# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_m-recl-02
_database_code_depnum_ccdc_archive 'CCDC 2090791'
loop_
_audit_author_name
_audit_author_address
'Aurelien Crochet'
;University of Fribourg, Chemistry Department
Switzerland
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2023-03-09 downloaded from the CCDC.
;
_audit_creation_date             2020-12-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
isabelle.kolly@unifr.ch
aurelien.crochet@unifr.ch
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H9 Br Cl N2 O3 Re'
_chemical_formula_sum            'C14 H9 Br Cl N2 O3 Re'
_chemical_formula_weight         554.79
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -5.2083 5.8923 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.9380(6)
_cell_length_b                   12.1342(11)
_cell_length_c                   12.3961(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.486(5)
_cell_angle_gamma                90
_cell_volume                     1631.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    34111
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      65.54
_cell_measurement_theta_min      4.07
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    19.068
_exptl_absorpt_correction_T_max  0.3089
_exptl_absorpt_correction_T_min  0.062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270. Afterwards scaling of
reflection intensities was performed within STOE LANA. J. Koziskova, F. Hahn,
J. Richter, J. Kozisek, Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136-140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.259
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1032
_exptl_crystal_recrystallization_method 'layering DCM/pentane'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.896
_diffrn_reflns_Laue_measured_fraction_max 0.896
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9479
_diffrn_reflns_point_group_measured_fraction_full 0.896
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_theta_full        66.731
_diffrn_reflns_theta_max         66.731
_diffrn_reflns_theta_min         5.122
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 Pilatus300K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'Dectris Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.896
_diffrn_measured_fraction_theta_max 0.896
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '1.2 mm, 0.6 diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Primux 100 micro'
_diffrn_special_details          'unsolved twinning problem'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2471
_reflns_number_total             2595
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         5.617
_refine_diff_density_min         -2.585
_refine_diff_density_rms         0.295
_refine_ls_extinction_coef       0.00080(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2595
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0829
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1395P)²+19.0354P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2252
_refine_ls_wR_factor_ref         0.2289
_refine_special_details          'unsolved twinning problem'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Re1 Re 0.65860(6) 0.54144(6) 0.28574(5) 0.0598(4) Uani 1 1 d . . . . .
Br1 Br 0.86712(16) 0.50283(17) 0.21245(13) 0.0661(5) Uani 1 1 d . . . . .
Cl1 Cl 0.8192(7) 0.0499(4) 0.3535(5) 0.1011(19) Uani 1 1 d . . . . .
O1 O 0.4221(13) 0.5888(19) 0.3869(14) 0.122(6) Uani 1 1 d . . . . .
O2 O 0.5091(13) 0.3895(15) 0.1224(12) 0.103(5) Uani 1 1 d . . . . .
O3 O 0.5995(14) 0.7395(14) 0.1325(13) 0.104(5) Uani 1 1 d . . . . .
N1 N 0.7730(11) 0.6323(12) 0.4147(10) 0.063(3) Uani 1 1 d . . . . .
N2 N 0.7262(11) 0.4162(11) 0.4050(10) 0.059(3) Uani 1 1 d . . . . .
C1 C 0.7915(17) 0.7389(14) 0.4155(16) 0.074(4) Uani 1 1 d . . . . .
H1 H 0.755476 0.781127 0.357309 0.089 Uiso 1 1 calc R U . . .
C2 C 0.8638(18) 0.7904(18) 0.5015(17) 0.084(5) Uani 1 1 d . . . . .
H2 H 0.875481 0.866304 0.500243 0.101 Uiso 1 1 calc R U . . .
C3 C 0.9166(17) 0.7312(18) 0.5861(17) 0.086(6) Uani 1 1 d . . . . .
H3 H 0.966471 0.764911 0.643154 0.103 Uiso 1 1 calc R U . . .
C4 C 0.8956(14) 0.6192(15) 0.5868(13) 0.068(4) Uani 1 1 d . . . . .
H4 H 0.929359 0.577384 0.646177 0.082 Uiso 1 1 calc R U . . .
C5 C 0.8248(12) 0.5680(13) 0.5000(12) 0.059(4) Uani 1 1 d . . . . .
C6 C 0.8012(15) 0.4491(12) 0.4926(13) 0.060(4) Uani 1 1 d . . . . .
C7 C 0.8510(15) 0.3753(15) 0.5698(13) 0.068(4) Uani 1 1 d . . . . .
H7 H 0.902626 0.399261 0.630826 0.082 Uiso 1 1 calc R U . . .
C8 C 0.8235(17) 0.2653(15) 0.5554(14) 0.074(4) Uani 1 1 d . . . . .
H8 H 0.856492 0.214197 0.607099 0.089 Uiso 1 1 calc R U . . .
C9 C 0.7464(14) 0.2304(14) 0.4637(14) 0.069(4) Uani 1 1 d . . . . .
C10 C 0.7003(14) 0.3106(16) 0.3898(13) 0.071(4) Uani 1 1 d . . . . .
H10 H 0.649435 0.289265 0.327272 0.085 Uiso 1 1 calc R U . . .
C11 C 0.7168(19) 0.1078(16) 0.4391(17) 0.083(5) Uani 1 1 d . . . . .
H11A H 0.632634 0.101103 0.403808 0.099 Uiso 1 1 calc R U . . .
H11B H 0.723546 0.066872 0.506878 0.099 Uiso 1 1 calc R U . . .
C12 C 0.5136(17) 0.5680(19) 0.3527(15) 0.083(5) Uani 1 1 d . . . . .
C13 C 0.5673(17) 0.4484(15) 0.1825(16) 0.072(5) Uani 1 1 d . . . . .
C14 C 0.6203(15) 0.6627(19) 0.1889(14) 0.078(5) 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 Br1 2.6051(17) . ?
Re1 N1 2.194(13) . ?
Re1 N2 2.180(14) . ?
Re1 C12 1.911(19) . ?
Re1 C13 1.89(2) . ?
Re1 C14 1.91(2) . ?
Cl1 C11 1.78(2) . ?
O1 C12 1.16(2) . ?
O2 C13 1.16(2) . ?
O3 C14 1.17(2) . ?
N1 C1 1.31(2) . ?
N1 C5 1.38(2) . ?
N2 C6 1.33(2) . ?
N2 C10 1.32(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.39(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.34(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.38(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.39(2) . ?
C5 C6 1.47(2) . ?
C6 C7 1.37(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.37(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.39(2) . ?
C9 C10 1.39(2) . ?
C9 C11 1.54(3) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Re1 Br1 84.4(3) . . ?
N2 Re1 Br1 82.9(3) . . ?
N2 Re1 N1 75.3(5) . . ?
C12 Re1 Br1 174.7(5) . . ?
C12 Re1 N1 91.5(7) . . ?
C12 Re1 N2 92.9(7) . . ?
C13 Re1 Br1 93.8(6) . . ?
C13 Re1 N1 173.5(6) . . ?
C13 Re1 N2 98.4(7) . . ?
C13 Re1 C12 90.0(8) . . ?
C13 Re1 C14 88.9(8) . . ?
C14 Re1 Br1 92.8(5) . . ?
C14 Re1 N1 97.3(7) . . ?
C14 Re1 N2 171.7(6) . . ?
C14 Re1 C12 90.9(8) . . ?
C1 N1 Re1 125.1(12) . . ?
C1 N1 C5 120.4(15) . . ?
C5 N1 Re1 114.4(11) . . ?
C6 N2 Re1 117.5(11) . . ?
C10 N2 Re1 122.2(11) . . ?
C10 N2 C6 120.2(14) . . ?
N1 C1 H1 119.2 . . ?
N1 C1 C2 121.5(18) . . ?
C2 C1 H1 119.2 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(19) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.7 . . ?
C2 C3 C4 118.6(17) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.9(18) . . ?
C5 C4 H4 119.6 . . ?
N1 C5 C4 118.3(16) . . ?
N1 C5 C6 117.3(14) . . ?
C4 C5 C6 124.4(15) . . ?
N2 C6 C5 115.4(14) . . ?
N2 C6 C7 121.3(15) . . ?
C7 C6 C5 123.3(15) . . ?
C6 C7 H7 120.5 . . ?
C6 C7 C8 118.9(17) . . ?
C8 C7 H7 120.5 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.1(16) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C11 123.0(16) . . ?
C10 C9 C8 117.1(17) . . ?
C10 C9 C11 119.8(16) . . ?
N2 C10 C9 122.3(16) . . ?
N2 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
Cl1 C11 H11A 109.3 . . ?
Cl1 C11 H11B 109.3 . . ?
C9 C11 Cl1 111.4(13) . . ?
C9 C11 H11A 109.3 . . ?
C9 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
O1 C12 Re1 175.0(19) . . ?
O2 C13 Re1 177.3(17) . . ?
O3 C14 Re1 177.5(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Re1 N1 C1 C2 178.8(13) . . . . ?
Re1 N1 C5 C4 -178.1(10) . . . . ?
Re1 N1 C5 C6 2.0(15) . . . . ?
Re1 N2 C6 C5 2.5(16) . . . . ?
Re1 N2 C6 C7 -177.9(11) . . . . ?
Re1 N2 C10 C9 177.9(11) . . . . ?
N1 C1 C2 C3 0(3) . . . . ?
N1 C5 C6 N2 -3.0(19) . . . . ?
N1 C5 C6 C7 177.4(13) . . . . ?
N2 C6 C7 C8 1(2) . . . . ?
C1 N1 C5 C4 1(2) . . . . ?
C1 N1 C5 C6 -179.3(14) . . . . ?
C1 C2 C3 C4 -1(3) . . . . ?
C2 C3 C4 C5 2(3) . . . . ?
C3 C4 C5 N1 -2(2) . . . . ?
C3 C4 C5 C6 178.0(16) . . . . ?
C4 C5 C6 N2 177.1(13) . . . . ?
C4 C5 C6 C7 -3(2) . . . . ?
C5 N1 C1 C2 0(2) . . . . ?
C5 C6 C7 C8 -179.9(15) . . . . ?
C6 N2 C10 C9 2(2) . . . . ?
C6 C7 C8 C9 0(2) . . . . ?
C7 C8 C9 C10 0(2) . . . . ?
C7 C8 C9 C11 176.7(16) . . . . ?
C8 C9 C10 N2 -1(2) . . . . ?
C8 C9 C11 Cl1 -93.4(18) . . . . ?
C10 N2 C6 C5 179.0(13) . . . . ?
C10 N2 C6 C7 -1(2) . . . . ?
C10 C9 C11 Cl1 83.1(18) . . . . ?
C11 C9 C10 N2 -177.6(15) . . . . ?

_olex2_exptl_crystal_mounting_method 'on loop with oil'
_olex2_submission_special_instructions 'No special instructions were received'
_vrf_PLAT029_m-recl-02           
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.897 Why?  
RESPONSE: low diffraction intensities in high angles
;
_vrf_PLAT342_m-recl-02           
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.025 Ang.  
RESPONSE: low crystal quality
;
_vrf_PLAT911_m-recl-02           
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.596        275 Report
RESPONSE: low diffraction intensities in high angles
;
_vrf_PLAT971_m-recl-02           
;
PROBLEM: Check Calcd Resid. Dens.  1.01A   From Re1             5.79 eA-3  
RESPONSE: Unsolved twinning problem
;
_vrf_PLAT972_m-recl-02           
;
PROBLEM: Check Calcd Resid. Dens.  0.92A   From Re1            -2.59 eA-3  
RESPONSE: Unsolved twinning problem
;
####################################################################### 
# 
# 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_m-rebr
_database_code_depnum_ccdc_archive 'CCDC 2090792'
loop_
_audit_author_name
_audit_author_address
'Aurelien Crochet'
;University of Fribourg, Chemistry Department
Switzerland
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2023-03-09 downloaded from the CCDC.
;
_audit_creation_date             2020-12-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
isabelle.kolly@unifr.ch
aurelien.crochet@unifr.ch
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H9 Br2 N2 O3 Re'
_chemical_formula_sum            'C14 H9 Br2 N2 O3 Re'
_chemical_formula_weight         599.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -5.2083 5.8923 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.9912(4)
_cell_length_b                   12.2942(4)
_cell_length_c                   12.4352(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.928(3)
_cell_angle_gamma                90
_cell_volume                     1664.28(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    40197
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      65.25
_cell_measurement_theta_min      5.42
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    20.026
_exptl_absorpt_correction_T_max  0.4428
_exptl_absorpt_correction_T_min  0.1089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270. Afterwards scaling of
reflection intensities was performed within STOE LANA. J. Koziskova, F. Hahn,
J. Richter, J. Kozisek, Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136-140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             1104
_exptl_crystal_recrystallization_method 'layering of DCM and hexane'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16392
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        64.823
_diffrn_reflns_theta_max         64.823
_diffrn_reflns_theta_min         5.428
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 Pilatus300K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'Dectris Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '1.2 mm, 0.6 diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Primux 100 micro'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2637
_reflns_number_total             2710
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         6.577
_refine_diff_density_min         -1.789
_refine_diff_density_rms         0.277
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2710
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0648
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0940P)²+23.1293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1665
_refine_ls_wR_factor_ref         0.1680
_refine_special_details          'possible unsolved twinning problem.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Re1 Re 0.34501(4) 0.45920(5) 0.71252(4) 0.0410(3) Uani 1 1 d . . . . .
Br1 Br 0.1677(2) 0.95251(14) 0.64314(17) 0.0882(7) Uani 1 1 d . . . . .
Br2 Br 0.13783(10) 0.49541(11) 0.78754(9) 0.0426(3) Uani 1 1 d . . . . .
O1 O 0.4952(10) 0.6078(10) 0.8786(9) 0.075(3) Uani 1 1 d . . . . .
O2 O 0.4036(10) 0.2605(9) 0.8625(10) 0.079(3) Uani 1 1 d . . . . .
O3 O 0.5760(11) 0.4161(14) 0.6094(11) 0.100(4) Uani 1 1 d . . . . .
N1 N 0.2313(9) 0.3743(8) 0.5829(7) 0.042(2) Uani 1 1 d . . . . .
N2 N 0.2770(8) 0.5841(8) 0.5962(7) 0.0367(19) Uani 1 1 d . . . . .
C1 C 0.2082(13) 0.2644(10) 0.5771(12) 0.057(3) Uani 1 1 d . . . . .
H1 H 0.241004 0.221556 0.635624 0.068 Uiso 1 1 calc R U . . .
C2 C 0.1420(15) 0.2155(12) 0.4936(14) 0.070(4) Uani 1 1 d . . . . .
H2 H 0.132489 0.140301 0.492982 0.084 Uiso 1 1 calc R U . . .
C3 C 0.0880(13) 0.2771(11) 0.4084(11) 0.057(3) Uani 1 1 d . . . . .
H3 H 0.040381 0.244581 0.349497 0.069 Uiso 1 1 calc R U . . .
C4 C 0.1054(11) 0.3872(11) 0.4116(10) 0.051(3) Uani 1 1 d . . . . .
H4 H 0.068892 0.430028 0.354486 0.061 Uiso 1 1 calc R U . . .
C5 C 0.1773(10) 0.4360(10) 0.4996(9) 0.041(2) Uani 1 1 d . . . . .
C6 C 0.1986(10) 0.5516(9) 0.5063(9) 0.040(3) Uani 1 1 d . . . . .
C7 C 0.1448(11) 0.6277(11) 0.4319(9) 0.049(3) Uani 1 1 d . . . . .
H7 H 0.090203 0.605904 0.371956 0.058 Uiso 1 1 calc R U . . .
C8 C 0.1742(12) 0.7371(11) 0.4487(11) 0.053(3) Uani 1 1 d . . . . .
H8 H 0.139665 0.788813 0.399013 0.063 Uiso 1 1 calc R U . . .
C9 C 0.2524(11) 0.7686(10) 0.5366(10) 0.047(3) Uani 1 1 d . . . . .
C10 C 0.3021(11) 0.6906(10) 0.6095(10) 0.047(3) Uani 1 1 d . . . . .
H10 H 0.355104 0.712691 0.670379 0.057 Uiso 1 1 calc R U . . .
C11 C 0.2862(13) 0.8873(11) 0.5602(13) 0.058(3) Uani 1 1 d . . . . .
H11A H 0.286447 0.926500 0.492528 0.070 Uiso 1 1 calc R U . . .
H11B H 0.367819 0.891755 0.601049 0.070 Uiso 1 1 calc R U . . .
C12 C 0.4396(11) 0.5520(11) 0.8180(11) 0.050(3) Uani 1 1 d . . . . .
C13 C 0.3823(11) 0.3350(14) 0.8079(12) 0.063(4) Uani 1 1 d . . . . .
C14 C 0.4905(12) 0.4318(14) 0.6468(12) 0.062(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
Re1 Br2 2.6154(12) . ?
Re1 N1 2.167(10) . ?
Re1 N2 2.170(9) . ?
Re1 C12 1.930(14) . ?
Re1 C13 1.942(17) . ?
Re1 C14 1.923(13) . ?
Br1 C11 1.942(14) . ?
O1 C12 1.133(17) . ?
O2 C13 1.145(19) . ?
O3 C14 1.121(17) . ?
N1 C1 1.374(17) . ?
N1 C5 1.353(15) . ?
N2 C6 1.374(15) . ?
N2 C10 1.344(16) . ?
C1 H1 0.9300 . ?
C1 C2 1.33(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.37(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.37(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.393(18) . ?
C5 C6 1.441(16) . ?
C6 C7 1.388(17) . ?
C7 H7 0.9300 . ?
C7 C8 1.392(19) . ?
C8 H8 0.9300 . ?
C8 C9 1.351(19) . ?
C9 C10 1.380(18) . ?
C9 C11 1.524(18) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Re1 Br2 84.6(2) . . ?
N1 Re1 N2 74.6(3) . . ?
N2 Re1 Br2 83.1(2) . . ?
C12 Re1 Br2 94.1(4) . . ?
C12 Re1 N1 172.5(5) . . ?
C12 Re1 N2 97.9(5) . . ?
C12 Re1 C13 90.1(6) . . ?
C13 Re1 Br2 92.1(4) . . ?
C13 Re1 N1 97.3(5) . . ?
C13 Re1 N2 170.9(5) . . ?
C14 Re1 Br2 175.7(4) . . ?
C14 Re1 N1 91.6(5) . . ?
C14 Re1 N2 94.1(5) . . ?
C14 Re1 C12 89.5(6) . . ?
C14 Re1 C13 90.2(6) . . ?
C1 N1 Re1 126.6(9) . . ?
C5 N1 Re1 116.5(8) . . ?
C5 N1 C1 116.9(11) . . ?
C6 N2 Re1 117.2(7) . . ?
C10 N2 Re1 124.2(8) . . ?
C10 N2 C6 118.6(10) . . ?
N1 C1 H1 117.8 . . ?
C2 C1 N1 124.3(14) . . ?
C2 C1 H1 117.8 . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.1(14) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.8(13) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.7(13) . . ?
C5 C4 H4 119.6 . . ?
N1 C5 C4 120.1(12) . . ?
N1 C5 C6 117.3(11) . . ?
C4 C5 C6 122.7(11) . . ?
N2 C6 C5 114.4(10) . . ?
N2 C6 C7 120.5(11) . . ?
C7 C6 C5 125.1(11) . . ?
C6 C7 H7 120.6 . . ?
C6 C7 C8 118.9(12) . . ?
C8 C7 H7 120.6 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.5(12) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 118.8(12) . . ?
C8 C9 C11 122.8(12) . . ?
C10 C9 C11 118.4(12) . . ?
N2 C10 C9 122.7(12) . . ?
N2 C10 H10 118.6 . . ?
C9 C10 H10 118.6 . . ?
Br1 C11 H11A 109.8 . . ?
Br1 C11 H11B 109.8 . . ?
C9 C11 Br1 109.5(9) . . ?
C9 C11 H11A 109.8 . . ?
C9 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
O1 C12 Re1 178.8(13) . . ?
O2 C13 Re1 178.7(14) . . ?
O3 C14 Re1 179.3(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Re1 N1 C1 C2 -176.9(11) . . . . ?
Re1 N1 C5 C4 178.3(8) . . . . ?
Re1 N1 C5 C6 -1.1(12) . . . . ?
Re1 N2 C6 C5 -2.9(11) . . . . ?
Re1 N2 C6 C7 175.7(8) . . . . ?
Re1 N2 C10 C9 -176.6(8) . . . . ?
N1 C1 C2 C3 -3(2) . . . . ?
N1 C5 C6 N2 2.7(14) . . . . ?
N1 C5 C6 C7 -175.9(10) . . . . ?
N2 C6 C7 C8 1.6(16) . . . . ?
C1 N1 C5 C4 -2.1(16) . . . . ?
C1 N1 C5 C6 178.5(10) . . . . ?
C1 C2 C3 C4 1(2) . . . . ?
C2 C3 C4 C5 0(2) . . . . ?
C3 C4 C5 N1 0.4(18) . . . . ?
C3 C4 C5 C6 179.7(11) . . . . ?
C4 C5 C6 N2 -176.7(10) . . . . ?
C4 C5 C6 C7 4.7(17) . . . . ?
C5 N1 C1 C2 3(2) . . . . ?
C5 C6 C7 C8 -179.9(11) . . . . ?
C6 N2 C10 C9 0.0(16) . . . . ?
C6 C7 C8 C9 -0.8(18) . . . . ?
C7 C8 C9 C10 -0.3(18) . . . . ?
C7 C8 C9 C11 -178.9(12) . . . . ?
C8 C9 C10 N2 0.8(17) . . . . ?
C8 C9 C11 Br1 87.7(13) . . . . ?
C10 N2 C6 C5 -179.8(9) . . . . ?
C10 N2 C6 C7 -1.1(15) . . . . ?
C10 C9 C11 Br1 -90.9(12) . . . . ?
C11 C9 C10 N2 179.5(10) . . . . ?

_olex2_exptl_crystal_mounting_method 'om loop with oil'
_olex2_submission_special_instructions 'No special instructions were received'
_vrf_PLAT029_m-rebr              
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.956 Why?  
RESPONSE: small crystal with low diffraction intensities in high angles
;
_vrf_PLAT971_m-rebr              
;
PROBLEM: Check Calcd Resid. Dens.  0.85A   From Re1             6.82 eA-3  
RESPONSE: possible unsolved problem of twinning
;
####################################################################### 
# 
# 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_m-reme-03_b
_database_code_depnum_ccdc_archive 'CCDC 2090794'
loop_
_audit_author_name
_audit_author_address
'Aurelien Crochet'
;University of Fribourg, Chemistry Department
Switzerland
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2023-03-09 downloaded from the CCDC.
;
_audit_creation_date             2021-01-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
isabelle.kolly@unifr.ch
aurelien.crochet@unifr.ch
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H10 Br N2 O3 Re'
_chemical_formula_sum            'C14 H10 Br N2 O3 Re'
_chemical_formula_weight         520.35
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -5.2083 5.8923 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   14.9333(5)
_cell_length_b                   11.3306(2)
_cell_length_c                   9.2074(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.894(2)
_cell_angle_gamma                90
_cell_volume                     1490.69(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    73121
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      67.92
_cell_measurement_theta_min      3.90
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    19.192
_exptl_absorpt_correction_T_max  0.1550
_exptl_absorpt_correction_T_min  0.0180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270. Afterwards scaling of
reflection intensities was performed within STOE LANA. J. Koziskova, F. Hahn,
J. Richter, J. Kozisek, Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136-140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             968
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'layering of DCm and pentane'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_Laue_measured_fraction_full 0.947
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            21439
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.240
_diffrn_reflns_theta_max         67.240
_diffrn_reflns_theta_min         4.982
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 Pilatus300K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'Dectris Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '1.2 mm, 0.6 diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Primux 100 micro'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.998
_reflns_Friedel_fraction_full    0.949
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                3849
_reflns_number_total             3882
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         3.136
_refine_diff_density_min         -2.008
_refine_diff_density_rms         0.186
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.41(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         3882
_refine_ls_number_restraints     152
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0859P)²+6.7127P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1207
_refine_special_details          
'refined as an inversion twin, but some problems of twinning still exist.'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.59(3)
 0.41(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
N1 \\sim C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5: within 2A with sigma of 0.001
and sigma for terminal atoms of 0.002 within 2A
N2 \\sim C6 \\sim C7 \\sim C8 \\sim C9 \\sim C10: within 2A with sigma of 0.001
and sigma for terminal atoms of 0.002 within 2A
N3 \\sim C15 \\sim C16 \\sim C17 \\sim C18 \\sim C19: within 2A with sigma of
0.001 and sigma for terminal atoms of 0.002 within 2A
N4 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24: within 2A with sigma of
0.001 and sigma for terminal atoms of 0.002 within 2A
4. Rigid body (RIGU) restrains
 C27, O5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C26, O4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C10(H10), C15(H15), C16(H16),
 C17(H17), C18(H18), C21(H21), C22(H22), C24(H24)
5.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Re1 Re 0.70535(4) 0.16372(6) 0.63491(6) 0.0407(3) Uani 1 1 d . . . . .
Br1 Br 0.84537(19) 0.2035(2) 0.5230(3) 0.0460(5) Uani 1 1 d . . . . .
O1 O 0.5661(13) 0.1520(14) 0.312(2) 0.063(6) Uani 1 1 d . . . . .
O2 O 0.7221(17) -0.1039(14) 0.636(3) 0.068(6) Uani 1 1 d . . . . .
O3 O 0.5477(13) 0.1184(14) 0.772(3) 0.065(5) Uani 1 1 d . . . . .
N1 N 0.8076(18) 0.200(2) 0.846(3) 0.063(2) Uani 1 1 d . U . . .
N2 N 0.7066(18) 0.3555(17) 0.662(3) 0.053(2) Uani 1 1 d . U . . .
C1 C 0.8601(17) 0.110(2) 0.941(3) 0.063(2) Uani 1 1 d . U . . .
H1 H 0.849822 0.032640 0.905538 0.076 Uiso 1 1 calc R U . . .
C2 C 0.9249(15) 0.126(2) 1.081(3) 0.063(2) Uani 1 1 d . U . . .
H2 H 0.956313 0.064086 1.139924 0.076 Uiso 1 1 calc R U . . .
C3 C 0.9388(14) 0.239(2) 1.124(2) 0.064(2) Uani 1 1 d . U . . .
H3 H 0.982429 0.254677 1.217538 0.076 Uiso 1 1 calc R U . . .
C4 C 0.8934(17) 0.334(2) 1.042(3) 0.063(2) Uani 1 1 d . U . . .
H4 H 0.905816 0.410643 1.077646 0.076 Uiso 1 1 calc R U . . .
C5 C 0.8277(18) 0.311(2) 0.901(3) 0.063(2) Uani 1 1 d . U . . .
C6 C 0.7707(15) 0.3951(16) 0.790(3) 0.053(2) Uani 1 1 d . U . . .
C7 C 0.7804(14) 0.5186(16) 0.818(2) 0.054(2) Uani 1 1 d . U . . .
H7 H 0.825060 0.547805 0.903190 0.065 Uiso 1 1 calc R U . . .
C8 C 0.7258(14) 0.5885(17) 0.723(2) 0.054(2) Uani 1 1 d . U . . .
H8 H 0.732507 0.669039 0.742699 0.065 Uiso 1 1 calc R U . . .
C9 C 0.6563(14) 0.5531(17) 0.590(2) 0.054(2) Uani 1 1 d . U . . .
C10 C 0.6525(15) 0.4276(18) 0.565(3) 0.053(2) Uani 1 1 d . U . . .
H10 H 0.610800 0.397347 0.476989 0.064 Uiso 1 1 calc R U . . .
C11 C 0.5950(16) 0.6275(17) 0.480(2) 0.064(5) Uani 1 1 d . . . . .
H11A H 0.561799 0.678852 0.529249 0.097 Uiso 1 1 calc R U . . .
H11B H 0.551061 0.579693 0.406623 0.097 Uiso 1 1 calc R U . . .
H11C H 0.630889 0.673866 0.429693 0.097 Uiso 1 1 calc R U . . .
C12 C 0.6197(16) 0.149(2) 0.440(3) 0.047(5) Uani 1 1 d . . . . .
C13 C 0.716(2) -0.0089(15) 0.632(3) 0.048(6) Uani 1 1 d . . . . .
C14 C 0.6047(14) 0.141(2) 0.738(3) 0.048(6) Uani 1 1 d . . . . .
Re2 Re 0.30325(4) 0.33155(6) 0.33598(7) 0.0432(3) Uani 1 1 d . . . . .
Br2 Br 0.1628(2) 0.2945(2) 0.4495(3) 0.0501(5) Uani 1 1 d . . . . .
O4 O 0.2871(15) 0.6021(13) 0.342(3) 0.058(5) Uani 1 1 d . . . . .
O5 O 0.4476(17) 0.364(2) 0.649(3) 0.076(5) Uani 1 1 d . . . . .
O6 O 0.4586(16) 0.365(2) 0.187(3) 0.086(7) Uani 1 1 d . . . . .
N3 N 0.3109(18) 0.1404(17) 0.323(3) 0.062(2) Uani 1 1 d . U . . .
N4 N 0.1989(17) 0.2855(16) 0.117(3) 0.054(2) Uani 1 1 d . U . . .
C15 C 0.3729(16) 0.0753(18) 0.431(3) 0.062(2) Uani 1 1 d . U . . .
H15 H 0.413750 0.114360 0.512260 0.075 Uiso 1 1 calc R U . . .
C16 C 0.3779(15) -0.0463(16) 0.424(3) 0.062(2) Uani 1 1 d . U . . .
H16 H 0.420844 -0.088138 0.500420 0.075 Uiso 1 1 calc R U . . .
C17 C 0.3188(15) -0.1032(17) 0.305(3) 0.063(2) Uani 1 1 d . U . . .
H17 H 0.319950 -0.185016 0.297738 0.075 Uiso 1 1 calc R U . . .
C18 C 0.2558(15) -0.0354(17) 0.193(3) 0.063(2) Uani 1 1 d . U . . .
H18 H 0.215875 -0.073329 0.109027 0.075 Uiso 1 1 calc R U . . .
C19 C 0.2517(16) 0.0834(17) 0.203(3) 0.062(2) Uani 1 1 d . U . . .
C20 C 0.1916(17) 0.1652(16) 0.092(3) 0.055(2) Uani 1 1 d . U . . .
C21 C 0.1292(13) 0.1203(18) -0.035(2) 0.055(2) Uani 1 1 d . U . . .
H21 H 0.120535 0.039414 -0.049044 0.066 Uiso 1 1 calc R U . . .
C22 C 0.0789(14) 0.2008(19) -0.142(3) 0.055(2) Uani 1 1 d . U . . .
H22 H 0.036757 0.173697 -0.231350 0.066 Uiso 1 1 calc R U . . .
C23 C 0.0912(15) 0.3219(18) -0.116(3) 0.055(2) Uani 1 1 d . U . . .
C24 C 0.1516(17) 0.3574(19) 0.023(3) 0.055(2) Uani 1 1 d . U . . .
H24 H 0.156776 0.437443 0.046577 0.066 Uiso 1 1 calc R U . . .
C25 C 0.0372(12) 0.4100(19) -0.228(2) 0.065(5) Uani 1 1 d . . . . .
H25A H 0.043454 0.392829 -0.326359 0.098 Uiso 1 1 calc R U . . .
H25B H 0.060962 0.487657 -0.197139 0.098 Uiso 1 1 calc R U . . .
H25C H -0.027605 0.406239 -0.231179 0.098 Uiso 1 1 calc R U . . .
C26 C 0.2884(14) 0.4951(15) 0.332(3) 0.046(5) Uani 1 1 d . . . . .
C27 C 0.393(2) 0.347(2) 0.529(4) 0.055(6) Uani 1 1 d . . . . .
C28 C 0.4010(19) 0.353(2) 0.254(3) 0.055(6) 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 Br1 2.624(3) . ?
Re1 N1 2.14(2) . ?
Re1 N2 2.187(19) . ?
Re1 C12 1.88(3) . ?
Re1 C13 1.963(18) . ?
Re1 C14 2.01(2) . ?
O1 C12 1.22(3) . ?
O2 C13 1.08(2) . ?
O3 C14 1.02(3) . ?
N1 C1 1.43(4) . ?
N1 C5 1.35(3) . ?
N2 C6 1.36(3) . ?
N2 C10 1.31(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.38(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.34(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.38(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.41(3) . ?
C5 C6 1.48(3) . ?
C6 C7 1.42(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.28(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.41(3) . ?
C9 C10 1.44(3) . ?
C9 C11 1.43(3) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
Re2 Br2 2.634(3) . ?
Re2 N3 2.17(2) . ?
Re2 N4 2.22(2) . ?
Re2 C26 1.865(18) . ?
Re2 C27 1.90(3) . ?
Re2 C28 1.84(3) . ?
O4 C26 1.22(2) . ?
O5 C27 1.19(4) . ?
O6 C28 1.20(3) . ?
N3 C15 1.36(3) . ?
N3 C19 1.36(4) . ?
N4 C20 1.38(3) . ?
N4 C24 1.25(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.38(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.36(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.41(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.35(3) . ?
C19 C20 1.47(3) . ?
C20 C21 1.36(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.39(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.39(3) . ?
C23 C24 1.40(3) . ?
C23 C25 1.49(3) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Re1 Br1 83.4(8) . . ?
N1 Re1 N2 73.8(9) . . ?
N2 Re1 Br1 83.9(6) . . ?
C12 Re1 Br1 92.3(9) . . ?
C12 Re1 N1 173.0(10) . . ?
C12 Re1 N2 100.3(10) . . ?
C12 Re1 C13 86.3(11) . . ?
C12 Re1 C14 92.5(11) . . ?
C13 Re1 Br1 95.0(7) . . ?
C13 Re1 N1 99.5(11) . . ?
C13 Re1 N2 173.4(12) . . ?
C13 Re1 C14 87.5(10) . . ?
C14 Re1 Br1 174.7(7) . . ?
C14 Re1 N1 91.7(10) . . ?
C14 Re1 N2 93.1(9) . . ?
C1 N1 Re1 122.5(17) . . ?
C5 N1 Re1 122.9(18) . . ?
C5 N1 C1 115(2) . . ?
C6 N2 Re1 114.1(16) . . ?
C10 N2 Re1 124.0(16) . . ?
C10 N2 C6 121.9(18) . . ?
N1 C1 H1 117.1 . . ?
C2 C1 N1 126(2) . . ?
C2 C1 H1 117.1 . . ?
C1 C2 H2 122.7 . . ?
C3 C2 C1 115(2) . . ?
C3 C2 H2 122.7 . . ?
C2 C3 H3 117.6 . . ?
C2 C3 C4 125(2) . . ?
C4 C3 H3 117.6 . . ?
C3 C4 H4 121.2 . . ?
C3 C4 C5 118(2) . . ?
C5 C4 H4 121.2 . . ?
N1 C5 C4 123(2) . . ?
N1 C5 C6 109(2) . . ?
C4 C5 C6 129(2) . . ?
N2 C6 C5 120.3(18) . . ?
N2 C6 C7 119.4(19) . . ?
C7 C6 C5 120(2) . . ?
C6 C7 H7 120.9 . . ?
C8 C7 C6 118(2) . . ?
C8 C7 H7 120.9 . . ?
C7 C8 H8 117.4 . . ?
C7 C8 C9 125.3(18) . . ?
C9 C8 H8 117.4 . . ?
C8 C9 C10 114.0(18) . . ?
C8 C9 C11 127.3(19) . . ?
C11 C9 C10 118.6(19) . . ?
N2 C10 C9 121(2) . . ?
N2 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 Re1 173(2) . . ?
O2 C13 Re1 177(3) . . ?
O3 C14 Re1 168(2) . . ?
N3 Re2 Br2 85.6(6) . . ?
N3 Re2 N4 75.6(9) . . ?
N4 Re2 Br2 83.8(6) . . ?
C26 Re2 Br2 93.6(8) . . ?
C26 Re2 N3 175.2(11) . . ?
C26 Re2 N4 99.7(9) . . ?
C26 Re2 C27 88.6(10) . . ?
C27 Re2 Br2 94.3(10) . . ?
C27 Re2 N3 96.1(10) . . ?
C27 Re2 N4 171.6(9) . . ?
C28 Re2 Br2 178.3(8) . . ?
C28 Re2 N3 92.9(10) . . ?
C28 Re2 N4 95.2(11) . . ?
C28 Re2 C26 87.9(11) . . ?
C28 Re2 C27 86.5(13) . . ?
C15 N3 Re2 122.4(18) . . ?
C15 N3 C19 118.6(19) . . ?
C19 N3 Re2 119.0(17) . . ?
C20 N4 Re2 112.7(18) . . ?
C24 N4 Re2 125.6(15) . . ?
C24 N4 C20 122(2) . . ?
N3 C15 H15 118.5 . . ?
N3 C15 C16 123(2) . . ?
C16 C15 H15 118.5 . . ?
C15 C16 H16 120.7 . . ?
C17 C16 C15 119(2) . . ?
C17 C16 H16 120.7 . . ?
C16 C17 H17 120.8 . . ?
C16 C17 C18 118.4(19) . . ?
C18 C17 H17 120.8 . . ?
C17 C18 H18 119.1 . . ?
C19 C18 C17 122(2) . . ?
C19 C18 H18 119.1 . . ?
N3 C19 C20 112.7(18) . . ?
C18 C19 N3 120(2) . . ?
C18 C19 C20 127(2) . . ?
N4 C20 C19 120(2) . . ?
C21 C20 N4 121(2) . . ?
C21 C20 C19 119.1(19) . . ?
C20 C21 H21 121.4 . . ?
C20 C21 C22 117.2(18) . . ?
C22 C21 H21 121.4 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120(2) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C24 117(2) . . ?
C22 C23 C25 122(2) . . ?
C24 C23 C25 121.0(19) . . ?
N4 C24 C23 122(2) . . ?
N4 C24 H24 118.8 . . ?
C23 C24 H24 118.8 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O4 C26 Re2 173(2) . . ?
O5 C27 Re2 175(2) . . ?
O6 C28 Re2 174(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Re1 N1 C1 C2 -177.8(19) . . . . ?
Re1 N1 C5 C4 178(2) . . . . ?
Re1 N1 C5 C6 -2(3) . . . . ?
Re1 N2 C6 C5 -4(3) . . . . ?
Re1 N2 C6 C7 178.0(15) . . . . ?
Re1 N2 C10 C9 179.4(14) . . . . ?
N1 C1 C2 C3 -2(3) . . . . ?
N1 C5 C6 N2 4(3) . . . . ?
N1 C5 C6 C7 -178(2) . . . . ?
N2 C6 C7 C8 2(3) . . . . ?
C1 N1 C5 C4 -2(4) . . . . ?
C1 N1 C5 C6 178(2) . . . . ?
C1 C2 C3 C4 1(3) . . . . ?
C2 C3 C4 C5 0(3) . . . . ?
C3 C4 C5 N1 1(4) . . . . ?
C3 C4 C5 C6 -179(2) . . . . ?
C4 C5 C6 N2 -176(2) . . . . ?
C4 C5 C6 C7 2(4) . . . . ?
C5 N1 C1 C2 2(4) . . . . ?
C5 C6 C7 C8 -176(2) . . . . ?
C6 N2 C10 C9 -2(3) . . . . ?
C6 C7 C8 C9 0(3) . . . . ?
C7 C8 C9 C10 -2(3) . . . . ?
C7 C8 C9 C11 -179(2) . . . . ?
C8 C9 C10 N2 3(3) . . . . ?
C10 N2 C6 C5 177(2) . . . . ?
C10 N2 C6 C7 -1(3) . . . . ?
C11 C9 C10 N2 -180(2) . . . . ?
Re2 N3 C15 C16 179.5(16) . . . . ?
Re2 N3 C19 C18 179.6(17) . . . . ?
Re2 N3 C19 C20 2(3) . . . . ?
Re2 N4 C20 C19 -2(3) . . . . ?
Re2 N4 C20 C21 178.2(16) . . . . ?
Re2 N4 C24 C23 176.1(16) . . . . ?
N3 C15 C16 C17 1(3) . . . . ?
N3 C19 C20 N4 0(3) . . . . ?
N3 C19 C20 C21 180(2) . . . . ?
N4 C20 C21 C22 5(3) . . . . ?
C15 N3 C19 C18 0(3) . . . . ?
C15 N3 C19 C20 -177(2) . . . . ?
C15 C16 C17 C18 1(3) . . . . ?
C16 C17 C18 C19 -1(3) . . . . ?
C17 C18 C19 N3 1(3) . . . . ?
C17 C18 C19 C20 178(2) . . . . ?
C18 C19 C20 N4 -177(2) . . . . ?
C18 C19 C20 C21 3(3) . . . . ?
C19 N3 C15 C16 -1(4) . . . . ?
C19 C20 C21 C22 -175.3(18) . . . . ?
C20 N4 C24 C23 -3(4) . . . . ?
C20 C21 C22 C23 -2(3) . . . . ?
C21 C22 C23 C24 -3(3) . . . . ?
C21 C22 C23 C25 -178.9(19) . . . . ?
C22 C23 C24 N4 6(3) . . . . ?
C24 N4 C20 C19 177(2) . . . . ?
C24 N4 C20 C21 -3(4) . . . . ?
C25 C23 C24 N4 -179(2) . . . . ?

_olex2_submission_original_sample_id m-ReMe
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.59(3)
2 0.41(3)

####################################################################### 
# 
# 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_rebrnn16
_database_code_depnum_ccdc_archive 'CCDC 2090795'
loop_
_audit_author_name
_audit_author_address
'Aurelien Crochet'
;University of Fribourg, Chemistry Department
Switzerland
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2023-03-09 downloaded from the CCDC.
;
_audit_creation_date             2020-09-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
isabelle.kolly@unifr.ch
aurelien.crochet@unifr.ch
fabio.zobi@unifr.ch
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H9 Br Cl N2 O3 Re'
_chemical_formula_sum            'C14 H9 Br Cl N2 O3 Re'
_chemical_formula_weight         554.79
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -5.2083 5.8923 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.8442(3)
_cell_length_b                   11.1458(3)
_cell_length_c                   21.9911(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.621(2)
_cell_angle_gamma                90
_cell_volume                     3144.93(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    30075
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      68.26
_cell_measurement_theta_min      4.02
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    19.781
_exptl_absorpt_correction_T_max  0.2917
_exptl_absorpt_correction_T_min  0.0962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270. Afterwards scaling of
reflection intensities was performed within STOE LANA. J. Koziskova, F. Hahn,
J. Richter, J. Kozisek, Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136-140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2064
_exptl_crystal_recrystallization_method 'diffusion of chloroform and pentane'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 0.942
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15339
_diffrn_reflns_point_group_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.377
_diffrn_reflns_theta_max         67.377
_diffrn_reflns_theta_min         4.025
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 Pilatus300K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'Dectris Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '1.2 mm, 0.6 diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Primux 100 micro'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2555
_reflns_number_total             2664
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.714
_refine_diff_density_min         -2.141
_refine_diff_density_rms         0.187
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2664
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.172
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²+97.7940P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1178
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Re1 Re 0.28357(3) 0.52660(4) 0.66419(2) 0.03085(17) Uani 1 1 d . . . . .
Br1 Br 0.18350(10) 0.55201(12) 0.55967(6) 0.0509(3) Uani 1 1 d . . . . .
Cl1 Cl 0.33080(19) 0.2122(2) 0.56301(11) 0.0382(5) Uani 1 1 d . . . . .
O1 O 0.1059(8) 0.6358(11) 0.7327(5) 0.082(3) Uani 1 1 d . . . . .
O2 O 0.1767(8) 0.2848(9) 0.6837(4) 0.072(3) Uani 1 1 d . . . . .
O3 O 0.3966(6) 0.4961(8) 0.7869(4) 0.054(2) Uani 1 1 d . . . . .
N1 N 0.3490(6) 0.7010(7) 0.6433(4) 0.0328(18) Uani 1 1 d . . . . .
N2 N 0.4272(6) 0.4875(7) 0.6133(4) 0.0297(17) Uani 1 1 d . . . . .
C1 C 0.3059(9) 0.8060(10) 0.6589(5) 0.043(2) Uani 1 1 d . . . . .
H1 H 0.249110 0.804026 0.683576 0.051 Uiso 1 1 calc R U . . .
C2 C 0.3411(10) 0.9158(10) 0.6404(6) 0.053(3) Uani 1 1 d . . . . .
H2 H 0.309941 0.986683 0.652548 0.063 Uiso 1 1 calc R U . . .
C3 C 0.4248(10) 0.9167(11) 0.6030(6) 0.055(3) Uani 1 1 d . . . . .
H3 H 0.450023 0.989193 0.588788 0.066 Uiso 1 1 calc R U . . .
C4 C 0.4707(9) 0.8115(11) 0.5868(6) 0.049(3) Uani 1 1 d . . . . .
H4 H 0.527381 0.811969 0.561973 0.058 Uiso 1 1 calc R U . . .
C5 C 0.4315(7) 0.7045(9) 0.6078(4) 0.031(2) Uani 1 1 d . . . . .
C6 C 0.4776(7) 0.5865(9) 0.5940(4) 0.031(2) Uani 1 1 d . . . . .
C7 C 0.5708(8) 0.5795(11) 0.5643(5) 0.040(2) Uani 1 1 d . . . . .
H7 H 0.604033 0.648825 0.551848 0.048 Uiso 1 1 calc R U . . .
C8 C 0.6130(8) 0.4685(11) 0.5537(5) 0.046(3) Uani 1 1 d . . . . .
H8 H 0.674402 0.461478 0.533114 0.055 Uiso 1 1 calc R U . . .
C9 C 0.5637(8) 0.3699(11) 0.5736(5) 0.045(3) Uani 1 1 d . . . . .
H9 H 0.592180 0.294406 0.567237 0.054 Uiso 1 1 calc R U . . .
C10 C 0.4724(8) 0.3797(9) 0.6030(4) 0.035(2) Uani 1 1 d . . . . .
C11 C 0.4230(9) 0.2683(10) 0.6232(5) 0.046(3) Uani 1 1 d . . . . .
H11A H 0.386193 0.283483 0.659949 0.055 Uiso 1 1 calc R U . . .
H11B H 0.476006 0.208193 0.632307 0.055 Uiso 1 1 calc R U . . .
C12 C 0.1717(9) 0.5929(13) 0.7064(5) 0.052(3) Uani 1 1 d . . . . .
C13 C 0.2194(9) 0.3731(11) 0.6751(5) 0.045(3) Uani 1 1 d . . . . .
C14 C 0.3598(8) 0.5080(10) 0.7424(5) 0.037(2) 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 Br1 2.5970(13) . ?
Re1 N1 2.175(8) . ?
Re1 N2 2.245(8) . ?
Re1 C12 1.896(12) . ?
Re1 C13 1.919(11) . ?
Re1 C14 1.950(12) . ?
Cl1 C11 1.843(11) . ?
O1 C12 1.150(15) . ?
O2 C13 1.147(14) . ?
O3 C14 1.076(13) . ?
N1 C1 1.346(13) . ?
N1 C5 1.344(12) . ?
N2 C6 1.357(12) . ?
N2 C10 1.357(13) . ?
C1 H1 0.9300 . ?
C1 C2 1.372(17) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(18) . ?
C3 H3 0.9300 . ?
C3 C4 1.366(17) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(15) . ?
C5 C6 1.480(14) . ?
C6 C7 1.391(14) . ?
C7 H7 0.9300 . ?
C7 C8 1.375(16) . ?
C8 H8 0.9300 . ?
C8 C9 1.352(17) . ?
C9 H9 0.9300 . ?
C9 C10 1.370(15) . ?
C10 C11 1.472(15) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Re1 Br1 84.0(2) . . ?
N1 Re1 N2 74.5(3) . . ?
N2 Re1 Br1 88.0(2) . . ?
C12 Re1 Br1 92.0(4) . . ?
C12 Re1 N1 93.7(5) . . ?
C12 Re1 N2 168.1(5) . . ?
C12 Re1 C13 87.0(6) . . ?
C12 Re1 C14 88.3(5) . . ?
C13 Re1 Br1 90.5(3) . . ?
C13 Re1 N1 174.5(4) . . ?
C13 Re1 N2 104.9(4) . . ?
C13 Re1 C14 89.8(4) . . ?
C14 Re1 Br1 179.5(3) . . ?
C14 Re1 N1 95.6(4) . . ?
C14 Re1 N2 91.6(4) . . ?
C1 N1 Re1 123.8(7) . . ?
C5 N1 Re1 118.1(6) . . ?
C5 N1 C1 117.8(9) . . ?
C6 N2 Re1 114.4(6) . . ?
C6 N2 C10 117.0(8) . . ?
C10 N2 Re1 128.4(7) . . ?
N1 C1 H1 118.1 . . ?
N1 C1 C2 123.8(11) . . ?
C2 C1 H1 118.1 . . ?
C1 C2 H2 121.4 . . ?
C1 C2 C3 117.2(11) . . ?
C3 C2 H2 121.4 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.3(11) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.0(11) . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.8(10) . . ?
N1 C5 C6 115.3(8) . . ?
C4 C5 C6 122.9(9) . . ?
N2 C6 C5 117.2(8) . . ?
N2 C6 C7 122.3(9) . . ?
C7 C6 C5 120.5(9) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 C6 119.0(10) . . ?
C8 C7 H7 120.5 . . ?
C7 C8 H8 120.6 . . ?
C9 C8 C7 118.9(10) . . ?
C9 C8 H8 120.6 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.8(11) . . ?
C10 C9 H9 119.6 . . ?
N2 C10 C9 122.1(10) . . ?
N2 C10 C11 120.2(9) . . ?
C9 C10 C11 117.7(10) . . ?
Cl1 C11 H11A 109.7 . . ?
Cl1 C11 H11B 109.7 . . ?
C10 C11 Cl1 110.0(7) . . ?
C10 C11 H11A 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
O1 C12 Re1 177.9(13) . . ?
O2 C13 Re1 175.8(12) . . ?
O3 C14 Re1 175.9(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Re1 N1 C1 C2 -173.1(9) . . . . ?
Re1 N1 C5 C4 172.7(8) . . . . ?
Re1 N1 C5 C6 -8.2(11) . . . . ?
Re1 N2 C6 C5 -1.0(10) . . . . ?
Re1 N2 C6 C7 176.8(7) . . . . ?
Re1 N2 C10 C9 -176.6(7) . . . . ?
Re1 N2 C10 C11 4.0(13) . . . . ?
N1 C1 C2 C3 0.9(18) . . . . ?
N1 C5 C6 N2 6.0(12) . . . . ?
N1 C5 C6 C7 -171.9(9) . . . . ?
N2 C6 C7 C8 0.5(15) . . . . ?
N2 C10 C11 Cl1 88.7(10) . . . . ?
C1 N1 C5 C4 -1.1(15) . . . . ?
C1 N1 C5 C6 177.9(9) . . . . ?
C1 C2 C3 C4 -1(2) . . . . ?
C2 C3 C4 C5 1(2) . . . . ?
C3 C4 C5 N1 0.6(17) . . . . ?
C3 C4 C5 C6 -178.3(11) . . . . ?
C4 C5 C6 N2 -175.0(10) . . . . ?
C4 C5 C6 C7 7.2(15) . . . . ?
C5 N1 C1 C2 0.3(16) . . . . ?
C5 C6 C7 C8 178.2(9) . . . . ?
C6 N2 C10 C9 -1.2(14) . . . . ?
C6 N2 C10 C11 179.4(9) . . . . ?
C6 C7 C8 C9 -1.4(16) . . . . ?
C7 C8 C9 C10 1.1(17) . . . . ?
C8 C9 C10 N2 0.3(16) . . . . ?
C8 C9 C10 C11 179.7(10) . . . . ?
C9 C10 C11 Cl1 -90.7(10) . . . . ?
C10 N2 C6 C5 -177.0(8) . . . . ?
C10 N2 C6 C7 0.8(14) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on Mitengen loop with oil'
_olex2_submission_special_instructions 'No special instructions were received'
_vrf_PLAT029_rebrnn16            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.942 Why?  
RESPONSE: low diffraction intensities in high angles
;
####################################################################### 
# 
# 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_m-ref2-02
_database_code_depnum_ccdc_archive 'CCDC 2090793'
loop_
_audit_author_name
_audit_author_address
'Aurelien Crochet'
;University of Fribourg, Chemistry Department
Switzerland
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2023-03-09 downloaded from the CCDC.
;
_audit_creation_date             2020-11-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
isabelle.kolly@unifr.ch
aurelien.crochet@unifr.ch
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 Br F2 N2 O3 Re'
_chemical_formula_sum            'C14 H8 Br F2 N2 O3 Re'
_chemical_formula_weight         556.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -5.2083 5.8923 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   14.7874(5)
_cell_length_b                   11.5066(2)
_cell_length_c                   8.8657(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.420(3)
_cell_angle_gamma                90
_cell_volume                     1507.18(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    35204
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      68.45
_cell_measurement_theta_min      3.84
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    19.246
_exptl_absorpt_correction_T_max  0.4785
_exptl_absorpt_correction_T_min  0.0792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270. Afterwards scaling of
reflection intensities was performed within STOE LANA. J. Koziskova, F. Hahn,
J. Richter, J. Kozisek, Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136-140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.452
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1032
_exptl_crystal_recrystallization_method 'layering of DCM and hexane'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.929
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            15368
_diffrn_reflns_point_group_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        67.536
_diffrn_reflns_theta_max         67.536
_diffrn_reflns_theta_min         4.872
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 Pilatus300K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'Dectris Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.929
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '1.2 mm, 0.6 diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Primux 100 micro'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2528
_reflns_number_total             2535
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.003
_refine_diff_density_min         -0.691
_refine_diff_density_rms         0.124
_refine_ls_extinction_coef       0.00038(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.236
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2535
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0241
_refine_ls_restrained_S_all      1.236
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0282P)²+4.0378P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0625
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Re1 Re 0.81739(2) 0.41388(2) 0.69705(2) 0.01939(10) Uani 1 1 d . . . . .
Br1 Br 0.68441(3) 0.45288(4) 0.87734(5) 0.02716(14) Uani 1 1 d . . . . .
F1 F 0.4567(3) 0.2982(4) 0.3293(4) 0.0587(10) Uani 1 1 d . . . . .
F2 F 0.5270(3) 0.3215(4) 0.1273(4) 0.0701(13) Uani 1 1 d . . . . .
O1 O 0.9655(3) 0.3775(4) 0.4724(5) 0.0439(9) Uani 1 1 d . . . . .
O2 O 0.8015(3) 0.1486(3) 0.7132(4) 0.0350(8) Uani 1 1 d . . . . .
O3 O 0.9543(3) 0.3904(3) 0.9649(5) 0.0417(9) Uani 1 1 d . . . . .
N1 N 0.8184(2) 0.6019(3) 0.6738(4) 0.0219(8) Uani 1 1 d . . . . .
N2 N 0.7131(2) 0.4520(3) 0.5246(4) 0.0200(7) Uani 1 1 d . . . . .
C1 C 0.8749(3) 0.6737(4) 0.7516(5) 0.0270(10) Uani 1 1 d . . . . .
H1 H 0.919161 0.641675 0.816678 0.032 Uiso 1 1 calc R U . . .
C2 C 0.8697(3) 0.7936(4) 0.7384(6) 0.0321(11) Uani 1 1 d . . . . .
H2 H 0.909547 0.841005 0.794196 0.039 Uiso 1 1 calc R U . . .
C3 C 0.8049(4) 0.8413(4) 0.6417(6) 0.0321(11) Uani 1 1 d . . . . .
H3 H 0.800367 0.921505 0.631158 0.039 Uiso 1 1 calc R U . . .
C4 C 0.7467(3) 0.7688(4) 0.5605(6) 0.0300(10) Uani 1 1 d . . . . .
H4 H 0.702414 0.799886 0.494595 0.036 Uiso 1 1 calc R U . . .
C5 C 0.7545(3) 0.6493(4) 0.5778(5) 0.0221(9) Uani 1 1 d . . . . .
C6 C 0.6966(3) 0.5658(4) 0.4938(5) 0.0240(9) Uani 1 1 d . . . . .
C7 C 0.6293(4) 0.5980(4) 0.3886(6) 0.0350(12) Uani 1 1 d . . . . .
H7 H 0.619156 0.676280 0.367727 0.042 Uiso 1 1 calc R U . . .
C8 C 0.5774(4) 0.5145(5) 0.3149(6) 0.0368(12) Uani 1 1 d . . . . .
H8 H 0.532367 0.535436 0.243558 0.044 Uiso 1 1 calc R U . . .
C9 C 0.5937(3) 0.3989(4) 0.3492(6) 0.0275(10) Uani 1 1 d . . . . .
C10 C 0.6614(3) 0.3707(4) 0.4531(5) 0.0250(9) Uani 1 1 d . . . . .
H10 H 0.672036 0.292719 0.475028 0.030 Uiso 1 1 calc R U . . .
C11 C 0.5398(3) 0.3022(5) 0.2758(6) 0.0372(12) Uani 1 1 d . . . . .
H11 H 0.570759 0.227795 0.293133 0.045 Uiso 1 1 calc R U . . .
C12 C 0.9105(3) 0.3931(4) 0.5548(6) 0.0257(10) Uani 1 1 d . . . . .
C13 C 0.8062(3) 0.2474(4) 0.7069(5) 0.0243(10) Uani 1 1 d . . . . .
C14 C 0.9039(3) 0.3996(4) 0.8626(6) 0.0279(10) 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 Br1 2.6247(5) . ?
Re1 N1 2.173(4) . ?
Re1 N2 2.170(4) . ?
Re1 C12 1.920(5) . ?
Re1 C13 1.925(5) . ?
Re1 C14 1.912(5) . ?
F1 C11 1.337(7) . ?
F2 C11 1.341(7) . ?
O1 C12 1.131(6) . ?
O2 C13 1.142(6) . ?
O3 C14 1.154(6) . ?
N1 C1 1.345(6) . ?
N1 C5 1.359(6) . ?
N2 C6 1.358(6) . ?
N2 C10 1.350(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.387(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.372(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(6) . ?
C5 C6 1.469(6) . ?
C6 C7 1.385(7) . ?
C7 H7 0.9300 . ?
C7 C8 1.378(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.383(7) . ?
C9 C10 1.371(7) . ?
C9 C11 1.501(7) . ?
C10 H10 0.9300 . ?
C11 H11 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
N1 Re1 Br1 84.03(10) . . ?
N2 Re1 Br1 82.30(10) . . ?
N2 Re1 N1 74.88(14) . . ?
C12 Re1 Br1 175.82(14) . . ?
C12 Re1 N1 93.09(17) . . ?
C12 Re1 N2 94.03(17) . . ?
C12 Re1 C13 88.34(19) . . ?
C13 Re1 Br1 94.26(14) . . ?
C13 Re1 N1 174.73(16) . . ?
C13 Re1 N2 99.97(16) . . ?
C14 Re1 Br1 92.37(16) . . ?
C14 Re1 N1 98.70(17) . . ?
C14 Re1 N2 171.99(16) . . ?
C14 Re1 C12 91.1(2) . . ?
C14 Re1 C13 86.33(18) . . ?
C1 N1 Re1 124.7(3) . . ?
C1 N1 C5 118.3(4) . . ?
C5 N1 Re1 116.9(3) . . ?
C6 N2 Re1 117.0(3) . . ?
C10 N2 Re1 124.2(3) . . ?
C10 N2 C6 118.7(4) . . ?
N1 C1 H1 118.8 . . ?
N1 C1 C2 122.5(4) . . ?
C2 C1 H1 118.8 . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.0(4) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.2(5) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.6(5) . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 121.3(4) . . ?
N1 C5 C6 115.4(4) . . ?
C4 C5 C6 123.2(4) . . ?
N2 C6 C5 115.6(4) . . ?
N2 C6 C7 120.8(4) . . ?
C7 C6 C5 123.6(4) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.2(4) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 120.7 . . ?
C7 C8 C9 118.5(5) . . ?
C9 C8 H8 120.7 . . ?
C8 C9 C11 122.3(4) . . ?
C10 C9 C8 119.4(4) . . ?
C10 C9 C11 118.3(4) . . ?
N2 C10 C9 122.3(4) . . ?
N2 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
F1 C11 F2 105.0(4) . . ?
F1 C11 C9 110.6(4) . . ?
F1 C11 H11 110.2 . . ?
F2 C11 C9 110.7(5) . . ?
F2 C11 H11 110.2 . . ?
C9 C11 H11 110.2 . . ?
O1 C12 Re1 178.0(4) . . ?
O2 C13 Re1 178.5(4) . . ?
O3 C14 Re1 178.2(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
Re1 N1 C1 C2 -176.5(4) . . . . ?
Re1 N1 C5 C4 176.8(3) . . . . ?
Re1 N1 C5 C6 -4.0(5) . . . . ?
Re1 N2 C6 C5 2.4(5) . . . . ?
Re1 N2 C6 C7 -178.0(4) . . . . ?
Re1 N2 C10 C9 177.2(4) . . . . ?
N1 C1 C2 C3 -0.4(7) . . . . ?
N1 C5 C6 N2 1.1(6) . . . . ?
N1 C5 C6 C7 -178.5(5) . . . . ?
N2 C6 C7 C8 0.7(8) . . . . ?
C1 N1 C5 C4 -0.6(7) . . . . ?
C1 N1 C5 C6 178.6(4) . . . . ?
C1 C2 C3 C4 0.1(8) . . . . ?
C2 C3 C4 C5 0.0(8) . . . . ?
C3 C4 C5 N1 0.3(7) . . . . ?
C3 C4 C5 C6 -178.8(5) . . . . ?
C4 C5 C6 N2 -179.8(4) . . . . ?
C4 C5 C6 C7 0.6(8) . . . . ?
C5 N1 C1 C2 0.6(7) . . . . ?
C5 C6 C7 C8 -179.7(5) . . . . ?
C6 N2 C10 C9 0.9(7) . . . . ?
C6 C7 C8 C9 0.5(9) . . . . ?
C7 C8 C9 C10 -1.0(8) . . . . ?
C7 C8 C9 C11 179.3(5) . . . . ?
C8 C9 C10 N2 0.3(8) . . . . ?
C8 C9 C11 F1 -73.1(7) . . . . ?
C8 C9 C11 F2 42.9(7) . . . . ?
C10 N2 C6 C5 179.0(4) . . . . ?
C10 N2 C6 C7 -1.4(7) . . . . ?
C10 C9 C11 F1 107.2(5) . . . . ?
C10 C9 C11 F2 -136.8(5) . . . . ?
C11 C9 C10 N2 -179.9(5) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on loop with oil'
_olex2_submission_special_instructions 'No special instructions were received'
_vrf_PLAT029_m-ref2-02           
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.929 Why?  
RESPONSE: very low diffraction intensities in high angles
;
_vrf_PLAT911_m-ref2-02           
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.599        193 Report
RESPONSE: very low diffraction intensities in high angles
;
####################################################################### 
# 
# 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_o-ref2
_database_code_depnum_ccdc_archive 'CCDC 2090796'
loop_
_audit_author_name
_audit_author_address
'Aurelien Crochet'
;University of Fribourg, Chemistry Department
Switzerland
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2023-03-09 downloaded from the CCDC.
;
_audit_creation_date             2020-11-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
isabelle.kolly@unifr.ch
aurelien.crochet@unifr.ch
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 Br F2 N2 O3 Re'
_chemical_formula_sum            'C14 H8 Br F2 N2 O3 Re'
_chemical_formula_weight         556.33
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -5.2083 5.8923 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   14.1812(2)
_cell_length_b                   7.88910(10)
_cell_length_c                   13.6693(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1529.28(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    84909
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      68.33
_cell_measurement_theta_min      4.49
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    18.968
_exptl_absorpt_correction_T_max  0.16
_exptl_absorpt_correction_T_min  0.0517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270. Afterwards scaling of
reflection intensities was performed within STOE LANA. J. Koziskova, F. Hahn,
J. Richter, J. Kozisek, Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136-140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             1032
_exptl_crystal_recrystallization_method 'layering of DCM and pentane'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0135
_diffrn_reflns_av_unetI/netI     0.0044
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            32442
_diffrn_reflns_point_group_measured_fraction_full 0.705
_diffrn_reflns_point_group_measured_fraction_max 0.704
_diffrn_reflns_theta_full        67.683
_diffrn_reflns_theta_max         67.683
_diffrn_reflns_theta_min         5.608
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 Pilatus300K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'Dectris Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '1.2 mm, 0.6 diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Primux 100 micro'
_reflns_Friedel_coverage         0.385
_reflns_Friedel_fraction_full    0.411
_reflns_Friedel_fraction_max     0.411
_reflns_number_gt                1961
_reflns_number_total             1961
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.792
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details 
;
 Flack x determined using 542 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.028(7)
_refine_ls_extinction_coef       0.00106(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.231
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         1961
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0147
_refine_ls_R_factor_gt           0.0147
_refine_ls_restrained_S_all      1.230
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0227P)²+1.6321P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0387
_refine_ls_wR_factor_ref         0.0387
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Re1 Re 0.76016(2) 0.40694(2) 0.45871(4) 0.02097(10) Uani 1 1 d . . . . .
Br1 Br 0.83490(4) 0.25755(8) 0.61101(5) 0.03155(16) Uani 1 1 d . . . . .
F1 F 0.5603(3) -0.0300(6) 0.3358(3) 0.0539(11) Uani 1 1 d . . . . .
F2 F 0.7002(3) -0.0515(5) 0.3989(3) 0.0475(10) Uani 1 1 d . . . . .
O1 O 0.6585(4) 0.5869(5) 0.2918(4) 0.0419(12) Uani 1 1 d . . . . .
O2 O 0.9406(3) 0.6077(6) 0.4186(4) 0.0488(12) Uani 1 1 d . . . . .
O3 O 0.8559(3) 0.1552(6) 0.3192(4) 0.0474(12) Uani 1 1 d . . . . .
N1 N 0.6998(4) 0.5760(6) 0.5656(4) 0.0224(12) Uani 1 1 d . . . . .
N2 N 0.6288(3) 0.2793(5) 0.5084(3) 0.0211(9) Uani 1 1 d . . . . .
C1 C 0.7339(4) 0.7315(7) 0.5873(5) 0.0275(14) Uani 1 1 d . . . . .
H1 H 0.785873 0.770891 0.552564 0.033 Uiso 1 1 calc R U . . .
C2 C 0.6957(4) 0.8340(7) 0.6578(5) 0.0330(13) Uani 1 1 d . . . . .
H2 H 0.721123 0.940375 0.670682 0.040 Uiso 1 1 calc R U . . .
C3 C 0.6186(5) 0.7757(7) 0.7093(5) 0.0368(14) Uani 1 1 d . . . . .
H3 H 0.591306 0.842753 0.757576 0.044 Uiso 1 1 calc R U . . .
C4 C 0.5822(4) 0.6174(7) 0.6888(5) 0.0317(14) Uani 1 1 d . . . . .
H4 H 0.529748 0.577244 0.722459 0.038 Uiso 1 1 calc R U . . .
C5 C 0.6252(4) 0.5183(6) 0.6168(4) 0.0236(11) Uani 1 1 d . . . . .
C6 C 0.5888(4) 0.3500(7) 0.5874(4) 0.0229(11) Uani 1 1 d . . . . .
C7 C 0.5162(4) 0.2720(8) 0.6389(4) 0.0310(13) Uani 1 1 d . . . . .
H7 H 0.491101 0.322988 0.694409 0.037 Uiso 1 1 calc R U . . .
C8 C 0.4817(4) 0.1175(7) 0.6066(5) 0.0340(13) Uani 1 1 d . . . . .
H8 H 0.434133 0.061901 0.640649 0.041 Uiso 1 1 calc R U . . .
C9 C 0.5194(4) 0.0484(7) 0.5231(5) 0.0303(13) Uani 1 1 d . . . . .
H9 H 0.496319 -0.053733 0.498895 0.036 Uiso 1 1 calc R U . . .
C10 C 0.5920(3) 0.1318(6) 0.4750(5) 0.0235(12) Uani 1 1 d . . . . .
C11 C 0.6301(4) 0.0601(7) 0.3805(5) 0.0303(13) Uani 1 1 d . . . . .
H11 H 0.652560 0.151299 0.337775 0.036 Uiso 1 1 calc R U . . .
C12 C 0.6972(5) 0.5174(7) 0.3528(5) 0.0257(14) Uani 1 1 d . . . . .
C13 C 0.8724(4) 0.5344(7) 0.4338(4) 0.0322(14) Uani 1 1 d . . . . .
C14 C 0.8162(4) 0.2448(7) 0.3706(5) 0.0301(14) 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 Br1 2.6165(8) . ?
Re1 N1 2.156(5) . ?
Re1 N2 2.224(4) . ?
Re1 C12 1.911(7) . ?
Re1 C13 1.914(6) . ?
Re1 C14 1.928(6) . ?
F1 C11 1.363(7) . ?
F2 C11 1.351(7) . ?
O1 C12 1.139(7) . ?
O2 C13 1.145(7) . ?
O3 C14 1.145(7) . ?
N1 C1 1.352(7) . ?
N1 C5 1.348(7) . ?
N2 C6 1.340(7) . ?
N2 C10 1.355(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.370(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.397(8) . ?
C5 C6 1.480(7) . ?
C6 C7 1.391(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.386(8) . ?
C8 H8 0.9300 . ?
C8 C9 1.373(9) . ?
C9 H9 0.9300 . ?
C9 C10 1.388(8) . ?
C10 C11 1.510(9) . ?
C11 H11 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
N1 Re1 Br1 84.27(13) . . ?
N1 Re1 N2 74.94(18) . . ?
N2 Re1 Br1 83.81(11) . . ?
C12 Re1 Br1 175.79(19) . . ?
C12 Re1 N1 92.6(2) . . ?
C12 Re1 N2 92.7(2) . . ?
C12 Re1 C13 90.8(2) . . ?
C12 Re1 C14 91.3(3) . . ?
C13 Re1 Br1 92.37(17) . . ?
C13 Re1 N1 97.2(2) . . ?
C13 Re1 N2 171.6(2) . . ?
C13 Re1 C14 84.0(2) . . ?
C14 Re1 Br1 91.79(19) . . ?
C14 Re1 N1 175.9(2) . . ?
C14 Re1 N2 103.6(2) . . ?
C1 N1 Re1 124.6(4) . . ?
C5 N1 Re1 117.0(4) . . ?
C5 N1 C1 118.3(5) . . ?
C6 N2 Re1 114.3(3) . . ?
C6 N2 C10 117.8(5) . . ?
C10 N2 Re1 127.5(4) . . ?
N1 C1 H1 118.4 . . ?
N1 C1 C2 123.2(6) . . ?
C2 C1 H1 118.4 . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.4(6) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.7(6) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.1(6) . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.3(5) . . ?
N1 C5 C6 115.8(5) . . ?
C4 C5 C6 122.8(5) . . ?
N2 C6 C5 116.4(5) . . ?
N2 C6 C7 122.5(5) . . ?
C7 C6 C5 121.1(5) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 C6 119.3(6) . . ?
C8 C7 H7 120.4 . . ?
C7 C8 H8 120.8 . . ?
C9 C8 C7 118.5(6) . . ?
C9 C8 H8 120.8 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.6(5) . . ?
C10 C9 H9 120.2 . . ?
N2 C10 C9 122.2(5) . . ?
N2 C10 C11 118.2(5) . . ?
C9 C10 C11 119.6(5) . . ?
F1 C11 C10 108.6(5) . . ?
F1 C11 H11 110.5 . . ?
F2 C11 F1 106.2(5) . . ?
F2 C11 C10 110.4(6) . . ?
F2 C11 H11 110.5 . . ?
C10 C11 H11 110.5 . . ?
O1 C12 Re1 177.8(5) . . ?
O2 C13 Re1 178.6(6) . . ?
O3 C14 Re1 174.7(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
Re1 N1 C1 C2 -177.9(5) . . . . ?
Re1 N1 C5 C4 178.9(4) . . . . ?
Re1 N1 C5 C6 -4.9(6) . . . . ?
Re1 N2 C6 C5 12.1(6) . . . . ?
Re1 N2 C6 C7 -168.7(4) . . . . ?
Re1 N2 C10 C9 168.0(4) . . . . ?
Re1 N2 C10 C11 -13.8(7) . . . . ?
N1 C1 C2 C3 0.0(10) . . . . ?
N1 C5 C6 N2 -5.1(7) . . . . ?
N1 C5 C6 C7 175.6(5) . . . . ?
N2 C6 C7 C8 -1.8(8) . . . . ?
N2 C10 C11 F1 -150.7(5) . . . . ?
N2 C10 C11 F2 93.4(6) . . . . ?
C1 N1 C5 C4 1.6(8) . . . . ?
C1 N1 C5 C6 177.8(5) . . . . ?
C1 C2 C3 C4 0.0(9) . . . . ?
C2 C3 C4 C5 0.8(9) . . . . ?
C3 C4 C5 N1 -1.7(9) . . . . ?
C3 C4 C5 C6 -177.6(5) . . . . ?
C4 C5 C6 N2 171.0(5) . . . . ?
C4 C5 C6 C7 -8.2(8) . . . . ?
C5 N1 C1 C2 -0.8(9) . . . . ?
C5 C6 C7 C8 177.5(5) . . . . ?
C6 N2 C10 C9 -4.2(8) . . . . ?
C6 N2 C10 C11 174.1(5) . . . . ?
C6 C7 C8 C9 -1.4(9) . . . . ?
C7 C8 C9 C10 1.7(9) . . . . ?
C8 C9 C10 N2 1.1(9) . . . . ?
C8 C9 C10 C11 -177.1(5) . . . . ?
C9 C10 C11 F1 27.6(7) . . . . ?
C9 C10 C11 F2 -88.4(6) . . . . ?
C10 N2 C6 C5 -174.8(5) . . . . ?
C10 N2 C6 C7 4.5(7) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on loop with oil'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_o-rebrnn14
_database_code_depnum_ccdc_archive 'CCDC 2090797'
loop_
_audit_author_name
_audit_author_address
'Aurelien Crochet'
;University of Fribourg, Chemistry Department
Switzerland
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2023-03-09 downloaded from the CCDC.
;
_audit_creation_date             2020-09-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
isabelle.kolly@unifr.ch
aurelien.crochet@unifr.ch
fabio.zobi@unifr.ch
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H10 Br N2 O4 Re'
_chemical_formula_sum            'C14 H10 Br N2 O4 Re'
_chemical_formula_weight         536.35
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -5.2083 5.8923 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7857(3)
_cell_length_b                   8.4162(3)
_cell_length_c                   11.3670(4)
_cell_angle_alpha                92.440(3)
_cell_angle_beta                 95.136(3)
_cell_angle_gamma                92.303(3)
_cell_volume                     740.45(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    47307
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      65.60
_cell_measurement_theta_min      3.91
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    19.401
_exptl_absorpt_correction_T_max  0.3471
_exptl_absorpt_correction_T_min  0.1315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270. Afterwards scaling of
reflection intensities was performed within STOE LANA. J. Koziskova, F. Hahn,
J. Richter, J. Kozisek, Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136-140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             500
_exptl_crystal_recrystallization_method 'layering of hexane and DCM'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0072
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18442
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        64.651
_diffrn_reflns_theta_max         64.651
_diffrn_reflns_theta_min         3.909
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 Pilatus300K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'Dectris Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '1.2 mm, 0.6 diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Primux 100 micro'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2420
_reflns_number_total             2424
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.757
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       0.00026(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2424
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0200
_refine_ls_R_factor_gt           0.0199
_refine_ls_restrained_S_all      1.208
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0144P)²+2.8051P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0480
_refine_ls_wR_factor_ref         0.0480
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Re1 Re 0.38281(2) 0.81553(2) 0.68771(2) 0.02423(9) Uani 1 1 d . . . . .
Br1 Br 0.25111(7) 0.92762(6) 0.87642(4) 0.03773(14) Uani 1 1 d . . . . .
O1 O 0.9009(5) 0.7170(5) 0.9462(4) 0.0627(12) Uani 1 1 d . . . . .
H1 H 0.975894 0.787087 0.941415 0.094 Uiso 1 1 calc R U . . .
O2 O 0.6866(5) 1.0619(4) 0.7076(4) 0.0506(10) Uani 1 1 d . . . . .
O3 O 0.1893(5) 1.0637(4) 0.5448(4) 0.0521(10) Uani 1 1 d . . . . .
O4 O 0.5049(5) 0.6808(4) 0.4597(3) 0.0420(8) Uani 1 1 d . . . . .
N1 N 0.4793(5) 0.6155(4) 0.7947(3) 0.0293(8) Uani 1 1 d . . . . .
N2 N 0.1676(5) 0.6398(4) 0.6770(3) 0.0307(8) Uani 1 1 d . . . . .
C1 C 0.6347(6) 0.6057(6) 0.8570(4) 0.0324(10) Uani 1 1 d . . . . .
C2 C 0.6834(7) 0.4639(6) 0.9070(4) 0.0376(11) Uani 1 1 d . . . . .
H2 H 0.791454 0.458996 0.948538 0.045 Uiso 1 1 calc R U . . .
C3 C 0.5750(7) 0.3336(6) 0.8957(4) 0.0411(12) Uani 1 1 d . . . . .
H3 H 0.609019 0.238567 0.927524 0.049 Uiso 1 1 calc R U . . .
C4 C 0.4139(7) 0.3427(6) 0.8368(4) 0.0382(11) Uani 1 1 d . . . . .
H4 H 0.337461 0.254303 0.829708 0.046 Uiso 1 1 calc R U . . .
C5 C 0.3657(6) 0.4853(5) 0.7875(4) 0.0271(9) Uani 1 1 d . . . . .
C6 C 0.1954(6) 0.5016(5) 0.7283(4) 0.0305(10) Uani 1 1 d . . . . .
C7 C 0.0626(7) 0.3837(6) 0.7246(4) 0.0403(12) Uani 1 1 d . . . . .
H7 H 0.081969 0.288445 0.761126 0.048 Uiso 1 1 calc R U . . .
C8 C -0.0942(7) 0.4084(6) 0.6679(5) 0.0431(12) Uani 1 1 d . . . . .
H8 H -0.181828 0.329414 0.664496 0.052 Uiso 1 1 calc R U . . .
C9 C -0.1240(7) 0.5523(6) 0.6148(5) 0.0417(12) Uani 1 1 d . . . . .
H9 H -0.230841 0.571159 0.575743 0.050 Uiso 1 1 calc R U . . .
C10 C 0.0094(6) 0.6656(6) 0.6217(4) 0.0316(10) Uani 1 1 d . . . . .
H10 H -0.009005 0.762672 0.587621 0.038 Uiso 1 1 calc R U . . .
C11 C 0.7508(6) 0.7499(6) 0.8712(4) 0.0345(10) Uani 1 1 d . . . . .
H11A H 0.783611 0.780236 0.794692 0.041 Uiso 1 1 calc R U . . .
H11B H 0.692028 0.837327 0.905848 0.041 Uiso 1 1 calc R U . . .
C12 C 0.5728(7) 0.9681(5) 0.7019(4) 0.0347(11) Uani 1 1 d . . . . .
C13 C 0.2633(6) 0.9698(5) 0.5973(4) 0.0345(11) Uani 1 1 d . . . . .
C14 C 0.4643(5) 0.7257(5) 0.5412(4) 0.0215(9) 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 Br1 2.6157(5) . ?
Re1 N1 2.234(4) . ?
Re1 N2 2.182(4) . ?
Re1 C12 1.910(5) . ?
Re1 C13 1.910(5) . ?
Re1 C14 1.967(5) . ?
O1 H1 0.8200 . ?
O1 C11 1.427(6) . ?
O2 C12 1.158(6) . ?
O3 C13 1.152(6) . ?
O4 C14 1.064(5) . ?
N1 C1 1.353(6) . ?
N1 C5 1.375(6) . ?
N2 C6 1.339(6) . ?
N2 C10 1.361(6) . ?
C1 C2 1.396(7) . ?
C1 C11 1.478(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.351(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.374(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.397(6) . ?
C5 C6 1.446(7) . ?
C6 C7 1.401(7) . ?
C7 H7 0.9300 . ?
C7 C8 1.357(8) . ?
C8 H8 0.9300 . ?
C8 C9 1.395(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.376(7) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Re1 Br1 87.78(9) . . ?
N2 Re1 Br1 84.82(10) . . ?
N2 Re1 N1 74.85(14) . . ?
C12 Re1 Br1 94.08(15) . . ?
C12 Re1 N1 103.83(17) . . ?
C12 Re1 N2 178.31(17) . . ?
C12 Re1 C14 89.71(19) . . ?
C13 Re1 Br1 89.20(15) . . ?
C13 Re1 N1 170.47(17) . . ?
C13 Re1 N2 95.88(17) . . ?
C13 Re1 C12 85.4(2) . . ?
C13 Re1 C14 89.14(18) . . ?
C14 Re1 Br1 175.72(11) . . ?
C14 Re1 N1 93.24(14) . . ?
C14 Re1 N2 91.42(15) . . ?
C11 O1 H1 109.5 . . ?
C1 N1 Re1 128.2(3) . . ?
C1 N1 C5 118.6(4) . . ?
C5 N1 Re1 113.1(3) . . ?
C6 N2 Re1 117.3(3) . . ?
C6 N2 C10 119.8(4) . . ?
C10 N2 Re1 122.9(3) . . ?
N1 C1 C2 120.9(5) . . ?
N1 C1 C11 118.1(4) . . ?
C2 C1 C11 120.9(4) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(5) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.4(5) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.7(5) . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 120.7(4) . . ?
N1 C5 C6 117.9(4) . . ?
C4 C5 C6 121.5(4) . . ?
N2 C6 C5 116.3(4) . . ?
N2 C6 C7 120.2(5) . . ?
C7 C6 C5 123.5(4) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.1(5) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 119.9(5) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 121.0 . . ?
C10 C9 C8 118.1(5) . . ?
C10 C9 H9 121.0 . . ?
N2 C10 C9 122.0(5) . . ?
N2 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
O1 C11 C1 108.9(4) . . ?
O1 C11 H11A 109.9 . . ?
O1 C11 H11B 109.9 . . ?
C1 C11 H11A 109.9 . . ?
C1 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
O2 C12 Re1 178.2(4) . . ?
O3 C13 Re1 178.5(5) . . ?
O4 C14 Re1 177.4(4) . . ?

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
O1 H1 Br1 0.82 2.59 3.365(4) 159.0 1_655 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Re1 N1 C1 C2 -171.7(3) . . . . ?
Re1 N1 C1 C11 8.8(6) . . . . ?
Re1 N1 C5 C4 172.0(3) . . . . ?
Re1 N1 C5 C6 -8.5(5) . . . . ?
Re1 N2 C6 C5 1.1(5) . . . . ?
Re1 N2 C6 C7 180.0(3) . . . . ?
Re1 N2 C10 C9 179.2(4) . . . . ?
N1 C1 C2 C3 -0.9(7) . . . . ?
N1 C1 C11 O1 175.8(4) . . . . ?
N1 C5 C6 N2 5.1(6) . . . . ?
N1 C5 C6 C7 -173.7(4) . . . . ?
N2 C6 C7 C8 0.8(7) . . . . ?
C1 N1 C5 C4 -4.1(6) . . . . ?
C1 N1 C5 C6 175.4(4) . . . . ?
C1 C2 C3 C4 -1.6(7) . . . . ?
C2 C1 C11 O1 -3.7(6) . . . . ?
C2 C3 C4 C5 1.2(8) . . . . ?
C3 C4 C5 N1 1.7(7) . . . . ?
C3 C4 C5 C6 -177.9(4) . . . . ?
C4 C5 C6 N2 -175.3(4) . . . . ?
C4 C5 C6 C7 5.9(7) . . . . ?
C5 N1 C1 C2 3.7(6) . . . . ?
C5 N1 C1 C11 -175.8(4) . . . . ?
C5 C6 C7 C8 179.5(5) . . . . ?
C6 N2 C10 C9 -1.1(7) . . . . ?
C6 C7 C8 C9 -1.0(8) . . . . ?
C7 C8 C9 C10 0.2(8) . . . . ?
C8 C9 C10 N2 0.9(7) . . . . ?
C10 N2 C6 C5 -178.6(4) . . . . ?
C10 N2 C6 C7 0.3(6) . . . . ?
C11 C1 C2 C3 178.6(5) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on MiTeGen loop with oil'
_olex2_submission_special_instructions 'No special instructions were received'
