# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_R20180617C1
_audit_block_doi                 10.5517/ccdc.csd.cc204f5s
_database_code_depnum_ccdc_archive 'CCDC 1851294'
_audit_update_record             
;
2018-06-24 deposited with the CCDC.
2018-10-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/8
_shelx_SHELXL_version_number     2014/8
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 N O3'
_chemical_formula_weight         309.35

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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   16.116(3)
_cell_length_b                   8.4159(17)
_cell_length_c                   23.178(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3143.7(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    6149
_cell_measurement_theta_min      1.7572
_cell_measurement_theta_max      27.8227

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6389
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            29353
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_av_R_equivalents  0.0838
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.165
_diffrn_reflns_theta_max         27.818
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3720
_reflns_number_gt                3203
_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.
;

_computing_data_collection       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_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          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1442P)²+0.5071P] 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     'SHELXL-2014/8 (Sheldrick 2014'
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3720
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0748
_refine_ls_wR_factor_ref         0.2370
_refine_ls_wR_factor_gt          0.2209
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.002
_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 0.02442(10) 0.54954(18) 0.41334(8) 0.0364(4) Uani 1 1 d . . . . .
O2 O 0.12388(12) 0.44408(19) 0.46643(8) 0.0423(5) Uani 1 1 d . . . . .
O3 O 0.14051(11) 0.9800(2) 0.71775(7) 0.0427(5) Uani 1 1 d . . . . .
N1 N 0.12028(12) 0.7135(2) 0.45896(8) 0.0303(5) Uani 1 1 d . . . . .
C1 C -0.07211(15) 0.6633(3) 0.35089(11) 0.0391(6) Uani 1 1 d . . . . .
H1A H -0.0732 0.5652 0.3306 0.047 Uiso 1 1 calc R U . . .
H1B H -0.1057 0.7494 0.3383 0.047 Uiso 1 1 calc R U . . .
C2 C -0.02380(14) 0.6799(3) 0.39660(10) 0.0322(5) Uani 1 1 d . . . . .
C3 C -0.01559(14) 0.8192(3) 0.43541(10) 0.0324(5) Uani 1 1 d . . . . .
H3A H -0.0406 0.7948 0.4734 0.039 Uiso 1 1 calc R U . . .
H3B H -0.0453 0.9114 0.4187 0.039 Uiso 1 1 calc R U . . .
C4 C 0.07633(14) 0.8595(2) 0.44296(9) 0.0296(5) Uani 1 1 d . . . . .
H4 H 0.0808 0.9345 0.4763 0.035 Uiso 1 1 calc R U . . .
C5 C 0.09254(15) 0.5656(3) 0.44847(10) 0.0313(5) Uani 1 1 d . . . . .
C6 C 0.11420(14) 0.9416(3) 0.39074(10) 0.0298(5) Uani 1 1 d . . . . .
C7 C 0.14105(15) 0.8573(3) 0.34281(10) 0.0356(6) Uani 1 1 d . . . . .
H7 H 0.1383 0.7445 0.3429 0.043 Uiso 1 1 calc R U . . .
C8 C 0.17196(17) 0.9362(3) 0.29464(11) 0.0413(6) Uani 1 1 d . . . . .
H8 H 0.1893 0.8779 0.2617 0.050 Uiso 1 1 calc R U . . .
C9 C 0.17738(16) 1.1013(3) 0.29503(12) 0.0434(6) Uani 1 1 d . . . . .
H9 H 0.1985 1.1559 0.2623 0.052 Uiso 1 1 calc R U . . .
C10 C 0.15220(17) 1.1853(3) 0.34283(12) 0.0436(6) Uani 1 1 d . . . . .
H10 H 0.1563 1.2979 0.3430 0.052 Uiso 1 1 calc R U . . .
C11 C 0.12080(15) 1.1066(3) 0.39083(11) 0.0360(6) Uani 1 1 d . . . . .
H11 H 0.1038 1.1654 0.4237 0.043 Uiso 1 1 calc R U . . .
C12 C 0.19675(14) 0.7347(3) 0.49224(10) 0.0320(5) Uani 1 1 d . . . . .
H12A H 0.2329 0.8120 0.4721 0.038 Uiso 1 1 calc R U . . .
H12B H 0.2267 0.6321 0.4941 0.038 Uiso 1 1 calc R U . . .
C13 C 0.18070(14) 0.7935(2) 0.55342(9) 0.0298(5) Uani 1 1 d . . . . .
C14 C 0.23722(14) 0.8947(3) 0.57998(10) 0.0323(5) Uani 1 1 d . . . . .
H14 H 0.2866 0.9236 0.5602 0.039 Uiso 1 1 calc R U . . .
C15 C 0.22249(15) 0.9539(3) 0.63482(10) 0.0359(6) Uani 1 1 d . . . . .
H15 H 0.2613 1.0241 0.6522 0.043 Uiso 1 1 calc R U . . .
C16 C 0.15067(15) 0.9105(3) 0.66450(9) 0.0327(5) Uani 1 1 d . . . . .
C17 C 0.09469(15) 0.8075(3) 0.63914(10) 0.0338(5) Uani 1 1 d . . . . .
H17 H 0.0460 0.7764 0.6593 0.041 Uiso 1 1 calc R U . . .
C18 C 0.10998(15) 0.7496(3) 0.58381(10) 0.0337(5) Uani 1 1 d . . . . .
H18 H 0.0714 0.6788 0.5666 0.040 Uiso 1 1 calc R U . . .
C19 C 0.06184(17) 0.9602(4) 0.74479(12) 0.0488(7) Uani 1 1 d . . . . .
H19A H 0.0182 1.0018 0.7195 0.073 Uiso 1 1 calc R U . . .
H19B H 0.0612 1.0181 0.7815 0.073 Uiso 1 1 calc R U . . .
H19C H 0.0520 0.8471 0.7520 0.073 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 C5 1.373(3) . ?
O1 C2 1.400(3) . ?
O2 C5 1.214(3) . ?
O3 C16 1.376(3) . ?
O3 C19 1.424(3) . ?
N1 C5 1.345(3) . ?
N1 C12 1.465(3) . ?
N1 C4 1.466(3) . ?
C1 C2 1.322(3) . ?
C1 H1A 0.9500 . ?
C1 H1B 0.9500 . ?
C2 C3 1.484(3) . ?
C3 C4 1.530(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C6 1.522(3) . ?
C4 H4 1.0000 . ?
C6 C7 1.388(3) . ?
C6 C11 1.392(3) . ?
C7 C8 1.392(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.392(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.376(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.524(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.390(3) . ?
C13 C14 1.391(3) . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.395(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(3) . ?
C17 C18 1.394(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C5 O1 C2 122.08(17) . . ?
C16 O3 C19 116.8(2) . . ?
C5 N1 C12 119.18(19) . . ?
C5 N1 C4 124.71(19) . . ?
C12 N1 C4 115.97(17) . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?
C1 C2 O1 117.8(2) . . ?
C1 C2 C3 128.5(2) . . ?
O1 C2 C3 113.7(2) . . ?
C2 C3 C4 109.31(18) . . ?
C2 C3 H3A 109.8 . . ?
C4 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
C4 C3 H3B 109.8 . . ?
H3A C3 H3B 108.3 . . ?
N1 C4 C6 112.84(18) . . ?
N1 C4 C3 108.15(17) . . ?
C6 C4 C3 113.46(18) . . ?
N1 C4 H4 107.4 . . ?
C6 C4 H4 107.4 . . ?
C3 C4 H4 107.4 . . ?
O2 C5 N1 125.4(2) . . ?
O2 C5 O1 116.9(2) . . ?
N1 C5 O1 117.64(19) . . ?
C7 C6 C11 119.2(2) . . ?
C7 C6 C4 121.96(19) . . ?
C11 C6 C4 118.9(2) . . ?
C6 C7 C8 120.6(2) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 119.6(2) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.4(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C6 120.1(2) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?
N1 C12 C13 112.75(19) . . ?
N1 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
N1 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C18 C13 C14 118.4(2) . . ?
C18 C13 C12 121.6(2) . . ?
C14 C13 C12 120.0(2) . . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 120.0(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
O3 C16 C17 124.8(2) . . ?
O3 C16 C15 115.4(2) . . ?
C17 C16 C15 119.8(2) . . ?
C16 C17 C18 119.7(2) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C13 C18 C17 121.2(2) . . ?
C13 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C5 O1 C2 C1 160.9(2) . . . . ?
C5 O1 C2 C3 -21.5(3) . . . . ?
C1 C2 C3 C4 -130.5(3) . . . . ?
O1 C2 C3 C4 52.3(2) . . . . ?
C5 N1 C4 C6 -104.5(2) . . . . ?
C12 N1 C4 C6 80.0(2) . . . . ?
C5 N1 C4 C3 21.9(3) . . . . ?
C12 N1 C4 C3 -153.65(19) . . . . ?
C2 C3 C4 N1 -50.6(2) . . . . ?
C2 C3 C4 C6 75.3(2) . . . . ?
C12 N1 C5 O2 3.2(4) . . . . ?
C4 N1 C5 O2 -172.2(2) . . . . ?
C12 N1 C5 O1 -174.97(19) . . . . ?
C4 N1 C5 O1 9.6(3) . . . . ?
C2 O1 C5 O2 170.9(2) . . . . ?
C2 O1 C5 N1 -10.8(3) . . . . ?
N1 C4 C6 C7 41.9(3) . . . . ?
C3 C4 C6 C7 -81.6(3) . . . . ?
N1 C4 C6 C11 -139.2(2) . . . . ?
C3 C4 C6 C11 97.3(2) . . . . ?
C11 C6 C7 C8 -1.9(3) . . . . ?
C4 C6 C7 C8 177.1(2) . . . . ?
C6 C7 C8 C9 1.2(4) . . . . ?
C7 C8 C9 C10 0.0(4) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C9 C10 C11 C6 -0.3(4) . . . . ?
C7 C6 C11 C10 1.5(3) . . . . ?
C4 C6 C11 C10 -177.5(2) . . . . ?
C5 N1 C12 C13 -106.1(2) . . . . ?
C4 N1 C12 C13 69.7(2) . . . . ?
N1 C12 C13 C18 33.0(3) . . . . ?
N1 C12 C13 C14 -146.4(2) . . . . ?
C18 C13 C14 C15 -1.7(3) . . . . ?
C12 C13 C14 C15 177.8(2) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
C19 O3 C16 C17 -8.6(3) . . . . ?
C19 O3 C16 C15 169.5(2) . . . . ?
C14 C15 C16 O3 -177.8(2) . . . . ?
C14 C15 C16 C17 0.4(4) . . . . ?
O3 C16 C17 C18 177.2(2) . . . . ?
C15 C16 C17 C18 -0.8(4) . . . . ?
C14 C13 C18 C17 1.3(3) . . . . ?
C12 C13 C18 C17 -178.2(2) . . . . ?
C16 C17 C18 C13 -0.1(4) . . . . ?

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.056



