# 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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data_Cpx1

_audit_update_record             
;
2014-11-15 # Formatted by publCIF

;
_publcif_datablock.id            {6d33e6f5-38bc-4d5b-a10d-974960020987}

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H22 N4 O4 Zn'
_chemical_formula_sum            'C28 H22 N4 O4 Zn'
_chemical_formula_weight         543.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   13.066(3)
_cell_length_b                   20.404(4)
_cell_length_c                   9.5822(19)
_cell_angle_alpha                90
_cell_angle_beta                 94.37(3)
_cell_angle_gamma                90
_cell_volume                     2547.2(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    3064
_cell_measurement_theta_min      4.0170
_cell_measurement_theta_max      73.0160

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.006
_shelx_estimated_absorpt_T_min   0.889
_shelx_estimated_absorpt_T_max   0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_T_max  0.904
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           ?

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4471
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5702
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.855
_diffrn_reflns_theta_max         24.710
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.943
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.943
_reflns_number_total             2248
_reflns_number_gt                1952
_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.
 A total of 457 least-squares restraints arises from the use of SIMU and
 DELU instructions to model the disordered imidazole ligand. These includes:
 SIMU N1 > C10A
 DELU N1 > C10A
;

_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)+(0.1869P)²+1.7364P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2248
_refine_ls_number_parameters     280
_refine_ls_number_restraints     457
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_ref         0.2350
_refine_ls_wR_factor_gt          0.2203
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 1.19827(6) 0.5000 0.11756(7) 0.0381(4) Uani 1 2 d S T P . .
N1 N 1.124(2) 0.4132(14) 0.138(3) 0.029(2) Uani 0.539(10) 1 d . U P A 1
N2 N 1.022(2) 0.3460(11) 0.229(3) 0.030(3) Uani 0.539(10) 1 d . U P A 1
C1 C 1.1695(11) 0.3491(7) 0.1250(14) 0.033(3) Uani 0.539(10) 1 d . U P A 1
C2 C 1.1055(15) 0.3058(9) 0.1818(17) 0.040(3) Uani 0.539(10) 1 d . U P A 1
H2 H 1.1130 0.2601 0.1891 0.048 Uiso 0.539(10) 1 calc R U P A 1
C3 C 1.0418(15) 0.4069(9) 0.2098(15) 0.029(2) Uani 0.539(10) 1 d . U P A 1
H3 H 1.0033 0.4419 0.2420 0.035 Uiso 0.539(10) 1 calc R U P A 1
C4 C 1.2722(10) 0.3384(7) 0.0755(17) 0.057(3) Uani 0.539(10) 1 d . U P A 1
H4A H 1.2699 0.3465 -0.0245 0.085 Uiso 0.539(10) 1 calc R U P A 1
H4B H 1.2935 0.2936 0.0947 0.085 Uiso 0.539(10) 1 calc R U P A 1
H4C H 1.3208 0.3682 0.1236 0.085 Uiso 0.539(10) 1 calc R U P A 1
C5 C 0.9372(5) 0.3210(3) 0.3014(8) 0.040(3) Uani 0.539(10) 1 d G U P A 1
C6 C 0.9109(7) 0.2551(3) 0.2884(8) 0.051(3) Uani 0.539(10) 1 d G U P A 1
H6 H 0.9449 0.2279 0.2278 0.062 Uiso 0.539(10) 1 calc R U P A 1
C7 C 0.8341(7) 0.2295(3) 0.3652(9) 0.051(3) Uani 0.539(10) 1 d G U P A 1
H7 H 0.8163 0.1850 0.3565 0.062 Uiso 0.539(10) 1 calc R U P A 1
C8 C 0.7838(5) 0.2697(3) 0.4550(8) 0.044(3) Uani 0.539(10) 1 d G U P A 1
C9 C 0.8101(5) 0.3355(3) 0.4679(9) 0.048(3) Uani 0.539(10) 1 d G U P A 1
H9 H 0.7761 0.3627 0.5286 0.058 Uiso 0.539(10) 1 calc R U P A 1
C10 C 0.8868(5) 0.3612(2) 0.3912(9) 0.046(2) Uani 0.539(10) 1 d G U P A 1
H10 H 0.9047 0.4057 0.3999 0.055 Uiso 0.539(10) 1 calc R U P A 1
N1A N 1.115(3) 0.4153(16) 0.114(3) 0.029(2) Uani 0.461(10) 1 d . U P A 2
N2A N 1.021(3) 0.3354(13) 0.206(4) 0.036(4) Uani 0.461(10) 1 d . U P A 2
C1A C 1.1474(12) 0.3589(8) 0.0880(17) 0.030(3) Uani 0.461(10) 1 d . U P A 2
C2A C 1.0877(17) 0.3119(11) 0.138(2) 0.044(4) Uani 0.461(10) 1 d . U P A 2
H2A H 1.0966 0.2668 0.1237 0.053 Uiso 0.461(10) 1 calc R U P A 2
C3A C 1.0323(19) 0.4043(11) 0.175(2) 0.029(2) Uani 0.461(10) 1 d . U P A 2
H3A H 0.9854 0.4369 0.1968 0.035 Uiso 0.461(10) 1 calc R U P A 2
C4A C 1.2397(11) 0.3480(6) 0.0049(17) 0.043(3) Uani 0.461(10) 1 d . U P A 2
H4A1 H 1.3013 0.3618 0.0599 0.065 Uiso 0.461(10) 1 calc R U P A 2
H4A2 H 1.2321 0.3734 -0.0809 0.065 Uiso 0.461(10) 1 calc R U P A 2
H4A3 H 1.2449 0.3018 -0.0178 0.065 Uiso 0.461(10) 1 calc R U P A 2
C5A C 0.9461(6) 0.3088(4) 0.2948(9) 0.036(3) Uani 0.461(10) 1 d G U P A 2
C6A C 0.9616(6) 0.2483(4) 0.3598(10) 0.046(3) Uani 0.461(10) 1 d G U P A 2
H6A H 1.0225 0.2248 0.3493 0.055 Uiso 0.461(10) 1 calc R U P A 2
C7A C 0.8871(7) 0.2225(3) 0.4401(10) 0.048(3) Uani 0.461(10) 1 d G U P A 2
H7A H 0.8976 0.1816 0.4841 0.057 Uiso 0.461(10) 1 calc R U P A 2
C8A C 0.7971(6) 0.2572(4) 0.4555(10) 0.044(4) Uani 0.461(10) 1 d G U P A 2
C9A C 0.7816(5) 0.3176(5) 0.3905(12) 0.057(3) Uani 0.461(10) 1 d G U P A 2
H9A H 0.7207 0.3411 0.4010 0.068 Uiso 0.461(10) 1 calc R U P A 2
C10A C 0.8561(7) 0.3434(4) 0.3102(12) 0.054(3) Uani 0.461(10) 1 d G U P A 2
H10A H 0.8456 0.3843 0.2662 0.065 Uiso 0.461(10) 1 calc R U P A 2
O1 O 1.2966(4) 0.5000 -0.0245(5) 0.0526(14) Uani 1 2 d S T P A .
O2 O 1.1620(4) 0.5000 -0.1821(5) 0.0442(11) Uani 1 2 d S T P A .
C12 C 1.3256(6) 0.5266(4) -0.2587(9) 0.0306(17) Uani 0.5 1 d . . P A -1
C13 C 1.4212(7) 0.5556(5) -0.2208(9) 0.0381(19) Uani 0.5 1 d . . P A -1
H13A H 1.4438 0.5595 -0.1257 0.046 Uiso 0.5 1 calc R U P A -1
C14 C 1.4819(8) 0.5783(5) -0.3207(11) 0.044(2) Uani 0.5 1 d . . P A -1
H14A H 1.5449 0.5987 -0.2938 0.053 Uiso 0.5 1 calc R U P A -1
C15 C 1.4505(7) 0.5712(4) -0.4615(10) 0.037(2) Uani 0.5 1 d . . P A -1
H15A H 1.4914 0.5878 -0.5301 0.045 Uiso 0.5 1 calc R U P A -1
C16 C 1.3578(8) 0.5395(4) -0.5015(9) 0.0348(19) Uani 0.5 1 d . . P A -1
C17 C 1.2966(6) 0.5185(4) -0.3996(8) 0.032(2) Uani 0.5 1 d . . P A -1
H17A H 1.2336 0.5000 -0.4263 0.038 Uiso 1 2 d R U P . .
C18 C 1.3240(8) 0.5307(5) -0.6556(9) 0.039(2) Uani 0.5 1 d . . P . .
O4 O 1.2590(5) 0.5000 -0.6841(6) 0.0613(16) Uani 1 2 d S T P A .
O3 O 1.3636(6) 0.5688(4) -0.7408(7) 0.0536(19) Uani 0.5 1 d . . P A .
C11 C 1.2556(5) 0.5000 -0.1493(7) 0.0448(17) Uani 1 2 d S T 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
Zn1 O1 1.942(5) . ?
Zn1 O4 2.003(6) 1_556 ?
Zn1 N1 2.04(3) . ?
Zn1 N1 2.04(3) 6_565 ?
Zn1 N1A 2.04(4) 6_565 ?
Zn1 N1A 2.04(4) . ?
N1 C3 1.324(17) . ?
N1 C1 1.45(3) . ?
N2 C3 1.28(3) . ?
N2 C5 1.45(2) . ?
N2 C2 1.46(3) . ?
C1 C2 1.36(2) . ?
C1 C4 1.473(19) . ?
C2 H2 0.9400 . ?
C3 H3 0.9400 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9700 . ?
C5 C6 1.3900 . ?
C5 C10 1.3900 . ?
C6 C7 1.3900 . ?
C6 H6 0.9400 . ?
C7 C8 1.3900 . ?
C7 H7 0.9400 . ?
C8 C9 1.3900 . ?
C8 C8 1.512(9) 7_656 ?
C9 C10 1.3900 . ?
C9 H9 0.9400 . ?
C10 H10 0.9400 . ?
N1A C1A 1.26(4) . ?
N1A C3A 1.28(2) . ?
N2A C2A 1.22(4) . ?
N2A C3A 1.45(4) . ?
N2A C5A 1.45(3) . ?
C1A C2A 1.35(3) . ?
C1A C4A 1.51(2) . ?
C1A C3A 2.00(3) . ?
C2A H2A 0.9400 . ?
C3A H3A 0.9400 . ?
C4A H4A1 0.9700 . ?
C4A H4A2 0.9700 . ?
C4A H4A3 0.9700 . ?
C5A C6A 1.3900 . ?
C5A C10A 1.3900 . ?
C6A C7A 1.3900 . ?
C6A H6A 0.9400 . ?
C7A C8A 1.3900 . ?
C7A H7A 0.9400 . ?
C8A C9A 1.3900 . ?
C8A C8A 1.576(11) 7_656 ?
C9A C10A 1.3900 . ?
C9A H9A 0.9400 . ?
C10A H10A 0.9400 . ?
O1 C11 1.272(9) . ?
O2 C11 1.239(9) . ?
C12 C17 1.384(12) . ?
C12 C13 1.405(13) . ?
C12 C11 1.542(10) . ?
C13 C14 1.369(14) . ?
C13 H13A 0.9400 . ?
C14 C15 1.388(14) . ?
C14 H14A 0.9400 . ?
C15 C16 1.402(13) . ?
C15 H15A 0.9400 . ?
C16 C17 1.377(13) . ?
C16 C18 1.519(12) . ?
C17 H17A 0.9240 . ?
C18 O4 1.073(11) . ?
C18 C18 1.25(2) 6_565 ?
C18 O3 1.267(13) . ?
O4 C18 1.073(11) 6_565 ?
O4 Zn1 2.003(6) 1_554 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O4 115.4(2) . 1_556 ?
O1 Zn1 N1 114.4(8) . . ?
O4 Zn1 N1 93.8(6) 1_556 . ?
O1 Zn1 N1 114.4(8) . 6_565 ?
O4 Zn1 N1 93.8(6) 1_556 6_565 ?
N1 Zn1 N1 120.8(15) . 6_565 ?
O1 Zn1 N1A 111.6(10) . 6_565 ?
O4 Zn1 N1A 100.9(8) 1_556 6_565 ?
O1 Zn1 N1A 111.6(10) . . ?
O4 Zn1 N1A 100.9(8) 1_556 . ?
N1A Zn1 N1A 115.6(17) 6_565 . ?
C3 N1 C1 108.1(16) . . ?
C3 N1 Zn1 123.1(15) . . ?
C1 N1 Zn1 125.2(18) . . ?
C3 N2 C5 125.2(18) . . ?
C3 N2 C2 110(2) . . ?
C5 N2 C2 124.4(19) . . ?
C2 C1 N1 106.5(17) . . ?
C2 C1 C4 129.6(14) . . ?
N1 C1 C4 123.5(17) . . ?
C1 C2 N2 104.6(17) . . ?
C1 C2 H2 127.7 . . ?
N2 C2 H2 127.7 . . ?
N2 C3 N1 110.2(16) . . ?
N2 C3 H3 124.9 . . ?
N1 C3 H3 124.9 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 120.0 . . ?
C6 C5 N2 119.5(9) . . ?
C10 C5 N2 120.3(9) . . ?
C7 C6 C5 120.0 . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.0 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C9 120.0 . . ?
C7 C8 C8 111.3(9) . 7_656 ?
C9 C8 C8 127.9(9) . 7_656 ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C5 120.0 . . ?
C9 C10 H10 120.0 . . ?
C5 C10 H10 120.0 . . ?
C1A N1A C3A 104(2) . . ?
C1A N1A Zn1 126(2) . . ?
C3A N1A Zn1 127.3(18) . . ?
C2A N2A C3A 100(2) . . ?
C2A N2A C5A 135(3) . . ?
C3A N2A C5A 125(2) . . ?
N1A C1A C2A 112(2) . . ?
N1A C1A C4A 122(2) . . ?
C2A C1A C4A 126.2(17) . . ?
N1A C1A C3A 38.6(13) . . ?
C2A C1A C3A 73.0(14) . . ?
C4A C1A C3A 160.5(13) . . ?
N2A C2A C1A 112(2) . . ?
N2A C2A H2A 124.2 . . ?
C1A C2A H2A 124.2 . . ?
N1A C3A N2A 111.6(19) . . ?
N1A C3A C1A 37.7(13) . . ?
N2A C3A C1A 74.3(17) . . ?
N1A C3A H3A 124.2 . . ?
N2A C3A H3A 124.2 . . ?
C1A C3A H3A 160.9 . . ?
C1A C4A H4A1 109.5 . . ?
C1A C4A H4A2 109.5 . . ?
H4A1 C4A H4A2 109.5 . . ?
C1A C4A H4A3 109.5 . . ?
H4A1 C4A H4A3 109.5 . . ?
H4A2 C4A H4A3 109.5 . . ?
C6A C5A C10A 120.0 . . ?
C6A C5A N2A 121.0(15) . . ?
C10A C5A N2A 118.9(15) . . ?
C5A C6A C7A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
C7A C6A H6A 120.0 . . ?
C8A C7A C6A 120.0 . . ?
C8A C7A H7A 120.0 . . ?
C6A C7A H7A 120.0 . . ?
C7A C8A C9A 120.0 . . ?
C7A C8A C8A 131.6(10) . 7_656 ?
C9A C8A C8A 108.3(10) . 7_656 ?
C10A C9A C8A 120.0 . . ?
C10A C9A H9A 120.0 . . ?
C8A C9A H9A 120.0 . . ?
C9A C10A C5A 120.0 . . ?
C9A C10A H10A 120.0 . . ?
C5A C10A H10A 120.0 . . ?
C11 O1 Zn1 113.9(5) . . ?
C17 C12 C13 118.3(8) . . ?
C17 C12 C11 119.3(7) . . ?
C13 C12 C11 122.3(7) . . ?
C14 C13 C12 120.9(8) . . ?
C14 C13 H13A 119.6 . . ?
C12 C13 H13A 119.6 . . ?
C13 C14 C15 120.0(9) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C14 C15 C16 119.9(8) . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C17 C16 C15 119.1(8) . . ?
C17 C16 C18 120.8(9) . . ?
C15 C16 C18 120.1(9) . . ?
C16 C17 C12 121.6(8) . . ?
C16 C17 H17A 118.9 . . ?
C12 C17 H17A 119.4 . . ?
O4 C18 C18 54.3(5) . 6_565 ?
O4 C18 O3 123.2(9) . . ?
C18 C18 O3 127.9(6) 6_565 . ?
O4 C18 C16 118.8(9) . . ?
C18 C18 C16 96.8(5) 6_565 . ?
O3 C18 C16 116.8(10) . . ?
C18 O4 C18 71.3(11) . 6_565 ?
C18 O4 Zn1 119.4(6) . 1_554 ?
C18 O4 Zn1 119.4(6) 6_565 1_554 ?
O2 C11 O1 125.2(6) . . ?
O2 C11 C12 116.9(6) . . ?
O1 C11 C12 114.2(6) . . ?

_refine_diff_density_max         1.910
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.147

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 1025328'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Cpx2

_audit_update_record             
;
2014-11-15 # Formatted by publCIF

;
_publcif_datablock.id            {2cd91889-060e-42c9-9adb-d0e2913beccc}

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H22 N4 O4 Zn'
_chemical_formula_sum            'C28 H22 N4 O4 Zn'
_chemical_formula_weight         543.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'

_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+1/2, -y, z'
'x, -y+1/2, -z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'-x, y-1/2, z-1/2'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.996(3)
_cell_length_b                   16.994(3)
_cell_length_c                   10.668(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2356.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    7977
_cell_measurement_theta_min      3.0623
_cell_measurement_theta_max      27.5204

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   0.641
_exptl_transmission_factor_max   0.647
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    1.087
_shelx_estimated_absorpt_T_min   0.670
_shelx_estimated_absorpt_T_max   0.670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
'Jacobson, R. (1998) Private communication to Rigaku Company, Tokyo, Japan.'

_exptl_special_details           ?

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku MercuryCCD area detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            20136
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.135
_diffrn_reflns_theta_max         27.461
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2692
_reflns_number_gt                2553
_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)+(0.0246P)²+15.7824P]
 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         2692
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0804
_refine_ls_wR_factor_ref         0.1490
_refine_ls_wR_factor_gt          0.1454
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.17577(5) 0.2500 0.2500 0.0259(2) Uani 1 2 d S T P . .
O1 O 0.0707(3) 0.18007(18) 0.3291(3) 0.0342(8) Uani 1 1 d . . . . .
O2 O 0.2055(3) 0.1009(2) 0.3284(3) 0.0380(8) Uani 1 1 d . . . . .
N1 N 0.2802(3) 0.2128(2) 0.1184(4) 0.0276(8) Uani 1 1 d . . . . .
N2 N 0.4282(3) 0.1599(2) 0.0615(4) 0.0321(9) Uani 1 1 d . . . . .
C1 C 0.3583(4) 0.1678(3) 0.1528(5) 0.0312(10) Uani 1 1 d . . . . .
H1A H 0.3641 0.1441 0.2321 0.037 Uiso 1 1 calc R U . . .
C2 C 0.3012(4) 0.2345(2) -0.0051(4) 0.0301(10) Uani 1 1 d . . . . .
C3 C 0.3917(4) 0.2020(3) -0.0404(5) 0.0357(11) Uani 1 1 d . . . . .
H3A H 0.4236 0.2070 -0.1191 0.043 Uiso 1 1 calc R U . . .
C4 C 0.5212(4) 0.1142(3) 0.0654(5) 0.0317(10) Uani 1 1 d . . . . .
C5 C 0.5603(4) 0.0833(3) -0.0439(5) 0.0372(12) Uani 1 1 d . . . . .
H5A H 0.5263 0.0921 -0.1204 0.045 Uiso 1 1 calc R U . . .
C6 C 0.6497(4) 0.0392(3) -0.0410(5) 0.0370(12) Uani 1 1 d . . . . .
H6A H 0.6764 0.0191 -0.1164 0.044 Uiso 1 1 calc R U . . .
C7 C 0.7012(3) 0.0239(3) 0.0703(5) 0.0319(10) Uani 1 1 d . . . . .
C8 C 0.6601(4) 0.0554(3) 0.1796(5) 0.0443(13) Uani 1 1 d . . . . .
H8A H 0.6933 0.0461 0.2565 0.053 Uiso 1 1 calc R U . . .
C9 C 0.5711(4) 0.1003(3) 0.1775(5) 0.0455(13) Uani 1 1 d . . . . .
H9A H 0.5447 0.1213 0.2524 0.055 Uiso 1 1 calc R U . . .
C10 C 0.2312(4) 0.2861(3) -0.0801(5) 0.0458(14) Uani 1 1 d . . . . .
H10A H 0.2283 0.3379 -0.0422 0.069 Uiso 1 1 calc R U . . .
H10B H 0.1628 0.2634 -0.0816 0.069 Uiso 1 1 calc R U . . .
H10C H 0.2571 0.2904 -0.1651 0.069 Uiso 1 1 calc R U . . .
C11 C 0.1154(4) 0.1154(3) 0.3569(4) 0.0275(9) Uani 1 1 d . . . . .
C12 C 0.0540(3) 0.0560(3) 0.4306(4) 0.0267(9) Uani 1 1 d . . . . .
C13 C 0.0974(4) -0.0178(3) 0.4546(5) 0.0328(11) Uani 1 1 d . . . . .
H13A H 0.1632 -0.0301 0.4237 0.039 Uiso 1 1 calc R U . . .
C14 C -0.0429(4) 0.0726(3) 0.4759(5) 0.0351(11) Uani 1 1 d . . . . .
H14A H -0.0725 0.1220 0.4594 0.042 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 1.998(3) . ?
Zn1 O1 1.998(3) 3 ?
Zn1 N1 2.052(4) 3 ?
Zn1 N1 2.052(4) . ?
O1 C11 1.277(5) . ?
O2 C11 1.235(6) . ?
N1 C1 1.324(6) . ?
N1 C2 1.396(6) . ?
N2 C1 1.338(6) . ?
N2 C3 1.386(6) . ?
N2 C4 1.437(6) . ?
C1 H1A 0.9400 . ?
C2 C3 1.353(7) . ?
C2 C10 1.495(7) . ?
C3 H3A 0.9400 . ?
C4 C5 1.377(7) . ?
C4 C9 1.381(7) . ?
C5 C6 1.383(7) . ?
C5 H5A 0.9400 . ?
C6 C7 1.388(7) . ?
C6 H6A 0.9400 . ?
C7 C8 1.390(7) . ?
C7 C7 1.505(9) 2_655 ?
C8 C9 1.385(7) . ?
C8 H8A 0.9400 . ?
C9 H9A 0.9400 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C11 C12 1.509(6) . ?
C12 C14 1.377(6) . ?
C12 C13 1.399(6) . ?
C13 C14 1.385(6) 5_556 ?
C13 H13A 0.9400 . ?
C14 C13 1.385(6) 5_556 ?
C14 H14A 0.9400 . ?

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 O1 93.73(19) . 3 ?
O1 Zn1 N1 110.26(15) . 3 ?
O1 Zn1 N1 123.90(14) 3 3 ?
O1 Zn1 N1 123.90(14) . . ?
O1 Zn1 N1 110.26(15) 3 . ?
N1 Zn1 N1 97.2(2) 3 . ?
C11 O1 Zn1 107.4(3) . . ?
C1 N1 C2 105.3(4) . . ?
C1 N1 Zn1 119.7(3) . . ?
C2 N1 Zn1 133.9(3) . . ?
C1 N2 C3 106.6(4) . . ?
C1 N2 C4 127.2(4) . . ?
C3 N2 C4 126.2(4) . . ?
N1 C1 N2 112.2(4) . . ?
N1 C1 H1A 123.9 . . ?
N2 C1 H1A 123.9 . . ?
C3 C2 N1 109.0(4) . . ?
C3 C2 C10 128.3(5) . . ?
N1 C2 C10 122.8(4) . . ?
C2 C3 N2 106.9(4) . . ?
C2 C3 H3A 126.6 . . ?
N2 C3 H3A 126.6 . . ?
C5 C4 C9 119.7(5) . . ?
C5 C4 N2 119.5(5) . . ?
C9 C4 N2 120.8(4) . . ?
C4 C5 C6 119.8(5) . . ?
C4 C5 H5A 120.1 . . ?
C6 C5 H5A 120.1 . . ?
C5 C6 C7 121.8(5) . . ?
C5 C6 H6A 119.1 . . ?
C7 C6 H6A 119.1 . . ?
C6 C7 C8 117.4(4) . . ?
C6 C7 C7 120.5(3) . 2_655 ?
C8 C7 C7 122.1(3) . 2_655 ?
C9 C8 C7 121.3(5) . . ?
C9 C8 H8A 119.3 . . ?
C7 C8 H8A 119.3 . . ?
C4 C9 C8 120.0(5) . . ?
C4 C9 H9A 120.0 . . ?
C8 C9 H9A 120.0 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 O1 123.1(4) . . ?
O2 C11 C12 119.8(4) . . ?
O1 C11 C12 117.1(4) . . ?
C14 C12 C13 119.2(4) . . ?
C14 C12 C11 122.0(4) . . ?
C13 C12 C11 118.8(4) . . ?
C14 C13 C12 119.6(4) 5_556 . ?
C14 C13 H13A 120.2 5_556 . ?
C12 C13 H13A 120.2 . . ?
C12 C14 C13 121.2(4) . 5_556 ?
C12 C14 H14A 119.4 . . ?
C13 C14 H14A 119.4 5_556 . ?

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.066

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 1025329'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Cpx3

_audit_update_record             
;
2014-11-15 # Formatted by publCIF

;
_publcif_datablock.id            {fd630064-4f15-496e-b33b-8d7f2dda020f}

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H22 Cd N4 O4'
_chemical_formula_sum            'C28 H22 Cd N4 O4'
_chemical_formula_weight         590.89

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'

_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                   10.362(2)
_cell_length_b                   10.649(2)
_cell_length_c                   11.096(2)
_cell_angle_alpha                92.16(3)
_cell_angle_beta                 100.28(3)
_cell_angle_gamma                92.65(3)
_cell_volume                     1202.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4685
_cell_measurement_theta_min      3.1461
_cell_measurement_theta_max      27.4778

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   0.796
_exptl_transmission_factor_max   0.909
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.952
_shelx_estimated_absorpt_T_min   0.702
_shelx_estimated_absorpt_T_max   0.911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS, (Sheldrick 2008)'

_exptl_special_details           ?

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku MercuryCCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       dtprofit.ref
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9676
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.146
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.959
_reflns_number_total             4725
_reflns_number_gt                4316
_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)+(0.1680P)²+1.7906P]
 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         4725
_refine_ls_number_parameters     324
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.2257
_refine_ls_wR_factor_gt          0.1947
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.66120(3) 0.61972(3) 0.54416(3) 0.0256(2) Uani 1 1 d . . . . .
O1 O 0.8933(5) 0.6025(5) 0.5404(5) 0.0429(12) Uani 1 1 d . . . . .
O2 O 0.8248(4) 0.7816(4) 0.6021(5) 0.0413(11) Uani 1 1 d . . . . .
O3 O 1.3848(5) 0.5742(5) 0.5539(5) 0.0425(11) Uani 1 1 d . . . . .
O4 O 1.5089(4) 0.7506(4) 0.5922(5) 0.0383(10) Uani 1 1 d . . . . .
N1 N 0.7091(5) 0.5147(5) 0.7251(5) 0.0331(11) Uani 1 1 d . . . . .
N2 N 0.8185(6) 0.3844(5) 0.8496(5) 0.0372(12) Uani 1 1 d . . . . .
N3 N 1.5074(5) -0.1837(5) 1.2088(5) 0.0333(7) Uani 1 1 d . . . . .
N4 N 1.6091(5) -0.3034(5) 1.3466(5) 0.0333(7) Uani 1 1 d . . . . .
C1 C 0.8040(6) 0.4356(6) 0.7378(6) 0.0356(14) Uani 1 1 d . . . . .
H1A H 0.8547 0.4170 0.6778 0.043 Uiso 1 1 calc R U . . .
C2 C 0.6582(7) 0.5139(6) 0.8314(6) 0.0346(14) Uani 1 1 d . . . . .
C3 C 0.7276(8) 0.4352(7) 0.9101(7) 0.0397(15) Uani 1 1 d . . . . .
H3A H 0.7152 0.4190 0.9901 0.048 Uiso 1 1 calc R U . . .
C4 C 0.9173(7) 0.3006(6) 0.8983(6) 0.0364(14) Uani 1 1 d . . . . .
C5 C 0.9485(7) 0.2033(7) 0.8280(6) 0.0421(16) Uani 1 1 d . . . . .
H5A H 0.9045 0.1899 0.7465 0.051 Uiso 1 1 calc R U . . .
C6 C 1.0454(7) 0.1236(7) 0.8761(6) 0.0410(15) Uani 1 1 d . . . . .
H6A H 1.0657 0.0566 0.8264 0.049 Uiso 1 1 calc R U . . .
C7 C 1.1124(6) 0.1409(6) 0.9957(6) 0.0348(13) Uani 1 1 d . . . . .
C8 C 1.0778(8) 0.2416(8) 1.0670(7) 0.0465(18) Uani 1 1 d . . . . .
H8A H 1.1206 0.2556 1.1489 0.056 Uiso 1 1 calc R U . . .
C9 C 0.9814(9) 0.3203(8) 1.0182(7) 0.0486(18) Uani 1 1 d . . . . .
H9A H 0.9595 0.3875 1.0668 0.058 Uiso 1 1 calc R U . . .
C10 C 1.2172(6) 0.0558(6) 1.0488(6) 0.0336(13) Uani 1 1 d . . . . .
C11 C 1.2697(8) -0.0296(7) 0.9761(6) 0.0452(17) Uani 1 1 d . . . . .
H11A H 1.2397 -0.0344 0.8909 0.054 Uiso 1 1 calc R U . . .
C12 C 1.3661(8) -0.1084(7) 1.0273(6) 0.0410(15) Uani 1 1 d . . . . .
H12A H 1.4008 -0.1662 0.9772 0.049 Uiso 1 1 calc R U . . .
C13 C 1.4102(6) -0.1010(6) 1.1521(6) 0.0327(13) Uani 1 1 d . . . . .
C14 C 1.3622(7) -0.0156(7) 1.2268(7) 0.0394(15) Uani 1 1 d . . . . .
H14A H 1.3944 -0.0099 1.3116 0.047 Uiso 1 1 calc R U . . .
C15 C 1.2646(7) 0.0628(7) 1.1743(7) 0.0420(15) Uani 1 1 d . . . . .
H15A H 1.2308 0.1210 1.2247 0.050 Uiso 1 1 calc R U . . .
C16 C 1.5161(7) -0.2270(6) 1.3232(6) 0.0333(7) Uani 1 1 d . . . . .
H16A H 1.4613 -0.2040 1.3784 0.040 Uiso 1 1 calc R U . . .
C17 C 1.6053(7) -0.2392(6) 1.1589(6) 0.0364(14) Uani 1 1 d . . . . .
H17A H 1.6244 -0.2282 1.0801 0.044 Uiso 1 1 calc R U . . .
C18 C 1.6678(7) -0.3120(6) 1.2448(6) 0.0351(14) Uani 1 1 d . . . . .
C19 C 0.5488(8) 0.5943(8) 0.8525(7) 0.0463(17) Uani 1 1 d . . . . .
H19A H 0.5439 0.5979 0.9390 0.069 Uiso 1 1 calc R U . . .
H19B H 0.4664 0.5586 0.8056 0.069 Uiso 1 1 calc R U . . .
H19C H 0.5652 0.6786 0.8265 0.069 Uiso 1 1 calc R U . . .
C20 C 1.7807(8) -0.3935(8) 1.2378(7) 0.0459(17) Uani 1 1 d . . . . .
H20A H 1.7581 -0.4783 1.2586 0.069 Uiso 1 1 calc R U . . .
H20B H 1.8575 -0.3599 1.2950 0.069 Uiso 1 1 calc R U . . .
H20C H 1.7996 -0.3949 1.1552 0.069 Uiso 1 1 calc R U . . .
C21 C 0.9140(5) 0.7158(6) 0.5765(5) 0.0294(12) Uani 1 1 d . . . . .
C22 C 1.3990(5) 0.6907(6) 0.5764(6) 0.0301(12) Uani 1 1 d . . . . .
C23 C 1.0494(5) 0.7768(5) 0.5885(5) 0.0269(11) Uani 1 1 d . . . . .
C24 C 1.1564(5) 0.7062(5) 0.5772(5) 0.0264(11) Uani 1 1 d . . . . .
H24A H 1.1447 0.6184 0.5637 0.032 Uiso 1 1 calc R U . . .
C25 C 1.2814(5) 0.7649(6) 0.5860(5) 0.0279(11) Uani 1 1 d . . . . .
C26 C 1.2971(6) 0.8954(6) 0.6058(7) 0.0392(15) Uani 1 1 d . . . . .
H26A H 1.3813 0.9351 0.6135 0.047 Uiso 1 1 calc R U . . .
C27 C 1.1902(7) 0.9676(6) 0.6144(8) 0.0461(18) Uani 1 1 d . . . . .
H27A H 1.2006 1.0558 0.6232 0.055 Uiso 1 1 calc R U . . .
C28 C 1.0677(6) 0.9068(6) 0.6096(6) 0.0345(13) Uani 1 1 d . . . . .
H28A H 0.9960 0.9541 0.6209 0.041 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
Cd1 O4 2.272(4) 1_455 ?
Cd1 O3 2.287(5) 2_766 ?
Cd1 N1 2.323(5) . ?
Cd1 O2 2.348(5) . ?
Cd1 N4 2.350(5) 1_464 ?
Cd1 O1 2.428(5) . ?
Cd1 C21 2.726(6) . ?
O1 C21 1.253(8) . ?
O2 C21 1.251(8) . ?
O3 C22 1.253(8) . ?
O3 Cd1 2.287(5) 2_766 ?
O4 C22 1.260(8) . ?
O4 Cd1 2.272(4) 1_655 ?
N1 C1 1.315(8) . ?
N1 C2 1.376(8) . ?
N2 C1 1.361(8) . ?
N2 C3 1.369(9) . ?
N2 C4 1.435(8) . ?
N3 C16 1.356(8) . ?
N3 C17 1.384(8) . ?
N3 C13 1.444(8) . ?
N4 C16 1.287(8) . ?
N4 C18 1.377(9) . ?
N4 Cd1 2.350(5) 1_646 ?
C1 H1A 0.9400 . ?
C2 C3 1.367(10) . ?
C2 C19 1.497(10) . ?
C3 H3A 0.9400 . ?
C4 C5 1.359(10) . ?
C4 C9 1.381(11) . ?
C5 C6 1.391(9) . ?
C5 H5A 0.9400 . ?
C6 C7 1.385(10) . ?
C6 H6A 0.9400 . ?
C7 C8 1.406(10) . ?
C7 C10 1.500(9) . ?
C8 C9 1.382(11) . ?
C8 H8A 0.9400 . ?
C9 H9A 0.9400 . ?
C10 C11 1.386(10) . ?
C10 C15 1.389(9) . ?
C11 C12 1.391(10) . ?
C11 H11A 0.9400 . ?
C12 C13 1.376(9) . ?
C12 H12A 0.9400 . ?
C13 C14 1.376(9) . ?
C14 C15 1.401(9) . ?
C14 H14A 0.9400 . ?
C15 H15A 0.9400 . ?
C16 H16A 0.9400 . ?
C17 C18 1.346(9) . ?
C17 H17A 0.9400 . ?
C18 C20 1.500(9) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 C23 1.500(8) . ?
C22 C25 1.500(8) . ?
C23 C24 1.389(8) . ?
C23 C28 1.393(9) . ?
C24 C25 1.397(8) . ?
C24 H24A 0.9400 . ?
C25 C26 1.396(9) . ?
C26 C27 1.393(9) . ?
C26 H26A 0.9400 . ?
C27 C28 1.389(9) . ?
C27 H27A 0.9400 . ?
C28 H28A 0.9400 . ?

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
O4 Cd1 O3 125.10(17) 1_455 2_766 ?
O4 Cd1 N1 100.39(19) 1_455 . ?
O3 Cd1 N1 86.9(2) 2_766 . ?
O4 Cd1 O2 89.58(16) 1_455 . ?
O3 Cd1 O2 144.32(17) 2_766 . ?
N1 Cd1 O2 95.4(2) . . ?
O4 Cd1 N4 85.14(19) 1_455 1_464 ?
O3 Cd1 N4 84.8(2) 2_766 1_464 ?
N1 Cd1 N4 171.61(19) . 1_464 ?
O2 Cd1 N4 90.9(2) . 1_464 ?
O4 Cd1 O1 144.20(17) 1_455 . ?
O3 Cd1 O1 90.47(18) 2_766 . ?
N1 Cd1 O1 83.9(2) . . ?
O2 Cd1 O1 54.62(16) . . ?
N4 Cd1 O1 95.3(2) 1_464 . ?
O4 Cd1 C21 116.86(18) 1_455 . ?
O3 Cd1 C21 117.42(18) 2_766 . ?
N1 Cd1 C21 90.39(19) . . ?
O2 Cd1 C21 27.28(18) . . ?
N4 Cd1 C21 92.72(19) 1_464 . ?
O1 Cd1 C21 27.37(18) . . ?
C21 O1 Cd1 89.6(4) . . ?
C21 O2 Cd1 93.4(4) . . ?
C22 O3 Cd1 163.1(5) . 2_766 ?
C22 O4 Cd1 108.8(4) . 1_655 ?
C1 N1 C2 106.8(5) . . ?
C1 N1 Cd1 119.1(4) . . ?
C2 N1 Cd1 134.1(5) . . ?
C1 N2 C3 107.1(6) . . ?
C1 N2 C4 126.3(6) . . ?
C3 N2 C4 126.5(6) . . ?
C16 N3 C17 106.0(5) . . ?
C16 N3 C13 125.4(6) . . ?
C17 N3 C13 128.5(5) . . ?
C16 N4 C18 107.3(6) . . ?
C16 N4 Cd1 119.4(5) . 1_646 ?
C18 N4 Cd1 132.9(4) . 1_646 ?
N1 C1 N2 110.7(6) . . ?
N1 C1 H1A 124.6 . . ?
N2 C1 H1A 124.6 . . ?
C3 C2 N1 108.8(6) . . ?
C3 C2 C19 128.5(7) . . ?
N1 C2 C19 122.6(6) . . ?
C2 C3 N2 106.6(6) . . ?
C2 C3 H3A 126.7 . . ?
N2 C3 H3A 126.7 . . ?
C5 C4 C9 119.9(6) . . ?
C5 C4 N2 121.0(6) . . ?
C9 C4 N2 119.1(7) . . ?
C4 C5 C6 120.3(6) . . ?
C4 C5 H5A 119.8 . . ?
C6 C5 H5A 119.8 . . ?
C7 C6 C5 121.4(7) . . ?
C7 C6 H6A 119.3 . . ?
C5 C6 H6A 119.3 . . ?
C6 C7 C8 117.3(6) . . ?
C6 C7 C10 122.0(6) . . ?
C8 C7 C10 120.7(6) . . ?
C9 C8 C7 120.8(7) . . ?
C9 C8 H8A 119.6 . . ?
C7 C8 H8A 119.6 . . ?
C4 C9 C8 120.3(7) . . ?
C4 C9 H9A 119.9 . . ?
C8 C9 H9A 119.9 . . ?
C11 C10 C15 118.5(6) . . ?
C11 C10 C7 121.9(6) . . ?
C15 C10 C7 119.6(6) . . ?
C10 C11 C12 121.0(6) . . ?
C10 C11 H11A 119.5 . . ?
C12 C11 H11A 119.5 . . ?
C13 C12 C11 119.4(6) . . ?
C13 C12 H12A 120.3 . . ?
C11 C12 H12A 120.3 . . ?
C12 C13 C14 121.1(6) . . ?
C12 C13 N3 120.9(6) . . ?
C14 C13 N3 117.9(6) . . ?
C13 C14 C15 118.9(6) . . ?
C13 C14 H14A 120.5 . . ?
C15 C14 H14A 120.5 . . ?
C10 C15 C14 121.0(7) . . ?
C10 C15 H15A 119.5 . . ?
C14 C15 H15A 119.5 . . ?
N4 C16 N3 111.4(6) . . ?
N4 C16 H16A 124.3 . . ?
N3 C16 H16A 124.3 . . ?
C18 C17 N3 106.8(6) . . ?
C18 C17 H17A 126.6 . . ?
N3 C17 H17A 126.6 . . ?
C17 C18 N4 108.6(6) . . ?
C17 C18 C20 128.8(6) . . ?
N4 C18 C20 122.7(6) . . ?
C2 C19 H19A 109.5 . . ?
C2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C21 O1 122.2(6) . . ?
O2 C21 C23 118.0(6) . . ?
O1 C21 C23 119.7(5) . . ?
O2 C21 Cd1 59.3(3) . . ?
O1 C21 Cd1 63.0(3) . . ?
C23 C21 Cd1 175.6(4) . . ?
O3 C22 O4 123.1(5) . . ?
O3 C22 C25 119.7(5) . . ?
O4 C22 C25 117.2(6) . . ?
C24 C23 C28 119.5(5) . . ?
C24 C23 C21 121.1(5) . . ?
C28 C23 C21 119.4(5) . . ?
C23 C24 C25 120.4(5) . . ?
C23 C24 H24A 119.8 . . ?
C25 C24 H24A 119.8 . . ?
C26 C25 C24 119.1(5) . . ?
C26 C25 C22 119.4(5) . . ?
C24 C25 C22 121.5(5) . . ?
C27 C26 C25 121.0(6) . . ?
C27 C26 H26A 119.5 . . ?
C25 C26 H26A 119.5 . . ?
C28 C27 C26 118.8(6) . . ?
C28 C27 H27A 120.6 . . ?
C26 C27 H27A 120.6 . . ?
C27 C28 C23 121.0(6) . . ?
C27 C28 H28A 119.5 . . ?
C23 C28 H28A 119.5 . . ?

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
C2 N1 C1 N2 -1.0(8) . . . . ?
Cd1 N1 C1 N2 179.4(4) . . . . ?
C3 N2 C1 N1 -0.3(8) . . . . ?
C4 N2 C1 N1 -175.8(6) . . . . ?
C1 N1 C2 C3 1.9(8) . . . . ?
Cd1 N1 C2 C3 -178.6(5) . . . . ?
C1 N1 C2 C19 179.0(7) . . . . ?
Cd1 N1 C2 C19 -1.4(11) . . . . ?
N1 C2 C3 N2 -2.0(8) . . . . ?
C19 C2 C3 N2 -179.0(7) . . . . ?
C1 N2 C3 C2 1.4(8) . . . . ?
C4 N2 C3 C2 177.0(6) . . . . ?
C1 N2 C4 C5 -44.0(10) . . . . ?
C3 N2 C4 C5 141.2(8) . . . . ?
C1 N2 C4 C9 135.6(8) . . . . ?
C3 N2 C4 C9 -39.1(11) . . . . ?
C9 C4 C5 C6 -0.2(11) . . . . ?
N2 C4 C5 C6 179.4(7) . . . . ?
C4 C5 C6 C7 -0.2(12) . . . . ?
C5 C6 C7 C8 0.6(11) . . . . ?
C5 C6 C7 C10 -179.9(7) . . . . ?
C6 C7 C8 C9 -0.7(12) . . . . ?
C10 C7 C8 C9 179.9(8) . . . . ?
C5 C4 C9 C8 0.2(12) . . . . ?
N2 C4 C9 C8 -179.5(7) . . . . ?
C7 C8 C9 C4 0.3(13) . . . . ?
C6 C7 C10 C11 12.1(11) . . . . ?
C8 C7 C10 C11 -168.4(7) . . . . ?
C6 C7 C10 C15 -168.5(6) . . . . ?
C8 C7 C10 C15 11.0(10) . . . . ?
C15 C10 C11 C12 1.1(11) . . . . ?
C7 C10 C11 C12 -179.5(7) . . . . ?
C10 C11 C12 C13 -0.2(12) . . . . ?
C11 C12 C13 C14 -1.1(11) . . . . ?
C11 C12 C13 N3 178.2(7) . . . . ?
C16 N3 C13 C12 -148.3(7) . . . . ?
C17 N3 C13 C12 28.6(10) . . . . ?
C16 N3 C13 C14 31.1(10) . . . . ?
C17 N3 C13 C14 -152.0(7) . . . . ?
C12 C13 C14 C15 1.5(11) . . . . ?
N3 C13 C14 C15 -177.9(6) . . . . ?
C11 C10 C15 C14 -0.8(11) . . . . ?
C7 C10 C15 C14 179.8(7) . . . . ?
C13 C14 C15 C10 -0.5(11) . . . . ?
C18 N4 C16 N3 0.8(8) . . . . ?
Cd1 N4 C16 N3 174.5(4) 1_646 . . . ?
C17 N3 C16 N4 -0.3(8) . . . . ?
C13 N3 C16 N4 177.1(6) . . . . ?
C16 N3 C17 C18 -0.2(8) . . . . ?
C13 N3 C17 C18 -177.6(6) . . . . ?
N3 C17 C18 N4 0.7(8) . . . . ?
N3 C17 C18 C20 179.4(7) . . . . ?
C16 N4 C18 C17 -0.9(8) . . . . ?
Cd1 N4 C18 C17 -173.5(5) 1_646 . . . ?
C16 N4 C18 C20 -179.8(7) . . . . ?
Cd1 N4 C18 C20 7.7(10) 1_646 . . . ?
Cd1 O2 C21 O1 -3.2(7) . . . . ?
Cd1 O2 C21 C23 176.0(5) . . . . ?
Cd1 O1 C21 O2 3.0(7) . . . . ?
Cd1 O1 C21 C23 -176.1(5) . . . . ?
Cd1 O3 C22 O4 -101.8(15) 2_766 . . . ?
Cd1 O3 C22 C25 78.4(16) 2_766 . . . ?
Cd1 O4 C22 O3 8.6(8) 1_655 . . . ?
Cd1 O4 C22 C25 -171.6(4) 1_655 . . . ?
O2 C21 C23 C24 171.6(6) . . . . ?
O1 C21 C23 C24 -9.2(9) . . . . ?
O2 C21 C23 C28 -9.3(9) . . . . ?
O1 C21 C23 C28 169.9(6) . . . . ?
C28 C23 C24 C25 -0.5(9) . . . . ?
C21 C23 C24 C25 178.6(5) . . . . ?
C23 C24 C25 C26 -0.2(9) . . . . ?
C23 C24 C25 C22 178.9(5) . . . . ?
O3 C22 C25 C26 -177.3(7) . . . . ?
O4 C22 C25 C26 2.9(9) . . . . ?
O3 C22 C25 C24 3.7(9) . . . . ?
O4 C22 C25 C24 -176.1(6) . . . . ?
C24 C25 C26 C27 -1.4(11) . . . . ?
C22 C25 C26 C27 179.6(7) . . . . ?
C25 C26 C27 C28 3.6(13) . . . . ?
C26 C27 C28 C23 -4.3(12) . . . . ?
C24 C23 C28 C27 2.8(10) . . . . ?
C21 C23 C28 C27 -176.3(7) . . . . ?

_refine_diff_density_max         1.469
_refine_diff_density_min         -1.312
_refine_diff_density_rms         0.228

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 1025330'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Cpx4

_audit_update_record             
;
2014-11-15 # Formatted by publCIF

;
_publcif_datablock.id            {7f27d4d4-453e-4dcb-816a-c2f1c0e8f839}

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H22 Cd N4 O4'
_chemical_formula_sum            'C28 H22 Cd N4 O4'
_chemical_formula_weight         590.89

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'

_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+1/2, -y, z'
'-x+1/2, y+1/2, -z+1/2'
'x, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'x-1/2, -y-1/2, z-1/2'
'-x, y-1/2, z-1/2'

_cell_length_a                   13.2835(4)
_cell_length_b                   17.3692(6)
_cell_length_c                   10.6116(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2448.35(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2720
_cell_measurement_theta_min      3.7870
_cell_measurement_theta_max      30.1360

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_F_000             1192
_exptl_transmission_factor_min   0.799
_exptl_transmission_factor_max   0.954
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.935
_shelx_estimated_absorpt_T_min   0.706
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           ?

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4471
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9582
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.067
_diffrn_reflns_theta_max         28.272
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3031
_reflns_number_gt                2212
_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)+(0.0278P)²+0.9721P]
 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         3031
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0707
_refine_ls_wR_factor_gt          0.0618
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
Cd1 Cd -0.18036(2) -0.2500 0.7500 0.03064(8) Uani 1 2 d S T P . .
O1 O -0.05973(13) -0.18034(10) 0.65969(17) 0.0496(5) Uani 1 1 d . . . . .
O2 O -0.19647(12) -0.10904(10) 0.66654(15) 0.0419(4) Uani 1 1 d . . . . .
N1 N -0.29282(15) -0.29106(13) 0.60788(18) 0.0400(5) Uani 1 1 d . . . . .
N2 N -0.43617(15) -0.34401(12) 0.55221(18) 0.0407(5) Uani 1 1 d . . . . .
C1 C -0.36713(19) -0.33616(15) 0.6436(2) 0.0438(6) Uani 1 1 d . . . . .
H1 H -0.3713 -0.3596 0.7222 0.053 Uiso 1 1 calc R U . . .
C2 C -0.31446(18) -0.26856(15) 0.4860(2) 0.0398(6) Uani 1 1 d . . . . .
C3 C -0.40230(19) -0.30119(16) 0.4510(2) 0.0443(6) Uani 1 1 d . . . . .
H3 H -0.4340 -0.2959 0.3734 0.053 Uiso 1 1 calc R U . . .
C4 C -0.52676(18) -0.38846(15) 0.5568(2) 0.0410(6) Uani 1 1 d . . . . .
C5 C -0.56313(19) -0.42075(16) 0.4474(2) 0.0449(6) Uani 1 1 d . . . . .
H5 H -0.5291 -0.4135 0.3717 0.054 Uiso 1 1 calc R U . . .
C6 C -0.65022(19) -0.46387(16) 0.4504(2) 0.0454(6) Uani 1 1 d . . . . .
H6 H -0.6744 -0.4850 0.3758 0.054 Uiso 1 1 calc R U . . .
C7 C -0.70318(18) -0.47678(15) 0.5616(2) 0.0405(6) Uani 1 1 d . . . . .
C8 C -0.6638(2) -0.44405(19) 0.6705(3) 0.0579(8) Uani 1 1 d . . . . .
H8 H -0.6968 -0.4519 0.7467 0.069 Uiso 1 1 calc R U . . .
C9 C -0.5771(2) -0.40017(18) 0.6690(3) 0.0563(8) Uani 1 1 d . . . . .
H9 H -0.5528 -0.3786 0.7432 0.068 Uiso 1 1 calc R U . . .
C10 C -0.2485(2) -0.21585(19) 0.4140(2) 0.0556(7) Uani 1 1 d . . . . .
H10A H -0.2767 -0.2072 0.3319 0.083 Uiso 1 1 calc R U . . .
H10B H -0.1829 -0.2385 0.4054 0.083 Uiso 1 1 calc R U . . .
H10C H -0.2430 -0.1677 0.4578 0.083 Uiso 1 1 calc R U . . .
C11 C -0.10748(18) -0.11893(14) 0.6354(2) 0.0338(5) Uani 1 1 d . . . . .
C12 C -0.05163(16) -0.05722(13) 0.56551(19) 0.0319(5) Uani 1 1 d . . . . .
C13 C -0.09459(18) 0.01460(14) 0.5492(2) 0.0389(6) Uani 1 1 d . . . . .
H13 H -0.1582 0.0248 0.5816 0.047 Uiso 1 1 calc R U . . .
C14 C 0.04265(18) -0.07162(14) 0.5159(2) 0.0400(6) Uani 1 1 d . . . . .
H14 H 0.0717 -0.1200 0.5260 0.048 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
Cd1 O1 2.2248(16) 4_546 ?
Cd1 O1 2.2249(16) . ?
Cd1 N1 2.2393(19) . ?
Cd1 N1 2.2394(19) 4_546 ?
Cd1 O2 2.6125(17) . ?
Cd1 O2 2.6125(17) 4_546 ?
Cd1 C11 2.757(2) 4_546 ?
Cd1 C11 2.757(2) . ?
O1 C11 1.267(3) . ?
O2 C11 1.239(3) . ?
N1 C1 1.316(3) . ?
N1 C2 1.381(3) . ?
N2 C1 1.342(3) . ?
N2 C3 1.382(3) . ?
N2 C4 1.431(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.349(3) . ?
C2 C10 1.481(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(3) . ?
C4 C9 1.381(4) . ?
C5 C6 1.378(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.391(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.391(3) . ?
C7 C7 1.483(5) 2_345 ?
C8 C9 1.381(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.500(3) . ?
C12 C14 1.381(3) . ?
C12 C13 1.383(3) . ?
C13 C14 1.390(3) 5_556 ?
C13 H13 0.9300 . ?
C14 C13 1.390(3) 5_556 ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cd1 O1 87.86(9) 4_546 . ?
O1 Cd1 N1 126.68(7) 4_546 . ?
O1 Cd1 N1 111.32(7) . . ?
O1 Cd1 N1 111.32(7) 4_546 4_546 ?
O1 Cd1 N1 126.68(7) . 4_546 ?
N1 Cd1 N1 96.31(11) . 4_546 ?
O1 Cd1 O2 135.62(6) 4_546 . ?
O1 Cd1 O2 53.36(6) . . ?
N1 Cd1 O2 90.89(7) . . ?
N1 Cd1 O2 82.83(6) 4_546 . ?
O1 Cd1 O2 53.36(6) 4_546 4_546 ?
O1 Cd1 O2 135.62(6) . 4_546 ?
N1 Cd1 O2 82.83(6) . 4_546 ?
N1 Cd1 O2 90.89(7) 4_546 4_546 ?
O2 Cd1 O2 170.60(7) . 4_546 ?
O1 Cd1 C11 26.86(6) 4_546 4_546 ?
O1 Cd1 C11 112.72(7) . 4_546 ?
N1 Cd1 C11 105.57(7) . 4_546 ?
N1 Cd1 C11 101.55(7) 4_546 4_546 ?
O2 Cd1 C11 162.24(7) . 4_546 ?
O2 Cd1 C11 26.52(6) 4_546 4_546 ?
O1 Cd1 C11 112.72(7) 4_546 . ?
O1 Cd1 C11 26.86(6) . . ?
N1 Cd1 C11 101.54(7) . . ?
N1 Cd1 C11 105.57(7) 4_546 . ?
O2 Cd1 C11 26.52(6) . . ?
O2 Cd1 C11 162.24(7) 4_546 . ?
C11 Cd1 C11 138.88(10) 4_546 . ?
C11 O1 Cd1 100.66(14) . . ?
C11 O2 Cd1 83.24(14) . . ?
C1 N1 C2 106.4(2) . . ?
C1 N1 Cd1 119.73(16) . . ?
C2 N1 Cd1 132.78(17) . . ?
C1 N2 C3 106.5(2) . . ?
C1 N2 C4 127.2(2) . . ?
C3 N2 C4 126.2(2) . . ?
N1 C1 N2 111.4(2) . . ?
N1 C1 H1 124.3 . . ?
N2 C1 H1 124.3 . . ?
C3 C2 N1 108.6(2) . . ?
C3 C2 C10 129.0(2) . . ?
N1 C2 C10 122.4(2) . . ?
C2 C3 N2 107.1(2) . . ?
C2 C3 H3 126.5 . . ?
N2 C3 H3 126.5 . . ?
C5 C4 C9 119.8(2) . . ?
C5 C4 N2 119.1(2) . . ?
C9 C4 N2 121.1(2) . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 122.1(2) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C8 C7 C6 116.7(2) . . ?
C8 C7 C7 122.54(16) . 2_345 ?
C6 C7 C7 120.80(15) . 2_345 ?
C7 C8 C9 122.0(3) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
C8 C9 C4 119.7(3) . . ?
C8 C9 H9 120.1 . . ?
C4 C9 H9 120.1 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 O1 122.7(2) . . ?
O2 C11 C12 120.3(2) . . ?
O1 C11 C12 117.0(2) . . ?
O2 C11 Cd1 70.24(13) . . ?
O1 C11 Cd1 52.48(11) . . ?
C12 C11 Cd1 169.15(17) . . ?
C14 C12 C13 119.3(2) . . ?
C14 C12 C11 120.5(2) . . ?
C13 C12 C11 120.2(2) . . ?
C12 C13 C14 120.0(2) . 5_556 ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 5_556 . ?
C12 C14 C13 120.7(2) . 5_556 ?
C12 C14 H14 119.7 . . ?
C13 C14 H14 119.7 5_556 . ?

_refine_diff_density_max         0.475
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.063

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 1025331'
