# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_9218
_database_code_depnum_ccdc_archive 'CCDC 1855464'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.	2022-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 Cd0.50 N3 O3'
_chemical_formula_weight         340.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd 0.1185 4.6533 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   21.3568(10)
_cell_length_b                   11.1344(7)
_cell_length_c                   14.8894(6)
_cell_angle_alpha                90
_cell_angle_beta                 128.656(4)
_cell_angle_gamma                90
_cell_volume                     2764.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1911
_cell_measurement_theta_min      4.7810
_cell_measurement_theta_max      65.1590

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_F_000             1384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    6.811
_shelx_estimated_absorpt_T_min   0.471
_shelx_estimated_absorpt_T_max   0.521
_exptl_absorpt_correction_T_min  0.73999
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Enhance (Cu) X-ray Source'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5738
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.775
_diffrn_reflns_theta_max         67.240
_diffrn_reflns_theta_full        67.240
_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             2480
_reflns_number_gt                2073
_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       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0493P)²+2.4437P] 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         2480
_refine_ls_number_parameters     197
_refine_ls_number_restraints     486
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1151
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.035
_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
Cd1 Cd 0.5000 0.33131(5) 0.2500 0.04489(18) Uani 1 2 d S TU P . .
N1 N 0.4025(2) 0.7312(4) 0.5550(3) 0.0459(9) Uani 1 1 d . U . . .
N2 N 0.2864(2) 0.8197(4) 0.4234(3) 0.0481(10) Uani 1 1 d . U . . .
H2 H 0.2454 0.8654 0.3939 0.058 Uiso 1 1 calc R U . . .
N3 N 0.4183(3) 0.8342(4) 0.7363(4) 0.0526(10) Uani 1 1 d . U . . .
O1 O 0.4719(2) 0.4775(4) 0.3282(3) 0.0605(10) Uani 1 1 d . U . . .
O2 O 0.3504(2) 0.4467(4) 0.1667(3) 0.0671(11) Uani 1 1 d . U . . .
O3 O 0.6154(5) 0.6371(8) 0.4813(7) 0.182(4) Uani 1 1 d . U . . .
H3 H 0.5761 0.5929 0.4452 0.272 Uiso 1 1 calc R U . . .
C1 C 0.3975(3) 0.4973(5) 0.2620(4) 0.0477(11) Uani 1 1 d . U . . .
C2 C 0.3641(3) 0.5856(5) 0.2996(4) 0.0452(11) Uani 1 1 d . U . . .
C3 C 0.2891(3) 0.6387(5) 0.2177(4) 0.0486(12) Uani 1 1 d . U . . .
H3A H 0.2604 0.6180 0.1407 0.058 Uiso 1 1 calc R U . . .
C4 C 0.2568(3) 0.7203(5) 0.2476(4) 0.0512(12) Uani 1 1 d . U . . .
H4 H 0.2076 0.7568 0.1923 0.061 Uiso 1 1 calc R U . . .
C5 C 0.3007(3) 0.7463(5) 0.3645(4) 0.0425(11) Uani 1 1 d . U . . .
C6 C 0.3740(3) 0.6915(4) 0.4463(4) 0.0450(11) Uani 1 1 d . U . . .
C7 C 0.4078(3) 0.6129(5) 0.4153(4) 0.0472(11) Uani 1 1 d . U . . .
H7 H 0.4581 0.5794 0.4703 0.057 Uiso 1 1 calc R U . . .
C8 C 0.3487(3) 0.8073(5) 0.5365(4) 0.0471(11) Uani 1 1 d . U . . .
C9 C 0.3565(3) 0.8708(5) 0.6295(5) 0.0486(11) Uani 1 1 d . U . . .
C10 C 0.3048(4) 0.9603(5) 0.6084(5) 0.0653(15) Uani 1 1 d . U . . .
H10 H 0.2618 0.9816 0.5334 0.078 Uiso 1 1 calc R U . . .
C11 C 0.3174(4) 1.0179(6) 0.6997(6) 0.0761(17) Uani 1 1 d . U . . .
H11 H 0.2825 1.0778 0.6876 0.091 Uiso 1 1 calc R U . . .
C12 C 0.3821(4) 0.9862(6) 0.8093(6) 0.0750(17) Uani 1 1 d . U . . .
H12 H 0.3936 1.0272 0.8725 0.090 Uiso 1 1 calc R U . . .
C13 C 0.4300(4) 0.8915(6) 0.8238(5) 0.0664(15) Uani 1 1 d . U . . .
H13 H 0.4721 0.8671 0.8982 0.080 Uiso 1 1 calc R U . . .
C14 C 0.5605(8) 0.8350(13) 0.4107(13) 0.222(7) Uani 1 1 d . U . . .
H14A H 0.5444 0.8192 0.4571 0.333 Uiso 1 1 calc R U . . .
H14B H 0.5139 0.8502 0.3329 0.333 Uiso 1 1 calc R U . . .
H14C H 0.5951 0.9039 0.4404 0.333 Uiso 1 1 calc R U . . .
C15 C 0.6040(9) 0.7293(14) 0.4135(12) 0.195(6) Uani 1 1 d . U . . .
H15A H 0.5747 0.6995 0.3356 0.234 Uiso 1 1 calc R U . . .
H15B H 0.6561 0.7560 0.4390 0.234 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
Cd1 O1 2.288(4) . ?
Cd1 O1 2.288(4) 2_655 ?
Cd1 N1 2.387(4) 6_565 ?
Cd1 N1 2.387(4) 5_666 ?
Cd1 N3 2.457(4) 6_565 ?
Cd1 N3 2.457(4) 5_666 ?
N1 C8 1.311(6) . ?
N1 C6 1.399(6) . ?
N1 Cd1 2.387(4) 5_666 ?
N2 C8 1.351(6) . ?
N2 C5 1.366(6) . ?
N3 C13 1.328(7) . ?
N3 C9 1.346(7) . ?
N3 Cd1 2.457(4) 5_666 ?
O1 C1 1.260(6) . ?
O2 C1 1.249(6) . ?
O3 C15 1.351(14) . ?
C1 C2 1.514(7) . ?
C2 C7 1.387(6) . ?
C2 C3 1.400(7) . ?
C3 C4 1.374(7) . ?
C4 C5 1.397(7) . ?
C5 C6 1.387(6) . ?
C6 C7 1.383(7) . ?
C8 C9 1.468(7) . ?
C9 C10 1.372(7) . ?
C10 C11 1.368(8) . ?
C11 C12 1.371(9) . ?
C12 C13 1.388(9) . ?
C14 C15 1.483(15) . ?

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 Cd1 O1 89.3(2) . 2_655 ?
O1 Cd1 N1 121.30(13) . 6_565 ?
O1 Cd1 N1 84.00(13) 2_655 6_565 ?
O1 Cd1 N1 84.00(13) . 5_666 ?
O1 Cd1 N1 121.30(13) 2_655 5_666 ?
N1 Cd1 N1 146.1(2) 6_565 5_666 ?
O1 Cd1 N3 100.22(14) . 6_565 ?
O1 Cd1 N3 152.78(13) 2_655 6_565 ?
N1 Cd1 N3 69.22(14) 6_565 6_565 ?
N1 Cd1 N3 85.25(14) 5_666 6_565 ?
O1 Cd1 N3 152.78(13) . 5_666 ?
O1 Cd1 N3 100.22(14) 2_655 5_666 ?
N1 Cd1 N3 85.25(14) 6_565 5_666 ?
N1 Cd1 N3 69.22(14) 5_666 5_666 ?
N3 Cd1 N3 82.8(2) 6_565 5_666 ?
C8 N1 C6 105.7(4) . . ?
C8 N1 Cd1 115.4(3) . 5_666 ?
C6 N1 Cd1 137.2(3) . 5_666 ?
C8 N2 C5 107.4(4) . . ?
C13 N3 C9 117.3(5) . . ?
C13 N3 Cd1 126.2(4) . 5_666 ?
C9 N3 Cd1 116.5(3) . 5_666 ?
C1 O1 Cd1 109.2(3) . . ?
O2 C1 O1 122.5(5) . . ?
O2 C1 C2 118.8(5) . . ?
O1 C1 C2 118.7(4) . . ?
C7 C2 C3 120.4(5) . . ?
C7 C2 C1 119.7(4) . . ?
C3 C2 C1 119.9(4) . . ?
C4 C3 C2 122.0(5) . . ?
C3 C4 C5 117.3(5) . . ?
N2 C5 C6 106.4(4) . . ?
N2 C5 C4 132.7(5) . . ?
C6 C5 C4 121.0(5) . . ?
C7 C6 C5 121.5(4) . . ?
C7 C6 N1 130.2(4) . . ?
C5 C6 N1 108.3(4) . . ?
C6 C7 C2 117.8(5) . . ?
N1 C8 N2 112.3(4) . . ?
N1 C8 C9 122.9(5) . . ?
N2 C8 C9 124.8(5) . . ?
N3 C9 C10 123.0(5) . . ?
N3 C9 C8 114.8(5) . . ?
C10 C9 C8 122.2(5) . . ?
C11 C10 C9 118.8(6) . . ?
C10 C11 C12 119.2(6) . . ?
C11 C12 C13 118.5(6) . . ?
N3 C13 C12 122.9(6) . . ?
O3 C15 C14 116.2(15) . . ?

_refine_diff_density_max         0.598
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.080

