# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_xl_165_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1968169'
loop_
_audit_author_name
_audit_author_address
'Xiaohe Miao'
;Westlake University
China
;
_audit_update_record             
;
2019-12-06 deposited with the CCDC.	2024-02-19 downloaded from the CCDC.
;
_audit_creation_date             2019-11-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H21 N'
_chemical_formula_sum            'C26 H21 N O0'
_chemical_formula_weight         347.44
_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                   9.0336(5)
_cell_length_b                   10.5141(5)
_cell_length_c                   12.1297(7)
_cell_angle_alpha                110.415(2)
_cell_angle_beta                 95.345(2)
_cell_angle_gamma                114.138(2)
_cell_volume                     947.12(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9990
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.29
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1315 before and 0.0447 after correction.
The Ratio of minimum to maximum transmission is 0.9663.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            36207
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.316
_diffrn_reflns_theta_min         2.292
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.990
_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                4243
_reflns_number_total             4665
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL n/a (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4665
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.047
_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)+(0.0529P)²+0.2757P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1064
_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:
 C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00M(H00N), C00N(H00O),
 C00O(H00P), C00P(H00Q), C00Q(H00R), C00R(H00S), C002(H002), C005(H005)
2.b Idealised Me refined as rotating group:
 C00L(H00F,H00L,H00M)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
N001 N 0.30505(11) 0.40633(10) 0.05199(8) 0.02507(19) Uani 1 1 d . . . . .
C00A C -0.10339(12) 0.52932(11) 0.17328(9) 0.0217(2) Uani 1 1 d . . . . .
H00A H -0.210345 0.512545 0.134676 0.026 Uiso 1 1 calc R U . . .
C00B C 1.19439(12) 0.75480(11) 0.69758(9) 0.0226(2) Uani 1 1 d . . . . .
H00B H 1.103562 0.660589 0.687652 0.027 Uiso 1 1 calc R U . . .
C00C C 0.49186(12) 0.73316(11) 0.44681(9) 0.02059(19) Uani 1 1 d . . . . .
H00C H 0.462820 0.812770 0.481936 0.025 Uiso 1 1 calc R U . . .
C00D C 0.14000(12) 0.21580(11) 0.11701(9) 0.0226(2) Uani 1 1 d . . . . .
H00D H 0.058939 0.183746 0.159348 0.027 Uiso 1 1 calc R U . . .
C00E C 0.94223(12) 0.94029(11) 0.63645(9) 0.02128(19) Uani 1 1 d . . . . .
H00E H 1.024289 1.043532 0.688406 0.026 Uiso 1 1 calc R U . . .
C00F C 0.98572(11) 0.82216(10) 0.61407(8) 0.01853(18) Uani 1 1 d . . . . .
C00G C 0.37884(11) 0.60809(11) 0.34763(9) 0.01964(19) Uani 1 1 d . . . . .
H00G H 0.407595 0.528207 0.312878 0.024 Uiso 1 1 calc R U . . .
C00H C 0.14488(12) 0.67771(11) 0.34444(9) 0.02114(19) Uani 1 1 d . . . . .
H00H H 0.205776 0.760415 0.423186 0.025 Uiso 1 1 calc R U . . .
C00I C 1.29749(12) 0.99493(11) 0.67980(8) 0.02107(19) Uani 1 1 d . . . . .
H00I H 1.277230 1.066067 0.658098 0.025 Uiso 1 1 calc R U . . .
C00J C 0.78126(12) 0.90899(11) 0.58398(9) 0.0217(2) Uani 1 1 d . . . . .
H00J H 0.754655 0.991216 0.601027 0.026 Uiso 1 1 calc R U . . .
C00K C -0.01139(12) 0.65184(11) 0.28708(9) 0.0224(2) Uani 1 1 d . . . . .
H00K H -0.055653 0.718240 0.325821 0.027 Uiso 1 1 calc R U . . .
C00L C -0.14933(12) 0.29349(11) -0.00527(9) 0.0239(2) Uani 1 1 d . . . . .
H00F H -0.224417 0.317300 -0.048377 0.036 Uiso 1 1 calc R U . . .
H00L H -0.216940 0.204401 0.010111 0.036 Uiso 1 1 calc R U . . .
H00M H -0.077213 0.269739 -0.055612 0.036 Uiso 1 1 calc R U . . .
C00M C 0.20960(13) 0.12333(11) 0.06099(10) 0.0258(2) Uani 1 1 d . . . . .
H00N H 0.177306 0.027175 0.064733 0.031 Uiso 1 1 calc R U . . .
C00N C 1.46217(12) 1.02845(12) 0.72579(9) 0.0245(2) Uani 1 1 d . . . . .
H00O H 1.553662 1.121786 0.734870 0.029 Uiso 1 1 calc R U . . .
C00O C 0.32644(13) 0.17281(12) -0.00031(10) 0.0279(2) Uani 1 1 d . . . . .
H00P H 0.375411 0.111364 -0.040181 0.034 Uiso 1 1 calc R U . . .
C00P C 1.49338(12) 0.92614(12) 0.75848(9) 0.0263(2) Uani 1 1 d . . . . .
H00Q H 1.606066 0.949494 0.790448 0.032 Uiso 1 1 calc R U . . .
C00Q C 1.35940(13) 0.78925(12) 0.74436(10) 0.0263(2) Uani 1 1 d . . . . .
H00R H 1.380623 0.718984 0.766749 0.032 Uiso 1 1 calc R U . . .
C00R C 0.37035(14) 0.31450(13) -0.00210(10) 0.0299(2) Uani 1 1 d . . . . .
H00S H 0.451238 0.348744 -0.043937 0.036 Uiso 1 1 calc R U . . .
C002 C 0.69845(12) 0.63935(10) 0.48794(9) 0.02023(19) Uani 1 1 d . . . . .
H002 H 0.615225 0.535699 0.438481 0.024 Uiso 1 1 calc R U . . .
C003 C 0.65668(11) 0.75827(10) 0.50615(8) 0.01932(19) Uani 1 1 d . . . . .
C004 C 0.11955(11) 0.45917(10) 0.17153(8) 0.01746(18) Uani 1 1 d . . . . .
C005 C 0.85931(11) 0.67057(10) 0.54099(9) 0.02003(19) Uani 1 1 d . . . . .
H005 H 0.884355 0.587891 0.527606 0.024 Uiso 1 1 calc R U . . .
C006 C 0.19051(11) 0.35592(10) 0.11032(8) 0.01801(18) Uani 1 1 d . . . . .
C007 C 1.16072(11) 0.85740(11) 0.66498(8) 0.01898(19) Uani 1 1 d . . . . .
C008 C -0.04062(11) 0.43057(10) 0.11496(9) 0.01924(19) Uani 1 1 d . . . . .
C009 C 0.21395(11) 0.58320(10) 0.28755(8) 0.01809(18) 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
N001 C00R 1.3441(13) . ?
N001 C006 1.3423(12) . ?
C00A H00A 0.9500 . ?
C00A C00K 1.3877(14) . ?
C00A C008 1.3942(13) . ?
C00B H00B 0.9500 . ?
C00B C00Q 1.3902(13) . ?
C00B C007 1.3986(13) . ?
C00C H00C 0.9500 . ?
C00C C00G 1.3373(13) . ?
C00C C003 1.4667(12) . ?
C00D H00D 0.9500 . ?
C00D C00M 1.3861(14) . ?
C00D C006 1.3876(13) . ?
C00E H00E 0.9500 . ?
C00E C00F 1.3980(13) . ?
C00E C00J 1.3849(13) . ?
C00F C005 1.4026(13) . ?
C00F C007 1.4823(12) . ?
C00G H00G 0.9500 . ?
C00G C009 1.4712(12) . ?
C00H H00H 0.9500 . ?
C00H C00K 1.3864(13) . ?
C00H C009 1.4006(13) . ?
C00I H00I 0.9500 . ?
C00I C00N 1.3886(13) . ?
C00I C007 1.4021(13) . ?
C00J H00J 0.9500 . ?
C00J C003 1.4031(13) . ?
C00K H00K 0.9500 . ?
C00L H00F 0.9800 . ?
C00L H00L 0.9800 . ?
C00L H00M 0.9800 . ?
C00L C008 1.5092(13) . ?
C00M H00N 0.9500 . ?
C00M C00O 1.3800(15) . ?
C00N H00O 0.9500 . ?
C00N C00P 1.3851(15) . ?
C00O H00P 0.9500 . ?
C00O C00R 1.3850(16) . ?
C00P H00Q 0.9500 . ?
C00P C00Q 1.3894(15) . ?
C00Q H00R 0.9500 . ?
C00R H00S 0.9500 . ?
C002 H002 0.9500 . ?
C002 C003 1.4011(13) . ?
C002 C005 1.3862(13) . ?
C004 C006 1.4954(12) . ?
C004 C008 1.4036(12) . ?
C004 C009 1.4124(12) . ?
C005 H005 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
C006 N001 C00R 117.34(9) . . ?
C00K C00A H00A 119.6 . . ?
C00K C00A C008 120.74(9) . . ?
C008 C00A H00A 119.6 . . ?
C00Q C00B H00B 119.7 . . ?
C00Q C00B C007 120.68(9) . . ?
C007 C00B H00B 119.7 . . ?
C00G C00C H00C 117.1 . . ?
C00G C00C C003 125.75(9) . . ?
C003 C00C H00C 117.1 . . ?
C00M C00D H00D 120.5 . . ?
C00M C00D C006 119.00(9) . . ?
C006 C00D H00D 120.5 . . ?
C00F C00E H00E 119.5 . . ?
C00J C00E H00E 119.5 . . ?
C00J C00E C00F 120.95(8) . . ?
C00E C00F C005 117.86(8) . . ?
C00E C00F C007 120.66(8) . . ?
C005 C00F C007 121.48(8) . . ?
C00C C00G H00G 117.1 . . ?
C00C C00G C009 125.81(9) . . ?
C009 C00G H00G 117.1 . . ?
C00K C00H H00H 119.6 . . ?
C00K C00H C009 120.71(9) . . ?
C009 C00H H00H 119.6 . . ?
C00N C00I H00I 119.6 . . ?
C00N C00I C007 120.82(9) . . ?
C007 C00I H00I 119.6 . . ?
C00E C00J H00J 119.3 . . ?
C00E C00J C003 121.33(9) . . ?
C003 C00J H00J 119.3 . . ?
C00A C00K H00K 119.9 . . ?
C00H C00K C00A 120.24(9) . . ?
C00H C00K H00K 119.9 . . ?
H00F C00L H00L 109.5 . . ?
H00F C00L H00M 109.5 . . ?
H00L C00L H00M 109.5 . . ?
C008 C00L H00F 109.5 . . ?
C008 C00L H00L 109.5 . . ?
C008 C00L H00M 109.5 . . ?
C00D C00M H00N 120.4 . . ?
C00O C00M C00D 119.11(9) . . ?
C00O C00M H00N 120.4 . . ?
C00I C00N H00O 119.9 . . ?
C00P C00N C00I 120.16(9) . . ?
C00P C00N H00O 119.9 . . ?
C00M C00O H00P 120.9 . . ?
C00M C00O C00R 118.17(10) . . ?
C00R C00O H00P 120.9 . . ?
C00N C00P H00Q 120.1 . . ?
C00N C00P C00Q 119.81(9) . . ?
C00Q C00P H00Q 120.1 . . ?
C00B C00Q H00R 119.9 . . ?
C00P C00Q C00B 120.21(9) . . ?
C00P C00Q H00R 119.9 . . ?
N001 C00R C00O 123.74(10) . . ?
N001 C00R H00S 118.1 . . ?
C00O C00R H00S 118.1 . . ?
C003 C002 H002 119.5 . . ?
C005 C002 H002 119.5 . . ?
C005 C002 C003 121.03(8) . . ?
C00J C003 C00C 118.94(8) . . ?
C002 C003 C00C 123.46(8) . . ?
C002 C003 C00J 117.59(8) . . ?
C008 C004 C006 120.08(8) . . ?
C008 C004 C009 120.67(8) . . ?
C009 C004 C006 119.24(8) . . ?
C00F C005 H005 119.4 . . ?
C002 C005 C00F 121.12(8) . . ?
C002 C005 H005 119.4 . . ?
N001 C006 C00D 122.64(9) . . ?
N001 C006 C004 117.18(8) . . ?
C00D C006 C004 120.17(8) . . ?
C00B C007 C00F 121.47(8) . . ?
C00B C007 C00I 118.32(9) . . ?
C00I C007 C00F 120.21(8) . . ?
C00A C008 C00L 118.90(8) . . ?
C00A C008 C004 119.02(8) . . ?
C004 C008 C00L 122.05(8) . . ?
C00H C009 C00G 121.41(8) . . ?
C00H C009 C004 118.59(8) . . ?
C004 C009 C00G 119.98(8) . . ?

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
C00C C00G C009 C00H -13.15(15) . . . . ?
C00C C00G C009 C004 168.71(9) . . . . ?
C00D C00M C00O C00R 0.59(15) . . . . ?
C00E C00F C005 C002 2.93(14) . . . . ?
C00E C00F C007 C00B 148.39(10) . . . . ?
C00E C00F C007 C00I -32.60(13) . . . . ?
C00E C00J C003 C00C -176.03(9) . . . . ?
C00E C00J C003 C002 2.99(14) . . . . ?
C00F C00E C00J C003 -0.39(15) . . . . ?
C00G C00C C003 C00J 160.64(10) . . . . ?
C00G C00C C003 C002 -18.31(15) . . . . ?
C00I C00N C00P C00Q 0.42(15) . . . . ?
C00J C00E C00F C005 -2.58(14) . . . . ?
C00J C00E C00F C007 176.61(8) . . . . ?
C00K C00A C008 C00L 176.47(8) . . . . ?
C00K C00A C008 C004 -1.71(14) . . . . ?
C00K C00H C009 C00G -179.39(8) . . . . ?
C00K C00H C009 C004 -1.22(14) . . . . ?
C00M C00D C006 N001 -0.27(14) . . . . ?
C00M C00D C006 C004 -179.06(8) . . . . ?
C00M C00O C00R N001 -0.33(17) . . . . ?
C00N C00I C007 C00B -0.06(14) . . . . ?
C00N C00I C007 C00F -179.11(9) . . . . ?
C00N C00P C00Q C00B 0.01(16) . . . . ?
C00Q C00B C007 C00F 179.53(9) . . . . ?
C00Q C00B C007 C00I 0.49(14) . . . . ?
C00R N001 C006 C00D 0.53(14) . . . . ?
C00R N001 C006 C004 179.35(9) . . . . ?
C003 C00C C00G C009 -179.57(8) . . . . ?
C003 C002 C005 C00F -0.32(14) . . . . ?
C005 C00F C007 C00B -32.45(13) . . . . ?
C005 C00F C007 C00I 146.56(9) . . . . ?
C005 C002 C003 C00C 176.34(9) . . . . ?
C005 C002 C003 C00J -2.63(14) . . . . ?
C006 N001 C00R C00O -0.23(16) . . . . ?
C006 C00D C00M C00O -0.31(15) . . . . ?
C006 C004 C008 C00A -179.39(8) . . . . ?
C006 C004 C008 C00L 2.49(13) . . . . ?
C006 C004 C009 C00G -0.98(13) . . . . ?
C006 C004 C009 C00H -179.18(8) . . . . ?
C007 C00B C00Q C00P -0.47(15) . . . . ?
C007 C00F C005 C002 -176.25(8) . . . . ?
C007 C00I C00N C00P -0.39(15) . . . . ?
C008 C00A C00K C00H 0.02(14) . . . . ?
C008 C004 C006 N001 100.95(10) . . . . ?
C008 C004 C006 C00D -80.20(11) . . . . ?
C008 C004 C009 C00G 177.70(8) . . . . ?
C008 C004 C009 C00H -0.49(13) . . . . ?
C009 C00H C00K C00A 1.47(14) . . . . ?
C009 C004 C006 N001 -80.36(11) . . . . ?
C009 C004 C006 C00D 98.49(10) . . . . ?
C009 C004 C008 C00A 1.94(13) . . . . ?
C009 C004 C008 C00L -176.18(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
