# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_K5
_database_code_depnum_ccdc_archive 'CCDC 1962326'
loop_
_audit_author_name
_audit_author_address
'Curtis Moore'
;Ohio State University
United States of America
;
_audit_update_record             
;
2019-10-29 deposited with the CCDC.	2019-12-12 downloaded from the CCDC.
;
_audit_creation_date             2018-06-04
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H13 N2 O5 Re'
_chemical_formula_sum            'C15 H13 N2 O5 Re'
_chemical_formula_weight         487.47
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.3450(2)
_cell_length_b                   14.5492(5)
_cell_length_c                   16.7909(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1550.05(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3384
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      23.820
_cell_measurement_theta_min      2.426
_shelx_estimated_absorpt_T_max   0.460
_shelx_estimated_absorpt_T_min   0.285
_exptl_absorpt_coefficient_mu    7.866
_exptl_absorpt_correction_T_max  0.0932
_exptl_absorpt_correction_T_min  0.0546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0956 before and 0.0572 after correction. The Ratio of minimum to maximum transmission is 0.5858. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'Light Yellow'
_exptl_crystal_colour_modifier   Light
_exptl_crystal_colour_primary    Yellow
_exptl_crystal_density_diffrn    2.089
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Rod
_exptl_crystal_F_000             928
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.117
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17683
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.396
_diffrn_reflns_theta_min         1.852
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2054
_reflns_number_total             3161
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.121
_refine_ls_abs_structure_details 
;
 Flack x determined using 745 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.025(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3161
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0239
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0072P)²+1.4757P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0424
_refine_ls_wR_factor_ref         0.0501
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
2. Shared sites
{C8B, N2}
{C8, N2B}
3. Uiso/Uaniso restraints and constraints
Uanis(C8B) = Uanis(N2)
Uanis(C8) = Uanis(N2B)
4. Others
 Sof(N2B)=Sof(H4B)=Sof(H7B)=Sof(H9BD)=Sof(H9BE)=Sof(H9BF)=Sof(H10D)=Sof(H10E)=
 Sof(H10F)=Sof(C8B)=1-FVAR(1)
 Sof(N2)=Sof(H4A)=Sof(H7A)=Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=Sof(H10A)=Sof(H10B)=
 Sof(H10C)=Sof(C8)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4A), C4(H4B), C7(H7A), C7(H7B), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
5.b Idealised Me refined as rotating group:
 C9(H9AA,H9AB,H9AC), C9(H9BD,H9BE,H9BF), C10(H10A,H10B,H10C), C10(H10D,H10E,
 H10F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.50183(6) -0.00029(3) 0.33915(2) 0.01650(9) Uani 1 1 d . . . . .
O1 O 0.6749(11) -0.1089(4) 0.4824(4) 0.0302(17) Uani 1 1 d . . . . .
O2 O 0.1216(10) -0.1292(4) 0.3505(4) 0.0371(19) Uani 1 1 d . . . . .
O3 O 0.7139(10) -0.1394(4) 0.2274(4) 0.0273(16) Uani 1 1 d . . . . .
O4 O 0.3664(9) 0.1093(4) 0.4052(3) 0.0168(14) Uani 1 1 d . . . . .
O5 O 0.7409(9) 0.1030(4) 0.3326(3) 0.0178(15) Uani 1 1 d . . . . .
N1 N 0.3767(12) 0.0843(5) 0.2398(4) 0.0173(18) Uani 1 1 d . . . . .
N2 N 0.5466(12) 0.3428(5) 0.4355(5) 0.017(3) Uani 0.64(8) 1 d . . P A 1
N2B N 0.7343(14) 0.3406(6) 0.3986(5) 0.017(3) Uani 0.36(8) 1 d . . P A 2
C1 C 0.6131(15) -0.0665(6) 0.4287(6) 0.023(2) Uani 1 1 d . . . . .
C2 C 0.2629(16) -0.0803(6) 0.3450(6) 0.026(2) Uani 1 1 d . . . . .
C3 C 0.6329(14) -0.0873(6) 0.2716(6) 0.021(2) Uani 1 1 d . . . . .
C4 C 0.4197(14) 0.2661(6) 0.4381(5) 0.017(2) Uani 1 1 d . . . . .
H4A H 0.287789 0.269284 0.464697 0.020 Uiso 0.64(8) 1 calc R . P A 1
H4B H 0.287789 0.269284 0.464697 0.020 Uiso 0.36(8) 1 calc R . P A 2
C5 C 0.4804(16) 0.1845(5) 0.4027(4) 0.0143(18) Uani 1 1 d . . . . .
C6 C 0.6812(13) 0.1810(6) 0.3639(5) 0.017(2) Uani 1 1 d . . . . .
C7 C 0.8018(14) 0.2599(6) 0.3628(5) 0.016(2) Uani 1 1 d . . . . .
H7A H 0.934817 0.258980 0.336855 0.020 Uiso 0.64(8) 1 calc R . P A 1
H7B H 0.934817 0.258980 0.336855 0.020 Uiso 0.36(8) 1 calc R . P A 2
C9 C 0.8731(14) 0.4235(5) 0.3994(5) 0.020(2) Uani 1 1 d . . . . .
H9AA H 0.800028 0.474923 0.373635 0.030 Uiso 0.64(8) 1 calc GR . P A 1
H9AB H 1.003708 0.410153 0.370441 0.030 Uiso 0.64(8) 1 calc GR . P A 1
H9AC H 0.906658 0.439984 0.454529 0.030 Uiso 0.64(8) 1 calc GR . P A 1
H9BD H 0.934728 0.431078 0.452487 0.030 Uiso 0.36(8) 1 calc GR . P A 2
H9BE H 0.789620 0.478080 0.386015 0.030 Uiso 0.36(8) 1 calc GR . P A 2
H9BF H 0.986048 0.415901 0.360102 0.030 Uiso 0.36(8) 1 calc GR . P A 2
C10 C 0.4712(15) 0.4278(5) 0.4755(5) 0.018(2) Uani 1 1 d . . . . .
H10A H 0.581639 0.451197 0.510898 0.027 Uiso 0.64(8) 1 calc GR . P A 1
H10B H 0.344697 0.413799 0.506768 0.027 Uiso 0.64(8) 1 calc GR . P A 1
H10C H 0.437451 0.474302 0.435305 0.027 Uiso 0.64(8) 1 calc GR . P A 1
H10D H 0.316762 0.427796 0.476952 0.027 Uiso 0.36(8) 1 calc GR . P A 2
H10E H 0.520826 0.481668 0.445990 0.027 Uiso 0.36(8) 1 calc GR . P A 2
H10F H 0.526200 0.429834 0.530029 0.027 Uiso 0.36(8) 1 calc GR . P A 2
C11 C 0.1746(14) 0.1141(6) 0.2415(6) 0.021(2) Uani 1 1 d . . . . .
H11 H 0.085368 0.095184 0.283932 0.025 Uiso 1 1 calc R . . . .
C12 C 0.0953(14) 0.1711(6) 0.1833(5) 0.022(2) Uani 1 1 d . . . . .
H12 H -0.046259 0.192039 0.186314 0.026 Uiso 1 1 calc R . . . .
C13 C 0.2212(15) 0.1975(6) 0.1210(7) 0.026(3) Uani 1 1 d . . . . .
H13 H 0.167593 0.235403 0.079685 0.031 Uiso 1 1 calc R . . . .
C14 C 0.4279(15) 0.1677(6) 0.1198(6) 0.026(2) Uani 1 1 d . . . . .
H14 H 0.519784 0.185692 0.077961 0.031 Uiso 1 1 calc R . . . .
C15 C 0.4978(18) 0.1121(5) 0.1793(4) 0.0218(18) Uani 1 1 d . . . . .
H15 H 0.640204 0.092059 0.177759 0.026 Uiso 1 1 calc R . . . .
C8 C 0.7343(14) 0.3406(6) 0.3986(5) 0.017(3) Uani 0.64(8) 1 d . . P A 1
C8B C 0.5466(12) 0.3428(5) 0.4355(5) 0.017(3) Uani 0.36(8) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 O4 2.124(5) . ?
Re1 O5 2.138(6) . ?
Re1 N1 2.220(7) . ?
Re1 C1 1.920(10) . ?
Re1 C2 1.914(10) . ?
Re1 C3 1.892(10) . ?
O1 C1 1.161(10) . ?
O2 C2 1.148(11) . ?
O3 C3 1.179(10) . ?
O4 C5 1.312(9) . ?
O5 C6 1.308(10) . ?
N1 C11 1.354(11) . ?
N1 C15 1.337(10) . ?
N2 C4 1.377(11) . ?
N2 C10 1.487(10) . ?
N2 C8 1.343(10) . ?
N2B C7 1.386(12) . ?
N2B C9 1.495(11) . ?
N2B C8B 1.343(10) . ?
C4 H4A 0.9500 . ?
C4 H4B 0.9500 . ?
C4 C5 1.382(11) . ?
C4 C8B 1.377(11) . ?
C5 C6 1.432(12) . ?
C6 C7 1.380(12) . ?
C7 H7A 0.9500 . ?
C7 H7B 0.9500 . ?
C7 C8 1.386(12) . ?
C9 H9AA 0.9800 . ?
C9 H9AB 0.9800 . ?
C9 H9AC 0.9800 . ?
C9 H9BD 0.9800 . ?
C9 H9BE 0.9800 . ?
C9 H9BF 0.9800 . ?
C9 C8 1.495(11) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 H10D 0.9800 . ?
C10 H10E 0.9800 . ?
C10 H10F 0.9800 . ?
C10 C8B 1.487(10) . ?
C11 H11 0.9500 . ?
C11 C12 1.377(12) . ?
C12 H12 0.9500 . ?
C12 C13 1.371(13) . ?
C13 H13 0.9500 . ?
C13 C14 1.381(12) . ?
C14 H14 0.9500 . ?
C14 C15 1.359(12) . ?
C15 H15 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
O4 Re1 O5 77.7(2) . . ?
O4 Re1 N1 80.3(2) . . ?
O5 Re1 N1 79.9(2) . . ?
C1 Re1 O4 96.7(3) . . ?
C1 Re1 O5 97.6(3) . . ?
C1 Re1 N1 176.4(3) . . ?
C2 Re1 O4 96.3(3) . . ?
C2 Re1 O5 172.8(3) . . ?
C2 Re1 N1 95.3(3) . . ?
C2 Re1 C1 86.9(4) . . ?
C3 Re1 O4 173.2(3) . . ?
C3 Re1 O5 97.3(3) . . ?
C3 Re1 N1 94.4(4) . . ?
C3 Re1 C1 88.4(4) . . ?
C3 Re1 C2 88.4(4) . . ?
C5 O4 Re1 112.7(5) . . ?
C6 O5 Re1 112.6(5) . . ?
C11 N1 Re1 120.0(6) . . ?
C15 N1 Re1 122.3(7) . . ?
C15 N1 C11 117.6(8) . . ?
C4 N2 C10 118.1(7) . . ?
C8 N2 C4 120.9(8) . . ?
C8 N2 C10 120.9(8) . . ?
C7 N2B C9 120.3(8) . . ?
C8B N2B C7 119.6(8) . . ?
C8B N2B C9 120.0(8) . . ?
O1 C1 Re1 177.6(8) . . ?
O2 C2 Re1 178.1(9) . . ?
O3 C3 Re1 177.7(9) . . ?
N2 C4 H4A 119.4 . . ?
N2 C4 C5 121.3(8) . . ?
C5 C4 H4A 119.4 . . ?
C5 C4 H4B 119.4 . . ?
C8B C4 H4B 119.4 . . ?
C8B C4 C5 121.3(8) . . ?
O4 C5 C4 123.3(9) . . ?
O4 C5 C6 118.4(7) . . ?
C4 C5 C6 118.3(8) . . ?
O5 C6 C5 118.1(8) . . ?
O5 C6 C7 123.8(8) . . ?
C7 C6 C5 118.0(8) . . ?
N2B C7 H7B 119.1 . . ?
C6 C7 N2B 121.8(9) . . ?
C6 C7 H7A 119.1 . . ?
C6 C7 H7B 119.1 . . ?
C6 C7 C8 121.8(9) . . ?
C8 C7 H7A 119.1 . . ?
N2B C9 H9BD 109.5 . . ?
N2B C9 H9BE 109.5 . . ?
N2B C9 H9BF 109.5 . . ?
H9AA C9 H9AB 109.5 . . ?
H9AA C9 H9AC 109.5 . . ?
H9AB C9 H9AC 109.5 . . ?
H9BD C9 H9BE 109.5 . . ?
H9BD C9 H9BF 109.5 . . ?
H9BE C9 H9BF 109.5 . . ?
C8 C9 H9AA 109.5 . . ?
C8 C9 H9AB 109.5 . . ?
C8 C9 H9AC 109.5 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
H10D C10 H10E 109.5 . . ?
H10D C10 H10F 109.5 . . ?
H10E C10 H10F 109.5 . . ?
C8B C10 H10D 109.5 . . ?
C8B C10 H10E 109.5 . . ?
C8B C10 H10F 109.5 . . ?
N1 C11 H11 119.2 . . ?
N1 C11 C12 121.6(9) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.8(9) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 120.8 . . ?
C12 C13 C14 118.5(10) . . ?
C14 C13 H13 120.8 . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 119.0(10) . . ?
C15 C14 H14 120.5 . . ?
N1 C15 C14 123.5(10) . . ?
N1 C15 H15 118.3 . . ?
C14 C15 H15 118.3 . . ?
N2 C8 C7 119.6(8) . . ?
N2 C8 C9 120.0(8) . . ?
C7 C8 C9 120.3(8) . . ?
N2B C8B C4 120.9(8) . . ?
N2B C8B C10 120.9(8) . . ?
C4 C8B C10 118.1(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM, hexanes'
####################################################################### 
# 
# 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_K8
_database_code_depnum_ccdc_archive 'CCDC 1962327'
loop_
_audit_author_name
_audit_author_address
'Curtis Moore'
;Ohio State University
United States of America
;
_audit_update_record             
;
2019-10-29 deposited with the CCDC.	2019-12-12 downloaded from the CCDC.
;
_audit_creation_date             2018-06-04
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 N2 O5 Re'
_chemical_formula_sum            'C13 H9 N2 O5 Re'
_chemical_formula_weight         459.42
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.1929(5)
_cell_length_b                   13.3161(7)
_cell_length_c                   11.3352(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.800(2)
_cell_angle_gamma                90
_cell_volume                     1328.36(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      26.384
_cell_measurement_theta_min      2.314
_shelx_estimated_absorpt_T_max   0.479
_shelx_estimated_absorpt_T_min   0.380
_exptl_absorpt_coefficient_mu    9.171
_exptl_absorpt_correction_T_max  0.0932
_exptl_absorpt_correction_T_min  0.0572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0924 before and 0.0459 after correction. The Ratio of minimum to maximum transmission is 0.6137. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'Light Yellow'
_exptl_crystal_colour_modifier   Light
_exptl_crystal_colour_primary    Yellow
_exptl_crystal_density_diffrn    2.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             864
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.131
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.094
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25383
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.404
_diffrn_reflns_theta_min         2.314
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2508
_reflns_number_total             2729
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2729
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0175
_refine_ls_R_factor_gt           0.0145
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0073P)²+1.6265P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0302
_refine_ls_wR_factor_ref         0.0309
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Shared sites
{C4, N2B}
{C4B, N2}
3. Uiso/Uaniso restraints and constraints
Uanis(C4) = Uanis(N2B)
Uanis(C4B) = Uanis(N2)
4. Others
 Sof(N2B)=Sof(H5B)=Sof(H8B)=Sof(C4B)=1-FVAR(1)
 Sof(N2)=Sof(H5A)=Sof(H8A)=Sof(C4)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C5(H5A), C5(H5B), C6(H6), C7(H7), C8(H8A), C8(H8B), C9(H9), C10(H10),
 C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.33901(2) 0.52165(2) 0.27449(2) 0.01268(4) Uani 1 1 d . . . . .
O1 O 0.4872(2) 0.31659(14) 0.35439(19) 0.0213(5) Uani 1 1 d . . . . .
O2 O 0.1678(2) 0.49735(15) 0.46784(18) 0.0216(5) Uani 1 1 d . . . . .
O3 O 0.0588(2) 0.41824(15) 0.10452(18) 0.0229(5) Uani 1 1 d . . . . .
O4 O 0.5433(2) 0.59874(14) 0.36732(16) 0.0151(4) Uani 1 1 d . . . . .
O5 O 0.4432(2) 0.55020(14) 0.13266(17) 0.0167(4) Uani 1 1 d . . . . .
N1 N 0.2624(3) 0.67963(17) 0.2424(2) 0.0143(5) Uani 1 1 d . . . . .
N2 N 0.6288(3) 0.61986(18) 0.2958(2) 0.0143(6) Uani 0.36(2) 1 d . . P A 1
N2B N 0.5799(3) 0.59289(17) 0.1749(2) 0.0145(6) Uani 0.64(2) 1 d . . P A 2
C1 C 0.4303(3) 0.3922(2) 0.3215(2) 0.0155(6) Uani 1 1 d . . . . .
C2 C 0.2381(3) 0.50683(19) 0.3986(3) 0.0163(6) Uani 1 1 d . . . . .
C3 C 0.1639(3) 0.4580(2) 0.1697(3) 0.0163(6) Uani 1 1 d . . . . .
C5 C 0.6681(3) 0.6085(2) 0.0966(3) 0.0167(6) Uani 1 1 d . . . . .
H5A H 0.632962 0.587434 0.013067 0.020 Uiso 0.36(2) 1 calc R . P A 1
H5B H 0.632962 0.587434 0.013067 0.020 Uiso 0.64(2) 1 calc R . P A 2
C6 C 0.8059(3) 0.6545(2) 0.1397(3) 0.0198(6) Uani 1 1 d . . . . .
H6 H 0.868083 0.664345 0.086740 0.024 Uiso 1 1 calc R . . . .
C7 C 0.8554(3) 0.6870(2) 0.2621(3) 0.0194(6) Uani 1 1 d . . . . .
H7 H 0.949789 0.720888 0.291924 0.023 Uiso 1 1 calc R . . . .
C8 C 0.7669(3) 0.6696(2) 0.3392(3) 0.0173(6) Uani 1 1 d . . . . .
H8A H 0.800295 0.691741 0.422369 0.021 Uiso 0.36(2) 1 calc R . P A 1
H8B H 0.800295 0.691741 0.422369 0.021 Uiso 0.64(2) 1 calc R . P A 2
C9 C 0.3009(3) 0.7448(2) 0.3370(3) 0.0177(6) Uani 1 1 d . . . . .
H9 H 0.360558 0.721336 0.415119 0.021 Uiso 1 1 calc R . . . .
C10 C 0.2574(3) 0.8446(2) 0.3252(3) 0.0189(6) Uani 1 1 d . . . . .
H10 H 0.286381 0.888586 0.393977 0.023 Uiso 1 1 calc R . . . .
C11 C 0.1706(3) 0.8793(2) 0.2110(3) 0.0197(6) Uani 1 1 d . . . . .
H11 H 0.138503 0.947317 0.200300 0.024 Uiso 1 1 calc R . . . .
C12 C 0.1319(3) 0.8127(2) 0.1133(3) 0.0182(6) Uani 1 1 d . . . . .
H12 H 0.072927 0.834601 0.034159 0.022 Uiso 1 1 calc R . . . .
C13 C 0.1794(3) 0.7145(2) 0.1317(3) 0.0165(6) Uani 1 1 d . . . . .
H13 H 0.152663 0.669471 0.063826 0.020 Uiso 1 1 calc R . . . .
C4 C 0.5799(3) 0.59289(17) 0.1749(2) 0.0145(6) Uani 0.36(2) 1 d . . P A 1
C4B C 0.6288(3) 0.61986(18) 0.2958(2) 0.0143(6) Uani 0.64(2) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 O4 2.1318(18) . ?
Re1 O5 2.1302(18) . ?
Re1 N1 2.215(2) . ?
Re1 C1 1.923(3) . ?
Re1 C2 1.906(3) . ?
Re1 C3 1.901(3) . ?
O1 C1 1.147(3) . ?
O2 C2 1.158(3) . ?
O3 C3 1.160(3) . ?
O4 N2 1.313(3) . ?
O4 C4B 1.313(3) . ?
O5 N2B 1.335(3) . ?
O5 C4 1.335(3) . ?
N1 C9 1.345(3) . ?
N1 C13 1.348(3) . ?
N2 C8 1.390(4) . ?
N2 C4 1.362(3) . ?
N2B C5 1.380(4) . ?
N2B C4B 1.362(3) . ?
C5 H5A 0.9500 . ?
C5 H5B 0.9500 . ?
C5 C6 1.364(4) . ?
C5 C4 1.380(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.398(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.374(4) . ?
C8 H8A 0.9500 . ?
C8 H8B 0.9500 . ?
C8 C4B 1.390(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.376(4) . ?
C13 H13 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
O4 Re1 N1 79.43(8) . . ?
O5 Re1 O4 76.26(7) . . ?
O5 Re1 N1 84.11(8) . . ?
C1 Re1 O4 92.48(9) . . ?
C1 Re1 O5 96.52(10) . . ?
C1 Re1 N1 171.52(10) . . ?
C2 Re1 O4 103.44(10) . . ?
C2 Re1 O5 175.24(9) . . ?
C2 Re1 N1 91.16(10) . . ?
C2 Re1 C1 88.23(11) . . ?
C3 Re1 O4 171.47(9) . . ?
C3 Re1 O5 95.32(10) . . ?
C3 Re1 N1 98.58(10) . . ?
C3 Re1 C1 89.79(11) . . ?
C3 Re1 C2 84.84(12) . . ?
N2 O4 Re1 113.44(15) . . ?
C4B O4 Re1 113.44(15) . . ?
N2B O5 Re1 112.80(15) . . ?
C4 O5 Re1 112.80(15) . . ?
C9 N1 Re1 118.95(18) . . ?
C9 N1 C13 117.9(2) . . ?
C13 N1 Re1 123.19(18) . . ?
O4 N2 C8 122.2(2) . . ?
O4 N2 C4 118.9(2) . . ?
C4 N2 C8 118.9(2) . . ?
O5 N2B C5 120.0(2) . . ?
O5 N2B C4B 118.4(2) . . ?
C4B N2B C5 121.5(2) . . ?
O1 C1 Re1 177.1(2) . . ?
O2 C2 Re1 175.4(2) . . ?
O3 C3 Re1 178.6(3) . . ?
N2B C5 H5B 120.2 . . ?
C6 C5 N2B 119.7(3) . . ?
C6 C5 H5A 120.2 . . ?
C6 C5 H5B 120.2 . . ?
C6 C5 C4 119.7(3) . . ?
C4 C5 H5A 120.2 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.7(3) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.8(3) . . ?
C8 C7 H7 120.1 . . ?
N2 C8 H8A 119.9 . . ?
C7 C8 N2 120.2(3) . . ?
C7 C8 H8A 119.9 . . ?
C7 C8 H8B 119.9 . . ?
C7 C8 C4B 120.2(3) . . ?
C4B C8 H8B 119.9 . . ?
N1 C9 H9 118.6 . . ?
N1 C9 C10 122.8(3) . . ?
C10 C9 H9 118.6 . . ?
C9 C10 H10 120.6 . . ?
C9 C10 C11 118.8(3) . . ?
C11 C10 H10 120.6 . . ?
C10 C11 H11 120.7 . . ?
C12 C11 C10 118.6(3) . . ?
C12 C11 H11 120.7 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.4(3) . . ?
C13 C12 H12 120.3 . . ?
N1 C13 C12 122.5(3) . . ?
N1 C13 H13 118.7 . . ?
C12 C13 H13 118.7 . . ?
O5 C4 N2 118.4(2) . . ?
O5 C4 C5 120.0(2) . . ?
N2 C4 C5 121.5(2) . . ?
O4 C4B N2B 118.9(2) . . ?
O4 C4B C8 122.2(2) . . ?
N2B C4B C8 118.9(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM, hexanes'
####################################################################### 
# 
# 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_K12
_database_code_depnum_ccdc_archive 'CCDC 1962330'
loop_
_audit_author_name
_audit_author_address
'Curtis Moore'
;Ohio State University
United States of America
;
_audit_update_record             
;
2019-10-29 deposited with the CCDC.	2019-12-12 downloaded from the CCDC.
;
_audit_creation_date             2018-06-04
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 N O4 Re S'
_chemical_formula_sum            'C15 H12 N O4 Re S'
_chemical_formula_weight         488.52
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.5304(5)
_cell_length_b                   8.1560(5)
_cell_length_c                   22.7941(15)
_cell_angle_alpha                90
_cell_angle_beta                 96.365(2)
_cell_angle_gamma                90
_cell_volume                     1576.10(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6720
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25.959
_cell_measurement_theta_min      2.654
_shelx_estimated_absorpt_T_max   0.637
_shelx_estimated_absorpt_T_min   0.548
_exptl_absorpt_coefficient_mu    7.858
_exptl_absorpt_correction_T_max  0.2602
_exptl_absorpt_correction_T_min  0.2290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0484 before and 0.0433 after correction. The Ratio of minimum to maximum transmission is 0.8801. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'Light Yellow'
_exptl_crystal_colour_modifier   Light
_exptl_crystal_colour_primary    Yellow
_exptl_crystal_density_diffrn    2.059
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.087
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.063
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            21549
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.379
_diffrn_reflns_theta_min         2.470
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2783
_reflns_number_total             3228
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.821
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0207
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0136P)²+0.4010P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0355
_refine_ls_wR_factor_ref         0.0372
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.78499(2) 0.63031(2) 0.41457(2) 0.01371(5) Uani 1 1 d . . . . .
S1 S 0.79836(10) 0.72065(10) 0.31116(4) 0.01666(19) Uani 1 1 d . . . . .
O1 O 0.9972(3) 0.3283(3) 0.40652(11) 0.0255(6) Uani 1 1 d . . . . .
O2 O 1.0721(3) 0.8178(3) 0.47329(11) 0.0274(6) Uani 1 1 d . . . . .
O3 O 0.7084(3) 0.5038(3) 0.53522(10) 0.0241(6) Uani 1 1 d . . . . .
O4 O 0.5750(3) 0.5232(3) 0.37451(10) 0.0171(5) Uani 1 1 d . . . . .
N1 N 0.6339(3) 0.8521(3) 0.41544(12) 0.0152(6) Uani 1 1 d . . . . .
C1 C 0.9157(4) 0.4421(4) 0.40919(14) 0.0178(8) Uani 1 1 d . . . . .
C2 C 0.9649(4) 0.7468(4) 0.45125(15) 0.0179(8) Uani 1 1 d . . . . .
C3 C 0.7389(4) 0.5543(4) 0.49102(16) 0.0170(8) Uani 1 1 d . . . . .
C4 C 0.5293(4) 0.5405(4) 0.31758(15) 0.0160(7) Uani 1 1 d . . . . .
C5 C 0.6207(4) 0.6269(4) 0.27963(14) 0.0163(7) Uani 1 1 d . . . . .
C6 C 0.5707(4) 0.6443(4) 0.21958(15) 0.0198(8) Uani 1 1 d . . . . .
H6 H 0.633471 0.703434 0.194899 0.024 Uiso 1 1 calc R . . . .
C7 C 0.4291(4) 0.5751(4) 0.19606(16) 0.0242(9) Uani 1 1 d . . . . .
H7 H 0.394839 0.585175 0.155122 0.029 Uiso 1 1 calc R . . . .
C8 C 0.3375(4) 0.4907(4) 0.23295(16) 0.0243(8) Uani 1 1 d . . . . .
H8 H 0.239824 0.444453 0.216926 0.029 Uiso 1 1 calc R . . . .
C9 C 0.3860(4) 0.4732(4) 0.29226(16) 0.0208(8) Uani 1 1 d . . . . .
H9 H 0.321491 0.414605 0.316450 0.025 Uiso 1 1 calc R . . . .
C10 C 0.9495(4) 0.6089(4) 0.27806(16) 0.0248(8) Uani 1 1 d . . . . .
H10A H 1.053606 0.641124 0.297052 0.037 Uiso 1 1 calc GR . . . .
H10B H 0.942180 0.634103 0.235813 0.037 Uiso 1 1 calc GR . . . .
H10C H 0.934412 0.490926 0.283410 0.037 Uiso 1 1 calc GR . . . .
C11 C 0.6925(4) 1.0032(4) 0.40769(14) 0.0188(8) Uani 1 1 d . . . . .
H11 H 0.800860 1.014097 0.402233 0.023 Uiso 1 1 calc R . . . .
C12 C 0.6005(4) 1.1426(4) 0.40740(15) 0.0218(8) Uani 1 1 d . . . . .
H12 H 0.645188 1.247106 0.401329 0.026 Uiso 1 1 calc R . . . .
C13 C 0.4445(4) 1.1294(4) 0.41592(15) 0.0226(8) Uani 1 1 d . . . . .
H13 H 0.379201 1.223902 0.415551 0.027 Uiso 1 1 calc R . . . .
C14 C 0.3844(4) 0.9752(4) 0.42507(15) 0.0232(8) Uani 1 1 d . . . . .
H14 H 0.277337 0.962618 0.432100 0.028 Uiso 1 1 calc R . . . .
C15 C 0.4808(4) 0.8395(4) 0.42393(15) 0.0197(8) Uani 1 1 d . . . . .
H15 H 0.437688 0.733915 0.429310 0.024 Uiso 1 1 calc R . . . .


_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 S1 2.4842(9) . ?
Re1 O4 2.108(2) . ?
Re1 N1 2.223(3) . ?
Re1 C1 1.909(4) . ?
Re1 C2 1.917(4) . ?
Re1 C3 1.931(4) . ?
S1 C5 1.777(3) . ?
S1 C10 1.810(3) . ?
O1 C1 1.166(4) . ?
O2 C2 1.149(4) . ?
O3 C3 1.145(4) . ?
O4 C4 1.320(4) . ?
N1 C11 1.349(4) . ?
N1 C15 1.345(4) . ?
C4 C5 1.415(4) . ?
C4 C9 1.405(5) . ?
C5 C6 1.395(5) . ?
C6 C7 1.386(5) . ?
C7 C8 1.391(5) . ?
C8 C9 1.377(5) . ?
C11 C12 1.381(4) . ?
C12 C13 1.371(5) . ?
C13 C14 1.383(5) . ?
C14 C15 1.381(5) . ?

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
O4 Re1 S1 80.68(6) . . ?
O4 Re1 N1 82.85(9) . . ?
N1 Re1 S1 81.65(7) . . ?
C1 Re1 S1 95.11(10) . . ?
C1 Re1 O4 96.50(11) . . ?
C1 Re1 N1 176.75(12) . . ?
C1 Re1 C2 88.93(14) . . ?
C1 Re1 C3 88.76(13) . . ?
C2 Re1 S1 98.52(10) . . ?
C2 Re1 O4 174.56(11) . . ?
C2 Re1 N1 91.70(12) . . ?
C2 Re1 C3 89.93(14) . . ?
C3 Re1 S1 170.76(10) . . ?
C3 Re1 O4 90.55(11) . . ?
C3 Re1 N1 94.43(11) . . ?
C5 S1 Re1 97.43(11) . . ?
C5 S1 C10 103.28(16) . . ?
C10 S1 Re1 110.84(12) . . ?
C4 O4 Re1 121.7(2) . . ?
C11 N1 Re1 121.2(2) . . ?
C15 N1 Re1 120.8(2) . . ?
C15 N1 C11 117.9(3) . . ?
O1 C1 Re1 179.0(3) . . ?
O2 C2 Re1 179.4(3) . . ?
O3 C3 Re1 177.2(3) . . ?
O4 C4 C5 122.1(3) . . ?
O4 C4 C9 120.7(3) . . ?
C9 C4 C5 117.2(3) . . ?
C4 C5 S1 118.0(2) . . ?
C6 C5 S1 120.5(3) . . ?
C6 C5 C4 121.4(3) . . ?
C7 C6 C5 119.8(3) . . ?
C6 C7 C8 119.4(3) . . ?
C9 C8 C7 121.1(3) . . ?
C8 C9 C4 121.1(3) . . ?
N1 C11 C12 122.3(3) . . ?
C13 C12 C11 119.7(3) . . ?
C12 C13 C14 118.3(3) . . ?
C15 C14 C13 119.6(3) . . ?
N1 C15 C14 122.1(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_K11
_database_code_depnum_ccdc_archive 'CCDC 1962329'
loop_
_audit_author_name
_audit_author_address
'Curtis Moore'
;Ohio State University
United States of America
;
_audit_update_record             
;
2019-10-29 deposited with the CCDC.	2019-12-12 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT307_K11                 
;
PROBLEM: Isolated Metal Atom found in Structure (Unusual)       Re1B Check
RESPONSE: Heavy Atom Position from alternate site/disorder around 1.5%.
;
# Added during the CSD deposition process: Tuesday 29 October 2019 05:37 PM
# end Validation Reply Form

_audit_creation_date             2018-06-04
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 N O5 Re, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C20.50 H15 Cl N O5 Re'
_chemical_formula_weight         576.98
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cl Cl 0.1484 0.1585 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.753(2)
_cell_length_b                   7.0352(8)
_cell_length_c                   13.7941(18)
_cell_angle_alpha                90
_cell_angle_beta                 105.388(7)
_cell_angle_gamma                90
_cell_volume                     1941.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4183
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      21.846
_cell_measurement_theta_min      3.054
_shelx_estimated_absorpt_T_max   0.475
_shelx_estimated_absorpt_T_min   0.440
_exptl_absorpt_coefficient_mu    6.428
_exptl_absorpt_correction_T_max  0.0439
_exptl_absorpt_correction_T_min  0.0166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1275 before and 0.0802 after correction. The Ratio of minimum to maximum transmission is 0.3781. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'Light Yellow'
_exptl_crystal_colour_modifier   Light
_exptl_crystal_colour_primary    Yellow
_exptl_crystal_density_diffrn    1.974
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1108
_exptl_crystal_size_max          0.153
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.136
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0959
_diffrn_reflns_av_unetI/netI     0.0639
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26253
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.381
_diffrn_reflns_theta_min         2.036
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2886
_reflns_number_total             3563
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.923
_refine_diff_density_min         -1.342
_refine_diff_density_rms         0.165
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3563
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0376
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0238P)²+4.8116P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0759
_refine_ls_wR_factor_ref         0.0815
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl1S-C1S
 1.8 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Re1B) = Uanis(Re1)
4. Others
 Sof(Re1B)=1-FVAR(1)
 Sof(Re1)=FVAR(1)
 Fixed Sof: C1S(0.5) H1SA(0.5) H1SB(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C1S(H1SA,H1SB)
5.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20)
5.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.83548(2) 0.78123(4) 0.55271(2) 0.02089(10) Uani 0.9851(7) 1 d . . P A
1
O1 O 0.7707(3) 1.0345(7) 0.6830(4) 0.0356(13) Uani 1 1 d . . . A 1
O2 O 0.8984(3) 0.5341(7) 0.7362(4) 0.0303(12) Uani 1 1 d . . . A 1
O3 O 0.9572(3) 1.0456(7) 0.6157(4) 0.0306(12) Uani 1 1 d . . . A 1
O4 O 0.7536(2) 0.5988(6) 0.4999(4) 0.0258(11) Uani 1 1 d . . . A 1
O5 O 0.7936(2) 0.9243(6) 0.4139(4) 0.0255(11) Uani 1 1 d . . . A 1
N1 N 0.8814(3) 0.5966(8) 0.4598(4) 0.0214(13) Uani 1 1 d . . . A 1
C1 C 0.7936(4) 0.9385(11) 0.6320(6) 0.0302(18) Uani 1 1 d . . . A 1
C2 C 0.8737(4) 0.6325(10) 0.6673(6) 0.0273(17) Uani 1 1 d . . . A 1
C3 C 0.9114(4) 0.9452(10) 0.5926(5) 0.0247(17) Uani 1 1 d . . . A 1
C4 C 0.7318(4) 1.0269(10) 0.2552(6) 0.0316(18) Uani 1 1 d . . . A 1
H4A H 0.687413 1.083651 0.244913 0.047 Uiso 1 1 calc GR . . A 1
H4B H 0.734453 0.960756 0.193872 0.047 Uiso 1 1 calc GR . . A 1
H4C H 0.765845 1.127057 0.271152 0.047 Uiso 1 1 calc GR . . A 1
C5 C 0.7439(4) 0.8870(10) 0.3412(6) 0.0291(18) Uani 1 1 d . . . A 1
C6 C 0.7007(4) 0.7256(10) 0.3358(5) 0.0262(16) Uani 1 1 d . . . A 1
C7 C 0.7090(4) 0.5895(10) 0.4132(5) 0.0260(17) Uani 1 1 d . . . A 1
C8 C 0.6663(4) 0.4234(10) 0.3989(6) 0.0264(17) Uani 1 1 d . . . A 1
C9 C 0.6143(4) 0.4013(11) 0.3084(6) 0.0323(19) Uani 1 1 d . . . A 1
C10 C 0.6058(4) 0.5441(11) 0.2327(6) 0.035(2) Uani 1 1 d . . . A 1
H10 H 0.570525 0.532752 0.172884 0.043 Uiso 1 1 calc R . . A 1
C11 C 0.6472(4) 0.6952(11) 0.2452(6) 0.0359(19) Uani 1 1 d . . . A 1
H11 H 0.641023 0.785608 0.192382 0.043 Uiso 1 1 calc R . . A 1
C12 C 0.6756(4) 0.2789(10) 0.4719(6) 0.0300(18) Uani 1 1 d . . . A 1
H12 H 0.709786 0.291982 0.532839 0.036 Uiso 1 1 calc R . . A 1
C13 C 0.6357(4) 0.1174(12) 0.4563(7) 0.040(2) Uani 1 1 d . . . A 1
H13 H 0.643311 0.020226 0.505814 0.048 Uiso 1 1 calc R . . A 1
C14 C 0.5845(4) 0.0976(12) 0.3684(7) 0.041(2) Uani 1 1 d . . . A 1
H14 H 0.556852 -0.012014 0.358814 0.049 Uiso 1 1 calc R . . A 1
C15 C 0.5736(4) 0.2378(12) 0.2943(7) 0.043(2) Uani 1 1 d . . . A 1
H15 H 0.538730 0.223113 0.234239 0.052 Uiso 1 1 calc R . . A 1
C16 C 0.8678(4) 0.4084(10) 0.4503(5) 0.0240(16) Uani 1 1 d . . . A 1
H16 H 0.836012 0.356508 0.481447 0.029 Uiso 1 1 calc R . . A 1
C17 C 0.8988(3) 0.2886(10) 0.3964(5) 0.0269(16) Uani 1 1 d . . . A 1
H17 H 0.888528 0.156735 0.391307 0.032 Uiso 1 1 calc R . . A 1
C18 C 0.9448(4) 0.3631(10) 0.3502(5) 0.0257(17) Uani 1 1 d . . . A 1
H18 H 0.966371 0.283617 0.312727 0.031 Uiso 1 1 calc R . . A 1
C19 C 0.9589(3) 0.5550(10) 0.3597(5) 0.0270(17) Uani 1 1 d . . . A 1
H19 H 0.990299 0.609941 0.328823 0.032 Uiso 1 1 calc R . . A 1
C20 C 0.9268(3) 0.6649(10) 0.4142(5) 0.0232(16) Uani 1 1 d . . . A 1
H20 H 0.937036 0.796716 0.420331 0.028 Uiso 1 1 calc R . . A 1
Cl1S Cl 0.53727(15) -0.3261(4) 0.4899(2) 0.0752(8) Uani 1 1 d D . . . .
C1S C 0.5253(14) -0.515(3) 0.5538(17) 0.094(9) Uani 0.5 1 d D . P . .
H1SA H 0.520125 -0.468600 0.618947 0.112 Uiso 0.5 1 calc R . P . .
H1SB H 0.567512 -0.588825 0.568995 0.112 Uiso 0.5 1 calc R . P . .
Re1B Re 0.8301(9) 0.232(3) 0.5602(14) 0.02089(10) Uani 0.0149(7) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 O4 2.100(5) . ?
Re1 O5 2.134(5) . ?
Re1 N1 2.211(5) . ?
Re1 C1 1.919(8) . ?
Re1 C2 1.886(8) . ?
Re1 C3 1.912(8) . ?
O1 C1 1.163(9) . ?
O2 C2 1.177(9) . ?
O3 C3 1.158(8) . ?
O4 C7 1.305(8) . ?
O5 C5 1.260(8) . ?
N1 C16 1.353(8) . ?
N1 C20 1.353(8) . ?
C4 C5 1.510(10) . ?
C5 C6 1.436(10) . ?
C6 C7 1.411(10) . ?
C6 C11 1.450(10) . ?
C7 C8 1.447(10) . ?
C8 C9 1.425(10) . ?
C8 C12 1.408(10) . ?
C9 C10 1.426(11) . ?
C9 C15 1.409(11) . ?
C10 C11 1.349(10) . ?
C12 C13 1.389(10) . ?
C13 C14 1.389(11) . ?
C14 C15 1.396(12) . ?
C16 C17 1.390(9) . ?
C17 C18 1.384(9) . ?
C18 C19 1.380(10) . ?
C19 C20 1.368(9) . ?
Cl1S C1S 1.653(14) . ?
Cl1S C1S 1.70(2) 3_646 ?

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
O4 Re1 O5 82.96(18) . . ?
O4 Re1 N1 82.73(19) . . ?
O5 Re1 N1 83.83(19) . . ?
C1 Re1 O4 95.9(3) . . ?
C1 Re1 O5 95.8(2) . . ?
C1 Re1 N1 178.6(3) . . ?
C2 Re1 O4 94.2(3) . . ?
C2 Re1 O5 174.0(2) . . ?
C2 Re1 N1 90.5(3) . . ?
C2 Re1 C1 89.8(3) . . ?
C2 Re1 C3 87.8(3) . . ?
C3 Re1 O4 176.3(2) . . ?
C3 Re1 O5 94.7(2) . . ?
C3 Re1 N1 94.2(3) . . ?
C3 Re1 C1 87.2(3) . . ?
C7 O4 Re1 131.3(4) . . ?
C5 O5 Re1 132.0(5) . . ?
C16 N1 Re1 121.3(4) . . ?
C16 N1 C20 117.1(6) . . ?
C20 N1 Re1 121.4(4) . . ?
O1 C1 Re1 177.2(7) . . ?
O2 C2 Re1 177.2(6) . . ?
O3 C3 Re1 179.2(7) . . ?
O5 C5 C4 114.8(6) . . ?
O5 C5 C6 125.0(7) . . ?
C6 C5 C4 120.2(7) . . ?
C5 C6 C11 119.1(7) . . ?
C7 C6 C5 123.2(7) . . ?
C7 C6 C11 117.6(7) . . ?
O4 C7 C6 125.0(7) . . ?
O4 C7 C8 115.2(6) . . ?
C6 C7 C8 119.8(7) . . ?
C9 C8 C7 120.1(7) . . ?
C12 C8 C7 121.5(7) . . ?
C12 C8 C9 118.4(7) . . ?
C8 C9 C10 118.8(7) . . ?
C15 C9 C8 119.8(7) . . ?
C15 C9 C10 121.3(7) . . ?
C11 C10 C9 120.7(8) . . ?
C10 C11 C6 122.9(7) . . ?
C13 C12 C8 121.1(7) . . ?
C12 C13 C14 120.2(8) . . ?
C13 C14 C15 120.4(8) . . ?
C14 C15 C9 120.0(8) . . ?
N1 C16 C17 122.0(7) . . ?
C18 C17 C16 119.4(7) . . ?
C19 C18 C17 118.8(7) . . ?
C20 C19 C18 118.9(7) . . ?
N1 C20 C19 123.7(6) . . ?
C1S Cl1S C1S 56.6(13) . 3_646 ?
Cl1S C1S Cl1S 123.4(13) . 3_646 ?

_olex2_submission_special_instructions 'No special instructions were received'

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

data_K9
_database_code_depnum_ccdc_archive 'CCDC 1962328'
loop_
_audit_author_name
_audit_author_address
'Curtis Moore'
;Ohio State University
United States of America
;
_audit_update_record             
;
2019-10-29 deposited with the CCDC.	2019-12-12 downloaded from the CCDC.
;
_audit_creation_date             2018-06-04
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 N2 O6 Re'
_chemical_formula_sum            'C13 H11 N2 O6 Re'
_chemical_formula_weight         477.44
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

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

_cell_length_a                   9.1080(5)
_cell_length_b                   9.5099(5)
_cell_length_c                   9.7673(5)
_cell_angle_alpha                70.669(2)
_cell_angle_beta                 80.012(2)
_cell_angle_gamma                61.781(2)
_cell_volume                     703.28(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5139
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      26.288
_cell_measurement_theta_min      2.538
_shelx_estimated_absorpt_T_max   0.523
_shelx_estimated_absorpt_T_min   0.406
_exptl_absorpt_coefficient_mu    8.671
_exptl_absorpt_correction_T_max  0.0932
_exptl_absorpt_correction_T_min  0.0602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0785 before and 0.0368 after correction. The Ratio of minimum to maximum transmission is 0.6459. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'Light Yellow'
_exptl_crystal_colour_modifier   Light
_exptl_crystal_colour_primary    Yellow
_exptl_crystal_density_diffrn    2.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.127
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.086
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10244
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.210
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2647
_reflns_number_total             2866
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.120
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2866
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0200
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0165P)²+0.0535P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0378
_refine_ls_wR_factor_ref         0.0387
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Re1) = Uanis(Re1B)
Uanis(O4) = Uanis(O5B)
Uanis(O5) = Uanis(O4B)
Uanis(O6) = Uanis(O6B)
Uanis(C6B) = Uanis(C7)
Uanis(C7B) = Uanis(C6)
Uanis(C5) = Uanis(C8B)
Uanis(C8) = Uanis(C5B)
Uanis(C9) = Uanis(C9B)
Uanis(C4) = Uanis(C4B)
Uanis(C2B) = Uanis(C3)
Uanis(O3) = Uanis(O2B)
Uanis(C3B) = Uanis(C2)
Uanis(O3B) = Uanis(O2)
3. Same fragment restrains
{Re1, O2, O3, O4, O5, O6, C2, C3, C4, C5, C6, C7, C8, C9} sigma for 1-2: 0.005,
1-3: 0.005
as
{Re1B, O2B, O3B, O4B, O5B, O6B, C2B, C3B, C4B, C5B, C6B, C7B, C8B, C9B}
4. Others
 Sof(Re1B)=Sof(O2B)=Sof(O3B)=Sof(O4B)=Sof(O5B)=Sof(O6B)=Sof(C2B)=Sof(C3B)=
 Sof(C4B)=Sof(H4B)=Sof(C5B)=Sof(H5B)=Sof(C6B)=Sof(C7B)=Sof(C8B)=Sof(C9B)=
 Sof(H9BA)=Sof(H9BB)=Sof(H9BC)=1-FVAR(1)
 Sof(Re1)=Sof(O2)=Sof(O3)=Sof(O4)=Sof(O5)=Sof(O6)=Sof(C2)=Sof(C3)=Sof(C4)=
 Sof(H4)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(C7)=Sof(C8)=Sof(C9)=Sof(H9A)=Sof(H9B)=
 Sof(H9C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C4(H4), C5(H5), C4B(H4B), C5B(H5B)
5.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C9(H9A,H9B,H9C), C9B(H9BA,H9BB,H9BC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
O1 O -0.1428(3) 0.8288(3) 0.4341(3) 0.0259(6) Uani 1 1 d . . . . .
N1 N 0.4687(4) 0.5127(4) 0.2469(3) 0.0225(7) Uani 1 1 d . . . . .
N2 N 0.7338(3) 0.3306(4) 0.2534(3) 0.0222(7) Uani 1 1 d . . . . .
C1 C -0.0109(4) 0.7587(4) 0.3902(4) 0.0196(8) Uani 1 1 d . . . . .
C10 C 0.5450(5) 0.5598(5) 0.1184(4) 0.0275(9) Uani 1 1 d . . . . .
H10 H 0.492038 0.655770 0.039837 0.033 Uiso 1 1 calc R . . . .
C11 C 0.7082(5) 0.4476(5) 0.1211(4) 0.0289(9) Uani 1 1 d . . . . .
H11 H 0.789021 0.449968 0.045607 0.035 Uiso 1 1 calc R . . . .
C12 C 0.5879(4) 0.3741(4) 0.3266(4) 0.0225(8) Uani 1 1 d . . . . .
H12 H 0.571514 0.314189 0.422423 0.027 Uiso 1 1 calc R . . . .
C13 C 0.8920(4) 0.1862(5) 0.3066(4) 0.0314(9) Uani 1 1 d . . . . .
H13A H 0.876629 0.126956 0.407074 0.047 Uiso 1 1 calc GR . . . .
H13B H 0.976343 0.223821 0.302690 0.047 Uiso 1 1 calc GR . . . .
H13C H 0.928815 0.111175 0.245734 0.047 Uiso 1 1 calc GR . . . .
Re1 Re 0.21082(7) 0.63902(6) 0.32135(7) 0.01602(8) Uani 0.928(3) 1 d D . P A 1
O2 O 0.0861(9) 0.4367(8) 0.2289(9) 0.0288(8) Uani 0.928(3) 1 d D . P A 1
O3 O 0.2750(11) 0.3894(5) 0.6254(5) 0.0229(10) Uani 0.928(3) 1 d D . P A 1
O4 O 0.1777(3) 0.8169(3) 0.1091(3) 0.0214(7) Uani 0.928(3) 1 d D . P A 1
O5 O 0.3012(3) 0.8009(3) 0.3458(3) 0.0184(6) Uani 0.928(3) 1 d D . P A 1
O6 O 0.3463(9) 1.1487(6) 0.0824(4) 0.0198(7) Uani 0.928(3) 1 d D . P A 1
C2 C 0.1354(7) 0.5095(5) 0.2678(4) 0.0211(9) Uani 0.928(3) 1 d D . P A 1
C3 C 0.2515(11) 0.4833(7) 0.5097(6) 0.0194(8) Uani 0.928(3) 1 d D . P A 1
C4 C 0.2723(5) 1.1618(5) -0.0328(4) 0.0226(9) Uani 0.928(3) 1 d D . P A 1
H4 H 0.262963 1.248741 -0.119544 0.027 Uiso 0.928(3) 1 calc R . P A 1
C5 C 0.2124(5) 1.0579(5) -0.0294(4) 0.0232(9) Uani 0.928(3) 1 d D . P A 1
H5 H 0.160502 1.071248 -0.112251 0.028 Uiso 0.928(3) 1 calc R . P A 1
C6 C 0.2264(4) 0.9256(5) 0.0999(4) 0.0188(9) Uani 0.928(3) 1 d D . P A 1
C7 C 0.2966(4) 0.9184(4) 0.2233(4) 0.0175(9) Uani 0.928(3) 1 d D . P A 1
C8 C 0.3575(4) 1.0285(4) 0.2108(4) 0.0175(8) Uani 0.928(3) 1 d D . P A 1
C9 C 0.4400(5) 1.0346(5) 0.3250(4) 0.0225(9) Uani 0.928(3) 1 d D . P A 1
H9A H 0.561194 0.975575 0.312817 0.034 Uiso 0.928(3) 1 calc GR . P A 1
H9B H 0.405889 0.981354 0.420642 0.034 Uiso 0.928(3) 1 calc GR . P A 1
H9C H 0.407590 1.150951 0.317266 0.034 Uiso 0.928(3) 1 calc GR . P A 1
Re1B Re 0.2125(10) 0.6482(9) 0.3460(8) 0.01602(8) Uani 0.072(3) 1 d D . P A 2
O2B O 0.286(16) 0.357(8) 0.624(6) 0.0229(10) Uani 0.072(3) 1 d D . P A 2
O3B O 0.092(13) 0.459(11) 0.229(13) 0.0288(8) Uani 0.072(3) 1 d D . P A 2
O4B O 0.316(4) 0.778(3) 0.4110(16) 0.0184(6) Uani 0.072(3) 1 d D . P A 2
O5B O 0.191(4) 0.851(3) 0.1550(17) 0.0214(7) Uani 0.072(3) 1 d D . P A 2
O6B O 0.336(11) 1.162(8) 0.084(4) 0.0198(7) Uani 0.072(3) 1 d D . P A 2
C2B C 0.263(14) 0.472(8) 0.522(5) 0.0194(8) Uani 0.072(3) 1 d D . P A 2
C3B C 0.130(8) 0.535(5) 0.276(3) 0.0211(9) Uani 0.072(3) 1 d D . P A 2
C4B C 0.406(5) 1.118(4) 0.212(3) 0.0226(9) Uani 0.072(3) 1 d D . P A 2
H4B H 0.455277 1.181283 0.224044 0.027 Uiso 0.072(3) 1 calc R . P A 2
C5B C 0.407(5) 0.990(4) 0.322(3) 0.0175(8) Uani 0.072(3) 1 d D . P A 2
H5B H 0.461099 0.959863 0.409227 0.021 Uiso 0.072(3) 1 calc R . P A 2
C6B C 0.328(4) 0.897(3) 0.307(2) 0.0175(9) Uani 0.072(3) 1 d D . P A 2
C7B C 0.264(5) 0.938(4) 0.169(2) 0.0188(9) Uani 0.072(3) 1 d D . P A 2
C8B C 0.269(5) 1.070(3) 0.060(2) 0.0232(9) Uani 0.072(3) 1 d D . P A 2
C9B C 0.202(6) 1.134(4) -0.087(2) 0.0225(9) Uani 0.072(3) 1 d D . P A 2
H9BA H 0.089217 1.144237 -0.080578 0.034 Uiso 0.072(3) 1 calc GR . P A 2
H9BB H 0.273985 1.056572 -0.143722 0.034 Uiso 0.072(3) 1 calc GR . P A 2
H9BC H 0.199517 1.243432 -0.135407 0.034 Uiso 0.072(3) 1 calc GR . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.151(4) . ?
N1 C10 1.371(4) . ?
N1 C12 1.335(4) . ?
N1 Re1 2.193(3) . ?
N1 Re1B 2.289(8) . ?
N2 C11 1.367(5) . ?
N2 C12 1.339(4) . ?
N2 C13 1.466(4) . ?
C1 Re1 1.920(4) . ?
C1 Re1B 1.845(9) . ?
C10 C11 1.358(5) . ?
Re1 O4 2.159(2) . ?
Re1 O5 2.148(2) . ?
Re1 C2 1.901(4) . ?
Re1 C3 1.905(4) . ?
O2 C2 1.163(5) . ?
O3 C3 1.164(5) . ?
O4 C6 1.277(4) . ?
O5 C7 1.331(4) . ?
O6 C4 1.352(5) . ?
O6 C8 1.370(4) . ?
C4 C5 1.326(5) . ?
C5 C6 1.431(5) . ?
C6 C7 1.427(5) . ?
C7 C8 1.364(5) . ?
C8 C9 1.479(5) . ?
Re1B O4B 2.159(5) . ?
Re1B O5B 2.149(5) . ?
Re1B C2B 1.903(6) . ?
Re1B C3B 1.906(6) . ?
O2B C2B 1.164(7) . ?
O3B C3B 1.165(7) . ?
O4B C6B 1.277(6) . ?
O5B C7B 1.332(6) . ?
O6B C4B 1.352(7) . ?
O6B C8B 1.369(6) . ?
C4B C5B 1.325(7) . ?
C5B C6B 1.431(6) . ?
C6B C7B 1.428(7) . ?
C7B C8B 1.364(6) . ?
C8B C9B 1.479(7) . ?

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
C10 N1 Re1 129.2(2) . . ?
C10 N1 Re1B 131.9(3) . . ?
C12 N1 C10 105.7(3) . . ?
C12 N1 Re1 124.9(2) . . ?
C12 N1 Re1B 121.3(3) . . ?
C11 N2 C13 126.5(3) . . ?
C12 N2 C11 107.3(3) . . ?
C12 N2 C13 126.2(3) . . ?
O1 C1 Re1 178.7(3) . . ?
O1 C1 Re1B 170.6(4) . . ?
C11 C10 N1 109.2(3) . . ?
C10 C11 N2 106.8(3) . . ?
N1 C12 N2 111.0(3) . . ?
C1 Re1 N1 176.26(13) . . ?
C1 Re1 O4 94.85(12) . . ?
C1 Re1 O5 94.60(13) . . ?
O4 Re1 N1 84.82(11) . . ?
O5 Re1 N1 81.70(11) . . ?
O5 Re1 O4 76.68(10) . . ?
C2 Re1 N1 94.87(19) . . ?
C2 Re1 C1 88.9(2) . . ?
C2 Re1 O4 94.76(13) . . ?
C2 Re1 O5 170.98(14) . . ?
C2 Re1 C3 88.01(15) . . ?
C3 Re1 N1 92.9(3) . . ?
C3 Re1 C1 87.2(3) . . ?
C3 Re1 O4 176.58(19) . . ?
C3 Re1 O5 100.46(13) . . ?
C6 O4 Re1 113.4(2) . . ?
C7 O5 Re1 112.9(2) . . ?
C4 O6 C8 120.6(3) . . ?
O2 C2 Re1 176.6(5) . . ?
O3 C3 Re1 179.3(9) . . ?
C5 C4 O6 122.5(3) . . ?
C4 C5 C6 119.6(4) . . ?
O4 C6 C5 123.0(3) . . ?
O4 C6 C7 119.6(3) . . ?
C7 C6 C5 117.5(4) . . ?
O5 C7 C6 117.4(3) . . ?
O5 C7 C8 123.1(3) . . ?
C8 C7 C6 119.5(3) . . ?
O6 C8 C9 113.0(3) . . ?
C7 C8 O6 120.3(3) . . ?
C7 C8 C9 126.7(3) . . ?
C1 Re1B N1 167.6(4) . . ?
C1 Re1B O4B 102.0(10) . . ?
C1 Re1B O5B 90.9(10) . . ?
C1 Re1B C2B 95(4) . . ?
C1 Re1B C3B 81(2) . . ?
O4B Re1B N1 87.4(10) . . ?
O5B Re1B N1 83.4(10) . . ?
O5B Re1B O4B 76.67(18) . . ?
C2B Re1B N1 92(4) . . ?
C2B Re1B O4B 94.7(3) . . ?
C2B Re1B O5B 170.3(18) . . ?
C2B Re1B C3B 87.9(3) . . ?
C3B Re1B N1 89(2) . . ?
C3B Re1B O4B 175.8(16) . . ?
C3B Re1B O5B 100.4(3) . . ?
C6B O4B Re1B 113.2(4) . . ?
C7B O5B Re1B 112.6(4) . . ?
C4B O6B C8B 120.5(5) . . ?
O2B C2B Re1B 173(4) . . ?
O3B C3B Re1B 175(6) . . ?
C5B C4B O6B 122.5(5) . . ?
C4B C5B C6B 119.5(5) . . ?
O4B C6B C5B 123.0(5) . . ?
O4B C6B C7B 119.6(4) . . ?
C7B C6B C5B 117.4(5) . . ?
O5B C7B C6B 117.4(5) . . ?
O5B C7B C8B 123.0(5) . . ?
C8B C7B C6B 119.4(5) . . ?
O6B C8B C9B 113.1(5) . . ?
C7B C8B O6B 120.3(5) . . ?
C7B C8B C9B 126.6(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
