# Electronic Supplementary Material (ESI) for ChemComm.
# 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.
# 
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#  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 H20 Cl2 Dy N3 O8'
_chemical_formula_weight         579.72

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Dy Dy -0.1892 4.4098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   14.9729(6)
_cell_length_b                   14.7878(6)
_cell_length_c                   17.7603(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3932.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9990
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.59

_exptl_crystal_description       column
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.958
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2264
_exptl_absorpt_coefficient_mu    4.117
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.3714
_exptl_absorpt_correction_T_max  0.8526
_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  '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            22585
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         27.60
_reflns_number_total             4563
_reflns_number_gt                3919
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0195P)²+3.8004P] 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         4563
_refine_ls_number_parameters     275
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0207
_refine_ls_wR_factor_ref         0.0497
_refine_ls_wR_factor_gt          0.0473
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.003
_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
C1 C 0.88680(19) 0.3916(2) 0.45704(16) 0.0380(7) Uani 1 1 d . . .
H1 H 0.9451 0.4127 0.4611 0.046 Uiso 1 1 calc R . .
C2 C 0.8384(2) 0.3760(2) 0.52069(16) 0.0435(7) Uani 1 1 d . . .
H2 H 0.8640 0.3858 0.5677 0.052 Uiso 1 1 calc R . .
C3 C 0.7514(2) 0.3457(2) 0.51562(16) 0.0441(7) Uani 1 1 d . . .
H3 H 0.7183 0.3332 0.5587 0.053 Uiso 1 1 calc R . .
C4 C 0.7152(2) 0.3344(2) 0.44509(16) 0.0384(7) Uani 1 1 d . . .
H4 H 0.6562 0.3154 0.4405 0.046 Uiso 1 1 calc R . .
C5 C 0.76450(17) 0.35074(18) 0.38110(14) 0.0288(5) Uani 1 1 d . . .
C6 C 0.71844(18) 0.34391(18) 0.30687(14) 0.0292(5) Uani 1 1 d . . .
C7 C 0.75446(18) 0.39206(19) 0.11940(15) 0.0322(6) Uani 1 1 d . . .
H7 H 0.8134 0.4104 0.1260 0.039 Uiso 1 1 calc R . .
C8 C 0.71926(18) 0.39293(18) 0.04439(14) 0.0311(6) Uani 1 1 d . . .
C9 C 0.77755(19) 0.4214(2) -0.01350(16) 0.0374(6) Uani 1 1 d . . .
H9 H 0.8354 0.4390 -0.0015 0.045 Uiso 1 1 calc R . .
C10 C 0.7502(2) 0.4235(2) -0.08704(16) 0.0402(7) Uani 1 1 d . . .
H10 H 0.7895 0.4415 -0.1247 0.048 Uiso 1 1 calc R . .
C11 C 0.6633(2) 0.3986(2) -0.10508(16) 0.0406(7) Uani 1 1 d . . .
H11 H 0.6445 0.4004 -0.1550 0.049 Uiso 1 1 calc R . .
C12 C 0.6049(2) 0.3713(2) -0.05005(15) 0.0370(6) Uani 1 1 d . . .
H12 H 0.5468 0.3557 -0.0633 0.044 Uiso 1 1 calc R . .
C13 C 0.63089(18) 0.36637(18) 0.02573(14) 0.0305(5) Uani 1 1 d . . .
Cl1 Cl 0.31962(5) 0.36398(5) 0.78032(4) 0.04147(16) Uani 1 1 d . . .
Cl2 Cl 0.97014(6) 0.52627(6) 0.10636(5) 0.0574(2) Uani 1 1 d . . .
Dy1 Dy 0.548121(7) 0.319316(8) 0.197211(6) 0.02550(5) Uani 1 1 d . . .
N1 N 0.85156(14) 0.37696(14) 0.38825(12) 0.0282(4) Uani 1 1 d . . .
N2 N 0.75903(14) 0.37267(15) 0.24553(12) 0.0306(5) Uani 1 1 d . . .
H2A H 0.8127 0.3934 0.2467 0.037 Uiso 1 1 calc R . .
N3 N 0.71050(14) 0.36776(15) 0.17858(12) 0.0288(5) Uani 1 1 d . . .
O1 O 0.90268(12) 0.39084(13) 0.32818(10) 0.0329(4) Uani 1 1 d . . .
O2 O 0.64064(14) 0.31443(14) 0.30589(10) 0.0399(5) Uani 1 1 d . . .
O3 O 0.57497(13) 0.33697(15) 0.07720(10) 0.0385(5) Uani 1 1 d . . .
O4 O 0.55357(15) 0.47036(15) 0.23964(16) 0.0542(6) Uani 1 1 d D . .
O5 O 0.45819(14) 0.28897(18) 0.30626(11) 0.0434(5) Uani 1 1 d D . .
O6 O 0.44378(13) 0.20692(14) 0.15069(12) 0.0373(4) Uani 1 1 d D . .
O7 O 0.62111(15) 0.17813(14) 0.19571(13) 0.0457(5) Uani 1 1 d D . .
O8 O 0.4870(2) 0.32039(17) 0.45874(15) 0.0605(7) Uani 1 1 d D . .
H4A H 0.592(2) 0.516(2) 0.224(2) 0.085(5) Uiso 1 1 d D . .
H5A H 0.421(3) 0.238(2) 0.302(2) 0.085(5) Uiso 1 1 d D . .
H6A H 0.397(2) 0.192(2) 0.183(2) 0.085(5) Uiso 1 1 d D . .
H7A H 0.6820(14) 0.175(3) 0.207(2) 0.085(5) Uiso 1 1 d D . .
H6B H 0.468(2) 0.1559(19) 0.129(2) 0.085(5) Uiso 1 1 d D . .
H7B H 0.603(2) 0.127(2) 0.171(2) 0.085(5) Uiso 1 1 d D . .
H5B H 0.472(3) 0.294(3) 0.3573(12) 0.085(5) Uiso 1 1 d D . .
H4B H 0.528(3) 0.488(3) 0.2855(15) 0.085(5) Uiso 1 1 d D . .
H8A H 0.489(3) 0.3818(12) 0.472(2) 0.085(5) Uiso 1 1 d D . .
H8B H 0.479(3) 0.288(2) 0.5031(16) 0.085(5) 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
C1 N1 1.348(3) . ?
C1 C2 1.363(4) . ?
C2 C3 1.380(4) . ?
C3 C4 1.375(4) . ?
C4 C5 1.377(4) . ?
C5 N1 1.366(3) . ?
C5 C6 1.491(3) . ?
C6 O2 1.244(3) . ?
C6 N2 1.318(3) . ?
C7 N3 1.291(3) . ?
C7 C8 1.433(4) . ?
C8 C9 1.413(4) . ?
C8 C13 1.419(4) . ?
C9 C10 1.369(4) . ?
C10 C11 1.390(4) . ?
C11 C12 1.372(4) . ?
C12 C13 1.403(4) . ?
C13 O3 1.314(3) . ?
Dy1 O3 2.1846(19) . ?
Dy1 O7 2.357(2) . ?
Dy1 O4 2.359(2) . ?
Dy1 O2 2.3769(19) . ?
Dy1 O5 2.4011(19) . ?
Dy1 O6 2.4261(19) . ?
Dy1 O1 2.4625(18) 6_556 ?
Dy1 N3 2.556(2) . ?
N1 O1 1.329(3) . ?
N2 N3 1.395(3) . ?
O1 Dy1 2.4625(18) 6_656 ?

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 C1 C2 121.1(3) . . ?
C1 C2 C3 120.2(3) . . ?
C4 C3 C2 118.1(3) . . ?
C3 C4 C5 121.3(3) . . ?
N1 C5 C4 119.0(2) . . ?
N1 C5 C6 122.9(2) . . ?
C4 C5 C6 118.0(2) . . ?
O2 C6 N2 122.2(2) . . ?
O2 C6 C5 118.0(2) . . ?
N2 C6 C5 119.7(2) . . ?
N3 C7 C8 124.9(2) . . ?
C9 C8 C13 119.2(2) . . ?
C9 C8 C7 116.9(2) . . ?
C13 C8 C7 123.9(2) . . ?
C10 C9 C8 121.1(3) . . ?
C9 C10 C11 119.6(3) . . ?
C12 C11 C10 120.7(3) . . ?
C11 C12 C13 121.5(3) . . ?
O3 C13 C12 120.5(2) . . ?
O3 C13 C8 121.5(2) . . ?
C12 C13 C8 117.9(2) . . ?
O3 Dy1 O7 90.54(8) . . ?
O3 Dy1 O4 101.08(9) . . ?
O7 Dy1 O4 145.74(8) . . ?
O3 Dy1 O2 133.52(7) . . ?
O7 Dy1 O2 73.26(8) . . ?
O4 Dy1 O2 75.47(9) . . ?
O3 Dy1 O5 155.85(7) . . ?
O7 Dy1 O5 95.95(9) . . ?
O4 Dy1 O5 86.49(9) . . ?
O2 Dy1 O5 70.50(7) . . ?
O3 Dy1 O6 82.42(7) . . ?
O7 Dy1 O6 71.81(7) . . ?
O4 Dy1 O6 141.25(8) . . ?
O2 Dy1 O6 129.13(7) . . ?
O5 Dy1 O6 77.61(7) . . ?
O3 Dy1 O1 86.14(7) . 6_556 ?
O7 Dy1 O1 142.04(7) . 6_556 ?
O4 Dy1 O1 71.48(7) . 6_556 ?
O2 Dy1 O1 132.62(7) . 6_556 ?
O5 Dy1 O1 74.46(7) . 6_556 ?
O6 Dy1 O1 70.27(7) . 6_556 ?
O3 Dy1 N3 70.44(7) . . ?
O7 Dy1 N3 78.80(8) . . ?
O4 Dy1 N3 75.11(7) . . ?
O2 Dy1 N3 63.85(7) . . ?
O5 Dy1 N3 133.65(7) . . ?
O6 Dy1 N3 139.50(7) . . ?
O1 Dy1 N3 134.19(7) 6_556 . ?
O1 N1 C1 118.5(2) . . ?
O1 N1 C5 121.3(2) . . ?
C1 N1 C5 120.2(2) . . ?
C6 N2 N3 116.6(2) . . ?
C7 N3 N2 114.4(2) . . ?
C7 N3 Dy1 131.94(17) . . ?
N2 N3 Dy1 113.55(15) . . ?
N1 O1 Dy1 126.16(14) . 6_656 ?
C6 O2 Dy1 123.13(17) . . ?
C13 O3 Dy1 146.69(18) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.60
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.809
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.077
_database_code_depnum_ccdc_archive 'CCDC 999017'
