# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 1504036'
_audit_update_record             
;
2017-09-29 deposited with the CCDC.
2017-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H6 Br N2 O4 Re'
_chemical_formula_weight         496.29

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   7.4456(2)
_cell_length_b                   14.2674(4)
_cell_length_c                   24.4414(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2596.39(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    17114
_cell_measurement_theta_min      3.0620
_cell_measurement_theta_max      36.5360

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.539
_exptl_crystal_F_000             1824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    12.448
_shelx_estimated_absorpt_T_min   0.147
_shelx_estimated_absorpt_T_max   0.369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.37931
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26383
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.860
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5924
_reflns_number_gt                5717
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.999

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'SHELXS (Sheldrick 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'CIFTAB (sheldrick)'
_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)+(0.0234P)²+3.7175P] 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_abs_structure_details 
;
 Flack x determined using 2361 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5924
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0246
_refine_ls_wR_factor_ref         0.0565
_refine_ls_wR_factor_gt          0.0557
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_restrained_S_all      1.148
_refine_ls_shift/su_max          0.004
_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 1.00573(4) 0.54360(2) 0.88908(2) 0.01883(7) Uani 1 1 d . . . . .
Re2 Re 0.98328(4) 0.30723(2) 1.10916(2) 0.01632(7) Uani 1 1 d . . . . .
Br2 Br 1.22343(11) 0.28276(6) 1.18763(3) 0.02527(18) Uani 1 1 d . . . . .
Br1 Br 0.78372(11) 0.58895(6) 0.96923(3) 0.02445(17) Uani 1 1 d . . . . .
C4 C 0.7956(11) 0.5233(6) 0.8392(3) 0.0226(17) Uani 1 1 d . . . . .
C16 C 0.9919(11) 0.4549(4) 1.1282(3) 0.0171(13) Uani 1 1 d . . . . .
C13 C 0.8054(11) 0.3288(6) 1.0531(4) 0.0244(17) Uani 1 1 d . . . . .
C1 C 1.1747(11) 0.5163(6) 0.8309(4) 0.0248(17) Uani 1 1 d . . . . .
C14 C 0.9870(11) 0.1705(5) 1.0943(3) 0.0207(14) Uani 1 1 d . . . . .
C5 C 1.0067(10) 0.6912(5) 0.8684(3) 0.0173(13) Uani 1 1 d . . . . .
C3 C 1.0001(12) 0.4099(6) 0.9117(3) 0.0272(16) Uani 1 1 d . . . . .
O6 O 0.6993(9) 0.3440(5) 1.0206(2) 0.0321(14) Uani 1 1 d . . . . .
C11 C 1.0518(9) 0.8294(5) 0.8247(3) 0.0188(15) Uani 1 1 d . . . . .
O7 O 0.9888(11) 0.0915(4) 1.0870(2) 0.0364(14) Uani 1 1 d . . . . .
N1 N 0.9643(9) 0.7621(4) 0.9021(2) 0.0215(14) Uani 1 1 d . . . . .
H1A H 0.927130 0.754092 0.936002 0.026 Uiso 1 1 calc R U . . .
O8 O 0.6826(8) 0.2745(5) 1.1963(2) 0.0332(14) Uani 1 1 d . . . . .
C22 C 0.9806(10) 0.6126(4) 1.1188(2) 0.0146(13) Uani 1 1 d . . . . .
O3 O 0.9992(11) 0.3334(4) 0.9247(2) 0.0406(15) Uani 1 1 d . . . . .
N4 N 0.9524(9) 0.5261(4) 1.0941(2) 0.0195(14) Uani 1 1 d . . . . .
H4A H 0.913655 0.518806 1.060376 0.023 Uiso 1 1 calc R U . . .
O4 O 0.6776(9) 0.5114(5) 0.8108(3) 0.0360(15) Uani 1 1 d . . . . .
O5 O 1.2894(9) 0.3564(5) 1.0254(3) 0.0369(15) Uani 1 1 d . . . . .
N2 N 1.0615(8) 0.7326(4) 0.8214(2) 0.0208(13) Uani 1 1 d . . . . .
H2A H 1.098779 0.701755 0.792380 0.025 Uiso 1 1 calc R U . . .
C17 C 1.0456(9) 0.5929(5) 1.1715(3) 0.0164(14) Uani 1 1 d . . . . .
N3 N 1.0503(8) 0.4958(4) 1.1752(2) 0.0179(12) Uani 1 1 d . . . . .
H3A H 1.086512 0.464712 1.204265 0.021 Uiso 1 1 calc R U . . .
C15 C 0.7906(10) 0.2868(6) 1.1643(3) 0.0208(15) Uani 1 1 d . . . . .
C21 C 0.9639(11) 0.7044(5) 1.1004(3) 0.0252(16) Uani 1 1 d . . . . .
H21A H 0.924784 0.718066 1.064283 0.030 Uiso 1 1 calc R U . . .
O1 O 1.2706(9) 0.5025(5) 0.7971(2) 0.0369(15) Uani 1 1 d . . . . .
C12 C 1.1820(10) 0.3353(6) 1.0558(3) 0.0196(16) Uani 1 1 d . . . . .
C20 C 1.0067(14) 0.7750(5) 1.1369(3) 0.0264(16) Uani 1 1 d . . . . .
H20A H 0.995147 0.838610 1.125851 0.032 Uiso 1 1 calc R U . . .
C8 C 1.0019(12) 1.0111(5) 0.8589(3) 0.0260(16) Uani 1 1 d . . . . .
H8A H 0.988070 1.074529 0.869996 0.031 Uiso 1 1 calc R U . . .
C7 C 0.9614(10) 0.9405(5) 0.8954(3) 0.0243(16) Uani 1 1 d . . . . .
H7A H 0.918598 0.954205 0.931104 0.029 Uiso 1 1 calc R U . . .
C6 C 0.9853(10) 0.8487(5) 0.8781(3) 0.0173(13) Uani 1 1 d . . . . .
C10 C 1.0894(11) 0.9004(6) 0.7877(3) 0.0272(17) Uani 1 1 d . . . . .
H10A H 1.131260 0.887485 0.751786 0.033 Uiso 1 1 calc R U . . .
O2 O 1.3059(9) 0.5950(6) 0.9744(3) 0.0442(17) Uani 1 1 d . . . . .
C19 C 1.0666(11) 0.7543(6) 1.1896(3) 0.0263(17) Uani 1 1 d . . . . .
H19A H 1.092987 0.804489 1.213879 0.032 Uiso 1 1 calc R U . . .
C18 C 1.0885(11) 0.6643(6) 1.2076(3) 0.0249(17) Uani 1 1 d . . . . .
H18A H 1.131414 0.651269 1.243394 0.030 Uiso 1 1 calc R U . . .
C9 C 1.0627(11) 0.9917(6) 0.8061(3) 0.0251(17) Uani 1 1 d . . . . .
H9A H 1.086493 1.042322 0.781928 0.030 Uiso 1 1 calc R U . . .
C2 C 1.2000(11) 0.5736(6) 0.9431(4) 0.0286(18) Uani 1 1 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
Re1 C1 1.938(9) . ?
Re1 C3 1.987(8) . ?
Re1 C2 2.004(9) . ?
Re1 C4 2.005(9) . ?
Re1 C5 2.166(6) . ?
Re1 Br1 2.6436(8) . ?
Re2 C13 1.931(9) . ?
Re2 C14 1.985(7) . ?
Re2 C15 1.989(8) . ?
Re2 C12 2.012(8) . ?
Re2 C16 2.159(6) . ?
Re2 Br2 2.6453(8) . ?
C4 O4 1.131(10) . ?
C16 N4 1.347(9) . ?
C16 N3 1.359(9) . ?
C13 O6 1.140(10) . ?
C1 O1 1.109(10) . ?
C14 O7 1.140(9) . ?
C5 N1 1.344(9) . ?
C5 N2 1.353(9) . ?
C3 O3 1.136(9) . ?
C11 N2 1.386(9) . ?
C11 C10 1.386(11) . ?
C11 C6 1.423(10) . ?
N1 C6 1.376(9) . ?
O8 C15 1.137(9) . ?
C22 N4 1.390(8) . ?
C22 C21 1.391(10) . ?
C22 C17 1.403(9) . ?
O5 C12 1.132(10) . ?
C17 C18 1.386(10) . ?
C17 N3 1.389(9) . ?
C21 C20 1.382(11) . ?
C20 C19 1.396(10) . ?
C8 C7 1.379(10) . ?
C8 C9 1.396(11) . ?
C7 C6 1.387(10) . ?
C10 C9 1.392(12) . ?
O2 C2 1.140(10) . ?
C19 C18 1.367(11) . ?

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
C1 Re1 C3 91.5(3) . . ?
C1 Re1 C2 93.3(4) . . ?
C3 Re1 C2 92.1(3) . . ?
C1 Re1 C4 91.8(3) . . ?
C3 Re1 C4 90.8(3) . . ?
C2 Re1 C4 174.1(3) . . ?
C1 Re1 C5 91.2(3) . . ?
C3 Re1 C5 177.2(3) . . ?
C2 Re1 C5 86.8(3) . . ?
C4 Re1 C5 90.0(3) . . ?
C1 Re1 Br1 177.1(2) . . ?
C3 Re1 Br1 90.9(2) . . ?
C2 Re1 Br1 84.9(3) . . ?
C4 Re1 Br1 89.9(2) . . ?
C5 Re1 Br1 86.41(19) . . ?
C13 Re2 C14 92.1(3) . . ?
C13 Re2 C15 90.5(3) . . ?
C14 Re2 C15 89.5(3) . . ?
C13 Re2 C12 90.7(3) . . ?
C14 Re2 C12 93.8(3) . . ?
C15 Re2 C12 176.5(3) . . ?
C13 Re2 C16 91.0(3) . . ?
C14 Re2 C16 176.8(3) . . ?
C15 Re2 C16 91.0(3) . . ?
C12 Re2 C16 85.7(3) . . ?
C13 Re2 Br2 178.1(2) . . ?
C14 Re2 Br2 89.6(2) . . ?
C15 Re2 Br2 88.7(2) . . ?
C12 Re2 Br2 89.9(2) . . ?
C16 Re2 Br2 87.26(19) . . ?
O4 C4 Re1 179.5(8) . . ?
N4 C16 N3 105.6(6) . . ?
N4 C16 Re2 126.6(5) . . ?
N3 C16 Re2 127.7(5) . . ?
O6 C13 Re2 178.1(7) . . ?
O1 C1 Re1 178.5(8) . . ?
O7 C14 Re2 178.4(6) . . ?
N1 C5 N2 105.3(6) . . ?
N1 C5 Re1 126.0(5) . . ?
N2 C5 Re1 128.6(5) . . ?
O3 C3 Re1 179.2(9) . . ?
N2 C11 C10 132.9(7) . . ?
N2 C11 C6 105.3(6) . . ?
C10 C11 C6 121.8(7) . . ?
C5 N1 C6 112.7(6) . . ?
N4 C22 C21 133.0(6) . . ?
N4 C22 C17 105.8(5) . . ?
C21 C22 C17 121.1(6) . . ?
C16 N4 C22 111.6(6) . . ?
C5 N2 C11 111.7(6) . . ?
C18 C17 N3 133.3(6) . . ?
C18 C17 C22 121.1(7) . . ?
N3 C17 C22 105.6(6) . . ?
C16 N3 C17 111.4(6) . . ?
O8 C15 Re2 178.8(7) . . ?
C20 C21 C22 117.2(7) . . ?
O5 C12 Re2 175.8(7) . . ?
C21 C20 C19 121.0(7) . . ?
C7 C8 C9 121.6(7) . . ?
C8 C7 C6 117.7(7) . . ?
N1 C6 C7 134.7(7) . . ?
N1 C6 C11 104.9(6) . . ?
C7 C6 C11 120.4(6) . . ?
C11 C10 C9 116.4(7) . . ?
C18 C19 C20 122.3(7) . . ?
C19 C18 C17 117.3(7) . . ?
C10 C9 C8 122.1(7) . . ?
O2 C2 Re1 176.4(8) . . ?

_refine_diff_density_max         1.789
_refine_diff_density_min         -1.381
_refine_diff_density_rms         0.146

####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 1504039'
_audit_update_record             
;
2017-10-04 deposited with the CCDC.
2017-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H27 N2 P'
_chemical_formula_weight         458.51

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'
P P 0.1023 0.0942 '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                   9.426(8)
_cell_length_b                   9.712(8)
_cell_length_c                   13.810(11)
_cell_angle_alpha                86.810(18)
_cell_angle_beta                 79.90(2)
_cell_angle_gamma                84.897(15)
_cell_volume                     1238.7(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3329
_cell_measurement_theta_min      2.923
_cell_measurement_theta_max      27.495

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_F_000             484
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.860
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12951
_diffrn_reflns_av_unetI/netI     0.1084
_diffrn_reflns_av_R_equivalents  0.1304
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.923
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5648
_reflns_number_gt                4462
_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       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXS (Sheldrick 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'CIFTAB (sheldrick)'
_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)+(0.0991P)²+0.0333P] 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         5648
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0683
_refine_ls_wR_factor_ref         0.1932
_refine_ls_wR_factor_gt          0.1757
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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_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
P1 P 0.29177(4) 0.53529(4) 0.27304(3) 0.03751(16) Uani 1 1 d . . . . .
N1 N 0.34482(16) 0.37994(15) 0.25183(12) 0.0450(4) Uani 1 1 d . . . . .
C1 C 0.10595(17) 0.58560(18) 0.25932(13) 0.0416(4) Uani 1 1 d . . . . .
C2 C 0.0251(2) 0.6999(2) 0.30292(18) 0.0574(5) Uani 1 1 d . . . . .
H2A H 0.065583 0.754335 0.344615 0.069 Uiso 1 1 calc R U . . .
N2 N 0.53340(17) 0.15674(16) 0.23718(13) 0.0511(4) Uani 1 1 d . . . . .
H2B H 0.534593 0.217396 0.187328 0.061 Uiso 1 1 calc R U . . .
C3 C -0.1143(2) 0.7344(3) 0.2855(2) 0.0694(6) Uani 1 1 d . . . . .
H3A H -0.169846 0.811618 0.316090 0.083 Uiso 1 1 calc R U . . .
C4 C -0.1724(2) 0.6575(3) 0.2242(2) 0.0718(7) Uani 1 1 d . . . . .
H4A H -0.267471 0.682706 0.211705 0.086 Uiso 1 1 calc R U . . .
C5 C -0.0942(2) 0.5441(3) 0.18065(19) 0.0686(6) Uani 1 1 d . . . . .
H5A H -0.135316 0.490939 0.138511 0.082 Uiso 1 1 calc R U . . .
C6 C 0.0451(2) 0.5074(2) 0.19849(16) 0.0543(5) Uani 1 1 d . . . . .
H6A H 0.098836 0.428567 0.168974 0.065 Uiso 1 1 calc R U . . .
C7 C 0.31272(18) 0.59499(18) 0.39089(13) 0.0405(4) Uani 1 1 d . . . . .
C8 C 0.2081(2) 0.5791(2) 0.47456(16) 0.0552(5) Uani 1 1 d . . . . .
H8A H 0.118552 0.545140 0.468947 0.066 Uiso 1 1 calc R U . . .
C9 C 0.2335(3) 0.6125(3) 0.56591(17) 0.0667(6) Uani 1 1 d . . . . .
H9A H 0.161907 0.600408 0.622715 0.080 Uiso 1 1 calc R U . . .
C10 C 0.3622(3) 0.6632(2) 0.57439(18) 0.0644(6) Uani 1 1 d . . . . .
H10A H 0.379133 0.686407 0.637095 0.077 Uiso 1 1 calc R U . . .
C11 C 0.4665(3) 0.6804(2) 0.49266(18) 0.0592(5) Uani 1 1 d . . . . .
H11A H 0.554996 0.716173 0.498743 0.071 Uiso 1 1 calc R U . . .
C12 C 0.4425(2) 0.64584(19) 0.40209(15) 0.0474(4) Uani 1 1 d . . . . .
H12A H 0.515616 0.656758 0.346035 0.057 Uiso 1 1 calc R U . . .
C13 C 0.39968(19) 0.64020(18) 0.18134(13) 0.0417(4) Uani 1 1 d . . . . .
C14 C 0.3779(2) 0.7833(2) 0.18179(17) 0.0563(5) Uani 1 1 d . . . . .
H14A H 0.303963 0.825669 0.229173 0.068 Uiso 1 1 calc R U . . .
C15 C 0.4632(3) 0.8654(2) 0.1137(2) 0.0684(7) Uani 1 1 d . . . . .
H15A H 0.449659 0.963430 0.115637 0.082 Uiso 1 1 calc R U . . .
C16 C 0.5679(2) 0.8030(3) 0.04311(19) 0.0671(7) Uani 1 1 d . . . . .
H16A H 0.625385 0.858429 -0.004417 0.080 Uiso 1 1 calc R U . . .
C17 C 0.5892(2) 0.6619(3) 0.04132(18) 0.0661(6) Uani 1 1 d . . . . .
H17A H 0.660942 0.619949 -0.007669 0.079 Uiso 1 1 calc R U . . .
C19 C 0.30465(18) 0.26414(17) 0.31266(14) 0.0411(4) Uani 1 1 d . . . . .
C20 C 0.1749(2) 0.2540(2) 0.37768(17) 0.0541(5) Uani 1 1 d . . . . .
H20A H 0.104107 0.330467 0.382781 0.065 Uiso 1 1 calc R U . . .
C21 C 0.1468(3) 0.1337(2) 0.43558(19) 0.0650(6) Uani 1 1 d . . . . .
H21A H 0.056779 0.128525 0.478567 0.078 Uiso 1 1 calc R U . . .
C22 C 0.2483(3) 0.0234(2) 0.43061(19) 0.0668(6) Uani 1 1 d . . . . .
H22A H 0.229929 -0.057488 0.471196 0.080 Uiso 1 1 calc R U . . .
C23 C 0.3787(2) 0.0301(2) 0.36591(18) 0.0588(5) Uani 1 1 d . . . . .
H23A H 0.449195 -0.046404 0.363014 0.071 Uiso 1 1 calc R U . . .
C18 C 0.5058(2) 0.5789(2) 0.11124(16) 0.0518(5) Uani 1 1 d . . . . .
H18A H 0.522009 0.480983 0.110520 0.062 Uiso 1 1 calc R U . . .
C25 C 0.6625(2) 0.0692(2) 0.24633(18) 0.0556(5) Uani 1 1 d . . . . .
H25A H 0.646799 -0.027481 0.234581 0.067 Uiso 1 1 calc R U . . .
H25B H 0.682348 0.072201 0.314202 0.067 Uiso 1 1 calc R U . . .
C26 C 0.7913(2) 0.1137(2) 0.17448(17) 0.0527(5) Uani 1 1 d . . . . .
C27 C 0.7793(2) 0.1554(3) 0.07846(19) 0.0669(6) Uani 1 1 d . . . . .
H27A H 0.687433 0.159310 0.058651 0.080 Uiso 1 1 calc R U . . .
C28 C 0.8985(3) 0.1917(3) 0.0104(2) 0.0830(8) Uani 1 1 d . . . . .
H28A H 0.888254 0.218607 -0.055391 0.100 Uiso 1 1 calc R U . . .
C29 C 1.0454(3) 0.1472(3) 0.1343(3) 0.0825(8) Uani 1 1 d . . . . .
H29A H 1.137499 0.143165 0.153776 0.099 Uiso 1 1 calc R U . . .
C30 C 1.0318(3) 0.1883(4) 0.0393(3) 0.0846(8) Uani 1 1 d . . . . .
H30A H 1.113759 0.214157 -0.006318 0.102 Uiso 1 1 calc R U . . .
C31 C 0.9259(2) 0.1117(3) 0.2021(2) 0.0662(6) Uani 1 1 d . . . . .
H31A H 0.936522 0.085754 0.267914 0.079 Uiso 1 1 calc R U . . .
C24 C 0.40730(19) 0.14736(18) 0.30532(15) 0.0444(4) Uani 1 1 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
P1 N1 1.5735(19) . ?
P1 C7 1.806(2) . ?
P1 C13 1.8071(19) . ?
P1 C1 1.816(2) . ?
N1 C19 1.405(2) . ?
C1 C6 1.389(3) . ?
C1 C2 1.392(3) . ?
C2 C3 1.387(3) . ?
N2 C24 1.387(3) . ?
N2 C25 1.441(3) . ?
C3 C4 1.371(4) . ?
C4 C5 1.376(4) . ?
C5 C6 1.390(3) . ?
C7 C8 1.393(3) . ?
C7 C12 1.395(3) . ?
C8 C9 1.385(3) . ?
C9 C10 1.375(4) . ?
C10 C11 1.374(4) . ?
C11 C12 1.374(3) . ?
C13 C18 1.382(3) . ?
C13 C14 1.387(3) . ?
C14 C15 1.390(3) . ?
C15 C16 1.384(4) . ?
C16 C17 1.368(4) . ?
C17 C18 1.400(3) . ?
C19 C20 1.392(3) . ?
C19 C24 1.420(3) . ?
C20 C21 1.397(3) . ?
C21 C22 1.368(3) . ?
C22 C23 1.391(3) . ?
C23 C24 1.392(3) . ?
C25 C26 1.506(3) . ?
C26 C27 1.386(4) . ?
C26 C31 1.386(3) . ?
C27 C28 1.390(3) . ?
C28 C30 1.381(4) . ?
C29 C30 1.374(5) . ?
C29 C31 1.389(4) . ?

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 P1 C7 116.48(9) . . ?
N1 P1 C13 106.81(10) . . ?
C7 P1 C13 106.04(9) . . ?
N1 P1 C1 115.26(9) . . ?
C7 P1 C1 106.31(8) . . ?
C13 P1 C1 104.99(9) . . ?
C19 N1 P1 126.12(14) . . ?
C6 C1 C2 119.18(18) . . ?
C6 C1 P1 117.10(15) . . ?
C2 C1 P1 123.67(15) . . ?
C3 C2 C1 120.0(2) . . ?
C24 N2 C25 121.37(17) . . ?
C4 C3 C2 120.2(2) . . ?
C3 C4 C5 120.5(2) . . ?
C4 C5 C6 119.8(2) . . ?
C1 C6 C5 120.3(2) . . ?
C8 C7 C12 118.02(18) . . ?
C8 C7 P1 121.79(15) . . ?
C12 C7 P1 119.88(14) . . ?
C9 C8 C7 120.5(2) . . ?
C10 C9 C8 120.0(2) . . ?
C11 C10 C9 120.3(2) . . ?
C10 C11 C12 119.8(2) . . ?
C11 C12 C7 121.25(19) . . ?
C18 C13 C14 119.47(18) . . ?
C18 C13 P1 120.46(15) . . ?
C14 C13 P1 120.07(16) . . ?
C13 C14 C15 120.7(2) . . ?
C16 C15 C14 119.3(2) . . ?
C17 C16 C15 120.4(2) . . ?
C16 C17 C18 120.4(2) . . ?
C20 C19 N1 126.13(17) . . ?
C20 C19 C24 118.07(17) . . ?
N1 C19 C24 115.79(16) . . ?
C19 C20 C21 121.3(2) . . ?
C22 C21 C20 120.3(2) . . ?
C21 C22 C23 119.7(2) . . ?
C22 C23 C24 121.0(2) . . ?
C13 C18 C17 119.7(2) . . ?
N2 C25 C26 111.77(18) . . ?
C27 C26 C31 118.0(2) . . ?
C27 C26 C25 121.05(19) . . ?
C31 C26 C25 120.9(2) . . ?
C26 C27 C28 121.6(2) . . ?
C30 C28 C27 119.4(3) . . ?
C30 C29 C31 120.7(2) . . ?
C29 C30 C28 119.7(3) . . ?
C26 C31 C29 120.6(3) . . ?
N2 C24 C23 123.00(18) . . ?
N2 C24 C19 117.46(16) . . ?
C23 C24 C19 119.54(18) . . ?

_refine_diff_density_max         0.719
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_4a
_database_code_depnum_ccdc_archive 'CCDC 1504038'
_audit_update_record             
;
2017-10-05 deposited with the CCDC.
2017-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H18 Br N4 O4 Re'
_chemical_formula_weight         656.50

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   10.1361(4)
_cell_length_b                   12.5694(4)
_cell_length_c                   17.6326(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.792(4)
_cell_angle_gamma                90
_cell_volume                     2243.81(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6390
_cell_measurement_theta_min      2.824
_cell_measurement_theta_max      29.997

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.943
_exptl_crystal_F_000             1256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    7.231
_shelx_estimated_absorpt_T_min   0.326
_shelx_estimated_absorpt_T_max   0.410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.69371
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37715
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.824
_diffrn_reflns_theta_max         29.997
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6390
_reflns_number_gt                5219
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'CIFTAB (sheldrick)'
_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)+(0.0175P)²] 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         6390
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0239
_refine_ls_wR_factor_ref         0.0445
_refine_ls_wR_factor_gt          0.0416
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.973
_refine_ls_shift/su_max          0.005
_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 0.76779(2) 0.31260(2) 0.64020(2) 0.02070(4) Uani 1 1 d . . . . .
Br1 Br 0.78746(3) 0.25525(3) 0.22693(2) 0.04109(8) Uani 1 1 d . . . . .
O1 O 0.9680(2) 0.13745(16) 0.60726(12) 0.0417(5) Uani 1 1 d . . . . .
N1 N 0.6267(2) 0.18861(16) 0.50242(12) 0.0228(5) Uani 1 1 d . . . . .
H1A H 0.698531 0.191712 0.476435 0.027 Uiso 1 1 calc R U . . .
C1 C 0.8930(3) 0.2031(2) 0.62130(15) 0.0275(6) Uani 1 1 d . . . . .
O2 O 0.9826(2) 0.44217(17) 0.73170(11) 0.0408(5) Uani 1 1 d . . . . .
N2 N 0.4908(2) 0.20957(16) 0.59124(12) 0.0249(5) Uani 1 1 d . . . . .
H2A H 0.457379 0.228717 0.634293 0.030 Uiso 1 1 calc R U . . .
C2 C 0.9035(3) 0.3944(2) 0.69890(14) 0.0269(6) Uani 1 1 d . . . . .
N3 N 0.7980(2) 0.40746(16) 0.53863(11) 0.0210(4) Uani 1 1 d . . . . .
O3 O 0.6925(2) 0.19000(18) 0.78287(12) 0.0502(6) Uani 1 1 d . . . . .
C3 C 0.7213(3) 0.2359(2) 0.72980(16) 0.0304(6) Uani 1 1 d . . . . .
N4 N 0.6290(2) 0.44505(16) 0.64584(11) 0.0215(4) Uani 1 1 d . . . . .
O4 O 0.8166(2) 0.17350(18) 0.39671(12) 0.0480(6) Uani 1 1 d . . . . .
H4 H 0.804611 0.199707 0.353089 0.072 Uiso 1 1 calc R U . . .
C4 C 0.6158(3) 0.23013(19) 0.57289(14) 0.0215(5) Uani 1 1 d . . . . .
C5 C 0.5086(3) 0.1402(2) 0.47654(15) 0.0250(6) Uani 1 1 d . . . . .
C6 C 0.4740(3) 0.0878(2) 0.40930(15) 0.0310(6) Uani 1 1 d . . . . .
H6A H 0.534948 0.077921 0.370660 0.037 Uiso 1 1 calc R U . . .
C7 C 0.3459(3) 0.0510(2) 0.40179(18) 0.0398(8) Uani 1 1 d . . . . .
H7A H 0.317392 0.015107 0.356490 0.048 Uiso 1 1 calc R U . . .
C8 C 0.2576(3) 0.0649(3) 0.45864(19) 0.0437(8) Uani 1 1 d . . . . .
H8A H 0.170439 0.037895 0.451216 0.052 Uiso 1 1 calc R U . . .
C9 C 0.2928(3) 0.1173(2) 0.52635(18) 0.0382(7) Uani 1 1 d . . . . .
H9A H 0.232038 0.126928 0.565104 0.046 Uiso 1 1 calc R U . . .
C10 C 0.4213(3) 0.1545(2) 0.53391(15) 0.0267(6) Uani 1 1 d . . . . .
C11 C 0.8808(3) 0.3814(2) 0.48452(15) 0.0273(6) Uani 1 1 d . . . . .
H11A H 0.934487 0.319954 0.491623 0.033 Uiso 1 1 calc R U . . .
C12 C 0.8912(3) 0.4404(2) 0.41878(15) 0.0334(7) Uani 1 1 d . . . . .
H12A H 0.948704 0.418242 0.380824 0.040 Uiso 1 1 calc R U . . .
C13 C 0.8173(3) 0.5313(2) 0.40929(16) 0.0365(7) Uani 1 1 d . . . . .
H13A H 0.823671 0.573602 0.364992 0.044 Uiso 1 1 calc R U . . .
C14 C 0.7334(3) 0.5602(2) 0.46530(15) 0.0319(6) Uani 1 1 d . . . . .
H14A H 0.682247 0.623330 0.459810 0.038 Uiso 1 1 calc R U . . .
C15 C 0.7236(2) 0.4974(2) 0.52947(14) 0.0230(5) Uani 1 1 d . . . . .
C16 C 0.6337(3) 0.5197(2) 0.59024(14) 0.0231(5) Uani 1 1 d . . . . .
C17 C 0.5573(3) 0.6105(2) 0.59249(17) 0.0352(7) Uani 1 1 d . . . . .
H17A H 0.562215 0.662477 0.553590 0.042 Uiso 1 1 calc R U . . .
C18 C 0.4742(3) 0.6260(2) 0.65089(17) 0.0375(7) Uani 1 1 d . . . . .
H18A H 0.422667 0.689002 0.653045 0.045 Uiso 1 1 calc R U . . .
C19 C 0.4664(3) 0.5494(2) 0.70602(16) 0.0326(7) Uani 1 1 d . . . . .
H19A H 0.407982 0.557369 0.746153 0.039 Uiso 1 1 calc R U . . .
C20 C 0.5459(3) 0.4604(2) 0.70164(15) 0.0278(6) Uani 1 1 d . . . . .
H20A H 0.541276 0.407686 0.740008 0.033 Uiso 1 1 calc R U . . .
C21 C 0.9192(5) 0.1062(4) 0.3974(2) 0.114(2) Uani 1 1 d . . . . .
H21A H 0.993551 0.140268 0.373471 0.170 Uiso 1 1 calc R U . . .
H21B H 0.893743 0.041556 0.369338 0.170 Uiso 1 1 calc R U . . .
H21C H 0.945376 0.087682 0.450013 0.170 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 C1 1.913(3) . ?
Re1 C3 1.929(3) . ?
Re1 C2 1.970(3) . ?
Re1 C4 2.163(3) . ?
Re1 N4 2.185(2) . ?
Re1 N3 2.185(2) . ?
O1 C1 1.157(3) . ?
N1 C4 1.357(3) . ?
N1 C5 1.399(3) . ?
N1 H1A 0.8800 . ?
O2 C2 1.137(3) . ?
N2 C4 1.347(3) . ?
N2 C10 1.389(3) . ?
N2 H2A 0.8800 . ?
N3 C11 1.342(3) . ?
N3 C15 1.363(3) . ?
O3 C3 1.149(3) . ?
N4 C20 1.341(3) . ?
N4 C16 1.360(3) . ?
O4 C21 1.340(4) . ?
O4 H4 0.8400 . ?
C5 C6 1.386(4) . ?
C5 C10 1.388(4) . ?
C6 C7 1.379(4) . ?
C6 H6A 0.9500 . ?
C7 C8 1.387(5) . ?
C7 H7A 0.9500 . ?
C8 C9 1.395(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.384(4) . ?
C9 H9A 0.9500 . ?
C11 C12 1.384(4) . ?
C11 H11A 0.9500 . ?
C12 C13 1.372(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.383(4) . ?
C13 H13A 0.9500 . ?
C14 C15 1.387(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.468(4) . ?
C16 C17 1.381(4) . ?
C17 C18 1.376(4) . ?
C17 H17A 0.9500 . ?
C18 C19 1.373(4) . ?
C18 H18A 0.9500 . ?
C19 C20 1.382(4) . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C1 Re1 C3 88.50(12) . . ?
C1 Re1 C2 90.83(11) . . ?
C3 Re1 C2 91.29(11) . . ?
C1 Re1 C4 91.18(10) . . ?
C3 Re1 C4 90.80(11) . . ?
C2 Re1 C4 177.14(10) . . ?
C1 Re1 N4 172.10(9) . . ?
C3 Re1 N4 99.19(10) . . ?
C2 Re1 N4 90.76(9) . . ?
C4 Re1 N4 86.98(8) . . ?
C1 Re1 N3 97.43(10) . . ?
C3 Re1 N3 173.46(10) . . ?
C2 Re1 N3 91.37(9) . . ?
C4 Re1 N3 86.34(8) . . ?
N4 Re1 N3 74.79(8) . . ?
C4 N1 C5 111.1(2) . . ?
C4 N1 H1A 124.5 . . ?
C5 N1 H1A 124.5 . . ?
O1 C1 Re1 177.7(2) . . ?
C4 N2 C10 111.7(2) . . ?
C4 N2 H2A 124.1 . . ?
C10 N2 H2A 124.1 . . ?
O2 C2 Re1 178.9(2) . . ?
C11 N3 C15 118.6(2) . . ?
C11 N3 Re1 124.55(17) . . ?
C15 N3 Re1 116.79(16) . . ?
O3 C3 Re1 179.4(3) . . ?
C20 N4 C16 118.3(2) . . ?
C20 N4 Re1 124.94(17) . . ?
C16 N4 Re1 116.63(16) . . ?
C21 O4 H4 109.5 . . ?
N2 C4 N1 105.4(2) . . ?
N2 C4 Re1 127.80(18) . . ?
N1 C4 Re1 126.80(19) . . ?
C6 C5 C10 122.7(3) . . ?
C6 C5 N1 131.5(3) . . ?
C10 C5 N1 105.8(2) . . ?
C7 C6 C5 116.1(3) . . ?
C7 C6 H6A 122.0 . . ?
C5 C6 H6A 122.0 . . ?
C6 C7 C8 121.7(3) . . ?
C6 C7 H7A 119.1 . . ?
C8 C7 H7A 119.1 . . ?
C7 C8 C9 122.1(3) . . ?
C7 C8 H8A 119.0 . . ?
C9 C8 H8A 119.0 . . ?
C10 C9 C8 116.2(3) . . ?
C10 C9 H9A 121.9 . . ?
C8 C9 H9A 121.9 . . ?
C9 C10 C5 121.1(3) . . ?
C9 C10 N2 132.9(3) . . ?
C5 C10 N2 106.0(2) . . ?
N3 C11 C12 122.8(2) . . ?
N3 C11 H11A 118.6 . . ?
C12 C11 H11A 118.6 . . ?
C13 C12 C11 119.0(3) . . ?
C13 C12 H12A 120.5 . . ?
C11 C12 H12A 120.5 . . ?
C12 C13 C14 118.9(3) . . ?
C12 C13 H13A 120.5 . . ?
C14 C13 H13A 120.5 . . ?
C13 C14 C15 120.2(3) . . ?
C13 C14 H14A 119.9 . . ?
C15 C14 H14A 119.9 . . ?
N3 C15 C14 120.5(2) . . ?
N3 C15 C16 115.6(2) . . ?
C14 C15 C16 123.9(2) . . ?
N4 C16 C17 120.7(2) . . ?
N4 C16 C15 116.0(2) . . ?
C17 C16 C15 123.3(2) . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17A 119.9 . . ?
C16 C17 H17A 119.9 . . ?
C19 C18 C17 119.3(3) . . ?
C19 C18 H18A 120.4 . . ?
C17 C18 H18A 120.4 . . ?
C18 C19 C20 118.3(3) . . ?
C18 C19 H19A 120.8 . . ?
C20 C19 H19A 120.8 . . ?
N4 C20 C19 123.1(2) . . ?
N4 C20 H20A 118.4 . . ?
C19 C20 H20A 118.4 . . ?
O4 C21 H21A 109.5 . . ?
O4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2A Br1 0.88 2.44 3.263(2) 156.2 4_566 yes
O4 H4 Br1 0.84 2.33 3.165(2) 172.9 . yes
N1 H1A O4 0.88 1.90 2.750(3) 160.9 . yes

_refine_diff_density_max         0.831
_refine_diff_density_min         -0.982
_refine_diff_density_rms         0.197

####################################################################### 
# 
# 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_4c
_database_code_depnum_ccdc_archive 'CCDC 1504043'
_audit_update_record             
;
2017-10-05 deposited with the CCDC.
2017-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H26 Br N4 O3 Re'
_chemical_formula_weight         756.66

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   11.1298(5)
_cell_length_b                   20.0627(9)
_cell_length_c                   14.1870(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.435(4)
_cell_angle_gamma                90
_cell_volume                     3105.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    11764
_cell_measurement_theta_min      3.1110
_cell_measurement_theta_max      33.8900

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    5.235
_shelx_estimated_absorpt_T_min   0.436
_shelx_estimated_absorpt_T_max   0.623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83771
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30694
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.945
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7097
_reflns_number_gt                5628
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'CIFTAB (sheldrick)'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0203P)²] 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         7097
_refine_ls_number_parameters     355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0635
_refine_ls_wR_factor_gt          0.0589
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Re1 Re 0.56274(2) 0.18412(2) 0.78017(2) 0.01854(5) Uani 1 1 d . . . . .
Br1 Br 0.36162(4) 0.31379(2) 1.01483(3) 0.03187(11) Uani 1 1 d . . . . .
O1 O 0.8407(2) 0.18351(15) 0.7897(2) 0.0322(7) Uani 1 1 d . . . . .
N1 N 0.5062(3) 0.33065(16) 0.8359(2) 0.0216(7) Uani 1 1 d . . . . .
H1A H 0.458240 0.314290 0.872557 0.026 Uiso 1 1 calc R U . . .
C1 C 0.7354(4) 0.1836(2) 0.7835(3) 0.0245(9) Uani 1 1 d . . . . .
O2 O 0.6324(3) 0.18401(17) 1.0011(2) 0.0400(8) Uani 1 1 d . . . . .
N2 N 0.6243(3) 0.33782(16) 0.7328(2) 0.0207(7) Uani 1 1 d . . . . .
C2 C 0.6055(4) 0.1853(2) 0.9184(3) 0.0248(9) Uani 1 1 d . . . . .
N3 N 0.4924(3) 0.17957(15) 0.6252(2) 0.0201(7) Uani 1 1 d . . . . .
O3 O 0.5661(3) 0.03045(16) 0.8006(3) 0.0498(9) Uani 1 1 d . . . . .
C3 C 0.5621(4) 0.0867(2) 0.7892(3) 0.0275(9) Uani 1 1 d . . . . .
N4 N 0.3636(3) 0.18939(16) 0.7619(2) 0.0218(7) Uani 1 1 d . . . . .
C4 C 0.5609(3) 0.29308(19) 0.7779(3) 0.0192(8) Uani 1 1 d . . . . .
C5 C 0.6961(4) 0.3179(2) 0.6602(3) 0.0248(9) Uani 1 1 d . . . . .
H5A H 0.659733 0.276763 0.628099 0.030 Uiso 1 1 calc R U . . .
H5B H 0.780598 0.307172 0.693689 0.030 Uiso 1 1 calc R U . . .
C6 C 0.7023(4) 0.3699(2) 0.5841(3) 0.0230(9) Uani 1 1 d . . . . .
C7 C 0.5967(4) 0.3919(2) 0.5223(3) 0.0280(9) Uani 1 1 d . . . . .
C8 C 0.4715(4) 0.3654(2) 0.5274(3) 0.0389(11) Uani 1 1 d . . . . .
H8A H 0.453191 0.375542 0.590683 0.058 Uiso 1 1 calc R U . . .
H8B H 0.469925 0.317003 0.517749 0.058 Uiso 1 1 calc R U . . .
H8C H 0.409921 0.386379 0.477264 0.058 Uiso 1 1 calc R U . . .
C9 C 0.6074(4) 0.4390(2) 0.4514(3) 0.0380(11) Uani 1 1 d . . . . .
H9A H 0.535457 0.455000 0.410016 0.046 Uiso 1 1 calc R U . . .
C10 C 0.7211(5) 0.4628(2) 0.4403(3) 0.0397(12) Uani 1 1 d . . . . .
C11 C 0.7303(6) 0.5124(3) 0.3605(4) 0.0607(16) Uani 1 1 d . . . . .
H11A H 0.772384 0.552776 0.388736 0.091 Uiso 1 1 calc R U . . .
H11B H 0.647838 0.523985 0.325828 0.091 Uiso 1 1 calc R U . . .
H11C H 0.776723 0.492351 0.315846 0.091 Uiso 1 1 calc R U . . .
C12 C 0.8249(4) 0.4401(2) 0.5024(3) 0.0314(10) Uani 1 1 d . . . . .
H12A H 0.902883 0.456429 0.495715 0.038 Uiso 1 1 calc R U . . .
C13 C 0.8182(4) 0.3941(2) 0.5741(3) 0.0259(9) Uani 1 1 d . . . . .
C14 C 0.9362(4) 0.3716(2) 0.6396(3) 0.0365(11) Uani 1 1 d . . . . .
H14A H 1.005960 0.394538 0.621400 0.055 Uiso 1 1 calc R U . . .
H14B H 0.945704 0.323357 0.633127 0.055 Uiso 1 1 calc R U . . .
H14C H 0.933025 0.382378 0.706407 0.055 Uiso 1 1 calc R U . . .
C15 C 0.6111(4) 0.4028(2) 0.7652(3) 0.0245(9) Uani 1 1 d . . . . .
C16 C 0.6605(4) 0.4647(2) 0.7465(3) 0.0320(10) Uani 1 1 d . . . . .
H16A H 0.713633 0.468963 0.702052 0.038 Uiso 1 1 calc R U . . .
C17 C 0.6284(5) 0.5187(2) 0.7955(3) 0.0425(12) Uani 1 1 d . . . . .
H17A H 0.660886 0.561159 0.784822 0.051 Uiso 1 1 calc R U . . .
C18 C 0.5487(5) 0.5133(2) 0.8613(3) 0.0397(12) Uani 1 1 d . . . . .
H18A H 0.527368 0.552174 0.892583 0.048 Uiso 1 1 calc R U . . .
C19 C 0.5018(4) 0.4526(2) 0.8804(3) 0.0329(10) Uani 1 1 d . . . . .
H19A H 0.449491 0.448451 0.925506 0.040 Uiso 1 1 calc R U . . .
C20 C 0.5336(4) 0.3978(2) 0.8315(3) 0.0250(9) Uani 1 1 d . . . . .
C21 C 0.3039(4) 0.1933(2) 0.8359(3) 0.0292(10) Uani 1 1 d . . . . .
H21A H 0.349821 0.193814 0.899949 0.035 Uiso 1 1 calc R U . . .
C22 C 0.1774(4) 0.1965(2) 0.8204(3) 0.0369(11) Uani 1 1 d . . . . .
H22A H 0.137421 0.199886 0.873470 0.044 Uiso 1 1 calc R U . . .
C23 C 0.1105(4) 0.1949(2) 0.7295(3) 0.0381(12) Uani 1 1 d . . . . .
H23A H 0.023533 0.196712 0.718543 0.046 Uiso 1 1 calc R U . . .
C24 C 0.1702(4) 0.1905(2) 0.6528(3) 0.0350(11) Uani 1 1 d . . . . .
H24A H 0.124662 0.188778 0.588702 0.042 Uiso 1 1 calc R U . . .
C25 C 0.2975(3) 0.18855(19) 0.6708(3) 0.0209(8) Uani 1 1 d . . . . .
C26 C 0.3687(3) 0.1829(2) 0.5944(3) 0.0229(8) Uani 1 1 d . . . . .
C27 C 0.3164(4) 0.1793(2) 0.4975(3) 0.0355(11) Uani 1 1 d . . . . .
H27A H 0.229907 0.181891 0.477337 0.043 Uiso 1 1 calc R U . . .
C28 C 0.3895(4) 0.1719(3) 0.4302(3) 0.0415(12) Uani 1 1 d . . . . .
H28A H 0.354249 0.169397 0.363547 0.050 Uiso 1 1 calc R U . . .
C29 C 0.5143(4) 0.1683(2) 0.4615(3) 0.0342(11) Uani 1 1 d . . . . .
H29A H 0.566787 0.163659 0.416651 0.041 Uiso 1 1 calc R U . . .
C30 C 0.5628(4) 0.1714(2) 0.5586(3) 0.0255(9) Uani 1 1 d . . . . .
H30A H 0.649019 0.167651 0.579617 0.031 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 C1 1.913(4) . ?
Re1 C2 1.924(4) . ?
Re1 C3 1.958(4) . ?
Re1 N4 2.183(3) . ?
Re1 N3 2.184(3) . ?
Re1 C4 2.186(4) . ?
O1 C1 1.158(4) . ?
N1 C4 1.347(4) . ?
N1 C20 1.385(5) . ?
N1 H1A 0.8800 . ?
O2 C2 1.152(5) . ?
N2 C4 1.376(4) . ?
N2 C15 1.401(5) . ?
N2 C5 1.477(4) . ?
N3 C30 1.351(4) . ?
N3 C26 1.361(5) . ?
O3 C3 1.140(5) . ?
N4 C21 1.352(5) . ?
N4 C25 1.354(5) . ?
C5 C6 1.513(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.391(6) . ?
C6 C13 1.412(5) . ?
C7 C9 1.403(6) . ?
C7 C8 1.507(6) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.390(6) . ?
C9 H9A 0.9500 . ?
C10 C12 1.384(6) . ?
C10 C11 1.525(6) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.386(5) . ?
C12 H12A 0.9500 . ?
C13 C14 1.519(6) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C20 1.400(5) . ?
C15 C16 1.404(5) . ?
C16 C17 1.372(6) . ?
C16 H16A 0.9500 . ?
C17 C18 1.413(6) . ?
C17 H17A 0.9500 . ?
C18 C19 1.374(6) . ?
C18 H18A 0.9500 . ?
C19 C20 1.384(5) . ?
C19 H19A 0.9500 . ?
C21 C22 1.382(6) . ?
C21 H21A 0.9500 . ?
C22 C23 1.356(6) . ?
C22 H22A 0.9500 . ?
C23 C24 1.386(6) . ?
C23 H23A 0.9500 . ?
C24 C25 1.389(5) . ?
C24 H24A 0.9500 . ?
C25 C26 1.469(5) . ?
C26 C27 1.383(6) . ?
C27 C28 1.380(6) . ?
C27 H27A 0.9500 . ?
C28 C29 1.374(6) . ?
C28 H28A 0.9500 . ?
C29 C30 1.378(6) . ?
C29 H29A 0.9500 . ?
C30 H30A 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
C1 Re1 C2 86.02(16) . . ?
C1 Re1 C3 90.53(16) . . ?
C2 Re1 C3 87.11(17) . . ?
C1 Re1 N4 174.15(14) . . ?
C2 Re1 N4 99.26(14) . . ?
C3 Re1 N4 92.26(14) . . ?
C1 Re1 N3 100.52(14) . . ?
C2 Re1 N3 173.24(13) . . ?
C3 Re1 N3 91.07(15) . . ?
N4 Re1 N3 74.29(11) . . ?
C1 Re1 C4 90.70(15) . . ?
C2 Re1 C4 90.12(15) . . ?
C3 Re1 C4 176.88(15) . . ?
N4 Re1 C4 86.77(12) . . ?
N3 Re1 C4 91.52(13) . . ?
C4 N1 C20 112.8(3) . . ?
C4 N1 H1A 123.6 . . ?
C20 N1 H1A 123.6 . . ?
O1 C1 Re1 177.1(3) . . ?
C4 N2 C15 111.0(3) . . ?
C4 N2 C5 123.1(3) . . ?
C15 N2 C5 126.0(3) . . ?
O2 C2 Re1 177.8(4) . . ?
C30 N3 C26 118.1(3) . . ?
C30 N3 Re1 124.5(3) . . ?
C26 N3 Re1 117.4(2) . . ?
O3 C3 Re1 175.4(4) . . ?
C21 N4 C25 119.0(3) . . ?
C21 N4 Re1 123.6(3) . . ?
C25 N4 Re1 117.4(2) . . ?
N1 C4 N2 104.8(3) . . ?
N1 C4 Re1 123.7(3) . . ?
N2 C4 Re1 130.9(3) . . ?
N2 C5 C6 114.8(3) . . ?
N2 C5 H5A 108.6 . . ?
C6 C5 H5A 108.6 . . ?
N2 C5 H5B 108.6 . . ?
C6 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
C7 C6 C13 120.1(4) . . ?
C7 C6 C5 121.1(3) . . ?
C13 C6 C5 118.8(4) . . ?
C6 C7 C9 119.0(4) . . ?
C6 C7 C8 122.1(4) . . ?
C9 C7 C8 118.9(4) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C7 121.4(4) . . ?
C10 C9 H9A 119.3 . . ?
C7 C9 H9A 119.3 . . ?
C12 C10 C9 118.5(4) . . ?
C12 C10 C11 121.2(4) . . ?
C9 C10 C11 120.3(5) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 C13 121.9(4) . . ?
C10 C12 H12A 119.1 . . ?
C13 C12 H12A 119.1 . . ?
C12 C13 C6 119.1(4) . . ?
C12 C13 C14 118.8(4) . . ?
C6 C13 C14 122.2(4) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 N2 105.8(3) . . ?
C20 C15 C16 120.5(4) . . ?
N2 C15 C16 133.7(4) . . ?
C17 C16 C15 116.8(4) . . ?
C17 C16 H16A 121.6 . . ?
C15 C16 H16A 121.6 . . ?
C16 C17 C18 122.4(4) . . ?
C16 C17 H17A 118.8 . . ?
C18 C17 H17A 118.8 . . ?
C19 C18 C17 120.7(4) . . ?
C19 C18 H18A 119.6 . . ?
C17 C18 H18A 119.6 . . ?
C18 C19 C20 117.5(4) . . ?
C18 C19 H19A 121.3 . . ?
C20 C19 H19A 121.3 . . ?
C19 C20 N1 132.1(4) . . ?
C19 C20 C15 122.1(4) . . ?
N1 C20 C15 105.7(3) . . ?
N4 C21 C22 121.4(4) . . ?
N4 C21 H21A 119.3 . . ?
C22 C21 H21A 119.3 . . ?
C23 C22 C21 120.0(4) . . ?
C23 C22 H22A 120.0 . . ?
C21 C22 H22A 120.0 . . ?
C22 C23 C24 119.3(4) . . ?
C22 C23 H23A 120.3 . . ?
C24 C23 H23A 120.3 . . ?
C23 C24 C25 119.2(4) . . ?
C23 C24 H24A 120.4 . . ?
C25 C24 H24A 120.4 . . ?
N4 C25 C24 121.1(3) . . ?
N4 C25 C26 115.8(3) . . ?
C24 C25 C26 123.1(4) . . ?
N3 C26 C27 121.1(3) . . ?
N3 C26 C25 115.2(3) . . ?
C27 C26 C25 123.7(3) . . ?
C28 C27 C26 120.3(4) . . ?
C28 C27 H27A 119.9 . . ?
C26 C27 H27A 119.9 . . ?
C29 C28 C27 118.6(4) . . ?
C29 C28 H28A 120.7 . . ?
C27 C28 H28A 120.7 . . ?
C28 C29 C30 119.4(4) . . ?
C28 C29 H29A 120.3 . . ?
C30 C29 H29A 120.3 . . ?
N3 C30 C29 122.6(4) . . ?
N3 C30 H30A 118.7 . . ?
C29 C30 H30A 118.7 . . ?

_refine_diff_density_max         1.230
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.114



####################################################################### 
# 
# 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_5c
_database_code_depnum_ccdc_archive 'CCDC 1564565'
_audit_update_record             
;
2017-10-04 deposited with the CCDC.
2017-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H30 Br N4 O4 Re'
_chemical_formula_weight         812.72

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.0169(4)
_cell_length_b                   28.4257(6)
_cell_length_c                   12.1002(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.558(2)
_cell_angle_gamma                90
_cell_volume                     6111.0(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    21257
_cell_measurement_theta_min      3.0790
_cell_measurement_theta_max      34.7910

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_F_000             3184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.125
_exptl_absorpt_coefficient_mu    5.329
_shelx_estimated_absorpt_T_min   0.349
_shelx_estimated_absorpt_T_max   0.556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75939
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            61683
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.864
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             14006
_reflns_number_gt                11730
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'SHELXS (Sheldrick 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'CIFTAB (sheldrick)'
_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)+(0.0274P)²+2.9239P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         14006
_refine_ls_number_parameters     788
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0695
_refine_ls_wR_factor_gt          0.0650
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.004
_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 0.66393(2) 0.69437(2) 0.60742(2) 0.01972(4) Uani 1 1 d . . . . .
Br1 Br 0.86372(2) 0.58082(2) 0.51385(4) 0.04186(12) Uani 1 1 d . . . . .
N1 N 0.68265(16) 0.60592(10) 0.4590(2) 0.0227(6) Uani 1 1 d . . . . .
H1A H 0.729918 0.604095 0.491978 0.027 Uiso 1 1 calc R U . . .
O1 O 0.81524(16) 0.70868(12) 0.5282(3) 0.0484(8) Uani 1 1 d . . . . .
C1 C 0.7584(2) 0.70273(13) 0.5562(3) 0.0289(9) Uani 1 1 d . . . . .
Re2 Re 0.17246(2) 0.68845(2) 0.08039(2) 0.02155(4) Uani 1 1 d . . . . .
Br2 Br 0.35653(2) 0.56438(2) 0.01185(3) 0.03008(9) Uani 1 1 d . . . . .
O2 O 0.70614(17) 0.77570(10) 0.7770(3) 0.0421(7) Uani 1 1 d . . . . .
N2 N 0.56706(16) 0.62767(10) 0.4183(2) 0.0208(6) Uani 1 1 d . . . . .
C2 C 0.6915(2) 0.74440(13) 0.7169(3) 0.0269(8) Uani 1 1 d . . . . .
N3 N 0.69925(15) 0.63575(10) 0.7201(2) 0.0192(6) Uani 1 1 d . . . . .
O3 O 0.60096(17) 0.76921(10) 0.4345(3) 0.0437(8) Uani 1 1 d . . . . .
C3 C 0.6235(2) 0.74114(13) 0.5007(3) 0.0274(8) Uani 1 1 d . . . . .
O4 O 0.31374(17) 0.68938(10) -0.0327(3) 0.0449(8) Uani 1 1 d . . . . .
N4 N 0.56587(16) 0.67940(10) 0.6869(2) 0.0213(6) Uani 1 1 d . . . . .
C4 C 0.63314(19) 0.63817(12) 0.4855(3) 0.0206(7) Uani 1 1 d . . . . .
N5 N 0.17716(16) 0.59329(10) -0.0484(2) 0.0220(6) Uani 1 1 d . . . . .
H5A H 0.223420 0.589079 -0.012918 0.026 Uiso 1 1 calc R U . . .
O5 O 0.11085(17) 0.76089(10) -0.0996(2) 0.0416(7) Uani 1 1 d . . . . .
C5 C 0.6501(2) 0.57610(13) 0.3737(3) 0.0235(8) Uani 1 1 d . . . . .
O6 O 0.23285(18) 0.77445(10) 0.2254(3) 0.0495(9) Uani 1 1 d . . . . .
N6 N 0.06504(15) 0.62141(10) -0.0957(2) 0.0210(6) Uani 1 1 d . . . . .
C6 C 0.6787(2) 0.53957(13) 0.3173(3) 0.0285(8) Uani 1 1 d . . . . .
H6A H 0.729692 0.529791 0.336114 0.034 Uiso 1 1 calc R U . . .
N7 N 0.20652(15) 0.63348(10) 0.2048(2) 0.0194(6) Uani 1 1 d . . . . .
C7 C 0.6296(2) 0.51819(14) 0.2328(3) 0.0322(9) Uani 1 1 d . . . . .
H7A H 0.647370 0.493304 0.191700 0.039 Uiso 1 1 calc R U . . .
O7 O 0.4442(2) 0.66017(15) 0.1388(3) 0.0656(11) Uani 1 1 d . . . . .
H7 H 0.419416 0.642508 0.090518 0.098 Uiso 1 1 calc R U . . .
N8 N 0.07574(16) 0.68000(11) 0.1668(2) 0.0243(7) Uani 1 1 d . . . . .
O8 O 0.9749(2) 0.67880(14) 0.6114(3) 0.0636(11) Uani 1 1 d . . . . .
C8 C 0.5546(2) 0.53212(13) 0.2060(3) 0.0304(9) Uani 1 1 d . . . . .
H8A H 0.522599 0.516678 0.146621 0.037 Uiso 1 1 calc R U . . .
C9 C 0.5255(2) 0.56785(13) 0.2636(3) 0.0260(8) Uani 1 1 d . . . . .
H9A H 0.474055 0.576743 0.246859 0.031 Uiso 1 1 calc R U . . .
C10 C 0.5757(2) 0.59017(12) 0.3475(3) 0.0228(8) Uani 1 1 d . . . . .
C11 C 0.49708(18) 0.65435(12) 0.4110(3) 0.0212(7) Uani 1 1 d . . . . .
H11A H 0.475684 0.657657 0.330570 0.025 Uiso 1 1 calc R U . . .
H11B H 0.510381 0.686361 0.439905 0.025 Uiso 1 1 calc R U . . .
C12 C 0.43498(19) 0.63622(12) 0.4703(3) 0.0215(7) Uani 1 1 d . . . . .
C13 C 0.3709(2) 0.66507(12) 0.4560(3) 0.0251(8) Uani 1 1 d . . . . .
C14 C 0.3662(2) 0.70878(14) 0.3827(3) 0.0334(9) Uani 1 1 d . . . . .
H14A H 0.316186 0.722995 0.377750 0.050 Uiso 1 1 calc R U . . .
H14B H 0.374771 0.700057 0.307448 0.050 Uiso 1 1 calc R U . . .
H14C H 0.404578 0.731452 0.415500 0.050 Uiso 1 1 calc R U . . .
C15 C 0.3107(2) 0.65457(14) 0.5098(3) 0.0314(9) Uani 1 1 d . . . . .
H15A H 0.267782 0.674471 0.498772 0.038 Uiso 1 1 calc R U . . .
C16 C 0.3117(2) 0.61575(15) 0.5794(3) 0.0357(10) Uani 1 1 d . . . . .
C17 C 0.2473(3) 0.6055(2) 0.6408(4) 0.0569(14) Uani 1 1 d . . . . .
H17A H 0.230709 0.572902 0.626718 0.085 Uiso 1 1 calc R U . . .
H17B H 0.205363 0.626863 0.614331 0.085 Uiso 1 1 calc R U . . .
H17C H 0.263792 0.610120 0.721429 0.085 Uiso 1 1 calc R U . . .
C18 C 0.3743(2) 0.58689(14) 0.5897(3) 0.0317(9) Uani 1 1 d . . . . .
H18A H 0.375017 0.559336 0.634268 0.038 Uiso 1 1 calc R U . . .
C19 C 0.4362(2) 0.59611(12) 0.5382(3) 0.0251(8) Uani 1 1 d . . . . .
C20 C 0.5009(2) 0.56099(13) 0.5598(3) 0.0315(9) Uani 1 1 d . . . . .
H20A H 0.490234 0.537444 0.614176 0.047 Uiso 1 1 calc R U . . .
H20B H 0.547605 0.577587 0.589598 0.047 Uiso 1 1 calc R U . . .
H20C H 0.506420 0.545354 0.489408 0.047 Uiso 1 1 calc R U . . .
C21 C 0.76473(19) 0.61272(12) 0.7315(3) 0.0226(8) Uani 1 1 d . . . . .
H21A H 0.803807 0.624995 0.695954 0.027 Uiso 1 1 calc R U . . .
C22 C 0.7779(2) 0.57124(13) 0.7937(3) 0.0275(8) Uani 1 1 d . . . . .
H22A H 0.824411 0.555156 0.797032 0.033 Uiso 1 1 calc R U . . .
C23 C 0.7245(2) 0.55391(13) 0.8492(3) 0.0317(9) Uani 1 1 d . . . . .
H23A H 0.733845 0.526094 0.892840 0.038 Uiso 1 1 calc R U . . .
C24 C 0.6550(2) 0.57749(12) 0.8418(3) 0.0261(8) Uani 1 1 d . . . . .
C25 C 0.5955(2) 0.56258(14) 0.8984(3) 0.0336(9) Uani 1 1 d . . . . .
H25A H 0.602119 0.535353 0.944466 0.040 Uiso 1 1 calc R U . . .
C26 C 0.5303(2) 0.58646(14) 0.8874(3) 0.0316(9) Uani 1 1 d . . . . .
H26A H 0.491777 0.575818 0.926292 0.038 Uiso 1 1 calc R U . . .
C27 C 0.5175(2) 0.62756(13) 0.8185(3) 0.0273(8) Uani 1 1 d . . . . .
C28 C 0.4507(2) 0.65404(15) 0.8043(3) 0.0313(9) Uani 1 1 d . . . . .
H28A H 0.411030 0.645571 0.843184 0.038 Uiso 1 1 calc R U . . .
C29 C 0.4433(2) 0.69208(15) 0.7342(3) 0.0324(10) Uani 1 1 d . . . . .
H29A H 0.398591 0.710353 0.725052 0.039 Uiso 1 1 calc R U . . .
C30 C 0.5016(2) 0.70422(13) 0.6757(3) 0.0268(8) Uani 1 1 d . . . . .
H30A H 0.495396 0.730644 0.626978 0.032 Uiso 1 1 calc R U . . .
C31 C 0.57415(19) 0.64242(12) 0.7596(3) 0.0213(7) Uani 1 1 d . . . . .
C32 C 0.64456(19) 0.61797(12) 0.7745(3) 0.0207(7) Uani 1 1 d . . . . .
C33 C 0.2618(2) 0.68880(12) 0.0112(3) 0.0291(9) Uani 1 1 d . . . . .
C34 C 0.1326(2) 0.73336(13) -0.0311(3) 0.0276(8) Uani 1 1 d . . . . .
C35 C 0.2106(2) 0.74150(13) 0.1760(3) 0.0315(9) Uani 1 1 d . . . . .
C36 C 0.13215(19) 0.62931(12) -0.0281(3) 0.0200(7) Uani 1 1 d . . . . .
C37 C 0.1410(2) 0.56358(12) -0.1328(3) 0.0227(8) Uani 1 1 d . . . . .
C38 C 0.1655(2) 0.52471(13) -0.1862(3) 0.0281(8) Uani 1 1 d . . . . .
H38A H 0.214382 0.511809 -0.164023 0.034 Uiso 1 1 calc R U . . .
C39 C 0.1150(2) 0.50580(13) -0.2735(3) 0.0325(9) Uani 1 1 d . . . . .
H39A H 0.129513 0.479393 -0.313079 0.039 Uiso 1 1 calc R U . . .
C40 C 0.0427(2) 0.52484(13) -0.3048(3) 0.0308(9) Uani 1 1 d . . . . .
H40A H 0.009680 0.511186 -0.365754 0.037 Uiso 1 1 calc R U . . .
C41 C 0.0181(2) 0.56276(13) -0.2497(3) 0.0278(8) Uani 1 1 d . . . . .
H41A H -0.031275 0.575116 -0.270124 0.033 Uiso 1 1 calc R U . . .
C42 C 0.0691(2) 0.58195(12) -0.1629(3) 0.0224(7) Uani 1 1 d . . . . .
C43 C -0.00032(18) 0.65210(12) -0.1080(3) 0.0215(7) Uani 1 1 d . . . . .
H43A H -0.020526 0.654489 -0.189056 0.026 Uiso 1 1 calc R U . . .
H43B H 0.017462 0.683870 -0.082576 0.026 Uiso 1 1 calc R U . . .
C44 C -0.06564(19) 0.63961(12) -0.0482(3) 0.0206(7) Uani 1 1 d . . . . .
C45 C -0.1238(2) 0.67279(12) -0.0648(3) 0.0231(8) Uani 1 1 d . . . . .
C46 C -0.1201(2) 0.71532(13) -0.1395(3) 0.0291(9) Uani 1 1 d . . . . .
H46A H -0.166554 0.733638 -0.143724 0.044 Uiso 1 1 calc R U . . .
H46B H -0.114336 0.704869 -0.214753 0.044 Uiso 1 1 calc R U . . .
H46C H -0.076972 0.734945 -0.108097 0.044 Uiso 1 1 calc R U . . .
C47 C -0.1871(2) 0.66728(13) -0.0138(3) 0.0272(8) Uani 1 1 d . . . . .
H47A H -0.226426 0.689859 -0.027569 0.033 Uiso 1 1 calc R U . . .
C48 C -0.1941(2) 0.62982(14) 0.0564(3) 0.0296(9) Uani 1 1 d . . . . .
C49 C -0.2612(2) 0.62473(17) 0.1151(4) 0.0462(12) Uani 1 1 d . . . . .
H49A H -0.246646 0.633145 0.194316 0.069 Uiso 1 1 calc R U . . .
H49B H -0.278871 0.592088 0.109210 0.069 Uiso 1 1 calc R U . . .
H49C H -0.301539 0.645647 0.080082 0.069 Uiso 1 1 calc R U . . .
C50 C -0.1360(2) 0.59716(13) 0.0719(3) 0.0289(9) Uani 1 1 d . . . . .
H50A H -0.140004 0.570972 0.119292 0.035 Uiso 1 1 calc R U . . .
C51 C -0.0719(2) 0.60085(12) 0.0214(3) 0.0234(8) Uani 1 1 d . . . . .
C52 C -0.0138(2) 0.56166(13) 0.0463(3) 0.0329(9) Uani 1 1 d . . . . .
H52A H -0.027625 0.540943 0.104410 0.049 Uiso 1 1 calc R U . . .
H52B H 0.035870 0.575397 0.072683 0.049 Uiso 1 1 calc R U . . .
H52C H -0.012302 0.543435 -0.021999 0.049 Uiso 1 1 calc R U . . .
C53 C 0.2716(2) 0.61061(13) 0.2230(3) 0.0249(8) Uani 1 1 d . . . . .
H53A H 0.311427 0.621497 0.187148 0.030 Uiso 1 1 calc R U . . .
C54 C 0.2841(2) 0.57097(13) 0.2929(3) 0.0297(9) Uani 1 1 d . . . . .
H54A H 0.331079 0.555101 0.301931 0.036 Uiso 1 1 calc R U . . .
C55 C 0.2289(2) 0.55542(14) 0.3474(3) 0.0328(9) Uani 1 1 d . . . . .
H55A H 0.236790 0.528457 0.394286 0.039 Uiso 1 1 calc R U . . .
C56 C 0.1598(2) 0.57969(13) 0.3338(3) 0.0285(8) Uani 1 1 d . . . . .
C57 C 0.0991(2) 0.56726(15) 0.3909(4) 0.0365(10) Uani 1 1 d . . . . .
H57A H 0.104386 0.540958 0.440010 0.044 Uiso 1 1 calc R U . . .
C58 C 0.0346(2) 0.59227(15) 0.3761(3) 0.0372(10) Uani 1 1 d . . . . .
H58A H -0.004696 0.583412 0.415367 0.045 Uiso 1 1 calc R U . . .
C59 C 0.0243(2) 0.63207(14) 0.3019(3) 0.0311(9) Uani 1 1 d . . . . .
C60 C -0.0411(2) 0.65980(15) 0.2845(4) 0.0358(10) Uani 1 1 d . . . . .
H60A H -0.081612 0.652905 0.323083 0.043 Uiso 1 1 calc R U . . .
C61 C -0.0459(2) 0.69667(16) 0.2118(4) 0.0363(10) Uani 1 1 d . . . . .
H61A H -0.089690 0.715887 0.200809 0.044 Uiso 1 1 calc R U . . .
C62 C 0.0132(2) 0.70654(14) 0.1530(3) 0.0298(9) Uani 1 1 d . . . . .
H62A H 0.008943 0.732409 0.102604 0.036 Uiso 1 1 calc R U . . .
C63 C 0.0817(2) 0.64418(13) 0.2428(3) 0.0241(8) Uani 1 1 d . . . . .
C64 C 0.1509(2) 0.61849(12) 0.2605(3) 0.0224(8) Uani 1 1 d . . . . .
C65 C 0.5148(4) 0.66866(19) 0.1104(5) 0.0739(19) Uani 1 1 d . . . . .
H65A H 0.545320 0.686838 0.170111 0.111 Uiso 1 1 calc R U . . .
H65B H 0.508957 0.686487 0.040123 0.111 Uiso 1 1 calc R U . . .
H65C H 0.539707 0.638646 0.100850 0.111 Uiso 1 1 calc R U . . .
C66 C 1.0503(3) 0.66688(17) 0.6107(4) 0.0486(12) Uani 1 1 d . . . . .
H66A H 1.064108 0.675571 0.538402 0.073 Uiso 1 1 calc R U . . .
H66B H 1.057026 0.632924 0.622363 0.073 Uiso 1 1 calc R U . . .
H66C H 1.082618 0.683816 0.670955 0.073 Uiso 1 1 calc R U . . .
H8 H 0.943(3) 0.653(2) 0.579(5) 0.10(2) Uiso 1 1 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
Re1 C3 1.912(4) . ?
Re1 C1 1.920(4) . ?
Re1 C2 1.951(4) . ?
Re1 N3 2.180(3) . ?
Re1 C4 2.182(3) . ?
Re1 N4 2.189(3) . ?
N1 C4 1.354(4) . ?
N1 C5 1.388(4) . ?
N1 H1A 0.8800 . ?
O1 C1 1.143(5) . ?
Re2 C34 1.909(4) . ?
Re2 C33 1.934(4) . ?
Re2 C35 1.955(4) . ?
Re2 C36 2.182(3) . ?
Re2 N7 2.186(3) . ?
Re2 N8 2.189(3) . ?
O2 C2 1.152(4) . ?
N2 C4 1.359(4) . ?
N2 C10 1.392(4) . ?
N2 C11 1.461(4) . ?
N3 C21 1.336(4) . ?
N3 C32 1.369(4) . ?
O3 C3 1.155(4) . ?
O4 C33 1.151(5) . ?
N4 C30 1.344(4) . ?
N4 C31 1.363(4) . ?
N5 C36 1.354(4) . ?
N5 C37 1.400(4) . ?
N5 H5A 0.8800 . ?
O5 C34 1.159(4) . ?
C5 C10 1.384(5) . ?
C5 C6 1.388(5) . ?
O6 C35 1.147(4) . ?
N6 C36 1.362(4) . ?
N6 C42 1.394(4) . ?
N6 C43 1.453(4) . ?
C6 C7 1.378(5) . ?
C6 H6A 0.9500 . ?
N7 C53 1.326(4) . ?
N7 C64 1.366(4) . ?
C7 C8 1.395(5) . ?
C7 H7A 0.9500 . ?
O7 C65 1.393(7) . ?
O7 H7 0.8400 . ?
N8 C62 1.343(5) . ?
N8 C63 1.365(5) . ?
O8 C66 1.402(6) . ?
O8 H8 0.98(6) . ?
C8 C9 1.383(5) . ?
C8 H8A 0.9500 . ?
C9 C10 1.395(5) . ?
C9 H9A 0.9500 . ?
C11 C12 1.516(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C19 1.403(5) . ?
C12 C13 1.404(5) . ?
C13 C15 1.386(5) . ?
C13 C14 1.521(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.386(6) . ?
C15 H15A 0.9500 . ?
C16 C18 1.384(6) . ?
C16 C17 1.507(6) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.390(5) . ?
C18 H18A 0.9500 . ?
C19 C20 1.523(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.398(5) . ?
C21 H21A 0.9500 . ?
C22 C23 1.354(5) . ?
C22 H22A 0.9500 . ?
C23 C24 1.411(5) . ?
C23 H23A 0.9500 . ?
C24 C32 1.404(5) . ?
C24 C25 1.428(5) . ?
C25 C26 1.344(6) . ?
C25 H25A 0.9500 . ?
C26 C27 1.432(5) . ?
C26 H26A 0.9500 . ?
C27 C31 1.403(5) . ?
C27 C28 1.405(5) . ?
C28 C29 1.367(6) . ?
C28 H28A 0.9500 . ?
C29 C30 1.402(6) . ?
C29 H29A 0.9500 . ?
C30 H30A 0.9500 . ?
C31 C32 1.431(5) . ?
C37 C42 1.388(5) . ?
C37 C38 1.389(5) . ?
C38 C39 1.384(5) . ?
C38 H38A 0.9500 . ?
C39 C40 1.403(6) . ?
C39 H39A 0.9500 . ?
C40 C41 1.379(5) . ?
C40 H40A 0.9500 . ?
C41 C42 1.387(5) . ?
C41 H41A 0.9500 . ?
C43 C44 1.522(5) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 C45 1.399(5) . ?
C44 C51 1.403(5) . ?
C45 C47 1.394(5) . ?
C45 C46 1.517(5) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 C48 1.380(5) . ?
C47 H47A 0.9500 . ?
C48 C50 1.388(5) . ?
C48 C49 1.507(5) . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 C51 1.397(5) . ?
C50 H50A 0.9500 . ?
C51 C52 1.524(5) . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 C54 1.405(5) . ?
C53 H53A 0.9500 . ?
C54 C55 1.354(6) . ?
C54 H54A 0.9500 . ?
C55 C56 1.410(5) . ?
C55 H55A 0.9500 . ?
C56 C64 1.408(5) . ?
C56 C57 1.430(5) . ?
C57 C58 1.349(6) . ?
C57 H57A 0.9500 . ?
C58 C59 1.437(6) . ?
C58 H58A 0.9500 . ?
C59 C63 1.396(5) . ?
C59 C60 1.404(5) . ?
C60 C61 1.362(6) . ?
C60 H60A 0.9500 . ?
C61 C62 1.405(6) . ?
C61 H61A 0.9500 . ?
C62 H62A 0.9500 . ?
C63 C64 1.429(5) . ?
C65 H65A 0.9800 . ?
C65 H65B 0.9800 . ?
C65 H65C 0.9800 . ?
C66 H66A 0.9800 . ?
C66 H66B 0.9800 . ?
C66 H66C 0.9800 . ?

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
C3 Re1 C1 87.41(16) . . ?
C3 Re1 C2 88.70(16) . . ?
C1 Re1 C2 89.41(16) . . ?
C3 Re1 N3 173.28(13) . . ?
C1 Re1 N3 96.56(13) . . ?
C2 Re1 N3 96.74(13) . . ?
C3 Re1 C4 91.54(15) . . ?
C1 Re1 C4 90.68(15) . . ?
C2 Re1 C4 179.74(14) . . ?
N3 Re1 C4 83.01(12) . . ?
C3 Re1 N4 100.78(14) . . ?
C1 Re1 N4 171.54(13) . . ?
C2 Re1 N4 88.64(13) . . ?
N3 Re1 N4 75.50(11) . . ?
C4 Re1 N4 91.24(12) . . ?
C4 N1 C5 112.1(3) . . ?
C4 N1 H1A 123.9 . . ?
C5 N1 H1A 123.9 . . ?
O1 C1 Re1 177.9(4) . . ?
C34 Re2 C33 86.19(16) . . ?
C34 Re2 C35 87.51(15) . . ?
C33 Re2 C35 90.95(17) . . ?
C34 Re2 C36 92.39(14) . . ?
C33 Re2 C36 87.79(15) . . ?
C35 Re2 C36 178.74(16) . . ?
C34 Re2 N7 173.97(13) . . ?
C33 Re2 N7 98.23(13) . . ?
C35 Re2 N7 96.48(13) . . ?
C36 Re2 N7 83.72(12) . . ?
C34 Re2 N8 100.05(14) . . ?
C33 Re2 N8 173.29(13) . . ?
C35 Re2 N8 91.79(15) . . ?
C36 Re2 N8 89.47(12) . . ?
N7 Re2 N8 75.37(11) . . ?
C4 N2 C10 111.1(3) . . ?
C4 N2 C11 125.7(3) . . ?
C10 N2 C11 122.9(3) . . ?
O2 C2 Re1 176.2(3) . . ?
C21 N3 C32 117.6(3) . . ?
C21 N3 Re1 126.9(2) . . ?
C32 N3 Re1 115.1(2) . . ?
O3 C3 Re1 177.8(3) . . ?
C30 N4 C31 118.0(3) . . ?
C30 N4 Re1 126.8(3) . . ?
C31 N4 Re1 115.1(2) . . ?
N1 C4 N2 104.8(3) . . ?
N1 C4 Re1 123.5(2) . . ?
N2 C4 Re1 131.6(2) . . ?
C36 N5 C37 111.6(3) . . ?
C36 N5 H5A 124.2 . . ?
C37 N5 H5A 124.2 . . ?
C10 C5 N1 105.5(3) . . ?
C10 C5 C6 121.9(3) . . ?
N1 C5 C6 132.6(3) . . ?
C36 N6 C42 110.9(3) . . ?
C36 N6 C43 125.9(3) . . ?
C42 N6 C43 122.9(3) . . ?
C7 C6 C5 116.7(3) . . ?
C7 C6 H6A 121.6 . . ?
C5 C6 H6A 121.6 . . ?
C53 N7 C64 117.8(3) . . ?
C53 N7 Re2 127.2(2) . . ?
C64 N7 Re2 114.7(2) . . ?
C6 C7 C8 121.7(4) . . ?
C6 C7 H7A 119.1 . . ?
C8 C7 H7A 119.1 . . ?
C65 O7 H7 109.5 . . ?
C62 N8 C63 118.3(3) . . ?
C62 N8 Re2 126.6(3) . . ?
C63 N8 Re2 115.1(2) . . ?
C66 O8 H8 109(4) . . ?
C9 C8 C7 121.6(3) . . ?
C9 C8 H8A 119.2 . . ?
C7 C8 H8A 119.2 . . ?
C8 C9 C10 116.6(3) . . ?
C8 C9 H9A 121.7 . . ?
C10 C9 H9A 121.7 . . ?
C5 C10 N2 106.5(3) . . ?
C5 C10 C9 121.4(3) . . ?
N2 C10 C9 132.1(3) . . ?
N2 C11 C12 119.5(3) . . ?
N2 C11 H11A 107.4 . . ?
C12 C11 H11A 107.4 . . ?
N2 C11 H11B 107.4 . . ?
C12 C11 H11B 107.4 . . ?
H11A C11 H11B 107.0 . . ?
C19 C12 C13 118.6(3) . . ?
C19 C12 C11 127.7(3) . . ?
C13 C12 C11 113.6(3) . . ?
C15 C13 C12 120.5(4) . . ?
C15 C13 C14 118.6(3) . . ?
C12 C13 C14 120.9(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 C16 121.7(4) . . ?
C13 C15 H15A 119.2 . . ?
C16 C15 H15A 119.2 . . ?
C18 C16 C15 117.0(4) . . ?
C18 C16 C17 121.6(4) . . ?
C15 C16 C17 121.3(4) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 C19 123.4(4) . . ?
C16 C18 H18A 118.3 . . ?
C19 C18 H18A 118.3 . . ?
C18 C19 C12 118.7(3) . . ?
C18 C19 C20 116.6(3) . . ?
C12 C19 C20 124.8(3) . . ?
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 . . ?
N3 C21 C22 122.4(3) . . ?
N3 C21 H21A 118.8 . . ?
C22 C21 H21A 118.8 . . ?
C23 C22 C21 120.2(3) . . ?
C23 C22 H22A 119.9 . . ?
C21 C22 H22A 119.9 . . ?
C22 C23 C24 119.5(3) . . ?
C22 C23 H23A 120.3 . . ?
C24 C23 H23A 120.3 . . ?
C32 C24 C23 117.3(3) . . ?
C32 C24 C25 118.8(4) . . ?
C23 C24 C25 123.9(3) . . ?
C26 C25 C24 121.1(4) . . ?
C26 C25 H25A 119.5 . . ?
C24 C25 H25A 119.5 . . ?
C25 C26 C27 121.5(4) . . ?
C25 C26 H26A 119.2 . . ?
C27 C26 H26A 119.2 . . ?
C31 C27 C28 117.2(4) . . ?
C31 C27 C26 118.8(3) . . ?
C28 C27 C26 124.0(4) . . ?
C29 C28 C27 119.5(4) . . ?
C29 C28 H28A 120.2 . . ?
C27 C28 H28A 120.2 . . ?
C28 C29 C30 120.3(4) . . ?
C28 C29 H29A 119.9 . . ?
C30 C29 H29A 119.9 . . ?
N4 C30 C29 121.6(4) . . ?
N4 C30 H30A 119.2 . . ?
C29 C30 H30A 119.2 . . ?
N4 C31 C27 123.3(3) . . ?
N4 C31 C32 117.1(3) . . ?
C27 C31 C32 119.6(3) . . ?
N3 C32 C24 122.9(3) . . ?
N3 C32 C31 117.0(3) . . ?
C24 C32 C31 120.1(3) . . ?
O4 C33 Re2 178.1(4) . . ?
O5 C34 Re2 177.6(4) . . ?
O6 C35 Re2 175.2(4) . . ?
N5 C36 N6 105.4(3) . . ?
N5 C36 Re2 122.8(2) . . ?
N6 C36 Re2 131.5(2) . . ?
C42 C37 C38 122.2(3) . . ?
C42 C37 N5 105.4(3) . . ?
C38 C37 N5 132.4(3) . . ?
C39 C38 C37 116.4(4) . . ?
C39 C38 H38A 121.8 . . ?
C37 C38 H38A 121.8 . . ?
C38 C39 C40 121.3(4) . . ?
C38 C39 H39A 119.3 . . ?
C40 C39 H39A 119.3 . . ?
C41 C40 C39 122.0(4) . . ?
C41 C40 H40A 119.0 . . ?
C39 C40 H40A 119.0 . . ?
C40 C41 C42 116.6(3) . . ?
C40 C41 H41A 121.7 . . ?
C42 C41 H41A 121.7 . . ?
C41 C42 C37 121.5(3) . . ?
C41 C42 N6 131.7(3) . . ?
C37 C42 N6 106.6(3) . . ?
N6 C43 C44 119.2(3) . . ?
N6 C43 H43A 107.5 . . ?
C44 C43 H43A 107.5 . . ?
N6 C43 H43B 107.5 . . ?
C44 C43 H43B 107.5 . . ?
H43A C43 H43B 107.0 . . ?
C45 C44 C51 118.9(3) . . ?
C45 C44 C43 113.2(3) . . ?
C51 C44 C43 127.9(3) . . ?
C47 C45 C44 120.6(3) . . ?
C47 C45 C46 118.2(3) . . ?
C44 C45 C46 121.2(3) . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C48 C47 C45 121.6(3) . . ?
C48 C47 H47A 119.2 . . ?
C45 C47 H47A 119.2 . . ?
C47 C48 C50 117.1(3) . . ?
C47 C48 C49 121.7(4) . . ?
C50 C48 C49 121.2(4) . . ?
C48 C49 H49A 109.5 . . ?
C48 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C48 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C48 C50 C51 123.4(4) . . ?
C48 C50 H50A 118.3 . . ?
C51 C50 H50A 118.3 . . ?
C50 C51 C44 118.4(3) . . ?
C50 C51 C52 116.7(3) . . ?
C44 C51 C52 124.9(3) . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
N7 C53 C54 122.8(4) . . ?
N7 C53 H53A 118.6 . . ?
C54 C53 H53A 118.6 . . ?
C55 C54 C53 119.9(4) . . ?
C55 C54 H54A 120.1 . . ?
C53 C54 H54A 120.1 . . ?
C54 C55 C56 119.3(4) . . ?
C54 C55 H55A 120.4 . . ?
C56 C55 H55A 120.4 . . ?
C64 C56 C55 117.6(4) . . ?
C64 C56 C57 118.8(4) . . ?
C55 C56 C57 123.6(4) . . ?
C58 C57 C56 121.1(4) . . ?
C58 C57 H57A 119.5 . . ?
C56 C57 H57A 119.5 . . ?
C57 C58 C59 121.2(4) . . ?
C57 C58 H58A 119.4 . . ?
C59 C58 H58A 119.4 . . ?
C63 C59 C60 117.4(4) . . ?
C63 C59 C58 118.9(4) . . ?
C60 C59 C58 123.7(4) . . ?
C61 C60 C59 119.4(4) . . ?
C61 C60 H60A 120.3 . . ?
C59 C60 H60A 120.3 . . ?
C60 C61 C62 120.6(4) . . ?
C60 C61 H61A 119.7 . . ?
C62 C61 H61A 119.7 . . ?
N8 C62 C61 121.1(4) . . ?
N8 C62 H62A 119.5 . . ?
C61 C62 H62A 119.5 . . ?
N8 C63 C59 123.2(3) . . ?
N8 C63 C64 116.9(3) . . ?
C59 C63 C64 120.0(3) . . ?
N7 C64 C56 122.7(3) . . ?
N7 C64 C63 117.3(3) . . ?
C56 C64 C63 120.0(3) . . ?
O7 C65 H65A 109.5 . . ?
O7 C65 H65B 109.5 . . ?
H65A C65 H65B 109.5 . . ?
O7 C65 H65C 109.5 . . ?
H65A C65 H65C 109.5 . . ?
H65B C65 H65C 109.5 . . ?
O8 C66 H66A 109.5 . . ?
O8 C66 H66B 109.5 . . ?
H66A C66 H66B 109.5 . . ?
O8 C66 H66C 109.5 . . ?
H66A C66 H66C 109.5 . . ?
H66B C66 H66C 109.5 . . ?

_refine_diff_density_max         2.907
_refine_diff_density_min         -1.023
_refine_diff_density_rms         0.122

####################################################################### 
# 
# 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_3c
_database_code_depnum_ccdc_archive 'CCDC 1504037'
_audit_update_record             
;
2017-09-29 deposited with the CCDC.
2017-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H18 Br N2 O4 Re'
_chemical_formula_weight         628.48

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.8757(5)
_cell_length_b                   19.1959(5)
_cell_length_c                   7.0599(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.732(2)
_cell_angle_gamma                90
_cell_volume                     2150.51(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4925
_cell_measurement_theta_min      3.076
_cell_measurement_theta_max      27.496

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.941
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    7.537
_shelx_estimated_absorpt_T_min   0.398
_shelx_estimated_absorpt_T_max   0.519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72052
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Oxford Xcalibur2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21527
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.076
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4925
_reflns_number_gt                4628
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'SHELXS (Sheldrick)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'CIFTAB (Sheldrick)'
_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)+(0.0230P)²+2.1102P] 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         4925
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0209
_refine_ls_wR_factor_ref         0.0514
_refine_ls_wR_factor_gt          0.0501
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Re1 Re 0.15255(2) -0.10912(2) 0.79417(2) 0.02174(5) Uani 1 1 d . . . . .
Br1 Br 0.08040(2) -0.07630(2) 1.11409(4) 0.02743(7) Uani 1 1 d . . . . .
O1 O 0.31436(16) -0.14292(18) 1.0400(4) 0.0544(7) Uani 1 1 d . . . . .
O3 O 0.07995(18) -0.25706(13) 0.8642(4) 0.0493(7) Uani 1 1 d . . . . .
O2 O 0.24639(18) -0.15655(15) 0.4456(4) 0.0487(7) Uani 1 1 d . . . . .
O4 O -0.01625(17) -0.08055(16) 0.5644(4) 0.0491(7) Uani 1 1 d . . . . .
N1 N 0.12601(16) 0.04998(13) 0.8315(4) 0.0251(5) Uani 1 1 d . . . . .
H1 H 0.073604 0.040359 0.859166 0.030 Uiso 1 1 calc R U . . .
N2 N 0.25443(15) 0.03776(12) 0.7455(3) 0.0214(5) Uani 1 1 d . . . . .
C1 C 0.2560(2) -0.12989(18) 0.9513(5) 0.0315(7) Uani 1 1 d . . . . .
C3 C 0.1091(2) -0.20413(16) 0.8359(5) 0.0300(7) Uani 1 1 d . . . . .
C2 C 0.2099(2) -0.13742(18) 0.5730(5) 0.0333(7) Uani 1 1 d . . . . .
C4 C 0.0447(2) -0.08878(17) 0.6446(5) 0.0290(6) Uani 1 1 d . . . . .
C5 C 0.18309(18) 0.00153(15) 0.7828(4) 0.0226(6) Uani 1 1 d . . . . .
C6 C 0.15956(19) 0.11652(15) 0.8328(4) 0.0239(6) Uani 1 1 d . . . . .
C7 C 0.1243(2) 0.18055(17) 0.8800(5) 0.0314(7) Uani 1 1 d . . . . .
H7 H 0.066990 0.184718 0.913085 0.038 Uiso 1 1 calc R U . . .
C8 C 0.1772(2) 0.23742(17) 0.8761(5) 0.0344(7) Uani 1 1 d . . . . .
H8 H 0.156271 0.282055 0.908845 0.041 Uiso 1 1 calc R U . . .
C9 C 0.2611(2) 0.23051(17) 0.8247(5) 0.0336(7) Uani 1 1 d . . . . .
H9 H 0.295858 0.270808 0.825009 0.040 Uiso 1 1 calc R U . . .
C10 C 0.2956(2) 0.16744(16) 0.7734(4) 0.0274(6) Uani 1 1 d . . . . .
H10 H 0.352551 0.163759 0.737013 0.033 Uiso 1 1 calc R U . . .
C11 C 0.24258(19) 0.10918(14) 0.7777(4) 0.0220(6) Uani 1 1 d . . . . .
C12 C 0.33328(18) 0.00546(16) 0.6821(4) 0.0263(6) Uani 1 1 d . . . . .
H12A H 0.319709 -0.039503 0.619671 0.032 Uiso 1 1 calc R U . . .
H12B H 0.370292 -0.004401 0.794292 0.032 Uiso 1 1 calc R U . . .
C13 C 0.38035(18) 0.05089(15) 0.5462(4) 0.0225(6) Uani 1 1 d . . . . .
C14 C 0.3421(2) 0.06948(16) 0.3713(4) 0.0275(6) Uani 1 1 d . . . . .
C15 C 0.2578(2) 0.0414(2) 0.3074(5) 0.0441(9) Uani 1 1 d . . . . .
H15A H 0.236600 0.009917 0.404423 0.066 Uiso 1 1 calc R U . . .
H15B H 0.218151 0.080019 0.287702 0.066 Uiso 1 1 calc R U . . .
H15C H 0.263476 0.015776 0.188349 0.066 Uiso 1 1 calc R U . . .
C16 C 0.3841(2) 0.11569(17) 0.2538(5) 0.0342(8) Uani 1 1 d . . . . .
H16 H 0.358662 0.128211 0.135081 0.041 Uiso 1 1 calc R U . . .
C17 C 0.4616(2) 0.14368(17) 0.3054(5) 0.0371(8) Uani 1 1 d . . . . .
C18 C 0.5027(3) 0.1976(2) 0.1809(7) 0.0632(14) Uani 1 1 d . . . . .
H18A H 0.557020 0.211626 0.238851 0.095 Uiso 1 1 calc R U . . .
H18B H 0.511799 0.177635 0.055470 0.095 Uiso 1 1 calc R U . . .
H18C H 0.465951 0.238459 0.168166 0.095 Uiso 1 1 calc R U . . .
C19 C 0.5006(2) 0.12234(16) 0.4748(5) 0.0340(8) Uani 1 1 d . . . . .
H19 H 0.555068 0.139722 0.508621 0.041 Uiso 1 1 calc R U . . .
C20 C 0.46120(18) 0.07573(15) 0.5962(4) 0.0248(6) Uani 1 1 d . . . . .
C21 C 0.5052(2) 0.05613(19) 0.7809(5) 0.0364(8) Uani 1 1 d . . . . .
H21A H 0.559070 0.080942 0.792796 0.055 Uiso 1 1 calc R U . . .
H21B H 0.515493 0.005797 0.783242 0.055 Uiso 1 1 calc R U . . .
H21C H 0.469695 0.068929 0.886526 0.055 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 C2 1.911(3) . ?
Re1 C3 1.975(3) . ?
Re1 C1 1.995(3) . ?
Re1 C4 2.022(3) . ?
Re1 C5 2.181(3) . ?
Re1 Br1 2.6394(3) . ?
O1 C1 1.130(4) . ?
O3 C3 1.137(4) . ?
O2 C2 1.144(4) . ?
O4 C4 1.117(4) . ?
N1 C5 1.350(4) . ?
N1 C6 1.384(4) . ?
N1 H1 0.8800 . ?
N2 C5 1.361(4) . ?
N2 C11 1.403(4) . ?
N2 C12 1.478(4) . ?
C6 C11 1.393(4) . ?
C6 C7 1.395(4) . ?
C7 C8 1.378(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.398(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.401(4) . ?
C10 H10 0.9500 . ?
C12 C13 1.511(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.405(4) . ?
C13 C20 1.404(4) . ?
C14 C16 1.398(5) . ?
C14 C15 1.500(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.382(5) . ?
C16 H16 0.9500 . ?
C17 C19 1.391(5) . ?
C17 C18 1.518(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.400(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.508(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C2 Re1 C3 92.09(14) . . ?
C2 Re1 C1 89.59(14) . . ?
C3 Re1 C1 91.02(13) . . ?
C2 Re1 C4 92.58(14) . . ?
C3 Re1 C4 87.84(13) . . ?
C1 Re1 C4 177.59(13) . . ?
C2 Re1 C5 97.74(13) . . ?
C3 Re1 C5 169.73(12) . . ?
C1 Re1 C5 92.00(12) . . ?
C4 Re1 C5 88.76(12) . . ?
C2 Re1 Br1 175.84(11) . . ?
C3 Re1 Br1 86.01(10) . . ?
C1 Re1 Br1 86.75(9) . . ?
C4 Re1 Br1 91.05(9) . . ?
C5 Re1 Br1 84.36(7) . . ?
C5 N1 C6 112.1(2) . . ?
C5 N1 H1 123.9 . . ?
C6 N1 H1 123.9 . . ?
C5 N2 C11 110.6(2) . . ?
C5 N2 C12 124.1(2) . . ?
C11 N2 C12 125.3(2) . . ?
O1 C1 Re1 178.7(3) . . ?
O3 C3 Re1 175.9(3) . . ?
O2 C2 Re1 176.8(3) . . ?
O4 C4 Re1 176.7(3) . . ?
N1 C5 N2 105.4(2) . . ?
N1 C5 Re1 120.7(2) . . ?
N2 C5 Re1 133.8(2) . . ?
N1 C6 C11 105.8(3) . . ?
N1 C6 C7 131.1(3) . . ?
C11 C6 C7 123.1(3) . . ?
C8 C7 C6 116.4(3) . . ?
C8 C7 H7 121.8 . . ?
C6 C7 H7 121.8 . . ?
C7 C8 C9 121.1(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C8 122.7(3) . . ?
C10 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
C9 C10 C11 116.8(3) . . ?
C9 C10 H10 121.6 . . ?
C11 C10 H10 121.6 . . ?
C6 C11 C10 120.0(3) . . ?
C6 C11 N2 106.1(2) . . ?
C10 C11 N2 133.9(3) . . ?
N2 C12 C13 112.9(2) . . ?
N2 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
N2 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C20 120.1(3) . . ?
C14 C13 C12 119.7(3) . . ?
C20 C13 C12 120.2(3) . . ?
C16 C14 C13 118.8(3) . . ?
C16 C14 C15 119.2(3) . . ?
C13 C14 C15 122.0(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C14 121.8(3) . . ?
C17 C16 H16 119.1 . . ?
C14 C16 H16 119.1 . . ?
C16 C17 C19 118.8(3) . . ?
C16 C17 C18 120.5(4) . . ?
C19 C17 C18 120.7(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 C20 121.2(3) . . ?
C17 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C19 C20 C13 119.1(3) . . ?
C19 C20 C21 119.0(3) . . ?
C13 C20 C21 121.9(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C6 N1 C5 N2 -2.0(3) . . . . ?
C6 N1 C5 Re1 174.2(2) . . . . ?
C11 N2 C5 N1 2.1(3) . . . . ?
C12 N2 C5 N1 -178.6(2) . . . . ?
C11 N2 C5 Re1 -173.4(2) . . . . ?
C12 N2 C5 Re1 6.0(4) . . . . ?
C5 N1 C6 C11 1.2(3) . . . . ?
C5 N1 C6 C7 -177.6(3) . . . . ?
N1 C6 C7 C8 176.5(3) . . . . ?
C11 C6 C7 C8 -2.2(5) . . . . ?
C6 C7 C8 C9 0.9(5) . . . . ?
C7 C8 C9 C10 0.7(5) . . . . ?
C8 C9 C10 C11 -1.0(5) . . . . ?
N1 C6 C11 C10 -177.0(3) . . . . ?
C7 C6 C11 C10 2.0(5) . . . . ?
N1 C6 C11 N2 0.1(3) . . . . ?
C7 C6 C11 N2 179.1(3) . . . . ?
C9 C10 C11 C6 -0.3(4) . . . . ?
C9 C10 C11 N2 -176.5(3) . . . . ?
C5 N2 C11 C6 -1.4(3) . . . . ?
C12 N2 C11 C6 179.3(3) . . . . ?
C5 N2 C11 C10 175.1(3) . . . . ?
C12 N2 C11 C10 -4.2(5) . . . . ?
C5 N2 C12 C13 145.6(3) . . . . ?
C11 N2 C12 C13 -35.1(4) . . . . ?
N2 C12 C13 C14 -61.5(4) . . . . ?
N2 C12 C13 C20 117.0(3) . . . . ?
C20 C13 C14 C16 -3.3(4) . . . . ?
C12 C13 C14 C16 175.3(3) . . . . ?
C20 C13 C14 C15 176.8(3) . . . . ?
C12 C13 C14 C15 -4.6(4) . . . . ?
C13 C14 C16 C17 -0.4(5) . . . . ?
C15 C14 C16 C17 179.6(3) . . . . ?
C14 C16 C17 C19 3.4(5) . . . . ?
C14 C16 C17 C18 -175.7(3) . . . . ?
C16 C17 C19 C20 -2.8(5) . . . . ?
C18 C17 C19 C20 176.2(3) . . . . ?
C17 C19 C20 C13 -0.7(4) . . . . ?
C17 C19 C20 C21 -178.1(3) . . . . ?
C14 C13 C20 C19 3.8(4) . . . . ?
C12 C13 C20 C19 -174.8(3) . . . . ?
C14 C13 C20 C21 -178.9(3) . . . . ?
C12 C13 C20 C21 2.5(4) . . . . ?

_refine_diff_density_max         1.072
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.096

####################################################################### 
# 
# 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_4b
_database_code_depnum_ccdc_archive 'CCDC 1504040'
_audit_update_record             
;
2017-10-04 deposited with the CCDC.
2017-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H22 Br Cl2 N4 O3 Re'
_chemical_formula_weight         799.50

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'
Br Br -0.2901 2.4595 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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                   28.4252(15)
_cell_length_b                   8.7539(5)
_cell_length_c                   23.4708(14)
_cell_angle_alpha                90
_cell_angle_beta                 93.646(5)
_cell_angle_gamma                90
_cell_volume                     5828.5(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    12733
_cell_measurement_theta_min      3.4090
_cell_measurement_theta_max      32.0120

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.822
_exptl_crystal_F_000             3088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    5.760
_shelx_estimated_absorpt_T_min   0.277
_shelx_estimated_absorpt_T_max   0.597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.53436
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27340
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.872
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6666
_reflns_number_gt                5650
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'SHELXS (Sheldrick 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'CIFTAB (sheldrick)'
_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)+(0.0216P)²] 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         6666
_refine_ls_number_parameters     380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0732
_refine_ls_wR_factor_gt          0.0669
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.133
_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 0.09271(2) 0.18185(2) -0.00385(2) 0.03176(6) Uani 1 1 d . . . . .
N1 N 0.15787(13) 0.1746(4) 0.10857(14) 0.0379(8) Uani 1 1 d . . . . .
H1A H 0.168039 0.084955 0.097691 0.045 Uiso 1 1 calc R U . . .
C1 C 0.03115(18) 0.2569(5) 0.00971(18) 0.0417(11) Uani 1 1 d . . . . .
O1 O -0.00596(13) 0.3039(5) 0.01475(16) 0.0678(11) Uani 1 1 d . . . . .
Br1 Br 0.19760(2) 0.82268(6) 0.11564(2) 0.05782(15) Uani 1 1 d . . . . .
N2 N 0.12066(13) 0.3883(4) 0.10920(13) 0.0371(8) Uani 1 1 d . . . . .
C2 C 0.06473(17) 0.0884(5) -0.07442(19) 0.0419(11) Uani 1 1 d . . . . .
O2 O 0.04697(14) 0.0257(4) -0.11218(14) 0.0695(11) Uani 1 1 d . . . . .
N3 N 0.11866(13) 0.3849(4) -0.04588(13) 0.0341(8) Uani 1 1 d . . . . .
C3 C 0.07768(17) -0.0004(6) 0.03685(18) 0.0450(11) Uani 1 1 d . . . . .
O3 O 0.06887(15) -0.1084(5) 0.06116(16) 0.0774(12) Uani 1 1 d . . . . .
C4 C 0.12582(15) 0.2614(5) 0.07754(16) 0.0332(9) Uani 1 1 d . . . . .
N4 N 0.16397(12) 0.1244(4) -0.02736(13) 0.0327(8) Uani 1 1 d . . . . .
C6 C 0.2049(2) 0.2028(7) 0.2038(2) 0.0617(15) Uani 1 1 d . . . . .
H6A H 0.221500 0.108768 0.202928 0.074 Uiso 1 1 calc R U . . .
C7 C 0.2115(2) 0.3038(8) 0.2489(2) 0.0741(19) Uani 1 1 d . . . . .
H7A H 0.233155 0.278947 0.280096 0.089 Uiso 1 1 calc R U . . .
C8 C 0.1871(2) 0.4404(8) 0.2492(2) 0.0747(19) Uani 1 1 d . . . . .
H8A H 0.192556 0.506906 0.280934 0.090 Uiso 1 1 calc R U . . .
C9 C 0.1551(2) 0.4849(6) 0.20521(19) 0.0576(14) Uani 1 1 d . . . . .
H9A H 0.138499 0.579058 0.205850 0.069 Uiso 1 1 calc R U . . .
C10 C 0.14888(17) 0.3826(5) 0.16033(17) 0.0416(11) Uani 1 1 d . . . . .
C11 C 0.08627(17) 0.5105(5) 0.09739(17) 0.0412(11) Uani 1 1 d . . . . .
H11A H 0.076005 0.508996 0.056289 0.049 Uiso 1 1 calc R U . . .
H11B H 0.101592 0.610259 0.105845 0.049 Uiso 1 1 calc R U . . .
C12 C 0.04324(17) 0.4956(5) 0.13230(16) 0.0415(11) Uani 1 1 d . . . . .
C13 C 0.02700(19) 0.3561(6) 0.14931(18) 0.0499(12) Uani 1 1 d . . . . .
H13A H 0.043786 0.265858 0.140891 0.060 Uiso 1 1 calc R U . . .
C14 C -0.0135(2) 0.3460(7) 0.1785(2) 0.0633(15) Uani 1 1 d . . . . .
H14A H -0.024489 0.248757 0.189739 0.076 Uiso 1 1 calc R U . . .
C15 C -0.0380(2) 0.4746(9) 0.1915(2) 0.0696(18) Uani 1 1 d . . . . .
H15A H -0.065897 0.466901 0.211598 0.084 Uiso 1 1 calc R U . . .
C16 C -0.0220(2) 0.6140(8) 0.1754(2) 0.0739(19) Uani 1 1 d . . . . .
H16A H -0.038798 0.703666 0.184550 0.089 Uiso 1 1 calc R U . . .
C17 C 0.0186(2) 0.6261(6) 0.14561(19) 0.0569(14) Uani 1 1 d . . . . .
H17A H 0.029400 0.723563 0.134411 0.068 Uiso 1 1 calc R U . . .
C18 C 0.09330(18) 0.5141(5) -0.05569(17) 0.0434(11) Uani 1 1 d . . . . .
H18A H 0.061467 0.516468 -0.045597 0.052 Uiso 1 1 calc R U . . .
C19 C 0.1120(2) 0.6423(6) -0.0798(2) 0.0552(14) Uani 1 1 d . . . . .
H19A H 0.093369 0.731755 -0.085648 0.066 Uiso 1 1 calc R U . . .
C20 C 0.1573(2) 0.6392(6) -0.0951(2) 0.0564(14) Uani 1 1 d . . . . .
H20A H 0.170562 0.726721 -0.111833 0.068 Uiso 1 1 calc R U . . .
C21 C 0.18368(19) 0.5096(6) -0.08642(19) 0.0509(12) Uani 1 1 d . . . . .
H21A H 0.215428 0.506297 -0.096808 0.061 Uiso 1 1 calc R U . . .
C22 C 0.16327(16) 0.3822(5) -0.06204(16) 0.0370(10) Uani 1 1 d . . . . .
C23 C 0.18792(16) 0.2355(5) -0.05360(16) 0.0380(10) Uani 1 1 d . . . . .
C24 C 0.23172(18) 0.2069(6) -0.0739(2) 0.0549(13) Uani 1 1 d . . . . .
H24A H 0.248023 0.285415 -0.092421 0.066 Uiso 1 1 calc R U . . .
C25 C 0.25157(19) 0.0640(7) -0.0670(2) 0.0623(15) Uani 1 1 d . . . . .
H25A H 0.281779 0.043106 -0.080349 0.075 Uiso 1 1 calc R U . . .
C26 C 0.22716(18) -0.0470(6) -0.04087(19) 0.0536(13) Uani 1 1 d . . . . .
H26A H 0.239875 -0.146974 -0.036426 0.064 Uiso 1 1 calc R U . . .
C27 C 0.18376(17) -0.0127(5) -0.02086(17) 0.0444(11) Uani 1 1 d . . . . .
H27A H 0.167399 -0.089980 -0.001716 0.053 Uiso 1 1 calc R U . . .
C60 C 0.17253(17) 0.2459(6) 0.15977(17) 0.0430(11) Uani 1 1 d . . . . .
Cl1A Cl 0.1512(5) 0.902(3) 0.3076(6) 0.183(6) Uani 0.54(2) 1 d . . P A 1
Cl2A Cl 0.0835(5) 1.0513(16) 0.2394(5) 0.180(5) Uani 0.54(2) 1 d . . P A 1
C29A C 0.1285(11) 0.949(4) 0.2535(11) 0.162(14) Uani 0.54(2) 1 d . . P A 1
H29A H 0.121549 0.851927 0.232916 0.194 Uiso 0.54(2) 1 calc R U P A 1
H29B H 0.153740 0.998775 0.233119 0.194 Uiso 0.54(2) 1 calc R U P A 1
Cl1B Cl 0.1411(4) 0.8269(15) 0.3022(5) 0.115(3) Uani 0.46(2) 1 d . . P A 2
Cl2B Cl 0.0693(4) 0.957(3) 0.2298(4) 0.183(5) Uani 0.46(2) 1 d . . P A 2
C29B C 0.1128(12) 0.884(3) 0.2341(11) 0.108(9) Uani 0.46(2) 1 d . . P A 2
H29C H 0.135201 0.951764 0.215628 0.130 Uiso 0.46(2) 1 calc R U P A 2
H29D H 0.109584 0.790722 0.210304 0.130 Uiso 0.46(2) 1 calc R U P A 2


_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 C1 1.915(5) . ?
Re1 C3 1.922(5) . ?
Re1 C2 1.969(5) . ?
Re1 N3 2.184(3) . ?
Re1 C4 2.189(4) . ?
Re1 N4 2.192(3) . ?
N1 C4 1.361(5) . ?
N1 C60 1.394(5) . ?
N1 H1A 0.8800 . ?
C1 O1 1.145(5) . ?
N2 C4 1.350(5) . ?
N2 C10 1.401(5) . ?
N2 C11 1.464(5) . ?
C2 O2 1.133(5) . ?
N3 C22 1.347(5) . ?
N3 C18 1.353(5) . ?
C3 O3 1.140(5) . ?
N4 C27 1.330(5) . ?
N4 C23 1.357(5) . ?
C6 C7 1.383(8) . ?
C6 C60 1.391(6) . ?
C6 H6A 0.9500 . ?
C7 C8 1.383(9) . ?
C7 H7A 0.9500 . ?
C8 C9 1.389(7) . ?
C8 H8A 0.9500 . ?
C9 C10 1.385(6) . ?
C9 H9A 0.9500 . ?
C10 C60 1.373(7) . ?
C11 C12 1.521(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.374(6) . ?
C12 C17 1.386(6) . ?
C13 C14 1.380(7) . ?
C13 H13A 0.9500 . ?
C14 C15 1.369(8) . ?
C14 H14A 0.9500 . ?
C15 C16 1.364(8) . ?
C15 H15A 0.9500 . ?
C16 C17 1.391(8) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C18 C19 1.378(6) . ?
C18 H18A 0.9500 . ?
C19 C20 1.359(8) . ?
C19 H19A 0.9500 . ?
C20 C21 1.369(7) . ?
C20 H20A 0.9500 . ?
C21 C22 1.396(6) . ?
C21 H21A 0.9500 . ?
C22 C23 1.470(6) . ?
C23 C24 1.384(6) . ?
C24 C25 1.378(7) . ?
C24 H24A 0.9500 . ?
C25 C26 1.362(7) . ?
C25 H25A 0.9500 . ?
C26 C27 1.381(6) . ?
C26 H26A 0.9500 . ?
C27 H27A 0.9500 . ?
Cl1A C29A 1.45(3) . ?
Cl2A C29A 1.58(3) . ?
C29A H29A 0.9900 . ?
C29A H29B 0.9900 . ?
Cl1B C29B 1.81(3) . ?
Cl2B C29B 1.39(3) . ?
C29B H29C 0.9900 . ?
C29B H29D 0.9900 . ?

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
C1 Re1 C3 88.2(2) . . ?
C1 Re1 C2 87.59(18) . . ?
C3 Re1 C2 89.00(18) . . ?
C1 Re1 N3 97.71(17) . . ?
C3 Re1 N3 172.99(16) . . ?
C2 Re1 N3 95.06(15) . . ?
C1 Re1 C4 95.30(16) . . ?
C3 Re1 C4 85.82(17) . . ?
C2 Re1 C4 173.97(17) . . ?
N3 Re1 C4 89.80(13) . . ?
C1 Re1 N4 171.80(16) . . ?
C3 Re1 N4 99.95(17) . . ?
C2 Re1 N4 91.33(16) . . ?
N3 Re1 N4 74.28(13) . . ?
C4 Re1 N4 86.55(13) . . ?
C4 N1 C60 111.4(4) . . ?
C4 N1 H1A 124.3 . . ?
C60 N1 H1A 124.3 . . ?
O1 C1 Re1 176.3(4) . . ?
C4 N2 C10 111.4(4) . . ?
C4 N2 C11 126.3(3) . . ?
C10 N2 C11 121.8(3) . . ?
O2 C2 Re1 174.2(4) . . ?
C22 N3 C18 117.9(4) . . ?
C22 N3 Re1 117.6(3) . . ?
C18 N3 Re1 124.4(3) . . ?
O3 C3 Re1 179.7(5) . . ?
N2 C4 N1 104.9(3) . . ?
N2 C4 Re1 133.3(3) . . ?
N1 C4 Re1 121.7(3) . . ?
C27 N4 C23 118.6(4) . . ?
C27 N4 Re1 124.7(3) . . ?
C23 N4 Re1 116.6(3) . . ?
C7 C6 C60 116.6(6) . . ?
C7 C6 H6A 121.7 . . ?
C60 C6 H6A 121.7 . . ?
C8 C7 C6 120.8(5) . . ?
C8 C7 H7A 119.6 . . ?
C6 C7 H7A 119.6 . . ?
C7 C8 C9 123.0(5) . . ?
C7 C8 H8A 118.5 . . ?
C9 C8 H8A 118.5 . . ?
C10 C9 C8 115.5(5) . . ?
C10 C9 H9A 122.3 . . ?
C8 C9 H9A 122.3 . . ?
C60 C10 C9 122.1(4) . . ?
C60 C10 N2 106.1(4) . . ?
C9 C10 N2 131.8(5) . . ?
N2 C11 C12 112.7(3) . . ?
N2 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
N2 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C17 118.9(5) . . ?
C13 C12 C11 122.0(4) . . ?
C17 C12 C11 119.1(4) . . ?
C12 C13 C14 120.5(5) . . ?
C12 C13 H13A 119.8 . . ?
C14 C13 H13A 119.8 . . ?
C15 C14 C13 120.7(6) . . ?
C15 C14 H14A 119.6 . . ?
C13 C14 H14A 119.6 . . ?
C16 C15 C14 119.4(5) . . ?
C16 C15 H15A 120.3 . . ?
C14 C15 H15A 120.3 . . ?
C15 C16 C17 120.6(6) . . ?
C15 C16 H16A 119.7 . . ?
C17 C16 H16A 119.7 . . ?
C12 C17 C16 119.9(5) . . ?
C12 C17 H17A 120.1 . . ?
C16 C17 H17A 120.1 . . ?
N3 C18 C19 122.4(5) . . ?
N3 C18 H18A 118.8 . . ?
C19 C18 H18A 118.8 . . ?
C20 C19 C18 119.2(5) . . ?
C20 C19 H19A 120.4 . . ?
C18 C19 H19A 120.4 . . ?
C19 C20 C21 119.8(5) . . ?
C19 C20 H20A 120.1 . . ?
C21 C20 H20A 120.1 . . ?
C20 C21 C22 119.0(5) . . ?
C20 C21 H21A 120.5 . . ?
C22 C21 H21A 120.5 . . ?
N3 C22 C21 121.6(4) . . ?
N3 C22 C23 115.3(4) . . ?
C21 C22 C23 123.1(4) . . ?
N4 C23 C24 121.0(4) . . ?
N4 C23 C22 116.0(4) . . ?
C24 C23 C22 122.9(4) . . ?
C25 C24 C23 119.7(5) . . ?
C25 C24 H24A 120.2 . . ?
C23 C24 H24A 120.2 . . ?
C26 C25 C24 118.9(5) . . ?
C26 C25 H25A 120.5 . . ?
C24 C25 H25A 120.5 . . ?
C25 C26 C27 119.3(5) . . ?
C25 C26 H26A 120.3 . . ?
C27 C26 H26A 120.3 . . ?
N4 C27 C26 122.5(5) . . ?
N4 C27 H27A 118.7 . . ?
C26 C27 H27A 118.7 . . ?
C10 C60 C6 122.0(4) . . ?
C10 C60 N1 106.2(4) . . ?
C6 C60 N1 131.8(5) . . ?
Cl1A C29A Cl2A 131.0(17) . . ?
Cl1A C29A H29A 104.5 . . ?
Cl2A C29A H29A 104.5 . . ?
Cl1A C29A H29B 104.5 . . ?
Cl2A C29A H29B 104.5 . . ?
H29A C29A H29B 105.7 . . ?
Cl2B C29B Cl1B 122.2(15) . . ?
Cl2B C29B H29C 106.8 . . ?
Cl1B C29B H29C 106.8 . . ?
Cl2B C29B H29D 106.8 . . ?
Cl1B C29B H29D 106.8 . . ?
H29C C29B H29D 106.6 . . ?

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
C10 N2 C4 N1 -0.5(5) . . . . ?
C11 N2 C4 N1 -173.0(4) . . . . ?
C10 N2 C4 Re1 177.2(3) . . . . ?
C11 N2 C4 Re1 4.6(7) . . . . ?
C60 N1 C4 N2 0.5(5) . . . . ?
C60 N1 C4 Re1 -177.5(3) . . . . ?
C60 C6 C7 C8 -0.3(9) . . . . ?
C6 C7 C8 C9 -0.1(10) . . . . ?
C7 C8 C9 C10 0.0(8) . . . . ?
C8 C9 C10 C60 0.6(7) . . . . ?
C8 C9 C10 N2 -179.0(5) . . . . ?
C4 N2 C10 C60 0.2(5) . . . . ?
C11 N2 C10 C60 173.2(4) . . . . ?
C4 N2 C10 C9 180.0(5) . . . . ?
C11 N2 C10 C9 -7.1(7) . . . . ?
C4 N2 C11 C12 99.0(5) . . . . ?
C10 N2 C11 C12 -72.8(5) . . . . ?
N2 C11 C12 C13 -30.2(6) . . . . ?
N2 C11 C12 C17 152.2(4) . . . . ?
C17 C12 C13 C14 0.8(7) . . . . ?
C11 C12 C13 C14 -176.8(4) . . . . ?
C12 C13 C14 C15 -0.6(7) . . . . ?
C13 C14 C15 C16 -0.1(8) . . . . ?
C14 C15 C16 C17 0.5(8) . . . . ?
C13 C12 C17 C16 -0.4(7) . . . . ?
C11 C12 C17 C16 177.2(4) . . . . ?
C15 C16 C17 C12 -0.2(8) . . . . ?
C22 N3 C18 C19 -1.9(6) . . . . ?
Re1 N3 C18 C19 176.7(3) . . . . ?
N3 C18 C19 C20 0.9(7) . . . . ?
C18 C19 C20 C21 -0.1(7) . . . . ?
C19 C20 C21 C22 0.3(7) . . . . ?
C18 N3 C22 C21 2.2(6) . . . . ?
Re1 N3 C22 C21 -176.5(3) . . . . ?
C18 N3 C22 C23 -176.2(3) . . . . ?
Re1 N3 C22 C23 5.1(4) . . . . ?
C20 C21 C22 N3 -1.4(7) . . . . ?
C20 C21 C22 C23 176.9(4) . . . . ?
C27 N4 C23 C24 0.8(6) . . . . ?
Re1 N4 C23 C24 -175.2(3) . . . . ?
C27 N4 C23 C22 177.1(3) . . . . ?
Re1 N4 C23 C22 1.1(4) . . . . ?
N3 C22 C23 N4 -4.1(5) . . . . ?
C21 C22 C23 N4 177.6(4) . . . . ?
N3 C22 C23 C24 172.2(4) . . . . ?
C21 C22 C23 C24 -6.2(6) . . . . ?
N4 C23 C24 C25 -0.5(7) . . . . ?
C22 C23 C24 C25 -176.5(4) . . . . ?
C23 C24 C25 C26 0.8(8) . . . . ?
C24 C25 C26 C27 -1.3(8) . . . . ?
C23 N4 C27 C26 -1.5(6) . . . . ?
Re1 N4 C27 C26 174.2(3) . . . . ?
C25 C26 C27 N4 1.8(7) . . . . ?
C9 C10 C60 C6 -1.2(7) . . . . ?
N2 C10 C60 C6 178.6(4) . . . . ?
C9 C10 C60 N1 -179.7(4) . . . . ?
N2 C10 C60 N1 0.1(5) . . . . ?
C7 C6 C60 C10 1.0(8) . . . . ?
C7 C6 C60 N1 179.0(5) . . . . ?
C4 N1 C60 C10 -0.4(5) . . . . ?
C4 N1 C60 C6 -178.7(5) . . . . ?

_refine_diff_density_max         1.466
_refine_diff_density_min         -0.932
_refine_diff_density_rms         0.143

####################################################################### 
# 
# 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_5a
_database_code_depnum_ccdc_archive 'CCDC 1504041'
_audit_update_record             
;
2017-10-04 deposited with the CCDC.
2017-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 Br N4 O5 Re'
_chemical_formula_weight         712.56

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   11.113(13)
_cell_length_b                   13.659(15)
_cell_length_c                   17.18(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.820(17)
_cell_angle_gamma                90
_cell_volume                     2607(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7943
_cell_measurement_theta_min      2.400
_cell_measurement_theta_max      27.500

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.816
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    6.235
_shelx_estimated_absorpt_T_min   0.369
_shelx_estimated_absorpt_T_max   0.574
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.710
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XTAlab mini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26529
_diffrn_reflns_av_unetI/netI     0.0683
_diffrn_reflns_av_R_equivalents  0.1136
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.363
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5939
_reflns_number_gt                5378
_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       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXS (Sheldrick 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'CIFTAB (sheldrick)'
_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)+(0.0241P)²+0.1621P] 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         5939
_refine_ls_number_parameters     320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0861
_refine_ls_wR_factor_gt          0.0834
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.10648(2) 0.72005(2) 0.19996(2) 0.02091(7) Uani 1 1 d . . . . .
N3 N 0.2996(3) 0.7115(2) 0.1854(2) 0.0228(7) Uani 1 1 d . . . . .
N4 N 0.1833(3) 0.8055(2) 0.29690(19) 0.0214(6) Uani 1 1 d . . . . .
C22 C 0.3683(3) 0.7625(3) 0.2402(2) 0.0210(7) Uani 1 1 d . . . . .
C14 C 0.4941(4) 0.7646(3) 0.2405(3) 0.0267(8) Uani 1 1 d . . . . .
N1 N 0.0476(3) 0.9383(2) 0.1485(2) 0.0301(8) Uani 1 1 d . . . . .
H1A H -0.009757 0.942172 0.182569 0.036 Uiso 1 1 calc R U . . .
C11 C 0.3568(4) 0.6608(3) 0.1316(2) 0.0277(8) Uani 1 1 d . . . . .
H11A H 0.310495 0.625281 0.093696 0.033 Uiso 1 1 calc R U . . .
C3 C -0.0591(4) 0.7391(3) 0.2204(3) 0.0353(10) Uani 1 1 d . . . . .
C1 C 0.1091(4) 0.5978(3) 0.2615(3) 0.0315(9) Uani 1 1 d . . . . .
C15 C 0.5581(4) 0.8211(3) 0.2996(3) 0.0322(9) Uani 1 1 d . . . . .
H15A H 0.643533 0.823833 0.299888 0.039 Uiso 1 1 calc R U . . .
C17 C 0.3697(3) 0.8681(3) 0.3564(2) 0.0236(8) Uani 1 1 d . . . . .
O2 O 0.0208(3) 0.6082(2) 0.05268(19) 0.0418(8) Uani 1 1 d . . . . .
N2 N 0.1918(3) 0.8823(2) 0.0812(2) 0.0290(7) Uani 1 1 d . . . . .
H2A H 0.246983 0.843028 0.063064 0.035 Uiso 1 1 calc R U . . .
C7 C 0.0877(6) 1.1632(4) 0.0313(3) 0.0539(15) Uani 1 1 d . . . . .
H7A H 0.059415 1.227936 0.021875 0.065 Uiso 1 1 calc R U . . .
C13 C 0.5507(4) 0.7093(4) 0.1826(3) 0.0355(10) Uani 1 1 d . . . . .
H13A H 0.636006 0.707796 0.180897 0.043 Uiso 1 1 calc R U . . .
C20 C 0.1216(4) 0.8521(3) 0.3510(2) 0.0274(8) Uani 1 1 d . . . . .
H20A H 0.036167 0.848311 0.349303 0.033 Uiso 1 1 calc R U . . .
C2 C 0.0542(4) 0.6490(3) 0.1083(2) 0.0271(8) Uani 1 1 d . . . . .
C16 C 0.4982(4) 0.8700(3) 0.3544(3) 0.0301(9) Uani 1 1 d . . . . .
H16A H 0.542404 0.906684 0.392579 0.036 Uiso 1 1 calc R U . . .
C18 C 0.3019(4) 0.9149(3) 0.4139(2) 0.0274(8) Uani 1 1 d . . . . .
H18A H 0.341136 0.951519 0.454248 0.033 Uiso 1 1 calc R U . . .
O1 O 0.1072(4) 0.5276(3) 0.2972(2) 0.0543(10) Uani 1 1 d . . . . .
C5 C 0.0805(4) 1.0140(3) 0.0988(3) 0.0325(9) Uani 1 1 d . . . . .
C10 C 0.1722(4) 0.9780(3) 0.0553(3) 0.0318(9) Uani 1 1 d . . . . .
O3 O -0.1599(3) 0.7512(3) 0.2323(3) 0.0613(12) Uani 1 1 d . . . . .
C12 C 0.4822(4) 0.6578(4) 0.1288(3) 0.0381(10) Uani 1 1 d . . . . .
H12A H 0.519966 0.620410 0.089861 0.046 Uiso 1 1 calc R U . . .
C21 C 0.3052(3) 0.8135(3) 0.2993(2) 0.0203(7) Uani 1 1 d . . . . .
C19 C 0.1799(4) 0.9069(3) 0.4108(2) 0.0304(9) Uani 1 1 d . . . . .
H19A H 0.133720 0.938287 0.449147 0.036 Uiso 1 1 calc R U . . .
Br1 Br 0.67509(4) 0.42449(3) 0.07693(3) 0.03630(12) Uani 1 1 d . . . . .
C4 C 0.1166(4) 0.8579(3) 0.1369(2) 0.0246(8) Uani 1 1 d . . . . .
C9 C 0.2275(5) 1.0344(4) -0.0006(3) 0.0493(13) Uani 1 1 d . . . . .
H9A H 0.293103 1.010380 -0.029133 0.059 Uiso 1 1 calc R U . . .
C8 C 0.1813(6) 1.1276(4) -0.0122(4) 0.0576(16) Uani 1 1 d . . . . .
H8A H 0.214625 1.168244 -0.050868 0.069 Uiso 1 1 calc R U . . .
C6 C 0.0347(5) 1.1079(3) 0.0873(3) 0.0460(13) Uani 1 1 d . . . . .
H6A H -0.029698 1.132357 0.116761 0.055 Uiso 1 1 calc R U . . .
O5 O -0.1405(4) 0.9880(3) 0.2431(2) 0.0644(12) Uani 1 1 d . . . . .
H5 H -0.145243 0.963893 0.287855 0.097 Uiso 1 1 calc R U . . .
O4 O 0.3494(5) 0.8035(3) -0.0248(3) 0.0731(14) Uani 1 1 d . . . . .
H4 H 0.342056 0.744994 -0.039173 0.110 Uiso 1 1 calc R U . . .
C23 C 0.4706(7) 0.8328(6) -0.0303(6) 0.101(3) Uani 1 1 d . . . . .
H23A H 0.481014 0.898271 -0.007857 0.151 Uiso 1 1 calc R U . . .
H23B H 0.492183 0.834028 -0.085180 0.151 Uiso 1 1 calc R U . . .
H23C H 0.522666 0.786298 -0.001810 0.151 Uiso 1 1 calc R U . . .
C24 C -0.2551(6) 1.0146(5) 0.2153(4) 0.0702(18) Uani 1 1 d . . . . .
H24A H -0.299286 1.045554 0.257199 0.105 Uiso 1 1 calc R U . . .
H24B H -0.298641 0.956141 0.197025 0.105 Uiso 1 1 calc R U . . .
H24C H -0.248083 1.060862 0.172049 0.105 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 C3 1.902(5) . ?
Re1 C2 1.924(4) . ?
Re1 C1 1.976(5) . ?
Re1 N3 2.172(4) . ?
Re1 C4 2.177(4) . ?
Re1 N4 2.185(4) . ?
N3 C11 1.333(5) . ?
N3 C22 1.382(5) . ?
N4 C20 1.334(5) . ?
N4 C21 1.359(5) . ?
C22 C14 1.398(6) . ?
C22 C21 1.432(5) . ?
C14 C13 1.413(6) . ?
C14 C15 1.444(6) . ?
N1 C4 1.358(5) . ?
N1 C5 1.398(6) . ?
C11 C12 1.397(6) . ?
C3 O3 1.157(6) . ?
C1 O1 1.139(5) . ?
C15 C16 1.347(6) . ?
C17 C21 1.410(5) . ?
C17 C18 1.414(6) . ?
C17 C16 1.430(6) . ?
O2 C2 1.157(5) . ?
N2 C4 1.332(5) . ?
N2 C10 1.395(5) . ?
C7 C6 1.372(8) . ?
C7 C8 1.388(9) . ?
C13 C12 1.372(7) . ?
C20 C19 1.412(6) . ?
C18 C19 1.359(6) . ?
C5 C10 1.373(6) . ?
C5 C6 1.392(6) . ?
C10 C9 1.390(7) . ?
C9 C8 1.385(8) . ?
O5 C24 1.394(7) . ?
O4 C23 1.411(9) . ?

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
C3 Re1 C2 87.2(2) . . ?
C3 Re1 C1 90.8(2) . . ?
C2 Re1 C1 90.64(19) . . ?
C3 Re1 N3 173.69(16) . . ?
C2 Re1 N3 98.78(15) . . ?
C1 Re1 N3 91.05(15) . . ?
C3 Re1 C4 92.27(19) . . ?
C2 Re1 C4 92.71(17) . . ?
C1 Re1 C4 175.55(16) . . ?
N3 Re1 C4 85.54(13) . . ?
C3 Re1 N4 98.20(17) . . ?
C2 Re1 N4 173.65(15) . . ?
C1 Re1 N4 92.58(17) . . ?
N3 Re1 N4 75.70(13) . . ?
C4 Re1 N4 83.81(15) . . ?
C11 N3 C22 118.0(4) . . ?
C11 N3 Re1 127.0(3) . . ?
C22 N3 Re1 114.9(3) . . ?
C20 N4 C21 118.4(3) . . ?
C20 N4 Re1 126.1(3) . . ?
C21 N4 Re1 115.5(2) . . ?
N3 C22 C14 122.9(4) . . ?
N3 C22 C21 117.1(4) . . ?
C14 C22 C21 119.9(4) . . ?
C22 C14 C13 117.0(4) . . ?
C22 C14 C15 118.9(4) . . ?
C13 C14 C15 124.1(4) . . ?
C4 N1 C5 110.4(4) . . ?
N3 C11 C12 122.5(4) . . ?
O3 C3 Re1 179.3(5) . . ?
O1 C1 Re1 178.1(4) . . ?
C16 C15 C14 120.9(4) . . ?
C21 C17 C18 117.1(4) . . ?
C21 C17 C16 118.6(4) . . ?
C18 C17 C16 124.3(4) . . ?
C4 N2 C10 111.7(4) . . ?
C6 C7 C8 122.0(5) . . ?
C12 C13 C14 120.0(4) . . ?
N4 C20 C19 121.7(4) . . ?
O2 C2 Re1 178.3(4) . . ?
C15 C16 C17 121.6(4) . . ?
C19 C18 C17 119.3(4) . . ?
C10 C5 C6 121.8(5) . . ?
C10 C5 N1 106.3(4) . . ?
C6 C5 N1 131.8(5) . . ?
C5 C10 C9 122.0(4) . . ?
C5 C10 N2 105.8(4) . . ?
C9 C10 N2 132.2(5) . . ?
C13 C12 C11 119.6(4) . . ?
N4 C21 C17 123.2(3) . . ?
N4 C21 C22 116.7(3) . . ?
C17 C21 C22 120.1(3) . . ?
C18 C19 C20 120.3(4) . . ?
N2 C4 N1 105.8(3) . . ?
N2 C4 Re1 128.2(3) . . ?
N1 C4 Re1 126.0(3) . . ?
C8 C9 C10 116.0(6) . . ?
C9 C8 C7 121.7(5) . . ?
C7 C6 C5 116.3(5) . . ?

_refine_diff_density_max         1.859
_refine_diff_density_min         -1.841
_refine_diff_density_rms         0.158

####################################################################### 
# 
# 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_6a
_database_code_depnum_ccdc_archive 'CCDC 1504042'
_audit_update_record             
;
2017-10-04 deposited with the CCDC.
2017-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H30 Br N4 O3 Re'
_chemical_formula_weight         736.67

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   10.943(2)
_cell_length_b                   21.014(4)
_cell_length_c                   14.500(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.75(3)
_cell_angle_gamma                90
_cell_volume                     3175.7(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    15635
_cell_measurement_theta_min      3.0730
_cell_measurement_theta_max      31.1010

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    5.116
_shelx_estimated_absorpt_T_min   0.309
_shelx_estimated_absorpt_T_max   0.629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.28435
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51233
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.154
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7250
_reflns_number_gt                6087
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'SHELXS (Shekdrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'CIFTAB (Sheldrick)'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0305P)²+5.8666P] 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         7250
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0818
_refine_ls_wR_factor_gt          0.0726
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      1.144
_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 0.30731(2) 0.18991(2) 0.39427(2) 0.03874(6) Uani 1 1 d . . . . .
Br1 Br 0.35152(6) 0.34488(3) 0.67342(4) 0.07143(17) Uani 1 1 d . . . . .
C15 C 0.2543(4) 0.05696(18) 0.4563(3) 0.0350(8) Uani 1 1 d . . . . .
N2 N 0.1426(3) 0.26000(15) 0.5093(2) 0.0367(7) Uani 1 1 d . . . . .
H2A H 0.212504 0.270314 0.555904 0.044 Uiso 1 1 calc R U . . .
C4 C 0.1416(3) 0.22451(17) 0.4313(3) 0.0327(8) Uani 1 1 d . . . . .
N1 N 0.0167(3) 0.21923(16) 0.3796(2) 0.0394(7) Uani 1 1 d . . . . .
H1A H -0.011910 0.197684 0.325242 0.047 Uiso 1 1 calc R U . . .
C16 C 0.3404(4) 0.08560(18) 0.5463(3) 0.0374(8) Uani 1 1 d . . . . .
N3 N 0.3716(3) 0.14746(15) 0.5377(3) 0.0419(8) Uani 1 1 d . . . . .
C2 C 0.3850(4) 0.2722(2) 0.4236(4) 0.0509(11) Uani 1 1 d . . . . .
C13 C 0.1236(4) -0.02882(19) 0.3671(3) 0.0409(9) Uani 1 1 d . . . . .
C18 C 0.4621(4) 0.0833(2) 0.7152(3) 0.0493(11) Uani 1 1 d . . . . .
C11 C 0.1407(4) 0.0725(2) 0.2961(3) 0.0434(9) Uani 1 1 d . . . . .
H11A H 0.116662 0.099038 0.240417 0.052 Uiso 1 1 calc R U . . .
C6 C -0.0246(5) 0.3154(2) 0.5692(4) 0.0533(12) Uani 1 1 d . . . . .
H6A H 0.031985 0.332857 0.626940 0.064 Uiso 1 1 calc R U . . .
C10 C -0.0611(4) 0.2521(2) 0.4232(3) 0.0414(9) Uani 1 1 d . . . . .
C14 C 0.2078(4) -0.00468(19) 0.4522(3) 0.0417(9) Uani 1 1 d . . . . .
H14A H 0.233713 -0.030783 0.508328 0.050 Uiso 1 1 calc R U . . .
C5 C 0.0197(4) 0.27814(19) 0.5067(3) 0.0399(9) Uani 1 1 d . . . . .
C20 C 0.4439(5) 0.1767(2) 0.6175(4) 0.0582(13) Uani 1 1 d . . . . .
H20A H 0.464655 0.220283 0.613198 0.070 Uiso 1 1 calc R U . . .
C1 C 0.2340(5) 0.2166(2) 0.2622(4) 0.0487(11) Uani 1 1 d . . . . .
C7 C -0.1549(6) 0.3255(3) 0.5428(5) 0.0649(15) Uani 1 1 d . . . . .
H7A H -0.189720 0.350662 0.583123 0.078 Uiso 1 1 calc R U . . .
C21 C 0.0708(5) -0.0963(2) 0.3641(4) 0.0535(12) Uani 1 1 d . . . . .
O2 O 0.4312(4) 0.32152(17) 0.4399(4) 0.0775(12) Uani 1 1 d . . . . .
O1 O 0.1886(4) 0.23151(19) 0.1833(3) 0.0711(10) Uani 1 1 d . . . . .
C3 C 0.4612(5) 0.1606(2) 0.3656(4) 0.0588(13) Uani 1 1 d . . . . .
C9 C -0.1931(4) 0.2622(3) 0.3960(4) 0.0589(13) Uani 1 1 d . . . . .
H9A H -0.249683 0.244392 0.338578 0.071 Uiso 1 1 calc R U . . .
N4 N 0.2221(3) 0.09558(15) 0.3781(2) 0.0369(7) Uani 1 1 d . . . . .
O3 O 0.5525(4) 0.1455(2) 0.3488(4) 0.1002(17) Uani 1 1 d . . . . .
C25 C 0.5123(5) 0.0474(3) 0.8114(4) 0.0634(14) Uani 1 1 d . . . . .
C19 C 0.4893(5) 0.1469(2) 0.7050(4) 0.0596(14) Uani 1 1 d . . . . .
H19A H 0.540162 0.169954 0.759582 0.071 Uiso 1 1 calc R U . . .
C8 C -0.2368(5) 0.2997(3) 0.4581(6) 0.0742(18) Uani 1 1 d . . . . .
H8A H -0.326098 0.308083 0.442096 0.089 Uiso 1 1 calc R U . . .
C17 C 0.3843(4) 0.0532(2) 0.6334(3) 0.0466(10) Uani 1 1 d . . . . .
H17A H 0.360893 0.009906 0.636940 0.056 Uiso 1 1 calc R U . . .
C23 C 0.1803(8) -0.1428(3) 0.4016(8) 0.123(3) Uani 1 1 d . . . . .
H23A H 0.231118 -0.130541 0.467345 0.184 Uiso 1 1 calc R U . . .
H23B H 0.145867 -0.185713 0.402644 0.184 Uiso 1 1 calc R U . . .
H23C H 0.234951 -0.142122 0.359181 0.184 Uiso 1 1 calc R U . . .
C27 C 0.6102(8) 0.0855(3) 0.8875(5) 0.115(3) Uani 1 1 d . . . . .
H27A H 0.571548 0.125546 0.899217 0.173 Uiso 1 1 calc R U . . .
H27B H 0.638450 0.060941 0.947811 0.173 Uiso 1 1 calc R U . . .
H27C H 0.684180 0.094626 0.864965 0.173 Uiso 1 1 calc R U . . .
C24 C -0.0130(8) -0.0993(3) 0.4299(7) 0.120(3) Uani 1 1 d . . . . .
H24A H 0.037428 -0.086965 0.495711 0.180 Uiso 1 1 calc R U . . .
H24B H -0.085597 -0.070080 0.406069 0.180 Uiso 1 1 calc R U . . .
H24C H -0.045098 -0.142777 0.430681 0.180 Uiso 1 1 calc R U . . .
C28 C 0.5738(10) -0.0131(3) 0.7953(5) 0.144(5) Uani 1 1 d . . . . .
H28A H 0.646100 -0.003464 0.770983 0.216 Uiso 1 1 calc R U . . .
H28B H 0.604927 -0.036400 0.856518 0.216 Uiso 1 1 calc R U . . .
H28C H 0.510898 -0.039160 0.747728 0.216 Uiso 1 1 calc R U . . .
C22 C -0.0064(14) -0.1152(4) 0.2638(6) 0.200(7) Uani 1 1 d . . . . .
H22A H -0.077434 -0.085185 0.239278 0.299 Uiso 1 1 calc R U . . .
H22B H 0.048429 -0.114571 0.221503 0.299 Uiso 1 1 calc R U . . .
H22C H -0.040654 -0.158162 0.264966 0.299 Uiso 1 1 calc R U . . .
C26 C 0.4001(9) 0.0354(8) 0.8489(7) 0.202(7) Uani 1 1 d . . . . .
H26A H 0.362181 0.076136 0.858602 0.304 Uiso 1 1 calc R U . . .
H26B H 0.335661 0.009776 0.801821 0.304 Uiso 1 1 calc R U . . .
H26C H 0.429690 0.012535 0.910610 0.304 Uiso 1 1 calc R U . . .
C12 C 0.0902(4) 0.0119(2) 0.2890(3) 0.0470(10) Uani 1 1 d . . . . .
H12A H 0.031751 -0.001951 0.229477 0.056 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 C2 1.917(4) . ?
Re1 C1 1.921(5) . ?
Re1 C3 1.953(5) . ?
Re1 C4 2.167(4) . ?
Re1 N4 2.173(3) . ?
Re1 N3 2.174(4) . ?
C15 N4 1.350(5) . ?
C15 C14 1.386(5) . ?
C15 C16 1.486(5) . ?
N2 C4 1.352(5) . ?
N2 C5 1.387(5) . ?
C4 N1 1.348(5) . ?
N1 C10 1.390(5) . ?
C16 N3 1.359(5) . ?
C16 C17 1.385(6) . ?
N3 C20 1.336(6) . ?
C2 O2 1.145(5) . ?
C13 C12 1.377(6) . ?
C13 C14 1.391(6) . ?
C13 C21 1.527(6) . ?
C18 C17 1.384(6) . ?
C18 C19 1.387(7) . ?
C18 C25 1.533(7) . ?
C11 N4 1.341(5) . ?
C11 C12 1.379(6) . ?
C6 C7 1.376(8) . ?
C6 C5 1.392(6) . ?
C10 C5 1.376(6) . ?
C10 C9 1.392(6) . ?
C20 C19 1.366(7) . ?
C1 O1 1.143(6) . ?
C7 C8 1.391(9) . ?
C21 C22 1.495(9) . ?
C21 C23 1.512(9) . ?
C21 C24 1.514(8) . ?
C3 O3 1.143(6) . ?
C9 C8 1.386(8) . ?
C25 C28 1.490(9) . ?
C25 C26 1.507(11) . ?
C25 C27 1.512(8) . ?

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
C2 Re1 C1 88.8(2) . . ?
C2 Re1 C3 88.78(19) . . ?
C1 Re1 C3 90.3(2) . . ?
C2 Re1 C4 89.47(16) . . ?
C1 Re1 C4 91.28(17) . . ?
C3 Re1 C4 177.62(18) . . ?
C2 Re1 N4 173.66(18) . . ?
C1 Re1 N4 97.11(17) . . ?
C3 Re1 N4 93.35(16) . . ?
C4 Re1 N4 88.23(13) . . ?
C2 Re1 N3 99.55(18) . . ?
C1 Re1 N3 171.46(16) . . ?
C3 Re1 N3 91.5(2) . . ?
C4 Re1 N3 87.24(14) . . ?
N4 Re1 N3 74.44(12) . . ?
N4 C15 C14 121.9(4) . . ?
N4 C15 C16 115.3(3) . . ?
C14 C15 C16 122.8(4) . . ?
C4 N2 C5 111.7(3) . . ?
N1 C4 N2 105.0(3) . . ?
N1 C4 Re1 128.2(3) . . ?
N2 C4 Re1 126.8(3) . . ?
C4 N1 C10 111.4(3) . . ?
N3 C16 C17 121.8(4) . . ?
N3 C16 C15 114.6(4) . . ?
C17 C16 C15 123.5(4) . . ?
C20 N3 C16 117.4(4) . . ?
C20 N3 Re1 125.0(3) . . ?
C16 N3 Re1 117.6(3) . . ?
O2 C2 Re1 179.2(5) . . ?
C12 C13 C14 116.2(4) . . ?
C12 C13 C21 123.4(4) . . ?
C14 C13 C21 120.4(4) . . ?
C17 C18 C19 116.5(4) . . ?
C17 C18 C25 120.8(4) . . ?
C19 C18 C25 122.8(4) . . ?
N4 C11 C12 122.9(4) . . ?
C7 C6 C5 116.3(5) . . ?
C5 C10 N1 106.2(3) . . ?
C5 C10 C9 121.5(4) . . ?
N1 C10 C9 132.3(4) . . ?
C15 C14 C13 120.9(4) . . ?
C10 C5 N2 105.8(4) . . ?
C10 C5 C6 122.6(4) . . ?
N2 C5 C6 131.6(4) . . ?
N3 C20 C19 123.0(4) . . ?
O1 C1 Re1 178.6(5) . . ?
C6 C7 C8 121.3(5) . . ?
C22 C21 C23 109.3(7) . . ?
C22 C21 C24 109.3(7) . . ?
C23 C21 C24 108.2(6) . . ?
C22 C21 C13 111.8(4) . . ?
C23 C21 C13 109.8(4) . . ?
C24 C21 C13 108.4(4) . . ?
O3 C3 Re1 177.7(5) . . ?
C8 C9 C10 115.8(5) . . ?
C11 N4 C15 117.4(3) . . ?
C11 N4 Re1 125.0(3) . . ?
C15 N4 Re1 117.7(3) . . ?
C28 C25 C26 111.7(9) . . ?
C28 C25 C27 108.2(6) . . ?
C26 C25 C27 107.4(7) . . ?
C28 C25 C18 109.3(5) . . ?
C26 C25 C18 107.8(5) . . ?
C27 C25 C18 112.5(5) . . ?
C20 C19 C18 120.8(4) . . ?
C9 C8 C7 122.6(5) . . ?
C18 C17 C16 120.5(4) . . ?
C13 C12 C11 120.8(4) . . ?

_refine_diff_density_max         1.250
_refine_diff_density_min         -0.916
_refine_diff_density_rms         0.106



