# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_hwang10
_database_code_depnum_ccdc_archive 'CCDC 1518410'
_audit_update_record             
;
2016-11-21 deposited with the CCDC.
2017-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H23 N O3'
_chemical_formula_sum            'C20 H23 N O3'
_chemical_formula_weight         325.39

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.6820(6)
_cell_length_b                   7.2674(4)
_cell_length_c                   20.0741(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.443(4)
_cell_angle_gamma                90
_cell_volume                     1657.55(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4019
_cell_measurement_theta_min      3.593
_cell_measurement_theta_max      66.899

_exptl_crystal_description       'transparent prism'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.699
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7490
_exptl_absorpt_correction_T_max  0.8299
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10702
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.021
_diffrn_reflns_theta_max         68.431
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             2980
_reflns_number_gt                2206
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.

All nonhydrogen atoms were located in a difference Fourier electron
 density map and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 (1.5Ueq for methyl groups) of the connected C atoms.  The N-H and O-H
 hydrogen atoms were located in a diff map and refined isotropically
 with Uiso = 1.2xUeqiv and restrained to 0.85(2) ang. 
;

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SAINT (Bruker, 2008) and XPREP (Bruker, 2008)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0597P)²+2.7815P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2980
_refine_ls_number_parameters     224
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0634
_refine_ls_wR_factor_ref         0.1652
_refine_ls_wR_factor_gt          0.1481
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.84027(17) 0.9067(3) 0.64689(10) 0.0279(5) Uani 1 1 d . . . . .
H6 H 0.997(2) 0.738(5) 0.6041(13) 0.033 Uiso 1 1 d D U . . .
O2 O 0.94019(17) 0.7733(3) 0.57141(11) 0.0308(5) Uani 1 1 d D . . . .
O3 O 0.63382(17) 0.8218(3) 0.17810(10) 0.0284(5) Uani 1 1 d . . . . .
N1 N 0.6066(2) 0.8504(4) 0.45109(13) 0.0305(6) Uani 1 1 d D . . . .
H1 H 0.556(2) 0.933(4) 0.4597(16) 0.037 Uiso 1 1 d D U . . .
C1 C 0.7387(2) 0.8035(4) 0.63786(15) 0.0234(6) Uani 1 1 d . . . . .
C2 C 0.7110(3) 0.7353(4) 0.69691(15) 0.0288(7) Uani 1 1 d . . . . .
H2 H 0.7612 0.7599 0.7405 0.035 Uiso 1 1 calc R U . . .
C3 C 0.6101(3) 0.6316(5) 0.69216(16) 0.0322(7) Uani 1 1 d . . . . .
H3 H 0.5915 0.5838 0.7324 0.039 Uiso 1 1 calc R U . . .
C4 C 0.5362(3) 0.5975(5) 0.62858(16) 0.0311(7) Uani 1 1 d . . . . .
H4 H 0.4667 0.5268 0.6252 0.037 Uiso 1 1 calc R U . . .
C5 C 0.5639(2) 0.6666(4) 0.57026(15) 0.0250(6) Uani 1 1 d . . . . .
H5 H 0.5123 0.6435 0.5270 0.030 Uiso 1 1 calc R U . . .
C6 C 0.6657(2) 0.7694(4) 0.57317(14) 0.0230(6) Uani 1 1 d . . . . .
C7 C 0.7057(2) 0.8239(4) 0.50870(15) 0.0274(7) Uani 1 1 d . . . . .
H7 H 0.7513 0.7172 0.4969 0.033 Uiso 1 1 calc R U . . .
C8 C 0.7919(2) 0.9860(4) 0.52470(15) 0.0261(7) Uani 1 1 d . . . . .
H8 H 0.8287 1.0017 0.4848 0.031 Uiso 1 1 calc R U . . .
C9 C 0.7355(3) 1.1678(5) 0.53602(16) 0.0316(7) Uani 1 1 d . . . . .
H9A H 0.6946 1.1541 0.5737 0.038 Uiso 1 1 calc R U . . .
H9B H 0.6761 1.2014 0.4940 0.038 Uiso 1 1 calc R U . . .
C10 C 0.8275(3) 1.3226(4) 0.55383(17) 0.0357(8) Uani 1 1 d . . . . .
H10A H 0.8643 1.3433 0.5147 0.043 Uiso 1 1 calc R U . . .
H10B H 0.7884 1.4382 0.5624 0.043 Uiso 1 1 calc R U . . .
C11 C 0.9227(3) 1.2714(5) 0.61772(17) 0.0349(8) Uani 1 1 d . . . . .
H11A H 0.9838 1.3685 0.6269 0.042 Uiso 1 1 calc R U . . .
H11B H 0.8871 1.2634 0.6578 0.042 Uiso 1 1 calc R U . . .
C12 C 0.9790(3) 1.0889(5) 0.60776(16) 0.0322(7) Uani 1 1 d . . . . .
H12A H 1.0351 1.0545 0.6510 0.039 Uiso 1 1 calc R U . . .
H12B H 1.0242 1.1032 0.5720 0.039 Uiso 1 1 calc R U . . .
C13 C 0.8898(2) 0.9340(4) 0.58699(14) 0.0259(7) Uani 1 1 d . . . . .
C14 C 0.6197(3) 0.8421(4) 0.38336(15) 0.0261(7) Uani 1 1 d . . . . .
C15 C 0.5299(3) 0.9076(4) 0.33134(16) 0.0291(7) Uani 1 1 d . . . . .
H15 H 0.4625 0.9614 0.3424 0.035 Uiso 1 1 calc R U . . .
C16 C 0.5360(2) 0.8967(4) 0.26430(15) 0.0282(7) Uani 1 1 d . . . . .
H16 H 0.4733 0.9425 0.2293 0.034 Uiso 1 1 calc R U . . .
C17 C 0.6343(2) 0.8185(4) 0.24734(14) 0.0233(6) Uani 1 1 d . . . . .
C18 C 0.7245(2) 0.7480(4) 0.29735(14) 0.0235(6) Uani 1 1 d . . . . .
H18 H 0.7907 0.6922 0.2856 0.028 Uiso 1 1 calc R U . . .
C19 C 0.7171(3) 0.7597(4) 0.36572(15) 0.0277(7) Uani 1 1 d . . . . .
H19 H 0.7789 0.7111 0.4007 0.033 Uiso 1 1 calc R U . . .
C20 C 0.7392(3) 0.7656(5) 0.15958(15) 0.0305(7) Uani 1 1 d . . . . .
H20A H 0.8059 0.8359 0.1862 0.046 Uiso 1 1 calc R U . . .
H20B H 0.7318 0.7883 0.1106 0.046 Uiso 1 1 calc R U . . .
H20C H 0.7523 0.6341 0.1691 0.046 Uiso 1 1 calc R U . . .


_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 C1 1.379(3) . ?
O1 C13 1.464(3) . ?
O2 C13 1.376(4) . ?
O2 H6 0.858(18) . ?
O3 C17 1.389(3) . ?
O3 C20 1.426(3) . ?
N1 C14 1.405(4) . ?
N1 C7 1.446(4) . ?
N1 H1 0.886(18) . ?
C1 C2 1.391(4) . ?
C1 C6 1.400(4) . ?
C2 C3 1.383(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.526(4) . ?
C7 C8 1.535(4) . ?
C7 H7 1.0000 . ?
C8 C9 1.516(4) . ?
C8 C13 1.533(4) . ?
C8 H8 1.0000 . ?
C9 C10 1.540(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.535(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.514(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.525(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 C15 1.382(4) . ?
C14 C19 1.402(4) . ?
C15 C16 1.367(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.392(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.375(4) . ?
C18 C19 1.398(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
C1 O1 C13 117.2(2) . . ?
C13 O2 H6 112(2) . . ?
C17 O3 C20 117.0(2) . . ?
C14 N1 C7 121.4(2) . . ?
C14 N1 H1 116(2) . . ?
C7 N1 H1 112(2) . . ?
O1 C1 C2 116.5(2) . . ?
O1 C1 C6 122.5(3) . . ?
C2 C1 C6 121.0(3) . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 121.7(3) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 117.6(3) . . ?
C5 C6 C7 122.0(3) . . ?
C1 C6 C7 120.0(3) . . ?
N1 C7 C6 111.5(2) . . ?
N1 C7 C8 115.4(3) . . ?
C6 C7 C8 109.7(2) . . ?
N1 C7 H7 106.6 . . ?
C6 C7 H7 106.6 . . ?
C8 C7 H7 106.6 . . ?
C9 C8 C13 111.1(2) . . ?
C9 C8 C7 114.4(2) . . ?
C13 C8 C7 108.1(2) . . ?
C9 C8 H8 107.7 . . ?
C13 C8 H8 107.7 . . ?
C7 C8 H8 107.7 . . ?
C8 C9 C10 111.6(2) . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C9 110.4(3) . . ?
C11 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C12 C11 C10 110.8(3) . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 C13 113.1(2) . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
O2 C13 O1 110.1(2) . . ?
O2 C13 C12 112.8(2) . . ?
O1 C13 C12 104.5(2) . . ?
O2 C13 C8 107.5(2) . . ?
O1 C13 C8 109.9(2) . . ?
C12 C13 C8 112.0(3) . . ?
C15 C14 C19 118.4(3) . . ?
C15 C14 N1 118.8(3) . . ?
C19 C14 N1 122.7(3) . . ?
C16 C15 C14 121.3(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 120.0(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 O3 124.1(3) . . ?
C18 C17 C16 120.6(3) . . ?
O3 C17 C16 115.2(2) . . ?
C17 C18 C19 118.8(3) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C18 C19 C14 120.9(3) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 O1 C1 C2 162.5(3) . . . . ?
C13 O1 C1 C6 -18.1(4) . . . . ?
O1 C1 C2 C3 179.6(3) . . . . ?
C6 C1 C2 C3 0.2(5) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
C4 C5 C6 C1 -1.1(4) . . . . ?
C4 C5 C6 C7 171.5(3) . . . . ?
O1 C1 C6 C5 -178.7(3) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
O1 C1 C6 C7 8.6(4) . . . . ?
C2 C1 C6 C7 -172.1(3) . . . . ?
C14 N1 C7 C6 -159.1(3) . . . . ?
C14 N1 C7 C8 74.8(4) . . . . ?
C5 C6 C7 N1 31.5(4) . . . . ?
C1 C6 C7 N1 -156.0(3) . . . . ?
C5 C6 C7 C8 160.7(3) . . . . ?
C1 C6 C7 C8 -26.9(4) . . . . ?
N1 C7 C8 C9 55.3(4) . . . . ?
C6 C7 C8 C9 -71.7(3) . . . . ?
N1 C7 C8 C13 179.6(3) . . . . ?
C6 C7 C8 C13 52.7(3) . . . . ?
C13 C8 C9 C10 55.6(3) . . . . ?
C7 C8 C9 C10 178.4(3) . . . . ?
C8 C9 C10 C11 -57.4(4) . . . . ?
C9 C10 C11 C12 55.8(4) . . . . ?
C10 C11 C12 C13 -54.0(4) . . . . ?
C1 O1 C13 O2 -72.7(3) . . . . ?
C1 O1 C13 C12 165.9(2) . . . . ?
C1 O1 C13 C8 45.6(3) . . . . ?
C11 C12 C13 O2 173.9(2) . . . . ?
C11 C12 C13 O1 -66.5(3) . . . . ?
C11 C12 C13 C8 52.5(4) . . . . ?
C9 C8 C13 O2 -177.0(2) . . . . ?
C7 C8 C13 O2 56.7(3) . . . . ?
C9 C8 C13 O1 63.2(3) . . . . ?
C7 C8 C13 O1 -63.2(3) . . . . ?
C9 C8 C13 C12 -52.6(3) . . . . ?
C7 C8 C13 C12 -178.9(2) . . . . ?
C7 N1 C14 C15 -165.8(3) . . . . ?
C7 N1 C14 C19 18.2(5) . . . . ?
C19 C14 C15 C16 -1.4(5) . . . . ?
N1 C14 C15 C16 -177.5(3) . . . . ?
C14 C15 C16 C17 -0.1(5) . . . . ?
C20 O3 C17 C18 -6.8(4) . . . . ?
C20 O3 C17 C16 171.9(3) . . . . ?
C15 C16 C17 C18 1.5(5) . . . . ?
C15 C16 C17 O3 -177.3(3) . . . . ?
O3 C17 C18 C19 177.3(3) . . . . ?
C16 C17 C18 C19 -1.4(4) . . . . ?
C17 C18 C19 C14 -0.1(4) . . . . ?
C15 C14 C19 C18 1.5(4) . . . . ?
N1 C14 C19 C18 177.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H6 O3 0.858(18) 1.960(19) 2.816(3) 175(3) 4_676

_refine_diff_density_max         0.499
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.063

_shelxl_version_number           2012-9

