# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

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

data_kr2
_database_code_depnum_ccdc_archive 'CCDC 1033482'
_audit_update_record             
;
2014-11-10 deposited with the CCDC.
2015-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 Cl2 N2 O2 Re'
_chemical_formula_weight         520.37

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.22100(10)
_cell_length_b                   9.5214(2)
_cell_length_c                   12.2908(2)
_cell_angle_alpha                74.2770(10)
_cell_angle_beta                 84.6040(10)
_cell_angle_gamma                68.1430(10)
_cell_volume                     754.93(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    250
_cell_measurement_theta_min      1.45
_cell_measurement_theta_max      27.38

_exptl_crystal_description       parallopiped
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             492
_exptl_absorpt_coefficient_mu    8.412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.223
_exptl_absorpt_correction_T_max  0.267
_exptl_absorpt_process_details   (SADABAS,SHELDRICK-1997)

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            12692
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_sigmaI/netI    0.0500
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         27.53
_reflns_number_total             3456
_reflns_number_gt                2849
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART APEX II (Bruker,2010)'
_computing_cell_refinement       'SMART APEX II'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3v2 for windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2008)'

_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)+(0.0224P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3456
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0565
_refine_ls_wR_factor_gt          0.0530
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9651(7) 0.7213(5) 0.5416(4) 0.0338(11) Uani 1 1 d . . .
C2 C 1.1049(7) 0.6410(6) 0.4717(4) 0.0395(12) Uani 1 1 d . . .
H2 H 1.1819 0.5358 0.4993 0.047 Uiso 1 1 calc R . .
C3 C 1.1282(7) 0.7175(6) 0.3626(4) 0.0419(12) Uani 1 1 d . . .
H3 H 1.2173 0.6627 0.3155 0.050 Uiso 1 1 calc R . .
C4 C 1.0192(7) 0.8771(6) 0.3212(4) 0.0413(12) Uani 1 1 d . . .
H4 H 1.0387 0.9288 0.2477 0.050 Uiso 1 1 calc R . .
C5 C 0.8849(7) 0.9564(6) 0.3888(4) 0.0365(11) Uani 1 1 d . . .
H5 H 0.8133 1.0628 0.3609 0.044 Uiso 1 1 calc R . .
C6 C 0.8513(7) 0.8803(5) 0.5014(4) 0.0320(10) Uani 1 1 d . . .
C7 C 0.7142(7) 0.9713(6) 0.5672(4) 0.0338(11) Uani 1 1 d . . .
C8 C 0.5251(7) 1.0316(5) 0.7280(4) 0.0338(11) Uani 1 1 d . . .
C9 C 0.4548(7) 1.1920(5) 0.6915(4) 0.0395(12) Uani 1 1 d . . .
H9 H 0.4994 1.2400 0.6234 0.047 Uiso 1 1 calc R . .
C10 C 0.3169(8) 1.2841(6) 0.7554(4) 0.0452(13) Uani 1 1 d . . .
H10 H 0.2727 1.3926 0.7301 0.054 Uiso 1 1 calc R . .
C11 C 0.2467(7) 1.2164(6) 0.8544(4) 0.0446(13) Uani 1 1 d . . .
H11 H 0.1543 1.2790 0.8960 0.054 Uiso 1 1 calc R . .
C12 C 0.3127(7) 1.0537(6) 0.8940(4) 0.0355(11) Uani 1 1 d . . .
C13 C 0.2475(7) 0.9738(7) 0.9954(4) 0.0449(13) Uani 1 1 d . . .
H13 H 0.1541 1.0300 1.0402 0.054 Uiso 1 1 calc R . .
C14 C 0.3210(8) 0.8153(7) 1.0275(4) 0.0488(14) Uani 1 1 d . . .
H14 H 0.2755 0.7625 1.0931 0.059 Uiso 1 1 calc R . .
C15 C 0.4645(8) 0.7317(6) 0.9620(4) 0.0468(13) Uani 1 1 d . . .
H15 H 0.5161 0.6231 0.9865 0.056 Uiso 1 1 calc R . .
C16 C 0.4551(6) 0.9607(5) 0.8310(4) 0.0311(10) Uani 1 1 d . . .
Cl1 Cl 0.5264(2) 0.66488(15) 0.64531(12) 0.0526(4) Uani 1 1 d . . .
Cl2 Cl 1.0010(2) 0.71900(17) 0.85540(12) 0.0549(4) Uani 1 1 d . . .
N1 N 0.6619(5) 0.9223(4) 0.6722(3) 0.0315(9) Uani 1 1 d . . .
N2 N 0.5312(6) 0.8009(4) 0.8654(3) 0.0362(9) Uani 1 1 d . . .
O1 O 0.7647(5) 0.5111(4) 0.8604(3) 0.0522(10) Uani 1 1 d . . .
O2 O 0.9502(5) 0.6437(4) 0.6468(3) 0.0454(9) Uani 1 1 d . . .
Re1 Re 0.75675(3) 0.67737(2) 0.766060(16) 0.03608(8) Uani 1 1 d . . .
H7 H 0.651(6) 1.083(5) 0.526(3) 0.029(12) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.035(3) 0.037(3) 0.032(3) -0.011(2) 0.004(2) -0.016(2)
C2 0.043(3) 0.036(3) 0.040(3) -0.014(2) 0.006(2) -0.014(2)
C3 0.043(3) 0.045(3) 0.040(3) -0.021(2) 0.013(2) -0.015(2)
C4 0.049(3) 0.048(3) 0.029(3) -0.010(2) 0.005(2) -0.021(3)
C5 0.041(3) 0.034(3) 0.034(3) -0.009(2) -0.002(2) -0.013(2)
C6 0.034(3) 0.033(3) 0.031(2) -0.012(2) 0.005(2) -0.012(2)
C7 0.035(3) 0.031(3) 0.035(3) -0.006(2) 0.000(2) -0.014(2)
C8 0.033(3) 0.032(3) 0.034(3) -0.010(2) -0.003(2) -0.008(2)
C9 0.041(3) 0.031(3) 0.041(3) -0.011(2) 0.003(2) -0.007(2)
C10 0.052(3) 0.034(3) 0.043(3) -0.011(2) -0.004(2) -0.005(2)
C11 0.037(3) 0.047(3) 0.048(3) -0.026(3) 0.001(2) -0.004(2)
C12 0.029(3) 0.043(3) 0.036(3) -0.016(2) -0.001(2) -0.010(2)
C13 0.040(3) 0.061(4) 0.043(3) -0.023(3) 0.008(2) -0.023(3)
C14 0.059(4) 0.054(4) 0.042(3) -0.014(3) 0.016(3) -0.033(3)
C15 0.061(4) 0.039(3) 0.044(3) -0.013(2) 0.013(3) -0.024(3)
C16 0.028(2) 0.034(3) 0.032(2) -0.010(2) 0.0016(19) -0.011(2)
Cl1 0.0544(8) 0.0394(7) 0.0619(9) -0.0196(7) -0.0069(7) -0.0082(6)
Cl2 0.0516(8) 0.0581(9) 0.0538(8) -0.0184(7) -0.0039(6) -0.0148(7)
N1 0.033(2) 0.028(2) 0.035(2) -0.0119(17) 0.0028(17) -0.0107(17)
N2 0.041(2) 0.033(2) 0.036(2) -0.0094(18) 0.0051(18) -0.0154(19)
O1 0.061(2) 0.038(2) 0.047(2) -0.0042(17) 0.0069(18) -0.0124(18)
O2 0.051(2) 0.0332(19) 0.0369(19) -0.0075(16) 0.0119(16) -0.0027(16)
Re1 0.04184(13) 0.02823(12) 0.03296(11) -0.00825(8) 0.00541(8) -0.00776(9)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.321(5) . ?
C1 C6 1.398(6) . ?
C1 C2 1.400(6) . ?
C2 C3 1.370(6) . ?
C3 C4 1.397(7) . ?
C4 C5 1.358(6) . ?
C5 C6 1.423(6) . ?
C6 C7 1.406(6) . ?
C7 N1 1.318(5) . ?
C8 C9 1.373(6) . ?
C8 C16 1.409(6) . ?
C8 N1 1.423(5) . ?
C9 C10 1.398(6) . ?
C10 C11 1.362(7) . ?
C11 C12 1.396(7) . ?
C12 C16 1.409(6) . ?
C12 C13 1.413(7) . ?
C13 C14 1.355(7) . ?
C14 C15 1.389(7) . ?
C15 N2 1.334(6) . ?
C16 N2 1.366(6) . ?
Cl1 Re1 2.3853(13) . ?
Cl2 Re1 2.3653(14) . ?
N1 Re1 2.177(4) . ?
N2 Re1 2.123(4) . ?
O1 Re1 1.675(3) . ?
O2 Re1 1.934(3) . ?

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 C1 C6 121.6(4) . . ?
O2 C1 C2 117.9(4) . . ?
C6 C1 C2 120.4(4) . . ?
C3 C2 C1 120.0(5) . . ?
C2 C3 C4 120.7(4) . . ?
C5 C4 C3 119.8(4) . . ?
C4 C5 C6 121.3(4) . . ?
C1 C6 C7 124.1(4) . . ?
C1 C6 C5 117.8(4) . . ?
C7 C6 C5 118.0(4) . . ?
N1 C7 C6 127.0(4) . . ?
C9 C8 C16 118.9(4) . . ?
C9 C8 N1 127.6(4) . . ?
C16 C8 N1 113.5(4) . . ?
C8 C9 C10 120.9(5) . . ?
C11 C10 C9 120.6(5) . . ?
C10 C11 C12 120.4(5) . . ?
C11 C12 C16 119.1(4) . . ?
C11 C12 C13 124.2(5) . . ?
C16 C12 C13 116.7(5) . . ?
C14 C13 C12 120.0(5) . . ?
C13 C14 C15 119.8(5) . . ?
N2 C15 C14 122.7(5) . . ?
N2 C16 C12 122.7(4) . . ?
N2 C16 C8 117.2(4) . . ?
C12 C16 C8 120.1(4) . . ?
C7 N1 C8 119.7(4) . . ?
C7 N1 Re1 124.1(3) . . ?
C8 N1 Re1 116.1(3) . . ?
C15 N2 C16 117.9(4) . . ?
C15 N2 Re1 123.7(3) . . ?
C16 N2 Re1 118.3(3) . . ?
C1 O2 Re1 135.3(3) . . ?
O1 Re1 O2 113.07(15) . . ?
O1 Re1 N2 88.07(16) . . ?
O2 Re1 N2 158.73(14) . . ?
O1 Re1 N1 162.08(15) . . ?
O2 Re1 N1 84.58(13) . . ?
N2 Re1 N1 74.47(14) . . ?
O1 Re1 Cl2 96.27(13) . . ?
O2 Re1 Cl2 85.36(11) . . ?
N2 Re1 Cl2 90.19(11) . . ?
N1 Re1 Cl2 87.91(10) . . ?
O1 Re1 Cl1 93.45(13) . . ?
O2 Re1 Cl1 87.03(11) . . ?
N2 Re1 Cl1 94.27(11) . . ?
N1 Re1 Cl1 84.08(10) . . ?
Cl2 Re1 Cl1 169.44(5) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.343
_refine_diff_density_min         -0.771
_refine_diff_density_rms         0.141
