# 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_WE2663
_database_code_depnum_ccdc_archive 'CCDC 1584016'
_audit_update_record             
;
2017-11-05 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H9 Fe N3 O3'
_chemical_formula_sum            'C12 H9 Fe N3 O3'
_chemical_formula_weight         299.07
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                            UNIT CELL INFORMATION                             #
#------------------------------------------------------------------------------#


_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8750(2)
_cell_length_b                   7.3536(3)
_cell_length_c                   14.1683(5)
_cell_angle_alpha                76.132(2)
_cell_angle_beta                 79.3330(10)
_cell_angle_gamma                79.2490(10)
_cell_volume                     577.47(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    295
_cell_measurement_reflns_used    2988
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      27.05
_cell_measurement_wavelength     0.71073

#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       board
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.030
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.720
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             304
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.313
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_T_max  0.961

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_r_equivalents  0.0324
_diffrn_reflns_av_uneti/neti     0.0400
_diffrn_reflns_number            7239
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.522
_diffrn_reflns_theta_max         27.455
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.962
_reflns_number_total             2552
_reflns_number_gt                2148
_reflns_threshold_expression     >2sigma(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.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2017)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0380P)²] 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         2552
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0797
_refine_ls_wR_factor_gt          0.0744
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.060

#...............................................................................
# .RES SHELXL file: job.res
# .HKL SHELXL file: job.hkl
#...............................................................................



# ............... End of .HKL file .............................................
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'

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 0.33068(4) 0.69261(4) 0.76014(2) 0.02743(12) Uani 1 1 d . . . . .
C1 C 0.5848(3) 0.8633(3) 0.71123(16) 0.0328(5) Uani 1 1 d . . . . .
H1 H 0.743354 0.827883 0.716074 0.039 Uiso 1 1 calc R U . . .
C2 C 0.4749(4) 0.8566(3) 0.63184(16) 0.0367(5) Uani 1 1 d . . . . .
H2 H 0.548604 0.815439 0.575058 0.044 Uiso 1 1 calc R U . . .
C3 C 0.2339(4) 0.9230(3) 0.65351(16) 0.0373(5) Uani 1 1 d . . . . .
H3 H 0.122129 0.933406 0.613053 0.045 Uiso 1 1 calc R U . . .
C4 C 0.1899(4) 0.9710(3) 0.74655(16) 0.0337(5) Uani 1 1 d . . . . .
H4 H 0.045337 1.017670 0.778238 0.040 Uiso 1 1 calc R U . . .
C5 C 0.4079(3) 0.9347(3) 0.78292(15) 0.0308(5) Uani 1 1 d . . . . .
C6 C 0.4472(4) 0.9556(3) 0.87855(16) 0.0349(5) Uani 1 1 d . . . . .
O7 O 0.2565(3) 1.0089(3) 0.93494(13) 0.0489(5) Uani 1 1 d . . . . .
H7 H 0.281(5) 1.026(4) 0.984(2) 0.059 Uiso 1 1 d . U . . .
O8 O 0.6432(3) 0.9297(3) 0.90159(12) 0.0494(4) Uani 1 1 d . . . . .
C11 C 0.1312(3) 0.4906(3) 0.76269(16) 0.0352(5) Uani 1 1 d . . . . .
H11 H 0.020023 0.499959 0.722109 0.042 Uiso 1 1 calc R U . . .
C12 C 0.0887(4) 0.5423(3) 0.85513(17) 0.0403(5) Uani 1 1 d . . . . .
H12 H -0.055236 0.592728 0.885693 0.048 Uiso 1 1 calc R U . . .
C13 C 0.3036(4) 0.5039(3) 0.89300(17) 0.0414(5) Uani 1 1 d . . . . .
H13 H 0.324249 0.523760 0.953085 0.050 Uiso 1 1 calc R U . . .
C14 C 0.4816(4) 0.4304(3) 0.82423(16) 0.0354(5) Uani 1 1 d . . . . .
H14 H 0.639225 0.394297 0.830725 0.042 Uiso 1 1 calc R U . . .
C15 C 0.3749(3) 0.4217(3) 0.74294(16) 0.0318(5) Uani 1 1 d . . . . .
C16 C 0.4892(4) 0.3700(3) 0.64993(16) 0.0333(5) Uani 1 1 d . . . . .
O17 O 0.3908(3) 0.3524(2) 0.58621(12) 0.0426(4) Uani 1 1 d . . . . .
N18 N 0.7385(3) 0.3432(3) 0.64463(15) 0.0433(3) Uani 1 1 d . . . . .
N19 N 0.8448(3) 0.3101(3) 0.56361(16) 0.0433(3) Uani 1 1 d . . . . .
N20 N 0.9578(4) 0.2810(3) 0.49519(17) 0.0581(6) Uani 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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 C5 2.027(2) . ?
Fe1 C15 2.028(2) . ?
Fe1 C14 2.037(2) . ?
Fe1 C4 2.037(2) . ?
Fe1 C1 2.046(2) . ?
Fe1 C11 2.047(2) . ?
Fe1 C3 2.051(2) . ?
Fe1 C13 2.053(2) . ?
Fe1 C12 2.054(2) . ?
Fe1 C2 2.058(2) . ?
C1 C2 1.412(3) . ?
C1 C5 1.431(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.411(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.411(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.424(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.463(3) . ?
C6 O8 1.223(3) . ?
C6 O7 1.305(3) . ?
O7 H7 0.78(3) . ?
C11 C12 1.416(3) . ?
C11 C15 1.427(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.417(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.414(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.428(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.466(3) . ?
C16 O17 1.201(2) . ?
C16 N18 1.431(3) . ?
N18 N19 1.257(3) . ?
N19 N20 1.111(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
C5 Fe1 C15 159.57(8) . . ?
C5 Fe1 C14 122.82(9) . . ?
C15 Fe1 C14 41.15(8) . . ?
C5 Fe1 C4 41.02(8) . . ?
C15 Fe1 C4 158.34(9) . . ?
C14 Fe1 C4 158.29(9) . . ?
C5 Fe1 C1 41.14(8) . . ?
C15 Fe1 C1 123.37(8) . . ?
C14 Fe1 C1 108.55(8) . . ?
C4 Fe1 C1 68.90(8) . . ?
C5 Fe1 C11 157.94(8) . . ?
C15 Fe1 C11 40.99(8) . . ?
C14 Fe1 C11 68.88(9) . . ?
C4 Fe1 C11 121.42(8) . . ?
C1 Fe1 C11 159.04(9) . . ?
C5 Fe1 C3 68.12(9) . . ?
C15 Fe1 C3 123.33(9) . . ?
C14 Fe1 C3 160.32(9) . . ?
C4 Fe1 C3 40.39(8) . . ?
C1 Fe1 C3 67.84(9) . . ?
C11 Fe1 C3 107.18(9) . . ?
C5 Fe1 C13 107.63(9) . . ?
C15 Fe1 C13 68.34(9) . . ?
C14 Fe1 C13 40.45(9) . . ?
C4 Fe1 C13 121.95(9) . . ?
C1 Fe1 C13 124.36(9) . . ?
C11 Fe1 C13 68.04(9) . . ?
C3 Fe1 C13 157.65(9) . . ?
C5 Fe1 C12 122.33(9) . . ?
C15 Fe1 C12 68.45(9) . . ?
C14 Fe1 C12 68.38(9) . . ?
C4 Fe1 C12 106.13(9) . . ?
C1 Fe1 C12 159.69(9) . . ?
C11 Fe1 C12 40.39(8) . . ?
C3 Fe1 C12 121.91(9) . . ?
C13 Fe1 C12 40.36(9) . . ?
C5 Fe1 C2 68.30(8) . . ?
C15 Fe1 C2 108.49(8) . . ?
C14 Fe1 C2 124.64(9) . . ?
C4 Fe1 C2 68.22(9) . . ?
C1 Fe1 C2 40.24(9) . . ?
C11 Fe1 C2 122.93(9) . . ?
C3 Fe1 C2 40.16(9) . . ?
C13 Fe1 C2 160.69(9) . . ?
C12 Fe1 C2 157.95(9) . . ?
C2 C1 C5 107.57(18) . . ?
C2 C1 Fe1 70.36(12) . . ?
C5 C1 Fe1 68.74(11) . . ?
C2 C1 H1 126.2 . . ?
C5 C1 H1 126.2 . . ?
Fe1 C1 H1 126.2 . . ?
C3 C2 C1 108.19(19) . . ?
C3 C2 Fe1 69.65(12) . . ?
C1 C2 Fe1 69.40(12) . . ?
C3 C2 H2 125.9 . . ?
C1 C2 H2 125.9 . . ?
Fe1 C2 H2 126.6 . . ?
C2 C3 C4 108.94(19) . . ?
C2 C3 Fe1 70.19(12) . . ?
C4 C3 Fe1 69.27(12) . . ?
C2 C3 H3 125.5 . . ?
C4 C3 H3 125.5 . . ?
Fe1 C3 H3 126.6 . . ?
C3 C4 C5 107.32(17) . . ?
C3 C4 Fe1 70.34(12) . . ?
C5 C4 Fe1 69.12(11) . . ?
C3 C4 H4 126.3 . . ?
C5 C4 H4 126.3 . . ?
Fe1 C4 H4 125.8 . . ?
C4 C5 C1 107.98(18) . . ?
C4 C5 C6 126.98(18) . . ?
C1 C5 C6 124.97(18) . . ?
C4 C5 Fe1 69.86(11) . . ?
C1 C5 Fe1 70.12(11) . . ?
C6 C5 Fe1 123.16(15) . . ?
O8 C6 O7 123.6(2) . . ?
O8 C6 C5 122.30(18) . . ?
O7 C6 C5 114.07(18) . . ?
C6 O7 H7 113(2) . . ?
C12 C11 C15 107.74(19) . . ?
C12 C11 Fe1 70.07(12) . . ?
C15 C11 Fe1 68.80(11) . . ?
C12 C11 H11 126.1 . . ?
C15 C11 H11 126.1 . . ?
Fe1 C11 H11 126.6 . . ?
C13 C12 C11 108.16(19) . . ?
C13 C12 Fe1 69.78(12) . . ?
C11 C12 Fe1 69.54(12) . . ?
C13 C12 H12 125.9 . . ?
C11 C12 H12 125.9 . . ?
Fe1 C12 H12 126.3 . . ?
C14 C13 C12 108.6(2) . . ?
C14 C13 Fe1 69.18(12) . . ?
C12 C13 Fe1 69.86(13) . . ?
C14 C13 H13 125.7 . . ?
C12 C13 H13 125.7 . . ?
Fe1 C13 H13 126.9 . . ?
C13 C14 C15 107.49(19) . . ?
C13 C14 Fe1 70.37(12) . . ?
C15 C14 Fe1 69.09(12) . . ?
C13 C14 H14 126.3 . . ?
C15 C14 H14 126.3 . . ?
Fe1 C14 H14 125.9 . . ?
C11 C15 C14 107.98(18) . . ?
C11 C15 C16 123.66(19) . . ?
C14 C15 C16 128.13(19) . . ?
C11 C15 Fe1 70.22(11) . . ?
C14 C15 Fe1 69.77(12) . . ?
C16 C15 Fe1 121.25(14) . . ?
O17 C16 N18 123.9(2) . . ?
O17 C16 C15 125.7(2) . . ?
N18 C16 C15 110.38(18) . . ?
N19 N18 C16 112.84(18) . . ?
N20 N19 N18 173.4(2) . . ?

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
C5 C1 C2 C3 0.2(2) . . . . ?
Fe1 C1 C2 C3 59.03(15) . . . . ?
C5 C1 C2 Fe1 -58.88(14) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
Fe1 C2 C3 C4 58.57(15) . . . . ?
C1 C2 C3 Fe1 -58.88(15) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
Fe1 C3 C4 C5 59.47(14) . . . . ?
C2 C3 C4 Fe1 -59.14(15) . . . . ?
C3 C4 C5 C1 -0.2(2) . . . . ?
Fe1 C4 C5 C1 60.01(14) . . . . ?
C3 C4 C5 C6 -177.2(2) . . . . ?
Fe1 C4 C5 C6 -116.9(2) . . . . ?
C3 C4 C5 Fe1 -60.25(15) . . . . ?
C2 C1 C5 C4 0.1(2) . . . . ?
Fe1 C1 C5 C4 -59.85(14) . . . . ?
C2 C1 C5 C6 177.09(19) . . . . ?
Fe1 C1 C5 C6 117.2(2) . . . . ?
C2 C1 C5 Fe1 59.90(14) . . . . ?
C4 C5 C6 O8 -176.4(2) . . . . ?
C1 C5 C6 O8 7.2(3) . . . . ?
Fe1 C5 C6 O8 94.9(2) . . . . ?
C4 C5 C6 O7 1.8(3) . . . . ?
C1 C5 C6 O7 -174.7(2) . . . . ?
Fe1 C5 C6 O7 -86.9(2) . . . . ?
C15 C11 C12 C13 -0.6(2) . . . . ?
Fe1 C11 C12 C13 -59.29(15) . . . . ?
C15 C11 C12 Fe1 58.67(14) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
Fe1 C12 C13 C14 -58.46(15) . . . . ?
C11 C12 C13 Fe1 59.14(15) . . . . ?
C12 C13 C14 C15 -0.5(2) . . . . ?
Fe1 C13 C14 C15 -59.35(14) . . . . ?
C12 C13 C14 Fe1 58.88(16) . . . . ?
C12 C11 C15 C14 0.3(2) . . . . ?
Fe1 C11 C15 C14 59.79(14) . . . . ?
C12 C11 C15 C16 -174.48(19) . . . . ?
Fe1 C11 C15 C16 -115.02(19) . . . . ?
C12 C11 C15 Fe1 -59.46(15) . . . . ?
C13 C14 C15 C11 0.1(2) . . . . ?
Fe1 C14 C15 C11 -60.08(14) . . . . ?
C13 C14 C15 C16 174.6(2) . . . . ?
Fe1 C14 C15 C16 114.4(2) . . . . ?
C13 C14 C15 Fe1 60.17(15) . . . . ?
C11 C15 C16 O17 -11.6(3) . . . . ?
C14 C15 C16 O17 174.7(2) . . . . ?
Fe1 C15 C16 O17 -97.5(2) . . . . ?
C11 C15 C16 N18 168.25(18) . . . . ?
C14 C15 C16 N18 -5.5(3) . . . . ?
Fe1 C15 C16 N18 82.4(2) . . . . ?
O17 C16 N18 N19 4.0(3) . . . . ?
C15 C16 N18 N19 -175.89(19) . . . . ?

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR WE2663                                                 #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
####################################################################### 
# 
# 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_WE2692
_database_code_depnum_ccdc_archive 'CCDC 1584017'
_audit_update_record             
;
2017-11-05 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H8 Fe N6 O2'
_chemical_formula_sum            'C12 H8 Fe N6 O2'
_chemical_formula_weight         324.09
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                            UNIT CELL INFORMATION                             #
#------------------------------------------------------------------------------#


_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_IT_number           61
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   5.8627(6)
_cell_length_b                   16.8493(16)
_cell_length_c                   25.022(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2471.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150
_cell_measurement_reflns_used    4513
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      27.50
_cell_measurement_wavelength     0.71073

#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.050
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1312
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.776
_exptl_absorpt_correction_T_max  0.940

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_reflns_av_r_equivalents  0.0344
_diffrn_reflns_av_uneti/neti     0.0367
_diffrn_reflns_number            8531
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.769
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.988
_reflns_number_total             2806
_reflns_number_gt                2369
_reflns_threshold_expression     >2sigma(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.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2017)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0151P)²+6.4308P] 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         2806
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.0965
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_restrained_S_all      1.171
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.731
_refine_diff_density_rms         0.086

#...............................................................................
# .RES SHELXL file: job.res
# .HKL SHELXL file: job.hkl
#...............................................................................



# ............... End of .HKL file ........................................... 
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0331(5) 0.32475(17) 0.67058(11) 0.0163(6) Uani 1 1 d . . . . .
H1 H 1.158118 0.291141 0.662165 0.020 Uiso 1 1 calc R U . . .
C2 C 1.0354(5) 0.40931(18) 0.67061(11) 0.0181(6) Uani 1 1 d . . . . .
H2 H 1.162372 0.442092 0.662278 0.022 Uiso 1 1 calc R U . . .
C3 C 0.8136(5) 0.43596(17) 0.68534(11) 0.0169(6) Uani 1 1 d . . . . .
H3 H 0.767972 0.489836 0.688605 0.020 Uiso 1 1 calc R U . . .
C4 C 0.6713(5) 0.36872(17) 0.69440(10) 0.0155(6) Uani 1 1 d . . . . .
H4 H 0.515027 0.369602 0.704452 0.019 Uiso 1 1 calc R U . . .
C5 C 0.8086(5) 0.29939(17) 0.68548(10) 0.0156(6) Uani 1 1 d . . . . .
C6 C 0.7330(5) 0.21665(17) 0.68694(10) 0.0165(6) Uani 1 1 d . . . . .
O7 O 0.8512(4) 0.15865(12) 0.67958(9) 0.0222(5) Uani 1 1 d . . . . .
N8 N 0.4955(5) 0.21223(14) 0.69946(10) 0.0202(5) Uani 1 1 d . . . . .
N9 N 0.4218(5) 0.14252(15) 0.70198(10) 0.0206(5) Uani 1 1 d . . . . .
N10 N 0.3345(5) 0.08326(16) 0.70572(12) 0.0288(7) Uani 1 1 d . . . . .
C11 C 0.5275(5) 0.36596(18) 0.56568(11) 0.0187(6) Uani 1 1 d . . . . .
H11 H 0.370408 0.367420 0.574940 0.022 Uiso 1 1 calc R U . . .
C12 C 0.6624(6) 0.29650(18) 0.55774(11) 0.0206(6) Uani 1 1 d . . . . .
H12 H 0.610610 0.243283 0.560953 0.025 Uiso 1 1 calc R U . . .
C13 C 0.8888(6) 0.32065(18) 0.54413(11) 0.0197(6) Uani 1 1 d . . . . .
H13 H 1.013094 0.286255 0.536589 0.024 Uiso 1 1 calc R U . . .
C14 C 0.8959(5) 0.40497(19) 0.54382(11) 0.0185(6) Uani 1 1 d . . . . .
H14 H 1.025606 0.436811 0.536154 0.022 Uiso 1 1 calc R U . . .
C15 C 0.6732(5) 0.43331(17) 0.55708(11) 0.0167(6) Uani 1 1 d . . . . .
C16 C 0.6166(5) 0.51762(17) 0.56361(11) 0.0177(6) Uani 1 1 d . . . . .
O17 O 0.7477(4) 0.57215(13) 0.55630(9) 0.0277(5) Uani 1 1 d . . . . .
N18 N 0.3828(5) 0.52780(15) 0.57854(11) 0.0223(6) Uani 1 1 d . . . . .
N19 N 0.3302(5) 0.60004(17) 0.58206(10) 0.0227(6) Uani 1 1 d . . . . .
N20 N 0.2633(6) 0.66175(17) 0.58566(11) 0.0311(7) Uani 1 1 d . . . . .
Fe1 Fe 0.79670(7) 0.36577(2) 0.61768(2) 0.01217(12) Uani 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.425(4) . ?
C1 C5 1.433(4) . ?
C1 Fe1 2.037(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.424(4) . ?
C2 Fe1 2.062(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.425(4) . ?
C3 Fe1 2.068(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.436(4) . ?
C4 Fe1 2.057(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.463(4) . ?
C5 Fe1 2.033(3) . ?
C6 O7 1.212(4) . ?
C6 N8 1.429(4) . ?
N8 N9 1.253(4) . ?
N9 N10 1.126(4) . ?
C11 C12 1.426(4) . ?
C11 C15 1.437(4) . ?
C11 Fe1 2.045(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.429(5) . ?
C12 Fe1 2.057(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.421(4) . ?
C13 Fe1 2.063(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.429(4) . ?
C14 Fe1 2.047(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.468(4) . ?
C15 Fe1 2.029(3) . ?
C16 O17 1.212(4) . ?
C16 N18 1.431(4) . ?
N18 N19 1.259(4) . ?
N19 N20 1.115(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 C1 C5 107.9(3) . . ?
C2 C1 Fe1 70.59(17) . . ?
C5 C1 Fe1 69.24(16) . . ?
C2 C1 H1 126.1 . . ?
C5 C1 H1 126.1 . . ?
Fe1 C1 H1 125.7 . . ?
C1 C2 C3 107.9(3) . . ?
C1 C2 Fe1 68.73(17) . . ?
C3 C2 Fe1 70.05(16) . . ?
C1 C2 H2 126.1 . . ?
C3 C2 H2 126.1 . . ?
Fe1 C2 H2 126.7 . . ?
C2 C3 C4 109.0(3) . . ?
C2 C3 Fe1 69.61(16) . . ?
C4 C3 Fe1 69.36(15) . . ?
C2 C3 H3 125.5 . . ?
C4 C3 H3 125.5 . . ?
Fe1 C3 H3 127.1 . . ?
C3 C4 C5 107.1(3) . . ?
C3 C4 Fe1 70.20(16) . . ?
C5 C4 Fe1 68.58(15) . . ?
C3 C4 H4 126.5 . . ?
C5 C4 H4 126.5 . . ?
Fe1 C4 H4 126.3 . . ?
C1 C5 C4 108.2(3) . . ?
C1 C5 C6 124.7(3) . . ?
C4 C5 C6 127.0(3) . . ?
C1 C5 Fe1 69.53(15) . . ?
C4 C5 Fe1 70.31(15) . . ?
C6 C5 Fe1 122.31(19) . . ?
O7 C6 N8 123.2(3) . . ?
O7 C6 C5 126.3(3) . . ?
N8 C6 C5 110.5(2) . . ?
N9 N8 C6 113.3(3) . . ?
N10 N9 N8 172.8(3) . . ?
C12 C11 C15 107.3(3) . . ?
C12 C11 Fe1 70.10(17) . . ?
C15 C11 Fe1 68.75(16) . . ?
C12 C11 H11 126.3 . . ?
C15 C11 H11 126.3 . . ?
Fe1 C11 H11 126.4 . . ?
C11 C12 C13 108.3(3) . . ?
C11 C12 Fe1 69.21(16) . . ?
C13 C12 Fe1 69.92(17) . . ?
C11 C12 H12 125.8 . . ?
C13 C12 H12 125.8 . . ?
Fe1 C12 H12 126.6 . . ?
C14 C13 C12 108.3(3) . . ?
C14 C13 Fe1 69.16(17) . . ?
C12 C13 Fe1 69.47(17) . . ?
C14 C13 H13 125.9 . . ?
C12 C13 H13 125.9 . . ?
Fe1 C13 H13 127.1 . . ?
C13 C14 C15 107.8(3) . . ?
C13 C14 Fe1 70.38(17) . . ?
C15 C14 Fe1 68.80(17) . . ?
C13 C14 H14 126.1 . . ?
C15 C14 H14 126.1 . . ?
Fe1 C14 H14 126.3 . . ?
C14 C15 C11 108.3(3) . . ?
C14 C15 C16 123.8(3) . . ?
C11 C15 C16 127.8(3) . . ?
C14 C15 Fe1 70.14(17) . . ?
C11 C15 Fe1 69.96(16) . . ?
C16 C15 Fe1 122.7(2) . . ?
O17 C16 N18 123.8(3) . . ?
O17 C16 C15 125.0(3) . . ?
N18 C16 C15 111.2(3) . . ?
N19 N18 C16 111.6(3) . . ?
N20 N19 N18 173.5(4) . . ?
C15 Fe1 C5 160.76(13) . . ?
C15 Fe1 C1 156.70(12) . . ?
C5 Fe1 C1 41.22(12) . . ?
C15 Fe1 C11 41.29(12) . . ?
C5 Fe1 C11 123.92(13) . . ?
C1 Fe1 C11 159.83(12) . . ?
C15 Fe1 C14 41.05(12) . . ?
C5 Fe1 C14 157.08(12) . . ?
C1 Fe1 C14 120.18(13) . . ?
C11 Fe1 C14 69.18(12) . . ?
C15 Fe1 C4 123.81(12) . . ?
C5 Fe1 C4 41.11(11) . . ?
C1 Fe1 C4 69.20(12) . . ?
C11 Fe1 C4 108.54(12) . . ?
C14 Fe1 C4 159.51(12) . . ?
C15 Fe1 C12 68.71(11) . . ?
C5 Fe1 C12 108.02(12) . . ?
C1 Fe1 C12 122.79(12) . . ?
C11 Fe1 C12 40.69(12) . . ?
C14 Fe1 C12 68.51(12) . . ?
C4 Fe1 C12 123.88(12) . . ?
C15 Fe1 C13 68.50(12) . . ?
C5 Fe1 C13 122.18(12) . . ?
C1 Fe1 C13 106.05(12) . . ?
C11 Fe1 C13 68.60(13) . . ?
C14 Fe1 C13 40.46(12) . . ?
C4 Fe1 C13 159.27(12) . . ?
C12 Fe1 C13 40.60(13) . . ?
C15 Fe1 C2 121.51(12) . . ?
C5 Fe1 C2 68.68(12) . . ?
C1 Fe1 C2 40.68(11) . . ?
C11 Fe1 C2 158.72(13) . . ?
C14 Fe1 C2 105.80(13) . . ?
C4 Fe1 C2 68.56(12) . . ?
C12 Fe1 C2 158.44(13) . . ?
C13 Fe1 C2 121.77(13) . . ?
C15 Fe1 C3 107.96(12) . . ?
C5 Fe1 C3 68.26(11) . . ?
C1 Fe1 C3 68.24(12) . . ?
C11 Fe1 C3 123.85(12) . . ?
C14 Fe1 C3 122.76(12) . . ?
C4 Fe1 C3 40.44(12) . . ?
C12 Fe1 C3 160.04(13) . . ?
C13 Fe1 C3 158.23(13) . . ?
C2 Fe1 C3 40.35(12) . . ?

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
C5 C1 C2 C3 -0.1(3) . . . . ?
Fe1 C1 C2 C3 59.3(2) . . . . ?
C5 C1 C2 Fe1 -59.44(19) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
Fe1 C2 C3 C4 58.30(19) . . . . ?
C1 C2 C3 Fe1 -58.5(2) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
Fe1 C3 C4 C5 58.90(18) . . . . ?
C2 C3 C4 Fe1 -58.44(19) . . . . ?
C2 C1 C5 C4 0.4(3) . . . . ?
Fe1 C1 C5 C4 -59.90(18) . . . . ?
C2 C1 C5 C6 176.1(3) . . . . ?
Fe1 C1 C5 C6 115.8(3) . . . . ?
C2 C1 C5 Fe1 60.3(2) . . . . ?
C3 C4 C5 C1 -0.5(3) . . . . ?
Fe1 C4 C5 C1 59.41(19) . . . . ?
C3 C4 C5 C6 -176.1(3) . . . . ?
Fe1 C4 C5 C6 -116.2(3) . . . . ?
C3 C4 C5 Fe1 -59.93(18) . . . . ?
C1 C5 C6 O7 5.5(5) . . . . ?
C4 C5 C6 O7 -179.6(3) . . . . ?
Fe1 C5 C6 O7 91.7(3) . . . . ?
C1 C5 C6 N8 -175.6(3) . . . . ?
C4 C5 C6 N8 -0.7(4) . . . . ?
Fe1 C5 C6 N8 -89.4(3) . . . . ?
O7 C6 N8 N9 -0.1(4) . . . . ?
C5 C6 N8 N9 -179.1(2) . . . . ?
C15 C11 C12 C13 -0.3(3) . . . . ?
Fe1 C11 C12 C13 -59.2(2) . . . . ?
C15 C11 C12 Fe1 58.90(19) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
Fe1 C12 C13 C14 -58.4(2) . . . . ?
C11 C12 C13 Fe1 58.7(2) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
Fe1 C13 C14 C15 -58.8(2) . . . . ?
C12 C13 C14 Fe1 58.6(2) . . . . ?
C13 C14 C15 C11 0.0(3) . . . . ?
Fe1 C14 C15 C11 -59.78(19) . . . . ?
C13 C14 C15 C16 176.5(3) . . . . ?
Fe1 C14 C15 C16 116.7(3) . . . . ?
C13 C14 C15 Fe1 59.8(2) . . . . ?
C12 C11 C15 C14 0.2(3) . . . . ?
Fe1 C11 C15 C14 59.9(2) . . . . ?
C12 C11 C15 C16 -176.2(3) . . . . ?
Fe1 C11 C15 C16 -116.4(3) . . . . ?
C12 C11 C15 Fe1 -59.75(19) . . . . ?
C14 C15 C16 O17 3.4(5) . . . . ?
C11 C15 C16 O17 179.2(3) . . . . ?
Fe1 C15 C16 O17 90.2(3) . . . . ?
C14 C15 C16 N18 -178.1(3) . . . . ?
C11 C15 C16 N18 -2.3(4) . . . . ?
Fe1 C15 C16 N18 -91.4(3) . . . . ?
O17 C16 N18 N19 1.3(4) . . . . ?
C15 C16 N18 N19 -177.2(2) . . . . ?

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR WE2692                                                 #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
####################################################################### 
# 
# 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_GL031
_database_code_depnum_ccdc_archive 'CCDC 1584018'
_audit_update_record             
;
2017-11-05 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H17 Fe N O4, H2 O'
_chemical_formula_sum            'C19 H19 Fe N O5'
_chemical_formula_weight         397.20
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                            UNIT CELL INFORMATION                             #
#------------------------------------------------------------------------------#


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
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                   14.4756(6)
_cell_length_b                   7.4476(3)
_cell_length_c                   17.2948(8)
_cell_angle_alpha                90
_cell_angle_beta                 114.161(2)
_cell_angle_gamma                90
_cell_volume                     1701.19(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    7956
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.52
_cell_measurement_wavelength     0.71073

#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.060
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             824
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.822
_exptl_absorpt_correction_T_max  0.938

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_reflns_av_r_equivalents  0.0260
_diffrn_reflns_av_uneti/neti     0.0323
_diffrn_reflns_number            10825
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.024
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_reflns_number_total             3871
_reflns_number_gt                3261
_reflns_threshold_expression     >2sigma(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.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2017)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0253P)²+1.4293P] 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         3871
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0729
_refine_ls_wR_factor_gt          0.0680
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.063

#...............................................................................
# .RES SHELXL file: job.res
# .HKL SHELXL file: job.hkl
#...............................................................................



# ............... End of .HKL file .............................................
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'

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 0.80188(2) 0.84566(3) 0.41002(2) 0.01350(8) Uani 1 1 d . . . . .
C1 C 0.78489(13) 0.7088(2) 0.30357(12) 0.0182(4) Uani 1 1 d . . . . .
H1 H 0.745707 0.746771 0.247082 0.022 Uiso 1 1 calc R U . . .
C2 C 0.88937(13) 0.7448(2) 0.35173(12) 0.0212(4) Uani 1 1 d . . . . .
H2 H 0.932401 0.810798 0.332843 0.025 Uiso 1 1 calc R U . . .
C3 C 0.91836(13) 0.6651(2) 0.43302(12) 0.0216(4) Uani 1 1 d . . . . .
H3 H 0.984187 0.669025 0.477652 0.026 Uiso 1 1 calc R U . . .
C4 C 0.83273(13) 0.5789(2) 0.43647(12) 0.0190(4) Uani 1 1 d . . . . .
H4 H 0.830951 0.515656 0.483555 0.023 Uiso 1 1 calc R U . . .
C5 C 0.74924(12) 0.6045(2) 0.35584(11) 0.0160(3) Uani 1 1 d . . . . .
C6 C 0.64448(12) 0.5477(2) 0.33293(11) 0.0155(3) Uani 1 1 d . . . . .
O7 O 0.57602(9) 0.57269(18) 0.26238(8) 0.0225(3) Uani 1 1 d . . . . .
O8 O 0.62944(9) 0.46831(18) 0.39479(8) 0.0205(3) Uani 1 1 d . . . . .
H8 H 0.5694(17) 0.431(3) 0.3779(14) 0.025 Uiso 1 1 d . U . . .
C11 C 0.76240(13) 0.9572(2) 0.50120(12) 0.0191(4) Uani 1 1 d . . . . .
H11 H 0.758698 0.895745 0.547969 0.023 Uiso 1 1 calc R U . . .
C12 C 0.84973(14) 1.0434(3) 0.49936(12) 0.0231(4) Uani 1 1 d . . . . .
H12 H 0.914415 1.050921 0.545325 0.028 Uiso 1 1 calc R U . . .
C13 C 0.82325(14) 1.1159(2) 0.41714(13) 0.0231(4) Uani 1 1 d . . . . .
H13 H 0.867241 1.179986 0.398643 0.028 Uiso 1 1 calc R U . . .
C14 C 0.71955(13) 1.0761(2) 0.36709(12) 0.0198(4) Uani 1 1 d . . . . .
H14 H 0.682260 1.107331 0.309306 0.024 Uiso 1 1 calc R U . . .
C15 C 0.68200(12) 0.9809(2) 0.41974(11) 0.0162(3) Uani 1 1 d . . . . .
N16 N 0.58086(11) 0.9239(2) 0.39114(10) 0.0173(3) Uani 1 1 d . . . . .
H16 H 0.5441(16) 0.943(3) 0.3424(14) 0.021 Uiso 1 1 d . U . . .
C17 C 0.54034(12) 0.8388(2) 0.43870(11) 0.0163(3) Uani 1 1 d . . . . .
O18 O 0.58442(9) 0.80478(19) 0.51408(8) 0.0236(3) Uani 1 1 d . . . . .
O19 O 0.44331(9) 0.79650(18) 0.39096(8) 0.0202(3) Uani 1 1 d . . . . .
C20 C 0.38993(12) 0.7116(3) 0.43579(11) 0.0182(4) Uani 1 1 d . . . . .
H20A H 0.393130 0.788116 0.483615 0.022 Uiso 1 1 calc R U . . .
H20B H 0.421306 0.594219 0.458771 0.022 Uiso 1 1 calc R U . . .
C21 C 0.28168(12) 0.6854(2) 0.37440(11) 0.0161(3) Uani 1 1 d . . . . .
C22 C 0.23150(13) 0.8118(2) 0.31241(12) 0.0213(4) Uani 1 1 d . . . . .
H22 H 0.266753 0.914557 0.306197 0.026 Uiso 1 1 calc R U . . .
C23 C 0.12953(14) 0.7885(3) 0.25922(12) 0.0244(4) Uani 1 1 d . . . . .
H23 H 0.095725 0.874343 0.216275 0.029 Uiso 1 1 calc R U . . .
C24 C 0.07755(13) 0.6406(3) 0.26889(13) 0.0258(4) Uani 1 1 d . . . . .
H24 H 0.007872 0.625452 0.233061 0.031 Uiso 1 1 calc R U . . .
C25 C 0.12729(14) 0.5144(3) 0.33097(13) 0.0273(4) Uani 1 1 d . . . . .
H25 H 0.091469 0.413182 0.337913 0.033 Uiso 1 1 calc R U . . .
C26 C 0.22942(13) 0.5356(3) 0.38310(12) 0.0223(4) Uani 1 1 d . . . . .
H26 H 0.263593 0.447448 0.424756 0.027 Uiso 1 1 calc R U . . .
OW1 O 0.44907(10) 0.34207(19) 0.35235(9) 0.0218(3) Uani 1 1 d . . . . .
HW1A H 0.4367(16) 0.259(3) 0.3153(15) 0.026 Uiso 1 1 d . U . . .
HW1B H 0.4423(16) 0.298(3) 0.3926(16) 0.026 Uiso 1 1 d . U . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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 C5 2.0250(17) . ?
Fe1 C1 2.0293(18) . ?
Fe1 C13 2.0323(18) . ?
Fe1 C12 2.0398(18) . ?
Fe1 C4 2.0468(18) . ?
Fe1 C14 2.0479(18) . ?
Fe1 C2 2.0566(17) . ?
Fe1 C11 2.0595(17) . ?
Fe1 C3 2.0639(17) . ?
Fe1 C15 2.0718(16) . ?
C1 C2 1.422(2) . ?
C1 C5 1.438(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.422(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.419(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.436(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.464(2) . ?
C6 O7 1.231(2) . ?
C6 O8 1.316(2) . ?
O8 H8 0.84(2) . ?
C11 C15 1.424(2) . ?
C11 C12 1.430(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.419(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.424(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.426(2) . ?
C14 H14 0.9500 . ?
C15 N16 1.406(2) . ?
N16 C17 1.348(2) . ?
N16 H16 0.80(2) . ?
C17 O18 1.221(2) . ?
C17 O19 1.343(2) . ?
O19 C20 1.445(2) . ?
C20 C21 1.503(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.388(2) . ?
C21 C26 1.390(2) . ?
C22 C23 1.394(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.386(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.390(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
OW1 HW1A 0.86(2) . ?
OW1 HW1B 0.81(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
C5 Fe1 C1 41.56(7) . . ?
C5 Fe1 C13 157.76(8) . . ?
C1 Fe1 C13 120.75(8) . . ?
C5 Fe1 C12 159.69(8) . . ?
C1 Fe1 C12 158.03(7) . . ?
C13 Fe1 C12 40.79(8) . . ?
C5 Fe1 C4 41.29(7) . . ?
C1 Fe1 C4 69.48(7) . . ?
C13 Fe1 C4 159.06(8) . . ?
C12 Fe1 C4 123.80(8) . . ?
C5 Fe1 C14 121.53(7) . . ?
C1 Fe1 C14 104.81(8) . . ?
C13 Fe1 C14 40.84(7) . . ?
C12 Fe1 C14 68.66(8) . . ?
C4 Fe1 C14 159.41(7) . . ?
C5 Fe1 C2 68.89(7) . . ?
C1 Fe1 C2 40.73(7) . . ?
C13 Fe1 C2 106.39(7) . . ?
C12 Fe1 C2 123.27(7) . . ?
C4 Fe1 C2 68.49(7) . . ?
C14 Fe1 C2 120.80(7) . . ?
C5 Fe1 C11 122.85(7) . . ?
C1 Fe1 C11 158.24(7) . . ?
C13 Fe1 C11 68.72(7) . . ?
C12 Fe1 C11 40.82(7) . . ?
C4 Fe1 C11 108.91(7) . . ?
C14 Fe1 C11 68.69(7) . . ?
C2 Fe1 C11 160.43(7) . . ?
C5 Fe1 C3 68.55(7) . . ?
C1 Fe1 C3 68.52(7) . . ?
C13 Fe1 C3 122.77(7) . . ?
C12 Fe1 C3 109.09(8) . . ?
C4 Fe1 C3 40.39(7) . . ?
C14 Fe1 C3 157.54(7) . . ?
C2 Fe1 C3 40.38(7) . . ?
C11 Fe1 C3 125.18(8) . . ?
C5 Fe1 C15 107.45(7) . . ?
C1 Fe1 C15 121.55(7) . . ?
C13 Fe1 C15 68.00(7) . . ?
C12 Fe1 C15 67.88(7) . . ?
C4 Fe1 C15 124.56(7) . . ?
C14 Fe1 C15 40.49(7) . . ?
C2 Fe1 C15 157.15(7) . . ?
C11 Fe1 C15 40.33(7) . . ?
C3 Fe1 C15 161.15(7) . . ?
C2 C1 C5 107.64(16) . . ?
C2 C1 Fe1 70.67(10) . . ?
C5 C1 Fe1 69.06(10) . . ?
C2 C1 H1 126.2 . . ?
C5 C1 H1 126.2 . . ?
Fe1 C1 H1 125.7 . . ?
C1 C2 C3 108.24(15) . . ?
C1 C2 Fe1 68.61(10) . . ?
C3 C2 Fe1 70.09(10) . . ?
C1 C2 H2 125.9 . . ?
C3 C2 H2 125.9 . . ?
Fe1 C2 H2 127.0 . . ?
C4 C3 C2 108.74(16) . . ?
C4 C3 Fe1 69.16(10) . . ?
C2 C3 Fe1 69.54(10) . . ?
C4 C3 H3 125.6 . . ?
C2 C3 H3 125.6 . . ?
Fe1 C3 H3 127.3 . . ?
C3 C4 C5 107.55(16) . . ?
C3 C4 Fe1 70.46(10) . . ?
C5 C4 Fe1 68.54(10) . . ?
C3 C4 H4 126.2 . . ?
C5 C4 H4 126.2 . . ?
Fe1 C4 H4 126.3 . . ?
C4 C5 C1 107.84(15) . . ?
C4 C5 C6 126.25(16) . . ?
C1 C5 C6 125.74(16) . . ?
C4 C5 Fe1 70.17(10) . . ?
C1 C5 Fe1 69.38(10) . . ?
C6 C5 Fe1 122.22(12) . . ?
O7 C6 O8 122.65(15) . . ?
O7 C6 C5 123.31(16) . . ?
O8 C6 C5 114.04(15) . . ?
C6 O8 H8 110.9(15) . . ?
C15 C11 C12 107.13(16) . . ?
C15 C11 Fe1 70.30(10) . . ?
C12 C11 Fe1 68.85(10) . . ?
C15 C11 H11 126.4 . . ?
C12 C11 H11 126.4 . . ?
Fe1 C11 H11 126.0 . . ?
C13 C12 C11 108.32(16) . . ?
C13 C12 Fe1 69.32(11) . . ?
C11 C12 Fe1 70.33(10) . . ?
C13 C12 H12 125.8 . . ?
C11 C12 H12 125.8 . . ?
Fe1 C12 H12 126.1 . . ?
C12 C13 C14 108.38(16) . . ?
C12 C13 Fe1 69.89(11) . . ?
C14 C13 Fe1 70.17(10) . . ?
C12 C13 H13 125.8 . . ?
C14 C13 H13 125.8 . . ?
Fe1 C13 H13 125.7 . . ?
C13 C14 C15 107.33(17) . . ?
C13 C14 Fe1 68.99(10) . . ?
C15 C14 Fe1 70.66(10) . . ?
C13 C14 H14 126.3 . . ?
C15 C14 H14 126.3 . . ?
Fe1 C14 H14 125.6 . . ?
N16 C15 C11 128.49(16) . . ?
N16 C15 C14 122.69(16) . . ?
C11 C15 C14 108.82(15) . . ?
N16 C15 Fe1 127.65(12) . . ?
C11 C15 Fe1 69.37(9) . . ?
C14 C15 Fe1 68.85(9) . . ?
C17 N16 C15 125.32(16) . . ?
C17 N16 H16 117.1(15) . . ?
C15 N16 H16 117.6(15) . . ?
O18 C17 O19 124.46(16) . . ?
O18 C17 N16 125.54(16) . . ?
O19 C17 N16 109.99(15) . . ?
C17 O19 C20 115.28(13) . . ?
O19 C20 C21 108.03(14) . . ?
O19 C20 H20A 110.1 . . ?
C21 C20 H20A 110.1 . . ?
O19 C20 H20B 110.1 . . ?
C21 C20 H20B 110.1 . . ?
H20A C20 H20B 108.4 . . ?
C22 C21 C26 119.48(16) . . ?
C22 C21 C20 121.50(16) . . ?
C26 C21 C20 118.93(16) . . ?
C21 C22 C23 120.22(17) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 120.08(18) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 119.88(17) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C26 120.19(18) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C21 120.14(18) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?
HW1A OW1 HW1B 107(2) . . ?

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
C5 C1 C2 C3 -0.4(2) . . . . ?
Fe1 C1 C2 C3 59.05(13) . . . . ?
C5 C1 C2 Fe1 -59.40(12) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
Fe1 C2 C3 C4 58.16(13) . . . . ?
C1 C2 C3 Fe1 -58.14(12) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
Fe1 C3 C4 C5 58.70(12) . . . . ?
C2 C3 C4 Fe1 -58.39(13) . . . . ?
C3 C4 C5 C1 -0.5(2) . . . . ?
Fe1 C4 C5 C1 59.38(12) . . . . ?
C3 C4 C5 C6 -175.91(16) . . . . ?
Fe1 C4 C5 C6 -116.00(17) . . . . ?
C3 C4 C5 Fe1 -59.91(12) . . . . ?
C2 C1 C5 C4 0.5(2) . . . . ?
Fe1 C1 C5 C4 -59.88(12) . . . . ?
C2 C1 C5 C6 175.96(16) . . . . ?
Fe1 C1 C5 C6 115.54(17) . . . . ?
C2 C1 C5 Fe1 60.42(12) . . . . ?
C4 C5 C6 O7 -179.62(17) . . . . ?
C1 C5 C6 O7 5.8(3) . . . . ?
Fe1 C5 C6 O7 92.40(19) . . . . ?
C4 C5 C6 O8 0.9(3) . . . . ?
C1 C5 C6 O8 -173.73(16) . . . . ?
Fe1 C5 C6 O8 -87.13(17) . . . . ?
C15 C11 C12 C13 -1.1(2) . . . . ?
Fe1 C11 C12 C13 59.10(13) . . . . ?
C15 C11 C12 Fe1 -60.18(12) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
Fe1 C12 C13 C14 59.85(13) . . . . ?
C11 C12 C13 Fe1 -59.73(13) . . . . ?
C12 C13 C14 C15 0.9(2) . . . . ?
Fe1 C13 C14 C15 60.56(12) . . . . ?
C12 C13 C14 Fe1 -59.67(13) . . . . ?
C12 C11 C15 N16 -178.44(17) . . . . ?
Fe1 C11 C15 N16 122.31(18) . . . . ?
C12 C11 C15 C14 1.6(2) . . . . ?
Fe1 C11 C15 C14 -57.62(12) . . . . ?
C12 C11 C15 Fe1 59.25(12) . . . . ?
C13 C14 C15 N16 178.50(16) . . . . ?
Fe1 C14 C15 N16 -122.00(16) . . . . ?
C13 C14 C15 C11 -1.6(2) . . . . ?
Fe1 C14 C15 C11 57.93(12) . . . . ?
C13 C14 C15 Fe1 -59.50(12) . . . . ?
C11 C15 N16 C17 2.4(3) . . . . ?
C14 C15 N16 C17 -177.70(17) . . . . ?
Fe1 C15 N16 C17 95.0(2) . . . . ?
C15 N16 C17 O18 2.9(3) . . . . ?
C15 N16 C17 O19 -177.34(15) . . . . ?
O18 C17 O19 C20 2.5(2) . . . . ?
N16 C17 O19 C20 -177.32(14) . . . . ?
C17 O19 C20 C21 176.26(14) . . . . ?
O19 C20 C21 C22 -37.0(2) . . . . ?
O19 C20 C21 C26 146.45(16) . . . . ?
C26 C21 C22 C23 -0.1(3) . . . . ?
C20 C21 C22 C23 -176.62(16) . . . . ?
C21 C22 C23 C24 1.0(3) . . . . ?
C22 C23 C24 C25 -0.7(3) . . . . ?
C23 C24 C25 C26 -0.5(3) . . . . ?
C24 C25 C26 C21 1.4(3) . . . . ?
C22 C21 C26 C25 -1.1(3) . . . . ?
C20 C21 C26 C25 175.53(17) . . . . ?

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
O8 H8 OW1 0.84(2) 1.74(2) 2.5828(18) 174(2) .
N16 H16 O7 0.80(2) 2.16(2) 2.916(2) 157(2) 2_655
OW1 HW1A O7 0.86(2) 1.89(2) 2.7394(19) 174(2) 2_645
OW1 HW1B O18 0.81(2) 1.96(3) 2.7720(19) 176(2) 3_666

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR GL031                                                  #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
####################################################################### 
# 
# 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_WE320X1
_database_code_depnum_ccdc_archive 'CCDC 1584021'
_audit_update_record             
;
2017-11-05 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H15 Fe N O4'
_chemical_formula_sum            'C15 H15 Fe N O4'
_chemical_formula_weight         329.13
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                            UNIT CELL INFORMATION                             #
#------------------------------------------------------------------------------#


_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4320(9)
_cell_length_b                   11.1582(11)
_cell_length_c                   15.5903(15)
_cell_angle_alpha                69.828(3)
_cell_angle_beta                 85.294(4)
_cell_angle_gamma                85.800(4)
_cell_volume                     1370.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9876
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      27.49
_cell_measurement_wavelength     0.71073

#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       stick
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             680
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.777
_exptl_absorpt_correction_T_max  0.967

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_reflns_av_r_equivalents  0.0672
_diffrn_reflns_av_uneti/neti     0.0467
_diffrn_reflns_number            32164
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.985
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             6273
_reflns_number_gt                5362
_reflns_threshold_expression     >2sigma(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.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2017)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0195P)²+4.4364P] 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         6273
_refine_ls_number_parameters     385
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1192
_refine_ls_wR_factor_gt          0.1152
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_restrained_S_all      1.141
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.986
_refine_diff_density_min         -0.798
_refine_diff_density_rms         0.100

#...............................................................................
# .RES SHELXL file: WE320x1.res
# .HKL SHELXL file: WE320x1.hkl
#...............................................................................



# ............... End of .HKL file ........................................... 
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'

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 1.00187(5) 0.24509(4) 0.50261(3) 0.00932(11) Uani 1 1 d . . . . .
C1 C 0.8464(4) 0.1020(3) 0.5351(2) 0.0131(6) Uani 1 1 d . . . . .
H1 H 0.832550 0.049157 0.500074 0.016 Uiso 1 1 calc R U . . .
C2 C 0.9519(4) 0.0762(3) 0.6062(2) 0.0144(6) Uani 1 1 d . . . . .
H2 H 1.021196 0.002376 0.627409 0.017 Uiso 1 1 calc R U . . .
C3 C 0.9365(4) 0.1795(3) 0.6405(2) 0.0154(6) Uani 1 1 d . . . . .
H3 H 0.994203 0.186666 0.688181 0.018 Uiso 1 1 calc R U . . .
C4 C 0.8207(4) 0.2699(3) 0.59139(19) 0.0128(6) Uani 1 1 d . . . . .
H4 H 0.786506 0.347927 0.600454 0.015 Uiso 1 1 calc R U . . .
C5 C 0.7644(4) 0.2226(3) 0.52588(19) 0.0116(6) Uani 1 1 d . . . . .
C6 C 0.6593(4) 0.2937(3) 0.4532(2) 0.0125(6) Uani 1 1 d . . . . .
O7 O 0.6010(3) 0.4033(2) 0.45970(16) 0.0197(5) Uani 1 1 d . . . . .
O8 O 0.6308(3) 0.2543(2) 0.39165(15) 0.0185(5) Uani 1 1 d . . . . .
C9 C 1.1477(4) 0.2376(3) 0.3913(2) 0.0136(6) Uani 1 1 d . . . . .
H9 H 1.152531 0.171683 0.365430 0.016 Uiso 1 1 calc R U . . .
C10 C 1.2393(4) 0.2410(3) 0.4638(2) 0.0160(6) Uani 1 1 d . . . . .
H10 H 1.317196 0.177887 0.493881 0.019 Uiso 1 1 calc R U . . .
C11 C 1.1937(4) 0.3549(3) 0.4831(2) 0.0158(6) Uani 1 1 d . . . . .
H11 H 1.235789 0.381007 0.528229 0.019 Uiso 1 1 calc R U . . .
C12 C 1.0740(4) 0.4226(3) 0.4231(2) 0.0137(6) Uani 1 1 d . . . . .
H12 H 1.020708 0.501137 0.421784 0.016 Uiso 1 1 calc R U . . .
C13 C 1.0480(4) 0.3516(3) 0.3650(2) 0.0121(6) Uani 1 1 d . . . . .
N14 N 0.9416(3) 0.3988(2) 0.29497(16) 0.0131(5) Uani 1 1 d . . . . .
H14 H 0.890556 0.471560 0.292193 0.016 Uiso 1 1 calc R U . . .
C15 C 0.9052(4) 0.3505(3) 0.2315(2) 0.0143(6) Uani 1 1 d . . . . .
O16 O 0.8189(3) 0.4079(2) 0.16931(16) 0.0206(5) Uani 1 1 d . . . . .
O17 O 0.9719(3) 0.2333(2) 0.24322(16) 0.0223(5) Uani 1 1 d . . . . .
C18 C 0.9385(4) 0.1756(3) 0.1765(2) 0.0230(7) Uani 1 1 d . . . . .
H18A H 0.860923 0.231292 0.134062 0.028 Uiso 1 1 calc R U . . .
H18B H 0.891070 0.091874 0.208282 0.028 Uiso 1 1 calc R U . . .
C19 C 1.0870(5) 0.1579(4) 0.1246(3) 0.0328(9) Uani 1 1 d . . . . .
H19 H 1.151929 0.229146 0.098294 0.039 Uiso 1 1 calc R U . . .
H7 H 0.540(6) 0.443(5) 0.416(4) 0.050 Uiso 1 1 d . . . . .
Fe2 Fe 0.34581(5) 0.67714(4) 0.07203(3) 0.01216(12) Uani 1 1 d . . . . .
C20 C 1.1353(7) 0.0507(6) 0.1124(3) 0.0554(15) Uani 1 1 d . . . . .
H20A H 1.073254 -0.022398 0.137774 0.067 Uiso 1 1 calc R U . . .
H20B H 1.232565 0.045936 0.078079 0.067 Uiso 1 1 calc R U . . .
C21 C 0.2307(4) 0.5095(3) 0.1270(2) 0.0175(6) Uani 1 1 d . . . . .
H21 H 0.264172 0.429794 0.120376 0.021 Uiso 1 1 calc R U . . .
C22 C 0.1285(4) 0.6046(3) 0.0695(2) 0.0208(7) Uani 1 1 d . . . . .
H22 H 0.082103 0.599917 0.017269 0.025 Uiso 1 1 calc R U . . .
C23 C 0.1076(4) 0.7082(4) 0.1033(2) 0.0219(7) Uani 1 1 d . . . . .
H23 H 0.043929 0.784336 0.077740 0.026 Uiso 1 1 calc R U . . .
C24 C 0.1981(4) 0.6789(3) 0.1822(2) 0.0190(7) Uani 1 1 d . . . . .
H24 H 0.206282 0.731537 0.218088 0.023 Uiso 1 1 calc R U . . .
C25 C 0.2745(4) 0.5545(3) 0.1968(2) 0.0145(6) Uani 1 1 d . . . . .
C26 C 0.3901(4) 0.4907(3) 0.2652(2) 0.0133(6) Uani 1 1 d . . . . .
O27 O 0.4280(3) 0.5365(2) 0.32186(14) 0.0167(5) Uani 1 1 d . . . . .
O28 O 0.4490(3) 0.3820(2) 0.25920(16) 0.0187(5) Uani 1 1 d . . . . .
C29 C 0.4936(4) 0.8262(3) 0.0464(2) 0.0181(7) Uani 1 1 d . . . . .
H29 H 0.482880 0.889486 0.074845 0.022 Uiso 1 1 calc R U . . .
C30 C 0.4223(4) 0.8322(3) -0.0354(2) 0.0203(7) Uani 1 1 d . . . . .
H30 H 0.357196 0.901443 -0.071369 0.024 Uiso 1 1 calc R U . . .
C31 C 0.4651(4) 0.7175(3) -0.0539(2) 0.0202(7) Uani 1 1 d . . . . .
H31 H 0.433649 0.696599 -0.103943 0.024 Uiso 1 1 calc R U . . .
C32 C 0.5640(4) 0.6393(3) 0.0166(2) 0.0152(6) Uani 1 1 d . . . . .
H32 H 0.608757 0.556534 0.022127 0.018 Uiso 1 1 calc R U . . .
C33 C 0.5837(4) 0.7076(3) 0.0772(2) 0.0138(6) Uani 1 1 d . . . . .
N34 N 0.6842(3) 0.6579(3) 0.15006(17) 0.0146(5) Uani 1 1 d . . . . .
H34 H 0.748996 0.593352 0.147857 0.017 Uiso 1 1 calc R U . . .
C35 C 0.6958(4) 0.6949(3) 0.2231(2) 0.0154(6) Uani 1 1 d . . . . .
O36 O 0.7824(3) 0.6392(2) 0.28507(16) 0.0197(5) Uani 1 1 d . . . . .
O37 O 0.6054(3) 0.8003(2) 0.21939(15) 0.0181(5) Uani 1 1 d . . . . .
C38 C 0.5912(4) 0.8302(3) 0.3039(2) 0.0203(7) Uani 1 1 d . . . . .
H38A H 0.697297 0.844510 0.320458 0.024 Uiso 1 1 calc R U . . .
H38B H 0.544187 0.758690 0.354780 0.024 Uiso 1 1 calc R U . . .
C39 C 0.4858(4) 0.9483(3) 0.2868(2) 0.0221(7) Uani 1 1 d . . . . .
H39 H 0.385522 0.950086 0.262571 0.027 Uiso 1 1 calc R U . . .
C40 C 0.5235(6) 1.0497(4) 0.3032(3) 0.0371(10) Uani 1 1 d . . . . .
H40A H 0.622980 1.050713 0.327385 0.045 Uiso 1 1 calc R U . . .
H40B H 0.451417 1.122314 0.290852 0.045 Uiso 1 1 calc R U . . .
H28 H 0.506(7) 0.345(5) 0.295(4) 0.050 Uiso 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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 C5 2.024(3) . ?
Fe1 C11 2.040(3) . ?
Fe1 C1 2.041(3) . ?
Fe1 C10 2.045(3) . ?
Fe1 C4 2.045(3) . ?
Fe1 C12 2.046(3) . ?
Fe1 C3 2.059(3) . ?
Fe1 C2 2.060(3) . ?
Fe1 C9 2.066(3) . ?
Fe1 C13 2.083(3) . ?
C1 C2 1.416(4) . ?
C1 C5 1.434(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.422(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.415(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.426(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.463(4) . ?
C6 O8 1.232(4) . ?
C6 O7 1.317(4) . ?
O7 H7 0.86(5) . ?
C9 C13 1.426(4) . ?
C9 C10 1.433(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.424(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.421(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.431(4) . ?
C12 H12 0.9500 . ?
C13 N14 1.403(4) . ?
N14 C15 1.343(4) . ?
N14 H14 0.8800 . ?
C15 O16 1.224(4) . ?
C15 O17 1.344(4) . ?
O17 C18 1.453(4) . ?
C18 C19 1.473(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.306(6) . ?
C19 H19 0.9500 . ?
Fe2 C25 2.028(3) . ?
Fe2 C24 2.042(3) . ?
Fe2 C32 2.046(3) . ?
Fe2 C31 2.049(3) . ?
Fe2 C21 2.050(3) . ?
Fe2 C30 2.050(3) . ?
Fe2 C29 2.060(3) . ?
Fe2 C23 2.061(3) . ?
Fe2 C22 2.065(3) . ?
Fe2 C33 2.072(3) . ?
C20 H20A 0.9500 . ?
C20 H20B 0.9500 . ?
C21 C22 1.418(5) . ?
C21 C25 1.429(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.422(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.429(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.439(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.463(4) . ?
C26 O27 1.234(4) . ?
C26 O28 1.308(4) . ?
O28 H28 0.75(5) . ?
C29 C33 1.426(4) . ?
C29 C30 1.433(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.421(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.431(5) . ?
C31 H31 0.9500 . ?
C32 C33 1.428(4) . ?
C32 H32 0.9500 . ?
C33 N34 1.404(4) . ?
N34 C35 1.351(4) . ?
N34 H34 0.8800 . ?
C35 O36 1.220(4) . ?
C35 O37 1.340(4) . ?
O37 C38 1.460(4) . ?
C38 C39 1.491(5) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.308(5) . ?
C39 H39 0.9500 . ?
C40 H40A 0.9500 . ?
C40 H40B 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
C5 Fe1 C11 150.34(13) . . ?
C5 Fe1 C1 41.32(12) . . ?
C11 Fe1 C1 166.95(13) . . ?
C5 Fe1 C10 167.50(13) . . ?
C11 Fe1 C10 40.81(13) . . ?
C1 Fe1 C10 128.77(13) . . ?
C5 Fe1 C4 41.04(12) . . ?
C11 Fe1 C4 116.77(13) . . ?
C1 Fe1 C4 69.10(12) . . ?
C10 Fe1 C4 150.50(13) . . ?
C5 Fe1 C12 117.15(12) . . ?
C11 Fe1 C12 40.70(12) . . ?
C1 Fe1 C12 151.27(12) . . ?
C10 Fe1 C12 68.44(13) . . ?
C4 Fe1 C12 107.45(12) . . ?
C5 Fe1 C3 68.34(12) . . ?
C11 Fe1 C3 107.93(13) . . ?
C1 Fe1 C3 68.36(12) . . ?
C10 Fe1 C3 118.01(13) . . ?
C4 Fe1 C3 40.34(12) . . ?
C12 Fe1 C3 128.40(13) . . ?
C5 Fe1 C2 68.42(12) . . ?
C11 Fe1 C2 128.87(13) . . ?
C1 Fe1 C2 40.41(12) . . ?
C10 Fe1 C2 108.77(13) . . ?
C4 Fe1 C2 68.20(12) . . ?
C12 Fe1 C2 166.76(13) . . ?
C3 Fe1 C2 40.40(12) . . ?
C5 Fe1 C9 128.81(12) . . ?
C11 Fe1 C9 68.74(13) . . ?
C1 Fe1 C9 108.18(12) . . ?
C10 Fe1 C9 40.79(12) . . ?
C4 Fe1 C9 167.15(12) . . ?
C12 Fe1 C9 68.52(12) . . ?
C3 Fe1 C9 151.54(12) . . ?
C2 Fe1 C9 118.45(12) . . ?
C5 Fe1 C13 108.51(12) . . ?
C11 Fe1 C13 68.07(12) . . ?
C1 Fe1 C13 118.36(12) . . ?
C10 Fe1 C13 67.80(12) . . ?
C4 Fe1 C13 129.06(12) . . ?
C12 Fe1 C13 40.55(12) . . ?
C3 Fe1 C13 166.85(12) . . ?
C2 Fe1 C13 151.68(12) . . ?
C9 Fe1 C13 40.20(12) . . ?
C2 C1 C5 107.3(3) . . ?
C2 C1 Fe1 70.52(17) . . ?
C5 C1 Fe1 68.70(17) . . ?
C2 C1 H1 126.3 . . ?
C5 C1 H1 126.3 . . ?
Fe1 C1 H1 126.0 . . ?
C1 C2 C3 108.4(3) . . ?
C1 C2 Fe1 69.07(17) . . ?
C3 C2 Fe1 69.75(17) . . ?
C1 C2 H2 125.8 . . ?
C3 C2 H2 125.8 . . ?
Fe1 C2 H2 127.0 . . ?
C4 C3 C2 108.4(3) . . ?
C4 C3 Fe1 69.32(16) . . ?
C2 C3 Fe1 69.85(17) . . ?
C4 C3 H3 125.8 . . ?
C2 C3 H3 125.8 . . ?
Fe1 C3 H3 126.6 . . ?
C3 C4 C5 107.6(3) . . ?
C3 C4 Fe1 70.34(17) . . ?
C5 C4 Fe1 68.67(17) . . ?
C3 C4 H4 126.2 . . ?
C5 C4 H4 126.2 . . ?
Fe1 C4 H4 126.4 . . ?
C4 C5 C1 108.2(3) . . ?
C4 C5 C6 125.4(3) . . ?
C1 C5 C6 125.8(3) . . ?
C4 C5 Fe1 70.29(17) . . ?
C1 C5 Fe1 69.98(17) . . ?
C6 C5 Fe1 118.7(2) . . ?
O8 C6 O7 123.9(3) . . ?
O8 C6 C5 122.5(3) . . ?
O7 C6 C5 113.6(3) . . ?
C6 O7 H7 112(4) . . ?
C13 C9 C10 107.3(3) . . ?
C13 C9 Fe1 70.54(17) . . ?
C10 C9 Fe1 68.83(17) . . ?
C13 C9 H9 126.3 . . ?
C10 C9 H9 126.3 . . ?
Fe1 C9 H9 125.9 . . ?
C11 C10 C9 108.4(3) . . ?
C11 C10 Fe1 69.41(18) . . ?
C9 C10 Fe1 70.38(18) . . ?
C11 C10 H10 125.8 . . ?
C9 C10 H10 125.8 . . ?
Fe1 C10 H10 126.0 . . ?
C12 C11 C10 107.9(3) . . ?
C12 C11 Fe1 69.89(17) . . ?
C10 C11 Fe1 69.79(18) . . ?
C12 C11 H11 126.0 . . ?
C10 C11 H11 126.0 . . ?
Fe1 C11 H11 125.9 . . ?
C11 C12 C13 108.0(3) . . ?
C11 C12 Fe1 69.41(17) . . ?
C13 C12 Fe1 71.09(16) . . ?
C11 C12 H12 126.0 . . ?
C13 C12 H12 126.0 . . ?
Fe1 C12 H12 125.1 . . ?
N14 C13 C9 130.8(3) . . ?
N14 C13 C12 121.0(3) . . ?
C9 C13 C12 108.3(3) . . ?
N14 C13 Fe1 129.1(2) . . ?
C9 C13 Fe1 69.26(16) . . ?
C12 C13 Fe1 68.36(16) . . ?
C15 N14 C13 130.3(3) . . ?
C15 N14 H14 114.8 . . ?
C13 N14 H14 114.8 . . ?
O16 C15 N14 123.1(3) . . ?
O16 C15 O17 123.4(3) . . ?
N14 C15 O17 113.5(3) . . ?
C15 O17 C18 116.5(2) . . ?
O17 C18 C19 109.7(3) . . ?
O17 C18 H18A 109.7 . . ?
C19 C18 H18A 109.7 . . ?
O17 C18 H18B 109.7 . . ?
C19 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
C20 C19 C18 124.3(4) . . ?
C20 C19 H19 117.8 . . ?
C18 C19 H19 117.8 . . ?
C25 Fe2 C24 41.40(13) . . ?
C25 Fe2 C32 117.49(13) . . ?
C24 Fe2 C32 150.91(13) . . ?
C25 Fe2 C31 152.17(14) . . ?
C24 Fe2 C31 165.89(14) . . ?
C32 Fe2 C31 40.90(13) . . ?
C25 Fe2 C21 41.03(12) . . ?
C24 Fe2 C21 69.18(14) . . ?
C32 Fe2 C21 108.47(13) . . ?
C31 Fe2 C21 119.14(13) . . ?
C25 Fe2 C30 165.16(13) . . ?
C24 Fe2 C30 127.14(14) . . ?
C32 Fe2 C30 68.36(13) . . ?
C31 Fe2 C30 40.57(14) . . ?
C21 Fe2 C30 152.89(13) . . ?
C25 Fe2 C29 126.39(13) . . ?
C24 Fe2 C29 105.96(14) . . ?
C32 Fe2 C29 68.64(13) . . ?
C31 Fe2 C29 68.77(13) . . ?
C21 Fe2 C29 165.32(13) . . ?
C30 Fe2 C29 40.81(13) . . ?
C25 Fe2 C23 68.59(13) . . ?
C24 Fe2 C23 40.75(13) . . ?
C32 Fe2 C23 167.27(13) . . ?
C31 Fe2 C23 128.98(14) . . ?
C21 Fe2 C23 68.08(14) . . ?
C30 Fe2 C23 108.75(14) . . ?
C29 Fe2 C23 117.89(14) . . ?
C25 Fe2 C22 68.48(13) . . ?
C24 Fe2 C22 68.65(14) . . ?
C32 Fe2 C22 129.30(14) . . ?
C31 Fe2 C22 109.53(14) . . ?
C21 Fe2 C22 40.31(13) . . ?
C30 Fe2 C22 119.62(13) . . ?
C29 Fe2 C22 152.29(14) . . ?
C23 Fe2 C22 40.33(14) . . ?
C25 Fe2 C33 106.96(12) . . ?
C24 Fe2 C33 116.80(13) . . ?
C32 Fe2 C33 40.58(12) . . ?
C31 Fe2 C33 68.29(13) . . ?
C21 Fe2 C33 128.27(13) . . ?
C30 Fe2 C33 67.89(13) . . ?
C29 Fe2 C33 40.39(12) . . ?
C23 Fe2 C33 151.12(14) . . ?
C22 Fe2 C33 166.72(14) . . ?
C19 C20 H20A 120.0 . . ?
C19 C20 H20B 120.0 . . ?
H20A C20 H20B 120.0 . . ?
C22 C21 C25 108.0(3) . . ?
C22 C21 Fe2 70.43(19) . . ?
C25 C21 Fe2 68.67(18) . . ?
C22 C21 H21 126.0 . . ?
C25 C21 H21 126.0 . . ?
Fe2 C21 H21 126.5 . . ?
C21 C22 C23 108.2(3) . . ?
C21 C22 Fe2 69.25(19) . . ?
C23 C22 Fe2 69.7(2) . . ?
C21 C22 H22 125.9 . . ?
C23 C22 H22 125.9 . . ?
Fe2 C22 H22 126.7 . . ?
C22 C23 C24 108.7(3) . . ?
C22 C23 Fe2 70.0(2) . . ?
C24 C23 Fe2 68.90(19) . . ?
C22 C23 H23 125.7 . . ?
C24 C23 H23 125.7 . . ?
Fe2 C23 H23 127.0 . . ?
C23 C24 C25 107.0(3) . . ?
C23 C24 Fe2 70.35(19) . . ?
C25 C24 Fe2 68.79(17) . . ?
C23 C24 H24 126.5 . . ?
C25 C24 H24 126.5 . . ?
Fe2 C24 H24 125.9 . . ?
C21 C25 C24 108.2(3) . . ?
C21 C25 C26 125.6(3) . . ?
C24 C25 C26 125.9(3) . . ?
C21 C25 Fe2 70.30(17) . . ?
C24 C25 Fe2 69.82(17) . . ?
C26 C25 Fe2 120.8(2) . . ?
O27 C26 O28 124.2(3) . . ?
O27 C26 C25 122.9(3) . . ?
O28 C26 C25 113.0(3) . . ?
C26 O28 H28 116(4) . . ?
C33 C29 C30 107.2(3) . . ?
C33 C29 Fe2 70.23(18) . . ?
C30 C29 Fe2 69.21(18) . . ?
C33 C29 H29 126.4 . . ?
C30 C29 H29 126.4 . . ?
Fe2 C29 H29 125.7 . . ?
C31 C30 C29 108.8(3) . . ?
C31 C30 Fe2 69.69(18) . . ?
C29 C30 Fe2 69.98(18) . . ?
C31 C30 H30 125.6 . . ?
C29 C30 H30 125.6 . . ?
Fe2 C30 H30 126.3 . . ?
C30 C31 C32 107.6(3) . . ?
C30 C31 Fe2 69.74(18) . . ?
C32 C31 Fe2 69.43(18) . . ?
C30 C31 H31 126.2 . . ?
C32 C31 H31 126.2 . . ?
Fe2 C31 H31 126.2 . . ?
C33 C32 C31 108.0(3) . . ?
C33 C32 Fe2 70.67(18) . . ?
C31 C32 Fe2 69.67(19) . . ?
C33 C32 H32 126.0 . . ?
C31 C32 H32 126.0 . . ?
Fe2 C32 H32 125.3 . . ?
N34 C33 C29 130.6(3) . . ?
N34 C33 C32 121.0(3) . . ?
C29 C33 C32 108.4(3) . . ?
N34 C33 Fe2 129.6(2) . . ?
C29 C33 Fe2 69.38(18) . . ?
C32 C33 Fe2 68.76(18) . . ?
C35 N34 C33 129.3(3) . . ?
C35 N34 H34 115.3 . . ?
C33 N34 H34 115.3 . . ?
O36 C35 O37 123.6(3) . . ?
O36 C35 N34 123.2(3) . . ?
O37 C35 N34 113.2(3) . . ?
C35 O37 C38 114.9(2) . . ?
O37 C38 C39 107.0(3) . . ?
O37 C38 H38A 110.3 . . ?
C39 C38 H38A 110.3 . . ?
O37 C38 H38B 110.3 . . ?
C39 C38 H38B 110.3 . . ?
H38A C38 H38B 108.6 . . ?
C40 C39 C38 123.8(4) . . ?
C40 C39 H39 118.1 . . ?
C38 C39 H39 118.1 . . ?
C39 C40 H40A 120.0 . . ?
C39 C40 H40B 120.0 . . ?
H40A C40 H40B 120.0 . . ?

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
C5 C1 C2 C3 -0.3(3) . . . . ?
Fe1 C1 C2 C3 58.8(2) . . . . ?
C5 C1 C2 Fe1 -59.1(2) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
Fe1 C2 C3 C4 58.8(2) . . . . ?
C1 C2 C3 Fe1 -58.4(2) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
Fe1 C3 C4 C5 58.8(2) . . . . ?
C2 C3 C4 Fe1 -59.1(2) . . . . ?
C3 C4 C5 C1 0.1(3) . . . . ?
Fe1 C4 C5 C1 60.0(2) . . . . ?
C3 C4 C5 C6 -171.6(3) . . . . ?
Fe1 C4 C5 C6 -111.8(3) . . . . ?
C3 C4 C5 Fe1 -59.8(2) . . . . ?
C2 C1 C5 C4 0.1(3) . . . . ?
Fe1 C1 C5 C4 -60.1(2) . . . . ?
C2 C1 C5 C6 171.8(3) . . . . ?
Fe1 C1 C5 C6 111.6(3) . . . . ?
C2 C1 C5 Fe1 60.2(2) . . . . ?
C4 C5 C6 O8 170.6(3) . . . . ?
C1 C5 C6 O8 0.2(5) . . . . ?
Fe1 C5 C6 O8 85.3(3) . . . . ?
C4 C5 C6 O7 -8.6(4) . . . . ?
C1 C5 C6 O7 -178.9(3) . . . . ?
Fe1 C5 C6 O7 -93.8(3) . . . . ?
C13 C9 C10 C11 1.2(3) . . . . ?
Fe1 C9 C10 C11 -59.2(2) . . . . ?
C13 C9 C10 Fe1 60.3(2) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
Fe1 C10 C11 C12 -59.7(2) . . . . ?
C9 C10 C11 Fe1 59.8(2) . . . . ?
C10 C11 C12 C13 -1.2(3) . . . . ?
Fe1 C11 C12 C13 -60.9(2) . . . . ?
C10 C11 C12 Fe1 59.7(2) . . . . ?
C10 C9 C13 N14 176.5(3) . . . . ?
Fe1 C9 C13 N14 -124.3(3) . . . . ?
C10 C9 C13 C12 -1.9(3) . . . . ?
Fe1 C9 C13 C12 57.3(2) . . . . ?
C10 C9 C13 Fe1 -59.2(2) . . . . ?
C11 C12 C13 N14 -176.6(3) . . . . ?
Fe1 C12 C13 N14 123.6(3) . . . . ?
C11 C12 C13 C9 2.0(3) . . . . ?
Fe1 C12 C13 C9 -57.9(2) . . . . ?
C11 C12 C13 Fe1 59.8(2) . . . . ?
C9 C13 N14 C15 -1.2(5) . . . . ?
C12 C13 N14 C15 177.0(3) . . . . ?
Fe1 C13 N14 C15 -96.8(4) . . . . ?
C13 N14 C15 O16 -173.7(3) . . . . ?
C13 N14 C15 O17 6.6(5) . . . . ?
O16 C15 O17 C18 0.7(5) . . . . ?
N14 C15 O17 C18 -179.6(3) . . . . ?
C15 O17 C18 C19 115.7(3) . . . . ?
O17 C18 C19 C20 129.5(4) . . . . ?
C25 C21 C22 C23 -0.4(4) . . . . ?
Fe2 C21 C22 C23 -59.0(2) . . . . ?
C25 C21 C22 Fe2 58.6(2) . . . . ?
C21 C22 C23 C24 0.5(4) . . . . ?
Fe2 C22 C23 C24 -58.2(2) . . . . ?
C21 C22 C23 Fe2 58.7(2) . . . . ?
C22 C23 C24 C25 -0.5(4) . . . . ?
Fe2 C23 C24 C25 -59.3(2) . . . . ?
C22 C23 C24 Fe2 58.8(2) . . . . ?
C22 C21 C25 C24 0.1(4) . . . . ?
Fe2 C21 C25 C24 59.8(2) . . . . ?
C22 C21 C25 C26 -174.0(3) . . . . ?
Fe2 C21 C25 C26 -114.3(3) . . . . ?
C22 C21 C25 Fe2 -59.7(2) . . . . ?
C23 C24 C25 C21 0.2(4) . . . . ?
Fe2 C24 C25 C21 -60.1(2) . . . . ?
C23 C24 C25 C26 174.3(3) . . . . ?
Fe2 C24 C25 C26 114.0(3) . . . . ?
C23 C24 C25 Fe2 60.3(2) . . . . ?
C21 C25 C26 O27 177.1(3) . . . . ?
C24 C25 C26 O27 4.0(5) . . . . ?
Fe2 C25 C26 O27 90.3(3) . . . . ?
C21 C25 C26 O28 -2.3(4) . . . . ?
C24 C25 C26 O28 -175.4(3) . . . . ?
Fe2 C25 C26 O28 -89.1(3) . . . . ?
C33 C29 C30 C31 1.2(4) . . . . ?
Fe2 C29 C30 C31 -59.0(2) . . . . ?
C33 C29 C30 Fe2 60.3(2) . . . . ?
C29 C30 C31 C32 -0.1(4) . . . . ?
Fe2 C30 C31 C32 -59.4(2) . . . . ?
C29 C30 C31 Fe2 59.2(2) . . . . ?
C30 C31 C32 C33 -1.0(4) . . . . ?
Fe2 C31 C32 C33 -60.5(2) . . . . ?
C30 C31 C32 Fe2 59.5(2) . . . . ?
C30 C29 C33 N34 175.4(3) . . . . ?
Fe2 C29 C33 N34 -125.0(3) . . . . ?
C30 C29 C33 C32 -1.8(4) . . . . ?
Fe2 C29 C33 C32 57.8(2) . . . . ?
C30 C29 C33 Fe2 -59.6(2) . . . . ?
C31 C32 C33 N34 -175.8(3) . . . . ?
Fe2 C32 C33 N34 124.3(3) . . . . ?
C31 C32 C33 C29 1.8(4) . . . . ?
Fe2 C32 C33 C29 -58.2(2) . . . . ?
C31 C32 C33 Fe2 59.9(2) . . . . ?
C29 C33 N34 C35 16.7(5) . . . . ?
C32 C33 N34 C35 -166.4(3) . . . . ?
Fe2 C33 N34 C35 -79.4(4) . . . . ?
C33 N34 C35 O36 175.8(3) . . . . ?
C33 N34 C35 O37 -5.6(5) . . . . ?
O36 C35 O37 C38 -12.2(5) . . . . ?
N34 C35 O37 C38 169.2(3) . . . . ?
C35 O37 C38 C39 -179.3(3) . . . . ?
O37 C38 C39 C40 -128.1(4) . . . . ?

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
O7 H7 O27 0.86(5) 1.78(5) 2.636(3) 174(5) . yes
O28 H28 O8 0.75(5) 1.86(6) 2.610(3) 175(6) . yes
N14 H14 O36 0.88 1.99 2.871(3) 178.0 . yes
N34 H34 O16 0.88 2.03 2.860(4) 156.8 . yes

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR WE320X1                                                #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
####################################################################### 
# 
# 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_WE326X2
_database_code_depnum_ccdc_archive 'CCDC 1584019'
_audit_update_record             
;
2017-11-05 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H22 Fe N2 O6'
_chemical_formula_sum            'C20 H22 Fe N2 O6'
_chemical_formula_weight         442.24
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                            UNIT CELL INFORMATION                             #
#------------------------------------------------------------------------------#


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
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                   21.3600(13)
_cell_length_b                   10.0652(5)
_cell_length_c                   9.5245(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.112(2)
_cell_angle_gamma                90
_cell_volume                     2036.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9980
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      27.46
_cell_measurement_wavelength     0.71073

#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       board
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             920
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.731
_exptl_absorpt_correction_T_max  0.977

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_reflns_av_r_equivalents  0.0766
_diffrn_reflns_av_uneti/neti     0.0523
_diffrn_reflns_number            25512
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.953
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             4645
_reflns_number_gt                3849
_reflns_threshold_expression     >2sigma(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.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2017)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+10.4562P] 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         4645
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0620
_refine_ls_wR_factor_ref         0.1731
_refine_ls_wR_factor_gt          0.1664
_refine_ls_goodness_of_fit_ref   1.258
_refine_ls_restrained_S_all      1.258
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.890
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.106

#...............................................................................
# .RES SHELXL file: WE326x2.res
# .HKL SHELXL file: WE326x2.hkl
#...............................................................................



# ............... End of .HKL file .............................................
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'

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 0.74909(3) 0.43668(6) 0.74123(6) 0.01470(17) Uani 1 1 d . . . . .
C1 C 0.7058(2) 0.4873(4) 0.9161(5) 0.0188(8) Uani 1 1 d . . . . .
H1 H 0.720068 0.466811 1.011481 0.023 Uiso 1 1 calc R U . . .
C2 C 0.7216(2) 0.6025(4) 0.8420(5) 0.0241(9) Uani 1 1 d . . . . .
H2 H 0.748311 0.672467 0.878935 0.029 Uiso 1 1 calc R U . . .
C3 C 0.6904(2) 0.5947(4) 0.7020(5) 0.0228(9) Uani 1 1 d . . . . .
H3 H 0.692826 0.658781 0.629548 0.027 Uiso 1 1 calc R U . . .
C4 C 0.65475(19) 0.4737(4) 0.6893(4) 0.0175(8) Uani 1 1 d . . . . .
H4 H 0.629383 0.443329 0.607622 0.021 Uiso 1 1 calc R U . . .
C5 C 0.66460(19) 0.4072(4) 0.8231(4) 0.0164(8) Uani 1 1 d . . . . .
N6 N 0.63715(16) 0.2889(4) 0.8641(4) 0.0166(7) Uani 1 1 d . . . . .
H6 H 0.634258 0.276947 0.954710 0.020 Uiso 1 1 calc R U . . .
C7 C 0.61472(19) 0.1914(4) 0.7740(4) 0.0169(8) Uani 1 1 d . . . . .
O8 O 0.61327(18) 0.1955(3) 0.6470(3) 0.0303(8) Uani 1 1 d . . . . .
O9 O 0.59458(16) 0.0888(3) 0.8487(3) 0.0231(7) Uani 1 1 d . . . . .
C10 C 0.5661(2) -0.0293(4) 0.7744(5) 0.0218(9) Uani 1 1 d . . . . .
C11 C 0.5029(2) 0.0105(6) 0.6975(6) 0.0378(12) Uani 1 1 d . . . . .
H11A H 0.477807 0.056123 0.763184 0.057 Uiso 1 1 calc R U . . .
H11B H 0.480440 -0.069074 0.660407 0.057 Uiso 1 1 calc R U . . .
H11C H 0.509631 0.070242 0.619214 0.057 Uiso 1 1 calc R U . . .
C12 C 0.5567(3) -0.1228(6) 0.8952(6) 0.0447(15) Uani 1 1 d . . . . .
H12A H 0.597171 -0.138396 0.951344 0.067 Uiso 1 1 calc R U . . .
H12B H 0.539631 -0.207355 0.857243 0.067 Uiso 1 1 calc R U . . .
H12C H 0.527155 -0.082922 0.955091 0.067 Uiso 1 1 calc R U . . .
C13 C 0.6095(3) -0.0906(5) 0.6770(6) 0.0385(13) Uani 1 1 d . . . . .
H13A H 0.611732 -0.032917 0.594767 0.058 Uiso 1 1 calc R U . . .
H13B H 0.593272 -0.177954 0.645543 0.058 Uiso 1 1 calc R U . . .
H13C H 0.651675 -0.100755 0.727426 0.058 Uiso 1 1 calc R U . . .
C21 C 0.8055(2) 0.4362(4) 0.5819(5) 0.0205(9) Uani 1 1 d . . . . .
H21 H 0.802202 0.494526 0.502997 0.025 Uiso 1 1 calc R U . . .
C22 C 0.7762(2) 0.3106(4) 0.5897(5) 0.0230(9) Uani 1 1 d . . . . .
H22 H 0.749745 0.269754 0.515571 0.028 Uiso 1 1 calc R U . . .
C23 C 0.7928(2) 0.2553(4) 0.7260(5) 0.0228(9) Uani 1 1 d . . . . .
H23 H 0.779256 0.171862 0.758193 0.027 Uiso 1 1 calc R U . . .
C24 C 0.8330(2) 0.3465(4) 0.8056(5) 0.0230(9) Uani 1 1 d . . . . .
H24 H 0.851021 0.335158 0.900367 0.028 Uiso 1 1 calc R U . . .
C25 C 0.84139(19) 0.4585(4) 0.7169(5) 0.0196(8) Uani 1 1 d . . . . .
C26 C 0.87270(19) 0.5814(4) 0.7641(5) 0.0208(9) Uani 1 1 d . . . . .
O27 O 0.89933(16) 0.6065(4) 0.8772(4) 0.0302(8) Uani 1 1 d . . . . .
O28 O 0.86846(16) 0.6708(3) 0.6515(4) 0.0290(7) Uani 1 1 d . . . . .
N29 N 0.89687(19) 0.7901(4) 0.6882(5) 0.0296(9) Uani 1 1 d . . . . .
C30 C 0.9604(2) 0.8093(5) 0.6733(7) 0.0391(13) Uani 1 1 d . . . . .
C31 C 0.9742(2) 0.9495(6) 0.7231(9) 0.0509(18) Uani 1 1 d . . . . .
H31A H 0.990042 1.003063 0.647248 0.061 Uiso 1 1 calc R U . . .
H31B H 1.006282 0.949790 0.806207 0.061 Uiso 1 1 calc R U . . .
C32 C 0.9111(3) 1.0063(6) 0.7627(11) 0.067(2) Uani 1 1 d . . . . .
H32A H 0.915195 1.034946 0.862733 0.080 Uiso 1 1 calc R U . . .
H32B H 0.897770 1.083413 0.702272 0.080 Uiso 1 1 calc R U . . .
C33 C 0.8645(2) 0.8946(5) 0.7387(7) 0.0384(13) Uani 1 1 d . . . . .
O34 O 0.99432(19) 0.7284(4) 0.6296(6) 0.0530(12) Uani 1 1 d . . . . .
O35 O 0.80947(18) 0.8932(4) 0.7565(5) 0.0507(12) Uani 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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 C25 2.021(4) . ?
Fe1 C3 2.035(4) . ?
Fe1 C21 2.036(4) . ?
Fe1 C2 2.042(4) . ?
Fe1 C24 2.044(4) . ?
Fe1 C22 2.051(4) . ?
Fe1 C1 2.054(4) . ?
Fe1 C4 2.057(4) . ?
Fe1 C23 2.062(4) . ?
Fe1 C5 2.062(4) . ?
C1 C2 1.417(6) . ?
C1 C5 1.429(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.428(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.434(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.435(6) . ?
C4 H4 0.9500 . ?
C5 N6 1.401(5) . ?
N6 C7 1.357(5) . ?
N6 H6 0.8800 . ?
C7 O8 1.207(5) . ?
C7 O9 1.350(5) . ?
O9 C10 1.480(5) . ?
C10 C13 1.512(7) . ?
C10 C12 1.516(7) . ?
C10 C11 1.520(7) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C21 C22 1.416(6) . ?
C21 C25 1.443(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.422(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.419(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.432(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.454(6) . ?
C26 O27 1.190(5) . ?
C26 O28 1.396(6) . ?
O28 N29 1.374(5) . ?
N29 C33 1.373(7) . ?
N29 C30 1.393(6) . ?
C30 O34 1.194(7) . ?
C30 C31 1.507(8) . ?
C31 C32 1.547(8) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.503(7) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 O35 1.206(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
C25 Fe1 C3 118.90(18) . . ?
C25 Fe1 C21 41.66(17) . . ?
C3 Fe1 C21 105.48(18) . . ?
C25 Fe1 C2 107.31(18) . . ?
C3 Fe1 C2 41.01(19) . . ?
C21 Fe1 C2 125.08(18) . . ?
C25 Fe1 C24 41.24(17) . . ?
C3 Fe1 C24 154.91(18) . . ?
C21 Fe1 C24 69.68(18) . . ?
C2 Fe1 C24 120.58(19) . . ?
C25 Fe1 C22 68.56(17) . . ?
C3 Fe1 C22 124.68(19) . . ?
C21 Fe1 C22 40.53(17) . . ?
C2 Fe1 C22 162.38(19) . . ?
C24 Fe1 C22 68.39(19) . . ?
C25 Fe1 C1 126.52(17) . . ?
C3 Fe1 C1 68.46(18) . . ?
C21 Fe1 C1 163.46(18) . . ?
C2 Fe1 C1 40.47(18) . . ?
C24 Fe1 C1 108.88(18) . . ?
C22 Fe1 C1 155.45(18) . . ?
C25 Fe1 C4 153.52(17) . . ?
C3 Fe1 C4 41.03(17) . . ?
C21 Fe1 C4 117.62(17) . . ?
C2 Fe1 C4 69.01(18) . . ?
C24 Fe1 C4 163.28(17) . . ?
C22 Fe1 C4 106.62(18) . . ?
C1 Fe1 C4 68.62(17) . . ?
C25 Fe1 C23 68.53(17) . . ?
C3 Fe1 C23 162.44(19) . . ?
C21 Fe1 C23 68.73(18) . . ?
C2 Fe1 C23 155.68(19) . . ?
C24 Fe1 C23 40.45(18) . . ?
C22 Fe1 C23 40.45(19) . . ?
C1 Fe1 C23 121.54(18) . . ?
C4 Fe1 C23 125.63(17) . . ?
C25 Fe1 C5 164.24(17) . . ?
C3 Fe1 C5 68.59(17) . . ?
C21 Fe1 C5 153.24(17) . . ?
C2 Fe1 C5 68.46(17) . . ?
C24 Fe1 C5 126.68(17) . . ?
C22 Fe1 C5 120.10(17) . . ?
C1 Fe1 C5 40.61(16) . . ?
C4 Fe1 C5 40.78(16) . . ?
C23 Fe1 C5 108.68(17) . . ?
C2 C1 C5 108.5(4) . . ?
C2 C1 Fe1 69.3(2) . . ?
C5 C1 Fe1 70.0(2) . . ?
C2 C1 H1 125.8 . . ?
C5 C1 H1 125.8 . . ?
Fe1 C1 H1 126.5 . . ?
C1 C2 C3 107.9(4) . . ?
C1 C2 Fe1 70.2(2) . . ?
C3 C2 Fe1 69.2(3) . . ?
C1 C2 H2 126.0 . . ?
C3 C2 H2 126.0 . . ?
Fe1 C2 H2 126.1 . . ?
C2 C3 C4 108.4(4) . . ?
C2 C3 Fe1 69.8(3) . . ?
C4 C3 Fe1 70.3(2) . . ?
C2 C3 H3 125.8 . . ?
C4 C3 H3 125.8 . . ?
Fe1 C3 H3 125.7 . . ?
C3 C4 C5 107.1(4) . . ?
C3 C4 Fe1 68.7(2) . . ?
C5 C4 Fe1 69.8(2) . . ?
C3 C4 H4 126.4 . . ?
C5 C4 H4 126.4 . . ?
Fe1 C4 H4 126.7 . . ?
N6 C5 C1 123.7(4) . . ?
N6 C5 C4 128.1(4) . . ?
C1 C5 C4 108.0(4) . . ?
N6 C5 Fe1 129.5(3) . . ?
C1 C5 Fe1 69.4(2) . . ?
C4 C5 Fe1 69.4(2) . . ?
C7 N6 C5 124.7(3) . . ?
C7 N6 H6 117.7 . . ?
C5 N6 H6 117.7 . . ?
O8 C7 O9 125.3(4) . . ?
O8 C7 N6 125.3(4) . . ?
O9 C7 N6 109.3(3) . . ?
C7 O9 C10 120.0(3) . . ?
O9 C10 C13 111.9(4) . . ?
O9 C10 C12 102.5(3) . . ?
C13 C10 C12 110.6(5) . . ?
O9 C10 C11 108.5(4) . . ?
C13 C10 C11 112.5(4) . . ?
C12 C10 C11 110.3(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C22 C21 C25 106.7(4) . . ?
C22 C21 Fe1 70.3(2) . . ?
C25 C21 Fe1 68.6(2) . . ?
C22 C21 H21 126.6 . . ?
C25 C21 H21 126.6 . . ?
Fe1 C21 H21 126.0 . . ?
C21 C22 C23 109.2(4) . . ?
C21 C22 Fe1 69.2(2) . . ?
C23 C22 Fe1 70.2(2) . . ?
C21 C22 H22 125.4 . . ?
C23 C22 H22 125.4 . . ?
Fe1 C22 H22 126.9 . . ?
C24 C23 C22 108.2(4) . . ?
C24 C23 Fe1 69.1(2) . . ?
C22 C23 Fe1 69.4(2) . . ?
C24 C23 H23 125.9 . . ?
C22 C23 H23 125.9 . . ?
Fe1 C23 H23 127.2 . . ?
C23 C24 C25 107.5(4) . . ?
C23 C24 Fe1 70.5(2) . . ?
C25 C24 Fe1 68.5(2) . . ?
C23 C24 H24 126.2 . . ?
C25 C24 H24 126.2 . . ?
Fe1 C24 H24 126.3 . . ?
C24 C25 C21 108.4(4) . . ?
C24 C25 C26 124.8(4) . . ?
C21 C25 C26 126.2(4) . . ?
C24 C25 Fe1 70.2(2) . . ?
C21 C25 Fe1 69.7(2) . . ?
C26 C25 Fe1 118.6(3) . . ?
O27 C26 O28 122.9(4) . . ?
O27 C26 C25 128.3(4) . . ?
O28 C26 C25 108.7(4) . . ?
N29 O28 C26 112.2(4) . . ?
C33 N29 O28 122.3(4) . . ?
C33 N29 C30 117.5(4) . . ?
O28 N29 C30 120.3(4) . . ?
O34 C30 N29 125.1(5) . . ?
O34 C30 C31 130.0(5) . . ?
N29 C30 C31 104.9(4) . . ?
C30 C31 C32 106.1(4) . . ?
C30 C31 H31A 110.5 . . ?
C32 C31 H31A 110.5 . . ?
C30 C31 H31B 110.5 . . ?
C32 C31 H31B 110.5 . . ?
H31A C31 H31B 108.7 . . ?
C33 C32 C31 105.4(5) . . ?
C33 C32 H32A 110.7 . . ?
C31 C32 H32A 110.7 . . ?
C33 C32 H32B 110.7 . . ?
C31 C32 H32B 110.7 . . ?
H32A C32 H32B 108.8 . . ?
O35 C33 N29 125.1(5) . . ?
O35 C33 C32 128.9(5) . . ?
N29 C33 C32 106.1(4) . . ?

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
C5 C1 C2 C3 -0.1(5) . . . . ?
Fe1 C1 C2 C3 59.2(3) . . . . ?
C5 C1 C2 Fe1 -59.2(3) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
Fe1 C2 C3 C4 59.9(3) . . . . ?
C1 C2 C3 Fe1 -59.8(3) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
Fe1 C3 C4 C5 59.4(3) . . . . ?
C2 C3 C4 Fe1 -59.6(3) . . . . ?
C2 C1 C5 N6 -176.7(4) . . . . ?
Fe1 C1 C5 N6 124.5(4) . . . . ?
C2 C1 C5 C4 0.0(5) . . . . ?
Fe1 C1 C5 C4 -58.8(3) . . . . ?
C2 C1 C5 Fe1 58.8(3) . . . . ?
C3 C4 C5 N6 176.6(4) . . . . ?
Fe1 C4 C5 N6 -124.7(4) . . . . ?
C3 C4 C5 C1 0.1(5) . . . . ?
Fe1 C4 C5 C1 58.8(3) . . . . ?
C3 C4 C5 Fe1 -58.7(3) . . . . ?
C1 C5 N6 C7 -158.6(4) . . . . ?
C4 C5 N6 C7 25.5(6) . . . . ?
Fe1 C5 N6 C7 -68.5(5) . . . . ?
C5 N6 C7 O8 -2.9(7) . . . . ?
C5 N6 C7 O9 176.8(4) . . . . ?
O8 C7 O9 C10 -2.1(7) . . . . ?
N6 C7 O9 C10 178.2(4) . . . . ?
C7 O9 C10 C13 56.1(5) . . . . ?
C7 O9 C10 C12 174.6(4) . . . . ?
C7 O9 C10 C11 -68.7(5) . . . . ?
C25 C21 C22 C23 0.3(5) . . . . ?
Fe1 C21 C22 C23 -58.9(3) . . . . ?
C25 C21 C22 Fe1 59.2(3) . . . . ?
C21 C22 C23 C24 -0.1(5) . . . . ?
Fe1 C22 C23 C24 -58.3(3) . . . . ?
C21 C22 C23 Fe1 58.3(3) . . . . ?
C22 C23 C24 C25 -0.2(5) . . . . ?
Fe1 C23 C24 C25 -58.7(3) . . . . ?
C22 C23 C24 Fe1 58.5(3) . . . . ?
C23 C24 C25 C21 0.4(5) . . . . ?
Fe1 C24 C25 C21 -59.5(3) . . . . ?
C23 C24 C25 C26 171.7(4) . . . . ?
Fe1 C24 C25 C26 111.7(4) . . . . ?
C23 C24 C25 Fe1 60.0(3) . . . . ?
C22 C21 C25 C24 -0.5(5) . . . . ?
Fe1 C21 C25 C24 59.8(3) . . . . ?
C22 C21 C25 C26 -171.6(4) . . . . ?
Fe1 C21 C25 C26 -111.3(4) . . . . ?
C22 C21 C25 Fe1 -60.3(3) . . . . ?
C24 C25 C26 O27 5.2(7) . . . . ?
C21 C25 C26 O27 174.9(4) . . . . ?
Fe1 C25 C26 O27 90.0(5) . . . . ?
C24 C25 C26 O28 -176.2(4) . . . . ?
C21 C25 C26 O28 -6.5(6) . . . . ?
Fe1 C25 C26 O28 -91.4(4) . . . . ?
O27 C26 O28 N29 -1.6(6) . . . . ?
C25 C26 O28 N29 179.7(3) . . . . ?
C26 O28 N29 C33 -91.3(6) . . . . ?
C26 O28 N29 C30 89.6(5) . . . . ?
C33 N29 C30 O34 -179.3(6) . . . . ?
O28 N29 C30 O34 0.0(9) . . . . ?
C33 N29 C30 C31 0.7(7) . . . . ?
O28 N29 C30 C31 179.9(5) . . . . ?
O34 C30 C31 C32 178.3(8) . . . . ?
N29 C30 C31 C32 -1.6(8) . . . . ?
C30 C31 C32 C33 2.0(9) . . . . ?
O28 N29 C33 O35 0.3(10) . . . . ?
C30 N29 C33 O35 179.5(6) . . . . ?
O28 N29 C33 C32 -178.6(5) . . . . ?
C30 N29 C33 C32 0.6(8) . . . . ?
C31 C32 C33 O35 179.6(7) . . . . ?
C31 C32 C33 N29 -1.6(8) . . . . ?

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR WE326X2                                                #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
####################################################################### 
# 
# 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_GL02SEL
_database_code_depnum_ccdc_archive 'CCDC 1584020'
_audit_update_record             
;
2017-11-05 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;


#----------------------------------------------------------------------------#
#                              CHEMICAL_INFORMATION                          #
#----------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H9 Fe O4, C6 H16 N'
_chemical_formula_sum            'C18 H25 Fe N O4'
_chemical_formula_weight         375.24
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                             UNIT CELL INFORMATION                          #
#----------------------------------------------------------------------------#


_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_IT_number           61
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.193(7)
_cell_length_b                   11.681(4)
_cell_length_c                   21.035(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3487(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6175
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      27.42
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                              CRYSTAL INFORMATION                           #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.470
_exptl_crystal_size_min          0.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1584
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                             ABSORPTION CORRECTION                          #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.460
_exptl_absorpt_correction_T_max  0.733

#----------------------------------------------------------------------------#
#                                DATA COLLECTION                             #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_reflns_av_r_equivalents  0.0863
_diffrn_reflns_av_uneti/neti     0.0575
_diffrn_reflns_number            27763
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.975
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             3990
_reflns_number_gt                3372
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                             COMPUTER PROGRAMS USED                         #
#----------------------------------------------------------------------------#

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2014)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2016)'

#----------------------------------------------------------------------------#
#                             REFINEMENT INFORMATION                         #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0718P)²+2.3229P] 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         3990
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1310
_refine_ls_wR_factor_gt          0.1203
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.911
_refine_diff_density_min         -0.945
_refine_diff_density_rms         0.126

#...............................................................................
# .RES SHELXL file: GL02SEL.res
# .HKL SHELXL file: GL02SEL.hkl
#...............................................................................



# ............... End of .HKL file .............................................
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS            #
#----------------------------------------------------------------------------#

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'

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 0.43592(2) 0.76599(3) 0.47126(2) 0.01515(13) Uani 1 1 d . . . . .
O1 O 0.35472(13) 0.46599(14) 0.44467(10) 0.0357(4) Uani 1 1 d . . . . .
O2 O 0.22533(11) 0.56926(14) 0.42324(8) 0.0276(4) Uani 1 1 d . . . . .
H2 H 0.215420 0.517016 0.396627 0.041 Uiso 1 1 calc R U . . .
O3 O 0.32937(11) 0.93008(13) 0.33622(8) 0.0231(3) Uani 1 1 d . . . . .
O4 O 0.37164(13) 0.77008(15) 0.28773(9) 0.0300(4) Uani 1 1 d . . . . .
C1 C 0.30761(15) 0.55183(18) 0.45135(11) 0.0212(4) Uani 1 1 d . . . . .
C2 C 0.33410(15) 0.64855(19) 0.49263(10) 0.0202(4) Uani 1 1 d . . . . .
C3 C 0.40889(18) 0.6472(2) 0.53894(11) 0.0269(5) Uani 1 1 d . . . . .
H3 H 0.448456 0.584138 0.548939 0.032 Uiso 1 1 calc R U . . .
C4 C 0.4124(2) 0.7583(2) 0.56695(12) 0.0303(5) Uani 1 1 d . . . . .
H4 H 0.454153 0.781805 0.599743 0.036 Uiso 1 1 calc R U . . .
C5 C 0.34247(17) 0.8282(2) 0.53730(11) 0.0280(5) Uani 1 1 d . . . . .
H5 H 0.330464 0.906420 0.546583 0.034 Uiso 1 1 calc R U . . .
C6 C 0.29398(16) 0.76093(19) 0.49164(11) 0.0212(4) Uani 1 1 d . . . . .
H6 H 0.243858 0.786019 0.465155 0.025 Uiso 1 1 calc R U . . .
C7 C 0.37989(14) 0.83957(18) 0.33138(10) 0.0186(4) Uani 1 1 d . . . . .
C8 C 0.45453(13) 0.82006(17) 0.38025(10) 0.0158(4) Uani 1 1 d . . . . .
C9 C 0.50288(14) 0.71391(18) 0.39032(11) 0.0194(4) Uani 1 1 d . . . . .
H9 H 0.492050 0.644769 0.367686 0.023 Uiso 1 1 calc R U . . .
C10 C 0.56954(14) 0.7294(2) 0.43970(12) 0.0225(5) Uani 1 1 d . . . . .
H10 H 0.610632 0.672482 0.456189 0.027 Uiso 1 1 calc R U . . .
C11 C 0.56405(14) 0.8458(2) 0.46033(11) 0.0212(5) Uani 1 1 d . . . . .
H11 H 0.601447 0.879880 0.492638 0.025 Uiso 1 1 calc R U . . .
C12 C 0.49280(14) 0.90187(18) 0.42409(10) 0.0186(4) Uani 1 1 d . . . . .
H12 H 0.474012 0.979569 0.428234 0.022 Uiso 1 1 calc R U . . .
N21 N 0.19249(13) 0.90049(17) 0.24789(9) 0.0248(4) Uani 1 1 d . . . . .
H21 H 0.249735 0.896862 0.275534 0.030 Uiso 1 1 calc R U . . .
C21 C 0.1419(2) 0.7889(2) 0.25734(14) 0.0355(6) Uani 1 1 d . . . . .
H21A H 0.082075 0.790678 0.233167 0.043 Uiso 1 1 calc R U . . .
H21B H 0.181021 0.726275 0.239766 0.043 Uiso 1 1 calc R U . . .
C22 C 0.1209(3) 0.7637(3) 0.32483(18) 0.0592(10) Uani 1 1 d . . . . .
H22A H 0.178088 0.774049 0.350306 0.089 Uiso 1 1 calc R U . . .
H22B H 0.098943 0.684493 0.328785 0.089 Uiso 1 1 calc R U . . .
H22C H 0.071799 0.815904 0.340071 0.089 Uiso 1 1 calc R U . . .
C23 C 0.13817(17) 1.0039(2) 0.26952(12) 0.0283(5) Uani 1 1 d . . . . .
H23A H 0.179274 1.072039 0.265806 0.034 Uiso 1 1 calc R U . . .
H23B H 0.122154 0.994349 0.315024 0.034 Uiso 1 1 calc R U . . .
C24 C 0.0487(2) 1.0258(3) 0.23291(17) 0.0469(8) Uani 1 1 d . . . . .
H24A H 0.062592 1.026923 0.187277 0.070 Uiso 1 1 calc R U . . .
H24B H 0.022174 1.099760 0.245657 0.070 Uiso 1 1 calc R U . . .
H24C H 0.003137 0.964888 0.241976 0.070 Uiso 1 1 calc R U . . .
C25 C 0.22828(19) 0.9072(2) 0.18059(12) 0.0341(6) Uani 1 1 d . . . . .
H25A H 0.173890 0.906164 0.151134 0.041 Uiso 1 1 calc R U . . .
H25B H 0.267081 0.838605 0.171632 0.041 Uiso 1 1 calc R U . . .
C26 C 0.2863(2) 1.0128(3) 0.16791(14) 0.0445(7) Uani 1 1 d . . . . .
H26A H 0.245274 1.080297 0.168134 0.067 Uiso 1 1 calc R U . . .
H26B H 0.316904 1.005957 0.126325 0.067 Uiso 1 1 calc R U . . .
H26C H 0.334405 1.020855 0.201024 0.067 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                               MOLECULAR GEOMETRY                           #
#----------------------------------------------------------------------------#

_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 C3 2.025(2) . ?
Fe1 C8 2.033(2) . ?
Fe1 C12 2.038(2) . ?
Fe1 C4 2.042(3) . ?
Fe1 C9 2.043(2) . ?
Fe1 C2 2.043(2) . ?
Fe1 C5 2.053(2) . ?
Fe1 C10 2.054(2) . ?
Fe1 C11 2.056(2) . ?
Fe1 C6 2.060(2) . ?
O1 C1 1.213(3) . ?
O2 C1 1.325(3) . ?
O2 H2 0.8400 . ?
O3 C7 1.282(3) . ?
O4 C7 1.231(3) . ?
C1 C2 1.474(3) . ?
C2 C6 1.431(3) . ?
C2 C3 1.441(3) . ?
C3 C4 1.426(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.429(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.419(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.494(3) . ?
C8 C9 1.433(3) . ?
C8 C12 1.435(3) . ?
C9 C10 1.417(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.429(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.426(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
N21 C21 1.501(3) . ?
N21 C23 1.503(3) . ?
N21 C25 1.506(3) . ?
N21 H21 1.0000 . ?
C21 C22 1.480(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.507(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.507(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 Fe1 C8 154.11(9) . . ?
C3 Fe1 C12 161.97(9) . . ?
C8 Fe1 C12 41.27(8) . . ?
C3 Fe1 C4 41.04(10) . . ?
C8 Fe1 C4 164.35(9) . . ?
C12 Fe1 C4 125.36(9) . . ?
C3 Fe1 C9 118.05(10) . . ?
C8 Fe1 C9 41.17(8) . . ?
C12 Fe1 C9 69.02(9) . . ?
C4 Fe1 C9 152.18(10) . . ?
C3 Fe1 C2 41.49(9) . . ?
C8 Fe1 C2 120.52(9) . . ?
C12 Fe1 C2 155.54(9) . . ?
C4 Fe1 C2 68.76(10) . . ?
C9 Fe1 C2 108.22(9) . . ?
C3 Fe1 C5 69.16(11) . . ?
C8 Fe1 C5 127.67(10) . . ?
C12 Fe1 C5 108.04(10) . . ?
C4 Fe1 C5 40.82(11) . . ?
C9 Fe1 C5 165.88(10) . . ?
C2 Fe1 C5 68.39(10) . . ?
C3 Fe1 C10 105.04(10) . . ?
C8 Fe1 C10 68.93(9) . . ?
C12 Fe1 C10 68.85(9) . . ?
C4 Fe1 C10 117.40(11) . . ?
C9 Fe1 C10 40.46(9) . . ?
C2 Fe1 C10 125.77(10) . . ?
C5 Fe1 C10 152.68(10) . . ?
C3 Fe1 C11 123.83(10) . . ?
C8 Fe1 C11 68.84(9) . . ?
C12 Fe1 C11 40.76(9) . . ?
C4 Fe1 C11 105.94(10) . . ?
C9 Fe1 C11 68.30(9) . . ?
C2 Fe1 C11 162.67(9) . . ?
C5 Fe1 C11 119.11(10) . . ?
C10 Fe1 C11 40.69(9) . . ?
C3 Fe1 C6 69.43(10) . . ?
C8 Fe1 C6 109.38(9) . . ?
C12 Fe1 C6 120.72(9) . . ?
C4 Fe1 C6 68.52(11) . . ?
C9 Fe1 C6 128.30(9) . . ?
C2 Fe1 C6 40.82(9) . . ?
C5 Fe1 C6 40.35(9) . . ?
C10 Fe1 C6 164.55(9) . . ?
C11 Fe1 C6 154.28(9) . . ?
C1 O2 H2 109.5 . . ?
O1 C1 O2 124.1(2) . . ?
O1 C1 C2 124.1(2) . . ?
O2 C1 C2 111.72(19) . . ?
C6 C2 C3 108.2(2) . . ?
C6 C2 C1 126.4(2) . . ?
C3 C2 C1 125.3(2) . . ?
C6 C2 Fe1 70.26(12) . . ?
C3 C2 Fe1 68.59(13) . . ?
C1 C2 Fe1 124.44(15) . . ?
C4 C3 C2 107.2(2) . . ?
C4 C3 Fe1 70.15(14) . . ?
C2 C3 Fe1 69.93(12) . . ?
C4 C3 H3 126.4 . . ?
C2 C3 H3 126.4 . . ?
Fe1 C3 H3 125.1 . . ?
C3 C4 C5 108.4(2) . . ?
C3 C4 Fe1 68.81(13) . . ?
C5 C4 Fe1 70.01(14) . . ?
C3 C4 H4 125.8 . . ?
C5 C4 H4 125.8 . . ?
Fe1 C4 H4 126.9 . . ?
C6 C5 C4 108.4(2) . . ?
C6 C5 Fe1 70.09(13) . . ?
C4 C5 Fe1 69.17(15) . . ?
C6 C5 H5 125.8 . . ?
C4 C5 H5 125.8 . . ?
Fe1 C5 H5 126.5 . . ?
C5 C6 C2 107.8(2) . . ?
C5 C6 Fe1 69.56(13) . . ?
C2 C6 Fe1 68.92(12) . . ?
C5 C6 H6 126.1 . . ?
C2 C6 H6 126.1 . . ?
Fe1 C6 H6 127.0 . . ?
O4 C7 O3 123.4(2) . . ?
O4 C7 C8 118.69(19) . . ?
O3 C7 C8 117.91(18) . . ?
C9 C8 C12 107.46(18) . . ?
C9 C8 C7 124.99(19) . . ?
C12 C8 C7 127.53(19) . . ?
C9 C8 Fe1 69.77(12) . . ?
C12 C8 Fe1 69.56(12) . . ?
C7 C8 Fe1 127.11(14) . . ?
C10 C9 C8 108.52(19) . . ?
C10 C9 Fe1 70.21(13) . . ?
C8 C9 Fe1 69.06(12) . . ?
C10 C9 H9 125.7 . . ?
C8 C9 H9 125.7 . . ?
Fe1 C9 H9 126.6 . . ?
C9 C10 C11 107.92(19) . . ?
C9 C10 Fe1 69.33(12) . . ?
C11 C10 Fe1 69.73(12) . . ?
C9 C10 H10 126.0 . . ?
C11 C10 H10 126.0 . . ?
Fe1 C10 H10 126.5 . . ?
C12 C11 C10 108.27(19) . . ?
C12 C11 Fe1 68.95(12) . . ?
C10 C11 Fe1 69.58(12) . . ?
C12 C11 H11 125.9 . . ?
C10 C11 H11 125.9 . . ?
Fe1 C11 H11 127.2 . . ?
C11 C12 C8 107.82(19) . . ?
C11 C12 Fe1 70.29(12) . . ?
C8 C12 Fe1 69.17(12) . . ?
C11 C12 H12 126.1 . . ?
C8 C12 H12 126.1 . . ?
Fe1 C12 H12 126.0 . . ?
C21 N21 C23 114.3(2) . . ?
C21 N21 C25 109.31(19) . . ?
C23 N21 C25 114.58(19) . . ?
C21 N21 H21 105.9 . . ?
C23 N21 H21 105.9 . . ?
C25 N21 H21 105.9 . . ?
C22 C21 N21 113.3(2) . . ?
C22 C21 H21A 108.9 . . ?
N21 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
N21 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N21 C23 C24 114.4(2) . . ?
N21 C23 H23A 108.7 . . ?
C24 C23 H23A 108.7 . . ?
N21 C23 H23B 108.7 . . ?
C24 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N21 C25 C26 113.1(2) . . ?
N21 C25 H25A 109.0 . . ?
C26 C25 H25A 109.0 . . ?
N21 C25 H25B 109.0 . . ?
C26 C25 H25B 109.0 . . ?
H25A C25 H25B 107.8 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
O1 C1 C2 C6 164.7(2) . . . . ?
O2 C1 C2 C6 -16.3(3) . . . . ?
O1 C1 C2 C3 -11.8(4) . . . . ?
O2 C1 C2 C3 167.1(2) . . . . ?
O1 C1 C2 Fe1 74.9(3) . . . . ?
O2 C1 C2 Fe1 -106.1(2) . . . . ?
C6 C2 C3 C4 1.3(3) . . . . ?
C1 C2 C3 C4 178.4(2) . . . . ?
Fe1 C2 C3 C4 60.57(17) . . . . ?
C6 C2 C3 Fe1 -59.25(15) . . . . ?
C1 C2 C3 Fe1 117.8(2) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
Fe1 C3 C4 C5 58.99(17) . . . . ?
C2 C3 C4 Fe1 -60.43(16) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
Fe1 C4 C5 C6 59.28(16) . . . . ?
C3 C4 C5 Fe1 -58.25(18) . . . . ?
C4 C5 C6 C2 -0.2(3) . . . . ?
Fe1 C5 C6 C2 58.51(15) . . . . ?
C4 C5 C6 Fe1 -58.71(17) . . . . ?
C3 C2 C6 C5 -0.7(2) . . . . ?
C1 C2 C6 C5 -177.7(2) . . . . ?
Fe1 C2 C6 C5 -58.91(16) . . . . ?
C3 C2 C6 Fe1 58.22(15) . . . . ?
C1 C2 C6 Fe1 -118.8(2) . . . . ?
O4 C7 C8 C9 -16.2(3) . . . . ?
O3 C7 C8 C9 165.75(19) . . . . ?
O4 C7 C8 C12 162.1(2) . . . . ?
O3 C7 C8 C12 -15.9(3) . . . . ?
O4 C7 C8 Fe1 -106.2(2) . . . . ?
O3 C7 C8 Fe1 75.7(2) . . . . ?
C12 C8 C9 C10 0.3(2) . . . . ?
C7 C8 C9 C10 178.90(19) . . . . ?
Fe1 C8 C9 C10 -59.31(16) . . . . ?
C12 C8 C9 Fe1 59.60(14) . . . . ?
C7 C8 C9 Fe1 -121.8(2) . . . . ?
C8 C9 C10 C11 -0.7(2) . . . . ?
Fe1 C9 C10 C11 -59.26(15) . . . . ?
C8 C9 C10 Fe1 58.60(14) . . . . ?
C9 C10 C11 C12 0.8(2) . . . . ?
Fe1 C10 C11 C12 -58.23(15) . . . . ?
C9 C10 C11 Fe1 59.00(15) . . . . ?
C10 C11 C12 C8 -0.6(2) . . . . ?
Fe1 C11 C12 C8 -59.21(14) . . . . ?
C10 C11 C12 Fe1 58.62(15) . . . . ?
C9 C8 C12 C11 0.2(2) . . . . ?
C7 C8 C12 C11 -178.38(19) . . . . ?
Fe1 C8 C12 C11 59.91(15) . . . . ?
C9 C8 C12 Fe1 -59.73(14) . . . . ?
C7 C8 C12 Fe1 121.7(2) . . . . ?
C23 N21 C21 C22 -61.7(3) . . . . ?
C25 N21 C21 C22 168.4(3) . . . . ?
C21 N21 C23 C24 -64.4(3) . . . . ?
C25 N21 C23 C24 62.9(3) . . . . ?
C21 N21 C25 C26 -175.8(2) . . . . ?
C23 N21 C25 C26 54.3(3) . . . . ?

#----------------------------------------------------------------------------#
#===END OF CIF FILE FOR GL02SEL                                              #
#----------------------------------------------------------------------------#
