# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1851659'
_audit_update_record             
;
2018-10-09 deposited with the CCDC.
2018-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 N O2'
_chemical_formula_weight         303.35

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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   13.8678(10)
_cell_length_b                   13.8895(10)
_cell_length_c                   8.3340(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1605.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6231
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      22.00

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   Sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focuse sealed tube'
_diffrn_measurement_device_type  'Bruker D8 - QUEST'
_diffrn_measurement_method       'omega/phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17077
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.075
_diffrn_reflns_theta_max         25.643
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2937
_reflns_number_gt                2143
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.857
_reflns_Friedel_fraction_max     0.964
_reflns_Friedel_fraction_full    0.991

_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       'APEX3 v2017.3-0 (Bruker AXS)'
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-III (1.0.3) (Farrugia, 2012)'
_computing_publication_material  'Platon (Spek, 2009)'
_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)+(0.0781P)²] 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         2937
_refine_ls_number_parameters     216
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1314
_refine_ls_wR_factor_gt          0.1184
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_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
O2 O 0.93987(19) 0.38178(19) 0.3228(3) 0.0597(8) Uani 1 1 d . . . . .
O1 O 0.9325(2) 0.5538(2) 0.0207(4) 0.0660(8) Uani 1 1 d . . . . .
N1 N 0.7962(2) 0.4573(2) 0.1714(4) 0.0434(8) Uani 1 1 d . . . . .
C1 C 0.8407(3) 0.5838(3) -0.0048(4) 0.0476(9) Uani 1 1 d . . . . .
C2 C 0.8178(3) 0.6630(3) -0.0992(5) 0.0554(10) Uani 1 1 d . . . . .
H2 H 0.866505 0.698655 -0.147829 0.067 Uiso 1 1 calc R U . . .
C3 C 0.7234(3) 0.6883(3) -0.1204(5) 0.0584(10) Uani 1 1 d . . . . .
H3 H 0.708874 0.741214 -0.184351 0.070 Uiso 1 1 calc R U . . .
C4 C 0.6476(3) 0.6369(3) -0.0489(4) 0.0521(10) Uani 1 1 d . . . . .
C5 C 0.5451(3) 0.6648(3) -0.0771(6) 0.0784(14) Uani 1 1 d . . . . .
H5A H 0.542862 0.719598 -0.147191 0.118 Uiso 1 1 calc R U . . .
H5B H 0.511321 0.611987 -0.125635 0.118 Uiso 1 1 calc R U . . .
H5C H 0.515313 0.680758 0.023374 0.118 Uiso 1 1 calc R U . . .
C6 C 0.6720(3) 0.5597(3) 0.0482(5) 0.0485(9) Uani 1 1 d . . . . .
H6 H 0.623552 0.525030 0.099366 0.058 Uiso 1 1 calc R U . . .
C7 C 0.7674(3) 0.5335(2) 0.0701(4) 0.0434(9) Uani 1 1 d . . . . .
C8 C 0.7434(3) 0.3897(2) 0.2354(5) 0.0463(8) Uani 1 1 d . . . . .
H8 H 0.677690 0.389342 0.213438 0.056 Uiso 1 1 calc R U . . .
C9 C 0.7807(3) 0.3177(2) 0.3354(4) 0.0456(9) Uani 1 1 d . . . . .
C10 C 0.8814(3) 0.3160(3) 0.3753(4) 0.0500(9) Uani 1 1 d . . . . .
C11 C 0.9120(3) 0.2391(3) 0.4725(5) 0.0637(11) Uani 1 1 d . . . . .
H11 H 0.976105 0.236621 0.504956 0.076 Uiso 1 1 calc R U . . .
C12 C 0.8510(3) 0.1686(3) 0.5204(5) 0.0623(11) Uani 1 1 d . . . . .
H12 H 0.875549 0.117808 0.580655 0.075 Uiso 1 1 calc R U . . .
C13 C 0.7522(3) 0.1688(2) 0.4831(5) 0.0530(10) Uani 1 1 d . . . . .
C14 C 0.7194(3) 0.2443(3) 0.3931(4) 0.0505(9) Uani 1 1 d . . . . .
H14 H 0.653981 0.247465 0.368865 0.061 Uiso 1 1 calc R U . . .
C15 C 0.6886(4) 0.0907(3) 0.5420(5) 0.0618(11) Uani 1 1 d . . . . .
C16 C 0.6005(4) 0.1094(3) 0.6085(6) 0.0732(13) Uani 1 1 d . . . . .
H16 H 0.577517 0.172304 0.611035 0.088 Uiso 1 1 calc R U . . .
C17 C 0.5445(4) 0.0352(4) 0.6726(7) 0.0948(17) Uani 1 1 d . . . . .
H17 H 0.484774 0.048910 0.718024 0.114 Uiso 1 1 calc R U . . .
C18 C 0.5772(6) -0.0574(4) 0.6688(8) 0.101(2) Uani 1 1 d . . . . .
H18 H 0.540853 -0.106535 0.714436 0.121 Uiso 1 1 calc R U . . .
C20 C 0.6636(7) -0.0775(4) 0.5976(8) 0.107(2) Uani 1 1 d . . . . .
H20 H 0.684602 -0.140938 0.591096 0.128 Uiso 1 1 calc R U . . .
C21 C 0.7197(4) -0.0055(3) 0.5358(7) 0.0862(16) Uani 1 1 d . . . . .
H21 H 0.778859 -0.020287 0.489373 0.103 Uiso 1 1 calc R U . . .
H1N1 H 0.856(3) 0.453(3) 0.204(6) 0.069(14) Uiso 1 1 d . . . . .
H1O1 H 0.973(4) 0.577(4) -0.052(7) 0.098(19) Uiso 1 1 d . . . . .


_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
O2 C10 1.297(5) . ?
O1 C1 1.356(5) . ?
O1 H1O1 0.89(6) . ?
N1 C8 1.305(5) . ?
N1 C7 1.411(5) . ?
N1 H1N1 0.88(5) . ?
C1 C7 1.383(5) . ?
C1 C2 1.389(5) . ?
C2 C3 1.368(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(6) . ?
C3 H3 0.9300 . ?
C4 C6 1.385(5) . ?
C4 C5 1.491(6) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.385(5) . ?
C6 H6 0.9300 . ?
C8 C9 1.401(5) . ?
C8 H8 0.9300 . ?
C9 C14 1.412(5) . ?
C9 C10 1.437(5) . ?
C10 C11 1.406(5) . ?
C11 C12 1.355(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.405(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.367(5) . ?
C13 C15 1.482(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.367(7) . ?
C15 C21 1.404(6) . ?
C16 C17 1.397(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.363(8) . ?
C17 H17 0.9300 . ?
C18 C20 1.367(9) . ?
C18 H18 0.9300 . ?
C20 C21 1.368(9) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?

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 H1O1 112(3) . . ?
C8 N1 C7 128.7(3) . . ?
C8 N1 H1N1 111(3) . . ?
C7 N1 H1N1 121(3) . . ?
O1 C1 C7 117.6(3) . . ?
O1 C1 C2 123.2(3) . . ?
C7 C1 C2 119.2(3) . . ?
C3 C2 C1 119.7(4) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 122.1(4) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C6 C4 C3 117.3(4) . . ?
C6 C4 C5 121.7(4) . . ?
C3 C4 C5 121.0(4) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C4 120.9(4) . . ?
C7 C6 H6 119.5 . . ?
C4 C6 H6 119.5 . . ?
C6 C7 C1 120.6(3) . . ?
C6 C7 N1 123.2(3) . . ?
C1 C7 N1 116.2(3) . . ?
N1 C8 C9 123.4(4) . . ?
N1 C8 H8 118.3 . . ?
C9 C8 H8 118.3 . . ?
C8 C9 C14 119.8(3) . . ?
C8 C9 C10 120.5(3) . . ?
C14 C9 C10 119.6(3) . . ?
O2 C10 C11 122.7(4) . . ?
O2 C10 C9 121.2(3) . . ?
C11 C10 C9 116.1(3) . . ?
C12 C11 C10 122.1(4) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 122.8(4) . . ?
C11 C12 H12 118.6 . . ?
C13 C12 H12 118.6 . . ?
C14 C13 C12 116.6(4) . . ?
C14 C13 C15 123.1(4) . . ?
C12 C13 C15 120.3(3) . . ?
C13 C14 C9 122.7(4) . . ?
C13 C14 H14 118.6 . . ?
C9 C14 H14 118.6 . . ?
C16 C15 C21 118.0(4) . . ?
C16 C15 C13 121.8(4) . . ?
C21 C15 C13 120.1(5) . . ?
C15 C16 C17 120.8(5) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 120.1(7) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C20 119.6(6) . . ?
C17 C18 H18 120.2 . . ?
C20 C18 H18 120.2 . . ?
C21 C20 C18 120.9(5) . . ?
C21 C20 H20 119.6 . . ?
C18 C20 H20 119.6 . . ?
C20 C21 C15 120.5(6) . . ?
C20 C21 H21 119.8 . . ?
C15 C21 H21 119.8 . . ?

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
O1 C1 C2 C3 179.4(4) . . . . ?
C7 C1 C2 C3 -1.9(5) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C2 C3 C4 C6 1.3(5) . . . . ?
C2 C3 C4 C5 -178.6(4) . . . . ?
C3 C4 C6 C7 -1.4(5) . . . . ?
C5 C4 C6 C7 178.5(4) . . . . ?
C4 C6 C7 C1 -0.1(5) . . . . ?
C4 C6 C7 N1 178.1(3) . . . . ?
O1 C1 C7 C6 -179.4(3) . . . . ?
C2 C1 C7 C6 1.8(5) . . . . ?
O1 C1 C7 N1 2.3(4) . . . . ?
C2 C1 C7 N1 -176.5(3) . . . . ?
C8 N1 C7 C6 13.7(5) . . . . ?
C8 N1 C7 C1 -168.1(4) . . . . ?
C7 N1 C8 C9 -179.7(3) . . . . ?
N1 C8 C9 C14 -176.8(3) . . . . ?
N1 C8 C9 C10 1.1(5) . . . . ?
C8 C9 C10 O2 1.5(5) . . . . ?
C14 C9 C10 O2 179.3(3) . . . . ?
C8 C9 C10 C11 -178.2(3) . . . . ?
C14 C9 C10 C11 -0.4(5) . . . . ?
O2 C10 C11 C12 -177.0(4) . . . . ?
C9 C10 C11 C12 2.7(6) . . . . ?
C10 C11 C12 C13 -2.9(6) . . . . ?
C11 C12 C13 C14 0.6(6) . . . . ?
C11 C12 C13 C15 -178.6(4) . . . . ?
C12 C13 C14 C9 1.8(5) . . . . ?
C15 C13 C14 C9 -179.0(3) . . . . ?
C8 C9 C14 C13 176.0(3) . . . . ?
C10 C9 C14 C13 -1.9(5) . . . . ?
C14 C13 C15 C16 -44.5(6) . . . . ?
C12 C13 C15 C16 134.7(5) . . . . ?
C14 C13 C15 C21 137.9(5) . . . . ?
C12 C13 C15 C21 -42.9(6) . . . . ?
C21 C15 C16 C17 1.9(7) . . . . ?
C13 C15 C16 C17 -175.8(4) . . . . ?
C15 C16 C17 C18 -0.3(8) . . . . ?
C16 C17 C18 C20 -2.0(9) . . . . ?
C17 C18 C20 C21 2.7(10) . . . . ?
C18 C20 C21 C15 -1.1(9) . . . . ?
C16 C15 C21 C20 -1.2(7) . . . . ?
C13 C15 C21 C20 176.5(5) . . . . ?

_refine_diff_density_max         0.143
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.044



