# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1959893'
loop_
_audit_author_name
_audit_author_address
'Amrita Saha'
;Jadavpur University
India
;
_audit_update_record             
;
2019-10-17 deposited with the CCDC.	2020-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H18.50 Br4 Cl3 N4 O2 Zn'
_chemical_formula_weight         994.38

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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                   11.5856(9)
_cell_length_b                   12.9455(10)
_cell_length_c                   13.6796(10)
_cell_angle_alpha                80.891(3)
_cell_angle_beta                 66.130(3)
_cell_angle_gamma                63.965(3)
_cell_volume                     1685.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      1.751
_cell_measurement_theta_max      27.202

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.959
_exptl_crystal_F_000             963
_exptl_transmission_factor_min   0.6025
_exptl_transmission_factor_max   0.7425
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    5.747
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABAS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52107
_diffrn_reflns_av_unetI/netI     0.1594
_diffrn_reflns_av_R_equivalents  0.2031
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.751
_diffrn_reflns_theta_max         27.202
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             7292
_reflns_number_gt                3548
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+14.0784P] 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         7292
_refine_ls_number_parameters     424
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2214
_refine_ls_R_factor_gt           0.1150
_refine_ls_wR_factor_ref         0.1781
_refine_ls_wR_factor_gt          0.1490
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_restrained_S_all      1.159
_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
Br3 Br 0.24112(15) 0.70132(14) 0.83989(11) 0.0767(5) Uani 1 1 d . . . . .
Br2 Br 0.45187(14) 0.99089(12) 0.32160(13) 0.0749(5) Uani 1 1 d . . . . .
Br1 Br 0.94650(14) 0.62083(14) 0.10427(12) 0.0759(5) Uani 1 1 d . . . . .
Br4 Br -0.30776(17) 1.02493(14) 1.00666(11) 0.0930(6) Uani 1 1 d . . . . .
Zn Zn 0.21795(12) 0.72076(11) 0.47990(9) 0.0339(3) Uani 1 1 d . . . . .
Cl3 Cl -0.3481(6) 0.5723(6) 1.0176(5) 0.157(2) Uani 1 1 d . . . . .
Cl1 Cl -0.4337(6) 0.6677(6) 0.8472(5) 0.169(3) Uani 1 1 d . . . . .
O1 O 0.3500(7) 0.8008(6) 0.4100(6) 0.0425(19) Uani 1 1 d . . . . .
O2 O 0.1921(7) 0.7466(6) 0.6326(5) 0.0416(19) Uani 1 1 d . . . . .
N4 N 0.0183(8) 0.8564(7) 0.5092(6) 0.030(2) Uani 1 1 d . . . . .
N2 N 0.3923(9) 0.5607(7) 0.4259(7) 0.035(2) Uani 1 1 d . . . . .
Cl2 Cl -0.2685(9) 0.7391(7) 0.8938(6) 0.213(4) Uani 1 1 d . . . . .
N1 N 0.1293(8) 0.5923(8) 0.5432(6) 0.037(2) Uani 1 1 d . . . . .
N3 N 0.1878(9) 0.7340(8) 0.3275(6) 0.040(2) Uani 1 1 d . . . . .
C24 C -0.0280(11) 0.8851(9) 0.4226(8) 0.033(2) Uani 1 1 d . . . . .
C25 C -0.1525(11) 0.9708(9) 0.4232(9) 0.042(3) Uani 1 1 d . . . . .
H25 H -0.215918 1.015775 0.484716 0.051 Uiso 1 1 calc R U . . .
C9 C 0.2241(10) 0.4824(9) 0.5166(8) 0.036(3) Uani 1 1 d . . . . .
C11 C 0.5624(10) 0.6389(9) 0.3218(8) 0.038(3) Uani 1 1 d . . . . .
C23 C -0.0672(11) 0.9086(9) 0.6011(8) 0.039(3) Uani 1 1 d . . . . .
H23 H -0.152145 0.966069 0.603002 0.047 Uiso 1 1 calc R U . . .
C32 C 0.0663(11) 0.8206(9) 0.3270(8) 0.035(3) Uani 1 1 d . . . . .
C16 C 0.4768(11) 0.7590(9) 0.3454(8) 0.039(3) Uani 1 1 d . . . . .
C8 C 0.3629(11) 0.4617(9) 0.4543(8) 0.036(3) Uani 1 1 d . . . . .
C19 C -0.0343(12) 0.8617(10) 0.9004(9) 0.050(3) Uani 1 1 d . . . . .
H19 H -0.031133 0.852171 0.968213 0.060 Uiso 1 1 calc R U . . .
C21 C -0.1578(11) 0.9514(10) 0.7876(8) 0.046(3) Uani 1 1 d . . . . .
H21 H -0.238711 1.004104 0.778624 0.056 Uiso 1 1 calc R U . . .
C22 C -0.0455(10) 0.8878(9) 0.6994(8) 0.036(3) Uani 1 1 d . . . . .
C26 C -0.1833(12) 0.9900(10) 0.3318(10) 0.051(3) Uani 1 1 d . . . . .
H26 H -0.268374 1.047258 0.333806 0.061 Uiso 1 1 calc R U . . .
C15 C 0.5468(11) 0.8313(9) 0.2909(8) 0.041(3) Uani 1 1 d . . . . .
C10 C 0.5154(11) 0.5506(9) 0.3654(8) 0.039(3) Uani 1 1 d . . . . .
H10 H 0.582667 0.475652 0.347846 0.047 Uiso 1 1 calc R U . . .
C17 C 0.0812(11) 0.8065(9) 0.7101(8) 0.038(3) Uani 1 1 d . . . . .
C13 C 0.7584(11) 0.6766(11) 0.2016(9) 0.049(3) Uani 1 1 d . . . . .
C28 C 0.0357(12) 0.8408(10) 0.2341(8) 0.040(3) Uani 1 1 d . . . . .
C14 C 0.6810(12) 0.7924(10) 0.2220(9) 0.049(3) Uani 1 1 d . . . . .
H14 H 0.720388 0.844000 0.188701 0.059 Uiso 1 1 calc R U . . .
C31 C 0.2757(12) 0.6729(10) 0.2396(9) 0.051(3) Uani 1 1 d . . . . .
H31 H 0.358292 0.613990 0.240741 0.061 Uiso 1 1 calc R U . . .
C18 C 0.0785(12) 0.7992(10) 0.8167(9) 0.048(3) Uani 1 1 d . . . . .
C1 C 0.0013(12) 0.6126(10) 0.6041(9) 0.051(3) Uani 1 1 d . . . . .
H1 H -0.062896 0.688392 0.622012 0.061 Uiso 1 1 calc R U . . .
C6 C 0.4192(13) 0.2582(10) 0.4587(10) 0.056(3) Uani 1 1 d . . . . .
H6 H 0.485179 0.183777 0.436105 0.067 Uiso 1 1 calc R U . . .
C4 C 0.1849(12) 0.3884(10) 0.5517(9) 0.045(3) Uani 1 1 d . . . . .
C20 C -0.1531(12) 0.9389(10) 0.8863(9) 0.051(3) Uani 1 1 d . . . . .
C12 C 0.7030(11) 0.6002(10) 0.2506(9) 0.045(3) Uani 1 1 d . . . . .
H12 H 0.757678 0.521777 0.237295 0.055 Uiso 1 1 calc R U . . .
C3 C 0.0456(13) 0.4153(12) 0.6183(10) 0.057(3) Uani 1 1 d . . . . .
H3 H 0.015754 0.356768 0.644488 0.069 Uiso 1 1 calc R U . . .
C7 C 0.4585(12) 0.3503(10) 0.4271(9) 0.050(3) Uani 1 1 d . . . . .
H7 H 0.551085 0.335476 0.386887 0.060 Uiso 1 1 calc R U . . .
C27 C -0.0944(13) 0.9289(11) 0.2414(9) 0.052(3) Uani 1 1 d . . . . .
H27 H -0.118702 0.944712 0.181912 0.062 Uiso 1 1 calc R U . . .
C29 C 0.1335(14) 0.7739(12) 0.1434(9) 0.060(4) Uani 1 1 d . . . . .
H29 H 0.115885 0.786742 0.080929 0.072 Uiso 1 1 calc R U . . .
C30 C 0.2536(13) 0.6906(12) 0.1450(10) 0.063(4) Uani 1 1 d . . . . .
H30 H 0.320255 0.645852 0.084182 0.075 Uiso 1 1 calc R U . . .
C5 C 0.2880(13) 0.2758(11) 0.5210(10) 0.056(3) Uani 1 1 d . . . . .
H5 H 0.264816 0.213429 0.543965 0.067 Uiso 1 1 calc R U . . .
C2 C -0.0435(13) 0.5243(12) 0.6437(10) 0.064(4) Uani 1 1 d . . . . .
H2 H -0.135765 0.542067 0.687851 0.077 Uiso 1 1 calc R U . . .
C33 C -0.391(3) 0.692(2) 0.950(2) 0.180(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
Br3 C18 1.875(11) . ?
Br2 C15 1.887(11) . ?
Br1 C13 1.902(10) . ?
Br4 C20 1.898(11) . ?
Zn O2 2.047(7) . ?
Zn O1 2.055(7) . ?
Zn N4 2.121(8) . ?
Zn N2 2.126(8) . ?
Zn N1 2.212(8) . ?
Zn N3 2.218(8) . ?
Cl3 C33 1.657(19) . ?
Cl1 C33 1.77(2) . ?
O1 C16 1.279(12) . ?
O2 C17 1.288(11) . ?
N4 C23 1.300(12) . ?
N4 C24 1.425(12) . ?
N2 C10 1.285(12) . ?
N2 C8 1.424(12) . ?
Cl2 C33 1.65(2) . ?
N1 C1 1.300(12) . ?
N1 C9 1.353(12) . ?
N3 C31 1.308(12) . ?
N3 C32 1.363(12) . ?
C24 C25 1.379(13) . ?
C24 C32 1.410(13) . ?
C25 C26 1.392(14) . ?
C9 C8 1.403(13) . ?
C9 C4 1.429(14) . ?
C11 C12 1.416(13) . ?
C11 C10 1.425(13) . ?
C11 C16 1.432(14) . ?
C23 C22 1.430(14) . ?
C32 C28 1.410(13) . ?
C16 C15 1.430(14) . ?
C8 C7 1.370(14) . ?
C19 C18 1.352(14) . ?
C19 C20 1.370(15) . ?
C21 C20 1.355(14) . ?
C21 C22 1.389(13) . ?
C22 C17 1.433(14) . ?
C26 C27 1.335(15) . ?
C15 C14 1.355(14) . ?
C17 C18 1.435(14) . ?
C13 C12 1.356(14) . ?
C13 C14 1.370(15) . ?
C28 C29 1.384(15) . ?
C28 C27 1.410(15) . ?
C31 C30 1.384(15) . ?
C1 C2 1.403(15) . ?
C6 C5 1.341(15) . ?
C6 C7 1.404(15) . ?
C4 C3 1.405(15) . ?
C4 C5 1.410(15) . ?
C3 C2 1.328(16) . ?
C29 C30 1.342(16) . ?

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 Zn O1 94.4(3) . . ?
O2 Zn N4 88.1(3) . . ?
O1 Zn N4 103.7(3) . . ?
O2 Zn N2 106.0(3) . . ?
O1 Zn N2 88.3(3) . . ?
N4 Zn N2 160.9(3) . . ?
O2 Zn N1 88.1(3) . . ?
O1 Zn N1 164.4(3) . . ?
N4 Zn N1 91.7(3) . . ?
N2 Zn N1 76.3(3) . . ?
O2 Zn N3 163.9(3) . . ?
O1 Zn N3 89.1(3) . . ?
N4 Zn N3 75.8(3) . . ?
N2 Zn N3 89.8(3) . . ?
N1 Zn N3 92.8(3) . . ?
C16 O1 Zn 129.2(7) . . ?
C17 O2 Zn 129.2(7) . . ?
C23 N4 C24 118.3(9) . . ?
C23 N4 Zn 125.1(7) . . ?
C24 N4 Zn 116.4(6) . . ?
C10 N2 C8 120.3(9) . . ?
C10 N2 Zn 124.2(7) . . ?
C8 N2 Zn 115.4(6) . . ?
C1 N1 C9 119.5(10) . . ?
C1 N1 Zn 126.8(8) . . ?
C9 N1 Zn 113.6(6) . . ?
C31 N3 C32 118.6(9) . . ?
C31 N3 Zn 127.1(8) . . ?
C32 N3 Zn 114.2(7) . . ?
C25 C24 C32 118.2(10) . . ?
C25 C24 N4 126.2(9) . . ?
C32 C24 N4 115.6(9) . . ?
C24 C25 C26 119.9(11) . . ?
N1 C9 C8 118.9(10) . . ?
N1 C9 C4 121.0(9) . . ?
C8 C9 C4 120.1(10) . . ?
C12 C11 C10 115.1(10) . . ?
C12 C11 C16 120.9(10) . . ?
C10 C11 C16 124.0(10) . . ?
N4 C23 C22 127.4(10) . . ?
N3 C32 C24 118.0(9) . . ?
N3 C32 C28 120.1(10) . . ?
C24 C32 C28 121.9(10) . . ?
O1 C16 C15 121.5(10) . . ?
O1 C16 C11 124.8(10) . . ?
C15 C16 C11 113.8(10) . . ?
C7 C8 C9 118.7(10) . . ?
C7 C8 N2 125.4(10) . . ?
C9 C8 N2 115.9(9) . . ?
C18 C19 C20 120.7(11) . . ?
C20 C21 C22 122.0(11) . . ?
C21 C22 C23 115.6(10) . . ?
C21 C22 C17 120.5(10) . . ?
C23 C22 C17 123.9(9) . . ?
C27 C26 C25 122.0(11) . . ?
C14 C15 C16 124.3(11) . . ?
C14 C15 Br2 116.8(9) . . ?
C16 C15 Br2 118.8(8) . . ?
N2 C10 C11 128.6(10) . . ?
O2 C17 C22 125.0(9) . . ?
O2 C17 C18 120.8(10) . . ?
C22 C17 C18 114.1(10) . . ?
C12 C13 C14 120.9(10) . . ?
C12 C13 Br1 119.0(9) . . ?
C14 C13 Br1 120.1(9) . . ?
C29 C28 C27 124.8(11) . . ?
C29 C28 C32 118.6(11) . . ?
C27 C28 C32 116.6(10) . . ?
C15 C14 C13 119.7(11) . . ?
N3 C31 C30 124.1(12) . . ?
C19 C18 C17 123.2(11) . . ?
C19 C18 Br3 118.5(9) . . ?
C17 C18 Br3 118.3(8) . . ?
N1 C1 C2 122.4(11) . . ?
C5 C6 C7 121.1(12) . . ?
C3 C4 C5 124.5(11) . . ?
C3 C4 C9 117.0(11) . . ?
C5 C4 C9 118.5(11) . . ?
C21 C20 C19 119.5(11) . . ?
C21 C20 Br4 121.7(9) . . ?
C19 C20 Br4 118.8(9) . . ?
C13 C12 C11 120.4(11) . . ?
C2 C3 C4 120.0(11) . . ?
C8 C7 C6 121.2(11) . . ?
C26 C27 C28 121.3(11) . . ?
C30 C29 C28 120.3(11) . . ?
C29 C30 C31 118.3(12) . . ?
C6 C5 C4 120.4(12) . . ?
C3 C2 C1 120.0(12) . . ?
Cl2 C33 Cl3 114.3(13) . . ?
Cl2 C33 Cl1 108.0(14) . . ?
Cl3 C33 Cl1 109.4(14) . . ?

_refine_diff_density_max         0.825
_refine_diff_density_min         -0.809
_refine_diff_density_rms         0.124

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1959894'
loop_
_audit_author_name
_audit_author_address
'Amrita Saha'
;Jadavpur University
India
;
_audit_update_record             
;
2019-10-17 deposited with the CCDC.	2020-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H20 Al N7 O9'
_chemical_formula_weight         673.53

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'
Al Al 0.0645 0.0514 '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                   12.5503(9)
_cell_length_b                   14.1977(10)
_cell_length_c                   16.8800(12)
_cell_angle_alpha                90
_cell_angle_beta                 101.622(2)
_cell_angle_gamma                90
_cell_volume                     2946.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    6508
_cell_measurement_theta_min      1.891
_cell_measurement_theta_max      27.110

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_F_000             1384
_exptl_transmission_factor_min   0.6434
_exptl_transmission_factor_max   0.7543
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.141
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42415
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.891
_diffrn_reflns_theta_max         27.110
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             6465
_reflns_number_gt                5168
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.2000P)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_number_reflns         6465
_refine_ls_number_parameters     450
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0936
_refine_ls_wR_factor_ref         0.3438
_refine_ls_wR_factor_gt          0.3187
_refine_ls_goodness_of_fit_ref   1.510
_refine_ls_restrained_S_all      1.510
_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
Al Al 0.37448(6) 0.44232(6) 0.73015(5) 0.0425(3) Uani 1 1 d . . . . .
O2 O 0.28746(16) 0.39714(16) 0.79590(14) 0.0569(6) Uani 1 1 d . . . . .
O1 O 0.36120(17) 0.33896(14) 0.66563(14) 0.0564(6) Uani 1 1 d . . . . .
N1 N 0.4099(2) 0.55318(16) 0.80776(15) 0.0463(6) Uani 1 1 d . . . . .
N2 N 0.50992(17) 0.39296(15) 0.79989(13) 0.0406(5) Uani 1 1 d . . . . .
N3 N 0.4579(2) 0.51213(17) 0.65595(14) 0.0464(6) Uani 1 1 d . . . . .
N4 N 0.24881(19) 0.50443(16) 0.65803(15) 0.0464(6) Uani 1 1 d . . . . .
C6 C 0.5229(2) 0.2536(2) 0.72013(18) 0.0457(6) Uani 1 1 d . . . . .
C1 C 0.4246(2) 0.26843(19) 0.66192(18) 0.0471(6) Uani 1 1 d . . . . .
C7 C 0.5582(2) 0.3162(2) 0.78808(17) 0.0445(6) Uani 1 1 d . . . . .
C8 C 0.5538(2) 0.45163(19) 0.86763(16) 0.0417(6) Uani 1 1 d . . . . .
C17 C 0.4987(2) 0.5376(2) 0.86785(17) 0.0442(6) Uani 1 1 d . . . . .
C24 C 0.1472(2) 0.4881(2) 0.65935(19) 0.0486(7) Uani 1 1 d . . . . .
O4 O 0.6053(3) -0.0182(2) 0.5880(2) 0.0946(10) Uani 1 1 d . . . . .
N5 N 0.6356(3) 0.0396(2) 0.6409(2) 0.0751(9) Uani 1 1 d . . . . .
C25 C 0.2782(3) 0.5624(2) 0.59694(19) 0.0495(7) Uani 1 1 d . . . . .
C2 C 0.3983(3) 0.2013(2) 0.5990(2) 0.0573(8) Uani 1 1 d . . . . .
H2 H 0.333750 0.207850 0.561153 0.069 Uiso 1 1 calc R U . . .
C9 C 0.6402(3) 0.4312(2) 0.92883(19) 0.0544(7) Uani 1 1 d . . . . .
H9 H 0.676516 0.374055 0.929183 0.065 Uiso 1 1 calc R U . . .
C16 C 0.3554(3) 0.6327(2) 0.8086(2) 0.0552(7) Uani 1 1 d . . . . .
H16 H 0.295451 0.643411 0.767231 0.066 Uiso 1 1 calc R U . . .
C29 C 0.4327(3) 0.6171(2) 0.5404(2) 0.0588(8) Uani 1 1 d . . . . .
C3 C 0.4645(3) 0.1280(3) 0.5924(2) 0.0615(8) Uani 1 1 d . . . . .
H3 H 0.445515 0.085211 0.550179 0.074 Uiso 1 1 calc R U . . .
C23 C 0.1106(2) 0.4311(2) 0.7180(2) 0.0523(7) Uani 1 1 d . . . . .
O6 O -0.1865(3) 0.2888(3) 0.8045(3) 0.1213(14) Uani 1 1 d . . . . .
C27 C 0.2503(4) 0.6657(3) 0.4824(2) 0.0778(11) Uani 1 1 d . . . . .
H27 H 0.202485 0.699589 0.443475 0.093 Uiso 1 1 calc R U . . .
C26 C 0.2088(3) 0.6135(3) 0.5399(2) 0.0651(9) Uani 1 1 d . . . . .
H26 H 0.134552 0.613517 0.539333 0.078 Uiso 1 1 calc R U . . .
C28 C 0.3584(4) 0.6681(3) 0.4821(2) 0.0720(10) Uani 1 1 d . . . . .
H28 H 0.383534 0.703587 0.443325 0.086 Uiso 1 1 calc R U . . .
C4 C 0.5614(3) 0.1166(2) 0.6489(2) 0.0569(8) Uani 1 1 d . . . . .
C14 C 0.3836(3) 0.7022(2) 0.8689(2) 0.0653(9) Uani 1 1 d . . . . .
H14 H 0.342339 0.756804 0.867682 0.078 Uiso 1 1 calc R U . . .
C10 C 0.6738(3) 0.4968(3) 0.9909(2) 0.0618(9) Uani 1 1 d . . . . .
H10 H 0.732521 0.482527 1.032264 0.074 Uiso 1 1 calc R U . . .
C13 C 0.4720(3) 0.6879(2) 0.9286(2) 0.0628(9) Uani 1 1 d . . . . .
H13 H 0.492173 0.733433 0.968462 0.075 Uiso 1 1 calc R U . . .
C11 C 0.6218(3) 0.5816(3) 0.9918(2) 0.0624(9) Uani 1 1 d . . . . .
H11 H 0.645685 0.624022 1.033615 0.075 Uiso 1 1 calc R U . . .
C19 C 0.1383(3) 0.3315(3) 0.8388(3) 0.0691(10) Uani 1 1 d . . . . .
H19 H 0.184450 0.303274 0.882332 0.083 Uiso 1 1 calc R U . . .
C31 C 0.6113(3) 0.5643(3) 0.6041(2) 0.0667(9) Uani 1 1 d . . . . .
H31 H 0.686356 0.563723 0.608157 0.080 Uiso 1 1 calc R U . . .
N6 N -0.1566(3) 0.3415(3) 0.7530(3) 0.0912(12) Uani 1 1 d . . . . .
C30 C 0.5464(3) 0.6152(3) 0.5446(2) 0.0689(10) Uani 1 1 d . . . . .
H30 H 0.576760 0.648378 0.507053 0.083 Uiso 1 1 calc R U . . .
C22 C -0.0017(3) 0.4153(3) 0.7087(2) 0.0615(9) Uani 1 1 d . . . . .
H22 H -0.050060 0.442247 0.665645 0.074 Uiso 1 1 calc R U . . .
C20 C 0.0298(3) 0.3185(3) 0.8288(3) 0.0743(11) Uani 1 1 d . . . . .
H20 H 0.001669 0.282045 0.865505 0.089 Uiso 1 1 calc R U . . .
C21 C -0.0396(3) 0.3596(3) 0.7635(3) 0.0696(10) Uani 1 1 d . . . . .
N100 N 0.3868(3) 0.8603(2) 1.0552(2) 0.0669(8) Uani 1 1 d . . . . .
C5 C 0.5897(2) 0.1778(2) 0.7126(2) 0.0529(7) Uani 1 1 d . . . . .
H5 H 0.653606 0.168362 0.750587 0.064 Uiso 1 1 calc R U . . .
C18 C 0.1834(2) 0.3878(2) 0.7839(2) 0.0511(7) Uani 1 1 d . . . . .
C12 C 0.5334(3) 0.6048(2) 0.93075(19) 0.0534(7) Uani 1 1 d . . . . .
C32 C 0.5640(3) 0.5129(2) 0.6591(2) 0.0559(8) Uani 1 1 d . . . . .
H32 H 0.608832 0.478198 0.699164 0.067 Uiso 1 1 calc R U . . .
C33 C 0.3916(3) 0.5639(2) 0.59729(18) 0.0487(7) Uani 1 1 d . . . . .
O5 O -0.2178(2) 0.3762(4) 0.6979(2) 0.1165(14) Uani 1 1 d . . . . .
O3 O 0.7213(3) 0.0360(3) 0.6852(2) 0.1189(15) Uani 1 1 d . . . . .
O103 O 0.3090(3) 0.8063(3) 1.0481(3) 0.1153(13) Uani 1 1 d . . . . .
O101 O 0.4769(5) 0.8247(4) 1.0931(4) 0.154(2) Uani 1 1 d . . . . .
O102 O 0.4305(5) 0.8977(5) 1.0025(4) 0.174(2) Uani 1 1 d . . . . .
H7 H 0.610(3) 0.289(2) 0.827(2) 0.056(9) Uiso 1 1 d . . . . .
H24 H 0.090(3) 0.521(2) 0.6246(19) 0.040(7) Uiso 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
Al O1 1.815(2) . ?
Al O2 1.823(2) . ?
Al N2 1.990(2) . ?
Al N4 1.993(2) . ?
Al N1 2.039(3) . ?
Al N3 2.044(3) . ?
O2 C18 1.288(4) . ?
O1 C1 1.289(3) . ?
N1 C16 1.321(4) . ?
N1 C17 1.365(4) . ?
N2 C7 1.282(4) . ?
N2 C8 1.432(3) . ?
N3 C32 1.321(4) . ?
N3 C33 1.372(4) . ?
N4 C24 1.301(4) . ?
N4 C25 1.425(4) . ?
C6 C5 1.386(4) . ?
C6 C1 1.430(4) . ?
C6 C7 1.448(4) . ?
C1 C2 1.416(4) . ?
C8 C9 1.370(4) . ?
C8 C17 1.403(4) . ?
C17 C12 1.428(4) . ?
C24 C23 1.424(5) . ?
O4 N5 1.215(4) . ?
N5 O3 1.181(5) . ?
N5 C4 1.460(4) . ?
C25 C26 1.368(4) . ?
C25 C33 1.421(4) . ?
C2 C3 1.349(5) . ?
C9 C10 1.402(5) . ?
C16 C14 1.411(5) . ?
C29 C33 1.399(5) . ?
C29 C28 1.412(5) . ?
C29 C30 1.415(6) . ?
C3 C4 1.396(5) . ?
C23 C22 1.404(4) . ?
C23 C18 1.429(4) . ?
O6 N6 1.260(6) . ?
C27 C28 1.358(6) . ?
C27 C26 1.402(6) . ?
C4 C5 1.371(5) . ?
C14 C13 1.356(5) . ?
C10 C11 1.371(5) . ?
C13 C12 1.407(5) . ?
C11 C12 1.393(5) . ?
C19 C20 1.351(5) . ?
C19 C18 1.424(5) . ?
C31 C30 1.366(6) . ?
C31 C32 1.403(5) . ?
N6 O5 1.187(5) . ?
N6 C21 1.467(5) . ?
C22 C21 1.373(6) . ?
C20 C21 1.388(6) . ?
N100 O103 1.229(5) . ?
N100 O102 1.254(6) . ?
N100 O101 1.286(6) . ?

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 Al O2 94.99(12) . . ?
O1 Al N2 91.97(10) . . ?
O2 Al N2 93.50(10) . . ?
O1 Al N4 91.46(10) . . ?
O2 Al N4 91.73(10) . . ?
N2 Al N4 173.47(10) . . ?
O1 Al N1 172.54(10) . . ?
O2 Al N1 87.72(11) . . ?
N2 Al N1 80.91(10) . . ?
N4 Al N1 95.41(10) . . ?
O1 Al N3 91.19(11) . . ?
O2 Al N3 170.91(11) . . ?
N2 Al N3 92.93(10) . . ?
N4 Al N3 81.44(10) . . ?
N1 Al N3 86.96(10) . . ?
C18 O2 Al 130.8(2) . . ?
C1 O1 Al 132.42(18) . . ?
C16 N1 C17 118.5(3) . . ?
C16 N1 Al 128.3(2) . . ?
C17 N1 Al 113.10(19) . . ?
C7 N2 C8 120.1(2) . . ?
C7 N2 Al 125.58(19) . . ?
C8 N2 Al 114.36(17) . . ?
C32 N3 C33 119.0(3) . . ?
C32 N3 Al 128.0(2) . . ?
C33 N3 Al 113.0(2) . . ?
C24 N4 C25 120.9(2) . . ?
C24 N4 Al 124.6(2) . . ?
C25 N4 Al 114.14(19) . . ?
C5 C6 C1 120.4(3) . . ?
C5 C6 C7 117.1(3) . . ?
C1 C6 C7 122.5(3) . . ?
O1 C1 C2 120.5(3) . . ?
O1 C1 C6 122.5(3) . . ?
C2 C1 C6 117.1(3) . . ?
N2 C7 C6 124.5(2) . . ?
C9 C8 C17 119.9(3) . . ?
C9 C8 N2 126.7(3) . . ?
C17 C8 N2 113.5(2) . . ?
N1 C17 C8 117.9(2) . . ?
N1 C17 C12 121.7(3) . . ?
C8 C17 C12 120.4(3) . . ?
N4 C24 C23 124.6(3) . . ?
O3 N5 O4 123.1(4) . . ?
O3 N5 C4 119.3(3) . . ?
O4 N5 C4 117.6(3) . . ?
C26 C25 C33 119.4(3) . . ?
C26 C25 N4 126.4(3) . . ?
C33 C25 N4 114.2(3) . . ?
C3 C2 C1 121.8(3) . . ?
C8 C9 C10 119.7(3) . . ?
N1 C16 C14 123.4(3) . . ?
C33 C29 C28 118.2(4) . . ?
C33 C29 C30 117.6(3) . . ?
C28 C29 C30 124.2(3) . . ?
C2 C3 C4 119.9(3) . . ?
C22 C23 C24 118.1(3) . . ?
C22 C23 C18 119.2(3) . . ?
C24 C23 C18 122.7(3) . . ?
C28 C27 C26 121.8(3) . . ?
C25 C26 C27 119.6(4) . . ?
C27 C28 C29 120.3(3) . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 N5 118.5(3) . . ?
C3 C4 N5 120.5(3) . . ?
C13 C14 C16 118.7(3) . . ?
C11 C10 C9 121.3(3) . . ?
C14 C13 C12 120.4(3) . . ?
C10 C11 C12 120.6(3) . . ?
C20 C19 C18 121.2(3) . . ?
C30 C31 C32 119.5(3) . . ?
O5 N6 O6 123.5(4) . . ?
O5 N6 C21 119.7(4) . . ?
O6 N6 C21 116.8(4) . . ?
C31 C30 C29 119.5(3) . . ?
C21 C22 C23 119.5(3) . . ?
C19 C20 C21 119.8(4) . . ?
C22 C21 C20 122.0(3) . . ?
C22 C21 N6 119.6(4) . . ?
C20 C21 N6 118.4(4) . . ?
O103 N100 O102 130.3(5) . . ?
O103 N100 O101 113.9(4) . . ?
O102 N100 O101 93.1(5) . . ?
C4 C5 C6 119.9(3) . . ?
O2 C18 C19 118.6(3) . . ?
O2 C18 C23 123.2(3) . . ?
C19 C18 C23 118.2(3) . . ?
C11 C12 C13 124.6(3) . . ?
C11 C12 C17 118.1(3) . . ?
C13 C12 C17 117.2(3) . . ?
N3 C32 C31 122.4(3) . . ?
N3 C33 C29 122.1(3) . . ?
N3 C33 C25 117.2(3) . . ?
C29 C33 C25 120.8(3) . . ?

_refine_diff_density_max         1.888
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.099

