# 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_global
_database_code_depnum_ccdc_archive 'CCDC 2095228'
loop_
_audit_author_name
_audit_author_address
'Youngmee Kim'
;Ewha Womans University
South Korea
;
_audit_update_record             
;
2021-07-08 deposited with the CCDC.	2021-09-27 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2019.11-0'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H33 N4 O2 Rh'
_chemical_formula_weight         656.57

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'
Rh Rh -1.1178 0.9187 '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                   12.8432(6)
_cell_length_b                   14.0502(6)
_cell_length_c                   16.6156(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.340(2)
_cell_angle_gamma                90
_cell_volume                     2993.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9908
_cell_measurement_theta_min      2.5219
_cell_measurement_theta_max      28.2445

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_F_000             1352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.610
_shelx_estimated_absorpt_T_min   0.888
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            112285
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.900
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_full        25.047
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5304
_reflns_number_gt                4740
_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 Instrument Service v2021.1.0.1'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (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)+(0.0409P)²+3.7289P] 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         5304
_refine_ls_number_parameters     394
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0868
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.063
_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
C1 C 0.8071(2) 0.7509(2) 0.26002(11) 0.0406(6) Uani 1 1 d D . . . .
C2 C 0.9102(2) 0.7381(2) 0.29989(18) 0.0423(6) Uani 1 1 d . . . . .
C3 C 1.0082(3) 0.7260(2) 0.2703(2) 0.0552(8) Uani 1 1 d . . . . .
H3 H 1.017113 0.724482 0.215171 0.066 Uiso 1 1 calc R U . . .
C4 C 1.0921(3) 0.7162(3) 0.3258(3) 0.0638(9) Uani 1 1 d . . . . .
H4 H 1.158848 0.708302 0.307911 0.077 Uiso 1 1 calc R U . . .
C5 C 1.0776(3) 0.7181(3) 0.4081(2) 0.0636(10) Uani 1 1 d . . . . .
H5 H 1.135393 0.710344 0.443956 0.076 Uiso 1 1 calc R U . . .
C6 C 0.9820(3) 0.7309(2) 0.4385(2) 0.0540(8) Uani 1 1 d . . . . .
H6 H 0.973449 0.731771 0.493660 0.065 Uiso 1 1 calc R U . . .
C7 C 0.8972(2) 0.7426(2) 0.38187(18) 0.0426(7) Uani 1 1 d . . . . .
C8 C 0.7439(2) 0.7238(2) 0.46171(17) 0.0425(7) Uani 1 1 d . . . . .
C9 C 0.7621(3) 0.7679(3) 0.53563(19) 0.0574(9) Uani 1 1 d . . . . .
H9 H 0.803053 0.822447 0.539692 0.069 Uiso 1 1 calc R U . . .
C10 C 0.7201(3) 0.7314(4) 0.6026(2) 0.0735(12) Uani 1 1 d . . . . .
H10 H 0.732149 0.761608 0.652064 0.088 Uiso 1 1 calc R U . . .
C11 C 0.6609(4) 0.6512(4) 0.5977(3) 0.0797(14) Uani 1 1 d . . . . .
H11 H 0.633603 0.626404 0.643859 0.096 Uiso 1 1 calc R U . . .
C12 C 0.6409(3) 0.6062(3) 0.5242(3) 0.0728(11) Uani 1 1 d . . . . .
H12 H 0.599356 0.551975 0.520822 0.087 Uiso 1 1 calc R U . . .
C13 C 0.6832(3) 0.6426(2) 0.4556(2) 0.0549(8) Uani 1 1 d . . . . .
H13 H 0.670712 0.612668 0.406071 0.066 Uiso 1 1 calc R U . . .
C14 C 0.54997(18) 0.6894(2) 0.16374(15) 0.0394(6) Uani 1 1 d D . . . .
C15 C 0.4793(2) 0.6124(2) 0.15312(19) 0.0441(7) Uani 1 1 d . . . . .
C16 C 0.4636(3) 0.5454(2) 0.0923(2) 0.0614(9) Uani 1 1 d . . . . .
H16 H 0.500961 0.547922 0.046078 0.074 Uiso 1 1 calc R U . . .
C17 C 0.3911(3) 0.4753(3) 0.1025(3) 0.0764(12) Uani 1 1 d . . . . .
H17 H 0.378617 0.429621 0.062618 0.092 Uiso 1 1 calc R U . . .
C18 C 0.3366(3) 0.4724(3) 0.1716(3) 0.0763(12) Uani 1 1 d . . . . .
H18 H 0.288389 0.423768 0.176986 0.092 Uiso 1 1 calc R U . . .
C19 C 0.3499(3) 0.5376(3) 0.2328(3) 0.0639(10) Uani 1 1 d . . . . .
H19 H 0.311904 0.534412 0.278722 0.077 Uiso 1 1 calc R U . . .
C20 C 0.4243(2) 0.6095(2) 0.2224(2) 0.0449(7) Uani 1 1 d . . . . .
C21 C 0.4476(2) 0.7111(2) 0.35009(18) 0.0435(7) Uani 1 1 d . . . . .
C22 C 0.3781(3) 0.6683(3) 0.4003(2) 0.0605(9) Uani 1 1 d . . . . .
H22 H 0.334318 0.619703 0.380805 0.073 Uiso 1 1 calc R U . . .
C23 C 0.3747(3) 0.6984(3) 0.4790(2) 0.0652(10) Uani 1 1 d . . . . .
H23 H 0.329045 0.669580 0.512894 0.078 Uiso 1 1 calc R U . . .
C24 C 0.4378(3) 0.7701(3) 0.5074(2) 0.0569(9) Uani 1 1 d . . . . .
H24 H 0.434705 0.790502 0.560449 0.068 Uiso 1 1 calc R U . . .
C25 C 0.5069(2) 0.8130(2) 0.45714(18) 0.0465(7) Uani 1 1 d . . . . .
H25 H 0.550234 0.861301 0.477705 0.056 Uiso 1 1 calc R U . . .
C26 C 0.5131(2) 0.7858(2) 0.37690(17) 0.0388(6) Uani 1 1 d . . . . .
C27 C 0.5358(2) 0.9862(2) 0.31377(18) 0.0435(7) Uani 1 1 d . . . . .
C28 C 0.5196(2) 0.9607(2) 0.23070(18) 0.0419(6) Uani 1 1 d . . . . .
C29 C 0.6196(2) 0.9580(2) 0.19536(17) 0.0403(6) Uani 1 1 d . . . . .
C30 C 0.6959(2) 0.9745(2) 0.25723(18) 0.0423(7) Uani 1 1 d . . . . .
C31 C 0.6459(2) 0.98847(19) 0.33204(17) 0.0420(7) Uani 1 1 d . . . . .
C32 C 0.4523(3) 1.0113(3) 0.3687(2) 0.0630(9) Uani 1 1 d . . . . .
H32A H 0.479979 1.008958 0.423598 0.095 Uiso 1 1 calc R U . . .
H32B H 0.395771 0.966873 0.361384 0.095 Uiso 1 1 calc R U . . .
H32C H 0.427295 1.074422 0.356535 0.095 Uiso 1 1 calc R U . . .
C33 C 0.4161(3) 0.9500(3) 0.1846(2) 0.0629(9) Uani 1 1 d . . . . .
H33A H 0.364429 0.930333 0.220680 0.094 Uiso 1 1 calc R U . . .
H33B H 0.421677 0.902952 0.143169 0.094 Uiso 1 1 calc R U . . .
H33C H 0.395972 1.009816 0.160521 0.094 Uiso 1 1 calc R U . . .
C34 C 0.6352(3) 0.9473(3) 0.10701(19) 0.0565(8) Uani 1 1 d . . . . .
H34A H 0.619231 1.006305 0.079985 0.085 Uiso 1 1 calc R U . . .
H34B H 0.590031 0.898211 0.084944 0.085 Uiso 1 1 calc R U . . .
H34C H 0.706480 0.930364 0.099582 0.085 Uiso 1 1 calc R U . . .
C35 C 0.8112(3) 0.9805(3) 0.2487(2) 0.0599(9) Uani 1 1 d . . . . .
H35A H 0.829406 0.944161 0.202672 0.090 Uiso 1 1 calc R U . . .
H35B H 0.847217 0.955294 0.296341 0.090 Uiso 1 1 calc R U . . .
H35C H 0.830903 1.045722 0.241791 0.090 Uiso 1 1 calc R U . . .
C36 C 0.7011(3) 1.0153(3) 0.4108(2) 0.0591(9) Uani 1 1 d . . . . .
H36A H 0.724190 1.080218 0.408400 0.089 Uiso 1 1 calc R U . . .
H36B H 0.760251 0.974416 0.421130 0.089 Uiso 1 1 calc R U . . .
H36C H 0.654236 1.008602 0.453422 0.089 Uiso 1 1 calc R U . . .
N1 N 0.73788(18) 0.76225(17) 0.31744(13) 0.0387(5) Uani 1 1 d . . . . .
N2 N 0.79342(19) 0.76121(18) 0.39391(14) 0.0423(6) Uani 1 1 d . . . . .
N3 N 0.53676(18) 0.73200(16) 0.23163(14) 0.0374(5) Uani 1 1 d . . . . .
N4 N 0.45830(19) 0.68386(18) 0.27000(15) 0.0434(6) Uani 1 1 d . . . . .
O1 O 0.78865(16) 0.75462(17) 0.18516(10) 0.0510(5) Uani 1 1 d D . . . .
O2 O 0.62258(16) 0.71603(16) 0.11391(11) 0.0476(5) Uani 1 1 d D . . . .
H2 H 0.675251 0.732965 0.140336 0.071 Uiso 1 1 calc R U . . .
Rh1 Rh 0.60155(2) 0.84694(2) 0.29261(2) 0.03282(9) 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
C1 O1 1.2538(10) . ?
C1 N1 1.351(3) . ?
C1 C2 1.456(4) . ?
C2 C7 1.383(4) . ?
C2 C3 1.388(4) . ?
C3 C4 1.384(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.366(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.407(4) . ?
C6 H6 0.9300 . ?
C7 N2 1.384(4) . ?
C8 C13 1.382(5) . ?
C8 C9 1.383(4) . ?
C8 N2 1.426(4) . ?
C9 C10 1.365(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.359(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.385(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 N3 1.297(3) . ?
C14 O2 1.3362(10) . ?
C14 C15 1.416(4) . ?
C15 C20 1.386(5) . ?
C15 C16 1.387(4) . ?
C16 C17 1.372(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.371(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.408(4) . ?
C19 H19 0.9300 . ?
C20 N4 1.367(4) . ?
C21 C22 1.394(4) . ?
C21 N4 1.399(4) . ?
C21 C26 1.401(4) . ?
C22 C23 1.378(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.360(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.391(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.394(4) . ?
C25 H25 0.9300 . ?
C26 Rh1 2.043(3) . ?
C27 C28 1.429(4) . ?
C27 C31 1.429(4) . ?
C27 C32 1.491(4) . ?
C27 Rh1 2.168(3) . ?
C28 C29 1.444(4) . ?
C28 C33 1.502(4) . ?
C28 Rh1 2.143(3) . ?
C29 C30 1.398(4) . ?
C29 C34 1.501(4) . ?
C29 Rh1 2.268(3) . ?
C30 C31 1.445(4) . ?
C30 C35 1.498(4) . ?
C30 Rh1 2.260(3) . ?
C31 C36 1.501(4) . ?
C31 Rh1 2.160(3) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
N1 N2 1.420(3) . ?
N1 Rh1 2.137(2) . ?
N3 N4 1.398(3) . ?
N3 Rh1 2.056(2) . ?
O2 H2 0.8200 . ?

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
O1 C1 N1 127.0(3) . . ?
O1 C1 C2 124.8(3) . . ?
N1 C1 C2 108.15(19) . . ?
C7 C2 C3 121.2(3) . . ?
C7 C2 C1 106.5(2) . . ?
C3 C2 C1 132.3(3) . . ?
C4 C3 C2 117.6(3) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 122.7(3) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C5 C6 C7 116.5(3) . . ?
C5 C6 H6 121.7 . . ?
C7 C6 H6 121.7 . . ?
C2 C7 N2 108.9(2) . . ?
C2 C7 C6 121.3(3) . . ?
N2 C7 C6 129.8(3) . . ?
C13 C8 C9 120.0(3) . . ?
C13 C8 N2 121.5(3) . . ?
C9 C8 N2 118.4(3) . . ?
C10 C9 C8 120.1(4) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 120.6(4) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.4(4) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C13 119.6(4) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C8 C13 C12 119.3(4) . . ?
C8 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
N3 C14 O2 122.7(2) . . ?
N3 C14 C15 110.2(2) . . ?
O2 C14 C15 127.0(3) . . ?
C20 C15 C16 121.7(3) . . ?
C20 C15 C14 105.8(2) . . ?
C16 C15 C14 132.4(3) . . ?
C17 C16 C15 117.9(4) . . ?
C17 C16 H16 121.0 . . ?
C15 C16 H16 121.0 . . ?
C16 C17 C18 120.3(4) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 123.4(4) . . ?
C19 C18 H18 118.3 . . ?
C17 C18 H18 118.3 . . ?
C18 C19 C20 116.3(4) . . ?
C18 C19 H19 121.8 . . ?
C20 C19 H19 121.8 . . ?
N4 C20 C15 107.3(3) . . ?
N4 C20 C19 132.3(3) . . ?
C15 C20 C19 120.4(3) . . ?
C22 C21 N4 123.5(3) . . ?
C22 C21 C26 121.8(3) . . ?
N4 C21 C26 114.7(3) . . ?
C23 C22 C21 119.4(3) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C24 C23 C22 120.4(3) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 120.0(3) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C26 122.0(3) . . ?
C24 C25 H25 119.0 . . ?
C26 C25 H25 119.0 . . ?
C25 C26 C21 116.3(3) . . ?
C25 C26 Rh1 127.3(2) . . ?
C21 C26 Rh1 116.4(2) . . ?
C28 C27 C31 107.3(3) . . ?
C28 C27 C32 125.5(3) . . ?
C31 C27 C32 127.1(3) . . ?
C28 C27 Rh1 69.72(16) . . ?
C31 C27 Rh1 70.41(16) . . ?
C32 C27 Rh1 127.9(2) . . ?
C27 C28 C29 108.4(3) . . ?
C27 C28 C33 126.3(3) . . ?
C29 C28 C33 124.9(3) . . ?
C27 C28 Rh1 71.56(16) . . ?
C29 C28 Rh1 75.63(16) . . ?
C33 C28 Rh1 124.4(2) . . ?
C30 C29 C28 107.4(3) . . ?
C30 C29 C34 127.5(3) . . ?
C28 C29 C34 125.0(3) . . ?
C30 C29 Rh1 71.73(16) . . ?
C28 C29 Rh1 66.28(16) . . ?
C34 C29 Rh1 130.8(2) . . ?
C29 C30 C31 109.1(3) . . ?
C29 C30 C35 126.5(3) . . ?
C31 C30 C35 124.4(3) . . ?
C29 C30 Rh1 72.32(16) . . ?
C31 C30 Rh1 67.18(15) . . ?
C35 C30 Rh1 128.1(2) . . ?
C27 C31 C30 107.3(2) . . ?
C27 C31 C36 127.0(3) . . ?
C30 C31 C36 125.0(3) . . ?
C27 C31 Rh1 71.02(16) . . ?
C30 C31 Rh1 74.74(16) . . ?
C36 C31 Rh1 126.8(2) . . ?
C27 C32 H32A 109.5 . . ?
C27 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C27 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C28 C33 H33A 109.5 . . ?
C28 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C28 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C29 C34 H34A 109.5 . . ?
C29 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C29 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C30 C35 H35A 109.5 . . ?
C30 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C30 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C31 C36 H36A 109.5 . . ?
C31 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C31 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C1 N1 N2 108.3(2) . . ?
C1 N1 Rh1 119.67(17) . . ?
N2 N1 Rh1 122.78(17) . . ?
C7 N2 N1 108.1(2) . . ?
C7 N2 C8 121.4(2) . . ?
N1 N2 C8 119.1(2) . . ?
C14 N3 N4 107.9(2) . . ?
C14 N3 Rh1 136.18(18) . . ?
N4 N3 Rh1 115.92(17) . . ?
C20 N4 N3 108.7(2) . . ?
C20 N4 C21 135.6(3) . . ?
N3 N4 C21 114.5(2) . . ?
C14 O2 H2 109.5 . . ?
C26 Rh1 N3 77.44(10) . . ?
C26 Rh1 N1 96.64(10) . . ?
N3 Rh1 N1 87.78(9) . . ?
C26 Rh1 C28 111.41(11) . . ?
N3 Rh1 C28 100.12(10) . . ?
N1 Rh1 C28 151.86(11) . . ?
C26 Rh1 C31 109.05(11) . . ?
N3 Rh1 C31 164.69(10) . . ?
N1 Rh1 C31 104.80(10) . . ?
C28 Rh1 C31 64.70(11) . . ?
C26 Rh1 C27 91.76(11) . . ?
N3 Rh1 C27 129.67(10) . . ?
N1 Rh1 C27 142.54(10) . . ?
C28 Rh1 C27 38.72(11) . . ?
C31 Rh1 C27 38.58(11) . . ?
C26 Rh1 C30 147.08(11) . . ?
N3 Rh1 C30 134.61(10) . . ?
N1 Rh1 C30 92.65(10) . . ?
C28 Rh1 C30 62.60(11) . . ?
C31 Rh1 C30 38.08(11) . . ?
C27 Rh1 C30 63.02(11) . . ?
C26 Rh1 C29 149.50(11) . . ?
N3 Rh1 C29 104.15(9) . . ?
N1 Rh1 C29 113.82(10) . . ?
C28 Rh1 C29 38.09(11) . . ?
C31 Rh1 C29 63.03(10) . . ?
C27 Rh1 C29 63.36(11) . . ?
C30 Rh1 C29 35.95(10) . . ?

_refine_diff_density_max         1.850
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.058



####################################################################### 
# 
# 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_yy020P-1_a
_database_code_depnum_ccdc_archive 'CCDC 2096892'
loop_
_audit_author_name
_audit_author_address
'Youngmee Kim'
;Ewha Womans University
South Korea
;
_audit_update_record             
;
2021-07-16 deposited with the CCDC.	2021-09-27 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            'C13 H10 N2 O'
_chemical_formula_weight         210.23

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      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                   6.772(2)
_cell_length_b                   9.153(2)
_cell_length_c                   9.331(2)
_cell_angle_alpha                70.250(7)
_cell_angle_beta                 87.119(8)
_cell_angle_gamma                72.184(8)
_cell_volume                     517.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5540
_cell_measurement_theta_min      2.3232
_cell_measurement_theta_max      27.5387

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             220
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            16137
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.323
_diffrn_reflns_theta_max         28.419
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2588
_reflns_number_gt                2051
_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 Instrument Service v2021.1.0.1'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (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)+(0.0515P)²+0.1255P] 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         2588
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1209
_refine_ls_wR_factor_gt          0.1134
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
C1 C 0.2204(2) 0.02157(16) 0.61760(15) 0.0349(3) Uani 1 1 d . . . . .
C2 C 0.3879(2) 0.06146(16) 0.66562(16) 0.0339(3) Uani 1 1 d . . . . .
C3 C 0.5245(2) -0.00202(18) 0.79570(17) 0.0434(4) Uani 1 1 d . . . . .
H3 H 0.519961 -0.094865 0.875668 0.052 Uiso 1 1 calc R U . . .
C4 C 0.6646(2) 0.0772(2) 0.80102(19) 0.0490(4) Uani 1 1 d . . . . .
H4 H 0.755911 0.037840 0.886323 0.059 Uiso 1 1 calc R U . . .
C5 C 0.6728(2) 0.2166(2) 0.6802(2) 0.0468(4) Uani 1 1 d . . . . .
H5 H 0.770607 0.266712 0.687355 0.056 Uiso 1 1 calc R U . . .
C6 C 0.5418(2) 0.28130(18) 0.55217(18) 0.0405(3) Uani 1 1 d . . . . .
H6 H 0.548172 0.373974 0.472773 0.049 Uiso 1 1 calc R U . . .
C7 C 0.3974(2) 0.20133(16) 0.54635(15) 0.0331(3) Uani 1 1 d . . . . .
C8 C 0.1710(2) 0.38125(16) 0.30941(15) 0.0340(3) Uani 1 1 d . . . . .
C9 C -0.0371(2) 0.47121(19) 0.29050(18) 0.0465(4) Uani 1 1 d . . . . .
H9 H -0.129585 0.437187 0.361386 0.056 Uiso 1 1 calc R U . . .
C10 C -0.1070(3) 0.6122(2) 0.1654(2) 0.0574(5) Uani 1 1 d . . . . .
H10 H -0.247016 0.672620 0.151802 0.069 Uiso 1 1 calc R U . . .
C11 C 0.0298(3) 0.6635(2) 0.06100(19) 0.0564(5) Uani 1 1 d . . . . .
H11 H -0.017631 0.757829 -0.023365 0.068 Uiso 1 1 calc R U . . .
C12 C 0.2368(3) 0.5747(2) 0.08195(18) 0.0527(4) Uani 1 1 d . . . . .
H12 H 0.329371 0.610728 0.012297 0.063 Uiso 1 1 calc R U . . .
C13 C 0.3093(2) 0.43257(18) 0.20520(17) 0.0420(3) Uani 1 1 d . . . . .
H13 H 0.449357 0.372224 0.217873 0.050 Uiso 1 1 calc R U . . .
N1 N 0.13324(17) 0.12638(14) 0.48492(13) 0.0363(3) Uani 1 1 d . . . . .
N2 N 0.24482(17) 0.23690(14) 0.43820(13) 0.0358(3) Uani 1 1 d . . . . .
O1 O 0.16032(17) -0.10786(13) 0.69579(12) 0.0467(3) Uani 1 1 d . . . . .
H1 H 0.067604 -0.112821 0.646073 0.070 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 N1 1.3136(18) . ?
C1 O1 1.3349(16) . ?
C1 C2 1.427(2) . ?
C2 C7 1.4008(19) . ?
C2 C3 1.405(2) . ?
C3 C4 1.371(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.402(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.368(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.401(2) . ?
C6 H6 0.9300 . ?
C7 N2 1.3673(18) . ?
C8 C13 1.383(2) . ?
C8 C9 1.383(2) . ?
C8 N2 1.4222(17) . ?
C9 C10 1.384(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.376(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.373(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
N1 N2 1.3859(16) . ?
O1 H1 0.8200 . ?

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
N1 C1 O1 123.56(13) . . ?
N1 C1 C2 111.87(12) . . ?
O1 C1 C2 124.56(12) . . ?
C7 C2 C3 120.14(13) . . ?
C7 C2 C1 104.14(12) . . ?
C3 C2 C1 135.69(13) . . ?
C4 C3 C2 117.90(14) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C3 C4 C5 121.20(14) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 122.24(14) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C7 116.84(14) . . ?
C5 C6 H6 121.6 . . ?
C7 C6 H6 121.6 . . ?
N2 C7 C2 107.32(12) . . ?
N2 C7 C6 130.99(13) . . ?
C2 C7 C6 121.67(13) . . ?
C13 C8 C9 120.35(14) . . ?
C13 C8 N2 119.58(13) . . ?
C9 C8 N2 120.05(13) . . ?
C8 C9 C10 119.57(15) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 120.31(16) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 119.72(15) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.89(16) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C8 119.15(15) . . ?
C12 C13 H13 120.4 . . ?
C8 C13 H13 120.4 . . ?
C1 N1 N2 106.10(11) . . ?
C7 N2 N1 110.54(11) . . ?
C7 N2 C8 127.98(12) . . ?
N1 N2 C8 120.27(11) . . ?
C1 O1 H1 109.5 . . ?

_refine_diff_density_max         0.221
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.037



