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

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

data_5
_database_code_depnum_ccdc_archive 'CCDC 2289494'
loop_
_audit_author_name
_audit_author_address
'Nicola Demitri'
;Elettra Synchrotron XRD BLs
Italy
;
_audit_update_record             
;
2023-08-18 deposited with the CCDC.	2023-09-21 downloaded from the CCDC.
;


# start Validation Reply Form

_vrf_PLAT342_5                   
;
PROBLEM:  Low Bond Precision on  C-C Bonds ...............    0.035 Ang.
RESPONSE: Crystals grew as tiny needles and diffracted poorly.
          Statistics are also impaired by radiation damage.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H16 N O2, Re O4'
_chemical_formula_sum            'C7 H16 N O6 Re'
_chemical_formula_weight         396.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0020 0.0012 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0042 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0077 0.0045 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -0.5008 5.8080 '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'

_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                   7.313(2)
_cell_length_b                   8.956(2)
_cell_length_c                   10.153(2)
_cell_angle_alpha                79.13(3)
_cell_angle_beta                 71.47(3)
_cell_angle_gamma                67.85(3)
_cell_volume                     582.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1514
_cell_measurement_theta_min      2.161
_cell_measurement_theta_max      27.812

_exptl_crystal_description       'Thin needles'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.261
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    7.282
_shelx_estimated_absorpt_T_min   0.712
_shelx_estimated_absorpt_T_max   0.868
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.620

_diffrn_measurement_method       'Rotating crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'Elettra Synchrotron - XRD2 BL'
_diffrn_measurement_device_type  
;
'Arinax MD2s Goniometer, Pilatus 6M detector'
;

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4770
_diffrn_reflns_av_unetI/netI     0.2208
_diffrn_reflns_av_R_equivalents  0.1587
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.724
_diffrn_reflns_theta_max         21.000
_diffrn_reflns_theta_full        21.000
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.960
_reflns_number_total             1814
_reflns_number_gt                1534
_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.
;


_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0

_computing_data_collection       'Elettra XRD2 Data Collection SW'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Ortep3 for Windows - Coot'
_computing_publication_material  'enCIFer - publCIF'

_refine_special_details          
;
Hydrogen atoms were included at calculated positions with isotropic 
Ufactors=1.2Ueq (Ufactors=1.5Ueq for methyl and hydroxyl groups). 
Anisotropic thermal motion modeling has been applied to all atoms. Refined
as a 2-component twin. Geometric and thermal restrains (SADI, SIMU) have
been used to prevent artifacts related to radiation damage effects on data.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0799P)²+11.2667P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         1814
_refine_ls_number_parameters     137
_refine_ls_number_restraints     107
_refine_ls_R_factor_all          0.1151
_refine_ls_R_factor_gt           0.1033
_refine_ls_wR_factor_ref         0.1859
_refine_ls_wR_factor_gt          0.1802
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.223
_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
Re_2 Re 0.16626(8) 0.79167(7) 0.33061(7) 0.0148(4) Uani 1 1 d D U . . .
O12_2 O 0.2772(18) 0.5844(8) 0.2833(14) 0.046(4) Uani 1 1 d D U . . .
O13_2 O 0.132(2) 0.9187(13) 0.1785(10) 0.038(4) Uani 1 1 d D U . . .
O14_2 O -0.0716(14) 0.8159(15) 0.4560(12) 0.052(5) Uani 1 1 d D U . . .
O15_2 O 0.3354(15) 0.8317(15) 0.3981(13) 0.044(4) Uani 1 1 d D U . . .
O7_1 O 0.738(3) 0.605(2) 0.109(2) 0.045(4) Uani 1 1 d . U . . .
C5_1 C 0.783(3) 0.510(3) 0.209(3) 0.029(4) Uani 1 1 d . U . . .
C6_1 C 0.781(3) 0.552(2) 0.347(3) 0.031(5) Uani 1 1 d . U . . .
H6A_1 H 0.823633 0.452086 0.405815 0.046 Uiso 1 1 calc R U . . .
H6B_1 H 0.876484 0.610463 0.330680 0.046 Uiso 1 1 calc R U . . .
H6C_1 H 0.642473 0.619734 0.393225 0.046 Uiso 1 1 calc R U . . .
O4_1 O 0.8353(19) 0.3479(16) 0.2079(17) 0.024(3) Uani 1 1 d . U . . .
C3_1 C 0.828(3) 0.292(2) 0.085(2) 0.022(3) Uani 1 1 d . U . . .
H3A_1 H 0.921248 0.179141 0.073435 0.026 Uiso 1 1 calc R U . . .
H3B_1 H 0.874553 0.359905 0.001075 0.026 Uiso 1 1 calc R U . . .
C2_1 C 0.606(3) 0.303(2) 0.098(2) 0.017(3) Uani 1 1 d . U . . .
H2A_1 H 0.512476 0.411550 0.128448 0.021 Uiso 1 1 calc R U . . .
H2B_1 H 0.597093 0.295885 0.004861 0.021 Uiso 1 1 calc R U . . .
N1_1 N 0.5293(17) 0.1768(16) 0.1986(15) 0.014(3) Uani 1 1 d D U . . .
C10_1 C 0.311(2) 0.229(2) 0.195(2) 0.024(4) Uani 1 1 d D U . . .
H10A_1 H 0.306369 0.229839 0.099674 0.036 Uiso 1 1 calc R U . . .
H10B_1 H 0.246144 0.154422 0.256594 0.036 Uiso 1 1 calc R U . . .
H10C_1 H 0.237669 0.338545 0.226878 0.036 Uiso 1 1 calc R U . . .
C9_1 C 0.538(2) 0.176(2) 0.3437(16) 0.018(4) Uani 1 1 d D U . . .
H9A_1 H 0.681446 0.141127 0.345314 0.027 Uiso 1 1 calc R U . . .
H9B_1 H 0.464913 0.284798 0.375689 0.027 Uiso 1 1 calc R U . . .
H9C_1 H 0.473388 0.100674 0.405405 0.027 Uiso 1 1 calc R U . . .
C8_1 C 0.644(2) 0.0111(19) 0.148(2) 0.024(4) Uani 1 1 d D U . . .
H8A_1 H 0.637513 0.012276 0.053079 0.036 Uiso 1 1 calc R U . . .
H8B_1 H 0.787014 -0.021977 0.149461 0.036 Uiso 1 1 calc R U . . .
H8C_1 H 0.581036 -0.065416 0.209539 0.036 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re_2 O15_2 1.759(7) . ?
Re_2 O14_2 1.762(8) . ?
Re_2 O13_2 1.764(7) . ?
Re_2 O12_2 1.813(6) . ?
O7_1 C5_1 1.23(3) . ?
C5_1 O4_1 1.36(3) . ?
C5_1 C6_1 1.51(3) . ?
C6_1 H6A_1 0.9800 . ?
C6_1 H6B_1 0.9800 . ?
C6_1 H6C_1 0.9800 . ?
O4_1 C3_1 1.45(2) . ?
C3_1 C2_1 1.55(2) . ?
C3_1 H3A_1 0.9900 . ?
C3_1 H3B_1 0.9900 . ?
C2_1 N1_1 1.52(3) . ?
C2_1 H2A_1 0.9900 . ?
C2_1 H2B_1 0.9900 . ?
N1_1 C9_1 1.494(13) . ?
N1_1 C10_1 1.494(12) . ?
N1_1 C8_1 1.496(12) . ?
C10_1 H10A_1 0.9800 . ?
C10_1 H10B_1 0.9800 . ?
C10_1 H10C_1 0.9800 . ?
C9_1 H9A_1 0.9800 . ?
C9_1 H9B_1 0.9800 . ?
C9_1 H9C_1 0.9800 . ?
C8_1 H8A_1 0.9800 . ?
C8_1 H8B_1 0.9800 . ?
C8_1 H8C_1 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
O15_2 Re_2 O14_2 110.8(4) . . ?
O15_2 Re_2 O13_2 110.5(4) . . ?
O14_2 Re_2 O13_2 110.5(4) . . ?
O15_2 Re_2 O12_2 108.9(4) . . ?
O14_2 Re_2 O12_2 108.5(4) . . ?
O13_2 Re_2 O12_2 107.7(4) . . ?
O7_1 C5_1 O4_1 122.3(18) . . ?
O7_1 C5_1 C6_1 127.4(19) . . ?
O4_1 C5_1 C6_1 110(2) . . ?
C5_1 C6_1 H6A_1 109.5 . . ?
C5_1 C6_1 H6B_1 109.5 . . ?
H6A_1 C6_1 H6B_1 109.5 . . ?
C5_1 C6_1 H6C_1 109.5 . . ?
H6A_1 C6_1 H6C_1 109.5 . . ?
H6B_1 C6_1 H6C_1 109.5 . . ?
C5_1 O4_1 C3_1 115.8(18) . . ?
O4_1 C3_1 C2_1 110.1(15) . . ?
O4_1 C3_1 H3A_1 109.6 . . ?
C2_1 C3_1 H3A_1 109.6 . . ?
O4_1 C3_1 H3B_1 109.6 . . ?
C2_1 C3_1 H3B_1 109.6 . . ?
H3A_1 C3_1 H3B_1 108.2 . . ?
N1_1 C2_1 C3_1 116.6(15) . . ?
N1_1 C2_1 H2A_1 108.1 . . ?
C3_1 C2_1 H2A_1 108.1 . . ?
N1_1 C2_1 H2B_1 108.1 . . ?
C3_1 C2_1 H2B_1 108.1 . . ?
H2A_1 C2_1 H2B_1 107.3 . . ?
C9_1 N1_1 C10_1 109.8(9) . . ?
C9_1 N1_1 C8_1 109.7(9) . . ?
C10_1 N1_1 C8_1 109.9(9) . . ?
C9_1 N1_1 C2_1 112.9(12) . . ?
C10_1 N1_1 C2_1 102.7(14) . . ?
C8_1 N1_1 C2_1 111.5(14) . . ?
N1_1 C10_1 H10A_1 109.5 . . ?
N1_1 C10_1 H10B_1 109.5 . . ?
H10A_1 C10_1 H10B_1 109.5 . . ?
N1_1 C10_1 H10C_1 109.5 . . ?
H10A_1 C10_1 H10C_1 109.5 . . ?
H10B_1 C10_1 H10C_1 109.5 . . ?
N1_1 C9_1 H9A_1 109.5 . . ?
N1_1 C9_1 H9B_1 109.5 . . ?
H9A_1 C9_1 H9B_1 109.5 . . ?
N1_1 C9_1 H9C_1 109.5 . . ?
H9A_1 C9_1 H9C_1 109.5 . . ?
H9B_1 C9_1 H9C_1 109.5 . . ?
N1_1 C8_1 H8A_1 109.5 . . ?
N1_1 C8_1 H8B_1 109.5 . . ?
H8A_1 C8_1 H8B_1 109.5 . . ?
N1_1 C8_1 H8C_1 109.5 . . ?
H8A_1 C8_1 H8C_1 109.5 . . ?
H8B_1 C8_1 H8C_1 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O7_1 C5_1 O4_1 C3_1 -2(3) . . . . ?
C6_1 C5_1 O4_1 C3_1 175.7(15) . . . . ?
C5_1 O4_1 C3_1 C2_1 -84(2) . . . . ?
O4_1 C3_1 C2_1 N1_1 -74.0(18) . . . . ?
C3_1 C2_1 N1_1 C9_1 57.4(15) . . . . ?
C3_1 C2_1 N1_1 C10_1 175.7(12) . . . . ?
C3_1 C2_1 N1_1 C8_1 -66.7(14) . . . . ?

_refine_diff_density_max         6.573
_refine_diff_density_min         -4.117
_refine_diff_density_rms         0.636



