# 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 2017

####################################################################### 
# 
# 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 1473381'
_audit_update_record             
;
2017-02-26 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 N3 O'
_chemical_formula_sum            'C19 H19 N3 O'
_chemical_formula_weight         305.37

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                   7.0070(4)
_cell_length_b                   17.952(2)
_cell_length_c                   26.4727(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3330.0(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3755
_cell_measurement_theta_min      3.7440
_cell_measurement_theta_max      23.7380

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.86199
_shelx_estimated_absorpt_T_max   1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean 15.9853
_diffrn_reflns_number            24793
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         3.078
_diffrn_reflns_theta_max         29.394
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4148
_reflns_number_gt                2489
_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       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-32 (Faruggia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0454P)²+9.5395P] 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
_refine_ls_extinction_coef       0.0022(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4148
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1200
_refine_ls_R_factor_gt           0.0671
_refine_ls_wR_factor_ref         0.1694
_refine_ls_wR_factor_gt          0.1339
_refine_ls_goodness_of_fit_ref   0.700
_refine_ls_restrained_S_all      0.700
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.020

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
C8 C 0.1329(5) 0.3659(2) 0.31817(13) 0.0750(10) Uani 1 1 d . . . . .
H8 H 0.1202 0.4175 0.3196 0.090 Uiso 1 1 calc R U . . .
C7 C 0.2459(5) 0.3345(2) 0.28208(13) 0.0801(10) Uani 1 1 d . . . . .
H7 H 0.3101 0.3646 0.2591 0.096 Uiso 1 1 calc R U . . .
C17 C 0.0979(5) 0.0114(2) 0.65060(12) 0.0732(10) Uani 1 1 d . . . . .
H17 H 0.0097 0.0132 0.6768 0.088 Uiso 1 1 calc R U . . .
C19 C 0.3169(6) -0.0588(2) 0.70875(13) 0.0950(13) Uani 1 1 d . . . . .
H19A H 0.2121 -0.0517 0.7316 0.143 Uiso 1 1 calc R U . . .
H19B H 0.4297 -0.0363 0.7226 0.143 Uiso 1 1 calc R U . . .
H19C H 0.3384 -0.1112 0.7040 0.143 Uiso 1 1 calc R U . . .
H12 H 0.231(4) 0.0680(16) 0.4892(10) 0.062(8) Uiso 1 1 d . . . . .
O1 O 0.2313(3) 0.13146(12) 0.41067(8) 0.0637(6) Uani 1 1 d . . . . .
N1 N -0.2056(3) 0.22167(12) 0.40921(8) 0.0470(5) Uani 1 1 d . . . . .
N3 N -0.0187(3) 0.11020(12) 0.50862(8) 0.0495(6) Uani 1 1 d . . . . .
N2 N -0.0369(3) 0.19743(13) 0.38528(8) 0.0482(6) Uani 1 1 d . . . . .
C1 C -0.2184(3) 0.18417(14) 0.45354(10) 0.0442(6) Uani 1 1 d . . . . .
C2 C -0.0553(4) 0.14449(14) 0.46230(9) 0.0424(6) Uani 1 1 d . . . . .
C3 C 0.0666(4) 0.15268(15) 0.41912(10) 0.0461(6) Uani 1 1 d . . . . .
C4 C 0.0550(4) 0.24518(16) 0.34997(9) 0.0468(6) Uani 1 1 d . . . . .
C12 C 0.1369(4) 0.07497(15) 0.51630(11) 0.0498(6) Uani 1 1 d . . . . .
C5 C 0.1688(4) 0.21332(19) 0.31322(11) 0.0598(8) Uani 1 1 d . . . . .
H5 H 0.1805 0.1618 0.3111 0.072 Uiso 1 1 calc R U . . .
C13 C 0.1805(4) 0.04191(15) 0.56515(10) 0.0488(6) Uani 1 1 d . . . . .
C14 C 0.3542(4) 0.00731(16) 0.57324(11) 0.0566(7) Uani 1 1 d . . . . .
H14 H 0.4430 0.0057 0.5471 0.068 Uiso 1 1 calc R U . . .
C9 C 0.0368(4) 0.32170(17) 0.35269(11) 0.0585(7) Uani 1 1 d . . . . .
H9 H -0.0393 0.3433 0.3775 0.070 Uiso 1 1 calc R U . . .
C15 C 0.3992(4) -0.02498(17) 0.61911(12) 0.0613(8) Uani 1 1 d . . . . .
H15 H 0.5169 -0.0481 0.6234 0.074 Uiso 1 1 calc R U . . .
C11 C -0.3911(4) 0.18881(18) 0.48583(12) 0.0638(8) Uani 1 1 d . . . . .
H11A H -0.4838 0.2205 0.4700 0.096 Uiso 1 1 calc R U . . .
H11B H -0.3572 0.2090 0.5182 0.096 Uiso 1 1 calc R U . . .
H11C H -0.4440 0.1399 0.4902 0.096 Uiso 1 1 calc R U . . .
C16 C 0.2708(5) -0.02312(17) 0.65855(11) 0.0624(8) Uani 1 1 d . . . . .
C10 C -0.3693(4) 0.23899(18) 0.37697(12) 0.0620(8) Uani 1 1 d . . . . .
H10A H -0.3265 0.2654 0.3476 0.093 Uiso 1 1 calc R U . . .
H10B H -0.4582 0.2693 0.3954 0.093 Uiso 1 1 calc R U . . .
H10C H -0.4306 0.1936 0.3668 0.093 Uiso 1 1 calc R U . . .
C6 C 0.2654(5) 0.2588(2) 0.27953(11) 0.0735(10) Uani 1 1 d . . . . .
H6 H 0.3438 0.2377 0.2551 0.088 Uiso 1 1 calc R U . . .
C18 C 0.0521(4) 0.04347(18) 0.60495(11) 0.0639(8) Uani 1 1 d . . . . .
H18 H -0.0660 0.0663 0.6008 0.077 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
C8 C7 1.364(5) . ?
C8 C9 1.385(4) . ?
C7 C6 1.367(5) . ?
C17 C18 1.376(4) . ?
C17 C16 1.377(4) . ?
C19 C16 1.511(4) . ?
O1 C3 1.235(3) . ?
N1 C1 1.356(3) . ?
N1 N2 1.409(3) . ?
N1 C10 1.463(3) . ?
N3 C12 1.277(3) . ?
N3 C2 1.396(3) . ?
N2 C3 1.405(3) . ?
N2 C4 1.423(3) . ?
C1 C2 1.366(3) . ?
C1 C11 1.484(4) . ?
C2 C3 1.435(4) . ?
C4 C9 1.382(4) . ?
C4 C5 1.382(4) . ?
C12 C13 1.455(4) . ?
C5 C6 1.385(4) . ?
C13 C18 1.386(4) . ?
C13 C14 1.383(4) . ?
C14 C15 1.382(4) . ?
C15 C16 1.379(4) . ?

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
C7 C8 C9 120.5(3) . . ?
C6 C7 C8 120.3(3) . . ?
C18 C17 C16 121.9(3) . . ?
C1 N1 N2 106.9(2) . . ?
C1 N1 C10 123.9(2) . . ?
N2 N1 C10 117.4(2) . . ?
C12 N3 C2 121.0(2) . . ?
C3 N2 N1 108.8(2) . . ?
C3 N2 C4 122.0(2) . . ?
N1 N2 C4 119.3(2) . . ?
N1 C1 C2 110.5(2) . . ?
N1 C1 C11 121.7(2) . . ?
C2 C1 C11 127.8(3) . . ?
C1 C2 N3 122.2(2) . . ?
C1 C2 C3 108.0(2) . . ?
N3 C2 C3 129.5(2) . . ?
O1 C3 N2 122.9(2) . . ?
O1 C3 C2 132.0(3) . . ?
N2 C3 C2 105.0(2) . . ?
C9 C4 C5 120.1(3) . . ?
C9 C4 N2 121.5(2) . . ?
C5 C4 N2 118.3(3) . . ?
N3 C12 C13 121.5(3) . . ?
C6 C5 C4 119.4(3) . . ?
C18 C13 C14 117.6(3) . . ?
C18 C13 C12 122.1(3) . . ?
C14 C13 C12 120.3(3) . . ?
C15 C14 C13 121.7(3) . . ?
C4 C9 C8 119.4(3) . . ?
C16 C15 C14 120.4(3) . . ?
C15 C16 C17 118.0(3) . . ?
C15 C16 C19 121.1(3) . . ?
C17 C16 C19 120.9(3) . . ?
C7 C6 C5 120.3(3) . . ?
C17 C18 C13 120.5(3) . . ?

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
C9 C8 C7 C6 0.1(6) . . . . ?
C1 N1 N2 C3 -8.5(3) . . . . ?
C10 N1 N2 C3 -153.1(2) . . . . ?
C1 N1 N2 C4 -154.9(2) . . . . ?
C10 N1 N2 C4 60.5(3) . . . . ?
N2 N1 C1 C2 7.8(3) . . . . ?
C10 N1 C1 C2 149.5(3) . . . . ?
N2 N1 C1 C11 -172.3(2) . . . . ?
C10 N1 C1 C11 -30.5(4) . . . . ?
N1 C1 C2 N3 169.9(2) . . . . ?
C11 C1 C2 N3 -10.0(4) . . . . ?
N1 C1 C2 C3 -4.2(3) . . . . ?
C11 C1 C2 C3 175.9(3) . . . . ?
C12 N3 C2 C1 -178.2(3) . . . . ?
C12 N3 C2 C3 -5.5(4) . . . . ?
N1 N2 C3 O1 -170.6(2) . . . . ?
C4 N2 C3 O1 -25.3(4) . . . . ?
N1 N2 C3 C2 5.9(3) . . . . ?
C4 N2 C3 C2 151.2(2) . . . . ?
C1 C2 C3 O1 174.8(3) . . . . ?
N3 C2 C3 O1 1.3(5) . . . . ?
C1 C2 C3 N2 -1.2(3) . . . . ?
N3 C2 C3 N2 -174.7(2) . . . . ?
C3 N2 C4 C9 -115.0(3) . . . . ?
N1 N2 C4 C9 26.8(4) . . . . ?
C3 N2 C4 C5 63.2(3) . . . . ?
N1 N2 C4 C5 -155.0(2) . . . . ?
C2 N3 C12 C13 177.2(2) . . . . ?
C9 C4 C5 C6 0.5(4) . . . . ?
N2 C4 C5 C6 -177.7(2) . . . . ?
N3 C12 C13 C18 3.4(4) . . . . ?
N3 C12 C13 C14 -176.7(3) . . . . ?
C18 C13 C14 C15 0.3(4) . . . . ?
C12 C13 C14 C15 -179.6(3) . . . . ?
C5 C4 C9 C8 0.3(4) . . . . ?
N2 C4 C9 C8 178.4(3) . . . . ?
C7 C8 C9 C4 -0.6(5) . . . . ?
C13 C14 C15 C16 -0.4(5) . . . . ?
C14 C15 C16 C17 0.2(5) . . . . ?
C14 C15 C16 C19 179.3(3) . . . . ?
C18 C17 C16 C15 0.0(5) . . . . ?
C18 C17 C16 C19 -179.1(4) . . . . ?
C8 C7 C6 C5 0.7(6) . . . . ?
C4 C5 C6 C7 -1.0(5) . . . . ?
C16 C17 C18 C13 -0.1(6) . . . . ?
C14 C13 C18 C17 -0.1(5) . . . . ?
C12 C13 C18 C17 179.8(3) . . . . ?

_refine_diff_density_max         0.283
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-4



