# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_pam
_database_code_depnum_ccdc_archive 'CCDC 1827974'
_audit_update_record             
;
2018-03-06 deposited with the CCDC.
2018-09-05 downloaded from the CCDC.
;

_audit_creation_method           
;
SHELXL-2014/7
;
_computing_data_collection       'CrysAlisPro (Rigaku Oxford Diffraction,2016)'

_computing_cell_refinement       'CrysAlisPro (Rigaku Oxford Diffraction,2016)'

_computing_data_reduction        'CrysAlisPro (Rigaku Oxford Diffraction,2016)'


_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H27 Fe0.50 I N9 O3'
_chemical_formula_weight         644.37


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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.8846(6)
_cell_length_b                   10.8052(6)
_cell_length_c                   13.4619(7)
_cell_angle_alpha                99.573(4)
_cell_angle_beta                 98.738(5)
_cell_angle_gamma                97.891(5)
_cell_volume                     1381.69(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3690
_cell_measurement_theta_min      4.4350
_cell_measurement_theta_max      30.0600
_exptl_crystal_description       plate
_exptl_crystal_colour            violet-brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    1.454
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_T_min  0.94067
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro (Rigaku Oxford Diffraction,2016)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.3426
_diffrn_orient_matrix_UB_11      0.0617640000
_diffrn_orient_matrix_UB_12      0.0132541000
_diffrn_orient_matrix_UB_13      -0.0198674000
_diffrn_orient_matrix_UB_21      -0.0400557000
_diffrn_orient_matrix_UB_22      -0.0028451000
_diffrn_orient_matrix_UB_23      -0.0489825000
_diffrn_orient_matrix_UB_31      -0.0015634000
_diffrn_orient_matrix_UB_32      0.0661421000
_diffrn_orient_matrix_UB_33      0.0124723000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -36.00   19.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       25.7227  -57.0000   90.0000 55

#__ type_ start__ end____ width___ exp.time_
  2 omega   31.00   63.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       25.7227  -99.0000  120.0000 32

#__ type_ start__ end____ width___ exp.time_
  3 omega  -40.00   70.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       25.7227  -19.0000  150.0000 110

#__ type_ start__ end____ width___ exp.time_
  4 omega  -41.00   -5.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6915  -77.0000 -120.0000 36

#__ type_ start__ end____ width___ exp.time_
  5 omega   26.00   63.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       25.7227  -99.0000 -150.0000 37

#__ type_ start__ end____ width___ exp.time_
  6 omega  -99.00    1.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6915  -77.0000  -30.0000 100

#__ type_ start__ end____ width___ exp.time_
  7 omega  -48.00    3.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6915   57.0000 -180.0000 51

#__ type_ start__ end____ width___ exp.time_
  8 omega -101.00  -46.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6915  179.0000  -60.0000 55
;
_diffrn_measurement_method       'ω scans'
_symmetry_space_group_name_H-M_alt 'P -1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_cell_setting           triclinic
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_theta     30.44
_reflns_odcompleteness_iscentric 1
_diffrn_ambient_temperature      293(2)
_diffrn_reflns_number            14255
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.231
_diffrn_reflns_theta_max         29.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             7309
_reflns_number_gt                5057
_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_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0308P)²] 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         7309
_refine_ls_number_parameters     346
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0843
_refine_ls_wR_factor_gt          0.0718
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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
Fe Fe 0.0000 0.5000 0.0000 0.03333(12) Uani 1 2 d S . P . .
I I 0.69941(2) 0.20592(2) 0.32886(2) 0.06434(9) Uani 1 1 d . . . . .
C1 C 0.1625(2) 0.5909(2) 0.09308(17) 0.0373(5) Uani 1 1 d . . . . .
C2 C 0.0233(2) 0.3519(2) 0.05897(17) 0.0384(6) Uani 1 1 d . . . . .
C2A C 0.2351(3) 0.3973(3) 0.3279(2) 0.0521(7) Uani 1 1 d . . . . .
H2A H 0.2134 0.3806 0.2568 0.062 Uiso 1 1 calc R U . . .
C2B C 1.5718(3) -0.2516(3) 1.0390(2) 0.0572(8) Uani 1 1 d . . . . .
H2B H 1.6559 -0.2775 1.0592 0.069 Uiso 1 1 calc R U . . .
C2C C 0.8616(3) 0.0957(3) 0.7029(2) 0.0581(8) Uani 1 1 d . . . . .
H2C H 0.8356 0.1675 0.7383 0.070 Uiso 1 1 calc R U . . .
C3 C 0.1120(2) 0.4428(2) -0.09775(17) 0.0377(5) Uani 1 1 d . . . . .
C3A C 0.3348(3) 0.3412(2) 0.37558(19) 0.0502(7) Uani 1 1 d . . . . .
H3A H 0.3802 0.2864 0.3369 0.060 Uiso 1 1 calc R U . . .
C3B C 1.5375(3) -0.1492(2) 1.0966(2) 0.0518(7) Uani 1 1 d . . . . .
H3B H 1.5970 -0.1069 1.1565 0.062 Uiso 1 1 calc R U . . .
C3C C 0.8061(3) 0.0532(2) 0.6016(2) 0.0554(7) Uani 1 1 d . . . . .
H3C H 0.7419 0.0955 0.5690 0.066 Uiso 1 1 calc R U . . .
C4A C 0.3689(2) 0.3651(2) 0.48142(18) 0.0393(5) Uani 1 1 d . . . . .
C4B C 1.4143(3) -0.1072(2) 1.06647(18) 0.0412(6) Uani 1 1 d . . . . .
C4C C 0.8451(3) -0.0529(2) 0.54725(18) 0.0404(6) Uani 1 1 d . . . . .
C5A C 0.3005(3) 0.4495(2) 0.53534(19) 0.0461(6) Uani 1 1 d . . . . .
H5A H 0.3220 0.4692 0.6064 0.055 Uiso 1 1 calc R U . . .
C5B C 1.3266(3) -0.1769(2) 0.97821(19) 0.0471(6) Uani 1 1 d . . . . .
H5B H 1.2424 -0.1522 0.9562 0.056 Uiso 1 1 calc R U . . .
C5C C 0.9392(3) -0.1133(2) 0.60017(19) 0.0455(6) Uani 1 1 d . . . . .
H5C H 0.9675 -0.1848 0.5663 0.055 Uiso 1 1 calc R U . . .
C6A C 0.2019(3) 0.5037(2) 0.48449(19) 0.0482(6) Uani 1 1 d . . . . .
H6A H 0.1572 0.5609 0.5214 0.058 Uiso 1 1 calc R U . . .
C6B C 1.3637(3) -0.2804(2) 0.9244(2) 0.0515(7) Uani 1 1 d . . . . .
H6B H 1.3035 -0.3275 0.8665 0.062 Uiso 1 1 calc R U . . .
C6C C 0.9905(3) -0.0684(2) 0.7017(2) 0.0485(6) Uani 1 1 d . . . . .
H6C H 1.0526 -0.1104 0.7367 0.058 Uiso 1 1 calc R U . . .
C7A C 0.0571(3) 0.5326(3) 0.3285(2) 0.0626(8) Uani 1 1 d . . . . .
H7A1 H 0.0815 0.5514 0.2656 0.094 Uiso 1 1 calc R U . . .
H7A2 H 0.0462 0.6096 0.3714 0.094 Uiso 1 1 calc R U . . .
H7A3 H -0.0284 0.4735 0.3138 0.094 Uiso 1 1 calc R U . . .
C7B C 1.5270(4) -0.4240(3) 0.8885(3) 0.0762(10) Uani 1 1 d . . . . .
H7B1 H 1.4510 -0.4939 0.8705 0.114 Uiso 1 1 calc R U . . .
H7B2 H 1.6061 -0.4499 0.9252 0.114 Uiso 1 1 calc R U . . .
H7B3 H 1.5501 -0.3984 0.8273 0.114 Uiso 1 1 calc R U . . .
C7C C 1.0146(3) 0.0856(3) 0.8608(2) 0.0636(8) Uani 1 1 d . . . . .
H7C1 H 1.1087 0.1262 0.8659 0.095 Uiso 1 1 calc R U . . .
H7C2 H 1.0132 0.0165 0.8974 0.095 Uiso 1 1 calc R U . . .
H7C3 H 0.9621 0.1463 0.8899 0.095 Uiso 1 1 calc R U . . .
C8A C 0.4735(3) 0.3021(2) 0.53181(19) 0.0456(6) Uani 1 1 d . . . . .
H8A H 0.5075 0.2370 0.4939 0.055 Uiso 1 1 calc R U . . .
C8B C 1.3799(3) 0.0060(2) 1.1262(2) 0.0516(7) Uani 1 1 d . . . . .
H8B H 1.4350 0.0442 1.1890 0.062 Uiso 1 1 calc R U . . .
C8C C 0.7877(3) -0.0957(2) 0.43773(19) 0.0447(6) Uani 1 1 d . . . . .
H8C H 0.7226 -0.0537 0.4059 0.054 Uiso 1 1 calc R U . . .
N1 N 0.2594(2) 0.6432(2) 0.15194(16) 0.0497(6) Uani 1 1 d . . . . .
N1A N 0.1680(2) 0.47614(19) 0.38168(16) 0.0440(5) Uani 1 1 d . . . . .
N1B N 1.4868(2) -0.3160(2) 0.95382(18) 0.0508(6) Uani 1 1 d . . . . .
N1C N 0.9523(2) 0.03596(19) 0.75154(15) 0.0457(5) Uani 1 1 d . . . . .
N2 N 0.0429(2) 0.2636(2) 0.09318(16) 0.0537(6) Uani 1 1 d . . . . .
N2A N 0.5182(2) 0.33619(19) 0.62770(15) 0.0449(5) Uani 1 1 d . . . . .
N2B N 1.2751(2) 0.05222(19) 1.09251(16) 0.0462(5) Uani 1 1 d . . . . .
N2C N 0.8264(2) -0.18951(18) 0.38626(15) 0.0431(5) Uani 1 1 d . . . . .
N3 N 0.1752(2) 0.4047(2) -0.15745(16) 0.0502(6) Uani 1 1 d . . . . .
O1A O 0.6133(2) 0.26382(19) 0.66046(14) 0.0644(6) Uani 1 1 d . . . . .
H1A H 0.6451 0.2906 0.7214 0.097 Uiso 1 1 calc R U . . .
O1B O 1.2591(2) 0.15832(18) 1.15959(15) 0.0625(6) Uani 1 1 d . . . . .
H1B H 1.1930 0.1882 1.1346 0.094 Uiso 1 1 calc R U . . .
O1C O 0.7604(2) -0.21234(17) 0.28545(13) 0.0549(5) Uani 1 1 d . . . . .
H1C H 0.7809 -0.2771 0.2544 0.082 Uiso 1 1 calc R 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
Fe C1 1.913(2) . ?
Fe C1 1.913(2) 2_565 ?
Fe C3 1.923(3) . ?
Fe C3 1.923(2) 2_565 ?
Fe C2 1.927(2) 2_565 ?
Fe C2 1.927(2) . ?
C1 N1 1.156(3) . ?
C2 N2 1.153(3) . ?
C2A N1A 1.337(3) . ?
C2A C3A 1.361(3) . ?
C2B N1B 1.337(3) . ?
C2B C3B 1.356(4) . ?
C2C N1C 1.331(3) . ?
C2C C3C 1.366(4) . ?
C3 N3 1.148(3) . ?
C3A C4A 1.385(3) . ?
C3B C4B 1.384(3) . ?
C3C C4C 1.388(3) . ?
C4A C5A 1.383(3) . ?
C4A C8A 1.458(3) . ?
C4B C5B 1.393(3) . ?
C4B C8B 1.459(3) . ?
C4C C5C 1.385(3) . ?
C4C C8C 1.468(3) . ?
C5A C6A 1.360(3) . ?
C5B C6B 1.354(3) . ?
C5C C6C 1.364(3) . ?
C6A N1A 1.346(3) . ?
C6B N1B 1.348(3) . ?
C6C N1C 1.344(3) . ?
C7A N1A 1.475(3) . ?
C7B N1B 1.479(3) . ?
C7C N1C 1.485(3) . ?
C8A N2A 1.273(3) . ?
C8B N2B 1.267(3) . ?
C8C N2C 1.268(3) . ?
N2A O1A 1.371(2) . ?
N2B O1B 1.379(2) . ?
N2C O1C 1.380(2) . ?

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 Fe C1 180.0 . 2_565 ?
C1 Fe C3 90.59(9) . . ?
C1 Fe C3 89.41(9) 2_565 . ?
C1 Fe C3 89.41(9) . 2_565 ?
C1 Fe C3 90.59(9) 2_565 2_565 ?
C3 Fe C3 180.0 . 2_565 ?
C1 Fe C2 91.24(9) . 2_565 ?
C1 Fe C2 88.76(9) 2_565 2_565 ?
C3 Fe C2 91.64(10) . 2_565 ?
C3 Fe C2 88.36(10) 2_565 2_565 ?
C1 Fe C2 88.76(9) . . ?
C1 Fe C2 91.24(9) 2_565 . ?
C3 Fe C2 88.36(10) . . ?
C3 Fe C2 91.64(10) 2_565 . ?
C2 Fe C2 180.0 2_565 . ?
N1 C1 Fe 177.5(2) . . ?
N2 C2 Fe 177.0(2) . . ?
N1A C2A C3A 121.0(2) . . ?
N1B C2B C3B 121.2(2) . . ?
N1C C2C C3C 121.0(2) . . ?
N3 C3 Fe 177.5(2) . . ?
C2A C3A C4A 120.4(2) . . ?
C2B C3B C4B 120.2(2) . . ?
C2C C3C C4C 120.2(2) . . ?
C5A C4A C3A 117.5(2) . . ?
C5A C4A C8A 122.5(2) . . ?
C3A C4A C8A 119.9(2) . . ?
C3B C4B C5B 117.5(2) . . ?
C3B C4B C8B 120.3(2) . . ?
C5B C4B C8B 122.2(2) . . ?
C5C C4C C3C 117.4(2) . . ?
C5C C4C C8C 122.8(2) . . ?
C3C C4C C8C 119.8(2) . . ?
C6A C5A C4A 120.1(2) . . ?
C6B C5B C4B 120.2(2) . . ?
C6C C5C C4C 120.4(2) . . ?
N1A C6A C5A 121.2(2) . . ?
N1B C6B C5B 120.8(2) . . ?
N1C C6C C5C 120.7(2) . . ?
N2A C8A C4A 120.0(2) . . ?
N2B C8B C4B 120.0(2) . . ?
N2C C8C C4C 120.4(2) . . ?
C2A N1A C6A 119.7(2) . . ?
C2A N1A C7A 120.1(2) . . ?
C6A N1A C7A 120.2(2) . . ?
C2B N1B C6B 120.0(2) . . ?
C2B N1B C7B 121.1(2) . . ?
C6B N1B C7B 118.8(2) . . ?
C2C N1C C6C 120.3(2) . . ?
C2C N1C C7C 120.3(2) . . ?
C6C N1C C7C 119.4(2) . . ?
C8A N2A O1A 110.9(2) . . ?
C8B N2B O1B 111.6(2) . . ?
C8C N2C O1C 110.6(2) . . ?

_refine_diff_density_max         0.655
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.060

# start Validation Reply Form
_vrf_PLAT910_shelx               
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         24 Note  
RESPONSE: These reflections are shielded by the beamstio
;
# end Validation Reply Form


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

data_bepa
_database_code_depnum_ccdc_archive 'CCDC 1827975'
_audit_update_record             
;
2018-03-06 deposited with the CCDC.
2018-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H36 Fe0.50 N7 O7'
_chemical_formula_weight         622.57

_computing_data_collection       'CrysAlisPro (Rigaku Oxford Diffraction,2016)'

_computing_cell_refinement       'CrysAlisPro (Rigaku Oxford Diffraction,2016)'

_computing_data_reduction        'CrysAlisPro (Rigaku Oxford Diffraction,2016)'

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.2150(5)
_cell_length_b                   12.2553(5)
_cell_length_c                   16.2052(8)
_cell_angle_alpha                108.627(4)
_cell_angle_beta                 95.042(4)
_cell_angle_gamma                105.537(4)
_cell_volume                     1640.43(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3781
_cell_measurement_theta_min      4.5490
_cell_measurement_theta_max      28.6510
_cell_oxdiff_length_a            9.2150(5)
_cell_oxdiff_length_b            12.2553(5)
_cell_oxdiff_length_c            16.2052(8)
_cell_oxdiff_angle_alpha         108.627(4)
_cell_oxdiff_angle_beta          95.042(4)
_cell_oxdiff_angle_gamma         105.537(4)
_cell_oxdiff_volume              1640.44(14)

_exptl_crystal_description       plate
_exptl_crystal_colour            red-brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             656

_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.301
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_T_min  0.93378
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro (Rigaku Oxford Diffraction,2016)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.3426

_diffrn_reflns_number            14585
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.231
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             7455
_reflns_number_gt                6036
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_diffrn_orient_matrix_UB_11      0.0311846000
_diffrn_orient_matrix_UB_12      -0.0386946000
_diffrn_orient_matrix_UB_13      -0.0307593000
_diffrn_orient_matrix_UB_21      -0.0479068000
_diffrn_orient_matrix_UB_22      0.0025924000
_diffrn_orient_matrix_UB_23      -0.0355962000
_diffrn_orient_matrix_UB_31      0.0579142000
_diffrn_orient_matrix_UB_32      0.0513116000
_diffrn_orient_matrix_UB_33      -0.0003251000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   42.00   68.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       28.6542   57.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega   70.00   99.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       28.6542   57.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
  3 omega   40.00   97.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       28.6542  179.0000  -60.0000 57

#__ type_ start__ end____ width___ exp.time_
  4 omega  -97.00   -1.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.4667  -77.0000    0.0000 96

#__ type_ start__ end____ width___ exp.time_
  5 omega  -24.00   34.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.4667   57.0000  150.0000 58

#__ type_ start__ end____ width___ exp.time_
  6 omega -104.00   -1.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.4667  -77.0000  -90.0000 103

#__ type_ start__ end____ width___ exp.time_
  7 omega  -93.00  -44.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.4667  133.0000   83.0000 49

#__ type_ start__ end____ width___ exp.time_
  8 omega  -31.00   40.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.4667   37.0000  120.0000 71

;
_diffrn_measurement_method       'ω scans'


_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_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0747P)²+0.1991P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7455
_refine_ls_number_parameters     420
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1470
_refine_ls_wR_factor_gt          0.1359
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.036
_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
Fe Fe 0.0000 0.5000 0.5000 0.03538(13) Uani 1 2 d S . P . .
C1 C 0.1823(2) 0.63390(16) 0.54923(13) 0.0429(4) Uani 1 1 d . . . . .
C2 C 0.1160(2) 0.39729(17) 0.44675(13) 0.0449(4) Uani 1 1 d . . . . .
C2A C 0.3586(3) 0.3122(2) 0.61377(17) 0.0627(6) Uani 1 1 d . . . . .
H2A H 0.2585 0.3148 0.6064 0.075 Uiso 1 1 calc R U . . .
C2B C 0.1087(5) 0.7527(4) 0.7725(2) 0.1077(12) Uani 1 1 d . . . . .
H2B H 0.1122 0.7171 0.7131 0.129 Uiso 1 1 calc R U . . .
C3 C 0.0211(2) 0.45665(16) 0.60265(13) 0.0420(4) Uani 1 1 d . . . . .
C3A C 0.3841(3) 0.2063(2) 0.60986(16) 0.0589(6) Uani 1 1 d . . . . .
H3A H 0.3018 0.1373 0.6000 0.071 Uiso 1 1 calc R U . . .
C3B C 0.0454(6) 0.6813(4) 0.8172(2) 0.1189(14) Uani 1 1 d . . . . .
H3B H 0.0075 0.5976 0.7884 0.143 Uiso 1 1 calc R U . . .
C4A C 0.5331(2) 0.20168(19) 0.62068(14) 0.0498(5) Uani 1 1 d . . . . .
C4B C 0.0369(4) 0.7322(3) 0.90526(18) 0.0875(9) Uani 1 1 d . . . . .
C5A C 0.6514(3) 0.3065(2) 0.63397(17) 0.0601(6) Uani 1 1 d . . . . .
H5A H 0.7525 0.3062 0.6411 0.072 Uiso 1 1 calc R U . . .
C5B C 0.0961(5) 0.8551(3) 0.94429(18) 0.0953(10) Uani 1 1 d . . . . .
H5B H 0.0954 0.8926 1.0040 0.114 Uiso 1 1 calc R U . . .
C6A C 0.6202(3) 0.4098(2) 0.63663(17) 0.0607(6) Uani 1 1 d . . . . .
H6A H 0.7003 0.4794 0.6445 0.073 Uiso 1 1 calc R U . . .
C6B C 0.1560(5) 0.9228(3) 0.8964(2) 0.1118(13) Uani 1 1 d . . . . .
H6B H 0.1915 1.0069 0.9228 0.134 Uiso 1 1 calc R U . . .
C7A C 0.4474(3) 0.5304(2) 0.64027(16) 0.0640(6) Uani 1 1 d . . . . .
H7A1 H 0.3409 0.5157 0.6163 0.077 Uiso 1 1 calc R U . . .
H7A2 H 0.5110 0.5725 0.6083 0.077 Uiso 1 1 calc R U . . .
C7B C 0.2193(6) 0.9443(4) 0.7558(2) 0.1253(15) Uani 1 1 d . . . . .
H37A H 0.1362 0.9704 0.7363 0.150 Uiso 1 1 calc R U . . .
H37B H 0.2455 0.8940 0.7034 0.150 Uiso 1 1 calc R U . . .
C8A C 0.4838(3) 0.6075(2) 0.73694(16) 0.0600(6) Uani 1 1 d . . . . .
C8B C 0.3573(4) 1.0549(4) 0.8045(2) 0.0970(11) Uani 1 1 d D . . . .
C9A C 0.6053(4) 0.7114(3) 0.7703(2) 0.0912(10) Uani 1 1 d . . . . .
H9A H 0.6666 0.7352 0.7325 0.109 Uiso 1 1 calc R U . . .
C9B C 0.4973(8) 1.0491(7) 0.8281(3) 0.158(2) Uani 1 1 d . . . . .
H9B H 0.5120 0.9741 0.8183 0.190 Uiso 1 1 calc R U . . .
C10A C 0.6387(5) 0.7819(3) 0.8594(3) 0.1138(13) Uani 1 1 d . . . . .
H10A H 0.7213 0.8531 0.8810 0.137 Uiso 1 1 calc R U . . .
C10B C 0.6177(9) 1.1522(13) 0.8664(6) 0.216(6) Uani 1 1 d . . . . .
H10B H 0.7131 1.1464 0.8845 0.260 Uiso 1 1 calc R U . . .
C11A C 0.5514(5) 0.7477(4) 0.9156(2) 0.1109(12) Uani 1 1 d . . . . .
H11A H 0.5741 0.7949 0.9756 0.133 Uiso 1 1 calc R U . . .
C11B C 0.6037(13) 1.2632(12) 0.8790(6) 0.235(7) Uani 1 1 d . . . . .
H11B H 0.6882 1.3329 0.9025 0.282 Uiso 1 1 calc R U . . .
C12A C 0.4300(5) 0.6434(4) 0.8831(2) 0.1271(16) Uani 1 1 d . . . . .
H12A H 0.3698 0.6191 0.9211 0.153 Uiso 1 1 calc R U . . .
C12B C 0.4621(9) 1.2684(5) 0.8561(4) 0.169(3) Uani 1 1 d D . . . .
H12B H 0.4478 1.3434 0.8653 0.203 Uiso 1 1 calc R U . . .
C13A C 0.3969(4) 0.5744(3) 0.7945(2) 0.1068(12) Uani 1 1 d . . . . .
H13A H 0.3136 0.5037 0.7731 0.128 Uiso 1 1 calc R U . . .
C13B C 0.3390(5) 1.1648(5) 0.8194(2) 0.1104(13) Uani 1 1 d D . . . .
H13B H 0.2421 1.1704 0.8046 0.132 Uiso 1 1 calc R U . . .
C14A C 0.5709(3) 0.0934(2) 0.61959(17) 0.0592(6) Uani 1 1 d . . . . .
H14A H 0.6733 0.0969 0.6297 0.071 Uiso 1 1 calc R U . . .
C14B C -0.0312(6) 0.6541(3) 0.9522(3) 0.1128(13) Uani 1 1 d . . . . .
H14B H -0.0771 0.5715 0.9210 0.135 Uiso 1 1 calc R U . . .
N1 N 0.2908(2) 0.71693(16) 0.57977(14) 0.0618(5) Uani 1 1 d . . . . .
N1A N 0.4755(2) 0.41251(16) 0.62811(12) 0.0536(4) Uani 1 1 d . . . . .
N1B N 0.1647(4) 0.8699(3) 0.81086(15) 0.0969(9) Uani 1 1 d . . . . .
N2 N 0.1844(3) 0.33376(19) 0.41519(16) 0.0708(6) Uani 1 1 d . . . . .
N2A N 0.4670(2) -0.00512(16) 0.60518(12) 0.0537(4) Uani 1 1 d . . . . .
N2B N -0.0291(4) 0.6958(2) 1.03316(18) 0.0910(8) Uani 1 1 d . . . . .
N3 N 0.0330(2) 0.42875(17) 0.66388(12) 0.0586(5) Uani 1 1 d . . . . .
O1A O 0.52731(19) -0.09588(14) 0.60750(14) 0.0733(5) Uani 1 1 d . . . . .
H1A H 0.4578 -0.1604 0.5924 0.110 Uiso 1 1 calc R U . . .
O1B O -0.0992(5) 0.6076(2) 1.0656(2) 0.1396(11) Uani 1 1 d . . . . .
H1B H -0.0794 0.6354 1.1200 0.209 Uiso 1 1 calc R U . . .
OW1 O 0.8201(2) 0.90175(16) 0.66486(17) 0.0874(6) Uani 1 1 d D . . . .
H11 H 0.825(4) 0.8315(16) 0.637(2) 0.131 Uiso 1 1 d D U . . .
H12 H 0.733(2) 0.906(3) 0.647(2) 0.131 Uiso 1 1 d D U . . .
OW2 O 0.9343(5) 1.0364(3) 0.8428(2) 0.1424(11) Uani 1 1 d D . . . .
H21 H 0.899(8) 1.003(4) 0.7871(10) 0.214 Uiso 1 1 d D U . . .
H22 H 0.962(8) 1.1133(7) 0.857(3) 0.214 Uiso 1 1 d D U . . .
OW3 O 0.1040(4) 0.8658(2) 0.5112(2) 0.1522(13) Uani 1 1 d . . . . .
H31 H 0.1531 0.8148 0.5026 0.228 Uiso 1 1 d . U . . .
H32 H 0.0215 0.8416 0.5251 0.228 Uiso 1 1 d . U . . .
OW4 O -0.0173(3) 0.9107(3) 0.3705(2) 0.1326(10) Uani 1 1 d D . . . .
H41 H 0.026(6) 0.892(4) 0.410(3) 0.199 Uiso 1 1 d D U . . .
H42 H 0.034(6) 0.982(2) 0.375(4) 0.199 Uiso 1 1 d D U . . .
OW5 O -0.0373(5) 0.7089(3) 0.23381(19) 0.1472(12) Uani 1 1 d D . . . .
H51 H -0.019(8) 0.667(4) 0.264(3) 0.221 Uiso 1 1 d D U . . .
H52 H -0.026(9) 0.780(2) 0.268(3) 0.221 Uiso 1 1 d 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
Fe C1 1.898(2) . ?
Fe C1 1.898(2) 2_566 ?
Fe C3 1.9106(19) . ?
Fe C3 1.9106(19) 2_566 ?
Fe C2 1.913(2) . ?
Fe C2 1.913(2) 2_566 ?
C1 N1 1.152(2) . ?
C2 N2 1.153(3) . ?
C2A N1A 1.338(3) . ?
C2A C3A 1.362(3) . ?
C2B N1B 1.301(5) . ?
C2B C3B 1.355(5) . ?
C3 N3 1.154(2) . ?
C3A C4A 1.388(3) . ?
C3B C4B 1.382(4) . ?
C4A C5A 1.384(3) . ?
C4A C14A 1.455(3) . ?
C4B C5B 1.362(4) . ?
C4B C14B 1.455(5) . ?
C5A C6A 1.361(3) . ?
C5B C6B 1.356(5) . ?
C6A N1A 1.339(3) . ?
C6B N1B 1.349(4) . ?
C7A N1A 1.490(3) . ?
C7A C8A 1.501(3) . ?
C7B N1B 1.495(5) . ?
C7B C8B 1.515(6) . ?
C8A C9A 1.363(4) . ?
C8A C13A 1.369(4) . ?
C8B C9B 1.341(6) . ?
C8B C13B 1.349(3) . ?
C9A C10A 1.382(5) . ?
C9B C10B 1.356(12) . ?
C10A C11A 1.358(5) . ?
C10B C11B 1.352(14) . ?
C11A C12A 1.365(5) . ?
C11B C12B 1.349(13) . ?
C12A C13A 1.370(5) . ?
C12B C13B 1.371(4) . ?
C14A N2A 1.261(3) . ?
C14B N2B 1.243(4) . ?
N2A O1A 1.379(2) . ?
N2B O1B 1.382(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
C1 Fe C1 180.0 . 2_566 ?
C1 Fe C3 90.95(8) . . ?
C1 Fe C3 89.05(8) 2_566 . ?
C1 Fe C3 89.05(8) . 2_566 ?
C1 Fe C3 90.95(8) 2_566 2_566 ?
C3 Fe C3 180.0 . 2_566 ?
C1 Fe C2 90.58(8) . . ?
C1 Fe C2 89.42(8) 2_566 . ?
C3 Fe C2 89.38(8) . . ?
C3 Fe C2 90.62(8) 2_566 . ?
C1 Fe C2 89.42(8) . 2_566 ?
C1 Fe C2 90.58(8) 2_566 2_566 ?
C3 Fe C2 90.62(8) . 2_566 ?
C3 Fe C2 89.38(8) 2_566 2_566 ?
C2 Fe C2 180.00(8) . 2_566 ?
N1 C1 Fe 178.4(2) . . ?
N2 C2 Fe 178.73(19) . . ?
N1A C2A C3A 121.0(2) . . ?
N1B C2B C3B 121.6(3) . . ?
N3 C3 Fe 179.02(17) . . ?
C2A C3A C4A 119.9(2) . . ?
C2B C3B C4B 120.3(4) . . ?
C5A C4A C3A 117.8(2) . . ?
C5A C4A C14A 118.7(2) . . ?
C3A C4A C14A 123.53(19) . . ?
C5B C4B C3B 117.3(3) . . ?
C5B C4B C14B 123.2(3) . . ?
C3B C4B C14B 119.5(3) . . ?
C6A C5A C4A 120.3(2) . . ?
C6B C5B C4B 120.2(3) . . ?
N1A C6A C5A 120.7(2) . . ?
N1B C6B C5B 120.9(3) . . ?
N1A C7A C8A 110.19(18) . . ?
N1B C7B C8B 113.4(3) . . ?
C9A C8A C13A 118.0(3) . . ?
C9A C8A C7A 121.1(2) . . ?
C13A C8A C7A 120.8(2) . . ?
C9B C8B C13B 118.8(5) . . ?
C9B C8B C7B 123.5(5) . . ?
C13B C8B C7B 117.6(4) . . ?
C8A C9A C10A 120.9(3) . . ?
C8B C9B C10B 120.2(7) . . ?
C11A C10A C9A 120.3(3) . . ?
C11B C10B C9B 122.2(9) . . ?
C10A C11A C12A 119.3(3) . . ?
C12B C11B C10B 117.2(9) . . ?
C11A C12A C13A 120.1(4) . . ?
C11B C12B C13B 121.0(8) . . ?
C8A C13A C12A 121.4(3) . . ?
C8B C13B C12B 120.6(5) . . ?
N2A C14A C4A 121.0(2) . . ?
N2B C14B C4B 121.1(3) . . ?
C2A N1A C6A 120.4(2) . . ?
C2A N1A C7A 120.5(2) . . ?
C6A N1A C7A 118.9(2) . . ?
C2B N1B C6B 119.7(3) . . ?
C2B N1B C7B 118.8(3) . . ?
C6B N1B C7B 121.1(3) . . ?
C14A N2A O1A 111.68(18) . . ?
C14B N2B O1B 112.6(3) . . ?

_refine_diff_density_max         0.327
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.045

