# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1854514'
_audit_update_record             
;
2018-07-09 deposited with the CCDC.
2018-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 N O3'
_chemical_formula_weight         307.33

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                   8.31350(10)
_cell_length_b                   7.85760(10)
_cell_length_c                   24.1360(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.4900(10)
_cell_angle_gamma                90
_cell_volume                     1555.09(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7421
_cell_measurement_theta_min      5.3910
_cell_measurement_theta_max      71.1220
_exptl_crystal_colour            'dull orangish orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    0.721
_shelx_estimated_absorpt_T_min   0.632
_shelx_estimated_absorpt_T_max   0.813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72034
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10584
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.714
_diffrn_reflns_theta_max         71.364
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2988
_reflns_number_gt                2830
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0842P)²+0.3549P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0066(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2988
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1411
_refine_ls_wR_factor_gt          0.1392
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 0.25521(15) 0.31270(17) 0.43154(6) 0.0326(3) Uani 1 1 d . . . . .
C2 C 0.35674(16) 0.42119(17) 0.40641(5) 0.0331(3) Uani 1 1 d . . . . .
C3 C 0.5350(2) 0.4510(2) 0.33957(8) 0.0567(5) Uani 1 1 d . . . . .
H3A H 0.5714 0.3887 0.3097 0.085 Uiso 1 1 calc R U . . .
H3B H 0.6269 0.4783 0.3678 0.085 Uiso 1 1 calc R U . . .
H3C H 0.4825 0.5541 0.3249 0.085 Uiso 1 1 calc R U . . .
C4 C 0.18759(17) 0.37145(18) 0.47643(6) 0.0375(3) Uani 1 1 d . . . . .
H4 H 0.1208 0.3000 0.4934 0.045 Uiso 1 1 calc R U . . .
C5 C 0.21795(16) 0.53625(19) 0.49672(6) 0.0368(3) Uani 1 1 d . . . . .
H5 H 0.1720 0.5740 0.5271 0.044 Uiso 1 1 calc R U . . .
C6 C 0.31640(15) 0.64376(17) 0.47167(5) 0.0313(3) Uani 1 1 d . . . . .
C7 C 0.38520(16) 0.58476(17) 0.42627(6) 0.0337(3) Uani 1 1 d . . . . .
H7 H 0.4511 0.6568 0.4092 0.040 Uiso 1 1 calc R U . . .
C8 C 0.36271(16) 0.82184(17) 0.49127(6) 0.0343(3) Uani 1 1 d . . . . .
H8A H 0.4776 0.8224 0.5074 0.041 Uiso 1 1 calc R U . . .
H8B H 0.3489 0.8961 0.4587 0.041 Uiso 1 1 calc R U . . .
C9 C 0.34349(16) 0.94844(16) 0.58143(5) 0.0326(3) Uani 1 1 d . . . . .
H9 H 0.4543 0.9258 0.5913 0.039 Uiso 1 1 calc R U . . .
C10 C 0.26909(16) 1.03839(16) 0.62044(5) 0.0319(3) Uani 1 1 d . . . . .
C11 C 0.09977(16) 1.08026(18) 0.60737(6) 0.0358(3) Uani 1 1 d . . . . .
C12 C 0.03219(19) 1.1862(2) 0.64608(7) 0.0484(4) Uani 1 1 d . . . . .
H12 H -0.0769 1.2180 0.6378 0.058 Uiso 1 1 calc R U . . .
C13 C 0.1233(2) 1.2410(2) 0.69430(7) 0.0476(4) Uani 1 1 d . . . . .
H13 H 0.0752 1.3108 0.7181 0.057 Uiso 1 1 calc R U . . .
C14 C 0.29122(18) 1.19546(19) 0.71008(6) 0.0384(3) Uani 1 1 d . . . . .
C15 C 0.36597(17) 1.09441(17) 0.67326(6) 0.0342(3) Uani 1 1 d . . . . .
C16 C 0.53260(19) 1.0531(2) 0.68985(7) 0.0456(4) Uani 1 1 d . . . . .
H16 H 0.5854 0.9863 0.6666 0.055 Uiso 1 1 calc R U . . .
C17 C 0.6173(2) 1.1111(3) 0.74031(8) 0.0565(5) Uani 1 1 d . . . . .
H17 H 0.7267 1.0825 0.7505 0.068 Uiso 1 1 calc R U . . .
C18 C 0.5431(2) 1.2108(3) 0.77610(7) 0.0569(5) Uani 1 1 d . . . . .
H18 H 0.6023 1.2493 0.8098 0.068 Uiso 1 1 calc R U . . .
C19 C 0.3820(2) 1.2520(2) 0.76139(6) 0.0486(4) Uani 1 1 d . . . . .
H19 H 0.3315 1.3182 0.7855 0.058 Uiso 1 1 calc R U . . .
N1 N 0.27142(14) 0.89316(15) 0.53229(5) 0.0339(3) Uani 1 1 d . . . . .
O1 O 0.42287(14) 0.35022(13) 0.36371(5) 0.0455(3) Uani 1 1 d . . . . .
O2 O 0.23493(13) 0.15241(12) 0.41015(5) 0.0416(3) Uani 1 1 d . . . . .
H2 H 0.1553 0.1083 0.4203 0.062 Uiso 1 1 calc R U . . .
O3 O 0.01001(11) 1.02652(14) 0.56262(4) 0.0418(3) Uani 1 1 d . . . . .
H3 H 0.0649 0.9682 0.5446 0.063 Uiso 1 1 calc R U . A 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.3611(16) . ?
C1 C4 1.380(2) . ?
C1 C2 1.4056(19) . ?
C2 O1 1.3647(16) . ?
C2 C7 1.3785(19) . ?
C3 O1 1.4191(19) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.393(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.3962(18) . ?
C6 C8 1.5067(18) . ?
C7 H7 0.9300 . ?
C8 N1 1.4553(17) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N1 1.3116(17) . ?
C9 C10 1.4002(19) . ?
C9 H9 0.9300 . ?
C10 C11 1.4293(19) . ?
C10 C15 1.4592(18) . ?
C11 O3 1.2790(17) . ?
C11 C12 1.434(2) . ?
C12 C13 1.350(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.431(2) . ?
C13 H13 0.9300 . ?
C14 C19 1.412(2) . ?
C14 C15 1.410(2) . ?
C15 C16 1.415(2) . ?
C16 C17 1.380(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.367(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
O2 H2 0.8200 . ?
O3 H3 0.8200 . ?

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
O2 C1 C4 124.50(12) . . ?
O2 C1 C2 116.31(12) . . ?
C4 C1 C2 119.16(12) . . ?
O1 C2 C7 125.18(12) . . ?
O1 C2 C1 115.05(12) . . ?
C7 C2 C1 119.76(12) . . ?
O1 C3 H3A 109.5 . . ?
O1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
O1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 C5 120.89(13) . . ?
C1 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 120.02(13) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 119.27(12) . . ?
C5 C6 C8 124.68(12) . . ?
C7 C6 C8 115.99(12) . . ?
C2 C7 C6 120.89(12) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
N1 C8 C6 115.87(11) . . ?
N1 C8 H8A 108.3 . . ?
C6 C8 H8A 108.3 . . ?
N1 C8 H8B 108.3 . . ?
C6 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
N1 C9 C10 126.06(12) . . ?
N1 C9 H9 117.0 . . ?
C10 C9 H9 117.0 . . ?
C9 C10 C11 119.73(12) . . ?
C9 C10 C15 119.89(12) . . ?
C11 C10 C15 120.34(12) . . ?
O3 C11 C10 121.78(13) . . ?
O3 C11 C12 120.36(13) . . ?
C10 C11 C12 117.86(12) . . ?
C13 C12 C11 121.51(14) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 122.26(14) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C19 C14 C15 120.19(14) . . ?
C19 C14 C13 120.79(14) . . ?
C15 C14 C13 119.02(13) . . ?
C14 C15 C16 117.62(13) . . ?
C14 C15 C10 118.91(12) . . ?
C16 C15 C10 123.47(13) . . ?
C17 C16 C15 120.46(15) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 121.54(16) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C19 C18 C17 119.37(14) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C14 120.83(15) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C9 N1 C8 122.07(11) . . ?
C2 O1 C3 117.11(12) . . ?
C1 O2 H2 109.5 . . ?
C11 O3 H3 109.5 . . ?

_refine_diff_density_max         0.711
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.046

