# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_mo_iagvb76_0m_ab
_database_code_depnum_ccdc_archive 'CCDC 1858654'
_audit_update_record             
;
2018-11-22 deposited with the CCDC.
2018-12-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        6d
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H12 Mn N O4'
_chemical_formula_sum            'C16 H12 Mn N O4'
_chemical_formula_weight         337.21

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'
Mn Mn 0.3368 0.7283 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   30.935(3)
_cell_length_b                   6.1805(5)
_cell_length_c                   15.1240(14)
_cell_angle_alpha                90
_cell_angle_beta                 108.124(4)
_cell_angle_gamma                90
_cell_volume                     2748.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9940
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      29.85

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.399
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.046
_exptl_absorpt_coefficient_mu    0.978
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6753
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35346
_diffrn_reflns_av_R_equivalents  0.0907
_diffrn_reflns_av_sigmaI/netI    0.0517
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.740
_diffrn_reflns_theta_max         30.174
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4058
_reflns_number_gt                3154
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0461P)²+14.0216P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4058
_refine_ls_number_parameters     199
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1227
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.57054(2) 0.30036(6) 0.42359(3) 0.00860(11) Uani 1 1 d . U . . .
O1 O 0.67748(6) 0.0205(3) 0.55751(13) 0.0132(4) Uani 1 1 d . . . . .
C1 C 0.59927(9) 0.2460(5) 0.56939(17) 0.0134(5) Uani 1 1 d . . . . .
H1 H 0.601569 0.103220 0.601597 0.016 Uiso 1 1 calc R U . . .
N1 N 0.71322(7) 0.3539(4) 0.61626(15) 0.0100(4) Uani 1 1 d . . . . .
H1N H 0.708298 0.479828 0.638506 0.012 Uiso 1 1 calc R U . . .
C2 C 0.56315(11) 0.3963(5) 0.55502(19) 0.0193(6) Uani 1 1 d . . . . .
H2 H 0.535264 0.374957 0.574133 0.023 Uiso 1 1 calc R U . . .
O2 O 0.61141(8) -0.0509(4) 0.34282(15) 0.0237(5) Uani 1 1 d . . . . .
O3 O 0.48225(8) 0.0740(4) 0.37371(17) 0.0263(5) Uani 1 1 d . . . . .
C3 C 0.57252(10) 0.5785(5) 0.50932(19) 0.0166(6) Uani 1 1 d . . . . .
H3 H 0.552989 0.710258 0.491454 0.020 Uiso 1 1 calc R U . . .
O4 O 0.54803(8) 0.5521(4) 0.24936(15) 0.0251(5) Uani 1 1 d . . . . .
C4 C 0.61666(9) 0.5478(4) 0.49760(19) 0.0140(5) Uani 1 1 d . . . . .
H4 H 0.633135 0.654085 0.469861 0.017 Uiso 1 1 calc R U . . .
C5 C 0.63308(8) 0.3396(4) 0.53484(17) 0.0091(5) Uani 1 1 d . . . . .
C7 C 0.75494(9) 0.2458(4) 0.65163(18) 0.0109(5) Uani 1 1 d . . . . .
C6 C 0.67877(9) 0.2489(4) 0.54177(18) 0.0109(5) Uani 1 1 d . . . . .
H6 H 0.685256 0.274394 0.481835 0.013 Uiso 1 1 calc R U . . .
C9 C 0.83215(10) 0.2334(5) 0.75550(19) 0.0150(5) Uani 1 1 d . . . . .
H9 H 0.856464 0.298891 0.802509 0.018 Uiso 1 1 calc R U . . .
C8 C 0.79107(10) 0.3420(4) 0.71971(19) 0.0143(5) Uani 1 1 d . . . . .
H8 H 0.787561 0.482749 0.741763 0.017 Uiso 1 1 calc R U . . .
C10 C 0.83767(9) 0.0270(5) 0.72216(19) 0.0156(5) Uani 1 1 d . . . . .
H10 H 0.866060 -0.045648 0.744478 0.019 Uiso 1 1 calc R U . . .
C11 C 0.80117(9) -0.0704(4) 0.65606(18) 0.0117(5) Uani 1 1 d . . . . .
H11 H 0.804587 -0.212328 0.635102 0.014 Uiso 1 1 calc R U . . .
C12 C 0.75932(9) 0.0370(4) 0.61964(17) 0.0099(5) Uani 1 1 d . . . . .
C13 C 0.71902(9) -0.0707(4) 0.55364(19) 0.0132(5) Uani 1 1 d . . . . .
H13A H 0.720698 -0.056731 0.489577 0.016 Uiso 1 1 calc R U . . .
H13B H 0.719616 -0.226743 0.568722 0.016 Uiso 1 1 calc R U . . .
C14 C 0.59514(10) 0.0871(5) 0.37354(19) 0.0142(5) Uani 1 1 d . U . . .
C15 C 0.51707(9) 0.1620(5) 0.3922(2) 0.0161(5) Uani 1 1 d . U . . .
C16 C 0.55653(9) 0.4514(5) 0.31686(19) 0.0147(5) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 C15 1.790(3) . ?
Mn1 C16 1.797(3) . ?
Mn1 C14 1.802(3) . ?
Mn1 C1 2.132(2) . ?
Mn1 C3 2.142(3) . ?
Mn1 C5 2.146(2) . ?
Mn1 C4 2.153(3) . ?
Mn1 C2 2.154(3) . ?
O1 C13 1.421(3) . ?
O1 C6 1.434(3) . ?
C1 C2 1.417(4) . ?
C1 C5 1.429(4) . ?
C1 H1 1.0000 . ?
N1 C7 1.403(3) . ?
N1 C6 1.442(3) . ?
N1 H1N 0.8800 . ?
C2 C3 1.398(4) . ?
C2 H2 1.0000 . ?
O2 C14 1.159(4) . ?
O3 C15 1.161(3) . ?
C3 C4 1.443(4) . ?
C3 H3 1.0000 . ?
O4 C16 1.154(3) . ?
C4 C5 1.433(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.494(3) . ?
C7 C8 1.395(4) . ?
C7 C12 1.400(4) . ?
C6 H6 1.0000 . ?
C9 C8 1.390(4) . ?
C9 C10 1.401(4) . ?
C9 H9 0.9500 . ?
C8 H8 0.9500 . ?
C10 C11 1.391(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.406(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.490(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?

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
C15 Mn1 C16 93.75(13) . . ?
C15 Mn1 C14 90.89(13) . . ?
C16 Mn1 C14 91.04(13) . . ?
C15 Mn1 C1 104.61(12) . . ?
C16 Mn1 C1 156.52(12) . . ?
C14 Mn1 C1 102.98(12) . . ?
C15 Mn1 C3 113.17(13) . . ?
C16 Mn1 C3 94.60(12) . . ?
C14 Mn1 C3 154.79(12) . . ?
C1 Mn1 C3 64.92(11) . . ?
C15 Mn1 C5 142.64(11) . . ?
C16 Mn1 C5 123.51(11) . . ?
C14 Mn1 C5 90.95(11) . . ?
C1 Mn1 C5 39.01(10) . . ?
C3 Mn1 C5 65.53(10) . . ?
C15 Mn1 C4 152.31(12) . . ?
C16 Mn1 C4 91.93(12) . . ?
C14 Mn1 C4 116.10(12) . . ?
C1 Mn1 C4 65.07(11) . . ?
C3 Mn1 C4 39.27(11) . . ?
C5 Mn1 C4 38.93(9) . . ?
C15 Mn1 C2 91.21(13) . . ?
C16 Mn1 C2 128.37(13) . . ?
C14 Mn1 C2 140.26(13) . . ?
C1 Mn1 C2 38.61(11) . . ?
C3 Mn1 C2 37.98(12) . . ?
C5 Mn1 C2 64.78(11) . . ?
C4 Mn1 C2 64.41(12) . . ?
C13 O1 C6 108.1(2) . . ?
C2 C1 C5 108.1(2) . . ?
C2 C1 Mn1 71.52(15) . . ?
C5 C1 Mn1 71.04(14) . . ?
C2 C1 H1 125.9 . . ?
C5 C1 H1 125.9 . . ?
Mn1 C1 H1 125.9 . . ?
C7 N1 C6 116.9(2) . . ?
C7 N1 H1N 121.5 . . ?
C6 N1 H1N 121.5 . . ?
C3 C2 C1 109.2(3) . . ?
C3 C2 Mn1 70.57(16) . . ?
C1 C2 Mn1 69.87(15) . . ?
C3 C2 H2 125.4 . . ?
C1 C2 H2 125.4 . . ?
Mn1 C2 H2 125.4 . . ?
C2 C3 C4 107.7(3) . . ?
C2 C3 Mn1 71.45(16) . . ?
C4 C3 Mn1 70.75(15) . . ?
C2 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
Mn1 C3 H3 126.1 . . ?
C5 C4 C3 107.6(2) . . ?
C5 C4 Mn1 70.30(15) . . ?
C3 C4 Mn1 69.98(15) . . ?
C5 C4 H4 126.2 . . ?
C3 C4 H4 126.2 . . ?
Mn1 C4 H4 126.2 . . ?
C1 C5 C4 107.3(2) . . ?
C1 C5 C6 127.3(2) . . ?
C4 C5 C6 125.2(2) . . ?
C1 C5 Mn1 69.95(14) . . ?
C4 C5 Mn1 70.77(14) . . ?
C6 C5 Mn1 127.95(18) . . ?
C8 C7 C12 120.4(2) . . ?
C8 C7 N1 120.6(2) . . ?
C12 C7 N1 118.9(2) . . ?
O1 C6 N1 111.4(2) . . ?
O1 C6 C5 107.9(2) . . ?
N1 C6 C5 109.8(2) . . ?
O1 C6 H6 109.2 . . ?
N1 C6 H6 109.2 . . ?
C5 C6 H6 109.2 . . ?
C8 C9 C10 119.9(3) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 121.4(2) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C7 C12 C11 118.4(2) . . ?
C7 C12 C13 119.5(2) . . ?
C11 C12 C13 121.9(2) . . ?
O1 C13 C12 112.0(2) . . ?
O1 C13 H13A 109.2 . . ?
C12 C13 H13A 109.2 . . ?
O1 C13 H13B 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
O2 C14 Mn1 178.9(3) . . ?
O3 C15 Mn1 178.5(3) . . ?
O4 C16 Mn1 178.6(3) . . ?

_refine_diff_density_max         1.649
_refine_diff_density_min         -0.616
_refine_diff_density_rms         0.106

####################################################################### 
# 
# 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_mo_IAGVB57_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 1858656'
_audit_update_record             
;
2018-07-27 deposited with the CCDC.
2018-12-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        6c
_chemical_name_common            ?
_chemical_melting_point          148
_chemical_formula_moiety         'C16 H12 N O4 Re'
_chemical_formula_sum            'C16 H12 N O4 Re'
_chemical_formula_weight         468.47

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   15.3555(7)
_cell_length_b                   6.1536(3)
_cell_length_c                   29.7559(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2811.7(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9882
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      29.53

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.213
_exptl_crystal_F_000             1776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.332
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.031
_exptl_absorpt_coefficient_mu    8.661
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5649
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25066
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         2.653
_diffrn_reflns_theta_max         29.554
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             7511
_reflns_number_gt                6741
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.875
_reflns_Friedel_fraction_max     0.904
_reflns_Friedel_fraction_full    0.949

_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. These statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0466P)²+1.0701P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.269(16)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7511
_refine_ls_number_parameters     386
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0791
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Re1A Re 0.33421(2) 0.47744(5) 0.57134(2) 0.00894(9) Uani 1 1 d . . . . .
O1A O 0.4499(5) 0.8224(12) 0.6150(3) 0.0220(18) Uani 1 1 d . . . . .
O2A O 0.2657(4) 0.7309(11) 0.6796(3) 0.0104(16) Uani 1 1 d . . . . .
O3A O 0.3304(5) 0.7565(14) 0.4863(4) 0.030(3) Uani 1 1 d . . . . .
O4A O 0.4919(5) 0.2156(15) 0.5393(3) 0.025(2) Uani 1 1 d . . . . .
N1A N 0.2252(5) 0.3974(13) 0.7145(3) 0.0115(10) Uani 1 1 d . . . . .
H1NA H 0.1984 0.2735 0.7094 0.014 Uiso 1 1 calc R U . . .
C1A C 0.1986(7) 0.5138(16) 0.6032(4) 0.0144(11) Uani 1 1 d . U . . .
H1A H 0.1654 0.6522 0.6074 0.017 Uiso 1 1 calc R U . . .
C2A C 0.1912(6) 0.3669(15) 0.5663(4) 0.0148(11) Uani 1 1 d . U . . .
H2A H 0.1529 0.3896 0.5396 0.018 Uiso 1 1 calc R U . . .
C3A C 0.2413(6) 0.1811(16) 0.5742(5) 0.0148(11) Uani 1 1 d . U . . .
H3A H 0.2441 0.0482 0.5549 0.018 Uiso 1 1 calc R U . . .
C4A C 0.2817(6) 0.2101(18) 0.6181(4) 0.0141(11) Uani 1 1 d . U . . .
H4A H 0.3176 0.0997 0.6344 0.017 Uiso 1 1 calc R U . . .
C5A C 0.2550(6) 0.4118(17) 0.6353(4) 0.0139(11) Uani 1 1 d . U . . .
C6A C 0.2796(8) 0.5030(15) 0.6806(4) 0.014(2) Uani 1 1 d . . . . .
H6A H 0.3423 0.4721 0.6869 0.017 Uiso 1 1 calc R U . . .
C7A C 0.2187(6) 0.5083(14) 0.7564(4) 0.0099(19) Uani 1 1 d . . . . .
C8A C 0.1754(6) 0.4084(15) 0.7923(4) 0.013(2) Uani 1 1 d . . . . .
H8A H 0.1512 0.2673 0.7889 0.015 Uiso 1 1 calc R U . . .
C9A C 0.1683(7) 0.5178(16) 0.8331(4) 0.018(2) Uani 1 1 d . . . . .
H9A H 0.1372 0.4534 0.8573 0.021 Uiso 1 1 calc R U . . .
C10A C 0.2063(6) 0.7197(17) 0.8386(4) 0.012(2) Uani 1 1 d . . . . .
H10A H 0.2037 0.7912 0.8668 0.014 Uiso 1 1 calc R U . . .
C11A C 0.2483(6) 0.8175(18) 0.8026(4) 0.013(2) Uani 1 1 d . . . . .
H11A H 0.2730 0.9579 0.8063 0.016 Uiso 1 1 calc R U . . .
C12A C 0.2551(6) 0.7139(17) 0.7611(4) 0.009(2) Uani 1 1 d . . . . .
C13A C 0.2960(6) 0.8218(15) 0.7213(3) 0.0103(14) Uani 1 1 d . . . . .
H13A H 0.2823 0.9790 0.7219 0.012 Uiso 1 1 calc R U . . .
H13B H 0.3600 0.8057 0.7231 0.012 Uiso 1 1 calc R U . . .
C14A C 0.4070(6) 0.692(2) 0.5985(4) 0.015(2) Uani 1 1 d . . . . .
C15A C 0.3326(7) 0.6526(19) 0.5176(4) 0.019(3) Uani 1 1 d . . . . .
C16A C 0.4347(7) 0.3220(17) 0.5512(4) 0.014(2) Uani 1 1 d . . . . .
Re1B Re 0.59402(2) 0.46867(5) 0.42950(2) 0.00866(9) Uani 1 1 d . . . . .
O1B O 0.5276(5) 0.7251(11) 0.3204(3) 0.0127(16) Uani 1 1 d . . . . .
O2B O 0.5853(5) 0.7068(17) 0.5201(4) 0.030(2) Uani 1 1 d . . . . .
O3B O 0.7064(5) 0.8308(12) 0.3890(3) 0.0235(18) Uani 1 1 d . . . . .
O4B O 0.7582(5) 0.2310(14) 0.4587(3) 0.026(2) Uani 1 1 d . . . . .
N1B N 0.4888(5) 0.3901(13) 0.2846(3) 0.0115(10) Uani 1 1 d . . . . .
H2NB H 0.4648 0.2620 0.2890 0.014 Uiso 1 1 calc R U . . .
C1B C 0.4595(6) 0.5008(16) 0.3956(4) 0.013(2) Uani 1 1 d . . . . .
H1B H 0.4252 0.6376 0.3915 0.016 Uiso 1 1 calc R U . . .
C2B C 0.4522(6) 0.3520(17) 0.4315(5) 0.019(2) Uani 1 1 d . . . . .
H2B H 0.4120 0.3683 0.4577 0.023 Uiso 1 1 calc R U . . .
C3B C 0.5050(6) 0.1692(17) 0.4230(4) 0.016(2) Uani 1 1 d . . . . .
H3B H 0.5081 0.0340 0.4416 0.019 Uiso 1 1 calc R U . . .
C4B C 0.5464(6) 0.2040(17) 0.3809(4) 0.012(2) Uani 1 1 d . . . . .
H4B H 0.5841 0.0971 0.3647 0.015 Uiso 1 1 calc R U . . .
C5B C 0.5189(6) 0.4074(17) 0.3641(4) 0.013(2) Uani 1 1 d . . . . .
C6B C 0.5407(7) 0.4986(15) 0.3181(4) 0.013(2) Uani 1 1 d . . . . .
H6B H 0.6035 0.4700 0.3117 0.015 Uiso 1 1 calc R U . . .
C7B C 0.5581(6) 0.8202(16) 0.2795(4) 0.014(2) Uani 1 1 d . . . . .
H7BA H 0.6221 0.8033 0.2775 0.017 Uiso 1 1 calc R U . . .
H7BB H 0.5446 0.9776 0.2795 0.017 Uiso 1 1 calc R U . . .
C8B C 0.5159(6) 0.7143(17) 0.2392(4) 0.011(2) Uani 1 1 d . . . . .
C9B C 0.5094(6) 0.8212(16) 0.1982(4) 0.011(2) Uani 1 1 d . . . . .
H9B H 0.5349 0.9609 0.1948 0.013 Uiso 1 1 calc R U . . .
C10B C 0.4669(6) 0.7280(17) 0.1626(4) 0.014(2) Uani 1 1 d . . . . .
H10B H 0.4628 0.8027 0.1347 0.017 Uiso 1 1 calc R U . . .
C11B C 0.4299(7) 0.5235(16) 0.1675(4) 0.013(2) Uani 1 1 d . . . . .
H11B H 0.4007 0.4576 0.1429 0.015 Uiso 1 1 calc R U . . .
C12B C 0.4356(6) 0.4154(15) 0.2082(4) 0.0114(19) Uani 1 1 d . . . . .
H12B H 0.4090 0.2770 0.2116 0.014 Uiso 1 1 calc R U . . .
C13B C 0.4798(6) 0.5071(14) 0.2440(4) 0.0103(14) Uani 1 1 d . . . . .
C14B C 0.5907(6) 0.620(2) 0.4862(4) 0.019(2) Uani 1 1 d . . . . .
C15B C 0.6644(6) 0.697(2) 0.4056(4) 0.015(2) Uani 1 1 d . . . . .
C16B C 0.6978(7) 0.3234(18) 0.4485(4) 0.015(2) 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
Re1A C14A 1.911(12) . ?
Re1A C16A 1.912(10) . ?
Re1A C15A 1.929(13) . ?
Re1A C5A 2.294(11) . ?
Re1A C1A 2.299(11) . ?
Re1A C4A 2.300(11) . ?
Re1A C2A 2.304(9) . ?
Re1A C3A 2.317(10) . ?
O1A C14A 1.147(14) . ?
O2A C6A 1.418(11) . ?
O2A C13A 1.438(13) . ?
O3A C15A 1.128(16) . ?
O4A C16A 1.151(12) . ?
N1A C7A 1.423(13) . ?
N1A C6A 1.462(14) . ?
N1A H1NA 0.8800 . ?
C1A C2A 1.426(15) . ?
C1A C5A 1.434(15) . ?
C1A H1A 1.0000 . ?
C2A C3A 1.397(13) . ?
C2A H2A 1.0000 . ?
C3A C4A 1.458(17) . ?
C3A H3A 1.0000 . ?
C4A C5A 1.403(14) . ?
C4A H4A 1.0000 . ?
C5A C6A 1.509(16) . ?
C6A H6A 1.0000 . ?
C7A C12A 1.390(13) . ?
C7A C8A 1.401(14) . ?
C8A C9A 1.393(16) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.383(14) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.386(15) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.394(15) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.497(14) . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
Re1B C15B 1.907(12) . ?
Re1B C16B 1.913(10) . ?
Re1B C14B 1.928(13) . ?
Re1B C5B 2.293(10) . ?
Re1B C2B 2.294(9) . ?
Re1B C4B 2.297(10) . ?
Re1B C3B 2.302(9) . ?
Re1B C1B 2.308(10) . ?
O1B C6B 1.409(11) . ?
O1B C7B 1.428(13) . ?
O2B C14B 1.143(16) . ?
O3B C15B 1.159(14) . ?
O4B C16B 1.129(13) . ?
N1B C13B 1.413(14) . ?
N1B C6B 1.441(14) . ?
N1B H2NB 0.8800 . ?
C1B C2B 1.412(17) . ?
C1B C5B 1.428(14) . ?
C1B H1B 1.0000 . ?
C2B C3B 1.410(14) . ?
C2B H2B 1.0000 . ?
C3B C4B 1.421(15) . ?
C3B H3B 1.0000 . ?
C4B C5B 1.413(15) . ?
C4B H4B 1.0000 . ?
C5B C6B 1.516(16) . ?
C6B H6B 1.0000 . ?
C7B C8B 1.511(15) . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C8B C9B 1.390(15) . ?
C8B C13B 1.398(13) . ?
C9B C10B 1.370(15) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.389(14) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.385(15) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.384(15) . ?
C12B H12B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14A Re1A C16A 90.4(5) . . ?
C14A Re1A C15A 88.4(5) . . ?
C16A Re1A C15A 91.7(5) . . ?
C14A Re1A C5A 94.6(4) . . ?
C16A Re1A C5A 126.8(4) . . ?
C15A Re1A C5A 141.2(4) . . ?
C14A Re1A C1A 106.7(4) . . ?
C16A Re1A C1A 155.4(4) . . ?
C15A Re1A C1A 106.0(4) . . ?
C5A Re1A C1A 36.4(4) . . ?
C14A Re1A C4A 116.3(5) . . ?
C16A Re1A C4A 96.6(4) . . ?
C15A Re1A C4A 153.7(4) . . ?
C5A Re1A C4A 35.6(4) . . ?
C1A Re1A C4A 60.2(4) . . ?
C14A Re1A C2A 142.1(4) . . ?
C16A Re1A C2A 127.0(4) . . ?
C15A Re1A C2A 95.7(4) . . ?
C5A Re1A C2A 59.8(4) . . ?
C1A Re1A C2A 36.1(4) . . ?
C4A Re1A C2A 59.6(4) . . ?
C14A Re1A C3A 152.8(5) . . ?
C16A Re1A C3A 96.6(4) . . ?
C15A Re1A C3A 117.5(5) . . ?
C5A Re1A C3A 60.3(4) . . ?
C1A Re1A C3A 60.3(4) . . ?
C4A Re1A C3A 36.8(4) . . ?
C2A Re1A C3A 35.2(3) . . ?
C6A O2A C13A 108.5(8) . . ?
C7A N1A C6A 115.5(8) . . ?
C7A N1A H1NA 122.2 . . ?
C6A N1A H1NA 122.2 . . ?
C2A C1A C5A 106.4(9) . . ?
C2A C1A Re1A 72.1(6) . . ?
C5A C1A Re1A 71.6(6) . . ?
C2A C1A H1A 126.6 . . ?
C5A C1A H1A 126.6 . . ?
Re1A C1A H1A 126.6 . . ?
C3A C2A C1A 110.3(10) . . ?
C3A C2A Re1A 72.9(5) . . ?
C1A C2A Re1A 71.8(6) . . ?
C3A C2A H2A 124.8 . . ?
C1A C2A H2A 124.8 . . ?
Re1A C2A H2A 124.8 . . ?
C2A C3A C4A 106.5(10) . . ?
C2A C3A Re1A 71.9(6) . . ?
C4A C3A Re1A 71.0(6) . . ?
C2A C3A H3A 126.6 . . ?
C4A C3A H3A 126.6 . . ?
Re1A C3A H3A 126.6 . . ?
C5A C4A C3A 108.1(9) . . ?
C5A C4A Re1A 72.0(6) . . ?
C3A C4A Re1A 72.2(6) . . ?
C5A C4A H4A 125.8 . . ?
C3A C4A H4A 125.8 . . ?
Re1A C4A H4A 125.8 . . ?
C4A C5A C1A 108.7(10) . . ?
C4A C5A C6A 125.6(10) . . ?
C1A C5A C6A 125.7(9) . . ?
C4A C5A Re1A 72.5(6) . . ?
C1A C5A Re1A 72.0(6) . . ?
C6A C5A Re1A 122.9(7) . . ?
O2A C6A N1A 111.7(8) . . ?
O2A C6A C5A 108.1(9) . . ?
N1A C6A C5A 108.0(9) . . ?
O2A C6A H6A 109.7 . . ?
N1A C6A H6A 109.7 . . ?
C5A C6A H6A 109.7 . . ?
C12A C7A C8A 120.8(9) . . ?
C12A C7A N1A 119.8(9) . . ?
C8A C7A N1A 119.4(8) . . ?
C9A C8A C7A 119.4(9) . . ?
C9A C8A H8A 120.3 . . ?
C7A C8A H8A 120.3 . . ?
C10A C9A C8A 120.2(10) . . ?
C10A C9A H9A 119.9 . . ?
C8A C9A H9A 119.9 . . ?
C9A C10A C11A 119.7(11) . . ?
C9A C10A H10A 120.1 . . ?
C11A C10A H10A 120.1 . . ?
C10A C11A C12A 121.4(10) . . ?
C10A C11A H11A 119.3 . . ?
C12A C11A H11A 119.3 . . ?
C7A C12A C11A 118.4(10) . . ?
C7A C12A C13A 119.5(9) . . ?
C11A C12A C13A 122.0(9) . . ?
O2A C13A C12A 112.0(8) . . ?
O2A C13A H13A 109.2 . . ?
C12A C13A H13A 109.2 . . ?
O2A C13A H13B 109.2 . . ?
C12A C13A H13B 109.2 . . ?
H13A C13A H13B 107.9 . . ?
O1A C14A Re1A 179.3(10) . . ?
O3A C15A Re1A 178.8(11) . . ?
O4A C16A Re1A 175.3(10) . . ?
C15B Re1B C16B 88.9(4) . . ?
C15B Re1B C14B 89.2(5) . . ?
C16B Re1B C14B 89.4(5) . . ?
C15B Re1B C5B 95.2(5) . . ?
C16B Re1B C5B 126.3(4) . . ?
C14B Re1B C5B 144.0(4) . . ?
C15B Re1B C2B 141.0(4) . . ?
C16B Re1B C2B 129.6(4) . . ?
C14B Re1B C2B 95.9(4) . . ?
C5B Re1B C2B 59.5(4) . . ?
C15B Re1B C4B 117.9(5) . . ?
C16B Re1B C4B 96.9(4) . . ?
C14B Re1B C4B 152.2(4) . . ?
C5B Re1B C4B 35.9(4) . . ?
C2B Re1B C4B 59.5(4) . . ?
C15B Re1B C3B 153.3(5) . . ?
C16B Re1B C3B 98.4(4) . . ?
C14B Re1B C3B 116.3(4) . . ?
C5B Re1B C3B 59.9(4) . . ?
C2B Re1B C3B 35.7(4) . . ?
C4B Re1B C3B 36.0(4) . . ?
C15B Re1B C1B 106.3(4) . . ?
C16B Re1B C1B 156.2(4) . . ?
C14B Re1B C1B 108.5(4) . . ?
C5B Re1B C1B 36.2(4) . . ?
C2B Re1B C1B 35.7(4) . . ?
C4B Re1B C1B 60.0(4) . . ?
C3B Re1B C1B 60.0(4) . . ?
C6B O1B C7B 108.6(8) . . ?
C13B N1B C6B 114.2(8) . . ?
C13B N1B H2NB 122.9 . . ?
C6B N1B H2NB 122.9 . . ?
C2B C1B C5B 106.6(9) . . ?
C2B C1B Re1B 71.6(5) . . ?
C5B C1B Re1B 71.4(6) . . ?
C2B C1B H1B 126.5 . . ?
C5B C1B H1B 126.5 . . ?
Re1B C1B H1B 126.5 . . ?
C3B C2B C1B 109.6(10) . . ?
C3B C2B Re1B 72.4(5) . . ?
C1B C2B Re1B 72.7(6) . . ?
C3B C2B H2B 125.1 . . ?
C1B C2B H2B 125.1 . . ?
Re1B C2B H2B 125.1 . . ?
C2B C3B C4B 107.2(10) . . ?
C2B C3B Re1B 71.8(5) . . ?
C4B C3B Re1B 71.8(6) . . ?
C2B C3B H3B 126.3 . . ?
C4B C3B H3B 126.3 . . ?
Re1B C3B H3B 126.3 . . ?
C5B C4B C3B 108.2(9) . . ?
C5B C4B Re1B 71.9(6) . . ?
C3B C4B Re1B 72.2(6) . . ?
C5B C4B H4B 125.8 . . ?
C3B C4B H4B 125.8 . . ?
Re1B C4B H4B 125.8 . . ?
C4B C5B C1B 108.4(10) . . ?
C4B C5B C6B 125.6(9) . . ?
C1B C5B C6B 125.7(9) . . ?
C4B C5B Re1B 72.2(6) . . ?
C1B C5B Re1B 72.5(6) . . ?
C6B C5B Re1B 126.4(7) . . ?
O1B C6B N1B 114.3(9) . . ?
O1B C6B C5B 107.0(9) . . ?
N1B C6B C5B 109.4(8) . . ?
O1B C6B H6B 108.7 . . ?
N1B C6B H6B 108.7 . . ?
C5B C6B H6B 108.7 . . ?
O1B C7B C8B 111.0(8) . . ?
O1B C7B H7BA 109.4 . . ?
C8B C7B H7BA 109.4 . . ?
O1B C7B H7BB 109.4 . . ?
C8B C7B H7BB 109.4 . . ?
H7BA C7B H7BB 108.0 . . ?
C9B C8B C13B 119.6(10) . . ?
C9B C8B C7B 121.6(9) . . ?
C13B C8B C7B 118.8(10) . . ?
C10B C9B C8B 121.0(10) . . ?
C10B C9B H9B 119.5 . . ?
C8B C9B H9B 119.5 . . ?
C9B C10B C11B 119.5(10) . . ?
C9B C10B H10B 120.3 . . ?
C11B C10B H10B 120.3 . . ?
C12B C11B C10B 120.1(10) . . ?
C12B C11B H11B 119.9 . . ?
C10B C11B H11B 119.9 . . ?
C13B C12B C11B 120.6(9) . . ?
C13B C12B H12B 119.7 . . ?
C11B C12B H12B 119.7 . . ?
C12B C13B C8B 119.2(10) . . ?
C12B C13B N1B 119.9(8) . . ?
C8B C13B N1B 120.9(9) . . ?
O2B C14B Re1B 177.3(10) . . ?
O3B C15B Re1B 176.6(11) . . ?
O4B C16B Re1B 177.4(10) . . ?

_refine_diff_density_max         6.051
_refine_diff_density_min         -2.263
_refine_diff_density_rms         0.247



####################################################################### 
# 
# 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_va_jom_fc30_06_17_170k_0m
_database_code_depnum_ccdc_archive 'CCDC 1858655'
_audit_update_record             
;
2018-07-27 deposited with the CCDC.
2018-12-12 downloaded from the CCDC.
;
_audit_creation_date             2018-01-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        6a
_chemical_formula_moiety         'C18 H17 Fe N O'
_chemical_formula_sum            'C18 H17 Fe N O'
_chemical_formula_weight         319.17
_chemical_absolute_configuration ad
_chemical_melting_point          96
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'
Fe Fe 0.3463 0.8444 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.9213(2)
_cell_length_b                   7.5337(3)
_cell_length_c                   16.2535(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.7714(15)
_cell_angle_gamma                90
_cell_volume                     720.00(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9921
_cell_measurement_temperature    170.0
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.903
_exptl_absorpt_coefficient_mu    1.044
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0599 before and 0.0534 after correction.
The Ratio of minimum to maximum transmission is 0.9391.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16003
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.416
_diffrn_reflns_theta_min         2.524
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.854
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2831
_reflns_number_total             2941
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.023(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2941
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0229
_refine_ls_restrained_S_all      0.968
_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)+(0.0330P)²+0.2690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0559
_refine_ls_wR_factor_ref         0.0569
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.977(18)
 0.023(18)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C17) = Uanis(C16) = Uanis(C15) = Uanis(C14) = Uanis(C18) = Uanis(C17A) =
Uanis(C16A) = Uanis(C15A) = Uanis(C14A) = Uanis(C18A)
4. Others
 Sof(C17A)=Sof(H17A)=Sof(C16A)=Sof(H16A)=Sof(C15A)=Sof(H15A)=Sof(C14A)=
 Sof(H14A)=Sof(C18A)=Sof(H18A)=1-FVAR(1)
 Sof(C17)=Sof(H17)=Sof(C16)=Sof(H16)=Sof(C15)=Sof(H15)=Sof(C14)=Sof(H14)=
 Sof(C18)=Sof(H18)=FVAR(1)
5.a Riding coordinates:
 N1(H1)
5.b Ternary CH refined with riding coordinates:
 C6(H6)
5.c Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
5.d Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C17(H17),
  C16(H16), C15(H15), C14(H14), C18(H18), C17A(H17A), C16A(H16A), C15A(H15A),
 C14A(H14A), C18A(H18A)
5.e Fitted pentagon refined as free rotating group:
 C17(C16,C15,C14,C18), C17A(C16A,C15A,C14A,C18A)
;
_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
Fe1 Fe 0.20558(5) 0.58549(5) 0.85738(2) 0.01846(11) Uani 1 1 d . . . . .
O1 O 0.4451(2) 0.5757(4) 0.65661(10) 0.0221(4) Uani 1 1 d . . . . .
N1 N 0.0729(4) 0.5187(3) 0.58973(13) 0.0209(5) Uani 1 1 d . . . . .
H1 H 0.050033 0.403949 0.594745 0.025 Uiso 1 1 d R . . . .
C1 C 0.2972(5) 0.3777(4) 0.78831(17) 0.0225(6) Uani 1 1 d . . . . .
H1A H 0.447801 0.345366 0.779871 0.027 Uiso 1 1 calc R . . . .
C2 C 0.1768(5) 0.3157(4) 0.85290(17) 0.0252(6) Uani 1 1 d . . . . .
H2 H 0.232703 0.235067 0.895445 0.030 Uiso 1 1 calc R . . . .
C3 C -0.0422(5) 0.3953(4) 0.84289(17) 0.0246(6) Uani 1 1 d . . . . .
H3 H -0.158588 0.376802 0.877519 0.029 Uiso 1 1 calc R . . . .
C4 C -0.0572(4) 0.5073(4) 0.77215(16) 0.0211(5) Uani 1 1 d . . . . .
H4 H -0.184811 0.576971 0.751156 0.025 Uiso 1 1 calc R . . . .
C5 C 0.1541(4) 0.4964(3) 0.73830(15) 0.0178(5) Uani 1 1 d . . . . .
C6 C 0.2072(3) 0.5908(5) 0.66200(13) 0.0179(4) Uani 1 1 d . . . . .
H6 H 0.168406 0.719210 0.666995 0.022 Uiso 1 1 calc R . . . .
C7 C 0.1457(4) 0.5607(4) 0.51297(15) 0.0171(6) Uani 1 1 d . . . . .
C8 C 0.0075(4) 0.5218(4) 0.43948(17) 0.0213(5) Uani 1 1 d . . . . .
H8 H -0.133190 0.462280 0.441416 0.026 Uiso 1 1 calc R . . . .
C9 C 0.0747(4) 0.5697(5) 0.36401(15) 0.0249(6) Uani 1 1 d . . . . .
H9 H -0.019083 0.542055 0.314140 0.030 Uiso 1 1 calc R . . . .
C10 C 0.2794(5) 0.6584(4) 0.36103(18) 0.0268(6) Uani 1 1 d . . . . .
H10 H 0.324230 0.693473 0.309203 0.032 Uiso 1 1 calc R . . . .
C11 C 0.4172(5) 0.6954(4) 0.43329(18) 0.0237(6) Uani 1 1 d . . . . .
H11 H 0.557336 0.755390 0.430746 0.028 Uiso 1 1 calc R . . . .
C12 C 0.3542(4) 0.6459(3) 0.51043(16) 0.0181(5) Uani 1 1 d . . . . .
C13 C 0.5070(4) 0.6798(4) 0.58909(17) 0.0229(6) Uani 1 1 d . . . . .
H13A H 0.665807 0.651922 0.580274 0.027 Uiso 1 1 calc R . . . .
H13B H 0.499966 0.807198 0.603468 0.027 Uiso 1 1 calc R . . . .
C17 C 0.1481(5) 0.8460(5) 0.8836(3) 0.0314(5) Uani 0.700(8) 1 d . . P A 1
H17 H 0.026100 0.917299 0.858996 0.038 Uiso 0.700(8) 1 calc R . P A 1
C16 C 0.1466(7) 0.7401(7) 0.9559(3) 0.0314(5) Uani 0.700(8) 1 d G . P A 1
H16 H 0.023516 0.728215 0.988028 0.038 Uiso 0.700(8) 1 calc R . P A 1
C15 C 0.3615(9) 0.6552(5) 0.97157(19) 0.0314(5) Uani 0.700(8) 1 d G . P A 1
H15 H 0.407355 0.576525 1.016094 0.038 Uiso 0.700(8) 1 calc R . P A 1
C14 C 0.4957(4) 0.7086(5) 0.9091(3) 0.0314(5) Uani 0.700(8) 1 d G . P A 1
H14 H 0.647166 0.671860 0.904409 0.038 Uiso 0.700(8) 1 calc R . P A 1
C18 C 0.3638(7) 0.8265(5) 0.85471(17) 0.0314(5) Uani 0.700(8) 1 d G . P A 1
H18 H 0.411537 0.882469 0.807317 0.038 Uiso 0.700(8) 1 calc R . P A 1
C17A C 0.1339(10) 0.8185(13) 0.9143(8) 0.0314(5) Uani 0.300(8) 1 d . . P A 2
H17A H -0.008839 0.877342 0.910484 0.038 Uiso 0.300(8) 1 calc R . P A 2
C16A C 0.2141(19) 0.6893(14) 0.9744(5) 0.0314(5) Uani 0.300(8) 1 d G . P A 2
H16A H 0.134401 0.646557 1.017789 0.038 Uiso 0.300(8) 1 calc R . P A 2
C15A C 0.4343(18) 0.6352(10) 0.9582(5) 0.0314(5) Uani 0.300(8) 1 d G . P A 2
H15A H 0.527798 0.549967 0.988850 0.038 Uiso 0.300(8) 1 calc R . P A 2
C14A C 0.4902(11) 0.7310(13) 0.8881(6) 0.0314(5) Uani 0.300(8) 1 d G . P A 2
H14A H 0.627689 0.721056 0.863660 0.038 Uiso 0.300(8) 1 calc R . P A 2
C18A C 0.3046(18) 0.8443(11) 0.8610(5) 0.0314(5) Uani 0.300(8) 1 d G . P A 2
H18A H 0.296029 0.923385 0.815228 0.038 Uiso 0.300(8) 1 calc R . 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
Fe1 C1 2.037(3) . ?
Fe1 C2 2.040(3) . ?
Fe1 C3 2.045(3) . ?
Fe1 C4 2.044(3) . ?
Fe1 C5 2.037(2) . ?
Fe1 C17 2.045(3) . ?
Fe1 C16 2.043(3) . ?
Fe1 C15 2.042(3) . ?
Fe1 C14 2.044(4) . ?
Fe1 C15A 2.034(8) . ?
Fe1 C14A 2.023(9) . ?
Fe1 C18A 2.035(9) . ?
O1 C6 1.426(3) . ?
O1 C13 1.431(3) . ?
N1 C6 1.445(3) . ?
N1 C7 1.403(3) . ?
C1 C2 1.416(4) . ?
C1 C5 1.420(4) . ?
C2 C3 1.421(4) . ?
C3 C4 1.420(4) . ?
C4 C5 1.427(4) . ?
C5 C6 1.495(4) . ?
C7 C8 1.397(3) . ?
C7 C12 1.396(3) . ?
C8 C9 1.381(4) . ?
C9 C10 1.390(4) . ?
C10 C11 1.377(4) . ?
C11 C12 1.400(4) . ?
C12 C13 1.499(4) . ?
C17 C16 1.4200 . ?
C17 C18 1.4200 . ?
C16 C15 1.4200 . ?
C15 C14 1.4200 . ?
C14 C18 1.4200 . ?
C17A C16A 1.4200 . ?
C17A C18A 1.4200 . ?
C16A C15A 1.4200 . ?
C15A C14A 1.4200 . ?
C14A C18A 1.4200 . ?

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 Fe1 C2 40.63(11) . . ?
C1 Fe1 C3 68.40(12) . . ?
C1 Fe1 C4 68.64(11) . . ?
C1 Fe1 C5 40.78(11) . . ?
C1 Fe1 C17 156.08(18) . . ?
C1 Fe1 C16 162.06(19) . . ?
C1 Fe1 C15 125.28(17) . . ?
C1 Fe1 C14 108.05(12) . . ?
C2 Fe1 C3 40.71(12) . . ?
C2 Fe1 C4 68.60(11) . . ?
C2 Fe1 C17 161.45(17) . . ?
C2 Fe1 C16 125.09(16) . . ?
C2 Fe1 C15 108.40(12) . . ?
C2 Fe1 C14 121.96(13) . . ?
C3 Fe1 C17 124.16(14) . . ?
C4 Fe1 C3 40.66(11) . . ?
C4 Fe1 C17 106.60(12) . . ?
C5 Fe1 C2 68.61(11) . . ?
C5 Fe1 C3 68.56(11) . . ?
C5 Fe1 C4 40.93(10) . . ?
C5 Fe1 C17 120.30(16) . . ?
C5 Fe1 C16 155.80(19) . . ?
C5 Fe1 C15 161.68(18) . . ?
C5 Fe1 C14 124.36(14) . . ?
C16 Fe1 C3 107.66(12) . . ?
C16 Fe1 C4 120.57(15) . . ?
C16 Fe1 C17 40.65(6) . . ?
C16 Fe1 C14 68.42(7) . . ?
C15 Fe1 C3 121.77(13) . . ?
C15 Fe1 C4 156.44(17) . . ?
C15 Fe1 C17 68.41(7) . . ?
C15 Fe1 C16 40.69(6) . . ?
C15 Fe1 C14 40.68(6) . . ?
C14 Fe1 C3 157.29(14) . . ?
C14 Fe1 C4 160.92(15) . . ?
C14 Fe1 C17 68.38(8) . . ?
C15A Fe1 C1 113.0(3) . . ?
C15A Fe1 C2 104.9(2) . . ?
C15A Fe1 C3 128.5(3) . . ?
C15A Fe1 C4 168.7(3) . . ?
C15A Fe1 C5 146.8(3) . . ?
C15A Fe1 C18A 68.77(19) . . ?
C14A Fe1 C1 106.5(2) . . ?
C14A Fe1 C2 127.7(3) . . ?
C14A Fe1 C3 166.9(3) . . ?
C14A Fe1 C4 150.3(3) . . ?
C14A Fe1 C5 116.1(2) . . ?
C14A Fe1 C15A 40.98(15) . . ?
C14A Fe1 C18A 40.97(16) . . ?
C18A Fe1 C1 131.1(3) . . ?
C18A Fe1 C2 168.0(3) . . ?
C18A Fe1 C3 151.1(3) . . ?
C18A Fe1 C4 119.3(2) . . ?
C18A Fe1 C5 110.7(2) . . ?
C6 O1 C13 110.3(2) . . ?
C7 N1 C6 116.1(2) . . ?
C2 C1 Fe1 69.81(16) . . ?
C2 C1 C5 108.3(2) . . ?
C5 C1 Fe1 69.62(15) . . ?
C1 C2 Fe1 69.56(16) . . ?
C1 C2 C3 108.0(2) . . ?
C3 C2 Fe1 69.80(17) . . ?
C2 C3 Fe1 69.49(16) . . ?
C4 C3 Fe1 69.65(16) . . ?
C4 C3 C2 108.2(2) . . ?
C3 C4 Fe1 69.69(15) . . ?
C3 C4 C5 107.7(2) . . ?
C5 C4 Fe1 69.28(14) . . ?
C1 C5 Fe1 69.60(15) . . ?
C1 C5 C4 107.9(2) . . ?
C1 C5 C6 127.2(2) . . ?
C4 C5 Fe1 69.79(15) . . ?
C4 C5 C6 124.9(2) . . ?
C6 C5 Fe1 127.5(2) . . ?
O1 C6 N1 111.9(2) . . ?
O1 C6 C5 108.6(2) . . ?
N1 C6 C5 110.2(3) . . ?
C8 C7 N1 120.2(2) . . ?
C12 C7 N1 119.7(2) . . ?
C12 C7 C8 120.1(2) . . ?
C9 C8 C7 120.2(2) . . ?
C8 C9 C10 120.0(2) . . ?
C11 C10 C9 119.9(2) . . ?
C10 C11 C12 121.1(3) . . ?
C7 C12 C11 118.6(2) . . ?
C7 C12 C13 120.0(2) . . ?
C11 C12 C13 121.4(2) . . ?
O1 C13 C12 112.2(2) . . ?
C16 C17 Fe1 69.58(13) . . ?
C18 C17 Fe1 69.71(14) . . ?
C18 C17 C16 108.0 . . ?
C17 C16 Fe1 69.77(13) . . ?
C15 C16 Fe1 69.62(13) . . ?
C15 C16 C17 108.0 . . ?
C16 C15 Fe1 69.70(13) . . ?
C14 C15 Fe1 69.73(14) . . ?
C14 C15 C16 108.0 . . ?
C15 C14 Fe1 69.59(13) . . ?
C15 C14 C18 108.0 . . ?
C18 C14 Fe1 69.76(13) . . ?
C17 C18 Fe1 69.67(13) . . ?
C17 C18 C14 108.0 . . ?
C14 C18 Fe1 69.60(13) . . ?
C16A C17A Fe1 69.7(3) . . ?
C18A C17A Fe1 69.0(3) . . ?
C18A C17A C16A 108.0 . . ?
C17A C16A Fe1 69.8(3) . . ?
C15A C16A Fe1 69.0(3) . . ?
C15A C16A C17A 108.0 . . ?
C16A C15A Fe1 70.3(3) . . ?
C16A C15A C14A 108.0 . . ?
C14A C15A Fe1 69.1(3) . . ?
C15A C14A Fe1 69.9(3) . . ?
C18A C14A Fe1 69.9(3) . . ?
C18A C14A C15A 108.0 . . ?
C17A C18A Fe1 70.3(3) . . ?
C17A C18A C14A 108.0 . . ?
C14A C18A Fe1 69.1(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C4 H4 O1 0.95 2.52 3.343(3) 144.5 1_455 yes

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.977(18)
2 0.023(18)

