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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1498769'
_audit_update_record             
;
2016-08-11 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H19 Cd N9 O'
_chemical_formula_weight         429.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.5203(2)
_cell_length_b                   12.5815(2)
_cell_length_c                   11.8042(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.088(2)
_cell_angle_gamma                90
_cell_volume                     1689.45(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    14191
_cell_measurement_theta_min      3.6620
_cell_measurement_theta_max      32.1000

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    1.314
_shelx_estimated_absorpt_T_min   0.752
_shelx_estimated_absorpt_T_max   0.837
_exptl_absorpt_correction_T_min  0.43553
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_reflns_number            11513
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.142
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2967
_reflns_number_gt                2899
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
  _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0269P)²+0.7961P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2967
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0178
_refine_ls_R_factor_gt           0.0174
_refine_ls_wR_factor_ref         0.0478
_refine_ls_wR_factor_gt          0.0475
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.22196(2) 0.21045(2) 0.32620(2) 0.01867(6) Uani 1 1 d . . . . .
O1 O -0.13833(12) 0.28267(9) 0.19492(12) 0.0253(3) Uani 1 1 d . . . . .
N1 N 0.42629(13) 0.18037(13) 0.39868(13) 0.0237(3) Uani 1 1 d . . . . .
N2 N 0.28773(13) 0.05883(11) 0.24789(12) 0.0211(3) Uani 1 1 d . . . . .
N3 N 0.04365(12) 0.12448(11) 0.22611(12) 0.0193(3) Uani 1 1 d . . . . .
N4 N 0.17692(14) 0.12173(13) 0.49357(13) 0.0267(3) Uani 1 1 d . . . . .
N5 N 0.22542(13) 0.15909(12) 0.58030(12) 0.0227(3) Uani 1 1 d . . . . .
N6 N 0.27551(14) 0.19432(15) 0.66692(13) 0.0306(4) Uani 1 1 d . . . . .
N7 N 0.19135(15) 0.36668(13) 0.40535(14) 0.0295(4) Uani 1 1 d . . . . .
N8 N 0.25258(14) 0.44190(13) 0.39786(13) 0.0267(3) Uani 1 1 d . . . . .
N9 N 0.30800(17) 0.51809(15) 0.39395(18) 0.0443(5) Uani 1 1 d . . . . .
C1 C 0.49147(18) 0.23729(17) 0.48001(17) 0.0300(4) Uani 1 1 d . . . . .
H1 H 0.4586 0.2976 0.5076 0.036 Uiso 1 1 calc R U . . .
C2 C 0.6066(2) 0.21069(16) 0.5257(2) 0.0355(5) Uani 1 1 d . . . . .
H2 H 0.6499 0.2520 0.5826 0.043 Uiso 1 1 calc R U . . .
C3 C 0.65440(18) 0.12142(18) 0.48393(19) 0.0384(5) Uani 1 1 d . . . . .
H3 H 0.7308 0.1009 0.5134 0.046 Uiso 1 1 calc R U . . .
C4 C 0.58828(17) 0.06215(16) 0.39776(18) 0.0332(4) Uani 1 1 d . . . . .
H4 H 0.6203 0.0026 0.3678 0.040 Uiso 1 1 calc R U . . .
C5 C 0.47341(16) 0.09317(15) 0.35691(16) 0.0248(4) Uani 1 1 d . . . . .
C6 C 0.39482(16) 0.03043(14) 0.26723(15) 0.0238(4) Uani 1 1 d . . . . .
C7 C 0.44642(19) -0.05992(18) 0.2085(2) 0.0405(5) Uani 1 1 d . . . . .
H7A H 0.4613 -0.1188 0.2605 0.061 Uiso 1 1 calc R U . . .
H7B H 0.5188 -0.0375 0.1854 0.061 Uiso 1 1 calc R U . . .
H7C H 0.3921 -0.0812 0.1422 0.061 Uiso 1 1 calc R U . . .
C8 C 0.19772(16) 0.00554(14) 0.16719(16) 0.0241(4) Uani 1 1 d . . . . .
H8A H 0.2186 -0.0685 0.1593 0.029 Uiso 1 1 calc R U . . .
H8B H 0.1907 0.0390 0.0924 0.029 Uiso 1 1 calc R U . . .
C9 C 0.08182(15) 0.01367(14) 0.21305(16) 0.0239(4) Uani 1 1 d . . . . .
H9A H 0.0215 -0.0234 0.1612 0.029 Uiso 1 1 calc R U . . .
H9B H 0.0899 -0.0215 0.2870 0.029 Uiso 1 1 calc R U . . .
C10 C -0.05536(15) 0.12343(14) 0.29292(15) 0.0233(4) Uani 1 1 d . . . . .
H10A H -0.0288 0.0942 0.3686 0.028 Uiso 1 1 calc R U . . .
H10B H -0.1181 0.0786 0.2546 0.028 Uiso 1 1 calc R U . . .
C11 C -0.10101(17) 0.23477(16) 0.30401(16) 0.0251(4) Uani 1 1 d . . . . .
H11A H -0.1666 0.2326 0.3464 0.030 Uiso 1 1 calc R U . . .
H11B H -0.0396 0.2779 0.3472 0.030 Uiso 1 1 calc R U . . .
C12 C -0.04359(17) 0.28412(14) 0.13014(17) 0.0239(4) Uani 1 1 d . . . . .
H12A H 0.0201 0.3269 0.1700 0.029 Uiso 1 1 calc R U . . .
H12B H -0.0700 0.3167 0.0560 0.029 Uiso 1 1 calc R U . . .
C13 C 0.00086(15) 0.17320(15) 0.11269(14) 0.0223(4) Uani 1 1 d . . . . .
H13A H -0.0620 0.1304 0.0714 0.027 Uiso 1 1 calc R U . . .
H13B H 0.0643 0.1762 0.0676 0.027 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N7 2.2281(15) . ?
Cd1 N2 2.2998(14) . ?
Cd1 N6 2.3912(16) 4_565 ?
Cd1 N4 2.3963(15) . ?
Cd1 N1 2.4042(15) . ?
Cd1 N3 2.4534(14) . ?
O1 C11 1.425(2) . ?
O1 C12 1.428(2) . ?
N1 C1 1.331(3) . ?
N1 C5 1.351(3) . ?
N2 C6 1.270(2) . ?
N2 C8 1.456(2) . ?
N3 C9 1.477(2) . ?
N3 C13 1.484(2) . ?
N3 C10 1.486(2) . ?
N4 N5 1.183(2) . ?
N5 N6 1.178(2) . ?
N6 Cd1 2.3912(16) 4_566 ?
N7 N8 1.192(2) . ?
N8 N9 1.157(2) . ?
C1 C2 1.391(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.376(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.504(3) . ?
C6 C7 1.502(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.521(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.509(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.512(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

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
N7 Cd1 N2 169.83(6) . . ?
N7 Cd1 N6 88.01(6) . 4_565 ?
N2 Cd1 N6 87.55(6) . 4_565 ?
N7 Cd1 N4 89.77(6) . . ?
N2 Cd1 N4 94.19(5) . . ?
N6 Cd1 N4 176.41(5) 4_565 . ?
N7 Cd1 N1 101.57(6) . . ?
N2 Cd1 N1 69.28(5) . . ?
N6 Cd1 N1 89.94(5) 4_565 . ?
N4 Cd1 N1 87.74(5) . . ?
N7 Cd1 N3 114.51(5) . . ?
N2 Cd1 N3 75.21(5) . . ?
N6 Cd1 N3 98.20(5) 4_565 . ?
N4 Cd1 N3 85.28(5) . . ?
N1 Cd1 N3 143.15(5) . . ?
C11 O1 C12 110.01(14) . . ?
C1 N1 C5 119.13(16) . . ?
C1 N1 Cd1 125.54(13) . . ?
C5 N1 Cd1 115.16(12) . . ?
C6 N2 C8 124.00(15) . . ?
C6 N2 Cd1 122.24(12) . . ?
C8 N2 Cd1 113.52(11) . . ?
C9 N3 C13 110.95(13) . . ?
C9 N3 C10 108.25(13) . . ?
C13 N3 C10 108.00(13) . . ?
C9 N3 Cd1 103.06(10) . . ?
C13 N3 Cd1 112.70(10) . . ?
C10 N3 Cd1 113.76(10) . . ?
N5 N4 Cd1 113.21(12) . . ?
N6 N5 N4 178.44(19) . . ?
N5 N6 Cd1 135.97(13) . 4_566 ?
N8 N7 Cd1 122.32(12) . . ?
N9 N8 N7 176.21(19) . . ?
N1 C1 C2 123.0(2) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 117.9(2) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 119.78(19) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 119.04(19) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.09(18) . . ?
N1 C5 C6 116.82(15) . . ?
C4 C5 C6 122.07(17) . . ?
N2 C6 C7 125.04(18) . . ?
N2 C6 C5 116.02(16) . . ?
C7 C6 C5 118.94(16) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C9 108.09(14) . . ?
N2 C8 H8A 110.1 . . ?
C9 C8 H8A 110.1 . . ?
N2 C8 H8B 110.1 . . ?
C9 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
N3 C9 C8 113.14(14) . . ?
N3 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
N3 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
N3 C10 C11 110.19(14) . . ?
N3 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
N3 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
O1 C11 C10 111.94(15) . . ?
O1 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
O1 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
O1 C12 C13 111.41(14) . . ?
O1 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
O1 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
N3 C13 C12 109.26(14) . . ?
N3 C13 H13A 109.8 . . ?
C12 C13 H13A 109.8 . . ?
N3 C13 H13B 109.8 . . ?
C12 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?

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
C5 N1 C1 C2 -0.7(3) . . . . ?
Cd1 N1 C1 C2 174.24(15) . . . . ?
N1 C1 C2 C3 0.2(3) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
C1 N1 C5 C4 0.2(3) . . . . ?
Cd1 N1 C5 C4 -175.29(14) . . . . ?
C1 N1 C5 C6 178.55(16) . . . . ?
Cd1 N1 C5 C6 3.08(19) . . . . ?
C3 C4 C5 N1 0.9(3) . . . . ?
C3 C4 C5 C6 -177.42(18) . . . . ?
C8 N2 C6 C7 1.7(3) . . . . ?
Cd1 N2 C6 C7 -172.44(15) . . . . ?
C8 N2 C6 C5 -177.81(15) . . . . ?
Cd1 N2 C6 C5 8.1(2) . . . . ?
N1 C5 C6 N2 -7.2(2) . . . . ?
C4 C5 C6 N2 171.14(17) . . . . ?
N1 C5 C6 C7 173.26(17) . . . . ?
C4 C5 C6 C7 -8.4(3) . . . . ?
C6 N2 C8 C9 147.35(17) . . . . ?
Cd1 N2 C8 C9 -38.07(16) . . . . ?
C13 N3 C9 C8 73.17(18) . . . . ?
C10 N3 C9 C8 -168.49(14) . . . . ?
Cd1 N3 C9 C8 -47.69(15) . . . . ?
N2 C8 C9 N3 60.38(19) . . . . ?
C9 N3 C10 C11 -177.49(15) . . . . ?
C13 N3 C10 C11 -57.29(18) . . . . ?
Cd1 N3 C10 C11 68.61(16) . . . . ?
C12 O1 C11 C10 -57.48(18) . . . . ?
N3 C10 C11 O1 57.72(19) . . . . ?
C11 O1 C12 C13 58.85(19) . . . . ?
C9 N3 C13 C12 176.85(14) . . . . ?
C10 N3 C13 C12 58.36(18) . . . . ?
Cd1 N3 C13 C12 -68.16(15) . . . . ?
O1 C12 C13 N3 -60.28(19) . . . . ?

_refine_diff_density_max         0.380
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.052

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sm093
_database_code_depnum_ccdc_archive 'CCDC 958288'
_audit_update_record             
;
2013-08-30 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H34 Cd Cl2 N6 O8'
_chemical_formula_weight         693.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'

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

_cell_length_a                   16.20890(10)
_cell_length_b                   14.13480(10)
_cell_length_c                   12.84340(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2942.55(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    25911
_cell_measurement_theta_min      2.8912
_cell_measurement_theta_max      32.5316

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1416
_exptl_absorpt_coefficient_mu    0.977
_exptl_absorpt_correction_T_min  0.8065
_exptl_absorpt_correction_T_max  0.8835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24292
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_sigmaI/netI    0.0138
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         24.99
_reflns_number_total             5171
_reflns_number_gt                5103
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0433P)²+1.9136P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_number_reflns         5171
_refine_ls_number_parameters     358
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0239
_refine_ls_wR_factor_ref         0.0678
_refine_ls_wR_factor_gt          0.0674
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.002
_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 0.729692(10) 0.417717(12) 0.00200(2) 0.02393(7) Uani 1 1 d . . .
Cl1 Cl 0.40231(5) 0.39915(6) 0.90986(7) 0.03658(18) Uani 1 1 d . . .
Cl2 Cl 1.01407(5) 0.65576(7) -0.04548(7) 0.0414(2) Uani 1 1 d . . .
O1 O 0.4792(2) 0.4208(3) 0.8661(4) 0.0846(13) Uani 1 1 d . . .
O2 O 0.3490(2) 0.3613(3) 0.8318(2) 0.0649(8) Uani 1 1 d . . .
O3 O 0.4136(3) 0.3275(3) 0.9855(3) 0.0944(13) Uani 1 1 d . . .
O4 O 0.3684(3) 0.4782(4) 0.9550(4) 0.1240(19) Uani 1 1 d . . .
O5 O 1.10189(19) 0.6596(3) -0.0512(2) 0.0715(10) Uani 1 1 d . . .
O6 O 0.9803(2) 0.5888(2) -0.1168(2) 0.0630(9) Uani 1 1 d . . .
O7 O 0.9842(3) 0.7487(2) -0.0718(3) 0.0889(13) Uani 1 1 d . . .
O8 O 0.9894(2) 0.6359(3) 0.0577(2) 0.0716(11) Uani 1 1 d . . .
N1 N 0.66221(16) 0.27438(19) 0.0419(2) 0.0314(6) Uani 1 1 d . . .
N2 N 0.61032(16) 0.44876(19) 0.09048(19) 0.0284(5) Uani 1 1 d . . .
N3 N 0.69993(18) 0.58021(16) -0.0286(2) 0.0285(6) Uani 1 1 d . . .
N4 N 0.81447(18) 0.4070(2) 0.1593(2) 0.0344(6) Uani 1 1 d . . .
N5 N 0.86257(16) 0.39824(19) -0.0532(2) 0.0290(6) Uani 1 1 d . . .
N6 N 0.72986(15) 0.37155(19) -0.1745(2) 0.0291(6) Uani 1 1 d . . .
C1 C 0.6925(2) 0.1895(2) 0.0199(3) 0.0399(8) Uani 1 1 d . . .
H1 H 0.7291 0.1828 -0.0374 0.048 Uiso 1 1 calc R . .
C2 C 0.6720(2) 0.1097(3) 0.0784(3) 0.0434(8) Uani 1 1 d . . .
H2 H 0.6952 0.0498 0.0623 0.052 Uiso 1 1 calc R . .
C3 C 0.6181(2) 0.1193(3) 0.1591(3) 0.0412(8) Uani 1 1 d . . .
H3 H 0.6035 0.0660 0.2002 0.049 Uiso 1 1 calc R . .
C4 C 0.5846(2) 0.2078(2) 0.1809(3) 0.0357(7) Uani 1 1 d . . .
H4 H 0.5469 0.2157 0.2369 0.043 Uiso 1 1 calc R . .
C5 C 0.60711(17) 0.2834(2) 0.1201(2) 0.0283(6) Uani 1 1 d . . .
C6 C 0.57273(18) 0.3815(2) 0.1352(2) 0.0279(6) Uani 1 1 d . . .
C7 C 0.4971(2) 0.3924(3) 0.2002(3) 0.0419(8) Uani 1 1 d . . .
H7A H 0.5127 0.3952 0.2739 0.063 Uiso 1 1 calc R . .
H7B H 0.4604 0.3383 0.1887 0.063 Uiso 1 1 calc R . .
H7C H 0.4685 0.4509 0.1808 0.063 Uiso 1 1 calc R . .
C8 C 0.5822(2) 0.5465(2) 0.0921(3) 0.0358(7) Uani 1 1 d . . .
H8A H 0.5613 0.5626 0.1624 0.043 Uiso 1 1 calc R . .
H8B H 0.5365 0.5548 0.0418 0.043 Uiso 1 1 calc R . .
C9 C 0.6544(2) 0.6132(2) 0.0632(3) 0.0353(7) Uani 1 1 d . . .
H9A H 0.6324 0.6773 0.0493 0.042 Uiso 1 1 calc R . .
H9B H 0.6927 0.6177 0.1230 0.042 Uiso 1 1 calc R . .
C10 C 0.7753(2) 0.6395(3) -0.0427(4) 0.0461(9) Uani 1 1 d . . .
H10A H 0.7591 0.7040 -0.0617 0.069 Uiso 1 1 calc R . .
H10B H 0.8096 0.6125 -0.0981 0.069 Uiso 1 1 calc R . .
H10C H 0.8067 0.6409 0.0225 0.069 Uiso 1 1 calc R . .
C11 C 0.6496(3) 0.5882(2) -0.1237(3) 0.0414(9) Uani 1 1 d . . .
H11A H 0.6039 0.5430 -0.1204 0.062 Uiso 1 1 calc R . .
H11B H 0.6839 0.5744 -0.1847 0.062 Uiso 1 1 calc R . .
H11C H 0.6276 0.6526 -0.1293 0.062 Uiso 1 1 calc R . .
C12 C 0.6637(2) 0.3634(3) -0.2355(3) 0.0395(8) Uani 1 1 d . . .
H12 H 0.6110 0.3619 -0.2032 0.047 Uiso 1 1 calc R . .
C13 C 0.6670(3) 0.3569(3) -0.3433(3) 0.0438(8) Uani 1 1 d . . .
H13 H 0.6185 0.3512 -0.3843 0.053 Uiso 1 1 calc R . .
C14 C 0.7453(3) 0.3593(3) -0.3879(3) 0.0422(8) Uani 1 1 d . . .
H14 H 0.7509 0.3575 -0.4615 0.051 Uiso 1 1 calc R . .
C15 C 0.8144(2) 0.3641(2) -0.3263(3) 0.0351(7) Uani 1 1 d . . .
H15 H 0.8678 0.3632 -0.3565 0.042 Uiso 1 1 calc R . .
C16 C 0.8050(2) 0.3704(2) -0.2200(2) 0.0287(6) Uani 1 1 d . . .
C17 C 0.87732(18) 0.3748(2) -0.1465(3) 0.0270(6) Uani 1 1 d . . .
C18 C 0.9625(2) 0.3520(3) -0.1867(3) 0.0428(8) Uani 1 1 d . . .
H18A H 0.9902 0.4105 -0.2078 0.064 Uiso 1 1 calc R . .
H18B H 0.9581 0.3095 -0.2467 0.064 Uiso 1 1 calc R . .
H18C H 0.9945 0.3211 -0.1316 0.064 Uiso 1 1 calc R . .
C19 C 0.9261(2) 0.4003(3) 0.0266(3) 0.0377(8) Uani 1 1 d . . .
H19A H 0.9743 0.4363 0.0008 0.045 Uiso 1 1 calc R . .
H19B H 0.9443 0.3350 0.0421 0.045 Uiso 1 1 calc R . .
C20 C 0.8939(2) 0.4458(3) 0.1244(3) 0.0421(8) Uani 1 1 d . . .
H20A H 0.9350 0.4374 0.1806 0.051 Uiso 1 1 calc R . .
H20B H 0.8875 0.5146 0.1122 0.051 Uiso 1 1 calc R . .
C21 C 0.8256(3) 0.3071(3) 0.1900(3) 0.0506(10) Uani 1 1 d . . .
H21A H 0.8442 0.2703 0.1297 0.076 Uiso 1 1 calc R . .
H21B H 0.7730 0.2816 0.2152 0.076 Uiso 1 1 calc R . .
H21C H 0.8669 0.3030 0.2455 0.076 Uiso 1 1 calc R . .
C22 C 0.7835(3) 0.4602(5) 0.2480(3) 0.0676(15) Uani 1 1 d . . .
H22A H 0.8239 0.4575 0.3048 0.101 Uiso 1 1 calc R . .
H22B H 0.7312 0.4327 0.2714 0.101 Uiso 1 1 calc R . .
H22C H 0.7747 0.5263 0.2277 0.101 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N5 2.284(3) . ?
Cd1 N2 2.286(2) . ?
Cd1 N6 2.359(3) . ?
Cd1 N1 2.359(3) . ?
Cd1 N3 2.380(2) . ?
Cd1 N4 2.448(3) . ?
Cl1 O4 1.375(4) . ?
Cl1 O1 1.401(4) . ?
Cl1 O3 1.415(3) . ?
Cl1 O2 1.428(3) . ?
Cl2 O8 1.412(3) . ?
Cl2 O6 1.426(3) . ?
Cl2 O5 1.426(3) . ?
Cl2 O7 1.441(4) . ?
N1 C1 1.327(4) . ?
N1 C5 1.350(4) . ?
N2 C6 1.267(4) . ?
N2 C8 1.456(4) . ?
N3 C9 1.467(4) . ?
N3 C11 1.473(5) . ?
N3 C10 1.493(4) . ?
N4 C22 1.455(5) . ?
N4 C20 1.469(5) . ?
N4 C21 1.477(5) . ?
N5 C17 1.266(4) . ?
N5 C19 1.453(4) . ?
N6 C12 1.333(5) . ?
N6 C16 1.351(4) . ?
C1 C2 1.395(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.362(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.373(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.507(4) . ?
C6 C7 1.491(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.548(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.387(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.373(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.505(5) . ?
C17 C18 1.509(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.505(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 Cd1 N2 167.26(10) . . ?
N5 Cd1 N6 70.56(9) . . ?
N2 Cd1 N6 122.12(9) . . ?
N5 Cd1 N1 113.66(9) . . ?
N2 Cd1 N1 70.39(9) . . ?
N6 Cd1 N1 88.39(9) . . ?
N5 Cd1 N3 104.84(10) . . ?
N2 Cd1 N3 74.06(9) . . ?
N6 Cd1 N3 96.23(9) . . ?
N1 Cd1 N3 140.44(9) . . ?
N5 Cd1 N4 73.70(10) . . ?
N2 Cd1 N4 94.41(9) . . ?
N6 Cd1 N4 140.82(9) . . ?
N1 Cd1 N4 91.58(10) . . ?
N3 Cd1 N4 108.06(9) . . ?
O4 Cl1 O1 110.3(3) . . ?
O4 Cl1 O3 110.1(3) . . ?
O1 Cl1 O3 108.5(3) . . ?
O4 Cl1 O2 111.0(3) . . ?
O1 Cl1 O2 109.8(2) . . ?
O3 Cl1 O2 107.0(2) . . ?
O8 Cl2 O6 111.2(2) . . ?
O8 Cl2 O5 109.8(2) . . ?
O6 Cl2 O5 112.0(2) . . ?
O8 Cl2 O7 107.9(3) . . ?
O6 Cl2 O7 109.0(2) . . ?
O5 Cl2 O7 106.8(3) . . ?
C1 N1 C5 119.2(3) . . ?
C1 N1 Cd1 124.0(2) . . ?
C5 N1 Cd1 112.8(2) . . ?
C6 N2 C8 123.7(3) . . ?
C6 N2 Cd1 119.2(2) . . ?
C8 N2 Cd1 117.0(2) . . ?
C9 N3 C11 111.3(3) . . ?
C9 N3 C10 109.3(3) . . ?
C11 N3 C10 108.1(3) . . ?
C9 N3 Cd1 106.01(19) . . ?
C11 N3 Cd1 108.86(19) . . ?
C10 N3 Cd1 113.3(2) . . ?
C22 N4 C20 110.3(4) . . ?
C22 N4 C21 109.1(3) . . ?
C20 N4 C21 109.4(3) . . ?
C22 N4 Cd1 114.9(2) . . ?
C20 N4 Cd1 102.6(2) . . ?
C21 N4 Cd1 110.4(2) . . ?
C17 N5 C19 122.7(3) . . ?
C17 N5 Cd1 120.2(2) . . ?
C19 N5 Cd1 116.5(2) . . ?
C12 N6 C16 118.0(3) . . ?
C12 N6 Cd1 126.0(2) . . ?
C16 N6 Cd1 114.8(2) . . ?
N1 C1 C2 121.8(3) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C1 118.8(3) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 121.7(3) . . ?
N1 C5 C6 115.2(3) . . ?
C4 C5 C6 123.0(3) . . ?
N2 C6 C7 124.8(3) . . ?
N2 C6 C5 117.1(3) . . ?
C7 C6 C5 118.1(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C9 109.7(3) . . ?
N2 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
N2 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
N3 C9 C8 112.3(3) . . ?
N3 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
N3 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N6 C12 C13 124.2(3) . . ?
N6 C12 H12 117.9 . . ?
C13 C12 H12 117.9 . . ?
C12 C13 C14 116.3(4) . . ?
C12 C13 H13 121.8 . . ?
C14 C13 H13 121.8 . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.1(3) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
N6 C16 C15 121.9(3) . . ?
N6 C16 C17 115.5(3) . . ?
C15 C16 C17 122.6(3) . . ?
N5 C17 C16 117.2(3) . . ?
N5 C17 C18 123.5(3) . . ?
C16 C17 C18 119.3(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N5 C19 C20 110.6(3) . . ?
N5 C19 H19A 109.5 . . ?
C20 C19 H19A 109.5 . . ?
N5 C19 H19B 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
N4 C20 C19 113.5(3) . . ?
N4 C20 H20A 108.9 . . ?
C19 C20 H20A 108.9 . . ?
N4 C20 H20B 108.9 . . ?
C19 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
N4 C21 H21A 109.5 . . ?
N4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N4 C22 H22A 109.5 . . ?
N4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N5 Cd1 N1 C1 -10.0(3) . . . . ?
N2 Cd1 N1 C1 -177.0(3) . . . . ?
N6 Cd1 N1 C1 57.9(3) . . . . ?
N3 Cd1 N1 C1 155.8(3) . . . . ?
N4 Cd1 N1 C1 -82.9(3) . . . . ?
N5 Cd1 N1 C5 147.3(2) . . . . ?
N2 Cd1 N1 C5 -19.7(2) . . . . ?
N6 Cd1 N1 C5 -144.8(2) . . . . ?
N3 Cd1 N1 C5 -46.9(3) . . . . ?
N4 Cd1 N1 C5 74.4(2) . . . . ?
N5 Cd1 N2 C6 -98.2(5) . . . . ?
N6 Cd1 N2 C6 87.6(2) . . . . ?
N1 Cd1 N2 C6 12.6(2) . . . . ?
N3 Cd1 N2 C6 174.9(3) . . . . ?
N4 Cd1 N2 C6 -77.5(2) . . . . ?
N5 Cd1 N2 C8 81.5(5) . . . . ?
N6 Cd1 N2 C8 -92.7(2) . . . . ?
N1 Cd1 N2 C8 -167.7(2) . . . . ?
N3 Cd1 N2 C8 -5.3(2) . . . . ?
N4 Cd1 N2 C8 102.2(2) . . . . ?
N5 Cd1 N3 C9 -138.1(2) . . . . ?
N2 Cd1 N3 C9 28.73(19) . . . . ?
N6 Cd1 N3 C9 150.4(2) . . . . ?
N1 Cd1 N3 C9 55.4(3) . . . . ?
N4 Cd1 N3 C9 -60.8(2) . . . . ?
N5 Cd1 N3 C11 102.1(2) . . . . ?
N2 Cd1 N3 C11 -91.1(2) . . . . ?
N6 Cd1 N3 C11 30.6(2) . . . . ?
N1 Cd1 N3 C11 -64.5(3) . . . . ?
N4 Cd1 N3 C11 179.4(2) . . . . ?
N5 Cd1 N3 C10 -18.2(3) . . . . ?
N2 Cd1 N3 C10 148.6(3) . . . . ?
N6 Cd1 N3 C10 -89.7(2) . . . . ?
N1 Cd1 N3 C10 175.3(2) . . . . ?
N4 Cd1 N3 C10 59.1(3) . . . . ?
N5 Cd1 N4 C22 149.3(4) . . . . ?
N2 Cd1 N4 C22 -26.0(3) . . . . ?
N6 Cd1 N4 C22 174.1(3) . . . . ?
N1 Cd1 N4 C22 -96.5(3) . . . . ?
N3 Cd1 N4 C22 48.6(4) . . . . ?
N5 Cd1 N4 C20 29.6(2) . . . . ?
N2 Cd1 N4 C20 -145.7(2) . . . . ?
N6 Cd1 N4 C20 54.4(3) . . . . ?
N1 Cd1 N4 C20 143.8(2) . . . . ?
N3 Cd1 N4 C20 -71.1(2) . . . . ?
N5 Cd1 N4 C21 -86.9(2) . . . . ?
N2 Cd1 N4 C21 97.8(2) . . . . ?
N6 Cd1 N4 C21 -62.0(3) . . . . ?
N1 Cd1 N4 C21 27.3(2) . . . . ?
N3 Cd1 N4 C21 172.5(2) . . . . ?
N2 Cd1 N5 C17 -173.7(4) . . . . ?
N6 Cd1 N5 C17 1.1(2) . . . . ?
N1 Cd1 N5 C17 80.3(3) . . . . ?
N3 Cd1 N5 C17 -90.4(2) . . . . ?
N4 Cd1 N5 C17 164.8(3) . . . . ?
N2 Cd1 N5 C19 15.1(6) . . . . ?
N6 Cd1 N5 C19 -170.2(2) . . . . ?
N1 Cd1 N5 C19 -90.9(2) . . . . ?
N3 Cd1 N5 C19 98.4(2) . . . . ?
N4 Cd1 N5 C19 -6.5(2) . . . . ?
N5 Cd1 N6 C12 -176.2(3) . . . . ?
N2 Cd1 N6 C12 2.5(3) . . . . ?
N1 Cd1 N6 C12 68.0(3) . . . . ?
N3 Cd1 N6 C12 -72.6(3) . . . . ?
N4 Cd1 N6 C12 158.5(3) . . . . ?
N5 Cd1 N6 C16 -8.7(2) . . . . ?
N2 Cd1 N6 C16 169.99(19) . . . . ?
N1 Cd1 N6 C16 -124.5(2) . . . . ?
N3 Cd1 N6 C16 94.9(2) . . . . ?
N4 Cd1 N6 C16 -34.0(3) . . . . ?
C5 N1 C1 C2 -3.2(5) . . . . ?
Cd1 N1 C1 C2 152.8(3) . . . . ?
N1 C1 C2 C3 1.3(6) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C1 N1 C5 C4 3.4(5) . . . . ?
Cd1 N1 C5 C4 -155.1(2) . . . . ?
C1 N1 C5 C6 -176.6(3) . . . . ?
Cd1 N1 C5 C6 24.8(3) . . . . ?
C3 C4 C5 N1 -1.8(5) . . . . ?
C3 C4 C5 C6 178.3(3) . . . . ?
C8 N2 C6 C7 -3.3(5) . . . . ?
Cd1 N2 C6 C7 176.4(3) . . . . ?
C8 N2 C6 C5 176.1(3) . . . . ?
Cd1 N2 C6 C5 -4.1(4) . . . . ?
N1 C5 C6 N2 -14.8(4) . . . . ?
C4 C5 C6 N2 165.2(3) . . . . ?
N1 C5 C6 C7 164.6(3) . . . . ?
C4 C5 C6 C7 -15.4(5) . . . . ?
C6 N2 C8 C9 161.4(3) . . . . ?
Cd1 N2 C8 C9 -18.4(3) . . . . ?
C11 N3 C9 C8 68.8(3) . . . . ?
C10 N3 C9 C8 -171.9(3) . . . . ?
Cd1 N3 C9 C8 -49.4(3) . . . . ?
N2 C8 C9 N3 46.5(4) . . . . ?
C16 N6 C12 C13 -2.2(5) . . . . ?
Cd1 N6 C12 C13 164.9(3) . . . . ?
N6 C12 C13 C14 0.0(6) . . . . ?
C12 C13 C14 C15 2.4(6) . . . . ?
C13 C14 C15 C16 -2.5(5) . . . . ?
C12 N6 C16 C15 2.1(5) . . . . ?
Cd1 N6 C16 C15 -166.5(2) . . . . ?
C12 N6 C16 C17 -177.0(3) . . . . ?
Cd1 N6 C16 C17 14.4(3) . . . . ?
C14 C15 C16 N6 0.3(5) . . . . ?
C14 C15 C16 C17 179.2(3) . . . . ?
C19 N5 C17 C16 176.7(3) . . . . ?
Cd1 N5 C17 C16 6.0(4) . . . . ?
C19 N5 C17 C18 -3.6(5) . . . . ?
Cd1 N5 C17 C18 -174.3(3) . . . . ?
N6 C16 C17 N5 -13.9(4) . . . . ?
C15 C16 C17 N5 167.0(3) . . . . ?
N6 C16 C17 C18 166.3(3) . . . . ?
C15 C16 C17 C18 -12.7(5) . . . . ?
C17 N5 C19 C20 170.6(3) . . . . ?
Cd1 N5 C19 C20 -18.4(4) . . . . ?
C22 N4 C20 C19 -174.6(3) . . . . ?
C21 N4 C20 C19 65.5(4) . . . . ?
Cd1 N4 C20 C19 -51.7(3) . . . . ?
N5 C19 C20 N4 49.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.687
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.061
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sm120
_database_code_depnum_ccdc_archive 'CCDC 958289'
_audit_update_record             
;
2013-08-30 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H22 Cd N4 O4'
_chemical_formula_weight         446.78

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           Triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   8.43810(10)
_cell_length_b                   10.1003(3)
_cell_length_c                   11.3030(2)
_cell_angle_alpha                76.078(2)
_cell_angle_beta                 81.463(2)
_cell_angle_gamma                89.501(2)
_cell_volume                     924.30(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6892
_cell_measurement_theta_min      3.1144
_cell_measurement_theta_max      32.5310

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_absorpt_coefficient_mu    1.209
_exptl_absorpt_correction_T_min  0.7685
_exptl_absorpt_correction_T_max  0.8587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6664
_diffrn_reflns_av_R_equivalents  0.0117
_diffrn_reflns_av_sigmaI/netI    0.0152
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3247
_reflns_number_gt                3172
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0205P)²+0.5172P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3247
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0181
_refine_ls_R_factor_gt           0.0177
_refine_ls_wR_factor_ref         0.0453
_refine_ls_wR_factor_gt          0.0451
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_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 0.369604(15) 0.235857(13) 0.775727(12) 0.02110(6) Uani 1 1 d . . .
O1 O 0.21673(17) 0.08508(14) 0.92608(13) 0.0287(3) Uani 1 1 d . . .
O2 O 0.18976(19) 0.27983(15) 0.98347(13) 0.0348(4) Uani 1 1 d . . .
O3 O 0.5642(2) 0.05112(17) 0.75437(14) 0.0424(4) Uani 1 1 d . . .
O4 O 0.49318(18) 0.19363(16) 0.59325(14) 0.0350(4) Uani 1 1 d . . .
N1 N 0.56468(19) 0.29533(17) 0.88292(15) 0.0253(4) Uani 1 1 d . . .
N2 N 0.41909(19) 0.47090(17) 0.72043(15) 0.0259(4) Uani 1 1 d . . .
N3 N 0.16090(19) 0.33591(18) 0.65793(15) 0.0261(4) Uani 1 1 d . . .
N4 N -0.0036(3) 0.2269(3) 1.2813(2) 0.0495(5) Uani 1 1 d . . .
C1 C 0.6287(2) 0.2060(2) 0.9689(2) 0.0301(5) Uani 1 1 d . . .
H1 H 0.6006 0.1120 0.9832 0.036 Uiso 1 1 calc R . .
C2 C 0.7343(3) 0.2441(3) 1.0381(2) 0.0356(5) Uani 1 1 d . . .
H2 H 0.7766 0.1780 1.0997 0.043 Uiso 1 1 calc R . .
C3 C 0.7765(3) 0.3797(3) 1.0158(2) 0.0374(5) Uani 1 1 d . . .
H3 H 0.8494 0.4088 1.0615 0.045 Uiso 1 1 calc R . .
C4 C 0.7119(2) 0.4739(2) 0.9260(2) 0.0332(5) Uani 1 1 d . . .
H4 H 0.7405 0.5681 0.9089 0.040 Uiso 1 1 calc R . .
C5 C 0.6047(2) 0.4282(2) 0.86136(19) 0.0262(4) Uani 1 1 d . . .
C6 C 0.5239(2) 0.5238(2) 0.76642(19) 0.0274(4) Uani 1 1 d . . .
C7 C 0.5711(3) 0.6723(2) 0.7341(3) 0.0432(6) Uani 1 1 d . . .
H7A H 0.5127 0.7216 0.6689 0.065 Uiso 1 1 calc R . .
H7B H 0.6866 0.6835 0.7050 0.065 Uiso 1 1 calc R . .
H7C H 0.5448 0.7089 0.8072 0.065 Uiso 1 1 calc R . .
C8 C 0.3220(3) 0.5501(2) 0.6332(2) 0.0333(5) Uani 1 1 d . . .
H8A H 0.3903 0.6202 0.5705 0.040 Uiso 1 1 calc R . .
H8B H 0.2378 0.5971 0.6772 0.040 Uiso 1 1 calc R . .
C9 C 0.2449(3) 0.4551(2) 0.57060(19) 0.0322(5) Uani 1 1 d . . .
H9A H 0.1676 0.5070 0.5206 0.039 Uiso 1 1 calc R . .
H9B H 0.3290 0.4231 0.5139 0.039 Uiso 1 1 calc R . .
C10 C 0.0226(3) 0.3767(3) 0.7351(2) 0.0363(5) Uani 1 1 d . . .
H10A H 0.0599 0.4324 0.7861 0.054 Uiso 1 1 calc R . .
H10B H -0.0350 0.2951 0.7884 0.054 Uiso 1 1 calc R . .
H10C H -0.0493 0.4299 0.6823 0.054 Uiso 1 1 calc R . .
C11 C 0.1078(3) 0.2426(3) 0.5896(2) 0.0383(5) Uani 1 1 d . . .
H11A H 0.0331 0.2890 0.5356 0.057 Uiso 1 1 calc R . .
H11B H 0.0539 0.1621 0.6478 0.057 Uiso 1 1 calc R . .
H11C H 0.2008 0.2142 0.5396 0.057 Uiso 1 1 calc R . .
C12 C 0.1745(2) 0.1549(2) 1.00451(17) 0.0229(4) Uani 1 1 d . . .
C13 C 0.1040(2) 0.0725(2) 1.13290(18) 0.0281(4) Uani 1 1 d . . .
H13A H 0.0153 0.0127 1.1259 0.034 Uiso 1 1 calc R . .
H13B H 0.1875 0.0133 1.1689 0.034 Uiso 1 1 calc R . .
C14 C 0.0434(3) 0.1592(3) 1.2162(2) 0.0349(5) Uani 1 1 d . . .
C15 C 0.5777(2) 0.0978(2) 0.64098(18) 0.0255(4) Uani 1 1 d . . .
C16 C 0.6980(3) 0.0396(3) 0.5554(2) 0.0366(5) Uani 1 1 d . . .
H16A H 0.7777 -0.0111 0.6019 0.055 Uiso 1 1 calc R . .
H16B H 0.7518 0.1141 0.4897 0.055 Uiso 1 1 calc R . .
H16C H 0.6426 -0.0220 0.5189 0.055 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 O1 2.2381(14) . ?
Cd1 O4 2.3022(15) . ?
Cd1 N2 2.3296(17) . ?
Cd1 N1 2.3448(16) . ?
Cd1 N3 2.4317(16) . ?
Cd1 O3 2.5066(16) . ?
Cd1 C15 2.745(2) . ?
O1 C12 1.270(2) . ?
O2 C12 1.231(3) . ?
O3 C15 1.243(3) . ?
O4 C15 1.260(2) . ?
N1 C1 1.332(3) . ?
N1 C5 1.342(3) . ?
N2 C6 1.271(3) . ?
N2 C8 1.460(3) . ?
N3 C11 1.466(3) . ?
N3 C10 1.468(3) . ?
N3 C9 1.470(3) . ?
N4 C14 1.148(3) . ?
C1 C2 1.384(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.371(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.501(3) . ?
C6 C7 1.499(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.523(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.524(3) . ?
C13 C14 1.470(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C15 C16 1.511(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cd1 O4 125.20(6) . . ?
O1 Cd1 N2 137.17(5) . . ?
O4 Cd1 N2 96.49(6) . . ?
O1 Cd1 N1 101.24(5) . . ?
O4 Cd1 N1 109.23(6) . . ?
N2 Cd1 N1 69.46(6) . . ?
O1 Cd1 N3 98.52(5) . . ?
O4 Cd1 N3 85.26(5) . . ?
N2 Cd1 N3 73.26(6) . . ?
N1 Cd1 N3 141.14(6) . . ?
O1 Cd1 O3 89.00(5) . . ?
O4 Cd1 O3 53.98(5) . . ?
N2 Cd1 O3 127.95(6) . . ?
N1 Cd1 O3 80.90(6) . . ?
N3 Cd1 O3 132.73(6) . . ?
O1 Cd1 C15 109.14(6) . . ?
O4 Cd1 C15 27.15(6) . . ?
N2 Cd1 C15 113.14(6) . . ?
N1 Cd1 C15 94.34(6) . . ?
N3 Cd1 C15 110.25(6) . . ?
O3 Cd1 C15 26.89(5) . . ?
C12 O1 Cd1 102.04(12) . . ?
C15 O3 Cd1 87.30(12) . . ?
C15 O4 Cd1 96.39(12) . . ?
C1 N1 C5 118.97(18) . . ?
C1 N1 Cd1 123.54(14) . . ?
C5 N1 Cd1 117.34(13) . . ?
C6 N2 C8 123.61(18) . . ?
C6 N2 Cd1 120.40(14) . . ?
C8 N2 Cd1 115.99(13) . . ?
C11 N3 C10 109.85(17) . . ?
C11 N3 C9 109.42(17) . . ?
C10 N3 C9 111.29(17) . . ?
C11 N3 Cd1 111.06(13) . . ?
C10 N3 Cd1 112.67(12) . . ?
C9 N3 Cd1 102.33(12) . . ?
N1 C1 C2 122.9(2) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 119.5(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.4(2) . . ?
N1 C5 C6 116.18(18) . . ?
C4 C5 C6 122.42(19) . . ?
N2 C6 C7 125.3(2) . . ?
N2 C6 C5 116.52(18) . . ?
C7 C6 C5 118.23(19) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C9 109.40(17) . . ?
N2 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
N2 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
N3 C9 C8 113.33(17) . . ?
N3 C9 H9A 108.9 . . ?
C8 C9 H9A 108.9 . . ?
N3 C9 H9B 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 O1 124.64(18) . . ?
O2 C12 C13 120.16(18) . . ?
O1 C12 C13 115.19(17) . . ?
C14 C13 C12 112.69(18) . . ?
C14 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
N4 C14 C13 179.8(3) . . ?
O3 C15 O4 122.07(19) . . ?
O3 C15 C16 120.18(19) . . ?
O4 C15 C16 117.74(18) . . ?
O3 C15 Cd1 65.81(11) . . ?
O4 C15 Cd1 56.47(10) . . ?
C16 C15 Cd1 172.54(15) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 Cd1 O1 C12 -178.85(11) . . . . ?
N2 Cd1 O1 C12 -14.13(15) . . . . ?
N1 Cd1 O1 C12 57.70(12) . . . . ?
N3 Cd1 O1 C12 -88.65(12) . . . . ?
O3 Cd1 O1 C12 138.22(12) . . . . ?
C15 Cd1 O1 C12 156.36(11) . . . . ?
O1 Cd1 O3 C15 139.43(13) . . . . ?
O4 Cd1 O3 C15 2.91(12) . . . . ?
N2 Cd1 O3 C15 -64.15(15) . . . . ?
N1 Cd1 O3 C15 -119.02(13) . . . . ?
N3 Cd1 O3 C15 38.74(16) . . . . ?
O1 Cd1 O4 C15 -60.24(14) . . . . ?
N2 Cd1 O4 C15 130.15(13) . . . . ?
N1 Cd1 O4 C15 59.67(14) . . . . ?
N3 Cd1 O4 C15 -157.33(13) . . . . ?
O3 Cd1 O4 C15 -2.89(12) . . . . ?
O1 Cd1 N1 C1 39.63(17) . . . . ?
O4 Cd1 N1 C1 -94.14(16) . . . . ?
N2 Cd1 N1 C1 176.02(17) . . . . ?
N3 Cd1 N1 C1 158.79(14) . . . . ?
O3 Cd1 N1 C1 -47.51(16) . . . . ?
C15 Cd1 N1 C1 -70.88(16) . . . . ?
O1 Cd1 N1 C5 -135.75(14) . . . . ?
O4 Cd1 N1 C5 90.48(14) . . . . ?
N2 Cd1 N1 C5 0.64(13) . . . . ?
N3 Cd1 N1 C5 -16.59(18) . . . . ?
O3 Cd1 N1 C5 137.11(14) . . . . ?
C15 Cd1 N1 C5 113.74(14) . . . . ?
O1 Cd1 N2 C6 85.91(16) . . . . ?
O4 Cd1 N2 C6 -106.61(15) . . . . ?
N1 Cd1 N2 C6 1.54(14) . . . . ?
N3 Cd1 N2 C6 170.35(16) . . . . ?
O3 Cd1 N2 C6 -58.05(17) . . . . ?
C15 Cd1 N2 C6 -84.32(16) . . . . ?
O1 Cd1 N2 C8 -93.28(15) . . . . ?
O4 Cd1 N2 C8 74.20(14) . . . . ?
N1 Cd1 N2 C8 -177.66(15) . . . . ?
N3 Cd1 N2 C8 -8.84(13) . . . . ?
O3 Cd1 N2 C8 122.76(13) . . . . ?
C15 Cd1 N2 C8 96.49(14) . . . . ?
O1 Cd1 N3 C11 -74.19(14) . . . . ?
O4 Cd1 N3 C11 50.73(14) . . . . ?
N2 Cd1 N3 C11 148.98(15) . . . . ?
N1 Cd1 N3 C11 165.81(13) . . . . ?
O3 Cd1 N3 C11 22.37(17) . . . . ?
C15 Cd1 N3 C11 39.93(15) . . . . ?
O1 Cd1 N3 C10 49.53(15) . . . . ?
O4 Cd1 N3 C10 174.45(15) . . . . ?
N2 Cd1 N3 C10 -87.30(15) . . . . ?
N1 Cd1 N3 C10 -70.47(17) . . . . ?
O3 Cd1 N3 C10 146.09(14) . . . . ?
C15 Cd1 N3 C10 163.65(14) . . . . ?
O1 Cd1 N3 C9 169.14(12) . . . . ?
O4 Cd1 N3 C9 -65.94(13) . . . . ?
N2 Cd1 N3 C9 32.31(12) . . . . ?
N1 Cd1 N3 C9 49.14(16) . . . . ?
O3 Cd1 N3 C9 -94.30(14) . . . . ?
C15 Cd1 N3 C9 -76.74(13) . . . . ?
C5 N1 C1 C2 0.5(3) . . . . ?
Cd1 N1 C1 C2 -174.79(16) . . . . ?
N1 C1 C2 C3 -1.0(3) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C1 N1 C5 C4 0.5(3) . . . . ?
Cd1 N1 C5 C4 176.10(14) . . . . ?
C1 N1 C5 C6 -177.99(17) . . . . ?
Cd1 N1 C5 C6 -2.4(2) . . . . ?
C3 C4 C5 N1 -1.0(3) . . . . ?
C3 C4 C5 C6 177.39(18) . . . . ?
C8 N2 C6 C7 -3.6(3) . . . . ?
Cd1 N2 C6 C7 177.29(16) . . . . ?
C8 N2 C6 C5 175.86(17) . . . . ?
Cd1 N2 C6 C5 -3.3(2) . . . . ?
N1 C5 C6 N2 3.7(3) . . . . ?
C4 C5 C6 N2 -174.74(18) . . . . ?
N1 C5 C6 C7 -176.78(18) . . . . ?
C4 C5 C6 C7 4.7(3) . . . . ?
C6 N2 C8 C9 164.32(18) . . . . ?
Cd1 N2 C8 C9 -16.5(2) . . . . ?
C11 N3 C9 C8 -173.17(17) . . . . ?
C10 N3 C9 C8 65.2(2) . . . . ?
Cd1 N3 C9 C8 -55.32(18) . . . . ?
N2 C8 C9 N3 50.8(2) . . . . ?
Cd1 O1 C12 O2 13.7(2) . . . . ?
Cd1 O1 C12 C13 -164.91(13) . . . . ?
O2 C12 C13 C14 6.8(3) . . . . ?
O1 C12 C13 C14 -174.54(17) . . . . ?
C12 C13 C14 N4 -98(100) . . . . ?
Cd1 O3 C15 O4 -5.1(2) . . . . ?
Cd1 O3 C15 C16 175.01(18) . . . . ?
Cd1 O4 C15 O3 5.6(2) . . . . ?
Cd1 O4 C15 C16 -174.53(16) . . . . ?
O1 Cd1 C15 O3 -43.50(14) . . . . ?
O4 Cd1 C15 O3 -174.8(2) . . . . ?
N2 Cd1 C15 O3 129.49(13) . . . . ?
N1 Cd1 C15 O3 59.99(13) . . . . ?
N3 Cd1 C15 O3 -150.66(12) . . . . ?
O1 Cd1 C15 O4 131.33(12) . . . . ?
N2 Cd1 C15 O4 -55.68(14) . . . . ?
N1 Cd1 C15 O4 -125.18(13) . . . . ?
N3 Cd1 C15 O4 24.16(14) . . . . ?
O3 Cd1 C15 O4 174.8(2) . . . . ?
O1 Cd1 C15 C16 171.9(11) . . . . ?
O4 Cd1 C15 C16 40.6(11) . . . . ?
N2 Cd1 C15 C16 -15.1(11) . . . . ?
N1 Cd1 C15 C16 -84.6(11) . . . . ?
N3 Cd1 C15 C16 64.7(11) . . . . ?
O3 Cd1 C15 C16 -144.6(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.053
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sm098
_database_code_depnum_ccdc_archive 'CCDC 958287'
_audit_update_record             
;
2013-08-30 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H17 Cd N9'
_chemical_formula_weight         387.74

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   8.7930(7)
_cell_length_b                   15.6776(13)
_cell_length_c                   11.6958(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.422(9)
_cell_angle_gamma                90.00
_cell_volume                     1538.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    22741
_cell_measurement_theta_min      3.0168
_cell_measurement_theta_max      32.5613

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    1.428
_exptl_absorpt_correction_T_min  0.6500
_exptl_absorpt_correction_T_max  0.7831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10003
_diffrn_reflns_av_R_equivalents  0.1076
_diffrn_reflns_av_sigmaI/netI    0.0561
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2712
_reflns_number_gt                2342
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0935P)²+15.9414P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2712
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0825
_refine_ls_wR_factor_ref         0.2302
_refine_ls_wR_factor_gt          0.2221
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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 0.12350(8) 0.00294(4) 0.66252(5) 0.0475(3) Uani 1 1 d . . .
N1 N 0.281(3) 0.1083(10) 0.7585(11) 0.181(10) Uani 1 1 d . . .
N2 N 0.3413(10) 0.1221(7) 0.8563(7) 0.065(3) Uani 1 1 d . . .
N3 N 0.4095(15) 0.1406(10) 0.9485(9) 0.108(5) Uani 1 1 d . . .
N4 N 0.0871(10) 0.0691(6) 0.4809(6) 0.058(2) Uani 1 1 d . . .
N5 N 0.1606(8) 0.1263(7) 0.4564(6) 0.055(2) Uani 1 1 d . . .
N6 N 0.2276(11) 0.1825(9) 0.4298(8) 0.090(4) Uani 1 1 d . . .
N7 N -0.0568(12) 0.0260(8) 0.7796(7) 0.076(3) Uani 1 1 d . . .
N8 N 0.1241(9) -0.1109(6) 0.7901(6) 0.049(2) Uani 1 1 d . . .
N9 N 0.3252(10) -0.0923(9) 0.6432(7) 0.090(4) Uani 1 1 d . . .
C1 C -0.129(2) 0.0976(12) 0.7926(10) 0.119(7) Uani 1 1 d . . .
H1 H -0.1103 0.1472 0.7520 0.143 Uiso 1 1 calc R . .
C2 C -0.232(2) 0.1036(16) 0.8646(14) 0.131(10) Uani 1 1 d . . .
H2 H -0.2814 0.1562 0.8730 0.157 Uiso 1 1 calc R . .
C3 C -0.258(2) 0.036(3) 0.9184(16) 0.178(15) Uani 1 1 d . . .
H3 H -0.3261 0.0404 0.9678 0.214 Uiso 1 1 calc R . .
C4 C -0.1889(15) -0.0471(16) 0.9076(10) 0.110(7) Uani 1 1 d . . .
H4 H -0.2116 -0.0975 0.9445 0.132 Uiso 1 1 calc R . .
C5 C -0.0857(12) -0.0447(11) 0.8371(8) 0.072(4) Uani 1 1 d . . .
C6 C 0.0055(12) -0.1216(9) 0.8278(8) 0.064(3) Uani 1 1 d . . .
C7 C -0.0390(18) -0.2071(12) 0.8679(12) 0.113(6) Uani 1 1 d . . .
H7A H -0.0087 -0.2525 0.8213 0.170 Uiso 1 1 calc R . .
H7B H -0.1543 -0.2090 0.8552 0.170 Uiso 1 1 calc R . .
H7C H 0.0171 -0.2152 0.9532 0.170 Uiso 1 1 calc R . .
C8 C 0.2305(16) -0.1799(9) 0.7814(11) 0.083(4) Uani 1 1 d . . .
H8A H 0.1736 -0.2204 0.7180 0.099 Uiso 1 1 calc R . .
H8B H 0.2657 -0.2112 0.8584 0.099 Uiso 1 1 calc R . .
C9 C 0.3712(15) -0.1444(11) 0.7525(9) 0.090(5) Uani 1 1 d . . .
H9A H 0.4339 -0.1090 0.8204 0.108 Uiso 1 1 calc R . .
H9B H 0.4400 -0.1919 0.7418 0.108 Uiso 1 1 calc R . .
C10 C 0.4601(18) -0.041(2) 0.639(2) 0.208(16) Uani 1 1 d . . .
H10A H 0.4967 -0.0063 0.7115 0.312 Uiso 1 1 calc R . .
H10B H 0.4281 -0.0033 0.5684 0.312 Uiso 1 1 calc R . .
H10C H 0.5468 -0.0782 0.6325 0.312 Uiso 1 1 calc R . .
C11 C 0.268(3) -0.1468(16) 0.5364(11) 0.189(14) Uani 1 1 d . . .
H11A H 0.2501 -0.1118 0.4641 0.283 Uiso 1 1 calc R . .
H11B H 0.1682 -0.1744 0.5364 0.283 Uiso 1 1 calc R . .
H11C H 0.3484 -0.1905 0.5375 0.283 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N1 2.231(12) . ?
Cd1 N4 2.299(7) . ?
Cd1 N8 2.325(8) . ?
Cd1 N4 2.379(8) 3_556 ?
Cd1 N9 2.380(9) . ?
Cd1 N7 2.412(10) . ?
N1 N2 1.128(13) . ?
N2 N3 1.104(13) . ?
N4 N5 1.190(12) . ?
N4 Cd1 2.379(8) 3_556 ?
N5 N6 1.153(14) . ?
N7 C1 1.319(16) . ?
N7 C5 1.359(19) . ?
N8 C6 1.259(13) . ?
N8 C8 1.453(14) . ?
N9 C10 1.45(2) . ?
N9 C9 1.467(15) . ?
N9 C11 1.47(2) . ?
C1 C2 1.42(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.29(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.46(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.470(18) . ?
C6 C7 1.509(19) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.49(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cd1 N4 91.4(4) . . ?
N1 Cd1 N8 111.3(4) . . ?
N4 Cd1 N8 155.8(3) . . ?
N1 Cd1 N4 160.3(5) . 3_556 ?
N4 Cd1 N4 72.5(4) . 3_556 ?
N8 Cd1 N4 86.5(3) . 3_556 ?
N1 Cd1 N9 98.3(7) . . ?
N4 Cd1 N9 95.6(3) . . ?
N8 Cd1 N9 73.8(3) . . ?
N4 Cd1 N9 94.6(4) 3_556 . ?
N1 Cd1 N7 91.1(7) . . ?
N4 Cd1 N7 121.6(3) . . ?
N8 Cd1 N7 68.1(3) . . ?
N4 Cd1 N7 88.1(3) 3_556 . ?
N9 Cd1 N7 141.5(4) . . ?
N2 N1 Cd1 133.2(12) . . ?
N3 N2 N1 173.3(17) . . ?
N5 N4 Cd1 128.9(6) . . ?
N5 N4 Cd1 123.5(5) . 3_556 ?
Cd1 N4 Cd1 107.5(4) . 3_556 ?
N6 N5 N4 177.9(9) . . ?
C1 N7 C5 118.0(13) . . ?
C1 N7 Cd1 127.7(12) . . ?
C5 N7 Cd1 114.3(7) . . ?
C6 N8 C8 122.9(11) . . ?
C6 N8 Cd1 118.9(7) . . ?
C8 N8 Cd1 113.9(7) . . ?
C10 N9 C9 109.1(11) . . ?
C10 N9 C11 111.4(16) . . ?
C9 N9 C11 110.5(15) . . ?
C10 N9 Cd1 107.2(14) . . ?
C9 N9 Cd1 106.6(6) . . ?
C11 N9 Cd1 111.8(7) . . ?
N7 C1 C2 122.7(19) . . ?
N7 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C3 C2 C1 118.3(18) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 123.6(17) . . ?
C2 C3 H3 118.2 . . ?
C4 C3 H3 118.2 . . ?
C5 C4 C3 113(2) . . ?
C5 C4 H4 123.6 . . ?
C3 C4 H4 123.6 . . ?
N7 C5 C4 124.4(15) . . ?
N7 C5 C6 116.4(9) . . ?
C4 C5 C6 119.1(15) . . ?
N8 C6 C5 116.4(11) . . ?
N8 C6 C7 123.1(13) . . ?
C5 C6 C7 120.5(12) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N8 C8 C9 109.6(12) . . ?
N8 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
N8 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
N9 C9 C8 112.0(9) . . ?
N9 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
N9 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N9 C10 H10A 109.5 . . ?
N9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N9 C11 H11A 109.5 . . ?
N9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 Cd1 N1 N2 176(3) . . . . ?
N8 Cd1 N1 N2 -13(3) . . . . ?
N4 Cd1 N1 N2 141.1(14) 3_556 . . . ?
N9 Cd1 N1 N2 -89(3) . . . . ?
N7 Cd1 N1 N2 54(3) . . . . ?
Cd1 N1 N2 N3 160(14) . . . . ?
N1 Cd1 N4 N5 14.7(12) . . . . ?
N8 Cd1 N4 N5 -145.8(9) . . . . ?
N4 Cd1 N4 N5 -176.8(13) 3_556 . . . ?
N9 Cd1 N4 N5 -83.8(10) . . . . ?
N7 Cd1 N4 N5 106.8(10) . . . . ?
N1 Cd1 N4 Cd1 -168.5(7) . . . 3_556 ?
N8 Cd1 N4 Cd1 31.0(9) . . . 3_556 ?
N4 Cd1 N4 Cd1 0.0 3_556 . . 3_556 ?
N9 Cd1 N4 Cd1 93.1(5) . . . 3_556 ?
N7 Cd1 N4 Cd1 -76.4(5) . . . 3_556 ?
Cd1 N4 N5 N6 -152(33) . . . . ?
Cd1 N4 N5 N6 31(34) 3_556 . . . ?
N1 Cd1 N7 C1 55.1(12) . . . . ?
N4 Cd1 N7 C1 -37.2(12) . . . . ?
N8 Cd1 N7 C1 167.8(12) . . . . ?
N4 Cd1 N7 C1 -105.2(11) 3_556 . . . ?
N9 Cd1 N7 C1 159.9(10) . . . . ?
N1 Cd1 N7 C5 -125.3(9) . . . . ?
N4 Cd1 N7 C5 142.4(7) . . . . ?
N8 Cd1 N7 C5 -12.7(7) . . . . ?
N4 Cd1 N7 C5 74.4(8) 3_556 . . . ?
N9 Cd1 N7 C5 -20.6(11) . . . . ?
N1 Cd1 N8 C6 104.3(11) . . . . ?
N4 Cd1 N8 C6 -96.7(10) . . . . ?
N4 Cd1 N8 C6 -67.2(8) 3_556 . . . ?
N9 Cd1 N8 C6 -163.0(9) . . . . ?
N7 Cd1 N8 C6 22.1(8) . . . . ?
N1 Cd1 N8 C8 -98.3(10) . . . . ?
N4 Cd1 N8 C8 60.7(11) . . . . ?
N4 Cd1 N8 C8 90.2(8) 3_556 . . . ?
N9 Cd1 N8 C8 -5.6(8) . . . . ?
N7 Cd1 N8 C8 179.5(8) . . . . ?
N1 Cd1 N9 C10 -28.9(10) . . . . ?
N4 Cd1 N9 C10 63.4(10) . . . . ?
N8 Cd1 N9 C10 -138.8(10) . . . . ?
N4 Cd1 N9 C10 136.2(10) 3_556 . . . ?
N7 Cd1 N9 C10 -131.1(10) . . . . ?
N1 Cd1 N9 C9 87.9(10) . . . . ?
N4 Cd1 N9 C9 -179.9(10) . . . . ?
N8 Cd1 N9 C9 -22.0(9) . . . . ?
N4 Cd1 N9 C9 -107.1(10) 3_556 . . . ?
N7 Cd1 N9 C9 -14.4(13) . . . . ?
N1 Cd1 N9 C11 -151.2(14) . . . . ?
N4 Cd1 N9 C11 -59.0(14) . . . . ?
N8 Cd1 N9 C11 98.9(14) . . . . ?
N4 Cd1 N9 C11 13.8(14) 3_556 . . . ?
N7 Cd1 N9 C11 106.5(13) . . . . ?
C5 N7 C1 C2 1(2) . . . . ?
Cd1 N7 C1 C2 -179.7(11) . . . . ?
N7 C1 C2 C3 -1(3) . . . . ?
C1 C2 C3 C4 -1(3) . . . . ?
C2 C3 C4 C5 3(3) . . . . ?
C1 N7 C5 C4 1.2(17) . . . . ?
Cd1 N7 C5 C4 -178.4(9) . . . . ?
C1 N7 C5 C6 -175.7(10) . . . . ?
Cd1 N7 C5 C6 4.8(12) . . . . ?
C3 C4 C5 N7 -2.8(18) . . . . ?
C3 C4 C5 C6 174.0(11) . . . . ?
C8 N8 C6 C5 176.9(9) . . . . ?
Cd1 N8 C6 C5 -27.9(11) . . . . ?
C8 N8 C6 C7 0.0(15) . . . . ?
Cd1 N8 C6 C7 155.2(8) . . . . ?
N7 C5 C6 N8 14.6(14) . . . . ?
C4 C5 C6 N8 -162.5(10) . . . . ?
N7 C5 C6 C7 -168.4(10) . . . . ?
C4 C5 C6 C7 14.5(16) . . . . ?
C6 N8 C8 C9 -171.2(9) . . . . ?
Cd1 N8 C8 C9 32.5(11) . . . . ?
C10 N9 C9 C8 163.9(17) . . . . ?
C11 N9 C9 C8 -73.2(14) . . . . ?
Cd1 N9 C9 C8 48.5(14) . . . . ?
N8 C8 C9 N9 -55.5(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         2.110
_refine_diff_density_min         -1.781
_refine_diff_density_rms         0.179
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1498770'
_audit_update_record             
;
2016-08-11 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H42 Cd2 N18'
_chemical_formula_weight         855.59

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   19.8810(4)
_cell_length_b                   10.8934(2)
_cell_length_c                   16.2898(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.828(2)
_cell_angle_gamma                90
_cell_volume                     3465.10(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    23281
_cell_measurement_theta_min      3.2300
_cell_measurement_theta_max      32.0270

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    1.277
_shelx_estimated_absorpt_T_min   0.678
_shelx_estimated_absorpt_T_max   0.775
_exptl_absorpt_correction_T_min  0.79925
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32482
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.911
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6087
_reflns_number_gt                5591
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
  _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0249P)²+2.5522P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6087
_refine_ls_number_parameters     435
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0220
_refine_ls_wR_factor_ref         0.0580
_refine_ls_wR_factor_gt          0.0554
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.28449(2) 0.67478(2) 1.06763(2) 0.03573(6) Uani 1 1 d . . . . .
Cd2 Cd 0.21688(2) 0.27621(2) 1.31018(2) 0.04013(6) Uani 1 1 d . . . . .
N1 N 0.40639(10) 0.65648(18) 1.07231(12) 0.0401(5) Uani 1 1 d . . . . .
N2 N 0.31245(11) 0.71494(19) 0.93809(13) 0.0429(5) Uani 1 1 d . . . . .
N3 N 0.17774(10) 0.73004(18) 0.97962(13) 0.0415(5) Uani 1 1 d . . . . .
N4 N 0.28028(14) 0.4607(2) 1.01451(15) 0.0606(6) Uani 1 1 d . . . . .
N5 N 0.27200(11) 0.43339(18) 0.94422(15) 0.0462(5) Uani 1 1 d . . . . .
N6 N 0.26416(15) 0.4086(2) 0.87304(16) 0.0664(7) Uani 1 1 d . . . . .
N7 N 0.30050(13) 0.8724(2) 1.11714(19) 0.0661(7) Uani 1 1 d . . . . .
N8 N 0.35236(12) 0.9227(2) 1.14313(14) 0.0489(5) Uani 1 1 d . . . . .
N9 N 0.40221(15) 0.9767(3) 1.16863(18) 0.0763(8) Uani 1 1 d . . . . .
N10 N 0.28478(12) 0.5890(2) 1.19248(13) 0.0518(6) Uani 1 1 d . . . . .
N11 N 0.23859(11) 0.53672(19) 1.21282(12) 0.0417(5) Uani 1 1 d . . . . .
N12 N 0.19437(12) 0.4856(2) 1.23637(15) 0.0542(6) Uani 1 1 d . . . . .
N13 N 0.32384(11) 0.3757(2) 1.35729(13) 0.0445(5) Uani 1 1 d . . . . .
N14 N 0.28674(11) 0.25906(19) 1.21179(13) 0.0416(5) Uani 1 1 d . . . . .
N15 N 0.14998(11) 0.16698(19) 1.19723(14) 0.0457(5) Uani 1 1 d . . . . .
N16 N 0.17335(14) 0.3405(3) 1.41670(16) 0.0691(8) Uani 1 1 d . . . . .
N17 N 0.11672(15) 0.3716(3) 1.41348(17) 0.0711(7) Uani 1 1 d . . . . .
N18 N 0.0619(2) 0.4039(5) 1.4144(3) 0.1348(18) Uani 1 1 d . . . . .
C1 C 0.45292(14) 0.6333(3) 1.14063(17) 0.0500(6) Uani 1 1 d . . . . .
H1 H 0.4377 0.6230 1.1921 0.060 Uiso 1 1 calc R U . . .
C2 C 0.52194(15) 0.6236(3) 1.1407(2) 0.0599(8) Uani 1 1 d . . . . .
H2 H 0.5535 0.6053 1.1906 0.072 Uiso 1 1 calc R U . . .
C3 C 0.54386(15) 0.6411(3) 1.0670(2) 0.0660(8) Uani 1 1 d . . . . .
H3 H 0.5912 0.6361 1.0649 0.079 Uiso 1 1 calc R U . . .
C4 C 0.49625(15) 0.6660(3) 0.9953(2) 0.0578(7) Uani 1 1 d . . . . .
H4 H 0.5108 0.6791 0.9437 0.069 Uiso 1 1 calc R U . . .
C5 C 0.42752(13) 0.6716(2) 0.99912(16) 0.0408(5) Uani 1 1 d . . . . .
C6 C 0.37248(14) 0.6958(2) 0.92412(16) 0.0452(6) Uani 1 1 d . . . . .
C7 C 0.3900(2) 0.6946(4) 0.83872(19) 0.0790(11) Uani 1 1 d . . . . .
H7A H 0.3803 0.6132 0.8136 0.118 Uiso 1 1 calc R U . . .
H7B H 0.4388 0.7135 0.8429 0.118 Uiso 1 1 calc R U . . .
H7C H 0.3625 0.7564 0.8037 0.118 Uiso 1 1 calc R U . . .
C8 C 0.25337(15) 0.7397(3) 0.87286(17) 0.0565(7) Uani 1 1 d . . . . .
H8A H 0.2357 0.6620 0.8456 0.068 Uiso 1 1 calc R U . . .
H8B H 0.2668 0.7940 0.8299 0.068 Uiso 1 1 calc R U . . .
C9 C 0.19836(15) 0.8011(3) 0.91111(19) 0.0553(7) Uani 1 1 d . . . . .
H9A H 0.2152 0.8826 0.9329 0.066 Uiso 1 1 calc R U . . .
H9B H 0.1575 0.8145 0.8668 0.066 Uiso 1 1 calc R U . . .
C10 C 0.13597(13) 0.6227(3) 0.94577(17) 0.0496(6) Uani 1 1 d . . . . .
H10A H 0.1634 0.5685 0.9161 0.059 Uiso 1 1 calc R U . . .
H10B H 0.0956 0.6510 0.9049 0.059 Uiso 1 1 calc R U . . .
C11 C 0.11212(15) 0.5509(3) 1.0146(2) 0.0610(8) Uani 1 1 d . . . . .
H11A H 0.0831 0.4816 0.9897 0.073 Uiso 1 1 calc R U . . .
H11B H 0.1524 0.5165 1.0527 0.073 Uiso 1 1 calc R U . . .
C12 C 0.07184(17) 0.6307(4) 1.0640(2) 0.0762(10) Uani 1 1 d . . . . .
H12A H 0.0280 0.6551 1.0282 0.091 Uiso 1 1 calc R U . . .
H12B H 0.0613 0.5837 1.1121 0.091 Uiso 1 1 calc R U . . .
C13 C 0.11263(17) 0.7438(3) 1.0952(2) 0.0684(9) Uani 1 1 d . . . . .
H13A H 0.0839 0.7995 1.1221 0.082 Uiso 1 1 calc R U . . .
H13B H 0.1528 0.7198 1.1378 0.082 Uiso 1 1 calc R U . . .
C14 C 0.13660(15) 0.8106(3) 1.0253(2) 0.0591(8) Uani 1 1 d . . . . .
H14A H 0.0963 0.8418 0.9857 0.071 Uiso 1 1 calc R U . . .
H14B H 0.1647 0.8820 1.0485 0.071 Uiso 1 1 calc R U . . .
C15 C 0.33956(15) 0.4367(3) 1.42914(17) 0.0539(7) Uani 1 1 d . . . . .
H15 H 0.3077 0.4365 1.4659 0.065 Uiso 1 1 calc R U . . .
C16 C 0.39975(16) 0.4997(3) 1.45231(19) 0.0649(8) Uani 1 1 d . . . . .
H16 H 0.4091 0.5437 1.5036 0.078 Uiso 1 1 calc R U . . .
C17 C 0.44639(16) 0.4980(3) 1.3996(2) 0.0670(8) Uani 1 1 d . . . . .
H17 H 0.4887 0.5404 1.4144 0.080 Uiso 1 1 calc R U . . .
C18 C 0.43125(14) 0.4341(3) 1.32531(18) 0.0543(7) Uani 1 1 d . . . . .
H18 H 0.4633 0.4307 1.2888 0.065 Uiso 1 1 calc R U . . .
C19 C 0.36853(12) 0.3748(2) 1.30465(16) 0.0432(6) Uani 1 1 d . . . . .
C20 C 0.34575(13) 0.3083(2) 1.22333(16) 0.0436(6) Uani 1 1 d . . . . .
C21 C 0.39257(15) 0.3056(3) 1.16057(19) 0.0593(7) Uani 1 1 d . . . . .
H21A H 0.3908 0.2241 1.1347 0.089 Uiso 1 1 calc R U . . .
H21B H 0.4396 0.3233 1.1888 0.089 Uiso 1 1 calc R U . . .
H21C H 0.3777 0.3675 1.1173 0.089 Uiso 1 1 calc R U . . .
C22 C 0.25501(15) 0.1985(3) 1.13491(17) 0.0517(7) Uani 1 1 d . . . . .
H22A H 0.2901 0.1532 1.1112 0.062 Uiso 1 1 calc R U . . .
H22B H 0.2339 0.2603 1.0935 0.062 Uiso 1 1 calc R U . . .
C23 C 0.20104(16) 0.1106(3) 1.15305(19) 0.0577(7) Uani 1 1 d . . . . .
H23A H 0.1767 0.0754 1.0996 0.069 Uiso 1 1 calc R U . . .
H23B H 0.2239 0.0421 1.1874 0.069 Uiso 1 1 calc R U . . .
C24 C 0.10328(15) 0.2488(3) 1.14264(18) 0.0556(7) Uani 1 1 d . . . . .
H24A H 0.0797 0.2023 1.0933 0.067 Uiso 1 1 calc R U . . .
H24B H 0.1298 0.3157 1.1226 0.067 Uiso 1 1 calc R U . . .
C25 C 0.05143(15) 0.3027(3) 1.1871(2) 0.0638(8) Uani 1 1 d . . . . .
H25A H 0.0201 0.3558 1.1480 0.077 Uiso 1 1 calc R U . . .
H25B H 0.0749 0.3548 1.2336 0.077 Uiso 1 1 calc R U . . .
C26 C 0.01008(17) 0.2056(4) 1.2217(2) 0.0770(10) Uani 1 1 d . . . . .
H26A H -0.0199 0.1627 1.1751 0.092 Uiso 1 1 calc R U . . .
H26B H -0.0193 0.2449 1.2569 0.092 Uiso 1 1 calc R U . . .
C27 C 0.05734(17) 0.1140(3) 1.2733(2) 0.0736(9) Uani 1 1 d . . . . .
H27A H 0.0809 0.1538 1.3255 0.088 Uiso 1 1 calc R U . . .
H27B H 0.0300 0.0447 1.2888 0.088 Uiso 1 1 calc R U . . .
C28 C 0.10973(16) 0.0658(3) 1.2261(2) 0.0631(8) Uani 1 1 d . . . . .
H28A H 0.1412 0.0096 1.2626 0.076 Uiso 1 1 calc R U . . .
H28B H 0.0864 0.0183 1.1771 0.076 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N10 2.237(2) . ?
Cd1 N7 2.299(2) . ?
Cd1 N2 2.322(2) . ?
Cd1 N3 2.404(2) . ?
Cd1 N1 2.419(2) . ?
Cd1 N4 2.483(2) . ?
Cd2 N16 2.194(2) . ?
Cd2 N14 2.317(2) . ?
Cd2 N6 2.372(2) 4_566 ?
Cd2 N15 2.377(2) . ?
Cd2 N13 2.382(2) . ?
Cd2 N12 2.578(2) . ?
N1 C1 1.331(3) . ?
N1 C5 1.347(3) . ?
N2 C6 1.273(3) . ?
N2 C8 1.454(3) . ?
N3 C9 1.478(3) . ?
N3 C10 1.479(3) . ?
N3 C14 1.491(4) . ?
N4 N5 1.164(3) . ?
N5 N6 1.172(3) . ?
N6 Cd2 2.372(2) 4_565 ?
N7 N8 1.174(3) . ?
N8 N9 1.160(3) . ?
N10 N11 1.180(3) . ?
N11 N12 1.165(3) . ?
N13 C15 1.331(3) . ?
N13 C19 1.346(3) . ?
N14 C20 1.271(3) . ?
N14 C22 1.451(3) . ?
N15 C24 1.462(3) . ?
N15 C23 1.483(3) . ?
N15 C28 1.489(4) . ?
N16 N17 1.167(4) . ?
N17 N18 1.148(4) . ?
C1 C2 1.376(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.365(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.502(4) . ?
C6 C7 1.497(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.512(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.515(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.512(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.510(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.502(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.370(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.377(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.503(4) . ?
C20 C21 1.507(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.508(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.487(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.512(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.513(5) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.501(5) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?

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
N10 Cd1 N7 95.48(10) . . ?
N10 Cd1 N2 160.82(8) . . ?
N7 Cd1 N2 95.82(9) . . ?
N10 Cd1 N3 119.86(8) . . ?
N7 Cd1 N3 91.34(8) . . ?
N2 Cd1 N3 75.29(7) . . ?
N10 Cd1 N1 96.06(8) . . ?
N7 Cd1 N1 89.67(8) . . ?
N2 Cd1 N1 68.58(7) . . ?
N3 Cd1 N1 143.77(7) . . ?
N10 Cd1 N4 85.34(8) . . ?
N7 Cd1 N4 174.02(9) . . ?
N2 Cd1 N4 81.86(8) . . ?
N3 Cd1 N4 93.39(8) . . ?
N1 Cd1 N4 84.35(8) . . ?
N16 Cd2 N14 161.70(10) . . ?
N16 Cd2 N6 96.48(10) . 4_566 ?
N14 Cd2 N6 89.41(8) . 4_566 ?
N16 Cd2 N15 121.69(9) . . ?
N14 Cd2 N15 75.24(8) . . ?
N6 Cd2 N15 91.60(9) 4_566 . ?
N16 Cd2 N13 93.49(9) . . ?
N14 Cd2 N13 69.18(7) . . ?
N6 Cd2 N13 89.42(9) 4_566 . ?
N15 Cd2 N13 144.39(7) . . ?
N16 Cd2 N12 91.53(10) . . ?
N14 Cd2 N12 79.80(7) . . ?
N6 Cd2 N12 166.54(9) 4_566 . ?
N15 Cd2 N12 93.39(8) . . ?
N13 Cd2 N12 79.27(7) . . ?
C1 N1 C5 118.7(2) . . ?
C1 N1 Cd1 125.24(18) . . ?
C5 N1 Cd1 116.06(16) . . ?
C6 N2 C8 123.7(2) . . ?
C6 N2 Cd1 121.60(17) . . ?
C8 N2 Cd1 113.63(16) . . ?
C9 N3 C10 110.4(2) . . ?
C9 N3 C14 109.0(2) . . ?
C10 N3 C14 109.2(2) . . ?
C9 N3 Cd1 104.03(15) . . ?
C10 N3 Cd1 113.29(15) . . ?
C14 N3 Cd1 110.80(17) . . ?
N5 N4 Cd1 124.88(19) . . ?
N4 N5 N6 178.4(3) . . ?
N5 N6 Cd2 126.2(2) . 4_565 ?
N8 N7 Cd1 128.2(2) . . ?
N9 N8 N7 177.4(3) . . ?
N11 N10 Cd1 126.00(18) . . ?
N12 N11 N10 177.1(3) . . ?
N11 N12 Cd2 120.05(18) . . ?
C15 N13 C19 119.3(2) . . ?
C15 N13 Cd2 123.95(18) . . ?
C19 N13 Cd2 116.61(17) . . ?
C20 N14 C22 124.0(2) . . ?
C20 N14 Cd2 121.33(18) . . ?
C22 N14 Cd2 114.44(16) . . ?
C24 N15 C23 111.8(2) . . ?
C24 N15 C28 109.0(2) . . ?
C23 N15 C28 107.7(2) . . ?
C24 N15 Cd2 111.39(16) . . ?
C23 N15 Cd2 104.39(16) . . ?
C28 N15 Cd2 112.44(17) . . ?
N17 N16 Cd2 125.3(2) . . ?
N18 N17 N16 176.6(4) . . ?
N1 C1 C2 123.5(3) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 119.2(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
N1 C5 C4 120.7(2) . . ?
N1 C5 C6 116.2(2) . . ?
C4 C5 C6 123.1(2) . . ?
N2 C6 C7 123.9(3) . . ?
N2 C6 C5 116.6(2) . . ?
C7 C6 C5 119.5(2) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C9 109.2(2) . . ?
N2 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
N2 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
N3 C9 C8 113.8(2) . . ?
N3 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
N3 C9 H9B 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
N3 C10 C11 111.4(2) . . ?
N3 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
N3 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 C10 111.6(3) . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C13 C12 C11 110.1(3) . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.2 . . ?
C14 C13 C12 111.5(3) . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
N3 C14 C13 112.1(2) . . ?
N3 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
N3 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
N13 C15 C16 122.8(3) . . ?
N13 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?
C15 C16 C17 118.5(3) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
C16 C17 C18 119.5(3) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C19 119.0(3) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
N13 C19 C18 120.9(3) . . ?
N13 C19 C20 116.0(2) . . ?
C18 C19 C20 123.1(2) . . ?
N14 C20 C19 116.8(2) . . ?
N14 C20 C21 124.2(3) . . ?
C19 C20 C21 119.0(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N14 C22 C23 109.3(2) . . ?
N14 C22 H22A 109.8 . . ?
C23 C22 H22A 109.8 . . ?
N14 C22 H22B 109.8 . . ?
C23 C22 H22B 109.8 . . ?
H22A C22 H22B 108.3 . . ?
N15 C23 C22 114.1(2) . . ?
N15 C23 H23A 108.7 . . ?
C22 C23 H23A 108.7 . . ?
N15 C23 H23B 108.7 . . ?
C22 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
N15 C24 C25 111.3(2) . . ?
N15 C24 H24A 109.4 . . ?
C25 C24 H24A 109.4 . . ?
N15 C24 H24B 109.4 . . ?
C25 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
C24 C25 C26 112.4(3) . . ?
C24 C25 H25A 109.1 . . ?
C26 C25 H25A 109.1 . . ?
C24 C25 H25B 109.1 . . ?
C26 C25 H25B 109.1 . . ?
H25A C25 H25B 107.9 . . ?
C25 C26 C27 110.1(3) . . ?
C25 C26 H26A 109.6 . . ?
C27 C26 H26A 109.6 . . ?
C25 C26 H26B 109.6 . . ?
C27 C26 H26B 109.6 . . ?
H26A C26 H26B 108.2 . . ?
C28 C27 C26 111.4(3) . . ?
C28 C27 H27A 109.4 . . ?
C26 C27 H27A 109.4 . . ?
C28 C27 H27B 109.4 . . ?
C26 C27 H27B 109.4 . . ?
H27A C27 H27B 108.0 . . ?
N15 C28 C27 111.6(2) . . ?
N15 C28 H28A 109.3 . . ?
C27 C28 H28A 109.3 . . ?
N15 C28 H28B 109.3 . . ?
C27 C28 H28B 109.3 . . ?
H28A C28 H28B 108.0 . . ?

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
C5 N1 C1 C2 -0.2(4) . . . . ?
Cd1 N1 C1 C2 -180.0(2) . . . . ?
N1 C1 C2 C3 1.3(4) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C1 N1 C5 C4 -1.4(4) . . . . ?
Cd1 N1 C5 C4 178.4(2) . . . . ?
C1 N1 C5 C6 179.2(2) . . . . ?
Cd1 N1 C5 C6 -1.0(3) . . . . ?
C3 C4 C5 N1 1.8(4) . . . . ?
C3 C4 C5 C6 -178.8(3) . . . . ?
C8 N2 C6 C7 -0.9(4) . . . . ?
Cd1 N2 C6 C7 166.7(2) . . . . ?
C8 N2 C6 C5 180.0(2) . . . . ?
Cd1 N2 C6 C5 -12.4(3) . . . . ?
N1 C5 C6 N2 8.5(3) . . . . ?
C4 C5 C6 N2 -170.9(3) . . . . ?
N1 C5 C6 C7 -170.7(3) . . . . ?
C4 C5 C6 C7 9.9(4) . . . . ?
C6 N2 C8 C9 -160.0(2) . . . . ?
Cd1 N2 C8 C9 31.5(3) . . . . ?
C10 N3 C9 C8 -73.4(3) . . . . ?
C14 N3 C9 C8 166.7(2) . . . . ?
Cd1 N3 C9 C8 48.4(3) . . . . ?
N2 C8 C9 N3 -56.1(3) . . . . ?
C9 N3 C10 C11 -178.0(2) . . . . ?
C14 N3 C10 C11 -58.2(3) . . . . ?
Cd1 N3 C10 C11 65.8(3) . . . . ?
N3 C10 C11 C12 57.1(3) . . . . ?
C10 C11 C12 C13 -53.3(4) . . . . ?
C11 C12 C13 C14 52.9(4) . . . . ?
C9 N3 C14 C13 179.0(2) . . . . ?
C10 N3 C14 C13 58.3(3) . . . . ?
Cd1 N3 C14 C13 -67.1(3) . . . . ?
C12 C13 C14 N3 -56.5(3) . . . . ?
C19 N13 C15 C16 0.2(4) . . . . ?
Cd2 N13 C15 C16 -175.7(2) . . . . ?
N13 C15 C16 C17 -1.2(5) . . . . ?
C15 C16 C17 C18 0.4(5) . . . . ?
C16 C17 C18 C19 1.2(5) . . . . ?
C15 N13 C19 C18 1.6(4) . . . . ?
Cd2 N13 C19 C18 177.76(19) . . . . ?
C15 N13 C19 C20 -177.6(2) . . . . ?
Cd2 N13 C19 C20 -1.4(3) . . . . ?
C17 C18 C19 N13 -2.3(4) . . . . ?
C17 C18 C19 C20 176.8(3) . . . . ?
C22 N14 C20 C19 175.8(2) . . . . ?
Cd2 N14 C20 C19 1.7(3) . . . . ?
C22 N14 C20 C21 -3.1(4) . . . . ?
Cd2 N14 C20 C21 -177.2(2) . . . . ?
N13 C19 C20 N14 -0.1(3) . . . . ?
C18 C19 C20 N14 -179.2(2) . . . . ?
N13 C19 C20 C21 178.8(2) . . . . ?
C18 C19 C20 C21 -0.3(4) . . . . ?
C20 N14 C22 C23 157.9(2) . . . . ?
Cd2 N14 C22 C23 -27.6(3) . . . . ?
C24 N15 C23 C22 71.8(3) . . . . ?
C28 N15 C23 C22 -168.4(2) . . . . ?
Cd2 N15 C23 C22 -48.7(3) . . . . ?
N14 C22 C23 N15 53.2(3) . . . . ?
C23 N15 C24 C25 178.8(2) . . . . ?
C28 N15 C24 C25 59.8(3) . . . . ?
Cd2 N15 C24 C25 -64.8(3) . . . . ?
N15 C24 C25 C26 -57.4(3) . . . . ?
C24 C25 C26 C27 51.9(4) . . . . ?
C25 C26 C27 C28 -51.0(4) . . . . ?
C24 N15 C28 C27 -59.6(3) . . . . ?
C23 N15 C28 C27 178.9(3) . . . . ?
Cd2 N15 C28 C27 64.4(3) . . . . ?
C26 C27 C28 N15 56.0(4) . . . . ?

_refine_diff_density_max         0.480
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.050

