# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 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_1
_audit_block_doi                 10.5517/ccdc.csd.cc2dqm4x
_database_code_depnum_ccdc_archive 'CCDC 2226269'
loop_
_audit_author_name
_audit_author_address
'Sheng xiang Gao'
;Jilin University
China
;
_audit_update_record             
;
2022-12-13 deposited with the CCDC.	2023-04-13 downloaded from the CCDC.
;
_audit_creation_date             2022-08-06
_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            VR-1
_chemical_name_systematic        3-methyl-1,5,6-triphenylverdazyl
_chemical_formula_moiety         'C21 H19 N4'
_chemical_formula_sum            'C21 H19 N4'
_chemical_formula_weight         327.40
_chemical_absolute_configuration ad
_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           36
_space_group_name_H-M_alt        'C m c 21'
_space_group_name_Hall           'C 2c -2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   18.2181(13)
_cell_length_b                   11.9406(13)
_cell_length_c                   8.1125(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1764.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7016
_cell_measurement_temperature    259
_cell_measurement_theta_max      27.27
_cell_measurement_theta_min      3.23
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  1
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ABSAD
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0729
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            23704
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         3.235
_diffrn_ambient_temperature      259.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                1724
_reflns_number_total             2099
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 685 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.3(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2099
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0476P)²+0.0259P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0848
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_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
N1 N 0.43646(9) 0.22311(12) 0.74714(17) 0.0354(4) Uani 1 1 d . . . . .
C2 C 0.500000 0.2859(2) 0.8040(3) 0.0323(5) Uani 1 2 d S T P . .
N3 N 0.43457(9) 0.11134(12) 0.77987(19) 0.0398(4) Uani 1 1 d . . . . .
C4 C 0.37616(10) 0.27059(16) 0.6656(2) 0.0354(4) Uani 1 1 d . . . . .
C5 C 0.32992(12) 0.2023(2) 0.5714(3) 0.0449(5) Uani 1 1 d . . . . .
C6 C 0.36150(11) 0.38458(18) 0.6774(3) 0.0443(5) Uani 1 1 d . . . . .
C7 C 0.500000 0.0649(2) 0.8067(3) 0.0394(6) Uani 1 2 d S T P . .
C8 C 0.43483(14) 0.34262(19) 1.2419(3) 0.0503(5) Uani 1 1 d . . . . .
C9 C 0.500000 -0.0563(3) 0.8535(5) 0.0570(9) Uani 1 2 d S T P . .
C10 C 0.43442(11) 0.31596(18) 1.0751(3) 0.0431(5) Uani 1 1 d . . . . .
C11 C 0.500000 0.3037(2) 0.9895(3) 0.0327(6) Uani 1 2 d S T P . .
C12 C 0.30131(13) 0.4293(2) 0.5962(3) 0.0557(6) Uani 1 1 d . . . . .
C13 C 0.27036(12) 0.2492(2) 0.4920(3) 0.0572(6) Uani 1 1 d . . . . .
C14 C 0.25532(13) 0.3620(2) 0.5035(3) 0.0622(7) Uani 1 1 d . . . . .
C15 C 0.500000 0.3561(3) 1.3238(4) 0.0512(8) Uani 1 2 d S T P . .
H2 H 0.500000 0.361(2) 0.746(3) 0.029(7) Uiso 1 2 d S T P . .
H6 H 0.3908(13) 0.4347(19) 0.746(3) 0.051(6) Uiso 1 1 d . . . . .
H15 H 0.500000 0.370(3) 1.436(5) 0.063(10) Uiso 1 2 d S T P . .
H9A H 0.5454(19) -0.090(3) 0.823(5) 0.110(11) Uiso 1 1 d . . . . .
H8 H 0.3871(15) 0.352(2) 1.301(4) 0.063(7) Uiso 1 1 d . . . . .
H5 H 0.3428(12) 0.123(2) 0.563(3) 0.048(6) Uiso 1 1 d . . . . .
H10 H 0.3882(14) 0.3026(16) 1.016(3) 0.047(6) Uiso 1 1 d . . . . .
H12 H 0.2903(13) 0.504(3) 0.608(3) 0.060(7) Uiso 1 1 d . . . . .
H14 H 0.2141(15) 0.392(2) 0.445(4) 0.074(8) Uiso 1 1 d . . . . .
H13 H 0.2400(18) 0.200(2) 0.428(5) 0.084(9) Uiso 1 1 d . . . . .
H9B H 0.500000 -0.060(4) 0.970(9) 0.122(18) Uiso 1 2 d S T P . .


_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
N1 C2 1.454(2) . ?
N1 N3 1.361(2) . ?
N1 C4 1.402(2) . ?
C2 C11 1.520(4) . ?
N3 C7 1.333(2) . ?
C4 C5 1.399(3) . ?
C4 C6 1.390(3) . ?
C5 C13 1.380(3) . ?
C6 C12 1.386(3) . ?
C7 C9 1.496(4) . ?
C8 C10 1.390(3) . ?
C8 C15 1.370(3) . ?
C10 C11 1.390(2) . ?
C12 C14 1.383(4) . ?
C13 C14 1.378(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
N3 N1 C2 117.63(16) . . ?
N3 N1 C4 117.95(15) . . ?
C4 N1 C2 124.39(16) . . ?
N1 C2 N1 105.5(2) . 3_655 ?
N1 C2 C11 112.74(14) . . ?
N1 C2 C11 112.74(14) 3_655 . ?
C7 N3 N1 114.65(16) . . ?
C5 C4 N1 119.60(18) . . ?
C6 C4 N1 120.91(17) . . ?
C6 C4 C5 119.49(18) . . ?
C13 C5 C4 119.5(2) . . ?
C12 C6 C4 119.8(2) . . ?
N3 C7 N3 126.9(2) 3_655 . ?
N3 C7 C9 116.35(11) . . ?
N3 C7 C9 116.35(11) 3_655 . ?
C15 C8 C10 120.2(2) . . ?
C11 C10 C8 120.4(2) . . ?
C10 C11 C2 120.63(12) 3_655 . ?
C10 C11 C2 120.63(12) . . ?
C10 C11 C10 118.6(2) . 3_655 ?
C14 C12 C6 120.9(2) . . ?
C14 C13 C5 121.4(2) . . ?
C13 C14 C12 119.0(2) . . ?
C8 C15 C8 120.1(3) 3_655 . ?

_olex2_submission_special_instructions 'No special instructions were received'
