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

#######################################################################
#
#                 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_Cd1D

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 Cd N12 O3.0'
_chemical_formula_weight         588.88

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'
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'
H H 0.0000 0.0000 '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                   7.563(6)
_cell_length_b                   8.340(7)
_cell_length_c                   9.721(6)
_cell_angle_alpha                68.15(3)
_cell_angle_beta                 79.933(15)
_cell_angle_gamma                63.506(9)
_cell_volume                     509.3(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1823
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      27.51

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.920
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    1.130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7068
_exptl_absorpt_correction_T_max  0.7426
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2848
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0546
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         26.49
_reflns_number_total             2045
_reflns_number_gt                1971
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0892P)²+5.9501P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2045
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1754
_refine_ls_wR_factor_gt          0.1737
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.0000 1.0000 0.0000 0.0205(3) Uani 1 2 d S . .
O1 O 0.0042(9) 1.2590(9) 0.0529(8) 0.0412(14) Uani 1 1 d . . .
H1A H -0.0852 1.3717 0.0208 0.062 Uiso 1 1 d R . .
H1B H 0.0153 1.2314 0.1452 0.062 Uiso 1 1 d R . .
N1 N 0.6672(9) 0.6306(9) -0.0124(7) 0.0281(14) Uani 1 1 d . . .
N2 N 0.5853(10) 0.6630(10) -0.1384(8) 0.0352(15) Uani 1 1 d . . .
N3 N 0.3992(10) 0.7745(9) -0.1406(7) 0.0293(14) Uani 1 1 d . . .
N4 N 0.3508(9) 0.8204(9) -0.0163(6) 0.0262(13) Uani 1 1 d . . .
N6 N 0.9814(9) 0.1667(9) 0.7519(7) 0.0290(14) Uani 1 1 d . . .
N5 N 0.8437(9) 0.3843(9) 0.5433(7) 0.0282(14) Uani 1 1 d . . .
C3 C 0.4326(12) 0.8825(11) 0.2532(8) 0.0308(17) Uani 1 1 d . . .
H3A H 0.3405 0.9920 0.1896 0.037 Uiso 1 1 calc R . .
C4 C 0.4571(12) 0.8755(11) 0.3919(9) 0.0289(16) Uani 1 1 d . . .
H4A H 0.3823 0.9813 0.4212 0.035 Uiso 1 1 calc R . .
C5 C 0.5917(12) 0.7128(11) 0.4894(9) 0.0297(16) Uani 1 1 d . . .
H5A H 0.6061 0.7079 0.5841 0.036 Uiso 1 1 calc R . .
C6 C 0.7050(11) 0.5568(11) 0.4428(8) 0.0273(15) Uani 1 1 d . . .
C7 C 0.6800(11) 0.5636(11) 0.3034(8) 0.0276(16) Uani 1 1 d . . .
H7A H 0.7539 0.4584 0.2733 0.033 Uiso 1 1 calc R . .
C2 C 0.5439(11) 0.7282(11) 0.2080(8) 0.0270(15) Uani 1 1 d . . .
C1 C 0.5176(11) 0.7292(11) 0.0603(8) 0.0262(15) Uani 1 1 d . . .
C8 C 0.8529(12) 0.3423(11) 0.6904(8) 0.0296(16) Uani 1 1 d . . .
H8A H 0.7783 0.4262 0.7416 0.035 Uiso 1 1 calc R . .
C9 C 1.0596(12) 0.0959(11) 0.6371(8) 0.0314(17) Uani 1 1 d . . .
H9A H 1.1557 -0.0261 0.6470 0.038 Uiso 1 1 calc R . .
C10 C 0.9767(12) 0.2289(12) 0.5085(9) 0.0343(18) Uani 1 1 d . . .
H10A H 1.0047 0.2170 0.4148 0.041 Uiso 1 1 calc R . .
O1W O 0.5000 0.0000 0.0000 0.133(9) Uani 1 2 d S . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cd1 0.0227(4) 0.0179(4) 0.0139(4) -0.0026(3) -0.0030(2) -0.0038(3)
O1 0.030(3) 0.030(3) 0.058(4) -0.014(3) -0.005(3) -0.007(3)
N1 0.028(3) 0.029(3) 0.020(3) -0.009(3) -0.002(2) -0.005(3)
N2 0.033(4) 0.035(4) 0.034(4) -0.013(3) -0.005(3) -0.007(3)
N3 0.033(3) 0.025(3) 0.024(3) -0.009(3) -0.004(3) -0.005(3)
N4 0.032(3) 0.024(3) 0.018(3) -0.005(2) -0.002(2) -0.008(3)
N6 0.028(3) 0.029(3) 0.020(3) -0.006(3) 0.000(2) -0.004(3)
N5 0.025(3) 0.027(3) 0.025(3) -0.007(3) -0.003(2) -0.005(3)
C3 0.031(4) 0.027(4) 0.025(4) -0.002(3) -0.006(3) -0.009(3)
C4 0.034(4) 0.024(4) 0.030(4) -0.015(3) -0.002(3) -0.006(3)
C5 0.035(4) 0.024(4) 0.025(4) -0.008(3) -0.003(3) -0.007(3)
C6 0.024(3) 0.027(4) 0.028(4) -0.008(3) 0.001(3) -0.010(3)
C7 0.028(4) 0.026(4) 0.023(4) -0.008(3) -0.002(3) -0.006(3)
C2 0.029(4) 0.026(4) 0.021(3) -0.005(3) 0.002(3) -0.010(3)
C1 0.023(3) 0.023(4) 0.027(4) -0.004(3) -0.004(3) -0.008(3)
C8 0.033(4) 0.025(4) 0.023(4) -0.007(3) -0.002(3) -0.006(3)
C9 0.034(4) 0.025(4) 0.024(4) -0.010(3) -0.001(3) -0.002(3)
C10 0.034(4) 0.028(4) 0.021(4) -0.007(3) -0.005(3) 0.004(3)
O1W 0.33(3) 0.046(7) 0.030(6) -0.011(5) 0.016(10) -0.098(12)

_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 N6 2.284(6) 2_666 ?
Cd1 N6 2.284(6) 1_464 ?
Cd1 N4 2.406(7) 2_575 ?
Cd1 N4 2.406(7) . ?
Cd1 O1 2.413(6) 2_575 ?
Cd1 O1 2.413(6) . ?
O1 H1A 0.8524 . ?
O1 H1B 0.8491 . ?
N1 C1 1.334(10) . ?
N1 N2 1.351(9) . ?
N2 N3 1.294(10) . ?
N3 N4 1.344(9) . ?
N4 C1 1.332(9) . ?
N6 C8 1.315(10) . ?
N6 C9 1.376(10) . ?
N6 Cd1 2.284(6) 1_646 ?
N5 C8 1.347(10) . ?
N5 C10 1.360(10) . ?
N5 C6 1.446(10) . ?
C3 C4 1.369(11) . ?
C3 C2 1.372(11) . ?
C3 H3A 0.9300 . ?
C4 C5 1.387(11) . ?
C4 H4A 0.9300 . ?
C5 C6 1.393(11) . ?
C5 H5A 0.9300 . ?
C6 C7 1.377(11) . ?
C7 C2 1.389(10) . ?
C7 H7A 0.9300 . ?
C2 C1 1.480(10) . ?
C8 H8A 0.9300 . ?
C9 C10 1.344(11) . ?
C9 H9A 0.9300 . ?
C10 H10A 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
N6 Cd1 N6 180.000(1) 2_666 1_464 ?
N6 Cd1 N4 92.0(2) 2_666 2_575 ?
N6 Cd1 N4 88.0(2) 1_464 2_575 ?
N6 Cd1 N4 88.0(2) 2_666 . ?
N6 Cd1 N4 92.0(2) 1_464 . ?
N4 Cd1 N4 180.000(1) 2_575 . ?
N6 Cd1 O1 90.6(2) 2_666 2_575 ?
N6 Cd1 O1 89.4(2) 1_464 2_575 ?
N4 Cd1 O1 98.6(2) 2_575 2_575 ?
N4 Cd1 O1 81.4(2) . 2_575 ?
N6 Cd1 O1 89.4(2) 2_666 . ?
N6 Cd1 O1 90.6(2) 1_464 . ?
N4 Cd1 O1 81.4(2) 2_575 . ?
N4 Cd1 O1 98.6(2) . . ?
O1 Cd1 O1 180.0(3) 2_575 . ?
Cd1 O1 H1A 121.6 . . ?
Cd1 O1 H1B 111.0 . . ?
H1A O1 H1B 107.6 . . ?
C1 N1 N2 104.3(6) . . ?
N3 N2 N1 110.1(6) . . ?
N2 N3 N4 109.2(6) . . ?
C1 N4 N3 105.2(6) . . ?
C1 N4 Cd1 143.2(5) . . ?
N3 N4 Cd1 111.1(4) . . ?
C8 N6 C9 105.3(6) . . ?
C8 N6 Cd1 125.0(5) . 1_646 ?
C9 N6 Cd1 127.7(5) . 1_646 ?
C8 N5 C10 107.6(6) . . ?
C8 N5 C6 126.1(6) . . ?
C10 N5 C6 126.0(6) . . ?
C4 C3 C2 120.1(7) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C5 120.9(7) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C4 C5 C6 118.8(7) . . ?
C4 C5 H5A 120.6 . . ?
C6 C5 H5A 120.6 . . ?
C7 C6 C5 120.3(7) . . ?
C7 C6 N5 119.8(7) . . ?
C5 C6 N5 119.8(7) . . ?
C6 C7 C2 119.8(7) . . ?
C6 C7 H7A 120.1 . . ?
C2 C7 H7A 120.1 . . ?
C3 C2 C7 120.1(7) . . ?
C3 C2 C1 121.5(7) . . ?
C7 C2 C1 118.4(7) . . ?
N4 C1 N1 111.2(7) . . ?
N4 C1 C2 127.0(7) . . ?
N1 C1 C2 121.7(6) . . ?
N6 C8 N5 110.9(7) . . ?
N6 C8 H8A 124.6 . . ?
N5 C8 H8A 124.6 . . ?
C10 C9 N6 110.1(7) . . ?
C10 C9 H9A 125.0 . . ?
N6 C9 H9A 125.0 . . ?
C9 C10 N5 106.0(7) . . ?
C9 C10 H10A 127.0 . . ?
N5 C10 H10A 127.0 . . ?

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
C1 N1 N2 N3 0.3(9) . . . . ?
N1 N2 N3 N4 0.1(9) . . . . ?
N2 N3 N4 C1 -0.4(8) . . . . ?
N2 N3 N4 Cd1 -173.9(5) . . . . ?
N6 Cd1 N4 C1 -28.7(9) 2_666 . . . ?
N6 Cd1 N4 C1 151.3(9) 1_464 . . . ?
N4 Cd1 N4 C1 90(100) 2_575 . . . ?
O1 Cd1 N4 C1 -119.6(9) 2_575 . . . ?
O1 Cd1 N4 C1 60.4(9) . . . . ?
N6 Cd1 N4 N3 140.6(5) 2_666 . . . ?
N6 Cd1 N4 N3 -39.4(5) 1_464 . . . ?
N4 Cd1 N4 N3 -101(100) 2_575 . . . ?
O1 Cd1 N4 N3 49.8(5) 2_575 . . . ?
O1 Cd1 N4 N3 -130.2(5) . . . . ?
C2 C3 C4 C5 -0.9(13) . . . . ?
C3 C4 C5 C6 1.2(12) . . . . ?
C4 C5 C6 C7 -1.4(12) . . . . ?
C4 C5 C6 N5 -178.8(7) . . . . ?
C8 N5 C6 C7 -164.4(8) . . . . ?
C10 N5 C6 C7 9.4(12) . . . . ?
C8 N5 C6 C5 13.0(12) . . . . ?
C10 N5 C6 C5 -173.1(8) . . . . ?
C5 C6 C7 C2 1.3(12) . . . . ?
N5 C6 C7 C2 178.8(7) . . . . ?
C4 C3 C2 C7 0.8(12) . . . . ?
C4 C3 C2 C1 178.4(7) . . . . ?
C6 C7 C2 C3 -1.0(12) . . . . ?
C6 C7 C2 C1 -178.7(7) . . . . ?
N3 N4 C1 N1 0.6(9) . . . . ?
Cd1 N4 C1 N1 170.4(6) . . . . ?
N3 N4 C1 C2 -178.4(7) . . . . ?
Cd1 N4 C1 C2 -8.6(14) . . . . ?
N2 N1 C1 N4 -0.6(9) . . . . ?
N2 N1 C1 C2 178.5(7) . . . . ?
C3 C2 C1 N4 -31.7(12) . . . . ?
C7 C2 C1 N4 146.0(8) . . . . ?
C3 C2 C1 N1 149.4(8) . . . . ?
C7 C2 C1 N1 -33.0(11) . . . . ?
C9 N6 C8 N5 1.1(9) . . . . ?
Cd1 N6 C8 N5 -163.9(5) 1_646 . . . ?
C10 N5 C8 N6 -1.5(10) . . . . ?
C6 N5 C8 N6 173.3(7) . . . . ?
C8 N6 C9 C10 -0.3(10) . . . . ?
Cd1 N6 C9 C10 164.1(6) 1_646 . . . ?
N6 C9 C10 N5 -0.6(10) . . . . ?
C8 N5 C10 C9 1.2(10) . . . . ?
C6 N5 C10 C9 -173.6(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.967
_diffrn_reflns_theta_full        26.49
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         2.139
_refine_diff_density_min         -1.093
_refine_diff_density_rms         0.213
_database_code_depnum_ccdc_archive 'CCDC 992090'
#######################################################################
#
#                 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_Cd2Dc

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 Cd N12 O3'
_chemical_formula_weight         588.88

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   'P2(1)/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                   12.584(2)
_cell_length_b                   11.4846(19)
_cell_length_c                   15.765(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.664(2)
_cell_angle_gamma                90.00
_cell_volume                     2231.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2536
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      24.99

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1184
_exptl_absorpt_coefficient_mu    1.032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7472
_exptl_absorpt_correction_T_max  0.8361
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8944
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         25.25
_reflns_number_total             3939
_reflns_number_gt                3160
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0380P)²+0.4477P] 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         3939
_refine_ls_number_parameters     331
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0785
_refine_ls_wR_factor_gt          0.0721
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      3.709
_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 0.70247(7) 0.86365(8) 0.39103(5) 0.0253(4) Uani 1 1 d . . .
C1 C 0.6591(10) 0.6418(11) 0.2361(8) 0.026(3) Uani 1 1 d . . .
C2 C 0.7261(10) 0.5483(11) 0.2838(7) 0.027(3) Uani 1 1 d . . .
C3 C 0.8241(10) 0.5700(12) 0.3389(8) 0.032(3) Uani 1 1 d . . .
H3A H 0.8508 0.6456 0.3465 0.038 Uiso 1 1 calc R . .
C4 C 0.8825(11) 0.4784(13) 0.3830(8) 0.037(3) Uani 1 1 d . . .
H4A H 0.9478 0.4938 0.4208 0.044 Uiso 1 1 calc R . .
C5 C 0.8461(10) 0.3655(12) 0.3721(8) 0.032(3) Uani 1 1 d . . .
H5A H 0.8867 0.3047 0.4012 0.039 Uiso 1 1 calc R . .
C6 C 0.7476(10) 0.3446(11) 0.3167(8) 0.026(3) Uani 1 1 d . . .
C7 C 0.6868(10) 0.4360(12) 0.2738(7) 0.029(3) Uani 1 1 d . . .
H7A H 0.6196 0.4213 0.2384 0.035 Uiso 1 1 calc RD . .
C8 C 0.7334(10) 0.1361(11) 0.3574(8) 0.027(3) Uani 1 1 d . . .
H8A H 0.7825 0.1395 0.4101 0.032 Uiso 1 1 calc R . .
C9 C 0.6324(11) 0.1867(12) 0.2333(8) 0.033(3) Uani 1 1 d . . .
H9A H 0.5988 0.2293 0.1851 0.040 Uiso 1 1 calc R . .
C10 C 0.6183(10) 0.0732(12) 0.2478(8) 0.032(3) Uani 1 1 d . . .
H10A H 0.5725 0.0235 0.2106 0.039 Uiso 1 1 calc R . .
C11 C 0.9589(10) 0.9294(11) 0.3673(7) 0.026(3) Uani 1 1 d . . .
C12 C 0.9264(10) 0.9921(11) 0.2840(7) 0.027(3) Uani 1 1 d . . .
C13 C 0.9578(11) 1.1059(12) 0.2751(8) 0.034(3) Uani 1 1 d . . .
H13A H 1.0046 1.1426 0.3205 0.041 Uiso 1 1 calc R . .
C14 C 0.9197(12) 1.1652(13) 0.1986(9) 0.041(4) Uani 1 1 d . . .
H14A H 0.9393 1.2425 0.1934 0.049 Uiso 1 1 calc R . .
C15 C 0.8527(12) 1.1104(12) 0.1298(8) 0.038(3) Uani 1 1 d . . .
H15A H 0.8276 1.1503 0.0784 0.045 Uiso 1 1 calc R . .
C16 C 0.8235(10) 0.9962(12) 0.1384(7) 0.029(3) Uani 1 1 d . . .
C17 C 0.8589(10) 0.9356(12) 0.2152(7) 0.029(3) Uani 1 1 d . . .
H17A H 0.8379 0.8588 0.2206 0.034 Uiso 1 1 calc R . .
C18 C 0.7703(12) 0.8265(13) 0.0411(8) 0.037(3) Uani 1 1 d . . .
H18A H 0.8281 0.7789 0.0658 0.044 Uiso 1 1 calc R . .
C19 C 0.6622(11) 0.9786(13) 0.0155(8) 0.040(4) Uani 1 1 d . . .
H19A H 0.6310 1.0517 0.0176 0.047 Uiso 1 1 calc R . .
C20 C 0.6256(12) 0.8908(13) -0.0405(9) 0.040(4) Uani 1 1 d . . .
H20A H 0.5633 0.8943 -0.0838 0.048 Uiso 1 1 calc R . .
N1 N 0.5976(9) 0.6256(9) 0.1577(6) 0.033(3) Uani 1 1 d . . .
N2 N 0.5478(9) 0.7291(10) 0.1366(6) 0.036(3) Uani 1 1 d . . .
N3 N 0.5786(9) 0.8044(10) 0.1992(6) 0.033(3) Uani 1 1 d . . .
N4 N 0.6502(8) 0.7511(9) 0.2636(6) 0.028(2) Uani 1 1 d . . .
N5 N 0.7068(8) 0.2280(9) 0.3040(6) 0.026(2) Uani 1 1 d . . .
N6 N 0.6817(8) 0.0413(9) 0.3261(6) 0.027(2) Uani 1 1 d . . .
N7 N 0.8916(8) 0.8656(9) 0.4035(6) 0.026(2) Uani 1 1 d . . .
N8 N 0.9538(9) 0.8222(11) 0.4773(7) 0.037(3) Uani 1 1 d . . .
N9 N 1.0532(9) 0.8601(10) 0.4827(7) 0.037(3) Uani 1 1 d . . .
N10 N 1.0588(8) 0.9288(10) 0.4147(6) 0.032(3) Uani 1 1 d . . .
N11 N 0.7549(9) 0.9368(10) 0.0684(6) 0.034(3) Uani 1 1 d . . .
N12 N 0.6935(9) 0.7962(10) -0.0243(7) 0.036(3) Uani 1 1 d . . .
O1W O 0.7326(7) 0.9787(9) 0.5294(5) 0.041(2) Uani 1 1 d . . .
H1WA H 0.7962 1.0029 0.5511 0.062 Uiso 1 1 d R . .
H1WB H 0.7100 0.9410 0.5688 0.062 Uiso 1 1 d R . .
O2W O 0.5224(7) 0.9041(9) 0.4022(6) 0.041(2) Uani 1 1 d . . .
H2WB H 0.4921 0.9832 0.3938 0.062 Uiso 1 1 d R . .
H2WA H 0.4818 0.8587 0.4302 0.062 Uiso 1 1 d RD . .
O3W O 0.6135(9) 0.2831(11) 0.0153(6) 0.051(3) Uani 1 1 d D . .
H3WB H 0.570(12) 0.278(16) -0.033(7) 0.076 Uiso 1 1 d D . .
H3WA H 0.648(13) 0.344(12) 0.013(11) 0.076 Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cd1 0.0274(6) 0.0191(6) 0.0270(5) 0.0028(4) -0.0001(4) -0.0005(4)
C1 0.030(7) 0.019(8) 0.029(6) 0.001(5) 0.004(5) -0.007(6)
C2 0.030(7) 0.021(8) 0.029(6) -0.001(5) 0.004(5) 0.001(6)
C3 0.031(7) 0.021(8) 0.041(7) -0.003(6) 0.003(6) -0.005(6)
C4 0.032(8) 0.030(9) 0.042(8) -0.005(7) -0.006(6) -0.004(7)
C5 0.029(7) 0.026(9) 0.038(7) 0.004(6) -0.001(6) 0.005(6)
C6 0.028(7) 0.019(8) 0.030(6) 0.002(5) 0.002(5) -0.004(6)
C7 0.028(7) 0.027(9) 0.030(7) 0.002(6) 0.001(5) -0.004(6)
C8 0.028(7) 0.022(8) 0.029(6) 0.002(6) 0.002(5) 0.002(6)
C9 0.042(8) 0.020(8) 0.032(7) 0.005(6) -0.006(6) 0.001(6)
C10 0.035(8) 0.024(9) 0.032(7) -0.002(6) -0.009(6) 0.002(6)
C11 0.027(7) 0.019(8) 0.032(7) -0.007(5) 0.003(5) -0.001(6)
C12 0.027(7) 0.024(8) 0.030(6) 0.002(6) 0.008(5) 0.003(6)
C13 0.037(8) 0.030(9) 0.032(7) -0.006(6) 0.003(6) -0.008(6)
C14 0.055(10) 0.025(9) 0.045(8) 0.003(6) 0.016(7) -0.005(7)
C15 0.048(9) 0.032(10) 0.032(7) 0.001(6) 0.006(6) -0.001(7)
C16 0.031(7) 0.029(9) 0.026(6) -0.002(6) 0.005(5) -0.004(6)
C17 0.032(7) 0.026(8) 0.028(7) -0.003(6) 0.004(5) -0.006(6)
C18 0.041(9) 0.032(9) 0.033(7) -0.002(6) 0.000(6) 0.005(7)
C19 0.043(9) 0.033(9) 0.039(8) 0.000(7) 0.000(6) 0.016(7)
C20 0.042(9) 0.037(10) 0.038(8) 0.000(7) -0.002(6) 0.006(7)
N1 0.043(7) 0.021(7) 0.031(6) -0.001(5) -0.004(5) 0.002(5)
N2 0.046(7) 0.026(7) 0.031(6) 0.001(5) -0.002(5) 0.000(6)
N3 0.042(7) 0.022(7) 0.031(6) 0.002(5) -0.002(5) 0.000(5)
N4 0.036(6) 0.016(6) 0.029(5) 0.001(5) -0.002(5) 0.000(5)
N5 0.028(6) 0.019(6) 0.029(5) 0.004(5) -0.002(4) 0.003(5)
N6 0.030(6) 0.016(6) 0.033(6) 0.001(5) 0.004(5) 0.000(5)
N7 0.026(6) 0.021(6) 0.026(5) 0.002(4) -0.003(4) -0.001(5)
N8 0.037(7) 0.035(8) 0.036(6) 0.005(5) -0.003(5) -0.001(6)
N9 0.031(6) 0.039(8) 0.036(6) 0.001(5) -0.005(5) 0.000(6)
N10 0.027(6) 0.033(8) 0.032(6) -0.002(5) -0.001(5) -0.001(5)
N11 0.042(7) 0.030(8) 0.026(6) -0.001(5) 0.000(5) 0.003(5)
N12 0.045(7) 0.030(8) 0.033(6) -0.002(5) 0.008(5) 0.000(6)
O1W 0.039(6) 0.050(7) 0.033(5) 0.000(5) 0.003(4) -0.012(5)
O2W 0.030(5) 0.037(6) 0.056(6) 0.015(5) 0.009(4) 0.005(5)
O3W 0.052(7) 0.059(9) 0.040(6) 0.000(6) 0.005(5) 0.003(6)

_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 N6 2.275(10) 1_565 ?
Cd1 N12 2.286(11) 4_576 ?
Cd1 N7 2.348(10) . ?
Cd1 N4 2.367(10) . ?
Cd1 O2W 2.355(9) . ?
Cd1 O1W 2.513(9) . ?
C1 N1 1.332(16) . ?
C1 N4 1.340(16) . ?
C1 C2 1.474(18) . ?
C2 C3 1.380(17) . ?
C2 C7 1.378(18) . ?
C3 C4 1.386(18) . ?
C4 C5 1.374(18) . ?
C5 C6 1.387(17) . ?
C6 C7 1.390(18) . ?
C6 N5 1.434(16) . ?
C8 N6 1.312(16) . ?
C8 N5 1.349(15) . ?
C9 C10 1.341(19) . ?
C9 N5 1.387(16) . ?
C10 N6 1.376(15) . ?
C11 N10 1.326(15) . ?
C11 N7 1.333(15) . ?
C11 C12 1.480(16) . ?
C12 C13 1.381(18) . ?
C12 C17 1.395(17) . ?
C13 C14 1.383(18) . ?
C14 C15 1.384(19) . ?
C15 C16 1.376(19) . ?
C16 C17 1.389(17) . ?
C16 N11 1.429(16) . ?
C18 N12 1.311(16) . ?
C18 N11 1.365(17) . ?
C19 C20 1.36(2) . ?
C19 N11 1.377(16) . ?
C20 N12 1.374(18) . ?
N1 N2 1.353(15) . ?
N2 N3 1.310(14) . ?
N3 N4 1.360(14) . ?
N6 Cd1 2.275(10) 1_545 ?
N7 N8 1.359(14) . ?
N8 N9 1.311(15) . ?
N9 N10 1.345(14) . ?
N12 Cd1 2.286(11) 4_575 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N6 Cd1 N12 165.6(4) 1_565 4_576 ?
N6 Cd1 N7 92.9(4) 1_565 . ?
N12 Cd1 N7 97.3(4) 4_576 . ?
N6 Cd1 N4 97.0(3) 1_565 . ?
N12 Cd1 N4 91.1(4) 4_576 . ?
N7 Cd1 N4 100.3(3) . . ?
N6 Cd1 O2W 80.3(3) 1_565 . ?
N12 Cd1 O2W 87.3(4) 4_576 . ?
N7 Cd1 O2W 165.1(4) . . ?
N4 Cd1 O2W 93.7(3) . . ?
N6 Cd1 O1W 84.4(3) 1_565 . ?
N12 Cd1 O1W 86.1(3) 4_576 . ?
N7 Cd1 O1W 87.1(3) . . ?
N4 Cd1 O1W 172.3(3) . . ?
O2W Cd1 O1W 79.0(3) . . ?
N1 C1 N4 111.1(11) . . ?
N1 C1 C2 122.5(11) . . ?
N4 C1 C2 126.4(11) . . ?
C3 C2 C7 119.6(12) . . ?
C3 C2 C1 122.4(12) . . ?
C7 C2 C1 118.0(11) . . ?
C2 C3 C4 119.6(13) . . ?
C5 C4 C3 121.6(12) . . ?
C4 C5 C6 118.3(12) . . ?
C7 C6 C5 120.6(12) . . ?
C7 C6 N5 119.4(11) . . ?
C5 C6 N5 119.9(11) . . ?
C6 C7 C2 120.1(12) . . ?
N6 C8 N5 111.8(11) . . ?
C10 C9 N5 106.6(11) . . ?
C9 C10 N6 109.8(12) . . ?
N10 C11 N7 111.6(11) . . ?
N10 C11 C12 124.3(11) . . ?
N7 C11 C12 124.1(11) . . ?
C13 C12 C17 120.2(12) . . ?
C13 C12 C11 121.1(12) . . ?
C17 C12 C11 118.7(12) . . ?
C12 C13 C14 119.9(13) . . ?
C13 C14 C15 120.6(14) . . ?
C16 C15 C14 119.2(13) . . ?
C15 C16 C17 121.3(12) . . ?
C15 C16 N11 120.7(12) . . ?
C17 C16 N11 118.1(12) . . ?
C12 C17 C16 118.8(13) . . ?
N12 C18 N11 111.5(13) . . ?
C20 C19 N11 105.7(13) . . ?
C19 C20 N12 110.5(12) . . ?
C1 N1 N2 105.0(10) . . ?
N3 N2 N1 110.1(10) . . ?
N2 N3 N4 108.4(11) . . ?
C1 N4 N3 105.4(10) . . ?
C1 N4 Cd1 139.4(8) . . ?
N3 N4 Cd1 114.6(8) . . ?
C8 N5 C9 106.0(11) . . ?
C8 N5 C6 127.4(10) . . ?
C9 N5 C6 126.6(10) . . ?
C8 N6 C10 105.7(11) . . ?
C8 N6 Cd1 124.9(8) . 1_545 ?
C10 N6 Cd1 129.4(9) . 1_545 ?
C11 N7 N8 105.2(10) . . ?
C11 N7 Cd1 133.7(8) . . ?
N8 N7 Cd1 117.8(8) . . ?
N9 N8 N7 108.1(10) . . ?
N8 N9 N10 110.3(10) . . ?
C11 N10 N9 104.8(10) . . ?
C18 N11 C19 106.8(11) . . ?
C18 N11 C16 125.8(11) . . ?
C19 N11 C16 127.4(12) . . ?
C18 N12 C20 105.6(12) . . ?
C18 N12 Cd1 123.8(10) . 4_575 ?
C20 N12 Cd1 129.0(9) . 4_575 ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.738
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.080
_database_code_depnum_ccdc_archive 'CCDC 992091'
#######################################################################
#
#                 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_Cd2Dt

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 Cd N12 O4'
_chemical_formula_weight         606.90

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'
Cd Cd -0.8075 1.2024 '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   'P2(1)/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                   7.784(4)
_cell_length_b                   13.039(6)
_cell_length_c                   11.761(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.106(6)
_cell_angle_gamma                90.00
_cell_volume                     1191.9(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1602
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      21.54

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             612
_exptl_absorpt_coefficient_mu    0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7336
_exptl_absorpt_correction_T_max  0.7726
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6779
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_sigmaI/netI    0.0679
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2584
_reflns_number_gt                1942
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1056P)²+42.0756P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2584
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1225
_refine_ls_R_factor_gt           0.1051
_refine_ls_wR_factor_ref         0.3133
_refine_ls_wR_factor_gt          0.3042
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.0000 0.0000 0.5000 0.0337(4) Uani 1 2 d S . .
C3 C 0.3322(18) 0.0053(9) 1.1804(10) 0.039(3) Uani 1 1 d . . .
H3A H 0.3772 0.0249 1.2519 0.046 Uiso 1 1 calc R . .
N5 N 0.1295(13) -0.0840(7) 0.8569(8) 0.031(2) Uani 1 1 d . . .
N1 N 0.3619(14) 0.2581(8) 1.0367(9) 0.037(2) Uani 1 1 d . . .
N6 N 0.0474(15) -0.0736(8) 0.6739(8) 0.037(2) Uani 1 1 d . . .
N4 N 0.5057(15) 0.2056(8) 1.1936(9) 0.039(2) Uani 1 1 d . . .
N3 N 0.5431(16) 0.3050(8) 1.1759(10) 0.043(3) Uani 1 1 d . . .
C6 C 0.1976(15) -0.0541(9) 0.9664(10) 0.031(2) Uani 1 1 d . . .
C2 C 0.3271(15) 0.0744(8) 1.0913(10) 0.031(2) Uani 1 1 d . . .
C4 C 0.2707(18) -0.0924(10) 1.1628(12) 0.041(3) Uani 1 1 d . . .
H4A H 0.2737 -0.1383 1.2234 0.050 Uiso 1 1 calc R . .
C5 C 0.2035(17) -0.1244(9) 1.0557(11) 0.036(3) Uani 1 1 d . . .
H5A H 0.1638 -0.1911 1.0445 0.043 Uiso 1 1 calc R . .
C9 C 0.063(2) -0.1793(10) 0.8229(12) 0.050(4) Uani 1 1 d . . .
H9A H 0.0544 -0.2374 0.8681 0.060 Uiso 1 1 calc R . .
C10 C 0.013(2) -0.1706(11) 0.7126(11) 0.046(3) Uani 1 1 d . . .
H10A H -0.0372 -0.2227 0.6684 0.055 Uiso 1 1 calc R . .
C1 C 0.3944(15) 0.1799(9) 1.1081(10) 0.032(2) Uani 1 1 d . . .
C8 C 0.1162(19) -0.0242(9) 0.7632(11) 0.040(3) Uani 1 1 d . . .
H8A H 0.1513 0.0440 0.7617 0.048 Uiso 1 1 calc R . .
N2 N 0.4576(15) 0.3351(8) 1.0835(9) 0.040(2) Uani 1 1 d . . .
C7 C 0.2633(16) 0.0448(9) 0.9853(10) 0.032(2) Uani 1 1 d . . .
H7A H 0.2636 0.0911 0.9251 0.038 Uiso 1 1 calc R . .
O1W O 0.2971(14) 0.0303(10) 0.5143(11) 0.067(3) Uani 1 1 d . . .
H1WA H 0.3211 0.0691 0.5710 0.100 Uiso 1 1 d R . .
H1WB H 0.3082 0.0653 0.4542 0.100 Uiso 1 1 d R . .
O2W O 0.5606(13) 0.1530(8) 0.4242(8) 0.046(2) Uani 1 1 d . . .
H2WA H 0.6643 0.1329 0.4332 0.069 Uiso 1 1 d R . .
H2WB H 0.5563 0.1984 0.3723 0.069 Uiso 1 1 d R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cd1 0.0423(8) 0.0295(7) 0.0287(6) -0.0028(5) -0.0052(5) 0.0039(5)
C3 0.053(8) 0.034(6) 0.027(6) 0.001(5) -0.005(5) -0.007(6)
N5 0.031(5) 0.028(5) 0.034(5) 0.000(4) 0.001(4) -0.003(4)
N1 0.042(6) 0.034(5) 0.033(5) 0.003(4) -0.009(4) -0.007(5)
N6 0.051(7) 0.031(5) 0.027(5) -0.004(4) -0.005(4) 0.000(5)
N4 0.051(7) 0.032(5) 0.035(5) 0.001(4) -0.011(5) -0.002(5)
N3 0.055(7) 0.028(5) 0.043(6) 0.004(4) -0.017(5) -0.004(5)
C6 0.023(5) 0.029(6) 0.041(6) 0.003(5) 0.004(5) -0.001(4)
C2 0.029(6) 0.024(5) 0.040(6) 0.005(5) 0.007(5) 0.003(4)
C4 0.045(7) 0.037(7) 0.042(7) 0.005(6) -0.002(6) 0.001(6)
C5 0.043(7) 0.026(6) 0.039(7) 0.000(5) 0.000(5) -0.002(5)
C9 0.078(11) 0.030(6) 0.041(7) 0.000(5) 0.003(7) -0.018(7)
C10 0.059(9) 0.039(7) 0.039(7) -0.005(6) -0.002(6) -0.017(6)
C1 0.034(6) 0.028(6) 0.033(6) 0.004(5) 0.000(5) -0.006(5)
C8 0.054(8) 0.026(6) 0.040(7) 0.000(5) -0.007(6) 0.001(5)
N2 0.049(6) 0.034(5) 0.035(5) 0.003(4) -0.007(5) -0.006(5)
C7 0.032(6) 0.026(6) 0.038(6) 0.005(5) 0.004(5) -0.001(5)
O1W 0.046(6) 0.078(8) 0.076(8) 0.042(7) 0.005(6) 0.005(6)
O2W 0.046(5) 0.050(6) 0.042(5) 0.013(4) -0.004(4) 0.001(4)

_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 N6 2.272(10) . ?
Cd1 N6 2.272(10) 3_556 ?
Cd1 O1W 2.343(11) . ?
Cd1 O1W 2.343(11) 3_556 ?
Cd1 N2 2.394(11) 2_546 ?
Cd1 N2 2.394(11) 4_565 ?
C3 C4 1.372(18) . ?
C3 C2 1.380(16) . ?
N5 C8 1.349(16) . ?
N5 C9 1.396(15) . ?
N5 C6 1.421(15) . ?
N1 C1 1.337(15) . ?
N1 N2 1.350(14) . ?
N6 C8 1.321(16) . ?
N6 C10 1.375(17) . ?
N4 C1 1.334(15) . ?
N4 N3 1.347(14) . ?
N3 N2 1.304(14) . ?
C6 C5 1.393(17) . ?
C6 C7 1.401(16) . ?
C2 C7 1.372(17) . ?
C2 C1 1.482(16) . ?
C4 C5 1.401(18) . ?
C9 C10 1.338(19) . ?
N2 Cd1 2.394(11) 2_556 ?

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
N6 Cd1 N6 180.000(1) . 3_556 ?
N6 Cd1 O1W 84.0(4) . . ?
N6 Cd1 O1W 96.0(4) 3_556 . ?
N6 Cd1 O1W 96.0(4) . 3_556 ?
N6 Cd1 O1W 84.0(4) 3_556 3_556 ?
O1W Cd1 O1W 180.000(1) . 3_556 ?
N6 Cd1 N2 88.3(4) . 2_546 ?
N6 Cd1 N2 91.7(4) 3_556 2_546 ?
O1W Cd1 N2 91.3(4) . 2_546 ?
O1W Cd1 N2 88.7(4) 3_556 2_546 ?
N6 Cd1 N2 91.7(4) . 4_565 ?
N6 Cd1 N2 88.3(4) 3_556 4_565 ?
O1W Cd1 N2 88.7(4) . 4_565 ?
O1W Cd1 N2 91.3(4) 3_556 4_565 ?
N2 Cd1 N2 180.000(1) 2_546 4_565 ?
C4 C3 C2 119.7(12) . . ?
C8 N5 C9 105.7(10) . . ?
C8 N5 C6 126.2(10) . . ?
C9 N5 C6 128.2(10) . . ?
C1 N1 N2 103.3(9) . . ?
C8 N6 C10 105.3(10) . . ?
C8 N6 Cd1 123.3(8) . . ?
C10 N6 Cd1 131.4(8) . . ?
C1 N4 N3 105.3(10) . . ?
N2 N3 N4 108.3(10) . . ?
C5 C6 C7 119.3(11) . . ?
C5 C6 N5 119.9(11) . . ?
C7 C6 N5 120.7(10) . . ?
C3 C2 C7 120.0(11) . . ?
C3 C2 C1 120.6(11) . . ?
C7 C2 C1 119.4(10) . . ?
C3 C4 C5 121.5(12) . . ?
C6 C5 C4 118.5(11) . . ?
C10 C9 N5 106.6(12) . . ?
C9 C10 N6 110.3(11) . . ?
N4 C1 N1 112.0(10) . . ?
N4 C1 C2 123.0(11) . . ?
N1 C1 C2 124.9(11) . . ?
N6 C8 N5 112.1(11) . . ?
N3 N2 N1 111.2(10) . . ?
N3 N2 Cd1 122.5(8) . 2_556 ?
N1 N2 Cd1 125.9(8) . 2_556 ?
C2 C7 C6 120.9(11) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         4.493
_refine_diff_density_min         -0.647
_refine_diff_density_rms         0.222
_database_code_depnum_ccdc_archive 'CCDC 992092'
#######################################################################
#
#                 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_CdCl2D

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 Cd Cl N6 O'
_chemical_formula_sum            'C10 H9 Cd Cl N6 O'
_chemical_formula_weight         377.09

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'
Cd Cd -0.8075 1.2024 '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'
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   'P 21/c  '
_symmetry_space_group_name_Hall  '-P 2ybc  '

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                   13.270(4)
_cell_length_b                   13.217(4)
_cell_length_c                   6.920(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.561(3)
_cell_angle_gamma                90.00
_cell_volume                     1193.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3736
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      27.91

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.099
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    2.055
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6841
_exptl_absorpt_correction_T_max  0.8209
_exptl_absorpt_process_details   '(North et al., 1968)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5863
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2098
_reflns_number_gt                1898
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0505P)²+7.9386P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2098
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1127
_refine_ls_wR_factor_gt          0.1108
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_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 0.77517(3) 0.31927(3) 0.80572(7) 0.02529(18) Uani 1 1 d . . .
Cl1 Cl 0.66122(12) 0.19666(12) 0.9519(2) 0.0321(4) Uani 1 1 d . . .
O1W O 0.8670(3) 0.3138(3) 1.1489(7) 0.0327(10) Uani 1 1 d . . .
H1W H 0.9250 0.2863 1.1428 0.049 Uiso 1 1 d R . .
H2W H 0.8734 0.3769 1.1824 0.049 Uiso 1 1 d R . .
N1 N 0.7017(4) 0.4682(4) 0.8636(8) 0.0270(11) Uani 1 1 d . . .
N2 N 0.6767(4) 0.6328(4) 0.8659(7) 0.0230(10) Uani 1 1 d . . .
N3 N 1.0004(4) 0.3402(4) 0.6976(9) 0.0319(12) Uani 1 1 d . . .
N4 N 0.9242(4) 0.3993(4) 0.7406(8) 0.0301(12) Uani 1 1 d . . .
N5 N 0.9558(4) 0.4940(4) 0.7641(8) 0.0312(12) Uani 1 1 d . . .
N6 N 1.0526(4) 0.4984(4) 0.7366(8) 0.0268(11) Uani 1 1 d . . .
C1 C 0.7461(4) 0.5569(4) 0.8719(9) 0.0271(13) Uani 1 1 d . . .
H1 H 0.8162 0.5666 0.8809 0.033 Uiso 1 1 calc R . .
C2 C 0.5990(5) 0.4868(5) 0.8534(10) 0.0347(15) Uani 1 1 d . . .
H2 H 0.5485 0.4375 0.8475 0.042 Uiso 1 1 calc R . .
C3 C 0.5828(5) 0.5877(5) 0.8533(10) 0.0330(14) Uani 1 1 d . . .
H3 H 0.5201 0.6202 0.8461 0.040 Uiso 1 1 calc R . .
C4 C 0.7002(4) 0.7390(4) 0.8657(8) 0.0224(12) Uani 1 1 d . . .
C5 C 0.6269(5) 0.8102(4) 0.8917(9) 0.0283(13) Uani 1 1 d . . .
H5 H 0.5621 0.7897 0.9089 0.034 Uiso 1 1 calc R . .
C6 C 0.6514(5) 0.9122(5) 0.8918(9) 0.0297(13) Uani 1 1 d . . .
H6 H 0.6025 0.9601 0.9090 0.036 Uiso 1 1 calc R . .
C7 C 0.7471(5) 0.9436(5) 0.8667(9) 0.0286(13) Uani 1 1 d . . .
H7 H 0.7626 1.0122 0.8674 0.034 Uiso 1 1 calc R . .
C8 C 0.8208(4) 0.8721(4) 0.8401(8) 0.0225(12) Uani 1 1 d . . .
C9 C 0.7971(5) 0.7694(4) 0.8404(9) 0.0259(13) Uani 1 1 d . . .
H9 H 0.8461 0.7214 0.8238 0.031 Uiso 1 1 calc R . .
C10 C 1.0779(4) 0.4030(4) 0.6961(9) 0.0241(12) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cd1 0.0249(3) 0.0217(3) 0.0299(3) 0.00006(17) 0.00677(18) -0.00179(16)
Cl1 0.0315(8) 0.0309(8) 0.0321(8) 0.0047(6) 0.0012(6) -0.0098(6)
O1W 0.025(2) 0.021(2) 0.050(3) -0.0039(19) 0.001(2) -0.0005(17)
N1 0.024(3) 0.025(3) 0.031(3) -0.002(2) 0.003(2) -0.002(2)
N2 0.024(2) 0.021(2) 0.025(3) 0.0000(19) 0.0053(19) 0.0010(19)
N3 0.027(3) 0.022(3) 0.047(3) -0.003(2) 0.009(2) 0.001(2)
N4 0.022(3) 0.028(3) 0.041(3) 0.000(2) 0.009(2) 0.003(2)
N5 0.027(3) 0.026(3) 0.041(3) -0.004(2) 0.007(2) -0.002(2)
N6 0.022(2) 0.024(3) 0.035(3) -0.002(2) 0.006(2) 0.003(2)
C1 0.021(3) 0.026(3) 0.035(3) 0.000(3) 0.005(2) 0.001(2)
C2 0.024(3) 0.032(3) 0.049(4) 0.002(3) 0.009(3) -0.006(3)
C3 0.022(3) 0.033(3) 0.046(4) 0.003(3) 0.012(3) 0.003(3)
C4 0.020(3) 0.025(3) 0.022(3) 0.004(2) 0.002(2) 0.000(2)
C5 0.026(3) 0.029(3) 0.031(3) -0.001(3) 0.008(3) 0.003(2)
C6 0.024(3) 0.027(3) 0.038(4) -0.002(3) 0.004(3) 0.008(2)
C7 0.029(3) 0.025(3) 0.031(3) -0.002(3) 0.004(3) 0.002(2)
C8 0.023(3) 0.024(3) 0.020(3) -0.001(2) 0.002(2) -0.002(2)
C9 0.027(3) 0.022(3) 0.029(3) 0.002(2) 0.006(2) 0.004(2)
C10 0.024(3) 0.021(3) 0.027(3) -0.002(2) 0.002(2) -0.003(2)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N1 2.264(5) . ?
Cd1 N4 2.358(5) . ?
Cd1 O1W 2.464(5) . ?
Cd1 O1W 2.498(4) 4_565 ?
Cd1 Cl1 2.5490(16) . ?
Cd1 Cl1 2.6396(17) 4_565 ?
Cl1 Cd1 2.6396(17) 4_566 ?
O1W Cd1 2.498(4) 4_566 ?
O1W H1W 0.8589 . ?
O1W H2W 0.8658 . ?
N1 C1 1.308(8) . ?
N1 C2 1.374(8) . ?
N2 C1 1.358(7) . ?
N2 C3 1.370(8) . ?
N2 C4 1.438(8) . ?
N3 C10 1.323(8) . ?
N3 N4 1.353(7) . ?
N4 N5 1.320(7) . ?
N5 N6 1.334(7) . ?
N6 C10 1.348(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.351(9) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 C5 1.389(8) . ?
C4 C9 1.389(8) . ?
C5 C6 1.387(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.396(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(8) . ?
C8 C10 1.470(8) 2_756 ?
C9 H9 0.9300 . ?
C10 C8 1.470(8) 2_746 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cd1 N4 92.70(17) . . ?
N1 Cd1 O1W 90.46(16) . . ?
N4 Cd1 O1W 85.03(17) . . ?
N1 Cd1 O1W 161.58(17) . 4_565 ?
N4 Cd1 O1W 74.91(16) . 4_565 ?
O1W Cd1 O1W 101.74(14) . 4_565 ?
N1 Cd1 Cl1 100.17(13) . . ?
N4 Cd1 Cl1 160.12(13) . . ?
O1W Cd1 Cl1 79.81(11) . . ?
O1W Cd1 Cl1 95.58(11) 4_565 . ?
N1 Cd1 Cl1 92.38(13) . 4_565 ?
N4 Cd1 Cl1 102.51(14) . 4_565 ?
O1W Cd1 Cl1 171.80(11) . 4_565 ?
O1W Cd1 Cl1 77.47(11) 4_565 4_565 ?
Cl1 Cd1 Cl1 92.11(5) . 4_565 ?
Cd1 Cl1 Cd1 97.94(5) . 4_566 ?
Cd1 O1W Cd1 104.19(15) . 4_566 ?
Cd1 O1W H1W 104.7 . . ?
Cd1 O1W H1W 103.7 4_566 . ?
Cd1 O1W H2W 103.7 . . ?
Cd1 O1W H2W 126.4 4_566 . ?
H1W O1W H2W 112.0 . . ?
C1 N1 C2 106.1(5) . . ?
C1 N1 Cd1 125.6(4) . . ?
C2 N1 Cd1 127.0(4) . . ?
C1 N2 C3 106.5(5) . . ?
C1 N2 C4 125.1(5) . . ?
C3 N2 C4 128.3(5) . . ?
C10 N3 N4 104.7(5) . . ?
N5 N4 N3 109.9(5) . . ?
N5 N4 Cd1 131.3(4) . . ?
N3 N4 Cd1 118.0(4) . . ?
N4 N5 N6 108.4(5) . . ?
N5 N6 C10 105.8(5) . . ?
N1 C1 N2 111.3(5) . . ?
N1 C1 H1 124.3 . . ?
N2 C1 H1 124.3 . . ?
C3 C2 N1 109.4(5) . . ?
C3 C2 H2 125.3 . . ?
N1 C2 H2 125.3 . . ?
C2 C3 N2 106.7(5) . . ?
C2 C3 H3 126.7 . . ?
N2 C3 H3 126.7 . . ?
C5 C4 C9 120.5(6) . . ?
C5 C4 N2 120.3(5) . . ?
C9 C4 N2 119.3(5) . . ?
C6 C5 C4 119.2(6) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C7 C6 C5 121.0(6) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 119.8(6) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 119.7(5) . . ?
C9 C8 C10 119.0(5) . 2_756 ?
C7 C8 C10 121.3(5) . 2_756 ?
C4 C9 C8 119.8(5) . . ?
C4 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
N3 C10 N6 111.2(5) . . ?
N3 C10 C8 124.3(5) . 2_746 ?
N6 C10 C8 124.5(5) . 2_746 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Cd1 Cl1 Cd1 -94.28(14) . . . 4_566 ?
N4 Cd1 Cl1 Cd1 35.3(4) . . . 4_566 ?
O1W Cd1 Cl1 Cd1 -5.65(10) . . . 4_566 ?
O1W Cd1 Cl1 Cd1 95.31(11) 4_565 . . 4_566 ?
Cl1 Cd1 Cl1 Cd1 172.92(6) 4_565 . . 4_566 ?
N1 Cd1 O1W Cd1 106.35(18) . . . 4_566 ?
N4 Cd1 O1W Cd1 -160.98(18) . . . 4_566 ?
O1W Cd1 O1W Cd1 -87.5(2) 4_565 . . 4_566 ?
Cl1 Cd1 O1W Cd1 6.11(11) . . . 4_566 ?
Cl1 Cd1 O1W Cd1 -3.9(9) 4_565 . . 4_566 ?
N4 Cd1 N1 C1 -6.4(5) . . . . ?
O1W Cd1 N1 C1 78.7(5) . . . . ?
O1W Cd1 N1 C1 -53.3(8) 4_565 . . . ?
Cl1 Cd1 N1 C1 158.4(5) . . . . ?
Cl1 Cd1 N1 C1 -109.0(5) 4_565 . . . ?
N4 Cd1 N1 C2 158.1(5) . . . . ?
O1W Cd1 N1 C2 -116.8(5) . . . . ?
O1W Cd1 N1 C2 111.2(6) 4_565 . . . ?
Cl1 Cd1 N1 C2 -37.1(5) . . . . ?
Cl1 Cd1 N1 C2 55.5(5) 4_565 . . . ?
C10 N3 N4 N5 -0.1(7) . . . . ?
C10 N3 N4 Cd1 -171.4(4) . . . . ?
N1 Cd1 N4 N5 9.7(6) . . . . ?
O1W Cd1 N4 N5 -80.5(5) . . . . ?
O1W Cd1 N4 N5 175.9(6) 4_565 . . . ?
Cl1 Cd1 N4 N5 -120.8(5) . . . . ?
Cl1 Cd1 N4 N5 102.7(5) 4_565 . . . ?
N1 Cd1 N4 N3 178.8(5) . . . . ?
O1W Cd1 N4 N3 88.6(4) . . . . ?
O1W Cd1 N4 N3 -15.0(4) 4_565 . . . ?
Cl1 Cd1 N4 N3 48.2(7) . . . . ?
Cl1 Cd1 N4 N3 -88.2(4) 4_565 . . . ?
N3 N4 N5 N6 0.1(7) . . . . ?
Cd1 N4 N5 N6 169.9(4) . . . . ?
N4 N5 N6 C10 -0.1(7) . . . . ?
C2 N1 C1 N2 -0.5(7) . . . . ?
Cd1 N1 C1 N2 166.6(4) . . . . ?
C3 N2 C1 N1 0.1(7) . . . . ?
C4 N2 C1 N1 -177.8(5) . . . . ?
C1 N1 C2 C3 0.8(8) . . . . ?
Cd1 N1 C2 C3 -166.2(5) . . . . ?
N1 C2 C3 N2 -0.7(8) . . . . ?
C1 N2 C3 C2 0.3(7) . . . . ?
C4 N2 C3 C2 178.2(6) . . . . ?
C1 N2 C4 C5 -169.4(6) . . . . ?
C3 N2 C4 C5 13.1(9) . . . . ?
C1 N2 C4 C9 10.2(8) . . . . ?
C3 N2 C4 C9 -167.3(6) . . . . ?
C9 C4 C5 C6 0.1(9) . . . . ?
N2 C4 C5 C6 179.8(5) . . . . ?
C4 C5 C6 C7 -0.1(10) . . . . ?
C5 C6 C7 C8 0.2(10) . . . . ?
C6 C7 C8 C9 -0.4(9) . . . . ?
C6 C7 C8 C10 177.2(5) . . . 2_756 ?
C5 C4 C9 C8 -0.3(9) . . . . ?
N2 C4 C9 C8 -180.0(5) . . . . ?
C7 C8 C9 C4 0.5(9) . . . . ?
C10 C8 C9 C4 -177.1(5) 2_756 . . . ?
N4 N3 C10 N6 0.1(7) . . . . ?
N4 N3 C10 C8 178.6(5) . . . 2_746 ?
N5 N6 C10 N3 0.0(7) . . . . ?
N5 N6 C10 C8 -178.5(5) . . . 2_746 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.764
_refine_diff_density_min         -1.227
_refine_diff_density_rms         0.139
_database_code_depnum_ccdc_archive 'CCDC 992093'
#######################################################################
#
#                 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_CdCl3D

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H7 Cd Cl N6'
_chemical_formula_weight         359.07

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/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                   9.7741(8)
_cell_length_b                   7.3309(6)
_cell_length_c                   16.1973(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.0050(10)
_cell_angle_gamma                90.00
_cell_volume                     1121.01(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4273
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      27.95

_exptl_crystal_description       block
_exptl_crystal_colour            'dark brown'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.128
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    2.175
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.4766
_exptl_absorpt_correction_T_max  0.6702
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5563
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2026
_reflns_number_gt                1873
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0223P)²+0.5632P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2026
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0199
_refine_ls_R_factor_gt           0.0178
_refine_ls_wR_factor_ref         0.0449
_refine_ls_wR_factor_gt          0.0438
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.072369(16) 0.15803(2) -0.076975(10) 0.02391(7) Uani 1 1 d . . .
Cl1 Cl -0.08718(6) 0.21556(9) 0.01445(4) 0.03324(14) Uani 1 1 d . . .
N6 N 0.29797(19) 0.1753(3) -0.00116(13) 0.0262(4) Uani 1 1 d . . .
N5 N 0.49400(19) 0.1505(2) 0.10197(12) 0.0238(4) Uani 1 1 d . . .
N1 N 1.03321(18) -0.0151(3) 0.20008(11) 0.0236(4) Uani 1 1 d . . .
N2 N 1.17481(19) 0.0089(3) 0.22569(12) 0.0284(4) Uani 1 1 d . . .
N3 N 1.20774(19) 0.0799(3) 0.30210(12) 0.0288(4) Uani 1 1 d . . .
N4 N 1.08726(19) 0.1029(3) 0.32849(12) 0.0254(4) Uani 1 1 d . . .
C8 C 0.3542(2) 0.1106(3) 0.07635(15) 0.0260(5) Uani 1 1 d . . .
H8A H 0.3045 0.0466 0.1088 0.031 Uiso 1 1 calc R . .
C10 C 0.4062(2) 0.2597(3) -0.02649(15) 0.0297(5) Uani 1 1 d . . .
H10A H 0.3972 0.3179 -0.0786 0.036 Uiso 1 1 calc R . .
C9 C 0.5272(2) 0.2450(3) 0.03584(15) 0.0295(5) Uani 1 1 d . . .
H9A H 0.6158 0.2895 0.0347 0.035 Uiso 1 1 calc R . .
C6 C 0.5908(2) 0.1034(3) 0.18189(15) 0.0237(5) Uani 1 1 d . . .
C5 C 0.5436(2) 0.0735(3) 0.25404(15) 0.0305(5) Uani 1 1 d . . .
H5A H 0.4478 0.0831 0.2518 0.037 Uiso 1 1 calc R . .
C4 C 0.6409(2) 0.0291(4) 0.32959(15) 0.0320(5) Uani 1 1 d . . .
H4A H 0.6096 0.0080 0.3783 0.038 Uiso 1 1 calc R . .
C3 C 0.7840(2) 0.0151(3) 0.33448(14) 0.0267(5) Uani 1 1 d . . .
H3A H 0.8481 -0.0164 0.3857 0.032 Uiso 1 1 calc R . .
C2 C 0.8307(2) 0.0489(3) 0.26177(14) 0.0225(5) Uani 1 1 d . . .
C7 C 0.7339(2) 0.0933(3) 0.18528(14) 0.0228(5) Uani 1 1 d . . .
H7A H 0.7649 0.1160 0.1366 0.027 Uiso 1 1 calc R . .
C1 C 0.9823(2) 0.0433(3) 0.26443(13) 0.0213(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cd1 0.01726(10) 0.03670(12) 0.01637(10) -0.00076(6) 0.00181(7) -0.00276(6)
Cl1 0.0347(3) 0.0388(3) 0.0310(3) 0.0037(3) 0.0172(3) 0.0027(3)
N6 0.0179(9) 0.0358(11) 0.0222(10) 0.0010(8) 0.0001(8) -0.0018(8)
N5 0.0168(9) 0.0324(11) 0.0201(10) 0.0019(7) 0.0010(8) -0.0001(7)
N1 0.0184(9) 0.0309(10) 0.0196(9) -0.0010(8) 0.0015(7) -0.0019(8)
N2 0.0205(9) 0.0388(11) 0.0244(10) -0.0048(8) 0.0031(8) -0.0008(8)
N3 0.0198(9) 0.0386(12) 0.0259(11) -0.0058(9) 0.0024(8) 0.0004(8)
N4 0.0175(9) 0.0355(11) 0.0212(10) -0.0036(8) 0.0012(8) 0.0015(8)
C8 0.0179(11) 0.0339(13) 0.0251(12) 0.0011(10) 0.0034(9) -0.0036(9)
C10 0.0248(12) 0.0398(14) 0.0237(12) 0.0070(10) 0.0046(10) -0.0012(10)
C9 0.0205(11) 0.0410(14) 0.0264(13) 0.0070(10) 0.0052(10) -0.0028(10)
C6 0.0190(11) 0.0270(12) 0.0222(12) -0.0009(9) -0.0001(9) -0.0005(9)
C5 0.0186(11) 0.0441(14) 0.0296(13) 0.0032(11) 0.0077(10) -0.0006(10)
C4 0.0291(12) 0.0454(15) 0.0233(12) 0.0051(11) 0.0100(10) -0.0016(11)
C3 0.0236(11) 0.0339(13) 0.0201(11) 0.0009(9) 0.0013(9) -0.0010(9)
C2 0.0182(10) 0.0265(12) 0.0206(11) -0.0003(9) 0.0011(9) 0.0007(9)
C7 0.0190(10) 0.0320(12) 0.0170(11) -0.0002(9) 0.0038(9) -0.0011(9)
C1 0.0198(10) 0.0252(11) 0.0170(11) 0.0011(8) 0.0015(8) 0.0014(9)

_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 N6 2.2325(19) . ?
Cd1 N1 2.2522(18) 3_655 ?
Cd1 N4 2.3565(19) 4_465 ?
Cd1 Cl1 2.4492(6) . ?
Cd1 Cl1 2.9105(7) 3 ?
Cl1 Cd1 2.9105(7) 3 ?
N6 C8 1.321(3) . ?
N6 C10 1.377(3) . ?
N5 C8 1.354(3) . ?
N5 C9 1.383(3) . ?
N5 C6 1.434(3) . ?
N1 C1 1.337(3) . ?
N1 N2 1.350(2) . ?
N1 Cd1 2.2522(18) 3_655 ?
N2 N3 1.304(3) . ?
N3 N4 1.363(3) . ?
N4 C1 1.330(3) . ?
N4 Cd1 2.3565(19) 4_666 ?
C8 H8A 0.9300 . ?
C10 C9 1.346(3) . ?
C10 H10A 0.9300 . ?
C9 H9A 0.9300 . ?
C6 C5 1.381(3) . ?
C6 C7 1.387(3) . ?
C5 C4 1.380(3) . ?
C5 H5A 0.9300 . ?
C4 C3 1.384(3) . ?
C4 H4A 0.9300 . ?
C3 C2 1.391(3) . ?
C3 H3A 0.9300 . ?
C2 C7 1.389(3) . ?
C2 C1 1.472(3) . ?
C7 H7A 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
N6 Cd1 N1 132.40(7) . 3_655 ?
N6 Cd1 N4 95.56(7) . 4_465 ?
N1 Cd1 N4 82.07(7) 3_655 4_465 ?
N6 Cd1 Cl1 110.51(5) . . ?
N1 Cd1 Cl1 113.45(5) 3_655 . ?
N4 Cd1 Cl1 114.89(5) 4_465 . ?
N6 Cd1 Cl1 84.78(5) . 3 ?
N1 Cd1 Cl1 80.82(5) 3_655 3 ?
N4 Cd1 Cl1 156.94(5) 4_465 3 ?
Cl1 Cd1 Cl1 86.20(2) . 3 ?
Cd1 Cl1 Cd1 93.80(2) . 3 ?
C8 N6 C10 106.38(19) . . ?
C8 N6 Cd1 127.64(15) . . ?
C10 N6 Cd1 125.98(15) . . ?
C8 N5 C9 106.96(19) . . ?
C8 N5 C6 127.07(19) . . ?
C9 N5 C6 125.97(19) . . ?
C1 N1 N2 106.13(17) . . ?
C1 N1 Cd1 131.43(14) . 3_655 ?
N2 N1 Cd1 122.08(13) . 3_655 ?
N3 N2 N1 108.99(17) . . ?
N2 N3 N4 109.03(17) . . ?
C1 N4 N3 105.62(18) . . ?
C1 N4 Cd1 125.89(14) . 4_666 ?
N3 N4 Cd1 119.97(14) . 4_666 ?
N6 C8 N5 110.6(2) . . ?
N6 C8 H8A 124.7 . . ?
N5 C8 H8A 124.7 . . ?
C9 C10 N6 109.5(2) . . ?
C9 C10 H10A 125.2 . . ?
N6 C10 H10A 125.2 . . ?
C10 C9 N5 106.5(2) . . ?
C10 C9 H9A 126.7 . . ?
N5 C9 H9A 126.7 . . ?
C5 C6 C7 120.8(2) . . ?
C5 C6 N5 121.02(19) . . ?
C7 C6 N5 118.1(2) . . ?
C4 C5 C6 118.9(2) . . ?
C4 C5 H5A 120.5 . . ?
C6 C5 H5A 120.5 . . ?
C5 C4 C3 121.5(2) . . ?
C5 C4 H4A 119.3 . . ?
C3 C4 H4A 119.3 . . ?
C4 C3 C2 119.1(2) . . ?
C4 C3 H3A 120.5 . . ?
C2 C3 H3A 120.5 . . ?
C7 C2 C3 120.03(19) . . ?
C7 C2 C1 118.73(19) . . ?
C3 C2 C1 121.23(19) . . ?
C6 C7 C2 119.6(2) . . ?
C6 C7 H7A 120.2 . . ?
C2 C7 H7A 120.2 . . ?
N4 C1 N1 110.23(18) . . ?
N4 C1 C2 125.53(19) . . ?
N1 C1 C2 124.16(19) . . ?

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
N6 Cd1 Cl1 Cd1 -82.98(5) . . . 3 ?
N1 Cd1 Cl1 Cd1 78.28(5) 3_655 . . 3 ?
N4 Cd1 Cl1 Cd1 170.31(5) 4_465 . . 3 ?
Cl1 Cd1 Cl1 Cd1 0.0 3 . . 3 ?
N1 Cd1 N6 C8 -114.8(2) 3_655 . . . ?
N4 Cd1 N6 C8 160.9(2) 4_465 . . . ?
Cl1 Cd1 N6 C8 41.7(2) . . . . ?
Cl1 Cd1 N6 C8 -42.25(19) 3 . . . ?
N1 Cd1 N6 C10 66.4(2) 3_655 . . . ?
N4 Cd1 N6 C10 -18.0(2) 4_465 . . . ?
Cl1 Cd1 N6 C10 -137.16(18) . . . . ?
Cl1 Cd1 N6 C10 138.88(19) 3 . . . ?
C1 N1 N2 N3 -0.4(2) . . . . ?
Cd1 N1 N2 N3 -174.25(15) 3_655 . . . ?
N1 N2 N3 N4 0.4(3) . . . . ?
N2 N3 N4 C1 -0.2(2) . . . . ?
N2 N3 N4 Cd1 -149.99(15) . . . 4_666 ?
C10 N6 C8 N5 0.2(3) . . . . ?
Cd1 N6 C8 N5 -178.84(14) . . . . ?
C9 N5 C8 N6 -0.5(3) . . . . ?
C6 N5 C8 N6 -180.0(2) . . . . ?
C8 N6 C10 C9 0.2(3) . . . . ?
Cd1 N6 C10 C9 179.23(16) . . . . ?
N6 C10 C9 N5 -0.4(3) . . . . ?
C8 N5 C9 C10 0.6(3) . . . . ?
C6 N5 C9 C10 -179.9(2) . . . . ?
C8 N5 C6 C5 -25.4(4) . . . . ?
C9 N5 C6 C5 155.2(2) . . . . ?
C8 N5 C6 C7 156.2(2) . . . . ?
C9 N5 C6 C7 -23.2(3) . . . . ?
C7 C6 C5 C4 -1.4(4) . . . . ?
N5 C6 C5 C4 -179.8(2) . . . . ?
C6 C5 C4 C3 0.4(4) . . . . ?
C5 C4 C3 C2 0.8(4) . . . . ?
C4 C3 C2 C7 -1.0(3) . . . . ?
C4 C3 C2 C1 177.5(2) . . . . ?
C5 C6 C7 C2 1.3(4) . . . . ?
N5 C6 C7 C2 179.7(2) . . . . ?
C3 C2 C7 C6 -0.1(3) . . . . ?
C1 C2 C7 C6 -178.5(2) . . . . ?
N3 N4 C1 N1 0.0(2) . . . . ?
Cd1 N4 C1 N1 147.42(15) 4_666 . . . ?
N3 N4 C1 C2 -177.0(2) . . . . ?
Cd1 N4 C1 C2 -29.6(3) 4_666 . . . ?
N2 N1 C1 N4 0.2(2) . . . . ?
Cd1 N1 C1 N4 173.29(15) 3_655 . . . ?
N2 N1 C1 C2 177.2(2) . . . . ?
Cd1 N1 C1 C2 -9.7(3) 3_655 . . . ?
C7 C2 C1 N4 140.4(2) . . . . ?
C3 C2 C1 N4 -38.1(3) . . . . ?
C7 C2 C1 N1 -36.2(3) . . . . ?
C3 C2 C1 N1 145.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.071
_database_code_depnum_ccdc_archive 'CCDC 992094'
#######################################################################
#
#                 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_CdI1D

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 Cd I2 N12'
_chemical_formula_weight         788.63

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'
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                   4.268(3)
_cell_length_b                   8.108(5)
_cell_length_c                   17.578(11)
_cell_angle_alpha                95.734(9)
_cell_angle_beta                 94.064(8)
_cell_angle_gamma                103.239(8)
_cell_volume                     586.4(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    331
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      16.78

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_absorpt_coefficient_mu    3.601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4431
_exptl_absorpt_correction_T_max  0.5634
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3983
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_sigmaI/netI    0.1603
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2490
_reflns_number_gt                1054
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0383P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2490
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1699
_refine_ls_R_factor_gt           0.0672
_refine_ls_wR_factor_ref         0.1439
_refine_ls_wR_factor_gt          0.1154
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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 0.0000 0.0000 0.0000 0.0614(5) Uani 1 2 d S . .
C1 C 0.191(3) 0.7284(17) 0.4574(7) 0.045(3) Uani 1 1 d . . .
C2 C 0.083(3) 0.6830(15) 0.3773(6) 0.039(3) Uani 1 1 d . . .
C3 C -0.074(3) 0.7887(16) 0.3398(7) 0.049(4) Uani 1 1 d . . .
H3A H -0.1021 0.8892 0.3658 0.059 Uiso 1 1 calc R . .
C4 C -0.190(3) 0.7417(18) 0.2622(8) 0.059(4) Uani 1 1 d . . .
H4A H -0.3031 0.8093 0.2372 0.071 Uiso 1 1 calc R . .
C5 C -0.139(3) 0.5988(17) 0.2232(7) 0.046(4) Uani 1 1 d . . .
H5A H -0.2130 0.5714 0.1713 0.056 Uiso 1 1 calc R . .
C6 C 0.020(3) 0.4932(16) 0.2591(6) 0.041(3) Uani 1 1 d . . .
C7 C 0.127(3) 0.5374(15) 0.3355(7) 0.042(3) Uani 1 1 d . . .
H7A H 0.2330 0.4666 0.3602 0.050 Uiso 1 1 calc R . .
C8 C 0.027(3) 0.2993(18) 0.1418(7) 0.059(4) Uani 1 1 d . . .
H8A H -0.0521 0.3641 0.1077 0.071 Uiso 1 1 calc R . .
C9 C 0.188(4) 0.2194(17) 0.2471(7) 0.065(5) Uani 1 1 d . . .
H9A H 0.2402 0.2127 0.2988 0.078 Uiso 1 1 calc R . .
C10 C 0.206(3) 0.1080(17) 0.1876(8) 0.061(4) Uani 1 1 d . . .
H10A H 0.2835 0.0105 0.1914 0.073 Uiso 1 1 calc R . .
N1 N 0.371(2) 0.6457(13) 0.5002(6) 0.050(3) Uani 1 1 d . . .
N2 N 0.429(3) 0.7329(14) 0.5725(6) 0.059(3) Uani 1 1 d . . .
N3 N 0.304(3) 0.8600(14) 0.5753(6) 0.060(3) Uani 1 1 d . . .
N4 N 0.149(2) 0.8613(13) 0.5041(6) 0.047(3) Uani 1 1 d . . .
N5 N 0.079(2) 0.3449(12) 0.2163(5) 0.040(3) Uani 1 1 d . . .
N6 N 0.097(2) 0.1552(14) 0.1202(5) 0.048(3) Uani 1 1 d . . .
I1 I 0.4062(2) -0.23521(13) 0.05118(5) 0.0576(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cd1 0.0807(12) 0.0751(12) 0.0318(8) -0.0132(8) -0.0122(8) 0.0394(10)
C1 0.056(9) 0.048(9) 0.031(7) 0.011(7) -0.001(6) 0.009(8)
C2 0.046(8) 0.039(8) 0.029(7) -0.012(6) -0.007(6) 0.018(7)
C3 0.059(9) 0.045(9) 0.039(8) -0.010(7) -0.007(7) 0.013(7)
C4 0.072(11) 0.054(10) 0.049(9) 0.014(8) -0.007(8) 0.013(8)
C5 0.067(10) 0.054(10) 0.017(6) -0.004(6) -0.007(6) 0.021(8)
C6 0.060(9) 0.040(9) 0.022(6) 0.006(6) -0.003(6) 0.010(7)
C7 0.064(9) 0.028(8) 0.032(7) 0.012(6) 0.006(6) 0.006(7)
C8 0.081(11) 0.068(11) 0.029(8) -0.009(7) -0.024(7) 0.030(9)
C9 0.131(14) 0.042(9) 0.025(7) -0.001(7) -0.010(8) 0.036(9)
C10 0.100(12) 0.048(10) 0.048(9) 0.011(8) 0.003(8) 0.045(9)
N1 0.069(8) 0.047(7) 0.031(6) -0.007(5) -0.008(5) 0.018(6)
N2 0.085(9) 0.058(9) 0.036(7) -0.004(6) -0.004(6) 0.031(7)
N3 0.100(10) 0.043(8) 0.043(7) 0.004(6) 0.002(7) 0.027(7)
N4 0.055(8) 0.042(7) 0.036(6) -0.011(6) -0.008(5) 0.009(6)
N5 0.058(7) 0.036(7) 0.025(5) -0.006(5) -0.008(5) 0.018(6)
N6 0.067(8) 0.052(8) 0.029(6) 0.005(5) 0.011(5) 0.019(6)
I1 0.0656(7) 0.0690(8) 0.0414(6) 0.0038(5) -0.0054(5) 0.0270(5)

_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 N6 2.308(10) 2 ?
Cd1 N6 2.308(10) . ?
Cd1 I1 3.0146(15) 2 ?
Cd1 I1 3.0146(15) . ?
Cd1 I1 3.0530(16) 1_455 ?
Cd1 I1 3.0530(16) 2_655 ?
C1 N4 1.342(14) . ?
C1 N1 1.366(14) . ?
C1 C2 1.432(15) . ?
C2 C7 1.384(14) . ?
C2 C3 1.391(16) . ?
C3 C4 1.402(16) . ?
C4 C5 1.355(16) . ?
C5 C6 1.381(16) . ?
C6 C7 1.373(14) . ?
C6 N5 1.434(14) . ?
C8 N6 1.298(15) . ?
C8 N5 1.314(13) . ?
C9 C10 1.331(16) . ?
C9 N5 1.357(14) . ?
C10 N6 1.364(14) . ?
N1 N2 1.368(12) . ?
N2 N3 1.264(13) . ?
N3 N4 1.376(13) . ?
I1 Cd1 3.0530(16) 1_655 ?

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
N6 Cd1 N6 180.0(6) 2 . ?
N6 Cd1 I1 90.8(3) 2 2 ?
N6 Cd1 I1 89.2(3) . 2 ?
N6 Cd1 I1 89.2(3) 2 . ?
N6 Cd1 I1 90.8(3) . . ?
I1 Cd1 I1 180.00(4) 2 . ?
N6 Cd1 I1 90.0(3) 2 1_455 ?
N6 Cd1 I1 90.0(3) . 1_455 ?
I1 Cd1 I1 90.60(5) 2 1_455 ?
I1 Cd1 I1 89.40(5) . 1_455 ?
N6 Cd1 I1 90.0(3) 2 2_655 ?
N6 Cd1 I1 90.0(3) . 2_655 ?
I1 Cd1 I1 89.40(5) 2 2_655 ?
I1 Cd1 I1 90.60(5) . 2_655 ?
I1 Cd1 I1 180.00(4) 1_455 2_655 ?
N4 C1 N1 106.5(10) . . ?
N4 C1 C2 127.9(12) . . ?
N1 C1 C2 125.5(12) . . ?
C7 C2 C3 118.2(11) . . ?
C7 C2 C1 122.9(11) . . ?
C3 C2 C1 118.9(11) . . ?
C2 C3 C4 119.1(12) . . ?
C5 C4 C3 120.7(13) . . ?
C4 C5 C6 121.1(11) . . ?
C5 C6 C7 118.1(12) . . ?
C5 C6 N5 120.2(10) . . ?
C7 C6 N5 121.6(11) . . ?
C2 C7 C6 122.7(12) . . ?
N6 C8 N5 113.7(12) . . ?
C10 C9 N5 105.3(11) . . ?
C9 C10 N6 111.3(12) . . ?
C1 N1 N2 106.7(10) . . ?
N3 N2 N1 110.3(11) . . ?
N2 N3 N4 108.3(10) . . ?
C1 N4 N3 108.2(10) . . ?
C8 N5 C9 106.6(10) . . ?
C8 N5 C6 128.1(11) . . ?
C9 N5 C6 125.3(10) . . ?
C8 N6 C10 103.1(10) . . ?
C8 N6 Cd1 128.4(9) . . ?
C10 N6 Cd1 128.1(9) . . ?
Cd1 I1 Cd1 89.40(5) . 1_655 ?

_diffrn_measured_fraction_theta_max 0.967
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         1.490
_refine_diff_density_min         -1.063
_refine_diff_density_rms         0.202
_database_code_depnum_ccdc_archive 'CCDC 992095'
#######################################################################
#
#                 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_CdI2D

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H7 Cd I N6'
_chemical_formula_weight         450.52

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'
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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/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                   9.8675(15)
_cell_length_b                   7.7516(13)
_cell_length_c                   17.034(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.209(2)
_cell_angle_gamma                90.00
_cell_volume                     1244.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4051
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      28.00

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    4.225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3361
_exptl_absorpt_correction_T_max  0.3842
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7079
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2708
_reflns_number_gt                2438
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0376P)²+0.5896P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0050(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2708
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0231
_refine_ls_wR_factor_ref         0.0643
_refine_ls_wR_factor_gt          0.0620
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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 -0.09507(2) 0.25415(3) 0.014037(14) 0.04142(10) Uani 1 1 d . . .
Cd1 Cd 0.06423(2) 0.20693(4) -0.087926(14) 0.03437(10) Uani 1 1 d . . .
C1 C 0.9695(3) 0.0258(4) 0.25480(17) 0.0278(6) Uani 1 1 d . . .
C2 C 0.8176(3) 0.0319(4) 0.24809(17) 0.0282(6) Uani 1 1 d . . .
C3 C 0.7681(3) -0.0063(5) 0.31476(19) 0.0369(7) Uani 1 1 d . . .
H3A H 0.8313 -0.0417 0.3643 0.044 Uiso 1 1 calc R . .
C4 C 0.6254(3) 0.0084(5) 0.3073(2) 0.0435(9) Uani 1 1 d . . .
H4A H 0.5931 -0.0168 0.3521 0.052 Uiso 1 1 calc R . .
C5 C 0.5295(3) 0.0605(5) 0.2337(2) 0.0397(8) Uani 1 1 d . . .
H5A H 0.4335 0.0707 0.2290 0.048 Uiso 1 1 calc R . .
C6 C 0.5788(3) 0.0970(4) 0.16756(17) 0.0285(6) Uani 1 1 d . . .
C7 C 0.7212(3) 0.0830(4) 0.17434(17) 0.0293(6) Uani 1 1 d . . .
H7A H 0.7528 0.1078 0.1293 0.035 Uiso 1 1 calc R . .
C8 C 0.3428(3) 0.1233(4) 0.06175(19) 0.0331(7) Uani 1 1 d . . .
H8A H 0.2906 0.0607 0.0894 0.040 Uiso 1 1 calc R . .
C9 C 0.5200(3) 0.2527(5) 0.0330(2) 0.0450(10) Uani 1 1 d . . .
H9A H 0.6096 0.2951 0.0361 0.054 Uiso 1 1 calc R . .
C10 C 0.4003(4) 0.2749(5) -0.0292(2) 0.0419(9) Uani 1 1 d . . .
H10A H 0.3937 0.3363 -0.0771 0.050 Uiso 1 1 calc R . .
N1 N 1.0234(2) -0.0359(4) 0.19694(14) 0.0306(6) Uani 1 1 d . . .
N2 N 1.1655(3) -0.0121(4) 0.22579(16) 0.0382(6) Uani 1 1 d . . .
N3 N 1.1951(3) 0.0615(4) 0.29718(16) 0.0379(6) Uani 1 1 d . . .
N4 N 1.0740(2) 0.0860(4) 0.31770(15) 0.0313(6) Uani 1 1 d . . .
N5 N 0.4838(2) 0.1548(4) 0.09128(15) 0.0292(5) Uani 1 1 d . . .
N6 N 0.2895(3) 0.1934(4) -0.01142(16) 0.0343(6) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.04027(15) 0.05172(17) 0.03867(16) -0.00391(9) 0.02155(11) -0.00883(10)
Cd1 0.02004(13) 0.05809(19) 0.02266(14) -0.00219(10) 0.00276(9) -0.00286(10)
C1 0.0227(14) 0.0355(16) 0.0219(14) 0.0029(12) 0.0016(11) 0.0019(12)
C2 0.0203(13) 0.0372(17) 0.0249(15) -0.0002(12) 0.0033(11) -0.0018(12)
C3 0.0289(16) 0.052(2) 0.0271(16) 0.0099(14) 0.0045(13) 0.0019(14)
C4 0.0310(17) 0.069(3) 0.0319(18) 0.0126(17) 0.0117(14) -0.0040(16)
C5 0.0224(15) 0.058(2) 0.0395(18) 0.0080(16) 0.0103(13) -0.0001(15)
C6 0.0207(13) 0.0372(17) 0.0252(15) 0.0010(12) 0.0033(11) -0.0008(12)
C7 0.0221(14) 0.0409(17) 0.0237(14) 0.0021(12) 0.0050(11) 0.0010(12)
C8 0.0216(14) 0.0430(18) 0.0313(16) -0.0009(14) 0.0028(12) -0.0054(13)
C9 0.0220(17) 0.065(3) 0.044(2) 0.0225(18) 0.0040(16) -0.0035(15)
C10 0.0254(16) 0.061(2) 0.0364(19) 0.0168(16) 0.0048(14) -0.0003(15)
N1 0.0205(12) 0.0441(16) 0.0245(13) 0.0008(11) 0.0024(10) -0.0005(11)
N2 0.0213(12) 0.0560(18) 0.0350(15) -0.0066(13) 0.0049(11) -0.0022(12)
N3 0.0239(13) 0.0528(18) 0.0337(15) -0.0069(13) 0.0033(11) 0.0001(12)
N4 0.0214(12) 0.0429(15) 0.0251(13) 0.0005(11) 0.0001(10) 0.0008(11)
N5 0.0167(11) 0.0391(15) 0.0289(13) 0.0031(11) 0.0023(10) 0.0005(10)
N6 0.0227(13) 0.0469(16) 0.0288(14) 0.0012(12) 0.0005(11) -0.0029(11)

_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 2.6901(4) . ?
Cd1 N6 2.222(3) . ?
Cd1 N1 2.237(3) 3_655 ?
Cd1 N4 2.294(3) 4_465 ?
C1 N4 1.332(4) . ?
C1 N1 1.339(4) . ?
C1 C2 1.470(4) . ?
C2 C7 1.390(4) . ?
C2 C3 1.395(4) . ?
C3 C4 1.381(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.389(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.383(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.379(4) . ?
C6 N5 1.431(4) . ?
C7 H7A 0.9300 . ?
C8 N6 1.318(4) . ?
C8 N5 1.354(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.344(5) . ?
C9 N5 1.378(4) . ?
C9 H9A 0.9300 . ?
C10 N6 1.372(4) . ?
C10 H10A 0.9300 . ?
N1 N2 1.354(3) . ?
N1 Cd1 2.237(3) 3_655 ?
N2 N3 1.296(3) . ?
N3 N4 1.354(3) . ?
N4 Cd1 2.294(3) 4_666 ?

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
N6 Cd1 N1 122.19(10) . 3_655 ?
N6 Cd1 N4 101.64(9) . 4_465 ?
N1 Cd1 N4 85.34(9) 3_655 4_465 ?
N6 Cd1 I1 107.58(7) . . ?
N1 Cd1 I1 117.43(6) 3_655 . ?
N4 Cd1 I1 120.74(7) 4_465 . ?
N4 C1 N1 109.6(3) . . ?
N4 C1 C2 125.4(3) . . ?
N1 C1 C2 124.9(3) . . ?
C7 C2 C3 119.0(3) . . ?
C7 C2 C1 119.3(3) . . ?
C3 C2 C1 121.6(3) . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C6 C5 C4 119.0(3) . . ?
C6 C5 H5A 120.5 . . ?
C4 C5 H5A 120.5 . . ?
C7 C6 C5 120.8(3) . . ?
C7 C6 N5 118.6(3) . . ?
C5 C6 N5 120.6(3) . . ?
C6 C7 C2 120.4(3) . . ?
C6 C7 H7A 119.8 . . ?
C2 C7 H7A 119.8 . . ?
N6 C8 N5 110.8(3) . . ?
N6 C8 H8A 124.6 . . ?
N5 C8 H8A 124.6 . . ?
C10 C9 N5 106.5(3) . . ?
C10 C9 H9A 126.7 . . ?
N5 C9 H9A 126.7 . . ?
C9 C10 N6 109.8(3) . . ?
C9 C10 H10A 125.1 . . ?
N6 C10 H10A 125.1 . . ?
C1 N1 N2 106.1(2) . . ?
C1 N1 Cd1 133.1(2) . 3_655 ?
N2 N1 Cd1 119.1(2) . 3_655 ?
N3 N2 N1 108.8(2) . . ?
N2 N3 N4 109.4(2) . . ?
C1 N4 N3 106.0(2) . . ?
C1 N4 Cd1 128.7(2) . 4_666 ?
N3 N4 Cd1 120.17(19) . 4_666 ?
C8 N5 C9 106.8(3) . . ?
C8 N5 C6 127.3(3) . . ?
C9 N5 C6 125.9(3) . . ?
C8 N6 C10 106.1(3) . . ?
C8 N6 Cd1 128.6(2) . . ?
C10 N6 Cd1 125.0(2) . . ?

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
N4 C1 C2 C7 135.1(3) . . . . ?
N1 C1 C2 C7 -42.3(5) . . . . ?
N4 C1 C2 C3 -42.6(5) . . . . ?
N1 C1 C2 C3 139.9(3) . . . . ?
C7 C2 C3 C4 -0.7(5) . . . . ?
C1 C2 C3 C4 177.1(3) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C4 C5 C6 C7 -0.4(5) . . . . ?
C4 C5 C6 N5 -178.6(3) . . . . ?
C5 C6 C7 C2 -0.1(5) . . . . ?
N5 C6 C7 C2 178.2(3) . . . . ?
C3 C2 C7 C6 0.6(5) . . . . ?
C1 C2 C7 C6 -177.2(3) . . . . ?
N5 C9 C10 N6 0.1(4) . . . . ?
N4 C1 N1 N2 0.0(3) . . . . ?
C2 C1 N1 N2 177.7(3) . . . . ?
N4 C1 N1 Cd1 164.5(2) . . . 3_655 ?
C2 C1 N1 Cd1 -17.8(5) . . . 3_655 ?
C1 N1 N2 N3 -0.5(4) . . . . ?
Cd1 N1 N2 N3 -167.6(2) 3_655 . . . ?
N1 N2 N3 N4 0.8(4) . . . . ?
N1 C1 N4 N3 0.5(3) . . . . ?
C2 C1 N4 N3 -177.3(3) . . . . ?
N1 C1 N4 Cd1 154.6(2) . . . 4_666 ?
C2 C1 N4 Cd1 -23.1(4) . . . 4_666 ?
N2 N3 N4 C1 -0.8(4) . . . . ?
N2 N3 N4 Cd1 -157.6(2) . . . 4_666 ?
N6 C8 N5 C9 0.8(4) . . . . ?
N6 C8 N5 C6 -178.5(3) . . . . ?
C10 C9 N5 C8 -0.5(4) . . . . ?
C10 C9 N5 C6 178.8(3) . . . . ?
C7 C6 N5 C8 155.6(3) . . . . ?
C5 C6 N5 C8 -26.2(5) . . . . ?
C7 C6 N5 C9 -23.6(5) . . . . ?
C5 C6 N5 C9 154.6(4) . . . . ?
N5 C8 N6 C10 -0.7(4) . . . . ?
N5 C8 N6 Cd1 -174.6(2) . . . . ?
C9 C10 N6 C8 0.4(4) . . . . ?
C9 C10 N6 Cd1 174.5(3) . . . . ?
N1 Cd1 N6 C8 -103.7(3) 3_655 . . . ?
N4 Cd1 N6 C8 164.5(3) 4_465 . . . ?
I1 Cd1 N6 C8 36.7(3) . . . . ?
N1 Cd1 N6 C10 83.5(3) 3_655 . . . ?
N4 Cd1 N6 C10 -8.3(3) 4_465 . . . ?
I1 Cd1 N6 C10 -136.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.950
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.093
_database_code_depnum_ccdc_archive 'CCDC 992096'
#######################################################################
#
#                 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_Cd3D

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 Cd N12'
_chemical_formula_weight         534.83

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'

_symmetry_cell_setting           Rhombohedral
_symmetry_space_group_name_H-M   'R-3   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   17.3547(15)
_cell_length_b                   17.3547(15)
_cell_length_c                   16.3898(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     4275.0(6)
_cell_formula_units_Z            9
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.870
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2394
_exptl_absorpt_coefficient_mu    1.190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6474
_exptl_absorpt_correction_T_max  0.7967
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7489
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0138
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         25.23
_reflns_number_total             1728
_reflns_number_gt                1667
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.0502P)²+4.9429P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1728
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0196
_refine_ls_R_factor_gt           0.0186
_refine_ls_wR_factor_ref         0.0642
_refine_ls_wR_factor_gt          0.0631
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_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 0.0000 0.0000 0.0000 0.01993(12) Uani 1 6 d S . .
Cd2 Cd 0.3333 0.6667 -0.087419(13) 0.01981(11) Uani 1 3 d S . .
N6 N 0.40505(12) 0.61314(12) -0.00801(12) 0.0301(4) Uani 1 1 d . . .
N5 N 0.42355(11) 0.52017(11) 0.06643(10) 0.0244(4) Uani 1 1 d . . .
N1 N 0.18409(11) 0.17818(11) 0.06581(10) 0.0266(4) Uani 1 1 d . . .
N2 N 0.11481(11) 0.10090(11) 0.08541(10) 0.0248(4) Uani 1 1 d . . .
N3 N 0.12082(11) 0.08335(11) 0.16056(11) 0.0272(4) Uani 1 1 d . . .
N4 N 0.19455(11) 0.14839(11) 0.19175(10) 0.0284(4) Uani 1 1 d . . .
C8 C 0.36556(14) 0.53899(15) 0.03236(14) 0.0325(5) Uani 1 1 d . . .
H8A H 0.3041 0.5034 0.0369 0.039 Uiso 1 1 calc R . .
C10 C 0.49351(14) 0.64388(14) 0.00083(14) 0.0305(5) Uani 1 1 d . . .
H10A H 0.5386 0.6962 -0.0219 0.037 Uiso 1 1 calc R . .
C9 C 0.50610(14) 0.58813(14) 0.04679(13) 0.0300(5) Uani 1 1 d . . .
H9A H 0.5604 0.5942 0.0624 0.036 Uiso 1 1 calc R . .
C6 C 0.40449(13) 0.44441(13) 0.11294(12) 0.0239(4) Uani 1 1 d . . .
C5 C 0.46070(14) 0.45360(14) 0.17444(13) 0.0302(5) Uani 1 1 d . . .
H5A H 0.5096 0.5090 0.1861 0.036 Uiso 1 1 calc R . .
C4 C 0.44480(15) 0.38074(15) 0.21893(14) 0.0333(5) Uani 1 1 d . . .
H4A H 0.4845 0.3859 0.2596 0.040 Uiso 1 1 calc R . .
C3 C 0.37077(14) 0.30007(14) 0.20417(13) 0.0280(4) Uani 1 1 d . . .
H3A H 0.3594 0.2512 0.2361 0.034 Uiso 1 1 calc R . .
C2 C 0.31364(12) 0.29067(13) 0.14317(12) 0.0224(4) Uani 1 1 d . . .
C7 C 0.33168(12) 0.36335(13) 0.09595(12) 0.0225(4) Uani 1 1 d . . .
H7A H 0.2945 0.3574 0.0526 0.027 Uiso 1 1 calc R . .
C1 C 0.23167(12) 0.20553(13) 0.13222(12) 0.0217(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cd1 0.02145(14) 0.02145(14) 0.01690(19) 0.000 0.000 0.01072(7)
Cd2 0.01997(13) 0.01997(13) 0.01947(16) 0.000 0.000 0.00999(6)
N6 0.0280(9) 0.0289(9) 0.0333(9) 0.0069(8) -0.0011(7) 0.0141(8)
N5 0.0210(8) 0.0218(8) 0.0275(9) 0.0038(7) -0.0015(6) 0.0086(7)
N1 0.0260(8) 0.0248(9) 0.0221(8) 0.0026(7) 0.0030(7) 0.0075(7)
N2 0.0213(8) 0.0239(8) 0.0230(8) 0.0010(6) 0.0018(6) 0.0066(7)
N3 0.0231(9) 0.0245(9) 0.0257(9) 0.0040(7) -0.0001(7) 0.0058(7)
N4 0.0218(8) 0.0277(9) 0.0255(9) 0.0046(7) -0.0004(7) 0.0048(7)
C8 0.0231(10) 0.0319(11) 0.0390(12) 0.0085(9) -0.0029(9) 0.0112(9)
C10 0.0265(11) 0.0254(10) 0.0356(11) 0.0051(9) 0.0043(9) 0.0099(9)
C9 0.0213(10) 0.0279(11) 0.0372(12) 0.0062(9) 0.0014(9) 0.0096(9)
C6 0.0229(9) 0.0241(10) 0.0251(10) 0.0035(8) 0.0013(8) 0.0121(8)
C5 0.0249(10) 0.0260(10) 0.0319(11) -0.0002(8) -0.0079(8) 0.0069(9)
C4 0.0261(11) 0.0365(12) 0.0327(11) 0.0050(9) -0.0083(9) 0.0123(10)
C3 0.0285(10) 0.0282(10) 0.0286(11) 0.0061(8) 0.0010(8) 0.0151(9)
C2 0.0199(9) 0.0229(9) 0.0231(9) -0.0002(8) 0.0027(7) 0.0099(8)
C7 0.0182(9) 0.0254(10) 0.0217(9) 0.0008(8) 0.0002(7) 0.0092(8)
C1 0.0210(9) 0.0207(9) 0.0237(10) 0.0007(7) 0.0025(7) 0.0107(8)

_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 N2 2.3466(16) . ?
Cd1 N2 2.3466(16) 3 ?
Cd1 N2 2.3466(16) 10 ?
Cd1 N2 2.3466(16) 2 ?
Cd1 N2 2.3466(16) 11 ?
Cd1 N2 2.3466(16) 12 ?
Cd2 N6 2.2940(17) 2_665 ?
Cd2 N6 2.2940(17) 3_565 ?
Cd2 N6 2.2940(17) . ?
Cd2 N3 2.3266(17) 8_554 ?
Cd2 N3 2.3267(17) 7_554 ?
Cd2 N3 2.3267(17) 9_554 ?
N6 C8 1.297(3) . ?
N6 C10 1.358(3) . ?
N5 C8 1.327(3) . ?
N5 C9 1.363(3) . ?
N5 C6 1.409(2) . ?
N1 C1 1.304(3) . ?
N1 N2 1.317(2) . ?
N2 N3 1.285(2) . ?
N3 N4 1.315(2) . ?
N3 Cd2 2.3267(17) 4_445 ?
N4 C1 1.308(3) . ?
C8 H8A 0.9300 . ?
C10 C9 1.328(3) . ?
C10 H10A 0.9300 . ?
C9 H9A 0.9300 . ?
C6 C5 1.355(3) . ?
C6 C7 1.370(3) . ?
C5 C4 1.363(3) . ?
C5 H5A 0.9300 . ?
C4 C3 1.368(3) . ?
C4 H4A 0.9300 . ?
C3 C2 1.359(3) . ?
C3 H3A 0.9300 . ?
C2 C7 1.376(3) . ?
C2 C1 1.462(3) . ?
C7 H7A 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
N2 Cd1 N2 88.06(6) . 3 ?
N2 Cd1 N2 180.00(11) . 10 ?
N2 Cd1 N2 91.94(6) 3 10 ?
N2 Cd1 N2 88.06(6) . 2 ?
N2 Cd1 N2 88.06(6) 3 2 ?
N2 Cd1 N2 91.94(6) 10 2 ?
N2 Cd1 N2 91.94(6) . 11 ?
N2 Cd1 N2 91.94(6) 3 11 ?
N2 Cd1 N2 88.06(6) 10 11 ?
N2 Cd1 N2 180.0 2 11 ?
N2 Cd1 N2 91.94(6) . 12 ?
N2 Cd1 N2 180.00(5) 3 12 ?
N2 Cd1 N2 88.06(6) 10 12 ?
N2 Cd1 N2 91.94(6) 2 12 ?
N2 Cd1 N2 88.06(6) 11 12 ?
N6 Cd2 N6 90.98(7) 2_665 3_565 ?
N6 Cd2 N6 90.98(7) 2_665 . ?
N6 Cd2 N6 90.98(7) 3_565 . ?
N6 Cd2 N3 95.17(6) 2_665 8_554 ?
N6 Cd2 N3 86.56(7) 3_565 8_554 ?
N6 Cd2 N3 173.41(6) . 8_554 ?
N6 Cd2 N3 86.56(7) 2_665 7_554 ?
N6 Cd2 N3 173.41(6) 3_565 7_554 ?
N6 Cd2 N3 95.17(6) . 7_554 ?
N3 Cd2 N3 87.57(6) 8_554 7_554 ?
N6 Cd2 N3 173.41(6) 2_665 9_554 ?
N6 Cd2 N3 95.17(6) 3_565 9_554 ?
N6 Cd2 N3 86.56(7) . 9_554 ?
N3 Cd2 N3 87.57(6) 8_554 9_554 ?
N3 Cd2 N3 87.57(6) 7_554 9_554 ?
C8 N6 C10 105.57(18) . . ?
C8 N6 Cd2 124.52(14) . . ?
C10 N6 Cd2 129.59(14) . . ?
C8 N5 C9 106.63(17) . . ?
C8 N5 C6 127.19(17) . . ?
C9 N5 C6 126.17(17) . . ?
C1 N1 N2 104.87(16) . . ?
N3 N2 N1 109.51(16) . . ?
N3 N2 Cd1 122.28(12) . . ?
N1 N2 Cd1 128.06(13) . . ?
N2 N3 N4 109.18(15) . . ?
N2 N3 Cd2 124.66(13) . 4_445 ?
N4 N3 Cd2 119.19(13) . 4_445 ?
N3 N4 C1 105.06(16) . . ?
N6 C8 N5 111.68(19) . . ?
N6 C8 H8A 124.2 . . ?
N5 C8 H8A 124.2 . . ?
C9 C10 N6 109.87(19) . . ?
C9 C10 H10A 125.1 . . ?
N6 C10 H10A 125.1 . . ?
C10 C9 N5 106.25(18) . . ?
C10 C9 H9A 126.9 . . ?
N5 C9 H9A 126.9 . . ?
C5 C6 C7 120.81(19) . . ?
C5 C6 N5 118.24(18) . . ?
C7 C6 N5 120.94(18) . . ?
C6 C5 C4 119.25(19) . . ?
C6 C5 H5A 120.4 . . ?
C4 C5 H5A 120.4 . . ?
C3 C4 C5 120.39(19) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C4 C3 C2 120.57(19) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C3 C2 C7 119.06(19) . . ?
C3 C2 C1 119.63(18) . . ?
C7 C2 C1 121.20(18) . . ?
C6 C7 C2 119.83(19) . . ?
C6 C7 H7A 120.1 . . ?
C2 C7 H7A 120.1 . . ?
N4 C1 N1 111.37(17) . . ?
N4 C1 C2 122.42(18) . . ?
N1 C1 C2 126.12(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N6 Cd2 N6 C8 119.35(16) 2_665 . . . ?
N6 Cd2 N6 C8 28.3(2) 3_565 . . . ?
N3 Cd2 N6 C8 -39.7(6) 8_554 . . . ?
N3 Cd2 N6 C8 -154.02(19) 7_554 . . . ?
N3 Cd2 N6 C8 -66.77(19) 9_554 . . . ?
N6 Cd2 N6 C10 -68.2(2) 2_665 . . . ?
N6 Cd2 N6 C10 -159.17(19) 3_565 . . . ?
N3 Cd2 N6 C10 132.8(5) 8_554 . . . ?
N3 Cd2 N6 C10 18.5(2) 7_554 . . . ?
N3 Cd2 N6 C10 105.7(2) 9_554 . . . ?
C1 N1 N2 N3 0.3(2) . . . . ?
C1 N1 N2 Cd1 -175.22(13) . . . . ?
N2 Cd1 N2 N3 -24.55(14) 3 . . . ?
N2 Cd1 N2 N3 -141(16) 10 . . . ?
N2 Cd1 N2 N3 63.58(13) 2 . . . ?
N2 Cd1 N2 N3 -116.42(13) 11 . . . ?
N2 Cd1 N2 N3 155.45(14) 12 . . . ?
N2 Cd1 N2 N1 150.49(19) 3 . . . ?
N2 Cd1 N2 N1 34(16) 10 . . . ?
N2 Cd1 N2 N1 -121.4(2) 2 . . . ?
N2 Cd1 N2 N1 58.6(2) 11 . . . ?
N2 Cd1 N2 N1 -29.51(19) 12 . . . ?
N1 N2 N3 N4 -0.5(2) . . . . ?
Cd1 N2 N3 N4 175.36(13) . . . . ?
N1 N2 N3 Cd2 149.76(14) . . . 4_445 ?
Cd1 N2 N3 Cd2 -34.4(2) . . . 4_445 ?
N2 N3 N4 C1 0.5(2) . . . . ?
Cd2 N3 N4 C1 -151.68(14) 4_445 . . . ?
C10 N6 C8 N5 -0.2(3) . . . . ?
Cd2 N6 C8 N5 173.79(14) . . . . ?
C9 N5 C8 N6 0.7(3) . . . . ?
C6 N5 C8 N6 -178.49(19) . . . . ?
C8 N6 C10 C9 -0.4(3) . . . . ?
Cd2 N6 C10 C9 -173.94(15) . . . . ?
N6 C10 C9 N5 0.8(3) . . . . ?
C8 N5 C9 C10 -0.9(2) . . . . ?
C6 N5 C9 C10 178.31(19) . . . . ?
C8 N5 C6 C5 -146.9(2) . . . . ?
C9 N5 C6 C5 34.1(3) . . . . ?
C8 N5 C6 C7 33.8(3) . . . . ?
C9 N5 C6 C7 -145.1(2) . . . . ?
C7 C6 C5 C4 0.9(3) . . . . ?
N5 C6 C5 C4 -178.4(2) . . . . ?
C6 C5 C4 C3 -3.0(4) . . . . ?
C5 C4 C3 C2 2.3(3) . . . . ?
C4 C3 C2 C7 0.5(3) . . . . ?
C4 C3 C2 C1 -175.6(2) . . . . ?
C5 C6 C7 C2 1.9(3) . . . . ?
N5 C6 C7 C2 -178.88(18) . . . . ?
C3 C2 C7 C6 -2.6(3) . . . . ?
C1 C2 C7 C6 173.49(18) . . . . ?
N3 N4 C1 N1 -0.3(2) . . . . ?
N3 N4 C1 C2 176.60(18) . . . . ?
N2 N1 C1 N4 0.0(2) . . . . ?
N2 N1 C1 C2 -176.74(18) . . . . ?
C3 C2 C1 N4 24.2(3) . . . . ?
C7 C2 C1 N4 -151.9(2) . . . . ?
C3 C2 C1 N1 -159.5(2) . . . . ?
C7 C2 C1 N1 24.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.23
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.058
#############################################################################
_database_code_depnum_ccdc_archive 'CCDC 992097'
