# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1881814'
_audit_update_record             
;
2018-11-28 deposited with the CCDC.
2019-02-06 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            'C22 H17 N3 O'
_chemical_formula_weight         339.38

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.624(3)
_cell_length_b                   8.992(3)
_cell_length_c                   13.312(4)
_cell_angle_alpha                92.425(5)
_cell_angle_beta                 103.464(5)
_cell_angle_gamma                118.016(4)
_cell_volume                     872.4(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2132
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      30.73

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_F_000             356
_exptl_transmission_factor_min   0.6336
_exptl_transmission_factor_max   0.7462
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_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 area detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 'fine-focus sealed tube'
_diffrn_reflns_number            6083
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.598
_diffrn_reflns_theta_max         31.160
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.809
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.809
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.809
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4564
_reflns_number_gt                3260
_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 SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0700P)²+0.1568P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4564
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1463
_refine_ls_wR_factor_gt          0.1301
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
N2 N 0.78305(13) 0.63289(13) 0.18837(8) 0.0348(2) Uani 1 1 d . . . . .
N1 N 0.46793(14) 0.42915(15) 0.13704(9) 0.0422(3) Uani 1 1 d . . . . .
C14 C 0.82860(16) 0.51792(16) 0.14657(10) 0.0343(3) Uani 1 1 d . . . . .
C7 C 0.60508(16) 0.57849(16) 0.18390(10) 0.0360(3) Uani 1 1 d . . . . .
C19 C 0.68706(17) 0.35546(16) 0.09690(10) 0.0367(3) Uani 1 1 d . . . . .
C8 C 0.92694(16) 0.80237(16) 0.24174(11) 0.0360(3) Uani 1 1 d . . . . .
C1 C 0.56270(16) 0.69616(17) 0.23888(11) 0.0380(3) Uani 1 1 d . . . . .
C20 C 0.49752(18) 0.31083(18) 0.08746(11) 0.0407(3) Uani 1 1 d . . . . .
C16 C 1.0476(2) 0.4417(2) 0.11841(12) 0.0471(3) Uani 1 1 d . . . . .
H16 H 1.1687 0.4703 0.1254 0.056 Uiso 1 1 calc R U . . .
C15 C 1.01038(18) 0.56126(18) 0.15695(11) 0.0422(3) Uani 1 1 d . . . . .
H15 H 1.1053 0.6703 0.1897 0.051 Uiso 1 1 calc R U . . .
C18 C 0.7301(2) 0.23705(18) 0.05836(11) 0.0434(3) Uani 1 1 d . . . . .
H18 H 0.6363 0.1280 0.0248 0.052 Uiso 1 1 calc R U . . .
C17 C 0.9081(2) 0.2792(2) 0.06930(12) 0.0471(3) Uani 1 1 d . . . . .
H17 H 0.9352 0.1990 0.0439 0.057 Uiso 1 1 calc R U . . .
C9 C 0.98660(18) 0.83551(18) 0.34939(11) 0.0440(3) Uani 1 1 d . . . . .
H9 H 0.9336 0.7505 0.3876 0.053 Uiso 1 1 calc R U . . .
C13 C 1.00404(19) 0.92586(18) 0.18362(12) 0.0454(3) Uani 1 1 d . . . . .
H13 H 0.9613 0.9021 0.1107 0.054 Uiso 1 1 calc R U . . .
C12 C 1.1462(2) 1.08609(19) 0.23530(15) 0.0541(4) Uani 1 1 d . . . . .
H12 H 1.2012 1.1706 0.1972 0.065 Uiso 1 1 calc R U . . .
C10 C 1.1262(2) 0.9965(2) 0.40011(13) 0.0541(4) Uani 1 1 d . . . . .
H10 H 1.1664 1.0213 0.4730 0.065 Uiso 1 1 calc R U . . .
C11 C 1.2055(2) 1.11972(19) 0.34298(15) 0.0556(4) Uani 1 1 d . . . . .
H11 H 1.3008 1.2276 0.3776 0.067 Uiso 1 1 calc R U . . .
C2 C 0.5070(2) 0.6554(2) 0.32809(12) 0.0500(4) Uani 1 1 d . . . . .
H2 H 0.5016 0.5592 0.3541 0.060 Uiso 1 1 calc R U . . .
C6 C 0.5668(2) 0.8368(2) 0.19937(13) 0.0497(4) Uani 1 1 d . . . . .
H6 H 0.6041 0.8646 0.1394 0.060 Uiso 1 1 calc R U . . .
C3 C 0.4594(2) 0.7585(2) 0.37823(14) 0.0596(4) Uani 1 1 d . . . . .
H3 H 0.4238 0.7327 0.4389 0.071 Uiso 1 1 calc R U . . .
C5 C 0.5150(2) 0.9359(2) 0.24951(15) 0.0608(4) Uani 1 1 d . . . . .
H5 H 0.5145 1.0291 0.2221 0.073 Uiso 1 1 calc R U . . .
C4 C 0.4645(2) 0.8984(2) 0.33920(15) 0.0610(5) Uani 1 1 d . . . . .
H4 H 0.4336 0.9680 0.3737 0.073 Uiso 1 1 calc R U . . .
O1 O 0.36707(14) 0.17347(14) 0.03910(9) 0.0585(3) Uani 1 1 d . . . . .
C22 C 0.9435(3) 0.3008(3) 0.36364(17) 0.0801(6) Uani 1 1 d . . . . .
H22A H 1.0684 0.3882 0.3954 0.120 Uiso 1 1 calc R U . . .
H22B H 0.9215 0.2778 0.2891 0.120 Uiso 1 1 calc R U . . .
H22C H 0.9211 0.1983 0.3916 0.120 Uiso 1 1 calc R U . . .
C21 C 0.8230(3) 0.3578(2) 0.38575(15) 0.0647(5) Uani 1 1 d . . . . .
N3 N 0.7288(3) 0.4028(3) 0.40334(16) 0.0884(6) 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
N2 C7 1.3595(16) . ?
N2 C14 1.4026(16) . ?
N2 C8 1.4451(16) . ?
N1 C7 1.2980(16) . ?
N1 C20 1.3808(18) . ?
C14 C19 1.3887(18) . ?
C14 C15 1.3962(18) . ?
C7 C1 1.4870(18) . ?
C19 C18 1.3958(19) . ?
C19 C20 1.4604(19) . ?
C8 C9 1.373(2) . ?
C8 C13 1.3756(19) . ?
C1 C6 1.379(2) . ?
C1 C2 1.383(2) . ?
C20 O1 1.2230(16) . ?
C16 C15 1.370(2) . ?
C16 C17 1.383(2) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
C18 C17 1.366(2) . ?
C18 H18 0.9300 . ?
C17 H17 0.9300 . ?
C9 C10 1.379(2) . ?
C9 H9 0.9300 . ?
C13 C12 1.384(2) . ?
C13 H13 0.9300 . ?
C12 C11 1.373(3) . ?
C12 H12 0.9300 . ?
C10 C11 1.370(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C2 C3 1.381(2) . ?
C2 H2 0.9300 . ?
C6 C5 1.379(2) . ?
C6 H6 0.9300 . ?
C3 C4 1.366(3) . ?
C3 H3 0.9300 . ?
C5 C4 1.367(3) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C22 C21 1.435(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C21 N3 1.125(3) . ?

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 N2 C14 119.07(10) . . ?
C7 N2 C8 121.24(10) . . ?
C14 N2 C8 119.53(10) . . ?
C7 N1 C20 120.07(11) . . ?
C19 C14 C15 120.19(12) . . ?
C19 C14 N2 118.00(11) . . ?
C15 C14 N2 121.77(11) . . ?
N1 C7 N2 125.07(12) . . ?
N1 C7 C1 116.78(11) . . ?
N2 C7 C1 118.12(11) . . ?
C14 C19 C18 118.86(12) . . ?
C14 C19 C20 119.76(12) . . ?
C18 C19 C20 121.37(12) . . ?
C9 C8 C13 121.41(13) . . ?
C9 C8 N2 119.22(12) . . ?
C13 C8 N2 119.36(12) . . ?
C6 C1 C2 120.02(13) . . ?
C6 C1 C7 121.59(12) . . ?
C2 C1 C7 118.26(13) . . ?
O1 C20 N1 119.82(12) . . ?
O1 C20 C19 122.50(13) . . ?
N1 C20 C19 117.68(11) . . ?
C15 C16 C17 121.02(13) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C15 C14 119.38(13) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C17 C18 C19 120.89(13) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C18 C17 C16 119.65(13) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C8 C9 C10 119.12(14) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C8 C13 C12 118.98(15) . . ?
C8 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C11 C12 C13 119.70(14) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C11 C10 C9 119.94(16) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.84(14) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C3 C2 C1 119.49(15) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C5 C6 C1 119.45(15) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C4 C3 C2 120.35(16) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C4 C5 C6 120.58(17) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C3 C4 C5 120.06(15) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N3 C21 C22 179.8(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
C7 N2 C14 C19 3.60(17) . . . . ?
C8 N2 C14 C19 179.25(11) . . . . ?
C7 N2 C14 C15 -174.26(12) . . . . ?
C8 N2 C14 C15 1.39(18) . . . . ?
C20 N1 C7 N2 0.6(2) . . . . ?
C20 N1 C7 C1 -177.74(12) . . . . ?
C14 N2 C7 N1 -5.0(2) . . . . ?
C8 N2 C7 N1 179.48(12) . . . . ?
C14 N2 C7 C1 173.41(11) . . . . ?
C8 N2 C7 C1 -2.16(18) . . . . ?
C15 C14 C19 C18 0.33(19) . . . . ?
N2 C14 C19 C18 -177.57(11) . . . . ?
C15 C14 C19 C20 179.34(12) . . . . ?
N2 C14 C19 C20 1.44(18) . . . . ?
C7 N2 C8 C9 76.10(16) . . . . ?
C14 N2 C8 C9 -99.45(14) . . . . ?
C7 N2 C8 C13 -105.37(15) . . . . ?
C14 N2 C8 C13 79.09(16) . . . . ?
N1 C7 C1 C6 -107.13(15) . . . . ?
N2 C7 C1 C6 74.37(17) . . . . ?
N1 C7 C1 C2 68.77(17) . . . . ?
N2 C7 C1 C2 -109.73(15) . . . . ?
C7 N1 C20 O1 -176.46(14) . . . . ?
C7 N1 C20 C19 4.5(2) . . . . ?
C14 C19 C20 O1 175.51(13) . . . . ?
C18 C19 C20 O1 -5.5(2) . . . . ?
C14 C19 C20 N1 -5.52(19) . . . . ?
C18 C19 C20 N1 173.47(13) . . . . ?
C17 C16 C15 C14 0.1(2) . . . . ?
C19 C14 C15 C16 -0.5(2) . . . . ?
N2 C14 C15 C16 177.33(12) . . . . ?
C14 C19 C18 C17 0.2(2) . . . . ?
C20 C19 C18 C17 -178.80(13) . . . . ?
C19 C18 C17 C16 -0.6(2) . . . . ?
C15 C16 C17 C18 0.4(2) . . . . ?
C13 C8 C9 C10 0.4(2) . . . . ?
N2 C8 C9 C10 178.86(13) . . . . ?
C9 C8 C13 C12 0.7(2) . . . . ?
N2 C8 C13 C12 -177.75(12) . . . . ?
C8 C13 C12 C11 -1.0(2) . . . . ?
C8 C9 C10 C11 -1.2(2) . . . . ?
C9 C10 C11 C12 0.9(2) . . . . ?
C13 C12 C11 C10 0.2(2) . . . . ?
C6 C1 C2 C3 -1.4(2) . . . . ?
C7 C1 C2 C3 -177.33(13) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
C7 C1 C6 C5 175.85(14) . . . . ?
C1 C2 C3 C4 1.0(2) . . . . ?
C1 C6 C5 C4 1.7(2) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C6 C5 C4 C3 -2.0(3) . . . . ?

_refine_diff_density_max         0.241
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.039

