# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1568257'
_audit_update_record             
;
2017-08-10 deposited with the CCDC.
2017-09-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C88 H60 Cl8 N12 O1.44 Zn4'
_chemical_formula_weight         1853.60

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'
Cl Cl 0.3639 0.7018 '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'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'C c c a'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z'
'-x, y, -z+1/2'
'x+1/2, -y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1, -y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'x+1, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'x, -y, z-1/2'
'-x-1/2, y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x, y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
'-x, y+1/2, z-1/2'

_cell_length_a                   18.5190(3)
_cell_length_b                   25.5918(5)
_cell_length_c                   17.2622(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     8181.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    19720
_cell_measurement_theta_min      2.5550
_cell_measurement_theta_max      77.5210

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3758
_exptl_absorpt_coefficient_mu    4.183
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.4884
_exptl_absorpt_correction_T_max  0.6798
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_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            32638
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0105
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.45
_diffrn_reflns_theta_max         77.80
_reflns_number_total             4320
_reflns_number_gt                4121
_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)+(0.0487P)²+10.7257P] 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         4320
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0941
_refine_ls_wR_factor_gt          0.0928
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
Zn1 Zn 0.5000 0.533232(14) 0.2500 0.03614(11) Uani 1 2 d S . .
Zn2 Zn 0.5000 0.2500 1.00516(2) 0.03821(11) Uani 1 2 d S . .
Cl1 Cl 0.55902(3) 0.57791(2) 0.34163(3) 0.04742(14) Uani 1 1 d . . .
Cl2 Cl 0.54927(3) 0.31670(3) 1.06920(4) 0.05818(17) Uani 1 1 d . . .
N1 N 0.42951(9) 0.48694(7) 0.30871(9) 0.0388(3) Uani 1 1 d . . .
N2 N 0.42172(8) 0.27386(7) 0.93057(9) 0.0379(3) Uani 1 1 d . . .
N3 N 0.10919(9) 0.36418(7) 0.60124(10) 0.0433(4) Uani 1 1 d . . .
H3 H 0.0617 0.3638 0.5998 0.052 Uiso 1 1 calc R . .
C1 C 0.36681(11) 0.47113(8) 0.27743(12) 0.0427(4) Uani 1 1 d . . .
H1 H 0.3588 0.4773 0.2239 0.051 Uiso 1 1 calc R . .
C2 C 0.31394(11) 0.44649(8) 0.31915(11) 0.0426(4) Uani 1 1 d . . .
H2 H 0.2709 0.4354 0.2940 0.051 Uiso 1 1 calc R . .
C3 C 0.32282(10) 0.43750(8) 0.39832(11) 0.0377(4) Uani 1 1 d . . .
C4 C 0.38933(11) 0.45226(8) 0.42947(11) 0.0413(4) Uani 1 1 d . . .
H4 H 0.3994 0.4456 0.4825 0.050 Uiso 1 1 calc R . .
C5 C 0.44009(10) 0.47629(8) 0.38423(12) 0.0418(4) Uani 1 1 d . . .
H5 H 0.4848 0.4859 0.4071 0.050 Uiso 1 1 calc R . .
C6 C 0.35248(11) 0.25915(9) 0.93910(12) 0.0456(5) Uani 1 1 d . . .
H6 H 0.3401 0.2379 0.9822 0.055 Uiso 1 1 calc R . .
C7 C 0.29894(11) 0.27337(9) 0.88849(12) 0.0462(5) Uani 1 1 d . . .
H7 H 0.2508 0.2621 0.8974 0.055 Uiso 1 1 calc R . .
C8 C 0.31453(10) 0.30429(8) 0.82394(11) 0.0366(4) Uani 1 1 d . . .
C9 C 0.38670(10) 0.31956(8) 0.81592(12) 0.0413(4) Uani 1 1 d . . .
H9 H 0.4008 0.3408 0.7734 0.050 Uiso 1 1 calc R . .
C10 C 0.43720(10) 0.30394(8) 0.86935(12) 0.0415(4) Uani 1 1 d . . .
H10 H 0.4857 0.3151 0.8625 0.050 Uiso 1 1 calc R . .
C11 C 0.13598(11) 0.40384(8) 0.47165(12) 0.0422(4) Uani 1 1 d . . .
H11 H 0.0872 0.4072 0.4555 0.051 Uiso 1 1 calc R . .
C12 C 0.19204(11) 0.42020(8) 0.42516(12) 0.0416(4) Uani 1 1 d . . .
H12 H 0.1811 0.4352 0.3762 0.050 Uiso 1 1 calc R . .
C13 C 0.26511(10) 0.41563(8) 0.44729(11) 0.0396(4) Uani 1 1 d . . .
C14 C 0.28171(10) 0.39313(9) 0.51876(12) 0.0440(5) Uani 1 1 d . . .
H14 H 0.3306 0.3891 0.5344 0.053 Uiso 1 1 calc R . .
C15 C 0.27775(10) 0.34111(8) 0.69644(11) 0.0412(4) Uani 1 1 d . . .
H15 H 0.3272 0.3466 0.6842 0.049 Uiso 1 1 calc R . .
C16 C 0.25848(10) 0.31979(8) 0.76758(11) 0.0377(4) Uani 1 1 d . . .
C17 C 0.18438(10) 0.31279(8) 0.78462(12) 0.0416(4) Uani 1 1 d . . .
H17 H 0.1712 0.2985 0.8334 0.050 Uiso 1 1 calc R . .
C18 C 0.13067(10) 0.32586(9) 0.73318(12) 0.0436(4) Uani 1 1 d . . .
H18 H 0.0812 0.3207 0.7457 0.052 Uiso 1 1 calc R . .
C19 C 0.15364(10) 0.38213(8) 0.54324(12) 0.0405(4) Uani 1 1 d . . .
C20 C 0.22624(10) 0.37670(9) 0.56660(12) 0.0428(4) Uani 1 1 d . . .
C21 C 0.22450(10) 0.35432(8) 0.64347(12) 0.0414(4) Uani 1 1 d . . .
C22 C 0.15107(10) 0.34685(8) 0.66215(12) 0.0403(4) Uani 1 1 d . . .
O1 O 0.2690(5) 0.5297(4) 0.1666(5) 0.079(2) Uani 0.220(4) 1 d P A -1
O2 O 0.2500 0.5000 0.1074(6) 0.079(3) Uani 0.282(8) 2 d SP B 2


_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 N1 2.0334(16) . ?
Zn1 N1 2.0334(16) 3_655 ?
Zn1 Cl1 2.2370(5) . ?
Zn1 Cl1 2.2370(5) 3_655 ?
Zn2 N2 2.0328(16) . ?
Zn2 N2 2.0328(16) 6 ?
Zn2 Cl2 2.2290(6) . ?
Zn2 Cl2 2.2290(6) 6 ?
N1 C1 1.343(3) . ?
N1 C5 1.346(3) . ?
N2 C10 1.338(3) . ?
N2 C6 1.344(2) . ?
N3 C19 1.375(2) . ?
N3 C22 1.380(3) . ?
N3 H3 0.8800 . ?
C1 C2 1.369(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.396(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.396(3) . ?
C3 C13 1.473(3) . ?
C4 C5 1.368(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.371(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.397(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.399(3) . ?
C8 C16 1.477(3) . ?
C9 C10 1.373(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.377(3) . ?
C11 C19 1.394(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.411(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.396(3) . ?
C14 C20 1.384(3) . ?
C14 H14 0.9500 . ?
C15 C21 1.387(3) . ?
C15 C16 1.391(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.415(3) . ?
C17 C18 1.375(3) . ?
C17 H17 0.9500 . ?
C18 C22 1.391(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.410(3) . ?
C20 C21 1.445(3) . ?
C21 C22 1.411(2) . ?

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
N1 Zn1 N1 108.73(10) . 3_655 ?
N1 Zn1 Cl1 105.02(5) . . ?
N1 Zn1 Cl1 109.66(5) 3_655 . ?
N1 Zn1 Cl1 109.66(5) . 3_655 ?
N1 Zn1 Cl1 105.02(5) 3_655 3_655 ?
Cl1 Zn1 Cl1 118.52(3) . 3_655 ?
N2 Zn2 N2 101.39(9) . 6 ?
N2 Zn2 Cl2 112.09(5) . . ?
N2 Zn2 Cl2 104.61(5) 6 . ?
N2 Zn2 Cl2 104.61(5) . 6 ?
N2 Zn2 Cl2 112.09(5) 6 6 ?
Cl2 Zn2 Cl2 120.54(4) . 6 ?
C1 N1 C5 117.02(17) . . ?
C1 N1 Zn1 122.02(13) . . ?
C5 N1 Zn1 120.47(13) . . ?
C10 N2 C6 116.86(17) . . ?
C10 N2 Zn2 121.34(13) . . ?
C6 N2 Zn2 121.78(13) . . ?
C19 N3 C22 109.01(15) . . ?
C19 N3 H3 125.5 . . ?
C22 N3 H3 125.5 . . ?
N1 C1 C2 123.07(19) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C1 C2 C3 120.44(18) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 115.88(18) . . ?
C2 C3 C13 122.63(17) . . ?
C4 C3 C13 121.45(17) . . ?
C5 C4 C3 120.53(18) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
N1 C5 C4 122.93(18) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
N2 C6 C7 123.08(19) . . ?
N2 C6 H6 118.5 . . ?
C7 C6 H6 118.5 . . ?
C6 C7 C8 120.63(18) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 115.75(18) . . ?
C7 C8 C16 122.17(17) . . ?
C9 C8 C16 122.08(17) . . ?
C10 C9 C8 120.19(18) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
N2 C10 C9 123.50(18) . . ?
N2 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
C12 C11 C19 117.44(18) . . ?
C12 C11 H11 121.3 . . ?
C19 C11 H11 121.3 . . ?
C11 C12 C13 122.69(18) . . ?
C11 C12 H12 118.7 . . ?
C13 C12 H12 118.7 . . ?
C14 C13 C12 118.99(18) . . ?
C14 C13 C3 120.28(17) . . ?
C12 C13 C3 120.60(17) . . ?
C20 C14 C13 119.30(18) . . ?
C20 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C21 C15 C16 119.70(17) . . ?
C21 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 118.83(18) . . ?
C15 C16 C8 120.45(17) . . ?
C17 C16 C8 120.71(17) . . ?
C18 C17 C16 122.46(18) . . ?
C18 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
C17 C18 C22 117.83(17) . . ?
C17 C18 H18 121.1 . . ?
C22 C18 H18 121.1 . . ?
N3 C19 C11 129.66(17) . . ?
N3 C19 C20 109.23(17) . . ?
C11 C19 C20 121.10(18) . . ?
C14 C20 C19 120.47(18) . . ?
C14 C20 C21 133.22(18) . . ?
C19 C20 C21 106.28(17) . . ?
C15 C21 C22 120.12(18) . . ?
C15 C21 C20 133.32(17) . . ?
C22 C21 C20 106.55(17) . . ?
N3 C22 C18 130.03(17) . . ?
N3 C22 C21 108.92(17) . . ?
C18 C22 C21 121.04(18) . . ?

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
N1 Zn1 N1 C1 -90.63(16) 3_655 . . . ?
Cl1 Zn1 N1 C1 152.05(15) . . . . ?
Cl1 Zn1 N1 C1 23.68(17) 3_655 . . . ?
N1 Zn1 N1 C5 97.63(16) 3_655 . . . ?
Cl1 Zn1 N1 C5 -19.68(16) . . . . ?
Cl1 Zn1 N1 C5 -148.05(14) 3_655 . . . ?
N2 Zn2 N2 C10 -45.88(14) 6 . . . ?
Cl2 Zn2 N2 C10 65.19(17) . . . . ?
Cl2 Zn2 N2 C10 -162.55(15) 6 . . . ?
N2 Zn2 N2 C6 132.34(19) 6 . . . ?
Cl2 Zn2 N2 C6 -116.59(16) . . . . ?
Cl2 Zn2 N2 C6 15.67(18) 6 . . . ?
C5 N1 C1 C2 1.8(3) . . . . ?
Zn1 N1 C1 C2 -170.22(17) . . . . ?
N1 C1 C2 C3 1.3(3) . . . . ?
C1 C2 C3 C4 -3.6(3) . . . . ?
C1 C2 C3 C13 174.2(2) . . . . ?
C2 C3 C4 C5 3.0(3) . . . . ?
C13 C3 C4 C5 -174.8(2) . . . . ?
C1 N1 C5 C4 -2.4(3) . . . . ?
Zn1 N1 C5 C4 169.74(17) . . . . ?
C3 C4 C5 N1 -0.1(3) . . . . ?
C10 N2 C6 C7 0.2(3) . . . . ?
Zn2 N2 C6 C7 -178.05(18) . . . . ?
N2 C6 C7 C8 0.4(4) . . . . ?
C6 C7 C8 C9 -0.7(3) . . . . ?
C6 C7 C8 C16 179.1(2) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C16 C8 C9 C10 -179.5(2) . . . . ?
C6 N2 C10 C9 -0.6(3) . . . . ?
Zn2 N2 C10 C9 177.70(17) . . . . ?
C8 C9 C10 N2 0.3(3) . . . . ?
C19 C11 C12 C13 0.1(3) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C11 C12 C13 C3 -175.1(2) . . . . ?
C2 C3 C13 C14 161.0(2) . . . . ?
C4 C3 C13 C14 -21.3(3) . . . . ?
C2 C3 C13 C12 -23.2(3) . . . . ?
C4 C3 C13 C12 154.4(2) . . . . ?
C12 C13 C14 C20 -1.1(3) . . . . ?
C3 C13 C14 C20 174.8(2) . . . . ?
C21 C15 C16 C17 -0.9(3) . . . . ?
C21 C15 C16 C8 178.5(2) . . . . ?
C7 C8 C16 C15 -166.7(2) . . . . ?
C9 C8 C16 C15 13.1(3) . . . . ?
C7 C8 C16 C17 12.7(3) . . . . ?
C9 C8 C16 C17 -167.4(2) . . . . ?
C15 C16 C17 C18 0.6(3) . . . . ?
C8 C16 C17 C18 -178.8(2) . . . . ?
C16 C17 C18 C22 -0.2(3) . . . . ?
C22 N3 C19 C11 -179.0(2) . . . . ?
C22 N3 C19 C20 -0.3(2) . . . . ?
C12 C11 C19 N3 178.0(2) . . . . ?
C12 C11 C19 C20 -0.6(3) . . . . ?
C13 C14 C20 C19 0.6(3) . . . . ?
C13 C14 C20 C21 -177.2(2) . . . . ?
N3 C19 C20 C14 -178.6(2) . . . . ?
C11 C19 C20 C14 0.3(3) . . . . ?
N3 C19 C20 C21 -0.3(3) . . . . ?
C11 C19 C20 C21 178.6(2) . . . . ?
C16 C15 C21 C22 0.9(3) . . . . ?
C16 C15 C21 C20 179.9(2) . . . . ?
C14 C20 C21 C15 -0.4(5) . . . . ?
C19 C20 C21 C15 -178.4(2) . . . . ?
C14 C20 C21 C22 178.7(3) . . . . ?
C19 C20 C21 C22 0.7(3) . . . . ?
C19 N3 C22 C18 179.5(2) . . . . ?
C19 N3 C22 C21 0.7(2) . . . . ?
C17 C18 C22 N3 -178.5(2) . . . . ?
C17 C18 C22 C21 0.2(3) . . . . ?
C15 C21 C22 N3 178.4(2) . . . . ?
C20 C21 C22 N3 -0.8(3) . . . . ?
C15 C21 C22 C18 -0.5(3) . . . . ?
C20 C21 C22 C18 -179.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        77.80
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1568258'
_audit_update_record             
;
2017-08-10 deposited with the CCDC.
2017-09-20 downloaded from the CCDC.
;
_audit_creation_date             2017-08-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5370)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
'C44 H32 F N6 O Zn, F6 P, 2(H2 O), 2(C3 H7 N O)'
_chemical_formula_sum            'C50 H50 F7 N8 O5 P Zn'
_chemical_formula_weight         1072.32
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
F F 0.0727 0.0534 '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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   23.5121(8)
_cell_length_b                   7.7408(3)
_cell_length_c                   15.3224(5)
_cell_angle_alpha                90
_cell_angle_beta                 118.548(3)
_cell_angle_gamma                90
_cell_volume                     2449.65(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2776
_cell_measurement_temperature    156(2)
_cell_measurement_theta_max      62.3540
_cell_measurement_theta_min      3.9470
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.722
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1108
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.861
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3599
_diffrn_reflns_point_group_measured_fraction_full 0.858
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         62.561
_diffrn_reflns_theta_min         3.283
_diffrn_ambient_temperature      156
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.861
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.844
_reflns_Friedel_fraction_full    0.854
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                2597
_reflns_number_total             2605
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.48(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         2605
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0290
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0470P)²+2.1670P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0797
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.52(3) 0.48(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
3. Others
 Fixed Sof: H1A(0.5) H1B(0.5)
4.a Free rotating group:
 O2(H2A,H2B)
4.b Rotating group:
 O1(H1A,H1B)
4.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C6(H6), C15(H15), C7(H7), C11(H11), C9(H9), C5(H5), C12(H12),
 C17(H17), C1(H1), C18(H18), C2(H2), C14(H14), C4(H4), C10(H10), C25(H25)
4.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.5000 0.15853(7) 0.5000 0.02626(17) Uani 1 2 d S T P . .
P1 P 0.5000 0.9629(3) 1.0000 0.0566(4) Uani 1 2 d S T P . .
F1 F 0.5000 0.4189(4) 0.5000 0.0372(8) Uani 1 2 d S T P . .
O2 O 0.50682(10) 0.6452(5) 0.62863(15) 0.0322(5) Uani 1 1 d . . . . .
H2A H 0.5001 0.5683 0.5851 0.048 Uiso 1 1 d G . . . .
H2B H 0.4797 0.6333 0.6500 0.048 Uiso 1 1 d G . . . .
N1 N 0.42454(12) 0.1505(6) -0.45348(17) 0.0299(6) Uani 1 1 d . . . . .
N3 N 0.14395(11) 0.1518(6) -0.25946(17) 0.0310(6) Uani 1 1 d . . . . .
H3 H 0.1014 0.1560 -0.2899 0.037 Uiso 1 1 calc R . . . .
O1 O 0.5000 -0.1125(5) 0.5000 0.0329(9) Uani 1 2 d S T P . .
H1A H 0.4860 -0.1507 0.4405 0.049 Uiso 0.5 1 d GR . . . .
H1B H 0.4754 -0.1507 0.5228 0.049 Uiso 0.5 1 d GR . . . .
N2 N 0.42717(11) 0.1567(6) 0.34335(17) 0.0289(6) Uani 1 1 d . . . . .
O3 O 0.41639(17) 0.5973(6) 0.6843(3) 0.0751(13) Uani 1 1 d . . . . .
N4 N 0.38406(17) 0.5373(6) 0.7991(3) 0.0474(9) Uani 1 1 d . . . . .
C8 C 0.33213(14) 0.1477(7) 0.1419(2) 0.0294(7) Uani 1 1 d . . . . .
C6 C 0.37191(17) 0.0682(5) 0.3128(2) 0.0311(8) Uani 1 1 d . . . . .
H6 H 0.3655 0.0063 0.3609 0.037 Uiso 1 1 calc R . . . .
F4 F 0.5107(2) 0.8163(6) 0.9381(3) 0.1095(14) Uani 1 1 d . . . . .
C22 C 0.18293(14) 0.1453(7) -0.1585(2) 0.0290(7) Uani 1 1 d . . . . .
C15 C 0.29512(14) 0.1306(5) -0.2624(2) 0.0263(8) Uani 1 1 d . . . . .
H15 H 0.3392 0.1142 -0.2145 0.032 Uiso 1 1 calc R . . . .
C19 C 0.18167(13) 0.1506(6) -0.3060(2) 0.0276(6) Uani 1 1 d . . . . .
C3 C 0.32818(13) 0.1503(7) -0.3947(2) 0.0271(6) Uani 1 1 d . . . . .
C16 C 0.27791(13) 0.1503(6) -0.3619(2) 0.0259(6) Uani 1 1 d . . . . .
C7 C 0.32400(16) 0.0621(5) 0.2154(2) 0.0307(8) Uani 1 1 d . . . . .
H7 H 0.2853 -0.0005 0.1981 0.037 Uiso 1 1 calc R . . . .
C21 C 0.24865(14) 0.1325(5) -0.1371(2) 0.0265(8) Uani 1 1 d . . . . .
C20 C 0.24741(14) 0.1349(5) -0.2328(2) 0.0264(8) Uani 1 1 d . . . . .
C13 C 0.28161(14) 0.1439(6) 0.0370(2) 0.0298(7) Uani 1 1 d . . . . .
C11 C 0.16644(14) 0.1575(8) -0.0830(2) 0.0349(7) Uani 1 1 d . . . . .
H11 H 0.1225 0.1667 -0.0974 0.042 Uiso 1 1 calc R . . . .
C9 C 0.39032(16) 0.2367(5) 0.1736(2) 0.0313(8) Uani 1 1 d . . . . .
H9 H 0.3991 0.2950 0.1268 0.038 Uiso 1 1 calc R . . . .
C5 C 0.42814(17) 0.0470(5) -0.3815(2) 0.0320(8) Uani 1 1 d . . . . .
H5 H 0.4643 -0.0282 -0.3505 0.038 Uiso 1 1 calc R . . . .
C12 C 0.21582(14) 0.1558(8) 0.0136(2) 0.0351(7) Uani 1 1 d . . . . .
H12 H 0.2054 0.1629 0.0662 0.042 Uiso 1 1 calc R . . . .
C17 C 0.21193(15) 0.1740(6) -0.4328(2) 0.0294(7) Uani 1 1 d . . . . .
H17 H 0.2007 0.1922 -0.5005 0.035 Uiso 1 1 calc R . . . .
C1 C 0.37261(16) 0.2550(5) -0.4964(2) 0.0311(8) Uani 1 1 d . . . . .
H1 H 0.3693 0.3318 -0.5469 0.037 Uiso 1 1 calc R . . . .
C18 C 0.16368(14) 0.1714(6) -0.4060(2) 0.0301(7) Uani 1 1 d . . . . .
H18 H 0.1195 0.1834 -0.4544 0.036 Uiso 1 1 calc R . . . .
C2 C 0.32399(16) 0.2560(5) -0.4705(2) 0.0309(8) Uani 1 1 d . . . . .
H2 H 0.2875 0.3293 -0.5048 0.037 Uiso 1 1 calc R . . . .
C14 C 0.29765(14) 0.1327(6) -0.0393(2) 0.0287(8) Uani 1 1 d . . . . .
H14 H 0.3417 0.1251 -0.0246 0.034 Uiso 1 1 calc R . . . .
C4 C 0.38241(16) 0.0425(5) -0.3493(2) 0.0309(8) Uani 1 1 d . . . . .
H4 H 0.3877 -0.0329 -0.2970 0.037 Uiso 1 1 calc R . . . .
C10 C 0.43502(16) 0.2394(5) 0.2733(2) 0.0311(8) Uani 1 1 d . . . . .
H10 H 0.4737 0.3038 0.2933 0.037 Uiso 1 1 calc R . . . .
F3 F 0.4270(2) 0.9609(10) 0.9258(4) 0.155(3) Uani 1 1 d . . . . .
C23 C 0.3987(3) 0.4746(8) 0.8964(4) 0.0627(14) Uani 1 1 d . . . . .
H23A H 0.4372 0.4008 0.9225 0.094 Uiso 1 1 calc GR . . . .
H23B H 0.3619 0.4077 0.8915 0.094 Uiso 1 1 calc GR . . . .
H23C H 0.4068 0.5728 0.9412 0.094 Uiso 1 1 calc GR . . . .
C25 C 0.4258(2) 0.5377(9) 0.7645(4) 0.0608(14) Uani 1 1 d . . . . .
H25 H 0.4670 0.4873 0.8054 0.073 Uiso 1 1 calc R . . . .
F2 F 0.4872(3) 1.1059(7) 1.0617(4) 0.141(2) Uani 1 1 d . . . . .
C24 C 0.3217(2) 0.6194(9) 0.7409(4) 0.0694(18) Uani 1 1 d . . . . .
H24A H 0.2872 0.5372 0.7294 0.104 Uiso 1 1 calc GR . . . .
H24B H 0.3176 0.6567 0.6769 0.104 Uiso 1 1 calc GR . . . .
H24C H 0.3183 0.7201 0.7769 0.104 Uiso 1 1 calc GR . . . .


_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 F1 2.015(3) . ?
Zn1 N1 2.207(2) 2_655 ?
Zn1 N1 2.207(2) 1_556 ?
Zn1 O1 2.098(4) . ?
Zn1 N2 2.183(2) 2_656 ?
Zn1 N2 2.183(2) . ?
P1 F4 1.574(4) . ?
P1 F4 1.574(4) 2_657 ?
P1 F3 1.540(4) . ?
P1 F3 1.540(4) 2_657 ?
P1 F2 1.575(5) 2_657 ?
P1 F2 1.575(5) . ?
O2 H2A 0.8499 . ?
O2 H2B 0.8504 . ?
N1 Zn1 2.207(2) 1_554 ?
N1 C5 1.332(5) . ?
N1 C1 1.345(5) . ?
N3 H3 0.8800 . ?
N3 C22 1.371(4) . ?
N3 C19 1.378(4) . ?
O1 H1A 0.8603 . ?
O1 H1B 0.8596 . ?
N2 C6 1.340(5) . ?
N2 C10 1.336(5) . ?
O3 C25 1.230(7) . ?
N4 C23 1.445(6) . ?
N4 C25 1.319(6) . ?
N4 C24 1.449(7) . ?
C8 C7 1.396(5) . ?
C8 C13 1.474(4) . ?
C8 C9 1.396(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.375(5) . ?
C22 C21 1.421(4) . ?
C22 C11 1.389(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(4) . ?
C15 C20 1.397(4) . ?
C19 C20 1.416(4) . ?
C19 C18 1.391(4) . ?
C3 C16 1.489(4) . ?
C3 C2 1.386(5) . ?
C3 C4 1.399(5) . ?
C16 C17 1.418(4) . ?
C7 H7 0.9500 . ?
C21 C20 1.453(4) . ?
C21 C14 1.386(4) . ?
C13 C12 1.414(4) . ?
C13 C14 1.393(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.376(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.380(5) . ?
C5 H5 0.9500 . ?
C5 C4 1.382(5) . ?
C12 H12 0.9500 . ?
C17 H17 0.9500 . ?
C17 C18 1.379(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.377(5) . ?
C18 H18 0.9500 . ?
C2 H2 0.9500 . ?
C14 H14 0.9500 . ?
C4 H4 0.9500 . ?
C10 H10 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C25 H25 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
F1 Zn1 N1 91.62(12) . 2_655 ?
F1 Zn1 N1 91.62(12) . 1_556 ?
F1 Zn1 O1 180.0 . . ?
F1 Zn1 N2 90.36(12) . 2_656 ?
F1 Zn1 N2 90.36(12) . . ?
N1 Zn1 N1 176.8(2) 1_556 2_655 ?
O1 Zn1 N1 88.38(12) . 1_556 ?
O1 Zn1 N1 88.38(12) . 2_655 ?
O1 Zn1 N2 89.64(12) . . ?
O1 Zn1 N2 89.64(12) . 2_656 ?
N2 Zn1 N1 88.51(9) 2_656 1_556 ?
N2 Zn1 N1 91.47(9) . 1_556 ?
N2 Zn1 N1 91.47(9) 2_656 2_655 ?
N2 Zn1 N1 88.51(9) . 2_655 ?
N2 Zn1 N2 179.3(2) 2_656 . ?
F4 P1 F4 87.7(4) 2_657 . ?
F4 P1 F2 90.8(3) 2_657 . ?
F4 P1 F2 178.0(3) 2_657 2_657 ?
F4 P1 F2 178.0(3) . . ?
F4 P1 F2 90.8(3) . 2_657 ?
F3 P1 F4 89.5(3) 2_657 2_657 ?
F3 P1 F4 89.5(3) . . ?
F3 P1 F4 89.7(3) 2_657 . ?
F3 P1 F4 89.7(3) . 2_657 ?
F3 P1 F3 178.9(6) . 2_657 ?
F3 P1 F2 91.7(4) . 2_657 ?
F3 P1 F2 89.1(4) . . ?
F3 P1 F2 89.1(4) 2_657 2_657 ?
F3 P1 F2 91.7(4) 2_657 . ?
F2 P1 F2 90.7(4) . 2_657 ?
H2A O2 H2B 109.4 . . ?
C5 N1 Zn1 122.8(2) . 1_554 ?
C5 N1 C1 116.7(3) . . ?
C1 N1 Zn1 120.5(2) . 1_554 ?
C22 N3 H3 125.2 . . ?
C22 N3 C19 109.5(2) . . ?
C19 N3 H3 125.2 . . ?
Zn1 O1 H1A 110.1 . . ?
Zn1 O1 H1B 110.1 . . ?
H1A O1 H1B 108.8 . . ?
C6 N2 Zn1 120.5(2) . . ?
C10 N2 Zn1 122.9(2) . . ?
C10 N2 C6 116.6(3) . . ?
C23 N4 C24 117.0(4) . . ?
C25 N4 C23 124.0(4) . . ?
C25 N4 C24 118.6(4) . . ?
C7 C8 C13 121.4(3) . . ?
C9 C8 C7 116.3(3) . . ?
C9 C8 C13 122.3(3) . . ?
N2 C6 H6 118.3 . . ?
N2 C6 C7 123.5(3) . . ?
C7 C6 H6 118.3 . . ?
N3 C22 C21 109.3(3) . . ?
N3 C22 C11 129.4(3) . . ?
C11 C22 C21 121.2(3) . . ?
C16 C15 H15 120.1 . . ?
C16 C15 C20 119.8(3) . . ?
C20 C15 H15 120.1 . . ?
N3 C19 C20 108.7(2) . . ?
N3 C19 C18 129.6(3) . . ?
C18 C19 C20 121.6(3) . . ?
C2 C3 C16 122.2(3) . . ?
C2 C3 C4 116.9(3) . . ?
C4 C3 C16 120.9(3) . . ?
C15 C16 C3 120.6(3) . . ?
C15 C16 C17 119.6(3) . . ?
C17 C16 C3 119.7(3) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 C8 120.1(3) . . ?
C6 C7 H7 119.9 . . ?
C22 C21 C20 105.7(3) . . ?
C14 C21 C22 120.0(3) . . ?
C14 C21 C20 134.1(3) . . ?
C15 C20 C19 119.2(3) . . ?
C15 C20 C21 134.0(3) . . ?
C19 C20 C21 106.7(3) . . ?
C12 C13 C8 119.3(3) . . ?
C14 C13 C8 121.1(3) . . ?
C14 C13 C12 119.6(3) . . ?
C22 C11 H11 121.1 . . ?
C12 C11 C22 117.8(3) . . ?
C12 C11 H11 121.1 . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
N1 C5 H5 118.0 . . ?
N1 C5 C4 124.0(3) . . ?
C4 C5 H5 118.0 . . ?
C13 C12 H12 118.9 . . ?
C11 C12 C13 122.2(3) . . ?
C11 C12 H12 118.9 . . ?
C16 C17 H17 119.2 . . ?
C18 C17 C16 121.6(3) . . ?
C18 C17 H17 119.2 . . ?
N1 C1 H1 118.4 . . ?
N1 C1 C2 123.2(3) . . ?
C2 C1 H1 118.4 . . ?
C19 C18 H18 121.0 . . ?
C17 C18 C19 118.0(3) . . ?
C17 C18 H18 121.0 . . ?
C3 C2 H2 119.9 . . ?
C1 C2 C3 120.1(3) . . ?
C1 C2 H2 119.9 . . ?
C21 C14 C13 119.3(3) . . ?
C21 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.1(3) . . ?
C5 C4 H4 120.4 . . ?
N2 C10 C9 123.9(3) . . ?
N2 C10 H10 118.0 . . ?
C9 C10 H10 118.0 . . ?
N4 C23 H23A 109.5 . . ?
N4 C23 H23B 109.5 . . ?
N4 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O3 C25 N4 126.1(5) . . ?
O3 C25 H25 117.0 . . ?
N4 C25 H25 117.0 . . ?
N4 C24 H24A 109.5 . . ?
N4 C24 H24B 109.5 . . ?
N4 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.52(3)
2 0.48(3)

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1568256'
_audit_update_record             
;
2017-08-10 deposited with the CCDC.
2017-09-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H15 Cl2 N3 Zn'
_chemical_formula_weight         457.64

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'
Cl Cl 0.3639 0.7018 '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'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.06863(11)
_cell_length_b                   15.72530(18)
_cell_length_c                   13.52583(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.2154(12)
_cell_angle_gamma                90.00
_cell_volume                     1892.04(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    13368
_cell_measurement_theta_min      2.8100
_cell_measurement_theta_max      77.4060

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    4.498
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_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            15387
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.36
_diffrn_reflns_theta_max         77.62
_reflns_number_total             3914
_reflns_number_gt                3801
_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)+(0.0690P)²+1.6040P] 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         3914
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1069
_refine_ls_wR_factor_gt          0.1025
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
Zn1 Zn 0.02218(3) 0.170098(17) 0.706424(19) 0.01880(12) Uani 1 1 d . . .
C15 C -0.4927(2) -0.09580(13) 0.06230(15) 0.0176(4) Uani 1 1 d . . .
H15 H -0.3901 -0.0906 0.0941 0.021 Uiso 1 1 calc R . .
C19 C -0.7488(2) 0.01314(13) 0.19909(15) 0.0189(4) Uani 1 1 d . . .
N1 N -0.1469(2) 0.13461(11) 0.59198(13) 0.0204(3) Uani 1 1 d . . .
N2 N -0.1870(2) -0.27109(11) -0.14772(13) 0.0207(4) Uani 1 1 d . . .
C11 C -0.7822(2) 0.06227(13) 0.27809(16) 0.0217(4) Uani 1 1 d . . .
H11 H -0.8827 0.0782 0.2799 0.026 Uiso 1 1 calc R . .
C7 C -0.4417(2) -0.22194(13) -0.16728(15) 0.0198(4) Uani 1 1 d . . .
H7 H -0.5389 -0.2183 -0.2088 0.024 Uiso 1 1 calc R . .
C14 C -0.4822(2) 0.01634(13) 0.27244(15) 0.0189(4) Uani 1 1 d . . .
H14 H -0.3816 0.0009 0.2701 0.023 Uiso 1 1 calc R . .
C12 C -0.6642(2) 0.08684(13) 0.35345(16) 0.0214(4) Uani 1 1 d . . .
H12 H -0.6851 0.1202 0.4076 0.026 Uiso 1 1 calc R . .
N3 N -0.84244(19) -0.01978(11) 0.11440(13) 0.0206(4) Uani 1 1 d . . .
H3 H -0.9406 -0.0134 0.0990 0.025 Uiso 1 1 calc R . .
C21 C -0.6039(2) -0.05820(12) 0.10495(14) 0.0172(4) Uani 1 1 d . . .
C3 C -0.3881(2) 0.08867(13) 0.43570(15) 0.0184(4) Uani 1 1 d . . .
C1 C -0.2902(2) 0.13822(13) 0.60450(15) 0.0213(4) Uani 1 1 d . . .
H1 H -0.3093 0.1570 0.6676 0.026 Uiso 1 1 calc R . .
C10 C -0.1588(2) -0.23397(14) -0.05647(16) 0.0224(4) Uani 1 1 d . . .
H10 H -0.0597 -0.2370 -0.0177 0.027 Uiso 1 1 calc R . .
C5 C -0.1235(2) 0.10687(15) 0.50235(16) 0.0251(4) Uani 1 1 d . . .
H5 H -0.0229 0.1024 0.4926 0.030 Uiso 1 1 calc R . .
C4 C -0.2380(2) 0.08459(15) 0.42391(16) 0.0257(4) Uani 1 1 d . . .
H4 H -0.2151 0.0664 0.3616 0.031 Uiso 1 1 calc R . .
C13 C -0.5129(2) 0.06401(13) 0.35295(15) 0.0187(4) Uani 1 1 d . . .
C16 C -0.5324(2) -0.14134(12) -0.02777(14) 0.0175(4) Uani 1 1 d . . .
C17 C -0.6860(2) -0.14567(13) -0.07444(15) 0.0201(4) Uani 1 1 d . . .
H17 H -0.7132 -0.1754 -0.1365 0.024 Uiso 1 1 calc R . .
C8 C -0.4143(2) -0.18415(13) -0.07112(15) 0.0174(4) Uani 1 1 d . . .
C9 C -0.2668(2) -0.19177(14) -0.01650(16) 0.0224(4) Uani 1 1 d . . .
H9 H -0.2410 -0.1675 0.0489 0.027 Uiso 1 1 calc R . .
C22 C -0.7561(2) -0.06435(12) 0.05790(15) 0.0178(4) Uani 1 1 d . . .
C6 C -0.3284(2) -0.26418(14) -0.20128(15) 0.0225(4) Uani 1 1 d . . .
H6 H -0.3510 -0.2899 -0.2660 0.027 Uiso 1 1 calc R . .
C20 C -0.5990(2) -0.00852(13) 0.19575(15) 0.0178(4) Uani 1 1 d . . .
C18 C -0.7979(2) -0.10825(13) -0.03307(15) 0.0202(4) Uani 1 1 d . . .
H18 H -0.9004 -0.1123 -0.0656 0.024 Uiso 1 1 calc R . .
C2 C -0.4111(2) 0.11586(13) 0.53003(16) 0.0207(4) Uani 1 1 d . . .
H2 H -0.5103 0.1190 0.5430 0.025 Uiso 1 1 calc R . .
Cl1 Cl 0.12977(5) 0.05261(3) 0.78286(4) 0.02094(13) Uani 1 1 d . . .
Cl2 Cl -0.07664(6) 0.25641(4) 0.80692(4) 0.02875(15) 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
Zn1 N1 2.0337(18) . ?
Zn1 N2 2.0450(18) 2 ?
Zn1 Cl2 2.2286(5) . ?
Zn1 Cl1 2.2454(5) . ?
C15 C21 1.387(3) . ?
C15 C16 1.399(3) . ?
C19 N3 1.387(3) . ?
C19 C11 1.399(3) . ?
C19 C20 1.409(3) . ?
N1 C5 1.343(3) . ?
N1 C1 1.344(3) . ?
N2 C10 1.344(3) . ?
N2 C6 1.349(3) . ?
N2 Zn1 2.0450(18) 2_545 ?
C11 C12 1.382(3) . ?
C7 C6 1.376(3) . ?
C7 C8 1.407(3) . ?
C14 C20 1.387(3) . ?
C14 C13 1.394(3) . ?
C12 C13 1.419(3) . ?
N3 C22 1.386(3) . ?
C21 C22 1.407(3) . ?
C21 C20 1.449(3) . ?
C3 C2 1.399(3) . ?
C3 C4 1.403(3) . ?
C3 C13 1.481(3) . ?
C1 C2 1.382(3) . ?
C10 C9 1.377(3) . ?
C5 C4 1.377(3) . ?
C16 C17 1.414(3) . ?
C16 C8 1.480(3) . ?
C17 C18 1.382(3) . ?
C8 C9 1.402(3) . ?
C22 C18 1.397(3) . ?

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
N1 Zn1 N2 109.18(7) . 2 ?
N1 Zn1 Cl2 107.35(5) . . ?
N2 Zn1 Cl2 111.86(5) 2 . ?
N1 Zn1 Cl1 108.69(5) . . ?
N2 Zn1 Cl1 105.42(5) 2 . ?
Cl2 Zn1 Cl1 114.24(2) . . ?
C21 C15 C16 119.72(18) . . ?
N3 C19 C11 130.42(19) . . ?
N3 C19 C20 108.82(17) . . ?
C11 C19 C20 120.74(19) . . ?
C5 N1 C1 116.97(18) . . ?
C5 N1 Zn1 123.23(15) . . ?
C1 N1 Zn1 119.80(13) . . ?
C10 N2 C6 116.70(18) . . ?
C10 N2 Zn1 122.02(15) . 2_545 ?
C6 N2 Zn1 121.21(14) . 2_545 ?
C12 C11 C19 117.80(19) . . ?
C6 C7 C8 120.22(19) . . ?
C20 C14 C13 119.74(18) . . ?
C11 C12 C13 122.43(19) . . ?
C22 N3 C19 108.87(16) . . ?
C15 C21 C22 120.74(18) . . ?
C15 C21 C20 132.66(19) . . ?
C22 C21 C20 106.60(17) . . ?
C2 C3 C4 115.97(19) . . ?
C2 C3 C13 122.80(18) . . ?
C4 C3 C13 121.23(18) . . ?
N1 C1 C2 123.15(18) . . ?
N2 C10 C9 123.2(2) . . ?
N1 C5 C4 123.4(2) . . ?
C5 C4 C3 120.22(19) . . ?
C14 C13 C12 118.68(19) . . ?
C14 C13 C3 119.45(18) . . ?
C12 C13 C3 121.86(18) . . ?
C15 C16 C17 118.54(18) . . ?
C15 C16 C8 119.64(18) . . ?
C17 C16 C8 121.81(18) . . ?
C18 C17 C16 122.38(19) . . ?
C9 C8 C7 115.48(18) . . ?
C9 C8 C16 121.35(18) . . ?
C7 C8 C16 123.14(18) . . ?
C10 C9 C8 120.84(19) . . ?
N3 C22 C18 130.56(19) . . ?
N3 C22 C21 109.00(17) . . ?
C18 C22 C21 120.41(18) . . ?
N2 C6 C7 123.59(19) . . ?
C14 C20 C19 120.56(18) . . ?
C14 C20 C21 132.74(18) . . ?
C19 C20 C21 106.68(17) . . ?
C17 C18 C22 118.19(19) . . ?
C1 C2 C3 120.29(19) . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        77.62
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.835
_refine_diff_density_rms         0.106
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1568259'
_audit_update_record             
;
2017-08-10 deposited with the CCDC.
2017-09-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H30 F6 N6 Si Zn'
_chemical_formula_weight         850.20

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'
F F 0.0727 0.0534 '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'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 '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                   26.5001(6)
_cell_length_b                   7.73830(10)
_cell_length_c                   27.4332(7)
_cell_angle_alpha                90
_cell_angle_beta                 112.066(3)
_cell_angle_gamma                90
_cell_volume                     5213.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    19299
_cell_measurement_theta_min      3.4250
_cell_measurement_theta_max      77.3230

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.083
_exptl_crystal_F_000             1736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.324
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21199
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.477
_diffrn_reflns_theta_max         65.985
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.936
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.936
_reflns_number_total             4424
_reflns_number_gt                3944
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0758P)²+17.0139P]
 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         4424
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1650
_refine_ls_wR_factor_gt          0.1627
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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
Zn1 Zn 0.5000 0.63659(8) 0.7500 0.0334(2) Uani 1 2 d S T P . .
Si1 Si 0.5000 0.13903(16) 0.7500 0.0328(3) Uani 1 2 d S T P . .
F1 F 0.5000 0.3604(4) 0.7500 0.0515(7) Uani 1 2 d S T P . .
F2 F 0.5000 -0.0829(4) 0.7500 0.0506(7) Uani 1 2 d S T P . .
F3 F 0.56536(8) 0.1393(3) 0.75789(9) 0.0496(5) Uani 1 1 d . . . . .
F4 F 0.51713(9) 0.1398(3) 0.81549(8) 0.0514(5) Uani 1 1 d . . . . .
N2 N 0.08636(11) 0.8575(4) 0.27152(10) 0.0379(6) Uani 1 1 d . . . . .
N3 N 0.42587(11) 0.8327(4) 0.34880(10) 0.0410(7) Uani 1 1 d . . . . .
H3 H 0.4468 0.8517 0.3309 0.049 Uiso 1 1 calc R U . . .
N1 N 0.48902(11) 0.6457(4) 0.66903(10) 0.0378(6) Uani 1 1 d . . . . .
C19 C 0.44379(13) 0.7894(5) 0.40167(12) 0.0385(7) Uani 1 1 d . . . . .
C21 C 0.35028(13) 0.7954(5) 0.36860(12) 0.0372(7) Uani 1 1 d . . . . .
C22 C 0.36979(13) 0.8411(4) 0.32895(13) 0.0369(7) Uani 1 1 d . . . . .
C20 C 0.39856(13) 0.7647(5) 0.41600(13) 0.0394(8) Uani 1 1 d . . . . .
C14 C 0.29494(13) 0.7933(5) 0.35781(13) 0.0402(8) Uani 1 1 d . . . . .
H14 H 0.2817 0.7585 0.3840 0.048 Uiso 1 1 calc R U . . .
C13 C 0.25854(13) 0.8431(5) 0.30790(13) 0.0397(8) Uani 1 1 d . . . . .
C11 C 0.33449(14) 0.8912(5) 0.27909(13) 0.0419(8) Uani 1 1 d . . . . .
H11 H 0.3477 0.9233 0.2526 0.050 Uiso 1 1 calc R U . . .
C3 C 0.46964(14) 0.6899(5) 0.56162(13) 0.0414(8) Uani 1 1 d . . . . .
C9 C 0.17385(13) 0.7298(5) 0.31785(13) 0.0415(8) Uani 1 1 d . . . . .
H9 H 0.1947 0.6450 0.3421 0.050 Uiso 1 1 calc R U . . .
C15 C 0.40655(14) 0.7279(5) 0.46818(13) 0.0430(8) Uani 1 1 d . . . . .
H15 H 0.3763 0.7098 0.4782 0.052 Uiso 1 1 calc R U . . .
C8 C 0.19931(13) 0.8451(5) 0.29545(12) 0.0382(7) Uani 1 1 d . . . . .
C7 C 0.16583(14) 0.9667(5) 0.26071(14) 0.0463(8) Uani 1 1 d . . . . .
H7 H 0.1811 1.0482 0.2442 0.056 Uiso 1 1 calc R U . . .
C5 C 0.44947(14) 0.5592(5) 0.63181(13) 0.0430(8) Uani 1 1 d . . . . .
H5 H 0.4280 0.4803 0.6423 0.052 Uiso 1 1 calc R U . . .
C1 C 0.51932(14) 0.7535(5) 0.65273(13) 0.0434(8) Uani 1 1 d . . . . .
H1 H 0.5476 0.8165 0.6785 0.052 Uiso 1 1 calc R U . . .
C10 C 0.11804(13) 0.7388(5) 0.30478(13) 0.0407(8) Uani 1 1 d . . . . .
H10 H 0.1015 0.6573 0.3200 0.049 Uiso 1 1 calc R U . . .
C2 C 0.51144(15) 0.7772(5) 0.60078(13) 0.0459(8) Uani 1 1 d . . . . .
H2 H 0.5345 0.8533 0.5915 0.055 Uiso 1 1 calc R U . . .
C6 C 0.11080(13) 0.9693(5) 0.25023(14) 0.0438(8) Uani 1 1 d . . . . .
H6 H 0.0891 1.0545 0.2267 0.053 Uiso 1 1 calc R U . . .
C16 C 0.45947(14) 0.7180(5) 0.50532(13) 0.0431(8) Uani 1 1 d . . . . .
C18 C 0.49672(14) 0.7777(5) 0.43801(14) 0.0458(9) Uani 1 1 d . . . . .
H18 H 0.5270 0.7933 0.4279 0.055 Uiso 1 1 calc R U . . .
C12 C 0.27955(14) 0.8926(5) 0.26964(13) 0.0448(8) Uani 1 1 d . . . . .
H12 H 0.2548 0.9282 0.2360 0.054 Uiso 1 1 calc R U . . .
C17 C 0.50369(14) 0.7425(5) 0.48958(14) 0.0475(9) Uani 1 1 d . . . . .
H17 H 0.5396 0.7346 0.5153 0.057 Uiso 1 1 calc R U . . .
C4 C 0.43829(14) 0.5792(5) 0.57873(13) 0.0460(8) Uani 1 1 d . . . . .
H4 H 0.4090 0.5171 0.5538 0.055 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 N1 2.130(3) . ?
Zn1 N1 2.130(3) 2_656 ?
Zn1 F1 2.137(3) . ?
Zn1 N2 2.138(3) 8_566 ?
Zn1 N2 2.138(3) 7_566 ?
Zn1 F2 2.171(3) 1_565 ?
Si1 F3 1.6628(19) . ?
Si1 F3 1.6629(19) 2_656 ?
Si1 F4 1.6795(19) . ?
Si1 F4 1.6795(19) 2_656 ?
Si1 F1 1.713(3) . ?
Si1 F2 1.717(3) . ?
F2 Zn1 2.171(3) 1_545 ?
N2 C6 1.339(4) . ?
N2 C10 1.344(4) . ?
N2 Zn1 2.139(3) 7_566 ?
N3 C22 1.379(4) . ?
N3 C19 1.387(4) . ?
N3 H3 0.8800 . ?
N1 C5 1.336(4) . ?
N1 C1 1.345(4) . ?
C19 C18 1.385(5) . ?
C19 C20 1.408(4) . ?
C21 C14 1.383(5) . ?
C21 C22 1.413(4) . ?
C21 C20 1.461(4) . ?
C22 C11 1.391(5) . ?
C20 C15 1.396(5) . ?
C14 C13 1.400(5) . ?
C14 H14 0.9500 . ?
C13 C12 1.413(5) . ?
C13 C8 1.476(4) . ?
C11 C12 1.380(5) . ?
C11 H11 0.9500 . ?
C3 C4 1.392(5) . ?
C3 C2 1.394(5) . ?
C3 C16 1.481(4) . ?
C9 C10 1.386(5) . ?
C9 C8 1.393(5) . ?
C9 H9 0.9500 . ?
C15 C16 1.392(5) . ?
C15 H15 0.9500 . ?
C8 C7 1.395(5) . ?
C7 C6 1.377(5) . ?
C7 H7 0.9500 . ?
C5 C4 1.381(5) . ?
C5 H5 0.9500 . ?
C1 C2 1.373(5) . ?
C1 H1 0.9500 . ?
C10 H10 0.9500 . ?
C2 H2 0.9500 . ?
C6 H6 0.9500 . ?
C16 C17 1.406(5) . ?
C18 C17 1.383(5) . ?
C18 H18 0.9500 . ?
C12 H12 0.9500 . ?
C17 H17 0.9500 . ?
C4 H4 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
N1 Zn1 N1 176.20(16) . 2_656 ?
N1 Zn1 F1 91.90(8) . . ?
N1 Zn1 F1 91.90(8) 2_656 . ?
N1 Zn1 N2 90.00(10) . 8_566 ?
N1 Zn1 N2 89.92(10) 2_656 8_566 ?
F1 Zn1 N2 91.23(8) . 8_566 ?
N1 Zn1 N2 89.92(10) . 7_566 ?
N1 Zn1 N2 90.00(10) 2_656 7_566 ?
F1 Zn1 N2 91.23(8) . 7_566 ?
N2 Zn1 N2 177.54(16) 8_566 7_566 ?
N1 Zn1 F2 88.10(8) . 1_565 ?
N1 Zn1 F2 88.10(8) 2_656 1_565 ?
F1 Zn1 F2 180.0 . 1_565 ?
N2 Zn1 F2 88.77(8) 8_566 1_565 ?
N2 Zn1 F2 88.77(8) 7_566 1_565 ?
F3 Si1 F3 179.86(17) . 2_656 ?
F3 Si1 F4 90.64(11) . . ?
F3 Si1 F4 89.36(11) 2_656 . ?
F3 Si1 F4 89.36(11) . 2_656 ?
F3 Si1 F4 90.64(11) 2_656 2_656 ?
F4 Si1 F4 179.60(17) . 2_656 ?
F3 Si1 F1 89.93(9) . . ?
F3 Si1 F1 89.93(9) 2_656 . ?
F4 Si1 F1 89.80(9) . . ?
F4 Si1 F1 89.80(9) 2_656 . ?
F3 Si1 F2 90.07(9) . . ?
F3 Si1 F2 90.07(9) 2_656 . ?
F4 Si1 F2 90.20(9) . . ?
F4 Si1 F2 90.20(9) 2_656 . ?
F1 Si1 F2 180.0 . . ?
Si1 F1 Zn1 180.0 . . ?
Si1 F2 Zn1 180.0 . 1_545 ?
C6 N2 C10 117.2(3) . . ?
C6 N2 Zn1 120.6(2) . 7_566 ?
C10 N2 Zn1 122.2(2) . 7_566 ?
C22 N3 C19 108.6(3) . . ?
C22 N3 H3 125.7 . . ?
C19 N3 H3 125.7 . . ?
C5 N1 C1 116.8(3) . . ?
C5 N1 Zn1 122.7(2) . . ?
C1 N1 Zn1 120.2(2) . . ?
C18 C19 N3 128.7(3) . . ?
C18 C19 C20 121.9(3) . . ?
N3 C19 C20 109.4(3) . . ?
C14 C21 C22 120.2(3) . . ?
C14 C21 C20 133.8(3) . . ?
C22 C21 C20 105.9(3) . . ?
N3 C22 C11 128.9(3) . . ?
N3 C22 C21 109.6(3) . . ?
C11 C22 C21 121.4(3) . . ?
C15 C20 C19 119.8(3) . . ?
C15 C20 C21 133.7(3) . . ?
C19 C20 C21 106.4(3) . . ?
C21 C14 C13 119.4(3) . . ?
C21 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C13 C12 118.8(3) . . ?
C14 C13 C8 120.7(3) . . ?
C12 C13 C8 120.4(3) . . ?
C12 C11 C22 117.3(3) . . ?
C12 C11 H11 121.3 . . ?
C22 C11 H11 121.3 . . ?
C4 C3 C2 116.1(3) . . ?
C4 C3 C16 123.0(3) . . ?
C2 C3 C16 120.9(3) . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C16 C15 C20 119.0(3) . . ?
C16 C15 H15 120.5 . . ?
C20 C15 H15 120.5 . . ?
C9 C8 C7 116.4(3) . . ?
C9 C8 C13 122.7(3) . . ?
C7 C8 C13 120.9(3) . . ?
C6 C7 C8 120.3(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
N1 C5 C4 123.1(3) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
N1 C1 C2 123.4(3) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
N2 C10 C9 122.9(3) . . ?
N2 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
C1 C2 C3 120.1(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
N2 C6 C7 123.2(3) . . ?
N2 C6 H6 118.4 . . ?
C7 C6 H6 118.4 . . ?
C15 C16 C17 119.7(3) . . ?
C15 C16 C3 120.7(3) . . ?
C17 C16 C3 119.6(3) . . ?
C17 C18 C19 117.3(3) . . ?
C17 C18 H18 121.3 . . ?
C19 C18 H18 121.3 . . ?
C11 C12 C13 122.7(3) . . ?
C11 C12 H12 118.6 . . ?
C13 C12 H12 118.6 . . ?
C18 C17 C16 122.3(3) . . ?
C18 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?

_refine_diff_density_max         0.822
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.076

_shelxl_version_number           2013-2



