N . 0.89(5) ?
C8 C9 . 1.508(3) ?
C8 C7 . 1.530(3) ?
C8 H8 . 1.0 ?
O3 C6 . 1.213(4) ?
C1 C5 . 1.518(3) ?
C1 C2 . 1.531(4) ?
C11 C12 . 1.368(4) ?
C11 C10 . 1.385(4) ?
C11 H11 . 0.95 ?
C9 C10 . 1.381(4) ?
C9 C14 . 1.385(4) ?
C10 H10 . 0.95 ?
C7 C15 . 1.502(4) ?
C7 H7 . 1.0 ?
C4 C5 . 1.508(4) ?
C4 C6 . 1.522(4) ?
C4 C3 . 1.541(4) ?
C4 H4 . 1.0 ?
C15 C16 . 1.385(4) ?
C15 C20 . 1.387(5) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C12 C13 . 1.371(5) ?
C12 H12 . 0.95 ?
C2 C3 . 1.513(4) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C18 C17 . 1.354(7) ?
C18 C19 . 1.396(7) ?
C18 H18 . 0.95 ?
C20 C19 . 1.393(5) ?
C20 H20 . 0.95 ?
C16 C17 . 1.382(6) ?
C16 H16 . 0.95 ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C17 H17 . 0.95 ?
C13 C14 . 1.387(4) ?
C13 H13 . 0.95 ?
C14 H14 . 0.95 ?
C19 H19 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 C7 . . 105.68(18) ?
C8 O2 C1 . . 109.26(19) ?
C6 N1 H1N . . 119.4(18) ?
C6 N1 H2N . . 121.(3) ?
H1N N1 H2N . . 118.(4) ?
O2 C8 C9 . . 111.5(2) ?
O2 C8 C7 . . 103.24(19) ?
C9 C8 C7 . . 115.3(2) ?
O2 C8 H8 . . 108.8 ?
C9 C8 H8 . . 108.8 ?
C7 C8 H8 . . 108.8 ?
O1 C1 O2 . . 105.72(19) ?
O1 C1 C5 . . 109.0(2) ?
O2 C1 C5 . . 113.3(2) ?
O1 C1 C2 . . 112.1(2) ?
O2 C1 C2 . . 112.2(2) ?
C5 C1 C2 . . 104.7(2) ?
C12 C11 C10 . . 120.7(3) ?
C12 C11 H11 . . 119.6 ?
C10 C11 H11 . . 119.6 ?
C10 C9 C14 . . 118.5(2) ?
C10 C9 C8 . . 122.3(2) ?
C14 C9 C8 . . 119.2(2) ?
C9 C10 C11 . . 120.4(2) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
O1 C7 C15 . . 109.9(2) ?
O1 C7 C8 . . 101.29(19) ?
C15 C7 C8 . . 114.9(2) ?
O1 C7 H7 . . 110.2 ?
C15 C7 H7 . . 110.2 ?
C8 C7 H7 . . 110.2 ?
C5 C4 C6 . . 113.0(2) ?
C5 C4 C3 . . 104.4(2) ?
C6 C4 C3 . . 112.4(2) ?
C5 C4 H4 . . 109.0 ?
C6 C4 H4 . . 109.0 ?
C3 C4 H4 . . 109.0 ?
C16 C15 C20 . . 119.5(3) ?
C16 C15 C7 . . 119.9(3) ?
C20 C15 C7 . . 120.6(3) ?
O3 C6 N1 . . 123.3(3) ?
O3 C6 C4 . . 121.2(3) ?
N1 C6 C4 . . 115.5(3) ?
C4 C5 C1 . . 103.4(2) ?
C4 C5 H5A . . 111.1 ?
C1 C5 H5A . . 111.1 ?
C4 C5 H5B . . 111.1 ?
C1 C5 H5B . . 111.1 ?
H5A C5 H5B . . 109.0 ?
C11 C12 C13 . . 119.4(3) ?
C11 C12 H12 . . 120.3 ?
C13 C12 H12 . . 120.3 ?
C3 C2 C1 . . 106.1(2) ?
C3 C2 H2A . . 110.5 ?
C1 C2 H2A . . 110.5 ?
C3 C2 H2B . . 110.5 ?
C1 C2 H2B . . 110.5 ?
H2A C2 H2B . . 108.7 ?
C17 C18 C19 . . 120.9(3) ?
C17 C18 H18 . . 119.6 ?
C19 C18 H18 . . 119.6 ?
C15 C20 C19 . . 119.9(4) ?
C15 C20 H20 . . 120.1 ?
C19 C20 H20 . . 120.1 ?
C17 C16 C15 . . 120.5(4) ?
C17 C16 H16 . . 119.7 ?
C15 C16 H16 . . 119.7 ?
C2 C3 C4 . . 106.4(2) ?
C2 C3 H3A . . 110.4 ?
C4 C3 H3A . . 110.4 ?
C2 C3 H3B . . 110.4 ?
C4 C3 H3B . . 110.4 ?
H3A C3 H3B . . 108.6 ?
C18 C17 C16 . . 120.1(4) ?
C18 C17 H17 . . 119.9 ?
C16 C17 H17 . . 119.9 ?
C12 C13 C14 . . 120.3(3) ?
C12 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C9 C14 C13 . . 120.6(3) ?
C9 C14 H14 . . 119.7 ?
C13 C14 H14 . . 119.7 ?
C20 C19 C18 . . 119.1(4) ?
C20 C19 H19 . . 120.4 ?
C18 C19 H19 . . 120.4 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 O2 C8 C9 . . . . 139.5(2) ?
C1 O2 C8 C7 . . . . 15.1(3) ?
C7 O1 C1 O2 . . . . -30.4(2) ?
C7 O1 C1 C5 . . . . -152.4(2) ?
C7 O1 C1 C2 . . . . 92.2(2) ?
C8 O2 C1 O1 . . . . 8.4(3) ?
C8 O2 C1 C5 . . . . 127.7(2) ?
C8 O2 C1 C2 . . . . -114.1(2) ?
O2 C8 C9 C10 . . . . -19.6(3) ?
C7 C8 C9 C10 . . . . 97.7(3) ?
O2 C8 C9 C14 . . . . 160.2(3) ?
C7 C8 C9 C14 . . . . -82.4(3) ?
C14 C9 C10 C11 . . . . -0.2(4) ?
C8 C9 C10 C11 . . . . 179.7(2) ?
C12 C11 C10 C9 . . . . -0.2(4) ?
C1 O1 C7 C15 . . . . 160.4(2) ?
C1 O1 C7 C8 . . . . 38.6(2) ?
O2 C8 C7 O1 . . . . -32.5(2) ?
C9 C8 C7 O1 . . . . -154.4(2) ?
O2 C8 C7 C15 . . . . -150.8(2) ?
C9 C8 C7 C15 . . . . 87.2(3) ?
O1 C7 C15 C16 . . . . 123.8(2) ?
C8 C7 C15 C16 . . . . -122.8(3) ?
O1 C7 C15 C20 . . . . -57.1(3) ?
C8 C7 C15 C20 . . . . 56.3(3) ?
C5 C4 C6 O3 . . . . 51.0(4) ?
C3 C4 C6 O3 . . . . -66.8(4) ?
C5 C4 C6 N1 . . . . -130.1(3) ?
C3 C4 C6 N1 . . . . 112.1(3) ?
C6 C4 C5 C1 . . . . -159.5(2) ?
C3 C4 C5 C1 . . . . -37.1(3) ?
O1 C1 C5 C4 . . . . -82.6(2) ?
O2 C1 C5 C4 . . . . 160.0(2) ?
C2 C1 C5 C4 . . . . 37.5(3) ?
C10 C11 C12 C13 . . . . 1.0(5) ?
O1 C1 C2 C3 . . . . 94.8(3) ?
O2 C1 C2 C3 . . . . -146.4(3) ?
C5 C1 C2 C3 . . . . -23.2(3) ?
C16 C15 C20 C19 . . . . 0.9(4) ?
C7 C15 C20 C19 . . . . -178.2(3) ?
C20 C15 C16 C17 . . . . -0.7(4) ?
C7 C15 C16 C17 . . . . 178.4(3) ?
C1 C2 C3 C4 . . . . 0.2(4) ?
C5 C4 C3 C2 . . . . 22.9(4) ?
C6 C4 C3 C2 . . . . 145.7(3) ?
C19 C18 C17 C16 . . . . 0.2(6) ?
C15 C16 C17 C18 . . . . 0.2(5) ?
C11 C12 C13 C14 . . . . -1.4(6) ?
C10 C9 C14 C13 . . . . -0.1(5) ?
C8 C9 C14 C13 . . . . 180.0(3) ?
C12 C13 C14 C9 . . . . 0.9(6) ?
C15 C20 C19 C18 . . . . -0.5(5) ?
C17 C18 C19 C20 . . . . -0.1(5) ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_(S)-3b
_database_code_depnum_ccdc_archive 'CCDC 1849797'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-09-10 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H23 N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         337.40
_chemical_absolute_configuration syn

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.5492(9)
_cell_length_b                   9.6708(9)
_cell_length_c                   19.5238(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1803.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4506
_cell_measurement_theta_min      2.3502
_cell_measurement_theta_max      27.1522
_cell_measurement_temperature    173

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.850
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.210
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720

_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           'SADABS (Sheldrick 1996)'

_diffrn_ambient_temperature      173

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            10381
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       25

_refine_special_details          
;
;

_reflns_number_total             4108
_reflns_number_gt                3746
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0815
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_number_reflns         4108
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0402P)²+0.1542P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.297
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 1499 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(4)

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'

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.65363(18) 0.73783(18) 0.48573(9) 0.0292(4) Uani d . . . 1 . .
C C2 0.5904(2) 0.81720(19) 0.53583(10) 0.0369(4) Uani d . . . 1 . .
H H2 0.5594 0.7753 0.5772 0.044 Uiso calc U . R 1 . .
C C3 0.5722(2) 0.9589(2) 0.52565(12) 0.0450(5) Uani d . . . 1 . .
H H3 0.529 1.0132 0.5603 0.054 Uiso calc U . R 1 . .
C C4 0.6163(2) 1.0208(2) 0.46576(11) 0.0442(5) Uani d . . . 1 . .
H H4 0.6037 1.1173 0.4592 0.053 Uiso calc U . R 1 . .
C C5 0.6788(2) 0.9418(2) 0.41544(11) 0.0438(5) Uani d . . . 1 . .
H H5 0.7083 0.984 0.3739 0.053 Uiso calc U . R 1 . .
C C6 0.6988(2) 0.8004(2) 0.42526(10) 0.0372(4) Uani d . . . 1 . .
H H6 0.7433 0.7467 0.3908 0.045 Uiso calc U . R 1 . .
C C7 0.67142(19) 0.58427(17) 0.49384(9) 0.0277(4) Uani d . . . 1 . .
H H7 0.7615 0.5544 0.4723 0.033 Uiso calc U . R 1 . .
C C8 0.55031(19) 0.49618(17) 0.46599(9) 0.0284(4) Uani d . . . 1 . .
H H8 0.4589 0.5417 0.4768 0.034 Uiso calc U . R 1 . .
C C9 0.55679(19) 0.46171(18) 0.39119(9) 0.0294(4) Uani d . . . 1 . .
C C10 0.4555(2) 0.51118(19) 0.34649(9) 0.0358(4) Uani d . . . 1 . .
H H10 0.3842 0.571 0.3629 0.043 Uiso calc U . R 1 . .
C C11 0.4580(3) 0.4736(2) 0.27769(10) 0.0474(6) Uani d . . . 1 . .
H H11 0.3885 0.508 0.2473 0.057 Uiso calc U . R 1 . .
C C12 0.5610(3) 0.3864(2) 0.25349(10) 0.0510(6) Uani d . . . 1 . .
H H12 0.5607 0.3584 0.2068 0.061 Uiso calc U . R 1 . .
C C13 0.6646(2) 0.3399(2) 0.29712(11) 0.0463(5) Uani d . . . 1 . .
H H13 0.7371 0.2819 0.2802 0.056 Uiso calc U . R 1 . .
C C14 0.6627(2) 0.3777(2) 0.36561(10) 0.0373(4) Uani d . . . 1 . .
H H14 0.7345 0.3459 0.3954 0.045 Uiso calc U . R 1 . .
C C15 0.63577(19) 0.40345(17) 0.56794(9) 0.0288(4) Uani d . . . 1 . .
C C16 0.53867(18) 0.38235(18) 0.62819(9) 0.0299(4) Uani d . . . 1 . .
H H16A 0.5039 0.2859 0.6281 0.036 Uiso calc U . R 1 . .
H H16B 0.4569 0.4447 0.6237 0.036 Uiso calc U . R 1 . .
C C17 0.61401(18) 0.41193(16) 0.69638(9) 0.0261(3) Uani d . . . 1 . .
H H17 0.6403 0.512 0.6978 0.031 Uiso calc U . R 1 . .
C C18 0.74692(17) 0.32505(17) 0.70231(9) 0.0274(3) Uani d . . . 1 . .
H H18A 0.7974 0.3503 0.7448 0.033 Uiso calc U . R 1 . .
H H18B 0.7215 0.226 0.7052 0.033 Uiso calc U . R 1 . .
C C19 0.84259(17) 0.34793(17) 0.64071(9) 0.0272(4) Uani d . . . 1 . .
H H19A 0.8749 0.4452 0.6402 0.033 Uiso calc U . R 1 . .
H H19B 0.926 0.2877 0.6449 0.033 Uiso calc U . R 1 . .
C C20 0.76726(18) 0.31604(18) 0.57380(9) 0.0289(4) Uani d . . . 1 . .
H H20A 0.8301 0.3357 0.5347 0.035 Uiso calc U . R 1 . .
H H20B 0.742 0.2168 0.5723 0.035 Uiso calc U . R 1 . .
C C21 0.5137(2) 0.38214(18) 0.75467(10) 0.0313(4) Uani d . . . 1 . .
N N1 0.44932(19) 0.49158(17) 0.78156(9) 0.0463(5) Uani d . . . 1 . .
H H1A 0.3881 0.4805 0.8148 0.056 Uiso calc U . R 1 . .
H H1B 0.468 0.575 0.7661 0.056 Uiso calc U . R 1 . .
O O1 0.56423(14) 0.37130(12) 0.50522(6) 0.0349(3) Uani d . . . 1 . .
O O2 0.67064(14) 0.54697(12) 0.56451(6) 0.0318(3) Uani d . . . 1 . .
O O3 0.48984(17) 0.26410(14) 0.77520(7) 0.0476(4) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.382(3) ?
C1 C6 . 1.395(3) ?
C1 C7 . 1.503(2) ?
C2 C3 . 1.396(3) ?
C2 H2 . 0.95 ?
C3 C4 . 1.379(3) ?
C3 H3 . 0.95 ?
C4 C5 . 1.380(3) ?
C4 H4 . 0.95 ?
C5 C6 . 1.394(3) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
C7 O2 . 1.426(2) ?
C7 C8 . 1.536(2) ?
C7 H7 . 1.0 ?
C8 O1 . 1.436(2) ?
C8 C9 . 1.499(2) ?
C8 H8 . 1.0 ?
C9 C10 . 1.388(3) ?
C9 C14 . 1.390(3) ?
C10 C11 . 1.392(3) ?
C10 H10 . 0.95 ?
C11 C12 . 1.379(3) ?
C11 H11 . 0.95 ?
C12 C13 . 1.381(3) ?
C12 H12 . 0.95 ?
C13 C14 . 1.387(3) ?
C13 H13 . 0.95 ?
C14 H14 . 0.95 ?
C15 O2 . 1.4289(19) ?
C15 O1 . 1.436(2) ?
C15 C16 . 1.512(2) ?
C15 C20 . 1.518(2) ?
C16 C17 . 1.540(2) ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
C17 C21 . 1.515(2) ?
C17 C18 . 1.526(2) ?
C17 H17 . 1.0 ?
C18 C19 . 1.526(2) ?
C18 H18A . 0.99 ?
C18 H18B . 0.99 ?
C19 C20 . 1.523(2) ?
C19 H19A . 0.99 ?
C19 H19B . 0.99 ?
C20 H20A . 0.99 ?
C20 H20B . 0.99 ?
C21 O3 . 1.231(2) ?
C21 N1 . 1.332(2) ?
N1 H1A . 0.88 ?
N1 H1B . 0.88 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 119.54(17) ?
C2 C1 C7 . . 121.56(16) ?
C6 C1 C7 . . 118.88(17) ?
C1 C2 C3 . . 119.94(19) ?
C1 C2 H2 . . 120.0 ?
C3 C2 H2 . . 120.0 ?
C4 C3 C2 . . 120.6(2) ?
C4 C3 H3 . . 119.7 ?
C2 C3 H3 . . 119.7 ?
C3 C4 C5 . . 119.71(18) ?
C3 C4 H4 . . 120.1 ?
C5 C4 H4 . . 120.1 ?
C4 C5 C6 . . 120.27(19) ?
C4 C5 H5 . . 119.9 ?
C6 C5 H5 . . 119.9 ?
C5 C6 C1 . . 120.0(2) ?
C5 C6 H6 . . 120.0 ?
C1 C6 H6 . . 120.0 ?
O2 C7 C1 . . 110.57(14) ?
O2 C7 C8 . . 101.44(13) ?
C1 C7 C8 . . 115.19(14) ?
O2 C7 H7 . . 109.8 ?
C1 C7 H7 . . 109.8 ?
C8 C7 H7 . . 109.8 ?
O1 C8 C9 . . 109.19(13) ?
O1 C8 C7 . . 102.00(13) ?
C9 C8 C7 . . 115.93(15) ?
O1 C8 H8 . . 109.8 ?
C9 C8 H8 . . 109.8 ?
C7 C8 H8 . . 109.8 ?
C10 C9 C14 . . 118.84(17) ?
C10 C9 C8 . . 120.49(17) ?
C14 C9 C8 . . 120.66(17) ?
C9 C10 C11 . . 120.3(2) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
C12 C11 C10 . . 120.2(2) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C11 C12 C13 . . 119.93(19) ?
C11 C12 H12 . . 120.0 ?
C13 C12 H12 . . 120.0 ?
C12 C13 C14 . . 120.0(2) ?
C12 C13 H13 . . 120.0 ?
C14 C13 H13 . . 120.0 ?
C13 C14 C9 . . 120.7(2) ?
C13 C14 H14 . . 119.7 ?
C9 C14 H14 . . 119.7 ?
O2 C15 O1 . . 106.33(13) ?
O2 C15 C16 . . 108.09(14) ?
O1 C15 C16 . . 110.03(14) ?
O2 C15 C20 . . 110.59(14) ?
O1 C15 C20 . . 109.71(14) ?
C16 C15 C20 . . 111.93(14) ?
C15 C16 C17 . . 111.16(14) ?
C15 C16 H16A . . 109.4 ?
C17 C16 H16A . . 109.4 ?
C15 C16 H16B . . 109.4 ?
C17 C16 H16B . . 109.4 ?
H16A C16 H16B . . 108.0 ?
C21 C17 C18 . . 111.36(14) ?
C21 C17 C16 . . 108.57(14) ?
C18 C17 C16 . . 110.60(13) ?
C21 C17 H17 . . 108.8 ?
C18 C17 H17 . . 108.8 ?
C16 C17 H17 . . 108.8 ?
C19 C18 C17 . . 110.98(13) ?
C19 C18 H18A . . 109.4 ?
C17 C18 H18A . . 109.4 ?
C19 C18 H18B . . 109.4 ?
C17 C18 H18B . . 109.4 ?
H18A C18 H18B . . 108.0 ?
C20 C19 C18 . . 111.33(14) ?
C20 C19 H19A . . 109.4 ?
C18 C19 H19A . . 109.4 ?
C20 C19 H19B . . 109.4 ?
C18 C19 H19B . . 109.4 ?
H19A C19 H19B . . 108.0 ?
C15 C20 C19 . . 110.04(14) ?
C15 C20 H20A . . 109.7 ?
C19 C20 H20A . . 109.7 ?
C15 C20 H20B . . 109.7 ?
C19 C20 H20B . . 109.7 ?
H20A C20 H20B . . 108.2 ?
O3 C21 N1 . . 121.56(17) ?
O3 C21 C17 . . 122.52(16) ?
N1 C21 C17 . . 115.90(15) ?
C21 N1 H1A . . 120.0 ?
C21 N1 H1B . . 120.0 ?
H1A N1 H1B . . 120.0 ?
C8 O1 C15 . . 108.47(12) ?
C7 O2 C15 . . 106.99(12) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.1(3) ?
C7 C1 C2 C3 . . . . -178.17(18) ?
C1 C2 C3 C4 . . . . 0.2(3) ?
C2 C3 C4 C5 . . . . 0.1(3) ?
C3 C4 C5 C6 . . . . -0.7(3) ?
C4 C5 C6 C1 . . . . 1.0(3) ?
C2 C1 C6 C5 . . . . -0.7(3) ?
C7 C1 C6 C5 . . . . 177.61(18) ?
C2 C1 C7 O2 . . . . -23.7(2) ?
C6 C1 C7 O2 . . . . 158.04(15) ?
C2 C1 C7 C8 . . . . 90.5(2) ?
C6 C1 C7 C8 . . . . -87.7(2) ?
O2 C7 C8 O1 . . . . -36.62(16) ?
C1 C7 C8 O1 . . . . -156.05(15) ?
O2 C7 C8 C9 . . . . -155.11(14) ?
C1 C7 C8 C9 . . . . 85.5(2) ?
O1 C8 C9 C10 . . . . 129.99(16) ?
C7 C8 C9 C10 . . . . -115.55(19) ?
O1 C8 C9 C14 . . . . -48.8(2) ?
C7 C8 C9 C14 . . . . 65.6(2) ?
C14 C9 C10 C11 . . . . 2.0(3) ?
C8 C9 C10 C11 . . . . -176.89(17) ?
C9 C10 C11 C12 . . . . 0.2(3) ?
C10 C11 C12 C13 . . . . -2.1(3) ?
C11 C12 C13 C14 . . . . 1.8(3) ?
C12 C13 C14 C9 . . . . 0.4(3) ?
C10 C9 C14 C13 . . . . -2.3(3) ?
C8 C9 C14 C13 . . . . 176.59(16) ?
O2 C15 C16 C17 . . . . -65.97(17) ?
O1 C15 C16 C17 . . . . 178.31(13) ?
C20 C15 C16 C17 . . . . 56.05(18) ?
C15 C16 C17 C21 . . . . -177.22(14) ?
C15 C16 C17 C18 . . . . -54.76(18) ?
C21 C17 C18 C19 . . . . 175.87(14) ?
C16 C17 C18 C19 . . . . 55.06(17) ?
C17 C18 C19 C20 . . . . -56.77(18) ?
O2 C15 C20 C19 . . . . 63.88(18) ?
O1 C15 C20 C19 . . . . -179.14(13) ?
C16 C15 C20 C19 . . . . -56.71(18) ?
C18 C19 C20 C15 . . . . 56.77(18) ?
C18 C17 C21 O3 . . . . -42.7(2) ?
C16 C17 C21 O3 . . . . 79.3(2) ?
C18 C17 C21 N1 . . . . 138.97(17) ?
C16 C17 C21 N1 . . . . -99.03(19) ?
C9 C8 O1 C15 . . . . 147.43(15) ?
C7 C8 O1 C15 . . . . 24.25(18) ?
O2 C15 O1 C8 . . . . -2.76(19) ?
C16 C15 O1 C8 . . . . 114.06(15) ?
C20 C15 O1 C8 . . . . -122.38(15) ?
C1 C7 O2 C15 . . . . 158.95(15) ?
C8 C7 O2 C15 . . . . 36.28(17) ?
O1 C15 O2 C7 . . . . -22.19(18) ?
C16 C15 O2 C7 . . . . -140.30(14) ?
C20 C15 O2 C7 . . . . 96.85(16) ?

