# Electronic Supplementary Material (ESI) for Analyst.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 978113'
_audit_update_record             
;
2014-04-16 deposited with the CCDC.
2015-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H24 Cl4 N2 O2 Zn'
_chemical_formula_sum            'C30 H24 Cl4 N2 O2 Zn'
_chemical_formula_weight         651.68

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   21.692(8)
_cell_length_b                   4.8468(16)
_cell_length_c                   28.611(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.442(16)
_cell_angle_gamma                90.00
_cell_volume                     2799.9(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328
_exptl_absorpt_coefficient_mu    1.291
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10474
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         27.96
_reflns_number_total             3305
_reflns_number_gt                2806
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0406P)²+1.8282P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3305
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0825
_refine_ls_wR_factor_gt          0.0781
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.08709(8) -0.0833(4) 0.19772(6) 0.0303(4) Uani 1 1 d . . .
C2 C 1.09882(9) -0.1699(4) 0.15437(6) 0.0319(4) Uani 1 1 d . . .
C3 C 1.14773(9) -0.0605(4) 0.14045(7) 0.0354(4) Uani 1 1 d . . .
H3 H 1.1537 -0.1223 0.1116 0.042 Uiso 1 1 calc R . .
C4 C 1.18816(9) 0.1428(4) 0.16985(7) 0.0364(4) Uani 1 1 d . . .
C5 C 1.13013(8) 0.1259(4) 0.22677(6) 0.0322(4) Uani 1 1 d . . .
C6 C 1.18048(9) 0.2341(4) 0.21228(7) 0.0373(4) Uani 1 1 d . . .
H6 H 1.2087 0.3690 0.2318 0.045 Uiso 1 1 calc R . .
C7 C 0.87397(9) 0.2416(4) 0.22784(6) 0.0359(4) Uani 1 1 d . . .
H7 H 0.8400 0.3599 0.2096 0.043 Uiso 1 1 calc R . .
C8 C 0.88199(11) 0.2444(4) 0.07013(7) 0.0434(5) Uani 1 1 d . . .
C9 C 0.91238(10) 0.3288(4) 0.16228(7) 0.0395(4) Uani 1 1 d . . .
H9A H 0.9548 0.4020 0.1641 0.047 Uiso 1 1 calc R . .
H9B H 0.8813 0.4811 0.1558 0.047 Uiso 1 1 calc R . .
C10 C 0.88766(13) 0.1204(5) 0.11969(7) 0.0538(6) Uani 1 1 d . . .
H10A H 0.9179 -0.0348 0.1270 0.065 Uiso 1 1 calc R . .
H10B H 0.8447 0.0519 0.1174 0.065 Uiso 1 1 calc R . .
C11 C 0.92689(12) 0.1794(5) 0.04820(8) 0.0537(6) Uani 1 1 d . . .
H11 H 0.9603 0.0528 0.0638 0.064 Uiso 1 1 calc R . .
C12 C 0.87530(15) 0.4816(5) -0.01979(9) 0.0649(7) Uani 1 1 d . . .
H12 H 0.8731 0.5609 -0.0500 0.078 Uiso 1 1 calc R . .
C13 C 0.83351(15) 0.4313(7) 0.04565(9) 0.0733(8) Uani 1 1 d . . .
H13 H 0.8022 0.4791 0.0594 0.088 Uiso 1 1 calc R . .
C14 C 0.92324(13) 0.2979(6) 0.00373(8) 0.0603(6) Uani 1 1 d . . .
H14 H 0.9542 0.2508 -0.0104 0.072 Uiso 1 1 calc R . .
C15 C 0.83024(17) 0.5499(7) 0.00092(10) 0.0891(11) Uani 1 1 d . . .
H15 H 0.7971 0.6769 -0.0150 0.107 Uiso 1 1 calc R . .
Cl2 Cl 1.04665(3) -0.41875(11) 0.117112(17) 0.04284(13) Uani 1 1 d . . .
Cl3 Cl 1.24906(3) 0.28862(13) 0.15108(2) 0.05390(16) Uani 1 1 d . . .
N1 N 0.91945(7) 0.1981(3) 0.21023(5) 0.0344(3) Uani 1 1 d . . .
O1 O 1.03902(6) -0.1962(3) 0.20785(5) 0.0390(3) Uani 1 1 d . . .
Zn1 Zn 1.0000 -0.02005(7) 0.2500 0.03479(10) Uani 1 2 d S . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0326(8) 0.0354(9) 0.0278(8) 0.0018(7) 0.0168(7) 0.0033(7)
C2 0.0361(9) 0.0348(9) 0.0284(8) -0.0005(7) 0.0160(7) 0.0035(7)
C3 0.0400(9) 0.0436(10) 0.0303(9) 0.0032(8) 0.0219(7) 0.0075(8)
C4 0.0324(9) 0.0481(11) 0.0354(9) 0.0094(8) 0.0202(7) 0.0032(8)
C5 0.0330(8) 0.0401(10) 0.0265(8) -0.0008(7) 0.0147(7) 0.0007(8)
C6 0.0338(9) 0.0450(11) 0.0345(9) -0.0008(8) 0.0142(7) -0.0022(8)
C7 0.0368(9) 0.0422(10) 0.0291(9) 0.0054(8) 0.0128(7) 0.0026(8)
C8 0.0557(12) 0.0477(11) 0.0256(9) -0.0009(8) 0.0134(8) -0.0114(9)
C9 0.0486(11) 0.0442(11) 0.0291(9) 0.0071(8) 0.0184(8) -0.0040(9)
C10 0.0767(15) 0.0522(13) 0.0346(10) 0.0042(9) 0.0228(10) -0.0195(12)
C11 0.0629(14) 0.0594(14) 0.0376(11) 0.0064(10) 0.0170(10) 0.0075(11)
C12 0.099(2) 0.0689(16) 0.0321(11) 0.0091(11) 0.0306(12) 0.0069(14)
C13 0.0737(17) 0.109(2) 0.0465(13) 0.0168(14) 0.0324(12) 0.0296(16)
C14 0.0713(16) 0.0773(17) 0.0413(12) 0.0004(12) 0.0310(11) 0.0015(14)
C15 0.111(3) 0.113(3) 0.0470(15) 0.0308(16) 0.0333(16) 0.058(2)
Cl2 0.0540(3) 0.0452(3) 0.0360(2) -0.01072(19) 0.0243(2) -0.0071(2)
Cl3 0.0436(3) 0.0739(4) 0.0558(3) 0.0088(3) 0.0318(2) -0.0061(3)
N1 0.0384(8) 0.0422(8) 0.0260(7) 0.0034(6) 0.0158(6) -0.0027(7)
O1 0.0450(7) 0.0445(8) 0.0386(7) -0.0095(6) 0.0284(6) -0.0094(6)
Zn1 0.03468(16) 0.0475(2) 0.02869(16) 0.000 0.01930(12) 0.000

_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 1.301(2) . ?
C1 C2 1.418(2) . ?
C1 C5 1.422(3) . ?
C2 C3 1.369(2) . ?
C2 Cl2 1.7292(19) . ?
C3 C4 1.382(3) . ?
C4 C6 1.358(3) . ?
C4 Cl3 1.7470(18) . ?
C5 C6 1.404(3) . ?
C5 C7 1.447(2) 2_755 ?
C7 N1 1.279(2) . ?
C7 C5 1.447(2) 2_755 ?
C8 C13 1.371(3) . ?
C8 C11 1.374(3) . ?
C8 C10 1.503(3) . ?
C9 N1 1.467(2) . ?
C9 C10 1.522(3) . ?
C11 C14 1.372(3) . ?
C12 C14 1.347(4) . ?
C12 C15 1.356(4) . ?
C13 C15 1.381(4) . ?
N1 Zn1 2.0030(16) . ?
O1 Zn1 1.9095(13) . ?
Zn1 O1 1.9095(13) 2_755 ?
Zn1 N1 2.0030(16) 2_755 ?

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 C2 119.03(16) . . ?
O1 C1 C5 125.32(15) . . ?
C2 C1 C5 115.65(15) . . ?
C3 C2 C1 123.10(17) . . ?
C3 C2 Cl2 119.52(14) . . ?
C1 C2 Cl2 117.36(14) . . ?
C2 C3 C4 119.07(16) . . ?
C6 C4 C3 121.24(17) . . ?
C6 C4 Cl3 119.78(16) . . ?
C3 C4 Cl3 118.97(14) . . ?
C6 C5 C1 120.61(16) . . ?
C6 C5 C7 115.45(17) . 2_755 ?
C1 C5 C7 123.94(16) . 2_755 ?
C4 C6 C5 120.33(18) . . ?
N1 C7 C5 126.81(17) . 2_755 ?
C13 C8 C11 117.2(2) . . ?
C13 C8 C10 121.9(2) . . ?
C11 C8 C10 120.8(2) . . ?
N1 C9 C10 110.36(16) . . ?
C8 C10 C9 111.95(17) . . ?
C14 C11 C8 121.2(2) . . ?
C14 C12 C15 119.4(2) . . ?
C8 C13 C15 121.2(3) . . ?
C12 C14 C11 120.8(2) . . ?
C12 C15 C13 120.1(3) . . ?
C7 N1 C9 117.72(16) . . ?
C7 N1 Zn1 120.11(12) . . ?
C9 N1 Zn1 122.03(12) . . ?
C1 O1 Zn1 121.94(12) . . ?
O1 Zn1 O1 126.87(8) 2_755 . ?
O1 Zn1 N1 111.92(6) 2_755 2_755 ?
O1 Zn1 N1 95.67(6) . 2_755 ?
O1 Zn1 N1 95.67(6) 2_755 . ?
O1 Zn1 N1 111.92(6) . . ?
N1 Zn1 N1 116.29(9) 2_755 . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        27.96
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.054
