# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_eb15144_refinalized
_database_code_depnum_ccdc_archive 'CCDC 1503662'
_audit_update_record             
;
2016-09-09 deposited with the CCDC.
2016-12-13 downloaded from the CCDC.
;
_audit_creation_date             2016-05-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 Cl4 O4 Re, C10 H10 N2'
_chemical_formula_sum            'C12 H10 Cl4 N2 O4 Re'
_chemical_formula_weight         574.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H8 Cl4 N2 O4'
_chemical_oxdiff_usercomment     '@ 120 K AHP261C'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -5.2083 5.8923 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_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                   9.3070(3)
_cell_length_b                   17.6267(4)
_cell_length_c                   10.8072(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.592(4)
_cell_angle_gamma                90
_cell_volume                     1624.75(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9109
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      75.9900
_cell_measurement_theta_min      5.0270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    20.879
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1084
_exptl_crystal_size_max          0.4829
_exptl_crystal_size_mid          0.0565
_exptl_crystal_size_min          0.0197
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12929
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.306
_diffrn_reflns_theta_min         5.018
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -50.00   29.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686   38.0000 -120.0000 79

#__ type_ start__ end____ width___ exp.time_
  2 omega -116.00  -21.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686  -38.0000 -120.0000 95

#__ type_ start__ end____ width___ exp.time_
  3 omega  -50.00   29.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686   38.0000   30.0000 79

#__ type_ start__ end____ width___ exp.time_
  4 omega -114.00  -62.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686 -143.0000  -23.0000 52

#__ type_ start__ end____ width___ exp.time_
  5 omega  -96.00   -2.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686  125.0000  120.0000 94

#__ type_ start__ end____ width___ exp.time_
  6 omega    1.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1686  -99.0000   30.0000 82

#__ type_ start__ end____ width___ exp.time_
  7 omega   30.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  -90.0000 79

#__ type_ start__ end____ width___ exp.time_
  8 omega   40.00   99.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000  -60.0000 59

#__ type_ start__ end____ width___ exp.time_
  9 omega   39.00  121.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000 -180.0000 82

#__ type_ start__ end____ width___ exp.time_
 10 omega   87.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000   90.0000 91

#__ type_ start__ end____ width___ exp.time_
 11 omega   87.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000   30.0000 91

#__ type_ start__ end____ width___ exp.time_
 12 omega   39.00  121.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000   30.0000 82

#__ type_ start__ end____ width___ exp.time_
 13 omega   30.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000 -150.0000 79

#__ type_ start__ end____ width___ exp.time_
 14 omega   87.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000  -60.0000 91

#__ type_ start__ end____ width___ exp.time_
 15 omega   36.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000  150.0000 55

#__ type_ start__ end____ width___ exp.time_
 16 omega   30.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000   30.0000 79

#__ type_ start__ end____ width___ exp.time_
 17 omega   39.00  121.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000  -30.0000 82

#__ type_ start__ end____ width___ exp.time_
 18 omega   40.00   99.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000    0.0000 59

#__ type_ start__ end____ width___ exp.time_
 19 omega   80.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000  120.0000 98

#__ type_ start__ end____ width___ exp.time_
 20 omega   39.00  121.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000  -60.0000 82

#__ type_ start__ end____ width___ exp.time_
 21 omega   93.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  127.0000 -138.0000 85

#__ type_ start__ end____ width___ exp.time_
 22 omega   30.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  -30.0000 79

#__ type_ start__ end____ width___ exp.time_
 23 omega   30.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  150.0000 79

#__ type_ start__ end____ width___ exp.time_
 24 omega   36.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000   30.0000 55

#__ type_ start__ end____ width___ exp.time_
 25 omega   30.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000 -180.0000 79

#__ type_ start__ end____ width___ exp.time_
 26 omega   87.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000    0.0000 91

#__ type_ start__ end____ width___ exp.time_
 27 omega   94.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  125.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
 28 omega -117.00  -12.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686  -77.0000    0.0000 105

#__ type_ start__ end____ width___ exp.time_
 29 omega -113.00  -17.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686  -57.0000 -180.0000 96

#__ type_ start__ end____ width___ exp.time_
 30 omega  -50.00   29.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686   38.0000  -30.0000 79

#__ type_ start__ end____ width___ exp.time_
 31 omega -117.00  -12.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686  -77.0000   90.0000 105

#__ type_ start__ end____ width___ exp.time_
 32 omega -113.00  -17.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686  -57.0000   90.0000 96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0150839000
_diffrn_orient_matrix_UB_12      0.0870688000
_diffrn_orient_matrix_UB_13      0.0083593000
_diffrn_orient_matrix_UB_21      -0.0919403000
_diffrn_orient_matrix_UB_22      0.0054168000
_diffrn_orient_matrix_UB_23      -0.1540335000
_diffrn_orient_matrix_UB_31      -0.1547988000
_diffrn_orient_matrix_UB_32      0.0052977000
_diffrn_orient_matrix_UB_33      0.0196650000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1661
_reflns_number_total             1700
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         2.788
_refine_diff_density_min         -1.231
_refine_diff_density_rms         0.198
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1700
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0686P)²+3.6307P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0857
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2A), C3(H3), C6(H6), C7(H7)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Re1 Re 0.0000 0.38665(2) 0.2500 0.01609(13) Uani 1 2 d S T P . .
Cl1 Cl 0.02615(14) 0.39039(5) 0.04317(11) 0.0232(3) Uani 1 1 d . . . . .
Cl2 Cl -0.19555(11) 0.29423(6) 0.16783(10) 0.0227(2) Uani 1 1 d . . . . .
O1 O -0.1539(4) 0.47579(16) 0.1862(3) 0.0206(6) Uani 1 1 d . . . . .
O2 O -0.1636(4) 0.60193(18) 0.1861(4) 0.0268(7) Uani 1 1 d . . . . .
C1 C -0.0900(5) 0.5430(2) 0.2136(4) 0.0237(8) Uani 1 1 d . . . . .
N1 N -0.5000 0.3632(3) -0.2500 0.0267(10) Uani 1 2 d S T P . .
H1 H -0.5000 0.3144 -0.2500 0.032 Uiso 1 2 calc RS T P . .
N2 N -0.5000 0.7559(4) -0.2500 0.050(2) Uani 1 2 d S T P . .
H2 H -0.5000 0.804(7) -0.2500 0.06(3) Uiso 1 2 d S T P . .
C2 C -0.3809(6) 0.3992(3) -0.1546(5) 0.0286(10) Uani 1 1 d . . . . .
H2A H -0.3000 0.3717 -0.0903 0.034 Uiso 1 1 calc R . . . .
C3 C -0.3786(5) 0.4771(2) -0.1519(4) 0.0256(9) Uani 1 1 d . . . . .
H3 H -0.2966 0.5027 -0.0851 0.031 Uiso 1 1 calc R . . . .
C4 C -0.5000 0.5181(3) -0.2500 0.0219(11) Uani 1 2 d S T P . .
C5 C -0.5000 0.6018(4) -0.2500 0.0274(14) Uani 1 2 d S T P . .
C6 C -0.4331(5) 0.6416(3) -0.1280(6) 0.0326(10) Uani 1 1 d . . . . .
H6 H -0.3870 0.6159 -0.0463 0.039 Uiso 1 1 calc R . . . .
C7 C -0.4376(6) 0.7202(3) -0.1324(7) 0.0418(13) Uani 1 1 d . . . . .
H7 H -0.3967 0.7479 -0.0526 0.050 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
Re1 Cl1 2.3443(11) 2 ?
Re1 Cl1 2.3442(11) . ?
Re1 Cl2 2.3369(10) 2 ?
Re1 Cl2 2.3369(10) . ?
Re1 O1 2.050(3) . ?
Re1 O1 2.050(3) 2 ?
O1 C1 1.305(5) . ?
O2 C1 1.214(6) . ?
C1 C1 1.539(9) 2 ?
N1 H1 0.8600 . ?
N1 C2 1.334(6) . ?
N1 C2 1.334(6) 2_454 ?
N2 H2 0.84(13) . ?
N2 C7 1.326(7) . ?
N2 C7 1.326(7) 2_454 ?
C2 H2A 0.9300 . ?
C2 C3 1.374(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.401(5) . ?
C4 C3 1.401(5) 2_454 ?
C4 C5 1.477(9) . ?
C5 C6 1.399(6) . ?
C5 C6 1.399(6) 2_454 ?
C6 H6 0.9300 . ?
C6 C7 1.386(7) . ?
C7 H7 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Re1 Cl1 176.78(4) . 2 ?
Cl2 Re1 Cl1 91.13(4) . 2 ?
Cl2 Re1 Cl1 91.12(4) 2 2 ?
Cl2 Re1 Cl1 91.12(4) . . ?
Cl2 Re1 Cl1 91.13(4) 2 . ?
Cl2 Re1 Cl2 91.61(5) . 2 ?
O1 Re1 Cl1 89.03(8) 2 2 ?
O1 Re1 Cl1 88.50(8) 2 . ?
O1 Re1 Cl1 88.50(8) . 2 ?
O1 Re1 Cl1 89.03(8) . . ?
O1 Re1 Cl2 94.22(9) . . ?
O1 Re1 Cl2 94.22(9) 2 2 ?
O1 Re1 Cl2 174.17(9) 2 . ?
O1 Re1 Cl2 174.17(9) . 2 ?
O1 Re1 O1 79.96(17) . 2 ?
C1 O1 Re1 115.2(3) . . ?
O1 C1 C1 114.8(2) . 2 ?
O2 C1 O1 124.0(4) . . ?
O2 C1 C1 121.1(3) . 2 ?
C2 N1 H1 118.4 . . ?
C2 N1 H1 118.4 2_454 . ?
C2 N1 C2 123.2(6) . 2_454 ?
C7 N2 H2 118.4(3) . . ?
C7 N2 H2 118.4(3) 2_454 . ?
C7 N2 C7 123.2(6) 2_454 . ?
N1 C2 H2A 120.2 . . ?
N1 C2 C3 119.5(5) . . ?
C3 C2 H2A 120.2 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.9(4) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C3 118.0(6) . 2_454 ?
C3 C4 C5 121.0(3) . . ?
C3 C4 C5 121.0(3) 2_454 . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 C4 120.0(3) 2_454 . ?
C6 C5 C6 120.0(7) . 2_454 ?
C5 C6 H6 120.9 . . ?
C7 C6 C5 118.1(5) . . ?
C7 C6 H6 120.9 . . ?
N2 C7 C6 120.2(5) . . ?
N2 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?

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
Re1 O1 C1 O2 -178.2(3) . . . . ?
Re1 O1 C1 C1 1.2(5) . . . 2 ?
N1 C2 C3 C4 -0.7(7) . . . . ?
C2 N1 C2 C3 0.4(4) 2_454 . . . ?
C2 C3 C4 C3 0.4(3) . . . 2_454 ?
C2 C3 C4 C5 -179.6(3) . . . . ?
C3 C4 C5 C6 -31.5(3) 2_454 . . 2_454 ?
C3 C4 C5 C6 148.5(3) . . . 2_454 ?
C3 C4 C5 C6 -31.5(3) . . . . ?
C3 C4 C5 C6 148.5(3) 2_454 . . . ?
C4 C5 C6 C7 -179.1(3) . . . . ?
C5 C6 C7 N2 -1.8(7) . . . . ?
C6 C5 C6 C7 0.9(3) 2_454 . . . ?
C7 N2 C7 C6 0.9(3) 2_454 . . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 -1 0 0.0098 0.0003 -0.9992 -0.0000 -0.0870 -0.0054 -0.0053
0 1 0 0.0098 -0.0003 0.9992 0.0000 0.0870 0.0054 0.0053
0 -1 5 0.0214 -0.0027 -0.9975 5.0013 -0.0451 -0.7755 0.0935
5 -1 -3 0.2172 5.0040 -0.9925 -3.0023 -0.0360 -0.0030 -0.8389
-5 1 3 0.2500 -5.0040 0.9925 3.0023 0.0360 0.0030 0.8389
0 5 -3 0.0180 0.0001 4.9950 -3.0007 0.4098 0.4892 -0.0326

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_preparation       ', Magnetic properties'
####################################################################### 
# 
# 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_eb15127
_database_code_depnum_ccdc_archive 'CCDC 1503663'
_audit_update_record             
;
2016-09-09 deposited with the CCDC.
2016-12-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 Cl4 O4 Re, 2(C6 H7 N4)'
_chemical_formula_sum            'C14 H14 Cl4 N8 O4 Re'
_chemical_formula_weight         686.33

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'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8643(2)
_cell_length_b                   9.9913(2)
_cell_length_c                   12.1357(2)
_cell_angle_alpha                93.3640(7)
_cell_angle_beta                 92.3297(7)
_cell_angle_gamma                119.5351(6)
_cell_volume                     1035.51(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9829
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      28.51

_exptl_crystal_description       tablet
_exptl_crystal_colour            yellow-green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.201
_exptl_crystal_F_000             658
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.434
_exptl_crystal_size_mid          0.345
_exptl_crystal_size_min          0.062
_exptl_absorpt_coefficient_mu    6.426
_shelx_estimated_absorpt_T_min   0.167
_shelx_estimated_absorpt_T_max   0.691
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.41
_exptl_absorpt_correction_T_max  0.67
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23688
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.686
_diffrn_reflns_theta_max         28.534
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.900
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.900
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4757
_reflns_number_gt                4729
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    DIAMOND
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0315P)²+1.4230P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4757
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0168
_refine_ls_R_factor_gt           0.0167
_refine_ls_wR_factor_ref         0.0458
_refine_ls_wR_factor_gt          0.0457
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Re1 Re 0.88016(2) 0.58234(2) 0.72194(2) 0.00839(4) Uani 1 1 d . . . . .
Cl1 Cl 0.84645(7) 0.52931(7) 0.90762(4) 0.01419(11) Uani 1 1 d . . . . .
Cl2 Cl 0.61860(7) 0.50879(7) 0.68672(5) 0.01575(11) Uani 1 1 d . . . . .
Cl3 Cl 0.95836(7) 0.84311(6) 0.76169(5) 0.01511(11) Uani 1 1 d . . . . .
Cl4 Cl 0.92943(7) 0.62547(7) 0.53678(4) 0.01381(11) Uani 1 1 d . . . . .
O1 O 0.8397(2) 0.36289(18) 0.68380(14) 0.0122(3) Uani 1 1 d . . . . .
O2 O 0.9497(2) 0.21404(19) 0.68854(13) 0.0138(3) Uani 1 1 d . . . . .
O3 O 1.2217(2) 0.4770(2) 0.78781(14) 0.0166(3) Uani 1 1 d . . . . .
O4 O 1.10059(19) 0.61168(19) 0.75620(14) 0.0117(3) Uani 1 1 d . . . . .
N1 N 0.5323(2) 1.0893(2) 0.31357(16) 0.0144(4) Uani 1 1 d . . . . .
N2 N 0.6617(2) 1.2322(2) 0.46825(17) 0.0148(4) Uani 1 1 d . . . . .
H2A H 0.7235 1.2652 0.5298 0.018 Uiso 1 1 calc R U . . .
N3 N 0.7769(2) 1.0038(2) 0.50265(16) 0.0130(4) Uani 1 1 d . . . . .
H3A H 0.8048 1.0665 0.5636 0.016 Uiso 1 1 calc R U . . .
N4 N 0.6764(2) 0.8951(2) 0.33836(16) 0.0137(4) Uani 1 1 d . . . . .
H4A H 0.6261 0.8732 0.2724 0.016 Uiso 1 1 calc R U . . .
N5 N 0.5832(3) 0.8201(2) 0.10826(17) 0.0154(4) Uani 1 1 d . . . . .
N6 N 0.4734(2) 0.6944(2) -0.05643(16) 0.0138(4) Uani 1 1 d . . . . .
H6A H 0.4085 0.6578 -0.1165 0.017 Uiso 1 1 calc R U . . .
N7 N 0.2350(2) 0.8022(2) -0.03378(16) 0.0142(4) Uani 1 1 d . . . . .
H7A H 0.2137 0.7494 -0.0989 0.017 Uiso 1 1 calc R U . . .
N8 N 0.3475(2) 0.9145(2) 0.12757(16) 0.0128(4) Uani 1 1 d . . . . .
H8A H 0.4128 0.9483 0.1873 0.015 Uiso 1 1 calc R U . . .
C1 C 0.9555(3) 0.3378(3) 0.70590(17) 0.0107(4) Uani 1 1 d . . . . .
C2 C 1.1084(3) 0.4842(3) 0.75473(18) 0.0111(4) Uani 1 1 d . . . . .
C3 C 0.4993(3) 1.2068(3) 0.3309(2) 0.0146(4) Uani 1 1 d . . . . .
H3B H 0.4311 1.2234 0.2833 0.018 Uiso 1 1 calc R U . . .
C4 C 0.5781(3) 1.2960(3) 0.4258(2) 0.0160(5) Uani 1 1 d . . . . .
H4B H 0.5757 1.3845 0.4563 0.019 Uiso 1 1 calc R U . . .
C5 C 0.6313(3) 1.1085(3) 0.39761(18) 0.0107(4) Uani 1 1 d . . . . .
C6 C 0.6960(3) 1.0078(3) 0.41294(19) 0.0120(4) Uani 1 1 d . . . . .
C7 C 0.8097(3) 0.8857(3) 0.4844(2) 0.0152(4) Uani 1 1 d . . . . .
H7B H 0.8652 0.8570 0.5347 0.018 Uiso 1 1 calc R U . . .
C8 C 0.7477(3) 0.8183(3) 0.3812(2) 0.0155(4) Uani 1 1 d . . . . .
H8B H 0.7524 0.7339 0.3450 0.019 Uiso 1 1 calc R U . . .
C9 C 0.6652(3) 0.7519(3) 0.0680(2) 0.0170(5) Uani 1 1 d . . . . .
H9A H 0.7551 0.7583 0.1053 0.020 Uiso 1 1 calc R U . . .
C10 C 0.5985(3) 0.6736(3) -0.0335(2) 0.0166(5) Uani 1 1 d . . . . .
H10A H 0.6322 0.6164 -0.0787 0.020 Uiso 1 1 calc R U . . .
C11 C 0.4688(3) 0.7823(3) 0.03108(18) 0.0120(4) Uani 1 1 d . . . . .
C12 C 0.3529(3) 0.8306(3) 0.03981(18) 0.0113(4) Uani 1 1 d . . . . .
C13 C 0.1525(3) 0.8686(3) 0.0085(2) 0.0168(5) Uani 1 1 d . . . . .
H13A H 0.0628 0.8652 -0.0265 0.020 Uiso 1 1 calc R U . . .
C14 C 0.2235(3) 0.9397(3) 0.1098(2) 0.0149(4) Uani 1 1 d . . . . .
H14A H 0.1933 0.9961 0.1590 0.018 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 O1 2.0456(16) . ?
Re1 O4 2.0665(16) . ?
Re1 Cl2 2.3204(6) . ?
Re1 Cl3 2.3359(5) . ?
Re1 Cl4 2.3382(5) . ?
Re1 Cl1 2.3444(5) . ?
O1 C1 1.305(3) . ?
O2 C1 1.215(3) . ?
O3 C2 1.209(3) . ?
O4 C2 1.312(3) . ?
N1 C5 1.320(3) . ?
N1 C3 1.372(3) . ?
N2 C5 1.357(3) . ?
N2 C4 1.369(3) . ?
N2 H2A 0.8800 . ?
N3 C6 1.338(3) . ?
N3 C7 1.377(3) . ?
N3 H3A 0.8800 . ?
N4 C6 1.333(3) . ?
N4 C8 1.380(3) . ?
N4 H4A 0.8800 . ?
N5 C11 1.321(3) . ?
N5 C9 1.376(3) . ?
N6 C11 1.354(3) . ?
N6 C10 1.370(3) . ?
N6 H6A 0.8800 . ?
N7 C12 1.338(3) . ?
N7 C13 1.376(3) . ?
N7 H7A 0.8800 . ?
N8 C12 1.335(3) . ?
N8 C14 1.376(3) . ?
N8 H8A 0.8800 . ?
C1 C2 1.554(3) . ?
C3 C4 1.360(3) . ?
C3 H3B 0.9500 . ?
C4 H4B 0.9500 . ?
C5 C6 1.448(3) . ?
C7 C8 1.353(3) . ?
C7 H7B 0.9500 . ?
C8 H8B 0.9500 . ?
C9 C10 1.370(3) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C12 1.449(3) . ?
C13 C14 1.358(3) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Re1 O4 78.90(7) . . ?
O1 Re1 Cl2 92.72(5) . . ?
O4 Re1 Cl2 171.01(5) . . ?
O1 Re1 Cl3 172.96(5) . . ?
O4 Re1 Cl3 94.64(5) . . ?
Cl2 Re1 Cl3 93.89(2) . . ?
O1 Re1 Cl4 87.52(5) . . ?
O4 Re1 Cl4 90.77(5) . . ?
Cl2 Re1 Cl4 92.10(2) . . ?
Cl3 Re1 Cl4 89.81(2) . . ?
O1 Re1 Cl1 88.88(5) . . ?
O4 Re1 Cl1 84.61(5) . . ?
Cl2 Re1 Cl1 92.06(2) . . ?
Cl3 Re1 Cl1 93.30(2) . . ?
Cl4 Re1 Cl1 174.622(19) . . ?
C1 O1 Re1 116.90(14) . . ?
C2 O4 Re1 115.61(15) . . ?
C5 N1 C3 105.39(19) . . ?
C5 N2 C4 107.17(19) . . ?
C5 N2 H2A 126.4 . . ?
C4 N2 H2A 126.4 . . ?
C6 N3 C7 109.1(2) . . ?
C6 N3 H3A 125.4 . . ?
C7 N3 H3A 125.4 . . ?
C6 N4 C8 109.03(19) . . ?
C6 N4 H4A 125.5 . . ?
C8 N4 H4A 125.5 . . ?
C11 N5 C9 104.9(2) . . ?
C11 N6 C10 106.8(2) . . ?
C11 N6 H6A 126.6 . . ?
C10 N6 H6A 126.6 . . ?
C12 N7 C13 109.2(2) . . ?
C12 N7 H7A 125.4 . . ?
C13 N7 H7A 125.4 . . ?
C12 N8 C14 109.24(19) . . ?
C12 N8 H8A 125.4 . . ?
C14 N8 H8A 125.4 . . ?
O2 C1 O1 124.8(2) . . ?
O2 C1 C2 121.4(2) . . ?
O1 C1 C2 113.83(19) . . ?
O3 C2 O4 124.8(2) . . ?
O3 C2 C1 121.5(2) . . ?
O4 C2 C1 113.73(19) . . ?
C4 C3 N1 110.3(2) . . ?
C4 C3 H3B 124.9 . . ?
N1 C3 H3B 124.9 . . ?
C3 C4 N2 105.9(2) . . ?
C3 C4 H4B 127.1 . . ?
N2 C4 H4B 127.1 . . ?
N1 C5 N2 111.3(2) . . ?
N1 C5 C6 124.0(2) . . ?
N2 C5 C6 124.7(2) . . ?
N4 C6 N3 107.8(2) . . ?
N4 C6 C5 124.1(2) . . ?
N3 C6 C5 128.0(2) . . ?
C8 C7 N3 106.9(2) . . ?
C8 C7 H7B 126.5 . . ?
N3 C7 H7B 126.5 . . ?
C7 C8 N4 107.1(2) . . ?
C7 C8 H8B 126.5 . . ?
N4 C8 H8B 126.5 . . ?
C10 C9 N5 110.2(2) . . ?
C10 C9 H9A 124.9 . . ?
N5 C9 H9A 124.9 . . ?
C9 C10 N6 106.0(2) . . ?
C9 C10 H10A 127.0 . . ?
N6 C10 H10A 127.0 . . ?
N5 C11 N6 112.2(2) . . ?
N5 C11 C12 123.4(2) . . ?
N6 C11 C12 124.4(2) . . ?
N8 C12 N7 107.7(2) . . ?
N8 C12 C11 123.8(2) . . ?
N7 C12 C11 128.4(2) . . ?
C14 C13 N7 107.0(2) . . ?
C14 C13 H13A 126.5 . . ?
N7 C13 H13A 126.5 . . ?
C13 C14 N8 106.9(2) . . ?
C13 C14 H14A 126.6 . . ?
N8 C14 H14A 126.6 . . ?

_refine_diff_density_max         0.914
_refine_diff_density_min         -1.049
_refine_diff_density_rms         0.114

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_preparation       ', Magnetic properties'
