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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H18 Cd N4 O4'
_chemical_formula_weight         406.71

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   8.9979(9)
_cell_length_b                   14.5904(14)
_cell_length_c                   13.4092(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.863(6)
_cell_angle_gamma                90.00
_cell_volume                     1609.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6100
_cell_measurement_theta_min      2.7386
_cell_measurement_theta_max      27.4544

_exptl_crystal_description       neddle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    1.379
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.668
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Smart CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11418
_diffrn_reflns_av_R_equivalents  0.1124
_diffrn_reflns_av_sigmaI/netI    0.0615
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2984
_reflns_number_gt                2378
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0896P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2984
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1379
_refine_ls_wR_factor_gt          0.1319
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.80416(3) 0.748034(12) 0.39170(2) 0.03964(18) Uani 1 1 d . . .
N1 N 0.8122(4) 0.6295(2) 0.2847(3) 0.0484(8) Uani 1 1 d . . .
N2 N 0.8486(5) 0.5463(2) 0.1610(3) 0.0570(8) Uani 1 1 d . . .
N3 N 0.7498(4) 0.8652(2) 0.2722(3) 0.0481(8) Uani 1 1 d . . .
N4 N 0.7660(4) 0.9598(2) 0.1496(3) 0.0512(8) Uani 1 1 d . . .
O1 O 1.0124(5) 0.7216(3) 0.5695(3) 0.0839(10) Uani 1 1 d . . .
O2 O 1.0778(3) 0.7896(2) 0.4490(3) 0.0826(9) Uani 1 1 d . . .
O3 O 1.6226(4) 0.8149(2) 0.4653(3) 0.0735(10) Uani 1 1 d . . .
O4 O 1.5996(4) 0.67082(18) 0.4183(2) 0.0607(8) Uani 1 1 d . . .
C1 C 1.1157(7) 0.7578(2) 0.5423(5) 0.0523(12) Uani 1 1 d . . .
C2 C 1.2892(7) 0.7648(3) 0.6246(5) 0.0653(13) Uani 1 1 d . . .
H2A H 1.3216 0.7060 0.6605 0.078 Uiso 1 1 calc R . .
H2B H 1.2941 0.8093 0.6797 0.078 Uiso 1 1 calc R . .
C3 C 1.4123(4) 0.7928(3) 0.5775(3) 0.0599(10) Uani 1 1 d . . .
H3A H 1.3777 0.8501 0.5383 0.072 Uiso 1 1 calc R . .
H3B H 1.5171 0.8031 0.6371 0.072 Uiso 1 1 calc R . .
C4 C 1.4309(5) 0.7226(3) 0.5025(4) 0.0559(10) Uani 1 1 d . . .
H4A H 1.3273 0.7168 0.4404 0.067 Uiso 1 1 calc R . .
H4B H 1.4532 0.6641 0.5402 0.067 Uiso 1 1 calc R . .
C5 C 1.5594(6) 0.7387(2) 0.4599(4) 0.0464(10) Uani 1 1 d . . .
C6 C 0.7537(7) 0.4965(3) 0.1975(4) 0.0755(14) Uani 1 1 d . . .
H6A H 0.7116 0.4383 0.1745 0.091 Uiso 1 1 calc R . .
C7 C 0.7329(6) 0.5478(2) 0.2732(3) 0.0645(11) Uani 1 1 d . . .
H7A H 0.6729 0.5305 0.3125 0.077 Uiso 1 1 calc R . .
C8 C 0.8787(5) 0.6255(2) 0.2144(3) 0.0521(9) Uani 1 1 d . . .
H8A H 0.9398 0.6726 0.2031 0.063 Uiso 1 1 calc R . .
C9 C 0.8951(7) 0.5206(3) 0.0718(4) 0.0831(16) Uani 1 1 d . . .
H9A H 0.9919 0.5531 0.0794 0.125 Uiso 1 1 calc R . .
H9B H 0.8087 0.5361 0.0033 0.125 Uiso 1 1 calc R . .
H9C H 0.9151 0.4559 0.0744 0.125 Uiso 1 1 calc R . .
C10 C 0.6474(5) 0.9387(2) 0.2599(3) 0.0561(10) Uani 1 1 d . . .
H10A H 0.5820 0.9471 0.2979 0.067 Uiso 1 1 calc R . .
C11 C 0.6569(5) 0.9960(2) 0.1844(3) 0.0558(10) Uani 1 1 d . . .
H11A H 0.5994 1.0504 0.1606 0.067 Uiso 1 1 calc R . .
C12 C 0.8174(6) 0.9975(3) 0.0676(4) 0.0660(12) Uani 1 1 d . . .
H12A H 0.7342 0.9999 0.0116 0.099 Uiso 1 1 d R . .
H12B H 0.8533 1.0568 0.0863 0.099 Uiso 1 1 d R . .
H12C H 0.8631 0.9598 0.0523 0.099 Uiso 1 1 d R . .
C13 C 0.8198(5) 0.8811(2) 0.2043(3) 0.0494(9) Uani 1 1 d . . .
H13A H 0.8963 0.8429 0.1954 0.059 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 N3 2.258(3) . ?
Cd1 N1 2.267(3) . ?
Cd1 O4 2.306(3) 1_455 ?
Cd1 O2 2.343(3) . ?
Cd1 O1 2.394(4) . ?
Cd1 O3 2.429(3) 1_455 ?
Cd1 C5 2.708(5) 1_455 ?
N1 C8 1.306(5) . ?
N1 C7 1.365(5) . ?
N2 C8 1.328(5) . ?
N2 C6 1.355(5) . ?
N2 C9 1.466(5) . ?
N3 C13 1.320(5) . ?
N3 C10 1.379(5) . ?
N4 C13 1.343(5) . ?
N4 C11 1.354(5) . ?
N4 C12 1.462(5) . ?
O1 C1 1.244(6) . ?
O2 C1 1.246(6) . ?
O3 C5 1.237(4) . ?
O3 Cd1 2.429(3) 1_655 ?
O4 C5 1.259(4) . ?
O4 Cd1 2.306(3) 1_655 ?
C1 C2 1.507(9) . ?
C2 C3 1.535(6) . ?
C3 C4 1.492(5) . ?
C4 C5 1.502(6) . ?
C5 Cd1 2.708(5) 1_655 ?
C6 C7 1.334(5) . ?
C10 C11 1.342(5) . ?

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
N3 Cd1 N1 100.47(14) . . ?
N3 Cd1 O4 121.52(11) . 1_455 ?
N1 Cd1 O4 87.54(10) . 1_455 ?
N3 Cd1 O2 86.21(10) . . ?
N1 Cd1 O2 96.11(13) . . ?
O4 Cd1 O2 150.98(11) 1_455 . ?
N3 Cd1 O1 133.36(12) . . ?
N1 Cd1 O1 107.14(13) . . ?
O4 Cd1 O1 96.86(12) 1_455 . ?
O2 Cd1 O1 54.52(12) . . ?
N3 Cd1 O3 89.79(11) . 1_455 ?
N1 Cd1 O3 139.69(11) . 1_455 ?
O4 Cd1 O3 54.76(11) 1_455 1_455 ?
O2 Cd1 O3 123.59(13) . 1_455 ?
O1 Cd1 O3 92.54(13) . 1_455 ?
N3 Cd1 C5 107.80(12) . 1_455 ?
N1 Cd1 C5 114.45(11) . 1_455 ?
O4 Cd1 C5 27.63(9) 1_455 1_455 ?
O2 Cd1 C5 142.43(14) . 1_455 ?
O1 Cd1 C5 94.10(14) . 1_455 ?
O3 Cd1 C5 27.18(9) 1_455 1_455 ?
C8 N1 C7 104.5(3) . . ?
C8 N1 Cd1 129.2(3) . . ?
C7 N1 Cd1 126.1(2) . . ?
C8 N2 C6 107.0(3) . . ?
C8 N2 C9 126.8(3) . . ?
C6 N2 C9 125.9(4) . . ?
C13 N3 C10 105.3(3) . . ?
C13 N3 Cd1 126.6(2) . . ?
C10 N3 Cd1 128.0(3) . . ?
C13 N4 C11 107.3(3) . . ?
C13 N4 C12 125.3(3) . . ?
C11 N4 C12 127.3(3) . . ?
C1 O1 Cd1 90.9(3) . . ?
C1 O2 Cd1 93.3(3) . . ?
C5 O3 Cd1 89.1(2) . 1_655 ?
C5 O4 Cd1 94.3(2) . 1_655 ?
O1 C1 O2 121.3(5) . . ?
O1 C1 C2 119.3(5) . . ?
O2 C1 C2 119.4(4) . . ?
C1 C2 C3 115.0(4) . . ?
C4 C3 C2 113.0(4) . . ?
C3 C4 C5 117.5(4) . . ?
O3 C5 O4 121.7(4) . . ?
O3 C5 C4 121.7(4) . . ?
O4 C5 C4 116.6(3) . . ?
O3 C5 Cd1 63.8(2) . 1_655 ?
O4 C5 Cd1 58.1(2) . 1_655 ?
C4 C5 Cd1 173.3(3) . 1_655 ?
C7 C6 N2 106.0(4) . . ?
C6 C7 N1 110.4(4) . . ?
N1 C8 N2 112.0(3) . . ?
C11 C10 N3 109.4(3) . . ?
C10 C11 N4 107.0(3) . . ?
N3 C13 N4 111.0(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
N3 Cd1 N1 C8 42.4(3) . . . . ?
O4 Cd1 N1 C8 164.0(3) 1_455 . . . ?
O2 Cd1 N1 C8 -44.9(3) . . . . ?
O1 Cd1 N1 C8 -99.6(3) . . . . ?
O3 Cd1 N1 C8 144.6(3) 1_455 . . . ?
C5 Cd1 N1 C8 157.6(3) 1_455 . . . ?
N3 Cd1 N1 C7 -130.9(3) . . . . ?
O4 Cd1 N1 C7 -9.3(3) 1_455 . . . ?
O2 Cd1 N1 C7 141.9(3) . . . . ?
O1 Cd1 N1 C7 87.2(3) . . . . ?
O3 Cd1 N1 C7 -28.6(4) 1_455 . . . ?
C5 Cd1 N1 C7 -15.7(4) 1_455 . . . ?
N1 Cd1 N3 C13 -45.1(3) . . . . ?
O4 Cd1 N3 C13 -138.7(3) 1_455 . . . ?
O2 Cd1 N3 C13 50.4(3) . . . . ?
O1 Cd1 N3 C13 80.8(3) . . . . ?
O3 Cd1 N3 C13 174.1(3) 1_455 . . . ?
C5 Cd1 N3 C13 -165.2(3) 1_455 . . . ?
N1 Cd1 N3 C10 140.3(3) . . . . ?
O4 Cd1 N3 C10 46.7(3) 1_455 . . . ?
O2 Cd1 N3 C10 -124.2(3) . . . . ?
O1 Cd1 N3 C10 -93.8(3) . . . . ?
O3 Cd1 N3 C10 -0.5(3) 1_455 . . . ?
C5 Cd1 N3 C10 20.2(3) 1_455 . . . ?
N3 Cd1 O1 C1 -38.7(3) . . . . ?
N1 Cd1 O1 C1 84.9(3) . . . . ?
O4 Cd1 O1 C1 174.4(3) 1_455 . . . ?
O2 Cd1 O1 C1 -0.3(2) . . . . ?
O3 Cd1 O1 C1 -130.8(3) 1_455 . . . ?
C5 Cd1 O1 C1 -158.0(3) 1_455 . . . ?
N3 Cd1 O2 C1 153.5(3) . . . . ?
N1 Cd1 O2 C1 -106.4(3) . . . . ?
O4 Cd1 O2 C1 -10.4(4) 1_455 . . . ?
O1 Cd1 O2 C1 0.3(2) . . . . ?
O3 Cd1 O2 C1 66.2(3) 1_455 . . . ?
C5 Cd1 O2 C1 38.9(4) 1_455 . . . ?
Cd1 O1 C1 O2 0.6(4) . . . . ?
Cd1 O1 C1 C2 179.5(3) . . . . ?
Cd1 O2 C1 O1 -0.6(5) . . . . ?
Cd1 O2 C1 C2 -179.5(3) . . . . ?
O1 C1 C2 C3 168.5(4) . . . . ?
O2 C1 C2 C3 -12.6(6) . . . . ?
C1 C2 C3 C4 -65.9(5) . . . . ?
C2 C3 C4 C5 -174.4(4) . . . . ?
Cd1 O3 C5 O4 -4.5(5) 1_655 . . . ?
Cd1 O3 C5 C4 175.5(4) 1_655 . . . ?
Cd1 O4 C5 O3 4.8(5) 1_655 . . . ?
Cd1 O4 C5 C4 -175.3(4) 1_655 . . . ?
C3 C4 C5 O3 -16.0(7) . . . . ?
C3 C4 C5 O4 164.0(4) . . . . ?
C3 C4 C5 Cd1 127(3) . . . 1_655 ?
C8 N2 C6 C7 -1.0(5) . . . . ?
C9 N2 C6 C7 -175.5(4) . . . . ?
N2 C6 C7 N1 0.3(6) . . . . ?
C8 N1 C7 C6 0.4(5) . . . . ?
Cd1 N1 C7 C6 175.0(3) . . . . ?
C7 N1 C8 N2 -1.1(4) . . . . ?
Cd1 N1 C8 N2 -175.5(3) . . . . ?
C6 N2 C8 N1 1.3(5) . . . . ?
C9 N2 C8 N1 175.8(4) . . . . ?
C13 N3 C10 C11 0.7(4) . . . . ?
Cd1 N3 C10 C11 176.2(3) . . . . ?
N3 C10 C11 N4 -0.6(4) . . . . ?
C13 N4 C11 C10 0.3(4) . . . . ?
C12 N4 C11 C10 179.9(4) . . . . ?
C10 N3 C13 N4 -0.5(4) . . . . ?
Cd1 N3 C13 N4 -176.1(2) . . . . ?
C11 N4 C13 N3 0.2(4) . . . . ?
C12 N4 C13 N3 -179.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.457
_refine_diff_density_min         -0.990
_refine_diff_density_rms         0.126
_database_code_depnum_ccdc_archive 'CCDC 1001916'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H28 Cd N4 O9'
_chemical_formula_weight         496.79

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           54
_space_group_name_H-M_alt        'P c c a'
_space_group_name_Hall           '-P 2a 2ac'

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

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

_cell_length_a                   16.9674(17)
_cell_length_b                   14.2074(14)
_cell_length_c                   8.7538(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2110.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8095
_cell_measurement_theta_min      2.7961
_cell_measurement_theta_max      27.4766

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.084
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.752
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Smart CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17448
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.796
_diffrn_reflns_theta_max         27.511
_diffrn_reflns_theta_full        25.242
_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             2432
_reflns_number_gt                1823
_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       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0326P)²+1.0212P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2432
_refine_ls_number_parameters     125
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0268
_refine_ls_wR_factor_ref         0.0680
_refine_ls_wR_factor_gt          0.0617
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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_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 0.5000 0.85677(2) 1.2500 0.02961(9) Uani 1 2 d S T P . .
N1 N 0.61989(12) 0.83957(14) 1.1336(2) 0.0427(5) Uani 1 1 d . . . . .
N2 N 0.70993(11) 0.76307(14) 1.0026(2) 0.0451(5) Uani 1 1 d . . . . .
O1 O 0.45798(9) 0.73118(10) 1.07573(17) 0.0380(4) Uani 1 1 d . . . . .
O2 O 0.45248(11) 0.87430(10) 0.98394(19) 0.0454(4) Uani 1 1 d . . . . .
O1W O 0.5000 1.01377(19) 1.2500 0.0957(15) Uani 1 2 d S T P . .
H1WA H 0.5121 1.0464 1.1680 0.144 Uiso 1 1 d R U . . .
O2W O 0.42828(10) 0.54262(11) 0.05264(19) 0.0479(4) Uani 1 1 d . . . . .
H2WA H 0.4373 0.6055 0.0599 0.072 Uiso 1 1 d R U . . .
H2WB H 0.4732 0.5417 0.0875 0.072 Uiso 1 1 d R U . . .
O3W O 0.33219(11) 0.50602(18) 0.3057(2) 0.0726(6) Uani 1 1 d . . . . .
H3WA H 0.3602 0.5114 0.2298 0.109 Uiso 1 1 d R U . . .
H3WB H 0.3526 0.4821 0.3895 0.109 Uiso 1 1 d R U . . .
C1 C 0.44786(12) 0.78703(15) 0.9654(2) 0.0337(5) Uani 1 1 d . . . . .
C2 C 0.43103(15) 0.74624(18) 0.8094(3) 0.0434(6) Uani 1 1 d . . . . .
H2A H 0.4204 0.7970 0.7383 0.052 Uiso 1 1 calc R U . . .
H2B H 0.3843 0.7070 0.8150 0.052 Uiso 1 1 calc R U . . .
C3 C 0.5000 0.6877(2) 0.7500 0.0514(10) Uani 1 2 d S T P . .
H3A H 0.5187 0.6474 0.8317 0.062 Uiso 0.5 1 calc R U P . .
H3B H 0.4813 0.6474 0.6683 0.062 Uiso 0.5 1 calc R U P . .
C4 C 0.64579(14) 0.75704(17) 1.0908(3) 0.0410(5) Uani 1 1 d . . . . .
H4A H 0.6223 0.7005 1.1186 0.049 Uiso 1 1 calc R U . . .
C5 C 0.75139(18) 0.6849(2) 0.9306(4) 0.0642(8) Uani 1 1 d . . . . .
H5A H 0.7439 0.6289 0.9901 0.096 Uiso 1 1 calc R U . . .
H5B H 0.8066 0.6992 0.9247 0.096 Uiso 1 1 calc R U . . .
H5C H 0.7310 0.6753 0.8295 0.096 Uiso 1 1 calc R U . . .
C6 C 0.7252(2) 0.8563(2) 0.9865(4) 0.0786(11) Uani 1 1 d . . . . .
H6A H 0.7661 0.8832 0.9309 0.094 Uiso 1 1 calc R U . . .
C7 C 0.66966(19) 0.9022(2) 1.0667(4) 0.0744(10) Uani 1 1 d . . . . .
H7A H 0.6658 0.9673 1.0752 0.089 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 O1W 2.230(3) . ?
Cd1 N1 2.288(2) 3_657 ?
Cd1 N1 2.288(2) . ?
Cd1 O1 2.4535(15) . ?
Cd1 O1 2.4535(15) 3_657 ?
Cd1 O2 2.4772(17) 3_657 ?
Cd1 O2 2.4772(17) . ?
N1 C4 1.307(3) . ?
N1 C7 1.360(3) . ?
N2 C4 1.337(3) . ?
N2 C6 1.357(3) . ?
N2 C5 1.458(3) . ?
O1 C1 1.262(3) . ?
O2 C1 1.253(3) . ?
O1W H1WA 0.8790 . ?
O2W H2WA 0.9084 . ?
O2W H2WB 0.8203 . ?
O3W H3WA 0.8199 . ?
O3W H3WB 0.8800 . ?
C1 C2 1.510(3) . ?
C2 C3 1.527(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C2 1.527(3) 3_656 ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.344(4) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1W Cd1 N1 96.13(5) . 3_657 ?
O1W Cd1 N1 96.13(5) . . ?
N1 Cd1 N1 167.73(10) 3_657 . ?
O1W Cd1 O1 136.66(4) . . ?
N1 Cd1 O1 86.60(6) 3_657 . ?
N1 Cd1 O1 84.48(6) . . ?
O1W Cd1 O1 136.66(4) . 3_657 ?
N1 Cd1 O1 84.48(6) 3_657 3_657 ?
N1 Cd1 O1 86.60(6) . 3_657 ?
O1 Cd1 O1 86.68(7) . 3_657 ?
O1W Cd1 O2 84.23(3) . 3_657 ?
N1 Cd1 O2 83.20(7) 3_657 3_657 ?
N1 Cd1 O2 98.04(7) . 3_657 ?
O1 Cd1 O2 138.79(5) . 3_657 ?
O1 Cd1 O2 52.69(5) 3_657 3_657 ?
O1W Cd1 O2 84.23(3) . . ?
N1 Cd1 O2 98.04(7) 3_657 . ?
N1 Cd1 O2 83.20(7) . . ?
O1 Cd1 O2 52.69(5) . . ?
O1 Cd1 O2 138.79(5) 3_657 . ?
O2 Cd1 O2 168.46(7) 3_657 . ?
C4 N1 C7 104.8(2) . . ?
C4 N1 Cd1 121.50(16) . . ?
C7 N1 Cd1 132.38(19) . . ?
C4 N2 C6 106.2(2) . . ?
C4 N2 C5 126.4(2) . . ?
C6 N2 C5 127.3(2) . . ?
C1 O1 Cd1 93.34(12) . . ?
C1 O2 Cd1 92.45(13) . . ?
Cd1 O1W H1WA 121.9 . . ?
H2WA O2W H2WB 80.4 . . ?
H3WA O3W H3WB 118.9 . . ?
O2 C1 O1 121.0(2) . . ?
O2 C1 C2 120.6(2) . . ?
O1 C1 C2 118.45(19) . . ?
C1 C2 C3 111.84(18) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C2 C3 C2 114.0(3) 3_656 . ?
C2 C3 H3A 108.8 3_656 . ?
C2 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 3_656 . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.6 . . ?
N1 C4 N2 112.4(2) . . ?
N1 C4 H4A 123.8 . . ?
N2 C4 H4A 123.8 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 N2 106.6(2) . . ?
C7 C6 H6A 126.7 . . ?
N2 C6 H6A 126.7 . . ?
C6 C7 N1 110.1(3) . . ?
C6 C7 H7A 125.0 . . ?
N1 C7 H7A 125.0 . . ?

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
Cd1 O2 C1 O1 7.5(2) . . . . ?
Cd1 O2 C1 C2 -171.66(18) . . . . ?
Cd1 O1 C1 O2 -7.6(2) . . . . ?
Cd1 O1 C1 C2 171.59(17) . . . . ?
O2 C1 C2 C3 115.7(2) . . . . ?
O1 C1 C2 C3 -63.6(3) . . . . ?
C1 C2 C3 C2 -76.55(17) . . . 3_656 ?
C7 N1 C4 N2 1.1(3) . . . . ?
Cd1 N1 C4 N2 169.29(15) . . . . ?
C6 N2 C4 N1 -0.9(3) . . . . ?
C5 N2 C4 N1 -177.2(2) . . . . ?
C4 N2 C6 C7 0.3(4) . . . . ?
C5 N2 C6 C7 176.6(3) . . . . ?
N2 C6 C7 N1 0.3(4) . . . . ?
C4 N1 C7 C6 -0.8(4) . . . . ?
Cd1 N1 C7 C6 -167.2(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WA O2 0.88 1.84 2.715(2) 171.0 5_677
O2W H2WA O1 0.91 1.83 2.733(2) 178.6 1_554
O3W H3WA O2W 0.82 1.98 2.799(3) 172.3 .
O3W H3WB O2W 0.88 1.95 2.795(3) 159.8 7_566
C5 H5B O1 0.96 2.61 3.567(3) 176.3 6_657

_refine_diff_density_max         0.290
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.075

_shelxl_version_number           2013-4



_database_code_depnum_ccdc_archive 'CCDC 1001917'
