# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_195
_audit_block_doi                 10.5517/ccdc.csd.cc1q5n9v
_database_code_depnum_ccdc_archive 'CCDC 1584357'
_audit_update_record             
;
2017-11-07 deposited with the CCDC.
2018-04-05 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            'C20 H20 N2 O'
_chemical_formula_weight         304.38

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      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                   9.5682(3)
_cell_length_b                   18.4465(7)
_cell_length_c                   9.7648(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.8076(17)
_cell_angle_gamma                90
_cell_volume                     1666.25(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4567
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      25.40

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11398
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.208
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        24.994
_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             2938
_reflns_number_gt                2253
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0477P)²+0.3653P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.027(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2938
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.0999
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
C1 C -0.15746(18) 0.43365(9) 0.87942(19) 0.0573(5) Uani 1 1 d . . . . .
H1 H -0.0998 0.4543 0.9614 0.069 Uiso 1 1 calc R U . . .
C2 C -0.3030(2) 0.44837(11) 0.8398(2) 0.0719(6) Uani 1 1 d . . . . .
H2 H -0.3439 0.4777 0.8967 0.086 Uiso 1 1 calc R U . . .
C3 C -0.3879(2) 0.42018(12) 0.7172(2) 0.0780(6) Uani 1 1 d . . . . .
H3 H -0.4861 0.4310 0.6900 0.094 Uiso 1 1 calc R U . . .
C4 C -0.3284(2) 0.37598(13) 0.6343(2) 0.0797(6) Uani 1 1 d . . . . .
H4 H -0.3862 0.3570 0.5506 0.096 Uiso 1 1 calc R U . . .
C5 C -0.18314(18) 0.35956(10) 0.67479(19) 0.0620(5) Uani 1 1 d . . . . .
H5 H -0.1434 0.3290 0.6189 0.074 Uiso 1 1 calc R U . . .
C6 C -0.09624(16) 0.38829(8) 0.79804(16) 0.0440(4) Uani 1 1 d . . . . .
C7 C 0.06146(16) 0.37235(8) 0.84588(16) 0.0428(4) Uani 1 1 d . . . . .
C8 C 0.23399(15) 0.27126(8) 0.84619(16) 0.0416(4) Uani 1 1 d . . . . .
C9 C 0.23288(15) 0.19685(8) 0.80579(15) 0.0403(4) Uani 1 1 d . . . . .
C10 C 0.09296(19) 0.09826(9) 0.7191(2) 0.0607(5) Uani 1 1 d . . . . .
H10 H 0.0023 0.0771 0.6868 0.073 Uiso 1 1 calc R U . . .
C11 C 0.2135(2) 0.05603(9) 0.7243(2) 0.0629(5) Uani 1 1 d . . . . .
H11 H 0.2032 0.0078 0.6957 0.075 Uiso 1 1 calc R U . . .
C12 C 0.34693(19) 0.08566(9) 0.77164(19) 0.0565(4) Uani 1 1 d . . . . .
H12 H 0.4282 0.0575 0.7740 0.068 Uiso 1 1 calc R U . . .
C13 C 0.36445(16) 0.15873(8) 0.81747(16) 0.0437(4) Uani 1 1 d . . . . .
C14 C 0.50022(15) 0.19539(9) 0.87286(16) 0.0469(4) Uani 1 1 d . . . . .
C15 C 0.49261(16) 0.26592(9) 0.91306(18) 0.0533(4) Uani 1 1 d . . . . .
H15 H 0.5790 0.2902 0.9511 0.064 Uiso 1 1 calc R U . . .
C16 C 0.36282(16) 0.30418(9) 0.90072(18) 0.0522(4) Uani 1 1 d . . . . .
H16 H 0.3654 0.3522 0.9301 0.063 Uiso 1 1 calc R U . . .
C17 C 0.64736(17) 0.15904(10) 0.88449(19) 0.0600(5) Uani 1 1 d . . . . .
C18 C 0.6608(2) 0.13937(13) 0.7352(2) 0.0830(7) Uani 1 1 d . . . . .
H18A H 0.5868 0.1051 0.6927 0.124 Uiso 1 1 calc R U . . .
H18B H 0.7540 0.1184 0.7417 0.124 Uiso 1 1 calc R U . . .
H18C H 0.6498 0.1823 0.6780 0.124 Uiso 1 1 calc R U . . .
C19 C 0.6678(2) 0.09177(12) 0.9817(2) 0.0860(7) Uani 1 1 d . . . . .
H19A H 0.6648 0.1062 1.0753 0.129 Uiso 1 1 calc R U . . .
H19B H 0.7596 0.0697 0.9852 0.129 Uiso 1 1 calc R U . . .
H19C H 0.5918 0.0576 0.9449 0.129 Uiso 1 1 calc R U . . .
C20 C 0.77297(18) 0.21070(13) 0.9487(2) 0.0808(6) Uani 1 1 d . . . . .
H20A H 0.7643 0.2537 0.8917 0.121 Uiso 1 1 calc R U . . .
H20B H 0.8631 0.1871 0.9513 0.121 Uiso 1 1 calc R U . . .
H20C H 0.7700 0.2236 1.0432 0.121 Uiso 1 1 calc R U . . .
N1 N 0.09751(14) 0.30325(7) 0.82292(15) 0.0486(4) Uani 1 1 d . . . . .
N2 N 0.09963(13) 0.16667(7) 0.75735(15) 0.0499(4) Uani 1 1 d . . . . .
O1 O 0.14977(12) 0.41808(6) 0.90229(13) 0.0584(3) Uani 1 1 d . . . . .
H1N H 0.0282(18) 0.2738(9) 0.7864(17) 0.052(5) 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
C1 C2 1.373(2) . ?
C1 C6 1.383(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.366(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.490(2) . ?
C7 O1 1.2210(17) . ?
C7 N1 1.3541(19) . ?
C8 C16 1.355(2) . ?
C8 N1 1.3978(19) . ?
C8 C9 1.427(2) . ?
C9 N2 1.3605(18) . ?
C9 C13 1.421(2) . ?
C10 N2 1.313(2) . ?
C10 C11 1.382(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.357(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.417(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.442(2) . ?
C14 C15 1.366(2) . ?
C14 C17 1.537(2) . ?
C15 C16 1.406(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C20 1.536(3) . ?
C17 C18 1.539(3) . ?
C17 C19 1.544(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 . ?
N1 H1N 0.861(17) . ?

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
C2 C1 C6 120.36(16) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C2 C1 120.32(17) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.97(17) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.15(18) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.25(17) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 118.92(15) . . ?
C5 C6 C7 122.21(14) . . ?
C1 C6 C7 118.87(14) . . ?
O1 C7 N1 123.29(14) . . ?
O1 C7 C6 122.25(13) . . ?
N1 C7 C6 114.46(13) . . ?
C16 C8 N1 126.37(14) . . ?
C16 C8 C9 118.77(13) . . ?
N1 C8 C9 114.86(12) . . ?
N2 C9 C13 123.90(14) . . ?
N2 C9 C8 115.45(13) . . ?
C13 C9 C8 120.65(13) . . ?
N2 C10 C11 123.51(16) . . ?
N2 C10 H10 118.2 . . ?
C11 C10 H10 118.2 . . ?
C12 C11 C10 119.30(16) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 121.05(15) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C12 C13 C9 114.50(14) . . ?
C12 C13 C14 125.97(14) . . ?
C9 C13 C14 119.54(14) . . ?
C15 C14 C13 116.45(13) . . ?
C15 C14 C17 120.61(15) . . ?
C13 C14 C17 122.93(15) . . ?
C14 C15 C16 124.32(14) . . ?
C14 C15 H15 117.8 . . ?
C16 C15 H15 117.8 . . ?
C8 C16 C15 120.23(15) . . ?
C8 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C20 C17 C14 111.45(16) . . ?
C20 C17 C18 106.67(16) . . ?
C14 C17 C18 109.23(14) . . ?
C20 C17 C19 106.54(16) . . ?
C14 C17 C19 111.46(15) . . ?
C18 C17 C19 111.38(17) . . ?
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 . . ?
C7 N1 C8 129.60(13) . . ?
C7 N1 H1N 117.5(11) . . ?
C8 N1 H1N 112.9(11) . . ?
C10 N2 C9 117.73(13) . . ?

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
C6 C1 C2 C3 -2.1(3) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C4 C5 C6 C7 -179.76(18) . . . . ?
C2 C1 C6 C5 1.6(3) . . . . ?
C2 C1 C6 C7 -178.77(16) . . . . ?
C5 C6 C7 O1 142.34(18) . . . . ?
C1 C6 C7 O1 -37.3(2) . . . . ?
C5 C6 C7 N1 -38.3(2) . . . . ?
C1 C6 C7 N1 141.98(16) . . . . ?
C16 C8 C9 N2 177.42(14) . . . . ?
N1 C8 C9 N2 -3.2(2) . . . . ?
C16 C8 C9 C13 -2.4(2) . . . . ?
N1 C8 C9 C13 176.99(13) . . . . ?
N2 C10 C11 C12 0.3(3) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
C11 C12 C13 C9 -1.5(2) . . . . ?
C11 C12 C13 C14 178.37(16) . . . . ?
N2 C9 C13 C12 1.1(2) . . . . ?
C8 C9 C13 C12 -179.11(14) . . . . ?
N2 C9 C13 C14 -178.76(14) . . . . ?
C8 C9 C13 C14 1.0(2) . . . . ?
C12 C13 C14 C15 -179.02(16) . . . . ?
C9 C13 C14 C15 0.8(2) . . . . ?
C12 C13 C14 C17 2.2(2) . . . . ?
C9 C13 C14 C17 -177.92(14) . . . . ?
C13 C14 C15 C16 -1.4(2) . . . . ?
C17 C14 C15 C16 177.35(15) . . . . ?
N1 C8 C16 C15 -177.45(15) . . . . ?
C9 C8 C16 C15 1.8(2) . . . . ?
C14 C15 C16 C8 0.1(3) . . . . ?
C15 C14 C17 C20 1.9(2) . . . . ?
C13 C14 C17 C20 -179.38(15) . . . . ?
C15 C14 C17 C18 -115.70(19) . . . . ?
C13 C14 C17 C18 63.0(2) . . . . ?
C15 C14 C17 C19 120.80(19) . . . . ?
C13 C14 C17 C19 -60.5(2) . . . . ?
O1 C7 N1 C8 -5.0(3) . . . . ?
C6 C7 N1 C8 175.66(15) . . . . ?
C16 C8 N1 C7 1.1(3) . . . . ?
C9 C8 N1 C7 -178.17(15) . . . . ?
C11 C10 N2 C9 -0.7(3) . . . . ?
C13 C9 N2 C10 -0.1(2) . . . . ?
C8 C9 N2 C10 -179.86(15) . . . . ?

_refine_diff_density_max         0.156
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.030

