# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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. 
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data_cd15218
_database_code_depnum_ccdc_archive 'CCDC 1435436'
_audit_update_record             
;
2015-11-06 deposited with the CCDC.
2016-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_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 0.0033 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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.6053(10)
_cell_length_b                   11.6403(14)
_cell_length_c                   17.468(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1749.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4360
_cell_measurement_theta_min      5.277
_cell_measurement_theta_max      54.145

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6763
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10517
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.102
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3444
_reflns_number_gt                3189
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0701P)²+0.0824P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1282 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.3(5)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3444
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1043
_refine_ls_wR_factor_gt          0.1014
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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
N1 N 0.8531(2) 0.95531(15) 0.30430(9) 0.0362(4) Uani 1 1 d . . . . .
O1 O 1.2477(2) 1.12764(16) 0.36932(11) 0.0597(5) Uani 1 1 d . . . . .
H1 H 1.2642 1.1892 0.3480 0.090 Uiso 1 1 calc R U . . .
O2 O 0.7705(2) 0.83527(15) 0.21133(10) 0.0559(5) Uani 1 1 d . . . . .
O3 O 0.67416(18) 1.01548(13) 0.22209(8) 0.0430(4) Uani 1 1 d . . . . .
C1 C 0.8322(3) 1.05736(17) 0.34814(10) 0.0357(4) Uani 1 1 d . . . . .
C2 C 0.6882(3) 1.0879(2) 0.37751(12) 0.0450(5) Uani 1 1 d . . . . .
H2 H 0.6011 1.0429 0.3678 0.054 Uiso 1 1 calc R U . . .
C3 C 0.6763(4) 1.1860(2) 0.42131(13) 0.0562(6) Uani 1 1 d . . . . .
H3 H 0.5802 1.2080 0.4407 0.067 Uiso 1 1 calc R U . . .
C4 C 0.8058(4) 1.2516(2) 0.43652(14) 0.0627(8) Uani 1 1 d . . . . .
H4 H 0.7965 1.3176 0.4662 0.075 Uiso 1 1 calc R U . . .
C5 C 0.9482(3) 1.2203(2) 0.40822(13) 0.0515(6) Uani 1 1 d . . . . .
H5 H 1.0350 1.2651 0.4189 0.062 Uiso 1 1 calc R U . . .
C6 C 0.9638(3) 1.12227(18) 0.36377(11) 0.0392(5) Uani 1 1 d . . . . .
C7 C 1.1166(2) 1.07472(19) 0.33619(12) 0.0426(5) Uani 1 1 d . . . . .
H7 H 1.1225 1.0800 0.2803 0.051 Uiso 1 1 calc R U . . .
C8 C 1.1171(2) 0.94950(19) 0.36066(12) 0.0416(5) Uani 1 1 d . . . . .
H8A H 1.1039 0.9452 0.4157 0.050 Uiso 1 1 calc R U . . .
H8B H 1.2169 0.9157 0.3481 0.050 Uiso 1 1 calc R U . . .
C9 C 0.9875(2) 0.88005(18) 0.32161(11) 0.0375(4) Uani 1 1 d . . . . .
H9 H 1.0282 0.8506 0.2730 0.045 Uiso 1 1 calc R U . . .
C10 C 0.9451(2) 0.77840(17) 0.37126(11) 0.0365(4) Uani 1 1 d . . . . .
C11 C 1.0161(3) 0.6737(2) 0.35967(14) 0.0490(5) Uani 1 1 d . . . . .
H11 H 1.0832 0.6638 0.3185 0.059 Uiso 1 1 calc R U . . .
C12 C 0.9877(4) 0.5830(2) 0.40936(16) 0.0621(7) Uani 1 1 d . . . . .
H12 H 1.0360 0.5125 0.4013 0.075 Uiso 1 1 calc R U . . .
C13 C 0.8893(3) 0.5967(2) 0.46998(16) 0.0618(7) Uani 1 1 d . . . . .
H13 H 0.8708 0.5358 0.5032 0.074 Uiso 1 1 calc R U . . .
C14 C 0.8177(4) 0.7006(2) 0.48168(15) 0.0600(7) Uani 1 1 d . . . . .
H14 H 0.7512 0.7103 0.5231 0.072 Uiso 1 1 calc R U . . .
C15 C 0.8441(3) 0.79013(19) 0.43225(13) 0.0490(5) Uani 1 1 d . . . . .
H15 H 0.7932 0.8597 0.4399 0.059 Uiso 1 1 calc R U . . .
C16 C 0.7630(2) 0.92784(17) 0.24287(12) 0.0371(4) Uani 1 1 d . . . . .
C17 C 0.5372(3) 1.0013(2) 0.17196(13) 0.0498(6) Uani 1 1 d . . . . .
C18 C 0.5849(4) 0.9676(3) 0.09179(13) 0.0693(8) Uani 1 1 d . . . . .
H18A H 0.6242 0.8904 0.0921 0.104 Uiso 1 1 calc R U . . .
H18B H 0.6643 1.0189 0.0739 0.104 Uiso 1 1 calc R U . . .
H18C H 0.4965 0.9720 0.0584 0.104 Uiso 1 1 calc R U . . .
C19 C 0.4297(3) 0.9146(3) 0.20799(18) 0.0777(9) Uani 1 1 d . . . . .
H19A H 0.4759 0.8397 0.2053 0.117 Uiso 1 1 calc R U . . .
H19B H 0.3325 0.9142 0.1810 0.117 Uiso 1 1 calc R U . . .
H19C H 0.4121 0.9347 0.2606 0.117 Uiso 1 1 calc R U . . .
C20 C 0.4679(4) 1.1202(3) 0.1739(2) 0.0907(12) Uani 1 1 d . . . . .
H20A H 0.3737 1.1212 0.1445 0.136 Uiso 1 1 calc R U . . .
H20B H 0.5405 1.1740 0.1526 0.136 Uiso 1 1 calc R U . . .
H20C H 0.4454 1.1410 0.2259 0.136 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
N1 C16 1.362(3) . ?
N1 C1 1.425(3) . ?
N1 C9 1.482(3) . ?
O1 C7 1.409(3) . ?
O1 H1 0.8200 . ?
O2 C16 1.212(3) . ?
O3 C16 1.326(3) . ?
O3 C17 1.478(3) . ?
C1 C6 1.389(3) . ?
C1 C2 1.387(3) . ?
C2 C3 1.378(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.505(3) . ?
C7 C8 1.519(3) . ?
C7 H7 0.9800 . ?
C8 C9 1.537(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.512(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.378(3) . ?
C10 C15 1.382(3) . ?
C11 C12 1.389(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.365(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.373(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C17 C19 1.507(4) . ?
C17 C20 1.508(4) . ?
C17 C18 1.511(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
C16 N1 C1 123.17(16) . . ?
C16 N1 C9 117.78(15) . . ?
C1 N1 C9 118.82(16) . . ?
C7 O1 H1 109.5 . . ?
C16 O3 C17 122.43(17) . . ?
C6 C1 C2 121.09(18) . . ?
C6 C1 N1 117.12(19) . . ?
C2 C1 N1 121.7(2) . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 118.6(2) . . ?
C5 C6 C7 124.5(2) . . ?
C1 C6 C7 116.71(18) . . ?
O1 C7 C6 114.00(19) . . ?
O1 C7 C8 107.55(17) . . ?
C6 C7 C8 105.38(18) . . ?
O1 C7 H7 109.9 . . ?
C6 C7 H7 109.9 . . ?
C8 C7 H7 109.9 . . ?
C7 C8 C9 112.19(17) . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N1 C9 C10 113.04(17) . . ?
N1 C9 C8 110.23(17) . . ?
C10 C9 C8 109.40(17) . . ?
N1 C9 H9 108.0 . . ?
C10 C9 H9 108.0 . . ?
C8 C9 H9 108.0 . . ?
C11 C10 C15 118.7(2) . . ?
C11 C10 C9 120.06(19) . . ?
C15 C10 C9 121.11(19) . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.8(2) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C10 120.9(2) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
O2 C16 O3 126.17(19) . . ?
O2 C16 N1 122.47(19) . . ?
O3 C16 N1 111.32(16) . . ?
O3 C17 C19 108.5(2) . . ?
O3 C17 C20 101.5(2) . . ?
C19 C17 C20 111.3(3) . . ?
O3 C17 C18 111.2(2) . . ?
C19 C17 C18 112.3(2) . . ?
C20 C17 C18 111.5(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 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
C16 N1 C1 C6 -131.9(2) . . . . ?
C9 N1 C1 C6 42.5(2) . . . . ?
C16 N1 C1 C2 51.4(3) . . . . ?
C9 N1 C1 C2 -134.2(2) . . . . ?
C6 C1 C2 C3 1.6(3) . . . . ?
N1 C1 C2 C3 178.16(18) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C4 C5 C6 C7 -174.1(2) . . . . ?
C2 C1 C6 C5 -1.4(3) . . . . ?
N1 C1 C6 C5 -178.11(17) . . . . ?
C2 C1 C6 C7 173.63(19) . . . . ?
N1 C1 C6 C7 -3.1(2) . . . . ?
C5 C6 C7 O1 9.7(3) . . . . ?
C1 C6 C7 O1 -165.05(17) . . . . ?
C5 C6 C7 C8 127.4(2) . . . . ?
C1 C6 C7 C8 -47.4(2) . . . . ?
O1 C7 C8 C9 -174.54(17) . . . . ?
C6 C7 C8 C9 63.5(2) . . . . ?
C16 N1 C9 C10 -86.4(2) . . . . ?
C1 N1 C9 C10 98.9(2) . . . . ?
C16 N1 C9 C8 150.85(17) . . . . ?
C1 N1 C9 C8 -23.9(2) . . . . ?
C7 C8 C9 N1 -29.3(2) . . . . ?
C7 C8 C9 C10 -154.21(18) . . . . ?
N1 C9 C10 C11 143.8(2) . . . . ?
C8 C9 C10 C11 -93.0(2) . . . . ?
N1 C9 C10 C15 -41.0(3) . . . . ?
C8 C9 C10 C15 82.2(3) . . . . ?
C15 C10 C11 C12 -1.0(4) . . . . ?
C9 C10 C11 C12 174.3(2) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
C12 C13 C14 C15 0.5(4) . . . . ?
C13 C14 C15 C10 -1.5(4) . . . . ?
C11 C10 C15 C14 1.7(4) . . . . ?
C9 C10 C15 C14 -173.5(2) . . . . ?
C17 O3 C16 O2 19.2(3) . . . . ?
C17 O3 C16 N1 -163.10(17) . . . . ?
C1 N1 C16 O2 -171.6(2) . . . . ?
C9 N1 C16 O2 14.0(3) . . . . ?
C1 N1 C16 O3 10.6(3) . . . . ?
C9 N1 C16 O3 -163.82(17) . . . . ?
C16 O3 C17 C19 56.2(3) . . . . ?
C16 O3 C17 C20 173.4(2) . . . . ?
C16 O3 C17 C18 -67.9(3) . . . . ?

_refine_diff_density_max         0.160
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.035

_shelxl_version_number           2013-4



