# 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 2020

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

data_MW1404
_database_code_depnum_ccdc_archive 'CCDC 2017023'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;ISCR
France
;
_audit_update_record             
;
2020-07-17 deposited with the CCDC.	2020-11-02 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of diffraction experiment: 08 juin 2020                                 #
#------------------------------------------------------------------------------#


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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H12 F N3 O2'
_chemical_formula_sum            'C13 H12 F N3 O2'
_chemical_formula_weight         261.26
_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                   7.2126(7)
_cell_length_b                   7.7988(7)
_cell_length_c                   11.6303(11)
_cell_angle_alpha                108.895(3)
_cell_angle_beta                 99.835(3)
_cell_angle_gamma                97.095(3)
_cell_volume                     598.52(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8607
_cell_measurement_theta_min      2.8128
_cell_measurement_theta_max      27.5084
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0548299
_diffrn_orient_matrix_UB_21      0.0971617
_diffrn_orient_matrix_UB_31      -0.0900579
_diffrn_orient_matrix_UB_12      -0.1083369
_diffrn_orient_matrix_UB_22      0.0240543
_diffrn_orient_matrix_UB_32      -0.0821837
_diffrn_orient_matrix_UB_13      -0.0434647
_diffrn_orient_matrix_UB_23      0.0786260
_diffrn_orient_matrix_UB_33      0.0250267


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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             272
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.111
_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  0.893
_exptl_absorpt_correction_T_max  0.970

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

# Software                   : BIS V6.2.1/2016-03-01                           #
# Number of scans            :        3                                        #
# Total number of frames [*] :      456                                        #
# Total length of scans  [*] :   456.00 (deg.)                                 #
# Rotation speed         [*] :     8.00 sec./deg.                              #
# Total exposition time  [*] :      1 h   0.8 min.                             #
#                                                                              #
#  [*] fast scan not included                                                  #
#                                                                              #
# Measurement mode           : shutterless mode                                #
#                                                                              #
#    Scan  Time(s)  Width  DX (mm)  Frames  Theta  Omega    Phi    Chi   T(K)  #
#..............................................................................#
#                                                                              #
#  1 Phi       8.0   1.00     34.0     360   0.27 270.94 360.00  23.00 150.01  #
#  2 Omega     8.0   1.00     34.0      96   0.27   3.16   0.00 315.50 150.00  #
#  3 Fast      1.0   1.00     34.0     180   0.00 360.00   0.00  54.74 150.00  #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_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_source_current           1.0
_diffrn_source_voltage           55.0
_diffrn_reflns_av_uneti/neti     0.0255
_diffrn_reflns_av_r_equivalents  0.0275
_diffrn_reflns_number            11230
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.813
_diffrn_reflns_theta_max         27.508
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_reflns_number_total             2726
_reflns_number_gt                2411
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

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

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2016)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2020)'

#------------------------------------------------------------------------------#
#                            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)+(0.0643P)²+0.3934P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018_3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.056(9)
_refine_ls_number_reflns         2726
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1229
_refine_ls_wR_factor_gt          0.1181
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.060

#------------------------------------------------------------------------------#
#               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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4331(2) 0.22854(18) 0.49357(13) 0.0210(3) Uani 1 1 d . . . . .
H1 H 0.559093 0.210102 0.519176 0.025 Uiso 1 1 calc R U . . .
C2 C 0.3874(2) 0.29279(18) 0.39706(12) 0.0212(3) Uani 1 1 d . . . . .
C5 C 0.1055(2) 0.22156(19) 0.51571(13) 0.0217(3) Uani 1 1 d . . . . .
H5 H 0.008089 0.196666 0.556905 0.026 Uiso 1 1 calc R U . A 1
C6 C 0.2888(2) 0.19176(18) 0.55195(12) 0.0195(3) Uani 1 1 d . . . . .
F7 F 0.52499(15) 0.32233(14) 0.33530(9) 0.0370(3) Uani 1 1 d . . . . .
C3A C 0.2056(2) 0.32292(18) 0.35536(12) 0.0213(3) Uani 0.901(3) 1 d . . P B 1
C4A C 0.0660(2) 0.28793(19) 0.41893(13) 0.0220(3) Uani 0.901(3) 1 d . . P B 1
H4A H -0.058950 0.310160 0.395259 0.026 Uiso 0.901(3) 1 calc R U P B 1
N9A N 0.1672(3) 0.3878(2) 0.25694(13) 0.0241(3) Uani 0.901(3) 1 d . . P B 1
H9A H 0.065(3) 0.364(3) 0.226(2) 0.029 Uiso 0.9015 1 d . U P B 1
H9B H 0.233(3) 0.371(3) 0.219(2) 0.029 Uiso 0.9015 1 d . U P B 1
C3B C 0.2056(2) 0.32292(18) 0.35536(12) 0.0213(3) Uani 0.099(3) 1 d . . P B 2
H3B H 0.178069 0.364977 0.287379 0.026 Uiso 0.099(3) 1 calc R U P B 2
C4B C 0.0660(2) 0.28793(19) 0.41893(13) 0.0220(3) Uani 0.099(3) 1 d . . P B 2
N9B N -0.1096(19) 0.3125(17) 0.3839(11) 0.0241(3) Uani 0.099(3) 1 d . . P B 2
H9B1 H -0.199171 0.286821 0.421814 0.029 Uiso 0.099(3) 1 calc R U P B 2
H9B2 H -0.137182 0.354536 0.322588 0.029 Uiso 0.099(3) 1 calc R U P B 2
O9 O 0.33057(17) 0.10633(14) 0.63980(9) 0.0253(3) Uani 1 1 d . . . C 2
C10 C 0.30596(19) 0.18622(18) 0.75821(12) 0.0175(3) Uani 1 1 d . . . C 2
C11 C 0.31445(19) 0.07703(18) 0.83168(13) 0.0185(3) Uani 1 1 d . . . C 2
H11 H 0.329590 -0.047605 0.798882 0.022 Uiso 1 1 calc R U . C 2
C12 C 0.3002(2) 0.15520(19) 0.95421(13) 0.0203(3) Uani 1 1 d . . . C 2
H12 H 0.308490 0.081254 1.005024 0.024 Uiso 1 1 calc R U . C 2
N13 N 0.27539(16) 0.32932(16) 1.00561(10) 0.0190(3) Uani 1 1 d . . . C 2
C14 C 0.26413(17) 0.43038(17) 0.93195(12) 0.0157(3) Uani 1 1 d . . . C 2
C15 C 0.27997(18) 0.36743(18) 0.80827(12) 0.0167(3) Uani 1 1 d . . . C 2
H15 H 0.273338 0.444920 0.759881 0.020 Uiso 1 1 calc R U . C 2
C16 C 0.23289(18) 0.62559(18) 0.98803(12) 0.0173(3) Uani 1 1 d . . . C 2
O17 O 0.21670(16) 0.72568(14) 0.92513(10) 0.0252(3) Uani 1 1 d . . . C 2
N18 N 0.22293(17) 0.67764(16) 1.10787(11) 0.0198(3) Uani 1 1 d . . . C 2
H18 H 0.237(3) 0.601(3) 1.1471(17) 0.024 Uiso 1 1 d . U . D 2
C19 C 0.1973(2) 0.86181(19) 1.17692(14) 0.0240(3) Uani 1 1 d . . . C 2
H19A H 0.318922 0.949099 1.199477 0.036 Uiso 1 1 calc R U . C 2
H19B H 0.155736 0.861664 1.252849 0.036 Uiso 1 1 calc R U . C 2
H19C H 0.099800 0.898873 1.125009 0.036 Uiso 1 1 calc R U . C 2



#------------------------------------------------------------------------------#
#                              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 1.3778(19) . ?
C1 C6 1.3857(19) . ?
C1 H1 0.9500 . ?
C2 F7 1.3594(16) . ?
C2 C3B 1.394(2) . ?
C2 C3A 1.394(2) . ?
C5 C4B 1.3858(19) . ?
C5 C4A 1.3858(19) . ?
C5 C6 1.389(2) . ?
C5 H5 0.9500 . ?
C6 O9 1.4013(15) . ?
C3A N9A 1.3946(18) . ?
C3A C4A 1.397(2) . ?
C4A H4A 0.9500 . ?
N9A H9A 0.74(2) . ?
N9A H9B 0.70(2) . ?
C3B C4B 1.397(2) . ?
C3B H3B 0.9500 . ?
C4B N9B 1.319(13) . ?
N9B H9B1 0.8800 . ?
N9B H9B2 0.8800 . ?
O9 C10 1.3680(15) . ?
C10 C11 1.3876(18) . ?
C10 C15 1.3932(18) . ?
C11 C12 1.3841(19) . ?
C11 H11 0.9500 . ?
C12 N13 1.3432(18) . ?
C12 H12 0.9500 . ?
N13 C14 1.3383(16) . ?
C14 C15 1.3913(18) . ?
C14 C16 1.5119(18) . ?
C15 H15 0.9500 . ?
C16 O17 1.2334(16) . ?
C16 N18 1.3369(17) . ?
N18 C19 1.4532(17) . ?
N18 H18 0.865(19) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C2 C1 C6 117.64(13) . . ?
C2 C1 H1 121.2 . . ?
C6 C1 H1 121.2 . . ?
F7 C2 C1 118.45(13) . . ?
F7 C2 C3B 117.61(12) . . ?
C1 C2 C3B 123.89(13) . . ?
F7 C2 C3A 117.61(12) . . ?
C1 C2 C3A 123.89(13) . . ?
C4B C5 C6 119.41(13) . . ?
C4A C5 C6 119.41(13) . . ?
C4A C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 121.11(12) . . ?
C1 C6 O9 117.10(12) . . ?
C5 C6 O9 121.48(12) . . ?
C2 C3A N9A 121.46(14) . . ?
C2 C3A C4A 116.40(12) . . ?
N9A C3A C4A 122.13(14) . . ?
C5 C4A C3A 121.53(13) . . ?
C5 C4A H4A 119.2 . . ?
C3A C4A H4A 119.2 . . ?
C3A N9A H9A 112.7(18) . . ?
C3A N9A H9B 112.4(19) . . ?
H9A N9A H9B 117(3) . . ?
C2 C3B C4B 116.40(12) . . ?
C2 C3B H3B 121.8 . . ?
C4B C3B H3B 121.8 . . ?
N9B C4B C5 118.8(5) . . ?
N9B C4B C3B 119.6(5) . . ?
C5 C4B C3B 121.53(13) . . ?
C4B N9B H9B1 120.0 . . ?
C4B N9B H9B2 120.0 . . ?
H9B1 N9B H9B2 120.0 . . ?
C10 O9 C6 119.77(10) . . ?
O9 C10 C11 115.96(11) . . ?
O9 C10 C15 124.34(12) . . ?
C11 C10 C15 119.67(12) . . ?
C12 C11 C10 117.99(12) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
N13 C12 C11 123.94(12) . . ?
N13 C12 H12 118.0 . . ?
C11 C12 H12 118.0 . . ?
C14 N13 C12 116.78(11) . . ?
N13 C14 C15 124.24(12) . . ?
N13 C14 C16 117.32(11) . . ?
C15 C14 C16 118.44(11) . . ?
C14 C15 C10 117.35(12) . . ?
C14 C15 H15 121.3 . . ?
C10 C15 H15 121.3 . . ?
O17 C16 N18 123.87(12) . . ?
O17 C16 C14 121.05(12) . . ?
N18 C16 C14 115.08(11) . . ?
C16 N18 C19 122.29(12) . . ?
C16 N18 H18 119.3(12) . . ?
C19 N18 H18 118.4(12) . . ?
N18 C19 H19A 109.5 . . ?
N18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C6 C1 C2 F7 -177.31(12) . . . . ?
C6 C1 C2 C3B 0.1(2) . . . . ?
C6 C1 C2 C3A 0.1(2) . . . . ?
C2 C1 C6 C5 -1.0(2) . . . . ?
C2 C1 C6 O9 172.71(11) . . . . ?
C4B C5 C6 C1 0.5(2) . . . . ?
C4A C5 C6 C1 0.5(2) . . . . ?
C4B C5 C6 O9 -173.00(12) . . . . ?
F7 C2 C3A N9A -2.4(2) . . . . ?
C1 C2 C3A N9A -179.86(13) . . . . ?
F7 C2 C3A C4A 178.75(12) . . . . ?
C1 C2 C3A C4A 1.3(2) . . . . ?
C6 C5 C4A C3A 1.0(2) . . . . ?
C2 C3A C4A C5 -1.9(2) . . . . ?
N9A C3A C4A C5 179.30(13) . . . . ?
F7 C2 C3B C4B 178.75(12) . . . . ?
C1 C2 C3B C4B 1.3(2) . . . . ?
C6 C5 C4B N9B 178.8(6) . . . . ?
C6 C5 C4B C3B 1.0(2) . . . . ?
C2 C3B C4B N9B -179.6(6) . . . . ?
C2 C3B C4B C5 -1.9(2) . . . . ?
C1 C6 O9 C10 125.11(14) . . . . ?
C5 C6 O9 C10 -61.17(18) . . . . ?
C6 O9 C10 C11 168.01(12) . . . . ?
C6 O9 C10 C15 -14.1(2) . . . . ?
O9 C10 C11 C12 176.74(12) . . . . ?
C15 C10 C11 C12 -1.23(19) . . . . ?
C10 C11 C12 N13 1.2(2) . . . . ?
C11 C12 N13 C14 0.0(2) . . . . ?
C12 N13 C14 C15 -1.23(19) . . . . ?
C12 N13 C14 C16 179.01(11) . . . . ?
N13 C14 C15 C10 1.1(2) . . . . ?
C16 C14 C15 C10 -179.10(11) . . . . ?
O9 C10 C15 C14 -177.63(12) . . . . ?
C11 C10 C15 C14 0.16(19) . . . . ?
N13 C14 C16 O17 -178.35(12) . . . . ?
C15 C14 C16 O17 1.87(19) . . . . ?
N13 C14 C16 N18 1.07(17) . . . . ?
C15 C14 C16 N18 -178.71(11) . . . . ?
O17 C16 N18 C19 -1.9(2) . . . . ?
C14 C16 N18 C19 178.73(11) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

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


####################################################################### 
# 
# 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_MW285
_database_code_depnum_ccdc_archive 'CCDC 2017024'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;ISCR
France
;
_audit_update_record             
;
2020-07-17 deposited with the CCDC.	2020-11-02 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of diffraction experiment: 10 juin 2020                                 #
#------------------------------------------------------------------------------#


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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H11 F N2 O2'
_chemical_formula_sum            'C13 H11 F N2 O2'
_chemical_formula_weight         246.24
_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                   9.7343(10)
_cell_length_b                   13.7655(14)
_cell_length_c                   9.5215(10)
_cell_angle_alpha                90
_cell_angle_beta                 107.930(4)
_cell_angle_gamma                90
_cell_volume                     1213.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8043
_cell_measurement_theta_min      2.6507
_cell_measurement_theta_max      27.4821
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0947509
_diffrn_orient_matrix_UB_21      0.0441069
_diffrn_orient_matrix_UB_31      -0.0355262
_diffrn_orient_matrix_UB_12      -0.0361328
_diffrn_orient_matrix_UB_22      0.0582566
_diffrn_orient_matrix_UB_32      -0.0240412
_diffrn_orient_matrix_UB_13      0.0414609
_diffrn_orient_matrix_UB_23      0.0589077
_diffrn_orient_matrix_UB_33      0.0804312


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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             512
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.103
_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  0.769
_exptl_absorpt_correction_T_max  0.961

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

# Software                   : BIS V6.2.1/2016-03-01                           #
# Number of scans            :        2                                        #
# Total number of frames [*] :      215                                        #
# Total length of scans  [*] :   215.00 (deg.)                                 #
# Rotation speed         [*] :     8.00 sec./deg.                              #
# Total exposition time  [*] :         28.7 min.                               #
#                                                                              #
#  [*] fast scan not included                                                  #
#                                                                              #
# Measurement mode           : shutterless mode                                #
#                                                                              #
#    Scan  Time(s)  Width  DX (mm)  Frames  Theta  Omega    Phi    Chi   T(K)  #
#..............................................................................#
#                                                                              #
#  1 Phi       8.0   1.00     34.0     215   0.27 270.94 288.51  23.00 150.00  #
#  2 Fast      1.0   1.00     34.0     180   0.00 360.00   0.00  54.74 150.00  #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_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_source_current           1.0
_diffrn_source_voltage           55.0
_diffrn_reflns_av_uneti/neti     0.0371
_diffrn_reflns_av_r_equivalents  0.0380
_diffrn_reflns_number            10320
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.199
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_reflns_number_total             2762
_reflns_number_gt                2371
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

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

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2016)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'

#------------------------------------------------------------------------------#
#                            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)+(0.0386P)²+0.9826P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018_3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.033(3)
_refine_ls_number_reflns         2762
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1190
_refine_ls_wR_factor_gt          0.1133
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.050

#------------------------------------------------------------------------------#
#               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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
F1 F 0.26304(13) 0.03288(7) 0.54284(12) 0.0365(3) Uani 1 1 d . . . . .
C2 C 0.34600(19) 0.11264(12) 0.54614(18) 0.0257(4) Uani 1 1 d . . . . .
C3 C 0.4893(2) 0.10872(14) 0.6301(2) 0.0360(4) Uani 1 1 d . . . . .
H3 H 0.529181 0.051653 0.683165 0.043 Uiso 1 1 calc R U . . .
C4 C 0.5732(2) 0.19040(16) 0.6345(3) 0.0450(5) Uani 1 1 d . . . . .
H4 H 0.672102 0.189789 0.692097 0.054 Uiso 1 1 calc R U . . .
C5 C 0.5146(2) 0.27322(14) 0.5558(2) 0.0377(5) Uani 1 1 d . . . . .
H5 H 0.572745 0.328938 0.557939 0.045 Uiso 1 1 calc R U . . .
C6 C 0.36996(17) 0.27330(11) 0.47432(18) 0.0239(3) Uani 1 1 d . . . . .
C7 C 0.28244(17) 0.19340(12) 0.46728(17) 0.0232(3) Uani 1 1 d . . . . .
H7 H 0.183204 0.194088 0.410808 0.028 Uiso 1 1 calc R U . . .
O8 O 0.31112(13) 0.35667(8) 0.39329(12) 0.0265(3) Uani 1 1 d . . . . .
C9 C 0.25525(16) 0.42575(11) 0.46363(16) 0.0195(3) Uani 1 1 d . . . . .
C10 C 0.24612(17) 0.41548(11) 0.60584(16) 0.0211(3) Uani 1 1 d . . . . .
H10 H 0.278264 0.358048 0.661610 0.025 Uiso 1 1 calc R U . . .
C11 C 0.18823(17) 0.49240(11) 0.66294(16) 0.0216(3) Uani 1 1 d . . . . .
H11 H 0.180420 0.485260 0.759430 0.026 Uiso 1 1 calc R U . . .
N12 N 0.14265(14) 0.57580(9) 0.59222(13) 0.0196(3) Uani 1 1 d . . . . .
C13 C 0.15134(15) 0.58272(10) 0.45421(15) 0.0171(3) Uani 1 1 d . . . . .
C14 C 0.20566(16) 0.51056(11) 0.38523(16) 0.0189(3) Uani 1 1 d . . . . .
H14 H 0.208989 0.518703 0.287249 0.023 Uiso 1 1 calc R U . . .
C15 C 0.09772(16) 0.67587(11) 0.37200(16) 0.0184(3) Uani 1 1 d . . . . .
O16 O 0.08145(14) 0.68125(8) 0.23796(12) 0.0281(3) Uani 1 1 d . . . . .
N17 N 0.07190(14) 0.74816(9) 0.45201(14) 0.0203(3) Uani 1 1 d . . . . .
H17 H 0.086(2) 0.7396(14) 0.546(2) 0.024 Uiso 1 1 d . U . . .
C18 C 0.0217(2) 0.84282(11) 0.38923(18) 0.0267(4) Uani 1 1 d . . . . .
H18A H 0.065715 0.858265 0.312172 0.040 Uiso 1 1 calc R U . . .
H18B H 0.049234 0.892289 0.466900 0.040 Uiso 1 1 calc R U . . .
H18C H -0.083600 0.841705 0.346308 0.040 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
F1 C2 1.3575(19) . ?
C2 C7 1.377(2) . ?
C2 C3 1.379(3) . ?
C3 C4 1.383(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.380(2) . ?
C6 O8 1.4029(19) . ?
C7 H7 0.9500 . ?
O8 C9 1.3685(18) . ?
C9 C14 1.390(2) . ?
C9 C10 1.391(2) . ?
C10 C11 1.387(2) . ?
C10 H10 0.9500 . ?
C11 N12 1.3358(19) . ?
C11 H11 0.9500 . ?
N12 C13 1.3459(19) . ?
C13 C14 1.383(2) . ?
C13 C15 1.509(2) . ?
C14 H14 0.9500 . ?
C15 O16 1.2389(18) . ?
C15 N17 1.324(2) . ?
N17 C18 1.4540(19) . ?
N17 H17 0.87(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
F1 C2 C7 118.43(15) . . ?
F1 C2 C3 118.06(15) . . ?
C7 C2 C3 123.51(16) . . ?
C2 C3 C4 117.94(17) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C3 C4 C5 120.72(18) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 118.86(17) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C7 C6 C5 122.23(15) . . ?
C7 C6 O8 118.93(14) . . ?
C5 C6 O8 118.83(15) . . ?
C2 C7 C6 116.73(15) . . ?
C2 C7 H7 121.6 . . ?
C6 C7 H7 121.6 . . ?
C9 O8 C6 117.11(12) . . ?
O8 C9 C14 116.46(13) . . ?
O8 C9 C10 124.04(13) . . ?
C14 C9 C10 119.51(14) . . ?
C11 C10 C9 117.35(14) . . ?
C11 C10 H10 121.3 . . ?
C9 C10 H10 121.3 . . ?
N12 C11 C10 124.79(14) . . ?
N12 C11 H11 117.6 . . ?
C10 C11 H11 117.6 . . ?
C11 N12 C13 116.23(13) . . ?
N12 C13 C14 124.14(13) . . ?
N12 C13 C15 116.80(13) . . ?
C14 C13 C15 119.06(13) . . ?
C13 C14 C9 117.95(13) . . ?
C13 C14 H14 121.0 . . ?
C9 C14 H14 121.0 . . ?
O16 C15 N17 124.15(14) . . ?
O16 C15 C13 119.95(13) . . ?
N17 C15 C13 115.90(13) . . ?
C15 N17 C18 122.44(13) . . ?
C15 N17 H17 119.5(13) . . ?
C18 N17 H17 118.1(13) . . ?
N17 C18 H18A 109.5 . . ?
N17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
F1 C2 C3 C4 -179.31(18) . . . . ?
C7 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
C4 C5 C6 O8 -179.21(18) . . . . ?
F1 C2 C7 C6 179.48(14) . . . . ?
C3 C2 C7 C6 0.3(2) . . . . ?
C5 C6 C7 C2 0.1(2) . . . . ?
O8 C6 C7 C2 178.59(14) . . . . ?
C7 C6 O8 C9 91.82(17) . . . . ?
C5 C6 O8 C9 -89.66(19) . . . . ?
C6 O8 C9 C14 176.07(13) . . . . ?
C6 O8 C9 C10 -3.9(2) . . . . ?
O8 C9 C10 C11 179.28(14) . . . . ?
C14 C9 C10 C11 -0.6(2) . . . . ?
C9 C10 C11 N12 -1.0(2) . . . . ?
C10 C11 N12 C13 1.8(2) . . . . ?
C11 N12 C13 C14 -1.1(2) . . . . ?
C11 N12 C13 C15 178.94(13) . . . . ?
N12 C13 C14 C9 -0.4(2) . . . . ?
C15 C13 C14 C9 179.57(13) . . . . ?
O8 C9 C14 C13 -178.66(13) . . . . ?
C10 C9 C14 C13 1.3(2) . . . . ?
N12 C13 C15 O16 -168.69(14) . . . . ?
C14 C13 C15 O16 11.3(2) . . . . ?
N12 C13 C15 N17 11.81(19) . . . . ?
C14 C13 C15 N17 -168.18(13) . . . . ?
O16 C15 N17 C18 -0.3(2) . . . . ?
C13 C15 N17 C18 179.14(13) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

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


####################################################################### 
# 
# 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_MW10441
_database_code_depnum_ccdc_archive 'CCDC 2017026'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;ISCR
France
;
_audit_update_record             
;
2020-07-17 deposited with the CCDC.	2020-11-02 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of diffraction experiment: 10 juin 2020                                 #
#------------------------------------------------------------------------------#


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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H15 Fe N O3'
_chemical_formula_sum            'C14 H15 Fe N O3'
_chemical_formula_weight         301.12
_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                   12.9052(17)
_cell_length_b                   10.4423(13)
_cell_length_c                   10.2490(14)
_cell_angle_alpha                90
_cell_angle_beta                 108.342(5)
_cell_angle_gamma                90
_cell_volume                     1311.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7574
_cell_measurement_theta_min      2.5630
_cell_measurement_theta_max      27.5115
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0923669
_diffrn_orient_matrix_UB_21      0.0086849
_diffrn_orient_matrix_UB_31      0.0442637
_diffrn_orient_matrix_UB_12      -0.0378198
_diffrn_orient_matrix_UB_22      -0.0260567
_diffrn_orient_matrix_UB_32      0.0840327
_diffrn_orient_matrix_UB_13      0.0379085
_diffrn_orient_matrix_UB_23      -0.0721063
_diffrn_orient_matrix_UB_33      -0.0052975


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

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.020
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             624
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    1.153
_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  0.730
_exptl_absorpt_correction_T_max  0.977

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

# Software                   : BIS V6.2.1/2016-03-01                           #
# Number of scans            :        3                                        #
# Total number of frames [*] :      227                                        #
# Total length of scans  [*] :   227.00 (deg.)                                 #
# Rotation speed         [*] :    60.00 sec./deg.                              #
# Total exposition time  [*] :      3 h  47.0 min.                             #
#                                                                              #
#  [*] fast scan not included                                                  #
#                                                                              #
# Measurement mode           : shutterless mode                                #
#                                                                              #
#    Scan  Time(s)  Width  DX (mm)  Frames  Theta  Omega    Phi    Chi   T(K)  #
#..............................................................................#
#                                                                              #
#  1 Omega    60.0   1.00     34.0      92   0.63 263.58  90.19  39.89 150.00  #
#  2 Phi      60.0   1.00     34.0     135   0.27 270.94 240.51  23.00 150.00  #
#  3 Fast      6.0   1.00     34.0     180   0.00 360.00   0.00  54.74 150.00  #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_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_source_current           1.0
_diffrn_source_voltage           55.0
_diffrn_reflns_av_uneti/neti     0.0441
_diffrn_reflns_av_r_equivalents  0.0450
_diffrn_reflns_number            10717
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.563
_diffrn_reflns_theta_max         27.528
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.984
_reflns_number_total             2963
_reflns_number_gt                2471
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

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

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2016)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'

#------------------------------------------------------------------------------#
#                            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)+(0.0455P)²+5.0225P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2963
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1149
_refine_ls_wR_factor_gt          0.1077
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_restrained_S_all      0.922
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.091

#------------------------------------------------------------------------------#
#               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 0.64368(3) 0.58428(4) 0.25252(4) 0.01447(13) Uani 1 1 d . . . . .
C1 C 0.7494(3) 0.6007(4) 0.1415(4) 0.0340(9) Uani 1 1 d . . . . .
H1 H 0.759362 0.539190 0.078244 0.041 Uiso 1 1 calc R U . . .
C2 C 0.8064(3) 0.6063(4) 0.2815(4) 0.0320(8) Uani 1 1 d . . . . .
H2 H 0.862466 0.549016 0.330225 0.038 Uiso 1 1 calc R U . . .
C3 C 0.7676(3) 0.7099(4) 0.3379(4) 0.0342(9) Uani 1 1 d . . . . .
H3 H 0.792522 0.734762 0.431849 0.041 Uiso 1 1 calc R U . . .
C4 C 0.6864(3) 0.7709(3) 0.2344(5) 0.0373(9) Uani 1 1 d . . . . .
H4 H 0.646559 0.844608 0.244788 0.045 Uiso 1 1 calc R U . . .
C5 C 0.6739(3) 0.7032(4) 0.1105(4) 0.0403(10) Uani 1 1 d . . . . .
H5 H 0.623966 0.722957 0.022709 0.048 Uiso 1 1 calc R U . . .
C6 C 0.6045(2) 0.4896(3) 0.4058(3) 0.0185(6) Uani 1 1 d . . . . .
H6 H 0.644106 0.492950 0.501073 0.022 Uiso 1 1 calc R U . . .
C7 C 0.5175(2) 0.5720(3) 0.3340(3) 0.0204(6) Uani 1 1 d . . . . .
H7 H 0.488129 0.639693 0.373370 0.024 Uiso 1 1 calc R U . . .
C8 C 0.4820(2) 0.5358(3) 0.1932(3) 0.0213(6) Uani 1 1 d . . . . .
H8 H 0.425009 0.575313 0.122371 0.026 Uiso 1 1 calc R U . . .
C9 C 0.5464(2) 0.4303(3) 0.1765(3) 0.0188(6) Uani 1 1 d . . . . .
H9 H 0.540582 0.387279 0.092860 0.023 Uiso 1 1 calc R U . . .
C10 C 0.6213(2) 0.4011(3) 0.3086(3) 0.0157(6) Uani 1 1 d . . . . .
N11 N 0.6998(2) 0.3030(2) 0.3445(3) 0.0169(5) Uani 1 1 d . . . . .
H11 H 0.723(3) 0.291(4) 0.423(4) 0.020 Uiso 1 1 d . U . . .
C12 C 0.7357(2) 0.2370(3) 0.2552(3) 0.0166(6) Uani 1 1 d . . . . .
O13 O 0.70566(18) 0.2498(2) 0.1303(2) 0.0224(5) Uani 1 1 d . . . . .
C14 C 0.8243(2) 0.1398(3) 0.3297(3) 0.0196(6) Uani 1 1 d . . . . .
O15 O 0.8603(2) 0.1335(3) 0.4523(3) 0.0375(7) Uani 1 1 d . . . . .
O16 O 0.85430(18) 0.0675(2) 0.2420(2) 0.0227(5) Uani 1 1 d . . . . .
C17 C 0.9425(3) -0.0226(3) 0.3051(4) 0.0267(7) Uani 1 1 d . . . . .
H17A H 0.925813 -0.071642 0.378680 0.032 Uiso 1 1 calc R U . . .
H17B H 1.011856 0.024316 0.346226 0.032 Uiso 1 1 calc R U . . .
C18 C 0.9529(3) -0.1114(4) 0.1954(4) 0.0338(8) Uani 1 1 d . . . . .
H18A H 0.885390 -0.160817 0.159002 0.051 Uiso 1 1 calc R U . . .
H18B H 1.014206 -0.170040 0.234322 0.051 Uiso 1 1 calc R U . . .
H18C H 0.966018 -0.061630 0.121079 0.051 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 C9 2.038(3) . ?
Fe1 C2 2.040(3) . ?
Fe1 C1 2.040(3) . ?
Fe1 C3 2.040(4) . ?
Fe1 C5 2.042(3) . ?
Fe1 C10 2.044(3) . ?
Fe1 C8 2.045(3) . ?
Fe1 C6 2.050(3) . ?
Fe1 C4 2.050(3) . ?
Fe1 C7 2.054(3) . ?
C1 C2 1.392(6) . ?
C1 C5 1.414(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.393(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.418(6) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.422(4) . ?
C6 C10 1.424(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.420(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.422(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.427(4) . ?
C9 H9 0.9500 . ?
C10 N11 1.407(4) . ?
N11 C12 1.340(4) . ?
N11 H11 0.78(4) . ?
C12 O13 1.222(4) . ?
C12 C14 1.539(4) . ?
C14 O15 1.196(4) . ?
C14 O16 1.321(4) . ?
O16 C17 1.462(4) . ?
C17 C18 1.496(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C9 Fe1 C2 128.82(14) . . ?
C9 Fe1 C1 107.04(13) . . ?
C2 Fe1 C1 39.90(16) . . ?
C9 Fe1 C3 167.61(15) . . ?
C2 Fe1 C3 39.92(15) . . ?
C1 Fe1 C3 67.28(14) . . ?
C9 Fe1 C5 116.10(15) . . ?
C2 Fe1 C5 67.43(15) . . ?
C1 Fe1 C5 40.53(17) . . ?
C3 Fe1 C5 67.38(15) . . ?
C9 Fe1 C10 40.94(11) . . ?
C2 Fe1 C10 107.15(13) . . ?
C1 Fe1 C10 114.48(13) . . ?
C3 Fe1 C10 129.95(14) . . ?
C5 Fe1 C10 147.69(16) . . ?
C9 Fe1 C8 40.76(12) . . ?
C2 Fe1 C8 168.20(15) . . ?
C1 Fe1 C8 130.84(15) . . ?
C3 Fe1 C8 151.09(15) . . ?
C5 Fe1 C8 110.16(14) . . ?
C10 Fe1 C8 68.31(12) . . ?
C9 Fe1 C6 68.98(12) . . ?
C2 Fe1 C6 115.73(14) . . ?
C1 Fe1 C6 146.89(15) . . ?
C3 Fe1 C6 109.30(14) . . ?
C5 Fe1 C6 171.19(16) . . ?
C10 Fe1 C6 40.71(11) . . ?
C8 Fe1 C6 68.50(12) . . ?
C9 Fe1 C4 150.06(15) . . ?
C2 Fe1 C4 67.17(14) . . ?
C1 Fe1 C4 67.87(15) . . ?
C3 Fe1 C4 39.70(16) . . ?
C5 Fe1 C4 40.56(17) . . ?
C10 Fe1 C4 168.87(16) . . ?
C8 Fe1 C4 119.15(14) . . ?
C6 Fe1 C4 131.79(15) . . ?
C9 Fe1 C7 68.54(12) . . ?
C2 Fe1 C7 149.28(15) . . ?
C1 Fe1 C7 170.58(15) . . ?
C3 Fe1 C7 118.70(14) . . ?
C5 Fe1 C7 132.94(15) . . ?
C10 Fe1 C7 68.09(12) . . ?
C8 Fe1 C7 40.54(13) . . ?
C6 Fe1 C7 40.55(12) . . ?
C4 Fe1 C7 111.49(13) . . ?
C2 C1 C5 107.7(3) . . ?
C2 C1 Fe1 70.0(2) . . ?
C5 C1 Fe1 69.8(2) . . ?
C2 C1 H1 126.2 . . ?
C5 C1 H1 126.2 . . ?
Fe1 C1 H1 125.6 . . ?
C1 C2 C3 108.5(3) . . ?
C1 C2 Fe1 70.1(2) . . ?
C3 C2 Fe1 70.1(2) . . ?
C1 C2 H2 125.7 . . ?
C3 C2 H2 125.7 . . ?
Fe1 C2 H2 125.7 . . ?
C4 C3 C2 108.8(3) . . ?
C4 C3 Fe1 70.5(2) . . ?
C2 C3 Fe1 70.0(2) . . ?
C4 C3 H3 125.6 . . ?
C2 C3 H3 125.6 . . ?
Fe1 C3 H3 125.5 . . ?
C3 C4 C5 107.5(3) . . ?
C3 C4 Fe1 69.8(2) . . ?
C5 C4 Fe1 69.4(2) . . ?
C3 C4 H4 126.2 . . ?
C5 C4 H4 126.2 . . ?
Fe1 C4 H4 126.1 . . ?
C1 C5 C4 107.4(3) . . ?
C1 C5 Fe1 69.66(19) . . ?
C4 C5 Fe1 70.0(2) . . ?
C1 C5 H5 126.3 . . ?
C4 C5 H5 126.3 . . ?
Fe1 C5 H5 125.6 . . ?
C7 C6 C10 107.4(3) . . ?
C7 C6 Fe1 69.91(17) . . ?
C10 C6 Fe1 69.42(16) . . ?
C7 C6 H6 126.3 . . ?
C10 C6 H6 126.3 . . ?
Fe1 C6 H6 126.0 . . ?
C8 C7 C6 108.3(3) . . ?
C8 C7 Fe1 69.36(17) . . ?
C6 C7 Fe1 69.54(17) . . ?
C8 C7 H7 125.8 . . ?
C6 C7 H7 125.8 . . ?
Fe1 C7 H7 126.8 . . ?
C7 C8 C9 108.3(3) . . ?
C7 C8 Fe1 70.10(17) . . ?
C9 C8 Fe1 69.36(17) . . ?
C7 C8 H8 125.8 . . ?
C9 C8 H8 125.8 . . ?
Fe1 C8 H8 126.3 . . ?
C8 C9 C10 107.3(3) . . ?
C8 C9 Fe1 69.88(17) . . ?
C10 C9 Fe1 69.75(16) . . ?
C8 C9 H9 126.3 . . ?
C10 C9 H9 126.3 . . ?
Fe1 C9 H9 125.6 . . ?
N11 C10 C6 123.1(3) . . ?
N11 C10 C9 128.4(3) . . ?
C6 C10 C9 108.5(3) . . ?
N11 C10 Fe1 127.0(2) . . ?
C6 C10 Fe1 69.87(16) . . ?
C9 C10 Fe1 69.31(16) . . ?
C12 N11 C10 124.9(3) . . ?
C12 N11 H11 122(3) . . ?
C10 N11 H11 113(3) . . ?
O13 C12 N11 126.5(3) . . ?
O13 C12 C14 122.2(3) . . ?
N11 C12 C14 111.3(3) . . ?
O15 C14 O16 125.6(3) . . ?
O15 C14 C12 122.7(3) . . ?
O16 C14 C12 111.7(3) . . ?
C14 O16 C17 114.9(2) . . ?
O16 C17 C18 108.0(3) . . ?
O16 C17 H17A 110.1 . . ?
C18 C17 H17A 110.1 . . ?
O16 C17 H17B 110.1 . . ?
C18 C17 H17B 110.1 . . ?
H17A C17 H17B 108.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C5 C1 C2 C3 0.2(4) . . . . ?
Fe1 C1 C2 C3 -59.7(2) . . . . ?
C5 C1 C2 Fe1 59.9(2) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
Fe1 C2 C3 C4 -60.1(2) . . . . ?
C1 C2 C3 Fe1 59.7(2) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
Fe1 C3 C4 C5 -59.4(2) . . . . ?
C2 C3 C4 Fe1 59.8(2) . . . . ?
C2 C1 C5 C4 0.0(4) . . . . ?
Fe1 C1 C5 C4 60.1(2) . . . . ?
C2 C1 C5 Fe1 -60.1(2) . . . . ?
C3 C4 C5 C1 -0.2(4) . . . . ?
Fe1 C4 C5 C1 -59.9(2) . . . . ?
C3 C4 C5 Fe1 59.6(2) . . . . ?
C10 C6 C7 C8 -0.8(3) . . . . ?
Fe1 C6 C7 C8 58.7(2) . . . . ?
C10 C6 C7 Fe1 -59.5(2) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
Fe1 C7 C8 C9 59.0(2) . . . . ?
C6 C7 C8 Fe1 -58.8(2) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
Fe1 C8 C9 C10 60.0(2) . . . . ?
C7 C8 C9 Fe1 -59.5(2) . . . . ?
C7 C6 C10 N11 -178.5(3) . . . . ?
Fe1 C6 C10 N11 121.7(3) . . . . ?
C7 C6 C10 C9 1.2(3) . . . . ?
Fe1 C6 C10 C9 -58.7(2) . . . . ?
C7 C6 C10 Fe1 59.8(2) . . . . ?
C8 C9 C10 N11 178.6(3) . . . . ?
Fe1 C9 C10 N11 -121.4(3) . . . . ?
C8 C9 C10 C6 -1.0(3) . . . . ?
Fe1 C9 C10 C6 59.0(2) . . . . ?
C8 C9 C10 Fe1 -60.0(2) . . . . ?
C6 C10 N11 C12 -164.1(3) . . . . ?
C9 C10 N11 C12 16.4(5) . . . . ?
Fe1 C10 N11 C12 -75.4(4) . . . . ?
C10 N11 C12 O13 -1.1(5) . . . . ?
C10 N11 C12 C14 178.1(3) . . . . ?
O13 C12 C14 O15 174.0(3) . . . . ?
N11 C12 C14 O15 -5.2(4) . . . . ?
O13 C12 C14 O16 -5.6(4) . . . . ?
N11 C12 C14 O16 175.2(3) . . . . ?
O15 C14 O16 C17 -2.8(5) . . . . ?
C12 C14 O16 C17 176.8(2) . . . . ?
C14 O16 C17 C18 170.2(3) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

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


####################################################################### 
# 
# 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_MW139pur
_database_code_depnum_ccdc_archive 'CCDC 2017027'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;ISCR
France
;
_audit_update_record             
;
2020-07-17 deposited with the CCDC.	2020-11-02 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of diffraction experiment: 03 juin 2020                                 #
#------------------------------------------------------------------------------#


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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H13 Cl Fe N2 O'
_chemical_formula_sum            'C16 H13 Cl Fe N2 O'
_chemical_formula_weight         340.58
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration rm/ad/rmad/syn/unk/.

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


_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
_space_group_IT_number           33
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
'-x, -y, z+1/2'

_cell_length_a                   13.2083(11)
_cell_length_b                   9.7083(8)
_cell_length_c                   10.6102(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1360.55(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9377
_cell_measurement_theta_min      2.6037
_cell_measurement_theta_max      27.4831
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.0858577
_diffrn_orient_matrix_UB_21      -0.0411974
_diffrn_orient_matrix_UB_31      0.0392584
_diffrn_orient_matrix_UB_12      -0.0275747
_diffrn_orient_matrix_UB_22      -0.0250359
_diffrn_orient_matrix_UB_32      -0.0865781
_diffrn_orient_matrix_UB_13      0.0354809
_diffrn_orient_matrix_UB_23      -0.0664123
_diffrn_orient_matrix_UB_33      0.0079040


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

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             696
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    1.303
_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  0.759
_exptl_absorpt_correction_T_max  0.878

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

#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_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_source_current           1.0
_diffrn_source_voltage           55.0
_diffrn_reflns_av_uneti/neti     0.0197
_diffrn_reflns_av_r_equivalents  0.0334
_diffrn_reflns_number            24782
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.604
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             2980
_reflns_number_gt                2882
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_max     0.903
_reflns_Friedel_fraction_full    0.916

_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 APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2016)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'

#------------------------------------------------------------------------------#
#                            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)+(0.0495P)²+0.6072P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2980
_refine_ls_number_parameters     193
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0236
_refine_ls_wR_factor_ref         0.0649
_refine_ls_wR_factor_gt          0.0633
_refine_ls_goodness_of_fit_ref   0.904
_refine_ls_restrained_S_all      0.904
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
Flack x determined using 1249 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(9)

#------------------------------------------------------------------------------#
#               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'
Cl Cl 0.1484 0.1585 '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 0.50331(2) 0.88512(3) 0.52782(7) 0.01376(10) Uani 1 1 d . . . . .
C1 C 0.3952(3) 0.9730(3) 0.6394(3) 0.0298(7) Uani 1 1 d . . . . .
H1 H 0.380792 0.948627 0.724274 0.036 Uiso 1 1 calc R U . . .
C2 C 0.4654(3) 1.0739(3) 0.5993(3) 0.0276(7) Uani 1 1 d . . . . .
H2 H 0.506348 1.129159 0.652866 0.033 Uiso 1 1 calc R U . . .
C3 C 0.4645(3) 1.0787(3) 0.4671(4) 0.0288(7) Uani 1 1 d . . . . .
H3 H 0.504474 1.137781 0.415894 0.035 Uiso 1 1 calc R U . . .
C4 C 0.3938(3) 0.9802(4) 0.4234(3) 0.0308(7) Uani 1 1 d . . . . .
H4 H 0.378280 0.961386 0.337736 0.037 Uiso 1 1 calc R U . . .
C5 C 0.34986(18) 0.9144(3) 0.5300(5) 0.0311(6) Uani 1 1 d . . . . .
H5 H 0.299652 0.844316 0.528471 0.037 Uiso 1 1 calc R U . . .
C6 C 0.5687(2) 0.7364(3) 0.4161(3) 0.0178(5) Uani 1 1 d . . . . .
H6 H 0.550062 0.714205 0.332028 0.021 Uiso 1 1 calc R U . . .
C7 C 0.6417(2) 0.8371(3) 0.4544(3) 0.0182(5) Uani 1 1 d . . . . .
H7 H 0.680801 0.893121 0.399497 0.022 Uiso 1 1 calc R U . . .
C8 C 0.6458(2) 0.8391(3) 0.5886(3) 0.0188(5) Uani 1 1 d . . . . .
H8 H 0.687976 0.896493 0.638630 0.023 Uiso 1 1 calc R U . . .
C9 C 0.5754(2) 0.7395(3) 0.6345(3) 0.0171(5) Uani 1 1 d . . . . .
H9 H 0.561880 0.719473 0.720548 0.021 Uiso 1 1 calc R U . . .
C10 C 0.52895(16) 0.6755(2) 0.5288(3) 0.0153(4) Uani 1 1 d . . . . .
N11 N 0.45798(15) 0.5686(2) 0.5411(2) 0.0169(4) Uani 1 1 d . . . . .
H11 H 0.445(3) 0.533(4) 0.617(3) 0.020 Uiso 1 1 d . U . . .
C12 C 0.4019(2) 0.5108(3) 0.4481(3) 0.0163(5) Uani 1 1 d . . . . .
O13 O 0.40704(16) 0.5409(2) 0.33632(18) 0.0260(4) Uani 1 1 d . . . . .
C14 C 0.32950(18) 0.4018(2) 0.4962(2) 0.0146(5) Uani 1 1 d . . . . .
N15 N 0.32341(18) 0.3859(2) 0.6215(2) 0.0179(5) Uani 1 1 d . . . . .
C16 C 0.2586(2) 0.2914(3) 0.6641(3) 0.0207(5) Uani 1 1 d . . . . .
H16 H 0.252376 0.280563 0.752761 0.025 Uiso 1 1 calc R U . . .
C17 C 0.1999(2) 0.2078(3) 0.5874(3) 0.0203(5) Uani 1 1 d . . . . .
H17 H 0.154959 0.141252 0.621890 0.024 Uiso 1 1 calc R U . . .
C18 C 0.2094(2) 0.2254(3) 0.4587(3) 0.0176(5) Uani 1 1 d . . . . .
C19 C 0.2739(2) 0.3255(3) 0.4105(2) 0.0163(5) Uani 1 1 d . . . . .
H19 H 0.279574 0.340920 0.322315 0.020 Uiso 1 1 calc R U . . .
Cl1 Cl 0.14241(5) 0.12072(7) 0.35704(8) 0.02793(17) 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 C8 2.039(3) . ?
Fe1 C7 2.041(3) . ?
Fe1 C1 2.042(3) . ?
Fe1 C4 2.043(3) . ?
Fe1 C2 2.046(3) . ?
Fe1 C9 2.046(3) . ?
Fe1 C5 2.047(2) . ?
Fe1 C3 2.052(3) . ?
Fe1 C6 2.058(3) . ?
Fe1 C10 2.063(2) . ?
C1 C2 1.415(5) . ?
C1 C5 1.425(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.403(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.415(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.423(6) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.432(4) . ?
C6 C10 1.433(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.425(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.428(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.421(4) . ?
C9 H9 0.9500 . ?
C10 N11 1.405(3) . ?
N11 C12 1.355(3) . ?
N11 H11 0.89(4) . ?
C12 O13 1.223(3) . ?
C12 C14 1.516(3) . ?
C14 N15 1.341(4) . ?
C14 C19 1.384(4) . ?
N15 C16 1.334(4) . ?
C16 C17 1.387(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.382(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.390(4) . ?
C18 Cl1 1.726(3) . ?
C19 H19 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
C8 Fe1 C7 40.89(10) . . ?
C8 Fe1 C1 123.62(14) . . ?
C7 Fe1 C1 160.61(13) . . ?
C8 Fe1 C4 157.56(14) . . ?
C7 Fe1 C4 122.05(14) . . ?
C1 Fe1 C4 68.30(11) . . ?
C8 Fe1 C2 107.74(13) . . ?
C7 Fe1 C2 124.43(13) . . ?
C1 Fe1 C2 40.51(14) . . ?
C4 Fe1 C2 67.84(13) . . ?
C8 Fe1 C9 40.91(11) . . ?
C7 Fe1 C9 68.70(11) . . ?
C1 Fe1 C9 107.04(13) . . ?
C4 Fe1 C9 160.36(13) . . ?
C2 Fe1 C9 121.85(13) . . ?
C8 Fe1 C5 160.20(16) . . ?
C7 Fe1 C5 157.34(16) . . ?
C1 Fe1 C5 40.79(17) . . ?
C4 Fe1 C5 40.72(17) . . ?
C2 Fe1 C5 68.25(13) . . ?
C9 Fe1 C5 123.38(14) . . ?
C8 Fe1 C3 122.03(13) . . ?
C7 Fe1 C3 108.25(13) . . ?
C1 Fe1 C3 67.96(14) . . ?
C4 Fe1 C3 40.43(14) . . ?
C2 Fe1 C3 40.06(12) . . ?
C9 Fe1 C3 157.34(13) . . ?
C5 Fe1 C3 68.24(14) . . ?
C8 Fe1 C6 68.98(12) . . ?
C7 Fe1 C6 40.89(11) . . ?
C1 Fe1 C6 157.00(13) . . ?
C4 Fe1 C6 107.58(13) . . ?
C2 Fe1 C6 160.86(13) . . ?
C9 Fe1 C6 68.83(9) . . ?
C5 Fe1 C6 121.28(13) . . ?
C3 Fe1 C6 124.52(14) . . ?
C8 Fe1 C10 68.32(10) . . ?
C7 Fe1 C10 68.24(10) . . ?
C1 Fe1 C10 121.61(12) . . ?
C4 Fe1 C10 124.40(13) . . ?
C2 Fe1 C10 157.24(13) . . ?
C9 Fe1 C10 40.47(11) . . ?
C5 Fe1 C10 107.42(10) . . ?
C3 Fe1 C10 161.11(14) . . ?
C6 Fe1 C10 40.70(11) . . ?
C2 C1 C5 107.9(3) . . ?
C2 C1 Fe1 69.89(18) . . ?
C5 C1 Fe1 69.78(17) . . ?
C2 C1 H1 126.1 . . ?
C5 C1 H1 126.1 . . ?
Fe1 C1 H1 125.8 . . ?
C3 C2 C1 108.5(3) . . ?
C3 C2 Fe1 70.20(19) . . ?
C1 C2 Fe1 69.60(17) . . ?
C3 C2 H2 125.7 . . ?
C1 C2 H2 125.7 . . ?
Fe1 C2 H2 126.1 . . ?
C2 C3 C4 108.1(3) . . ?
C2 C3 Fe1 69.7(2) . . ?
C4 C3 Fe1 69.44(18) . . ?
C2 C3 H3 126.0 . . ?
C4 C3 H3 126.0 . . ?
Fe1 C3 H3 126.4 . . ?
C3 C4 C5 108.2(3) . . ?
C3 C4 Fe1 70.13(18) . . ?
C5 C4 Fe1 69.80(17) . . ?
C3 C4 H4 125.9 . . ?
C5 C4 H4 125.9 . . ?
Fe1 C4 H4 125.8 . . ?
C4 C5 C1 107.3(2) . . ?
C4 C5 Fe1 69.49(17) . . ?
C1 C5 Fe1 69.42(17) . . ?
C4 C5 H5 126.4 . . ?
C1 C5 H5 126.4 . . ?
Fe1 C5 H5 126.3 . . ?
C7 C6 C10 106.9(2) . . ?
C7 C6 Fe1 68.92(16) . . ?
C10 C6 Fe1 69.84(14) . . ?
C7 C6 H6 126.5 . . ?
C10 C6 H6 126.5 . . ?
Fe1 C6 H6 126.3 . . ?
C8 C7 C6 108.6(3) . . ?
C8 C7 Fe1 69.50(18) . . ?
C6 C7 Fe1 70.19(16) . . ?
C8 C7 H7 125.7 . . ?
C6 C7 H7 125.7 . . ?
Fe1 C7 H7 126.2 . . ?
C7 C8 C9 107.9(3) . . ?
C7 C8 Fe1 69.60(19) . . ?
C9 C8 Fe1 69.80(15) . . ?
C7 C8 H8 126.1 . . ?
C9 C8 H8 126.1 . . ?
Fe1 C8 H8 126.1 . . ?
C10 C9 C8 107.9(2) . . ?
C10 C9 Fe1 70.39(14) . . ?
C8 C9 Fe1 69.29(16) . . ?
C10 C9 H9 126.0 . . ?
C8 C9 H9 126.0 . . ?
Fe1 C9 H9 125.8 . . ?
N11 C10 C9 122.5(3) . . ?
N11 C10 C6 128.8(3) . . ?
C9 C10 C6 108.70(19) . . ?
N11 C10 Fe1 128.31(16) . . ?
C9 C10 Fe1 69.14(14) . . ?
C6 C10 Fe1 69.46(14) . . ?
C12 N11 C10 127.1(2) . . ?
C12 N11 H11 113(2) . . ?
C10 N11 H11 120(2) . . ?
O13 C12 N11 125.3(2) . . ?
O13 C12 C14 121.9(2) . . ?
N11 C12 C14 112.9(2) . . ?
N15 C14 C19 124.0(2) . . ?
N15 C14 C12 116.9(2) . . ?
C19 C14 C12 119.2(2) . . ?
C16 N15 C14 117.0(2) . . ?
N15 C16 C17 124.3(3) . . ?
N15 C16 H16 117.9 . . ?
C17 C16 H16 117.9 . . ?
C18 C17 C16 117.1(3) . . ?
C18 C17 H17 121.4 . . ?
C16 C17 H17 121.4 . . ?
C17 C18 C19 120.4(3) . . ?
C17 C18 Cl1 119.8(2) . . ?
C19 C18 Cl1 119.7(2) . . ?
C14 C19 C18 117.2(2) . . ?
C14 C19 H19 121.4 . . ?
C18 C19 H19 121.4 . . ?

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(4) . . . . ?
Fe1 C1 C2 C3 59.6(3) . . . . ?
C5 C1 C2 Fe1 -59.7(2) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
Fe1 C2 C3 C4 59.0(2) . . . . ?
C1 C2 C3 Fe1 -59.2(2) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
Fe1 C3 C4 C5 59.6(2) . . . . ?
C2 C3 C4 Fe1 -59.2(3) . . . . ?
C3 C4 C5 C1 -0.4(3) . . . . ?
Fe1 C4 C5 C1 59.39(18) . . . . ?
C3 C4 C5 Fe1 -59.8(2) . . . . ?
C2 C1 C5 C4 0.3(3) . . . . ?
Fe1 C1 C5 C4 -59.43(18) . . . . ?
C2 C1 C5 Fe1 59.8(2) . . . . ?
C10 C6 C7 C8 -0.7(3) . . . . ?
Fe1 C6 C7 C8 59.1(2) . . . . ?
C10 C6 C7 Fe1 -59.77(17) . . . . ?
C6 C7 C8 C9 0.0(4) . . . . ?
Fe1 C7 C8 C9 59.55(19) . . . . ?
C6 C7 C8 Fe1 -59.5(2) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
Fe1 C8 C9 C10 60.05(17) . . . . ?
C7 C8 C9 Fe1 -59.4(2) . . . . ?
C8 C9 C10 N11 177.7(2) . . . . ?
Fe1 C9 C10 N11 -122.9(2) . . . . ?
C8 C9 C10 C6 -1.1(3) . . . . ?
Fe1 C9 C10 C6 58.30(15) . . . . ?
C8 C9 C10 Fe1 -59.36(18) . . . . ?
C7 C6 C10 N11 -177.6(2) . . . . ?
Fe1 C6 C10 N11 123.2(2) . . . . ?
C7 C6 C10 C9 1.1(3) . . . . ?
Fe1 C6 C10 C9 -58.11(15) . . . . ?
C7 C6 C10 Fe1 59.18(18) . . . . ?
C9 C10 N11 C12 172.6(2) . . . . ?
C6 C10 N11 C12 -8.9(4) . . . . ?
Fe1 C10 N11 C12 84.6(3) . . . . ?
C10 N11 C12 O13 2.4(4) . . . . ?
C10 N11 C12 C14 -177.5(2) . . . . ?
O13 C12 C14 N15 -174.0(2) . . . . ?
N11 C12 C14 N15 5.9(3) . . . . ?
O13 C12 C14 C19 5.7(4) . . . . ?
N11 C12 C14 C19 -174.3(2) . . . . ?
C19 C14 N15 C16 -0.7(4) . . . . ?
C12 C14 N15 C16 179.1(2) . . . . ?
C14 N15 C16 C17 1.4(4) . . . . ?
N15 C16 C17 C18 -0.4(4) . . . . ?
C16 C17 C18 C19 -1.4(4) . . . . ?
C16 C17 C18 Cl1 177.51(19) . . . . ?
N15 C14 C19 C18 -1.1(4) . . . . ?
C12 C14 C19 C18 179.2(2) . . . . ?
C17 C18 C19 C14 2.1(4) . . . . ?
Cl1 C18 C19 C14 -176.83(19) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

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


####################################################################### 
# 
# 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_MW1426
_database_code_depnum_ccdc_archive 'CCDC 2017028'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;ISCR
France
;
_audit_update_record             
;
2020-07-17 deposited with the CCDC.	2020-11-02 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of diffraction experiment: 08 juin 2020                                 #
#------------------------------------------------------------------------------#


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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H18 F Fe N3 O2'
_chemical_formula_sum            'C22 H18 F Fe N3 O2'
_chemical_formula_weight         431.24
_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                   11.2927(11)
_cell_length_b                   13.7746(14)
_cell_length_c                   14.1675(15)
_cell_angle_alpha                65.688(3)
_cell_angle_beta                 68.371(4)
_cell_angle_gamma                88.915(4)
_cell_volume                     1843.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9948
_cell_measurement_theta_min      2.8782
_cell_measurement_theta_max      27.5688
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.0485586
_diffrn_orient_matrix_UB_21      0.0496067
_diffrn_orient_matrix_UB_31      -0.0669657
_diffrn_orient_matrix_UB_12      0.0593674
_diffrn_orient_matrix_UB_22      0.0103208
_diffrn_orient_matrix_UB_32      -0.0536185
_diffrn_orient_matrix_UB_13      -0.0275822
_diffrn_orient_matrix_UB_23      -0.0791444
_diffrn_orient_matrix_UB_33      0.0094796


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

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             888
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.852
_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  0.786
_exptl_absorpt_correction_T_max  0.895

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

# Software                   : BIS V6.2.1/2016-03-01                           #
# Number of scans            :        3                                        #
# Total number of frames [*] :      456                                        #
# Total length of scans  [*] :   456.00 (deg.)                                 #
# Rotation speed         [*] :     8.00 sec./deg.                              #
# Total exposition time  [*] :      1 h   0.8 min.                             #
#                                                                              #
#  [*] fast scan not included                                                  #
#                                                                              #
# Measurement mode           : shutterless mode                                #
#                                                                              #
#    Scan  Time(s)  Width  DX (mm)  Frames  Theta  Omega    Phi    Chi   T(K)  #
#..............................................................................#
#                                                                              #
#  1 Phi       8.0   1.00     34.0     360   0.27 270.94 360.00  23.00 150.00  #
#  2 Omega     8.0   1.00     34.0      96   0.27   3.16 144.00 315.50 150.00  #
#  3 Fast      1.0   1.00     34.0     180   0.00 360.00   0.00  54.74 150.01  #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_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_source_current           1.0
_diffrn_source_voltage           55.0
_diffrn_reflns_av_uneti/neti     0.0403
_diffrn_reflns_av_r_equivalents  0.0500
_diffrn_reflns_number            34410
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.355
_diffrn_reflns_theta_max         27.558
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.982
_reflns_number_total             8364
_reflns_number_gt                6413
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

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

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2016)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2020)'

#------------------------------------------------------------------------------#
#                            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)+(0.0315P)²+3.4463P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8364
_refine_ls_number_parameters     526
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1115
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.184
_refine_diff_density_min         -0.920
_refine_diff_density_rms         0.075

#------------------------------------------------------------------------------#
#               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'
F F 0.0171 0.0103 '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 0.25059(4) 0.36421(3) 0.11578(3) 0.02296(10) Uani 1 1 d . . . . .
C1 C 0.2672(3) 0.2299(3) 0.2413(3) 0.0402(4) Uani 1 1 d . . . . .
H1 H 0.299291 0.168093 0.233912 0.048 Uiso 1 1 calc R U . . .
C2 C 0.1376(3) 0.2465(3) 0.2717(3) 0.0402(4) Uani 1 1 d . . . . .
H2 H 0.066438 0.197451 0.288737 0.048 Uiso 1 1 calc R U . . .
C3 C 0.1319(3) 0.3494(3) 0.2723(3) 0.0402(4) Uani 1 1 d . . . . .
H3 H 0.056085 0.380943 0.290147 0.048 Uiso 1 1 calc R U . . .
C4 C 0.2579(3) 0.3965(3) 0.2417(3) 0.0402(4) Uani 1 1 d . . . . .
H4 H 0.282102 0.465611 0.234602 0.048 Uiso 1 1 calc R U . . .
C5 C 0.3415(3) 0.3233(3) 0.2237(3) 0.0402(4) Uani 1 1 d . . . . .
H5 H 0.431958 0.333956 0.203285 0.048 Uiso 1 1 calc R U . . .
C6 C 0.1776(3) 0.3605(2) 0.0042(2) 0.0268(6) Uani 1 1 d . . . . .
H6 H 0.104670 0.312912 0.021873 0.032 Uiso 1 1 calc R U . . .
C7 C 0.1768(3) 0.4632(2) 0.0054(2) 0.0305(6) Uani 1 1 d . . . . .
H7 H 0.102560 0.496432 0.023665 0.037 Uiso 1 1 calc R U . . .
C8 C 0.3047(3) 0.5079(2) -0.0249(2) 0.0310(6) Uani 1 1 d . . . . .
H8 H 0.330991 0.575777 -0.030368 0.037 Uiso 1 1 calc R U . . .
C9 C 0.3870(3) 0.4324(2) -0.0456(2) 0.0280(6) Uani 1 1 d . . . . .
H9 H 0.477761 0.440819 -0.066923 0.034 Uiso 1 1 calc R U . . .
C10 C 0.3080(3) 0.3423(2) -0.0286(2) 0.0245(6) Uani 1 1 d . . . . .
N11 N 0.3568(2) 0.25538(19) -0.0503(2) 0.0273(5) Uani 1 1 d . . . . .
H11 H 0.426(3) 0.266(3) -0.102(3) 0.033 Uiso 1 1 d . U . . .
C12 C 0.2961(3) 0.1534(2) 0.0003(2) 0.0254(6) Uani 1 1 d . . . . .
O13 O 0.1907(2) 0.11998(17) 0.07941(19) 0.0391(5) Uani 1 1 d . . . . .
C14 C 0.3687(2) 0.0820(2) -0.0509(2) 0.0224(5) Uani 1 1 d . . . . .
N15 N 0.4797(2) 0.13021(19) -0.14100(18) 0.0265(5) Uani 1 1 d . . . . .
C16 C 0.5417(3) 0.0691(2) -0.1900(2) 0.0294(6) Uani 1 1 d . . . . .
H16 H 0.619971 0.101804 -0.254673 0.035 Uiso 1 1 calc R U . . .
C17 C 0.4994(3) -0.0378(2) -0.1528(2) 0.0286(6) Uani 1 1 d . . . . .
H17 H 0.546511 -0.077389 -0.191552 0.034 Uiso 1 1 calc R U . . .
C18 C 0.3860(3) -0.0870(2) -0.0571(2) 0.0258(6) Uani 1 1 d . . . . .
C19 C 0.3176(3) -0.0257(2) -0.0054(2) 0.0242(6) Uani 1 1 d . . . . .
H19 H 0.238543 -0.056221 0.058795 0.029 Uiso 1 1 calc R U . . .
O20 O 0.3515(2) -0.19458(16) -0.02181(17) 0.0341(5) Uani 1 1 d . . . . .
C21 C 0.2439(3) -0.2529(2) 0.0788(2) 0.0266(6) Uani 1 1 d . . . . .
C22 C 0.1421(3) -0.3001(2) 0.0724(3) 0.0311(6) Uani 1 1 d . . . . .
H22 H 0.141773 -0.286872 0.001198 0.037 Uiso 1 1 calc R U . . .
C23 C 0.0403(3) -0.3669(2) 0.1711(3) 0.0321(7) Uani 1 1 d . . . . .
H23 H -0.029510 -0.399549 0.166639 0.038 Uiso 1 1 calc R U . . .
C24 C 0.0377(3) -0.3874(2) 0.2766(2) 0.0266(6) Uani 1 1 d . . . . .
C25 C 0.1407(3) -0.3348(2) 0.2769(2) 0.0270(6) Uani 1 1 d . . . . .
C26 C 0.2451(3) -0.2700(2) 0.1817(2) 0.0278(6) Uani 1 1 d . . . . .
H26 H 0.315485 -0.238062 0.186197 0.033 Uiso 1 1 calc R U . . .
N27 N -0.0630(3) -0.4540(2) 0.3764(2) 0.0399(7) Uani 1 1 d . . . . .
H27A H -0.112(4) -0.504(3) 0.373(3) 0.048 Uiso 1 1 d . U . . .
H27B H -0.057(4) -0.467(3) 0.440(3) 0.048 Uiso 1 1 d . U . . .
F28 F 0.13940(17) -0.35208(16) 0.37963(14) 0.0399(4) Uani 1 1 d . . . . .
Fe2 Fe 0.25458(3) 0.86936(3) 0.62253(3) 0.01771(10) Uani 1 1 d . . . . .
C51 C 0.1723(3) 0.9620(3) 0.5150(2) 0.0357(7) Uani 1 1 d . . . . .
H51 H 0.094443 0.990525 0.534704 0.043 Uiso 1 1 calc R U . . .
C52 C 0.2979(3) 1.0139(2) 0.4824(2) 0.0322(7) Uani 1 1 d . . . . .
H52 H 0.318830 1.083004 0.476874 0.039 Uiso 1 1 calc R U . . .
C53 C 0.3867(3) 0.9436(2) 0.4594(2) 0.0279(6) Uani 1 1 d . . . . .
H53 H 0.477557 0.957840 0.435355 0.033 Uiso 1 1 calc R U . . .
C54 C 0.3157(3) 0.8490(2) 0.4787(2) 0.0288(6) Uani 1 1 d . . . . .
H54 H 0.350711 0.788508 0.469985 0.035 Uiso 1 1 calc R U . . .
C55 C 0.1837(3) 0.8600(3) 0.5130(2) 0.0344(7) Uani 1 1 d . . . . .
H55 H 0.114675 0.808170 0.531549 0.041 Uiso 1 1 calc R U . . .
C56 C 0.3566(3) 0.8303(2) 0.7226(2) 0.0211(5) Uani 1 1 d . . . . .
H56 H 0.447347 0.847418 0.697392 0.025 Uiso 1 1 calc R U . . .
C57 C 0.2631(3) 0.8949(2) 0.7527(2) 0.0246(6) Uani 1 1 d . . . . .
H57 H 0.280688 0.962818 0.751187 0.029 Uiso 1 1 calc R U . . .
C58 C 0.1389(3) 0.8402(2) 0.7853(2) 0.0241(6) Uani 1 1 d . . . . .
H58 H 0.059260 0.865040 0.809503 0.029 Uiso 1 1 calc R U . . .
C59 C 0.1550(2) 0.7415(2) 0.7752(2) 0.0209(5) Uani 1 1 d . . . . .
H59 H 0.088142 0.689235 0.790832 0.025 Uiso 1 1 calc R U . . .
C60 C 0.2893(2) 0.7355(2) 0.7374(2) 0.0188(5) Uani 1 1 d . . . . .
N61 N 0.3521(2) 0.65339(17) 0.71525(19) 0.0204(4) Uani 1 1 d . . . . .
H61 H 0.427(3) 0.654(2) 0.707(3) 0.024 Uiso 1 1 d . U . . .
C62 C 0.3036(3) 0.5773(2) 0.6980(2) 0.0230(5) Uani 1 1 d . . . . .
O63 O 0.19403(19) 0.56833(17) 0.7007(2) 0.0369(5) Uani 1 1 d . . . . .
C64 C 0.3964(2) 0.5023(2) 0.6731(2) 0.0204(5) Uani 1 1 d . . . . .
N65 N 0.5163(2) 0.52795(18) 0.66026(19) 0.0229(5) Uani 1 1 d . . . . .
C66 C 0.6002(3) 0.4637(2) 0.6349(2) 0.0268(6) Uani 1 1 d . . . . .
H66 H 0.686585 0.480871 0.624400 0.032 Uiso 1 1 calc R U . . .
C67 C 0.5693(3) 0.3745(2) 0.6230(3) 0.0290(6) Uani 1 1 d . . . . .
H67 H 0.632290 0.330852 0.605819 0.035 Uiso 1 1 calc R U . . .
C68 C 0.4434(3) 0.3498(2) 0.6369(3) 0.0274(6) Uani 1 1 d . . . . .
C69 C 0.3540(3) 0.4146(2) 0.6632(2) 0.0252(6) Uani 1 1 d . . . . .
H69 H 0.267057 0.399536 0.673924 0.030 Uiso 1 1 calc R U . . .
O70 O 0.4182(2) 0.26230(18) 0.6214(2) 0.0431(6) Uani 1 1 d . . . . .
C71 C 0.2898(3) 0.2255(2) 0.6459(3) 0.0341(7) Uani 1 1 d . . . . .
C72 C 0.2518(3) 0.2484(2) 0.5585(3) 0.0354(7) Uani 1 1 d . . . . .
H72 H 0.307588 0.294637 0.483040 0.042 Uiso 1 1 calc R U . A 1
C73A C 0.1295(3) 0.2020(2) 0.5835(3) 0.0350(7) Uani 0.5 1 d . . P B 1
F77 F 0.0862(4) 0.2200(4) 0.5090(3) 0.0511(11) Uani 0.5 1 d . . P B 1
C73B C 0.1295(3) 0.2020(2) 0.5835(3) 0.0350(7) Uani 0.5 1 d . . P B 2
H73B H 0.102633 0.217877 0.523265 0.042 Uiso 0.5 1 calc R U P B 2
C74 C 0.0447(3) 0.1337(2) 0.6917(3) 0.0293(6) Uani 1 1 d . . . . .
C75A C 0.0872(3) 0.1165(3) 0.7767(3) 0.0376(7) Uani 0.5 1 d . . P B 1
H75A H 0.031018 0.072136 0.852529 0.045 Uiso 0.5 1 calc R U P B 1
C75B C 0.0872(3) 0.1165(3) 0.7767(3) 0.0376(7) Uani 0.5 1 d . . P B 2
F79 F 0.0151(4) 0.0594(3) 0.8737(3) 0.0496(11) Uani 0.5 1 d . . P B 2
C76 C 0.2084(3) 0.1614(3) 0.7554(3) 0.0407(8) Uani 1 1 d . . . . .
H76 H 0.234643 0.147950 0.815494 0.049 Uiso 1 1 calc R U . B 1
N78 N -0.0769(3) 0.0881(2) 0.7145(2) 0.0330(6) Uani 1 1 d . . . . .
H78A H -0.093(3) 0.091(3) 0.657(3) 0.040 Uiso 1 1 d . U . . .
H78B H -0.108(3) 0.032(3) 0.775(3) 0.040 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 2.033(3) . ?
Fe1 C1 2.035(3) . ?
Fe1 C4 2.037(3) . ?
Fe1 C7 2.039(3) . ?
Fe1 C8 2.040(3) . ?
Fe1 C9 2.043(3) . ?
Fe1 C2 2.046(3) . ?
Fe1 C3 2.049(3) . ?
Fe1 C6 2.053(3) . ?
Fe1 C10 2.054(3) . ?
C1 C2 1.408(5) . ?
C1 C5 1.429(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.421(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.409(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.404(5) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.422(4) . ?
C6 C10 1.423(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.417(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.430(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.425(4) . ?
C9 H9 0.9500 . ?
C10 N11 1.410(4) . ?
N11 C12 1.342(4) . ?
N11 H11 0.81(3) . ?
C12 O13 1.224(3) . ?
C12 C14 1.511(4) . ?
C14 N15 1.341(3) . ?
C14 C19 1.385(4) . ?
N15 C16 1.334(4) . ?
C16 C17 1.370(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(4) . ?
C17 H17 0.9500 . ?
C18 O20 1.366(3) . ?
C18 C19 1.384(4) . ?
C19 H19 0.9500 . ?
O20 C21 1.404(3) . ?
C21 C22 1.380(4) . ?
C21 C26 1.383(4) . ?
C22 C23 1.385(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.391(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.385(4) . ?
C24 N27 1.386(4) . ?
C25 F28 1.368(3) . ?
C25 C26 1.372(4) . ?
C26 H26 0.9500 . ?
N27 H27A 0.92(4) . ?
N27 H27B 0.87(4) . ?
Fe2 C54 2.034(3) . ?
Fe2 C55 2.037(3) . ?
Fe2 C60 2.043(2) . ?
Fe2 C56 2.045(3) . ?
Fe2 C53 2.045(3) . ?
Fe2 C59 2.047(3) . ?
Fe2 C57 2.049(3) . ?
Fe2 C51 2.052(3) . ?
Fe2 C52 2.052(3) . ?
Fe2 C58 2.054(3) . ?
C51 C55 1.419(5) . ?
C51 C52 1.420(4) . ?
C51 H51 0.9500 . ?
C52 C53 1.425(4) . ?
C52 H52 0.9500 . ?
C53 C54 1.414(4) . ?
C53 H53 0.9500 . ?
C54 C55 1.414(4) . ?
C54 H54 0.9500 . ?
C55 H55 0.9500 . ?
C56 C60 1.422(3) . ?
C56 C57 1.426(4) . ?
C56 H56 0.9500 . ?
C57 C58 1.423(4) . ?
C57 H57 0.9500 . ?
C58 C59 1.425(4) . ?
C58 H58 0.9500 . ?
C59 C60 1.425(4) . ?
C59 H59 0.9500 . ?
C60 N61 1.406(3) . ?
N61 C62 1.338(3) . ?
N61 H61 0.82(3) . ?
C62 O63 1.230(3) . ?
C62 C64 1.509(4) . ?
C64 N65 1.332(3) . ?
C64 C69 1.386(4) . ?
N65 C66 1.337(3) . ?
C66 C67 1.376(4) . ?
C66 H66 0.9500 . ?
C67 C68 1.390(4) . ?
C67 H67 0.9500 . ?
C68 O70 1.364(3) . ?
C68 C69 1.384(4) . ?
C69 H69 0.9500 . ?
O70 C71 1.412(3) . ?
C71 C76 1.372(5) . ?
C71 C72 1.372(4) . ?
C72 C73B 1.389(4) . ?
C72 C73A 1.389(4) . ?
C72 H72 0.9500 . ?
C73A F77 1.255(4) . ?
C73A C74 1.384(4) . ?
C73B C74 1.384(4) . ?
C73B H73B 0.9500 . ?
C74 C75B 1.387(4) . ?
C74 C75A 1.387(4) . ?
C74 N78 1.387(4) . ?
C75A C76 1.385(5) . ?
C75A H75A 0.9500 . ?
C75B F79 1.216(5) . ?
C75B C76 1.385(5) . ?
C76 H76 0.9500 . ?
N78 H78A 0.89(4) . ?
N78 H78B 0.83(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
C5 Fe1 C1 41.12(13) . . ?
C5 Fe1 C4 40.35(14) . . ?
C1 Fe1 C4 68.65(14) . . ?
C5 Fe1 C7 157.07(13) . . ?
C1 Fe1 C7 159.54(13) . . ?
C4 Fe1 C7 120.96(13) . . ?
C5 Fe1 C8 122.12(13) . . ?
C1 Fe1 C8 158.95(13) . . ?
C4 Fe1 C8 106.60(13) . . ?
C7 Fe1 C8 40.65(12) . . ?
C5 Fe1 C9 108.50(13) . . ?
C1 Fe1 C9 123.35(13) . . ?
C4 Fe1 C9 123.64(12) . . ?
C7 Fe1 C9 68.55(12) . . ?
C8 Fe1 C9 41.00(12) . . ?
C5 Fe1 C2 68.19(13) . . ?
C1 Fe1 C2 40.36(13) . . ?
C4 Fe1 C2 68.30(14) . . ?
C7 Fe1 C2 122.89(13) . . ?
C8 Fe1 C2 158.78(13) . . ?
C9 Fe1 C2 158.85(13) . . ?
C5 Fe1 C3 67.74(14) . . ?
C1 Fe1 C3 68.15(14) . . ?
C4 Fe1 C3 40.32(13) . . ?
C7 Fe1 C3 106.55(13) . . ?
C8 Fe1 C3 122.33(13) . . ?
C9 Fe1 C3 159.35(13) . . ?
C2 Fe1 C3 40.59(14) . . ?
C5 Fe1 C6 161.41(13) . . ?
C1 Fe1 C6 123.84(13) . . ?
C4 Fe1 C6 156.57(13) . . ?
C7 Fe1 C6 40.67(11) . . ?
C8 Fe1 C6 68.76(12) . . ?
C9 Fe1 C6 68.82(11) . . ?
C2 Fe1 C6 107.28(12) . . ?
C3 Fe1 C6 121.38(12) . . ?
C5 Fe1 C10 125.57(13) . . ?
C1 Fe1 C10 109.02(13) . . ?
C4 Fe1 C10 161.03(12) . . ?
C7 Fe1 C10 68.00(11) . . ?
C8 Fe1 C10 68.43(11) . . ?
C9 Fe1 C10 40.72(11) . . ?
C2 Fe1 C10 122.96(13) . . ?
C3 Fe1 C10 157.87(12) . . ?
C6 Fe1 C10 40.55(11) . . ?
C2 C1 C5 107.4(3) . . ?
C2 C1 Fe1 70.25(19) . . ?
C5 C1 Fe1 69.36(19) . . ?
C2 C1 H1 126.3 . . ?
C5 C1 H1 126.3 . . ?
Fe1 C1 H1 125.7 . . ?
C1 C2 C3 108.0(3) . . ?
C1 C2 Fe1 69.39(19) . . ?
C3 C2 Fe1 69.82(19) . . ?
C1 C2 H2 126.0 . . ?
C3 C2 H2 126.0 . . ?
Fe1 C2 H2 126.4 . . ?
C4 C3 C2 108.2(3) . . ?
C4 C3 Fe1 69.38(19) . . ?
C2 C3 Fe1 69.59(19) . . ?
C4 C3 H3 125.9 . . ?
C2 C3 H3 125.9 . . ?
Fe1 C3 H3 126.7 . . ?
C5 C4 C3 108.0(3) . . ?
C5 C4 Fe1 69.66(19) . . ?
C3 C4 Fe1 70.29(19) . . ?
C5 C4 H4 126.0 . . ?
C3 C4 H4 126.0 . . ?
Fe1 C4 H4 125.6 . . ?
C4 C5 C1 108.3(3) . . ?
C4 C5 Fe1 69.99(19) . . ?
C1 C5 Fe1 69.52(19) . . ?
C4 C5 H5 125.8 . . ?
C1 C5 H5 125.8 . . ?
Fe1 C5 H5 126.2 . . ?
C7 C6 C10 107.1(2) . . ?
C7 C6 Fe1 69.17(16) . . ?
C10 C6 Fe1 69.77(15) . . ?
C7 C6 H6 126.4 . . ?
C10 C6 H6 126.4 . . ?
Fe1 C6 H6 126.2 . . ?
C8 C7 C6 109.0(3) . . ?
C8 C7 Fe1 69.69(16) . . ?
C6 C7 Fe1 70.17(16) . . ?
C8 C7 H7 125.5 . . ?
C6 C7 H7 125.5 . . ?
Fe1 C7 H7 126.2 . . ?
C7 C8 C9 107.7(3) . . ?
C7 C8 Fe1 69.65(16) . . ?
C9 C8 Fe1 69.62(16) . . ?
C7 C8 H8 126.1 . . ?
C9 C8 H8 126.1 . . ?
Fe1 C8 H8 126.2 . . ?
C10 C9 C8 107.5(2) . . ?
C10 C9 Fe1 70.04(15) . . ?
C8 C9 Fe1 69.37(16) . . ?
C10 C9 H9 126.3 . . ?
C8 C9 H9 126.3 . . ?
Fe1 C9 H9 125.9 . . ?
N11 C10 C6 127.4(2) . . ?
N11 C10 C9 123.7(3) . . ?
C6 C10 C9 108.7(2) . . ?
N11 C10 Fe1 130.70(19) . . ?
C6 C10 Fe1 69.69(15) . . ?
C9 C10 Fe1 69.25(16) . . ?
C12 N11 C10 126.8(2) . . ?
C12 N11 H11 113(2) . . ?
C10 N11 H11 120(2) . . ?
O13 C12 N11 124.2(3) . . ?
O13 C12 C14 122.0(2) . . ?
N11 C12 C14 113.8(2) . . ?
N15 C14 C19 124.4(3) . . ?
N15 C14 C12 115.9(2) . . ?
C19 C14 C12 119.7(2) . . ?
C16 N15 C14 116.4(2) . . ?
N15 C16 C17 124.1(3) . . ?
N15 C16 H16 118.0 . . ?
C17 C16 H16 118.0 . . ?
C16 C17 C18 118.5(3) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
O20 C18 C19 125.2(2) . . ?
O20 C18 C17 115.8(3) . . ?
C19 C18 C17 119.0(3) . . ?
C18 C19 C14 117.5(2) . . ?
C18 C19 H19 121.2 . . ?
C14 C19 H19 121.2 . . ?
C18 O20 C21 119.8(2) . . ?
C22 C21 C26 121.2(3) . . ?
C22 C21 O20 118.0(3) . . ?
C26 C21 O20 120.6(2) . . ?
C21 C22 C23 119.2(3) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C22 C23 C24 121.8(3) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 H23 119.1 . . ?
C25 C24 N27 121.1(3) . . ?
C25 C24 C23 116.1(3) . . ?
N27 C24 C23 122.8(3) . . ?
F28 C25 C26 118.4(2) . . ?
F28 C25 C24 117.3(2) . . ?
C26 C25 C24 124.3(3) . . ?
C25 C26 C21 117.4(3) . . ?
C25 C26 H26 121.3 . . ?
C21 C26 H26 121.3 . . ?
C24 N27 H27A 116(2) . . ?
C24 N27 H27B 119(3) . . ?
H27A N27 H27B 119(3) . . ?
C54 Fe2 C55 40.65(12) . . ?
C54 Fe2 C60 105.01(11) . . ?
C55 Fe2 C60 121.70(12) . . ?
C54 Fe2 C56 121.53(12) . . ?
C55 Fe2 C56 157.82(12) . . ?
C60 Fe2 C56 40.71(10) . . ?
C54 Fe2 C53 40.58(11) . . ?
C55 Fe2 C53 68.32(12) . . ?
C60 Fe2 C53 120.25(11) . . ?
C56 Fe2 C53 106.60(11) . . ?
C54 Fe2 C59 120.05(11) . . ?
C55 Fe2 C59 106.48(11) . . ?
C60 Fe2 C59 40.77(10) . . ?
C56 Fe2 C59 68.79(10) . . ?
C53 Fe2 C59 155.71(11) . . ?
C54 Fe2 C57 159.28(12) . . ?
C55 Fe2 C57 159.53(12) . . ?
C60 Fe2 C57 68.30(10) . . ?
C56 Fe2 C57 40.78(10) . . ?
C53 Fe2 C57 124.48(12) . . ?
C59 Fe2 C57 68.50(11) . . ?
C54 Fe2 C51 68.28(12) . . ?
C55 Fe2 C51 40.61(13) . . ?
C60 Fe2 C51 159.26(12) . . ?
C56 Fe2 C51 159.53(12) . . ?
C53 Fe2 C51 68.22(12) . . ?
C59 Fe2 C51 124.21(12) . . ?
C57 Fe2 C51 124.65(12) . . ?
C54 Fe2 C52 68.39(12) . . ?
C55 Fe2 C52 68.35(13) . . ?
C60 Fe2 C52 157.20(12) . . ?
C56 Fe2 C52 122.77(12) . . ?
C53 Fe2 C52 40.70(12) . . ?
C59 Fe2 C52 161.51(12) . . ?
C57 Fe2 C52 109.75(12) . . ?
C51 Fe2 C52 40.50(13) . . ?
C54 Fe2 C58 157.08(12) . . ?
C55 Fe2 C58 122.85(12) . . ?
C60 Fe2 C58 68.28(10) . . ?
C56 Fe2 C58 68.54(11) . . ?
C53 Fe2 C58 161.79(11) . . ?
C59 Fe2 C58 40.68(10) . . ?
C57 Fe2 C58 40.57(11) . . ?
C51 Fe2 C58 109.83(12) . . ?
C52 Fe2 C58 126.04(12) . . ?
C55 C51 C52 108.0(3) . . ?
C55 C51 Fe2 69.13(16) . . ?
C52 C51 Fe2 69.77(16) . . ?
C55 C51 H51 126.0 . . ?
C52 C51 H51 126.0 . . ?
Fe2 C51 H51 126.7 . . ?
C51 C52 C53 107.7(3) . . ?
C51 C52 Fe2 69.73(16) . . ?
C53 C52 Fe2 69.39(16) . . ?
C51 C52 H52 126.1 . . ?
C53 C52 H52 126.1 . . ?
Fe2 C52 H52 126.3 . . ?
C54 C53 C52 107.9(3) . . ?
C54 C53 Fe2 69.27(15) . . ?
C52 C53 Fe2 69.91(16) . . ?
C54 C53 H53 126.0 . . ?
C52 C53 H53 126.0 . . ?
Fe2 C53 H53 126.4 . . ?
C55 C54 C53 108.3(3) . . ?
C55 C54 Fe2 69.79(16) . . ?
C53 C54 Fe2 70.16(15) . . ?
C55 C54 H54 125.9 . . ?
C53 C54 H54 125.9 . . ?
Fe2 C54 H54 125.8 . . ?
C54 C55 C51 108.1(3) . . ?
C54 C55 Fe2 69.56(16) . . ?
C51 C55 Fe2 70.26(17) . . ?
C54 C55 H55 126.0 . . ?
C51 C55 H55 126.0 . . ?
Fe2 C55 H55 125.8 . . ?
C60 C56 C57 107.5(2) . . ?
C60 C56 Fe2 69.58(14) . . ?
C57 C56 Fe2 69.77(15) . . ?
C60 C56 H56 126.2 . . ?
C57 C56 H56 126.2 . . ?
Fe2 C56 H56 126.0 . . ?
C58 C57 C56 108.2(2) . . ?
C58 C57 Fe2 69.90(15) . . ?
C56 C57 Fe2 69.45(14) . . ?
C58 C57 H57 125.9 . . ?
C56 C57 H57 125.9 . . ?
Fe2 C57 H57 126.3 . . ?
C57 C58 C59 108.1(2) . . ?
C57 C58 Fe2 69.53(15) . . ?
C59 C58 Fe2 69.39(14) . . ?
C57 C58 H58 126.0 . . ?
C59 C58 H58 126.0 . . ?
Fe2 C58 H58 126.7 . . ?
C60 C59 C58 107.6(2) . . ?
C60 C59 Fe2 69.48(14) . . ?
C58 C59 Fe2 69.93(15) . . ?
C60 C59 H59 126.2 . . ?
C58 C59 H59 126.2 . . ?
Fe2 C59 H59 126.0 . . ?
N61 C60 C56 122.9(2) . . ?
N61 C60 C59 128.6(2) . . ?
C56 C60 C59 108.6(2) . . ?
N61 C60 Fe2 125.81(18) . . ?
C56 C60 Fe2 69.71(14) . . ?
C59 C60 Fe2 69.75(14) . . ?
C62 N61 C60 126.5(2) . . ?
C62 N61 H61 115(2) . . ?
C60 N61 H61 118(2) . . ?
O63 C62 N61 124.1(3) . . ?
O63 C62 C64 122.0(2) . . ?
N61 C62 C64 113.8(2) . . ?
N65 C64 C69 124.7(2) . . ?
N65 C64 C62 116.0(2) . . ?
C69 C64 C62 119.3(2) . . ?
C64 N65 C66 116.3(2) . . ?
N65 C66 C67 124.2(3) . . ?
N65 C66 H66 117.9 . . ?
C67 C66 H66 117.9 . . ?
C66 C67 C68 118.2(3) . . ?
C66 C67 H67 120.9 . . ?
C68 C67 H67 120.9 . . ?
O70 C68 C69 124.7(2) . . ?
O70 C68 C67 116.0(2) . . ?
C69 C68 C67 119.2(2) . . ?
C68 C69 C64 117.4(2) . . ?
C68 C69 H69 121.3 . . ?
C64 C69 H69 121.3 . . ?
C68 O70 C71 119.1(2) . . ?
C76 C71 C72 121.3(3) . . ?
C76 C71 O70 119.6(3) . . ?
C72 C71 O70 118.9(3) . . ?
C71 C72 C73B 118.0(3) . . ?
C71 C72 C73A 118.0(3) . . ?
C71 C72 H72 121.0 . . ?
C73A C72 H72 121.0 . . ?
F77 C73A C74 114.4(3) . . ?
F77 C73A C72 122.2(3) . . ?
C74 C73A C72 123.4(3) . . ?
C74 C73B C72 123.4(3) . . ?
C74 C73B H73B 118.3 . . ?
C72 C73B H73B 118.3 . . ?
C73B C74 C75B 115.8(3) . . ?
C73A C74 C75A 115.8(3) . . ?
C73B C74 N78 122.3(3) . . ?
C73A C74 N78 122.3(3) . . ?
C75B C74 N78 121.9(3) . . ?
C75A C74 N78 121.9(3) . . ?
C76 C75A C74 122.6(3) . . ?
C76 C75A H75A 118.7 . . ?
C74 C75A H75A 118.7 . . ?
F79 C75B C76 118.9(3) . . ?
F79 C75B C74 118.5(3) . . ?
C76 C75B C74 122.6(3) . . ?
C71 C76 C75B 118.9(3) . . ?
C71 C76 C75A 118.9(3) . . ?
C71 C76 H76 120.6 . . ?
C75A C76 H76 120.6 . . ?
C74 N78 H78A 118(2) . . ?
C74 N78 H78B 113(2) . . ?
H78A N78 H78B 118(3) . . ?

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 -59.4(2) . . . . ?
C5 C1 C2 Fe1 59.6(2) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
Fe1 C2 C3 C4 -58.8(2) . . . . ?
C1 C2 C3 Fe1 59.1(2) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
Fe1 C3 C4 C5 -59.7(2) . . . . ?
C2 C3 C4 Fe1 58.9(2) . . . . ?
C3 C4 C5 C1 1.0(4) . . . . ?
Fe1 C4 C5 C1 -59.1(2) . . . . ?
C3 C4 C5 Fe1 60.1(2) . . . . ?
C2 C1 C5 C4 -0.8(3) . . . . ?
Fe1 C1 C5 C4 59.4(2) . . . . ?
C2 C1 C5 Fe1 -60.2(2) . . . . ?
C10 C6 C7 C8 -0.6(3) . . . . ?
Fe1 C6 C7 C8 59.1(2) . . . . ?
C10 C6 C7 Fe1 -59.70(18) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
Fe1 C7 C8 C9 59.4(2) . . . . ?
C6 C7 C8 Fe1 -59.4(2) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
Fe1 C8 C9 C10 59.95(19) . . . . ?
C7 C8 C9 Fe1 -59.5(2) . . . . ?
C7 C6 C10 N11 -174.4(3) . . . . ?
Fe1 C6 C10 N11 126.3(3) . . . . ?
C7 C6 C10 C9 0.9(3) . . . . ?
Fe1 C6 C10 C9 -58.38(19) . . . . ?
C7 C6 C10 Fe1 59.32(19) . . . . ?
C8 C9 C10 N11 174.6(2) . . . . ?
Fe1 C9 C10 N11 -125.8(3) . . . . ?
C8 C9 C10 C6 -0.9(3) . . . . ?
Fe1 C9 C10 C6 58.64(19) . . . . ?
C8 C9 C10 Fe1 -59.53(19) . . . . ?
C6 C10 N11 C12 -33.0(4) . . . . ?
C9 C10 N11 C12 152.4(3) . . . . ?
Fe1 C10 N11 C12 61.7(4) . . . . ?
C10 N11 C12 O13 -5.2(5) . . . . ?
C10 N11 C12 C14 173.6(2) . . . . ?
O13 C12 C14 N15 176.5(3) . . . . ?
N11 C12 C14 N15 -2.3(3) . . . . ?
O13 C12 C14 C19 -2.2(4) . . . . ?
N11 C12 C14 C19 179.0(2) . . . . ?
C19 C14 N15 C16 1.5(4) . . . . ?
C12 C14 N15 C16 -177.1(2) . . . . ?
C14 N15 C16 C17 -0.9(4) . . . . ?
N15 C16 C17 C18 -1.0(4) . . . . ?
C16 C17 C18 O20 -177.6(3) . . . . ?
C16 C17 C18 C19 2.4(4) . . . . ?
O20 C18 C19 C14 178.2(3) . . . . ?
C17 C18 C19 C14 -1.8(4) . . . . ?
N15 C14 C19 C18 -0.2(4) . . . . ?
C12 C14 C19 C18 178.3(2) . . . . ?
C19 C18 O20 C21 -4.7(4) . . . . ?
C17 C18 O20 C21 175.2(2) . . . . ?
C18 O20 C21 C22 118.3(3) . . . . ?
C18 O20 C21 C26 -67.1(4) . . . . ?
C26 C21 C22 C23 -0.9(4) . . . . ?
O20 C21 C22 C23 173.6(3) . . . . ?
C21 C22 C23 C24 0.3(5) . . . . ?
C22 C23 C24 C25 1.8(4) . . . . ?
C22 C23 C24 N27 -180.0(3) . . . . ?
N27 C24 C25 F28 0.6(4) . . . . ?
C23 C24 C25 F28 178.9(2) . . . . ?
N27 C24 C25 C26 178.3(3) . . . . ?
C23 C24 C25 C26 -3.5(4) . . . . ?
F28 C25 C26 C21 -179.5(2) . . . . ?
C24 C25 C26 C21 2.9(4) . . . . ?
C22 C21 C26 C25 -0.6(4) . . . . ?
O20 C21 C26 C25 -174.9(3) . . . . ?
C55 C51 C52 C53 0.5(3) . . . . ?
Fe2 C51 C52 C53 59.2(2) . . . . ?
C55 C51 C52 Fe2 -58.75(19) . . . . ?
C51 C52 C53 C54 -0.4(3) . . . . ?
Fe2 C52 C53 C54 59.02(19) . . . . ?
C51 C52 C53 Fe2 -59.4(2) . . . . ?
C52 C53 C54 C55 0.2(3) . . . . ?
Fe2 C53 C54 C55 59.61(19) . . . . ?
C52 C53 C54 Fe2 -59.42(19) . . . . ?
C53 C54 C55 C51 0.1(3) . . . . ?
Fe2 C54 C55 C51 59.9(2) . . . . ?
C53 C54 C55 Fe2 -59.84(19) . . . . ?
C52 C51 C55 C54 -0.4(3) . . . . ?
Fe2 C51 C55 C54 -59.50(19) . . . . ?
C52 C51 C55 Fe2 59.1(2) . . . . ?
C60 C56 C57 C58 -0.2(3) . . . . ?
Fe2 C56 C57 C58 59.34(18) . . . . ?
C60 C56 C57 Fe2 -59.58(17) . . . . ?
C56 C57 C58 C59 -0.2(3) . . . . ?
Fe2 C57 C58 C59 58.86(18) . . . . ?
C56 C57 C58 Fe2 -59.06(18) . . . . ?
C57 C58 C59 C60 0.6(3) . . . . ?
Fe2 C58 C59 C60 59.52(17) . . . . ?
C57 C58 C59 Fe2 -58.95(18) . . . . ?
C57 C56 C60 N61 180.0(2) . . . . ?
Fe2 C56 C60 N61 120.3(2) . . . . ?
C57 C56 C60 C59 0.6(3) . . . . ?
Fe2 C56 C60 C59 -59.10(17) . . . . ?
C57 C56 C60 Fe2 59.70(18) . . . . ?
C58 C59 C60 N61 180.0(2) . . . . ?
Fe2 C59 C60 N61 -120.2(3) . . . . ?
C58 C59 C60 C56 -0.7(3) . . . . ?
Fe2 C59 C60 C56 59.08(17) . . . . ?
C58 C59 C60 Fe2 -59.80(18) . . . . ?
C56 C60 N61 C62 -161.2(3) . . . . ?
C59 C60 N61 C62 18.0(4) . . . . ?
Fe2 C60 N61 C62 -73.7(3) . . . . ?
C60 N61 C62 O63 -1.0(4) . . . . ?
C60 N61 C62 C64 178.4(2) . . . . ?
O63 C62 C64 N65 172.8(3) . . . . ?
N61 C62 C64 N65 -6.7(3) . . . . ?
O63 C62 C64 C69 -6.0(4) . . . . ?
N61 C62 C64 C69 174.6(2) . . . . ?
C69 C64 N65 C66 0.6(4) . . . . ?
C62 C64 N65 C66 -178.1(2) . . . . ?
C64 N65 C66 C67 -0.7(4) . . . . ?
N65 C66 C67 C68 0.8(5) . . . . ?
C66 C67 C68 O70 178.3(3) . . . . ?
C66 C67 C68 C69 -0.7(4) . . . . ?
O70 C68 C69 C64 -178.3(3) . . . . ?
C67 C68 C69 C64 0.6(4) . . . . ?
N65 C64 C69 C68 -0.6(4) . . . . ?
C62 C64 C69 C68 178.1(2) . . . . ?
C69 C68 O70 C71 -7.9(5) . . . . ?
C67 C68 O70 C71 173.2(3) . . . . ?
C68 O70 C71 C76 -81.3(4) . . . . ?
C68 O70 C71 C72 103.5(3) . . . . ?
C76 C71 C72 C73B -1.9(5) . . . . ?
O70 C71 C72 C73B 173.3(3) . . . . ?
C76 C71 C72 C73A -1.9(5) . . . . ?
O70 C71 C72 C73A 173.3(3) . . . . ?
C71 C72 C73A F77 178.7(4) . . . . ?
C71 C72 C73A C74 -0.3(5) . . . . ?
C71 C72 C73B C74 -0.3(5) . . . . ?
C72 C73B C74 C75B 2.2(5) . . . . ?
C72 C73B C74 N78 -179.8(3) . . . . ?
F77 C73A C74 C75A -176.9(4) . . . . ?
C72 C73A C74 C75A 2.2(5) . . . . ?
F77 C73A C74 N78 1.1(5) . . . . ?
C72 C73A C74 N78 -179.8(3) . . . . ?
C73A C74 C75A C76 -2.1(5) . . . . ?
N78 C74 C75A C76 179.9(3) . . . . ?
C73B C74 C75B F79 178.1(4) . . . . ?
N78 C74 C75B F79 0.2(5) . . . . ?
C73B C74 C75B C76 -2.1(5) . . . . ?
N78 C74 C75B C76 179.9(3) . . . . ?
C72 C71 C76 C75B 2.0(5) . . . . ?
O70 C71 C76 C75B -173.1(3) . . . . ?
C72 C71 C76 C75A 2.0(5) . . . . ?
O70 C71 C76 C75A -173.1(3) . . . . ?
F79 C75B C76 C71 179.8(4) . . . . ?
C74 C75B C76 C71 0.1(5) . . . . ?
C74 C75A C76 C71 0.1(5) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

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


####################################################################### 
# 
# 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_MW1521
_database_code_depnum_ccdc_archive 'CCDC 2017025'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;ISCR
France
;
_audit_update_record             
;
2020-07-17 deposited with the CCDC.	2020-11-02 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of diffraction experiment: 27 mai 2020                                  #
#------------------------------------------------------------------------------#


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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C11 H9 Cl F3 N O3'
_chemical_formula_sum            'C11 H9 Cl F3 N O3'
_chemical_formula_weight         295.64
_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                   12.3325(13)
_cell_length_b                   11.1364(10)
_cell_length_c                   9.0892(8)
_cell_angle_alpha                90
_cell_angle_beta                 108.654(5)
_cell_angle_gamma                90
_cell_volume                     1182.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7166
_cell_measurement_theta_min      2.5256
_cell_measurement_theta_max      27.6280
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0991304
_diffrn_orient_matrix_UB_21      0.0401693
_diffrn_orient_matrix_UB_31      -0.0448497
_diffrn_orient_matrix_UB_12      -0.0431734
_diffrn_orient_matrix_UB_22      0.0725086
_diffrn_orient_matrix_UB_32      -0.0304835
_diffrn_orient_matrix_UB_13      0.0392143
_diffrn_orient_matrix_UB_23      0.0481232
_diffrn_orient_matrix_UB_33      0.0589282


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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.460
_exptl_crystal_size_min          0.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             600
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.366
_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  0.794
_exptl_absorpt_correction_T_max  1.000

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

#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_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_source_current           1.0
_diffrn_source_voltage           55.0
_diffrn_reflns_av_uneti/neti     0.0492
_diffrn_reflns_av_r_equivalents  0.0433
_diffrn_reflns_number            6976
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.990
_diffrn_reflns_theta_max         27.601
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.960
_reflns_number_total             2633
_reflns_number_gt                2155
_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 APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2016)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'

#------------------------------------------------------------------------------#
#                            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)+(0.0608P)²+0.3918P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2633
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1158
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.063

#------------------------------------------------------------------------------#
#               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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.89484(4) 0.47765(4) 0.28351(5) 0.02774(16) Uani 1 1 d . . . . .
C1 C 0.79884(16) 0.39633(15) 0.34872(19) 0.0190(4) Uani 1 1 d . . . . .
C2 C 0.70403(16) 0.45473(15) 0.3620(2) 0.0204(4) Uani 1 1 d . . . . .
H2 H 0.692382 0.537142 0.334510 0.025 Uiso 1 1 calc R U . . .
C3 C 0.62527(16) 0.39458(14) 0.41524(19) 0.0186(4) Uani 1 1 d . . . . .
H3 H 0.560694 0.435854 0.425626 0.022 Uiso 1 1 calc R U . . .
C4 C 0.64156(15) 0.27318(14) 0.45332(18) 0.0163(3) Uani 1 1 d . . . . .
C5 C 0.73713(15) 0.21407(14) 0.43834(19) 0.0173(4) Uani 1 1 d . . . . .
H5 H 0.747843 0.131167 0.463419 0.021 Uiso 1 1 calc R U . . .
C6 C 0.81679(15) 0.27449(15) 0.38737(18) 0.0171(4) Uani 1 1 d . . . . .
C7 C 0.92119(16) 0.20893(16) 0.3804(2) 0.0221(4) Uani 1 1 d . . . . .
F7 F 1.01810(10) 0.25834(11) 0.47274(14) 0.0325(3) Uani 1 1 d . . . . .
F8 F 0.93060(11) 0.20630(12) 0.23765(13) 0.0336(3) Uani 1 1 d . . . . .
F9 F 0.92256(11) 0.09452(10) 0.42570(16) 0.0377(3) Uani 1 1 d . . . . .
N11 N 0.56269(13) 0.20580(13) 0.50224(17) 0.0176(3) Uani 1 1 d . . . . .
H11 H 0.557(2) 0.132(2) 0.482(2) 0.021 Uiso 1 1 d . U . . .
C12 C 0.49246(15) 0.24971(15) 0.57587(19) 0.0173(4) Uani 1 1 d . . . . .
O13 O 0.48887(12) 0.35292(11) 0.61914(15) 0.0243(3) Uani 1 1 d . . . . .
C14 C 0.41069(15) 0.15272(15) 0.59989(19) 0.0179(3) Uani 1 1 d . . . . .
O15 O 0.40014(12) 0.05525(11) 0.53905(16) 0.0264(3) Uani 1 1 d . . . . .
O16 O 0.35264(11) 0.19164(11) 0.68964(14) 0.0210(3) Uani 1 1 d . . . . .
C17 C 0.26643(17) 0.10728(16) 0.7085(2) 0.0240(4) Uani 1 1 d . . . . .
H17A H 0.303868 0.032571 0.758973 0.029 Uiso 1 1 calc R U . . .
H17B H 0.211410 0.086362 0.605897 0.029 Uiso 1 1 calc R U . . .
C18 C 0.20541(18) 0.16664(18) 0.8070(2) 0.0272(4) Uani 1 1 d . . . . .
H18A H 0.258945 0.179188 0.911842 0.041 Uiso 1 1 calc R U . . .
H18B H 0.142220 0.115371 0.812502 0.041 Uiso 1 1 calc R U . . .
H18C H 0.175063 0.244267 0.761359 0.041 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
Cl1 C1 1.7384(19) . ?
C1 C2 1.377(3) . ?
C1 C6 1.401(2) . ?
C2 C3 1.388(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(2) . ?
C4 N11 1.408(2) . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.499(3) . ?
C7 F9 1.337(2) . ?
C7 F7 1.339(2) . ?
C7 F8 1.339(2) . ?
N11 C12 1.345(2) . ?
N11 H11 0.84(2) . ?
C12 O13 1.220(2) . ?
C12 C14 1.540(2) . ?
C14 O15 1.206(2) . ?
C14 O16 1.319(2) . ?
O16 C17 1.469(2) . ?
C17 C18 1.495(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C2 C1 C6 120.39(17) . . ?
C2 C1 Cl1 118.30(13) . . ?
C6 C1 Cl1 121.31(14) . . ?
C1 C2 C3 120.75(16) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C2 C3 C4 119.55(17) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 119.53(17) . . ?
C3 C4 N11 122.41(16) . . ?
C5 C4 N11 118.03(15) . . ?
C6 C5 C4 120.98(15) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 118.79(17) . . ?
C5 C6 C7 119.18(15) . . ?
C1 C6 C7 122.00(16) . . ?
F9 C7 F7 106.12(15) . . ?
F9 C7 F8 106.31(15) . . ?
F7 C7 F8 106.24(16) . . ?
F9 C7 C6 112.17(15) . . ?
F7 C7 C6 112.32(15) . . ?
F8 C7 C6 113.16(14) . . ?
C12 N11 C4 125.67(15) . . ?
C12 N11 H11 116.4(16) . . ?
C4 N11 H11 117.9(16) . . ?
O13 C12 N11 126.77(17) . . ?
O13 C12 C14 121.47(16) . . ?
N11 C12 C14 111.76(14) . . ?
O15 C14 O16 125.38(17) . . ?
O15 C14 C12 123.07(16) . . ?
O16 C14 C12 111.52(14) . . ?
C14 O16 C17 114.73(14) . . ?
O16 C17 C18 107.99(14) . . ?
O16 C17 H17A 110.1 . . ?
C18 C17 H17A 110.1 . . ?
O16 C17 H17B 110.1 . . ?
C18 C17 H17B 110.1 . . ?
H17A C17 H17B 108.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C6 C1 C2 C3 0.6(3) . . . . ?
Cl1 C1 C2 C3 -179.24(13) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C2 C3 C4 N11 -177.51(15) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
N11 C4 C5 C6 178.55(15) . . . . ?
C4 C5 C6 C1 -0.9(2) . . . . ?
C4 C5 C6 C7 177.03(14) . . . . ?
C2 C1 C6 C5 0.3(2) . . . . ?
Cl1 C1 C6 C5 -179.81(12) . . . . ?
C2 C1 C6 C7 -177.56(15) . . . . ?
Cl1 C1 C6 C7 2.3(2) . . . . ?
C5 C6 C7 F9 0.5(2) . . . . ?
C1 C6 C7 F9 178.42(15) . . . . ?
C5 C6 C7 F7 -118.89(17) . . . . ?
C1 C6 C7 F7 59.0(2) . . . . ?
C5 C6 C7 F8 120.82(17) . . . . ?
C1 C6 C7 F8 -61.3(2) . . . . ?
C3 C4 N11 C12 -27.9(3) . . . . ?
C5 C4 N11 C12 154.19(16) . . . . ?
C4 N11 C12 O13 -3.8(3) . . . . ?
C4 N11 C12 C14 175.24(15) . . . . ?
O13 C12 C14 O15 168.69(17) . . . . ?
N11 C12 C14 O15 -10.4(2) . . . . ?
O13 C12 C14 O16 -9.2(2) . . . . ?
N11 C12 C14 O16 171.67(14) . . . . ?
O15 C14 O16 C17 -2.3(2) . . . . ?
C12 C14 O16 C17 175.62(14) . . . . ?
C14 O16 C17 C18 -177.61(15) . . . . ?

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# .RES SHELXL file: job.res
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