# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_l1034a
_database_code_depnum_ccdc_archive 'CCDC 1978458'
loop_
_audit_author_name
_audit_author_address
'Martin Lutz'
;Utrecht University
Netherlands
;
_audit_update_record             
;
2020-01-17 deposited with the CCDC.	2020-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H19 N2 O4 Re'
_chemical_formula_sum            'C15 H19 N2 O4 Re'
_chemical_formula_weight         477.52

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

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

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

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

_cell_length_a                   14.6069(6)
_cell_length_b                   8.8710(4)
_cell_length_c                   12.0927(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.801(3)
_cell_angle_gamma                90
_cell_volume                     1566.80(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    19368
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      27.53

loop_
_diffrn_orient_matrix_type
_diffrn_orient_matrix_UB_11
_diffrn_orient_matrix_UB_12
_diffrn_orient_matrix_UB_13
_diffrn_orient_matrix_UB_21
_diffrn_orient_matrix_UB_22
_diffrn_orient_matrix_UB_23
_diffrn_orient_matrix_UB_31
_diffrn_orient_matrix_UB_32
_diffrn_orient_matrix_UB_33
'Nonius RMAT' -0.0403150 0.0906629 -0.0072743 -0.0538512 -0.0616137 0.0228477
0.0129133 0.0261050 0.0791895
'Nonius RMAT' -0.0426709 0.0877822 -0.0066647 -0.0516635 -0.0646807 0.0254356
0.0142152 0.0284285 0.0784507

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.024
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    7.775
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1658
_exptl_absorpt_correction_T_max  0.4305
_exptl_absorpt_process_details   TWINABS-2012/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa ApexII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54428
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.686
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3685
_reflns_number_gt                3281
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       Apex3
_computing_cell_refinement       Peakref
_computing_data_reduction        'Eval15, Twinabs'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0698P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3685
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0913
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Re1 Re 0.32977(2) 0.52110(2) 0.39318(2) 0.01638(10) Uani 1 1 d . . . . .
O1 O 0.2135(2) 0.6522(4) 0.4301(3) 0.0220(7) Uani 1 1 d . . . . .
O2 O 0.3649(2) 0.4253(4) 0.6332(3) 0.0288(8) Uani 1 1 d . . . . .
O3 O 0.4921(2) 0.3231(5) 0.3301(3) 0.0328(8) Uani 1 1 d . . . . .
O4 O 0.4634(2) 0.7857(4) 0.4234(3) 0.0331(8) Uani 1 1 d . . . . .
N1 N 0.2877(2) 0.5734(5) 0.2190(3) 0.0178(7) Uani 1 1 d . . . . .
N2 N 0.2280(2) 0.3311(5) 0.3606(3) 0.0202(8) Uani 1 1 d . . . . .
C1 C 0.1668(3) 0.7545(5) 0.3720(4) 0.0194(9) Uani 1 1 d . . . . .
C2 C 0.0904(3) 0.8214(6) 0.4221(4) 0.0235(10) Uani 1 1 d . . . . .
H2 H 0.074357 0.792926 0.495048 0.028 Uiso 1 1 calc R U . . .
C3 C 0.0381(3) 0.9287(6) 0.3659(4) 0.0284(11) Uani 1 1 d . . . . .
H3 H -0.012722 0.973309 0.401549 0.034 Uiso 1 1 calc R U . . .
C4 C 0.0585(3) 0.9709(5) 0.2608(5) 0.0241(11) Uani 1 1 d . . . . .
H4 H 0.022363 1.044483 0.223414 0.029 Uiso 1 1 calc R U . . .
C5 C 0.1327(3) 0.9050(5) 0.2089(4) 0.0238(10) Uani 1 1 d . . . . .
H5 H 0.146226 0.932319 0.134953 0.029 Uiso 1 1 calc R U . . .
C6 C 0.1880(3) 0.7988(5) 0.2638(4) 0.0193(9) Uani 1 1 d . . . . .
C7 C 0.2694(3) 0.7388(5) 0.2025(4) 0.0202(9) Uani 1 1 d . . . . .
H7A H 0.259785 0.757834 0.122540 0.024 Uiso 1 1 calc R U . . .
H7B H 0.324412 0.795861 0.226463 0.024 Uiso 1 1 calc R U . . .
C8 C 0.2022(3) 0.4858(5) 0.1933(4) 0.0198(10) Uani 1 1 d . . . . .
H8A H 0.192289 0.481516 0.112217 0.024 Uiso 1 1 calc R U . . .
H8B H 0.148944 0.537094 0.226260 0.024 Uiso 1 1 calc R U . . .
C9 C 0.2101(3) 0.3281(5) 0.2389(4) 0.0218(9) Uani 1 1 d . . . . .
H9A H 0.152638 0.272445 0.223279 0.026 Uiso 1 1 calc R U . . .
H9B H 0.260635 0.274611 0.201821 0.026 Uiso 1 1 calc R U . . .
C10 C 0.3593(3) 0.5317(5) 0.1384(4) 0.0223(10) Uani 1 1 d . . . . .
H10A H 0.369308 0.422500 0.140768 0.033 Uiso 1 1 calc R U . . .
H10B H 0.416483 0.583864 0.157523 0.033 Uiso 1 1 calc R U . . .
H10C H 0.339273 0.561195 0.063804 0.033 Uiso 1 1 calc R U . . .
C11 C 0.1392(3) 0.3487(6) 0.4197(4) 0.0277(11) Uani 1 1 d . . . . .
H11A H 0.097517 0.267092 0.397857 0.041 Uiso 1 1 calc R U . . .
H11B H 0.111615 0.445968 0.400267 0.041 Uiso 1 1 calc R U . . .
H11C H 0.150434 0.344477 0.499776 0.041 Uiso 1 1 calc R U . . .
C12 C 0.2655(3) 0.1815(5) 0.3945(4) 0.0273(11) Uani 1 1 d . . . . .
H12A H 0.279686 0.182539 0.473988 0.041 Uiso 1 1 calc R U . . .
H12B H 0.321487 0.160814 0.353407 0.041 Uiso 1 1 calc R U . . .
H12C H 0.220102 0.102970 0.378497 0.041 Uiso 1 1 calc R U . . .
C13 C 0.3523(3) 0.4636(5) 0.5429(4) 0.0199(9) Uani 1 1 d . . . . .
C14 C 0.4309(3) 0.3968(5) 0.3550(4) 0.0218(9) Uani 1 1 d . . . . .
C15 C 0.4132(3) 0.6849(5) 0.4121(4) 0.0217(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 C13 1.906(5) . ?
Re1 C14 1.905(4) . ?
Re1 C15 1.908(5) . ?
Re1 O1 2.111(3) . ?
Re1 N1 2.235(4) . ?
Re1 N2 2.278(4) . ?
O1 C1 1.330(5) . ?
O2 C13 1.155(6) . ?
O3 C14 1.151(5) . ?
O4 C15 1.164(6) . ?
N1 C10 1.486(6) . ?
N1 C8 1.499(6) . ?
N1 C7 1.504(6) . ?
N2 C12 1.490(6) . ?
N2 C9 1.492(6) . ?
N2 C11 1.498(6) . ?
C1 C6 1.404(6) . ?
C1 C2 1.409(6) . ?
C2 C3 1.391(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.362(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.402(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.507(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.507(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C13 Re1 C14 87.2(2) . . ?
C13 Re1 C15 89.35(19) . . ?
C14 Re1 C15 88.53(19) . . ?
C13 Re1 O1 94.32(17) . . ?
C14 Re1 O1 177.10(15) . . ?
C15 Re1 O1 93.96(16) . . ?
C13 Re1 N1 173.16(16) . . ?
C14 Re1 N1 95.52(17) . . ?
C15 Re1 N1 96.98(17) . . ?
O1 Re1 N1 82.71(13) . . ?
C13 Re1 N2 93.99(16) . . ?
C14 Re1 N2 92.04(17) . . ?
C15 Re1 N2 176.64(16) . . ?
O1 Re1 N2 85.39(13) . . ?
N1 Re1 N2 79.66(14) . . ?
C1 O1 Re1 132.2(3) . . ?
C10 N1 C8 109.1(4) . . ?
C10 N1 C7 106.4(3) . . ?
C8 N1 C7 109.4(3) . . ?
C10 N1 Re1 112.3(3) . . ?
C8 N1 Re1 107.8(3) . . ?
C7 N1 Re1 111.9(3) . . ?
C12 N2 C9 108.3(4) . . ?
C12 N2 C11 106.2(4) . . ?
C9 N2 C11 109.4(3) . . ?
C12 N2 Re1 112.0(3) . . ?
C9 N2 Re1 106.8(3) . . ?
C11 N2 Re1 114.1(3) . . ?
O1 C1 C6 124.4(4) . . ?
O1 C1 C2 117.6(4) . . ?
C6 C1 C2 118.0(4) . . ?
C3 C2 C1 120.7(4) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 121.2(4) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 119.2(4) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 121.1(5) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 119.8(4) . . ?
C1 C6 C7 123.0(4) . . ?
C5 C6 C7 117.3(4) . . ?
N1 C7 C6 114.8(4) . . ?
N1 C7 H7A 108.6 . . ?
C6 C7 H7A 108.6 . . ?
N1 C7 H7B 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.5 . . ?
N1 C8 C9 110.3(4) . . ?
N1 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
N2 C9 C8 110.9(4) . . ?
N2 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 Re1 178.3(4) . . ?
O3 C14 Re1 178.7(5) . . ?
O4 C15 Re1 179.4(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Re1 O1 C1 C6 0.2(6) . . . . ?
Re1 O1 C1 C2 179.5(3) . . . . ?
O1 C1 C2 C3 -179.7(4) . . . . ?
C6 C1 C2 C3 -0.4(7) . . . . ?
C1 C2 C3 C4 0.8(8) . . . . ?
C2 C3 C4 C5 0.2(7) . . . . ?
C3 C4 C5 C6 -1.5(7) . . . . ?
O1 C1 C6 C5 178.3(4) . . . . ?
C2 C1 C6 C5 -0.9(6) . . . . ?
O1 C1 C6 C7 -2.5(7) . . . . ?
C2 C1 C6 C7 178.3(4) . . . . ?
C4 C5 C6 C1 1.9(7) . . . . ?
C4 C5 C6 C7 -177.3(4) . . . . ?
C10 N1 C7 C6 170.7(4) . . . . ?
C8 N1 C7 C6 53.1(5) . . . . ?
Re1 N1 C7 C6 -66.3(4) . . . . ?
C1 C6 C7 N1 39.9(6) . . . . ?
C5 C6 C7 N1 -140.9(4) . . . . ?
C10 N1 C8 C9 79.9(5) . . . . ?
C7 N1 C8 C9 -164.1(4) . . . . ?
Re1 N1 C8 C9 -42.2(4) . . . . ?
C12 N2 C9 C8 -161.3(4) . . . . ?
C11 N2 C9 C8 83.3(5) . . . . ?
Re1 N2 C9 C8 -40.5(4) . . . . ?
N1 C8 C9 N2 57.5(5) . . . . ?

_refine_diff_density_max         3.402
_refine_diff_density_min         -3.154
_refine_diff_density_rms         0.230

####################################################################### 
# 
# 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_l1061a
_database_code_depnum_ccdc_archive 'CCDC 1978460'
loop_
_audit_author_name
_audit_author_address
'Martin Lutz'
;Utrecht University
Netherlands
;
_audit_update_record             
;
2020-01-17 deposited with the CCDC.	2020-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H35 N2 O4 Re'
_chemical_formula_sum            'C23 H35 N2 O4 Re'
_chemical_formula_weight         589.73

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'
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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   23.9270(7)
_cell_length_b                   9.4928(3)
_cell_length_c                   22.1646(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.575(2)
_cell_angle_gamma                90
_cell_volume                     4825.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    25392
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      27.55

loop_
_diffrn_orient_matrix_type
_diffrn_orient_matrix_UB_11
_diffrn_orient_matrix_UB_12
_diffrn_orient_matrix_UB_13
_diffrn_orient_matrix_UB_21
_diffrn_orient_matrix_UB_22
_diffrn_orient_matrix_UB_23
_diffrn_orient_matrix_UB_31
_diffrn_orient_matrix_UB_32
_diffrn_orient_matrix_UB_33
'Nonius RMAT' 0.0099641 0.1008382 0.0110674 -0.0424395 0.0232322 -0.0101971
0.0009537 -0.0197088 0.0446051

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_F_000             2352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    5.066
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.2599
_exptl_absorpt_correction_T_max  0.7995
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa ApexII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43450
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.211
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5540
_reflns_number_gt                4228
_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       Apex3
_computing_cell_refinement       Peakref
_computing_data_reduction        'Eval15, Sadabs'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0249P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5540
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0611
_refine_ls_wR_factor_gt          0.0562
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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 0.84599(2) 0.59689(2) 0.65796(2) 0.01729(5) Uani 1 1 d . . . . .
O1 O 0.76889(11) 0.5558(3) 0.58241(12) 0.0184(6) Uani 1 1 d . . . . .
O2 O 0.79314(14) 0.5177(4) 0.76355(14) 0.0359(8) Uani 1 1 d . . . . .
O3 O 0.94690(14) 0.6800(4) 0.77147(15) 0.0414(9) Uani 1 1 d . . . . .
O4 O 0.89793(14) 0.3010(3) 0.66170(15) 0.0392(8) Uani 1 1 d . . . . .
N1 N 0.81197(14) 0.8189(3) 0.64650(15) 0.0189(7) Uani 1 1 d . . . . .
N2 N 0.88599(14) 0.6745(4) 0.58310(15) 0.0203(8) Uani 1 1 d . . . . .
C1 C 0.71900(16) 0.5833(4) 0.59750(17) 0.0164(8) Uani 1 1 d . . . . .
C2 C 0.67574(17) 0.4786(4) 0.59636(17) 0.0186(9) Uani 1 1 d . . . . .
C3 C 0.62552(17) 0.5223(5) 0.61010(18) 0.0205(9) Uani 1 1 d . . . . .
H3 H 0.596386 0.453337 0.608564 0.025 Uiso 1 1 calc R U . . .
C4 C 0.61415(17) 0.6603(4) 0.62611(18) 0.0197(9) Uani 1 1 d . . . . .
C5 C 0.65728(17) 0.7589(4) 0.62783(17) 0.0186(9) Uani 1 1 d . . . . .
H5 H 0.651975 0.853483 0.639023 0.022 Uiso 1 1 calc R U . . .
C6 C 0.70843(17) 0.7214(4) 0.61338(18) 0.0184(9) Uani 1 1 d . . . . .
C7 C 0.75037(16) 0.8323(4) 0.60496(19) 0.0195(9) Uani 1 1 d . . . . .
H7A H 0.735187 0.925573 0.612673 0.023 Uiso 1 1 calc R U . . .
H7B H 0.751154 0.830532 0.560548 0.023 Uiso 1 1 calc R U . . .
C8 C 0.85161(17) 0.8972(5) 0.61672(19) 0.0236(9) Uani 1 1 d . . . . .
H8A H 0.889899 0.912116 0.648130 0.028 Uiso 1 1 calc R U . . .
H8B H 0.834677 0.990629 0.602175 0.028 Uiso 1 1 calc R U . . .
C9 C 0.85974(18) 0.8150(4) 0.56175(19) 0.0247(10) Uani 1 1 d . . . . .
H9A H 0.821563 0.802196 0.529873 0.030 Uiso 1 1 calc R U . . .
H9B H 0.885519 0.868041 0.541977 0.030 Uiso 1 1 calc R U . . .
C10 C 0.81492(19) 0.8850(5) 0.70835(19) 0.0273(10) Uani 1 1 d . . . . .
H10A H 0.805706 0.985559 0.702252 0.041 Uiso 1 1 calc R U . . .
H10B H 0.854291 0.873683 0.736971 0.041 Uiso 1 1 calc R U . . .
H10C H 0.786703 0.839352 0.726492 0.041 Uiso 1 1 calc R U . . .
C11 C 0.87277(19) 0.5770(4) 0.52815(19) 0.0270(10) Uani 1 1 d . . . . .
H11A H 0.885469 0.619748 0.494020 0.041 Uiso 1 1 calc R U . . .
H11B H 0.830695 0.559310 0.513641 0.041 Uiso 1 1 calc R U . . .
H11C H 0.893452 0.487801 0.540653 0.041 Uiso 1 1 calc R U . . .
C12 C 0.95011(17) 0.6902(5) 0.6065(2) 0.0302(11) Uani 1 1 d . . . . .
H12A H 0.965305 0.720106 0.571917 0.045 Uiso 1 1 calc R U . . .
H12B H 0.967634 0.599738 0.623129 0.045 Uiso 1 1 calc R U . . .
H12C H 0.959850 0.761085 0.640046 0.045 Uiso 1 1 calc R U . . .
C13 C 0.68269(18) 0.3248(4) 0.57742(19) 0.0205(9) Uani 1 1 d . . . . .
C14 C 0.63335(19) 0.2291(4) 0.5850(2) 0.0309(11) Uani 1 1 d . . . . .
H14A H 0.631306 0.234339 0.628489 0.046 Uiso 1 1 calc R U . . .
H14B H 0.641085 0.131704 0.575122 0.046 Uiso 1 1 calc R U . . .
H14C H 0.596201 0.260256 0.556273 0.046 Uiso 1 1 calc R U . . .
C15 C 0.68174(19) 0.3224(5) 0.50800(19) 0.0273(10) Uani 1 1 d . . . . .
H15A H 0.687516 0.225692 0.495555 0.041 Uiso 1 1 calc R U . . .
H15B H 0.713051 0.382551 0.502067 0.041 Uiso 1 1 calc R U . . .
H15C H 0.644047 0.357573 0.481988 0.041 Uiso 1 1 calc R U . . .
C16 C 0.74038(19) 0.2636(4) 0.6182(2) 0.0301(11) Uani 1 1 d . . . . .
H16A H 0.772953 0.318433 0.611918 0.045 Uiso 1 1 calc R U . . .
H16B H 0.743903 0.165342 0.606249 0.045 Uiso 1 1 calc R U . . .
H16C H 0.741170 0.267872 0.662651 0.045 Uiso 1 1 calc R U . . .
C17 C 0.55583(17) 0.6964(5) 0.6380(2) 0.0244(10) Uani 1 1 d . . . . .
C18 C 0.5543(2) 0.8471(5) 0.6610(3) 0.0493(15) Uani 1 1 d . . . . .
H18A H 0.558197 0.912785 0.628336 0.074 Uiso 1 1 calc R U . . .
H18B H 0.586572 0.861562 0.699283 0.074 Uiso 1 1 calc R U . . .
H18C H 0.517189 0.863983 0.670261 0.074 Uiso 1 1 calc R U . . .
C19 C 0.5068(2) 0.6783(8) 0.5775(3) 0.070(2) Uani 1 1 d . . . . .
H19A H 0.507517 0.582150 0.561619 0.105 Uiso 1 1 calc R U . . .
H19B H 0.511977 0.745610 0.545941 0.105 Uiso 1 1 calc R U . . .
H19C H 0.469299 0.695587 0.585754 0.105 Uiso 1 1 calc R U . . .
C20 C 0.5447(2) 0.5997(6) 0.6881(3) 0.0530(15) Uani 1 1 d . . . . .
H20A H 0.574620 0.615655 0.728157 0.079 Uiso 1 1 calc R U . . .
H20B H 0.546189 0.501325 0.675242 0.079 Uiso 1 1 calc R U . . .
H20C H 0.506151 0.619860 0.693240 0.079 Uiso 1 1 calc R U . . .
C21 C 0.81107(17) 0.5444(5) 0.7224(2) 0.0236(10) Uani 1 1 d . . . . .
C22 C 0.91085(19) 0.6487(5) 0.7264(2) 0.0264(10) Uani 1 1 d . . . . .
C23 C 0.87800(18) 0.4103(5) 0.6606(2) 0.0255(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 C22 1.900(5) . ?
Re1 C21 1.914(4) . ?
Re1 C23 1.924(4) . ?
Re1 O1 2.144(3) . ?
Re1 N1 2.247(3) . ?
Re1 N2 2.262(3) . ?
O1 C1 1.354(4) . ?
O2 C21 1.142(5) . ?
O3 C22 1.157(5) . ?
O4 C23 1.140(5) . ?
N1 C10 1.491(5) . ?
N1 C8 1.498(5) . ?
N1 C7 1.504(5) . ?
N2 C12 1.480(5) . ?
N2 C11 1.490(5) . ?
N2 C9 1.493(5) . ?
C1 C6 1.399(5) . ?
C1 C2 1.430(5) . ?
C2 C3 1.385(5) . ?
C2 C13 1.541(5) . ?
C3 C4 1.404(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(5) . ?
C4 C17 1.530(5) . ?
C5 C6 1.397(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.503(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.505(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C15 1.532(5) . ?
C13 C16 1.533(6) . ?
C13 C14 1.536(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C20 1.522(6) . ?
C17 C19 1.519(6) . ?
C17 C18 1.524(6) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C22 Re1 C21 84.42(17) . . ?
C22 Re1 C23 89.22(19) . . ?
C21 Re1 C23 89.54(18) . . ?
C22 Re1 O1 174.69(15) . . ?
C21 Re1 O1 94.22(14) . . ?
C23 Re1 O1 95.91(15) . . ?
C22 Re1 N1 91.98(16) . . ?
C21 Re1 N1 96.17(15) . . ?
C23 Re1 N1 174.25(14) . . ?
O1 Re1 N1 83.05(11) . . ?
C22 Re1 N2 94.67(15) . . ?
C21 Re1 N2 176.07(15) . . ?
C23 Re1 N2 94.27(15) . . ?
O1 Re1 N2 86.35(11) . . ?
N1 Re1 N2 80.03(12) . . ?
C1 O1 Re1 113.3(2) . . ?
C10 N1 C8 109.0(3) . . ?
C10 N1 C7 107.9(3) . . ?
C8 N1 C7 108.7(3) . . ?
C10 N1 Re1 111.7(2) . . ?
C8 N1 Re1 105.1(2) . . ?
C7 N1 Re1 114.1(2) . . ?
C12 N2 C11 107.8(3) . . ?
C12 N2 C9 108.8(3) . . ?
C11 N2 C9 108.9(3) . . ?
C12 N2 Re1 112.9(2) . . ?
C11 N2 Re1 111.2(2) . . ?
C9 N2 Re1 107.2(2) . . ?
O1 C1 C6 118.6(3) . . ?
O1 C1 C2 123.1(4) . . ?
C6 C1 C2 118.3(4) . . ?
C3 C2 C1 117.2(4) . . ?
C3 C2 C13 120.8(4) . . ?
C1 C2 C13 122.0(3) . . ?
C2 C3 C4 125.3(4) . . ?
C2 C3 H3 117.3 . . ?
C4 C3 H3 117.3 . . ?
C5 C4 C3 116.1(4) . . ?
C5 C4 C17 123.6(4) . . ?
C3 C4 C17 120.2(4) . . ?
C4 C5 C6 121.1(4) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 122.0(4) . . ?
C5 C6 C7 120.7(4) . . ?
C1 C6 C7 116.8(3) . . ?
C6 C7 N1 115.9(3) . . ?
C6 C7 H7A 108.3 . . ?
N1 C7 H7A 108.3 . . ?
C6 C7 H7B 108.3 . . ?
N1 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
N1 C8 C9 110.1(3) . . ?
N1 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.2 . . ?
N2 C9 C8 110.3(3) . . ?
N2 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
N2 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C15 C13 C16 109.9(3) . . ?
C15 C13 C14 108.0(3) . . ?
C16 C13 C14 107.6(3) . . ?
C15 C13 C2 108.4(3) . . ?
C16 C13 C2 110.3(3) . . ?
C14 C13 C2 112.6(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C20 C17 C19 109.0(4) . . ?
C20 C17 C18 107.2(4) . . ?
C19 C17 C18 108.4(4) . . ?
C20 C17 C4 110.4(4) . . ?
C19 C17 C4 109.6(4) . . ?
C18 C17 C4 112.2(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C21 Re1 175.5(4) . . ?
O3 C22 Re1 173.8(4) . . ?
O4 C23 Re1 178.5(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Re1 O1 C1 C6 62.0(4) . . . . ?
Re1 O1 C1 C2 -119.7(3) . . . . ?
O1 C1 C2 C3 -177.1(4) . . . . ?
C6 C1 C2 C3 1.1(5) . . . . ?
O1 C1 C2 C13 -0.2(6) . . . . ?
C6 C1 C2 C13 178.1(3) . . . . ?
C1 C2 C3 C4 -1.2(6) . . . . ?
C13 C2 C3 C4 -178.2(4) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
C2 C3 C4 C17 177.8(4) . . . . ?
C3 C4 C5 C6 0.9(6) . . . . ?
C17 C4 C5 C6 -176.6(4) . . . . ?
C4 C5 C6 C1 -1.0(6) . . . . ?
C4 C5 C6 C7 169.9(4) . . . . ?
O1 C1 C6 C5 178.2(3) . . . . ?
C2 C1 C6 C5 -0.1(6) . . . . ?
O1 C1 C6 C7 7.0(5) . . . . ?
C2 C1 C6 C7 -171.3(3) . . . . ?
C5 C6 C7 N1 123.6(4) . . . . ?
C1 C6 C7 N1 -65.1(5) . . . . ?
C10 N1 C7 C6 -83.6(4) . . . . ?
C8 N1 C7 C6 158.3(3) . . . . ?
Re1 N1 C7 C6 41.3(4) . . . . ?
C10 N1 C8 C9 167.6(3) . . . . ?
C7 N1 C8 C9 -74.9(4) . . . . ?
Re1 N1 C8 C9 47.7(3) . . . . ?
C12 N2 C9 C8 -84.4(4) . . . . ?
C11 N2 C9 C8 158.4(3) . . . . ?
Re1 N2 C9 C8 38.0(4) . . . . ?
N1 C8 C9 N2 -60.0(4) . . . . ?
C3 C2 C13 C15 111.5(4) . . . . ?
C1 C2 C13 C15 -65.3(5) . . . . ?
C3 C2 C13 C16 -128.2(4) . . . . ?
C1 C2 C13 C16 55.0(5) . . . . ?
C3 C2 C13 C14 -8.0(5) . . . . ?
C1 C2 C13 C14 175.2(4) . . . . ?
C5 C4 C17 C20 -127.8(4) . . . . ?
C3 C4 C17 C20 54.8(5) . . . . ?
C5 C4 C17 C19 112.2(5) . . . . ?
C3 C4 C17 C19 -65.2(5) . . . . ?
C5 C4 C17 C18 -8.3(6) . . . . ?
C3 C4 C17 C18 174.3(4) . . . . ?

_refine_diff_density_max         1.157
_refine_diff_density_min         -0.601
_refine_diff_density_rms         0.137

####################################################################### 
# 
# 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_l1048a
_database_code_depnum_ccdc_archive 'CCDC 1978459'
loop_
_audit_author_name
_audit_author_address
'Martin Lutz'
;Utrecht University
Netherlands
;
_audit_update_record             
;
2020-01-17 deposited with the CCDC.	2020-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 N3 O6 Re'
_chemical_formula_sum            'C15 H18 N3 O6 Re'
_chemical_formula_weight         522.52

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   8.90063(16)
_cell_length_b                   11.9803(3)
_cell_length_c                   31.8099(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3391.95(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    29749
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      27.57

loop_
_diffrn_orient_matrix_type
_diffrn_orient_matrix_UB_11
_diffrn_orient_matrix_UB_12
_diffrn_orient_matrix_UB_13
_diffrn_orient_matrix_UB_21
_diffrn_orient_matrix_UB_22
_diffrn_orient_matrix_UB_23
_diffrn_orient_matrix_UB_31
_diffrn_orient_matrix_UB_32
_diffrn_orient_matrix_UB_33
'Nonius RMAT' -0.0456330 -0.0146474 0.0281763 -0.0932658 -0.0282554 -0.0139042
0.0428312 -0.0771323 -0.0002572

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.046
_exptl_crystal_F_000             2016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    7.202
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.2953
_exptl_absorpt_correction_T_max  0.9125
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa ApexII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52093
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         2.561
_diffrn_reflns_theta_max         27.514
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3901
_reflns_number_gt                3027
_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       Apex3
_computing_cell_refinement       Peakref
_computing_data_reduction        'Eval15, Sadabs'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0136P)²+6.7529P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3901
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0229
_refine_ls_wR_factor_ref         0.0443
_refine_ls_wR_factor_gt          0.0403
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Re1 Re 0.47838(2) 0.39887(2) 0.07771(2) 0.01047(4) Uani 1 1 d . . . . .
O1 O 0.3438(3) 0.4452(2) 0.12994(8) 0.0140(5) Uani 1 1 d . . . . .
O2 O 0.5778(3) 0.6398(2) 0.06132(9) 0.0215(6) Uani 1 1 d . . . . .
O3 O 0.6751(3) 0.3259(2) 0.00396(9) 0.0233(7) Uani 1 1 d . . . . .
O4 O 0.2187(3) 0.4278(2) 0.01524(9) 0.0229(7) Uani 1 1 d . . . . .
O5 O -0.1007(3) 0.2739(2) 0.26597(9) 0.0288(7) Uani 1 1 d . . . . .
O6 O -0.1030(4) 0.1321(2) 0.22422(10) 0.0359(8) Uani 1 1 d . . . . .
N1 N 0.4201(3) 0.2255(2) 0.09817(9) 0.0094(6) Uani 1 1 d . . . . .
N2 N 0.6641(3) 0.3668(2) 0.12535(10) 0.0136(7) Uani 1 1 d . . . . .
N3 N -0.0612(3) 0.2270(3) 0.23346(10) 0.0193(7) Uani 1 1 d . . . . .
C1 C 0.2426(4) 0.3916(3) 0.15192(11) 0.0115(7) Uani 1 1 d . . . . .
C2 C 0.1776(4) 0.4471(3) 0.18679(12) 0.0149(8) Uani 1 1 d . . . . .
H2 H 0.203927 0.522661 0.192119 0.018 Uiso 1 1 calc R U . . .
C3 C 0.0772(4) 0.3945(3) 0.21319(11) 0.0155(7) Uani 1 1 d . . . . .
H3 H 0.035092 0.432906 0.236515 0.019 Uiso 1 1 calc R U . . .
C4 C 0.0388(4) 0.2843(3) 0.20500(11) 0.0151(8) Uani 1 1 d . . . . .
C5 C 0.0973(4) 0.2280(3) 0.17084(12) 0.0135(8) Uani 1 1 d . . . . .
H5 H 0.068353 0.152789 0.165845 0.016 Uiso 1 1 calc R U . . .
C6 C 0.1979(4) 0.2796(3) 0.14366(11) 0.0109(7) Uani 1 1 d . . . . .
C7 C 0.2551(4) 0.2140(3) 0.10640(12) 0.0124(7) Uani 1 1 d . . . . .
H7A H 0.231878 0.134117 0.110954 0.015 Uiso 1 1 calc R U . . .
H7B H 0.199725 0.238465 0.081026 0.015 Uiso 1 1 calc R U . . .
C8 C 0.5070(4) 0.2003(3) 0.13718(11) 0.0137(7) Uani 1 1 d . . . . .
H8A H 0.509360 0.118656 0.141922 0.016 Uiso 1 1 calc R U . . .
H8B H 0.457532 0.235665 0.161662 0.016 Uiso 1 1 calc R U . . .
C9 C 0.6656(4) 0.2441(3) 0.13291(13) 0.0153(8) Uani 1 1 d . . . . .
H9A H 0.722580 0.227777 0.158915 0.018 Uiso 1 1 calc R U . . .
H9B H 0.716364 0.206120 0.109218 0.018 Uiso 1 1 calc R U . . .
C10 C 0.4579(4) 0.1406(3) 0.06531(12) 0.0148(8) Uani 1 1 d . . . . .
H10A H 0.566273 0.141934 0.059860 0.022 Uiso 1 1 calc R U . . .
H10B H 0.403548 0.157979 0.039333 0.022 Uiso 1 1 calc R U . . .
H10C H 0.428678 0.066220 0.075212 0.022 Uiso 1 1 calc R U . . .
C11 C 0.6428(4) 0.4268(3) 0.16590(13) 0.0219(9) Uani 1 1 d . . . . .
H11A H 0.726608 0.409711 0.184806 0.033 Uiso 1 1 calc R U . . .
H11B H 0.548291 0.402872 0.178895 0.033 Uiso 1 1 calc R U . . .
H11C H 0.639380 0.507412 0.160694 0.033 Uiso 1 1 calc R U . . .
C12 C 0.8140(4) 0.3999(3) 0.10893(13) 0.0204(8) Uani 1 1 d . . . . .
H12A H 0.814937 0.480406 0.103410 0.031 Uiso 1 1 calc R U . . .
H12B H 0.834561 0.359438 0.082789 0.031 Uiso 1 1 calc R U . . .
H12C H 0.891323 0.381805 0.129777 0.031 Uiso 1 1 calc R U . . .
C13 C 0.5383(4) 0.5492(3) 0.06711(11) 0.0155(8) Uani 1 1 d . . . . .
C14 C 0.6017(4) 0.3542(3) 0.03200(12) 0.0147(8) Uani 1 1 d . . . . .
C15 C 0.3163(4) 0.4164(3) 0.03865(12) 0.0135(8) 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 C14 1.899(4) . ?
Re1 C13 1.909(4) . ?
Re1 C15 1.916(4) . ?
Re1 O1 2.122(2) . ?
Re1 N1 2.238(3) . ?
Re1 N2 2.275(3) . ?
O1 C1 1.309(4) . ?
O2 C13 1.156(4) . ?
O3 C14 1.157(5) . ?
O4 C15 1.152(4) . ?
O5 N3 1.229(4) . ?
O6 N3 1.231(4) . ?
N1 C8 1.493(4) . ?
N1 C10 1.497(4) . ?
N1 C7 1.499(4) . ?
N2 C12 1.487(4) . ?
N2 C9 1.489(4) . ?
N2 C11 1.489(5) . ?
N3 C4 1.444(5) . ?
C1 C2 1.417(5) . ?
C1 C6 1.424(5) . ?
C2 C3 1.379(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(5) . ?
C5 C6 1.390(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.510(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.512(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C14 Re1 C13 88.22(15) . . ?
C14 Re1 C15 88.25(16) . . ?
C13 Re1 C15 89.54(15) . . ?
C14 Re1 O1 178.30(13) . . ?
C13 Re1 O1 92.82(13) . . ?
C15 Re1 O1 93.10(13) . . ?
C14 Re1 N1 95.46(13) . . ?
C13 Re1 N1 172.86(13) . . ?
C15 Re1 N1 96.66(13) . . ?
O1 Re1 N1 83.36(10) . . ?
C14 Re1 N2 92.43(14) . . ?
C13 Re1 N2 94.26(13) . . ?
C15 Re1 N2 176.15(12) . . ?
O1 Re1 N2 86.15(11) . . ?
N1 Re1 N2 79.51(10) . . ?
C1 O1 Re1 132.7(2) . . ?
C8 N1 C10 109.1(3) . . ?
C8 N1 C7 110.1(3) . . ?
C10 N1 C7 106.3(3) . . ?
C8 N1 Re1 108.0(2) . . ?
C10 N1 Re1 112.1(2) . . ?
C7 N1 Re1 111.3(2) . . ?
C12 N2 C9 108.2(3) . . ?
C12 N2 C11 106.8(3) . . ?
C9 N2 C11 109.7(3) . . ?
C12 N2 Re1 111.9(2) . . ?
C9 N2 Re1 106.3(2) . . ?
C11 N2 Re1 113.7(2) . . ?
O5 N3 O6 122.5(3) . . ?
O5 N3 C4 119.1(3) . . ?
O6 N3 C4 118.4(3) . . ?
O1 C1 C2 118.0(3) . . ?
O1 C1 C6 123.8(3) . . ?
C2 C1 C6 118.2(3) . . ?
C3 C2 C1 121.8(3) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 118.7(3) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 N3 119.5(3) . . ?
C3 C4 N3 119.1(3) . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 119.0(3) . . ?
C5 C6 C7 118.2(3) . . ?
C1 C6 C7 122.8(3) . . ?
N1 C7 C6 114.8(3) . . ?
N1 C7 H7A 108.6 . . ?
C6 C7 H7A 108.6 . . ?
N1 C7 H7B 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.5 . . ?
N1 C8 C9 109.8(3) . . ?
N1 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
N1 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
N2 C9 C8 110.4(3) . . ?
N2 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
N2 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 Re1 178.2(3) . . ?
O3 C14 Re1 178.9(3) . . ?
O4 C15 Re1 179.5(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 O1 C1 C2 177.1(2) . . . . ?
Re1 O1 C1 C6 -0.7(5) . . . . ?
O1 C1 C2 C3 -175.9(3) . . . . ?
C6 C1 C2 C3 2.1(5) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C2 C3 C4 C5 -1.0(5) . . . . ?
C2 C3 C4 N3 177.4(3) . . . . ?
O5 N3 C4 C5 172.7(3) . . . . ?
O6 N3 C4 C5 -6.8(5) . . . . ?
O5 N3 C4 C3 -5.7(5) . . . . ?
O6 N3 C4 C3 174.8(4) . . . . ?
C3 C4 C5 C6 0.6(6) . . . . ?
N3 C4 C5 C6 -177.8(3) . . . . ?
C4 C5 C6 C1 1.2(5) . . . . ?
C4 C5 C6 C7 -178.7(3) . . . . ?
O1 C1 C6 C5 175.4(3) . . . . ?
C2 C1 C6 C5 -2.4(5) . . . . ?
O1 C1 C6 C7 -4.7(5) . . . . ?
C2 C1 C6 C7 177.5(3) . . . . ?
C8 N1 C7 C6 52.6(4) . . . . ?
C10 N1 C7 C6 170.7(3) . . . . ?
Re1 N1 C7 C6 -67.1(3) . . . . ?
C5 C6 C7 N1 -136.7(3) . . . . ?
C1 C6 C7 N1 43.3(5) . . . . ?
C10 N1 C8 C9 80.5(3) . . . . ?
C7 N1 C8 C9 -163.3(3) . . . . ?
Re1 N1 C8 C9 -41.6(3) . . . . ?
C12 N2 C9 C8 -163.3(3) . . . . ?
C11 N2 C9 C8 80.4(4) . . . . ?
Re1 N2 C9 C8 -43.0(3) . . . . ?
N1 C8 C9 N2 58.8(4) . . . . ?

_refine_diff_density_max         1.139
_refine_diff_density_min         -0.642
_refine_diff_density_rms         0.133

