# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_ctc567
_database_code_depnum_ccdc_archive 'CCDC 2196220'
loop_
_audit_author_name
_audit_author_address
'Chi-Tien Chen'
;National Chung Hsing University
Taiwan
;
_audit_update_record             
;
2022-08-11 deposited with the CCDC.	2022-09-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C28 H20 Al Cl N2 O2'
_chemical_formula_sum            'C28 H20 Al Cl N2 O2'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            red
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         478.89

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'
Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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                   15.5736(7)
_cell_length_b                   10.6795(7)
_cell_length_c                   14.9564(9)
_cell_angle_alpha                90
_cell_angle_beta                 113.626(3)
_cell_angle_gamma                90
_cell_volume                     2279.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9936
_cell_measurement_theta_min      2.855
_cell_measurement_theta_max      27.093
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.370
_exptl_absorpt_coefficient_mu    0.236
_shelx_estimated_absorpt_T_min   0.895
_shelx_estimated_absorpt_T_max   0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8970
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_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            22697
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.855
_diffrn_reflns_theta_max         27.135
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2514
_reflns_number_gt                2252
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0423P)²+2.8165P] 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         2514
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0876
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
Cl Cl 1.0000 0.62732(4) 0.2500 0.02313(13) Uani 1 2 d S T P . .
Al Al 1.0000 0.83275(5) 0.2500 0.01501(14) Uani 1 2 d S T P . .
O O 0.89597(6) 0.90845(10) 0.24111(7) 0.0209(2) Uani 1 1 d . . . . .
N N 0.95642(8) 0.84319(10) 0.10391(8) 0.0155(2) Uani 1 1 d . . . . .
C1 C 1.01179(9) 0.81795(13) 0.04935(10) 0.0169(3) Uani 1 1 d . . . . .
C2 C 1.10173(10) 0.76825(13) 0.08355(11) 0.0209(3) Uani 1 1 d . . . . .
H2A H 1.1352 0.7482 0.1505 0.025 Uiso 1 1 calc R U . . .
C3 C 1.14071(11) 0.74903(15) 0.01551(12) 0.0256(3) Uani 1 1 d . . . . .
H3A H 1.2019 0.7144 0.0364 0.031 Uiso 1 1 calc R U . . .
C4 C 1.09189(12) 0.77951(16) -0.08228(12) 0.0302(4) Uani 1 1 d . . . . .
H4A H 1.1207 0.7673 -0.1268 0.036 Uiso 1 1 calc R U . . .
C5 C 1.00140(11) 0.82771(15) -0.11581(11) 0.0271(3) Uani 1 1 d . . . . .
H5A H 0.9679 0.8481 -0.1827 0.033 Uiso 1 1 calc R U . . .
C6 C 0.96138(10) 0.84520(13) -0.04905(10) 0.0198(3) Uani 1 1 d . . . . .
C7 C 0.86581(10) 0.88647(14) -0.06098(10) 0.0199(3) Uani 1 1 d . . . . .
H7A H 0.8168 0.8297 -0.1049 0.024 Uiso 1 1 calc R U . . .
H7B H 0.8526 0.9731 -0.0865 0.024 Uiso 1 1 calc R U . . .
C8 C 0.87269(9) 0.87859(12) 0.04236(10) 0.0162(3) Uani 1 1 d . . . . .
C9 C 0.79582(9) 0.90572(12) 0.07022(10) 0.0165(3) Uani 1 1 d . . . . .
C10 C 0.70390(9) 0.91800(13) -0.00194(10) 0.0201(3) Uani 1 1 d . . . . .
H10A H 0.6935 0.9118 -0.0689 0.024 Uiso 1 1 calc R U . . .
C11 C 0.62897(10) 0.93887(14) 0.02292(11) 0.0228(3) Uani 1 1 d . . . . .
H11A H 0.5674 0.9458 -0.0264 0.027 Uiso 1 1 calc R U . . .
C12 C 0.64415(10) 0.94982(14) 0.12107(11) 0.0242(3) Uani 1 1 d . . . . .
H12A H 0.5927 0.9642 0.1385 0.029 Uiso 1 1 calc R U . . .
C13 C 0.73376(10) 0.93983(14) 0.19316(11) 0.0231(3) Uani 1 1 d . . . . .
H13A H 0.7432 0.9484 0.2597 0.028 Uiso 1 1 calc R U . . .
C14 C 0.81091(9) 0.91723(13) 0.16937(10) 0.0178(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
Cl Al 2.1939(8) . ?
Al O 1.7672(10) 2_755 ?
Al O 1.7673(10) . ?
Al N 2.0146(11) . ?
Al N 2.0146(11) 2_755 ?
O C14 1.3326(15) . ?
N C8 1.3147(17) . ?
N C1 1.4304(17) . ?
C1 C6 1.3932(19) . ?
C1 C2 1.390(2) . ?
C2 C3 1.393(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.390(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.391(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.385(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.493(2) . ?
C7 C8 1.5082(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.4459(19) . ?
C9 C10 1.4118(18) . ?
C9 C14 1.4107(19) . ?
C10 C11 1.377(2) . ?
C10 H10A 0.9500 . ?
C11 C12 1.395(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.384(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.404(2) . ?
C13 H13A 0.9500 . ?

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
O Al O 125.55(8) 2_755 . ?
O Al N 87.51(5) 2_755 . ?
O Al N 89.59(5) . . ?
O Al N 89.59(5) 2_755 2_755 ?
O Al N 87.51(5) . 2_755 ?
N Al N 173.65(7) . 2_755 ?
O Al Cl 117.22(4) 2_755 . ?
O Al Cl 117.22(4) . . ?
N Al Cl 93.17(4) . . ?
N Al Cl 93.17(4) 2_755 . ?
C14 O Al 132.71(9) . . ?
C8 N C1 108.07(11) . . ?
C8 N Al 125.72(10) . . ?
C1 N Al 126.17(9) . . ?
C6 C1 C2 121.78(13) . . ?
C6 C1 N 110.49(12) . . ?
C2 C1 N 127.67(12) . . ?
C3 C2 C1 117.22(14) . . ?
C3 C2 H2A 121.4 . . ?
C1 C2 H2A 121.4 . . ?
C2 C3 C4 121.29(14) . . ?
C2 C3 H3A 119.4 . . ?
C4 C3 H3A 119.4 . . ?
C5 C4 C3 120.91(15) . . ?
C5 C4 H4A 119.5 . . ?
C3 C4 H4A 119.5 . . ?
C6 C5 C4 118.25(14) . . ?
C6 C5 H5A 120.9 . . ?
C4 C5 H5A 120.9 . . ?
C5 C6 C1 120.50(14) . . ?
C5 C6 C7 131.96(13) . . ?
C1 C6 C7 107.49(12) . . ?
C6 C7 C8 101.72(11) . . ?
C6 C7 H7A 111.4 . . ?
C8 C7 H7A 111.4 . . ?
C6 C7 H7B 111.4 . . ?
C8 C7 H7B 111.4 . . ?
H7A C7 H7B 109.3 . . ?
N C8 C9 124.00(12) . . ?
N C8 C7 112.14(12) . . ?
C9 C8 C7 123.86(12) . . ?
C10 C9 C14 119.09(13) . . ?
C10 C9 C8 120.09(12) . . ?
C14 C9 C8 120.80(12) . . ?
C11 C10 C9 121.19(13) . . ?
C11 C10 H10A 119.4 . . ?
C9 C10 H10A 119.4 . . ?
C10 C11 C12 119.54(13) . . ?
C10 C11 H11A 120.2 . . ?
C12 C11 H11A 120.2 . . ?
C13 C12 C11 120.40(14) . . ?
C13 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C12 C13 C14 120.92(14) . . ?
C12 C13 H13A 119.5 . . ?
C14 C13 H13A 119.5 . . ?
O C14 C13 118.92(13) . . ?
O C14 C9 122.23(12) . . ?
C13 C14 C9 118.85(12) . . ?

_refine_diff_density_max         0.321
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.050

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   C2/c
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

