# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_01788_250k_0m
_database_code_depnum_ccdc_archive 'CCDC 1895056'
loop_
_audit_author_name
_audit_author_address
'Josefina Perles Hernaez'
;Universidad Aut?noma de Madrid
Spain
;
_audit_update_record             
;
2019-02-01 deposited with the CCDC.	2019-06-12 downloaded from the CCDC.
;
_audit_creation_date             2019-01-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(B F4), C8 H11 Fe N4 O2, 2(C2 H1.5 N)'
_chemical_formula_sum            'C12 H14 B2 F8 Fe N6 O2'
_chemical_formula_weight         503.76
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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'
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'
O O 0.0106 0.0060 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_H-M_alt        'C m c e'
_space_group_name_Hall           '-C 2bc 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'x+1/2, -y, z-1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   7.2430(17)
_cell_length_b                   12.882(2)
_cell_length_c                   23.908(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2230.8(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3634
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      75.2900
_cell_measurement_theta_min      3.2152
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.761
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0766
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            15810
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.339
_diffrn_reflns_theta_min         3.337
_diffrn_ambient_temperature      250.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                862
_reflns_number_total             1102
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.367
_refine_diff_density_min         -1.109
_refine_diff_density_rms         0.147
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1102
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1058
_refine_ls_R_factor_gt           0.0897
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1785P)²+13.8267P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2520
_refine_ls_wR_factor_ref         0.2711
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1-H1A = H1B-O1
 0.88 with sigma of 0.02
3. Others
 Fixed Sof: H3A(0.25) H3B(0.25) H3C(0.25) H5A(0.25) H5B(0.25) H5C(0.25)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1)
4.b Idealised Me refined with riding coordinates:
 C3(H3A,H3B,H3C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.500000 0.2254(9) 0.6663(4) 0.047(2) Uani 1 2 d S T P . .
C1 C 0.9042(7) 0.5611(4) 0.5347(2) 0.0328(12) Uani 1 1 d . . . . .
H1 H 0.840814 0.604912 0.559613 0.039 Uiso 1 1 calc R . . . .
C2 C 0.500000 0.5369(8) 0.6367(3) 0.0406(19) Uani 1 2 d S T P . .
C3 C 0.500000 0.5510(13) 0.6972(4) 0.079(4) Uani 1 2 d S T P . .
H3A H 0.617360 0.580055 0.708917 0.118 Uiso 0.25 1 calc R . . . .
H3B H 0.481652 0.484373 0.715345 0.118 Uiso 0.25 1 calc R . . . .
H3C H 0.400987 0.597785 0.707725 0.118 Uiso 0.25 1 calc R . . . .
C4 C 0.500000 0.1695(8) 0.3830(4) 0.064(3) Uani 1 2 d S T P . .
C5 C 0.500000 0.1212(13) 0.3280(5) 0.095(5) Uani 1 2 d S T P . .
H5A H 0.401664 0.150691 0.305513 0.143 Uiso 0.25 1 calc R . . . .
H5B H 0.480580 0.047062 0.331973 0.143 Uiso 0.25 1 calc R . . . .
H5C H 0.617756 0.133601 0.309877 0.143 Uiso 0.25 1 calc R . . . .
F1 F 0.500000 0.2970(14) 0.7010(7) 0.188(6) Uiso 1 2 d S T P . .
F2 F 0.3778(18) 0.1517(11) 0.6728(5) 0.251(7) Uani 1 1 d . . . . .
F3 F 0.500000 0.2596(7) 0.6157(3) 0.152(5) Uani 1 2 d S T P . .
Fe1 Fe 0.500000 0.500000 0.500000 0.0277(6) Uani 1 4 d S T P . .
N1 N 0.8075(9) 0.500000 0.500000 0.0289(14) Uani 1 2 d S T P . .
N2 N 0.500000 0.5258(6) 0.5892(3) 0.0370(16) Uani 1 2 d S T P . .
N3 N 0.500000 0.2065(8) 0.4248(4) 0.086(4) Uani 1 2 d S T P . .
O1 O 0.500000 0.3422(5) 0.5134(2) 0.0433(15) Uani 1 2 d DS T P . .
H1A H 0.500000 0.301(7) 0.484(3) 0.05(3) Uiso 1 2 d DS T P . .
H1B H 0.500000 0.307(11) 0.545(4) 0.13(6) Uiso 1 2 d DS T P . .


_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
B1 F1 1.239(18) . ?
B1 F2 1.307(12) 12_655 ?
B1 F2 1.307(12) . ?
B1 F3 1.287(12) . ?
C1 C1 1.387(11) 12_755 ?
C1 H1 0.9400 . ?
C1 N1 1.342(6) . ?
C2 C3 1.460(12) . ?
C2 N2 1.144(10) . ?
C3 H3A 0.9701 12_655 ?
C3 H3A 0.9700 . ?
C3 H3B 0.9699 12_655 ?
C3 H3B 0.9700 . ?
C3 H3C 0.9700 . ?
C3 H3C 0.9700 12_655 ?
C4 C5 1.454(15) . ?
C4 N3 1.108(13) . ?
C5 H5A 0.9700 12_655 ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5B 0.9700 12_655 ?
C5 H5C 0.9700 . ?
C5 H5C 0.9700 12_655 ?
F2 F2 1.77(3) 12_655 ?
Fe1 N1 2.227(7) . ?
Fe1 N1 2.227(7) 9_666 ?
Fe1 N2 2.158(7) 9_666 ?
Fe1 N2 2.158(7) . ?
Fe1 O1 2.058(6) 9_666 ?
Fe1 O1 2.058(6) . ?
O1 H1A 0.88(2) . ?
O1 H1B 0.88(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 B1 F2 117.5(10) . 12_655 ?
F1 B1 F2 117.5(10) . . ?
F1 B1 F3 111.9(13) . . ?
F2 B1 F2 85.2(16) . 12_655 ?
F3 B1 F2 111.0(8) . 12_655 ?
F3 B1 F2 111.0(8) . . ?
C1 C1 H1 119.3 12_755 . ?
N1 C1 C1 121.5(3) . 12_755 ?
N1 C1 H1 119.3 . . ?
N2 C2 C3 179.9(11) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5(3) . 12_655 ?
C2 C3 H3B 109.5(7) . 12_655 ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5(5) . 12_655 ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3A 122.4 . 12_655 ?
H3A C3 H3B 109.5 12_655 12_655 ?
H3A C3 H3B 95.3 . 12_655 ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3A C3 H3C 15.8 . 12_655 ?
H3A C3 H3C 109.5 12_655 12_655 ?
H3B C3 H3A 95.3 . 12_655 ?
H3B C3 H3B 15.7 . 12_655 ?
H3B C3 H3C 109.5 12_655 12_655 ?
H3B C3 H3C 122.4 . 12_655 ?
H3B C3 H3C 109.5 . . ?
H3C C3 H3A 15.7 . 12_655 ?
H3C C3 H3B 122.4 . 12_655 ?
H3C C3 H3C 95.3 . 12_655 ?
N3 C4 C5 179.9(13) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5(5) . 12_655 ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5(8) . 12_655 ?
C4 C5 H5C 109.5(3) . 12_655 ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5A 94.5 . 12_655 ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 12_655 12_655 ?
H5A C5 H5B 123.1 . 12_655 ?
H5A C5 H5C 109.5 . . ?
H5A C5 H5C 16.7 . 12_655 ?
H5A C5 H5C 109.5 12_655 12_655 ?
H5B C5 H5A 123.1 . 12_655 ?
H5B C5 H5B 16.7 . 12_655 ?
H5B C5 H5C 94.5 . 12_655 ?
H5B C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 12_655 12_655 ?
H5C C5 H5A 16.7 . 12_655 ?
H5C C5 H5B 94.5 . 12_655 ?
H5C C5 H5C 123.1 . 12_655 ?
B1 F2 F2 47.4(8) . 12_655 ?
N1 Fe1 N1 180.0 . 9_666 ?
N2 Fe1 N1 90.000(2) 9_666 . ?
N2 Fe1 N1 90.000(2) . . ?
N2 Fe1 N1 90.000(2) . 9_666 ?
N2 Fe1 N1 90.000(2) 9_666 9_666 ?
N2 Fe1 N2 180.0 . 9_666 ?
O1 Fe1 N1 90.000(1) 9_666 9_666 ?
O1 Fe1 N1 90.000(3) . 9_666 ?
O1 Fe1 N1 90.000(3) 9_666 . ?
O1 Fe1 N1 90.000(1) . . ?
O1 Fe1 N2 89.9(2) . . ?
O1 Fe1 N2 89.9(2) 9_666 9_666 ?
O1 Fe1 N2 90.1(2) . 9_666 ?
O1 Fe1 N2 90.1(2) 9_666 . ?
O1 Fe1 O1 180.0 . 9_666 ?
C1 N1 C1 117.0(7) . 4_566 ?
C1 N1 Fe1 121.5(3) . . ?
C1 N1 Fe1 121.5(3) 4_566 . ?
C2 N2 Fe1 178.4(7) . . ?
Fe1 O1 H1A 118(7) . . ?
Fe1 O1 H1B 130(10) . . ?
H1A O1 H1B 112(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H3A F2 0.97 2.27 3.085(13) 140.9 5 yes
C3 H3B F1 0.97 2.44 3.27(3) 143.5 . yes
C3 H3C F2 0.97 2.29 3.085(13) 138.2 16 yes
O1 H1A N3 0.88(2) 1.87(2) 2.747(11) 177(10) . yes
O1 H1B F3 0.88(2) 1.80(4) 2.668(9) 169(16) . yes

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
C1 C1 N1 C1 -0.001(3) 12_755 . . 4_566 ?
C1 C1 N1 Fe1 180.000(2) 12_755 . . . ?
F1 B1 F2 F2 -118.6(13) . . . 12_655 ?
F3 B1 F2 F2 110.7(10) . . . 12_655 ?

_olex2_submission_special_instructions 'No special instructions were received'
