# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_ic20904
_audit_block_doi                 10.5517/ccdc.csd.cc2fj4ch
_database_code_depnum_ccdc_archive 'CCDC 2249836'
loop_
_audit_author_name
_audit_author_address
'Kai-Hsin Chang'
;National Taiwan University
Taiwan
;
_audit_update_record             
;
2023-03-19 deposited with the CCDC.	2023-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8 N2'
_chemical_formula_weight         168.19

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.7781(2)
_cell_length_b                   10.1450(4)
_cell_length_c                   14.0978(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     826.40(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    8321
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      30.01

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.079
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8198
_exptl_absorpt_correction_T_max  0.9602
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15065
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.473
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2423
_reflns_number_gt                2235
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'Bruker SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0547P)²+0.1496P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 864 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.4(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2423
_refine_ls_number_parameters     122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1111
_refine_ls_wR_factor_gt          0.1069
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.2372(3) 0.94471(16) 0.29335(11) 0.0342(4) Uani 1 1 d . . . . .
H1 H 0.131(5) 0.963(3) 0.250(2) 0.054(7) Uiso 1 1 d . . . . .
C2 C 0.4168(3) 1.0271(2) 0.31803(13) 0.0369(4) Uani 1 1 d . . . . .
H2 H 0.426892 1.117323 0.300562 0.044 Uiso 1 1 calc R U . . .
C3 C 0.5779(3) 0.9621(2) 0.37073(13) 0.0379(4) Uani 1 1 d . . . . .
H3 H 0.714933 0.998364 0.397355 0.045 Uiso 1 1 calc R U . . .
C4 C 0.5861(3) 0.7141(2) 0.41941(12) 0.0341(4) Uani 1 1 d . . . . .
H4 H 0.728269 0.716687 0.453236 0.041 Uiso 1 1 calc R U . . .
C5 C 0.5472(4) 0.4741(2) 0.44768(13) 0.0390(4) Uani 1 1 d . . . . .
H5 H 0.689783 0.471645 0.481195 0.047 Uiso 1 1 calc R U . . .
C6 C 0.4239(4) 0.3618(2) 0.43475(14) 0.0424(5) Uani 1 1 d . . . . .
H6 H 0.479517 0.280173 0.458655 0.051 Uiso 1 1 calc R U . . .
C7 C 0.2125(4) 0.3678(2) 0.38549(14) 0.0397(5) Uani 1 1 d . . . . .
H7 H 0.128884 0.288009 0.377057 0.048 Uiso 1 1 calc R U . . .
N8 N 0.1232(3) 0.47621(17) 0.35041(11) 0.0344(4) Uani 1 1 d . . . . .
C9 C 0.1559(3) 0.70648(18) 0.32042(12) 0.0302(4) Uani 1 1 d . . . . .
H9 H 0.011814 0.705525 0.287987 0.036 Uiso 1 1 calc R U . . .
C10 C 0.2827(3) 0.82114(19) 0.32831(11) 0.0298(4) Uani 1 1 d . . . . .
C11 C 0.4996(3) 0.8274(2) 0.37821(12) 0.0311(4) Uani 1 1 d . . . . .
C12 C 0.4632(3) 0.59478(19) 0.41115(12) 0.0317(4) Uani 1 1 d . . . . .
C13 C 0.2451(3) 0.59156(18) 0.36144(11) 0.0290(3) 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
N1 C10 1.372(2) . ?
N1 C2 1.377(3) . ?
C2 C3 1.361(3) . ?
C3 C11 1.444(3) . ?
C4 C11 1.381(3) . ?
C4 C12 1.409(3) . ?
C5 C6 1.356(3) . ?
C5 C12 1.415(3) . ?
C6 C7 1.406(3) . ?
C7 N8 1.312(3) . ?
N8 C13 1.375(2) . ?
C9 C10 1.379(2) . ?
C9 C13 1.400(2) . ?
C10 C11 1.439(2) . ?
C12 C13 1.442(2) . ?

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
C10 N1 C2 108.62(16) . . ?
C3 C2 N1 111.09(18) . . ?
C2 C3 C11 106.47(17) . . ?
C11 C4 C12 119.86(16) . . ?
C6 C5 C12 119.87(18) . . ?
C5 C6 C7 119.12(19) . . ?
N8 C7 C6 124.34(19) . . ?
C7 N8 C13 118.01(16) . . ?
C10 C9 C13 118.28(15) . . ?
N1 C10 C9 129.78(16) . . ?
N1 C10 C11 107.57(16) . . ?
C9 C10 C11 122.65(16) . . ?
C4 C11 C10 118.94(17) . . ?
C4 C11 C3 134.84(17) . . ?
C10 C11 C3 106.22(17) . . ?
C4 C12 C5 122.75(16) . . ?
C4 C12 C13 120.02(16) . . ?
C5 C12 C13 117.21(17) . . ?
N8 C13 C9 118.28(15) . . ?
N8 C13 C12 121.46(16) . . ?
C9 C13 C12 120.23(16) . . ?

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.036



