# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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 1419735'
_audit_update_record             
;
2015-08-20 deposited with the CCDC.
2015-10-07 downloaded from the CCDC.
;
_audit_creation_date             2015-07-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        6.Cl4
_chemical_formula_moiety         'C24 H30 N8, 2(C H4 O), 4(Cl), H2 O'
_chemical_formula_sum            'C26 H40 Cl4 N8 O3'
_chemical_formula_weight         654.46
_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'

_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                   9.8817(3)
_cell_length_b                   12.7702(6)
_cell_length_c                   13.4397(5)
_cell_angle_alpha                107.655(4)
_cell_angle_beta                 95.924(3)
_cell_angle_gamma                92.500(3)
_cell_volume                     1602.43(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    173
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.697
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11313
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.045
_diffrn_reflns_theta_min         3.477
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5701
_reflns_number_total             6306
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.807
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         6306
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.098
_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)+(0.0672P)²+0.8883P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1321
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O3(H3A,H3B)
2.b Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C18(H18), C9(H9), C11(H11), C15(H15), C3(H3), C10(H10),
 C22(H22), C6(H6), C2(H2), C21(H21), C5(H5), C19(H19), C23(H23), C17(H17)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C16(H16A,H16B,H16C), C12(H12A,H12B,H12C), C20(H20A,H20B,
 H20C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
N1 N 1.01018(18) 0.68171(15) 0.22575(14) 0.0310(4) Uani 1 1 d . . . . .
N3 N 0.85177(18) 0.79184(15) 0.32230(14) 0.0312(4) Uani 1 1 d . . . . .
N5 N 0.62893(18) 0.20220(15) 0.19656(15) 0.0322(4) Uani 1 1 d . . . . .
N7 N 0.46074(19) 0.29952(15) 0.29301(15) 0.0343(4) Uani 1 1 d . . . . .
N4 N 0.7791(2) 0.90749(16) 0.45479(15) 0.0362(4) Uani 1 1 d . . . . .
N8 N 0.27132(19) 0.36223(16) 0.33864(15) 0.0353(4) Uani 1 1 d . . . . .
N6 N 0.7318(2) 0.06862(16) 0.10404(16) 0.0373(4) Uani 1 1 d . . . . .
N2 N 1.1919(2) 0.64706(16) 0.15032(16) 0.0393(4) Uani 1 1 d . . . . .
C13 C 0.7722(2) 0.80204(18) 0.39869(17) 0.0338(4) Uani 1 1 d . . . . .
H13 H 0.7209 0.7451 0.4104 0.041 Uiso 1 1 calc R . . . .
C14 C 0.9114(2) 0.89498(18) 0.33030(19) 0.0361(5) Uani 1 1 d . . . . .
H14 H 0.9708 0.9113 0.2868 0.043 Uiso 1 1 calc R . . . .
C18 C 0.5681(2) 0.17798(19) 0.09472(19) 0.0376(5) Uani 1 1 d . . . . .
H18 H 0.4968 0.2125 0.0704 0.045 Uiso 1 1 calc R . . . .
C7 C 0.8643(2) 0.69124(18) 0.23625(17) 0.0324(4) Uani 1 1 d . . . . .
H7 H 0.8191 0.6999 0.1711 0.039 Uiso 1 1 calc R . . . .
C9 C 1.0589(2) 0.65357(18) 0.13315(18) 0.0369(5) Uani 1 1 d . . . . .
H9 H 1.0081 0.6407 0.0678 0.044 Uiso 1 1 calc R . . . .
C11 C 1.2299(2) 0.6730(2) 0.2566(2) 0.0399(5) Uani 1 1 d . . . . .
H11 H 1.3180 0.6751 0.2895 0.048 Uiso 1 1 calc R . . . .
C15 C 0.8661(2) 0.96653(19) 0.41336(19) 0.0382(5) Uani 1 1 d . . . . .
H15 H 0.8891 1.0421 0.4385 0.046 Uiso 1 1 calc R . . . .
C3 C 0.7860(2) 0.45372(18) 0.34237(18) 0.0342(4) Uani 1 1 d . . . . .
H3 H 0.8221 0.4243 0.3938 0.041 Uiso 1 1 calc R . . . .
C1 C 0.7961(2) 0.59080(17) 0.25308(17) 0.0316(4) Uani 1 1 d . . . . .
C8 C 0.6081(2) 0.29722(18) 0.28720(18) 0.0338(4) Uani 1 1 d . . . . .
H8 H 0.6527 0.2865 0.3516 0.041 Uiso 1 1 calc R . . . .
C10 C 1.1168(2) 0.69483(19) 0.30477(18) 0.0355(5) Uani 1 1 d . . . . .
H10 H 1.1115 0.7147 0.3767 0.043 Uiso 1 1 calc R . . . .
C4 C 0.6695(2) 0.40329(17) 0.27605(17) 0.0321(4) Uani 1 1 d . . . . .
C22 C 0.3688(2) 0.2092(2) 0.27731(19) 0.0390(5) Uani 1 1 d . . . . .
H22 H 0.3859 0.1353 0.2522 0.047 Uiso 1 1 calc R . . . .
C6 C 0.6783(2) 0.54088(18) 0.18824(17) 0.0338(4) Uani 1 1 d . . . . .
H6 H 0.6417 0.5705 0.1370 0.041 Uiso 1 1 calc R . . . .
C2 C 0.8491(2) 0.54842(19) 0.33193(18) 0.0357(5) Uani 1 1 d . . . . .
H2 H 0.9265 0.5835 0.3773 0.043 Uiso 1 1 calc R . . . .
C21 C 0.3991(2) 0.39079(19) 0.33144(18) 0.0347(5) Uani 1 1 d . . . . .
H21 H 0.4389 0.4625 0.3501 0.042 Uiso 1 1 calc R . . . .
C5 C 0.6143(2) 0.44666(19) 0.19930(17) 0.0349(5) Uani 1 1 d . . . . .
H5 H 0.5352 0.4129 0.1556 0.042 Uiso 1 1 calc R . . . .
C19 C 0.6324(2) 0.0947(2) 0.0376(2) 0.0397(5) Uani 1 1 d . . . . .
H19 H 0.6134 0.0603 -0.0345 0.048 Uiso 1 1 calc R . . . .
C23 C 0.2504(2) 0.2492(2) 0.30540(19) 0.0394(5) Uani 1 1 d . . . . .
H23 H 0.1694 0.2081 0.3029 0.047 Uiso 1 1 calc R . . . .
C17 C 0.7281(2) 0.13551(19) 0.20059(19) 0.0374(5) Uani 1 1 d . . . . .
H17 H 0.7847 0.1359 0.2605 0.045 Uiso 1 1 calc R . . . .
C24 C 0.1689(3) 0.4405(2) 0.3731(2) 0.0459(6) Uani 1 1 d . . . . .
H24A H 0.2138 0.5109 0.4139 0.069 Uiso 1 1 calc GR . . . .
H24B H 0.1116 0.4139 0.4152 0.069 Uiso 1 1 calc GR . . . .
H24C H 0.1143 0.4480 0.3126 0.069 Uiso 1 1 calc GR . . . .
C16 C 0.7069(3) 0.9528(2) 0.5464(2) 0.0508(6) Uani 1 1 d . . . . .
H16A H 0.6393 0.8982 0.5501 0.076 Uiso 1 1 calc GR . . . .
H16B H 0.6633 1.0166 0.5401 0.076 Uiso 1 1 calc GR . . . .
H16C H 0.7708 0.9733 0.6092 0.076 Uiso 1 1 calc GR . . . .
C12 C 1.2833(3) 0.6229(3) 0.0692(3) 0.0598(8) Uani 1 1 d . . . . .
H12A H 1.2305 0.5995 0.0010 0.090 Uiso 1 1 calc GR . . . .
H12B H 1.3389 0.5653 0.0767 0.090 Uiso 1 1 calc GR . . . .
H12C H 1.3408 0.6880 0.0762 0.090 Uiso 1 1 calc GR . . . .
C20 C 0.8244(3) -0.0183(2) 0.0706(3) 0.0529(7) Uani 1 1 d . . . . .
H20A H 0.7775 -0.0886 0.0612 0.079 Uiso 1 1 calc GR . . . .
H20B H 0.9017 -0.0061 0.1234 0.079 Uiso 1 1 calc GR . . . .
H20C H 0.8548 -0.0170 0.0054 0.079 Uiso 1 1 calc GR . . . .
C25 C 0.4686(4) 0.1136(3) 0.7585(4) 0.0752(10) Uani 1 1 d . . . . .
H25A H 0.5103 0.1314 0.7036 0.113 Uiso 1 1 calc GR . . . .
H25B H 0.4694 0.1789 0.8175 0.113 Uiso 1 1 calc GR . . . .
H25C H 0.3761 0.0842 0.7329 0.113 Uiso 1 1 calc GR . . . .
O1 O 0.5389(2) 0.0381(2) 0.7887(3) 0.0782(7) Uani 1 1 d . . . . .
H1 H 0.6208 0.0570 0.7978 0.117 Uiso 1 1 calc GR . . . .
C26 C -0.0296(4) 0.2878(3) 0.1146(3) 0.0647(8) Uani 1 1 d . . . . .
H26A H -0.0240 0.2302 0.0502 0.097 Uiso 1 1 calc GR . . . .
H26B H -0.1237 0.2988 0.1234 0.097 Uiso 1 1 calc GR . . . .
H26C H 0.0134 0.2673 0.1727 0.097 Uiso 1 1 calc GR . . . .
O2 O 0.0376(2) 0.38677(18) 0.11130(17) 0.0588(5) Uani 1 1 d . . . . .
H2A H 0.1183 0.3778 0.1051 0.088 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.05069(5) 0.76003(4) 0.56615(4) 0.03708(14) Uani 1 1 d . . . . .
Cl2 Cl 0.15463(6) 0.92479(6) 0.16873(5) 0.04745(16) Uani 1 1 d . . . . .
Cl3 Cl 0.50015(6) 0.33794(5) 0.55687(5) 0.04767(17) Uani 1 1 d . . . . .
Cl4 Cl 0.30344(6) 0.32146(5) 0.01449(5) 0.04752(17) Uani 1 1 d . . . . .
O3 O 0.6456(4) 0.1443(3) 0.4424(3) 0.1010(10) Uani 1 1 d . . . . .
H3A H 0.5895 0.1837 0.4780 0.152 Uiso 1 1 d G . . . .
H3B H 0.7204 0.1826 0.4488 0.152 Uiso 1 1 d G . . . .


_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
N1 C7 1.470(3) . ?
N1 C9 1.333(3) . ?
N1 C10 1.383(3) . ?
N3 C13 1.336(3) . ?
N3 C14 1.388(3) . ?
N3 C7 1.465(3) . ?
N5 C18 1.374(3) . ?
N5 C8 1.475(3) . ?
N5 C17 1.334(3) . ?
N7 C8 1.468(3) . ?
N7 C22 1.386(3) . ?
N7 C21 1.326(3) . ?
N4 C13 1.324(3) . ?
N4 C15 1.384(3) . ?
N4 C16 1.465(3) . ?
N8 C21 1.320(3) . ?
N8 C23 1.375(3) . ?
N8 C24 1.463(3) . ?
N6 C19 1.379(3) . ?
N6 C17 1.325(3) . ?
N6 C20 1.463(3) . ?
N2 C9 1.322(3) . ?
N2 C11 1.372(3) . ?
N2 C12 1.457(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.342(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.337(4) . ?
C7 H7 0.9800 . ?
C7 C1 1.511(3) . ?
C9 H9 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.346(3) . ?
C15 H15 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.383(3) . ?
C3 C2 1.388(3) . ?
C1 C6 1.382(3) . ?
C1 C2 1.396(3) . ?
C8 H8 0.9800 . ?
C8 C4 1.515(3) . ?
C10 H10 0.9300 . ?
C4 C5 1.387(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.341(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.390(3) . ?
C2 H2 0.9300 . ?
C21 H21 0.9300 . ?
C5 H5 0.9300 . ?
C19 H19 0.9300 . ?
C23 H23 0.9300 . ?
C17 H17 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C25 O1 1.347(4) . ?
O1 H1 0.8200 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C26 O2 1.417(4) . ?
O2 H2A 0.8200 . ?
O3 H3A 0.8502 . ?
O3 H3B 0.8500 . ?

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
C9 N1 C7 123.07(18) . . ?
C9 N1 C10 109.00(19) . . ?
C10 N1 C7 127.88(18) . . ?
C13 N3 C14 109.13(19) . . ?
C13 N3 C7 126.28(18) . . ?
C14 N3 C7 124.28(19) . . ?
C18 N5 C8 127.21(19) . . ?
C17 N5 C18 109.6(2) . . ?
C17 N5 C8 122.46(19) . . ?
C22 N7 C8 126.31(19) . . ?
C21 N7 C8 123.96(18) . . ?
C21 N7 C22 108.87(19) . . ?
C13 N4 C15 108.9(2) . . ?
C13 N4 C16 125.0(2) . . ?
C15 N4 C16 126.1(2) . . ?
C21 N8 C23 109.2(2) . . ?
C21 N8 C24 124.3(2) . . ?
C23 N8 C24 126.4(2) . . ?
C19 N6 C20 124.6(2) . . ?
C17 N6 C19 108.3(2) . . ?
C17 N6 C20 127.1(2) . . ?
C9 N2 C11 108.9(2) . . ?
C9 N2 C12 124.9(2) . . ?
C11 N2 C12 126.1(2) . . ?
N3 C13 H13 126.0 . . ?
N4 C13 N3 108.00(19) . . ?
N4 C13 H13 126.0 . . ?
N3 C14 H14 126.8 . . ?
C15 C14 N3 106.3(2) . . ?
C15 C14 H14 126.8 . . ?
N5 C18 H18 127.0 . . ?
C19 C18 N5 106.0(2) . . ?
C19 C18 H18 127.0 . . ?
N1 C7 H7 108.1 . . ?
N1 C7 C1 112.79(18) . . ?
N3 C7 N1 107.72(16) . . ?
N3 C7 H7 108.1 . . ?
N3 C7 C1 111.95(18) . . ?
C1 C7 H7 108.1 . . ?
N1 C9 H9 125.9 . . ?
N2 C9 N1 108.1(2) . . ?
N2 C9 H9 125.9 . . ?
N2 C11 H11 126.1 . . ?
C10 C11 N2 107.8(2) . . ?
C10 C11 H11 126.1 . . ?
N4 C15 H15 126.2 . . ?
C14 C15 N4 107.6(2) . . ?
C14 C15 H15 126.2 . . ?
C4 C3 H3 120.1 . . ?
C4 C3 C2 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C6 C1 C7 118.37(19) . . ?
C6 C1 C2 120.0(2) . . ?
C2 C1 C7 121.61(19) . . ?
N5 C8 H8 108.9 . . ?
N5 C8 C4 110.75(18) . . ?
N7 C8 N5 107.55(17) . . ?
N7 C8 H8 108.9 . . ?
N7 C8 C4 111.86(18) . . ?
C4 C8 H8 108.9 . . ?
N1 C10 H10 126.9 . . ?
C11 C10 N1 106.2(2) . . ?
C11 C10 H10 126.9 . . ?
C3 C4 C8 117.81(19) . . ?
C3 C4 C5 120.7(2) . . ?
C5 C4 C8 121.47(19) . . ?
N7 C22 H22 126.7 . . ?
C23 C22 N7 106.5(2) . . ?
C23 C22 H22 126.7 . . ?
C1 C6 H6 119.9 . . ?
C1 C6 C5 120.2(2) . . ?
C5 C6 H6 119.9 . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
N7 C21 H21 125.9 . . ?
N8 C21 N7 108.1(2) . . ?
N8 C21 H21 125.9 . . ?
C4 C5 C6 119.5(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
N6 C19 H19 125.9 . . ?
C18 C19 N6 108.2(2) . . ?
C18 C19 H19 125.9 . . ?
N8 C23 H23 126.4 . . ?
C22 C23 N8 107.2(2) . . ?
C22 C23 H23 126.4 . . ?
N5 C17 H17 126.1 . . ?
N6 C17 N5 107.8(2) . . ?
N6 C17 H17 126.1 . . ?
N8 C24 H24A 109.5 . . ?
N8 C24 H24B 109.5 . . ?
N8 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N4 C16 H16A 109.5 . . ?
N4 C16 H16B 109.5 . . ?
N4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N6 C20 H20A 109.5 . . ?
N6 C20 H20B 109.5 . . ?
N6 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O1 C25 H25A 109.5 . . ?
O1 C25 H25B 109.5 . . ?
O1 C25 H25C 109.5 . . ?
C25 O1 H1 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O2 C26 H26A 109.5 . . ?
O2 C26 H26B 109.5 . . ?
O2 C26 H26C 109.5 . . ?
C26 O2 H2A 109.5 . . ?
H3A O3 H3B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C7 C1 C6 -128.1(2) . . . . ?
N1 C7 C1 C2 52.0(3) . . . . ?
N3 C14 C15 N4 -0.5(3) . . . . ?
N3 C7 C1 C6 110.2(2) . . . . ?
N3 C7 C1 C2 -69.6(3) . . . . ?
N5 C18 C19 N6 -0.2(3) . . . . ?
N5 C8 C4 C3 -108.9(2) . . . . ?
N5 C8 C4 C5 68.6(3) . . . . ?
N7 C8 C4 C3 131.1(2) . . . . ?
N7 C8 C4 C5 -51.4(3) . . . . ?
N7 C22 C23 N8 -0.6(3) . . . . ?
N2 C11 C10 N1 0.0(3) . . . . ?
C13 N3 C14 C15 0.3(2) . . . . ?
C13 N3 C7 N1 -135.4(2) . . . . ?
C13 N3 C7 C1 -10.9(3) . . . . ?
C13 N4 C15 C14 0.5(3) . . . . ?
C14 N3 C13 N4 -0.1(2) . . . . ?
C14 N3 C7 N1 51.6(3) . . . . ?
C14 N3 C7 C1 176.19(19) . . . . ?
C18 N5 C8 N7 52.8(3) . . . . ?
C18 N5 C8 C4 -69.8(3) . . . . ?
C18 N5 C17 N6 -0.5(2) . . . . ?
C7 N1 C9 N2 -176.92(18) . . . . ?
C7 N1 C10 C11 177.1(2) . . . . ?
C7 N3 C13 N4 -173.87(18) . . . . ?
C7 N3 C14 C15 174.30(19) . . . . ?
C7 C1 C6 C5 178.3(2) . . . . ?
C7 C1 C2 C3 -177.7(2) . . . . ?
C9 N1 C7 N3 -136.3(2) . . . . ?
C9 N1 C7 C1 99.6(2) . . . . ?
C9 N1 C10 C11 -0.4(3) . . . . ?
C9 N2 C11 C10 0.5(3) . . . . ?
C11 N2 C9 N1 -0.8(3) . . . . ?
C15 N4 C13 N3 -0.2(2) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C1 C6 C5 C4 0.2(3) . . . . ?
C8 N5 C18 C19 170.9(2) . . . . ?
C8 N5 C17 N6 -171.53(19) . . . . ?
C8 N7 C22 C23 170.9(2) . . . . ?
C8 N7 C21 N8 -171.3(2) . . . . ?
C8 C4 C5 C6 -176.5(2) . . . . ?
C10 N1 C7 N3 46.5(3) . . . . ?
C10 N1 C7 C1 -77.6(3) . . . . ?
C10 N1 C9 N2 0.7(2) . . . . ?
C4 C3 C2 C1 -1.4(4) . . . . ?
C22 N7 C8 N5 41.1(3) . . . . ?
C22 N7 C8 C4 162.9(2) . . . . ?
C22 N7 C21 N8 -1.3(3) . . . . ?
C6 C1 C2 C3 2.4(3) . . . . ?
C2 C3 C4 C8 177.2(2) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C2 C1 C6 C5 -1.8(3) . . . . ?
C21 N7 C8 N5 -150.7(2) . . . . ?
C21 N7 C8 C4 -28.9(3) . . . . ?
C21 N7 C22 C23 1.2(3) . . . . ?
C21 N8 C23 C22 -0.2(3) . . . . ?
C19 N6 C17 N5 0.4(3) . . . . ?
C23 N8 C21 N7 0.9(3) . . . . ?
C17 N5 C18 C19 0.4(3) . . . . ?
C17 N5 C8 N7 -137.8(2) . . . . ?
C17 N5 C8 C4 99.7(2) . . . . ?
C17 N6 C19 C18 -0.1(3) . . . . ?
C24 N8 C21 N7 -176.9(2) . . . . ?
C24 N8 C23 C22 177.6(2) . . . . ?
C16 N4 C13 N3 -179.6(2) . . . . ?
C16 N4 C15 C14 179.8(2) . . . . ?
C12 N2 C9 N1 -177.3(2) . . . . ?
C12 N2 C11 C10 177.0(2) . . . . ?
C20 N6 C19 C18 -179.7(2) . . . . ?
C20 N6 C17 N5 179.9(2) . . . . ?

_olex2_date_sample_data_collection 2011-12-02
_olex2_date_sample_submission    2015-07-07
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_18
_database_code_depnum_ccdc_archive 'CCDC 1419736'
_audit_update_record             
;
2015-08-20 deposited with the CCDC.
2015-10-07 downloaded from the CCDC.
;
_audit_creation_date             2015-07-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        18
_chemical_formula_moiety         'C22 H25 Cl N5 O3 Re, C2 H3 N'
_chemical_formula_sum            'C24 H28 Cl N6 O3 Re'
_chemical_formula_weight         670.17
_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      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                   8.0075(3)
_cell_length_b                   12.8704(5)
_cell_length_c                   13.4782(5)
_cell_angle_alpha                102.922(3)
_cell_angle_beta                 100.733(3)
_cell_angle_gamma                98.285(3)
_cell_volume                     1304.93(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    173.20
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.795
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11684
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.830
_diffrn_ambient_temperature      173.20
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4925
_reflns_number_total             5314
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         5314
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0224
_refine_ls_R_factor_gt           0.0192
_refine_ls_restrained_S_all      1.047
_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)+(0.0156P)²+0.3103P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0408
_refine_ls_wR_factor_ref         0.0422
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1A-C1A
 1.15 with sigma of 0.02
 C1-O1
 1.15 with sigma of 0.02
 C1A-Re1
 1.94 with sigma of 0.02
 C1-Re1
 1.94 with sigma of 0.02
 Re1-Cl1A
 2.51 with sigma of 0.02
 Re1-Cl1
 2.51 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Cl1) = Uanis(Cl1A)
Uanis(C1) = Uanis(C1A)
Uanis(O1) = Uanis(O1A)
4. Others
 Fixed Sof: Cl1(0.7) C1(0.7) Cl1A(0.3) O1(0.7) C1A(0.3) O1A(0.3)
5.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C16(H16A,H16B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
5.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9), C6(H6), C10(H10), C18(H18), C22(H22), C20(H20), C19(H19),
 C21(H21)
5.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C11(H11A,H11B,H11C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_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
Re1 Re 0.58072(2) 0.81714(2) 0.69285(2) 0.01989(4) Uani 1 1 d D . . . .
Cl1 Cl 0.68608(16) 0.73177(10) 0.53588(9) 0.0280(2) Uani 0.7 1 d D . P A 1
C1 C 0.5080(9) 0.8931(4) 0.8110(4) 0.0407(15) Uani 0.7 1 d D . P A 1
N1 N 0.3846(3) 0.56853(17) 0.65300(15) 0.0209(5) Uani 1 1 d . . . . .
N5 N 0.7550(3) 0.43261(18) 0.72404(15) 0.0225(5) Uani 1 1 d . . . . .
O2 O 0.8298(3) 0.73843(19) 0.85133(15) 0.0400(5) Uani 1 1 d . . . . .
N3 N 0.2704(3) 0.81153(18) 0.49605(16) 0.0237(5) Uani 1 1 d . . . . .
C3 C 0.7672(4) 0.9406(2) 0.7166(2) 0.0300(7) Uani 1 1 d . . . . .
N2 N 0.2063(3) 0.67546(19) 0.67914(16) 0.0237(5) Uani 1 1 d . . . . .
C4 C 0.3756(3) 0.6767(2) 0.67349(18) 0.0199(5) Uani 1 1 d . . . . .
C12 C 0.5379(3) 0.5219(2) 0.64233(19) 0.0207(5) Uani 1 1 d . . . . .
H12A H 0.6290 0.5771 0.6327 0.025 Uiso 1 1 calc R . . . .
H12B H 0.5083 0.4597 0.5796 0.025 Uiso 1 1 calc R . . . .
C8 C 0.3931(4) 0.8704(2) 0.58315(19) 0.0227(6) Uani 1 1 d . . . . .
C2 C 0.7362(4) 0.7653(2) 0.7901(2) 0.0260(6) Uani 1 1 d . . . . .
N4 N 0.3621(3) 0.97328(18) 0.59277(17) 0.0271(5) Uani 1 1 d . . . . .
C16 C 0.8814(4) 0.4469(2) 0.8236(2) 0.0271(6) Uani 1 1 d . . . . .
H16A H 0.9281 0.5255 0.8539 0.032 Uiso 1 1 calc R . . . .
H16B H 0.9792 0.4118 0.8083 0.032 Uiso 1 1 calc R . . . .
C13 C 0.6074(4) 0.4834(2) 0.73840(19) 0.0243(6) Uani 1 1 d . . . . .
H13A H 0.6428 0.5461 0.8008 0.029 Uiso 1 1 calc R . . . .
H13B H 0.5150 0.4307 0.7501 0.029 Uiso 1 1 calc R . . . .
O3 O 0.8839(3) 1.0106(2) 0.73680(18) 0.0532(7) Uani 1 1 d . . . . .
C14 C 0.2459(4) 0.6959(2) 0.44364(19) 0.0234(6) Uani 1 1 d . . . . .
H14A H 0.1231 0.6610 0.4331 0.028 Uiso 1 1 calc R . . . .
H14B H 0.3181 0.6601 0.4883 0.028 Uiso 1 1 calc R . . . .
C15 C 0.7042(4) 0.3192(2) 0.6614(2) 0.0294(6) Uani 1 1 d . . . . .
H15A H 0.5773 0.2956 0.6497 0.035 Uiso 1 1 calc R . . . .
H15B H 0.7607 0.2724 0.7007 0.035 Uiso 1 1 calc R . . . .
C5 C 0.2270(4) 0.5043(2) 0.6462(2) 0.0293(6) Uani 1 1 d . . . . .
H5 H 0.2019 0.4273 0.6324 0.035 Uiso 1 1 calc R . . . .
C17 C 0.8097(4) 0.4008(2) 0.9051(2) 0.0286(6) Uani 1 1 d . . . . .
C9 C 0.1664(4) 0.8759(3) 0.4563(2) 0.0364(7) Uani 1 1 d . . . . .
H9 H 0.0714 0.8527 0.3974 0.044 Uiso 1 1 calc R . . . .
C7 C 0.1254(4) 0.7698(3) 0.7036(2) 0.0328(7) Uani 1 1 d . . . . .
H7A H 0.1099 0.7820 0.7755 0.049 Uiso 1 1 calc GR . . . .
H7B H 0.0123 0.7567 0.6553 0.049 Uiso 1 1 calc GR . . . .
H7C H 0.1997 0.8340 0.6966 0.049 Uiso 1 1 calc GR . . . .
C6 C 0.1167(4) 0.5714(2) 0.6628(2) 0.0315(7) Uani 1 1 d . . . . .
H6 H -0.0020 0.5510 0.6632 0.038 Uiso 1 1 calc R . . . .
C10 C 0.2249(4) 0.9774(3) 0.5167(2) 0.0371(8) Uani 1 1 d . . . . .
H10 H 0.1800 1.0401 0.5084 0.045 Uiso 1 1 calc R . . . .
C18 C 0.7434(4) 0.4672(3) 0.9784(2) 0.0377(8) Uani 1 1 d . . . . .
H18 H 0.7462 0.5411 0.9781 0.045 Uiso 1 1 calc R . . . .
C11 C 0.4605(5) 1.0701(2) 0.6715(2) 0.0391(8) Uani 1 1 d . . . . .
H11A H 0.4633 1.0587 0.7412 0.059 Uiso 1 1 calc GR . . . .
H11B H 0.4056 1.1322 0.6646 0.059 Uiso 1 1 calc GR . . . .
H11C H 0.5791 1.0846 0.6617 0.059 Uiso 1 1 calc GR . . . .
C23 C 0.2154(5) 0.2209(4) 0.8256(3) 0.0580(11) Uani 1 1 d . . . . .
Cl1A Cl 0.4924(5) 0.9143(3) 0.8488(3) 0.0280(2) Uani 0.3 1 d D . P A 2
C22 C 0.8074(5) 0.2938(3) 0.9087(2) 0.0412(8) Uani 1 1 d . . . . .
H22 H 0.8546 0.2476 0.8605 0.049 Uiso 1 1 calc R . . . .
C20 C 0.6692(5) 0.3209(4) 1.0535(3) 0.0565(11) Uani 1 1 d . . . . .
H20 H 0.6200 0.2933 1.1036 0.068 Uiso 1 1 calc R . . . .
C19 C 0.6734(5) 0.4264(4) 1.0515(2) 0.0526(10) Uani 1 1 d . . . . .
H19 H 0.6280 0.4725 1.1009 0.063 Uiso 1 1 calc R . . . .
C21 C 0.7365(5) 0.2538(3) 0.9825(3) 0.0571(11) Uani 1 1 d . . . . .
H21 H 0.7343 0.1802 0.9841 0.069 Uiso 1 1 calc R . . . .
N6 N 0.1944(5) 0.2638(3) 0.7603(3) 0.0741(11) Uani 1 1 d . . . . .
C24 C 0.2396(6) 0.1609(4) 0.9067(3) 0.0780(14) Uani 1 1 d . . . . .
H24A H 0.3233 0.2070 0.9691 0.117 Uiso 1 1 calc GR . . . .
H24B H 0.2830 0.0951 0.8803 0.117 Uiso 1 1 calc GR . . . .
H24C H 0.1285 0.1406 0.9247 0.117 Uiso 1 1 calc GR . . . .
O1 O 0.4743(6) 0.9407(4) 0.8846(3) 0.0611(14) Uani 0.7 1 d D . P A 1
C1A C 0.675(2) 0.7544(11) 0.5783(10) 0.0407(15) Uani 0.3 1 d D . P A 2
O1A O 0.7371(16) 0.7197(9) 0.5039(7) 0.0611(14) Uani 0.3 1 d D . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 Cl1 2.5075(13) . ?
Re1 C1 1.909(6) . ?
Re1 C3 1.941(3) . ?
Re1 C4 2.192(3) . ?
Re1 C8 2.199(3) . ?
Re1 C2 1.933(3) . ?
Re1 Cl1A 2.473(4) . ?
Re1 C1A 1.912(11) . ?
C1 O1 1.142(5) . ?
N1 C4 1.372(3) . ?
N1 C12 1.458(3) . ?
N1 C5 1.381(3) . ?
N5 C16 1.479(3) . ?
N5 C13 1.454(3) . ?
N5 C15 1.469(3) . ?
O2 C2 1.155(3) . ?
N3 C8 1.369(3) . ?
N3 C14 1.465(3) . ?
N3 C9 1.377(4) . ?
C3 O3 1.145(3) . ?
N2 C4 1.370(3) . ?
N2 C7 1.459(4) . ?
N2 C6 1.374(4) . ?
C12 C13 1.526(3) . ?
C8 N4 1.364(3) . ?
N4 C10 1.372(4) . ?
N4 C11 1.454(4) . ?
C16 C17 1.522(4) . ?
C14 C15 1.520(3) 2_666 ?
C15 C14 1.520(3) 2_666 ?
C5 C6 1.336(4) . ?
C17 C18 1.390(4) . ?
C17 C22 1.387(4) . ?
C9 C10 1.340(4) . ?
C18 C19 1.384(4) . ?
C23 N6 1.139(5) . ?
C23 C24 1.474(6) . ?
C22 C21 1.390(4) . ?
C20 C19 1.360(6) . ?
C20 C21 1.382(5) . ?
C1A O1A 1.226(11) . ?

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
C1 Re1 Cl1 175.46(18) . . ?
C1 Re1 C3 88.9(2) . . ?
C1 Re1 C4 89.81(19) . . ?
C1 Re1 C8 92.4(2) . . ?
C1 Re1 C2 86.8(2) . . ?
C3 Re1 Cl1 87.07(9) . . ?
C3 Re1 C4 177.22(10) . . ?
C3 Re1 C8 96.11(11) . . ?
C3 Re1 Cl1A 88.59(13) . . ?
C4 Re1 Cl1 94.31(7) . . ?
C4 Re1 C8 86.41(10) . . ?
C4 Re1 Cl1A 90.05(12) . . ?
C8 Re1 Cl1 85.97(7) . . ?
C8 Re1 Cl1A 93.82(12) . . ?
C2 Re1 Cl1 94.98(8) . . ?
C2 Re1 C3 86.62(12) . . ?
C2 Re1 C4 90.85(10) . . ?
C2 Re1 C8 177.16(10) . . ?
C2 Re1 Cl1A 85.44(13) . . ?
C1A Re1 C3 84.7(4) . . ?
C1A Re1 C4 96.6(4) . . ?
C1A Re1 C8 88.8(5) . . ?
C1A Re1 C2 92.3(5) . . ?
C1A Re1 Cl1A 173.1(5) . . ?
O1 C1 Re1 176.0(5) . . ?
C4 N1 C12 126.8(2) . . ?
C4 N1 C5 111.6(2) . . ?
C5 N1 C12 121.6(2) . . ?
C13 N5 C16 112.57(19) . . ?
C13 N5 C15 112.9(2) . . ?
C15 N5 C16 113.2(2) . . ?
C8 N3 C14 128.0(2) . . ?
C8 N3 C9 111.5(2) . . ?
C9 N3 C14 120.5(2) . . ?
O3 C3 Re1 174.7(3) . . ?
C4 N2 C7 126.6(2) . . ?
C4 N2 C6 111.5(2) . . ?
C6 N2 C7 121.8(2) . . ?
N1 C4 Re1 128.79(18) . . ?
N2 C4 Re1 128.40(19) . . ?
N2 C4 N1 102.8(2) . . ?
N1 C12 C13 111.23(19) . . ?
N3 C8 Re1 130.50(19) . . ?
N4 C8 Re1 126.53(19) . . ?
N4 C8 N3 102.7(2) . . ?
O2 C2 Re1 177.1(2) . . ?
C8 N4 C10 112.0(2) . . ?
C8 N4 C11 126.0(2) . . ?
C10 N4 C11 122.0(2) . . ?
N5 C16 C17 115.1(2) . . ?
N5 C13 C12 110.32(19) . . ?
N3 C14 C15 110.8(2) . 2_666 ?
N5 C15 C14 112.3(2) . 2_666 ?
C6 C5 N1 106.7(3) . . ?
C18 C17 C16 119.6(3) . . ?
C22 C17 C16 122.0(3) . . ?
C22 C17 C18 118.4(3) . . ?
C10 C9 N3 106.9(3) . . ?
C5 C6 N2 107.4(3) . . ?
C9 C10 N4 106.8(3) . . ?
C19 C18 C17 120.6(3) . . ?
N6 C23 C24 177.5(5) . . ?
C17 C22 C21 120.4(3) . . ?
C19 C20 C21 119.9(3) . . ?
C20 C19 C18 120.6(3) . . ?
C20 C21 C22 120.1(4) . . ?
O1A C1A Re1 176.5(13) . . ?

_olex2_date_sample_data_collection 2013-01-04
_olex2_exptl_crystal_mounting_method 
'Crystals were removed from the crystallisation vial and immediately coated with Paratone oil on a glass slide. A suitable single crystal was mounted in Paratone oil on a glass fibre and cooled rapidly to 173 K in a stream of cold N2 using an Oxford low temperature device. '
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_17ReO4
_database_code_depnum_ccdc_archive 'CCDC 1419737'
_audit_update_record             
;
2015-08-20 deposited with the CCDC.
2015-10-07 downloaded from the CCDC.
;
_audit_creation_date             2015-07-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H25 N5 O3 Re, O4 Re'
_chemical_formula_sum            'C22 H25 N5 O7 Re2'
_chemical_formula_weight         843.87
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.1406(3)
_cell_length_b                   20.5194(6)
_cell_length_c                   13.4977(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.194(3)
_cell_angle_gamma                90
_cell_volume                     2529.75(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    173.02
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    9.613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.216
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1592
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14835
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.364
_diffrn_reflns_theta_min         2.986
_diffrn_ambient_temperature      173.02
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4639
_reflns_number_total             5170
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.863
_refine_diff_density_min         -0.978
_refine_diff_density_rms         0.151
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         5170
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0267
_refine_ls_restrained_S_all      1.104
_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)+(0.0251P)²+1.0755P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0570
_refine_ls_wR_factor_ref         0.0592
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Re2-O6 = Re2A-O6A = Re2A-O4 = Re2-O4 = Re2-O5 = Re2A-O5 = Re2-O7 = Re2A-O7A
 1.72 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O6) = Uanis(O6A)
Uanis(Re2) = Uanis(Re2A)
Uanis(O7) = Uanis(O7A)
4. Others
 Sof(O6A)=Sof(Re2A)=Sof(O7A)=1-FVAR(1)
 Sof(Re2)=Sof(O6)=Sof(O7)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C15(H15A,H15B), C13(H13A,H13B), C12(H12A,H12B), C14(H14A,H14B)
5.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C18(H18), C22(H22), C6(H6), C10(H10), C21(H21), C20(H20), C19(H19),
 C9(H9)
5.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_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
Re1 Re 0.08360(2) 0.12428(2) 0.77327(2) 0.01387(6) Uani 1 1 d . . . . .
Re2 Re 0.5341(2) 0.16928(6) 1.11355(9) 0.0292(2) Uani 0.842(9) 1 d D . P A 1
N5 N 0.3325(3) 0.11085(18) 0.7450(3) 0.0144(7) Uani 1 1 d . . . . .
O1 O 0.0203(3) -0.01469(17) 0.6952(3) 0.0300(8) Uani 1 1 d . . . . .
O2 O 0.0111(4) 0.18281(19) 0.5655(2) 0.0347(9) Uani 1 1 d . . . . .
N1 N 0.2314(3) 0.03662(18) 0.9360(3) 0.0181(8) Uani 1 1 d . . . . .
C2 C 0.0402(4) 0.1604(2) 0.6420(4) 0.0213(10) Uani 1 1 d . . . . .
N2 N 0.0854(4) 0.0989(2) 1.0107(3) 0.0213(8) Uani 1 1 d . . . . .
C4 C 0.1385(4) 0.0868(2) 0.9199(3) 0.0171(9) Uani 1 1 d . . . . .
C16 C 0.3420(4) 0.0799(2) 0.6434(3) 0.0186(9) Uani 1 1 d . . . . .
H16A H 0.2942 0.0367 0.6454 0.022 Uiso 1 1 calc R . . . .
H16B H 0.2845 0.1070 0.5954 0.022 Uiso 1 1 calc R . . . .
C1 C 0.0482(4) 0.0366(2) 0.7257(3) 0.0221(10) Uani 1 1 d . . . . .
C15 C 0.4105(4) 0.1748(2) 0.7416(3) 0.0182(9) Uani 1 1 d . . . . .
H15A H 0.3717 0.1997 0.6834 0.022 Uiso 1 1 calc R . . . .
H15B H 0.5156 0.1665 0.7317 0.022 Uiso 1 1 calc R . . . .
C13 C 0.4152(4) 0.0692(2) 0.8188(3) 0.0182(9) Uani 1 1 d . . . . .
H13A H 0.4510 0.0971 0.8744 0.022 Uiso 1 1 calc R . . . .
H13B H 0.5020 0.0511 0.7868 0.022 Uiso 1 1 calc R . . . .
N3 N 0.2590(4) 0.25248(18) 0.8335(3) 0.0197(8) Uani 1 1 d . . . . .
O3 O -0.2422(3) 0.12196(19) 0.8135(3) 0.0371(9) Uani 1 1 d . . . . .
N4 N 0.0337(4) 0.2765(2) 0.8232(3) 0.0232(9) Uani 1 1 d . . . . .
C17 C 0.4930(4) 0.0709(2) 0.6045(3) 0.0183(9) Uani 1 1 d . . . . .
C12 C 0.3286(5) 0.0131(2) 0.8610(3) 0.0218(10) Uani 1 1 d . . . . .
H12A H 0.2704 -0.0084 0.8069 0.026 Uiso 1 1 calc R . . . .
H12B H 0.3970 -0.0195 0.8907 0.026 Uiso 1 1 calc R . . . .
C8 C 0.1261(4) 0.2252(2) 0.8181(3) 0.0170(9) Uani 1 1 d . . . . .
C3 C -0.1194(5) 0.1252(2) 0.7995(3) 0.0242(11) Uani 1 1 d . . . . .
C14 C 0.3967(4) 0.2166(2) 0.8334(3) 0.0233(10) Uani 1 1 d . . . . .
H14A H 0.4041 0.1884 0.8929 0.028 Uiso 1 1 calc R . . . .
H14B H 0.4791 0.2479 0.8376 0.028 Uiso 1 1 calc R . . . .
C5 C 0.2389(5) 0.0174(2) 1.0338(3) 0.0253(11) Uani 1 1 d . . . . .
H5 H 0.2978 -0.0165 1.0622 0.030 Uiso 1 1 calc R . . . .
C18 C 0.5559(5) 0.1202(3) 0.5501(3) 0.0263(11) Uani 1 1 d . . . . .
H18 H 0.5047 0.1599 0.5387 0.032 Uiso 1 1 calc R . . . .
C22 C 0.5685(5) 0.0129(3) 0.6185(3) 0.0239(10) Uani 1 1 d . . . . .
H22 H 0.5260 -0.0215 0.6546 0.029 Uiso 1 1 calc R . . . .
C6 C 0.1457(5) 0.0563(3) 1.0807(3) 0.0291(11) Uani 1 1 d . . . . .
H6 H 0.1251 0.0549 1.1491 0.035 Uiso 1 1 calc R . . . .
C10 C 0.1094(5) 0.3333(2) 0.8413(4) 0.0304(12) Uani 1 1 d . . . . .
H10 H 0.0686 0.3756 0.8478 0.036 Uiso 1 1 calc R . . . .
C21 C 0.7059(5) 0.0048(3) 0.5800(3) 0.0306(12) Uani 1 1 d . . . . .
H21 H 0.7568 -0.0351 0.5899 0.037 Uiso 1 1 calc R . . . .
C20 C 0.7681(5) 0.0535(3) 0.5282(4) 0.0369(14) Uani 1 1 d . . . . .
H20 H 0.8629 0.0476 0.5031 0.044 Uiso 1 1 calc R . . . .
C19 C 0.6952(5) 0.1113(3) 0.5118(4) 0.0360(13) Uani 1 1 d . . . . .
H19 H 0.7387 0.1450 0.4748 0.043 Uiso 1 1 calc R . . . .
O6 O 0.5451(8) 0.1319(4) 1.2270(4) 0.064(2) Uani 0.842(9) 1 d D . P A 1
O7 O 0.6567(7) 0.2315(3) 1.1138(6) 0.073(2) Uani 0.842(9) 1 d D . P A 1
C7 C -0.0164(6) 0.1505(3) 1.0334(4) 0.0363(13) Uani 1 1 d . . . . .
H7A H 0.0070 0.1896 0.9956 0.054 Uiso 1 1 calc GR . . . .
H7B H -0.0086 0.1602 1.1045 0.054 Uiso 1 1 calc GR . . . .
H7C H -0.1164 0.1364 1.0156 0.054 Uiso 1 1 calc GR . . . .
C11 C -0.1257(5) 0.2742(3) 0.8100(4) 0.0357(13) Uani 1 1 d . . . . .
H11A H -0.1525 0.2491 0.7503 0.054 Uiso 1 1 calc GR . . . .
H11B H -0.1639 0.3187 0.8030 0.054 Uiso 1 1 calc GR . . . .
H11C H -0.1675 0.2535 0.8678 0.054 Uiso 1 1 calc GR . . . .
C9 C 0.2504(5) 0.3180(3) 0.8479(4) 0.0307(12) Uani 1 1 d . . . . .
H9 H 0.3299 0.3470 0.8603 0.037 Uiso 1 1 calc R . . . .
O6A O 0.468(4) 0.1065(16) 1.212(2) 0.064(2) Uani 0.158(9) 1 d D . P A 2
Re2A Re 0.5022(7) 0.1624(3) 1.1232(4) 0.0292(2) Uani 0.158(9) 1 d D . P A 2
O7A O 0.622(4) 0.2189(15) 1.171(3) 0.073(2) Uani 0.158(9) 1 d D . P A 2
O4 O 0.5740(4) 0.11572(18) 1.0235(2) 0.0383(9) Uani 1 1 d D . . . .
O5 O 0.3591(4) 0.2005(2) 1.0893(3) 0.0562(12) Uani 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 N5 2.338(3) . ?
Re1 C2 1.947(5) . ?
Re1 C4 2.165(4) . ?
Re1 C1 1.934(5) . ?
Re1 C8 2.188(4) . ?
Re1 C3 1.903(5) . ?
Re2 O6 1.711(5) . ?
Re2 O7 1.699(5) . ?
Re2 O4 1.689(3) . ?
Re2 O5 1.743(4) . ?
N5 C16 1.516(5) . ?
N5 C15 1.496(5) . ?
N5 C13 1.496(5) . ?
O1 C1 1.155(6) . ?
O2 C2 1.152(6) . ?
N1 C4 1.347(5) . ?
N1 C12 1.455(5) . ?
N1 C5 1.377(5) . ?
N2 C4 1.357(5) . ?
N2 C6 1.386(6) . ?
N2 C7 1.450(6) . ?
C16 C17 1.507(5) . ?
C15 C14 1.516(6) . ?
C13 C12 1.519(6) . ?
N3 C8 1.346(5) . ?
N3 C14 1.459(5) . ?
N3 C9 1.361(6) . ?
O3 C3 1.147(5) . ?
N4 C8 1.352(5) . ?
N4 C10 1.374(6) . ?
N4 C11 1.462(6) . ?
C17 C18 1.387(6) . ?
C17 C22 1.385(6) . ?
C5 C6 1.344(7) . ?
C18 C19 1.404(7) . ?
C22 C21 1.388(6) . ?
C10 C9 1.326(7) . ?
C21 C20 1.356(8) . ?
C20 C19 1.374(8) . ?
O6A Re2A 1.699(18) . ?
Re2A O7A 1.706(18) . ?
Re2A O4 1.796(6) . ?
Re2A O5 1.577(6) . ?

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 Re1 N5 93.56(15) . . ?
C2 Re1 C4 177.84(17) . . ?
C2 Re1 C8 85.37(17) . . ?
C4 Re1 N5 85.08(13) . . ?
C4 Re1 C8 92.92(16) . . ?
C1 Re1 N5 89.30(14) . . ?
C1 Re1 C2 91.52(19) . . ?
C1 Re1 C4 90.15(18) . . ?
C1 Re1 C8 176.64(17) . . ?
C8 Re1 N5 89.61(14) . . ?
C3 Re1 N5 173.65(17) . . ?
C3 Re1 C2 89.96(18) . . ?
C3 Re1 C4 91.54(17) . . ?
C3 Re1 C1 85.33(19) . . ?
C3 Re1 C8 95.94(18) . . ?
O6 Re2 O5 110.8(2) . . ?
O7 Re2 O6 108.6(3) . . ?
O7 Re2 O5 109.0(3) . . ?
O4 Re2 O6 110.2(2) . . ?
O4 Re2 O7 109.3(3) . . ?
O4 Re2 O5 109.05(19) . . ?
C16 N5 Re1 106.6(2) . . ?
C15 N5 Re1 111.7(2) . . ?
C15 N5 C16 107.2(3) . . ?
C13 N5 Re1 115.4(2) . . ?
C13 N5 C16 108.5(3) . . ?
C13 N5 C15 107.1(3) . . ?
C4 N1 C12 122.6(4) . . ?
C4 N1 C5 112.5(4) . . ?
C5 N1 C12 124.2(4) . . ?
O2 C2 Re1 177.9(4) . . ?
C4 N2 C6 110.7(4) . . ?
C4 N2 C7 125.4(4) . . ?
C6 N2 C7 123.9(4) . . ?
N1 C4 Re1 122.8(3) . . ?
N1 C4 N2 103.9(4) . . ?
N2 C4 Re1 133.0(3) . . ?
C17 C16 N5 116.8(3) . . ?
O1 C1 Re1 176.5(4) . . ?
N5 C15 C14 114.6(3) . . ?
N5 C13 C12 115.2(3) . . ?
C8 N3 C14 124.3(4) . . ?
C8 N3 C9 112.1(4) . . ?
C9 N3 C14 123.6(4) . . ?
C8 N4 C10 111.0(4) . . ?
C8 N4 C11 126.2(4) . . ?
C10 N4 C11 122.7(4) . . ?
C18 C17 C16 119.9(4) . . ?
C22 C17 C16 121.1(4) . . ?
C22 C17 C18 118.9(4) . . ?
N1 C12 C13 110.5(4) . . ?
N3 C8 Re1 125.8(3) . . ?
N3 C8 N4 103.3(4) . . ?
N4 C8 Re1 130.2(3) . . ?
O3 C3 Re1 176.0(4) . . ?
N3 C14 C15 112.6(4) . . ?
C6 C5 N1 105.7(4) . . ?
C17 C18 C19 120.0(5) . . ?
C17 C22 C21 120.4(5) . . ?
C5 C6 N2 107.3(4) . . ?
C9 C10 N4 106.9(4) . . ?
C20 C21 C22 120.5(5) . . ?
C21 C20 C19 120.5(4) . . ?
C20 C19 C18 119.6(5) . . ?
C10 C9 N3 106.7(4) . . ?
O6A Re2A O7A 108.8(18) . . ?
O6A Re2A O4 104.7(12) . . ?
O7A Re2A O4 113.6(15) . . ?
O5 Re2A O6A 111.5(12) . . ?
O5 Re2A O7A 106.6(13) . . ?
O5 Re2A O4 111.7(3) . . ?

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'ShelXS (Sheldrick, 2008)'
_olex2_date_sample_data_collection 18/02/2013
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_12Cl3
_database_code_depnum_ccdc_archive 'CCDC 1419738'
_audit_update_record             
;
2015-08-20 deposited with the CCDC.
2015-10-07 downloaded from the CCDC.
;
_audit_creation_date             2015-07-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2.73(Cl), C14 H24 N5 O2, 0.27(Br)'
_chemical_formula_sum            'C14 H24 Br0.27 Cl2.73 N5 O2'
_chemical_formula_weight         412.85
_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'
Br Br -0.2901 2.4595 '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'

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

_cell_length_a                   10.5678(5)
_cell_length_b                   18.0774(9)
_cell_length_c                   10.1355(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.809(5)
_cell_angle_gamma                90
_cell_volume                     1853.54(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.060
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9524
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.022
_diffrn_ambient_temperature      173.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3293
_reflns_number_total             3783
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3783
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0289
_refine_ls_restrained_S_all      1.084
_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)+(0.0375P)²+0.4752P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0779
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Cl1) = Uanis(Br1)
3. Others
 Sof(Br1)=1-FVAR(1)
 Sof(Cl1)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 N5(H5)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C10(H10A,H10B), C9(H9A,H9B)
4.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5A), C1(H1A), C3(H3), C6(H6), C2(H2)
4.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C4(H4A,H4B,H4C)
4.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.3121(11) 0.1169(6) 0.4948(11) 0.0236(6) Uani 0.7285(19) 1 d . . P A 1
Cl2 Cl 0.75813(4) 0.23874(2) 0.18724(4) 0.02718(13) Uani 1 1 d . . . . .
N5 N 0.75194(13) 0.38924(8) 1.06296(14) 0.0187(3) Uani 1 1 d . . . . .
H5 H 0.7829 0.3444 1.1211 0.022 Uiso 1 1 calc R . . . .
N3 N 1.00547(13) 0.31049(8) 1.06201(14) 0.0213(3) Uani 1 1 d . . . . .
N1 N 0.51463(14) 0.39154(8) 0.70521(14) 0.0231(3) Uani 1 1 d . . . . .
C11 C 0.95305(17) 0.37543(10) 0.97673(18) 0.0245(4) Uani 1 1 d . . . . .
H11A H 0.8962 0.3587 0.8859 0.029 Uiso 1 1 calc R . . . .
H11B H 1.0275 0.4039 0.9612 0.029 Uiso 1 1 calc R . . . .
O1 O 0.69940(13) 0.48316(8) 1.35907(13) 0.0330(3) Uani 1 1 d . . . . .
H1 H 0.7446 0.4868 1.4419 0.049 Uiso 1 1 calc GR . . . .
N4 N 1.05309(14) 0.19752(8) 1.12459(15) 0.0233(3) Uani 1 1 d . . . . .
C12 C 0.87322(16) 0.42550(10) 1.04296(18) 0.0227(4) Uani 1 1 d . . . . .
H12A H 0.9305 0.4421 1.1337 0.027 Uiso 1 1 calc R . . . .
H12B H 0.8460 0.4700 0.9846 0.027 Uiso 1 1 calc R . . . .
O2 O 0.86244(14) 0.40750(8) 1.34198(13) 0.0389(4) Uani 1 1 d . . . . .
C7 C 1.11623(17) 0.24171(11) 1.23421(19) 0.0266(4) Uani 1 1 d . . . . .
H7 H 1.1701 0.2253 1.3214 0.032 Uiso 1 1 calc R . . . .
C13 C 0.68569(17) 0.43792(10) 1.14182(17) 0.0225(4) Uani 1 1 d . . . . .
H13A H 0.5951 0.4194 1.1313 0.027 Uiso 1 1 calc R . . . .
H13B H 0.6785 0.4887 1.1036 0.027 Uiso 1 1 calc R . . . .
N2 N 0.46172(15) 0.35169(9) 0.49696(15) 0.0298(4) Uani 1 1 d . . . . .
C10 C 0.65444(17) 0.36283(10) 0.93220(17) 0.0212(4) Uani 1 1 d . . . . .
H10A H 0.5839 0.3344 0.9558 0.025 Uiso 1 1 calc R . . . .
H10B H 0.7000 0.3290 0.8841 0.025 Uiso 1 1 calc R . . . .
C9 C 0.59134(18) 0.42552(10) 0.83474(17) 0.0257(4) Uani 1 1 d . . . . .
H9A H 0.5330 0.4553 0.8748 0.031 Uiso 1 1 calc R . . . .
H9B H 0.6604 0.4583 0.8186 0.031 Uiso 1 1 calc R . . . .
C8 C 1.0541(2) 0.11642(10) 1.1278(2) 0.0331(5) Uani 1 1 d . . . . .
H8A H 1.1248 0.0993 1.2078 0.050 Uiso 1 1 calc GR . . . .
H8B H 1.0696 0.0974 1.0432 0.050 Uiso 1 1 calc GR . . . .
H8C H 0.9688 0.0984 1.1345 0.050 Uiso 1 1 calc GR . . . .
C5 C 0.98575(17) 0.24019(10) 1.02225(18) 0.0231(4) Uani 1 1 d . . . . .
H5A H 0.9323 0.2235 0.9351 0.028 Uiso 1 1 calc R . . . .
C14 C 0.76132(18) 0.44009(10) 1.29251(18) 0.0248(4) Uani 1 1 d . . . . .
C1 C 0.54635(18) 0.39344(10) 0.58847(18) 0.0266(4) Uani 1 1 d . . . . .
H1A H 0.6179 0.4203 0.5728 0.032 Uiso 1 1 calc R . . . .
C3 C 0.3747(2) 0.32129(12) 0.5586(2) 0.0371(5) Uani 1 1 d . . . . .
H3 H 0.3043 0.2884 0.5171 0.044 Uiso 1 1 calc R . . . .
C6 C 1.08778(17) 0.31262(11) 1.19542(18) 0.0268(4) Uani 1 1 d . . . . .
H6 H 1.1183 0.3555 1.2493 0.032 Uiso 1 1 calc R . . . .
C4 C 0.4627(2) 0.34047(15) 0.3542(2) 0.0479(6) Uani 1 1 d . . . . .
H4A H 0.4339 0.3859 0.3014 0.072 Uiso 1 1 calc GR . . . .
H4B H 0.4025 0.3000 0.3131 0.072 Uiso 1 1 calc GR . . . .
H4C H 0.5525 0.3280 0.3524 0.072 Uiso 1 1 calc GR . . . .
C2 C 0.40726(19) 0.34667(12) 0.6886(2) 0.0335(5) Uani 1 1 d . . . . .
H2 H 0.3638 0.3355 0.7562 0.040 Uiso 1 1 calc R . . . .
Cl3 Cl 0.19004(4) 0.01341(3) 0.83923(4) 0.02832(13) Uani 1 1 d . . . . .
Br1 Br 0.3207(12) 0.1224(7) 0.4988(12) 0.0236(6) Uani 0.2715(19) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N5 C12 1.504(2) . ?
N5 C13 1.492(2) . ?
N5 C10 1.502(2) . ?
N3 C11 1.468(2) . ?
N3 C5 1.331(2) . ?
N3 C6 1.381(2) . ?
N1 C9 1.464(2) . ?
N1 C1 1.320(2) . ?
N1 C2 1.365(2) . ?
C11 C12 1.520(3) . ?
O1 C14 1.321(2) . ?
N4 C7 1.374(2) . ?
N4 C8 1.466(2) . ?
N4 C5 1.323(2) . ?
O2 C14 1.196(2) . ?
C7 C6 1.349(3) . ?
C13 C14 1.506(2) . ?
N2 C1 1.323(2) . ?
N2 C3 1.367(3) . ?
N2 C4 1.464(2) . ?
C10 C9 1.524(2) . ?
C3 C2 1.343(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N5 C12 111.41(13) . . ?
C13 N5 C10 110.59(13) . . ?
C10 N5 C12 114.42(13) . . ?
C5 N3 C11 125.86(14) . . ?
C5 N3 C6 108.79(15) . . ?
C6 N3 C11 125.31(15) . . ?
C1 N1 C9 125.07(15) . . ?
C1 N1 C2 108.80(15) . . ?
C2 N1 C9 125.81(16) . . ?
N3 C11 C12 112.30(15) . . ?
C7 N4 C8 124.37(15) . . ?
C5 N4 C7 108.67(15) . . ?
C5 N4 C8 126.81(15) . . ?
N5 C12 C11 113.79(14) . . ?
C6 C7 N4 107.55(15) . . ?
N5 C13 C14 111.41(14) . . ?
C1 N2 C3 108.47(16) . . ?
C1 N2 C4 125.11(17) . . ?
C3 N2 C4 126.42(17) . . ?
N5 C10 C9 113.28(14) . . ?
N1 C9 C10 107.11(14) . . ?
N4 C5 N3 108.52(15) . . ?
O1 C14 C13 109.72(15) . . ?
O2 C14 O1 126.21(17) . . ?
O2 C14 C13 124.07(17) . . ?
N1 C1 N2 108.54(16) . . ?
C2 C3 N2 107.18(17) . . ?
C7 C6 N3 106.45(16) . . ?
C3 C2 N1 106.99(18) . . ?

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'ShelXS (Sheldrick, 2008)'
_olex2_date_sample_data_collection 2013-03-19
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_trans-trans-16
_database_code_depnum_ccdc_archive 'CCDC 1419739'
_audit_update_record             
;
2015-08-20 deposited with the CCDC.
2015-10-07 downloaded from the CCDC.
;
_audit_creation_date             2015-07-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C15 H13 Cl N4 O3 Re), C3 H6 O, C H4 O'
_chemical_formula_sum            'C34 H36 Cl2 N8 O8 Re2'
_chemical_formula_weight         1128.01
_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      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                   9.4195(3)
_cell_length_b                   13.0035(3)
_cell_length_c                   16.2478(6)
_cell_angle_alpha                96.224(3)
_cell_angle_beta                 93.276(3)
_cell_angle_gamma                100.399(2)
_cell_volume                     1939.91(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    172.9
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.432
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.931
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20675
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.298
_diffrn_reflns_theta_min         2.827
_diffrn_ambient_temperature      172.9
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8363
_reflns_number_total             10178
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.174
_refine_diff_density_min         -1.264
_refine_diff_density_rms         0.132
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         10178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0284
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0255P)²+0.7181P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0591
_refine_ls_wR_factor_ref         0.0648
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C24(H24), C23(H23)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C17(H17), C26(H26), C30(H30), C27(H27), C29(H29), C20(H20), C10(H10),
 C5(H5), C21(H21), C16(H16), C6(H6)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C7(H7A,H7B,H7C), C18(H18A,H18B,H18C), C22(H22A,H22B,
 H22C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C)
2.d Idealised tetrahedral OH refined as rotating group:
 O8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Re1 Re 0.68145(2) 0.26386(2) 0.33487(2) 0.02130(4) Uani 1 1 d . . . . .
Re2 Re 0.76288(2) 0.24841(2) 0.91047(2) 0.02319(5) Uani 1 1 d . . . . .
Cl1 Cl 0.62867(11) 0.43239(7) 0.28651(6) 0.0326(2) Uani 1 1 d . . . . .
Cl2 Cl 0.83541(14) 0.15312(9) 0.78005(7) 0.0457(3) Uani 1 1 d . . . . .
O3 O 0.7594(3) 0.0635(2) 0.39042(19) 0.0377(7) Uani 1 1 d . . . . .
N5 N 0.5098(3) 0.3191(2) 0.80749(19) 0.0235(6) Uani 1 1 d . . . . .
C8 C 0.6099(4) 0.3261(3) 0.4507(2) 0.0245(8) Uani 1 1 d . . . . .
C3 C 0.7249(4) 0.1377(3) 0.3710(2) 0.0248(8) Uani 1 1 d . . . . .
C14 C 0.7111(4) 0.3211(3) 1.0079(3) 0.0291(8) Uani 1 1 d . . . . .
C1 C 0.8843(5) 0.3196(3) 0.3633(3) 0.0319(9) Uani 1 1 d . . . . .
C12 C 0.9491(5) 0.2601(3) 0.9714(3) 0.0368(10) Uani 1 1 d . . . . .
N1 N 0.3539(3) 0.1832(2) 0.3669(2) 0.0309(8) Uani 1 1 d . . . . .
N6 N 0.4631(4) 0.1523(2) 0.7991(2) 0.0296(7) Uani 1 1 d . . . . .
C13 C 0.7008(5) 0.1176(3) 0.9565(3) 0.0340(9) Uani 1 1 d . . . . .
C28 C 0.5365(4) 0.4635(3) 0.9221(2) 0.0223(7) Uani 1 1 d . . . . .
N2 N 0.3634(4) 0.1939(2) 0.2372(2) 0.0351(8) Uani 1 1 d . . . . .
O6 O 0.6862(4) 0.3628(2) 1.07096(19) 0.0417(8) Uani 1 1 d . . . . .
N8 N 0.9501(4) 0.4405(3) 0.8297(2) 0.0342(8) Uani 1 1 d . . . . .
N7 N 0.7265(3) 0.4489(2) 0.8234(2) 0.0248(7) Uani 1 1 d . . . . .
N4 N 0.6609(4) 0.4176(2) 0.5005(2) 0.0291(7) Uani 1 1 d . . . . .
N3 N 0.4886(3) 0.2846(2) 0.4863(2) 0.0277(7) Uani 1 1 d . . . . .
C15 C 0.5612(4) 0.2371(3) 0.8357(2) 0.0233(8) Uani 1 1 d . . . . .
O5 O 0.6666(4) 0.0404(2) 0.9849(2) 0.0571(9) Uani 1 1 d . . . . .
C2 C 0.7385(5) 0.2178(3) 0.2253(3) 0.0330(9) Uani 1 1 d . . . . .
C24 C 0.5721(4) 0.4289(3) 0.8342(2) 0.0243(8) Uani 1 1 d . . . . .
H24 H 0.5263 0.4715 0.7964 0.029 Uiso 1 1 calc R . . . .
C9 C 0.4672(5) 0.3496(3) 0.5564(3) 0.0388(11) Uani 1 1 d . . . . .
H9 H 0.3902 0.3374 0.5915 0.047 Uiso 1 1 calc R . . . .
C19 C 0.8217(4) 0.3909(3) 0.8513(2) 0.0256(8) Uani 1 1 d . . . . .
C17 C 0.3552(5) 0.1815(3) 0.7502(3) 0.0346(9) Uani 1 1 d . . . . .
H17 H 0.2763 0.1357 0.7185 0.041 Uiso 1 1 calc R . . . .
C25 C 0.4538(4) 0.0897(3) 0.4768(3) 0.0290(9) Uani 1 1 d . . . . .
O2 O 0.7794(4) 0.1906(2) 0.1631(2) 0.0521(9) Uani 1 1 d . . . . .
C26 C 0.4194(4) -0.0050(3) 0.4250(3) 0.0316(9) Uani 1 1 d . . . . .
H26 H 0.3635 -0.0094 0.3738 0.038 Uiso 1 1 calc R . . . .
C30 C 0.5325(4) 0.0940(3) 0.5513(3) 0.0320(9) Uani 1 1 d . . . . .
H30 H 0.5546 0.1584 0.5873 0.038 Uiso 1 1 calc R . . . .
C4 C 0.4495(4) 0.2065(3) 0.3085(3) 0.0278(8) Uani 1 1 d . . . . .
C27 C 0.4189(4) 0.4107(3) 0.9561(2) 0.0245(8) Uani 1 1 d . . . . .
H27 H 0.3624 0.3487 0.9259 0.029 Uiso 1 1 calc R . . . .
O4 O 1.0568(4) 0.2644(3) 1.0099(3) 0.0596(10) Uani 1 1 d . . . . .
C29 C 0.6183(4) 0.5537(3) 0.9666(2) 0.0240(8) Uani 1 1 d . . . . .
H29 H 0.7002 0.5910 0.9439 0.029 Uiso 1 1 calc R . . . .
C23 C 0.3933(4) 0.1854(3) 0.4552(3) 0.0300(9) Uani 1 1 d . . . . .
H23 H 0.3021 0.1843 0.4840 0.036 Uiso 1 1 calc R . . . .
C11 C 0.7882(5) 0.4946(3) 0.4879(3) 0.0399(11) Uani 1 1 d . . . . .
H11A H 0.8758 0.4683 0.5037 0.060 Uiso 1 1 calc GR . . . .
H11B H 0.7871 0.5611 0.5223 0.060 Uiso 1 1 calc GR . . . .
H11C H 0.7873 0.5061 0.4293 0.060 Uiso 1 1 calc GR . . . .
C20 C 0.7961(5) 0.5320(3) 0.7852(3) 0.0340(10) Uani 1 1 d . . . . .
H20 H 0.7527 0.5831 0.7608 0.041 Uiso 1 1 calc R . . . .
O1 O 1.0069(3) 0.3447(3) 0.3795(2) 0.0536(9) Uani 1 1 d . . . . .
C10 C 0.5758(5) 0.4325(3) 0.5649(3) 0.0400(11) Uani 1 1 d . . . . .
H10 H 0.5912 0.4906 0.6073 0.048 Uiso 1 1 calc R . . . .
C5 C 0.2130(5) 0.1560(3) 0.3309(4) 0.0470(12) Uani 1 1 d . . . . .
H5 H 0.1279 0.1363 0.3585 0.056 Uiso 1 1 calc R . . . .
C21 C 0.9356(5) 0.5261(3) 0.7896(3) 0.0421(11) Uani 1 1 d . . . . .
H21 H 1.0113 0.5724 0.7688 0.051 Uiso 1 1 calc R . . . .
C16 C 0.3840(4) 0.2873(3) 0.7565(2) 0.0298(9) Uani 1 1 d . . . . .
H16 H 0.3288 0.3312 0.7310 0.036 Uiso 1 1 calc R . . . .
C7 C 0.4131(6) 0.2115(4) 0.1551(3) 0.0470(12) Uani 1 1 d . . . . .
H7A H 0.4825 0.2782 0.1596 0.070 Uiso 1 1 calc GR . . . .
H7B H 0.3300 0.2146 0.1169 0.070 Uiso 1 1 calc GR . . . .
H7C H 0.4599 0.1536 0.1340 0.070 Uiso 1 1 calc GR . . . .
C18 C 0.4684(5) 0.0424(3) 0.8077(3) 0.0458(12) Uani 1 1 d . . . . .
H18A H 0.5663 0.0297 0.7993 0.069 Uiso 1 1 calc GR . . . .
H18B H 0.3993 -0.0037 0.7661 0.069 Uiso 1 1 calc GR . . . .
H18C H 0.4432 0.0273 0.8634 0.069 Uiso 1 1 calc GR . . . .
C6 C 0.2202(5) 0.1629(3) 0.2502(4) 0.0474(12) Uani 1 1 d . . . . .
H6 H 0.1410 0.1489 0.2091 0.057 Uiso 1 1 calc R . . . .
C22 C 1.0887(5) 0.4083(4) 0.8447(4) 0.0500(13) Uani 1 1 d . . . . .
H22A H 1.1210 0.4248 0.9038 0.075 Uiso 1 1 calc GR . . . .
H22B H 1.1605 0.4462 0.8119 0.075 Uiso 1 1 calc GR . . . .
H22C H 1.0778 0.3324 0.8283 0.075 Uiso 1 1 calc GR . . . .
C32 C 0.9764(6) 0.1079(4) 0.5817(4) 0.0600(15) Uani 1 1 d . . . . .
H32A H 0.9086 0.0857 0.5323 0.090 Uiso 1 1 calc GR . . . .
H32B H 0.9286 0.0867 0.6309 0.090 Uiso 1 1 calc GR . . . .
H32C H 1.0611 0.0744 0.5755 0.090 Uiso 1 1 calc GR . . . .
C31 C 1.0223(5) 0.2220(4) 0.5913(3) 0.0493(12) Uani 1 1 d . . . . .
O7 O 1.1483(5) 0.2605(4) 0.5892(4) 0.1028(18) Uani 1 1 d . . . . .
C33 C 0.9115(6) 0.2884(4) 0.6031(4) 0.0626(15) Uani 1 1 d . . . . .
H33A H 0.8464 0.2787 0.5525 0.094 Uiso 1 1 calc GR . . . .
H33B H 0.9590 0.3626 0.6148 0.094 Uiso 1 1 calc GR . . . .
H33C H 0.8557 0.2681 0.6497 0.094 Uiso 1 1 calc GR . . . .
O8 O 0.9291(5) 0.9877(4) 0.1962(4) 0.0932(16) Uani 1 1 d . . . . .
H8 H 0.9835 0.9488 0.2134 0.140 Uiso 1 1 calc GR . . . .
C34 C 0.9181(12) 0.9755(8) 0.1073(6) 0.165(5) Uani 1 1 d . . . . .
H34A H 0.8586 1.0236 0.0873 0.248 Uiso 1 1 calc GR . . . .
H34B H 0.8732 0.9027 0.0862 0.248 Uiso 1 1 calc GR . . . .
H34C H 1.0150 0.9918 0.0875 0.248 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 Cl1 2.5277(9) . ?
Re1 C8 2.159(4) . ?
Re1 C3 1.905(4) . ?
Re1 C1 1.928(4) . ?
Re1 C2 1.952(4) . ?
Re1 C4 2.179(4) . ?
Re2 Cl2 2.5287(10) . ?
Re2 C14 1.888(4) . ?
Re2 C12 1.937(5) . ?
Re2 C13 1.940(4) . ?
Re2 C15 2.169(4) . ?
Re2 C19 2.178(4) . ?
O3 C3 1.141(4) . ?
N5 C15 1.359(4) . ?
N5 C24 1.451(4) . ?
N5 C16 1.378(5) . ?
C8 N4 1.357(5) . ?
C8 N3 1.361(5) . ?
C14 O6 1.163(5) . ?
C1 O1 1.149(5) . ?
C12 O4 1.150(5) . ?
N1 C4 1.367(5) . ?
N1 C23 1.457(5) . ?
N1 C5 1.388(5) . ?
N6 C15 1.362(5) . ?
N6 C17 1.385(5) . ?
N6 C18 1.460(5) . ?
C13 O5 1.151(5) . ?
C28 C24 1.524(5) . ?
C28 C27 1.372(5) . ?
C28 C29 1.386(5) . ?
N2 C4 1.353(5) . ?
N2 C7 1.466(6) . ?
N2 C6 1.371(6) . ?
N8 C19 1.348(5) . ?
N8 C21 1.373(5) . ?
N8 C22 1.456(5) . ?
N7 C24 1.455(5) . ?
N7 C19 1.360(5) . ?
N7 C20 1.384(5) . ?
N4 C11 1.456(5) . ?
N4 C10 1.372(5) . ?
N3 C9 1.391(5) . ?
N3 C23 1.453(5) . ?
C2 O2 1.145(5) . ?
C9 C10 1.334(6) . ?
C17 C16 1.345(5) . ?
C25 C26 1.390(5) . ?
C25 C30 1.373(6) . ?
C25 C23 1.524(5) . ?
C26 C30 1.399(5) 2_656 ?
C30 C26 1.399(5) 2_656 ?
C27 C29 1.378(5) 2_667 ?
C29 C27 1.378(5) 2_667 ?
C20 C21 1.329(6) . ?
C5 C6 1.328(7) . ?
C32 C31 1.458(7) . ?
C31 O7 1.205(6) . ?
C31 C33 1.478(7) . ?
O8 C34 1.433(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
C8 Re1 Cl1 83.55(9) . . ?
C8 Re1 C4 81.48(14) . . ?
C3 Re1 Cl1 178.96(11) . . ?
C3 Re1 C8 96.91(14) . . ?
C3 Re1 C1 84.75(16) . . ?
C3 Re1 C2 88.38(15) . . ?
C3 Re1 C4 96.34(14) . . ?
C1 Re1 Cl1 94.28(12) . . ?
C1 Re1 C8 95.51(15) . . ?
C1 Re1 C2 86.07(18) . . ?
C1 Re1 C4 176.89(15) . . ?
C2 Re1 Cl1 91.18(11) . . ?
C2 Re1 C8 174.59(15) . . ?
C2 Re1 C4 96.86(17) . . ?
C4 Re1 Cl1 84.65(9) . . ?
C14 Re2 Cl2 179.18(13) . . ?
C14 Re2 C12 85.14(18) . . ?
C14 Re2 C13 88.46(17) . . ?
C14 Re2 C15 97.49(15) . . ?
C14 Re2 C19 93.73(15) . . ?
C12 Re2 Cl2 94.37(13) . . ?
C12 Re2 C13 87.86(18) . . ?
C12 Re2 C15 176.61(16) . . ?
C12 Re2 C19 95.71(16) . . ?
C13 Re2 Cl2 92.17(13) . . ?
C13 Re2 C15 94.34(16) . . ?
C13 Re2 C19 175.95(16) . . ?
C15 Re2 Cl2 82.98(9) . . ?
C15 Re2 C19 82.01(14) . . ?
C19 Re2 Cl2 85.66(9) . . ?
C15 N5 C24 123.9(3) . . ?
C15 N5 C16 112.8(3) . . ?
C16 N5 C24 123.1(3) . . ?
N4 C8 Re1 130.5(3) . . ?
N4 C8 N3 103.2(3) . . ?
N3 C8 Re1 126.0(3) . . ?
O3 C3 Re1 175.5(3) . . ?
O6 C14 Re2 175.2(4) . . ?
O1 C1 Re1 174.6(3) . . ?
O4 C12 Re2 177.1(4) . . ?
C4 N1 C23 125.0(3) . . ?
C4 N1 C5 110.8(4) . . ?
C5 N1 C23 124.2(4) . . ?
C15 N6 C17 112.0(3) . . ?
C15 N6 C18 125.4(3) . . ?
C17 N6 C18 122.6(3) . . ?
O5 C13 Re2 178.5(4) . . ?
C27 C28 C24 121.1(3) . . ?
C27 C28 C29 119.1(3) . . ?
C29 C28 C24 119.7(3) . . ?
C4 N2 C7 125.4(4) . . ?
C4 N2 C6 111.8(4) . . ?
C6 N2 C7 122.7(4) . . ?
C19 N8 C21 111.7(3) . . ?
C19 N8 C22 125.5(4) . . ?
C21 N8 C22 122.8(4) . . ?
C19 N7 C24 124.7(3) . . ?
C19 N7 C20 111.3(3) . . ?
C20 N7 C24 123.9(3) . . ?
C8 N4 C11 125.5(3) . . ?
C8 N4 C10 112.2(3) . . ?
C10 N4 C11 122.3(3) . . ?
C8 N3 C9 111.1(3) . . ?
C8 N3 C23 124.7(3) . . ?
C9 N3 C23 124.2(3) . . ?
N5 C15 Re2 125.8(3) . . ?
N5 C15 N6 102.5(3) . . ?
N6 C15 Re2 131.5(3) . . ?
O2 C2 Re1 176.2(4) . . ?
N5 C24 C28 111.8(3) . . ?
N5 C24 N7 110.3(3) . . ?
N7 C24 C28 113.3(3) . . ?
C10 C9 N3 106.8(4) . . ?
N8 C19 Re2 131.6(3) . . ?
N8 C19 N7 103.4(3) . . ?
N7 C19 Re2 125.0(3) . . ?
C16 C17 N6 106.6(4) . . ?
C26 C25 C23 120.5(4) . . ?
C30 C25 C26 119.3(3) . . ?
C30 C25 C23 120.0(3) . . ?
C25 C26 C30 119.7(4) . 2_656 ?
C25 C30 C26 121.0(4) . 2_656 ?
N1 C4 Re1 124.9(3) . . ?
N2 C4 Re1 131.5(3) . . ?
N2 C4 N1 103.4(3) . . ?
C28 C27 C29 120.9(3) . 2_667 ?
C27 C29 C28 120.0(3) 2_667 . ?
N1 C23 C25 113.9(3) . . ?
N3 C23 N1 109.7(3) . . ?
N3 C23 C25 112.9(3) . . ?
C21 C20 N7 106.3(4) . . ?
C9 C10 N4 106.7(4) . . ?
C6 C5 N1 106.7(4) . . ?
C20 C21 N8 107.3(4) . . ?
C17 C16 N5 106.0(4) . . ?
C5 C6 N2 107.2(4) . . ?
C32 C31 C33 118.6(5) . . ?
O7 C31 C32 120.1(5) . . ?
O7 C31 C33 121.3(5) . . ?

_olex2_date_sample_data_collection 2013-10-28
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_14
_database_code_depnum_ccdc_archive 'CCDC 1419740'
_audit_update_record             
;
2015-08-20 deposited with the CCDC.
2015-10-07 downloaded from the CCDC.
;
_audit_creation_date             2015-07-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H12 Cl N4 O3 Re'
_chemical_formula_sum            'C12 H12 Cl N4 O3 Re'
_chemical_formula_weight         481.91
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.6760(3)
_cell_length_b                   17.0407(7)
_cell_length_c                   11.3204(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.879(4)
_cell_angle_gamma                90
_cell_volume                     1479.97(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    150
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.405
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.163
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7793
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.912
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2717
_reflns_number_total             3031
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.201
_refine_diff_density_min         -0.878
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3031
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0196
_refine_ls_restrained_S_all      1.025
_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)+(0.0114P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0383
_refine_ls_wR_factor_ref         0.0399
_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:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C10(H10), C9(H9)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Re1 Re 0.22643(2) 0.41855(2) 0.19506(2) 0.01586(5) Uani 1 1 d . . . . .
Cl1 Cl 0.08123(9) 0.39808(5) 0.38935(8) 0.02365(18) Uani 1 1 d . . . . .
C2 C 0.0617(4) 0.3460(2) 0.1193(3) 0.0253(8) Uani 1 1 d . . . . .
N1 N 0.5826(3) 0.48107(14) 0.3007(3) 0.0179(6) Uani 1 1 d . . . . .
C6 C 0.5445(4) 0.58286(18) 0.4106(3) 0.0273(8) Uani 1 1 d . . . . .
H6 H 0.5622 0.6262 0.4624 0.033 Uiso 1 1 calc R . . . .
C8 C 0.4101(4) 0.32967(18) 0.2561(3) 0.0206(7) Uani 1 1 d . . . . .
C1 C 0.0770(4) 0.5061(2) 0.1521(3) 0.0264(8) Uani 1 1 d . . . . .
O3 O 0.3970(3) 0.43466(13) -0.0425(2) 0.0295(6) Uani 1 1 d . . . . .
N3 N 0.5845(3) 0.34331(14) 0.2711(3) 0.0197(6) Uani 1 1 d . . . . .
O1 O -0.0100(4) 0.55821(17) 0.1240(3) 0.0483(8) Uani 1 1 d . . . . .
O2 O -0.0403(3) 0.30566(15) 0.0742(3) 0.0424(7) Uani 1 1 d . . . . .
C4 C 0.4074(4) 0.49516(17) 0.2912(3) 0.0169(7) Uani 1 1 d . . . . .
N4 N 0.3912(3) 0.25563(15) 0.2968(3) 0.0239(7) Uani 1 1 d . . . . .
C3 C 0.3348(4) 0.42957(17) 0.0482(3) 0.0190(7) Uani 1 1 d . . . . .
C12 C 0.6651(4) 0.41687(16) 0.2395(3) 0.0207(7) Uani 1 1 d . . . . .
H12A H 0.6528 0.4250 0.1530 0.025 Uiso 1 1 calc R . . . .
H12B H 0.7910 0.4154 0.2614 0.025 Uiso 1 1 calc R . . . .
N2 N 0.3868(3) 0.55904(15) 0.3594(3) 0.0214(6) Uani 1 1 d . . . . .
C5 C 0.6670(4) 0.53383(18) 0.3737(3) 0.0239(8) Uani 1 1 d . . . . .
H5 H 0.7880 0.5352 0.3940 0.029 Uiso 1 1 calc R . . . .
C10 C 0.5484(4) 0.2248(2) 0.3378(4) 0.0319(9) Uani 1 1 d . . . . .
H10 H 0.5669 0.1741 0.3709 0.038 Uiso 1 1 calc R . . . .
C7 C 0.2221(4) 0.59814(19) 0.3810(4) 0.0297(9) Uani 1 1 d . . . . .
H7A H 0.2361 0.6324 0.4502 0.045 Uiso 1 1 calc GR . . . .
H7B H 0.1324 0.5587 0.3957 0.045 Uiso 1 1 calc GR . . . .
H7C H 0.1869 0.6296 0.3118 0.045 Uiso 1 1 calc GR . . . .
C9 C 0.6690(4) 0.27979(18) 0.3222(3) 0.0269(8) Uani 1 1 d . . . . .
H9 H 0.7898 0.2759 0.3423 0.032 Uiso 1 1 calc R . . . .
C11 C 0.2260(4) 0.2134(2) 0.3001(4) 0.0337(10) Uani 1 1 d . . . . .
H11A H 0.1447 0.2426 0.3486 0.051 Uiso 1 1 calc GR . . . .
H11B H 0.2459 0.1612 0.3344 0.051 Uiso 1 1 calc GR . . . .
H11C H 0.1765 0.2080 0.2196 0.051 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 Cl1 2.5223(8) . ?
Re1 C2 1.948(4) . ?
Re1 C8 2.167(3) . ?
Re1 C1 1.934(4) . ?
Re1 C4 2.173(3) . ?
Re1 C3 1.892(4) . ?
C2 O2 1.148(4) . ?
N1 C4 1.366(4) . ?
N1 C12 1.452(4) . ?
N1 C5 1.370(4) . ?
C6 N2 1.385(4) . ?
C6 C5 1.335(5) . ?
C8 N3 1.364(4) . ?
C8 N4 1.353(4) . ?
C1 O1 1.150(4) . ?
O3 C3 1.150(4) . ?
N3 C12 1.448(4) . ?
N3 C9 1.379(4) . ?
C4 N2 1.347(4) . ?
N4 C10 1.382(4) . ?
N4 C11 1.460(4) . ?
N2 C7 1.457(4) . ?
C10 C9 1.333(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
C2 Re1 Cl1 89.84(11) . . ?
C2 Re1 C8 95.91(13) . . ?
C2 Re1 C4 175.96(13) . . ?
C8 Re1 Cl1 85.81(9) . . ?
C8 Re1 C4 82.04(12) . . ?
C1 Re1 Cl1 92.90(11) . . ?
C1 Re1 C2 90.45(14) . . ?
C1 Re1 C8 173.51(13) . . ?
C1 Re1 C4 91.54(13) . . ?
C4 Re1 Cl1 86.55(8) . . ?
C3 Re1 Cl1 177.72(9) . . ?
C3 Re1 C2 88.51(14) . . ?
C3 Re1 C8 92.81(13) . . ?
C3 Re1 C1 88.67(14) . . ?
C3 Re1 C4 95.05(12) . . ?
O2 C2 Re1 177.2(3) . . ?
C4 N1 C12 122.6(3) . . ?
C4 N1 C5 112.1(3) . . ?
C5 N1 C12 125.3(3) . . ?
C5 C6 N2 107.5(3) . . ?
N3 C8 Re1 123.1(2) . . ?
N4 C8 Re1 133.2(2) . . ?
N4 C8 N3 103.4(3) . . ?
O1 C1 Re1 178.4(3) . . ?
C8 N3 C12 122.9(3) . . ?
C8 N3 C9 111.4(3) . . ?
C9 N3 C12 125.7(3) . . ?
N1 C4 Re1 123.0(2) . . ?
N2 C4 Re1 133.4(2) . . ?
N2 C4 N1 103.3(3) . . ?
C8 N4 C10 111.5(3) . . ?
C8 N4 C11 124.9(3) . . ?
C10 N4 C11 123.6(3) . . ?
O3 C3 Re1 177.9(3) . . ?
N3 C12 N1 109.7(2) . . ?
C6 N2 C7 123.2(3) . . ?
C4 N2 C6 111.0(3) . . ?
C4 N2 C7 125.8(3) . . ?
C6 C5 N1 106.0(3) . . ?
C9 C10 N4 106.9(3) . . ?
C10 C9 N3 106.8(3) . . ?

_olex2_date_sample_data_collection 2014-07-11
_olex2_submission_original_sample_id PJB290
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_trans-15
_database_code_depnum_ccdc_archive 'CCDC 1419741'
_audit_update_record             
;
2015-08-20 deposited with the CCDC.
2015-10-07 downloaded from the CCDC.
;
_audit_creation_date             2015-07-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H16 Cl N4 O3 Re, C H Cl3'
_chemical_formula_sum            'C19 H17 Cl4 N4 O3 Re'
_chemical_formula_weight         677.36
_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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   15.0212(4)
_cell_length_b                   12.3025(4)
_cell_length_c                   12.4828(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2306.80(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    173
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.760
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.950
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19918
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.165
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2281
_reflns_number_total             2472
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         2.129
_refine_diff_density_min         -2.180
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2472
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0236
_refine_ls_restrained_S_all      1.044
_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)+(0.0251P)²+9.2713P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0555
_refine_ls_wR_factor_ref         0.0580
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C2(H2), C3(H3), C8(H8)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Re1 Re 0.83194(2) 0.2500 0.46816(2) 0.01685(7) Uani 1 2 d S T P . .
Cl1 Cl 0.92803(9) 0.2500 0.30243(11) 0.0313(3) Uani 1 2 d S T P . .
O2 O 0.7260(3) 0.2500 0.6764(3) 0.0269(8) Uani 1 2 d S T P . .
N1 N 0.66656(18) 0.3466(2) 0.3433(2) 0.0192(6) Uani 1 1 d . . . . .
C5 C 0.5776(3) 0.2500 0.4804(4) 0.0244(11) Uani 1 2 d S T P . .
C10 C 0.9060(2) 0.3586(3) 0.5369(3) 0.0255(8) Uani 1 1 d . . . . .
N2 N 0.7694(2) 0.4649(3) 0.3403(3) 0.0269(7) Uani 1 1 d . . . . .
O1 O 0.9495(2) 0.4193(3) 0.5836(2) 0.0414(8) Uani 1 1 d . . . . .
C4 C 0.6145(3) 0.2500 0.3669(4) 0.0188(10) Uani 1 2 d S T P . .
H4 H 0.5625 0.2500 0.3170 0.023 Uiso 1 2 calc RS T P . .
C6 C 0.5576(3) 0.3472(4) 0.5307(3) 0.0349(10) Uani 1 1 d . . . . .
H6 H 0.5705 0.4143 0.4963 0.042 Uiso 1 1 calc R . . . .
C7 C 0.5187(3) 0.3463(5) 0.6318(4) 0.0528(14) Uani 1 1 d . . . . .
H7 H 0.5053 0.4130 0.6665 0.063 Uiso 1 1 calc R . . . .
C1 C 0.7506(2) 0.3655(3) 0.3806(3) 0.0203(7) Uani 1 1 d . . . . .
C2 C 0.6350(3) 0.4312(3) 0.2820(3) 0.0279(8) Uani 1 1 d . . . . .
H2 H 0.5789 0.4357 0.2473 0.034 Uiso 1 1 calc R . . . .
C11 C 0.7624(3) 0.2500 0.5943(4) 0.0189(10) Uani 1 2 d S T P . .
C3 C 0.6996(3) 0.5057(4) 0.2813(4) 0.0355(10) Uani 1 1 d . . . . .
H3 H 0.6978 0.5744 0.2465 0.043 Uiso 1 1 calc R . . . .
C9 C 0.8532(3) 0.5233(4) 0.3550(4) 0.0377(10) Uani 1 1 d . . . . .
H9A H 0.8578 0.5482 0.4294 0.057 Uiso 1 1 calc GR . . . .
H9B H 0.8548 0.5862 0.3069 0.057 Uiso 1 1 calc GR . . . .
H9C H 0.9031 0.4749 0.3387 0.057 Uiso 1 1 calc GR . . . .
C8 C 0.4994(5) 0.2500 0.6817(5) 0.058(2) Uani 1 2 d S T P . .
H8 H 0.4727 0.2500 0.7507 0.070 Uiso 1 2 calc RS T P . .
C12 C 0.7716(5) 0.2500 0.0938(6) 0.060(2) Uani 1 2 d S T P . .
H12 H 0.7826 0.2500 0.1728 0.072 Uiso 1 2 calc RS T P . .
Cl2 Cl 0.65564(11) 0.2500 0.07477(14) 0.0499(4) Uani 1 2 d S T P . .
Cl3 Cl 0.81826(14) 0.3679(3) 0.0427(2) 0.1782(19) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 Cl1 2.5225(13) . ?
Re1 C10 1.939(4) . ?
Re1 C10 1.939(4) 8_565 ?
Re1 C1 2.169(4) 8_565 ?
Re1 C1 2.169(4) . ?
Re1 C11 1.889(5) . ?
O2 C11 1.161(6) . ?
N1 C4 1.453(4) . ?
N1 C1 1.365(4) . ?
N1 C2 1.376(5) . ?
C5 C4 1.522(7) . ?
C5 C6 1.383(5) . ?
C5 C6 1.383(5) 8_565 ?
C10 O1 1.151(5) . ?
N2 C1 1.352(5) . ?
N2 C3 1.377(5) . ?
N2 C9 1.460(5) . ?
C4 N1 1.453(4) 8_565 ?
C6 C7 1.391(6) . ?
C7 C8 1.370(7) . ?
C2 C3 1.335(6) . ?
C8 C7 1.370(7) 8_565 ?
C12 Cl2 1.758(7) . ?
C12 Cl3 1.733(5) . ?
C12 Cl3 1.733(5) 8_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 Re1 Cl1 91.99(11) 8_565 . ?
C10 Re1 Cl1 91.99(11) . . ?
C10 Re1 C10 87.1(2) . 8_565 ?
C10 Re1 C1 95.44(15) . . ?
C10 Re1 C1 175.93(14) 8_565 . ?
C10 Re1 C1 95.44(15) 8_565 8_565 ?
C10 Re1 C1 175.93(14) . 8_565 ?
C1 Re1 Cl1 84.78(9) 8_565 . ?
C1 Re1 Cl1 84.78(9) . . ?
C1 Re1 C1 81.83(18) 8_565 . ?
C11 Re1 Cl1 178.67(14) . . ?
C11 Re1 C10 87.04(15) . 8_565 ?
C11 Re1 C10 87.04(15) . . ?
C11 Re1 C1 96.22(14) . 8_565 ?
C11 Re1 C1 96.22(14) . . ?
C1 N1 C4 124.6(3) . . ?
C1 N1 C2 112.3(3) . . ?
C2 N1 C4 123.1(3) . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 C4 120.1(3) 8_565 . ?
C6 C5 C6 119.7(5) 8_565 . ?
O1 C10 Re1 175.7(3) . . ?
C1 N2 C3 111.7(3) . . ?
C1 N2 C9 125.4(3) . . ?
C3 N2 C9 123.0(3) . . ?
N1 C4 N1 109.8(4) 8_565 . ?
N1 C4 C5 112.6(3) 8_565 . ?
N1 C4 C5 112.6(3) . . ?
C5 C6 C7 119.7(5) . . ?
C8 C7 C6 120.6(5) . . ?
N1 C1 Re1 125.5(3) . . ?
N2 C1 Re1 131.4(3) . . ?
N2 C1 N1 102.7(3) . . ?
C3 C2 N1 105.8(3) . . ?
O2 C11 Re1 174.5(4) . . ?
C2 C3 N2 107.4(4) . . ?
C7 C8 C7 119.7(6) 8_565 . ?
Cl3 C12 Cl2 110.6(3) 8_565 . ?
Cl3 C12 Cl2 110.6(3) . . ?
Cl3 C12 Cl3 113.7(5) 8_565 . ?

_olex2_date_sample_data_collection 2014-07-29
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20
_database_code_depnum_ccdc_archive 'CCDC 1419742'
_audit_update_record             
;
2015-08-20 deposited with the CCDC.
2015-10-07 downloaded from the CCDC.
;
_audit_creation_date             2015-08-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H25 N5 O5 Re, F6 P'
_chemical_formula_sum            'C19 H25 F6 N5 O5 P Re'
_chemical_formula_weight         734.61
_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'
F F 0.0171 0.0103 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.7542(4)
_cell_length_b                   18.0646(8)
_cell_length_c                   13.7100(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.253(4)
_cell_angle_gamma                90
_cell_volume                     2401.41(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    173
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.216
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.032
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1432
_exptl_crystal_preparation       'Fragment cut from larger cubic crystal'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13156
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.933
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4262
_reflns_number_total             4904
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.733
_refine_diff_density_min         -1.856
_refine_diff_density_rms         0.141
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4904
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0281
_refine_ls_restrained_S_all      1.090
_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)+(0.0233P)²+0.9179P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0610
_refine_ls_wR_factor_ref         0.0646
_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:
 C15(H15A,H15B), C12(H12A,H12B), C14(H14A,H14B), C18(H18A,H18B), C16(H16A,
 H16B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C5(H5), C10(H10)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C19(H19A,H19B,H19C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Re1 Re 0.35417(2) 0.19636(2) 0.14929(2) 0.01034(7) Uani 1 1 d . . . . .
P1 P -0.08658(12) 0.40292(6) 0.22949(8) 0.0178(2) Uani 1 1 d . . . . .
F2 F -0.1556(3) 0.35124(16) 0.14375(18) 0.0309(7) Uani 1 1 d . . . . .
O5 O -0.1588(3) 0.09823(17) 0.13184(19) 0.0182(7) Uani 1 1 d . . . . .
C8 C 0.3080(4) 0.2972(2) 0.0629(3) 0.0145(9) Uani 1 1 d . . . . .
N5 N 0.1236(3) 0.15881(18) 0.1064(2) 0.0110(7) Uani 1 1 d . . . . .
N3 N 0.1906(4) 0.31247(18) 0.0047(2) 0.0165(8) Uani 1 1 d . . . . .
C2 C 0.3051(4) 0.2519(2) 0.2621(3) 0.0174(9) Uani 1 1 d . . . . .
O1 O 0.6555(3) 0.22963(18) 0.2209(2) 0.0273(8) Uani 1 1 d . . . . .
N2 N 0.5059(3) 0.14090(19) -0.0371(2) 0.0152(8) Uani 1 1 d . . . . .
N4 N 0.3828(4) 0.36014(19) 0.0596(2) 0.0168(8) Uani 1 1 d . . . . .
C15 C 0.0325(4) 0.2231(2) 0.0730(3) 0.0189(9) Uani 1 1 d . . . . .
H15A H -0.0631 0.2048 0.0580 0.023 Uiso 1 1 calc R . . . .
H15B H 0.0330 0.2588 0.1279 0.023 Uiso 1 1 calc R . . . .
O4 O -0.0949(3) 0.10093(16) 0.29412(19) 0.0190(7) Uani 1 1 d . . . . .
C12 C 0.2183(4) 0.0428(2) 0.0338(3) 0.0181(9) Uani 1 1 d . . . . .
H12A H 0.2456 0.0288 0.1030 0.022 Uiso 1 1 calc R . . . .
H12B H 0.1846 -0.0023 -0.0024 0.022 Uiso 1 1 calc R . . . .
C3 C 0.3936(4) 0.1086(2) 0.2280(3) 0.0150(9) Uani 1 1 d . . . . .
F1 F -0.0182(3) 0.45530(15) 0.31560(19) 0.0369(7) Uani 1 1 d . . . . .
C14 C 0.0732(5) 0.2631(3) -0.0153(3) 0.0241(11) Uani 1 1 d . . . . .
H14A H 0.0950 0.2261 -0.0645 0.029 Uiso 1 1 calc R . . . .
H14B H -0.0068 0.2924 -0.0446 0.029 Uiso 1 1 calc R . . . .
C1 C 0.5424(5) 0.2196(2) 0.1901(3) 0.0169(9) Uani 1 1 d . . . . .
C6 C 0.5012(4) 0.0838(2) -0.1038(3) 0.0183(9) Uani 1 1 d . . . . .
H6 H 0.5616 0.0766 -0.1529 0.022 Uiso 1 1 calc R . . . .
C7 C 0.6048(5) 0.2020(3) -0.0354(3) 0.0270(11) Uani 1 1 d . . . . .
H7A H 0.6646 0.2013 0.0269 0.041 Uiso 1 1 calc GR . . . .
H7B H 0.5548 0.2491 -0.0419 0.041 Uiso 1 1 calc GR . . . .
H7C H 0.6610 0.1965 -0.0899 0.041 Uiso 1 1 calc GR . . . .
C17 C -0.0730(4) 0.1091(2) 0.2008(3) 0.0158(9) Uani 1 1 d . . . . .
C9 C 0.1931(5) 0.3828(2) -0.0345(3) 0.0224(10) Uani 1 1 d . . . . .
H9 H 0.1226 0.4055 -0.0775 0.027 Uiso 1 1 calc R . . . .
C5 C 0.3959(5) 0.0405(2) -0.0865(3) 0.0180(9) Uani 1 1 d . . . . .
H5 H 0.3665 -0.0034 -0.1208 0.022 Uiso 1 1 calc R . . . .
O2 O 0.2836(4) 0.28473(19) 0.3298(2) 0.0315(8) Uani 1 1 d . . . . .
F4 F -0.2272(4) 0.4022(2) 0.2784(2) 0.0638(11) Uani 1 1 d . . . . .
F5 F -0.1380(4) 0.47393(17) 0.1693(2) 0.0616(12) Uani 1 1 d . . . . .
C10 C 0.3131(5) 0.4122(2) -0.0003(3) 0.0224(10) Uani 1 1 d . . . . .
H10 H 0.3451 0.4603 -0.0144 0.027 Uiso 1 1 calc R . . . .
C18 C -0.2280(4) 0.0715(3) 0.3138(3) 0.0202(10) Uani 1 1 d . . . . .
H18A H -0.2254 0.0167 0.3146 0.024 Uiso 1 1 calc R . . . .
H18B H -0.3008 0.0876 0.2621 0.024 Uiso 1 1 calc R . . . .
C16 C 0.0763(4) 0.1314(2) 0.1996(3) 0.0154(9) Uani 1 1 d . . . . .
H16A H 0.0965 0.1705 0.2497 0.018 Uiso 1 1 calc R . . . .
H16B H 0.1339 0.0881 0.2213 0.018 Uiso 1 1 calc R . . . .
O3 O 0.4259(3) 0.05785(17) 0.2763(2) 0.0267(8) Uani 1 1 d . . . . .
C4 C 0.4052(4) 0.1346(2) 0.0226(3) 0.0127(8) Uani 1 1 d . . . . .
F6 F 0.0516(4) 0.4034(2) 0.1796(3) 0.0678(11) Uani 1 1 d . . . . .
C19 C -0.2575(5) 0.1003(3) 0.4112(3) 0.0342(12) Uani 1 1 d . . . . .
H19A H -0.2565 0.1546 0.4102 0.051 Uiso 1 1 calc GR . . . .
H19B H -0.1870 0.0824 0.4621 0.051 Uiso 1 1 calc GR . . . .
H19C H -0.3484 0.0830 0.4254 0.051 Uiso 1 1 calc GR . . . .
C13 C 0.1040(4) 0.0992(2) 0.0294(3) 0.0173(9) Uani 1 1 d . . . . .
H13A H 0.0953 0.1229 -0.0361 0.021 Uiso 1 1 calc R . . . .
H13B H 0.0163 0.0731 0.0362 0.021 Uiso 1 1 calc R . . . .
C11 C 0.5146(5) 0.3762(3) 0.1171(3) 0.0253(11) Uani 1 1 d . . . . .
H11A H 0.5086 0.3637 0.1861 0.038 Uiso 1 1 calc GR . . . .
H11B H 0.5358 0.4290 0.1117 0.038 Uiso 1 1 calc GR . . . .
H11C H 0.5876 0.3468 0.0922 0.038 Uiso 1 1 calc GR . . . .
F3 F -0.0364(4) 0.33201(17) 0.2898(2) 0.0576(11) Uani 1 1 d . . . . .
N1 N 0.3378(4) 0.07198(19) -0.0088(2) 0.0143(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
Re1 C8 2.193(4) . ?
Re1 N5 2.362(3) . ?
Re1 C2 1.946(4) . ?
Re1 C3 1.932(4) . ?
Re1 C1 1.907(4) . ?
Re1 C4 2.167(4) . ?
P1 F2 1.592(3) . ?
P1 F1 1.601(3) . ?
P1 F4 1.591(3) . ?
P1 F5 1.577(3) . ?
P1 F6 1.577(4) . ?
P1 F3 1.574(3) . ?
O5 C17 1.209(5) . ?
C8 N3 1.351(5) . ?
C8 N4 1.353(5) . ?
N5 C15 1.502(5) . ?
N5 C16 1.490(5) . ?
N5 C13 1.506(5) . ?
N3 C14 1.454(5) . ?
N3 C9 1.380(5) . ?
C2 O2 1.141(5) . ?
O1 C1 1.152(5) . ?
N2 C6 1.376(5) . ?
N2 C7 1.464(6) . ?
N2 C4 1.350(5) . ?
N4 C10 1.378(5) . ?
N4 C11 1.463(5) . ?
C15 C14 1.501(6) . ?
O4 C17 1.327(5) . ?
O4 C18 1.455(5) . ?
C12 C13 1.506(6) . ?
C12 N1 1.458(5) . ?
C3 O3 1.155(5) . ?
C6 C5 1.333(6) . ?
C17 C16 1.513(6) . ?
C9 C10 1.324(6) . ?
C5 N1 1.382(5) . ?
C18 C19 1.490(6) . ?
C4 N1 1.356(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 Re1 N5 88.29(14) . . ?
C2 Re1 C8 86.98(16) . . ?
C2 Re1 N5 92.06(14) . . ?
C2 Re1 C4 179.03(16) . . ?
C3 Re1 C8 178.69(16) . . ?
C3 Re1 N5 91.71(14) . . ?
C3 Re1 C2 91.71(17) . . ?
C3 Re1 C4 88.66(15) . . ?
C1 Re1 C8 96.32(17) . . ?
C1 Re1 N5 175.39(14) . . ?
C1 Re1 C2 88.05(18) . . ?
C1 Re1 C3 83.68(17) . . ?
C1 Re1 C4 92.88(17) . . ?
C4 Re1 C8 92.65(14) . . ?
C4 Re1 N5 87.04(13) . . ?
F2 P1 F1 179.53(17) . . ?
F4 P1 F2 89.50(17) . . ?
F4 P1 F1 90.18(17) . . ?
F5 P1 F2 90.34(15) . . ?
F5 P1 F1 89.31(16) . . ?
F5 P1 F4 89.3(2) . . ?
F6 P1 F2 89.77(17) . . ?
F6 P1 F1 90.55(18) . . ?
F6 P1 F4 179.2(2) . . ?
F6 P1 F5 90.4(2) . . ?
F3 P1 F2 89.60(16) . . ?
F3 P1 F1 90.74(15) . . ?
F3 P1 F4 90.3(2) . . ?
F3 P1 F5 179.6(2) . . ?
F3 P1 F6 90.1(2) . . ?
N3 C8 Re1 126.8(3) . . ?
N3 C8 N4 103.6(3) . . ?
N4 C8 Re1 129.5(3) . . ?
C15 N5 Re1 111.7(2) . . ?
C15 N5 C13 108.3(3) . . ?
C16 N5 Re1 104.9(2) . . ?
C16 N5 C15 106.8(3) . . ?
C16 N5 C13 109.7(3) . . ?
C13 N5 Re1 115.1(2) . . ?
C8 N3 C14 125.9(3) . . ?
C8 N3 C9 111.6(4) . . ?
C9 N3 C14 122.5(4) . . ?
O2 C2 Re1 176.3(4) . . ?
C6 N2 C7 123.4(4) . . ?
C4 N2 C6 111.5(3) . . ?
C4 N2 C7 125.1(4) . . ?
C8 N4 C10 111.1(3) . . ?
C8 N4 C11 126.4(3) . . ?
C10 N4 C11 122.2(3) . . ?
C14 C15 N5 114.8(4) . . ?
C17 O4 C18 117.3(3) . . ?
N1 C12 C13 111.1(3) . . ?
O3 C3 Re1 175.5(3) . . ?
N3 C14 C15 114.6(3) . . ?
O1 C1 Re1 174.5(4) . . ?
C5 C6 N2 107.0(4) . . ?
O5 C17 O4 124.4(4) . . ?
O5 C17 C16 128.3(4) . . ?
O4 C17 C16 107.2(3) . . ?
C10 C9 N3 106.5(4) . . ?
C6 C5 N1 106.5(4) . . ?
C9 C10 N4 107.2(4) . . ?
O4 C18 C19 107.5(3) . . ?
N5 C16 C17 119.1(3) . . ?
N2 C4 Re1 133.5(3) . . ?
N2 C4 N1 103.7(3) . . ?
N1 C4 Re1 122.6(3) . . ?
N5 C13 C12 114.8(3) . . ?
C5 N1 C12 124.9(4) . . ?
C4 N1 C12 123.7(3) . . ?
C4 N1 C5 111.3(4) . . ?

_olex2_date_sample_data_collection 2015-06-30
_olex2_submission_original_sample_id 20
_olex2_submission_special_instructions 'No special instructions were received'
