# 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_KA142
_database_code_depnum_ccdc_archive 'CCDC 1563687'
_audit_update_record             
;
2017-07-21 deposited with the CCDC.
2018-06-12 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         'C20 H19 N3 O'
_chemical_formula_sum            'C20 H19 N3 O'
_chemical_formula_weight         317.38

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

_cell_length_a                   19.497(5)
_cell_length_b                   8.597(2)
_cell_length_c                   19.553(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3277.4(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9981
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      28.32

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_process_details   'SADABS; Bruker, 2016'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7095

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45870
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.330
_diffrn_reflns_theta_max         28.295
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4069
_reflns_number_gt                3476
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0551P)²+0.9106P] 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       0.0061(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4069
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1199
_refine_ls_wR_factor_gt          0.1133
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.21864(11) 1.0294(3) 0.20954(9) 0.0905(7) Uani 1 1 d . . . . .
H1A H 0.2593 0.9977 0.1856 0.136 Uiso 1 1 calc R U . . .
H1B H 0.2270 1.0267 0.2579 0.136 Uiso 1 1 calc R U . . .
H1C H 0.2066 1.1333 0.1962 0.136 Uiso 1 1 calc R U . . .
C2 C 0.15998(7) 0.9193(2) 0.19205(7) 0.0530(4) Uani 1 1 d . . . . .
H2A H 0.1735 0.8134 0.2027 0.064 Uiso 1 1 calc R U . . .
H2B H 0.1203 0.9449 0.2198 0.064 Uiso 1 1 calc R U . . .
C3 C 0.14083(6) 0.93036(16) 0.11676(6) 0.0418(3) Uani 1 1 d . . . . .
H3A H 0.1299 1.0377 0.1060 0.050 Uiso 1 1 calc R U . . .
H3B H 0.1802 0.9009 0.0894 0.050 Uiso 1 1 calc R U . . .
C4 C 0.08031(6) 0.82823(14) 0.09687(6) 0.0361(3) Uani 1 1 d . . . . .
H4A H 0.0917 0.7205 0.1062 0.043 Uiso 1 1 calc R U . . .
H4B H 0.0411 0.8557 0.1249 0.043 Uiso 1 1 calc R U . . .
C5 C 0.06112(6) 0.84408(13) 0.02295(6) 0.0330(2) Uani 1 1 d . . . . .
C6 C -0.07484(6) 0.65460(14) -0.06847(6) 0.0378(3) Uani 1 1 d . . . . .
C7 C -0.08313(6) 0.60731(13) 0.00172(6) 0.0334(2) Uani 1 1 d . . . . .
C9 C 0.01775(6) 0.83540(14) -0.11663(6) 0.0357(3) Uani 1 1 d . . . . .
C10 C 0.07201(6) 0.93012(14) -0.09582(6) 0.0373(3) Uani 1 1 d . . . . .
C11 C 0.09234(6) 0.93143(14) -0.02462(6) 0.0379(3) Uani 1 1 d . . . . .
H11 H 0.1284 0.9953 -0.0113 0.045 Uiso 1 1 calc R U . . .
C12 C -0.00145(8) 0.82395(17) -0.18514(6) 0.0462(3) Uani 1 1 d . . . . .
H12 H -0.0376 0.7600 -0.1983 0.055 Uiso 1 1 calc R U . . .
C13 C 0.03455(8) 0.90999(18) -0.23314(7) 0.0530(4) Uani 1 1 d . . . . .
H13 H 0.0222 0.9039 -0.2790 0.064 Uiso 1 1 calc R U . . .
C14 C 0.08835(8) 1.00440(19) -0.21407(7) 0.0535(4) Uani 1 1 d . . . . .
H14 H 0.1122 1.0607 -0.2470 0.064 Uiso 1 1 calc R U . . .
C15 C 0.10681(7) 1.01533(17) -0.14601(7) 0.0479(3) Uani 1 1 d . . . . .
H15 H 0.1428 1.0802 -0.1334 0.058 Uiso 1 1 calc R U . . .
C16 C -0.13554(6) 0.50239(13) 0.02881(6) 0.0343(3) Uani 1 1 d . . . . .
C17 C -0.13433(7) 0.45498(15) 0.09721(7) 0.0408(3) Uani 1 1 d . . . . .
H17 H -0.1011 0.4943 0.1266 0.049 Uiso 1 1 calc R U . . .
C18 C -0.18216(7) 0.35024(16) 0.12149(7) 0.0482(3) Uani 1 1 d . . . . .
H18 H -0.1807 0.3191 0.1670 0.058 Uiso 1 1 calc R U . . .
C19 C -0.23229(7) 0.29119(17) 0.07864(8) 0.0508(3) Uani 1 1 d . . . . .
H19 H -0.2639 0.2194 0.0951 0.061 Uiso 1 1 calc R U . . .
C20 C -0.23505(7) 0.33935(16) 0.01146(8) 0.0477(3) Uani 1 1 d . . . . .
H20 H -0.2692 0.3011 -0.0172 0.057 Uiso 1 1 calc R U . . .
C21 C -0.18735(6) 0.44449(14) -0.01379(7) 0.0403(3) Uani 1 1 d . . . . .
H21 H -0.1898 0.4766 -0.0591 0.048 Uiso 1 1 calc R U . . .
N1 N -0.03442(5) 0.66881(11) 0.04143(5) 0.0342(2) Uani 1 1 d . . . . .
N2 N -0.01690(5) 0.75012(12) -0.06555(5) 0.0350(2) Uani 1 1 d . . . . .
N3 N 0.00531(5) 0.75409(11) 0.00174(5) 0.0333(2) Uani 1 1 d . . . . .
O1 O -0.10723(6) 0.62569(13) -0.12122(5) 0.0570(3) Uani 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 1.523(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.5219(18) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.5214(17) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.4992(16) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C11 1.3414(17) . ?
C5 N3 1.3981(15) . ?
C6 O1 1.2346(15) . ?
C6 N2 1.3978(16) . ?
C6 C7 1.4405(17) . ?
C7 N1 1.3358(15) . ?
C7 C16 1.4623(16) . ?
C9 C12 1.3944(17) . ?
C9 C10 1.3956(17) . ?
C9 N2 1.4111(15) . ?
C10 C15 1.3999(18) . ?
C10 C11 1.4475(17) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.3984(18) . ?
C16 C21 1.4007(17) . ?
C17 C18 1.3805(19) . ?
C17 H17 0.9300 . ?
C18 C19 1.384(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.3877(18) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
N1 N3 1.3190(14) . ?
N2 N3 1.3856(14) . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 111.26(13) . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C2 113.68(11) . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 C3 112.80(10) . . ?
C5 C4 H4A 109.0 . . ?
C3 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C11 C5 N3 117.21(11) . . ?
C11 C5 C4 127.31(11) . . ?
N3 C5 C4 115.46(10) . . ?
O1 C6 N2 124.45(11) . . ?
O1 C6 C7 132.98(12) . . ?
N2 C6 C7 102.57(9) . . ?
N1 C7 C6 111.24(10) . . ?
N1 C7 C16 122.04(11) . . ?
C6 C7 C16 126.70(10) . . ?
C12 C9 C10 121.66(12) . . ?
C12 C9 N2 120.98(12) . . ?
C10 C9 N2 117.36(10) . . ?
C9 C10 C15 117.92(12) . . ?
C9 C10 C11 119.50(11) . . ?
C15 C10 C11 122.51(12) . . ?
C5 C11 C10 122.57(11) . . ?
C5 C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
C13 C12 C9 118.48(13) . . ?
C13 C12 H12 120.8 . . ?
C9 C12 H12 120.8 . . ?
C14 C13 C12 121.12(13) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 119.93(13) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 120.89(14) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C17 C16 C21 118.51(11) . . ?
C17 C16 C7 120.96(11) . . ?
C21 C16 C7 120.52(11) . . ?
C18 C17 C16 120.50(12) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 120.55(13) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 119.62(13) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 120.57(13) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C16 120.21(12) . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?
N3 N1 C7 107.19(10) . . ?
N3 N2 C6 107.80(9) . . ?
N3 N2 C9 120.64(10) . . ?
C6 N2 C9 131.55(10) . . ?
N1 N3 N2 111.19(9) . . ?
N1 N3 C5 126.17(10) . . ?
N2 N3 C5 122.58(10) . . ?

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
C1 C2 C3 C4 -177.39(15) . . . . ?
C2 C3 C4 C5 178.46(11) . . . . ?
C3 C4 C5 C11 2.25(17) . . . . ?
C3 C4 C5 N3 -179.37(10) . . . . ?
O1 C6 C7 N1 179.73(14) . . . . ?
N2 C6 C7 N1 -0.34(13) . . . . ?
O1 C6 C7 C16 1.5(2) . . . . ?
N2 C6 C7 C16 -178.54(10) . . . . ?
C12 C9 C10 C15 0.47(18) . . . . ?
N2 C9 C10 C15 180.00(11) . . . . ?
C12 C9 C10 C11 -176.63(12) . . . . ?
N2 C9 C10 C11 2.91(16) . . . . ?
N3 C5 C11 C10 -2.48(17) . . . . ?
C4 C5 C11 C10 175.87(11) . . . . ?
C9 C10 C11 C5 0.25(18) . . . . ?
C15 C10 C11 C5 -176.70(12) . . . . ?
C10 C9 C12 C13 -0.3(2) . . . . ?
N2 C9 C12 C13 -179.79(12) . . . . ?
C9 C12 C13 C14 0.3(2) . . . . ?
C12 C13 C14 C15 -0.5(2) . . . . ?
C13 C14 C15 C10 0.7(2) . . . . ?
C9 C10 C15 C14 -0.7(2) . . . . ?
C11 C10 C15 C14 176.30(13) . . . . ?
N1 C7 C16 C17 -3.70(17) . . . . ?
C6 C7 C16 C17 174.33(11) . . . . ?
N1 C7 C16 C21 177.66(10) . . . . ?
C6 C7 C16 C21 -4.31(18) . . . . ?
C21 C16 C17 C18 1.70(17) . . . . ?
C7 C16 C17 C18 -176.97(11) . . . . ?
C16 C17 C18 C19 -0.4(2) . . . . ?
C17 C18 C19 C20 -1.0(2) . . . . ?
C18 C19 C20 C21 1.0(2) . . . . ?
C19 C20 C21 C16 0.30(19) . . . . ?
C17 C16 C21 C20 -1.65(17) . . . . ?
C7 C16 C21 C20 177.02(11) . . . . ?
C6 C7 N1 N3 0.20(13) . . . . ?
C16 C7 N1 N3 178.50(10) . . . . ?
O1 C6 N2 N3 -179.72(12) . . . . ?
C7 C6 N2 N3 0.33(12) . . . . ?
O1 C6 N2 C9 1.1(2) . . . . ?
C7 C6 N2 C9 -178.89(11) . . . . ?
C12 C9 N2 N3 175.71(11) . . . . ?
C10 C9 N2 N3 -3.83(16) . . . . ?
C12 C9 N2 C6 -5.2(2) . . . . ?
C10 C9 N2 C6 175.31(11) . . . . ?
C7 N1 N3 N2 0.03(12) . . . . ?
C7 N1 N3 C5 177.33(10) . . . . ?
C6 N2 N3 N1 -0.24(12) . . . . ?
C9 N2 N3 N1 179.08(10) . . . . ?
C6 N2 N3 C5 -177.66(10) . . . . ?
C9 N2 N3 C5 1.66(16) . . . . ?
C11 C5 N3 N1 -175.47(11) . . . . ?
C4 C5 N3 N1 5.99(16) . . . . ?
C11 C5 N3 N2 1.55(16) . . . . ?
C4 C5 N3 N2 -177.00(10) . . . . ?

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.039

