# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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. 
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data_190423_lf_190423_1_0m
_database_code_depnum_ccdc_archive 'CCDC 1914003'
loop_
_audit_author_name
_audit_author_address
'Feng Luo'
;zhejiang university
China
;
_audit_update_record             
;
2019-05-05 deposited with the CCDC.	2020-02-21 downloaded from the CCDC.
;
_audit_creation_date             2019-04-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H19 N O2'
_chemical_formula_sum            'C26 H19 N O2'
_chemical_formula_weight         377.42
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3803(4)
_cell_length_b                   10.8364(7)
_cell_length_c                   11.0444(6)
_cell_angle_alpha                77.127(2)
_cell_angle_beta                 89.613(2)
_cell_angle_gamma                76.222(2)
_cell_volume                     948.49(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6910
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      3.19
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1020 before and 0.0376 after correction.
The Ratio of minimum to maximum transmission is 0.9438.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.449
_exptl_crystal_size_mid          0.357
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10918
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.414
_diffrn_reflns_theta_min         2.505
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3282
_reflns_number_total             3830
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3830
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0419
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0579P)²+0.2857P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1154
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C15(H15), C17(H17), C18(H18),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.34375(11) 0.35163(9) 0.66121(8) 0.0279(2) Uani 1 1 d . . . . .
O2 O -0.08135(12) 0.21465(9) 0.46485(9) 0.0340(2) Uani 1 1 d . . . . .
N1 N 0.96145(14) 0.05156(11) 0.81644(10) 0.0294(3) Uani 1 1 d . . . . .
C1 C 0.96446(18) 0.35394(15) 0.89669(13) 0.0341(3) Uani 1 1 d . . . . .
H1 H 0.889419 0.436255 0.890689 0.041 Uiso 1 1 calc R . . . .
C2 C 1.12061(19) 0.32931(17) 0.95029(15) 0.0406(4) Uani 1 1 d . . . . .
H2 H 1.152216 0.395063 0.981965 0.049 Uiso 1 1 calc R . . . .
C3 C 1.23295(19) 0.20901(17) 0.95864(15) 0.0411(4) Uani 1 1 d . . . . .
H3 H 1.340165 0.195088 0.994738 0.049 Uiso 1 1 calc R . . . .
C4 C 1.19130(17) 0.11028(16) 0.91560(13) 0.0358(3) Uani 1 1 d . . . . .
H4 H 1.267832 0.028647 0.921592 0.043 Uiso 1 1 calc R . . . .
C5 C 1.03274(17) 0.13432(14) 0.86288(12) 0.0294(3) Uani 1 1 d . . . . .
C6 C 0.91817(17) 0.25632(14) 0.85139(12) 0.0285(3) Uani 1 1 d . . . . .
C7 C 0.76908(16) 0.24565(13) 0.79283(12) 0.0265(3) Uani 1 1 d . . . . .
C8 C 0.80162(16) 0.11605(13) 0.77435(12) 0.0265(3) Uani 1 1 d . . . . .
C9 C 0.68598(16) 0.06760(13) 0.72275(12) 0.0272(3) Uani 1 1 d . . . . .
H9 H 0.709547 -0.019553 0.712461 0.033 Uiso 1 1 calc R . . . .
C10 C 0.53370(16) 0.15369(12) 0.68695(12) 0.0259(3) Uani 1 1 d . . . . .
C11 C 0.50248(16) 0.28153(13) 0.70537(12) 0.0260(3) Uani 1 1 d . . . . .
C12 C 0.61423(16) 0.33320(13) 0.75619(12) 0.0258(3) Uani 1 1 d . . . . .
C13 C 0.38457(16) 0.14509(12) 0.62794(11) 0.0256(3) Uani 1 1 d . . . . .
C14 C 0.27515(16) 0.26669(12) 0.61543(11) 0.0252(3) Uani 1 1 d . . . . .
C15 C 0.11677(16) 0.29871(13) 0.56300(12) 0.0269(3) Uani 1 1 d . . . . .
H15 H 0.044973 0.382416 0.556867 0.032 Uiso 1 1 calc R . . . .
C16 C 0.06894(16) 0.20087(13) 0.51975(12) 0.0271(3) Uani 1 1 d . . . . .
C17 C 0.17677(17) 0.07739(13) 0.53053(12) 0.0282(3) Uani 1 1 d . . . . .
H17 H 0.141211 0.012454 0.500184 0.034 Uiso 1 1 calc R . . . .
C18 C 0.33266(17) 0.04880(13) 0.58412(12) 0.0274(3) Uani 1 1 d . . . . .
H18 H 0.404158 -0.035200 0.591297 0.033 Uiso 1 1 calc R . . . .
C19 C 1.03934(18) -0.08206(14) 0.81202(13) 0.0334(3) Uani 1 1 d . . . . .
H19A H 0.961487 -0.136796 0.836271 0.050 Uiso 1 1 calc GR . . . .
H19B H 1.136497 -0.114387 0.869476 0.050 Uiso 1 1 calc GR . . . .
H19C H 1.072646 -0.085241 0.727317 0.050 Uiso 1 1 calc GR . . . .
C20 C 0.57342(16) 0.47106(13) 0.76875(12) 0.0261(3) Uani 1 1 d . . . . .
C21 C 0.44880(17) 0.51463(14) 0.84350(13) 0.0319(3) Uani 1 1 d . . . . .
H21 H 0.387603 0.456203 0.885892 0.038 Uiso 1 1 calc R . . . .
C22 C 0.41230(19) 0.64228(15) 0.85723(14) 0.0372(3) Uani 1 1 d . . . . .
H22 H 0.327488 0.670360 0.909624 0.045 Uiso 1 1 calc R . . . .
C23 C 0.49875(19) 0.72869(14) 0.79504(13) 0.0350(3) Uani 1 1 d . . . . .
H23 H 0.474293 0.815959 0.805037 0.042 Uiso 1 1 calc R . . . .
C24 C 0.6210(2) 0.68773(14) 0.71821(14) 0.0382(4) Uani 1 1 d . . . . .
H24 H 0.679493 0.747303 0.674053 0.046 Uiso 1 1 calc R . . . .
C25 C 0.65830(19) 0.55980(14) 0.70547(14) 0.0351(3) Uani 1 1 d . . . . .
H25 H 0.743024 0.532231 0.652811 0.042 Uiso 1 1 calc R . . . .
C26 C -0.19411(19) 0.33894(15) 0.44389(15) 0.0396(4) Uani 1 1 d . . . . .
H26A H -0.146280 0.403817 0.389327 0.059 Uiso 1 1 calc GR . . . .
H26B H -0.217254 0.363777 0.523454 0.059 Uiso 1 1 calc GR . . . .
H26C H -0.296592 0.334945 0.404443 0.059 Uiso 1 1 calc GR . . . .


_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 C11 1.3953(16) . ?
O1 C14 1.3772(16) . ?
O2 C16 1.3626(16) . ?
O2 C26 1.4206(17) . ?
N1 C5 1.3743(19) . ?
N1 C8 1.3843(17) . ?
N1 C19 1.4512(18) . ?
C1 H1 0.9500 . ?
C1 C2 1.381(2) . ?
C1 C6 1.398(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.399(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.378(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3966(19) . ?
C5 C6 1.4170(19) . ?
C6 C7 1.4511(19) . ?
C7 C8 1.4258(19) . ?
C7 C12 1.4133(18) . ?
C8 C9 1.3866(19) . ?
C9 H9 0.9500 . ?
C9 C10 1.3894(18) . ?
C10 C11 1.4076(18) . ?
C10 C13 1.4454(19) . ?
C11 C12 1.3793(19) . ?
C12 C20 1.4887(18) . ?
C13 C14 1.3933(18) . ?
C13 C18 1.3987(19) . ?
C14 C15 1.3853(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.3941(19) . ?
C16 C17 1.4056(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.3744(19) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.3865(19) . ?
C20 C25 1.3924(19) . ?
C21 H21 0.9500 . ?
C21 C22 1.386(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.380(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.380(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.385(2) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

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
C14 O1 C11 105.72(10) . . ?
C16 O2 C26 118.05(11) . . ?
C5 N1 C8 108.96(11) . . ?
C5 N1 C19 126.04(12) . . ?
C8 N1 C19 125.00(12) . . ?
C2 C1 H1 120.4 . . ?
C2 C1 C6 119.21(14) . . ?
C6 C1 H1 120.4 . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.01(15) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.37(14) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 121.1 . . ?
C3 C4 C5 117.73(14) . . ?
C5 C4 H4 121.1 . . ?
N1 C5 C4 128.67(13) . . ?
N1 C5 C6 109.55(12) . . ?
C4 C5 C6 121.78(14) . . ?
C1 C6 C5 118.88(13) . . ?
C1 C6 C7 134.72(13) . . ?
C5 C6 C7 106.38(12) . . ?
C8 C7 C6 106.05(11) . . ?
C12 C7 C6 133.42(13) . . ?
C12 C7 C8 120.52(12) . . ?
N1 C8 C7 109.04(12) . . ?
N1 C8 C9 127.78(13) . . ?
C9 C8 C7 123.18(12) . . ?
C8 C9 H9 121.9 . . ?
C8 C9 C10 116.24(12) . . ?
C10 C9 H9 121.9 . . ?
C9 C10 C11 120.27(13) . . ?
C9 C10 C13 134.12(13) . . ?
C11 C10 C13 105.60(11) . . ?
O1 C11 C10 110.81(11) . . ?
C12 C11 O1 124.00(12) . . ?
C12 C11 C10 125.15(12) . . ?
C7 C12 C20 123.47(12) . . ?
C11 C12 C7 114.62(12) . . ?
C11 C12 C20 121.91(12) . . ?
C14 C13 C10 106.09(12) . . ?
C14 C13 C18 118.32(12) . . ?
C18 C13 C10 135.59(12) . . ?
O1 C14 C13 111.77(11) . . ?
O1 C14 C15 123.98(12) . . ?
C15 C14 C13 124.25(12) . . ?
C14 C15 H15 122.0 . . ?
C14 C15 C16 116.06(12) . . ?
C16 C15 H15 122.0 . . ?
O2 C16 C15 124.39(12) . . ?
O2 C16 C17 114.58(12) . . ?
C15 C16 C17 121.04(13) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.26(13) . . ?
C18 C17 H17 119.4 . . ?
C13 C18 H18 120.5 . . ?
C17 C18 C13 119.08(12) . . ?
C17 C18 H18 120.5 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C12 120.69(12) . . ?
C21 C20 C25 118.21(13) . . ?
C25 C20 C12 121.10(12) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.90(13) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.20(13) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 120.2 . . ?
C22 C23 C24 119.69(13) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 120.03(14) . . ?
C25 C24 H24 120.0 . . ?
C20 C25 H25 119.5 . . ?
C24 C25 C20 120.94(14) . . ?
C24 C25 H25 119.5 . . ?
O2 C26 H26A 109.5 . . ?
O2 C26 H26B 109.5 . . ?
O2 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
