# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 2094782'
loop_
_audit_author_name
_audit_author_address
'Olivier Blacque'
;Department of Chemistry, University of Zurich
Switzerland
;
_audit_update_record             
;
2021-07-06 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;

_audit_creation_date             2021-04-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H14 Cl O5 Re'
_chemical_formula_sum            'C18 H14 Cl O5 Re'
_chemical_formula_weight         531.94
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -5.2083 5.8923 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.1670(2)
_cell_length_b                   9.36020(10)
_cell_length_c                   10.2239(2)
_cell_angle_alpha                90.583(2)
_cell_angle_beta                 103.616(2)
_cell_angle_gamma                90.8300(10)
_cell_volume                     852.43(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    17565
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      79.0920
_cell_measurement_theta_min      4.4380
_shelx_estimated_absorpt_T_max   0.236
_shelx_estimated_absorpt_T_min   0.082
_exptl_absorpt_coefficient_mu    15.623
_exptl_absorpt_correction_T_max  0.281
_exptl_absorpt_correction_T_min  0.033
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.072
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             508
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0911
0 -1 0 0.0731
-1 0 0 0.1258
1 0 0 0.1528
1 1 0 0.1137
-1 -1 0 0.1137
0 0 -1 0.0601
0 0 1 0.0721
-1 1 1 0.1258
5 -2 -3 0.1745

_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13

_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.999
_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       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16835
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.483
_diffrn_reflns_theta_min         4.450
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -122.00 -55.00   0.50    0.10    --  -49.87-150.00 143.00  134
  2  ω   -125.00 -75.00   0.50    0.10    --  -49.87-122.00 -54.00  100
  3  ω   -105.00 -25.00   0.50    0.10    --  -49.87 150.00-171.00  160
  4  ω    -85.00 -10.00   0.50    0.10    --  -49.87 122.00  26.00  150
  5  ω     32.00  97.00   0.50    0.10    --   49.87-122.00 -54.00  130
  6  ω     47.00 114.00   0.50    0.10    --   49.87-150.00 143.00  134
  7  ω    -85.00 -13.00   0.50    0.20    --  -88.50 122.00  26.00  144
  8  ω   -150.00 -55.00   0.50    0.20    --  -88.50-150.00 143.00  190
  9  ω     77.00 166.00   0.50    0.20    --  110.00 150.00-171.00  178
 10  ω     96.00 178.00   0.50    0.20    --  110.00 122.00  26.00  164
 11  ω     35.00 111.00   0.50    0.20    --  110.00-122.00 -54.00  152
 12  ω     47.00 130.00   0.50    0.20    --  110.00-150.00 143.00  166
 13  ω   -123.00 -34.00   0.50    0.10    --  -49.87 -57.00 -60.00  178
 14  ω   -124.00 -26.00   0.50    0.10    --  -49.87 -77.00  60.00  196
 15  ω   -125.00 -73.00   0.50    0.10    --  -49.87-125.00 -30.00  104
 16  ω   -128.00 -35.00   0.50    0.10    --  -49.87 -37.00-180.00  186
 17  ω   -162.00 -65.00   0.50    0.20    --  -88.50 -76.00  15.48  194
 18  ω   -164.00 -75.00   0.50    0.20    --  -88.50-122.00 -54.00  178
 19  ω     91.00 178.00   0.50    0.20    --  110.00  66.00   8.29  174
 20  ω     34.00 124.00   0.50    0.20    --  110.00 -45.00  90.00  180
 21  ω     36.00 134.00   0.50    0.20    --  110.00 -77.00  90.00  196
 22  ω     34.00 108.00   0.50    0.20    --  110.00-111.00  30.00  148
 23  ω     34.00 107.00   0.50    0.20    --  110.00 -94.00 120.00  146
 24  ω     34.00 108.00   0.50    0.20    --  110.00-111.00 -30.00  148
 25  ω     94.00 178.00   0.50    0.20    --  110.00  15.00  90.00  168
 26  ω    102.00 178.00   0.50    0.20    --  110.00 111.00  90.00  152
 27  ω     38.00 127.00   0.50    0.20    --  110.00 -61.00  90.00  178
 28  ω     96.00 178.00   0.50    0.20    --  110.00  45.00 120.00  164
 29  ω     62.00 146.00   0.50    0.20    --  110.00 178.00  90.00  168
 30  ω     34.00 124.00   0.50    0.20    --  110.00 -45.00-180.00  180
 31  ω     34.00 107.00   0.50    0.20    --  110.00 -94.00  60.00  146
 32  ω     94.00 178.00   0.50    0.20    --  110.00  15.00 -60.00  168
 33  ω     34.00 108.00   0.50    0.20    --  110.00-111.00-120.00  148
 34  ω     33.00 108.00   0.50    0.20    --  110.00-103.00 106.14  150
 35  ω     35.00 124.00   0.50    0.20    --  110.00 -30.00 -60.00  178
 36  ω     69.00 103.00   0.50    0.20    --  110.00 -94.00-150.00   68
 37  ω     57.00 107.00   0.50    0.20    --  110.00 -94.00  30.00  100
 38  ω     54.00  80.00   0.50    0.20    --  110.00 -94.00 -30.00   52
 39  ω    102.00 178.00   0.50    0.20    --  110.00 111.00 150.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0823467000
_diffrn_orient_matrix_UB_12      -0.0078723000
_diffrn_orient_matrix_UB_13      -0.1498247000
_diffrn_orient_matrix_UB_21      -0.1323986000
_diffrn_orient_matrix_UB_22      -0.0800189000
_diffrn_orient_matrix_UB_23      0.0370445000
_diffrn_orient_matrix_UB_31      -0.0748211000
_diffrn_orient_matrix_UB_32      0.1436483000
_diffrn_orient_matrix_UB_33      0.0149094000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3469
_reflns_number_total             3480

_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       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_refine_diff_density_max         2.630
_refine_diff_density_min         -2.658
_refine_diff_density_rms         0.193
_refine_ls_extinction_coef       0.0065(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3480
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0312
_refine_ls_restrained_S_all      1.184
_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)+(0.0532P)²+1.6665P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0818
_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.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C11(H11), C12(H12), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7791(5) 0.4619(5) 0.4245(4) 0.0256(9) Uani 1 1 d . . . . .
C2 C 0.9212(5) 0.6808(5) 0.3236(5) 0.0249(9) Uani 1 1 d . . . . .
C3 C 0.6289(5) 0.6260(5) 0.2212(5) 0.0252(9) Uani 1 1 d . . . . .
C4 C 0.8182(5) 0.7932(4) 0.5948(4) 0.0192(8) Uani 1 1 d . . . . .
C5 C 0.7614(5) 0.8905(4) 0.4873(4) 0.0191(8) Uani 1 1 d . . . . .
H5 H 0.817135 0.964990 0.458048 0.023 Uiso 1 1 calc R U . . .
C6 C 0.6073(5) 0.8556(4) 0.4324(4) 0.0203(8) Uani 1 1 d . . . . .
C7 C 0.5697(5) 0.7369(5) 0.5077(4) 0.0201(8) Uani 1 1 d . . . . .
H7 H 0.473931 0.690953 0.492120 0.024 Uiso 1 1 calc R U . . .
C8 C 0.6971(5) 0.6995(5) 0.6084(4) 0.0206(8) Uani 1 1 d . . . . .
C9 C 0.6976(5) 0.5869(5) 0.7122(4) 0.0249(9) Uani 1 1 d . . . . .
H9A H 0.612198 0.521028 0.680668 0.037 Uiso 1 1 calc R U . . .
H9B H 0.689768 0.632392 0.796960 0.037 Uiso 1 1 calc R U . . .
H9C H 0.791314 0.533766 0.726696 0.037 Uiso 1 1 calc R U . . .
C10 C 0.5033(5) 0.9275(4) 0.3202(4) 0.0208(8) Uani 1 1 d . . . . .
C11 C 0.3497(5) 0.8941(5) 0.2898(5) 0.0253(9) Uani 1 1 d . . . . .
H11 H 0.311728 0.826647 0.342845 0.030 Uiso 1 1 calc R U . . .
C12 C 0.2524(5) 0.9583(5) 0.1831(5) 0.0269(10) Uani 1 1 d . . . . .
H12 H 0.148705 0.932838 0.160883 0.032 Uiso 1 1 calc R U . . .
C13 C 0.3073(5) 1.0592(5) 0.1098(5) 0.0267(9) Uani 1 1 d . . . . .
C14 C 0.4587(5) 1.0962(5) 0.1376(5) 0.0273(9) Uani 1 1 d . . . . .
H14 H 0.494703 1.165927 0.085532 0.033 Uiso 1 1 calc R U . . .
C15 C 0.5568(5) 1.0298(5) 0.2427(5) 0.0258(9) Uani 1 1 d . . . . .
H15 H 0.660826 1.053618 0.262327 0.031 Uiso 1 1 calc R U . . .
C16 C 0.9714(5) 0.8124(5) 0.6820(4) 0.0204(8) Uani 1 1 d . . . . .
C17 C 1.1512(5) 0.7258(5) 0.8688(5) 0.0272(9) Uani 1 1 d . . . . .
H17A H 1.161121 0.822681 0.910057 0.033 Uiso 1 1 calc R U . . .
H17B H 1.233205 0.713238 0.821824 0.033 Uiso 1 1 calc R U . . .
C18 C 1.1602(5) 0.6154(6) 0.9746(5) 0.0319(10) Uani 1 1 d . . . . .
H18A H 1.152863 0.519981 0.932886 0.048 Uiso 1 1 calc R U . . .
H18B H 1.077526 0.627720 1.019170 0.048 Uiso 1 1 calc R U . . .
H18C H 1.256189 0.625937 1.041055 0.048 Uiso 1 1 calc R U . . .
Cl1 Cl 0.18485(13) 1.14190(13) -0.02394(12) 0.0345(3) Uani 1 1 d . . . . .
O1 O 0.7891(4) 0.3410(4) 0.4435(4) 0.0341(8) Uani 1 1 d . . . . .
O2 O 1.0231(4) 0.6975(4) 0.2773(4) 0.0351(8) Uani 1 1 d . . . . .
O3 O 0.5524(4) 0.6096(5) 0.1151(4) 0.0397(9) Uani 1 1 d . . . . .
O4 O 1.0529(4) 0.9103(4) 0.6730(3) 0.0294(7) Uani 1 1 d . . . . .
O5 O 1.0055(3) 0.7084(3) 0.7736(3) 0.0257(6) Uani 1 1 d . . . . .
Re1 Re 0.74878(2) 0.66278(2) 0.39852(2) 0.01761(12) 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
C1 O1 1.151(6) . ?
C1 Re1 1.917(5) . ?
C2 O2 1.151(6) . ?
C2 Re1 1.918(5) . ?
C3 O3 1.153(6) . ?
C3 Re1 1.910(5) . ?
C4 C5 1.440(6) . ?
C4 C8 1.438(6) . ?
C4 C16 1.483(6) . ?
C4 Re1 2.291(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.424(6) . ?
C5 Re1 2.298(4) . ?
C6 C7 1.441(6) . ?
C6 C10 1.482(6) . ?
C6 Re1 2.307(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.414(6) . ?
C7 Re1 2.303(4) . ?
C8 C9 1.503(6) . ?
C8 Re1 2.327(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.399(6) . ?
C10 C15 1.403(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.373(7) . ?
C13 C14 1.388(7) . ?
C13 Cl1 1.747(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(6) . ?
C15 H15 0.9500 . ?
C16 O4 1.192(6) . ?
C16 O5 1.346(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.493(6) . ?
C17 O5 1.461(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
O1 C1 Re1 175.5(4) . . ?
O2 C2 Re1 177.1(4) . . ?
O3 C3 Re1 176.6(4) . . ?
C5 C4 C16 121.0(4) . . ?
C5 C4 Re1 72.0(2) . . ?
C8 C4 C5 108.2(3) . . ?
C8 C4 C16 130.3(4) . . ?
C8 C4 Re1 73.2(2) . . ?
C16 C4 Re1 127.4(3) . . ?
C4 C5 H5 125.9 . . ?
C4 C5 Re1 71.4(2) . . ?
C6 C5 C4 108.2(3) . . ?
C6 C5 H5 125.9 . . ?
C6 C5 Re1 72.3(2) . . ?
Re1 C5 H5 122.0 . . ?
C5 C6 C7 107.0(4) . . ?
C5 C6 C10 127.1(4) . . ?
C5 C6 Re1 71.6(2) . . ?
C7 C6 C10 125.9(4) . . ?
C7 C6 Re1 71.6(2) . . ?
C10 C6 Re1 122.5(3) . . ?
C6 C7 H7 125.2 . . ?
C6 C7 Re1 71.9(2) . . ?
C8 C7 C6 109.5(4) . . ?
C8 C7 H7 125.2 . . ?
C8 C7 Re1 73.1(2) . . ?
Re1 C7 H7 121.3 . . ?
C4 C8 C9 128.2(4) . . ?
C4 C8 Re1 70.5(2) . . ?
C7 C8 C4 107.1(4) . . ?
C7 C8 C9 124.6(4) . . ?
C7 C8 Re1 71.3(2) . . ?
C9 C8 Re1 125.7(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C6 120.3(4) . . ?
C11 C10 C15 118.9(4) . . ?
C15 C10 C6 120.8(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.6(4) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.3(4) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 C14 121.7(4) . . ?
C12 C13 Cl1 119.6(4) . . ?
C14 C13 Cl1 118.7(4) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 119.0(4) . . ?
C15 C14 H14 120.5 . . ?
C10 C15 H15 119.8 . . ?
C14 C15 C10 120.4(4) . . ?
C14 C15 H15 119.8 . . ?
O4 C16 C4 123.5(4) . . ?
O4 C16 O5 124.4(4) . . ?
O5 C16 C4 112.1(4) . . ?
H17A C17 H17B 108.5 . . ?
C18 C17 H17A 110.2 . . ?
C18 C17 H17B 110.2 . . ?
O5 C17 H17A 110.2 . . ?
O5 C17 H17B 110.2 . . ?
O5 C17 C18 107.7(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 O5 C17 114.9(3) . . ?
C1 Re1 C2 91.60(19) . . ?
C1 Re1 C4 112.89(17) . . ?
C1 Re1 C5 149.46(16) . . ?
C1 Re1 C6 145.48(17) . . ?
C1 Re1 C7 109.36(17) . . ?
C1 Re1 C8 93.77(17) . . ?
C2 Re1 C4 102.90(17) . . ?
C2 Re1 C5 96.56(17) . . ?
C2 Re1 C6 122.81(17) . . ?
C2 Re1 C7 156.58(18) . . ?
C2 Re1 C8 136.30(17) . . ?
C3 Re1 C1 90.23(19) . . ?
C3 Re1 C2 88.72(19) . . ?
C3 Re1 C4 153.43(17) . . ?
C3 Re1 C5 119.24(17) . . ?
C3 Re1 C6 93.00(17) . . ?
C3 Re1 C7 101.15(17) . . ?
C3 Re1 C8 134.52(17) . . ?
C4 Re1 C5 36.57(14) . . ?
C4 Re1 C6 60.57(15) . . ?
C4 Re1 C7 59.91(14) . . ?
C4 Re1 C8 36.27(14) . . ?
C5 Re1 C6 36.02(14) . . ?
C5 Re1 C7 60.07(15) . . ?
C5 Re1 C8 60.52(14) . . ?
C6 Re1 C8 60.44(15) . . ?
C7 Re1 C6 36.43(14) . . ?
C7 Re1 C8 35.57(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H5 O4 0.95 2.31 3.216(5) 160.1 2_776 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C5 C6 C7 0.5(5) . . . . ?
C4 C5 C6 C10 179.8(4) . . . . ?
C4 C5 C6 Re1 -62.9(3) . . . . ?
C4 C16 O5 C17 -176.1(4) . . . . ?
C5 C4 C8 C7 1.6(5) . . . . ?
C5 C4 C8 C9 -175.4(4) . . . . ?
C5 C4 C8 Re1 64.0(3) . . . . ?
C5 C4 C16 O4 3.4(7) . . . . ?
C5 C4 C16 O5 -178.0(4) . . . . ?
C5 C6 C7 C8 0.6(5) . . . . ?
C5 C6 C7 Re1 -63.3(3) . . . . ?
C5 C6 C10 C11 -171.0(4) . . . . ?
C5 C6 C10 C15 9.2(7) . . . . ?
C6 C7 C8 C4 -1.4(5) . . . . ?
C6 C7 C8 C9 175.8(4) . . . . ?
C6 C7 C8 Re1 -63.2(3) . . . . ?
C6 C10 C11 C12 -178.4(4) . . . . ?
C6 C10 C15 C14 179.7(4) . . . . ?
C7 C6 C10 C11 8.2(7) . . . . ?
C7 C6 C10 C15 -171.6(4) . . . . ?
C8 C4 C5 C6 -1.3(5) . . . . ?
C8 C4 C5 Re1 -64.8(3) . . . . ?
C8 C4 C16 O4 -166.5(4) . . . . ?
C8 C4 C16 O5 12.1(6) . . . . ?
C10 C6 C7 C8 -178.7(4) . . . . ?
C10 C6 C7 Re1 117.3(4) . . . . ?
C10 C11 C12 C13 -2.2(7) . . . . ?
C11 C10 C15 C14 -0.1(7) . . . . ?
C11 C12 C13 C14 1.6(8) . . . . ?
C11 C12 C13 Cl1 -179.4(4) . . . . ?
C12 C13 C14 C15 -0.3(8) . . . . ?
C13 C14 C15 C10 -0.5(7) . . . . ?
C15 C10 C11 C12 1.4(7) . . . . ?
C16 C4 C5 C6 -173.2(4) . . . . ?
C16 C4 C5 Re1 123.3(4) . . . . ?
C16 C4 C8 C7 172.5(4) . . . . ?
C16 C4 C8 C9 -4.5(7) . . . . ?
C16 C4 C8 Re1 -125.2(5) . . . . ?
C18 C17 O5 C16 171.4(4) . . . . ?
Cl1 C13 C14 C15 -179.3(4) . . . . ?
O4 C16 O5 C17 2.4(6) . . . . ?
Re1 C4 C5 C6 63.5(3) . . . . ?
Re1 C4 C8 C7 -62.3(3) . . . . ?
Re1 C4 C8 C9 120.6(4) . . . . ?
Re1 C4 C16 O4 93.7(5) . . . . ?
Re1 C4 C16 O5 -87.8(4) . . . . ?
Re1 C5 C6 C7 63.3(3) . . . . ?
Re1 C5 C6 C10 -117.4(4) . . . . ?
Re1 C6 C7 C8 63.9(3) . . . . ?
Re1 C6 C10 C11 98.2(4) . . . . ?
Re1 C6 C10 C15 -81.6(5) . . . . ?
Re1 C7 C8 C4 61.8(3) . . . . ?
Re1 C7 C8 C9 -121.0(4) . . . . ?

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

data_3
_database_code_depnum_ccdc_archive 'CCDC 2094783'
loop_
_audit_author_name
_audit_author_address
'Olivier Blacque'
;Department of Chemistry, University of Zurich
Switzerland
;
_audit_update_record             
;
2021-07-06 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;

_audit_creation_date             2021-04-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H15 Cl O2'
_chemical_formula_sum            'C15 H15 Cl O2'
_chemical_formula_weight         262.72
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   25.9451(7)
_cell_length_b                   4.24250(10)
_cell_length_c                   11.7127(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1289.24(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7092
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      75.9660
_cell_measurement_theta_min      3.3830
_shelx_estimated_absorpt_T_max   0.862
_shelx_estimated_absorpt_T_min   0.461
_exptl_absorpt_coefficient_mu    2.546
_exptl_absorpt_correction_T_max  0.860
_exptl_absorpt_correction_T_min  0.613
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0389
-1 0 0 0.0249
0 0 -1 0.0849
1 0 5 0.0968
0 1 5 0.0737
-1 2 -3 0.1668
1 -3 1 0.1627
-5 1 0 0.1218
-11 1 -6 0.0746
-14 1 4 0.0486
14 0 -4 0.0610
10 0 -6 0.0722

_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06

_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18917
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.313
_diffrn_reflns_theta_min         3.407
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00  37.00   0.80    0.80    --  -41.74  19.00 120.00  145
  2  ω    -64.00  30.40   0.80    0.80    --  -41.74  37.00-150.00  118
  3  ω     10.00  41.20   0.80    0.80    --   41.74  78.00  54.93   39
  4  ω    -31.00  63.40   0.80    0.80    --   41.74 -37.00 -90.00  118
  5  ω     27.00  95.80   0.80    0.80    --   41.74-125.00 -60.00   86
  6  ω    -31.00  63.40   0.80    0.80    --   41.74 -37.00 120.00  118
  7  ω    103.00 177.40   0.80    1.50    --  111.00  77.00  90.00   93
  8  ω     31.00 155.00   0.80    1.50    --  111.00 -15.00 -30.00  155
  9  ω     41.00 123.40   0.80    1.50    --  111.00-140.00  58.84  103
 10  ω     36.00 108.00   0.80    1.50    --  111.00-111.00 -60.00   90
 11  ω     36.00 108.00   0.80    1.50    --  111.00-111.00  30.00   90
 12  ω     31.00 155.00   0.80    1.50    --  111.00 -15.00-180.00  155
 13  ω     36.00 108.00   0.80    1.50    --  111.00-111.00-150.00   90
 14  ω     41.00 138.60   0.80    1.50    --  111.00 -61.00 -30.00  122
 15  ω     40.00 134.40   0.80    1.50    --  111.00 -45.00 150.00  118
 16  ω     87.00 177.40   0.80    1.50    --  111.00  45.00   0.00  113
 17  ω    104.00 177.60   0.80    1.50    --  111.00 111.00 -60.00   92
 18  ω     40.00 134.40   0.80    1.50    --  111.00 -45.00   0.00  118
 19  ω     36.00 108.00   0.80    1.50    --  111.00-111.00-120.00   90
 20  ω     36.00 108.00   0.80    1.50    --  111.00-111.00-180.00   90
 21  ω     30.00 106.00   0.80    1.50    --  111.00 -94.00  30.00   95
 22  ω     36.00 108.00   0.80    1.50    --  111.00-111.00 120.00   90
 23  ω     36.00 108.00   0.80    1.50    --  111.00-111.00 -30.00   90
 24  ω    104.00 177.60   0.80    1.50    --  111.00 111.00 -30.00   92
 25  ω     34.00 106.80   0.80    1.50    --  111.00-104.00 -12.32   91
 26  ω     41.00 122.60   0.80    1.50    --  111.00-138.00-170.94  102
 27  ω   -112.00 -16.00   0.80    0.80    --  -41.74 -57.00  60.00  120
 28  ω     11.00  40.60   0.80    0.80    --   41.74  76.00-119.50   37
 29  ω      9.00  41.00   0.80    0.80    --   41.74  82.00 117.07   40
 30  ω     10.00  41.20   0.80    0.80    --   41.74  77.00  -1.86   39
 31  ω     10.00  41.20   0.80    0.80    --   41.74  78.00 -39.84   39
 32  ω     10.00  41.20   0.80    0.80    --   41.74  78.00-153.36   39
 33  ω     87.00 177.40   0.80    1.50    --  111.00  30.00-150.00  113
 34  ω     66.00 178.00   0.80    1.50    --  111.00  15.00 -60.00  140
 35  ω     87.00 177.40   0.80    1.50    --  111.00  45.00  60.00  113
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0521355000
_diffrn_orient_matrix_UB_12      -0.0289264000
_diffrn_orient_matrix_UB_13      0.0621588000
_diffrn_orient_matrix_UB_21      0.0284642000
_diffrn_orient_matrix_UB_22      -0.0361291000
_diffrn_orient_matrix_UB_23      0.1147417000
_diffrn_orient_matrix_UB_31      -0.0013120000
_diffrn_orient_matrix_UB_32      0.3599232000
_diffrn_orient_matrix_UB_33      0.0165482000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.882
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                2567
_reflns_number_total             2682

_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       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Flack x determined using 1127 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2682
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0545
_refine_ls_restrained_S_all      1.160
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0506P)²+2.2480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1522
_refine_ls_wR_factor_ref         0.1533
_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.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6147(2) 0.2841(12) 0.3809(4) 0.0283(10) Uani 1 1 d . . . . .
C2 C 0.5633(2) 0.3682(14) 0.3817(5) 0.0356(12) Uani 1 1 d . . . . .
H2 H 0.550858 0.499992 0.441213 0.043 Uiso 1 1 calc R U . . .
C3 C 0.5291(2) 0.2658(15) 0.2981(5) 0.0380(13) Uani 1 1 d . . . . .
H3 H 0.494121 0.331907 0.299055 0.046 Uiso 1 1 calc R U . . .
C4 C 0.5469(2) 0.0663(15) 0.2136(5) 0.0373(13) Uani 1 1 d . . . . .
C5 C 0.5977(2) -0.0263(15) 0.2106(5) 0.0374(13) Uani 1 1 d . . . . .
H5 H 0.609655 -0.160675 0.151369 0.045 Uiso 1 1 calc R U . . .
C6 C 0.6316(2) 0.0780(14) 0.2948(4) 0.0342(12) Uani 1 1 d . . . . .
H6 H 0.666444 0.009136 0.293990 0.041 Uiso 1 1 calc R U . . .
C7 C 0.6508(2) 0.3939(12) 0.4694(4) 0.0284(10) Uani 1 1 d . . . . .
C8 C 0.7019(2) 0.3476(12) 0.4755(4) 0.0323(11) Uani 1 1 d . . . . .
H8 H 0.721646 0.232786 0.421199 0.039 Uiso 1 1 calc R U . . .
C9 C 0.7229(2) 0.4986(14) 0.5773(5) 0.0349(12) Uani 1 1 d . . . . .
C10 C 0.6843(2) 0.6465(12) 0.6325(5) 0.0336(12) Uani 1 1 d . . . . .
C11 C 0.6344(2) 0.5903(13) 0.5698(4) 0.0324(11) Uani 1 1 d . . . . .
H11A H 0.609461 0.475424 0.618300 0.039 Uiso 1 1 calc R U . . .
H11B H 0.618805 0.791504 0.544645 0.039 Uiso 1 1 calc R U . . .
C12 C 0.7790(2) 0.4814(16) 0.6079(6) 0.0448(14) Uani 1 1 d . . . . .
H12A H 0.790824 0.262589 0.602233 0.067 Uiso 1 1 calc R U . . .
H12B H 0.783906 0.557200 0.686175 0.067 Uiso 1 1 calc R U . . .
H12C H 0.798926 0.613289 0.555222 0.067 Uiso 1 1 calc R U . . .
C13 C 0.6890(2) 0.8296(14) 0.7380(5) 0.0369(12) Uani 1 1 d . . . . .
C14 C 0.6437(3) 1.1309(15) 0.8749(5) 0.0424(14) Uani 1 1 d . . . . .
H14A H 0.670633 1.295775 0.870917 0.051 Uiso 1 1 calc R U . . .
H14B H 0.651226 0.992278 0.940855 0.051 Uiso 1 1 calc R U . . .
C15 C 0.5918(3) 1.2783(18) 0.8882(6) 0.0509(16) Uani 1 1 d . . . . .
H15A H 0.586105 1.429701 0.826280 0.076 Uiso 1 1 calc R U . . .
H15B H 0.589978 1.387723 0.961792 0.076 Uiso 1 1 calc R U . . .
H15C H 0.565225 1.114326 0.885271 0.076 Uiso 1 1 calc R U . . .
Cl1 Cl 0.50406(6) -0.0667(4) 0.11017(14) 0.0492(4) Uani 1 1 d . . . . .
O1 O 0.72796(17) 0.8743(11) 0.7913(4) 0.0476(11) Uani 1 1 d . . . . .
O2 O 0.64294(15) 0.9480(10) 0.7698(3) 0.0361(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
C1 C2 1.381(7) . ?
C1 C6 1.405(7) . ?
C1 C7 1.473(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(8) . ?
C4 C5 1.376(8) . ?
C4 Cl1 1.739(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.343(8) . ?
C7 C11 1.502(7) . ?
C8 H8 0.9500 . ?
C8 C9 1.459(8) . ?
C9 C10 1.347(8) . ?
C9 C12 1.501(7) . ?
C10 C11 1.506(7) . ?
C10 C13 1.464(8) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 O1 1.203(7) . ?
C13 O2 1.349(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.493(9) . ?
C14 O2 1.456(7) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C2 C1 C6 117.9(5) . . ?
C2 C1 C7 121.8(5) . . ?
C6 C1 C7 120.3(5) . . ?
C1 C2 H2 119.0 . . ?
C1 C2 C3 122.0(5) . . ?
C3 C2 H2 119.0 . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.8(5) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 Cl1 119.0(5) . . ?
C5 C4 C3 120.9(5) . . ?
C5 C4 Cl1 120.1(5) . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.7(5) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.6(5) . . ?
C5 C6 H6 119.7 . . ?
C1 C7 C11 123.2(5) . . ?
C8 C7 C1 128.2(5) . . ?
C8 C7 C11 108.6(5) . . ?
C7 C8 H8 124.9 . . ?
C7 C8 C9 110.3(5) . . ?
C9 C8 H8 124.9 . . ?
C8 C9 C12 122.4(5) . . ?
C10 C9 C8 108.7(5) . . ?
C10 C9 C12 129.0(6) . . ?
C9 C10 C11 109.3(5) . . ?
C9 C10 C13 126.2(5) . . ?
C13 C10 C11 124.5(5) . . ?
C7 C11 C10 103.1(4) . . ?
C7 C11 H11A 111.1 . . ?
C7 C11 H11B 111.1 . . ?
C10 C11 H11A 111.1 . . ?
C10 C11 H11B 111.1 . . ?
H11A C11 H11B 109.1 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 C10 126.3(6) . . ?
O1 C13 O2 122.9(6) . . ?
O2 C13 C10 110.9(5) . . ?
H14A C14 H14B 108.5 . . ?
C15 C14 H14A 110.2 . . ?
C15 C14 H14B 110.2 . . ?
O2 C14 H14A 110.2 . . ?
O2 C14 H14B 110.2 . . ?
O2 C14 C15 107.4(5) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 O2 C14 114.8(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C12 H12B O1 0.98 2.33 3.024(8) 127.1 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 2.0(9) . . . . ?
C1 C7 C8 C9 179.7(5) . . . . ?
C1 C7 C11 C10 -178.8(4) . . . . ?
C2 C1 C6 C5 2.6(8) . . . . ?
C2 C1 C7 C8 -175.5(5) . . . . ?
C2 C1 C7 C11 3.1(8) . . . . ?
C2 C3 C4 C5 -1.1(8) . . . . ?
C2 C3 C4 Cl1 179.1(5) . . . . ?
C3 C4 C5 C6 1.1(9) . . . . ?
C4 C5 C6 C1 -1.9(8) . . . . ?
C6 C1 C2 C3 -2.7(8) . . . . ?
C6 C1 C7 C8 7.1(8) . . . . ?
C6 C1 C7 C11 -174.3(5) . . . . ?
C7 C1 C2 C3 179.8(5) . . . . ?
C7 C1 C6 C5 -179.8(5) . . . . ?
C7 C8 C9 C10 -1.7(6) . . . . ?
C7 C8 C9 C12 178.8(5) . . . . ?
C8 C7 C11 C10 0.1(6) . . . . ?
C8 C9 C10 C11 1.7(6) . . . . ?
C8 C9 C10 C13 -179.3(5) . . . . ?
C9 C10 C11 C7 -1.1(6) . . . . ?
C9 C10 C13 O1 -0.3(9) . . . . ?
C9 C10 C13 O2 179.5(5) . . . . ?
C10 C13 O2 C14 179.3(5) . . . . ?
C11 C7 C8 C9 0.9(6) . . . . ?
C11 C10 C13 O1 178.5(6) . . . . ?
C11 C10 C13 O2 -1.6(7) . . . . ?
C12 C9 C10 C11 -178.8(6) . . . . ?
C12 C9 C10 C13 0.2(10) . . . . ?
C13 C10 C11 C7 179.8(5) . . . . ?
C15 C14 O2 C13 172.4(5) . . . . ?
Cl1 C4 C5 C6 -179.1(4) . . . . ?
O1 C13 O2 C14 -0.9(8) . . . . ?

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 2094784'
loop_
_audit_author_name
_audit_author_address
'Olivier Blacque'
;Department of Chemistry, University of Zurich
Switzerland
;
_audit_update_record             
;
2021-07-06 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;

_audit_creation_date             2021-04-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 Cl N2 O4 Re'
_chemical_formula_sum            'C22 H16 Cl N2 O4 Re'
_chemical_formula_weight         594.02
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -5.2083 5.8923 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   8.39430(10)
_cell_length_b                   10.47450(10)
_cell_length_c                   23.0911(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.3950(10)
_cell_angle_gamma                90
_cell_volume                     2021.32(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16650
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      76.1410
_cell_measurement_theta_min      3.8250
_shelx_estimated_absorpt_T_max   0.258
_shelx_estimated_absorpt_T_min   0.059
_exptl_absorpt_coefficient_mu    13.257
_exptl_absorpt_correction_T_max  0.397
_exptl_absorpt_correction_T_min  0.026
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.952
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1144
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -1 0.1455
-1 0 0 0.1576
0 1 -1 0.0695
0 -1 1 0.0745
0 -4 -5 0.1644
0 4 5 0.1014
-5 -1 -2 0.1668

_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.14

_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            20066
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.491
_diffrn_reflns_theta_min         3.846
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -20.60   0.80    1.00    --  -42.49 -37.00 150.00  118
  2  ω   -115.00 -20.60   0.80    1.00    --  -42.49 -37.00-120.00  118
  3  ω    -69.00  27.00   0.80    1.00    --  -42.49  57.00  30.00  120
  4  ω    -30.00  64.40   0.80    1.00    --   42.49 -37.00  90.00  118
  5  ω     40.00 136.00   0.80    1.00    --  111.00 -51.00-149.98  120
  6  ω     87.00 177.40   0.80    1.00    --  111.00  30.00-120.00  113
  7  ω     36.00 134.40   0.80    1.00    --  111.00 -30.00   0.00  123
  8  ω     84.00 178.40   0.80    1.00    --  111.00  60.00 -63.09  118
  9  ω     36.00 134.40   0.80    1.00    --  111.00 -30.00-150.00  123
 10  ω     41.00 137.00   0.80    1.00    --  111.00 -54.00  62.12  120
 11  ω     87.00 177.40   0.80    1.00    --  111.00  45.00  90.00  113
 12  ω     87.00 177.40   0.80    1.00    --  111.00  45.00 150.00  113
 13  ω     41.00 137.80   0.80    1.00    --  111.00 -58.00 144.37  121
 14  ω   -113.00 -17.00   0.80    1.00    --  -42.49 -57.00   0.00  120
 15  ω   -113.00 -17.00   0.80    1.00    --  -42.49 -57.00  60.00  120
 16  ω    -28.00  68.00   0.80    1.00    --   42.49 -57.00-150.00  120
 17  ω     85.00 134.60   0.80    1.00    --  111.00  55.00-179.55   62
 18  ω     41.00 138.60   0.80    1.00    --  111.00 -60.00 -35.45  122
 19  ω     87.00 177.40   0.80    1.00    --  111.00  30.00  30.00  113
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1386085000
_diffrn_orient_matrix_UB_12      0.0794592000
_diffrn_orient_matrix_UB_13      0.0300423000
_diffrn_orient_matrix_UB_21      0.1207745000
_diffrn_orient_matrix_UB_22      -0.0800142000
_diffrn_orient_matrix_UB_23      -0.0308688000
_diffrn_orient_matrix_UB_31      -0.0142638000
_diffrn_orient_matrix_UB_32      0.0943919000
_diffrn_orient_matrix_UB_33      -0.0513234000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4129
_reflns_number_total             4135

_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       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_refine_diff_density_max         0.870
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       0.00237(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.223
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0211
_refine_ls_R_factor_gt           0.0210
_refine_ls_restrained_S_all      1.223
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0238P)²+2.5431P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0534
_refine_ls_wR_factor_ref         0.0534
_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.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C11(H11), C12(H12), C14(H14), C15(H15), C19(H19), C20(H20),
 C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6717(4) 0.6366(3) 0.52207(16) 0.0381(8) Uani 1 1 d . . . . .
C2 C 0.6968(4) 0.8168(4) 0.60785(16) 0.0433(9) Uani 1 1 d . . . . .
C3 C 0.4653(4) 0.6389(3) 0.60428(15) 0.0310(7) Uani 1 1 d . . . . .
C4 C 0.7984(3) 0.5683(2) 0.69567(12) 0.0214(5) Uani 1 1 d . . . . .
C5 C 0.7388(3) 0.4583(3) 0.66292(12) 0.0224(5) Uani 1 1 d . . . . .
H5 H 0.652737 0.405518 0.672173 0.027 Uiso 1 1 calc R U . . .
C6 C 0.8295(3) 0.4416(3) 0.61465(12) 0.0219(5) Uani 1 1 d . . . . .
C7 C 0.9457(3) 0.5431(3) 0.61718(13) 0.0248(6) Uani 1 1 d . . . . .
H7 H 1.022008 0.556555 0.589904 0.030 Uiso 1 1 calc R U . . .
C8 C 0.9283(3) 0.6199(3) 0.66675(13) 0.0238(6) Uani 1 1 d . . . . .
C9 C 1.0333(4) 0.7310(3) 0.68600(14) 0.0312(6) Uani 1 1 d . . . . .
H9A H 1.091552 0.759745 0.653546 0.047 Uiso 1 1 calc R U . . .
H9B H 1.109816 0.704692 0.718481 0.047 Uiso 1 1 calc R U . . .
H9C H 0.967053 0.800939 0.698522 0.047 Uiso 1 1 calc R U . . .
C10 C 0.8122(3) 0.3371(3) 0.57150(12) 0.0236(5) Uani 1 1 d . . . . .
C11 C 0.6780(4) 0.2578(3) 0.56739(13) 0.0284(6) Uani 1 1 d . . . . .
H11 H 0.596677 0.270929 0.592731 0.034 Uiso 1 1 calc R U . . .
C12 C 0.6621(4) 0.1602(3) 0.52669(15) 0.0327(6) Uani 1 1 d . . . . .
H12 H 0.569746 0.107314 0.523508 0.039 Uiso 1 1 calc R U . . .
C13 C 0.7823(5) 0.1411(3) 0.49101(15) 0.0348(7) Uani 1 1 d . . . . .
C14 C 0.9175(4) 0.2149(3) 0.49461(15) 0.0364(7) Uani 1 1 d . . . . .
H14 H 1.000124 0.198586 0.470161 0.044 Uiso 1 1 calc R U . . .
H1 H 0.535(5) 0.543(4) 0.7415(19) 0.044 Uiso 1 1 d . U . . .
C15 C 0.9317(4) 0.3145(3) 0.53485(14) 0.0309(6) Uani 1 1 d . . . . .
H15 H 1.023852 0.367571 0.537271 0.037 Uiso 1 1 calc R U . . .
C16 C 0.7450(3) 0.6162(2) 0.75163(12) 0.0237(6) Uani 1 1 d . . . . .
C17 C 0.5293(4) 0.6228(3) 0.81529(13) 0.0270(6) Uani 1 1 d . . . . .
H17A H 0.616874 0.647540 0.844882 0.032 Uiso 1 1 calc R U . . .
H17B H 0.469211 0.552206 0.831659 0.032 Uiso 1 1 calc R U . . .
C18 C 0.4184(3) 0.7353(3) 0.80386(12) 0.0244(5) Uani 1 1 d . . . . .
C19 C 0.3010(4) 0.7600(3) 0.84085(13) 0.0282(6) Uani 1 1 d . . . . .
H19 H 0.289715 0.706080 0.873305 0.034 Uiso 1 1 calc R U . . .
C20 C 0.2004(4) 0.8636(3) 0.83008(15) 0.0323(7) Uani 1 1 d . . . . .
H20 H 0.121204 0.878651 0.856077 0.039 Uiso 1 1 calc R U . . .
C21 C 0.3230(4) 0.9208(3) 0.75063(14) 0.0318(6) Uani 1 1 d . . . . .
H21 H 0.332357 0.977379 0.718965 0.038 Uiso 1 1 calc R U . . .
C22 C 0.4296(4) 0.8198(3) 0.75774(13) 0.0288(6) Uani 1 1 d . . . . .
H22 H 0.509133 0.808199 0.731551 0.035 Uiso 1 1 calc R U . . .
Cl1 Cl 0.76029(14) 0.01936(9) 0.43900(5) 0.0585(3) Uani 1 1 d . . . . .
N1 N 0.5982(3) 0.5772(2) 0.76402(11) 0.0264(5) Uani 1 1 d . . . . .
N2 N 0.2075(3) 0.9438(2) 0.78560(12) 0.0314(5) Uani 1 1 d . . . . .
O1 O 0.6663(4) 0.6317(4) 0.47227(12) 0.0664(11) Uani 1 1 d . . . . .
O2 O 0.7048(5) 0.9250(3) 0.61254(18) 0.0843(14) Uani 1 1 d . . . . .
O3 O 0.3293(3) 0.6398(3) 0.60443(14) 0.0510(7) Uani 1 1 d . . . . .
O4 O 0.8317(3) 0.6851(2) 0.78388(10) 0.0340(5) Uani 1 1 d . . . . .
Re1 Re 0.69450(2) 0.63431(2) 0.60500(2) 0.02090(7) 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
C1 O1 1.148(5) . ?
C1 Re1 1.907(4) . ?
C2 O2 1.140(6) . ?
C2 Re1 1.912(4) . ?
C3 O3 1.142(4) . ?
C3 Re1 1.923(3) . ?
C4 C5 1.441(4) . ?
C4 C8 1.437(4) . ?
C4 C16 1.494(4) . ?
C4 Re1 2.298(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.419(4) . ?
C5 Re1 2.288(3) . ?
C6 C7 1.440(4) . ?
C6 C10 1.478(4) . ?
C6 Re1 2.316(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.418(4) . ?
C7 Re1 2.308(3) . ?
C8 C9 1.501(4) . ?
C8 Re1 2.320(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.395(4) . ?
C10 C15 1.392(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.376(5) . ?
C13 C14 1.369(5) . ?
C13 Cl1 1.749(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.395(4) . ?
C15 H15 0.9500 . ?
C16 N1 1.354(4) . ?
C16 O4 1.226(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.509(4) . ?
C17 N1 1.447(4) . ?
C18 C19 1.388(4) . ?
C18 C22 1.394(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.383(4) . ?
C20 H20 0.9500 . ?
C20 N2 1.332(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.385(4) . ?
C21 N2 1.340(4) . ?
C22 H22 0.9500 . ?
N1 H1 0.79(4) . ?

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
O1 C1 Re1 175.2(3) . . ?
O2 C2 Re1 175.7(3) . . ?
O3 C3 Re1 178.9(3) . . ?
C5 C4 C16 127.2(2) . . ?
C5 C4 Re1 71.30(15) . . ?
C8 C4 C5 107.3(2) . . ?
C8 C4 C16 125.3(2) . . ?
C8 C4 Re1 72.71(15) . . ?
C16 C4 Re1 124.59(18) . . ?
C4 C5 H5 125.5 . . ?
C4 C5 Re1 72.06(15) . . ?
C6 C5 C4 109.0(2) . . ?
C6 C5 H5 125.5 . . ?
C6 C5 Re1 73.13(15) . . ?
Re1 C5 H5 121.0 . . ?
C5 C6 C7 106.8(2) . . ?
C5 C6 C10 126.5(2) . . ?
C5 C6 Re1 70.98(15) . . ?
C7 C6 C10 126.7(3) . . ?
C7 C6 Re1 71.56(15) . . ?
C10 C6 Re1 124.37(18) . . ?
C6 C7 H7 125.3 . . ?
C6 C7 Re1 72.14(15) . . ?
C8 C7 C6 109.3(2) . . ?
C8 C7 H7 125.3 . . ?
C8 C7 Re1 72.62(15) . . ?
Re1 C7 H7 121.6 . . ?
C4 C8 C9 127.2(3) . . ?
C4 C8 Re1 71.04(15) . . ?
C7 C8 C4 107.6(2) . . ?
C7 C8 C9 125.2(3) . . ?
C7 C8 Re1 71.71(15) . . ?
C9 C8 Re1 124.8(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C6 120.9(3) . . ?
C15 C10 C6 120.3(3) . . ?
C15 C10 C11 118.7(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 118.9(3) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 Cl1 118.7(3) . . ?
C14 C13 C12 122.1(3) . . ?
C14 C13 Cl1 119.1(3) . . ?
C13 C14 H14 120.6 . . ?
C13 C14 C15 118.8(3) . . ?
C15 C14 H14 120.6 . . ?
C10 C15 C14 120.7(3) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
N1 C16 C4 115.7(2) . . ?
O4 C16 C4 120.9(3) . . ?
O4 C16 N1 123.3(3) . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
N1 C17 H17A 108.8 . . ?
N1 C17 H17B 108.8 . . ?
N1 C17 C18 113.7(2) . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 C22 117.0(3) . . ?
C22 C18 C17 123.0(3) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 C18 119.5(3) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 117.9 . . ?
N2 C20 C19 124.2(3) . . ?
N2 C20 H20 117.9 . . ?
C22 C21 H21 117.9 . . ?
N2 C21 H21 117.9 . . ?
N2 C21 C22 124.1(3) . . ?
C18 C22 H22 120.5 . . ?
C21 C22 C18 119.1(3) . . ?
C21 C22 H22 120.5 . . ?
C16 N1 H1 124(3) . . ?
C16 N1 C17 121.0(2) . . ?
C17 N1 H1 113(3) . . ?
C20 N2 C21 116.0(3) . . ?
C1 Re1 C2 91.25(16) . . ?
C1 Re1 C3 89.14(14) . . ?
C1 Re1 C4 155.87(12) . . ?
C1 Re1 C5 126.35(13) . . ?
C1 Re1 C6 96.29(12) . . ?
C1 Re1 C7 97.58(12) . . ?
C1 Re1 C8 128.13(13) . . ?
C2 Re1 C3 88.99(14) . . ?
C2 Re1 C4 105.54(12) . . ?
C2 Re1 C5 141.70(12) . . ?
C2 Re1 C6 149.85(12) . . ?
C2 Re1 C7 113.79(13) . . ?
C2 Re1 C8 92.22(12) . . ?
C3 Re1 C4 108.00(12) . . ?
C3 Re1 C5 97.62(11) . . ?
C3 Re1 C6 120.18(11) . . ?
C3 Re1 C7 155.95(11) . . ?
C3 Re1 C8 142.64(13) . . ?
C4 Re1 C6 60.62(9) . . ?
C4 Re1 C7 60.01(10) . . ?
C4 Re1 C8 36.25(10) . . ?
C5 Re1 C4 36.64(9) . . ?
C5 Re1 C6 35.89(9) . . ?
C5 Re1 C7 59.91(10) . . ?
C5 Re1 C8 60.42(10) . . ?
C6 Re1 C8 60.39(9) . . ?
C7 Re1 C6 36.30(9) . . ?
C7 Re1 C8 35.67(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H5 O4 0.95 2.52 3.191(4) 127.7 2_646 yes
N1 H1 N2 0.79(4) 2.32(4) 3.050(4) 153(4) 2_546 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C5 C6 C7 -0.6(3) . . . . ?
C4 C5 C6 C10 177.2(2) . . . . ?
C4 C5 C6 Re1 -63.59(18) . . . . ?
C4 C16 N1 C17 -176.5(2) . . . . ?
C5 C4 C8 C7 0.5(3) . . . . ?
C5 C4 C8 C9 -176.9(3) . . . . ?
C5 C4 C8 Re1 63.32(18) . . . . ?
C5 C4 C16 N1 -20.7(4) . . . . ?
C5 C4 C16 O4 158.4(3) . . . . ?
C5 C6 C7 C8 0.9(3) . . . . ?
C5 C6 C7 Re1 -62.66(18) . . . . ?
C5 C6 C10 C11 14.2(4) . . . . ?
C5 C6 C10 C15 -164.6(3) . . . . ?
C6 C7 C8 C4 -0.9(3) . . . . ?
C6 C7 C8 C9 176.6(3) . . . . ?
C6 C7 C8 Re1 -63.24(19) . . . . ?
C6 C10 C11 C12 179.8(3) . . . . ?
C6 C10 C15 C14 179.0(3) . . . . ?
C7 C6 C10 C11 -168.5(3) . . . . ?
C7 C6 C10 C15 12.7(4) . . . . ?
C8 C4 C5 C6 0.0(3) . . . . ?
C8 C4 C5 Re1 -64.25(18) . . . . ?
C8 C4 C16 N1 163.9(3) . . . . ?
C8 C4 C16 O4 -17.0(4) . . . . ?
C10 C6 C7 C8 -176.9(3) . . . . ?
C10 C6 C7 Re1 119.6(3) . . . . ?
C10 C11 C12 C13 1.1(5) . . . . ?
C11 C10 C15 C14 0.2(5) . . . . ?
C11 C12 C13 C14 0.4(5) . . . . ?
C11 C12 C13 Cl1 -179.0(3) . . . . ?
C12 C13 C14 C15 -1.6(5) . . . . ?
C13 C14 C15 C10 1.3(5) . . . . ?
C15 C10 C11 C12 -1.4(4) . . . . ?
C16 C4 C5 C6 -176.0(2) . . . . ?
C16 C4 C5 Re1 119.7(3) . . . . ?
C16 C4 C8 C7 176.7(2) . . . . ?
C16 C4 C8 C9 -0.7(4) . . . . ?
C16 C4 C8 Re1 -120.5(3) . . . . ?
C17 C18 C19 C20 179.7(3) . . . . ?
C17 C18 C22 C21 -179.8(3) . . . . ?
C18 C17 N1 C16 95.7(3) . . . . ?
C18 C19 C20 N2 0.2(5) . . . . ?
C19 C18 C22 C21 -1.2(4) . . . . ?
C19 C20 N2 C21 -1.3(5) . . . . ?
C22 C18 C19 C20 1.1(4) . . . . ?
C22 C21 N2 C20 1.2(5) . . . . ?
Cl1 C13 C14 C15 177.9(3) . . . . ?
N1 C17 C18 C19 156.2(3) . . . . ?
N1 C17 C18 C22 -25.2(4) . . . . ?
N2 C21 C22 C18 0.0(5) . . . . ?
O4 C16 N1 C17 4.5(4) . . . . ?
Re1 C4 C5 C6 64.28(19) . . . . ?
Re1 C4 C8 C7 -62.80(19) . . . . ?
Re1 C4 C8 C9 119.8(3) . . . . ?
Re1 C4 C16 N1 71.3(3) . . . . ?
Re1 C4 C16 O4 -109.6(3) . . . . ?
Re1 C5 C6 C7 63.04(18) . . . . ?
Re1 C5 C6 C10 -119.2(3) . . . . ?
Re1 C6 C7 C8 63.55(19) . . . . ?
Re1 C6 C10 C11 -76.7(3) . . . . ?
Re1 C6 C10 C15 104.5(3) . . . . ?
Re1 C7 C8 C4 62.37(18) . . . . ?
Re1 C7 C8 C9 -120.2(3) . . . . ?

