# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_w20220222_h_0m
_database_code_depnum_ccdc_archive 'CCDC 2211762'
loop_
_audit_author_name
_audit_author_address
llp
;Gannan Normal University,
China
;
_audit_update_record             
;
2022-10-08 deposited with the CCDC.	2022-12-05 downloaded from the CCDC.
;
_audit_creation_date             2022-02-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 N2'
_chemical_formula_sum            'C21 H18 N2'
_chemical_formula_weight         298.37
_chemical_absolute_configuration ?
_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'

_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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   15.298(2)
_cell_length_b                   17.949(2)
_cell_length_c                   5.9450(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1632.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2414
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.294
_cell_measurement_theta_min      3.500
_shelx_estimated_absorpt_T_max   1.000
_shelx_estimated_absorpt_T_min   0.993
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.60a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1515
_diffrn_reflns_av_unetI/netI     0.1374
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            25379
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         28.212
_diffrn_reflns_theta_min         2.895
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Hybrid Pixel Array Detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_source                   ?
_reflns_Friedel_coverage         0.801
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                1960
_reflns_number_total             3908
_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         0.190
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 515 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3908
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2102
_refine_ls_R_factor_gt           0.1089
_refine_ls_restrained_S_all      1.088
_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)+(0.0528P)²+0.5701P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1572
_refine_ls_wR_factor_ref         0.1877
_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:
 C005(H005), C007(H007), C009(H009), C00B(H00B), C00C(H00C), C00F(H00F),
 C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00M(H00M)
2.b Idealised Me refined as rotating group:
 C00L(H00A,H00D,H00E), C00N(H00L,H00N,H00O)
;
_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
N001 N 0.7151(3) 0.6593(3) 0.4862(10) 0.0421(13) Uani 1 1 d . . . . .
N002 N 0.8015(3) 0.5640(3) 0.5854(11) 0.0507(16) Uani 1 1 d . . . . .
C003 C 0.7809(4) 0.6336(3) 0.6259(11) 0.0391(16) Uani 1 1 d . . . . .
C004 C 0.6712(4) 0.7302(3) 0.4867(12) 0.0360(14) Uani 1 1 d . . . . .
C005 C 0.6342(4) 0.5943(3) 0.1662(11) 0.0455(18) Uani 1 1 d . . . . .
H005 H 0.597223 0.633538 0.128727 0.055 Uiso 1 1 calc R . . . .
C006 C 0.8250(4) 0.6797(4) 0.7962(12) 0.0411(17) Uani 1 1 d . . . . .
C007 C 0.6815(4) 0.7783(3) 0.3141(12) 0.0450(17) Uani 1 1 d . . . . .
H007 H 0.716250 0.765508 0.191675 0.054 Uiso 1 1 calc R . . . .
C008 C 0.6941(4) 0.6008(3) 0.3455(12) 0.0384(17) Uani 1 1 d . . . . .
C009 C 0.8415(4) 0.7548(4) 0.7699(12) 0.053(2) Uani 1 1 d . . . . .
H009 H 0.821959 0.778683 0.640624 0.064 Uiso 1 1 calc R . . . .
C00A C 0.5887(4) 0.8684(3) 0.4998(14) 0.0467(17) Uani 1 1 d . . . . .
C00B C 0.6183(4) 0.7493(4) 0.6667(13) 0.0515(19) Uani 1 1 d . . . . .
H00B H 0.610121 0.715660 0.783860 0.062 Uiso 1 1 calc R . . . .
C00C C 0.5778(4) 0.8177(4) 0.6729(14) 0.053(2) Uani 1 1 d . . . . .
H00C H 0.542617 0.830086 0.794980 0.064 Uiso 1 1 calc R . . . .
C00D C 0.6320(5) 0.5283(4) 0.0480(13) 0.055(2) Uani 1 1 d . . . . .
C00E C 0.7483(4) 0.5425(4) 0.4101(12) 0.0451(17) Uani 1 1 d . . . . .
C00F C 0.6397(4) 0.8475(4) 0.3211(13) 0.0508(19) Uani 1 1 d . . . . .
H00F H 0.646576 0.880246 0.201126 0.061 Uiso 1 1 calc R . . . .
C00G C 0.9000(4) 0.6855(5) 1.1524(14) 0.061(2) Uani 1 1 d . . . . .
H00G H 0.919355 0.661950 1.282503 0.073 Uiso 1 1 calc R . . . .
C00H C 0.8862(5) 0.7952(4) 0.9292(14) 0.064(2) Uani 1 1 d . . . . .
H00H H 0.896296 0.845776 0.907438 0.077 Uiso 1 1 calc R . . . .
C00I C 0.7435(5) 0.4753(4) 0.2896(14) 0.058(2) Uani 1 1 d . . . . .
H00I H 0.778777 0.435218 0.329013 0.069 Uiso 1 1 calc R . . . .
C00J C 0.8551(4) 0.6453(4) 0.9899(12) 0.0498(18) Uani 1 1 d . . . . .
H00J H 0.845077 0.594718 1.011302 0.060 Uiso 1 1 calc R . . . .
C00K C 0.6867(5) 0.4697(4) 0.1151(15) 0.066(2) Uani 1 1 d . . . . .
H00K H 0.683996 0.424933 0.036468 0.080 Uiso 1 1 calc R . . . .
C00L C 0.5457(5) 0.9436(3) 0.5116(17) 0.073(3) Uani 1 1 d . . . . .
H00A H 0.483727 0.937479 0.528217 0.110 Uiso 1 1 calc GR . . . .
H00D H 0.557692 0.970786 0.375906 0.110 Uiso 1 1 calc GR . . . .
H00E H 0.568330 0.970684 0.638177 0.110 Uiso 1 1 calc GR . . . .
C00M C 0.9160(4) 0.7605(5) 1.1212(14) 0.063(2) Uani 1 1 d . . . . .
H00M H 0.946621 0.787415 1.229088 0.075 Uiso 1 1 calc R . . . .
C00N C 0.5716(5) 0.5189(5) -0.1472(14) 0.077(3) Uani 1 1 d . . . . .
H00L H 0.538540 0.563816 -0.168333 0.115 Uiso 1 1 calc GR . . . .
H00N H 0.532457 0.478207 -0.118474 0.115 Uiso 1 1 calc GR . . . .
H00O H 0.605007 0.508669 -0.280413 0.115 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
N001 C003 1.384(7) . ?
N001 C004 1.439(7) . ?
N001 C008 1.380(8) . ?
N002 C003 1.310(7) . ?
N002 C00E 1.378(9) . ?
C003 C006 1.472(9) . ?
C004 C007 1.350(8) . ?
C004 C00B 1.384(9) . ?
C005 C008 1.410(9) . ?
C005 C00D 1.379(8) . ?
C006 C009 1.380(8) . ?
C006 C00J 1.385(9) . ?
C007 C00F 1.398(8) . ?
C008 C00E 1.389(8) . ?
C009 C00H 1.375(9) . ?
C00A C00C 1.383(9) . ?
C00A C00F 1.370(10) . ?
C00A C00L 1.504(8) . ?
C00B C00C 1.377(8) . ?
C00D C00K 1.402(10) . ?
C00D C00N 1.493(10) . ?
C00E C00I 1.404(9) . ?
C00G C00J 1.388(10) . ?
C00G C00M 1.380(10) . ?
C00H C00M 1.378(10) . ?
C00I C00K 1.357(10) . ?

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
C003 N001 C004 129.3(6) . . ?
C008 N001 C003 106.2(5) . . ?
C008 N001 C004 124.4(5) . . ?
C003 N002 C00E 105.3(6) . . ?
N001 C003 C006 123.9(5) . . ?
N002 C003 N001 112.5(6) . . ?
N002 C003 C006 123.5(6) . . ?
C007 C004 N001 120.6(6) . . ?
C007 C004 C00B 119.9(6) . . ?
C00B C004 N001 119.5(6) . . ?
C00D C005 C008 118.1(6) . . ?
C009 C006 C003 123.7(6) . . ?
C009 C006 C00J 117.9(7) . . ?
C00J C006 C003 118.3(6) . . ?
C004 C007 C00F 119.5(7) . . ?
N001 C008 C005 132.2(6) . . ?
N001 C008 C00E 105.5(6) . . ?
C00E C008 C005 122.3(7) . . ?
C00H C009 C006 121.9(7) . . ?
C00C C00A C00L 120.2(7) . . ?
C00F C00A C00C 117.8(6) . . ?
C00F C00A C00L 122.1(7) . . ?
C00C C00B C004 120.3(7) . . ?
C00B C00C C00A 120.8(7) . . ?
C005 C00D C00K 119.1(7) . . ?
C005 C00D C00N 120.5(7) . . ?
C00K C00D C00N 120.4(7) . . ?
N002 C00E C008 110.5(6) . . ?
N002 C00E C00I 131.1(7) . . ?
C008 C00E C00I 118.3(7) . . ?
C00A C00F C007 121.8(7) . . ?
C00M C00G C00J 120.1(7) . . ?
C009 C00H C00M 119.7(8) . . ?
C00K C00I C00E 119.2(7) . . ?
C006 C00J C00G 120.8(7) . . ?
C00I C00K C00D 122.9(7) . . ?
C00H C00M C00G 119.6(8) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
