# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_Zn-BCP
_database_code_depnum_ccdc_archive 'CCDC 1837110'
_audit_update_record             
;
2018-04-15 deposited with the CCDC.
2018-08-24 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         'C21 H12 N O7 Zn'
_chemical_formula_sum            'C21 H12 N O7 Zn'
_chemical_formula_weight         455.69

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'
Zn Zn 0.2839 1.4301 '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                   8.7799(7)
_cell_length_b                   9.6790(7)
_cell_length_c                   12.5229(11)
_cell_angle_alpha                109.152(7)
_cell_angle_beta                 96.773(7)
_cell_angle_gamma                99.480(6)
_cell_volume                     974.54(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2476
_cell_measurement_theta_min      2.4980
_cell_measurement_theta_max      29.5110

_exptl_crystal_description       needlelike
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_F_000             462
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    1.304
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76891
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7101
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.692
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             3320
_reflns_number_gt                2646
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0902P)²] 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         3320
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1475
_refine_ls_wR_factor_gt          0.1377
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
Zn1 Zn 0.48886(5) 0.52262(5) 0.75992(4) 0.0321(2) Uani 1 1 d . . . . .
O1 O 0.5491(3) 0.3291(3) 0.7072(2) 0.0339(7) Uani 1 1 d . . . . .
O4 O 0.3602(3) 0.5419(3) 0.8812(3) 0.0368(7) Uani 1 1 d . . . . .
O5 O 0.6840(3) 0.6709(3) 0.8482(3) 0.0364(7) Uani 1 1 d . . . . .
O6 O 0.6388(3) 0.8531(3) 0.7837(3) 0.0392(7) Uani 1 1 d . . . . .
O7 O 0.4038(3) 0.6314(3) 0.6614(2) 0.0365(7) Uani 1 1 d . . . . .
O2 O 0.6346(4) 0.4181(3) 0.5775(3) 0.0444(8) Uani 1 1 d . . . . .
N1 N 0.7756(4) 0.0069(4) 0.2292(3) 0.0289(8) Uani 1 1 d . . . . .
O3 O 0.1762(4) 0.3754(4) 0.7428(3) 0.0677(12) Uani 1 1 d . . . . .
C19 C 0.8674(5) 0.9025(4) 0.9232(3) 0.0278(9) Uani 1 1 d . . . . .
C4 C 0.8089(4) 0.0306(5) 0.4321(3) 0.0284(9) Uani 1 1 d . . . . .
C11 C 0.5589(4) 0.0014(4) 0.0486(3) 0.0278(9) Uani 1 1 d . . . . .
C7 C 0.6583(4) 0.0657(4) 0.6205(3) 0.0296(9) Uani 1 1 d . . . . .
H7 H 0.6098 0.0776 0.6841 0.036 Uiso 1 1 calc R U . . .
C3 C 0.7576(5) 0.1623(5) 0.4826(3) 0.0313(9) Uani 1 1 d . . . . .
H3 H 0.7756 0.2394 0.4537 0.038 Uiso 1 1 calc R U . . .
C15 C 0.1060(5) 0.4832(4) 0.9244(4) 0.0300(9) Uani 1 1 d . . . . .
C5 C 0.7824(5) -0.0826(4) 0.4769(3) 0.0293(9) Uani 1 1 d . . . . .
H5 H 0.8146 -0.1713 0.4436 0.035 Uiso 1 1 calc R U . . .
C8 C 0.8908(5) 0.0127(5) 0.3302(3) 0.0356(10) Uani 1 1 d . . . . .
C18 C 0.7195(5) 0.8016(4) 0.8439(3) 0.0296(9) Uani 1 1 d . . . . .
C9 C 0.7870(5) 0.1268(4) 0.1950(4) 0.0318(10) Uani 1 1 d . . . . .
H9 H 0.8674 0.2109 0.2329 0.038 Uiso 1 1 calc R U . . .
C10 C 0.6813(5) 0.1245(4) 0.1056(3) 0.0294(9) Uani 1 1 d . . . . .
H10 H 0.6913 0.2069 0.0823 0.035 Uiso 1 1 calc R U . . .
C2 C 0.6807(4) 0.1800(4) 0.5750(3) 0.0289(9) Uani 1 1 d . . . . .
C6 C 0.7082(5) -0.0647(5) 0.5710(4) 0.0341(10) Uani 1 1 d . . . . .
H6 H 0.6920 -0.1411 0.6008 0.041 Uiso 1 1 calc R U . . .
C13 C 0.6588(5) -0.1157(5) 0.1750(4) 0.0344(10) Uani 1 1 d . . . . .
H13 H 0.6514 -0.1969 0.1997 0.041 Uiso 1 1 calc R U . . .
C1 C 0.6176(5) 0.3187(5) 0.6216(4) 0.0331(10) Uani 1 1 d . . . . .
C14 C 0.2196(5) 0.4632(5) 0.8419(4) 0.0352(10) Uani 1 1 d . . . . .
C12 C 0.5525(5) -0.1216(4) 0.0850(4) 0.0316(10) Uani 1 1 d . . . . .
H12 H 0.4747 -0.2079 0.0471 0.038 Uiso 1 1 calc R U . . .
C17 C 0.1588(5) 0.5589(4) 1.0429(4) 0.0295(9) Uani 1 1 d . . . . .
H17 H 0.2653 0.5988 1.0717 0.035 Uiso 1 1 calc R U . . .
C21 C 0.9186(5) 1.0466(4) 0.9207(4) 0.0291(9) Uani 1 1 d . . . . .
H21 H 0.8642 1.0778 0.8677 0.035 Uiso 1 1 calc R U . . .
C20 C 0.9505(4) 0.8583(4) 1.0030(3) 0.0291(9) Uani 1 1 d . . . . .
H20 H 0.9173 0.7630 1.0050 0.035 Uiso 1 1 calc R U . . .
C16 C -0.0528(5) 0.4259(4) 0.8832(4) 0.0306(9) Uani 1 1 d . . . . .
H16 H -0.0888 0.3763 0.8047 0.037 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
Zn1 O1 1.954(3) . ?
Zn1 O4 1.976(3) . ?
Zn1 O5 1.980(3) . ?
Zn1 O7 2.020(3) . ?
O1 C1 1.274(5) . ?
O4 C14 1.283(5) . ?
O5 C18 1.272(5) . ?
O6 C18 1.247(5) . ?
O2 C1 1.254(5) . ?
N1 C13 1.351(5) . ?
N1 C9 1.355(5) . ?
N1 C8 1.504(5) . ?
O3 C14 1.223(5) . ?
C19 C20 1.387(5) . ?
C19 C21 1.405(5) . ?
C19 C18 1.506(6) . ?
C4 C5 1.385(6) . ?
C4 C3 1.398(6) . ?
C4 C8 1.513(6) . ?
C11 C10 1.387(5) . ?
C11 C12 1.403(5) . ?
C11 C11 1.492(8) 2_655 ?
C7 C6 1.379(6) . ?
C7 C2 1.398(5) . ?
C7 H7 0.9300 . ?
C3 C2 1.385(6) . ?
C3 H3 0.9300 . ?
C15 C16 1.380(6) . ?
C15 C17 1.401(6) . ?
C15 C14 1.509(6) . ?
C5 C6 1.389(6) . ?
C5 H5 0.9300 . ?
C9 C10 1.359(6) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C2 C1 1.502(6) . ?
C6 H6 0.9300 . ?
C13 C12 1.355(6) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?
C17 C16 1.379(6) 2_567 ?
C17 H17 0.9300 . ?
C21 C20 1.377(6) 2_777 ?
C21 H21 0.9300 . ?
C20 C21 1.377(6) 2_777 ?
C20 H20 0.9300 . ?
C16 C17 1.379(6) 2_567 ?
C16 H16 0.9300 . ?

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 Zn1 O4 113.23(12) . . ?
O1 Zn1 O5 105.81(12) . . ?
O4 Zn1 O5 100.56(12) . . ?
O1 Zn1 O7 127.15(12) . . ?
O4 Zn1 O7 105.90(12) . . ?
O5 Zn1 O7 100.19(12) . . ?
C1 O1 Zn1 109.8(3) . . ?
C14 O4 Zn1 112.4(3) . . ?
C18 O5 Zn1 123.7(3) . . ?
C13 N1 C9 120.4(3) . . ?
C13 N1 C8 120.0(3) . . ?
C9 N1 C8 119.6(3) . . ?
C20 C19 C21 119.1(4) . . ?
C20 C19 C18 121.1(3) . . ?
C21 C19 C18 119.8(4) . . ?
C5 C4 C3 118.7(4) . . ?
C5 C4 C8 121.0(4) . . ?
C3 C4 C8 120.3(4) . . ?
C10 C11 C12 117.0(4) . . ?
C10 C11 C11 121.5(4) . 2_655 ?
C12 C11 C11 121.4(4) . 2_655 ?
C6 C7 C2 120.0(4) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
C2 C3 C4 121.2(4) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C16 C15 C17 119.1(4) . . ?
C16 C15 C14 119.8(4) . . ?
C17 C15 C14 121.1(4) . . ?
C4 C5 C6 120.6(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
N1 C8 C4 108.8(3) . . ?
O6 C18 O5 125.3(4) . . ?
O6 C18 C19 118.5(3) . . ?
O5 C18 C19 116.1(4) . . ?
N1 C9 C10 120.2(4) . . ?
N1 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C11 121.1(4) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C3 C2 C7 119.2(4) . . ?
C3 C2 C1 119.5(4) . . ?
C7 C2 C1 121.3(4) . . ?
C7 C6 C5 120.3(4) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
N1 C13 C12 120.7(4) . . ?
N1 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
O2 C1 O1 123.0(4) . . ?
O2 C1 C2 120.4(4) . . ?
O1 C1 C2 116.6(4) . . ?
O3 C14 O4 123.1(4) . . ?
O3 C14 C15 120.1(4) . . ?
O4 C14 C15 116.8(4) . . ?
C13 C12 C11 120.5(4) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C16 C17 C15 120.1(4) 2_567 . ?
C16 C17 H17 120.0 2_567 . ?
C15 C17 H17 120.0 . . ?
C20 C21 C19 119.9(4) 2_777 . ?
C20 C21 H21 120.1 2_777 . ?
C19 C21 H21 120.1 . . ?
C21 C20 C19 121.0(4) 2_777 . ?
C21 C20 H20 119.5 2_777 . ?
C19 C20 H20 119.5 . . ?
C15 C16 C17 120.8(4) . 2_567 ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 2_567 . ?

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 C4 C3 C2 -0.5(6) . . . . ?
C8 C4 C3 C2 179.2(3) . . . . ?
C3 C4 C5 C6 -0.8(6) . . . . ?
C8 C4 C5 C6 179.5(4) . . . . ?
C13 N1 C8 C4 -72.1(4) . . . . ?
C9 N1 C8 C4 106.1(4) . . . . ?
C5 C4 C8 N1 113.1(4) . . . . ?
C3 C4 C8 N1 -66.6(5) . . . . ?
Zn1 O5 C18 O6 -0.8(6) . . . . ?
Zn1 O5 C18 C19 176.0(2) . . . . ?
C20 C19 C18 O6 171.3(4) . . . . ?
C21 C19 C18 O6 -5.5(5) . . . . ?
C20 C19 C18 O5 -5.6(5) . . . . ?
C21 C19 C18 O5 177.5(4) . . . . ?
C13 N1 C9 C10 -0.2(6) . . . . ?
C8 N1 C9 C10 -178.4(3) . . . . ?
N1 C9 C10 C11 0.9(6) . . . . ?
C12 C11 C10 C9 -2.0(6) . . . . ?
C11 C11 C10 C9 179.2(4) 2_655 . . . ?
C4 C3 C2 C7 1.9(6) . . . . ?
C4 C3 C2 C1 -175.8(4) . . . . ?
C6 C7 C2 C3 -2.1(6) . . . . ?
C6 C7 C2 C1 175.6(4) . . . . ?
C2 C7 C6 C5 0.8(6) . . . . ?
C4 C5 C6 C7 0.7(6) . . . . ?
C9 N1 C13 C12 0.8(6) . . . . ?
C8 N1 C13 C12 178.9(4) . . . . ?
Zn1 O1 C1 O2 -3.0(5) . . . . ?
Zn1 O1 C1 C2 176.3(3) . . . . ?
C3 C2 C1 O2 -0.1(6) . . . . ?
C7 C2 C1 O2 -177.8(4) . . . . ?
C3 C2 C1 O1 -179.5(4) . . . . ?
C7 C2 C1 O1 2.9(6) . . . . ?
Zn1 O4 C14 O3 6.6(6) . . . . ?
Zn1 O4 C14 C15 -173.2(3) . . . . ?
C16 C15 C14 O3 -12.6(6) . . . . ?
C17 C15 C14 O3 167.1(4) . . . . ?
C16 C15 C14 O4 167.2(4) . . . . ?
C17 C15 C14 O4 -13.1(6) . . . . ?
N1 C13 C12 C11 -1.9(6) . . . . ?
C10 C11 C12 C13 2.5(6) . . . . ?
C11 C11 C12 C13 -178.7(4) 2_655 . . . ?
C16 C15 C17 C16 0.6(6) . . . 2_567 ?
C14 C15 C17 C16 -179.2(3) . . . 2_567 ?
C20 C19 C21 C20 -0.1(6) . . . 2_777 ?
C18 C19 C21 C20 176.8(3) . . . 2_777 ?
C21 C19 C20 C21 0.1(6) . . . 2_777 ?
C18 C19 C20 C21 -176.8(3) . . . 2_777 ?
C17 C15 C16 C17 -0.6(6) . . . 2_567 ?
C14 C15 C16 C17 179.1(3) . . . 2_567 ?

_refine_diff_density_max         0.775
_refine_diff_density_min         -1.004
_refine_diff_density_rms         0.103



