# Electronic Supplementary Material (ESI) for ChemComm.
# 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_ac488
_database_code_depnum_ccdc_archive 'CCDC 1991846'
loop_
_audit_author_name
_audit_author_address
'Wolfgang Frey'
;Institut feur Organische Chemie, Universitaet Stuttgart
Germany
;
_audit_update_record             
;
2020-03-21 deposited with the CCDC.	2020-08-05 downloaded from the CCDC.
;
_audit_creation_date             2020-03-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.01.31 svn.r88ba2a32 for OlexSys, GUI svn.r6032)
;
_chemical_formula_moiety         'C10 H5 Cl N5 O3 Re, C0.5 H Cl'
_chemical_formula_sum            'C10.5 H6 Cl2 N5 O3 Re'
_chemical_formula_weight         507.308
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36842 0.69938 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03376 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Re -4.73661 6.09050 28.76210 15.71890 14.55640 5.44174 1.67191 9.09227 0.35050
52.08610 10.4720001221
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   16.0600(8)
_cell_length_b                   13.0072(8)
_cell_length_c                   13.9753(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.720(6)
_cell_angle_gamma                90
_cell_volume                     2877.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    135.01
_cell_measurement_reflns_used    17080
_cell_measurement_theta_min      5.16
_cell_measurement_theta_max      66
_exptl_absorpt_coefficient_mu    20.131
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'R.H. Blessing, Acta Crystallogr., Sect A 1995, 51, 33-38'
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.342
_exptl_crystal_description       plate
_exptl_crystal_F_000             1869.829
_exptl_crystal_preparation       'See manuscript'
_exptl_crystal_recrystallization_method 'Slow evaporation of CH2Cl2'
_exptl_crystal_size_max          0.146
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.029
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.9515
_diffrn_reflns_Laue_measured_fraction_max 0.9515
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17080
_diffrn_reflns_point_group_measured_fraction_full 0.9515
_diffrn_reflns_point_group_measured_fraction_max 0.9515
_diffrn_reflns_theta_full        66.3264
_diffrn_reflns_theta_max         66.33
_diffrn_reflns_theta_min         5.16
_diffrn_ambient_temperature      135.01
_diffrn_measured_fraction_theta_full 0.9515
_diffrn_measured_fraction_theta_max 0.9515
_diffrn_measurement_device_type  'Brucker Apex II'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              18
_reflns_limit_h_min              -18
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                1954
_reflns_number_total             2412
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         6.2654
_refine_diff_density_min         -2.5716
_refine_diff_density_rms         0.4075
_refine_ls_d_res_high            0.8417
_refine_ls_d_res_low             8.5676
_refine_ls_goodness_of_fit_ref   1.0465
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    13
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2412
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0750
_refine_ls_restrained_S_all      1.0465
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1839P)²+6.2117P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1901
_refine_ls_wR_factor_ref         0.2250
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: H11a(0.5) H11b(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C4(H4), C5(H5), C10(H10)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Re1 Re 0.82619(3) 0.47112(4) 0.81074(3) 0.0411(4) Uani 1.000000 1 . . .
Cl1 Cl 0.7245(2) 0.6166(2) 0.7968(2) 0.0468(7) Uani 1.000000 1 . . .
Cl2 Cl 0.4942(4) 0.5240(3) 0.8532(5) 0.0907(17) Uani 1.000000 1 . . .
O3 O 0.9551(7) 0.2980(8) 0.8373(8) 0.059(3) Uani 1.000000 1 . . .
N1 N 0.7368(6) 0.3952(8) 0.8897(7) 0.041(2) Uani 1.000000 1 . . .
O2 O 0.9345(7) 0.5843(8) 0.9831(8) 0.065(3) Uani 1.000000 1 . . .
C8 C 0.6714(8) 0.3459(8) 0.8349(8) 0.037(3) Uani 1.000000 1 . . .
N5 N 0.6095(7) 0.3024(9) 0.6687(9) 0.051(3) Uani 1.000000 1 . . .
C9 C 0.6727(7) 0.3464(9) 0.7311(9) 0.041(3) Uani 1.000000 1 . . .
N2 N 0.7396(7) 0.3958(8) 0.7019(7) 0.042(2) Uani 1.000000 1 . . .
C3 C 0.9032(9) 0.3628(10) 0.8251(8) 0.046(3) Uani 1.000000 1 . . .
N3 N 0.7434(8) 0.3953(9) 0.6073(8) 0.052(3) Uani 1.000000 1 . . .
N4 N 0.6114(8) 0.3039(9) 0.5747(8) 0.054(3) Uani 1.000000 1 . . .
C6 C 0.6077(9) 0.3046(11) 0.9727(10) 0.050(3) Uani 1.000000 1 . . .
H6 H 0.5632(9) 0.2759(11) 1.0009(10) 0.060(4) Uiso 1.000000 1 R . .
C7 C 0.6065(9) 0.3013(11) 0.8729(10) 0.053(3) Uani 1.000000 1 . . .
H7 H 0.5613(9) 0.2686(11) 0.8314(10) 0.064(4) Uiso 1.000000 1 R . .
C1 C 0.8880(10) 0.5324(9) 0.7218(11) 0.046(3) Uani 1.000000 1 . . .
C2 C 0.8951(9) 0.5415(11) 0.9189(13) 0.054(4) Uani 1.000000 1 . . .
C4 C 0.7392(9) 0.3958(10) 0.9859(9) 0.047(3) Uani 1.000000 1 . . .
H4 H 0.7856(9) 0.4280(10) 1.0257(9) 0.056(4) Uiso 1.000000 1 R . .
C5 C 0.6771(10) 0.3519(13) 1.0295(10) 0.058(4) Uani 1.000000 1 . . .
H5 H 0.6815(10) 0.3537(13) 1.0981(10) 0.070(4) Uiso 1.000000 1 R . .
C11 C 0.5 0.5986(14) 0.75 0.069(6) Uani 1.000000 2 S T P
H11a H 0.550431993144 0.6435(14) 0.763398725335 0.082(8) Uiso 0.500000 1 R . .
H11b H 0.449568006856 0.6435(14) 0.736601274665 0.082(8) Uiso 0.500000 1 R . .
O1 O 0.9261(6) 0.5680(8) 0.6650(7) 0.055(2) Uani 1.000000 1 . . .
C10 C 0.6793(9) 0.3494(11) 0.5492(10) 0.050(3) Uani 1.000000 1 . . .
H10 H 0.6823(9) 0.3489(11) 0.4819(10) 0.060(4) Uiso 1.000000 1 R . .


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 Cl1 2.486(3) . ?
Re1 N1 2.188(10) . ?
Re1 N2 2.120(11) . ?
Re1 C3 1.863(13) . ?
Re1 C1 1.892(17) . ?
Re1 C2 1.945(18) . ?
Cl2 C11 1.754(12) 2_656 ?
O3 C3 1.178(16) . ?
N1 C8 1.352(16) . ?
N1 C4 1.339(16) . ?
O2 C2 1.15(2) . ?
C8 C9 1.455(17) . ?
C8 C7 1.374(18) . ?
N5 C9 1.349(17) . ?
N5 N4 1.320(16) . ?
C9 N2 1.372(17) . ?
N2 N3 1.334(15) . ?
N3 C10 1.339(18) . ?
N4 C10 1.341(19) . ?
C6 H6 0.9500 . ?
C6 C7 1.392(19) . ?
C6 C5 1.40(2) . ?
C7 H7 0.9500 . ?
C1 O1 1.176(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.38(2) . ?
C5 H5 0.9500 . ?
C11 H11a 0.9900 . ?
C11 H11a 0.9900 2_656 ?
C11 H11b 0.9900 2_656 ?
C11 H11b 0.9900 . ?
H11a H11b 0.0000 2_656 ?
C10 H10 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
N1 Re1 Cl1 84.5(3) . . ?
N2 Re1 Cl1 87.3(3) . . ?
N2 Re1 N1 75.3(4) . . ?
C3 Re1 Cl1 178.3(3) . . ?
C3 Re1 N1 94.8(5) . . ?
C3 Re1 N2 94.1(5) . . ?
C1 Re1 Cl1 92.2(4) . . ?
C1 Re1 N1 169.3(5) . . ?
C1 Re1 N2 94.4(5) . . ?
C1 Re1 C3 88.7(5) . . ?
C2 Re1 Cl1 89.0(4) . . ?
C2 Re1 N1 99.0(5) . . ?
C2 Re1 N2 173.5(5) . . ?
C2 Re1 C3 89.5(6) . . ?
C2 Re1 C1 91.1(6) . . ?
C8 N1 Re1 116.2(8) . . ?
C4 N1 Re1 126.4(9) . . ?
C4 N1 C8 117.3(11) . . ?
C9 C8 N1 114.9(10) . . ?
C7 C8 N1 123.3(11) . . ?
C7 C8 C9 121.7(12) . . ?
N4 N5 C9 119.7(12) . . ?
N5 C9 C8 120.5(11) . . ?
N2 C9 C8 116.2(11) . . ?
N2 C9 N5 123.3(12) . . ?
C9 N2 Re1 117.1(8) . . ?
N3 N2 Re1 125.4(9) . . ?
N3 N2 C9 117.5(11) . . ?
O3 C3 Re1 176.2(12) . . ?
C10 N3 N2 116.4(12) . . ?
C10 N4 N5 115.3(12) . . ?
C7 C6 H6 121.4(9) . . ?
C5 C6 H6 121.4(8) . . ?
C5 C6 C7 117.3(13) . . ?
C6 C7 C8 119.4(13) . . ?
H7 C7 C8 120.3(8) . . ?
H7 C7 C6 120.3(9) . . ?
O1 C1 Re1 178.1(11) . . ?
O2 C2 Re1 178.7(13) . . ?
H4 C4 N1 118.6(8) . . ?
C5 C4 N1 122.9(14) . . ?
C5 C4 H4 118.6(9) . . ?
C4 C5 C6 119.9(13) . . ?
H5 C5 C6 120.1(8) . . ?
H5 C5 C4 120.1(9) . . ?
Cl2 C11 Cl2 112.8(11) . 2_656 ?
H11a C11 Cl2 109.0(3) 2_656 2_656 ?
H11a C11 Cl2 109.0(3) . 2_656 ?
H11a C11 Cl2 109.0(3) 2_656 . ?
H11a C11 Cl2 109.0(3) . . ?
H11a C11 H11a 107.8 2_656 . ?
H11b C11 Cl2 109.0(3) 2_656 . ?
H11b C11 Cl2 109.0(3) 2_656 2_656 ?
H11b C11 Cl2 109.0(3) . . ?
H11b C11 Cl2 109.0(3) . 2_656 ?
H11b C11 H11a 107.799399147(15) 2_656 2_656 ?
H11b C11 H11a 0.0 2_656 . ?
H11b C11 H11a 107.8 . . ?
H11b C11 H11a 0.0 . 2_656 ?
H11b C11 H11b 107.8 . 2_656 ?
H11b H11a C11 126.10(5) 2_656 . ?
H11a H11b C11 53.90(5) 2_656 2_656 ?
N4 C10 N3 127.7(13) . . ?
H10 C10 N3 116.1(8) . . ?
H10 C10 N4 116.1(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Re1 N1 C8 C9 3.0(9) . . . . ?
Re1 N1 C8 C7 -174.9(9) . . . . ?
Re1 N1 C4 C5 175.4(11) . . . . ?
Re1 N2 C9 C8 -3.5(9) . . . . ?
Re1 N2 C9 N5 174.7(8) . . . . ?
Re1 N2 N3 C10 -175.4(11) . . . . ?
N1 C8 C9 N5 -178.0(10) . . . . ?
N1 C8 C9 N2 0.2(12) . . . . ?
N1 C8 C7 C6 -1.1(14) . . . . ?
N1 C4 C5 C6 -0.4(15) . . . . ?
C8 C9 N5 N4 179.7(11) . . . . ?
C8 C9 N2 N3 178.4(10) . . . . ?
C8 C7 C6 C5 -1.5(15) . . . . ?
N5 C9 N2 N3 -3.4(14) . . . . ?
N5 N4 C10 N3 -2.0(15) . . . . ?
C9 N2 N3 C10 2.4(13) . . . . ?
N2 N3 C10 N4 0.2(14) . . . . ?


_olex2_exptl_crystal_mounting_method cryroloop
_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT971_ac488               
;
PROBLEM: Check Calcd Resid. Dens.  1.11A   From Re1             5.75 eA-3  
RESPONSE: Residual density resides near the heavy atom and is due to small size of crystals and strong absorption of X-rays of Re. Platon did not indicate twinning.
;
_vrf_PLAT973_ac488               
;
PROBLEM: Check Calcd Positive Resid. Density on       Re1       5.05 eA-3  
RESPONSE:Residual density resides near the heavy atom and is due to small size of crystals and strong absorption of X-rays of Re. Platon did not indicate twinning.
;
_vrf_PLAT029_ac488               
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.951 Why?  
RESPONSE: Cusp of data  collection by rotation around the spindle axis due to small size of crystal.
;
_vrf_PLAT972_ac488               
;
PROBLEM: Check Calcd Resid. Dens.  0.78A   From Re1            -2.54 eA-3  
RESPONSE: Residual density resides near the heavy atom and is due to small size of crystals and strong absorption of X-rays of Re. Platon did not indicate twinning.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_ac444_a
_database_code_depnum_ccdc_archive 'CCDC 1991847'
loop_
_audit_author_name
_audit_author_address
'Wolfgang Frey'
;Institut feur Organische Chemie, Universitaet Stuttgart
Germany
;
_audit_update_record             
;
2020-03-21 deposited with the CCDC.	2020-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H5 N5'
_chemical_formula_sum            'C7 H5 N5'
_chemical_formula_weight         159.16

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'

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

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

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

_cell_length_a                   7.2794(4)
_cell_length_b                   9.3608(4)
_cell_length_c                   10.4528(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.970(3)
_cell_angle_gamma                90
_cell_volume                     707.00(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    135(2)
_cell_measurement_reflns_used    1273
_cell_measurement_theta_min      2.819
_cell_measurement_theta_max      28.338

_exptl_crystal_description       clock
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.647
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.165
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8344
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      135(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa ApexII Duo'
_diffrn_measurement_method       'Omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13031
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.819
_diffrn_reflns_theta_max         28.338
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1759
_reflns_number_gt                1273
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker ApexII Software Suite, 2008'
_computing_cell_refinement       'Bruker ApexII Software Suite, 2008'
_computing_data_reduction        'Bruker ApexII Software Suite, 2008'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'SHELXS plus XP (Sheldrick, 1991)'
_computing_publication_material  'SHELXL-2016/4 (Sheldrick, 2016)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0760P)²+0.0995P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.023(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1759
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1396
_refine_ls_wR_factor_gt          0.1227
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.22328(14) 0.56985(11) 0.46389(10) 0.0167(3) Uani 1 1 d . . . . .
N1 N 0.12454(13) 0.55682(10) 0.34714(9) 0.0215(3) Uani 1 1 d . . . . .
N2 N 0.08442(13) 0.67483(10) 0.27971(9) 0.0256(3) Uani 1 1 d . . . . .
C2 C 0.14520(17) 0.79742(13) 0.33488(12) 0.0284(3) Uani 1 1 d . . . . .
H2 H 0.123040 0.881826 0.284922 0.034 Uiso 1 1 calc R U . . .
N3 N 0.23398(15) 0.81273(10) 0.45336(10) 0.0266(3) Uani 1 1 d . . . . .
N4 N 0.27475(13) 0.69441(10) 0.52103(9) 0.0226(3) Uani 1 1 d . . . . .
C3 C 0.27355(14) 0.43569(11) 0.53555(10) 0.0171(3) Uani 1 1 d . . . . .
C4 C 0.21904(16) 0.30366(12) 0.48319(11) 0.0221(3) Uani 1 1 d . . . . .
H4 H 0.148533 0.296915 0.400755 0.026 Uiso 1 1 calc R U . . .
C5 C 0.27037(18) 0.18189(12) 0.55456(12) 0.0286(3) Uani 1 1 d . . . . .
H5 H 0.235346 0.089946 0.521693 0.034 Uiso 1 1 calc R U . . .
C6 C 0.37286(18) 0.19614(12) 0.67378(12) 0.0284(3) Uani 1 1 d . . . . .
H6 H 0.409854 0.114577 0.724562 0.034 Uiso 1 1 calc R U . . .
C7 C 0.42038(16) 0.33213(12) 0.71750(11) 0.0262(3) Uani 1 1 d . . . . .
H7 H 0.490900 0.341393 0.799720 0.031 Uiso 1 1 calc R U . . .
N5 N 0.37336(13) 0.45108(10) 0.65140(9) 0.0215(3) 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 N4 1.3425(13) . ?
C1 N1 1.3446(14) . ?
C1 C3 1.4851(15) . ?
N1 N2 1.3238(12) . ?
N2 C2 1.3354(15) . ?
C2 N3 1.3333(17) . ?
C2 H2 0.9500 . ?
N3 N4 1.3282(12) . ?
C3 N5 1.3422(14) . ?
C3 C4 1.3899(14) . ?
C4 C5 1.3885(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.3790(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.3823(16) . ?
C6 H6 0.9500 . ?
C7 N5 1.3331(13) . ?
C7 H7 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
N4 C1 N1 124.90(9) . . ?
N4 C1 C3 118.14(10) . . ?
N1 C1 C3 116.93(9) . . ?
N2 N1 C1 117.82(9) . . ?
N1 N2 C2 116.55(9) . . ?
N3 C2 N2 126.25(10) . . ?
N3 C2 H2 116.9 . . ?
N2 C2 H2 116.9 . . ?
N4 N3 C2 117.18(9) . . ?
N3 N4 C1 117.07(9) . . ?
N5 C3 C4 123.24(9) . . ?
N5 C3 C1 115.95(9) . . ?
C4 C3 C1 120.81(10) . . ?
C5 C4 C3 118.23(11) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C6 C5 C4 119.14(11) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C7 118.30(10) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
N5 C7 C6 124.03(11) . . ?
N5 C7 H7 118.0 . . ?
C6 C7 H7 118.0 . . ?
C7 N5 C3 117.05(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 C1 N1 N2 4.38(18) . . . . ?
C3 C1 N1 N2 -177.49(9) . . . . ?
C1 N1 N2 C2 -0.50(16) . . . . ?
N1 N2 C2 N3 -3.6(2) . . . . ?
N2 C2 N3 N4 3.7(2) . . . . ?
C2 N3 N4 C1 0.17(17) . . . . ?
N1 C1 N4 N3 -4.19(17) . . . . ?
C3 C1 N4 N3 177.70(9) . . . . ?
N4 C1 C3 N5 -2.26(16) . . . . ?
N1 C1 C3 N5 179.48(8) . . . . ?
N4 C1 C3 C4 177.93(9) . . . . ?
N1 C1 C3 C4 -0.33(17) . . . . ?
N5 C3 C4 C5 0.09(18) . . . . ?
C1 C3 C4 C5 179.89(10) . . . . ?
C3 C4 C5 C6 -0.06(18) . . . . ?
C4 C5 C6 C7 0.04(19) . . . . ?
C5 C6 C7 N5 -0.1(2) . . . . ?
C6 C7 N5 C3 0.08(19) . . . . ?
C4 C3 N5 C7 -0.10(18) . . . . ?
C1 C3 N5 C7 -179.91(9) . . . . ?

_refine_diff_density_max         0.434
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_stams02
_database_code_depnum_ccdc_archive 'CCDC 2008845'
loop_
_audit_author_name
_audit_author_address
'Mark Ringenberg'
;University of Stuttgart
Germany
;
_audit_update_record             
;
2020-06-09 deposited with the CCDC.	2020-08-05 downloaded from the CCDC.
;
_audit_creation_date             2020-06-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C18 H19 Cl N3 O3 Re)'
_chemical_formula_sum            'C36 H38 Cl2 N6 O6 Re2'
_chemical_formula_weight         1094.02
_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 0.0033 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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.9274(18)
_cell_length_b                   12.2202(9)
_cell_length_c                   17.9025(19)
_cell_angle_alpha                90
_cell_angle_beta                 103.284(8)
_cell_angle_gamma                90
_cell_volume                     3817.1(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    24957
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.2
_cell_measurement_theta_min      2.2
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.529
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark brown'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.904
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2112
_exptl_crystal_preparation       'see manuscript'
_exptl_crystal_recrystallization_method 'see manuscript'
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2298
_diffrn_reflns_av_unetI/netI     0.3791
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            24957
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.919
_diffrn_reflns_theta_min         2.035
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  'Apex II, Brucker'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          n/a
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2964
_reflns_number_total             6069
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         3.834
_refine_diff_density_min         -1.598
_refine_diff_density_rms         0.318
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         6069
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1927
_refine_ls_R_factor_gt           0.0675
_refine_ls_restrained_S_all      0.948
_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)+(0.0629P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1503
_refine_special_details          n/a
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C16) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C13)
\\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C11) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C10(H10)
3.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,
 H15B), C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C18(H18), N3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.4525(6) 0.7812(9) 0.3395(6) 0.032(3) Uani 1 1 d . . . . .
C2 C 0.4059(7) 0.6520(8) 0.4385(6) 0.032(3) Uani 1 1 d . . . . .
C3 C 0.4509(6) 0.8573(8) 0.4786(6) 0.028(2) Uani 1 1 d . . . . .
C4 C 0.6343(6) 0.8696(7) 0.4073(6) 0.023(2) Uani 1 1 d . . . . .
H4 H 0.603404 0.872189 0.357884 0.028 Uiso 1 1 calc R . . . .
C5 C 0.7038(6) 0.9207(8) 0.4205(7) 0.032(3) Uani 1 1 d . . . . .
H5 H 0.719905 0.955686 0.380782 0.038 Uiso 1 1 calc R . . . .
C6 C 0.7489(6) 0.9195(8) 0.4924(6) 0.030(2) Uani 1 1 d . . . . .
H6 H 0.796400 0.953978 0.503426 0.036 Uiso 1 1 calc R . . . .
C7 C 0.7221(6) 0.8652(7) 0.5490(6) 0.027(2) Uani 1 1 d . . . . .
H7 H 0.751501 0.864743 0.599097 0.032 Uiso 1 1 calc R . . . .
C8 C 0.6536(6) 0.8126(7) 0.5323(5) 0.020(2) Uani 1 1 d . . . . .
C9 C 0.6245(6) 0.7458(7) 0.5885(6) 0.024(2) Uani 1 1 d . . . . .
C10 C 0.6602(7) 0.7482(8) 0.6740(5) 0.031(3) Uani 1 1 d . . . . .
H10 H 0.715247 0.763636 0.683371 0.038 Uiso 1 1 calc R . . . .
C11 C 0.6171(8) 0.8441(10) 0.7052(7) 0.047(3) Uani 1 1 d . U . . .
H11A H 0.626645 0.910968 0.679670 0.057 Uiso 1 1 calc R . . . .
H11B H 0.562535 0.829538 0.689569 0.057 Uiso 1 1 calc R . . . .
C12 C 0.6361(9) 0.8653(11) 0.7890(8) 0.060(4) Uani 1 1 d . U . . .
H12A H 0.607332 0.929255 0.798048 0.071 Uiso 1 1 calc R . . . .
H12B H 0.689953 0.884442 0.803878 0.071 Uiso 1 1 calc R . . . .
C13 C 0.6216(9) 0.7747(11) 0.8432(8) 0.053(3) Uani 1 1 d . U . . .
H13A H 0.600278 0.808418 0.882680 0.064 Uiso 1 1 calc R . . . .
H13B H 0.582671 0.726256 0.814099 0.064 Uiso 1 1 calc R . . . .
C14 C 0.6887(9) 0.7053(12) 0.8823(8) 0.061(4) Uani 1 1 d . U . . .
H14A H 0.718556 0.747569 0.924701 0.073 Uiso 1 1 calc R . . . .
H14B H 0.668619 0.642477 0.904363 0.073 Uiso 1 1 calc R . . . .
C15 C 0.7427(8) 0.6637(10) 0.8361(7) 0.046(3) Uani 1 1 d . U . . .
H15A H 0.784026 0.624466 0.870059 0.055 Uiso 1 1 calc R . . . .
H15B H 0.765075 0.725841 0.815578 0.055 Uiso 1 1 calc R . . . .
C16 C 0.7061(8) 0.5879(10) 0.7694(7) 0.047(3) Uani 1 1 d . U . . .
H16A H 0.746810 0.558366 0.747920 0.057 Uiso 1 1 calc R . . . .
H16B H 0.682958 0.526892 0.790431 0.057 Uiso 1 1 calc R . . . .
C17 C 0.6465(8) 0.6359(8) 0.7049(7) 0.037(3) Uani 1 1 d . . . . .
C18 C 0.5813(6) 0.5856(7) 0.6723(5) 0.025(2) Uani 1 1 d . . . . .
H18 H 0.568354 0.520860 0.693509 0.030 Uiso 1 1 calc R . . . .
Cl1 Cl 0.56899(16) 0.58245(19) 0.39973(17) 0.0323(6) Uani 1 1 d . . . . .
N1 N 0.6078(5) 0.8164(6) 0.4609(5) 0.027(2) Uani 1 1 d . . . . .
N2 N 0.5590(5) 0.6945(6) 0.5585(5) 0.025(2) Uani 1 1 d . . . . .
N3 N 0.5315(5) 0.6289(6) 0.6062(5) 0.0234(18) Uani 1 1 d . . . . .
H3 H 0.483442 0.613351 0.596467 0.028 Uiso 1 1 calc R . . . .
O1 O 0.4236(5) 0.8129(8) 0.2814(5) 0.051(2) Uani 1 1 d . . . . .
O2 O 0.3499(5) 0.6036(6) 0.4332(4) 0.036(2) Uani 1 1 d . . . . .
O3 O 0.4191(5) 0.9331(6) 0.4951(5) 0.044(2) Uani 1 1 d . . . . .
Re1 Re 0.49814(2) 0.73473(3) 0.44324(2) 0.02202(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 1.120(13) . ?
C1 Re1 1.934(11) . ?
C2 O2 1.149(12) . ?
C2 Re1 1.924(11) . ?
C3 O3 1.161(12) . ?
C3 Re1 1.900(11) . ?
C4 C5 1.366(14) . ?
C4 N1 1.334(10) . ?
C5 C6 1.353(16) . ?
C6 C7 1.387(13) . ?
C7 C8 1.357(14) . ?
C8 C9 1.481(12) . ?
C8 N1 1.352(13) . ?
C9 C10 1.517(14) . ?
C9 N2 1.331(13) . ?
C10 C11 1.576(15) . ?
C10 C17 1.520(13) . ?
C11 C12 1.483(17) . ?
C12 C13 1.533(17) . ?
C13 C14 1.51(2) . ?
C14 C15 1.500(17) . ?
C15 C16 1.534(16) . ?
C16 C17 1.501(18) . ?
C17 C18 1.331(15) . ?
C18 N3 1.412(13) . ?
Cl1 Re1 2.477(2) . ?
N1 Re1 2.162(8) . ?
N2 N3 1.345(10) . ?
N2 Re1 2.157(9) . ?

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 175.6(11) . . ?
O2 C2 Re1 177.8(10) . . ?
O3 C3 Re1 175.4(11) . . ?
N1 C4 C5 124.1(11) . . ?
C6 C5 C4 118.8(9) . . ?
C5 C6 C7 118.0(10) . . ?
C8 C7 C6 120.9(11) . . ?
C7 C8 C9 123.6(10) . . ?
N1 C8 C7 121.0(9) . . ?
N1 C8 C9 115.4(9) . . ?
C8 C9 C10 122.8(9) . . ?
N2 C9 C8 113.6(9) . . ?
N2 C9 C10 123.1(8) . . ?
C9 C10 C11 104.1(9) . . ?
C9 C10 C17 106.5(8) . . ?
C17 C10 C11 114.1(8) . . ?
C12 C11 C10 118.1(11) . . ?
C11 C12 C13 118.8(12) . . ?
C14 C13 C12 117.9(12) . . ?
C15 C14 C13 118.8(12) . . ?
C14 C15 C16 114.8(12) . . ?
C17 C16 C15 117.7(11) . . ?
C16 C17 C10 119.2(11) . . ?
C18 C17 C10 117.1(11) . . ?
C18 C17 C16 123.7(10) . . ?
C17 C18 N3 121.1(9) . . ?
C4 N1 C8 117.2(9) . . ?
C4 N1 Re1 125.6(8) . . ?
C8 N1 Re1 117.2(6) . . ?
C9 N2 N3 116.2(9) . . ?
C9 N2 Re1 119.0(6) . . ?
N3 N2 Re1 124.4(7) . . ?
N2 N3 C18 120.2(9) . . ?
C1 Re1 Cl1 93.0(3) . . ?
C1 Re1 N1 100.1(4) . . ?
C1 Re1 N2 173.9(4) . . ?
C2 Re1 C1 86.6(4) . . ?
C2 Re1 Cl1 95.1(3) . . ?
C2 Re1 N1 173.1(4) . . ?
C2 Re1 N2 99.4(4) . . ?
C3 Re1 C1 88.0(5) . . ?
C3 Re1 C2 89.1(4) . . ?
C3 Re1 Cl1 175.7(3) . . ?
C3 Re1 N1 92.7(4) . . ?
C3 Re1 N2 91.6(4) . . ?
N1 Re1 Cl1 83.0(2) . . ?
N2 Re1 Cl1 86.9(2) . . ?
N2 Re1 N1 73.9(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_RINTA01_stams02             
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: Due to heavy atom Re absorption correction did not lower this value.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_ac479a
_database_code_depnum_ccdc_archive 'CCDC 1991849'
loop_
_audit_author_name
_audit_author_address
'Wolfgang Frey'
;Institut feur Organische Chemie, Universitaet Stuttgart
Germany
;
_audit_update_record             
;
2020-03-21 deposited with the CCDC.	2020-08-05 downloaded from the CCDC.
;
_audit_creation_date             2019-12-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C22 H17 Cl Fe N3 O3 Re'
_chemical_formula_sum            'C22 H17 Cl Fe N3 O3 Re'
_chemical_formula_weight         648.90
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Re -0.86767 7.12843 28.76210 15.71890 14.55640 5.44174 1.67191 9.09227 0.35050
52.08610 10.4720001221
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Fe 0.35822 0.84933 11.76950 7.35730 3.52220 2.30450 4.76110 0.30720 15.35350
76.88050 1.03690004349
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   12.9074(3)
_cell_length_b                   12.0184(3)
_cell_length_c                   14.9765(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.9810(10)
_cell_angle_gamma                90
_cell_volume                     2122.71(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    135.02
_cell_measurement_reflns_used    58206
_cell_measurement_theta_min      1.73
_cell_measurement_theta_max      33.17
_exptl_absorpt_coefficient_mu    6.537
_exptl_absorpt_correction_T_max  0.8095
_exptl_absorpt_correction_T_min  0.3323
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
'J. de Meulenaar and H. Tompa, Acta Crystallogr., Sect A 1965, 19, 1014-1018'
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.0303
_exptl_crystal_description       plank
_exptl_crystal_F_000             1247.1337
_exptl_crystal_preparation       'see manuscript'
_exptl_crystal_recrystallization_method 'see manuscript'
_exptl_crystal_size_max          0.286
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.035
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            58206
_diffrn_reflns_theta_full        33.1750
_diffrn_reflns_theta_max         33.17
_diffrn_reflns_theta_min         1.73
_diffrn_ambient_temperature      135.02
_diffrn_measured_fraction_theta_full 0.9991
_diffrn_measured_fraction_theta_max 0.9991
_diffrn_measurement_device_type  'Apex II, Brucker'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_special_details          n/a
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              18
_reflns_limit_h_min              -19
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                6575
_reflns_number_total             8110
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.8257
_refine_diff_density_min         -0.8531
_refine_diff_density_rms         0.1971
_refine_ls_d_res_high            0.6494
_refine_ls_d_res_low             11.7932
_refine_ls_goodness_of_fit_ref   0.9942
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    33
_refine_ls_number_parameters     280
_refine_ls_number_reflns         8110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0197
_refine_ls_restrained_S_all      0.9942
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0163P)²+1.0544P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0374
_refine_ls_wR_factor_ref         0.0415
_refine_special_details          n/a
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C22(H22), C21(H21),
 C20(H20), C19(H19), C4(H4), C7(H7), C6(H6), C5(H5), C12(H12)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
C1 C 0.31186(18) 0.35991(16) 0.11984(17) 0.0225(4) Uani 1.000000 .
C2 C 0.3764(2) 0.24454(19) 0.29143(16) 0.0280(5) Uani 1.000000 .
C3 C 0.42040(19) 0.46570(19) 0.29082(17) 0.0270(5) Uani 1.000000 .
C4 C 0.26232(19) 0.37165(18) 0.43737(15) 0.0243(4) Uani 1.000000 .
H4 H 0.31430(19) 0.31138(18) 0.45263(15) 0.0292(5) Uiso 1.000000 R
C5 C 0.2212(2) 0.40387(19) 0.50529(16) 0.0287(5) Uani 1.000000 .
H5 H 0.2449(2) 0.36638(19) 0.56623(16) 0.0345(6) Uiso 1.000000 R
C6 C 0.1457(2) 0.49064(19) 0.48398(15) 0.0266(5) Uani 1.000000 .
H6 H 0.1165(2) 0.51351(19) 0.52993(15) 0.0319(5) Uiso 1.000000 R
C7 C 0.11264(18) 0.54440(17) 0.39502(15) 0.0213(4) Uani 1.000000 .
H7 H 0.05976(18) 0.60398(17) 0.37862(15) 0.0256(5) Uiso 1.000000 R
C8 C 0.15817(16) 0.50967(16) 0.33006(14) 0.0165(3) Uani 1.000000 .
C9 C 0.13135(16) 0.56256(15) 0.23508(13) 0.0157(3) Uani 1.000000 .
C10 C 0.06041(16) 0.66566(16) 0.20142(14) 0.0175(4) Uani 1.000000 .
H10 H 0.00829(16) 0.67105(16) 0.23565(14) 0.0210(4) Uiso 1.000000 R
C11 C -0.01004(18) 0.65233(18) 0.09184(15) 0.0239(4) Uani 1.000000 .
H11a H -0.07129(18) 0.59743(18) 0.08047(15) 0.0286(5) Uiso 1.000000 R
H11b H -0.04526(18) 0.72435(18) 0.06336(15) 0.0286(5) Uiso 1.000000 R
C12 C 0.06466(19) 0.61403(18) 0.04459(15) 0.0245(4) Uani 1.000000 .
H12 H 0.04511(19) 0.63600(18) -0.02121(15) 0.0294(5) Uiso 1.000000 R
C13 C 0.13366(18) 0.76890(16) 0.22334(14) 0.0197(4) Uani 1.000000 .
C14 C 0.2269(2) 0.7913(2) 0.19763(16) 0.0291(5) Uani 1.000000 .
H14 H 0.2612(2) 0.7397(2) 0.16988(16) 0.0350(6) Uiso 1.000000 R
C15 C 0.2595(2) 0.9047(2) 0.22099(18) 0.0365(6) Uani 1.000000 .
H15 H 0.3186(2) 0.9421(2) 0.21079(18) 0.0438(7) Uiso 1.000000 R
C16 C 0.1882(2) 0.9517(2) 0.26200(19) 0.0366(6) Uani 1.000000 .
H16 H 0.1914(2) 1.0261(2) 0.28442(19) 0.0440(7) Uiso 1.000000 R
C17 C 0.11118(19) 0.86848(18) 0.26384(17) 0.0276(4) Uani 1.000000 .
H17 H 0.05413(19) 0.87766(18) 0.28803(17) 0.0331(5) Uiso 1.000000 R
C18 C 0.35938(19) 0.69295(19) 0.43763(16) 0.0287(5) Uani 1.000000 .
H18 H 0.34741(19) 0.61533(19) 0.42604(16) 0.0344(6) Uiso 1.000000 R
C19 C 0.43610(19) 0.75887(19) 0.41574(18) 0.0303(5) Uani 1.000000 .
H19 H 0.48506(19) 0.73339(19) 0.38685(18) 0.0364(6) Uiso 1.000000 R
C20 C 0.4277(2) 0.8703(2) 0.44434(18) 0.0321(5) Uani 1.000000 .
H20 H 0.4697(2) 0.9324(2) 0.43787(18) 0.0386(6) Uiso 1.000000 R
C21 C 0.3453(2) 0.8716(2) 0.48420(17) 0.0347(5) Uani 1.000000 .
H21 H 0.3223(2) 0.9350(2) 0.50944(17) 0.0417(6) Uiso 1.000000 R
C22 C 0.3032(2) 0.7626(2) 0.47994(16) 0.0317(5) Uani 1.000000 .
H22 H 0.2469(2) 0.7399(2) 0.50172(16) 0.0380(6) Uiso 1.000000 R
Cl1 Cl 0.11597(4) 0.25676(4) 0.17264(4) 0.02283(10) Uani 1.000000 .
Fe1 Fe 0.27509(3) 0.81904(2) 0.34265(2) 0.01902(6) Uani 1.000000 .
N1 N 0.23143(14) 0.42251(14) 0.35040(12) 0.0187(3) Uani 1.000000 .
N2 N 0.17480(14) 0.51375(13) 0.18098(11) 0.0166(3) Uani 1.000000 .
N3 N 0.15315(15) 0.55390(14) 0.08509(12) 0.0208(3) Uani 1.000000 .
O1 O 0.32086(15) 0.35535(13) 0.04647(13) 0.0313(4) Uani 1.000000 .
O2 O 0.42591(18) 0.16416(16) 0.32159(14) 0.0484(5) Uani 1.000000 .
O3 O 0.50280(15) 0.51663(16) 0.32480(15) 0.0434(5) Uani 1.000000 .
Re1 Re 0.287438(6) 0.376442(6) 0.236358(6) 0.01668(2) Uani 1.000000 .


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 1.152(3) . ?
C1 Re1 1.906(2) . ?
C2 O2 1.145(3) . ?
C2 Re1 1.934(2) . ?
C3 O3 1.151(3) . ?
C3 Re1 1.904(2) . ?
C4 C5 1.380(3) . ?
C4 N1 1.344(2) . ?
C5 C6 1.373(3) . ?
C6 C7 1.383(3) . ?
C7 C8 1.390(3) . ?
C8 C9 1.465(3) . ?
C8 N1 1.360(2) . ?
C9 C10 1.501(3) . ?
C9 N2 1.298(2) . ?
C10 C11 1.527(3) . ?
C10 C13 1.513(3) . ?
C11 C12 1.482(3) . ?
C12 N3 1.277(3) . ?
C13 C14 1.431(3) . ?
C13 C17 1.424(3) . ?
C13 Fe1 2.058(2) . ?
C14 C15 1.427(3) . ?
C14 Fe1 2.029(2) . ?
C15 C16 1.415(4) . ?
C15 Fe1 2.030(2) . ?
C16 C17 1.418(3) . ?
C16 Fe1 2.039(2) . ?
C17 Fe1 2.048(2) . ?
C18 C19 1.407(3) . ?
C18 C22 1.415(3) . ?
C18 Fe1 2.060(2) . ?
C19 C20 1.423(3) . ?
C19 Fe1 2.047(2) . ?
C20 C21 1.416(4) . ?
C20 Fe1 2.035(2) . ?
C21 C22 1.410(3) . ?
C21 Fe1 2.038(2) . ?
C22 Fe1 2.053(2) . ?
Cl1 Re1 2.4822(5) . ?
N1 Re1 2.1795(16) . ?
N2 N3 1.431(2) . ?
N2 Re1 2.1317(16) . ?

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
Re1 C1 O1 175.26(19) . . ?
Re1 C2 O2 177.5(2) . . ?
Re1 C3 O3 177.8(2) . . ?
N1 C4 C5 122.3(2) . . ?
C6 C5 C4 119.4(2) . . ?
C7 C6 C5 119.37(19) . . ?
C8 C7 C6 118.8(2) . . ?
C9 C8 C7 123.31(18) . . ?
N1 C8 C7 121.86(18) . . ?
N1 C8 C9 114.83(16) . . ?
C10 C9 C8 123.74(16) . . ?
N2 C9 C8 114.74(17) . . ?
N2 C9 C10 121.52(16) . . ?
C11 C10 C9 106.85(16) . . ?
C13 C10 C9 111.23(16) . . ?
C13 C10 C11 111.46(16) . . ?
C12 C11 C10 109.08(17) . . ?
N3 C12 C11 125.36(19) . . ?
C14 C13 C10 128.00(19) . . ?
C17 C13 C10 124.35(18) . . ?
C17 C13 C14 107.23(19) . . ?
Fe1 C13 C10 133.16(14) . . ?
Fe1 C13 C14 68.42(12) . . ?
Fe1 C13 C17 69.31(12) . . ?
C15 C14 C13 108.0(2) . . ?
Fe1 C14 C13 70.61(12) . . ?
Fe1 C14 C15 69.45(13) . . ?
C16 C15 C14 108.0(2) . . ?
Fe1 C15 C14 69.37(13) . . ?
Fe1 C15 C16 69.98(14) . . ?
C17 C16 C15 108.2(2) . . ?
Fe1 C16 C15 69.33(14) . . ?
Fe1 C16 C17 70.02(13) . . ?
C16 C17 C13 108.6(2) . . ?
Fe1 C17 C13 70.11(12) . . ?
Fe1 C17 C16 69.35(13) . . ?
C22 C18 C19 108.0(2) . . ?
Fe1 C18 C19 69.46(13) . . ?
Fe1 C18 C22 69.58(13) . . ?
C20 C19 C18 108.2(2) . . ?
Fe1 C19 C18 70.48(13) . . ?
Fe1 C19 C20 69.13(13) . . ?
C21 C20 C19 107.4(2) . . ?
Fe1 C20 C19 70.05(13) . . ?
Fe1 C20 C21 69.76(13) . . ?
C22 C21 C20 108.2(2) . . ?
Fe1 C21 C20 69.54(13) . . ?
Fe1 C21 C22 70.40(13) . . ?
C21 C22 C18 108.2(2) . . ?
Fe1 C22 C18 70.18(13) . . ?
Fe1 C22 C21 69.28(13) . . ?
C14 Fe1 C13 40.97(8) . . ?
C15 Fe1 C13 68.89(9) . . ?
C15 Fe1 C14 41.17(10) . . ?
C16 Fe1 C13 68.56(9) . . ?
C16 Fe1 C14 68.84(11) . . ?
C16 Fe1 C15 40.69(11) . . ?
C17 Fe1 C13 40.58(8) . . ?
C17 Fe1 C14 68.63(10) . . ?
C17 Fe1 C15 68.48(11) . . ?
C17 Fe1 C16 40.62(9) . . ?
C18 Fe1 C13 114.66(8) . . ?
C18 Fe1 C14 117.65(10) . . ?
C18 Fe1 C15 145.53(11) . . ?
C18 Fe1 C16 173.22(11) . . ?
C18 Fe1 C17 138.02(9) . . ?
C19 Fe1 C13 135.25(9) . . ?
C19 Fe1 C14 108.48(10) . . ?
C19 Fe1 C15 111.59(11) . . ?
C19 Fe1 C16 141.94(10) . . ?
C19 Fe1 C17 175.78(9) . . ?
C19 Fe1 C18 40.06(9) . . ?
C20 Fe1 C13 170.25(9) . . ?
C20 Fe1 C14 129.27(10) . . ?
C20 Fe1 C15 103.35(10) . . ?
C20 Fe1 C16 109.79(10) . . ?
C20 Fe1 C17 143.39(9) . . ?
C20 Fe1 C18 68.10(10) . . ?
C20 Fe1 C19 40.82(9) . . ?
C21 Fe1 C13 148.89(9) . . ?
C21 Fe1 C14 167.88(10) . . ?
C21 Fe1 C15 128.05(11) . . ?
C21 Fe1 C16 106.18(11) . . ?
C21 Fe1 C17 115.33(10) . . ?
C21 Fe1 C18 67.87(10) . . ?
C21 Fe1 C19 68.16(10) . . ?
C21 Fe1 C20 40.70(10) . . ?
C22 Fe1 C13 120.41(9) . . ?
C22 Fe1 C14 150.51(10) . . ?
C22 Fe1 C15 168.31(10) . . ?
C22 Fe1 C16 133.04(11) . . ?
C22 Fe1 C17 113.19(10) . . ?
C22 Fe1 C18 40.24(9) . . ?
C22 Fe1 C19 67.67(10) . . ?
C22 Fe1 C20 68.11(10) . . ?
C22 Fe1 C21 40.32(10) . . ?
C8 N1 C4 118.20(17) . . ?
Re1 N1 C4 125.56(14) . . ?
Re1 N1 C8 116.23(12) . . ?
N3 N2 C9 121.09(16) . . ?
Re1 N2 C9 120.42(13) . . ?
Re1 N2 N3 118.41(11) . . ?
N2 N3 C12 116.08(16) . . ?
C2 Re1 C1 90.83(9) . . ?
C3 Re1 C1 89.73(9) . . ?
C3 Re1 C2 90.20(10) . . ?
Cl1 Re1 C1 92.35(6) . . ?
Cl1 Re1 C2 88.34(7) . . ?
Cl1 Re1 C3 177.48(7) . . ?
N1 Re1 C1 167.20(8) . . ?
N1 Re1 C2 101.68(8) . . ?
N1 Re1 C3 92.84(8) . . ?
N1 Re1 Cl1 85.44(5) . . ?
N2 Re1 C1 93.72(7) . . ?
N2 Re1 C2 173.23(8) . . ?
N2 Re1 C3 94.82(8) . . ?
N2 Re1 Cl1 86.47(5) . . ?
N2 Re1 N1 73.58(6) . . ?

_olex2_exptl_crystal_mounting_method cyroloop
_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT973_ac479a              
;
PROBLEM: Check Calcd Positive Resid. Density on       Re1       1.46 eA-3  
RESPONSE: large positive density close to heavy metal atom 
;
# end Validation Reply Form
####################################################################### 
# 
# 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_ac484
_database_code_depnum_ccdc_archive 'CCDC 1991848'
loop_
_audit_author_name
_audit_author_address
'Wolfgang Frey'
;Institut feur Organische Chemie, Universitaet Stuttgart
Germany
;
_audit_update_record             
;
2020-03-21 deposited with the CCDC.	2020-08-05 downloaded from the CCDC.
;
_audit_creation_date             2020-03-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.01.31 svn.r88ba2a32 for OlexSys, GUI svn.r6032)
;
_chemical_formula_moiety         'C18 H13 Cl N3 O3 Re'
_chemical_formula_sum            'C18 H13 Cl N3 O3 Re'
_chemical_formula_weight         540.981
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Re -0.86767 7.12843 28.76210 15.71890 14.55640 5.44174 1.67191 9.09227 0.35050
52.08610 10.4720001221
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   9.0781(7)
_cell_length_b                   10.9568(10)
_cell_length_c                   22.080(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.870(2)
_cell_angle_gamma                90
_cell_volume                     2193.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22000
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      27
_cell_measurement_temperature    135.0
_exptl_absorpt_coefficient_mu    5.681
_exptl_absorpt_correction_T_max  0.6576
_exptl_absorpt_correction_T_min  0.5411
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
'J. de Meulenaar and H. Tompa, Acta Crystallogr., Sect A 1965, 19, 1014-1018'
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_description       'red-brown prisms'
_exptl_crystal_F_000             1030.636
_exptl_crystal_preparation       'See Manuscript'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2/n-hexanes'
_exptl_crystal_size_max          0.149
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.085
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_Laue_measured_fraction_full 0.9962
_diffrn_reflns_Laue_measured_fraction_max 0.9958
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            22804
_diffrn_reflns_point_group_measured_fraction_full 0.9962
_diffrn_reflns_point_group_measured_fraction_max 0.9958
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.85
_diffrn_ambient_temperature      135.0
_diffrn_measured_fraction_theta_full 0.9962
_diffrn_measured_fraction_theta_max 0.9958
_diffrn_measurement_device_type  'Brucker Apex II'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -12
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              29
_reflns_limit_l_min              -10
_reflns_number_gt                3970
_reflns_number_total             5438
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         2.2243
_refine_diff_density_min         -1.7079
_refine_diff_density_rms         0.3393
_refine_ls_d_res_high            0.7492
_refine_ls_d_res_low             11.0261
_refine_ls_goodness_of_fit_ref   0.9574
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     211
_refine_ls_number_reflns         5438
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      0.9541
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0301P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0785
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(N1) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim
Ueq, Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C10(H10)
3.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C18(H18), C17(H17), C16(H16), C15(H15), C14(H14), C4(H4),
 C5(H5), C6(H6), C7(H7), N3(H3)
3.c Fitted hexagon refined as free rotating group:
 C13(C18,C17,C16,C15,C14), N1(C4,C5,C6,C7,C8)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.9087(6) 0.6623(6) -0.0578(3) 0.0242(13) Uani 1.000000 . .
C2 C 0.7671(5) 0.4907(5) 0.0022(3) 0.0173(11) Uani 1.000000 . .
C3 C 0.9188(5) 0.6615(6) 0.0647(3) 0.0215(12) Uani 1.000000 . .
C9 C 0.5713(5) 0.8055(5) 0.0855(3) 0.0170(12) Uani 1.000000 . .
C10 C 0.4790(5) 0.8357(6) 0.1388(3) 0.0186(11) Uani 1.000000 . .
H10 H 0.4237(5) 0.9131(6) 0.1298(3) 0.0223(13) Uiso 1.000000 R .
C11 C 0.3687(5) 0.7323(5) 0.1447(3) 0.0191(12) Uani 1.000000 . .
H11 H 0.2776(5) 0.7472(5) 0.1628(3) 0.0230(15) Uiso 1.000000 R .
C12 C 0.3986(6) 0.6235(6) 0.1251(3) 0.0235(14) Uani 1.000000 . .
H12 H 0.3316(6) 0.5586(6) 0.1314(3) 0.0282(16) Uiso 1.000000 R .
C13 C 0.5753(4) 0.8530(3) 0.19687(14) 0.0185(12) Uani 1.000000 . .
C18 C 0.5515(4) 0.9517(3) 0.23472(19) 0.0297(15) Uani 1.000000 G .
H18 H 0.4766(4) 1.0095(3) 0.22402(19) 0.0357(18) Uiso 1.000000 R .
C17 C 0.6371(5) 0.9657(4) 0.28823(18) 0.0387(18) Uani 1.000000 G .
H17 H 0.6208(5) 1.0332(4) 0.31411(18) 0.046(2) Uiso 1.000000 R .
C16 C 0.7466(4) 0.8811(4) 0.30389(15) 0.0379(18) Uani 1.000000 G .
H16 H 0.8051(4) 0.8907(4) 0.34046(15) 0.045(2) Uiso 1.000000 R .
C15 C 0.7704(4) 0.7825(4) 0.26604(19) 0.0382(18) Uani 1.000000 G .
H15 H 0.8452(4) 0.7247(4) 0.27674(19) 0.046(2) Uiso 1.000000 R .
C14 C 0.6848(4) 0.7684(3) 0.21253(17) 0.0292(15) Uani 1.000000 G .
H14 H 0.7011(4) 0.7010(3) 0.18665(17) 0.0351(18) Uiso 1.000000 R .
Cl1 Cl 0.56173(13) 0.68250(13) -0.07524(7) 0.0205(3) Uani 1.000000 . .
N1 N 0.7396(3) 0.8611(2) 0.01095(15) 0.0165(11) Uani 1.000000 . U
C4 C 0.8130(3) 0.9456(3) -0.02356(14) 0.0226(13) Uani 1.000000 G U
H4 H 0.8771(3) 0.9184(3) -0.05350(14) 0.0271(16) Uiso 1.000000 R .
C5 C 0.7927(4) 1.0698(3) -0.01425(16) 0.0244(14) Uani 1.000000 G U
H5 H 0.8429(4) 1.1275(3) -0.03783(16) 0.0293(16) Uiso 1.000000 R .
C6 C 0.6990(4) 1.1095(2) 0.02957(18) 0.0257(14) Uani 1.000000 G U
H6 H 0.6851(4) 1.1944(2) 0.03593(18) 0.0309(17) Uiso 1.000000 R .
C7 C 0.6255(3) 1.0251(3) 0.06407(15) 0.0231(13) Uani 1.000000 G U
H7 H 0.5615(3) 1.0523(3) 0.09402(15) 0.0277(16) Uiso 1.000000 R .
C8 C 0.6458(3) 0.9009(3) 0.05476(14) 0.0124(11) Uani 1.000000 G U
N2 N 0.5993(4) 0.6946(4) 0.0682(2) 0.0142(10) Uani 1.000000 . .
N3 N 0.5277(4) 0.6000(4) 0.0948(2) 0.0170(10) Uani 1.000000 . .
H3 H 0.5624(4) 0.5252(4) 0.0928(2) 0.0204(12) Uiso 1.000000 R .
O1 O 0.9928(4) 0.6613(5) -0.0949(2) 0.0398(12) Uani 1.000000 . .
O2 O 0.7696(4) 0.3865(4) 0.0016(2) 0.0285(10) Uani 1.000000 . .
O3 O 1.0128(4) 0.6617(4) 0.1021(2) 0.0312(10) Uani 1.000000 . .
Re1 Re 0.765389(19) 0.66616(2) 0.003190(11) 0.01488(7) Uani 1.000000 . .


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(7) . ?
C1 Re1 1.919(6) . ?
C2 O2 1.142(7) . ?
C2 Re1 1.922(6) . ?
C3 O3 1.158(6) . ?
C3 Re1 1.896(6) . ?
C9 C10 1.516(8) . ?
C9 C8 1.434(6) . ?
C9 N2 1.302(7) . ?
C10 C11 1.523(7) . ?
C10 C13 1.527(6) . ?
C11 C12 1.302(8) . ?
C12 N3 1.402(7) . ?
C13 C18 1.3900 . ?
C13 C14 1.3900 . ?
C18 C17 1.3900 . ?
C17 C16 1.3900 . ?
C16 C15 1.3900 . ?
C15 C14 1.3900 . ?
Cl1 Re1 2.4755(13) . ?
N1 C4 1.3900 . ?
N1 C8 1.3900 . ?
N1 Re1 2.157(2) . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C6 C7 1.3900 . ?
C7 C8 1.3900 . ?
N2 N3 1.370(6) . ?
N2 Re1 2.156(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
Re1 C1 O1 178.8(5) . . ?
Re1 C2 O2 179.3(4) . . ?
Re1 C3 O3 178.3(5) . . ?
C8 C9 C10 120.0(5) . . ?
N2 C9 C10 123.7(5) . . ?
N2 C9 C8 116.0(5) . . ?
C11 C10 C9 107.2(5) . . ?
C13 C10 C9 111.3(4) . . ?
C13 C10 C11 111.8(5) . . ?
C12 C11 C10 120.3(5) . . ?
N3 C12 C11 121.4(5) . . ?
C18 C13 C10 120.1 . . ?
C14 C13 C10 119.9 . . ?
C14 C13 C18 120.0 . . ?
C17 C18 C13 120.0 . . ?
C16 C17 C18 120.0 . . ?
C15 C16 C17 120.0 . . ?
C14 C15 C16 120.0 . . ?
C15 C14 C13 120.0 . . ?
C8 N1 C4 120.0 . . ?
Re1 N1 C4 124.0 . . ?
Re1 N1 C8 116.0 . . ?
C5 C4 N1 120.0 . . ?
C6 C5 C4 120.0 . . ?
C7 C6 C5 120.0 . . ?
C8 C7 C6 120.0 . . ?
N1 C8 C9 114.8(3) . . ?
C7 C8 C9 125.1(3) . . ?
C7 C8 N1 120.0 . . ?
N3 N2 C9 118.5(5) . . ?
Re1 N2 C9 118.8(4) . . ?
Re1 N2 N3 122.6(3) . . ?
N2 N3 C12 119.4(5) . . ?
C2 Re1 C1 88.0(3) . . ?
C3 Re1 C1 90.1(2) . . ?
C3 Re1 C2 88.6(2) . . ?
Cl1 Re1 C1 91.12(16) . . ?
Cl1 Re1 C2 94.06(16) . . ?
Cl1 Re1 C3 177.14(19) . . ?
N1 Re1 C1 99.1(2) . . ?
N1 Re1 C2 172.83(18) . . ?
N1 Re1 C3 92.8(2) . . ?
N1 Re1 Cl1 84.47(9) . . ?
N2 Re1 C1 172.6(2) . . ?
N2 Re1 C2 99.1(2) . . ?
N2 Re1 C3 92.3(2) . . ?
N2 Re1 Cl1 86.15(11) . . ?
N2 Re1 N1 73.85(14) . . ?

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
C9 C10 C11 C12 26.2(5) . . . . ?
C9 C10 C13 C18 134.4(4) . . . . ?
C9 C10 C13 C14 -47.0(5) . . . . ?
C9 C8 N1 C4 177.3(2) . . . . ?
C9 C8 N1 Re1 -4.4(3) . . . . ?
C9 C8 C7 C6 -177.0(3) . . . . ?
C9 N2 N3 C12 18.7(5) . . . . ?
C10 C11 C12 N3 -4.1(7) . . . . ?
C10 C13 C18 C17 178.6(3) . . . . ?
C10 C13 C14 C15 -178.6(3) . . . . ?
C11 C12 N3 N2 -21.0(7) . . . . ?
C12 N3 N2 Re1 -165.0(4) . . . . ?
C13 C18 C17 C16 0.0(3) . . . . ?
C13 C14 C15 C16 -0.0(3) . . . . ?
C18 C17 C16 C15 -0.0(3) . . . . ?
C17 C16 C15 C14 0.0(3) . . . . ?
N1 C4 C5 C6 0.0(3) . . . . ?
N1 C8 C7 C6 -0.0(3) . . . . ?
C4 C5 C6 C7 -0.0(3) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?


# end Validation Reply Form
_olex2_exptl_crystal_mounting_method 'cyroloop '
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_U_iso_atom_site_label
_restr_U_iso_weight_param
N1 0.0100
C4 0.0100
C5 0.0100
C6 0.0100
C7 0.0100
C8 0.0100

# start Validation Reply Form
_vrf_PLAT601_ac484               
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of .        271 Ang**3
RESPONSE: Co-crystallized CH2Cl2 was removed using 'squeeze' protocol found in the PLATON program package.
;
_refine_special_details          SQUEEZE
