# 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            'C20 H21 Br Cd N4 O4'
_chemical_formula_weight         573.72

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'
Br Br -0.2901 2.4595 '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   'Pnna '

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

_cell_length_a                   21.2969(15)
_cell_length_b                   26.3582(19)
_cell_length_c                   8.7744(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4925.5(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2523
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      20.08

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2272
_exptl_absorpt_coefficient_mu    2.539
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5367
_exptl_absorpt_correction_T_max  0.6868
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.108 0.250 0.069 206 37 ' '
2 0.608 0.250 -0.121 206 37 ' '
3 0.392 0.750 0.075 206 37 ' '
4 0.892 0.750 -0.118 206 37 ' '
_platon_squeeze_details          
;
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22920
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_av_sigmaI/netI    0.0562
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4305
_reflns_number_gt                2967
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0574P)²+0.0844P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4305
_refine_ls_number_parameters     274
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1146
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.033
_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 0.08430(3) 0.7500 1.2500 0.04332(18) Uani 1 2 d S . .
Cd2 Cd -0.2500 1.0000 1.13919(6) 0.04422(18) Uani 1 2 d S . .
N1 N 0.1493(2) 0.78496(16) 1.0748(5) 0.0509(11) Uani 1 1 d . . .
N2 N 0.1789(3) 0.8215(2) 0.8620(5) 0.0709(15) Uani 1 1 d D . .
N3 N 0.1910(4) 0.9128(3) 0.2578(7) 0.118(3) Uani 1 1 d D . .
N4 N 0.2062(2) 0.94753(17) 0.0340(5) 0.0559(12) Uani 1 1 d . . .
O1 O -0.1725(2) 0.93947(18) 1.1893(6) 0.0896(15) Uani 1 1 d . . .
O2 O -0.1707(2) 1.00598(19) 1.3303(5) 0.0891(15) Uani 1 1 d . . .
O3 O 0.0014(2) 0.81229(16) 1.2322(6) 0.0771(13) Uani 1 1 d . . .
O4 O 0.0597(2) 0.81219(16) 1.4352(5) 0.0755(13) Uani 1 1 d . . .
Br3 Br -0.01210(4) 0.96571(3) 1.80350(9) 0.0922(3) Uani 1 1 d . . .
C1 C -0.0810(3) 0.9614(2) 1.5262(7) 0.0554(14) Uani 1 1 d . . .
H1 H -0.1013 0.9902 1.5630 0.066 Uiso 1 1 calc R . .
C2 C -0.0336(3) 0.9391(2) 1.6096(6) 0.0550(15) Uani 1 1 d . . .
C3 C -0.0024(3) 0.8966(2) 1.5547(7) 0.0565(15) Uani 1 1 d . . .
H3 H 0.0296 0.8819 1.6120 0.068 Uiso 1 1 calc R . .
C4 C -0.0183(2) 0.8763(2) 1.4175(7) 0.0479(13) Uani 1 1 d . . .
C5 C -0.0669(3) 0.8983(2) 1.3335(6) 0.0510(14) Uani 1 1 d . . .
H5 H -0.0784 0.8843 1.2404 0.061 Uiso 1 1 calc R . .
C6 C -0.0981(2) 0.9408(2) 1.3871(6) 0.0484(14) Uani 1 1 d . . .
C7 C -0.1503(3) 0.9633(3) 1.2965(7) 0.0599(16) Uani 1 1 d . . .
C8 C 0.0159(3) 0.8303(2) 1.3591(8) 0.0578(15) Uani 1 1 d . . .
C9 C 0.2130(3) 0.7898(2) 1.0751(7) 0.0697(18) Uani 1 1 d . . .
H9 H 0.2395 0.7793 1.1534 0.084 Uiso 1 1 calc R . .
C10 C 0.2319(4) 0.8120(3) 0.9451(8) 0.095(2) Uani 1 1 d . . .
H10 H 0.2729 0.8195 0.9171 0.114 Uiso 1 1 calc R . .
C11 C 0.1298(3) 0.8049(2) 0.9442(6) 0.0531(14) Uani 1 1 d . . .
C12 C 0.0651(3) 0.8096(3) 0.8924(8) 0.081(2) Uani 1 1 d . . .
H12A H 0.0384 0.7890 0.9550 0.121 Uiso 1 1 calc R . .
H12B H 0.0621 0.7987 0.7884 0.121 Uiso 1 1 calc R . .
H12C H 0.0521 0.8444 0.8998 0.121 Uiso 1 1 calc R . .
C13 C 0.1746(4) 0.8480(4) 0.7145(8) 0.109(3) Uani 1 1 d D . .
H13A H 0.1394 0.8343 0.6576 0.131 Uiso 1 1 calc R . .
H13B H 0.1662 0.8836 0.7330 0.131 Uiso 1 1 calc R . .
C14 C 0.2315(5) 0.8435(5) 0.6216(9) 0.169(5) Uani 1 1 d D . .
H14A H 0.2496 0.8101 0.6361 0.202 Uiso 1 1 calc R . .
H14B H 0.2620 0.8684 0.6558 0.202 Uiso 1 1 calc R . .
C15 C 0.2179(5) 0.8521(4) 0.4442(11) 0.171(5) Uani 1 1 d D . .
H15A H 0.2551 0.8453 0.3839 0.205 Uiso 1 1 calc R . .
H15B H 0.1842 0.8302 0.4094 0.205 Uiso 1 1 calc R . .
C16 C 0.1997(6) 0.9057(4) 0.4332(10) 0.174(5) Uani 1 1 d D . .
H16A H 0.2323 0.9277 0.4725 0.209 Uiso 1 1 calc R . .
H16B H 0.1609 0.9122 0.4877 0.209 Uiso 1 1 calc R . .
C17 C 0.1342(4) 0.9180(3) 0.1884(10) 0.094(2) Uani 1 1 d . . .
H17 H 0.0956 0.9077 0.2278 0.113 Uiso 1 1 calc R . .
C18 C 0.1433(3) 0.9400(2) 0.0560(8) 0.0640(16) Uani 1 1 d . . .
H18 H 0.1119 0.9490 -0.0124 0.077 Uiso 1 1 calc R . .
C19 C 0.2342(3) 0.9300(3) 0.1575(8) 0.084(2) Uani 1 1 d . . .
C20 C 0.3027(4) 0.9278(5) 0.1795(11) 0.161(5) Uani 1 1 d . . .
H20A H 0.3233 0.9417 0.0916 0.242 Uiso 1 1 calc R . .
H20B H 0.3154 0.8932 0.1930 0.242 Uiso 1 1 calc R . .
H20C H 0.3139 0.9471 0.2681 0.242 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 2.265(4) . ?
Cd1 N1 2.265(4) 4_567 ?
Cd1 O4 2.367(4) . ?
Cd1 O4 2.367(4) 4_567 ?
Cd1 O3 2.416(4) 4_567 ?
Cd1 O3 2.416(4) . ?
Cd1 C8 2.741(6) 4_567 ?
Cd2 N4 2.257(4) 6_556 ?
Cd2 N4 2.257(4) 5_576 ?
Cd2 O1 2.337(4) . ?
Cd2 O1 2.337(4) 2_475 ?
Cd2 O2 2.385(4) 2_475 ?
Cd2 C7 2.712(6) 2_475 ?
N1 C11 1.328(6) . ?
N1 C9 1.364(7) . ?
N2 C11 1.342(7) . ?
N2 C10 1.366(8) . ?
N2 C13 1.474(6) . ?
N3 C19 1.352(9) . ?
N3 C17 1.361(10) . ?
N3 C16 1.562(8) . ?
N4 C19 1.321(7) . ?
N4 C18 1.366(7) . ?
N4 Cd2 2.257(4) 5_576 ?
O1 C7 1.226(7) . ?
O2 C7 1.243(7) . ?
O3 C8 1.249(7) . ?
O4 C8 1.242(7) . ?
Br3 C2 1.896(6) . ?
C1 C2 1.379(7) . ?
C1 C6 1.385(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.390(8) . ?
C3 C4 1.361(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(7) . ?
C4 C8 1.505(8) . ?
C5 C6 1.384(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.489(8) . ?
C9 C10 1.344(8) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.456(8) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.464(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.600(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.468(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.313(9) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.472(10) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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 N1 104.6(2) . 4_567 ?
N1 Cd1 O4 108.64(16) . . ?
N1 Cd1 O4 87.20(15) 4_567 . ?
N1 Cd1 O4 87.20(15) . 4_567 ?
N1 Cd1 O4 108.64(16) 4_567 4_567 ?
O4 Cd1 O4 154.4(2) . 4_567 ?
N1 Cd1 O3 140.10(16) . 4_567 ?
N1 Cd1 O3 97.25(16) 4_567 4_567 ?
O4 Cd1 O3 105.32(17) . 4_567 ?
O4 Cd1 O3 53.99(16) 4_567 4_567 ?
N1 Cd1 O3 97.25(16) . . ?
N1 Cd1 O3 140.10(16) 4_567 . ?
O4 Cd1 O3 53.99(16) . . ?
O4 Cd1 O3 105.32(17) 4_567 . ?
O3 Cd1 O3 86.1(2) 4_567 . ?
N1 Cd1 C8 113.70(18) . 4_567 ?
N1 Cd1 C8 104.35(16) 4_567 4_567 ?
O4 Cd1 C8 131.0(2) . 4_567 ?
O4 Cd1 C8 26.89(17) 4_567 4_567 ?
O3 Cd1 C8 27.10(16) 4_567 4_567 ?
O3 Cd1 C8 96.51(18) . 4_567 ?
N4 Cd2 N4 95.4(2) 6_556 5_576 ?
N4 Cd2 O1 90.02(17) 6_556 . ?
N4 Cd2 O1 104.64(18) 5_576 . ?
N4 Cd2 O1 104.64(18) 6_556 2_475 ?
N4 Cd2 O1 90.02(17) 5_576 2_475 ?
O1 Cd2 O1 158.3(3) . 2_475 ?
N4 Cd2 O2 98.06(18) 6_556 2_475 ?
N4 Cd2 O2 143.79(16) 5_576 2_475 ?
O1 Cd2 O2 108.81(18) . 2_475 ?
O1 Cd2 O2 54.06(16) 2_475 2_475 ?
N4 Cd2 C7 103.73(18) 6_556 2_475 ?
N4 Cd2 C7 116.6(2) 5_576 2_475 ?
O1 Cd2 C7 134.5(2) . 2_475 ?
O1 Cd2 C7 26.81(16) 2_475 2_475 ?
O2 Cd2 C7 27.29(17) 2_475 2_475 ?
C11 N1 C9 106.0(5) . . ?
C11 N1 Cd1 123.8(4) . . ?
C9 N1 Cd1 130.2(4) . . ?
C11 N2 C10 107.3(5) . . ?
C11 N2 C13 125.3(5) . . ?
C10 N2 C13 127.3(6) . . ?
C19 N3 C17 106.3(6) . . ?
C19 N3 C16 126.9(8) . . ?
C17 N3 C16 123.9(8) . . ?
C19 N4 C18 106.0(5) . . ?
C19 N4 Cd2 125.4(4) . 5_576 ?
C18 N4 Cd2 126.1(4) . 5_576 ?
C7 O1 Cd2 93.9(4) . . ?
C8 O3 Cd1 91.1(4) . . ?
C8 O4 Cd1 93.6(4) . . ?
C2 C1 C6 119.5(5) . . ?
C2 C1 H1 120.2 . . ?
C6 C1 H1 120.2 . . ?
C1 C2 C3 120.7(5) . . ?
C1 C2 Br3 119.7(4) . . ?
C3 C2 Br3 119.6(4) . . ?
C4 C3 C2 120.3(5) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.3(5) . . ?
C3 C4 C8 119.8(5) . . ?
C5 C4 C8 121.0(6) . . ?
C6 C5 C4 120.8(5) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 119.4(5) . . ?
C5 C6 C7 119.9(5) . . ?
C1 C6 C7 120.7(5) . . ?
O1 C7 O2 120.7(6) . . ?
O1 C7 C6 119.7(6) . . ?
O2 C7 C6 119.6(6) . . ?
O4 C8 O3 121.3(6) . . ?
O4 C8 C4 119.3(6) . . ?
O3 C8 C4 119.3(6) . . ?
C10 C9 N1 109.6(6) . . ?
C10 C9 H9 125.2 . . ?
N1 C9 H9 125.2 . . ?
C9 C10 N2 106.6(6) . . ?
C9 C10 H10 126.7 . . ?
N2 C10 H10 126.7 . . ?
N1 C11 N2 110.4(5) . . ?
N1 C11 C12 126.8(5) . . ?
N2 C11 C12 122.8(5) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N2 113.6(6) . . ?
C14 C13 H13A 108.8 . . ?
N2 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
N2 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 C15 112.4(8) . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C14 104.3(8) . . ?
C16 C15 H15A 110.9 . . ?
C14 C15 H15A 110.9 . . ?
C16 C15 H15B 110.9 . . ?
C14 C15 H15B 110.9 . . ?
H15A C15 H15B 108.9 . . ?
C15 C16 N3 102.2(8) . . ?
C15 C16 H16A 111.3 . . ?
N3 C16 H16A 111.3 . . ?
C15 C16 H16B 111.3 . . ?
N3 C16 H16B 111.3 . . ?
H16A C16 H16B 109.2 . . ?
C18 C17 N3 107.9(6) . . ?
C18 C17 H17 126.0 . . ?
N3 C17 H17 126.0 . . ?
C17 C18 N4 109.6(6) . . ?
C17 C18 H18 125.2 . . ?
N4 C18 H18 125.2 . . ?
N4 C19 N3 110.1(6) . . ?
N4 C19 C20 124.7(6) . . ?
N3 C19 C20 125.2(6) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
N1 Cd1 N1 C11 172.8(5) 4_567 . . . ?
O4 Cd1 N1 C11 -95.2(4) . . . . ?
O4 Cd1 N1 C11 64.3(4) 4_567 . . . ?
O3 Cd1 N1 C11 51.8(5) 4_567 . . . ?
O3 Cd1 N1 C11 -40.8(4) . . . . ?
C8 Cd1 N1 C11 59.6(4) 4_567 . . . ?
N1 Cd1 N1 C9 -6.1(5) 4_567 . . . ?
O4 Cd1 N1 C9 85.9(5) . . . . ?
O4 Cd1 N1 C9 -114.6(5) 4_567 . . . ?
O3 Cd1 N1 C9 -127.1(5) 4_567 . . . ?
O3 Cd1 N1 C9 140.3(5) . . . . ?
C8 Cd1 N1 C9 -119.3(5) 4_567 . . . ?
N4 Cd2 O1 C7 -172.9(4) 6_556 . . . ?
N4 Cd2 O1 C7 91.5(4) 5_576 . . . ?
O1 Cd2 O1 C7 -39.7(4) 2_475 . . . ?
O2 Cd2 O1 C7 -74.4(4) 2_475 . . . ?
C7 Cd2 O1 C7 -63.5(6) 2_475 . . . ?
N1 Cd1 O3 C8 -107.4(4) . . . . ?
N1 Cd1 O3 C8 15.9(5) 4_567 . . . ?
O4 Cd1 O3 C8 0.4(3) . . . . ?
O4 Cd1 O3 C8 163.5(3) 4_567 . . . ?
O3 Cd1 O3 C8 112.5(4) 4_567 . . . ?
C8 Cd1 O3 C8 137.6(3) 4_567 . . . ?
N1 Cd1 O4 C8 85.0(4) . . . . ?
N1 Cd1 O4 C8 -170.5(4) 4_567 . . . ?
O4 Cd1 O4 C8 -40.8(3) 4_567 . . . ?
O3 Cd1 O4 C8 -73.7(4) 4_567 . . . ?
O3 Cd1 O4 C8 -0.4(3) . . . . ?
C8 Cd1 O4 C8 -63.8(5) 4_567 . . . ?
C6 C1 C2 C3 0.9(9) . . . . ?
C6 C1 C2 Br3 -177.6(4) . . . . ?
C1 C2 C3 C4 -0.1(9) . . . . ?
Br3 C2 C3 C4 178.3(4) . . . . ?
C2 C3 C4 C5 -0.8(9) . . . . ?
C2 C3 C4 C8 179.9(5) . . . . ?
C3 C4 C5 C6 1.0(8) . . . . ?
C8 C4 C5 C6 -179.7(5) . . . . ?
C4 C5 C6 C1 -0.3(8) . . . . ?
C4 C5 C6 C7 -179.3(5) . . . . ?
C2 C1 C6 C5 -0.7(8) . . . . ?
C2 C1 C6 C7 178.4(5) . . . . ?
Cd2 O1 C7 O2 -3.9(7) . . . . ?
Cd2 O1 C7 C6 176.1(5) . . . . ?
C5 C6 C7 O1 12.6(9) . . . . ?
C1 C6 C7 O1 -166.4(6) . . . . ?
C5 C6 C7 O2 -167.4(6) . . . . ?
C1 C6 C7 O2 13.6(9) . . . . ?
Cd1 O4 C8 O3 0.7(6) . . . . ?
Cd1 O4 C8 C4 -176.3(4) . . . . ?
Cd1 O3 C8 O4 -0.6(6) . . . . ?
Cd1 O3 C8 C4 176.3(4) . . . . ?
C3 C4 C8 O4 -2.1(8) . . . . ?
C5 C4 C8 O4 178.6(5) . . . . ?
C3 C4 C8 O3 -179.1(6) . . . . ?
C5 C4 C8 O3 1.6(8) . . . . ?
C11 N1 C9 C10 -0.6(7) . . . . ?
Cd1 N1 C9 C10 178.5(5) . . . . ?
N1 C9 C10 N2 0.2(9) . . . . ?
C11 N2 C10 C9 0.2(8) . . . . ?
C13 N2 C10 C9 176.4(7) . . . . ?
C9 N1 C11 N2 0.7(7) . . . . ?
Cd1 N1 C11 N2 -178.4(4) . . . . ?
C9 N1 C11 C12 -178.7(6) . . . . ?
Cd1 N1 C11 C12 2.2(8) . . . . ?
C10 N2 C11 N1 -0.6(8) . . . . ?
C13 N2 C11 N1 -176.9(6) . . . . ?
C10 N2 C11 C12 178.8(7) . . . . ?
C13 N2 C11 C12 2.5(10) . . . . ?
C11 N2 C13 C14 -156.4(9) . . . . ?
C10 N2 C13 C14 28.1(13) . . . . ?
N2 C13 C14 C15 157.1(9) . . . . ?
C13 C14 C15 C16 66.8(14) . . . . ?
C14 C15 C16 N3 176.7(8) . . . . ?
C19 N3 C16 C15 -94.3(11) . . . . ?
C17 N3 C16 C15 107.4(11) . . . . ?
C19 N3 C17 C18 -3.3(10) . . . . ?
C16 N3 C17 C18 158.8(8) . . . . ?
N3 C17 C18 N4 2.6(9) . . . . ?
C19 N4 C18 C17 -0.7(8) . . . . ?
Cd2 N4 C18 C17 -163.7(5) 5_576 . . . ?
C18 N4 C19 N3 -1.4(8) . . . . ?
Cd2 N4 C19 N3 161.7(5) 5_576 . . . ?
C18 N4 C19 C20 176.4(9) . . . . ?
Cd2 N4 C19 C20 -20.5(12) 5_576 . . . ?
C17 N3 C19 N4 3.0(10) . . . . ?
C16 N3 C19 N4 -158.5(8) . . . . ?
C17 N3 C19 C20 -174.8(10) . . . . ?
C16 N3 C19 C20 23.8(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.944
_refine_diff_density_min         -0.800
_refine_diff_density_rms         0.096
_database_code_depnum_ccdc_archive 'CCDC 990994'
#######################################################################
#
#                 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_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H27 Br2 Cd2 N4 O9'
_chemical_formula_weight         960.17

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'
Br Br -0.2901 2.4595 '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                   9.449(3)
_cell_length_b                   10.386(4)
_cell_length_c                   17.553(6)
_cell_angle_alpha                76.519(8)
_cell_angle_beta                 89.167(7)
_cell_angle_gamma                79.774(8)
_cell_volume                     1648.0(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    548
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      19.0

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.935
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             934
_exptl_absorpt_coefficient_mu    3.772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4181
_exptl_absorpt_correction_T_max  0.5836
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8978
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_sigmaI/netI    0.1702
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         26.02
_reflns_number_total             6360
_reflns_number_gt                3371
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0060P)²+0.5000P] 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         6360
_refine_ls_number_parameters     418
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1435
_refine_ls_R_factor_gt           0.0728
_refine_ls_wR_factor_ref         0.1255
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.006
_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 0.82281(8) 0.58782(8) 0.29964(5) 0.0277(2) Uani 1 1 d . . .
Cd2 Cd 0.78836(9) 0.41965(9) 0.14193(5) 0.0301(2) Uani 1 1 d . . .
Br1 Br 0.11540(14) 1.02191(13) 0.19873(9) 0.0549(4) Uani 1 1 d . . .
Br2 Br 0.6513(2) 0.01449(15) 0.60777(8) 0.0769(6) Uani 1 1 d . . .
O1 O 0.6027(7) 0.6498(8) 0.2303(4) 0.038(2) Uani 1 1 d . . .
O2 O 0.5631(7) 0.4975(8) 0.1666(5) 0.047(2) Uani 1 1 d . . .
O3 O -0.1098(7) 0.5889(7) 0.1691(4) 0.035(2) Uani 1 1 d . . .
O4 O 0.0507(8) 0.4680(8) 0.1079(4) 0.039(2) Uani 1 1 d . . .
O5 O 0.7594(8) 0.3940(8) 0.3588(4) 0.041(2) Uani 1 1 d . . .
O6 O 0.8464(8) 0.2928(8) 0.2646(5) 0.044(2) Uani 1 1 d . . .
O7 O 0.7590(9) -0.3026(8) 0.3997(5) 0.051(2) Uani 1 1 d . . .
O8 O 0.8056(8) -0.1781(7) 0.2865(4) 0.037(2) Uani 1 1 d . . .
O9 O 0.7562(9) 0.5474(9) 0.0114(4) 0.058(3) Uani 1 1 d . . .
H9A H 0.8186 0.5488 -0.0215 0.070 Uiso 1 1 calc R . .
N1 N 1.0620(10) 0.5054(10) 0.3365(5) 0.035(2) Uani 1 1 d . . .
N2 N 1.2891(10) 0.4896(10) 0.3678(5) 0.033(2) Uani 1 1 d . . .
N3 N 0.7686(9) 0.2392(10) 0.0975(5) 0.033(2) Uani 1 1 d . . .
N4 N 0.7116(10) 0.0508(10) 0.0793(6) 0.041(3) Uani 1 1 d . . .
C1 C 0.5228(12) 0.5955(13) 0.1949(6) 0.034(3) Uani 1 1 d . . .
C2 C 0.3682(11) 0.6566(12) 0.1855(6) 0.029(3) Uani 1 1 d . . .
C3 C 0.2680(10) 0.5886(11) 0.1646(6) 0.025(3) Uani 1 1 d . . .
H3A H 0.2985 0.5044 0.1542 0.030 Uiso 1 1 calc R . .
C4 C 0.1227(11) 0.6432(10) 0.1589(5) 0.022(2) Uani 1 1 d . . .
C5 C 0.0782(12) 0.7722(11) 0.1688(6) 0.031(3) Uani 1 1 d . . .
H5A H -0.0187 0.8113 0.1625 0.037 Uiso 1 1 calc R . .
C6 C 0.1773(12) 0.8430(11) 0.1880(6) 0.034(3) Uani 1 1 d . . .
C7 C 0.3247(11) 0.7870(12) 0.1970(6) 0.035(3) Uani 1 1 d . . .
H7A H 0.3912 0.8348 0.2102 0.042 Uiso 1 1 calc R . .
C8 C 0.0161(11) 0.5585(11) 0.1445(6) 0.024(3) Uani 1 1 d . . .
C9 C 0.7956(12) 0.2926(12) 0.3301(8) 0.035(3) Uani 1 1 d . . .
C10 C 0.7714(11) 0.1619(11) 0.3789(6) 0.031(3) Uani 1 1 d . . .
C11 C 0.7909(12) 0.0465(11) 0.3492(7) 0.042(3) Uani 1 1 d . . .
H11A H 0.8238 0.0516 0.2986 0.050 Uiso 1 1 calc R . .
C12 C 0.7625(12) -0.0767(11) 0.3935(6) 0.030(3) Uani 1 1 d . . .
C13 C 0.7207(14) -0.0840(12) 0.4715(7) 0.047(4) Uani 1 1 d . . .
H13A H 0.7025 -0.1649 0.5022 0.057 Uiso 1 1 calc R . .
C14 C 0.7069(15) 0.0243(12) 0.5017(6) 0.050(4) Uani 1 1 d . . .
C15 C 0.7276(11) 0.1493(11) 0.4579(6) 0.034(3) Uani 1 1 d . . .
H15A H 0.7129 0.2237 0.4799 0.041 Uiso 1 1 calc R . .
C16 C 0.7734(13) -0.1929(11) 0.3572(7) 0.038(3) Uani 1 1 d . . .
C17 C 1.1357(13) 0.3852(13) 0.3243(6) 0.043(3) Uani 1 1 d . . .
H17A H 1.0974 0.3216 0.3057 0.051 Uiso 1 1 calc R . .
C18 C 1.2780(13) 0.3778(13) 0.3454(7) 0.042(3) Uani 1 1 d . . .
H18B H 1.3529 0.3070 0.3441 0.051 Uiso 1 1 calc R . .
C19 C 1.1537(13) 0.5652(12) 0.3635(7) 0.038(3) Uani 1 1 d . . .
C20 C 1.4202(11) 0.5179(13) 0.3969(7) 0.046(3) Uani 1 1 d . . .
H20A H 1.4222 0.6132 0.3789 0.055 Uiso 1 1 calc R . .
H20B H 1.5022 0.4689 0.3755 0.055 Uiso 1 1 calc R . .
C21 C 1.4331(10) 0.4787(12) 0.4858(6) 0.033(3) Uani 1 1 d . . .
H21C H 1.4401 0.3821 0.5039 0.049 Uiso 1 1 calc R . .
H21D H 1.3478 0.5220 0.5076 0.049 Uiso 1 1 calc R . .
C22 C 1.1259(12) 0.6924(11) 0.3885(7) 0.045(3) Uani 1 1 d . . .
H22A H 1.0637 0.7590 0.3504 0.067 Uiso 1 1 calc R . .
H22B H 1.2152 0.7224 0.3930 0.067 Uiso 1 1 calc R . .
H22C H 1.0807 0.6792 0.4383 0.067 Uiso 1 1 calc R . .
C23 C 0.8483(12) 0.2004(12) 0.0365(6) 0.039(3) Uani 1 1 d . . .
H23A H 0.9139 0.2480 0.0079 0.047 Uiso 1 1 calc R . .
C24 C 0.8176(13) 0.0850(12) 0.0245(7) 0.041(3) Uani 1 1 d . . .
C25 C 0.6871(13) 0.1501(13) 0.1208(7) 0.038(3) Uani 1 1 d . . .
C26 C 0.6408(12) -0.0647(12) 0.0866(7) 0.047(3) Uani 1 1 d . . .
H26A H 0.6258 -0.1015 0.1416 0.056 Uiso 1 1 calc R . .
H26B H 0.7031 -0.1337 0.0669 0.056 Uiso 1 1 calc R . .
C27 C 0.4996(13) -0.0301(14) 0.0431(6) 0.055(4) Uani 1 1 d . . .
H27A H 0.4356 0.0325 0.0668 0.083 Uiso 1 1 calc R . .
H27B H 0.4587 -0.1113 0.0507 0.083 Uiso 1 1 calc R . .
C28 C 0.5803(12) 0.1454(13) 0.1851(7) 0.055(4) Uani 1 1 d . . .
H28A H 0.5656 0.2289 0.2011 0.082 Uiso 1 1 calc R . .
H28B H 0.6164 0.0729 0.2289 0.082 Uiso 1 1 calc R . .
H28C H 0.4907 0.1313 0.1664 0.082 Uiso 1 1 calc R . .
C29 C 0.6293(18) 0.6314(18) -0.0220(9) 0.139(9) Uani 1 1 d . . .
H29A H 0.6514 0.7143 -0.0528 0.208 Uiso 1 1 calc R . .
H29B H 0.5656 0.6498 0.0188 0.208 Uiso 1 1 calc R . .
H29C H 0.5838 0.5878 -0.0548 0.208 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 O5 2.219(8) . ?
Cd1 N1 2.314(9) . ?
Cd1 O7 2.325(8) 1_565 ?
Cd1 O1 2.336(7) . ?
Cd1 O8 2.364(7) 1_565 ?
Cd1 O3 2.368(7) 1_655 ?
Cd1 C16 2.665(11) 1_565 ?
Cd2 O2 2.213(7) . ?
Cd2 N3 2.228(10) . ?
Cd2 O6 2.264(8) . ?
Cd2 O3 2.290(7) 1_655 ?
Cd2 O9 2.358(8) . ?
Cd2 O4 2.648(7) 1_655 ?
Br1 C6 1.899(11) . ?
Br2 C14 1.912(11) . ?
O1 C1 1.266(12) . ?
O2 C1 1.234(12) . ?
O3 C8 1.272(11) . ?
O3 Cd2 2.290(7) 1_455 ?
O3 Cd1 2.368(7) 1_455 ?
O4 C8 1.252(12) . ?
O4 Cd2 2.648(7) 1_455 ?
O5 C9 1.263(13) . ?
O6 C9 1.240(13) . ?
O7 C16 1.237(13) . ?
O7 Cd1 2.325(8) 1_545 ?
O8 C16 1.253(12) . ?
O8 Cd1 2.364(7) 1_545 ?
O9 C29 1.397(13) . ?
O9 H9A 0.8200 . ?
N1 C19 1.306(13) . ?
N1 C17 1.378(13) . ?
N2 C18 1.331(14) . ?
N2 C19 1.370(12) . ?
N2 C20 1.449(13) . ?
N3 C25 1.298(14) . ?
N3 C23 1.395(12) . ?
N4 C25 1.381(14) . ?
N4 C24 1.411(14) . ?
N4 C26 1.455(14) . ?
C1 C2 1.481(14) . ?
C2 C3 1.377(13) . ?
C2 C7 1.404(14) . ?
C3 C4 1.385(12) . ?
C3 H3A 0.9300 . ?
C4 C5 1.382(13) . ?
C4 C8 1.510(14) . ?
C5 C6 1.378(14) . ?
C5 H5A 0.9300 . ?
C6 C7 1.406(13) . ?
C7 H7A 0.9300 . ?
C9 C10 1.479(15) . ?
C10 C11 1.397(14) . ?
C10 C15 1.425(14) . ?
C11 C12 1.402(15) . ?
C11 H11A 0.9300 . ?
C12 C13 1.407(14) . ?
C12 C16 1.479(14) . ?
C13 C14 1.337(14) . ?
C13 H13A 0.9300 . ?
C14 C15 1.392(15) . ?
C15 H15A 0.9300 . ?
C16 Cd1 2.665(11) 1_545 ?
C17 C18 1.383(15) . ?
C17 H17A 0.9300 . ?
C18 H18B 0.9300 . ?
C19 C22 1.466(14) . ?
C20 C21 1.519(14) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C21 1.536(18) 2_866 ?
C21 H21C 0.9700 . ?
C21 H21D 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.344(15) . ?
C23 H23A 0.9300 . ?
C25 C28 1.501(15) . ?
C26 C27 1.491(14) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C27 1.50(2) 2_655 ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?

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
O5 Cd1 N1 91.7(3) . . ?
O5 Cd1 O7 96.5(3) . 1_565 ?
N1 Cd1 O7 98.3(3) . 1_565 ?
O5 Cd1 O1 89.3(3) . . ?
N1 Cd1 O1 163.5(3) . . ?
O7 Cd1 O1 97.9(3) 1_565 . ?
O5 Cd1 O8 149.9(3) . 1_565 ?
N1 Cd1 O8 102.6(3) . 1_565 ?
O7 Cd1 O8 55.7(3) 1_565 1_565 ?
O1 Cd1 O8 84.3(3) . 1_565 ?
O5 Cd1 O3 111.3(3) . 1_655 ?
N1 Cd1 O3 87.5(3) . 1_655 ?
O7 Cd1 O3 151.5(3) 1_565 1_655 ?
O1 Cd1 O3 76.9(2) . 1_655 ?
O8 Cd1 O3 95.9(3) 1_565 1_655 ?
O5 Cd1 C16 123.5(3) . 1_565 ?
N1 Cd1 C16 101.2(4) . 1_565 ?
O7 Cd1 C16 27.6(3) 1_565 1_565 ?
O1 Cd1 C16 91.9(3) . 1_565 ?
O8 Cd1 C16 28.1(3) 1_565 1_565 ?
O3 Cd1 C16 123.9(3) 1_655 1_565 ?
O2 Cd2 N3 102.7(3) . . ?
O2 Cd2 O6 95.9(3) . . ?
N3 Cd2 O6 91.9(3) . . ?
O2 Cd2 O3 97.8(3) . 1_655 ?
N3 Cd2 O3 159.0(3) . 1_655 ?
O6 Cd2 O3 90.5(3) . 1_655 ?
O2 Cd2 O9 90.5(3) . . ?
N3 Cd2 O9 88.0(3) . . ?
O6 Cd2 O9 173.5(3) . . ?
O3 Cd2 O9 87.3(3) 1_655 . ?
O2 Cd2 O4 148.4(3) . 1_655 ?
N3 Cd2 O4 106.1(3) . 1_655 ?
O6 Cd2 O4 95.8(3) . 1_655 ?
O3 Cd2 O4 52.8(2) 1_655 1_655 ?
O9 Cd2 O4 77.9(3) . 1_655 ?
C1 O1 Cd1 137.7(8) . . ?
C1 O2 Cd2 125.6(8) . . ?
C8 O3 Cd2 99.7(7) . 1_455 ?
C8 O3 Cd1 127.5(6) . 1_455 ?
Cd2 O3 Cd1 103.1(3) 1_455 1_455 ?
C8 O4 Cd2 83.7(6) . 1_455 ?
C9 O5 Cd1 119.3(8) . . ?
C9 O6 Cd2 134.5(8) . . ?
C16 O7 Cd1 91.7(7) . 1_545 ?
C16 O8 Cd1 89.5(7) . 1_545 ?
C29 O9 Cd2 125.9(8) . . ?
C29 O9 H9A 109.5 . . ?
Cd2 O9 H9A 124.7 . . ?
C19 N1 C17 108.0(10) . . ?
C19 N1 Cd1 128.3(8) . . ?
C17 N1 Cd1 123.4(8) . . ?
C18 N2 C19 107.3(10) . . ?
C18 N2 C20 125.0(10) . . ?
C19 N2 C20 127.5(10) . . ?
C25 N3 C23 106.2(10) . . ?
C25 N3 Cd2 129.6(8) . . ?
C23 N3 Cd2 124.2(8) . . ?
C25 N4 C24 106.6(11) . . ?
C25 N4 C26 128.2(11) . . ?
C24 N4 C26 125.2(11) . . ?
O2 C1 O1 125.5(11) . . ?
O2 C1 C2 117.3(11) . . ?
O1 C1 C2 117.1(10) . . ?
C3 C2 C7 120.0(10) . . ?
C3 C2 C1 121.2(11) . . ?
C7 C2 C1 118.8(11) . . ?
C2 C3 C4 121.2(10) . . ?
C2 C3 H3A 119.4 . . ?
C4 C3 H3A 119.4 . . ?
C5 C4 C3 119.5(10) . . ?
C5 C4 C8 121.5(10) . . ?
C3 C4 C8 119.1(9) . . ?
C6 C5 C4 120.0(10) . . ?
C6 C5 H5A 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C5 C6 C7 121.3(11) . . ?
C5 C6 Br1 119.6(8) . . ?
C7 C6 Br1 119.1(9) . . ?
C2 C7 C6 117.9(11) . . ?
C2 C7 H7A 121.0 . . ?
C6 C7 H7A 121.0 . . ?
O4 C8 O3 123.3(11) . . ?
O4 C8 C4 121.0(9) . . ?
O3 C8 C4 115.7(10) . . ?
O6 C9 O5 126.2(12) . . ?
O6 C9 C10 117.2(11) . . ?
O5 C9 C10 116.6(12) . . ?
C11 C10 C15 117.6(11) . . ?
C11 C10 C9 121.3(11) . . ?
C15 C10 C9 121.1(11) . . ?
C10 C11 C12 122.0(11) . . ?
C10 C11 H11A 119.0 . . ?
C12 C11 H11A 119.0 . . ?
C11 C12 C13 118.0(10) . . ?
C11 C12 C16 119.8(10) . . ?
C13 C12 C16 122.1(11) . . ?
C14 C13 C12 120.7(12) . . ?
C14 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
C13 C14 C15 122.4(11) . . ?
C13 C14 Br2 120.8(10) . . ?
C15 C14 Br2 116.8(8) . . ?
C14 C15 C10 119.1(10) . . ?
C14 C15 H15A 120.4 . . ?
C10 C15 H15A 120.4 . . ?
O7 C16 O8 123.1(10) . . ?
O7 C16 C12 117.8(11) . . ?
O8 C16 C12 118.9(11) . . ?
O7 C16 Cd1 60.7(6) . 1_545 ?
O8 C16 Cd1 62.5(6) . 1_545 ?
C12 C16 Cd1 173.4(9) . 1_545 ?
N1 C17 C18 106.5(11) . . ?
N1 C17 H17A 126.7 . . ?
C18 C17 H17A 126.7 . . ?
N2 C18 C17 108.2(11) . . ?
N2 C18 H18B 125.9 . . ?
C17 C18 H18B 125.9 . . ?
N1 C19 N2 109.9(10) . . ?
N1 C19 C22 128.4(11) . . ?
N2 C19 C22 121.6(11) . . ?
N2 C20 C21 112.3(9) . . ?
N2 C20 H20A 109.2 . . ?
C21 C20 H20A 109.2 . . ?
N2 C20 H20B 109.2 . . ?
C21 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C20 C21 C21 110.4(11) . 2_866 ?
C20 C21 H21C 109.6 . . ?
C21 C21 H21C 109.6 2_866 . ?
C20 C21 H21D 109.6 . . ?
C21 C21 H21D 109.6 2_866 . ?
H21C C21 H21D 108.1 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 N3 111.0(11) . . ?
C24 C23 H23A 124.5 . . ?
N3 C23 H23A 124.5 . . ?
C23 C24 N4 105.0(11) . . ?
N3 C25 N4 111.2(11) . . ?
N3 C25 C28 127.7(12) . . ?
N4 C25 C28 121.1(12) . . ?
N4 C26 C27 112.6(10) . . ?
N4 C26 H26A 109.1 . . ?
C27 C26 H26A 109.1 . . ?
N4 C26 H26B 109.1 . . ?
C27 C26 H26B 109.1 . . ?
H26A C26 H26B 107.8 . . ?
C26 C27 C27 117.0(14) . 2_655 ?
C26 C27 H27A 108.1 . . ?
C27 C27 H27A 108.1 2_655 . ?
C26 C27 H27B 108.1 . . ?
C27 C27 H27B 108.1 2_655 . ?
H27A C27 H27B 107.3 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O9 C29 H29A 109.5 . . ?
O9 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O9 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        26.02
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         1.211
_refine_diff_density_min         -1.060
_refine_diff_density_rms         0.193
_database_code_depnum_ccdc_archive 'CCDC 990995'
#######################################################################
#
#                 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_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 Br Cd N4 O4'
_chemical_formula_weight         573.72

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Pnna '

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

_cell_length_a                   8.7933(7)
_cell_length_b                   17.7457(16)
_cell_length_c                   14.8568(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2318.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1796
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      22.63

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    2.697
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5189
_exptl_absorpt_correction_T_max  0.6722
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10906
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         25.10
_reflns_number_total             2073
_reflns_number_gt                1472
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0300P)²+0.0869P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2073
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0706
_refine_ls_wR_factor_gt          0.0630
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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 0.08690(4) 0.2500 0.2500 0.03505(13) Uani 1 2 d S . .
N1 N 0.2523(4) 0.27625(16) 0.14027(18) 0.0391(7) Uani 1 1 d . . .
N2 N 0.4210(3) 0.33649(16) 0.0588(2) 0.0424(7) Uani 1 1 d . . .
O1 O -0.0735(4) 0.38332(19) 0.1996(2) 0.0944(12) Uani 1 1 d . . .
O2 O -0.0362(3) 0.33023(16) 0.33018(19) 0.0623(8) Uani 1 1 d . . .
Br1 Br -0.2500 0.5000 0.59589(4) 0.0717(2) Uani 1 2 d S . .
C1 C -0.2500 0.5000 0.4681(3) 0.0450(13) Uani 1 2 d S . .
C2 C -0.1734(4) 0.4438(2) 0.4230(2) 0.0438(9) Uani 1 1 d . . .
H2 H -0.1218 0.4066 0.4548 0.053 Uiso 1 1 calc R . .
C3 C -0.1740(4) 0.4434(2) 0.3294(2) 0.0401(9) Uani 1 1 d . . .
C4 C -0.2500 0.5000 0.2836(3) 0.0400(12) Uani 1 2 d S . .
H4 H -0.2500 0.5000 0.2210 0.048 Uiso 1 2 calc SR . .
C5 C -0.0882(4) 0.3818(2) 0.2815(3) 0.0501(10) Uani 1 1 d . . .
C6 C 0.2575(4) 0.24456(19) 0.0560(2) 0.0425(9) Uani 1 1 d . . .
H6 H 0.1992 0.2039 0.0368 0.051 Uiso 1 1 calc R . .
C7 C 0.3598(5) 0.2814(2) 0.0058(3) 0.0491(10) Uani 1 1 d . . .
H7 H 0.3845 0.2714 -0.0539 0.059 Uiso 1 1 calc R . .
C8 C 0.3532(4) 0.3314(2) 0.1400(2) 0.0428(9) Uani 1 1 d . . .
C9 C 0.3881(6) 0.3809(3) 0.2184(3) 0.0830(17) Uani 1 1 d . . .
H9A H 0.3261 0.3664 0.2687 0.124 Uiso 1 1 calc R . .
H9B H 0.3673 0.4324 0.2028 0.124 Uiso 1 1 calc R . .
H9C H 0.4935 0.3758 0.2341 0.124 Uiso 1 1 calc R . .
C10 C 0.5279(4) 0.3954(2) 0.0311(3) 0.0524(11) Uani 1 1 d . . .
H10A H 0.5815 0.3793 -0.0227 0.063 Uiso 1 1 calc R . .
H10B H 0.6024 0.4033 0.0783 0.063 Uiso 1 1 calc R . .
C11 C 0.4462(4) 0.4685(2) 0.0122(3) 0.0490(10) Uani 1 1 d . . .
H11A H 0.3884 0.4830 0.0651 0.059 Uiso 1 1 calc R . .
H11B H 0.3750 0.4609 -0.0368 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 O2 2.149(3) . ?
Cd1 O2 2.149(3) 4 ?
Cd1 N1 2.233(3) 4 ?
Cd1 N1 2.234(3) . ?
N1 C8 1.321(4) . ?
N1 C6 1.374(4) . ?
N2 C8 1.349(4) . ?
N2 C7 1.365(5) . ?
N2 C10 1.465(4) . ?
O1 C5 1.223(5) . ?
O2 C5 1.253(5) . ?
Br1 C1 1.898(5) . ?
C1 C2 1.377(4) 2_465 ?
C1 C2 1.377(4) . ?
C2 C3 1.391(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(4) . ?
C3 C5 1.507(5) . ?
C4 C3 1.386(4) 2_465 ?
C4 H4 0.9300 . ?
C6 C7 1.339(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.491(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.508(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C11 1.509(7) 5_665 ?
C11 H11A 0.9700 . ?
C11 H11B 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
O2 Cd1 O2 119.49(16) . 4 ?
O2 Cd1 N1 93.53(11) . 4 ?
O2 Cd1 N1 126.47(11) 4 4 ?
O2 Cd1 N1 126.47(11) . . ?
O2 Cd1 N1 93.53(11) 4 . ?
N1 Cd1 N1 98.77(16) 4 . ?
C8 N1 C6 106.1(3) . . ?
C8 N1 Cd1 126.4(2) . . ?
C6 N1 Cd1 127.0(2) . . ?
C8 N2 C7 107.1(3) . . ?
C8 N2 C10 125.6(3) . . ?
C7 N2 C10 127.0(3) . . ?
C5 O2 Cd1 110.3(3) . . ?
C2 C1 C2 121.8(5) 2_465 . ?
C2 C1 Br1 119.1(2) 2_465 . ?
C2 C1 Br1 119.1(2) . . ?
C1 C2 C3 119.2(4) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 119.3(4) . . ?
C4 C3 C5 122.3(4) . . ?
C2 C3 C5 118.4(3) . . ?
C3 C4 C3 121.1(5) . 2_465 ?
C3 C4 H4 119.5 . . ?
C3 C4 H4 119.5 2_465 . ?
O1 C5 O2 123.5(4) . . ?
O1 C5 C3 120.5(4) . . ?
O2 C5 C3 116.0(4) . . ?
C7 C6 N1 109.3(3) . . ?
C7 C6 H6 125.3 . . ?
N1 C6 H6 125.3 . . ?
C6 C7 N2 107.0(3) . . ?
C6 C7 H7 126.5 . . ?
N2 C7 H7 126.5 . . ?
N1 C8 N2 110.4(3) . . ?
N1 C8 C9 124.9(3) . . ?
N2 C8 C9 124.6(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C11 111.1(3) . . ?
N2 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
N2 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 C11 112.5(4) . 5_665 ?
C10 C11 H11A 109.1 . . ?
C11 C11 H11A 109.1 5_665 . ?
C10 C11 H11B 109.1 . . ?
C11 C11 H11B 109.1 5_665 . ?
H11A C11 H11B 107.8 . . ?

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
O2 Cd1 N1 C8 38.9(4) . . . . ?
O2 Cd1 N1 C8 170.1(3) 4 . . . ?
N1 Cd1 N1 C8 -62.2(3) 4 . . . ?
O2 Cd1 N1 C6 -132.7(3) . . . . ?
O2 Cd1 N1 C6 -1.5(3) 4 . . . ?
N1 Cd1 N1 C6 126.2(3) 4 . . . ?
O2 Cd1 O2 C5 -76.4(3) 4 . . . ?
N1 Cd1 O2 C5 147.6(3) 4 . . . ?
N1 Cd1 O2 C5 44.0(3) . . . . ?
C2 C1 C2 C3 -0.4(2) 2_465 . . . ?
Br1 C1 C2 C3 179.6(2) . . . . ?
C1 C2 C3 C4 0.8(5) . . . . ?
C1 C2 C3 C5 179.5(3) . . . . ?
C2 C3 C4 C3 -0.4(2) . . . 2_465 ?
C5 C3 C4 C3 -179.0(4) . . . 2_465 ?
Cd1 O2 C5 O1 2.3(5) . . . . ?
Cd1 O2 C5 C3 -178.4(3) . . . . ?
C4 C3 C5 O1 5.7(6) . . . . ?
C2 C3 C5 O1 -172.9(4) . . . . ?
C4 C3 C5 O2 -173.7(3) . . . . ?
C2 C3 C5 O2 7.7(5) . . . . ?
C8 N1 C6 C7 -0.8(4) . . . . ?
Cd1 N1 C6 C7 172.2(3) . . . . ?
N1 C6 C7 N2 0.5(4) . . . . ?
C8 N2 C7 C6 -0.1(4) . . . . ?
C10 N2 C7 C6 -174.2(3) . . . . ?
C6 N1 C8 N2 0.7(4) . . . . ?
Cd1 N1 C8 N2 -172.4(2) . . . . ?
C6 N1 C8 C9 -179.1(4) . . . . ?
Cd1 N1 C8 C9 7.9(6) . . . . ?
C7 N2 C8 N1 -0.3(4) . . . . ?
C10 N2 C8 N1 173.8(3) . . . . ?
C7 N2 C8 C9 179.4(4) . . . . ?
C10 N2 C8 C9 -6.5(6) . . . . ?
C8 N2 C10 C11 -75.0(5) . . . . ?
C7 N2 C10 C11 98.0(4) . . . . ?
N2 C10 C11 C11 177.3(4) . . . 5_665 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.085
_database_code_depnum_ccdc_archive 'CCDC 990996'
#######################################################################
#
#                 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_4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 Br Cd N2 O7'
_chemical_formula_weight         518.61

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   17.051(2)
_cell_length_b                   11.4036(14)
_cell_length_c                   19.722(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.910(2)
_cell_angle_gamma                90.00
_cell_volume                     3605.7(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    960
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      19.6

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.911
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2040
_exptl_absorpt_coefficient_mu    3.465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4437
_exptl_absorpt_correction_T_max  0.6071
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9366
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_sigmaI/netI    0.0907
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         26.07
_reflns_number_total             3546
_reflns_number_gt                2488
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0450P)²+3.2000P] 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         3546
_refine_ls_number_parameters     254
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0613
_refine_ls_wR_factor_ref         0.1259
_refine_ls_wR_factor_gt          0.1102
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.019
_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 0.83116(3) 0.57273(5) 0.47029(3) 0.03096(18) Uani 1 1 d . . .
O1 O 0.7474(3) 0.5571(5) 0.5376(3) 0.0383(13) Uani 1 1 d . . .
O2 O 0.6871(4) 0.4342(6) 0.4508(3) 0.068(2) Uani 1 1 d . . .
O3 O 0.3958(3) 0.2335(5) 0.5547(3) 0.0470(15) Uani 1 1 d . . .
O4 O 0.4520(3) 0.1847(5) 0.4743(3) 0.0417(14) Uani 1 1 d . . .
N1 N 0.8324(4) 0.4810(6) 0.3709(3) 0.0369(16) Uani 1 1 d . . .
N2 N 0.8540(4) 0.4394(6) 0.2696(3) 0.0410(17) Uani 1 1 d . . .
C1 C 0.6918(5) 0.4834(7) 0.5077(4) 0.0355(19) Uani 1 1 d . . .
C2 C 0.6320(5) 0.4523(7) 0.5471(4) 0.0332(18) Uani 1 1 d . . .
C3 C 0.6445(4) 0.4986(7) 0.6134(4) 0.0336(18) Uani 1 1 d . . .
H3A H 0.6882 0.5504 0.6340 0.040 Uiso 1 1 calc R . .
C4 C 0.5902(5) 0.4670(7) 0.6505(4) 0.0362(19) Uani 1 1 d . . .
C5 C 0.5265(4) 0.3900(7) 0.6209(4) 0.0360(19) Uani 1 1 d . . .
H5A H 0.4903 0.3714 0.6455 0.043 Uiso 1 1 calc R . .
C6 C 0.5156(4) 0.3396(6) 0.5546(4) 0.0298(17) Uani 1 1 d . . .
C7 C 0.5684(4) 0.3711(6) 0.5178(4) 0.0301(17) Uani 1 1 d . . .
H7A H 0.5614 0.3378 0.4730 0.036 Uiso 1 1 calc R . .
C8 C 0.4502(4) 0.2479(6) 0.5260(4) 0.0315(18) Uani 1 1 d . . .
C9 C 0.8258(5) 0.3617(7) 0.3600(5) 0.045(2) Uani 1 1 d . . .
H9A H 0.8146 0.3071 0.3905 0.054 Uiso 1 1 calc R . .
C10 C 0.8384(5) 0.3374(8) 0.2972(4) 0.046(2) Uani 1 1 d . . .
H10A H 0.8367 0.2635 0.2768 0.055 Uiso 1 1 calc R . .
C11 C 0.8494(5) 0.5254(7) 0.3152(4) 0.0358(19) Uani 1 1 d . . .
C12 C 0.8788(5) 0.4516(9) 0.2055(4) 0.051(3) Uani 1 1 d . . .
H12A H 0.8433 0.5086 0.1740 0.061 Uiso 1 1 d R . .
H12B H 0.8700 0.3778 0.1806 0.061 Uiso 1 1 d R . .
C13 C 0.9713(10) 0.4880(17) 0.2234(8) 0.041(4) Uani 0.50 1 d P . .
H13D H 0.9792 0.5656 0.2434 0.049 Uiso 0.50 1 d PR . .
H13E H 0.9844 0.4896 0.1798 0.049 Uiso 0.50 1 d PR . .
C14 C 1.0312(11) 0.4023(18) 0.2777(9) 0.047(5) Uani 0.50 1 d P . .
H14A H 1.0269 0.3253 0.2571 0.057 Uiso 0.50 1 d PR . .
H14B H 1.0177 0.3977 0.3211 0.057 Uiso 0.50 1 d PR . .
C15 C 0.8600(6) 0.6539(7) 0.3023(4) 0.054(2) Uani 1 1 d . . .
H13A H 0.8257 0.6995 0.3221 0.080 Uiso 1 1 calc R . .
H13B H 0.8437 0.6682 0.2514 0.080 Uiso 1 1 calc R . .
H13C H 0.9174 0.6756 0.3252 0.080 Uiso 1 1 calc R . .
Br1 Br 0.61425(7) 0.52273(11) 0.74646(5) 0.0701(4) Uani 1 1 d . . .
O1W O 0.9156(4) 0.4331(6) 0.5445(3) 0.0554(17) Uani 1 1 d D . .
H1A H 0.956(4) 0.406(8) 0.536(4) 0.083 Uiso 1 1 d D . .
H1B H 0.905(5) 0.403(7) 0.578(4) 0.083 Uiso 1 1 d D . .
O2W O 0.7395(3) 0.7200(5) 0.4049(3) 0.0398(13) Uani 1 1 d D . .
H2A H 0.6912(19) 0.701(6) 0.399(4) 0.060 Uiso 1 1 d D . .
H2B H 0.757(4) 0.778(5) 0.431(4) 0.060 Uiso 1 1 d D . .
O3W O 0.8702(9) 0.2617(9) 0.6249(5) 0.155(5) Uani 1 1 d D . .
H3B H 0.890(8) 0.196(6) 0.630(10) 0.232 Uiso 1 1 d D . .
H3C H 0.822(3) 0.267(11) 0.596(7) 0.232 Uiso 1 1 d D . .


_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 2.228(6) . ?
Cd1 O1 2.264(5) . ?
Cd1 O1W 2.306(6) . ?
Cd1 O2W 2.356(6) . ?
Cd1 O4 2.402(5) 3 ?
Cd1 O3 2.469(5) 3 ?
O1 C1 1.254(9) . ?
O2 C1 1.233(9) . ?
O3 C8 1.249(8) . ?
O3 Cd1 2.469(5) 3_445 ?
O4 C8 1.258(8) . ?
O4 Cd1 2.402(5) 3_445 ?
N1 C11 1.328(9) . ?
N1 C9 1.376(10) . ?
N2 C10 1.348(10) . ?
N2 C11 1.350(10) . ?
N2 C12 1.470(9) . ?
C1 C2 1.520(10) . ?
C2 C3 1.357(10) . ?
C2 C7 1.393(10) . ?
C3 C4 1.407(10) . ?
C3 H3A 0.9300 . ?
C4 C5 1.364(10) . ?
C4 Br1 1.904(7) . ?
C5 C6 1.383(10) . ?
C5 H5A 0.9300 . ?
C6 C7 1.383(9) . ?
C6 C8 1.493(9) . ?
C7 H7A 0.9300 . ?
C9 C10 1.356(10) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C15 1.508(11) . ?
C12 C13 1.551(19) . ?
C12 C14 1.560(19) 2_755 ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C13 C14 0.98(2) 2_755 ?
C13 C13 1.17(3) 2_755 ?
C13 C14 1.549(19) . ?
C13 H13D 0.9600 . ?
C13 H13E 0.9601 . ?
C14 C13 0.98(2) 2_755 ?
C14 C14 1.24(3) 2_755 ?
C14 C12 1.560(19) 2_755 ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C15 H13A 0.9600 . ?
C15 H13B 0.9600 . ?
C15 H13C 0.9600 . ?
O1W H1A 0.819(10) . ?
O1W H1B 0.819(10) . ?
O2W H2A 0.822(10) . ?
O2W H2B 0.822(10) . ?
O3W H3B 0.821(10) . ?
O3W H3C 0.822(10) . ?

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 O1 132.5(2) . . ?
N1 Cd1 O1W 92.5(2) . . ?
O1 Cd1 O1W 87.48(19) . . ?
N1 Cd1 O2W 93.2(2) . . ?
O1 Cd1 O2W 86.77(18) . . ?
O1W Cd1 O2W 173.75(18) . . ?
N1 Cd1 O4 90.8(2) . 3 ?
O1 Cd1 O4 136.72(18) . 3 ?
O1W Cd1 O4 90.2(2) . 3 ?
O2W Cd1 O4 92.35(19) . 3 ?
N1 Cd1 O3 143.6(2) . 3 ?
O1 Cd1 O3 83.67(17) . 3 ?
O1W Cd1 O3 92.6(2) . 3 ?
O2W Cd1 O3 84.29(19) . 3 ?
O4 Cd1 O3 53.27(17) 3 3 ?
C1 O1 Cd1 107.8(5) . . ?
C8 O3 Cd1 91.3(5) . 3_445 ?
C8 O4 Cd1 94.2(4) . 3_445 ?
C11 N1 C9 106.1(7) . . ?
C11 N1 Cd1 128.3(6) . . ?
C9 N1 Cd1 125.2(5) . . ?
C10 N2 C11 107.1(7) . . ?
C10 N2 C12 125.6(7) . . ?
C11 N2 C12 127.1(7) . . ?
O2 C1 O1 122.5(7) . . ?
O2 C1 C2 120.8(7) . . ?
O1 C1 C2 116.6(7) . . ?
C3 C2 C7 120.2(7) . . ?
C3 C2 C1 119.3(7) . . ?
C7 C2 C1 120.4(7) . . ?
C2 C3 C4 119.1(7) . . ?
C2 C3 H3A 120.5 . . ?
C4 C3 H3A 120.5 . . ?
C5 C4 C3 120.8(7) . . ?
C5 C4 Br1 120.7(6) . . ?
C3 C4 Br1 118.3(6) . . ?
C4 C5 C6 120.2(7) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C5 C6 C7 119.1(6) . . ?
C5 C6 C8 119.4(6) . . ?
C7 C6 C8 121.4(7) . . ?
C6 C7 C2 120.5(7) . . ?
C6 C7 H7A 119.7 . . ?
C2 C7 H7A 119.7 . . ?
O3 C8 O4 121.2(7) . . ?
O3 C8 C6 119.7(7) . . ?
O4 C8 C6 119.1(6) . . ?
C10 C9 N1 108.3(8) . . ?
C10 C9 H9A 125.8 . . ?
N1 C9 H9A 125.8 . . ?
N2 C10 C9 107.8(8) . . ?
N2 C10 H10A 126.1 . . ?
C9 C10 H10A 126.1 . . ?
N1 C11 N2 110.7(7) . . ?
N1 C11 C15 125.6(7) . . ?
N2 C11 C15 123.7(7) . . ?
N2 C12 C13 113.4(8) . . ?
N2 C12 C14 109.5(9) . 2_755 ?
C13 C12 C14 36.6(8) . 2_755 ?
N2 C12 H12A 108.6 . . ?
C13 C12 H12A 109.5 . . ?
C14 C12 H12A 137.7 2_755 . ?
N2 C12 H12B 108.5 . . ?
C13 C12 H12B 108.7 . . ?
C14 C12 H12B 76.4 2_755 . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C13 92.1(15) 2_755 2_755 ?
C14 C13 C14 53.0(18) 2_755 . ?
C13 C13 C14 39.1(8) 2_755 . ?
C14 C13 C12 72.2(17) 2_755 . ?
C13 C13 C12 133(2) 2_755 . ?
C14 C13 C12 111.6(12) . . ?
C14 C13 H13D 158.3 2_755 . ?
C13 C13 H13D 70.9 2_755 . ?
C14 C13 H13D 109.3 . . ?
C12 C13 H13D 109.2 . . ?
C14 C13 H13E 91.2 2_755 . ?
C13 C13 H13E 115.2 2_755 . ?
C14 C13 H13E 109.4 . . ?
C12 C13 H13E 109.3 . . ?
H13D C13 H13E 108.0 . . ?
C13 C14 C14 87.9(16) 2_755 2_755 ?
C13 C14 C13 48.8(16) 2_755 . ?
C14 C14 C13 39.1(8) 2_755 . ?
C13 C14 C12 71.2(16) 2_755 2_755 ?
C14 C14 C12 132.4(19) 2_755 2_755 ?
C13 C14 C12 106.8(12) . 2_755 ?
C13 C14 H14A 155.3 2_755 . ?
C14 C14 H14A 73.0 2_755 . ?
C13 C14 H14A 110.3 . . ?
C12 C14 H14A 110.3 2_755 . ?
C13 C14 H14B 93.0 2_755 . ?
C14 C14 H14B 113.0 2_755 . ?
C13 C14 H14B 110.4 . . ?
C12 C14 H14B 110.3 2_755 . ?
H14A C14 H14B 108.6 . . ?
C11 C15 H13A 109.5 . . ?
C11 C15 H13B 109.5 . . ?
H13A C15 H13B 109.5 . . ?
C11 C15 H13C 109.5 . . ?
H13A C15 H13C 109.5 . . ?
H13B C15 H13C 109.5 . . ?
Cd1 O1W H1A 121(5) . . ?
Cd1 O1W H1B 122(5) . . ?
H1A O1W H1B 116(2) . . ?
Cd1 O2W H2A 109(6) . . ?
Cd1 O2W H2B 102(6) . . ?
H2A O2W H2B 115(2) . . ?
H3B O3W H3C 115(2) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.07
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         1.008
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.130
_database_code_depnum_ccdc_archive 'CCDC 990997'
#######################################################################
#
#                 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_5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Br Cd N2 O5'
_chemical_formula_weight         482.58

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'
Br Br -0.2901 2.4595 '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                   8.3536(9)
_cell_length_b                   10.0782(10)
_cell_length_c                   11.2967(12)
_cell_angle_alpha                74.969(2)
_cell_angle_beta                 74.612(2)
_cell_angle_gamma                68.4250(10)
_cell_volume                     838.73(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2729
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      26.895

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.911
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             470
_exptl_absorpt_coefficient_mu    3.708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4233
_exptl_absorpt_correction_T_max  0.5884
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4148
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         25.10
_reflns_number_total             2923
_reflns_number_gt                2667
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?


_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)+(0.1000P)²+0.3520P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0101(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2923
_refine_ls_number_parameters     210
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.1104
_refine_ls_wR_factor_gt          0.1029
_refine_ls_goodness_of_fit_ref   0.878
_refine_ls_restrained_S_all      0.878
_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
O2 O 0.2040(4) 0.7825(3) 0.6028(3) 0.0462(8) Uani 1 1 d . . .
O1 O 0.3389(5) 0.6874(4) 0.4353(4) 0.0557(10) Uani 1 1 d . . .
C8 C 0.2456(6) 0.6848(5) 0.5390(5) 0.0399(10) Uani 1 1 d . . .
Cd1 Cd 0.34914(3) -0.07457(3) 0.44144(3) 0.02992(17) Uani 1 1 d . . .
N1 N 0.5233(4) -0.0820(4) 0.2501(3) 0.0325(8) Uani 1 1 d . . .
N2 N 0.6853(5) -0.0429(5) 0.0652(3) 0.0396(9) Uani 1 1 d . . .
O3 O 0.1593(5) 0.1052(4) 0.5533(4) 0.0524(9) Uani 1 1 d . . .
O4 O 0.3993(4) 0.1609(3) 0.4667(3) 0.0388(7) Uani 1 1 d . . .
O5 O 0.1080(4) 0.0082(4) 0.3382(3) 0.0425(7) Uani 1 1 d D . .
H5B H 0.0470 0.0939 0.3497 0.051 Uiso 1 1 d RD . .
H5C H 0.0438 -0.0457 0.3705 0.051 Uiso 1 1 d RD . .
Br1 Br -0.20576(11) 0.46268(7) 0.89138(7) 0.0905(3) Uani 1 1 d . . .
C1 C 0.2475(6) 0.1894(4) 0.5333(4) 0.0324(9) Uani 1 1 d . . .
C2 C 0.1694(5) 0.3245(4) 0.5872(4) 0.0282(8) Uani 1 1 d . . .
C3 C 0.0318(6) 0.3348(5) 0.6892(4) 0.0377(10) Uani 1 1 d . . .
H3 H -0.0200 0.2621 0.7189 0.045 Uiso 1 1 calc R . .
C4 C -0.0265(6) 0.4539(5) 0.7454(5) 0.0425(11) Uani 1 1 d . . .
C5 C 0.0414(7) 0.5672(5) 0.7010(5) 0.0427(11) Uani 1 1 d . . .
H5 H 0.0001 0.6465 0.7411 0.051 Uiso 1 1 calc R . .
C6 C 0.1728(5) 0.5601(4) 0.5952(4) 0.0303(8) Uani 1 1 d . . .
C7 C 0.2378(5) 0.4377(4) 0.5403(4) 0.0318(9) Uani 1 1 d . . .
H7 H 0.3286 0.4318 0.4712 0.038 Uiso 1 1 calc R . .
C9 C 0.5634(7) 0.1628(6) 0.1832(5) 0.0534(13) Uani 1 1 d . . .
H9A H 0.4520 0.1980 0.2361 0.080 Uiso 1 1 calc R . .
H9B H 0.5659 0.2257 0.1032 0.080 Uiso 1 1 calc R . .
H9C H 0.6551 0.1608 0.2206 0.080 Uiso 1 1 calc R . .
C10 C 0.5899(5) 0.0144(5) 0.1671(4) 0.0365(10) Uani 1 1 d . . .
C11 C 0.5790(6) -0.2047(6) 0.1968(4) 0.0418(10) Uani 1 1 d . . .
H11 H 0.5519 -0.2896 0.2337 0.050 Uiso 1 1 calc R . .
C12 C 0.6787(6) -0.1815(6) 0.0833(5) 0.0456(12) Uani 1 1 d . . .
H12 H 0.7324 -0.2462 0.0280 0.055 Uiso 1 1 calc R . .
C13 C 0.7810(6) 0.0264(7) -0.0488(4) 0.0521(13) Uani 1 1 d . . .
H13A H 0.7349 0.1308 -0.0543 0.062 Uiso 1 1 calc R . .
H13B H 0.7621 0.0039 -0.1214 0.062 Uiso 1 1 calc R . .
C14 C 0.9771(6) -0.0249(6) -0.0496(4) 0.0464(12) Uani 1 1 d . . .
H14A H 1.0205 -0.1300 -0.0367 0.056 Uiso 1 1 calc R . .
H14B H 1.0364 0.0111 -0.1311 0.056 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
O2 C8 1.262(6) . ?
O2 Cd1 2.370(3) 1_565 ?
O1 C8 1.223(6) . ?
O1 Cd1 2.451(3) 1_565 ?
C8 C6 1.515(6) . ?
C8 Cd1 2.738(4) 1_565 ?
Cd1 N1 2.265(3) . ?
Cd1 O3 2.325(3) . ?
Cd1 O4 2.365(3) 2_656 ?
Cd1 O2 2.370(3) 1_545 ?
Cd1 O5 2.370(3) . ?
Cd1 O1 2.451(3) 1_545 ?
Cd1 C8 2.738(4) 1_545 ?
N1 C10 1.335(6) . ?
N1 C11 1.386(6) . ?
N2 C10 1.347(6) . ?
N2 C12 1.378(7) . ?
N2 C13 1.477(6) . ?
O3 C1 1.259(5) . ?
O4 C1 1.263(5) . ?
O4 Cd1 2.365(3) 2_656 ?
O5 H5B 0.8500 . ?
O5 H5C 0.8500 . ?
Br1 C4 1.907(5) . ?
C1 C2 1.489(5) . ?
C2 C7 1.384(6) . ?
C2 C3 1.390(6) . ?
C3 C4 1.372(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(7) . ?
C5 C6 1.388(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.388(6) . ?
C7 H7 0.9300 . ?
C9 C10 1.481(7) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C11 C12 1.347(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.524(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C14 1.522(10) 2_755 ?
C14 H14A 0.9700 . ?
C14 H14B 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
C8 O2 Cd1 92.7(3) . 1_565 ?
C8 O1 Cd1 89.9(3) . 1_565 ?
O1 C8 O2 123.3(4) . . ?
O1 C8 C6 119.5(4) . . ?
O2 C8 C6 117.3(4) . . ?
O1 C8 Cd1 63.5(2) . 1_565 ?
O2 C8 Cd1 59.8(2) . 1_565 ?
C6 C8 Cd1 175.2(3) . 1_565 ?
N1 Cd1 O3 136.26(13) . . ?
N1 Cd1 O4 89.79(11) . 2_656 ?
O3 Cd1 O4 102.83(12) . 2_656 ?
N1 Cd1 O2 140.83(12) . 1_545 ?
O3 Cd1 O2 81.03(12) . 1_545 ?
O4 Cd1 O2 92.51(12) 2_656 1_545 ?
N1 Cd1 O5 86.90(11) . . ?
O3 Cd1 O5 80.15(12) . . ?
O4 Cd1 O5 176.60(10) 2_656 . ?
O2 Cd1 O5 89.57(12) 1_545 . ?
N1 Cd1 O1 86.97(13) . 1_545 ?
O3 Cd1 O1 131.49(12) . 1_545 ?
O4 Cd1 O1 96.75(13) 2_656 1_545 ?
O2 Cd1 O1 53.92(12) 1_545 1_545 ?
O5 Cd1 O1 82.31(13) . 1_545 ?
N1 Cd1 C8 113.50(14) . 1_545 ?
O3 Cd1 C8 106.64(13) . 1_545 ?
O4 Cd1 C8 96.08(12) 2_656 1_545 ?
O2 Cd1 C8 27.42(14) 1_545 1_545 ?
O5 Cd1 C8 84.55(13) . 1_545 ?
O1 Cd1 C8 26.53(14) 1_545 1_545 ?
C10 N1 C11 106.4(4) . . ?
C10 N1 Cd1 132.9(3) . . ?
C11 N1 Cd1 120.7(3) . . ?
C10 N2 C12 108.1(4) . . ?
C10 N2 C13 127.8(5) . . ?
C12 N2 C13 124.1(4) . . ?
C1 O3 Cd1 101.7(3) . . ?
C1 O4 Cd1 120.8(3) . 2_656 ?
Cd1 O5 H5B 108.9 . . ?
Cd1 O5 H5C 109.0 . . ?
H5B O5 H5C 107.8 . . ?
O3 C1 O4 120.5(4) . . ?
O3 C1 C2 119.2(4) . . ?
O4 C1 C2 120.2(4) . . ?
C7 C2 C3 119.5(4) . . ?
C7 C2 C1 120.6(4) . . ?
C3 C2 C1 119.8(4) . . ?
C4 C3 C2 119.0(4) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 122.4(4) . . ?
C3 C4 Br1 119.0(3) . . ?
C5 C4 Br1 118.6(3) . . ?
C4 C5 C6 118.5(4) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C7 C6 C5 119.7(4) . . ?
C7 C6 C8 119.7(4) . . ?
C5 C6 C8 120.7(4) . . ?
C2 C7 C6 120.8(4) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 N2 109.8(4) . . ?
N1 C10 C9 125.7(4) . . ?
N2 C10 C9 124.5(4) . . ?
C12 C11 N1 109.2(4) . . ?
C12 C11 H11 125.4 . . ?
N1 C11 H11 125.4 . . ?
C11 C12 N2 106.5(4) . . ?
C11 C12 H12 126.8 . . ?
N2 C12 H12 126.8 . . ?
N2 C13 C14 111.9(4) . . ?
N2 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
N2 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C14 C14 C13 113.4(5) 2_755 . ?
C14 C14 H14A 108.9 2_755 . ?
C13 C14 H14A 108.9 . . ?
C14 C14 H14B 108.9 2_755 . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?

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 O1 C8 O2 -3.5(5) 1_565 . . . ?
Cd1 O1 C8 C6 175.8(4) 1_565 . . . ?
Cd1 O2 C8 O1 3.6(5) 1_565 . . . ?
Cd1 O2 C8 C6 -175.7(3) 1_565 . . . ?
O3 Cd1 N1 C10 19.0(5) . . . . ?
O4 Cd1 N1 C10 -89.5(4) 2_656 . . . ?
O2 Cd1 N1 C10 176.8(3) 1_545 . . . ?
O5 Cd1 N1 C10 91.3(4) . . . . ?
O1 Cd1 N1 C10 173.7(4) 1_545 . . . ?
C8 Cd1 N1 C10 174.0(4) 1_545 . . . ?
O3 Cd1 N1 C11 -159.8(3) . . . . ?
O4 Cd1 N1 C11 91.7(3) 2_656 . . . ?
O2 Cd1 N1 C11 -2.0(4) 1_545 . . . ?
O5 Cd1 N1 C11 -87.5(3) . . . . ?
O1 Cd1 N1 C11 -5.1(3) 1_545 . . . ?
C8 Cd1 N1 C11 -4.8(4) 1_545 . . . ?
N1 Cd1 O3 C1 -44.9(4) . . . . ?
O4 Cd1 O3 C1 58.5(3) 2_656 . . . ?
O2 Cd1 O3 C1 149.1(3) 1_545 . . . ?
O5 Cd1 O3 C1 -119.8(3) . . . . ?
O1 Cd1 O3 C1 169.8(3) 1_545 . . . ?
C8 Cd1 O3 C1 159.0(3) 1_545 . . . ?
Cd1 O3 C1 O4 -0.4(5) . . . . ?
Cd1 O3 C1 C2 178.4(3) . . . . ?
Cd1 O4 C1 O3 -105.2(4) 2_656 . . . ?
Cd1 O4 C1 C2 75.9(5) 2_656 . . . ?
O3 C1 C2 C7 -161.6(4) . . . . ?
O4 C1 C2 C7 17.3(6) . . . . ?
O3 C1 C2 C3 21.4(6) . . . . ?
O4 C1 C2 C3 -159.7(4) . . . . ?
C7 C2 C3 C4 -3.6(7) . . . . ?
C1 C2 C3 C4 173.4(4) . . . . ?
C2 C3 C4 C5 2.9(8) . . . . ?
C2 C3 C4 Br1 -176.3(3) . . . . ?
C3 C4 C5 C6 0.4(8) . . . . ?
Br1 C4 C5 C6 179.6(4) . . . . ?
C4 C5 C6 C7 -2.9(7) . . . . ?
C4 C5 C6 C8 177.0(4) . . . . ?
O1 C8 C6 C7 12.1(7) . . . . ?
O2 C8 C6 C7 -168.6(4) . . . . ?
Cd1 C8 C6 C7 140(4) 1_565 . . . ?
O1 C8 C6 C5 -167.8(5) . . . . ?
O2 C8 C6 C5 11.4(6) . . . . ?
Cd1 C8 C6 C5 -40(4) 1_565 . . . ?
C3 C2 C7 C6 1.1(6) . . . . ?
C1 C2 C7 C6 -175.9(4) . . . . ?
C5 C6 C7 C2 2.2(7) . . . . ?
C8 C6 C7 C2 -177.7(4) . . . . ?
C11 N1 C10 N2 -0.4(5) . . . . ?
Cd1 N1 C10 N2 -179.3(3) . . . . ?
C11 N1 C10 C9 179.3(4) . . . . ?
Cd1 N1 C10 C9 0.4(7) . . . . ?
C12 N2 C10 N1 0.4(5) . . . . ?
C13 N2 C10 N1 179.7(4) . . . . ?
C12 N2 C10 C9 -179.4(4) . . . . ?
C13 N2 C10 C9 0.0(7) . . . . ?
C10 N1 C11 C12 0.3(5) . . . . ?
Cd1 N1 C11 C12 179.3(3) . . . . ?
N1 C11 C12 N2 0.0(5) . . . . ?
C10 N2 C12 C11 -0.2(5) . . . . ?
C13 N2 C12 C11 -179.6(4) . . . . ?
C10 N2 C13 C14 101.5(6) . . . . ?
C12 N2 C13 C14 -79.2(6) . . . . ?
N2 C13 C14 C14 -67.5(7) . . . 2_755 ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.999
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.110
_database_code_depnum_ccdc_archive 'CCDC 990998'
