# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_wrm-1
_database_code_depnum_ccdc_archive 'CCDC 2119650'
loop_
_audit_author_name
_audit_author_address
'Wang Wang'
;Shandong University, Weihai,
China
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2022-03-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 N2'
_chemical_formula_weight         362.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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                   9.1788(6)
_cell_length_b                   9.5316(6)
_cell_length_c                   12.5301(9)
_cell_angle_alpha                70.240(6)
_cell_angle_beta                 75.746(6)
_cell_angle_gamma                83.129(5)
_cell_volume                     999.12(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4696
_cell_measurement_theta_min      4.9610
_cell_measurement_theta_max      70.3450

_exptl_crystal_description       bloc
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.540
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8074
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.843
_diffrn_reflns_theta_max         70.990
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3755
_reflns_number_gt                3176
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1017P)²+0.2260P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3755
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1812
_refine_ls_wR_factor_gt          0.1708
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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
C1 C 0.68655(18) 0.65517(17) 0.15183(14) 0.0466(4) Uani 1 1 d . . . . .
C2 C 0.53166(18) 0.61274(17) 0.22280(14) 0.0450(4) Uani 1 1 d . . . . .
C3 C 0.48754(18) 0.47061(18) 0.27147(15) 0.0477(4) Uani 1 1 d . . . . .
C4 C 0.7309(2) 0.3272(2) 0.29923(16) 0.0538(4) Uani 1 1 d . . . . .
H4 H 0.759309 0.402171 0.321041 0.065 Uiso 1 1 calc R U . . .
C5 C 0.32915(19) 0.43226(19) 0.33216(15) 0.0501(4) Uani 1 1 d . . . . .
C6 C 0.7711(2) 0.7360(2) 0.18726(18) 0.0566(4) Uani 1 1 d . . . . .
H6 H 0.730179 0.760694 0.254556 0.068 Uiso 1 1 calc R U . . .
C7 C 0.2087(2) 0.5041(2) 0.28463(17) 0.0551(4) Uani 1 1 d . . . . .
H7 H 0.226300 0.580218 0.213642 0.066 Uiso 1 1 calc R U . . .
C8 C 0.5935(2) 0.34039(17) 0.26869(15) 0.0498(4) Uani 1 1 d . . . . .
N9 N 0.6653(2) 0.5520(2) 0.00422(16) 0.0786(6) Uani 1 1 d . . . . .
H9A H 0.702272 0.537780 -0.061560 0.094 Uiso 1 1 calc R U . . .
H9B H 0.576504 0.523422 0.042148 0.094 Uiso 1 1 calc R U . . .
C10 C 0.42995(18) 0.74153(18) 0.24018(15) 0.0490(4) Uani 1 1 d . . . . .
C11 C 0.7490(2) 0.62096(19) 0.04913(16) 0.0554(4) Uani 1 1 d . . . . .
N12 N 0.4004(3) 0.8219(3) 0.04468(19) 0.0941(7) Uani 1 1 d . . . . .
H12A H 0.449122 0.742525 0.035293 0.113 Uiso 1 1 calc R U . . .
H12B H 0.367091 0.886318 -0.011822 0.113 Uiso 1 1 calc R U . . .
C13 C 0.3897(2) 0.7622(2) 0.34899(19) 0.0637(5) Uani 1 1 d . . . . .
H13 H 0.422777 0.692207 0.411425 0.076 Uiso 1 1 calc R U . . .
C14 C 0.3762(2) 0.8455(2) 0.14827(18) 0.0617(5) Uani 1 1 d . . . . .
C15 C 0.8263(2) 0.2033(2) 0.29759(18) 0.0660(5) Uani 1 1 d . . . . .
H15 H 0.918260 0.196110 0.318116 0.079 Uiso 1 1 calc R U . . .
C16 C 0.9742(2) 0.7450(2) 0.0257(2) 0.0750(6) Uani 1 1 d . . . . .
H16 H 1.070589 0.773742 -0.016148 0.090 Uiso 1 1 calc R U . . .
C17 C 0.9135(2) 0.7805(2) 0.1257(2) 0.0713(6) Uani 1 1 d . . . . .
H17 H 0.968012 0.833938 0.151502 0.086 Uiso 1 1 calc R U . . .
C18 C 0.8930(2) 0.6672(2) -0.01249(18) 0.0688(6) Uani 1 1 d . . . . .
H18 H 0.934746 0.644938 -0.080728 0.083 Uiso 1 1 calc R U . . .
C19 C 0.0636(2) 0.4650(3) 0.3402(2) 0.0733(6) Uani 1 1 d . . . . .
H19 H -0.015656 0.514621 0.306528 0.088 Uiso 1 1 calc R U . . .
C20 C 0.2980(3) 0.3176(2) 0.43694(19) 0.0713(6) Uani 1 1 d . . . . .
H20 H 0.376593 0.265167 0.470230 0.086 Uiso 1 1 calc R U . . .
C21 C 0.5527(3) 0.2239(2) 0.2394(2) 0.0684(6) Uani 1 1 d . . . . .
H21 H 0.459739 0.228941 0.220873 0.082 Uiso 1 1 calc R U . . .
C22 C 0.3021(3) 0.8840(3) 0.3659(3) 0.0853(8) Uani 1 1 d . . . . .
H22 H 0.278643 0.897439 0.438434 0.102 Uiso 1 1 calc R U . . .
C23 C 0.7864(3) 0.0916(2) 0.26608(19) 0.0715(6) Uani 1 1 d . . . . .
H23 H 0.851808 0.009710 0.263791 0.086 Uiso 1 1 calc R U . . .
C24 C 0.2855(3) 0.9674(2) 0.1676(3) 0.0864(8) Uani 1 1 d . . . . .
H24 H 0.248836 1.037233 0.106938 0.104 Uiso 1 1 calc R U . . .
C25 C 0.0346(3) 0.3535(3) 0.4451(2) 0.0812(7) Uani 1 1 d . . . . .
H25 H -0.063902 0.328241 0.483330 0.097 Uiso 1 1 calc R U . . .
C26 C 0.1510(3) 0.2804(3) 0.4925(2) 0.0851(7) Uani 1 1 d . . . . .
H26 H 0.131979 0.204102 0.563385 0.102 Uiso 1 1 calc R U . . .
C27 C 0.6491(3) 0.1012(2) 0.2378(2) 0.0768(6) Uani 1 1 d . . . . .
H27 H 0.620973 0.024717 0.217490 0.092 Uiso 1 1 calc R U . . .
C28 C 0.2504(3) 0.9843(3) 0.2755(3) 0.0945(9) Uani 1 1 d . . . . .
H28 H 0.190105 1.065852 0.287012 0.113 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
C1 C6 1.391(2) . ?
C1 C11 1.402(2) . ?
C1 C2 1.499(2) . ?
C2 C3 1.350(2) . ?
C2 C10 1.494(2) . ?
C3 C8 1.487(2) . ?
C3 C5 1.490(2) . ?
C4 C8 1.385(2) . ?
C4 C15 1.386(3) . ?
C5 C7 1.383(3) . ?
C5 C20 1.385(3) . ?
C6 C17 1.378(3) . ?
C7 C19 1.372(3) . ?
C8 C21 1.396(3) . ?
N9 C11 1.386(3) . ?
C10 C14 1.393(3) . ?
C10 C13 1.397(3) . ?
C11 C18 1.395(3) . ?
N12 C14 1.352(3) . ?
C13 C22 1.378(3) . ?
C14 C24 1.401(3) . ?
C15 C23 1.368(3) . ?
C16 C18 1.372(3) . ?
C16 C17 1.377(3) . ?
C19 C25 1.371(3) . ?
C20 C26 1.384(3) . ?
C21 C27 1.383(3) . ?
C22 C28 1.359(4) . ?
C23 C27 1.376(4) . ?
C24 C28 1.369(4) . ?
C25 C26 1.355(4) . ?

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
C6 C1 C11 118.22(16) . . ?
C6 C1 C2 118.74(15) . . ?
C11 C1 C2 123.01(15) . . ?
C3 C2 C10 122.00(15) . . ?
C3 C2 C1 123.71(15) . . ?
C10 C2 C1 114.24(13) . . ?
C2 C3 C8 122.49(15) . . ?
C2 C3 C5 122.59(15) . . ?
C8 C3 C5 114.92(14) . . ?
C8 C4 C15 120.59(18) . . ?
C7 C5 C20 117.48(17) . . ?
C7 C5 C3 121.91(15) . . ?
C20 C5 C3 120.55(16) . . ?
C17 C6 C1 122.06(19) . . ?
C19 C7 C5 121.24(18) . . ?
C4 C8 C21 118.14(17) . . ?
C4 C8 C3 121.90(15) . . ?
C21 C8 C3 119.90(16) . . ?
C14 C10 C13 118.52(18) . . ?
C14 C10 C2 121.10(17) . . ?
C13 C10 C2 120.36(16) . . ?
N9 C11 C18 119.92(18) . . ?
N9 C11 C1 120.80(17) . . ?
C18 C11 C1 119.11(18) . . ?
C22 C13 C10 121.5(2) . . ?
N12 C14 C10 120.29(19) . . ?
N12 C14 C24 120.3(2) . . ?
C10 C14 C24 119.1(2) . . ?
C23 C15 C4 120.7(2) . . ?
C18 C16 C17 120.21(19) . . ?
C16 C17 C6 119.2(2) . . ?
C16 C18 C11 121.22(19) . . ?
C25 C19 C7 120.5(2) . . ?
C26 C20 C5 120.6(2) . . ?
C27 C21 C8 120.7(2) . . ?
C28 C22 C13 119.3(3) . . ?
C15 C23 C27 119.61(19) . . ?
C28 C24 C14 120.4(2) . . ?
C26 C25 C19 119.2(2) . . ?
C25 C26 C20 120.9(2) . . ?
C23 C27 C21 120.3(2) . . ?
C22 C28 C24 121.1(2) . . ?

_refine_diff_density_max         0.405
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.044

