# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_d8v19160
_database_code_depnum_ccdc_archive 'CCDC 1908616'
loop_
_audit_author_name
_audit_author_address
'Jie Sun'
;Shanghai Institute of Organic Chemistry Chinese Academy of Scicence
China
;
_audit_update_record             
;
2019-04-08 deposited with the CCDC.	2019-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 N O'
_chemical_formula_weight         287.35

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                   14.5964(5)
_cell_length_b                   13.9382(5)
_cell_length_c                   14.6669(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2983.94(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    194(2)
_cell_measurement_reflns_used    9992
_cell_measurement_theta_min      4.903
_cell_measurement_theta_max      54.958

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6536
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      194(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            28649
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.452
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2907
_reflns_number_gt                2551
_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)+(0.0422P)²+0.9163P] 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       0.018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2907
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0931
_refine_ls_wR_factor_gt          0.0880
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_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 0.47581(6) 0.79704(6) 0.37593(6) 0.0358(2) Uani 1 1 d . . . . .
N1 N 0.59325(7) 0.60780(7) 0.26633(6) 0.0269(2) Uani 1 1 d . . . . .
C1 C 0.59194(9) 0.53847(9) 0.19665(8) 0.0324(3) Uani 1 1 d . . . . .
H1 H 0.6277 0.4820 0.2034 0.039 Uiso 1 1 calc R U . . .
C2 C 0.54210(10) 0.54986(10) 0.12171(9) 0.0400(3) Uani 1 1 d . . . . .
H2 H 0.5473 0.5036 0.0745 0.048 Uiso 1 1 calc R U . . .
C3 C 0.47813(10) 0.63257(10) 0.10860(9) 0.0399(3) Uani 1 1 d . . . . .
H3A H 0.4215 0.6102 0.0782 0.048 Uiso 1 1 calc R U . . .
H3B H 0.5073 0.6814 0.0691 0.048 Uiso 1 1 calc R U . . .
C4 C 0.45416(8) 0.67727(9) 0.20086(8) 0.0333(3) Uani 1 1 d . . . . .
H4A H 0.4145 0.6329 0.2358 0.040 Uiso 1 1 calc R U . . .
H4B H 0.4200 0.7378 0.1913 0.040 Uiso 1 1 calc R U . . .
C5 C 0.54200(8) 0.69758(8) 0.25490(8) 0.0261(3) Uani 1 1 d . . . . .
C6 C 0.52155(7) 0.72666(8) 0.35494(8) 0.0267(3) Uani 1 1 d . . . . .
C7 C 0.56708(8) 0.65756(8) 0.41128(8) 0.0276(3) Uani 1 1 d . . . . .
H7 H 0.5696 0.6590 0.4760 0.033 Uiso 1 1 calc R U . . .
C8 C 0.60616(7) 0.58932(8) 0.35722(8) 0.0248(3) Uani 1 1 d . . . . .
C9 C 0.65929(8) 0.50487(8) 0.38758(7) 0.0258(3) Uani 1 1 d . . . . .
C10 C 0.62001(8) 0.43768(8) 0.44556(8) 0.0290(3) Uani 1 1 d . . . . .
H10 H 0.5579 0.4446 0.4639 0.035 Uiso 1 1 calc R U . . .
C11 C 0.67084(9) 0.36071(9) 0.47676(9) 0.0374(3) Uani 1 1 d . . . . .
H11 H 0.6433 0.3142 0.5154 0.045 Uiso 1 1 calc R U . . .
C12 C 0.76179(10) 0.35136(10) 0.45183(9) 0.0419(3) Uani 1 1 d . . . . .
H12 H 0.7969 0.2991 0.4743 0.050 Uiso 1 1 calc R U . . .
C13 C 0.80161(9) 0.41784(11) 0.39446(9) 0.0421(3) Uani 1 1 d . . . . .
H13 H 0.8642 0.4115 0.3777 0.050 Uiso 1 1 calc R U . . .
C14 C 0.75033(9) 0.49376(10) 0.36139(8) 0.0353(3) Uani 1 1 d . . . . .
H14 H 0.7774 0.5385 0.3206 0.042 Uiso 1 1 calc R U . . .
C15 C 0.60116(8) 0.77442(8) 0.20943(7) 0.0258(3) Uani 1 1 d . . . . .
C16 C 0.69156(8) 0.75837(9) 0.18389(8) 0.0315(3) Uani 1 1 d . . . . .
H16 H 0.7188 0.6976 0.1951 0.038 Uiso 1 1 calc R U . . .
C17 C 0.74253(9) 0.83010(9) 0.14223(8) 0.0348(3) Uani 1 1 d . . . . .
H17 H 0.8043 0.8182 0.1254 0.042 Uiso 1 1 calc R U . . .
C18 C 0.70372(9) 0.91874(9) 0.12516(8) 0.0330(3) Uani 1 1 d . . . . .
H18 H 0.7381 0.9674 0.0954 0.040 Uiso 1 1 calc R U . . .
C19 C 0.61417(9) 0.93598(9) 0.15181(8) 0.0320(3) Uani 1 1 d . . . . .
H19 H 0.5875 0.9972 0.1413 0.038 Uiso 1 1 calc R U . . .
C20 C 0.56330(8) 0.86477(8) 0.19368(8) 0.0296(3) Uani 1 1 d . . . . .
H20 H 0.5020 0.8775 0.2119 0.035 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 C6 1.2258(14) . ?
N1 C8 1.3708(15) . ?
N1 C1 1.4067(15) . ?
N1 C5 1.4674(14) . ?
C1 C2 1.3276(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.496(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.5302(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5337(16) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C15 1.5289(15) . ?
C5 C6 1.5513(16) . ?
C6 C7 1.4325(16) . ?
C7 C8 1.3634(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.4782(16) . ?
C9 C10 1.3888(16) . ?
C9 C14 1.3920(17) . ?
C10 C11 1.3824(17) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3839(18) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.3897(17) . ?
C15 C20 1.3944(16) . ?
C16 C17 1.3880(17) . ?
C16 H16 0.9500 . ?
C17 C18 1.3820(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.3854(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.3833(17) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

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
C8 N1 C1 125.40(10) . . ?
C8 N1 C5 109.96(9) . . ?
C1 N1 C5 119.73(9) . . ?
C2 C1 N1 121.79(12) . . ?
C2 C1 H1 119.1 . . ?
N1 C1 H1 119.1 . . ?
C1 C2 C3 122.72(12) . . ?
C1 C2 H2 118.6 . . ?
C3 C2 H2 118.6 . . ?
C2 C3 C4 110.05(10) . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C3 C4 C5 109.94(10) . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
N1 C5 C15 111.06(9) . . ?
N1 C5 C4 109.14(9) . . ?
C15 C5 C4 112.09(9) . . ?
N1 C5 C6 102.29(9) . . ?
C15 C5 C6 109.76(9) . . ?
C4 C5 C6 112.10(10) . . ?
O1 C6 C7 130.23(11) . . ?
O1 C6 C5 123.46(10) . . ?
C7 C6 C5 106.30(9) . . ?
C8 C7 C6 109.13(10) . . ?
C8 C7 H7 125.4 . . ?
C6 C7 H7 125.4 . . ?
C7 C8 N1 112.14(10) . . ?
C7 C8 C9 126.86(10) . . ?
N1 C8 C9 120.98(10) . . ?
C10 C9 C14 119.22(11) . . ?
C10 C9 C8 120.32(10) . . ?
C14 C9 C8 120.41(10) . . ?
C11 C10 C9 120.29(11) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.05(12) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 120.15(12) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 119.95(12) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 120.31(12) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?
C16 C15 C20 118.49(11) . . ?
C16 C15 C5 122.75(10) . . ?
C20 C15 C5 118.76(10) . . ?
C17 C16 C15 120.77(11) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 120.26(11) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 119.39(11) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C20 C19 C18 120.48(11) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C15 120.59(11) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?

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
C8 N1 C1 C2 149.63(13) . . . . ?
C5 N1 C1 C2 -3.01(17) . . . . ?
N1 C1 C2 C3 -5.0(2) . . . . ?
C1 C2 C3 C4 -19.83(18) . . . . ?
C2 C3 C4 C5 50.40(14) . . . . ?
C8 N1 C5 C15 113.91(10) . . . . ?
C1 N1 C5 C15 -89.57(12) . . . . ?
C8 N1 C5 C4 -122.03(10) . . . . ?
C1 N1 C5 C4 34.49(14) . . . . ?
C8 N1 C5 C6 -3.14(12) . . . . ?
C1 N1 C5 C6 153.38(10) . . . . ?
C3 C4 C5 N1 -57.70(13) . . . . ?
C3 C4 C5 C15 65.75(13) . . . . ?
C3 C4 C5 C6 -170.29(10) . . . . ?
N1 C5 C6 O1 -176.88(10) . . . . ?
C15 C5 C6 O1 65.14(14) . . . . ?
C4 C5 C6 O1 -60.10(14) . . . . ?
N1 C5 C6 C7 4.09(11) . . . . ?
C15 C5 C6 C7 -113.89(10) . . . . ?
C4 C5 C6 C7 120.87(10) . . . . ?
O1 C6 C7 C8 177.32(12) . . . . ?
C5 C6 C7 C8 -3.74(12) . . . . ?
C6 C7 C8 N1 1.84(13) . . . . ?
C6 C7 C8 C9 -179.73(10) . . . . ?
C1 N1 C8 C7 -153.85(11) . . . . ?
C5 N1 C8 C7 1.02(13) . . . . ?
C1 N1 C8 C9 27.62(17) . . . . ?
C5 N1 C8 C9 -177.51(9) . . . . ?
C7 C8 C9 C10 58.47(16) . . . . ?
N1 C8 C9 C10 -123.23(12) . . . . ?
C7 C8 C9 C14 -118.95(14) . . . . ?
N1 C8 C9 C14 59.35(15) . . . . ?
C14 C9 C10 C11 -0.04(18) . . . . ?
C8 C9 C10 C11 -177.48(11) . . . . ?
C9 C10 C11 C12 1.36(19) . . . . ?
C10 C11 C12 C13 -1.2(2) . . . . ?
C11 C12 C13 C14 -0.3(2) . . . . ?
C12 C13 C14 C9 1.7(2) . . . . ?
C10 C9 C14 C13 -1.48(19) . . . . ?
C8 C9 C14 C13 175.96(12) . . . . ?
N1 C5 C15 C16 -0.36(15) . . . . ?
C4 C5 C15 C16 -122.72(12) . . . . ?
C6 C5 C15 C16 112.03(12) . . . . ?
N1 C5 C15 C20 -179.69(10) . . . . ?
C4 C5 C15 C20 57.95(14) . . . . ?
C6 C5 C15 C20 -67.31(13) . . . . ?
C20 C15 C16 C17 -1.09(17) . . . . ?
C5 C15 C16 C17 179.58(11) . . . . ?
C15 C16 C17 C18 -0.29(19) . . . . ?
C16 C17 C18 C19 1.40(18) . . . . ?
C17 C18 C19 C20 -1.14(18) . . . . ?
C18 C19 C20 C15 -0.25(18) . . . . ?
C16 C15 C20 C19 1.35(17) . . . . ?
C5 C15 C20 C19 -179.29(10) . . . . ?

_refine_diff_density_max         0.254
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.031

_shelxl_version_number           2013-4



