# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_PO19049_029
_database_code_depnum_ccdc_archive 'CCDC 2113438'
loop_
_audit_author_name
_audit_author_address
'Dongwook Kim'
;Institute for Basic Science (IBS)
South Korea
;
_audit_update_record             
;
2021-10-03 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H24 Ir N'
_chemical_formula_weight         458.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0024 0.0013 '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 0.0048 0.0027 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -0.8791 6.9422 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   14.834(3)
_cell_length_b                   8.0960(16)
_cell_length_c                   14.131(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1697.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    45870
_cell_measurement_theta_min      0.372
_cell_measurement_theta_max      34.080

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.042
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.031
_exptl_absorpt_coefficient_mu    6.224
_shelx_estimated_absorpt_T_min   0.780
_shelx_estimated_absorpt_T_max   0.830
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'HKL3000sm Scalepack'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.650
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12196
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.301
_diffrn_reflns_theta_max         23.996
_diffrn_reflns_theta_full        22.955
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3480
_reflns_number_gt                3272
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

_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       'PAL BL2D-SMDC Program'
_computing_cell_refinement       HKL3000sm
_computing_data_reduction        HKL3000sm
_computing_structure_solution    SHELXS
_computing_structure_refinement  SHELXL
_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)+(0.0291P)²] 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 1517 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3480
_refine_ls_number_parameters     202
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0209
_refine_ls_R_factor_gt           0.0193
_refine_ls_wR_factor_ref         0.0497
_refine_ls_wR_factor_gt          0.0492
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_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
Ir1 Ir 0.20671(2) 0.54839(2) 0.49108(6) 0.02563(8) Uani 1 1 d . . . . .
N2 N 0.2456(4) 0.6855(6) 0.3864(4) 0.0309(10) Uani 1 1 d D . . . .
H2 H 0.214(4) 0.667(11) 0.342(4) 0.046 Uiso 1 1 d D U . . .
C3 C 0.3131(4) 0.7986(7) 0.3752(5) 0.0295(13) Uani 1 1 d . . . . .
C4 C 0.3256(5) 0.8708(7) 0.2854(5) 0.0381(13) Uani 1 1 d . . . . .
H4 H 0.286065 0.842155 0.236059 0.046 Uiso 1 1 calc R U . . .
C5 C 0.3935(5) 0.9811(9) 0.2676(6) 0.0479(19) Uani 1 1 d . . . . .
H5 H 0.400515 1.026968 0.206901 0.058 Uiso 1 1 calc R U . . .
C6 C 0.4519(5) 1.0245(7) 0.3407(7) 0.050(2) Uani 1 1 d . . . . .
H6 H 0.499267 1.099160 0.329543 0.060 Uiso 1 1 calc R U . . .
C7 C 0.4403(5) 0.9588(7) 0.4277(7) 0.0430(17) Uani 1 1 d . . . . .
H7 H 0.480037 0.991379 0.476034 0.052 Uiso 1 1 calc R U . . .
C8 C 0.3715(4) 0.8435(7) 0.4503(5) 0.0306(14) Uani 1 1 d . . . . .
C9 C 0.3625(4) 0.7747(7) 0.5437(5) 0.0295(14) Uani 1 1 d . . . . .
C10 C 0.3010(4) 0.6570(9) 0.5672(5) 0.0303(13) Uani 1 1 d . . . . .
H10 H 0.304(4) 0.634(10) 0.624(6) 0.036 Uiso 1 1 d . U . . .
C11 C 0.4273(4) 0.8355(8) 0.6210(5) 0.0437(16) Uani 1 1 d . . . . .
H11A H 0.416270 0.774789 0.679070 0.066 Uiso 1 1 calc R U . . .
H11B H 0.417535 0.952378 0.632046 0.066 Uiso 1 1 calc R U . . .
H11C H 0.489009 0.817660 0.600767 0.066 Uiso 1 1 calc R U . . .
C12 C 0.0744(6) 0.4310(9) 0.4495(7) 0.042(2) Uani 1 1 d . . . . .
C13 C 0.0744(5) 0.4986(8) 0.5455(6) 0.0303(15) Uani 1 1 d . . . . .
C14 C 0.1395(4) 0.4085(7) 0.6016(4) 0.0274(12) Uani 1 1 d . . . . .
C15 C 0.1841(5) 0.2978(7) 0.5394(5) 0.0283(14) Uani 1 1 d . . . . .
C16 C 0.1426(5) 0.3108(9) 0.4473(6) 0.0408(18) Uani 1 1 d . . . . .
C17 C 0.0129(7) 0.4834(12) 0.3722(7) 0.069(3) Uani 1 1 d . . . . .
H17A H 0.046841 0.495181 0.313980 0.103 Uiso 1 1 calc R U . . .
H17B H -0.014543 0.588368 0.388562 0.103 Uiso 1 1 calc R U . . .
H17C H -0.033832 0.400881 0.363725 0.103 Uiso 1 1 calc R U . . .
C18 C 0.0100(4) 0.6238(8) 0.5845(6) 0.0464(17) Uani 1 1 d . . . . .
H18A H -0.042155 0.567888 0.610776 0.070 Uiso 1 1 calc R U . . .
H18B H -0.009249 0.697410 0.534191 0.070 Uiso 1 1 calc R U . . .
H18C H 0.039584 0.687252 0.633707 0.070 Uiso 1 1 calc R U . . .
C19 C 0.1564(6) 0.4267(8) 0.7049(5) 0.0412(15) Uani 1 1 d . . . . .
H19A H 0.116257 0.354161 0.739705 0.062 Uiso 1 1 calc R U . . .
H19B H 0.145470 0.540258 0.723678 0.062 Uiso 1 1 calc R U . . .
H19C H 0.218440 0.397671 0.718784 0.062 Uiso 1 1 calc R U . . .
C20 C 0.2571(5) 0.1757(8) 0.5673(6) 0.055(2) Uani 1 1 d . . . . .
H20A H 0.230816 0.066660 0.574542 0.083 Uiso 1 1 calc R U . . .
H20B H 0.284035 0.209768 0.626712 0.083 Uiso 1 1 calc R U . . .
H20C H 0.303024 0.172509 0.518490 0.083 Uiso 1 1 calc R U . . .
C21 C 0.1703(7) 0.2057(11) 0.3646(6) 0.072(3) Uani 1 1 d . . . . .
H21A H 0.153618 0.091780 0.376460 0.108 Uiso 1 1 calc R U . . .
H21B H 0.235056 0.213149 0.355930 0.108 Uiso 1 1 calc R U . . .
H21C H 0.140123 0.244532 0.307863 0.108 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
Ir1 N2 1.937(5) . ?
Ir1 C10 1.972(6) . ?
Ir1 C13 2.147(7) . ?
Ir1 C15 2.167(6) . ?
Ir1 C14 2.171(6) . ?
Ir1 C16 2.233(7) . ?
Ir1 C12 2.259(8) . ?
N2 C3 1.366(7) . ?
N2 H2 0.79(3) . ?
C3 C4 1.409(9) . ?
C3 C8 1.418(9) . ?
C4 C5 1.369(9) . ?
C4 H4 0.9400 . ?
C5 C6 1.395(13) . ?
C5 H5 0.9400 . ?
C6 C7 1.350(13) . ?
C6 H6 0.9400 . ?
C7 C8 1.419(9) . ?
C7 H7 0.9400 . ?
C8 C9 1.439(8) . ?
C9 C10 1.360(9) . ?
C9 C11 1.537(8) . ?
C10 H10 0.83(9) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 C16 1.405(12) . ?
C12 C13 1.462(10) . ?
C12 C17 1.485(13) . ?
C13 C14 1.447(9) . ?
C13 C18 1.498(9) . ?
C14 C15 1.419(9) . ?
C14 C19 1.490(9) . ?
C15 C16 1.443(9) . ?
C15 C20 1.518(10) . ?
C16 C21 1.503(10) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?

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
N2 Ir1 C10 87.1(3) . . ?
N2 Ir1 C13 130.8(3) . . ?
C10 Ir1 C13 122.5(3) . . ?
N2 Ir1 C15 145.4(2) . . ?
C10 Ir1 C15 110.8(3) . . ?
C13 Ir1 C15 64.5(3) . . ?
N2 Ir1 C14 170.0(2) . . ?
C10 Ir1 C14 99.6(3) . . ?
C13 Ir1 C14 39.2(2) . . ?
C15 Ir1 C14 38.2(2) . . ?
N2 Ir1 C16 114.1(3) . . ?
C10 Ir1 C16 146.8(3) . . ?
C13 Ir1 C16 63.1(3) . . ?
C15 Ir1 C16 38.2(2) . . ?
C14 Ir1 C16 63.5(3) . . ?
N2 Ir1 C12 107.5(3) . . ?
C10 Ir1 C12 161.1(3) . . ?
C13 Ir1 C12 38.7(3) . . ?
C15 Ir1 C12 63.5(3) . . ?
C14 Ir1 C12 64.4(3) . . ?
C16 Ir1 C12 36.4(3) . . ?
C3 N2 Ir1 133.7(5) . . ?
C3 N2 H2 118(6) . . ?
Ir1 N2 H2 108(6) . . ?
N2 C3 C4 118.6(6) . . ?
N2 C3 C8 122.2(6) . . ?
C4 C3 C8 119.1(5) . . ?
C5 C4 C3 122.2(7) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C4 C5 C6 119.0(7) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C7 C6 C5 119.8(6) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 123.8(8) . . ?
C6 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C3 C8 C7 116.1(7) . . ?
C3 C8 C9 122.0(5) . . ?
C7 C8 C9 121.9(6) . . ?
C10 C9 C8 123.9(5) . . ?
C10 C9 C11 118.1(6) . . ?
C8 C9 C11 118.0(5) . . ?
C9 C10 Ir1 130.9(5) . . ?
C9 C10 H10 111(5) . . ?
Ir1 C10 H10 118(5) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C16 C12 C13 106.3(7) . . ?
C16 C12 C17 128.7(9) . . ?
C13 C12 C17 125.1(9) . . ?
C16 C12 Ir1 70.8(4) . . ?
C13 C12 Ir1 66.5(4) . . ?
C17 C12 Ir1 127.2(5) . . ?
C14 C13 C12 108.6(7) . . ?
C14 C13 C18 124.4(7) . . ?
C12 C13 C18 126.5(8) . . ?
C14 C13 Ir1 71.3(4) . . ?
C12 C13 Ir1 74.8(5) . . ?
C18 C13 Ir1 126.0(5) . . ?
C15 C14 C13 106.9(6) . . ?
C15 C14 C19 126.3(6) . . ?
C13 C14 C19 126.8(6) . . ?
C15 C14 Ir1 70.7(3) . . ?
C13 C14 Ir1 69.5(4) . . ?
C19 C14 Ir1 125.2(4) . . ?
C14 C15 C16 108.3(6) . . ?
C14 C15 C20 125.7(7) . . ?
C16 C15 C20 125.9(7) . . ?
C14 C15 Ir1 71.1(3) . . ?
C16 C15 Ir1 73.4(4) . . ?
C20 C15 Ir1 125.5(5) . . ?
C12 C16 C15 109.7(6) . . ?
C12 C16 C21 127.3(9) . . ?
C15 C16 C21 122.9(8) . . ?
C12 C16 Ir1 72.8(4) . . ?
C15 C16 Ir1 68.4(4) . . ?
C21 C16 Ir1 125.9(5) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ir1 N2 C3 C4 176.5(5) . . . . ?
Ir1 N2 C3 C8 -2.5(9) . . . . ?
N2 C3 C4 C5 -177.9(6) . . . . ?
C8 C3 C4 C5 1.1(9) . . . . ?
C3 C4 C5 C6 -0.4(10) . . . . ?
C4 C5 C6 C7 -0.7(11) . . . . ?
C5 C6 C7 C8 1.0(10) . . . . ?
N2 C3 C8 C7 178.1(5) . . . . ?
C4 C3 C8 C7 -0.8(8) . . . . ?
N2 C3 C8 C9 -1.1(9) . . . . ?
C4 C3 C8 C9 180.0(5) . . . . ?
C6 C7 C8 C3 -0.2(9) . . . . ?
C6 C7 C8 C9 179.0(6) . . . . ?
C3 C8 C9 C10 3.1(9) . . . . ?
C7 C8 C9 C10 -176.1(6) . . . . ?
C3 C8 C9 C11 -178.1(5) . . . . ?
C7 C8 C9 C11 2.7(8) . . . . ?
C8 C9 C10 Ir1 -1.7(10) . . . . ?
C11 C9 C10 Ir1 179.5(5) . . . . ?
C16 C12 C13 C14 -3.9(7) . . . . ?
C17 C12 C13 C14 176.1(7) . . . . ?
Ir1 C12 C13 C14 -63.8(4) . . . . ?
C16 C12 C13 C18 -176.2(6) . . . . ?
C17 C12 C13 C18 3.8(10) . . . . ?
Ir1 C12 C13 C18 123.9(7) . . . . ?
C16 C12 C13 Ir1 60.0(4) . . . . ?
C17 C12 C13 Ir1 -120.0(7) . . . . ?
C12 C13 C14 C15 4.9(7) . . . . ?
C18 C13 C14 C15 177.4(6) . . . . ?
Ir1 C13 C14 C15 -61.2(4) . . . . ?
C12 C13 C14 C19 -174.6(6) . . . . ?
C18 C13 C14 C19 -2.1(10) . . . . ?
Ir1 C13 C14 C19 119.3(6) . . . . ?
C12 C13 C14 Ir1 66.1(5) . . . . ?
C18 C13 C14 Ir1 -121.4(6) . . . . ?
C13 C14 C15 C16 -4.0(7) . . . . ?
C19 C14 C15 C16 175.5(6) . . . . ?
Ir1 C14 C15 C16 -64.4(4) . . . . ?
C13 C14 C15 C20 -178.9(6) . . . . ?
C19 C14 C15 C20 0.6(10) . . . . ?
Ir1 C14 C15 C20 120.7(7) . . . . ?
C13 C14 C15 Ir1 60.4(4) . . . . ?
C19 C14 C15 Ir1 -120.1(6) . . . . ?
C13 C12 C16 C15 1.4(7) . . . . ?
C17 C12 C16 C15 -178.6(7) . . . . ?
Ir1 C12 C16 C15 58.6(5) . . . . ?
C13 C12 C16 C21 -179.6(6) . . . . ?
C17 C12 C16 C21 0.4(12) . . . . ?
Ir1 C12 C16 C21 -122.4(7) . . . . ?
C13 C12 C16 Ir1 -57.2(4) . . . . ?
C17 C12 C16 Ir1 122.8(8) . . . . ?
C14 C15 C16 C12 1.7(7) . . . . ?
C20 C15 C16 C12 176.6(6) . . . . ?
Ir1 C15 C16 C12 -61.3(5) . . . . ?
C14 C15 C16 C21 -177.4(6) . . . . ?
C20 C15 C16 C21 -2.5(10) . . . . ?
Ir1 C15 C16 C21 119.7(7) . . . . ?
C14 C15 C16 Ir1 62.9(4) . . . . ?
C20 C15 C16 Ir1 -122.2(7) . . . . ?

_refine_diff_density_max         1.241
_refine_diff_density_min         -1.126
_refine_diff_density_rms         0.091





















####################################################################### 
# 
# 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_A21255_014
_database_code_depnum_ccdc_archive 'CCDC 2115124'
loop_
_audit_author_name
_audit_author_address
'Dongwook Kim'
;Institute for Basic Science (IBS)
South Korea
;
_audit_update_record             
;
2021-10-12 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H11 N O'
_chemical_formula_sum            'C11 H11 N O'
_chemical_formula_weight         173.21

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'

_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                   9.9622(9)
_cell_length_b                   5.7301(4)
_cell_length_c                   15.9848(13)
_cell_angle_alpha                90
_cell_angle_beta                 106.083(3)
_cell_angle_gamma                90
_cell_volume                     876.77(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5247
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      27.10

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.024
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.3951
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\^I1/4S 3.0 Microfocus'
_diffrn_measurement_device_type  'PHOTON II 14'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9045
_diffrn_reflns_av_unetI/netI     0.0772
_diffrn_reflns_av_R_equivalents  0.1088
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.652
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             1590
_reflns_number_gt                1341
_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 APEXIII'
_computing_cell_refinement       'Bruker APEXIII'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_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)+(0.1435P)²+1.4958P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.46(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1590
_refine_ls_number_parameters     121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1289
_refine_ls_R_factor_gt           0.1139
_refine_ls_wR_factor_ref         0.2778
_refine_ls_wR_factor_gt          0.2674
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.162
_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 0.5832(3) 0.0972(6) 0.3085(2) 0.0260(10) Uani 1 1 d . . . . .
H1 H 0.618276 -0.033636 0.334242 0.031 Uiso 1 1 calc R U . . .
C2 C 0.6095(4) 0.1905(7) 0.2362(3) 0.0245(10) Uani 1 1 d . . . . .
H2 H 0.670346 0.123304 0.206387 0.029 Uiso 1 1 calc R U . . .
C3 C 0.5368(4) 0.3934(7) 0.2121(3) 0.0229(10) Uani 1 1 d . . . . .
C4 C 0.4618(4) 0.4317(6) 0.2750(2) 0.0207(10) Uani 1 1 d . . . . .
C5 C 0.4928(4) 0.2419(6) 0.3342(2) 0.0207(10) Uani 1 1 d . . . . .
C6 C 0.4355(4) 0.2241(7) 0.4041(3) 0.0224(10) Uani 1 1 d . . . . .
H6 H 0.455570 0.094014 0.442389 0.027 Uiso 1 1 calc R U . . .
C7 C 0.3480(4) 0.4022(7) 0.4163(2) 0.0212(10) Uani 1 1 d . . . . .
C8 C 0.3174(4) 0.5932(6) 0.3584(3) 0.0225(10) Uani 1 1 d . . . . .
H8 H 0.257836 0.713828 0.367843 0.027 Uiso 1 1 calc R U . . .
C9 C 0.3723(4) 0.6083(7) 0.2882(3) 0.0233(10) Uani 1 1 d . . . . .
H9 H 0.349727 0.736781 0.249247 0.028 Uiso 1 1 calc R U . . .
C10 C 0.5337(5) 0.5445(8) 0.1355(3) 0.0311(11) Uani 1 1 d . . . . .
H10A H 0.569335 0.700004 0.155776 0.047 Uiso 1 1 calc R U . . .
H10B H 0.437472 0.557675 0.098591 0.047 Uiso 1 1 calc R U . . .
H10C H 0.592362 0.475151 0.101992 0.047 Uiso 1 1 calc R U . . .
C11 C 0.2901(4) 0.3850(7) 0.4922(2) 0.0227(10) Uani 1 1 d . . . . .
O12 O 0.3154(3) 0.2173(6) 0.5412(2) 0.0358(10) Uani 1 1 d . . . . .
C13 C 0.1964(5) 0.5766(8) 0.5074(3) 0.0346(12) Uani 1 1 d . . . . .
H13A H 0.248228 0.723979 0.517507 0.052 Uiso 1 1 calc R U . . .
H13B H 0.164134 0.538570 0.558394 0.052 Uiso 1 1 calc R U . . .
H13C H 0.115644 0.591973 0.456142 0.052 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
N1 C2 1.364(5) . ?
N1 C5 1.368(5) . ?
N1 H1 0.8800 . ?
C2 C3 1.367(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.426(6) . ?
C3 C10 1.493(6) . ?
C4 C9 1.403(5) . ?
C4 C5 1.418(5) . ?
C5 C6 1.392(6) . ?
C6 C7 1.390(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.412(5) . ?
C7 C11 1.484(5) . ?
C8 C9 1.380(6) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O12 1.221(5) . ?
C11 C13 1.503(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
C2 N1 C5 108.3(3) . . ?
C2 N1 H1 125.8 . . ?
C5 N1 H1 125.8 . . ?
N1 C2 C3 111.1(3) . . ?
N1 C2 H2 124.4 . . ?
C3 C2 H2 124.4 . . ?
C2 C3 C4 105.8(3) . . ?
C2 C3 C10 127.8(4) . . ?
C4 C3 C10 126.4(4) . . ?
C9 C4 C5 118.9(4) . . ?
C9 C4 C3 134.1(4) . . ?
C5 C4 C3 107.0(3) . . ?
N1 C5 C6 130.3(4) . . ?
N1 C5 C4 107.7(3) . . ?
C6 C5 C4 122.0(3) . . ?
C7 C6 C5 118.1(3) . . ?
C7 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C6 C7 C8 120.5(4) . . ?
C6 C7 C11 117.8(3) . . ?
C8 C7 C11 121.7(4) . . ?
C9 C8 C7 121.3(4) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C4 119.2(4) . . ?
C8 C9 H9 120.4 . . ?
C4 C9 H9 120.4 . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O12 C11 C7 121.2(4) . . ?
O12 C11 C13 119.9(4) . . ?
C7 C11 C13 118.9(3) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 C3 -0.9(4) . . . . ?
N1 C2 C3 C4 1.2(4) . . . . ?
N1 C2 C3 C10 -178.1(4) . . . . ?
C2 C3 C4 C9 178.3(4) . . . . ?
C10 C3 C4 C9 -2.4(7) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C10 C3 C4 C5 178.3(4) . . . . ?
C2 N1 C5 C6 -179.6(4) . . . . ?
C2 N1 C5 C4 0.2(4) . . . . ?
C9 C4 C5 N1 -178.9(3) . . . . ?
C3 C4 C5 N1 0.5(4) . . . . ?
C9 C4 C5 C6 0.9(5) . . . . ?
C3 C4 C5 C6 -179.6(3) . . . . ?
N1 C5 C6 C7 178.4(4) . . . . ?
C4 C5 C6 C7 -1.5(5) . . . . ?
C5 C6 C7 C8 0.9(5) . . . . ?
C5 C6 C7 C11 -178.5(3) . . . . ?
C6 C7 C8 C9 0.3(6) . . . . ?
C11 C7 C8 C9 179.7(3) . . . . ?
C7 C8 C9 C4 -0.9(6) . . . . ?
C5 C4 C9 C8 0.3(5) . . . . ?
C3 C4 C9 C8 -178.9(4) . . . . ?
C6 C7 C11 O12 -1.8(6) . . . . ?
C8 C7 C11 O12 178.8(4) . . . . ?
C6 C7 C11 C13 179.4(3) . . . . ?
C8 C7 C11 C13 0.0(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O12 0.88 2.19 2.949(4) 144.8 3_656 yes

_refine_diff_density_max         0.613
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.109



























