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

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1400312'
_audit_update_record             
;
2015-05-11 deposited with the CCDC.
2015-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 Br1 N4 O3 Re1'
_chemical_formula_sum            'C25 H22 Br N4 O3 Re'
_chemical_formula_weight         692.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      Monoclinic
_space_group_IT_number           ?
_space_group_name_H-M_alt        'P 21/a'
_space_group_name_Hall           '-P 2yab'

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

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

_cell_length_a                   13.2087(9)
_cell_length_b                   7.5055(5)
_cell_length_c                   24.8936(18)
_cell_angle_alpha                90.000
_cell_angle_beta                 104.400(5)
_cell_angle_gamma                90.000
_cell_volume                     2390.3(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.925
_exptl_crystal_F_000             1336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    6.790
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15745
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.843
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             5378
_reflns_number_gt                4317
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0223P)²+2.5924P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5378
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0598
_refine_ls_wR_factor_gt          0.0545
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Re1 Re 0.13582(2) 0.55767(2) 0.22563(2) 0.01431(5) Uani 1 1 d . . . . .
Br1 Br 0.31569(3) 0.43139(6) 0.28181(2) 0.02183(10) Uani 1 1 d . . . . .
N2 N 0.0926(3) 0.5421(5) 0.30632(14) 0.0154(7) Uani 1 1 d . . . . .
O1 O 0.1908(3) 0.5419(4) 0.11287(13) 0.0290(8) Uani 1 1 d . . . . .
N1 N 0.0862(3) 0.2725(5) 0.22659(15) 0.0161(8) Uani 1 1 d . . . . .
O2 O -0.0774(2) 0.7102(4) 0.16797(13) 0.0278(7) Uani 1 1 d . . . . .
C19 C 0.1605(4) 0.6233(6) 0.5886(2) 0.0275(11) Uani 1 1 d . . . . .
H19 H 0.1713 0.6274 0.6269 0.033 Uiso 1 1 calc R U . . .
N4 N 0.1221(3) 0.6099(5) 0.41742(15) 0.0189(8) Uani 1 1 d . . . . .
O3 O 0.2321(3) 0.9312(4) 0.24464(14) 0.0285(7) Uani 1 1 d . . . . .
C12 C 0.0297(3) 0.3777(6) 0.30701(17) 0.0183(9) Uani 1 1 d . . . . .
H12A H -0.0411 0.3955 0.2849 0.022 Uiso 1 1 calc R U . . .
H12B H 0.0268 0.3507 0.3447 0.022 Uiso 1 1 calc R U . . .
C23 C 0.1718(3) 0.5463(6) 0.15544(19) 0.0209(9) Uani 1 1 d . . . . .
C16 C -0.0232(3) 0.7966(6) 0.46040(18) 0.0204(9) Uani 1 1 d . . . . .
H16 H -0.0729 0.8567 0.4743 0.025 Uiso 1 1 calc R U . . .
C5 C 0.0616(3) 0.2058(5) -0.03008(16) 0.0161(8) Uani 1 1 d . . . . .
H5 H 0.0209 0.2698 -0.0596 0.019 Uiso 1 1 calc R U . . .
C1 C 0.1039(3) 0.1218(5) 0.06798(17) 0.0164(9) Uani 1 1 d . . . . .
C24 C 0.0020(4) 0.6512(6) 0.18891(18) 0.0214(10) Uani 1 1 d . . . . .
C6 C 0.0410(3) 0.2187(5) 0.02292(17) 0.0170(9) Uani 1 1 d . . . . .
C9 C 0.0079(3) 0.2222(5) 0.12713(17) 0.0178(9) Uani 1 1 d . . . . .
C14 C 0.0442(3) 0.6974(6) 0.38499(17) 0.0194(9) Uani 1 1 d . . . . .
C17 C 0.0606(3) 0.7082(6) 0.49698(18) 0.0195(9) Uani 1 1 d . . . . .
C13 C 0.0414(4) 0.6989(6) 0.32374(17) 0.0209(9) Uani 1 1 d . . . . .
H13A H -0.0308 0.7030 0.3024 0.025 Uiso 1 1 calc R U . . .
H13B H 0.0757 0.8060 0.3154 0.025 Uiso 1 1 calc R U . . .
C3 C 0.2019(3) 0.0024(6) 0.00595(19) 0.0206(9) Uani 1 1 d . . . . .
H3 H 0.2556 -0.0690 -0.0001 0.025 Uiso 1 1 calc R U . . .
C18 C 0.0776(4) 0.7104(6) 0.55525(18) 0.0224(10) Uani 1 1 d . . . . .
H18 H 0.0315 0.7723 0.5712 0.027 Uiso 1 1 calc R U . . .
C7 C -0.0409(3) 0.3223(6) 0.03303(18) 0.0185(9) Uani 1 1 d . . . . .
H7 H -0.0834 0.3885 0.0046 0.022 Uiso 1 1 calc R U . . .
N3 N 0.0865(3) 0.1239(5) 0.11992(14) 0.0179(8) Uani 1 1 d . . . . .
C10 C -0.0101(3) 0.2164(6) 0.18473(17) 0.0202(9) Uani 1 1 d . . . . .
H10A H -0.0674 0.2952 0.1865 0.024 Uiso 1 1 calc R U . . .
H10B H -0.0291 0.0964 0.1929 0.024 Uiso 1 1 calc R U . . .
C22 C 0.1320(4) 0.6132(6) 0.47311(18) 0.0191(9) Uani 1 1 d . . . . .
C4 C 0.1403(3) 0.1010(5) -0.03832(18) 0.0197(9) Uani 1 1 d . . . . .
H4 H 0.1534 0.0944 -0.0733 0.024 Uiso 1 1 calc R U . . .
C20 C 0.2300(4) 0.5265(6) 0.5644(2) 0.0271(10) Uani 1 1 d . . . . .
H20 H 0.2860 0.4660 0.5870 0.033 Uiso 1 1 calc R U . . .
C2 C 0.1839(3) 0.0101(6) 0.05801(18) 0.0179(9) Uani 1 1 d . . . . .
H2 H 0.2242 -0.0580 0.0867 0.021 Uiso 1 1 calc R U . . .
C11 C 0.0800(3) 0.2258(5) 0.28378(17) 0.0176(9) Uani 1 1 d . . . . .
H11A H 0.1495 0.2041 0.3070 0.021 Uiso 1 1 calc R U . . .
H11B H 0.0389 0.1183 0.2830 0.021 Uiso 1 1 calc R U . . .
C21 C 0.2156(3) 0.5211(6) 0.50828(19) 0.0229(10) Uani 1 1 d . . . . .
H21 H 0.2616 0.4560 0.4931 0.027 Uiso 1 1 calc R U . . .
C25 C 0.1933(3) 0.7931(6) 0.23632(17) 0.0214(10) Uani 1 1 d . . . . .
C8 C -0.0574(3) 0.3247(6) 0.08498(18) 0.0200(9) Uani 1 1 d . . . . .
H8 H -0.1111 0.3930 0.0925 0.024 Uiso 1 1 calc R U . . .
C15 C -0.0314(3) 0.7936(6) 0.40474(18) 0.0209(9) Uani 1 1 d . . . . .
H15 H -0.0853 0.8534 0.3803 0.025 Uiso 1 1 calc R U . . .
H001 H 0.147(3) 0.516(5) 0.3316(17) 0.008(11) Uiso 1 1 d . . . . .
H002 H 0.134(3) 0.226(5) 0.2205(17) 0.006(11) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 C24 1.911(5) . ?
Re1 C25 1.916(5) . ?
Re1 C23 1.924(4) . ?
Re1 N2 2.223(3) . ?
Re1 N1 2.240(4) . ?
Re1 Br1 2.6165(9) . ?
N2 C13 1.475(5) . ?
N2 C12 1.490(5) . ?
O1 C23 1.148(5) . ?
N1 C11 1.488(5) . ?
N1 C10 1.491(5) . ?
O2 C24 1.138(5) . ?
C19 C18 1.365(6) . ?
C19 C20 1.417(7) . ?
N4 C14 1.315(5) . ?
N4 C22 1.360(5) . ?
O3 C25 1.151(5) . ?
C12 C11 1.505(6) . ?
C16 C15 1.363(6) . ?
C16 C17 1.412(6) . ?
C5 C4 1.358(6) . ?
C5 C6 1.415(5) . ?
C1 N3 1.368(5) . ?
C1 C2 1.418(6) . ?
C1 C6 1.419(6) . ?
C6 C7 1.406(6) . ?
C9 N3 1.322(5) . ?
C9 C8 1.410(6) . ?
C9 C10 1.512(5) . ?
C14 C15 1.415(6) . ?
C14 C13 1.516(5) . ?
C17 C18 1.412(6) . ?
C17 C22 1.424(6) . ?
C3 C2 1.376(6) . ?
C3 C4 1.407(6) . ?
C7 C8 1.364(6) . ?
C22 C21 1.408(6) . ?
C20 C21 1.362(6) . ?

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
C24 Re1 C25 90.87(19) . . ?
C24 Re1 C23 89.43(18) . . ?
C25 Re1 C23 89.31(18) . . ?
C24 Re1 N2 92.11(15) . . ?
C25 Re1 N2 96.03(15) . . ?
C23 Re1 N2 174.42(15) . . ?
C24 Re1 N1 96.77(16) . . ?
C25 Re1 N1 170.66(16) . . ?
C23 Re1 N1 96.10(16) . . ?
N2 Re1 N1 78.39(13) . . ?
C24 Re1 Br1 176.40(12) . . ?
C25 Re1 Br1 89.08(13) . . ?
C23 Re1 Br1 94.17(13) . . ?
N2 Re1 Br1 84.32(10) . . ?
N1 Re1 Br1 82.95(10) . . ?
C13 N2 C12 111.0(3) . . ?
C13 N2 Re1 117.6(3) . . ?
C12 N2 Re1 108.9(2) . . ?
C11 N1 C10 111.2(3) . . ?
C11 N1 Re1 108.7(2) . . ?
C10 N1 Re1 117.6(3) . . ?
C18 C19 C20 119.6(4) . . ?
C14 N4 C22 118.6(4) . . ?
N2 C12 C11 108.8(3) . . ?
O1 C23 Re1 178.1(4) . . ?
C15 C16 C17 119.9(4) . . ?
C4 C5 C6 120.8(4) . . ?
N3 C1 C2 118.6(4) . . ?
N3 C1 C6 122.6(4) . . ?
C2 C1 C6 118.7(4) . . ?
O2 C24 Re1 178.3(4) . . ?
C7 C6 C5 122.7(4) . . ?
C7 C6 C1 117.9(4) . . ?
C5 C6 C1 119.4(4) . . ?
N3 C9 C8 124.0(4) . . ?
N3 C9 C10 115.3(4) . . ?
C8 C9 C10 120.6(4) . . ?
N4 C14 C15 123.6(4) . . ?
N4 C14 C13 116.1(4) . . ?
C15 C14 C13 120.2(4) . . ?
C18 C17 C16 123.7(4) . . ?
C18 C17 C22 118.8(4) . . ?
C16 C17 C22 117.4(4) . . ?
N2 C13 C14 113.0(3) . . ?
C2 C3 C4 120.9(4) . . ?
C19 C18 C17 121.1(4) . . ?
C8 C7 C6 119.3(4) . . ?
C9 N3 C1 117.2(4) . . ?
N1 C10 C9 110.2(3) . . ?
N4 C22 C21 119.1(4) . . ?
N4 C22 C17 121.9(4) . . ?
C21 C22 C17 119.0(4) . . ?
C5 C4 C3 120.1(4) . . ?
C21 C20 C19 120.8(4) . . ?
C3 C2 C1 120.1(4) . . ?
N1 C11 C12 108.9(3) . . ?
C20 C21 C22 120.7(4) . . ?
O3 C25 Re1 176.6(4) . . ?
C7 C8 C9 119.0(4) . . ?
C16 C15 C14 118.5(4) . . ?

_refine_diff_density_max         0.797
_refine_diff_density_min         -0.841
_refine_diff_density_rms         0.140


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1400313'
_audit_update_record             
;
2015-05-11 deposited with the CCDC.
2015-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H25 Br Cl0 N4 O3 Re'
_chemical_formula_weight         731.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.2026(7)
_cell_length_b                   11.8088(8)
_cell_length_c                   13.1060(9)
_cell_angle_alpha                63.263(4)
_cell_angle_beta                 86.265(5)
_cell_angle_gamma                73.684(4)
_cell_volume                     1349.94(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.800
_exptl_crystal_F_000             710
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.000
_exptl_crystal_size_min          0.000
_exptl_absorpt_coefficient_mu    6.017
_shelx_estimated_absorpt_T_min   0.532
_shelx_estimated_absorpt_T_max   1.000
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17641
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.456
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6179
_reflns_number_gt                6004
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0337P)²+3.0255P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6179
_refine_ls_number_parameters     389
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0229
_refine_ls_wR_factor_ref         0.0598
_refine_ls_wR_factor_gt          0.0593
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.117
_refine_ls_shift/su_mean         0.002

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
C1 C 0.4675(3) 0.0356(3) 0.2929(3) 0.0173(4) Uani 1 1 d . . . . .
C2 C 0.5549(4) 0.0606(3) 0.2014(3) 0.0261(7) Uani 1 1 d . . . . .
H2 H 0.5858 -0.0016 0.1716 0.031 Uiso 1 1 calc R U . . .
C3 C 0.5947(5) 0.1733(4) 0.1560(4) 0.0398(10) Uani 1 1 d . . . . .
H3 H 0.6542 0.1882 0.0953 0.048 Uiso 1 1 calc R U . . .
C4 C 0.5491(5) 0.2686(3) 0.1974(3) 0.0375(10) Uani 1 1 d . . . . .
H4 H 0.5778 0.3468 0.1645 0.045 Uiso 1 1 calc R U . . .
C5 C 0.4638(4) 0.2480(3) 0.2849(3) 0.0251(7) Uani 1 1 d . . . . .
H5 H 0.4333 0.3121 0.3127 0.030 Uiso 1 1 calc R U . . .
C6 C 0.4208(3) 0.1318(3) 0.3342(3) 0.0172(6) Uani 1 1 d . . . . .
C7 C 0.3319(3) 0.1082(3) 0.4241(3) 0.0177(6) Uani 1 1 d . . . . .
H7 H 0.2997 0.1707 0.4534 0.021 Uiso 1 1 calc R U . . .
C8 C 0.2929(3) -0.0055(3) 0.4685(3) 0.0169(6) Uani 1 1 d . . . . .
H8 H 0.2330 -0.0225 0.5288 0.020 Uiso 1 1 calc R U . . .
C9 C 0.3421(3) -0.0975(3) 0.4244(2) 0.0133(5) Uani 1 1 d . . . . .
C10 C 0.3049(3) -0.2282(3) 0.4772(2) 0.0136(5) Uani 1 1 d . . . . .
H10 H 0.3833 -0.2961 0.5325 0.016 Uiso 1 1 calc R U . . .
C11 C 0.1691(3) -0.1893(3) 0.3097(3) 0.0185(6) Uani 1 1 d . . . . .
H11A H 0.1655 -0.2231 0.2535 0.022 Uiso 1 1 calc R U . . .
H11B H 0.1694 -0.0957 0.2662 0.022 Uiso 1 1 calc R U . . .
C12 C 0.0394(3) -0.1950(3) 0.3758(3) 0.0187(6) Uani 1 1 d . . . . .
C13 C 0.0174(3) -0.3331(3) 0.4250(3) 0.0232(6) Uani 1 1 d . . . . .
H13A H -0.0603 -0.3367 0.4733 0.035 Uiso 1 1 calc R U . . .
H13B H 0.1000 -0.3998 0.4709 0.035 Uiso 1 1 calc R U . . .
H13C H -0.0016 -0.3507 0.3620 0.035 Uiso 1 1 calc R U . . .
C14 C -0.0836(3) -0.0933(3) 0.2947(3) 0.0244(7) Uani 1 1 d . . . . .
H14A H -0.0694 -0.0054 0.2622 0.037 Uiso 1 1 calc R U . . .
H14B H -0.1665 -0.0936 0.3369 0.037 Uiso 1 1 calc R U . . .
H14C H -0.0940 -0.1157 0.2327 0.037 Uiso 1 1 calc R U . . .
C15 C 0.0558(3) -0.1552(3) 0.4700(3) 0.0176(6) Uani 1 1 d . . . . .
H15A H 0.0513 -0.0602 0.4339 0.021 Uiso 1 1 calc R U . . .
H15B H -0.0214 -0.1675 0.5199 0.021 Uiso 1 1 calc R U . . .
C26 C 0.3899(3) -0.1223(4) 0.1379(3) 0.0254(7) Uani 1 1 d . . . . .
C27 C 0.6568(3) -0.2313(3) 0.2169(3) 0.0158(5) Uani 1 1 d . . . . .
C28 C 0.4995(3) -0.3828(3) 0.2492(3) 0.0241(7) Uani 1 1 d . . . . .
C16 C 0.1875(6) -0.2496(6) 0.6517(5) 0.0168(8) Uani 0.518(4) 1 d . . P A 1
H16A H 0.1668 -0.1625 0.6518 0.020 Uiso 0.518(4) 1 calc R U P A 1
H16B H 0.2806 -0.3016 0.6889 0.020 Uiso 0.518(4) 1 calc R U P A 1
N4 N -0.0013(4) -0.2563(3) 0.7736(3) 0.0154(11) Uani 0.518(4) 1 d G . P A 1
C17 C 0.0878(4) -0.3188(4) 0.7176(3) 0.0173(4) Uani 0.518(4) 1 d G . P A 1
C18 C 0.0831(4) -0.4413(4) 0.7312(3) 0.0192(12) Uani 0.518(4) 1 d G . P A 1
H18 H 0.1440 -0.4840 0.6929 0.023 Uiso 0.518(4) 1 calc R U P A 1
C19 C -0.0105(4) -0.5013(3) 0.8007(3) 0.0245(14) Uani 0.518(4) 1 d G . P A 1
H19 H -0.0137 -0.5850 0.8100 0.029 Uiso 0.518(4) 1 calc R U P A 1
C20 C -0.0996(3) -0.4388(3) 0.8567(3) 0.0173(4) Uani 0.518(4) 1 d G U P A 1
C25 C -0.0950(3) -0.3163(2) 0.8431(2) 0.0174(19) Uani 0.518(4) 1 d G . P A 1
C24 C -0.1840(4) -0.2538(3) 0.8991(3) 0.0218(13) Uani 0.518(4) 1 d G . P A 1
H24 H -0.1809 -0.1701 0.8898 0.026 Uiso 0.518(4) 1 calc R U P A 1
C23 C -0.2777(4) -0.3138(4) 0.9686(4) 0.0277(15) Uani 0.518(4) 1 d G . P A 1
H23 H -0.3386 -0.2710 1.0069 0.033 Uiso 0.518(4) 1 calc R U P A 1
C22 C -0.2824(4) -0.4363(5) 0.9822(4) 0.033(4) Uani 0.518(4) 1 d G . P A 1
H22 H -0.3464 -0.4773 1.0297 0.039 Uiso 0.518(4) 1 calc R U P A 1
C21 C -0.1933(4) -0.4988(4) 0.9262(4) 0.0330(17) Uani 0.518(4) 1 d G . P A 1
H21 H -0.1965 -0.5825 0.9355 0.040 Uiso 0.518(4) 1 calc R U P A 1
Br1 Br 0.63347(3) -0.38766(3) 0.48315(2) 0.01619(7) Uani 1 1 d . . . . .
N1 N 0.3002(2) -0.2663(2) 0.3831(2) 0.0149(5) Uani 1 1 d . . . . .
N2 N 0.1841(2) -0.2315(2) 0.5402(2) 0.0171(5) Uani 1 1 d . . . . .
N3 N 0.4275(2) -0.0803(2) 0.3407(2) 0.0126(4) Uani 1 1 d . . . . .
O1 O 0.3394(3) -0.0543(3) 0.0519(3) 0.0468(6) Uani 1 1 d . . . . .
O2 O 0.7604(2) -0.2314(2) 0.1768(2) 0.0241(5) Uani 1 1 d . . . . .
O3 O 0.5036(3) -0.4644(3) 0.2226(3) 0.0457(8) Uani 1 1 d . . . . .
Re1 Re 0.48548(2) -0.24118(2) 0.28575(2) 0.01186(5) Uani 1 1 d . . . . .
C116 C 0.1934(6) -0.3621(6) 0.6435(5) 0.0168(8) Uani 0.482(4) 1 d . . P A 2
H11C H 0.2843 -0.3954 0.6851 0.020 Uiso 0.482(4) 1 calc R U P A 2
H11D H 0.1856 -0.4269 0.6175 0.020 Uiso 0.482(4) 1 calc R U P A 2
C118 C 0.0604(8) -0.2558(8) 0.7644(7) 0.0216(16) Uani 0.482(4) 1 d . . P A 2
H118 H 0.1113 -0.1929 0.7362 0.026 Uiso 0.482(4) 1 calc R U P A 2
C117 C 0.0803(7) -0.3522(7) 0.7272(6) 0.0173(4) Uani 0.482(4) 1 d . . P A 2
N14 N 0.0139(7) -0.4407(6) 0.7551(5) 0.0193(12) Uani 0.482(4) 1 d . . P A 2
C125 C -0.0819(7) -0.4420(6) 0.8341(6) 0.0173(4) Uani 0.482(4) 1 d . . P A 2
C124 C -0.1539(9) -0.5361(8) 0.8718(8) 0.0346(19) Uani 0.482(4) 1 d . . P A 2
H124 H -0.1390 -0.5976 0.8412 0.042 Uiso 0.482(4) 1 calc R U P A 2
C119 C -0.0342(7) -0.2540(7) 0.8425(7) 0.0249(15) Uani 0.482(4) 1 d . . P A 2
H119 H -0.0511 -0.1902 0.8706 0.030 Uiso 0.482(4) 1 calc R U P A 2
C120 C -0.1065(10) -0.3508(9) 0.8803(8) 0.027(2) Uani 0.482(4) 1 d . U P A 2
C121 C -0.2058(8) -0.3563(9) 0.9650(6) 0.0297(17) Uani 0.482(4) 1 d . . P A 2
H121 H -0.2266 -0.2928 0.9938 0.036 Uiso 0.482(4) 1 calc R U P A 2
C122 C -0.2683(13) -0.4533(14) 1.0027(14) 0.030(3) Uani 0.482(4) 1 d . . P A 2
H122 H -0.3277 -0.4631 1.0631 0.036 Uiso 0.482(4) 1 calc R U P A 2
C123 C -0.2454(10) -0.5399(10) 0.9525(8) 0.040(2) Uani 0.482(4) 1 d . . P A 2
H123 H -0.2957 -0.6031 0.9758 0.048 Uiso 0.482(4) 1 calc R U P A 2
O4 O 0.0496(6) -0.1287(6) 1.0160(4) 0.0468(6) Uani 0.586(6) 1 d . . P B 3
O5 O -0.0295(8) 0.0412(9) 0.9922(7) 0.0468(6) Uani 0.414(6) 1 d . . P B 4


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N3 1.393(4) . ?
C1 C2 1.418(4) . ?
C1 C6 1.423(4) . ?
C2 C3 1.360(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.415(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.368(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.413(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.413(4) . ?
C7 C8 1.367(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.410(4) . ?
C8 H8 0.9500 . ?
C9 N3 1.333(4) . ?
C9 C10 1.530(4) . ?
C10 N2 1.438(4) . ?
C10 N1 1.498(4) . ?
C10 H10 1.0000 . ?
C11 N1 1.496(4) . ?
C11 C12 1.535(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C14 1.525(4) . ?
C12 C13 1.538(4) . ?
C12 C15 1.539(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 N2 1.456(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C26 O1 1.099(5) . ?
C26 Re1 1.925(4) . ?
C27 O2 1.149(4) . ?
C27 Re1 1.923(3) . ?
C28 O3 1.153(4) . ?
C28 Re1 1.904(3) . ?
C16 N2 1.380(6) . ?
C16 C17 1.472(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
N4 C17 1.3900 . ?
N4 C25 1.3900 . ?
C17 C18 1.3900 . ?
C18 C19 1.3900 . ?
C18 H18 0.9500 . ?
C19 C20 1.3900 . ?
C19 H19 0.9500 . ?
C20 C25 1.3900 . ?
C20 C21 1.3900 . ?
C25 C24 1.3900 . ?
C24 C23 1.3900 . ?
C24 H24 0.9500 . ?
C23 C22 1.3900 . ?
C23 H23 0.9500 . ?
C22 C21 1.3900 . ?
C22 H22 0.9500 . ?
C21 H21 0.9500 . ?
Br1 Re1 2.6419(4) . ?
N1 Re1 2.225(2) . ?
N2 C116 1.509(6) . ?
N3 Re1 2.242(2) . ?
C116 C117 1.556(9) . ?
C116 H11C 0.9900 . ?
C116 H11D 0.9900 . ?
C118 C119 1.364(10) . ?
C118 C117 1.390(10) . ?
C118 H118 0.9500 . ?
C117 N14 1.306(9) . ?
N14 C125 1.376(9) . ?
C125 C124 1.391(10) . ?
C125 C120 1.414(12) . ?
C124 C123 1.357(11) . ?
C124 H124 0.9500 . ?
C119 C120 1.419(12) . ?
C119 H119 0.9500 . ?
C120 C121 1.446(12) . ?
C121 C122 1.350(13) . ?
C121 H121 0.9500 . ?
C122 C123 1.410(15) . ?
C122 H122 0.9500 . ?
C123 H123 0.9500 . ?
O5 O5 0.927(16) 2_557 ?

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
N3 C1 C2 120.7(3) . . ?
N3 C1 C6 120.8(3) . . ?
C2 C1 C6 118.6(3) . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 121.2(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 121.5(3) . . ?
C7 C6 C1 118.8(3) . . ?
C5 C6 C1 119.7(3) . . ?
C8 C7 C6 119.3(3) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 119.7(3) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
N3 C9 C8 123.2(3) . . ?
N3 C9 C10 116.6(2) . . ?
C8 C9 C10 120.2(3) . . ?
N2 C10 N1 112.8(2) . . ?
N2 C10 C9 116.3(2) . . ?
N1 C10 C9 107.1(2) . . ?
N2 C10 H10 106.7 . . ?
N1 C10 H10 106.7 . . ?
C9 C10 H10 106.7 . . ?
N1 C11 C12 114.5(3) . . ?
N1 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
N1 C11 H11B 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C14 C12 C11 108.8(3) . . ?
C14 C12 C13 109.1(2) . . ?
C11 C12 C13 111.2(2) . . ?
C14 C12 C15 108.3(2) . . ?
C11 C12 C15 107.0(2) . . ?
C13 C12 C15 112.3(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 C12 112.9(2) . . ?
N2 C15 H15A 109.0 . . ?
C12 C15 H15A 109.0 . . ?
N2 C15 H15B 109.0 . . ?
C12 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
O1 C26 Re1 177.7(3) . . ?
O2 C27 Re1 176.9(2) . . ?
O3 C28 Re1 176.7(4) . . ?
N2 C16 C17 111.4(4) . . ?
N2 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
N2 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C17 N4 C25 120.0 . . ?
C18 C17 N4 120.0 . . ?
C18 C17 C16 124.8(3) . . ?
N4 C17 C16 115.1(3) . . ?
C19 C18 C17 120.0 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C25 C20 C19 120.0 . . ?
C25 C20 C21 120.0 . . ?
C19 C20 C21 120.0 . . ?
C24 C25 C20 120.0 . . ?
C24 C25 N4 120.0 . . ?
C20 C25 N4 120.0 . . ?
C23 C24 C25 120.0 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C22 C23 C24 120.0 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C22 C21 120.0 . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C21 C20 120.0 . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C11 N1 C10 110.9(2) . . ?
C11 N1 Re1 113.27(18) . . ?
C10 N1 Re1 108.38(16) . . ?
C16 N2 C10 121.2(3) . . ?
C16 N2 C15 117.9(3) . . ?
C10 N2 C15 114.7(2) . . ?
C10 N2 C116 114.3(3) . . ?
C15 N2 C116 120.1(3) . . ?
C9 N3 C1 118.4(2) . . ?
C9 N3 Re1 115.27(18) . . ?
C1 N3 Re1 126.29(19) . . ?
C28 Re1 C27 85.89(12) . . ?
C28 Re1 C26 88.06(15) . . ?
C27 Re1 C26 89.52(13) . . ?
C28 Re1 N1 94.53(11) . . ?
C27 Re1 N1 173.92(11) . . ?
C26 Re1 N1 96.55(12) . . ?
C28 Re1 N3 168.38(11) . . ?
C27 Re1 N3 105.69(10) . . ?
C26 Re1 N3 91.04(11) . . ?
N1 Re1 N3 74.05(9) . . ?
C28 Re1 Br1 95.78(11) . . ?
C27 Re1 Br1 86.09(9) . . ?
C26 Re1 Br1 173.93(11) . . ?
N1 Re1 Br1 87.84(7) . . ?
N3 Re1 Br1 86.13(6) . . ?
N2 C116 C117 112.9(5) . . ?
N2 C116 H11C 109.0 . . ?
C117 C116 H11C 109.0 . . ?
N2 C116 H11D 109.0 . . ?
C117 C116 H11D 109.0 . . ?
H11C C116 H11D 107.8 . . ?
C119 C118 C117 118.2(7) . . ?
C119 C118 H118 120.9 . . ?
C117 C118 H118 120.9 . . ?
N14 C117 C118 127.2(7) . . ?
N14 C117 C116 113.3(6) . . ?
C118 C117 C116 119.4(6) . . ?
C117 N14 C125 116.1(6) . . ?
N14 C125 C124 119.9(7) . . ?
N14 C125 C120 121.0(7) . . ?
C124 C125 C120 119.1(7) . . ?
C123 C124 C125 119.8(8) . . ?
C123 C124 H124 120.1 . . ?
C125 C124 H124 120.1 . . ?
C118 C119 C120 117.6(7) . . ?
C118 C119 H119 121.2 . . ?
C120 C119 H119 121.2 . . ?
C125 C120 C119 119.8(8) . . ?
C125 C120 C121 119.8(8) . . ?
C119 C120 C121 120.4(8) . . ?
C122 C121 C120 118.8(9) . . ?
C122 C121 H121 120.6 . . ?
C120 C121 H121 120.6 . . ?
C121 C122 C123 120.1(10) . . ?
C121 C122 H122 120.0 . . ?
C123 C122 H122 120.0 . . ?
C124 C123 C122 122.2(10) . . ?
C124 C123 H123 118.9 . . ?
C122 C123 H123 118.9 . . ?

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
N3 C1 C2 C3 -179.3(4) . . . . ?
C6 C1 C2 C3 1.2(5) . . . . ?
C1 C2 C3 C4 -0.8(7) . . . . ?
C2 C3 C4 C5 0.2(7) . . . . ?
C3 C4 C5 C6 0.0(6) . . . . ?
C4 C5 C6 C7 -179.6(4) . . . . ?
C4 C5 C6 C1 0.5(5) . . . . ?
N3 C1 C6 C7 -0.5(4) . . . . ?
C2 C1 C6 C7 179.0(3) . . . . ?
N3 C1 C6 C5 179.4(3) . . . . ?
C2 C1 C6 C5 -1.1(5) . . . . ?
C5 C6 C7 C8 179.8(3) . . . . ?
C1 C6 C7 C8 -0.3(4) . . . . ?
C6 C7 C8 C9 0.2(4) . . . . ?
C7 C8 C9 N3 0.7(4) . . . . ?
C7 C8 C9 C10 177.0(3) . . . . ?
N3 C9 C10 N2 -161.5(2) . . . . ?
C8 C9 C10 N2 22.0(4) . . . . ?
N3 C9 C10 N1 -34.3(3) . . . . ?
C8 C9 C10 N1 149.2(3) . . . . ?
N1 C11 C12 C14 169.6(2) . . . . ?
N1 C11 C12 C13 -70.1(3) . . . . ?
N1 C11 C12 C15 52.8(3) . . . . ?
C14 C12 C15 N2 -169.6(3) . . . . ?
C11 C12 C15 N2 -52.4(3) . . . . ?
C13 C12 C15 N2 69.8(3) . . . . ?
C25 N4 C17 C18 0.0 . . . . ?
C25 N4 C17 C16 -176.7(4) . . . . ?
N2 C16 C17 C18 56.3(5) . . . . ?
N2 C16 C17 N4 -127.2(3) . . . . ?
N4 C17 C18 C19 0.0 . . . . ?
C16 C17 C18 C19 176.3(4) . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
C18 C19 C20 C25 0.0 . . . . ?
C18 C19 C20 C21 180.0 . . . . ?
C19 C20 C25 C24 180.0 . . . . ?
C21 C20 C25 C24 0.0 . . . . ?
C19 C20 C25 N4 0.0 . . . . ?
C21 C20 C25 N4 180.0 . . . . ?
C17 N4 C25 C24 180.0 . . . . ?
C17 N4 C25 C20 0.0 . . . . ?
C20 C25 C24 C23 0.0 . . . . ?
N4 C25 C24 C23 180.0 . . . . ?
C25 C24 C23 C22 0.0 . . . . ?
C24 C23 C22 C21 0.0 . . . . ?
C23 C22 C21 C20 0.0 . . . . ?
C25 C20 C21 C22 0.0 . . . . ?
C19 C20 C21 C22 180.0 . . . . ?
C12 C11 N1 C10 -52.8(3) . . . . ?
C12 C11 N1 Re1 -174.96(19) . . . . ?
N2 C10 N1 C11 50.7(3) . . . . ?
C9 C10 N1 C11 -78.6(3) . . . . ?
N2 C10 N1 Re1 175.59(18) . . . . ?
C9 C10 N1 Re1 46.4(2) . . . . ?
C17 C16 N2 C10 -149.3(3) . . . . ?
C17 C16 N2 C15 59.9(5) . . . . ?
C17 C16 N2 C116 -49.3(4) . . . . ?
N1 C10 N2 C16 155.1(3) . . . . ?
C9 C10 N2 C16 -80.6(4) . . . . ?
N1 C10 N2 C15 -53.2(3) . . . . ?
C9 C10 N2 C15 71.0(3) . . . . ?
N1 C10 N2 C116 91.2(4) . . . . ?
C9 C10 N2 C116 -144.5(3) . . . . ?
C12 C15 N2 C16 -152.0(3) . . . . ?
C12 C15 N2 C10 55.3(3) . . . . ?
C12 C15 N2 C116 -86.9(4) . . . . ?
C8 C9 N3 C1 -1.5(4) . . . . ?
C10 C9 N3 C1 -177.9(2) . . . . ?
C8 C9 N3 Re1 -179.0(2) . . . . ?
C10 C9 N3 Re1 4.7(3) . . . . ?
C2 C1 N3 C9 -178.1(3) . . . . ?
C6 C1 N3 C9 1.4(4) . . . . ?
C2 C1 N3 Re1 -1.0(4) . . . . ?
C6 C1 N3 Re1 178.5(2) . . . . ?
C16 N2 C116 C117 52.2(5) . . . . ?
C10 N2 C116 C117 164.6(4) . . . . ?
C15 N2 C116 C117 -53.1(6) . . . . ?
C119 C118 C117 N14 3.0(12) . . . . ?
C119 C118 C117 C116 -176.5(6) . . . . ?
N2 C116 C117 N14 129.4(6) . . . . ?
N2 C116 C117 C118 -51.1(8) . . . . ?
C118 C117 N14 C125 -3.2(11) . . . . ?
C116 C117 N14 C125 176.3(6) . . . . ?
C117 N14 C125 C124 -177.7(7) . . . . ?
C117 N14 C125 C120 0.7(10) . . . . ?
N14 C125 C124 C123 178.0(8) . . . . ?
C120 C125 C124 C123 -0.5(13) . . . . ?
C117 C118 C119 C120 -0.2(11) . . . . ?
N14 C125 C120 C119 1.7(12) . . . . ?
C124 C125 C120 C119 -179.8(8) . . . . ?
N14 C125 C120 C121 -178.7(7) . . . . ?
C124 C125 C120 C121 -0.2(12) . . . . ?
C118 C119 C120 C125 -1.9(12) . . . . ?
C118 C119 C120 C121 178.5(8) . . . . ?
C125 C120 C121 C122 3.3(15) . . . . ?
C119 C120 C121 C122 -177.1(11) . . . . ?
C120 C121 C122 C123 -5(2) . . . . ?
C125 C124 C123 C122 -1.8(16) . . . . ?
C121 C122 C123 C124 5(2) . . . . ?

_refine_diff_density_max         2.153
_refine_diff_density_min         -1.409
_refine_diff_density_rms         0.122

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_2013ncs0530
_database_code_depnum_ccdc_archive 'CCDC 1400314'
_audit_update_record             
;
2015-05-11 deposited with the CCDC.
2015-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H26 Br N4 O3 Re, C7 H8'
_chemical_formula_sum            'C35 H34 Br N4 O3 Re'
_chemical_formula_weight         824.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   8.9603(5)
_cell_length_b                   11.1814(8)
_cell_length_c                   17.0562(11)
_cell_angle_alpha                71.987(3)
_cell_angle_beta                 79.252(4)
_cell_angle_gamma                86.961(4)
_cell_volume                     1596.55(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    21568
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Blade
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             812
_exptl_absorpt_coefficient_mu    5.098
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.763
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21710
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         27.48
_reflns_number_total             7305
_reflns_number_gt                7030
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0323P)²+1.4997P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7305
_refine_ls_number_parameters     404
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0233
_refine_ls_wR_factor_ref         0.0597
_refine_ls_wR_factor_gt          0.0591
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Re1 Re 0.656592(10) 0.670233(8) 0.103830(6) 0.01677(4) Uani 1 1 d . . .
Br1 Br 0.48568(3) 0.71945(2) 0.232183(17) 0.02229(6) Uani 1 1 d . . .
O2 O 0.3983(2) 0.5199(2) 0.08295(15) 0.0342(5) Uani 1 1 d . . .
O3 O 0.5505(2) 0.89339(19) -0.03066(13) 0.0290(4) Uani 1 1 d . . .
N3 N 0.8470(2) 0.7564(2) 0.13549(14) 0.0173(4) Uani 1 1 d . . .
O1 O 0.8617(2) 0.5945(2) -0.03476(15) 0.0301(5) Uani 1 1 d . . .
C26 C 0.4956(3) 0.5765(3) 0.09047(18) 0.0239(5) Uani 1 1 d . . .
N1 N 0.7435(3) 0.5242(2) 0.20297(15) 0.0198(4) Uani 1 1 d . . .
C2 C 0.7576(3) 0.9720(2) 0.09901(16) 0.0202(5) Uani 1 1 d . . .
H2 H 0.6597 0.9437 0.0985 0.024 Uiso 1 1 calc R . .
C27 C 0.7914(3) 0.6195(3) 0.01482(17) 0.0232(6) Uani 1 1 d . . .
C28 C 0.5901(3) 0.8105(3) 0.02078(17) 0.0204(5) Uani 1 1 d . . .
N2 N 0.9729(3) 0.4643(2) 0.26622(14) 0.0206(4) Uani 1 1 d . . .
C15 C 0.9311(3) 0.3311(2) 0.28631(18) 0.0219(5) Uani 1 1 d . . .
H15A H 0.9639 0.2839 0.3397 0.026 Uiso 1 1 calc R . .
H15B H 0.9894 0.2982 0.2422 0.026 Uiso 1 1 calc R . .
N4 N 0.9804(3) 0.3596(2) 0.46724(14) 0.0212(4) Uani 1 1 d . . .
C10 C 0.9120(3) 0.5371(2) 0.19269(17) 0.0195(5) Uani 1 1 d . . .
H10 H 0.9585 0.5028 0.1461 0.023 Uiso 1 1 calc R . .
C5 C 1.0431(3) 1.0589(3) 0.10048(18) 0.0249(6) Uani 1 1 d . . .
H5 H 1.1399 1.0892 0.1010 0.030 Uiso 1 1 calc R . .
C11 C 0.7040(3) 0.3899(2) 0.21755(18) 0.0227(5) Uani 1 1 d . . .
H11A H 0.7497 0.3647 0.1675 0.027 Uiso 1 1 calc R . .
H11B H 0.5924 0.3813 0.2255 0.027 Uiso 1 1 calc R . .
C1 C 0.8749(3) 0.8842(2) 0.11715(16) 0.0184(5) Uani 1 1 d . . .
C3 C 0.7840(3) 1.0980(3) 0.08208(17) 0.0237(5) Uani 1 1 d . . .
H3 H 0.7038 1.1562 0.0705 0.028 Uiso 1 1 calc R . .
C9 C 0.9533(3) 0.6758(2) 0.16395(16) 0.0187(5) Uani 1 1 d . . .
C102 C 0.2811(3) 0.1923(3) 0.34516(19) 0.0281(6) Uani 1 1 d . . .
H102 H 0.2460 0.2377 0.3838 0.034 Uiso 1 1 calc R . .
C12 C 0.7610(3) 0.3021(2) 0.29461(18) 0.0227(5) Uani 1 1 d . . .
C14 C 0.7468(4) 0.1663(3) 0.2952(2) 0.0284(6) Uani 1 1 d . . .
H14A H 0.6407 0.1482 0.2957 0.043 Uiso 1 1 calc R . .
H14B H 0.7797 0.1091 0.3452 0.043 Uiso 1 1 calc R . .
H14C H 0.8109 0.1544 0.2449 0.043 Uiso 1 1 calc R . .
C16 C 0.9406(3) 0.5135(2) 0.33846(17) 0.0215(5) Uani 1 1 d . . .
H16A H 0.8328 0.4972 0.3656 0.026 Uiso 1 1 calc R . .
H16B H 0.9574 0.6056 0.3188 0.026 Uiso 1 1 calc R . .
C6 C 1.0197(3) 0.9279(3) 0.11927(16) 0.0202(5) Uani 1 1 d . . .
C8 C 1.0998(3) 0.7132(3) 0.16623(17) 0.0227(5) Uani 1 1 d . . .
H8 H 1.1740 0.6521 0.1844 0.027 Uiso 1 1 calc R . .
C17 C 1.0413(3) 0.4524(2) 0.40157(16) 0.0200(5) Uani 1 1 d . . .
C7 C 1.1335(3) 0.8385(3) 0.14188(17) 0.0240(5) Uani 1 1 d . . .
H7 H 1.2332 0.8654 0.1402 0.029 Uiso 1 1 calc R . .
C25 C 1.0701(3) 0.3027(2) 0.52596(17) 0.0223(5) Uani 1 1 d . . .
C13 C 0.6615(3) 0.3168(3) 0.37500(18) 0.0267(6) Uani 1 1 d . . .
H13A H 0.5652 0.2718 0.3860 0.040 Uiso 1 1 calc R . .
H13B H 0.6413 0.4062 0.3679 0.040 Uiso 1 1 calc R . .
H13C H 0.7148 0.2819 0.4223 0.040 Uiso 1 1 calc R . .
C106 C 0.3582(3) 0.0004(3) 0.3171(2) 0.0292(6) Uani 1 1 d . . .
H106 H 0.3767 -0.0874 0.3363 0.035 Uiso 1 1 calc R . .
C103 C 0.3046(3) 0.2556(3) 0.2596(2) 0.0288(6) Uani 1 1 d . . .
H103 H 0.2861 0.3434 0.2403 0.035 Uiso 1 1 calc R . .
C4 C 0.9283(3) 1.1421(3) 0.08167(18) 0.0255(6) Uani 1 1 d . . .
H4 H 0.9459 1.2298 0.0683 0.031 Uiso 1 1 calc R . .
C105 C 0.3817(3) 0.0627(3) 0.2320(2) 0.0289(6) Uani 1 1 d . . .
H105 H 0.4164 0.0175 0.1932 0.035 Uiso 1 1 calc R . .
C24 C 1.0052(4) 0.2030(3) 0.59638(18) 0.0276(6) Uani 1 1 d . . .
H24 H 0.9032 0.1775 0.6022 0.033 Uiso 1 1 calc R . .
C20 C 1.2222(3) 0.3410(3) 0.51803(18) 0.0248(6) Uani 1 1 d . . .
C18 C 1.1919(3) 0.4964(3) 0.38912(18) 0.0242(5) Uani 1 1 d . . .
H18 H 1.2306 0.5637 0.3408 0.029 Uiso 1 1 calc R . .
C104 C 0.3547(3) 0.1908(3) 0.20304(19) 0.0292(6) Uani 1 1 d . . .
H104 H 0.3707 0.2335 0.1446 0.035 Uiso 1 1 calc R . .
C19 C 1.2804(3) 0.4415(3) 0.44705(19) 0.0256(6) Uani 1 1 d . . .
H19 H 1.3813 0.4707 0.4397 0.031 Uiso 1 1 calc R . .
C101 C 0.3077(3) 0.0649(3) 0.37493(19) 0.0286(6) Uani 1 1 d . . .
C100 C 0.2834(5) -0.0020(3) 0.4680(2) 0.0431(8) Uani 1 1 d . . .
H10A H 0.2798 0.0599 0.4983 0.065 Uiso 1 1 calc R . .
H10B H 0.3673 -0.0604 0.4808 0.065 Uiso 1 1 calc R . .
H10C H 0.1873 -0.0489 0.4851 0.065 Uiso 1 1 calc R . .
C21 C 1.3059(4) 0.2764(3) 0.5817(2) 0.0317(6) Uani 1 1 d . . .
H21 H 1.4078 0.3006 0.5774 0.038 Uiso 1 1 calc R . .
C23 C 1.0907(4) 0.1434(3) 0.65629(19) 0.0329(7) Uani 1 1 d . . .
H23 H 1.0470 0.0762 0.7034 0.040 Uiso 1 1 calc R . .
C22 C 1.2416(4) 0.1800(3) 0.6490(2) 0.0357(7) Uani 1 1 d . . .
H22 H 1.2989 0.1376 0.6910 0.043 Uiso 1 1 calc R . .
H500 H 0.706(4) 0.543(3) 0.249(2) 0.025(8) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C28 1.913(3) . ?
Re1 C26 1.914(3) . ?
Re1 C27 1.965(3) . ?
Re1 N1 2.186(2) . ?
Re1 N3 2.229(2) . ?
Re1 Br1 2.6165(3) . ?
O2 C26 1.152(3) . ?
O3 C28 1.155(3) . ?
N3 C9 1.329(3) . ?
N3 C1 1.390(3) . ?
O1 C27 1.058(4) . ?
N1 C11 1.495(3) . ?
N1 C10 1.497(3) . ?
N1 H500 0.87(4) . ?
C2 C3 1.373(4) . ?
C2 C1 1.410(4) . ?
C2 H2 0.9500 . ?
N2 C10 1.452(3) . ?
N2 C15 1.474(3) . ?
N2 C16 1.474(3) . ?
C15 C12 1.546(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
N4 C17 1.320(3) . ?
N4 C25 1.381(3) . ?
C10 C9 1.519(4) . ?
C10 H10 1.0000 . ?
C5 C4 1.365(4) . ?
C5 C6 1.418(4) . ?
C5 H5 0.9500 . ?
C11 C12 1.533(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C1 C6 1.422(3) . ?
C3 C4 1.406(4) . ?
C3 H3 0.9500 . ?
C9 C8 1.410(3) . ?
C102 C101 1.381(4) . ?
C102 C103 1.391(4) . ?
C102 H102 0.9500 . ?
C12 C14 1.527(4) . ?
C12 C13 1.540(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 C17 1.510(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C6 C7 1.409(4) . ?
C8 C7 1.366(4) . ?
C8 H8 0.9500 . ?
C17 C18 1.417(4) . ?
C7 H7 0.9500 . ?
C25 C24 1.415(4) . ?
C25 C20 1.421(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C106 C105 1.384(4) . ?
C106 C101 1.391(4) . ?
C106 H106 0.9500 . ?
C103 C104 1.377(4) . ?
C103 H103 0.9500 . ?
C4 H4 0.9500 . ?
C105 C104 1.388(4) . ?
C105 H105 0.9500 . ?
C24 C23 1.376(4) . ?
C24 H24 0.9500 . ?
C20 C19 1.409(4) . ?
C20 C21 1.423(4) . ?
C18 C19 1.360(4) . ?
C18 H18 0.9500 . ?
C104 H104 0.9500 . ?
C19 H19 0.9500 . ?
C101 C100 1.509(4) . ?
C100 H10A 0.9800 . ?
C100 H10B 0.9800 . ?
C100 H10C 0.9800 . ?
C21 C22 1.365(5) . ?
C21 H21 0.9500 . ?
C23 C22 1.405(5) . ?
C23 H23 0.9500 . ?
C22 H22 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C28 Re1 C26 86.78(11) . . ?
C28 Re1 C27 89.66(11) . . ?
C26 Re1 C27 89.02(11) . . ?
C28 Re1 N1 174.04(9) . . ?
C26 Re1 N1 98.75(10) . . ?
C27 Re1 N1 92.65(10) . . ?
C28 Re1 N3 101.21(9) . . ?
C26 Re1 N3 171.84(10) . . ?
C27 Re1 N3 92.67(9) . . ?
N1 Re1 N3 73.21(8) . . ?
C28 Re1 Br1 95.61(8) . . ?
C26 Re1 Br1 91.10(9) . . ?
C27 Re1 Br1 174.73(8) . . ?
N1 Re1 Br1 82.13(7) . . ?
N3 Re1 Br1 86.48(6) . . ?
C9 N3 C1 118.2(2) . . ?
C9 N3 Re1 114.54(17) . . ?
C1 N3 Re1 126.57(16) . . ?
O2 C26 Re1 179.6(3) . . ?
C11 N1 C10 109.4(2) . . ?
C11 N1 Re1 118.90(16) . . ?
C10 N1 Re1 110.29(16) . . ?
C11 N1 H500 107(2) . . ?
C10 N1 H500 106(2) . . ?
Re1 N1 H500 104(2) . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
O1 C27 Re1 177.9(3) . . ?
O3 C28 Re1 178.4(2) . . ?
C10 N2 C15 108.9(2) . . ?
C10 N2 C16 115.7(2) . . ?
C15 N2 C16 114.2(2) . . ?
N2 C15 C12 116.7(2) . . ?
N2 C15 H15A 108.1 . . ?
C12 C15 H15A 108.1 . . ?
N2 C15 H15B 108.1 . . ?
C12 C15 H15B 108.1 . . ?
H15A C15 H15B 107.3 . . ?
C17 N4 C25 117.5(2) . . ?
N2 C10 N1 113.3(2) . . ?
N2 C10 C9 113.6(2) . . ?
N1 C10 C9 108.9(2) . . ?
N2 C10 H10 106.8 . . ?
N1 C10 H10 106.8 . . ?
C9 C10 H10 106.8 . . ?
C4 C5 C6 120.8(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
N1 C11 C12 111.8(2) . . ?
N1 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N1 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
N3 C1 C2 120.2(2) . . ?
N3 C1 C6 120.7(2) . . ?
C2 C1 C6 119.0(2) . . ?
C2 C3 C4 120.8(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
N3 C9 C8 123.3(2) . . ?
N3 C9 C10 116.7(2) . . ?
C8 C9 C10 119.9(2) . . ?
C101 C102 C103 121.2(3) . . ?
C101 C102 H102 119.4 . . ?
C103 C102 H102 119.4 . . ?
C14 C12 C11 108.8(2) . . ?
C14 C12 C13 108.1(2) . . ?
C11 C12 C13 109.8(2) . . ?
C14 C12 C15 108.2(2) . . ?
C11 C12 C15 108.1(2) . . ?
C13 C12 C15 113.7(2) . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C16 C17 111.0(2) . . ?
N2 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
N2 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C7 C6 C5 122.6(2) . . ?
C7 C6 C1 118.5(2) . . ?
C5 C6 C1 118.9(2) . . ?
C7 C8 C9 119.0(2) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
N4 C17 C18 123.4(2) . . ?
N4 C17 C16 116.5(2) . . ?
C18 C17 C16 120.0(2) . . ?
C8 C7 C6 119.7(2) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
N4 C25 C24 117.7(3) . . ?
N4 C25 C20 122.5(2) . . ?
C24 C25 C20 119.8(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C105 C106 C101 120.7(3) . . ?
C105 C106 H106 119.6 . . ?
C101 C106 H106 119.6 . . ?
C104 C103 C102 119.9(3) . . ?
C104 C103 H103 120.1 . . ?
C102 C103 H103 120.1 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C106 C105 C104 120.3(3) . . ?
C106 C105 H105 119.9 . . ?
C104 C105 H105 119.9 . . ?
C23 C24 C25 119.6(3) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C19 C20 C25 117.4(2) . . ?
C19 C20 C21 124.2(3) . . ?
C25 C20 C21 118.4(3) . . ?
C19 C18 C17 119.3(3) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C103 C104 C105 119.5(3) . . ?
C103 C104 H104 120.2 . . ?
C105 C104 H104 120.2 . . ?
C18 C19 C20 119.8(3) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C102 C101 C106 118.3(3) . . ?
C102 C101 C100 120.5(3) . . ?
C106 C101 C100 121.1(3) . . ?
C101 C100 H10A 109.5 . . ?
C101 C100 H10B 109.5 . . ?
H10A C100 H10B 109.5 . . ?
C101 C100 H10C 109.5 . . ?
H10A C100 H10C 109.5 . . ?
H10B C100 H10C 109.5 . . ?
C22 C21 C20 120.9(3) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C24 C23 C22 121.1(3) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C21 C22 C23 120.1(3) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.357
_refine_diff_density_min         -0.867
_refine_diff_density_rms         0.106
####################################################################### 
# 
# 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_2013ncs0531
_database_code_depnum_ccdc_archive 'CCDC 1400315'
_audit_update_record             
;
2015-05-11 deposited with the CCDC.
2015-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H26 N4'
_chemical_formula_sum            'C25 H26 N4'
_chemical_formula_weight         382.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   16.3443(11)
_cell_length_b                   5.9490(4)
_cell_length_c                   21.3716(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.773(3)
_cell_angle_gamma                90.00
_cell_volume                     1989.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9726
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Lath
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.774
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17443
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.57
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4497
_reflns_number_gt                3413
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0523P)²+0.3982P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4497
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1019
_refine_ls_wR_factor_gt          0.0927
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N3 N 0.04817(6) 0.41881(18) 0.22041(5) 0.0168(2) Uani 1 1 d . . .
N4 N 0.14565(6) 0.32415(18) 0.52252(5) 0.0181(2) Uani 1 1 d . . .
C9 C 0.09451(8) 0.5290(2) 0.27218(5) 0.0163(3) Uani 1 1 d . . .
N1 N 0.24577(6) 0.4922(2) 0.28980(5) 0.0181(2) Uani 1 1 d . . .
N2 N 0.18800(6) 0.45815(18) 0.38339(5) 0.0162(2) Uani 1 1 d . . .
C17 C 0.11711(7) 0.4539(2) 0.47052(6) 0.0175(3) Uani 1 1 d . . .
C1 C -0.02262(8) 0.5254(2) 0.18085(6) 0.0167(3) Uani 1 1 d . . .
C16 C 0.11838(8) 0.3581(2) 0.40516(6) 0.0188(3) Uani 1 1 d . . .
H16A H 0.1262 0.1931 0.4090 0.023 Uiso 1 1 calc R . .
H16B H 0.0630 0.3885 0.3723 0.023 Uiso 1 1 calc R . .
C10 C 0.17513(8) 0.4131(2) 0.31277(5) 0.0165(3) Uani 1 1 d . . .
H10 H 0.1686 0.2474 0.3051 0.020 Uiso 1 1 calc R . .
C7 C 0.00409(8) 0.8554(2) 0.25039(6) 0.0192(3) Uani 1 1 d . . .
H7 H -0.0101 1.0025 0.2611 0.023 Uiso 1 1 calc R . .
C2 C -0.07246(8) 0.4088(2) 0.12496(6) 0.0198(3) Uani 1 1 d . . .
H2 H -0.0556 0.2632 0.1153 0.024 Uiso 1 1 calc R . .
C6 C -0.04803(8) 0.7439(2) 0.19428(6) 0.0177(3) Uani 1 1 d . . .
C18 C 0.08674(8) 0.6751(2) 0.47354(6) 0.0205(3) Uani 1 1 d . . .
H18 H 0.0685 0.7636 0.4350 0.025 Uiso 1 1 calc R . .
C8 C 0.07470(8) 0.7492(2) 0.28873(6) 0.0183(3) Uani 1 1 d . . .
H8 H 0.1104 0.8221 0.3263 0.022 Uiso 1 1 calc R . .
C11 C 0.32897(8) 0.4108(2) 0.32979(5) 0.0188(3) Uani 1 1 d . . .
H11A H 0.3743 0.4843 0.3148 0.023 Uiso 1 1 calc R . .
H11B H 0.3325 0.2471 0.3227 0.023 Uiso 1 1 calc R . .
C25 C 0.14385(7) 0.4096(2) 0.58192(6) 0.0175(3) Uani 1 1 d . . .
C5 C -0.12373(8) 0.8381(2) 0.15202(6) 0.0221(3) Uani 1 1 d . . .
H5 H -0.1418 0.9833 0.1609 0.026 Uiso 1 1 calc R . .
C22 C 0.14030(8) 0.5640(2) 0.70528(6) 0.0246(3) Uani 1 1 d . . .
H22 H 0.1385 0.6138 0.7471 0.030 Uiso 1 1 calc R . .
C15 C 0.26989(8) 0.3621(2) 0.42271(6) 0.0174(3) Uani 1 1 d . . .
H15A H 0.2680 0.1967 0.4174 0.021 Uiso 1 1 calc R . .
H15B H 0.2775 0.3955 0.4694 0.021 Uiso 1 1 calc R . .
C19 C 0.08381(8) 0.7607(2) 0.53208(6) 0.0208(3) Uani 1 1 d . . .
H19 H 0.0631 0.9086 0.5346 0.025 Uiso 1 1 calc R . .
C21 C 0.11085(8) 0.7002(2) 0.65204(6) 0.0224(3) Uani 1 1 d . . .
H21 H 0.0894 0.8453 0.6572 0.027 Uiso 1 1 calc R . .
C23 C 0.17339(8) 0.3500(2) 0.69831(6) 0.0251(3) Uani 1 1 d . . .
H23 H 0.1944 0.2572 0.7357 0.030 Uiso 1 1 calc R . .
C20 C 0.11204(8) 0.6266(2) 0.58900(6) 0.0182(3) Uani 1 1 d . . .
C14 C 0.42627(8) 0.3242(2) 0.44023(6) 0.0212(3) Uani 1 1 d . . .
H14A H 0.4363 0.3443 0.4874 0.032 Uiso 1 1 calc R . .
H14B H 0.4757 0.3804 0.4277 0.032 Uiso 1 1 calc R . .
H14C H 0.4181 0.1641 0.4293 0.032 Uiso 1 1 calc R . .
C4 C -0.17079(8) 0.7214(2) 0.09862(6) 0.0239(3) Uani 1 1 d . . .
H4 H -0.2212 0.7864 0.0706 0.029 Uiso 1 1 calc R . .
C12 C 0.34640(8) 0.4546(2) 0.40328(6) 0.0166(3) Uani 1 1 d . . .
C24 C 0.17572(8) 0.2737(2) 0.63831(6) 0.0216(3) Uani 1 1 d . . .
H24 H 0.1987 0.1295 0.6345 0.026 Uiso 1 1 calc R . .
C13 C 0.35806(8) 0.7051(2) 0.41831(6) 0.0215(3) Uani 1 1 d . . .
H13A H 0.3052 0.7850 0.3961 0.032 Uiso 1 1 calc R . .
H13B H 0.4050 0.7627 0.4029 0.032 Uiso 1 1 calc R . .
H13C H 0.3714 0.7285 0.4656 0.032 Uiso 1 1 calc R . .
C3 C -0.14496(8) 0.5051(2) 0.08478(6) 0.0235(3) Uani 1 1 d . . .
H3 H -0.1780 0.4258 0.0474 0.028 Uiso 1 1 calc R . .
H100 H 0.2449(9) 0.652(3) 0.2876(7) 0.028(4) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
N3 C9 1.3205(15) . ?
N3 C1 1.3752(15) . ?
N4 C17 1.3226(15) . ?
N4 C25 1.3756(15) . ?
C9 C8 1.4184(18) . ?
C9 C10 1.5182(17) . ?
N1 C10 1.4568(15) . ?
N1 C11 1.4639(15) . ?
N1 H100 0.950(16) . ?
N2 C16 1.4736(15) . ?
N2 C15 1.4746(15) . ?
N2 C10 1.4868(14) . ?
C17 C18 1.4147(18) . ?
C17 C16 1.5142(16) . ?
C1 C2 1.4175(17) . ?
C1 C6 1.4189(18) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C10 H10 1.0000 . ?
C7 C8 1.3626(17) . ?
C7 C6 1.4192(17) . ?
C7 H7 0.9500 . ?
C2 C3 1.3720(18) . ?
C2 H2 0.9500 . ?
C6 C5 1.4198(17) . ?
C18 C19 1.3643(17) . ?
C18 H18 0.9500 . ?
C8 H8 0.9500 . ?
C11 C12 1.5353(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C25 C20 1.4160(19) . ?
C25 C24 1.4197(17) . ?
C5 C4 1.3671(19) . ?
C5 H5 0.9500 . ?
C22 C21 1.3663(19) . ?
C22 C23 1.408(2) . ?
C22 H22 0.9500 . ?
C15 C12 1.5292(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C19 C20 1.4161(17) . ?
C19 H19 0.9500 . ?
C21 C20 1.4221(17) . ?
C21 H21 0.9500 . ?
C23 C24 1.3711(18) . ?
C23 H23 0.9500 . ?
C14 C12 1.5281(17) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C4 C3 1.412(2) . ?
C4 H4 0.9500 . ?
C12 C13 1.5244(18) . ?
C24 H24 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C3 H3 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N3 C1 117.62(11) . . ?
C17 N4 C25 117.61(11) . . ?
N3 C9 C8 123.39(11) . . ?
N3 C9 C10 116.52(11) . . ?
C8 C9 C10 120.00(11) . . ?
C10 N1 C11 112.92(10) . . ?
C10 N1 H100 109.7(9) . . ?
C11 N1 H100 110.9(9) . . ?
C16 N2 C15 108.67(9) . . ?
C16 N2 C10 110.60(9) . . ?
C15 N2 C10 110.36(9) . . ?
N4 C17 C18 123.22(11) . . ?
N4 C17 C16 117.39(11) . . ?
C18 C17 C16 119.38(11) . . ?
N3 C1 C2 118.01(11) . . ?
N3 C1 C6 122.78(11) . . ?
C2 C1 C6 119.21(11) . . ?
N2 C16 C17 110.90(10) . . ?
N2 C16 H16A 109.5 . . ?
C17 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 108.0 . . ?
N1 C10 N2 112.96(10) . . ?
N1 C10 C9 107.60(10) . . ?
N2 C10 C9 110.08(9) . . ?
N1 C10 H10 108.7 . . ?
N2 C10 H10 108.7 . . ?
C9 C10 H10 108.7 . . ?
C8 C7 C6 119.27(12) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C3 C2 C1 120.38(12) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C1 C6 C7 117.38(11) . . ?
C1 C6 C5 119.01(11) . . ?
C7 C6 C5 123.60(12) . . ?
C19 C18 C17 119.65(12) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C7 C8 C9 119.54(11) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
N1 C11 C12 114.08(10) . . ?
N1 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
N1 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
N4 C25 C20 122.82(11) . . ?
N4 C25 C24 118.19(12) . . ?
C20 C25 C24 118.99(11) . . ?
C4 C5 C6 120.52(12) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C21 C22 C23 120.13(12) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
N2 C15 C12 112.63(10) . . ?
N2 C15 H15A 109.1 . . ?
C12 C15 H15A 109.1 . . ?
N2 C15 H15B 109.1 . . ?
C12 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C18 C19 C20 119.24(12) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C22 C21 C20 120.56(13) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C24 C23 C22 120.90(12) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C25 C20 C19 117.41(11) . . ?
C25 C20 C21 119.20(11) . . ?
C19 C20 C21 123.38(12) . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C4 C3 120.48(12) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C13 C12 C14 110.57(10) . . ?
C13 C12 C15 110.89(10) . . ?
C14 C12 C15 108.70(10) . . ?
C13 C12 C11 110.87(10) . . ?
C14 C12 C11 108.73(10) . . ?
C15 C12 C11 106.97(10) . . ?
C23 C24 C25 120.19(13) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 C3 C4 120.39(12) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.043
