# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_d8v21221
_database_code_depnum_ccdc_archive 'CCDC 2074397'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2021-03-31 deposited with the CCDC.	2021-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H19 N O'
_chemical_formula_weight         325.39

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      tetragonal
_space_group_IT_number           114
_space_group_name_H-M_alt        'P -4 21 c'
_space_group_name_Hall           'P -4 2n'

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

_cell_length_a                   21.3009(5)
_cell_length_b                   21.3009(5)
_cell_length_c                   7.7405(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3512.1(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9825
_cell_measurement_theta_min      5.409
_cell_measurement_theta_max      49.313

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6518
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            52311
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.705
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3454
_reflns_number_gt                3108
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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-2013 (Sheldrick, 2013)'
_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)+(0.0412P)²+0.3507P] 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
_refine_ls_extinction_coef       0.0110(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1239 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.0(5)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3454
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0845
_refine_ls_wR_factor_gt          0.0797
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
N1 N 0.37858(8) 0.25217(8) 0.6131(2) 0.0459(4) Uani 1 1 d . . . . .
O1 O 0.32415(7) 0.21855(8) 0.8483(2) 0.0691(5) Uani 1 1 d . . . . .
C1 C 0.32916(9) 0.25636(9) 0.7298(3) 0.0484(5) Uani 1 1 d . . . . .
C2 C 0.28544(9) 0.30791(9) 0.7016(3) 0.0453(4) Uani 1 1 d . . . . .
C3 C 0.23355(9) 0.31411(10) 0.8116(3) 0.0554(5) Uani 1 1 d . . . . .
H3 H 0.2280 0.2859 0.9019 0.066 Uiso 1 1 calc R U . . .
C4 C 0.19110(10) 0.36132(11) 0.7871(3) 0.0609(6) Uani 1 1 d . . . . .
H4 H 0.1568 0.3652 0.8606 0.073 Uiso 1 1 calc R U . . .
C5 C 0.19936(11) 0.40348(10) 0.6519(3) 0.0583(6) Uani 1 1 d . . . . .
H5 H 0.1703 0.4355 0.6349 0.070 Uiso 1 1 calc R U . . .
C6 C 0.24993(10) 0.39825(9) 0.5436(3) 0.0523(5) Uani 1 1 d . . . . .
H6 H 0.2547 0.4268 0.4535 0.063 Uiso 1 1 calc R U . . .
C7 C 0.29456(9) 0.35065(9) 0.5662(3) 0.0428(4) Uani 1 1 d . . . . .
C8 C 0.34835(9) 0.34371(9) 0.4544(2) 0.0439(4) Uani 1 1 d . . . . .
C9 C 0.38854(9) 0.29494(9) 0.4783(2) 0.0439(4) Uani 1 1 d . . . . .
C10 C 0.44369(10) 0.28370(11) 0.3624(3) 0.0546(5) Uani 1 1 d . . . . .
H10A H 0.4775 0.2659 0.4304 0.065 Uiso 1 1 calc R U . . .
H10B H 0.4581 0.3237 0.3178 0.065 Uiso 1 1 calc R U . . .
C11 C 0.43020(14) 0.24037(14) 0.2115(4) 0.0781(7) Uani 1 1 d . . . . .
H11A H 0.4159 0.2005 0.2541 0.117 Uiso 1 1 calc R U . . .
H11B H 0.4678 0.2345 0.1451 0.117 Uiso 1 1 calc R U . . .
H11C H 0.3983 0.2586 0.1397 0.117 Uiso 1 1 calc R U . . .
C12 C 0.42196(9) 0.20091(10) 0.6438(3) 0.0477(5) Uani 1 1 d . . . . .
C13 C 0.41139(11) 0.14332(10) 0.5702(3) 0.0591(6) Uani 1 1 d . . . . .
H13 H 0.3770 0.1371 0.4984 0.071 Uiso 1 1 calc R U . . .
C14 C 0.45265(12) 0.09451(12) 0.6042(4) 0.0734(7) Uani 1 1 d . . . . .
H14 H 0.4463 0.0554 0.5536 0.088 Uiso 1 1 calc R U . . .
C15 C 0.50308(12) 0.10377(13) 0.7126(4) 0.0729(7) Uani 1 1 d . . . . .
H15 H 0.5306 0.0709 0.7353 0.088 Uiso 1 1 calc R U . . .
C16 C 0.51286(11) 0.16086(13) 0.7865(3) 0.0685(7) Uani 1 1 d . . . . .
H16 H 0.5471 0.1669 0.8593 0.082 Uiso 1 1 calc R U . . .
C17 C 0.47221(9) 0.20992(12) 0.7537(3) 0.0556(5) Uani 1 1 d . . . . .
H17 H 0.4786 0.2488 0.8054 0.067 Uiso 1 1 calc R U . . .
C18 C 0.35875(9) 0.39107(9) 0.3140(3) 0.0462(5) Uani 1 1 d . . . . .
C19 C 0.39145(12) 0.44580(11) 0.3463(3) 0.0635(6) Uani 1 1 d . . . . .
H19 H 0.4079 0.4528 0.4558 0.076 Uiso 1 1 calc R U . . .
C20 C 0.40016(13) 0.49033(11) 0.2187(4) 0.0712(7) Uani 1 1 d . . . . .
H20 H 0.4223 0.5269 0.2431 0.085 Uiso 1 1 calc R U . . .
C21 C 0.37627(11) 0.48091(11) 0.0566(3) 0.0621(6) Uani 1 1 d . . . . .
H21 H 0.3824 0.5107 -0.0296 0.075 Uiso 1 1 calc R U . . .
C22 C 0.34336(12) 0.42736(11) 0.0227(3) 0.0636(6) Uani 1 1 d . . . . .
H22 H 0.3266 0.4209 -0.0868 0.076 Uiso 1 1 calc R U . . .
C23 C 0.33472(11) 0.38268(11) 0.1499(3) 0.0578(6) Uani 1 1 d . . . . .
H23 H 0.3123 0.3463 0.1245 0.069 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
N1 C1 1.390(3) . ?
N1 C9 1.401(2) . ?
N1 C12 1.450(2) . ?
O1 C1 1.225(2) . ?
C1 C2 1.456(3) . ?
C2 C3 1.401(3) . ?
C2 C7 1.402(3) . ?
C3 C4 1.365(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.370(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.401(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.443(3) . ?
C8 C9 1.359(3) . ?
C8 C18 1.499(3) . ?
C9 C10 1.497(3) . ?
C10 C11 1.516(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.371(3) . ?
C12 C17 1.380(3) . ?
C13 C14 1.387(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.360(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.381(3) . ?
C18 C23 1.382(3) . ?
C19 C20 1.382(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.369(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.364(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.382(3) . ?
C22 H22 0.9300 . ?
C23 H23 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 N1 C9 123.84(16) . . ?
C1 N1 C12 115.09(16) . . ?
C9 N1 C12 121.02(16) . . ?
O1 C1 N1 120.68(19) . . ?
O1 C1 C2 123.50(19) . . ?
N1 C1 C2 115.82(16) . . ?
C3 C2 C7 120.16(18) . . ?
C3 C2 C1 118.99(17) . . ?
C7 C2 C1 120.85(18) . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 121.1(2) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C2 117.99(18) . . ?
C6 C7 C8 122.53(18) . . ?
C2 C7 C8 119.47(17) . . ?
C9 C8 C7 119.79(17) . . ?
C9 C8 C18 121.32(17) . . ?
C7 C8 C18 118.88(17) . . ?
C8 C9 N1 120.19(17) . . ?
C8 C9 C10 122.36(17) . . ?
N1 C9 C10 117.44(17) . . ?
C9 C10 C11 114.21(19) . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 120.51(19) . . ?
C13 C12 N1 120.05(17) . . ?
C17 C12 N1 119.38(19) . . ?
C12 C13 C14 119.2(2) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.2(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 119.6(2) . . ?
C12 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C19 C18 C23 117.53(19) . . ?
C19 C18 C8 120.79(18) . . ?
C23 C18 C8 121.66(18) . . ?
C18 C19 C20 121.2(2) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C21 C20 C19 120.3(2) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 119.3(2) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C21 C22 C23 120.5(2) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 121.1(2) . . ?
C22 C23 H23 119.4 . . ?
C18 C23 H23 119.4 . . ?

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 N1 C1 O1 -177.68(19) . . . . ?
C12 N1 C1 O1 -0.1(3) . . . . ?
C9 N1 C1 C2 1.9(3) . . . . ?
C12 N1 C1 C2 179.50(16) . . . . ?
O1 C1 C2 C3 -2.0(3) . . . . ?
N1 C1 C2 C3 178.38(18) . . . . ?
O1 C1 C2 C7 178.35(19) . . . . ?
N1 C1 C2 C7 -1.2(3) . . . . ?
C7 C2 C3 C4 0.7(3) . . . . ?
C1 C2 C3 C4 -178.9(2) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C5 C6 C7 C2 0.9(3) . . . . ?
C5 C6 C7 C8 179.93(19) . . . . ?
C3 C2 C7 C6 -1.1(3) . . . . ?
C1 C2 C7 C6 178.46(18) . . . . ?
C3 C2 C7 C8 179.81(18) . . . . ?
C1 C2 C7 C8 -0.6(3) . . . . ?
C6 C7 C8 C9 -177.12(19) . . . . ?
C2 C7 C8 C9 1.9(3) . . . . ?
C6 C7 C8 C18 3.1(3) . . . . ?
C2 C7 C8 C18 -177.86(17) . . . . ?
C7 C8 C9 N1 -1.3(3) . . . . ?
C18 C8 C9 N1 178.46(17) . . . . ?
C7 C8 C9 C10 177.51(18) . . . . ?
C18 C8 C9 C10 -2.8(3) . . . . ?
C1 N1 C9 C8 -0.7(3) . . . . ?
C12 N1 C9 C8 -178.14(18) . . . . ?
C1 N1 C9 C10 -179.53(18) . . . . ?
C12 N1 C9 C10 3.0(3) . . . . ?
C8 C9 C10 C11 -91.6(3) . . . . ?
N1 C9 C10 C11 87.2(2) . . . . ?
C1 N1 C12 C13 89.3(2) . . . . ?
C9 N1 C12 C13 -93.0(2) . . . . ?
C1 N1 C12 C17 -87.8(2) . . . . ?
C9 N1 C12 C17 89.9(2) . . . . ?
C17 C12 C13 C14 -1.5(4) . . . . ?
N1 C12 C13 C14 -178.6(2) . . . . ?
C12 C13 C14 C15 0.9(4) . . . . ?
C13 C14 C15 C16 -0.2(4) . . . . ?
C14 C15 C16 C17 0.2(4) . . . . ?
C13 C12 C17 C16 1.5(3) . . . . ?
N1 C12 C17 C16 178.6(2) . . . . ?
C15 C16 C17 C12 -0.8(4) . . . . ?
C9 C8 C18 C19 -92.9(3) . . . . ?
C7 C8 C18 C19 86.8(3) . . . . ?
C9 C8 C18 C23 89.0(3) . . . . ?
C7 C8 C18 C23 -91.3(2) . . . . ?
C23 C18 C19 C20 -0.4(4) . . . . ?
C8 C18 C19 C20 -178.6(2) . . . . ?
C18 C19 C20 C21 0.0(4) . . . . ?
C19 C20 C21 C22 0.5(4) . . . . ?
C20 C21 C22 C23 -0.7(4) . . . . ?
C21 C22 C23 C18 0.3(4) . . . . ?
C19 C18 C23 C22 0.3(4) . . . . ?
C8 C18 C23 C22 178.5(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C13 H13 O1 0.93 2.48 3.331(3) 151.4 7_554

_refine_diff_density_max         0.137
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.035

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mo_d8v21490_0m
_database_code_depnum_ccdc_archive 'CCDC 2091583'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2021-06-23 deposited with the CCDC.	2021-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 N2 O'
_chemical_formula_weight         326.38

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                   5.5414(5)
_cell_length_b                   9.7020(10)
_cell_length_c                   16.4455(17)
_cell_angle_alpha                98.437(3)
_cell_angle_beta                 98.614(3)
_cell_angle_gamma                97.851(3)
_cell_volume                     853.28(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    6407
_cell_measurement_theta_min      5.085
_cell_measurement_theta_max      54.821

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7143
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(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            14816
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.763
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3320
_reflns_number_gt                2719
_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-2013 (Sheldrick, 2013)'
_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)+(0.0432P)²+0.2046P] 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       0.048(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3320
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.0978
_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
O1 O 0.80058(18) 0.60781(11) 0.55179(5) 0.0445(3) Uani 1 1 d . . . . .
N1 N 0.8247(2) 0.55648(11) 0.41469(6) 0.0345(3) Uani 1 1 d . . . . .
H1 H 0.944(3) 0.5018(17) 0.4274(9) 0.052(4) Uiso 1 1 d . . . . .
N2 N 0.9144(2) 0.25156(13) 0.12764(7) 0.0478(3) Uani 1 1 d . . . . .
C1 C 0.7306(2) 0.62301(14) 0.47862(8) 0.0347(3) Uani 1 1 d . . . . .
C2 C 0.5480(2) 0.71132(13) 0.45480(8) 0.0330(3) Uani 1 1 d . . . . .
C3 C 0.4319(3) 0.77778(14) 0.51607(8) 0.0400(3) Uani 1 1 d . . . . .
H3 H 0.4739 0.7663 0.5719 0.048 Uiso 1 1 calc R U . . .
C4 C 0.2568(3) 0.85959(15) 0.49478(9) 0.0465(4) Uani 1 1 d . . . . .
H4 H 0.1785 0.9039 0.5359 0.056 Uiso 1 1 calc R U . . .
C5 C 0.1956(3) 0.87656(15) 0.41198(9) 0.0456(4) Uani 1 1 d . . . . .
H5 H 0.0756 0.9326 0.3976 0.055 Uiso 1 1 calc R U . . .
C6 C 0.3078(2) 0.81277(14) 0.35104(9) 0.0393(3) Uani 1 1 d . . . . .
H6 H 0.2638 0.8256 0.2955 0.047 Uiso 1 1 calc R U . . .
C7 C 0.4887(2) 0.72803(13) 0.37090(8) 0.0325(3) Uani 1 1 d . . . . .
C8 C 0.6066(2) 0.65570(13) 0.30798(7) 0.0326(3) Uani 1 1 d . . . . .
C9 C 0.7697(2) 0.57125(13) 0.33183(7) 0.0326(3) Uani 1 1 d . . . . .
C10 C 0.9040(2) 0.48540(13) 0.27556(8) 0.0338(3) Uani 1 1 d . . . . .
H10A H 1.0792 0.4987 0.3008 0.041 Uiso 1 1 calc R U . . .
H10B H 0.8932 0.5191 0.2220 0.041 Uiso 1 1 calc R U . . .
C11 C 0.7964(3) 0.32795(15) 0.26033(9) 0.0443(4) Uani 1 1 d . . . . .
H11A H 0.7971 0.2956 0.3141 0.053 Uiso 1 1 calc R U . . .
H11B H 0.6244 0.3139 0.2316 0.053 Uiso 1 1 calc R U . . .
C12 C 0.9420(2) 0.24147(14) 0.20864(8) 0.0379(3) Uani 1 1 d . . . . .
C13 C 1.1025(3) 0.15991(16) 0.24336(9) 0.0477(4) Uani 1 1 d . . . . .
H13 H 1.1198 0.1550 0.3006 0.057 Uiso 1 1 calc R U . . .
C14 C 1.2369(3) 0.08574(17) 0.19321(11) 0.0561(4) Uani 1 1 d . . . . .
H14 H 1.3452 0.0289 0.2156 0.067 Uiso 1 1 calc R U . . .
C15 C 1.2094(3) 0.09655(17) 0.11015(11) 0.0552(4) Uani 1 1 d . . . . .
H15 H 1.2989 0.0478 0.0745 0.066 Uiso 1 1 calc R U . . .
C16 C 1.0481(3) 0.18025(18) 0.08057(9) 0.0548(4) Uani 1 1 d . . . . .
H16 H 1.0306 0.1879 0.0237 0.066 Uiso 1 1 calc R U . . .
C17 C 0.5546(2) 0.67751(14) 0.21926(8) 0.0354(3) Uani 1 1 d . . . . .
C18 C 0.3991(3) 0.57707(17) 0.15820(8) 0.0469(4) Uani 1 1 d . . . . .
H18 H 0.3225 0.4935 0.1725 0.056 Uiso 1 1 calc R U . . .
C19 C 0.3560(3) 0.5992(2) 0.07615(9) 0.0594(5) Uani 1 1 d . . . . .
H19 H 0.2498 0.5307 0.0352 0.071 Uiso 1 1 calc R U . . .
C20 C 0.4681(3) 0.7209(2) 0.05428(9) 0.0589(5) Uani 1 1 d . . . . .
H20 H 0.4386 0.7354 -0.0014 0.071 Uiso 1 1 calc R U . . .
C21 C 0.6229(3) 0.82078(19) 0.11415(10) 0.0545(4) Uani 1 1 d . . . . .
H21 H 0.7006 0.9036 0.0994 0.065 Uiso 1 1 calc R U . . .
C22 C 0.6649(3) 0.79958(16) 0.19625(9) 0.0436(4) Uani 1 1 d . . . . .
H22 H 0.7697 0.8690 0.2370 0.052 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
O1 C1 1.2443(15) . ?
N1 C1 1.3605(16) . ?
N1 C9 1.3840(15) . ?
N1 H1 0.923(17) . ?
N2 C16 1.3346(19) . ?
N2 C12 1.3375(17) . ?
C1 C2 1.4586(18) . ?
C2 C3 1.4009(18) . ?
C2 C7 1.4080(17) . ?
C3 C4 1.373(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.392(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.3725(19) . ?
C5 H5 0.9400 . ?
C6 C7 1.4116(18) . ?
C6 H6 0.9400 . ?
C7 C8 1.4509(17) . ?
C8 C9 1.3534(18) . ?
C8 C17 1.4961(17) . ?
C9 C10 1.5012(16) . ?
C10 C11 1.5316(19) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 C12 1.5027(18) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C12 C13 1.384(2) . ?
C13 C14 1.382(2) . ?
C13 H13 0.9400 . ?
C14 C15 1.373(2) . ?
C14 H14 0.9400 . ?
C15 C16 1.371(2) . ?
C15 H15 0.9400 . ?
C16 H16 0.9400 . ?
C17 C22 1.3866(19) . ?
C17 C18 1.3872(19) . ?
C18 C19 1.388(2) . ?
C18 H18 0.9400 . ?
C19 C20 1.379(3) . ?
C19 H19 0.9400 . ?
C20 C21 1.373(2) . ?
C20 H20 0.9400 . ?
C21 C22 1.3856(19) . ?
C21 H21 0.9400 . ?
C22 H22 0.9400 . ?

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 N1 C9 125.58(11) . . ?
C1 N1 H1 118.1(9) . . ?
C9 N1 H1 116.2(9) . . ?
C16 N2 C12 117.77(13) . . ?
O1 C1 N1 120.71(11) . . ?
O1 C1 C2 123.84(11) . . ?
N1 C1 C2 115.45(11) . . ?
C3 C2 C7 120.72(12) . . ?
C3 C2 C1 119.26(12) . . ?
C7 C2 C1 120.02(11) . . ?
C4 C3 C2 120.20(13) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.67(13) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 121.05(13) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 120.67(13) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C6 117.69(11) . . ?
C2 C7 C8 119.94(11) . . ?
C6 C7 C8 122.35(12) . . ?
C9 C8 C7 118.51(11) . . ?
C9 C8 C17 120.84(11) . . ?
C7 C8 C17 120.63(11) . . ?
C8 C9 N1 120.44(11) . . ?
C8 C9 C10 126.07(11) . . ?
N1 C9 C10 113.49(11) . . ?
C9 C10 C11 111.83(10) . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C10 111.59(11) . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
N2 C12 C13 121.78(13) . . ?
N2 C12 C11 116.23(12) . . ?
C13 C12 C11 121.96(13) . . ?
C14 C13 C12 119.42(14) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C15 C14 C13 118.82(15) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C16 C15 C14 118.28(14) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
N2 C16 C15 123.92(15) . . ?
N2 C16 H16 118.0 . . ?
C15 C16 H16 118.0 . . ?
C22 C17 C18 118.46(13) . . ?
C22 C17 C8 120.02(12) . . ?
C18 C17 C8 121.52(13) . . ?
C17 C18 C19 120.38(15) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 120.41(15) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 119.70(14) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 120.06(16) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C17 120.99(14) . . ?
C21 C22 H22 119.5 . . ?
C17 C22 H22 119.5 . . ?

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 N1 C1 O1 -176.61(12) . . . . ?
C9 N1 C1 C2 3.04(19) . . . . ?
O1 C1 C2 C3 -3.7(2) . . . . ?
N1 C1 C2 C3 176.65(12) . . . . ?
O1 C1 C2 C7 176.83(12) . . . . ?
N1 C1 C2 C7 -2.80(18) . . . . ?
C7 C2 C3 C4 0.4(2) . . . . ?
C1 C2 C3 C4 -179.01(13) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C4 C5 C6 C7 0.0(2) . . . . ?
C3 C2 C7 C6 -0.46(19) . . . . ?
C1 C2 C7 C6 178.99(12) . . . . ?
C3 C2 C7 C8 -178.55(12) . . . . ?
C1 C2 C7 C8 0.89(18) . . . . ?
C5 C6 C7 C2 0.2(2) . . . . ?
C5 C6 C7 C8 178.28(13) . . . . ?
C2 C7 C8 C9 1.06(18) . . . . ?
C6 C7 C8 C9 -176.94(12) . . . . ?
C2 C7 C8 C17 -177.15(11) . . . . ?
C6 C7 C8 C17 4.84(19) . . . . ?
C7 C8 C9 N1 -1.01(19) . . . . ?
C17 C8 C9 N1 177.20(11) . . . . ?
C7 C8 C9 C10 178.28(11) . . . . ?
C17 C8 C9 C10 -3.5(2) . . . . ?
C1 N1 C9 C8 -1.2(2) . . . . ?
C1 N1 C9 C10 179.45(11) . . . . ?
C8 C9 C10 C11 -105.26(15) . . . . ?
N1 C9 C10 C11 74.08(14) . . . . ?
C9 C10 C11 C12 -176.24(11) . . . . ?
C16 N2 C12 C13 -0.2(2) . . . . ?
C16 N2 C12 C11 177.54(13) . . . . ?
C10 C11 C12 N2 -72.94(16) . . . . ?
C10 C11 C12 C13 104.79(15) . . . . ?
N2 C12 C13 C14 -0.5(2) . . . . ?
C11 C12 C13 C14 -178.14(13) . . . . ?
C12 C13 C14 C15 0.8(2) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C12 N2 C16 C15 0.7(2) . . . . ?
C14 C15 C16 N2 -0.4(3) . . . . ?
C9 C8 C17 C22 -100.79(16) . . . . ?
C7 C8 C17 C22 77.38(16) . . . . ?
C9 C8 C17 C18 78.45(17) . . . . ?
C7 C8 C17 C18 -103.37(15) . . . . ?
C22 C17 C18 C19 0.0(2) . . . . ?
C8 C17 C18 C19 -179.28(13) . . . . ?
C17 C18 C19 C20 0.3(2) . . . . ?
C18 C19 C20 C21 -0.1(2) . . . . ?
C19 C20 C21 C22 -0.4(2) . . . . ?
C20 C21 C22 C17 0.7(2) . . . . ?
C18 C17 C22 C21 -0.5(2) . . . . ?
C8 C17 C22 C21 178.78(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.923(17) 1.903(17) 2.8240(15) 176.6(14) 2_766

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.028

_shelxl_version_number           2013-4

