# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_f:\single~1\d2018a\ygz
_database_code_depnum_ccdc_archive 'CCDC 1024557'
_audit_update_record             
;
2014-09-16 deposited with the CCDC.
2015-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 Cl N2 O Zn'
_chemical_formula_weight         348.09

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   p21/n

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

_cell_length_a                   7.767(4)
_cell_length_b                   9.670(5)
_cell_length_c                   19.707(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.545(10)
_cell_angle_gamma                90.00
_cell_volume                     1463.7(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2561
_cell_measurement_theta_min      2.09
_cell_measurement_theta_max      25

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    1.858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7075
_exptl_absorpt_correction_T_max  0.7429
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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            9994
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2561
_reflns_number_gt                1906
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1268P)²+3.5573P] 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         2561
_refine_ls_number_parameters     190
_refine_ls_number_restraints     184
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0600
_refine_ls_wR_factor_ref         0.2075
_refine_ls_wR_factor_gt          0.1823
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.027
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.48541(10) 0.39637(7) 0.06630(3) 0.0383(3) Uani 1 1 d U . .
Cl1 Cl 0.7229(5) 0.3530(3) 0.14015(14) 0.1053(11) Uani 1 1 d U . .
O1 O 0.4530(7) 0.3959(4) -0.0354(2) 0.0454(11) Uani 1 1 d U . .
N1 N 0.3660(7) 0.1914(5) 0.0434(2) 0.0357(11) Uani 1 1 d U . .
C1 C 0.3913(8) 0.2813(6) -0.0673(3) 0.0364(13) Uani 1 1 d U . .
N2 N 0.2027(7) -0.0149(5) 0.3822(2) 0.0394(12) Uani 1 1 d U . .
C2 C 0.3715(9) 0.2625(7) -0.1375(3) 0.0444(15) Uani 1 1 d U . .
H2B H 0.4069 0.3338 -0.1656 0.053 Uiso 1 1 calc R . .
C3 C 0.3008(10) 0.1410(7) -0.1681(3) 0.0492(16) Uani 1 1 d U . .
H3A H 0.2889 0.1315 -0.2165 0.059 Uiso 1 1 calc R . .
C4 C 0.2482(9) 0.0348(7) -0.1298(3) 0.0479(16) Uani 1 1 d U . .
H4A H 0.1996 -0.0470 -0.1516 0.058 Uiso 1 1 calc R . .
C5 C 0.2671(8) 0.0485(7) -0.0574(3) 0.0409(14) Uani 1 1 d U . .
C6 C 0.3405(8) 0.1705(6) -0.0262(3) 0.0347(12) Uani 1 1 d U . .
C7 C 0.2205(9) -0.0554(8) -0.0134(4) 0.0505(16) Uani 1 1 d U . .
H7A H 0.1704 -0.1395 -0.0319 0.061 Uiso 1 1 calc R . .
C8 C 0.2474(9) -0.0352(7) 0.0555(3) 0.0493(16) Uani 1 1 d U . .
H8A H 0.2177 -0.1062 0.0850 0.059 Uiso 1 1 calc R . .
C9 C 0.3191(8) 0.0901(6) 0.0839(3) 0.0376(13) Uani 1 1 d U . .
C10 C 0.3493(9) 0.1131(6) 0.1571(3) 0.0416(15) Uani 1 1 d U . .
H10A H 0.4317 0.1817 0.1745 0.050 Uiso 1 1 calc R . .
C11 C 0.2680(9) 0.0434(8) 0.2023(3) 0.0478(16) Uani 1 1 d U . .
H11A H 0.1822 -0.0216 0.1835 0.057 Uiso 1 1 calc R . .
C12 C 0.2967(9) 0.0563(7) 0.2767(3) 0.0423(14) Uani 1 1 d U . .
C13 C 0.4278(9) 0.1347(8) 0.3143(4) 0.0531(17) Uani 1 1 d U . .
H13A H 0.5056 0.1864 0.2913 0.064 Uiso 1 1 calc R . .
C14 C 0.4446(10) 0.1372(8) 0.3848(4) 0.0550(18) Uani 1 1 d U . .
H14A H 0.5341 0.1903 0.4108 0.066 Uiso 1 1 calc R . .
C15 C 0.3296(9) 0.0615(7) 0.4172(3) 0.0452(15) Uani 1 1 d U . .
H15A H 0.3410 0.0637 0.4659 0.054 Uiso 1 1 calc R . .
C16 C 0.1894(9) -0.0172(7) 0.3140(3) 0.0419(14) Uani 1 1 d U . .
H16A H 0.1006 -0.0728 0.2893 0.050 Uiso 1 1 calc R . .


_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 1.983(4) . ?
Zn1 N2 2.084(5) 2 ?
Zn1 O1 2.173(4) 3_665 ?
Zn1 N1 2.206(5) . ?
Zn1 Cl1 2.213(3) . ?
O1 C1 1.327(7) . ?
O1 Zn1 2.173(4) 3_665 ?
N1 C9 1.348(7) . ?
N1 C6 1.371(7) . ?
C1 C2 1.382(8) . ?
C1 C6 1.433(8) . ?
N2 C16 1.333(7) . ?
N2 C15 1.338(8) . ?
N2 Zn1 2.084(5) 2_545 ?
C2 C3 1.395(10) . ?
C2 H2B 0.9500 . ?
C3 C4 1.371(10) . ?
C3 H3A 0.9500 . ?
C4 C5 1.419(8) . ?
C4 H4A 0.9500 . ?
C5 C7 1.410(10) . ?
C5 C6 1.411(9) . ?
C7 C8 1.357(10) . ?
C7 H7A 0.9500 . ?
C8 C9 1.414(10) . ?
C8 H8A 0.9500 . ?
C9 C10 1.444(9) . ?
C10 C11 1.346(9) . ?
C10 H10A 0.9500 . ?
C11 C12 1.455(9) . ?
C11 H11A 0.9500 . ?
C12 C16 1.386(8) . ?
C12 C13 1.391(10) . ?
C13 C14 1.376(10) . ?
C13 H13A 0.9500 . ?
C14 C15 1.384(10) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 H16A 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
O1 Zn1 N2 120.0(2) . 2 ?
O1 Zn1 O1 73.70(19) . 3_665 ?
N2 Zn1 O1 87.43(19) 2 3_665 ?
O1 Zn1 N1 78.73(17) . . ?
N2 Zn1 N1 99.55(19) 2 . ?
O1 Zn1 N1 151.23(17) 3_665 . ?
O1 Zn1 Cl1 129.22(18) . . ?
N2 Zn1 Cl1 109.51(17) 2 . ?
O1 Zn1 Cl1 99.37(15) 3_665 . ?
N1 Zn1 Cl1 104.37(15) . . ?
C1 O1 Zn1 117.5(3) . . ?
C1 O1 Zn1 135.9(4) . 3_665 ?
Zn1 O1 Zn1 106.30(19) . 3_665 ?
C9 N1 C6 118.3(5) . . ?
C9 N1 Zn1 132.4(4) . . ?
C6 N1 Zn1 109.3(4) . . ?
O1 C1 C2 124.2(5) . . ?
O1 C1 C6 117.9(5) . . ?
C2 C1 C6 118.0(6) . . ?
C16 N2 C15 118.1(5) . . ?
C16 N2 Zn1 122.0(4) . 2_545 ?
C15 N2 Zn1 119.4(4) . 2_545 ?
C1 C2 C3 121.4(6) . . ?
C1 C2 H2B 119.3 . . ?
C3 C2 H2B 119.3 . . ?
C4 C3 C2 121.6(6) . . ?
C4 C3 H3A 119.2 . . ?
C2 C3 H3A 119.2 . . ?
C3 C4 C5 119.2(6) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
C7 C5 C6 116.8(6) . . ?
C7 C5 C4 123.7(6) . . ?
C6 C5 C4 119.5(6) . . ?
N1 C6 C5 123.3(5) . . ?
N1 C6 C1 116.4(5) . . ?
C5 C6 C1 120.4(5) . . ?
C8 C7 C5 119.8(6) . . ?
C8 C7 H7A 120.1 . . ?
C5 C7 H7A 120.1 . . ?
C7 C8 C9 120.8(6) . . ?
C7 C8 H8A 119.6 . . ?
C9 C8 H8A 119.6 . . ?
N1 C9 C8 120.9(5) . . ?
N1 C9 C10 117.5(6) . . ?
C8 C9 C10 121.6(5) . . ?
C11 C10 C9 124.1(6) . . ?
C11 C10 H10A 117.9 . . ?
C9 C10 H10A 117.9 . . ?
C10 C11 C12 127.3(7) . . ?
C10 C11 H11A 116.3 . . ?
C12 C11 H11A 116.3 . . ?
C16 C12 C13 116.5(6) . . ?
C16 C12 C11 118.4(6) . . ?
C13 C12 C11 125.0(6) . . ?
C14 C13 C12 120.0(6) . . ?
C14 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C13 C14 C15 119.1(7) . . ?
C13 C14 H14A 120.5 . . ?
C15 C14 H14A 120.5 . . ?
N2 C15 C14 122.0(6) . . ?
N2 C15 H15A 119.0 . . ?
C14 C15 H15A 119.0 . . ?
N2 C16 C12 124.3(6) . . ?
N2 C16 H16A 117.8 . . ?
C12 C16 H16A 117.8 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         2.379
_refine_diff_density_min         -0.845
_refine_diff_density_rms         0.292
####################################################################### 
# 
# 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_f:\single~1\r8009d\ygz
_database_code_depnum_ccdc_archive 'CCDC 1024558'
_audit_update_record             
;
2014-09-16 deposited with the CCDC.
2015-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 I N2 O Zn'
_chemical_formula_weight         439.54

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   7.4490(8)
_cell_length_b                   10.1689(11)
_cell_length_c                   20.082(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.345(2)
_cell_angle_gamma                90.00
_cell_volume                     1511.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3460
_cell_measurement_theta_min      2.04
_cell_measurement_theta_max      27.49

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.931
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    3.665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5277
_exptl_absorpt_correction_T_max  0.5583
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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            12827
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3460
_reflns_number_gt                2679
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0667P)²+1.8335P] 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         3460
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1193
_refine_ls_wR_factor_gt          0.1095
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.28500(5) 1.15232(4) -0.136953(18) 0.04859(15) Uani 1 1 d . . .
Zn1 Zn 0.01642(8) 1.10003(5) -0.06586(2) 0.02989(16) Uani 1 1 d . . .
O1 O 0.0544(5) 1.1001(3) 0.03275(14) 0.0340(7) Uani 1 1 d . . .
N1 N 0.1406(5) 1.2957(3) -0.04700(17) 0.0247(7) Uani 1 1 d . . .
C1 C 0.1106(6) 1.2107(4) 0.0613(2) 0.0270(9) Uani 1 1 d . . .
N2 N 0.2974(5) 1.5070(4) -0.38140(18) 0.0318(8) Uani 1 1 d . . .
C2 C 0.1224(7) 1.2330(5) 0.1304(2) 0.0342(10) Uani 1 1 d . . .
H2B H 0.0873 1.1652 0.1589 0.041 Uiso 1 1 calc R . .
C3 C 0.1844(8) 1.3520(5) 0.1585(2) 0.0390(11) Uani 1 1 d . . .
H3A H 0.1886 1.3635 0.2055 0.047 Uiso 1 1 calc R . .
C4 C 0.2393(7) 1.4524(5) 0.1206(2) 0.0376(11) Uani 1 1 d . . .
H4A H 0.2856 1.5314 0.1412 0.045 Uiso 1 1 calc R . .
C5 C 0.2260(6) 1.4372(4) 0.0497(2) 0.0289(9) Uani 1 1 d . . .
C6 C 0.1589(6) 1.3171(4) 0.0207(2) 0.0255(9) Uani 1 1 d . . .
C7 C 0.2712(7) 1.5363(5) 0.0055(2) 0.0380(11) Uani 1 1 d . . .
H7A H 0.3167 1.6182 0.0226 0.046 Uiso 1 1 calc R . .
C8 C 0.2497(7) 1.5145(5) -0.0615(2) 0.0373(11) Uani 1 1 d . . .
H8A H 0.2789 1.5819 -0.0912 0.045 Uiso 1 1 calc R . .
C9 C 0.1842(6) 1.3925(4) -0.0873(2) 0.0297(9) Uani 1 1 d . . .
C10 C 0.1589(7) 1.3689(4) -0.1596(2) 0.0320(10) Uani 1 1 d . . .
H10A H 0.0827 1.2982 -0.1756 0.038 Uiso 1 1 calc R . .
C11 C 0.2350(7) 1.4397(5) -0.2042(2) 0.0405(12) Uani 1 1 d . . .
H11A H 0.3171 1.5058 -0.1867 0.049 Uiso 1 1 calc R . .
C12 C 0.2071(7) 1.4277(5) -0.2772(2) 0.0331(10) Uani 1 1 d . . .
C13 C 0.0884(7) 1.3414(5) -0.3122(3) 0.0390(11) Uani 1 1 d . . .
H13A H 0.0168 1.2839 -0.2888 0.047 Uiso 1 1 calc R . .
C14 C 0.0743(7) 1.3392(5) -0.3813(3) 0.0400(11) Uani 1 1 d . . .
H14A H -0.0071 1.2802 -0.4058 0.048 Uiso 1 1 calc R . .
C15 C 0.1791(7) 1.4232(5) -0.4147(2) 0.0366(11) Uani 1 1 d . . .
H15A H 0.1677 1.4220 -0.4622 0.044 Uiso 1 1 calc R . .
C16 C 0.3118(7) 1.5073(5) -0.3144(2) 0.0349(11) Uani 1 1 d . . .
H16A H 0.3976 1.5646 -0.2909 0.042 Uiso 1 1 calc R . .


_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
I1 Zn1 2.5795(7) . ?
Zn1 O1 1.969(3) . ?
Zn1 N2 2.065(4) 2_544 ?
Zn1 N1 2.209(4) . ?
Zn1 O1 2.222(3) 3_575 ?
O1 C1 1.310(5) . ?
O1 Zn1 2.222(3) 3_575 ?
N1 C9 1.337(5) . ?
N1 C6 1.368(5) . ?
C1 C2 1.399(6) . ?
C1 C6 1.426(6) . ?
N2 C16 1.338(6) . ?
N2 C15 1.349(6) . ?
N2 Zn1 2.065(4) 2_554 ?
C2 C3 1.392(7) . ?
C3 C4 1.363(7) . ?
C4 C5 1.425(6) . ?
C5 C7 1.407(6) . ?
C5 C6 1.421(6) . ?
C7 C8 1.355(7) . ?
C8 C9 1.411(6) . ?
C9 C10 1.463(6) . ?
C10 C11 1.324(6) . ?
C11 C12 1.463(7) . ?
C12 C13 1.381(7) . ?
C12 C16 1.397(6) . ?
C13 C14 1.381(7) . ?
C14 C15 1.380(7) . ?

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 N2 119.09(15) . 2_544 ?
O1 Zn1 N1 79.42(13) . . ?
N2 Zn1 N1 102.02(14) 2_544 . ?
O1 Zn1 O1 73.25(13) . 3_575 ?
N2 Zn1 O1 85.94(14) 2_544 3_575 ?
N1 Zn1 O1 151.89(12) . 3_575 ?
O1 Zn1 I1 125.16(11) . . ?
N2 Zn1 I1 113.78(11) 2_544 . ?
N1 Zn1 I1 103.39(10) . . ?
O1 Zn1 I1 97.68(9) 3_575 . ?
C1 O1 Zn1 116.4(3) . . ?
C1 O1 Zn1 136.9(3) . 3_575 ?
Zn1 O1 Zn1 106.75(13) . 3_575 ?
C9 N1 C6 118.7(4) . . ?
C9 N1 Zn1 133.2(3) . . ?
C6 N1 Zn1 107.9(3) . . ?
O1 C1 C2 123.7(4) . . ?
O1 C1 C6 119.3(4) . . ?
C2 C1 C6 116.9(4) . . ?
C16 N2 C15 118.3(4) . . ?
C16 N2 Zn1 122.1(3) . 2_554 ?
C15 N2 Zn1 118.3(3) . 2_554 ?
C3 C2 C1 121.6(4) . . ?
C4 C3 C2 122.2(4) . . ?
C3 C4 C5 118.9(4) . . ?
C7 C5 C6 117.0(4) . . ?
C7 C5 C4 123.9(4) . . ?
C6 C5 C4 119.1(4) . . ?
N1 C6 C5 122.5(4) . . ?
N1 C6 C1 116.4(4) . . ?
C5 C6 C1 121.1(4) . . ?
C8 C7 C5 119.9(4) . . ?
C7 C8 C9 120.4(4) . . ?
N1 C9 C8 121.5(4) . . ?
N1 C9 C10 117.8(4) . . ?
C8 C9 C10 120.7(4) . . ?
C11 C10 C9 124.3(5) . . ?
C10 C11 C12 127.5(5) . . ?
C13 C12 C16 117.4(4) . . ?
C13 C12 C11 125.1(4) . . ?
C16 C12 C11 117.5(4) . . ?
C12 C13 C14 119.7(4) . . ?
C15 C14 C13 119.6(5) . . ?
N2 C15 C14 121.6(4) . . ?
N2 C16 C12 123.3(5) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.103
_refine_diff_density_min         -0.884
_refine_diff_density_rms         0.123
####################################################################### 
# 
# 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_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1024559'
_audit_update_record             
;
2014-09-16 deposited with the CCDC.
2015-01-08 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H22 Br2 N4 O3 Zn2'
_chemical_formula_weight         849.14

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'
Br Br -0.2901 2.4595 '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                   23.908(4)
_cell_length_b                   11.2970(17)
_cell_length_c                   16.294(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 130.487(2)
_cell_angle_gamma                90.00
_cell_volume                     3347.0(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      25.79

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1680
_exptl_absorpt_coefficient_mu    3.863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5121
_exptl_absorpt_correction_T_max  0.5273
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14309
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         27.59
_reflns_number_total             3832
_reflns_number_gt                2822
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0482P)²+4.0697P] 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         3832
_refine_ls_number_parameters     202
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0983
_refine_ls_wR_factor_gt          0.0872
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.023
_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
Br1 Br 0.57429(2) 0.78278(4) 0.41455(3) 0.05848(14) Uani 1 1 d . . .
Zn1 Zn 0.67584(2) 0.67814(3) 0.45614(3) 0.03903(12) Uani 1 1 d . . .
O1 O 0.78124(12) 0.6980(2) 0.58785(18) 0.0497(6) Uani 1 1 d . . .
N1 N 0.68947(14) 0.5388(2) 0.5657(2) 0.0400(6) Uani 1 1 d . . .
C1 C 0.80822(18) 0.6283(3) 0.6719(2) 0.0416(7) Uani 1 1 d . . .
N2 N 0.34767(15) 0.5480(2) 0.1536(2) 0.0423(6) Uani 1 1 d . . .
C2 C 0.87891(19) 0.6355(3) 0.7678(3) 0.0490(8) Uani 1 1 d . . .
H2 H 0.9118 0.6917 0.7760 0.059 Uiso 1 1 calc R . .
C3 C 0.9034(2) 0.5605(4) 0.8543(3) 0.0579(10) Uani 1 1 d . . .
H3 H 0.9524 0.5682 0.9204 0.069 Uiso 1 1 calc R . .
C4 C 0.8585(2) 0.4769(4) 0.8458(3) 0.0594(10) Uani 1 1 d . . .
H4 H 0.8764 0.4272 0.9054 0.071 Uiso 1 1 calc R . .
C5 C 0.7857(2) 0.4646(3) 0.7481(3) 0.0472(8) Uani 1 1 d . . .
C6 C 0.76015(17) 0.5424(3) 0.6612(2) 0.0380(7) Uani 1 1 d . . .
C7 C 0.7343(2) 0.3815(3) 0.7289(3) 0.0553(9) Uani 1 1 d . . .
H7 H 0.7490 0.3266 0.7839 0.066 Uiso 1 1 calc R . .
C8 C 0.6645(2) 0.3782(3) 0.6340(3) 0.0528(9) Uani 1 1 d . . .
H8 H 0.6308 0.3209 0.6220 0.063 Uiso 1 1 calc R . .
C9 C 0.64185(19) 0.4619(3) 0.5517(3) 0.0436(7) Uani 1 1 d . . .
C10 C 0.5663(2) 0.4706(3) 0.4498(3) 0.0494(8) Uani 1 1 d . . .
H10 H 0.5590 0.5227 0.3978 0.059 Uiso 1 1 calc R . .
C11 C 0.5070(2) 0.4159(3) 0.4203(3) 0.0497(8) Uani 1 1 d . . .
H11 H 0.5132 0.3600 0.4691 0.060 Uiso 1 1 calc R . .
C12 C 0.43222(19) 0.4349(3) 0.3178(3) 0.0472(8) Uani 1 1 d . . .
C13 C 0.3749(2) 0.3600(4) 0.2837(4) 0.0644(11) Uani 1 1 d . . .
H13 H 0.3833 0.2957 0.3280 0.077 Uiso 1 1 calc R . .
C14 C 0.3061(2) 0.3782(4) 0.1861(4) 0.0724(12) Uani 1 1 d . . .
H14 H 0.2669 0.3264 0.1626 0.087 Uiso 1 1 calc R . .
C15 C 0.2941(2) 0.4716(4) 0.1226(3) 0.0593(10) Uani 1 1 d . . .
H15 H 0.2465 0.4824 0.0545 0.071 Uiso 1 1 calc R . .
C16 C 0.41464(19) 0.5297(3) 0.2495(3) 0.0433(7) Uani 1 1 d . . .
H16 H 0.4525 0.5846 0.2724 0.052 Uiso 1 1 calc R . .
C17 C 0.4733(7) 0.8629(11) 0.6954(6) 0.224(5) Uiso 1 1 d D . .
C18 C 0.3952(5) 0.8625(8) 0.6197(7) 0.150(3) Uiso 1 1 d . . .
O19 O 0.5086(6) 0.8647(10) 0.6536(9) 0.146(4) Uiso 0.50 1 d P . .


_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
Br1 Zn1 2.3697(6) . ?
Zn1 O1 1.996(2) . ?
Zn1 N2 2.090(3) 2_655 ?
Zn1 O1 2.117(2) 7_666 ?
Zn1 N1 2.239(2) . ?
O1 C1 1.328(4) . ?
O1 Zn1 2.117(2) 7_666 ?
N1 C9 1.329(4) . ?
N1 C6 1.366(4) . ?
C1 C2 1.369(5) . ?
C1 C6 1.426(5) . ?
N2 C16 1.342(4) . ?
N2 C15 1.342(5) . ?
N2 Zn1 2.090(3) 2_655 ?
C2 C3 1.405(5) . ?
C3 C4 1.367(6) . ?
C4 C5 1.409(5) . ?
C5 C7 1.411(5) . ?
C5 C6 1.423(4) . ?
C7 C8 1.351(5) . ?
C8 C9 1.428(5) . ?
C9 C10 1.460(5) . ?
C10 C11 1.318(5) . ?
C11 C12 1.468(5) . ?
C12 C13 1.383(5) . ?
C12 C16 1.399(5) . ?
C13 C14 1.371(6) . ?
C14 C15 1.371(6) . ?
C17 C17 1.360(15) 2_656 ?
C17 O19 1.386(16) . ?
C17 C18 1.421(14) . ?

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 N2 116.70(11) . 2_655 ?
O1 Zn1 O1 74.85(10) . 7_666 ?
N2 Zn1 O1 95.50(10) 2_655 7_666 ?
O1 Zn1 N1 78.06(9) . . ?
N2 Zn1 N1 90.37(10) 2_655 . ?
O1 Zn1 N1 152.01(9) 7_666 . ?
O1 Zn1 Br1 126.54(8) . . ?
N2 Zn1 Br1 116.72(8) 2_655 . ?
O1 Zn1 Br1 101.84(7) 7_666 . ?
N1 Zn1 Br1 99.82(7) . . ?
C1 O1 Zn1 118.1(2) . . ?
C1 O1 Zn1 136.3(2) . 7_666 ?
Zn1 O1 Zn1 105.15(9) . 7_666 ?
C9 N1 C6 120.2(3) . . ?
C9 N1 Zn1 131.1(2) . . ?
C6 N1 Zn1 108.7(2) . . ?
O1 C1 C2 123.7(3) . . ?
O1 C1 C6 117.6(3) . . ?
C2 C1 C6 118.6(3) . . ?
C16 N2 C15 117.7(3) . . ?
C16 N2 Zn1 124.0(2) . 2_655 ?
C15 N2 Zn1 118.0(2) . 2_655 ?
C1 C2 C3 120.7(3) . . ?
C4 C3 C2 121.7(3) . . ?
C3 C4 C5 119.7(3) . . ?
C4 C5 C7 125.2(3) . . ?
C4 C5 C6 118.7(3) . . ?
C7 C5 C6 116.1(3) . . ?
N1 C6 C5 122.0(3) . . ?
N1 C6 C1 117.5(3) . . ?
C5 C6 C1 120.5(3) . . ?
C8 C7 C5 121.5(3) . . ?
C7 C8 C9 119.4(3) . . ?
N1 C9 C8 120.7(3) . . ?
N1 C9 C10 116.1(3) . . ?
C8 C9 C10 123.2(3) . . ?
C11 C10 C9 128.8(3) . . ?
C10 C11 C12 125.1(3) . . ?
C13 C12 C16 116.2(3) . . ?
C13 C12 C11 121.7(3) . . ?
C16 C12 C11 122.1(3) . . ?
C14 C13 C12 120.3(4) . . ?
C13 C14 C15 119.7(4) . . ?
N2 C15 C14 122.1(4) . . ?
N2 C16 C12 124.0(3) . . ?
C17 C17 O19 106.8(18) 2_656 . ?
C17 C17 C18 136(2) 2_656 . ?
O19 C17 C18 116.8(9) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.59
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.077
####################################################################### 
# 
# 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_f:\single~1\r7066f\ygz
_database_code_depnum_ccdc_archive 'CCDC 1024560'
_audit_update_record             
;
2014-09-16 deposited with the CCDC.
2015-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 Cd N2 O3'
_chemical_formula_weight         418.71

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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   8.0700(9)
_cell_length_b                   9.9439(11)
_cell_length_c                   20.676(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.206(2)
_cell_angle_gamma                90.00
_cell_volume                     1649.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3871
_cell_measurement_theta_min      1.98
_cell_measurement_theta_max      27.74

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    1.342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7752
_exptl_absorpt_correction_T_max  0.7846
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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            26848
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         27.74
_reflns_number_total             3871
_reflns_number_gt                3210
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0281P)²+0.7085P] 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         3871
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0259
_refine_ls_wR_factor_ref         0.0648
_refine_ls_wR_factor_gt          0.0607
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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
Cd1 Cd 0.50397(2) 0.900275(18) 0.073284(7) 0.03105(7) Uani 1 1 d . . .
O1 O 0.4425(3) 0.89144(18) -0.03414(8) 0.0418(5) Uani 1 1 d . . .
N1 N 0.3718(2) 0.6900(2) 0.04828(9) 0.0302(4) Uani 1 1 d . . .
C1 C 0.3817(3) 0.7789(3) -0.05978(11) 0.0323(5) Uani 1 1 d . . .
O2 O 0.6607(3) 0.8606(2) 0.17669(11) 0.0552(6) Uani 1 1 d . . .
N2 N 0.1978(3) 0.5057(2) 0.37366(10) 0.0363(5) Uani 1 1 d . . .
C2 C 0.3518(4) 0.7581(3) -0.12649(12) 0.0407(6) Uani 1 1 d . . .
H2B H 0.3784 0.8272 -0.1553 0.049 Uiso 1 1 calc R . .
O3 O 0.7821(3) 0.8390(2) 0.08800(11) 0.0572(6) Uani 1 1 d . . .
C3 C 0.2833(4) 0.6377(3) -0.15211(13) 0.0472(7) Uani 1 1 d . . .
H3A H 0.2649 0.6268 -0.1980 0.057 Uiso 1 1 calc R . .
C4 C 0.2423(4) 0.5357(3) -0.11277(14) 0.0489(7) Uani 1 1 d . . .
H4A H 0.1950 0.4551 -0.1312 0.059 Uiso 1 1 calc R . .
C5 C 0.2704(4) 0.5504(3) -0.04473(13) 0.0394(6) Uani 1 1 d . . .
C6 C 0.3411(3) 0.6709(2) -0.01771(11) 0.0307(5) Uani 1 1 d . . .
C7 C 0.2346(4) 0.4486(3) -0.00065(15) 0.0523(8) Uani 1 1 d . . .
H7A H 0.1892 0.3653 -0.0165 0.063 Uiso 1 1 calc R . .
C8 C 0.2649(4) 0.4697(3) 0.06425(14) 0.0504(8) Uani 1 1 d . . .
H8A H 0.2404 0.4011 0.0937 0.060 Uiso 1 1 calc R . .
C9 C 0.3328(3) 0.5928(3) 0.08845(12) 0.0357(6) Uani 1 1 d . . .
C10 C 0.3620(4) 0.6188(3) 0.15858(12) 0.0372(6) Uani 1 1 d . . .
H10A H 0.4433 0.6838 0.1737 0.045 Uiso 1 1 calc R . .
C11 C 0.2796(4) 0.5554(3) 0.20208(12) 0.0390(6) Uani 1 1 d . . .
H11A H 0.1988 0.4915 0.1851 0.047 Uiso 1 1 calc R . .
C12 C 0.2985(3) 0.5722(3) 0.27269(12) 0.0352(6) Uani 1 1 d . . .
C13 C 0.4225(4) 0.6491(3) 0.30794(14) 0.0455(7) Uani 1 1 d . . .
H13A H 0.5004 0.6983 0.2859 0.055 Uiso 1 1 calc R . .
C14 C 0.4307(4) 0.6529(3) 0.37476(15) 0.0515(8) Uani 1 1 d . . .
H14A H 0.5139 0.7052 0.3992 0.062 Uiso 1 1 calc R . .
C15 C 0.3169(4) 0.5801(3) 0.40615(14) 0.0458(7) Uani 1 1 d . . .
H15A H 0.3239 0.5833 0.4523 0.055 Uiso 1 1 calc R . .
C16 C 0.1898(3) 0.5031(3) 0.30856(11) 0.0348(5) Uani 1 1 d . . .
H16A H 0.1044 0.4508 0.2855 0.042 Uiso 1 1 calc R . .
C17 C 0.7856(4) 0.8339(3) 0.14827(15) 0.0441(7) Uani 1 1 d . . .
C18 C 0.9438(4) 0.7893(4) 0.18824(19) 0.0672(10) Uani 1 1 d . . .
H18A H 1.0047 0.8683 0.2064 0.101 Uiso 1 1 calc R . .
H18B H 1.0136 0.7396 0.1605 0.101 Uiso 1 1 calc R . .
H18C H 0.9158 0.7310 0.2237 0.101 Uiso 1 1 calc R . .


_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
Cd1 O1 2.2246(17) . ?
Cd1 O1 2.2819(17) 3_675 ?
Cd1 N2 2.311(2) 2 ?
Cd1 O3 2.314(2) . ?
Cd1 N1 2.379(2) . ?
Cd1 O2 2.396(2) . ?
Cd1 C17 2.691(3) . ?
O1 C1 1.311(3) . ?
O1 Cd1 2.2819(17) 3_675 ?
N1 C9 1.334(3) . ?
N1 C6 1.374(3) . ?
C1 C2 1.390(3) . ?
C1 C6 1.442(3) . ?
O2 C17 1.249(4) . ?
N2 C15 1.336(4) . ?
N2 C16 1.341(3) . ?
N2 Cd1 2.311(2) 2_545 ?
C2 C3 1.399(4) . ?
O3 C17 1.244(4) . ?
C3 C4 1.363(4) . ?
C4 C5 1.408(4) . ?
C5 C7 1.413(4) . ?
C5 C6 1.416(4) . ?
C7 C8 1.354(4) . ?
C8 C9 1.410(4) . ?
C9 C10 1.467(4) . ?
C10 C11 1.333(3) . ?
C11 C12 1.461(4) . ?
C12 C16 1.390(3) . ?
C12 C13 1.400(4) . ?
C13 C14 1.377(4) . ?
C14 C15 1.384(4) . ?
C17 C18 1.511(4) . ?

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 Cd1 O1 73.26(7) . 3_675 ?
O1 Cd1 N2 113.54(8) . 2 ?
O1 Cd1 N2 85.80(8) 3_675 2 ?
O1 Cd1 O3 103.26(8) . . ?
O1 Cd1 O3 93.88(8) 3_675 . ?
N2 Cd1 O3 141.29(8) 2 . ?
O1 Cd1 N1 72.66(6) . . ?
O1 Cd1 N1 144.93(6) 3_675 . ?
N2 Cd1 N1 100.35(7) 2 . ?
O3 Cd1 N1 101.70(8) . . ?
O1 Cd1 O2 157.45(8) . . ?
O1 Cd1 O2 111.35(8) 3_675 . ?
N2 Cd1 O2 88.98(8) 2 . ?
O3 Cd1 O2 55.13(8) . . ?
N1 Cd1 O2 103.31(8) . . ?
O1 Cd1 C17 130.45(9) . . ?
O1 Cd1 C17 104.28(8) 3_675 . ?
N2 Cd1 C17 115.61(9) 2 . ?
O3 Cd1 C17 27.49(8) . . ?
N1 Cd1 C17 103.90(8) . . ?
O2 Cd1 C17 27.65(8) . . ?
C1 O1 Cd1 118.09(14) . . ?
C1 O1 Cd1 135.10(15) . 3_675 ?
Cd1 O1 Cd1 106.74(7) . 3_675 ?
C9 N1 C6 119.3(2) . . ?
C9 N1 Cd1 129.21(16) . . ?
C6 N1 Cd1 111.47(15) . . ?
O1 C1 C2 123.1(2) . . ?
O1 C1 C6 119.4(2) . . ?
C2 C1 C6 117.5(2) . . ?
C17 O2 Cd1 89.44(18) . . ?
C15 N2 C16 118.0(2) . . ?
C15 N2 Cd1 121.23(17) . 2_545 ?
C16 N2 Cd1 120.51(17) . 2_545 ?
C1 C2 C3 121.5(2) . . ?
C17 O3 Cd1 93.40(18) . . ?
C4 C3 C2 121.5(3) . . ?
C3 C4 C5 119.7(3) . . ?
C4 C5 C7 123.2(3) . . ?
C4 C5 C6 119.8(3) . . ?
C7 C5 C6 117.0(2) . . ?
N1 C6 C5 122.1(2) . . ?
N1 C6 C1 117.9(2) . . ?
C5 C6 C1 120.0(2) . . ?
C8 C7 C5 120.0(3) . . ?
C7 C8 C9 120.5(3) . . ?
N1 C9 C8 121.1(2) . . ?
N1 C9 C10 117.7(2) . . ?
C8 C9 C10 121.2(2) . . ?
C11 C10 C9 123.0(3) . . ?
C10 C11 C12 127.9(3) . . ?
C16 C12 C13 116.7(2) . . ?
C16 C12 C11 118.2(2) . . ?
C13 C12 C11 125.1(2) . . ?
C14 C13 C12 119.4(3) . . ?
C13 C14 C15 119.6(3) . . ?
N2 C15 C14 122.1(3) . . ?
N2 C16 C12 124.1(2) . . ?
O3 C17 O2 122.0(3) . . ?
O3 C17 C18 119.1(3) . . ?
O2 C17 C18 118.9(3) . . ?
O3 C17 Cd1 59.11(15) . . ?
O2 C17 Cd1 62.91(16) . . ?
C18 C17 Cd1 176.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.74
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.087
####################################################################### 
# 
# 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_d:\r7050a\sad
_database_code_depnum_ccdc_archive 'CCDC 1024561'
_audit_update_record             
;
2014-09-16 deposited with the CCDC.
2015-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 Cd N3 O4'
_chemical_formula_weight         421.68

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'
Cd Cd -0.8075 1.2024 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/C

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                   8.0362(17)
_cell_length_b                   9.919(2)
_cell_length_c                   21.302(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.484(7)
_cell_angle_gamma                90.00
_cell_volume                     1636.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2856
_cell_measurement_theta_min      1.98
_cell_measurement_theta_max      25

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    1.359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7634
_exptl_absorpt_correction_T_max  0.7823
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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            10993
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2856
_reflns_number_gt                2675
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0269P)²+3.1166P] 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         2856
_refine_ls_number_parameters     197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0727
_refine_ls_wR_factor_gt          0.0705
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.07089(3) 0.40032(2) 0.073267(10) 0.03258(10) Uani 1 1 d . . .
O1 O 0.0197(4) 0.3900(2) -0.03448(11) 0.0439(6) Uani 1 1 d . . .
N1 N 0.1761(3) 0.1893(3) 0.04769(12) 0.0318(6) Uani 1 1 d . . .
C1 C 0.0555(4) 0.2772(3) -0.06045(15) 0.0331(7) Uani 1 1 d . . .
O2 O -0.1966(4) 0.3407(3) 0.08813(15) 0.0593(7) Uiso 1 1 d . . .
N2 N 0.6736(4) 0.0049(3) 0.37316(13) 0.0382(6) Uani 1 1 d . . .
C2 C 0.0176(5) 0.2564(4) -0.12706(16) 0.0419(8) Uani 1 1 d . . .
H2B H -0.0392 0.3255 -0.1558 0.050 Uiso 1 1 calc R . .
O3 O 0.0150(4) 0.3604(3) 0.17634(14) 0.0555(7) Uiso 1 1 d . . .
C3 C 0.0614(5) 0.1355(4) -0.15310(18) 0.0480(9) Uani 1 1 d . . .
H3A H 0.0325 0.1240 -0.1990 0.058 Uiso 1 1 calc R . .
O4 O -0.2554(6) 0.2904(5) 0.1891(2) 0.1153(15) Uiso 1 1 d . . .
C4 C 0.1446(6) 0.0342(4) -0.11365(18) 0.0506(10) Uani 1 1 d . . .
H4B H 0.1751 -0.0462 -0.1321 0.061 Uiso 1 1 calc R . .
C5 C 0.1849(5) 0.0491(4) -0.04563(18) 0.0411(8) Uani 1 1 d . . .
C6 C 0.1409(4) 0.1699(3) -0.01821(15) 0.0317(7) Uani 1 1 d . . .
C7 C 0.2672(6) -0.0523(4) -0.0016(2) 0.0528(10) Uani 1 1 d . . .
H7A H 0.2982 -0.1354 -0.0176 0.063 Uiso 1 1 calc R . .
N8 N -0.1399(5) 0.3341(4) 0.14869(18) 0.0607(9) Uiso 1 1 d . . .
C8 C 0.3019(5) -0.0308(4) 0.06349(19) 0.0518(10) Uani 1 1 d . . .
H8A H 0.3571 -0.0992 0.0930 0.062 Uiso 1 1 calc R . .
C9 C 0.2569(4) 0.0921(3) 0.08777(17) 0.0372(8) Uani 1 1 d . . .
C10 C 0.2971(5) 0.1177(4) 0.15789(17) 0.0387(8) Uani 1 1 d . . .
H10A H 0.2300 0.1825 0.1731 0.046 Uiso 1 1 calc R . .
C11 C 0.4232(5) 0.0548(4) 0.20150(17) 0.0417(8) Uani 1 1 d . . .
H11A H 0.4888 -0.0084 0.1846 0.050 Uiso 1 1 calc R . .
C12 C 0.4727(4) 0.0713(4) 0.27225(16) 0.0375(8) Uani 1 1 d . . .
C13 C 0.3832(5) 0.1479(4) 0.30738(19) 0.0476(9) Uani 1 1 d . . .
H13A H 0.2832 0.1969 0.2852 0.057 Uiso 1 1 calc R . .
C14 C 0.4400(5) 0.1522(5) 0.3740(2) 0.0531(10) Uani 1 1 d . . .
H14A H 0.3802 0.2046 0.3983 0.064 Uiso 1 1 calc R . .
C15 C 0.5857(5) 0.0794(4) 0.40563(18) 0.0466(9) Uani 1 1 d . . .
H15A H 0.6240 0.0826 0.4518 0.056 Uiso 1 1 calc R . .
C16 C 0.6177(4) 0.0024(4) 0.30799(16) 0.0381(8) Uani 1 1 d . . .
H16A H 0.6809 -0.0497 0.2848 0.046 Uiso 1 1 calc R . .


_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
Cd1 O1 2.223(2) . ?
Cd1 O1 2.284(2) 3_565 ?
Cd1 N2 2.312(3) 2_655 ?
Cd1 O2 2.331(3) . ?
Cd1 N1 2.374(3) . ?
Cd1 O3 2.389(3) . ?
O1 C1 1.314(4) . ?
O1 Cd1 2.284(2) 3_565 ?
N1 C9 1.336(4) . ?
N1 C6 1.369(4) . ?
C1 C2 1.385(5) . ?
C1 C6 1.444(4) . ?
O2 N8 1.250(5) . ?
N2 C15 1.336(5) . ?
N2 C16 1.340(4) . ?
N2 Cd1 2.312(3) 2_645 ?
C2 C3 1.406(5) . ?
C2 H2B 0.9500 . ?
O3 N8 1.255(5) . ?
C3 C4 1.364(6) . ?
C3 H3A 0.9500 . ?
O4 N8 1.490(6) . ?
C4 C5 1.406(5) . ?
C4 H4B 0.9500 . ?
C5 C7 1.413(5) . ?
C5 C6 1.419(5) . ?
C7 C8 1.357(6) . ?
C7 H7A 0.9500 . ?
C8 C9 1.409(5) . ?
C8 H8A 0.9500 . ?
C9 C10 1.464(5) . ?
C10 C11 1.333(5) . ?
C10 H10A 0.9500 . ?
C11 C12 1.462(5) . ?
C11 H11A 0.9500 . ?
C12 C16 1.390(5) . ?
C12 C13 1.393(5) . ?
C13 C14 1.370(6) . ?
C13 H13A 0.9500 . ?
C14 C15 1.387(6) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 H16A 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
O1 Cd1 O1 73.44(9) . 3_565 ?
O1 Cd1 N2 115.18(10) . 2_655 ?
O1 Cd1 N2 85.71(10) 3_565 2_655 ?
O1 Cd1 O2 101.85(11) . . ?
O1 Cd1 O2 93.66(11) 3_565 . ?
N2 Cd1 O2 140.95(10) 2_655 . ?
O1 Cd1 N1 72.65(9) . . ?
O1 Cd1 N1 144.90(9) 3_565 . ?
N2 Cd1 N1 100.66(10) 2_655 . ?
O2 Cd1 N1 101.86(10) . . ?
O1 Cd1 O3 155.91(11) . . ?
O1 Cd1 O3 111.32(10) 3_565 . ?
N2 Cd1 O3 88.89(10) 2_655 . ?
O2 Cd1 O3 55.02(10) . . ?
N1 Cd1 O3 103.35(10) . . ?
C1 O1 Cd1 118.22(19) . . ?
C1 O1 Cd1 135.0(2) . 3_565 ?
Cd1 O1 Cd1 106.55(9) . 3_565 ?
C9 N1 C6 119.1(3) . . ?
C9 N1 Cd1 129.2(2) . . ?
C6 N1 Cd1 111.7(2) . . ?
O1 C1 C2 123.1(3) . . ?
O1 C1 C6 119.1(3) . . ?
C2 C1 C6 117.8(3) . . ?
N8 O2 Cd1 93.3(2) . . ?
C15 N2 C16 118.0(3) . . ?
C15 N2 Cd1 121.0(2) . 2_645 ?
C16 N2 Cd1 120.7(2) . 2_645 ?
C1 C2 C3 121.4(3) . . ?
C1 C2 H2B 119.3 . . ?
C3 C2 H2B 119.3 . . ?
N8 O3 Cd1 90.5(2) . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3A 119.4 . . ?
C2 C3 H3A 119.4 . . ?
C3 C4 C5 119.9(4) . . ?
C3 C4 H4B 120.1 . . ?
C5 C4 H4B 120.1 . . ?
C4 C5 C7 123.2(3) . . ?
C4 C5 C6 119.9(3) . . ?
C7 C5 C6 116.9(3) . . ?
N1 C6 C5 122.3(3) . . ?
N1 C6 C1 118.0(3) . . ?
C5 C6 C1 119.7(3) . . ?
C8 C7 C5 119.9(4) . . ?
C8 C7 H7A 120.1 . . ?
C5 C7 H7A 120.1 . . ?
O2 N8 O3 121.1(4) . . ?
O2 N8 O4 120.1(4) . . ?
O3 N8 O4 118.8(4) . . ?
C7 C8 C9 120.6(3) . . ?
C7 C8 H8A 119.7 . . ?
C9 C8 H8A 119.7 . . ?
N1 C9 C8 121.2(3) . . ?
N1 C9 C10 117.7(3) . . ?
C8 C9 C10 121.1(3) . . ?
C11 C10 C9 123.4(3) . . ?
C11 C10 H10A 118.3 . . ?
C9 C10 H10A 118.3 . . ?
C10 C11 C12 127.8(4) . . ?
C10 C11 H11A 116.1 . . ?
C12 C11 H11A 116.1 . . ?
C16 C12 C13 116.8(3) . . ?
C16 C12 C11 117.8(3) . . ?
C13 C12 C11 125.3(3) . . ?
C14 C13 C12 119.8(3) . . ?
C14 C13 H13A 120.1 . . ?
C12 C13 H13A 120.1 . . ?
C13 C14 C15 119.4(4) . . ?
C13 C14 H14A 120.3 . . ?
C15 C14 H14A 120.3 . . ?
N2 C15 C14 122.0(3) . . ?
N2 C15 H15A 119.0 . . ?
C14 C15 H15A 119.0 . . ?
N2 C16 C12 124.0(3) . . ?
N2 C16 H16A 118.0 . . ?
C12 C16 H16A 118.0 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.741
_refine_diff_density_min         -0.843
_refine_diff_density_rms         0.093
####################################################################### 
# 
# 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_f:\paper-~1\rllani~1\d2076f~1\d2076f
_database_code_depnum_ccdc_archive 'CCDC 1024562'
_audit_update_record             
;
2014-09-16 deposited with the CCDC.
2015-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 Cd I N2 O'
_chemical_formula_weight         486.57

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'
Cd Cd -0.8075 1.2024 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8073(6)
_cell_length_b                   9.0322(6)
_cell_length_c                   10.2851(7)
_cell_angle_alpha                77.7640(10)
_cell_angle_beta                 79.3150(10)
_cell_angle_gamma                78.0290(10)
_cell_volume                     773.59(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      25

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.089
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460
_exptl_absorpt_coefficient_mu    3.406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5491
_exptl_absorpt_correction_T_max  0.5952
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4015
_diffrn_reflns_av_R_equivalents  0.0100
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2691
_reflns_number_gt                2507
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0277P)²+1.4195P] 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         2691
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0259
_refine_ls_wR_factor_ref         0.0643
_refine_ls_wR_factor_gt          0.0627
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.67977(4) -0.09710(4) 0.13062(3) 0.06022(12) Uani 1 1 d . . .
Cd1 Cd 0.58037(3) 0.06832(3) 0.33063(3) 0.03227(10) Uani 1 1 d . . .
O1 O 0.6370(3) 0.0094(3) 0.5400(3) 0.0398(6) Uani 1 1 d . . .
N1 N 0.7784(3) 0.2062(3) 0.3405(3) 0.0290(6) Uani 1 1 d . . .
C1 C 0.7509(4) 0.0668(4) 0.5670(4) 0.0313(8) Uani 1 1 d . . .
N2 N 0.5672(4) 0.6900(3) -0.2637(3) 0.0345(7) Uani 1 1 d . . .
C2 C 0.8052(5) 0.0300(4) 0.6897(4) 0.0372(8) Uani 1 1 d . . .
H2B H 0.7589 -0.0414 0.7596 0.045 Uiso 1 1 calc R . .
C3 C 0.9262(5) 0.0945(5) 0.7142(4) 0.0390(9) Uani 1 1 d . . .
H3A H 0.9615 0.0639 0.7993 0.047 Uiso 1 1 calc R . .
C4 C 0.9949(5) 0.2005(5) 0.6187(4) 0.0396(9) Uani 1 1 d . . .
H4A H 1.0760 0.2440 0.6376 0.048 Uiso 1 1 calc R . .
C5 C 0.9437(4) 0.2446(4) 0.4916(4) 0.0339(8) Uani 1 1 d . . .
C6 C 0.8258(4) 0.1748(4) 0.4635(4) 0.0288(7) Uani 1 1 d . . .
C7 C 1.0014(5) 0.3571(5) 0.3870(4) 0.0424(9) Uani 1 1 d . . .
H7A H 1.0788 0.4089 0.4011 0.051 Uiso 1 1 calc R . .
C8 C 0.9478(5) 0.3924(5) 0.2667(4) 0.0424(9) Uani 1 1 d . . .
H8A H 0.9847 0.4709 0.1982 0.051 Uiso 1 1 calc R . .
C9 C 0.8365(4) 0.3115(4) 0.2438(4) 0.0342(8) Uani 1 1 d . . .
C10 C 0.7799(4) 0.3389(4) 0.1140(4) 0.0351(8) Uani 1 1 d . . .
H10A H 0.7602 0.2524 0.0850 0.042 Uiso 1 1 calc R . .
C11 C 0.7539(4) 0.4745(4) 0.0337(4) 0.0365(8) Uani 1 1 d . . .
H11A H 0.7795 0.5599 0.0599 0.044 Uiso 1 1 calc R . .
C12 C 0.6885(4) 0.5029(4) -0.0925(4) 0.0320(8) Uani 1 1 d . . .
C13 C 0.6785(5) 0.3871(5) -0.1587(4) 0.0431(9) Uani 1 1 d . . .
H13A H 0.7135 0.2825 -0.1219 0.052 Uiso 1 1 calc R . .
C14 C 0.6175(5) 0.4244(5) -0.2779(4) 0.0472(10) Uani 1 1 d . . .
H14A H 0.6123 0.3464 -0.3252 0.057 Uiso 1 1 calc R . .
C15 C 0.5642(5) 0.5771(5) -0.3272(4) 0.0400(9) Uani 1 1 d . . .
H15A H 0.5237 0.6027 -0.4101 0.048 Uiso 1 1 calc R . .
C16 C 0.6292(4) 0.6532(4) -0.1496(4) 0.0337(8) Uani 1 1 d . . .
H16A H 0.6330 0.7339 -0.1049 0.040 Uiso 1 1 calc R . .


_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
I1 Cd1 2.7061(4) . ?
Cd1 O1 2.230(2) . ?
Cd1 O1 2.268(3) 2_656 ?
Cd1 N2 2.333(3) 2_665 ?
Cd1 N1 2.371(3) . ?
O1 C1 1.316(4) . ?
O1 Cd1 2.268(3) 2_656 ?
N1 C9 1.330(5) . ?
N1 C6 1.360(4) . ?
C1 C2 1.383(5) . ?
C1 C6 1.444(5) . ?
N2 C15 1.329(5) . ?
N2 C16 1.335(5) . ?
N2 Cd1 2.333(3) 2_665 ?
C2 C3 1.399(6) . ?
C2 H2B 0.9500 . ?
C3 C4 1.367(6) . ?
C3 H3A 0.9500 . ?
C4 C5 1.412(5) . ?
C4 H4A 0.9500 . ?
C5 C7 1.413(5) . ?
C5 C6 1.421(5) . ?
C7 C8 1.357(6) . ?
C7 H7A 0.9500 . ?
C8 C9 1.417(5) . ?
C8 H8A 0.9500 . ?
C9 C10 1.465(5) . ?
C10 C11 1.327(5) . ?
C10 H10A 0.9500 . ?
C11 C12 1.469(5) . ?
C11 H11A 0.9500 . ?
C12 C13 1.389(6) . ?
C12 C16 1.393(5) . ?
C13 C14 1.378(6) . ?
C13 H13A 0.9500 . ?
C14 C15 1.380(6) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 H16A 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
O1 Cd1 O1 74.97(10) . 2_656 ?
O1 Cd1 N2 117.87(11) . 2_665 ?
O1 Cd1 N2 89.96(10) 2_656 2_665 ?
O1 Cd1 N1 72.11(9) . . ?
O1 Cd1 N1 139.60(10) 2_656 . ?
N2 Cd1 N1 85.31(10) 2_665 . ?
O1 Cd1 I1 128.31(8) . . ?
O1 Cd1 I1 109.68(7) 2_656 . ?
N2 Cd1 I1 113.64(8) 2_665 . ?
N1 Cd1 I1 108.92(7) . . ?
C1 O1 Cd1 118.4(2) . . ?
C1 O1 Cd1 132.4(2) . 2_656 ?
Cd1 O1 Cd1 105.03(10) . 2_656 ?
C9 N1 C6 120.0(3) . . ?
C9 N1 Cd1 127.0(2) . . ?
C6 N1 Cd1 112.9(2) . . ?
O1 C1 C2 124.0(3) . . ?
O1 C1 C6 119.0(3) . . ?
C2 C1 C6 117.0(3) . . ?
C15 N2 C16 118.0(3) . . ?
C15 N2 Cd1 118.3(2) . 2_665 ?
C16 N2 Cd1 122.4(3) . 2_665 ?
C1 C2 C3 122.1(4) . . ?
C1 C2 H2B 119.0 . . ?
C3 C2 H2B 119.0 . . ?
C4 C3 C2 121.7(3) . . ?
C4 C3 H3A 119.2 . . ?
C2 C3 H3A 119.2 . . ?
C3 C4 C5 119.1(4) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
C4 C5 C7 124.3(4) . . ?
C4 C5 C6 119.7(3) . . ?
C7 C5 C6 116.0(3) . . ?
N1 C6 C5 122.3(3) . . ?
N1 C6 C1 117.4(3) . . ?
C5 C6 C1 120.4(3) . . ?
C8 C7 C5 121.0(4) . . ?
C8 C7 H7A 119.5 . . ?
C5 C7 H7A 119.5 . . ?
C7 C8 C9 119.6(4) . . ?
C7 C8 H8A 120.2 . . ?
C9 C8 H8A 120.2 . . ?
N1 C9 C8 121.0(3) . . ?
N1 C9 C10 116.8(3) . . ?
C8 C9 C10 122.2(3) . . ?
C11 C10 C9 125.3(4) . . ?
C11 C10 H10A 117.3 . . ?
C9 C10 H10A 117.3 . . ?
C10 C11 C12 125.1(4) . . ?
C10 C11 H11A 117.4 . . ?
C12 C11 H11A 117.4 . . ?
C13 C12 C16 116.9(3) . . ?
C13 C12 C11 123.7(3) . . ?
C16 C12 C11 119.4(3) . . ?
C14 C13 C12 119.8(4) . . ?
C14 C13 H13A 120.1 . . ?
C12 C13 H13A 120.1 . . ?
C13 C14 C15 118.8(4) . . ?
C13 C14 H14A 120.6 . . ?
C15 C14 H14A 120.6 . . ?
N2 C15 C14 122.8(4) . . ?
N2 C15 H15A 118.6 . . ?
C14 C15 H15A 118.6 . . ?
N2 C16 C12 123.7(4) . . ?
N2 C16 H16A 118.2 . . ?
C12 C16 H16A 118.2 . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         1.344
_refine_diff_density_min         -1.453
_refine_diff_density_rms         0.096
