# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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#  from this site to visualise CIF-encoded structures and 
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data_shelx

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
Tetrafluoro-1,4-diiodobenzene bis(N-(4-acetophenyl)-2-oxy-1-naphthaldiminato)-copper(ii)
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H28 Cu N2 O4, C6 F4 I2'
_chemical_formula_sum            'C44 H28 Cu F4 I2 N2 O4'
_chemical_formula_weight         1042.02

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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                   8.093(5)
_cell_length_b                   9.502(5)
_cell_length_c                   12.751(5)
_cell_angle_alpha                82.472(5)
_cell_angle_beta                 82.927(5)
_cell_angle_gamma                86.586(5)
_cell_volume                     963.8(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    295
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_F_000             509
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    2.235
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.41600
_exptl_absorpt_correction_T_max  0.77617
_exptl_absorpt_process_details   'N.W. Alcock (1970). Cryst. Computing, p271'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11870
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_av_R_equivalents  0.0730
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.787
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4192
_reflns_number_gt                3055
_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    ?
_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)+(0.0417P)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         4192
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0938
_refine_ls_wR_factor_gt          0.0879
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.003
_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
C1 C 0.2306(4) 0.9380(3) -0.1821(3) 0.0431(7) Uani 1 1 d . . . . .
C2 C 0.3672(4) 0.9883(4) -0.2558(3) 0.0539(9) Uani 1 1 d . . . . .
H2 H 0.4243 1.0648 -0.2421 0.065 Uiso 1 1 calc R U . . .
C3 C 0.4157(4) 0.9277(4) -0.3451(3) 0.0567(9) Uani 1 1 d . . . . .
H3 H 0.5033 0.9653 -0.3926 0.068 Uiso 1 1 calc R U . . .
C4 C 0.3368(4) 0.8080(4) -0.3685(3) 0.0519(9) Uani 1 1 d . . . . .
C5 C 0.3947(5) 0.7423(4) -0.4599(3) 0.0621(10) Uani 1 1 d . . . . .
H5 H 0.4835 0.7797 -0.5065 0.074 Uiso 1 1 calc R U . . .
C6 C 0.3218(6) 0.6239(5) -0.4809(4) 0.0731(13) Uani 1 1 d . . . . .
H6 H 0.3619 0.5797 -0.5404 0.088 Uiso 1 1 calc R U . . .
C7 C 0.1883(5) 0.5716(4) -0.4123(4) 0.0655(11) Uani 1 1 d . . . . .
H7 H 0.1356 0.4939 -0.4282 0.079 Uiso 1 1 calc R U . . .
C8 C 0.1305(5) 0.6303(4) -0.3215(3) 0.0589(10) Uani 1 1 d . . . . .
H8 H 0.0433 0.5896 -0.2753 0.071 Uiso 1 1 calc R U . . .
C9 C 0.2026(4) 0.7525(3) -0.2974(3) 0.0448(8) Uani 1 1 d . . . . .
C10 C 0.1452(4) 0.8208(3) -0.2026(3) 0.0410(7) Uani 1 1 d . . . . .
C11 C 0.0025(4) 0.7734(3) -0.1352(3) 0.0425(8) Uani 1 1 d . . . . .
H023 H -0.0412 0.6905 -0.1495 0.051 Uiso 1 1 calc R U . . .
C12 C -0.2203(4) 0.7618(3) -0.0020(3) 0.0391(7) Uani 1 1 d . . . . .
C13 C -0.2020(4) 0.6415(3) 0.0674(3) 0.0539(9) Uani 1 1 d . . . . .
H13 H -0.0961 0.6060 0.0809 0.065 Uiso 1 1 calc R U . . .
C14 C -0.3411(4) 0.5724(3) 0.1175(3) 0.0548(9) Uani 1 1 d . . . . .
H14 H -0.3277 0.4903 0.1647 0.066 Uiso 1 1 calc R U . . .
C15 C -0.5001(4) 0.6229(3) 0.0988(3) 0.0397(7) Uani 1 1 d . . . . .
C16 C -0.5166(4) 0.7446(4) 0.0284(3) 0.0510(9) Uani 1 1 d . . . . .
H16 H -0.6224 0.7801 0.0145 0.061 Uiso 1 1 calc R U . . .
C17 C -0.3781(4) 0.8144(4) -0.0218(3) 0.0531(9) Uani 1 1 d . . . . .
H17 H -0.3908 0.8967 -0.0689 0.064 Uiso 1 1 calc R U . . .
C18 C -0.6511(4) 0.5497(3) 0.1527(3) 0.0462(8) Uani 1 1 d . . . . .
C19 C -0.6314(5) 0.4271(4) 0.2360(3) 0.0686(11) Uani 1 1 d . . . . .
H19A H -0.7388 0.3912 0.2631 0.103 Uiso 1 1 calc R U . . .
H19B H -0.5805 0.4572 0.2929 0.103 Uiso 1 1 calc R U . . .
H19C H -0.5621 0.3536 0.2057 0.103 Uiso 1 1 calc R U . . .
C20 C 0.0749(4) 1.1250(3) -0.5030(3) 0.0533(9) Uani 1 1 d . . . . .
C21 C -0.0289(4) 1.0793(3) -0.4130(3) 0.0474(8) Uani 1 1 d . . . . .
C22 C -0.1039(4) 0.9496(4) -0.4111(3) 0.0510(8) Uani 1 1 d . . . . .
N1 N -0.0751(3) 0.8323(2) -0.0553(2) 0.0409(6) Uani 1 1 d . . . . .
O1 O 0.1928(3) 1.0035(2) -0.09889(19) 0.0513(6) Uani 1 1 d . . . . .
O2 O -0.7893(3) 0.5886(3) 0.1297(2) 0.0638(7) Uani 1 1 d . . . . .
F1 F 0.1534(3) 1.2476(2) -0.5092(2) 0.0753(7) Uani 1 1 d . . . . .
F2 F -0.2032(3) 0.8983(2) -0.3258(2) 0.0713(6) Uani 1 1 d . . . . .
Cu1 Cu 0.0000 1.0000 0.0000 0.04035(15) Uani 1 2 d S . P . .
I1 I -0.08204(4) 1.19808(3) -0.28691(2) 0.07013(13) 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
C1 O1 1.295(4) . ?
C1 C10 1.414(4) . ?
C1 C2 1.422(5) . ?
C2 C3 1.348(5) . ?
C3 C4 1.419(5) . ?
C4 C9 1.407(5) . ?
C4 C5 1.410(5) . ?
C5 C6 1.372(6) . ?
C6 C7 1.377(6) . ?
C7 C8 1.369(5) . ?
C8 C9 1.414(5) . ?
C9 C10 1.460(4) . ?
C10 C11 1.412(5) . ?
C11 N1 1.302(4) . ?
C12 C13 1.363(5) . ?
C12 C17 1.384(4) . ?
C12 N1 1.439(4) . ?
C13 C14 1.381(5) . ?
C14 C15 1.383(4) . ?
C15 C16 1.379(5) . ?
C15 C18 1.490(5) . ?
C16 C17 1.381(5) . ?
C18 O2 1.215(4) . ?
C18 C19 1.485(5) . ?
C20 F1 1.349(4) . ?
C20 C22 1.370(5) 2_574 ?
C20 C21 1.373(5) . ?
C21 C22 1.402(5) . ?
C21 I1 2.072(3) . ?
C22 F2 1.326(4) . ?
C22 C20 1.370(5) 2_574 ?
N1 Cu1 1.980(2) . ?
O1 Cu1 1.881(2) . ?
Cu1 O1 1.881(2) 2_575 ?
Cu1 N1 1.980(2) 2_575 ?

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 C10 123.9(3) . . ?
O1 C1 C2 117.0(3) . . ?
C10 C1 C2 119.1(3) . . ?
C3 C2 C1 121.5(3) . . ?
C2 C3 C4 121.8(3) . . ?
C9 C4 C5 120.2(3) . . ?
C9 C4 C3 119.1(3) . . ?
C5 C4 C3 120.7(4) . . ?
C6 C5 C4 120.8(4) . . ?
C5 C6 C7 118.9(4) . . ?
C8 C7 C6 122.1(4) . . ?
C7 C8 C9 120.5(4) . . ?
C4 C9 C8 117.5(3) . . ?
C4 C9 C10 119.5(3) . . ?
C8 C9 C10 123.0(3) . . ?
C11 C10 C1 120.9(3) . . ?
C11 C10 C9 120.1(3) . . ?
C1 C10 C9 119.0(3) . . ?
N1 C11 C10 127.5(3) . . ?
C13 C12 C17 119.9(3) . . ?
C13 C12 N1 119.7(3) . . ?
C17 C12 N1 120.4(3) . . ?
C12 C13 C14 119.9(3) . . ?
C13 C14 C15 121.2(3) . . ?
C16 C15 C14 118.3(3) . . ?
C16 C15 C18 120.0(3) . . ?
C14 C15 C18 121.8(3) . . ?
C15 C16 C17 120.8(3) . . ?
C16 C17 C12 119.9(3) . . ?
O2 C18 C19 119.8(3) . . ?
O2 C18 C15 121.2(3) . . ?
C19 C18 C15 119.1(3) . . ?
F1 C20 C22 117.3(4) . 2_574 ?
F1 C20 C21 120.0(3) . . ?
C22 C20 C21 122.6(3) 2_574 . ?
C20 C21 C22 117.0(3) . . ?
C20 C21 I1 122.4(2) . . ?
C22 C21 I1 120.6(3) . . ?
F2 C22 C20 119.6(3) . 2_574 ?
F2 C22 C21 120.1(3) . . ?
C20 C22 C21 120.3(4) 2_574 . ?
C11 N1 C12 115.3(2) . . ?
C11 N1 Cu1 124.9(2) . . ?
C12 N1 Cu1 119.67(19) . . ?
C1 O1 Cu1 130.58(19) . . ?
O1 Cu1 O1 180.0 2_575 . ?
O1 Cu1 N1 89.34(10) 2_575 . ?
O1 Cu1 N1 90.66(10) . . ?
O1 Cu1 N1 90.66(10) 2_575 2_575 ?
O1 Cu1 N1 89.34(10) . 2_575 ?
N1 Cu1 N1 180.0 . 2_575 ?

_refine_diff_density_max         0.363
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.110

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 1013917'
