# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_NEt2_EtCN2-2
_database_code_depnum_ccdc_archive 'CCDC 2091666'
loop_
_audit_author_name
_audit_author_address
'Kang Mun Lee'
;Kangwon National University
South Korea
;
_audit_update_record             
;
2021-06-23 deposited with the CCDC.	2021-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        2
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C27H31InN6O2
_chemical_formula_sum            'C27 H31 In N6 O2'
_chemical_formula_weight         586.40

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'
In In -0.7276 1.3100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.744(2)
_cell_length_b                   20.929(4)
_cell_length_c                   12.803(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.00(3)
_cell_angle_gamma                90
_cell_volume                     2878.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    27424
_cell_measurement_theta_min      3.149
_cell_measurement_theta_max      27.276

_exptl_crystal_description       block
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    0.853
_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_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27424
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.149
_diffrn_reflns_theta_max         27.276
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6409
_reflns_number_gt                3866
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0900P)²+0.2054P] 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         6409
_refine_ls_number_parameters     330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1557
_refine_ls_wR_factor_gt          0.1263
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
In1 In 0.20612(3) 0.02483(2) 0.60126(2) 0.06333(16) Uani 1 1 d . . . . .
N1 N 0.1642(3) -0.07103(14) 0.5214(2) 0.0611(8) Uani 1 1 d . . . . .
N2 N 0.1824(3) 0.04422(16) 0.4270(2) 0.0612(8) Uani 1 1 d . . . . .
N3 N 0.0271(4) -0.16447(18) 1.0008(3) 0.0840(11) Uani 1 1 d . . . . .
N4 N 0.1028(4) 0.34134(16) 0.5779(3) 0.0881(13) Uani 1 1 d . . . . .
N5 N 0.2007(5) -0.17489(19) 0.3068(3) 0.0949(13) Uani 1 1 d . . . . .
N6 N 0.2389(5) 0.0005(2) 0.1654(3) 0.0946(14) Uani 1 1 d . . . . .
O1 O 0.0904(3) -0.01678(12) 0.7196(2) 0.0742(9) Uani 1 1 d . . . . .
O2 O 0.1113(3) 0.11397(12) 0.6129(2) 0.0705(8) Uani 1 1 d . . . . .
C1 C 0.4024(7) 0.0328(3) 0.6403(6) 0.126(2) Uani 1 1 d . . . . .
H24A H 0.4359 0.0710 0.6097 0.189 Uiso 1 1 calc R U . . .
H24B H 0.4463 -0.0037 0.6137 0.189 Uiso 1 1 calc R U . . .
H24C H 0.4118 0.0347 0.7148 0.189 Uiso 1 1 calc R U . . .
C2 C 0.0913(4) -0.07694(19) 0.7512(3) 0.0630(10) Uani 1 1 d . . . . .
C3 C 0.1179(4) -0.13063(18) 0.6806(3) 0.0632(10) Uani 1 1 d . . . . .
C4 C 0.1083(4) -0.1930(2) 0.7240(4) 0.0759(12) Uani 1 1 d . . . . .
H4 H 0.1225 -0.2277 0.6801 0.091 Uiso 1 1 calc R U . . .
C5 C 0.0794(5) -0.2053(2) 0.8267(4) 0.0792(13) Uani 1 1 d . . . . .
H3 H 0.0766 -0.2471 0.8510 0.095 Uiso 1 1 calc R U . . .
C6 C 0.0535(4) -0.1527(2) 0.8966(3) 0.0717(12) Uani 1 1 d . . . . .
C7 C 0.0576(4) -0.09023(19) 0.8560(3) 0.0662(11) Uani 1 1 d . . . . .
H1 H 0.0375 -0.0563 0.8997 0.079 Uiso 1 1 calc R U . . .
C8 C 0.1428(4) -0.12464(19) 0.5725(3) 0.0622(10) Uani 1 1 d . . . . .
H14 H 0.1442 -0.1622 0.5337 0.075 Uiso 1 1 calc R U . . .
C9 C 0.1290(4) 0.16457(17) 0.5522(3) 0.0596(10) Uani 1 1 d . . . . .
C10 C 0.1061(4) 0.22527(18) 0.5934(3) 0.0684(11) Uani 1 1 d . . . . .
H8 H 0.0814 0.2283 0.6628 0.082 Uiso 1 1 calc R U . . .
C11 C 0.1187(4) 0.28251(18) 0.5348(3) 0.0672(11) Uani 1 1 d . . . . .
C12 C 0.1529(4) 0.2770(2) 0.4268(3) 0.0708(11) Uani 1 1 d . . . . .
H10 H 0.1606 0.3134 0.3857 0.085 Uiso 1 1 calc R U . . .
C13 C 0.1743(4) 0.21800(19) 0.3843(3) 0.0658(11) Uani 1 1 d . . . . .
H11 H 0.1961 0.2158 0.3141 0.079 Uiso 1 1 calc R U . . .
C14 C 0.1653(4) 0.15955(17) 0.4416(3) 0.0574(9) Uani 1 1 d . . . . .
C15 C 0.1822(4) 0.10243(19) 0.3861(3) 0.0614(10) Uani 1 1 d . . . . .
H15 H 0.1943 0.1057 0.3143 0.074 Uiso 1 1 calc R U . . .
C16 C 0.1827(4) -0.06924(19) 0.4128(3) 0.0620(10) Uani 1 1 d . . . . .
C17 C 0.1928(4) -0.01069(18) 0.3652(3) 0.0602(10) Uani 1 1 d . . . . .
C18 C -0.0085(6) -0.1119(3) 1.0752(4) 0.0948(16) Uani 1 1 d . . . . .
H18A H 0.0414 -0.0746 1.0593 0.114 Uiso 1 1 calc R U . . .
H18B H 0.0125 -0.1254 1.1455 0.114 Uiso 1 1 calc R U . . .
C19 C -0.1446(6) -0.0927(3) 1.0733(5) 0.121(2) Uani 1 1 d . . . . .
H19A H -0.1676 -0.0806 1.0036 0.182 Uiso 1 1 calc R U . . .
H19B H -0.1574 -0.0573 1.1197 0.182 Uiso 1 1 calc R U . . .
H19C H -0.1949 -0.1281 1.0954 0.182 Uiso 1 1 calc R U . . .
C20 C 0.0175(6) -0.2302(3) 1.0423(4) 0.1007(18) Uani 1 1 d . . . . .
H16A H 0.0289 -0.2291 1.1175 0.121 Uiso 1 1 calc R U . . .
H16B H 0.0838 -0.2559 1.0129 0.121 Uiso 1 1 calc R U . . .
C21 C -0.1072(6) -0.2616(3) 1.0178(6) 0.142(3) Uani 1 1 d . . . . .
H17A H -0.1732 -0.2371 1.0487 0.212 Uiso 1 1 calc R U . . .
H17B H -0.1082 -0.3042 1.0457 0.212 Uiso 1 1 calc R U . . .
H17C H -0.1187 -0.2633 0.9434 0.212 Uiso 1 1 calc R U . . .
C22 C 0.0785(6) 0.3501(2) 0.6933(5) 0.1092(19) Uani 1 1 d . . . . .
H22A H 0.1196 0.3166 0.7326 0.131 Uiso 1 1 calc R U . . .
H22B H 0.1113 0.3910 0.7162 0.131 Uiso 1 1 calc R U . . .
C23 C -0.0539(7) 0.3477(3) 0.7115(7) 0.148(3) Uani 1 1 d . . . . .
H23A H -0.0938 0.3818 0.6742 0.221 Uiso 1 1 calc R U . . .
H23B H -0.0701 0.3523 0.7849 0.221 Uiso 1 1 calc R U . . .
H23C H -0.0861 0.3075 0.6877 0.221 Uiso 1 1 calc R U . . .
C24 C 0.1144(5) 0.4005(2) 0.5155(4) 0.0899(15) Uani 1 1 d . . . . .
H20A H 0.1852 0.3963 0.4689 0.108 Uiso 1 1 calc R U . . .
H20B H 0.1310 0.4360 0.5622 0.108 Uiso 1 1 calc R U . . .
C25 C -0.0003(6) 0.4157(3) 0.4514(5) 0.114(2) Uani 1 1 d . . . . .
H21A H -0.0216 0.3794 0.4091 0.171 Uiso 1 1 calc R U . . .
H21B H 0.0163 0.4517 0.4071 0.171 Uiso 1 1 calc R U . . .
H21C H -0.0683 0.4255 0.4972 0.171 Uiso 1 1 calc R U . . .
C26 C 0.1917(4) -0.1279(2) 0.3518(3) 0.0715(12) Uani 1 1 d . . . . .
C27 C 0.2154(4) -0.0060(2) 0.2529(3) 0.0673(11) 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
In1 O2 2.131(3) . ?
In1 O1 2.145(3) . ?
In1 C1 2.174(7) . ?
In1 N2 2.282(3) . ?
In1 N1 2.297(3) . ?
N1 C8 1.319(5) . ?
N1 C16 1.405(5) . ?
N2 C15 1.326(5) . ?
N2 C17 1.400(5) . ?
N3 C6 1.386(6) . ?
N3 C20 1.478(6) . ?
N3 C18 1.504(6) . ?
N4 C11 1.360(5) . ?
N4 C24 1.478(5) . ?
N4 C22 1.511(7) . ?
N5 C26 1.144(5) . ?
N6 C27 1.156(5) . ?
O1 C2 1.322(4) . ?
O2 C9 1.328(4) . ?
C2 C7 1.417(6) . ?
C2 C3 1.470(6) . ?
C3 C8 1.415(6) . ?
C3 C4 1.422(6) . ?
C4 C5 1.376(6) . ?
C5 C6 1.446(6) . ?
C6 C7 1.407(6) . ?
C9 C10 1.397(5) . ?
C9 C14 1.471(5) . ?
C10 C11 1.420(5) . ?
C11 C12 1.437(6) . ?
C12 C13 1.368(5) . ?
C13 C14 1.430(5) . ?
C14 C15 1.403(5) . ?
C16 C17 1.373(5) . ?
C16 C26 1.458(5) . ?
C17 C27 1.462(6) . ?
C18 C19 1.516(8) . ?
C20 C21 1.525(8) . ?
C22 C23 1.443(9) . ?
C24 C25 1.515(8) . ?

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
O2 In1 O1 91.66(10) . . ?
O2 In1 C1 112.35(19) . . ?
O1 In1 C1 115.5(2) . . ?
O2 In1 N2 81.91(11) . . ?
O1 In1 N2 134.29(13) . . ?
C1 In1 N2 108.6(2) . . ?
O2 In1 N1 134.61(12) . . ?
O1 In1 N1 81.15(11) . . ?
C1 In1 N1 111.1(2) . . ?
N2 In1 N1 72.43(11) . . ?
C8 N1 C16 122.6(3) . . ?
C8 N1 In1 123.8(2) . . ?
C16 N1 In1 112.9(2) . . ?
C15 N2 C17 122.1(3) . . ?
C15 N2 In1 123.4(2) . . ?
C17 N2 In1 113.4(3) . . ?
C6 N3 C20 121.8(4) . . ?
C6 N3 C18 122.1(4) . . ?
C20 N3 C18 115.7(4) . . ?
C11 N4 C24 121.9(4) . . ?
C11 N4 C22 121.9(4) . . ?
C24 N4 C22 116.2(4) . . ?
C2 O1 In1 126.8(3) . . ?
C9 O2 In1 126.1(2) . . ?
O1 C2 C7 118.3(4) . . ?
O1 C2 C3 122.8(3) . . ?
C7 C2 C3 118.8(4) . . ?
C8 C3 C4 118.5(4) . . ?
C8 C3 C2 124.8(4) . . ?
C4 C3 C2 116.6(4) . . ?
C5 C4 C3 124.1(4) . . ?
C4 C5 C6 119.5(4) . . ?
N3 C6 C7 121.9(4) . . ?
N3 C6 C5 119.9(4) . . ?
C7 C6 C5 118.2(4) . . ?
C6 C7 C2 122.7(4) . . ?
N1 C8 C3 126.4(4) . . ?
O2 C9 C10 118.6(3) . . ?
O2 C9 C14 123.0(3) . . ?
C10 C9 C14 118.3(3) . . ?
C9 C10 C11 123.4(4) . . ?
N4 C11 C10 122.6(4) . . ?
N4 C11 C12 119.7(4) . . ?
C10 C11 C12 117.7(3) . . ?
C13 C12 C11 119.9(4) . . ?
C12 C13 C14 123.8(4) . . ?
C15 C14 C13 117.4(3) . . ?
C15 C14 C9 125.7(3) . . ?
C13 C14 C9 116.8(3) . . ?
N2 C15 C14 125.6(3) . . ?
C17 C16 N1 118.3(3) . . ?
C17 C16 C26 120.5(4) . . ?
N1 C16 C26 121.1(4) . . ?
C16 C17 N2 118.4(3) . . ?
C16 C17 C27 120.7(3) . . ?
N2 C17 C27 120.9(4) . . ?
N3 C18 C19 115.4(5) . . ?
N3 C20 C21 112.8(5) . . ?
C23 C22 N4 109.0(6) . . ?
N4 C24 C25 113.6(5) . . ?
N5 C26 C16 177.6(5) . . ?
N6 C27 C17 175.8(5) . . ?

_refine_diff_density_max         0.520
_refine_diff_density_min         -0.730
_refine_diff_density_rms         0.080

_shelxl_version_number           2013-4

