# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_j18008_r(obv)
_database_code_depnum_ccdc_archive 'CCDC 2051272'
loop_
_audit_author_name
_audit_author_address
'Karlotta van Rees'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2021-01-18 deposited with the CCDC.	2021-01-22 downloaded from the CCDC.
;
_audit_creation_date             2020-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H7 F5 N2 O2'
_chemical_formula_sum            'C17 H7 F5 N2 O2'
_chemical_formula_weight         366.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 F5 O2 N2 H7'
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'

_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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   32.738(2)
_cell_length_b                   32.738(2)
_cell_length_c                   7.4920(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     6953.9(11)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    3165
_cell_measurement_temperature    170
_cell_measurement_theta_max      21.4020
_cell_measurement_theta_min      3.0740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.999
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3312
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-13 45 0 0.0377
-10 3 -10 0.0918
43 -6 0 0.0322
-43 6 0 0.0322
-41 6 3 0.0279
31 -4 -7 0.0638
45 -31 1 0.0187
-39 40 2 0.0344
-39 37 -3 0.0425
23 -46 1 0.0165
8 -7 10 0.0798

_exptl_crystal_preparation       
'Oxidation of dipyrromethane with DDQ in DCM (dry)'
_exptl_crystal_recrystallization_method 
'Grown from a concentrated DCM solution at -30 oC'
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.059
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-12.9903 44.9968 0.0018 0.3406 0.9442 0.0006
-10.0054 3.0131 -10.0001 0.0070 0.0119 -0.9723
43.0066 -6.0197 -0.0007 0.9554 -0.2275 0.2316
-43.0066 6.0197 0.0007 -0.9554 0.2275 -0.2316
-41.0050 6.0160 3.0008 -0.9686 0.2446 0.0560
31.0019 -4.0081 -7.0007 0.8376 -0.2089 -0.4773
45.0007 -31.0162 0.9983 0.6189 -0.7318 0.2940
-38.9958 40.0087 2.0020 -0.4040 0.9215 0.0307
-38.9987 37.0138 -2.9983 -0.3448 0.8239 -0.4347
22.9923 -46.0023 0.9981 -0.1332 -0.9817 0.1460
8.0039 -7.0112 9.9999 -0.1138 -0.0880 0.9545

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1359
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            39210
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        23.254
_diffrn_reflns_theta_max         23.254
_diffrn_reflns_theta_min         2.812
_diffrn_ambient_temperature      170
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1042
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00 -34.00   1.00   15.00    --  -16.53-179.00   0.00   53
  2  ω    -25.00  20.00   1.00   15.00    --  -16.53 -99.00 -60.00   45
  3  ω    -85.00   9.00   1.00   15.00    --  -16.53 -19.00 120.00   94
  4  ω    -76.00  -4.00   1.00   15.00    --  -16.53 136.00  18.59   72
  5  ω      1.00  87.00   1.00   15.00    --   18.25  37.00  90.00   86
  6  ω    -47.00  33.00   1.00   15.00    --   18.25 -57.00-180.00   80
  7  ω      3.00  84.00   1.00   15.00    --   18.25  57.00-180.00   81
  8  ω    -47.00  33.00   1.00   15.00    --   18.25 -57.00 -30.00   80
  9  ω      3.00  84.00   1.00   15.00    --   18.25  57.00 -60.00   81
 10  ω    -82.00  -2.00   1.00   15.00    --  -16.53 -57.00 -60.00   80
 11  ω    -75.00  -3.00   1.00   15.00    --  -16.53 134.00-152.83   72
 12  ω    -25.00  20.00   1.00   15.00    --  -16.53 -99.00-180.00   45
 13  ω      8.00  45.00   1.00   15.00    --   18.25-143.00-124.00   37
 14  ω    -47.00  33.00   1.00   15.00    --   18.25 -57.00 -90.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0242534000
_diffrn_orient_matrix_UB_12      0.0145713000
_diffrn_orient_matrix_UB_13      -0.0205798000
_diffrn_orient_matrix_UB_21      -0.0024508000
_diffrn_orient_matrix_UB_22      0.0202751000
_diffrn_orient_matrix_UB_23      0.0073752000
_diffrn_orient_matrix_UB_31      0.0056141000
_diffrn_orient_matrix_UB_32      0.0016312000
_diffrn_orient_matrix_UB_33      0.0921013000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1582
_reflns_number_total             2221
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     23.21
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0360P)²+3.2180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0963
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H4), C14(H5), C3(H2), C4(H3), C17(H7), C15(H6), C1(H1)
3. Residual lattive electron density (presumably from highly disordered lattive solvent)
was modelled using the "solvent mask" feature on Olex2 (75 electrons/cell).
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
F5 F 0.52717(6) 0.72244(5) 0.80692(19) 0.0368(5) Uani 1 1 d . . . . .
F4 F 0.43844(6) 0.65057(6) 0.7599(2) 0.0429(5) Uani 1 1 d . . . . .
F1 F 0.54724(6) 0.73802(6) 0.1819(2) 0.0430(5) Uani 1 1 d . . . . .
F2 F 0.45822(6) 0.66716(6) 0.1384(2) 0.0481(5) Uani 1 1 d . . . . .
F3 F 0.40393(6) 0.62318(6) 0.4264(2) 0.0523(5) Uani 1 1 d . . . . .
O2 O 0.76433(8) 0.80834(8) 0.8400(3) 0.0508(6) Uani 1 1 d . . . . .
N1 N 0.63529(8) 0.86035(8) 0.4662(3) 0.0281(6) Uani 1 1 d . . . . .
H4 H 0.661496 0.864132 0.507210 0.034 Uiso 1 1 calc R . . . .
N2 N 0.66814(8) 0.80822(8) 0.6313(3) 0.0293(6) Uani 1 1 d . . . . .
O1 O 0.70564(9) 0.95806(8) 0.4498(3) 0.0566(7) Uani 1 1 d . . . . .
C6 C 0.58809(9) 0.77445(10) 0.5204(3) 0.0238(7) Uani 1 1 d . . . . .
C5 C 0.59423(10) 0.81851(10) 0.4567(3) 0.0265(7) Uani 1 1 d . . . . .
C12 C 0.51121(10) 0.70925(10) 0.6392(3) 0.0257(7) Uani 1 1 d . . . . .
C7 C 0.54036(9) 0.73296(9) 0.4960(3) 0.0249(7) Uani 1 1 d . . . . .
C13 C 0.62289(10) 0.76947(10) 0.6027(3) 0.0263(7) Uani 1 1 d . . . . .
C11 C 0.46587(10) 0.67288(10) 0.6184(4) 0.0291(7) Uani 1 1 d . . . . .
C2 C 0.62857(11) 0.89531(10) 0.4009(4) 0.0300(7) Uani 1 1 d . . . . .
C16 C 0.69164(10) 0.79067(10) 0.7120(3) 0.0296(7) Uani 1 1 d . . . . .
C10 C 0.44811(10) 0.65887(10) 0.4495(4) 0.0338(8) Uani 1 1 d . . . . .
C8 C 0.52103(11) 0.71723(10) 0.3278(4) 0.0300(7) Uani 1 1 d . . . . .
C9 C 0.47577(11) 0.68121(10) 0.3034(4) 0.0327(8) Uani 1 1 d . . . . .
C14 C 0.62071(11) 0.72694(10) 0.6713(4) 0.0323(7) Uani 1 1 d . . . . .
H5 H 0.594838 0.696554 0.668237 0.039 Uiso 1 1 calc R . . . .
C3 C 0.58237(11) 0.87562(11) 0.3471(4) 0.0348(8) Uani 1 1 d . . . . .
H2 H 0.568419 0.891562 0.296242 0.042 Uiso 1 1 calc R . . . .
C4 C 0.56047(10) 0.82787(11) 0.3824(4) 0.0328(8) Uani 1 1 d . . . . .
H3 H 0.528986 0.805877 0.360715 0.039 Uiso 1 1 calc R . . . .
C17 C 0.74124(11) 0.82171(12) 0.7611(4) 0.0372(8) Uani 1 1 d . . . . .
H7 H 0.755538 0.853376 0.729446 0.045 Uiso 1 1 calc R . . . .
C15 C 0.66351(11) 0.74018(11) 0.7403(4) 0.0359(8) Uani 1 1 d . . . . .
H6 H 0.673110 0.720867 0.794975 0.043 Uiso 1 1 calc R . . . .
C1 C 0.66595(12) 0.94355(11) 0.3946(4) 0.0413(8) Uani 1 1 d . . . . .
H1 H 0.659144 0.965420 0.344087 0.050 Uiso 1 1 calc R . . . .


_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
F5 C12 1.346(3) . ?
F4 C11 1.345(3) . ?
F1 C8 1.346(3) . ?
F2 C9 1.344(3) . ?
F3 C10 1.341(3) . ?
O2 C17 1.202(3) . ?
N1 C5 1.359(3) . ?
N1 C2 1.360(3) . ?
N2 C13 1.404(3) . ?
N2 C16 1.315(3) . ?
O1 C1 1.212(4) . ?
C6 C5 1.435(4) . ?
C6 C7 1.483(4) . ?
C6 C13 1.375(4) . ?
C5 C4 1.401(4) . ?
C12 C7 1.387(4) . ?
C12 C11 1.370(4) . ?
C7 C8 1.388(4) . ?
C13 C14 1.452(4) . ?
C11 C10 1.372(4) . ?
C2 C3 1.375(4) . ?
C2 C1 1.436(4) . ?
C16 C17 1.468(4) . ?
C16 C15 1.450(4) . ?
C10 C9 1.375(4) . ?
C8 C9 1.368(4) . ?
C14 C15 1.346(4) . ?
C3 C4 1.381(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 N1 C2 109.6(2) . . ?
C16 N2 C13 105.0(2) . . ?
C5 C6 C7 115.7(2) . . ?
C13 C6 C5 124.1(3) . . ?
C13 C6 C7 120.2(2) . . ?
N1 C5 C6 124.5(3) . . ?
N1 C5 C4 106.9(2) . . ?
C4 C5 C6 128.5(3) . . ?
F5 C12 C7 119.6(2) . . ?
F5 C12 C11 117.6(2) . . ?
C11 C12 C7 122.8(2) . . ?
C12 C7 C6 122.1(2) . . ?
C12 C7 C8 115.9(3) . . ?
C8 C7 C6 121.9(2) . . ?
N2 C13 C14 109.6(2) . . ?
C6 C13 N2 121.6(3) . . ?
C6 C13 C14 128.8(3) . . ?
F4 C11 C12 121.4(3) . . ?
F4 C11 C10 119.3(3) . . ?
C12 C11 C10 119.3(3) . . ?
N1 C2 C3 108.3(3) . . ?
N1 C2 C1 122.0(3) . . ?
C3 C2 C1 129.7(3) . . ?
N2 C16 C17 119.9(3) . . ?
N2 C16 C15 112.9(3) . . ?
C15 C16 C17 127.2(3) . . ?
F3 C10 C11 120.1(3) . . ?
F3 C10 C9 119.8(3) . . ?
C11 C10 C9 120.0(3) . . ?
F1 C8 C7 119.5(3) . . ?
F1 C8 C9 118.0(2) . . ?
C9 C8 C7 122.5(3) . . ?
F2 C9 C10 119.7(3) . . ?
F2 C9 C8 120.8(3) . . ?
C8 C9 C10 119.6(3) . . ?
C15 C14 C13 106.4(3) . . ?
C2 C3 C4 107.5(3) . . ?
C3 C4 C5 107.7(3) . . ?
O2 C17 C16 123.4(3) . . ?
C14 C15 C16 106.0(3) . . ?
O1 C1 C2 125.2(3) . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 75 electrons were found in 
a volume of 420Å³ in 1 void per unit cell.
This is consistent with the presence of 0.5[H2O] per Formula 
Unit which account for 90 electrons per unit cell.
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 -0.672 139.6 24.7 '3 water'
2 0.333 0.667 -0.121 139.6 24.7 '3 water'
3 0.667 0.333 -0.312 139.6 24.7 '3 water'

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.175
_oxdiff_exptl_absorpt_empirical_full_min 0.893
# start Validation Reply Form
_vrf_THETM01_j18008_robv         
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: Crystal could only be collected up to 0.90 due to poor diffraction.
Crystal will therefor only be used for connectivity. 
;
# end Validation Reply Form
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_jl20003_0m
_database_code_depnum_ccdc_archive 'CCDC 2051275'
loop_
_audit_author_name
_audit_author_address
'Karlotta van Rees'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2020-12-18 deposited with the CCDC.	2021-01-22 downloaded from the CCDC.
;
_audit_creation_date             2020-08-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H22 F5 Li N4'
_chemical_formula_sum            'C29 H22 F5 Li N4'
_chemical_formula_weight         528.44
_chemical_absolute_configuration ?
_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'
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'
Li Li -0.0003 0.0001 '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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.0585(6)
_cell_length_b                   13.2365(7)
_cell_length_c                   22.1369(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2947.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9516
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.939
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7250
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic brownish red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1088
_exptl_crystal_preparation       "Deprotonation of LH with LN''"
_exptl_crystal_recrystallization_method 
'Sow evaporation from a diluted n-hexane solution'
_exptl_crystal_size_max          0.686
_exptl_crystal_size_mid          0.537
_exptl_crystal_size_min          0.31
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            99392
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.395
_diffrn_reflns_theta_min         2.399
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                5691
_reflns_number_total             6038
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 2403 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         6038
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0257
_refine_ls_restrained_S_all      1.038
_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)+(0.0405P)²+0.3522P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0672
_refine_ls_wR_factor_ref         0.0688
_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.a Aromatic/amide H refined with riding coordinates:
 C21(H21), C1(H1), C8(H8), C28(H28), C20(H20), C2(H2), C23(H23), C3(H3),
 C11(H11), C10(H10)
2.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C7(H7A,H7B,H7C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
F3 F 0.68892(10) 0.00318(7) 0.38331(4) 0.0299(2) Uani 1 1 d . . . . .
F5 F 0.68191(10) 0.35631(7) 0.40034(5) 0.0318(2) Uani 1 1 d . . . . .
F1 F 0.40147(10) 0.15691(7) 0.52239(5) 0.0317(2) Uani 1 1 d . . . . .
F4 F 0.78115(11) 0.18748(8) 0.34957(5) 0.0380(3) Uani 1 1 d . . . . .
F2 F 0.49501(10) -0.01087(7) 0.46848(5) 0.0334(2) Uani 1 1 d . . . . .
N2 N 0.50014(13) 0.45511(9) 0.58644(6) 0.0217(3) Uani 1 1 d . . . . .
N3 N 0.34589(12) 0.50214(10) 0.48969(6) 0.0195(3) Uani 1 1 d . . . . .
N1 N 0.47035(14) 0.60384(10) 0.66769(6) 0.0242(3) Uani 1 1 d . . . . .
N4 N 0.23181(12) 0.68200(10) 0.51296(6) 0.0206(3) Uani 1 1 d . . . . .
C9 C 0.57687(17) 0.45578(12) 0.63543(7) 0.0247(3) Uani 1 1 d . . . . .
C18 C 0.63547(16) 0.26644(12) 0.41825(8) 0.0239(3) Uani 1 1 d . . . . .
C21 C 0.26418(16) 0.48611(13) 0.39369(7) 0.0253(3) Uani 1 1 d . . . . .
H21 H 0.215852 0.500884 0.357898 0.030 Uiso 1 1 calc R . . . .
C17 C 0.68685(17) 0.18055(13) 0.39196(7) 0.0257(3) Uani 1 1 d . . . . .
C22 C 0.26760(15) 0.54443(11) 0.44827(7) 0.0203(3) Uani 1 1 d . . . . .
C19 C 0.39619(15) 0.41550(11) 0.46396(7) 0.0199(3) Uani 1 1 d . . . . .
C12 C 0.54070(16) 0.37383(11) 0.55223(7) 0.0223(3) Uani 1 1 d . . . . .
C1 C 0.30092(15) 0.75232(11) 0.62577(7) 0.0207(3) Uani 1 1 d . . . . .
H1 H 0.261078 0.687250 0.625890 0.025 Uiso 1 1 calc R . . . .
C8 C 0.55818(18) 0.53731(13) 0.67907(7) 0.0260(3) Uani 1 1 d . . . . .
H8 H 0.610042 0.540582 0.714881 0.031 Uiso 1 1 calc R . . . .
C16 C 0.63970(16) 0.08696(12) 0.40915(7) 0.0241(3) Uani 1 1 d . . . . .
C14 C 0.49469(16) 0.16636(12) 0.47930(7) 0.0231(3) Uani 1 1 d . . . . .
C28 C 0.31285(17) 0.91844(12) 0.58465(7) 0.0244(3) Uani 1 1 d . . . . .
H28 H 0.286860 0.967491 0.555630 0.029 Uiso 1 1 calc R . . . .
C13 C 0.48862(15) 0.35423(11) 0.49450(7) 0.0211(3) Uani 1 1 d . . . . .
C00N C 0.53904(16) 0.26187(11) 0.46315(7) 0.0215(3) Uani 1 1 d . . . . .
C20 C 0.34495(16) 0.40484(12) 0.40391(7) 0.0234(3) Uani 1 1 d . . . . .
H20 H 0.363535 0.351508 0.376461 0.028 Uiso 1 1 calc R . . . .
C4 C 0.39434(16) 0.77482(12) 0.67027(7) 0.0221(3) Uani 1 1 d . . . . .
C27 C 0.26328(15) 0.82051(11) 0.58124(7) 0.0205(3) Uani 1 1 d . . . . .
C2 C 0.40048(18) 0.94427(12) 0.63062(8) 0.0272(4) Uani 1 1 d . . . . .
H2 H 0.431941 1.011789 0.633368 0.033 Uiso 1 1 calc R . . . .
C23 C 0.20565(15) 0.64142(11) 0.46252(7) 0.0214(3) Uani 1 1 d . . . . .
H23 H 0.147250 0.673228 0.434669 0.026 Uiso 1 1 calc R . . . .
C3 C 0.44302(17) 0.87341(13) 0.67263(8) 0.0261(3) Uani 1 1 d . . . . .
H3 H 0.505217 0.892046 0.702938 0.031 Uiso 1 1 calc R . . . .
C11 C 0.64692(18) 0.32212(13) 0.58274(8) 0.0301(4) Uani 1 1 d . . . . .
H11 H 0.692064 0.263246 0.569259 0.036 Uiso 1 1 calc R . . . .
C15 C 0.54214(17) 0.07992(11) 0.45270(8) 0.0242(3) Uani 1 1 d . . . . .
C24 C 0.17374(16) 0.78142(12) 0.53031(8) 0.0251(3) Uani 1 1 d . . . . .
C10 C 0.67020(19) 0.37429(13) 0.63497(8) 0.0312(4) Uani 1 1 d . . . . .
H10 H 0.735110 0.359447 0.664856 0.037 Uiso 1 1 calc R . . . .
C5 C 0.44092(19) 0.68776(13) 0.71064(7) 0.0285(4) Uani 1 1 d . . . . .
C25 C 0.03368(17) 0.76037(15) 0.55512(10) 0.0398(5) Uani 1 1 d . . . . .
H25A H -0.023600 0.736218 0.522352 0.060 Uiso 1 1 calc GR . . . .
H25B H -0.003474 0.822692 0.572042 0.060 Uiso 1 1 calc GR . . . .
H25C H 0.038831 0.708781 0.586791 0.060 Uiso 1 1 calc GR . . . .
C26 C 0.1651(2) 0.85509(13) 0.47753(9) 0.0389(5) Uani 1 1 d . . . . .
H26A H 0.253983 0.865816 0.460615 0.058 Uiso 1 1 calc GR . . . .
H26B H 0.129057 0.919660 0.491721 0.058 Uiso 1 1 calc GR . . . .
H26C H 0.106561 0.827140 0.446320 0.058 Uiso 1 1 calc GR . . . .
C7 C 0.5574(2) 0.71727(15) 0.75058(9) 0.0429(5) Uani 1 1 d . . . . .
H7A H 0.580661 0.660482 0.776955 0.064 Uiso 1 1 calc GR . . . .
H7B H 0.532817 0.775756 0.775319 0.064 Uiso 1 1 calc GR . . . .
H7C H 0.634006 0.734619 0.725248 0.064 Uiso 1 1 calc GR . . . .
C6 C 0.3257(2) 0.65046(15) 0.75049(8) 0.0415(5) Uani 1 1 d . . . . .
H6A H 0.251345 0.629364 0.724794 0.062 Uiso 1 1 calc GR . . . .
H6B H 0.296594 0.705229 0.777194 0.062 Uiso 1 1 calc GR . . . .
H6C H 0.355618 0.593020 0.774886 0.062 Uiso 1 1 calc GR . . . .
Li1 Li 0.3762(3) 0.5682(2) 0.56932(12) 0.0261(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F3 C16 1.3424(17) . ?
F3 Li1 2.354(3) 4_556 ?
F5 C18 1.3380(18) . ?
F1 C14 1.3433(18) . ?
F4 C17 1.3373(19) . ?
F2 C15 1.3383(18) . ?
N2 C9 1.331(2) . ?
N2 C12 1.377(2) . ?
N2 Li1 1.985(3) . ?
N3 C22 1.332(2) . ?
N3 C19 1.3767(19) . ?
N3 Li1 1.991(3) . ?
N1 C8 1.273(2) . ?
N1 C5 1.492(2) . ?
N1 Li1 2.421(3) . ?
N4 C23 1.267(2) . ?
N4 C24 1.4902(19) . ?
N4 Li1 2.436(3) . ?
C9 C8 1.461(2) . ?
C9 C10 1.430(2) . ?
C18 C17 1.378(2) . ?
C18 C00N 1.390(2) . ?
C21 C22 1.434(2) . ?
C21 C20 1.367(2) . ?
C17 C16 1.380(2) . ?
C22 C23 1.462(2) . ?
C19 C13 1.407(2) . ?
C19 C20 1.433(2) . ?
C12 C13 1.405(2) . ?
C12 C11 1.437(2) . ?
C1 C4 1.394(2) . ?
C1 C27 1.389(2) . ?
C16 C15 1.379(2) . ?
C14 C00N 1.387(2) . ?
C14 C15 1.372(2) . ?
C28 C27 1.391(2) . ?
C28 C2 1.389(2) . ?
C13 C00N 1.494(2) . ?
C4 C3 1.395(2) . ?
C4 C5 1.532(2) . ?
C27 C24 1.533(2) . ?
C2 C3 1.388(2) . ?
C11 C10 1.367(3) . ?
C24 C25 1.538(2) . ?
C24 C26 1.524(2) . ?
C5 C7 1.519(3) . ?
C5 C6 1.538(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 F3 Li1 115.90(11) . 4_556 ?
C9 N2 C12 106.35(13) . . ?
C9 N2 Li1 120.98(13) . . ?
C12 N2 Li1 132.08(14) . . ?
C22 N3 C19 106.41(12) . . ?
C22 N3 Li1 121.01(13) . . ?
C19 N3 Li1 132.52(13) . . ?
C8 N1 C5 121.79(14) . . ?
C8 N1 Li1 108.35(12) . . ?
C5 N1 Li1 129.84(12) . . ?
C23 N4 C24 121.35(13) . . ?
C23 N4 Li1 108.25(12) . . ?
C24 N4 Li1 130.37(12) . . ?
N2 C9 C8 117.98(14) . . ?
N2 C9 C10 111.70(15) . . ?
C10 C9 C8 130.29(15) . . ?
F5 C18 C17 118.52(14) . . ?
F5 C18 C00N 119.62(14) . . ?
C17 C18 C00N 121.86(14) . . ?
C20 C21 C22 105.66(14) . . ?
F4 C17 C18 120.39(15) . . ?
F4 C17 C16 119.92(14) . . ?
C18 C17 C16 119.69(14) . . ?
N3 C22 C21 111.58(13) . . ?
N3 C22 C23 118.20(13) . . ?
C21 C22 C23 130.13(14) . . ?
N3 C19 C13 121.62(14) . . ?
N3 C19 C20 109.49(13) . . ?
C13 C19 C20 128.82(14) . . ?
N2 C12 C13 122.26(14) . . ?
N2 C12 C11 109.49(15) . . ?
C13 C12 C11 128.06(15) . . ?
C27 C1 C4 123.13(14) . . ?
N1 C8 C9 118.02(14) . . ?
F3 C16 C17 119.82(14) . . ?
F3 C16 C15 120.31(14) . . ?
C15 C16 C17 119.87(14) . . ?
F1 C14 C00N 119.48(13) . . ?
F1 C14 C15 118.02(13) . . ?
C15 C14 C00N 122.50(15) . . ?
C2 C28 C27 119.78(15) . . ?
C19 C13 C00N 118.21(14) . . ?
C12 C13 C19 125.24(14) . . ?
C12 C13 C00N 116.54(14) . . ?
C18 C00N C13 122.22(14) . . ?
C14 C00N C18 116.63(14) . . ?
C14 C00N C13 121.11(14) . . ?
C21 C20 C19 106.85(14) . . ?
C1 C4 C3 117.58(15) . . ?
C1 C4 C5 117.26(14) . . ?
C3 C4 C5 125.08(15) . . ?
C1 C27 C28 117.99(14) . . ?
C1 C27 C24 117.56(13) . . ?
C28 C27 C24 124.40(14) . . ?
C3 C2 C28 121.33(15) . . ?
N4 C23 C22 118.31(14) . . ?
C2 C3 C4 119.92(15) . . ?
C10 C11 C12 106.51(15) . . ?
F2 C15 C16 119.68(14) . . ?
F2 C15 C14 120.90(14) . . ?
C14 C15 C16 119.42(14) . . ?
N4 C24 C27 104.91(12) . . ?
N4 C24 C25 106.93(13) . . ?
N4 C24 C26 112.94(14) . . ?
C27 C24 C25 109.68(14) . . ?
C26 C24 C27 112.43(14) . . ?
C26 C24 C25 109.71(15) . . ?
C11 C10 C9 105.94(15) . . ?
N1 C5 C4 104.42(12) . . ?
N1 C5 C7 114.16(16) . . ?
N1 C5 C6 106.03(14) . . ?
C4 C5 C6 110.22(16) . . ?
C7 C5 C4 112.47(15) . . ?
C7 C5 C6 109.27(16) . . ?
F3 Li1 N1 89.46(10) 4_456 . ?
F3 Li1 N4 89.97(10) 4_456 . ?
N2 Li1 F3 96.59(12) . 4_456 ?
N2 Li1 N3 86.21(12) . . ?
N2 Li1 N1 74.30(10) . . ?
N2 Li1 N4 159.82(15) . . ?
N3 Li1 F3 95.49(12) . 4_456 ?
N3 Li1 N1 160.33(15) . . ?
N3 Li1 N4 74.15(10) . . ?
N1 Li1 N4 124.99(12) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 -0.172 0.750 347.0 76.1 n-hexane
2 0.500 -0.007 0.250 347.0 76.1 n-hexane

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_j2008_239_1
_database_code_depnum_ccdc_archive 'CCDC 2051276'
loop_
_audit_author_name
_audit_author_address
'Karlotta van Rees'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2020-12-18 deposited with the CCDC.	2021-01-22 downloaded from the CCDC.
;
_audit_creation_date             2020-08-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H22 Br F5 Fe N4, C H2 Cl2'
_chemical_formula_sum            'C30 H24 Br Cl2 F5 Fe N4'
_chemical_formula_weight         742.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C29 H22 F5 N4 Fe1 Br1'
_chemical_oxdiff_usercomment     '@ 190 K'
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'
Br Br -0.2901 2.4595 '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'
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'

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

_cell_length_a                   9.6171(6)
_cell_length_b                   12.2102(9)
_cell_length_c                   13.8745(10)
_cell_angle_alpha                108.864(6)
_cell_angle_beta                 98.831(6)
_cell_angle_gamma                90.523(5)
_cell_volume                     1520.44(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4462
_cell_measurement_temperature    170
_cell_measurement_theta_max      21.0380
_cell_measurement_theta_min      3.8540
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.044
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.996
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull bluish red'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 17 -2 0.0306
2 -17 2 0.0306
7 4 -18 0.0847
-7 -4 18 0.0847
-12 5 -4 0.0565
-7 -15 5 0.0399
5 15 -1 0.0378
-3 -15 -3 0.0503
10 -12 5 0.0358
7 1 14 0.0543
12 1 5 0.0396
-11 -6 -4 0.0558
-7 11 -13 0.0740

_exptl_crystal_preparation       'Transmetallation with the lithium salt'
_exptl_crystal_recrystallization_method 
'Slow evaporation of a diluted n-hexane solution'
_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.061
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.3167 16.7026 -2.3578 0.9496 0.1766 0.2592
2.3167 -16.7026 2.3578 -0.9496 -0.1766 -0.2592
7.2884 3.8467 -17.8831 0.2391 0.0437 -0.9700
-7.2884 -3.8467 17.8831 -0.2391 -0.0437 0.9700
-12.4893 4.6523 -4.1547 0.1246 0.9515 0.2814
-6.5381 -14.9029 5.1234 -0.9285 0.3285 0.1731
4.6946 15.1742 -0.9600 0.9399 -0.3324 0.0778
-2.6131 -14.5175 -3.1553 -0.8940 0.3160 -0.3176
9.5208 -12.0282 5.3212 -0.5863 -0.7651 -0.2662
6.8554 0.6778 13.9318 0.1644 -0.8872 0.4310
12.0251 0.5513 5.4833 0.1815 -0.9766 -0.1151
-10.9294 -5.8558 -4.1159 -0.4770 0.8775 0.0497
-6.7705 10.7403 -13.4944 0.5101 0.8334 -0.2127

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1238
_diffrn_reflns_av_unetI/netI     0.0902
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            41369
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         3.231
_diffrn_ambient_temperature      170
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  25.00   1.00   22.50    --  -17.39 -99.00 -30.00   45
  2  ω     -2.00  88.00   1.00   22.50    --   19.11  57.00 120.00   90
  3  ω     -7.00  92.00   1.00   22.50    --   19.11  37.00 -30.00   99
  4  ω    -39.00  49.00   1.00   22.50    --   19.11 -77.00 -30.00   88
  5  ω    -20.00  61.00   1.00   22.50    --   19.11 -99.00  90.00   81
  6  ω    -20.00  61.00   1.00   22.50    --   19.11 -99.00-180.00   81
  7  ω     -7.00  92.00   1.00   22.50    --   19.11  37.00-120.00   99
  8  ω     -7.00  92.00   1.00   22.50    --   19.11  37.00  30.00   99
  9  ω    -50.00  41.00   1.00   22.50    --   19.11 -57.00-150.00   91
 10  ω    -93.00 -39.00   1.00   22.50    --  -17.39-178.00  30.00   54
 11  ω    -39.00  13.00   1.00   22.50    --  -17.39 -77.00 -90.00   52
 12  ω     -2.00  88.00   1.00   22.50    --   19.11  57.00-180.00   90
 13  ω    -20.00  61.00   1.00   22.50    --   19.11 -99.00   0.00   81
 14  ω    -11.00  39.00   1.00   22.50    --   19.11  77.00-180.00   50
 15  ω    -54.00  92.00   1.00   22.50    --   19.11   0.00-180.00  146
 16  ω    -20.00  61.00   1.00   22.50    --   19.11 -99.00 -90.00   81
 17  ω    -54.00  92.00   1.00   22.50    --   19.11   0.00-120.00  146
 18  ω    -54.00  -4.00   1.00   22.50    --   19.11   0.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0107277000
_diffrn_orient_matrix_UB_12      0.0588554000
_diffrn_orient_matrix_UB_13      0.0036594000
_diffrn_orient_matrix_UB_21      -0.0671783000
_diffrn_orient_matrix_UB_22      -0.0030488000
_diffrn_orient_matrix_UB_23      -0.0304789000
_diffrn_orient_matrix_UB_31      -0.0310645000
_diffrn_orient_matrix_UB_32      0.0176114000
_diffrn_orient_matrix_UB_33      0.0453687000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4175
_reflns_number_total             5570
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.793
_refine_diff_density_min         -0.728
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         5570
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1248
_refine_ls_R_factor_gt           0.0897
_refine_ls_restrained_S_all      1.184
_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)+(0.0535P)²+4.4748P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1593
_refine_ls_wR_factor_ref         0.1718
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1(0.034) H24(0.034) H8(0.031) H10(0.033) H11(0.033) H21(0.038)
 H22(0.042) H6A(0.05) H6B(0.05) H6C(0.05) H7A(0.058) H7B(0.058) H7C(0.058)
 H30A(0.06) H30B(0.06) H2(0.051) H29(0.046) H3(0.044) H26A(0.066) H26B(0.066)
 H26C(0.066) H27A(0.075) H27B(0.075) H27C(0.075)
 Fixed X: H1(0.063431) H24(0.113115) H8(0.281714) H10(0.344969) H11(0.347949)
 H21(0.227883) H22(0.156814) H6A(-0.02415) H6B(0.019216) H6C(0.020095)
 H7A(0.260306) H7B(0.280625) H7C(0.386352) H30A(0.62738) H30B(0.475883)
 H2(0.427951) H29(0.308144) H3(0.388965) H26A(-0.103662) H26B(-0.077188) H26C(-
 0.092838) H27A(0.255254) H27B(0.149758) H27C(0.100537)
 Fixed Y: H1(0.773534) H24(0.790207) H8(0.5055) H10(0.273465) H11(0.194875)
 H21(0.393322) H22(0.591483) H6A(0.696554) H6B(0.76976) H6C(0.631315)
 H7A(0.634044) H7B(0.772578) H7C(0.698774) H30A(0.614206) H30B(0.557943)
 H2(1.048679) H29(1.050971) H3(0.897472) H26A(0.883766) H26B(0.973376)
 H26C(0.837008) H27A(0.964306) H27B(1.056268) H27C(0.967875)
 Fixed Z: H1(0.432039) H24(0.119807) H8(0.557763) H10(0.427064) H11(0.237727)
 H21(-0.067648) H22(-0.057818) H6A(0.532758) H6B(0.652717) H6C(0.614962)
 H7A(0.69306) H7B(0.736244) H7C(0.665478) H30A(0.29158) H30B(0.228199)
 H2(0.605916) H29(0.449197) H3(0.667692) H26A(0.236072) H26B(0.35143)
 H26C(0.33207) H27A(0.258232) H27B(0.312191) H27C(0.197773)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Br1 Br -0.10366(8) 0.56917(7) 0.29619(6) 0.0334(2) Uani 1 1 d . . . . .
Fe1 Fe 0.15586(10) 0.60779(8) 0.31370(7) 0.0243(3) Uani 1 1 d . . . . .
Cl2 Cl 0.4524(2) 0.7031(2) 0.37609(16) 0.0502(6) Uani 1 1 d . . . . .
Cl1 Cl 0.5360(3) 0.7162(3) 0.1900(2) 0.0938(11) Uani 1 1 d . . . . .
F5 F 0.5459(5) 0.3431(4) 0.1014(4) 0.0547(13) Uani 1 1 d . . . . .
N2 N 0.2452(6) 0.4513(5) 0.3102(4) 0.0222(13) Uani 1 1 d . . . . .
N3 N 0.1868(6) 0.5493(5) 0.1596(4) 0.0262(13) Uani 1 1 d . . . . .
F1 F 0.0969(5) 0.1484(4) 0.0038(4) 0.0641(15) Uani 1 1 d . . . . .
N4 N 0.1277(6) 0.7669(5) 0.2523(4) 0.0275(14) Uani 1 1 d . . . . .
N1 N 0.2088(5) 0.6111(5) 0.4859(4) 0.0231(13) Uani 1 1 d . . . . .
F3 F 0.4802(7) -0.0280(4) -0.1434(4) 0.081(2) Uani 1 1 d . . . . .
F4 F 0.6504(6) 0.1589(5) -0.0279(4) 0.0760(18) Uani 1 1 d . . . . .
F2 F 0.2026(7) -0.0334(4) -0.1265(4) 0.085(2) Uani 1 1 d . . . . .
C9 C 0.2750(7) 0.4262(6) 0.3977(5) 0.0229(15) Uani 1 1 d . . . . .
C1 C 0.1438(8) 0.8255(6) 0.4645(5) 0.0286(17) Uani 1 1 d . . . . .
H1 H 0.063431 0.773534 0.432039 0.034 Uiso 1 1 calc R . . . .
C24 C 0.1303(7) 0.7363(6) 0.1560(6) 0.0280(17) Uani 1 1 d . . . . .
H24 H 0.113115 0.790207 0.119807 0.034 Uiso 1 1 calc R . . . .
C12 C 0.2735(7) 0.3553(6) 0.2322(5) 0.0233(16) Uani 1 1 d . . . . .
C4 C 0.2231(7) 0.8162(6) 0.5539(5) 0.0273(17) Uani 1 1 d . . . . .
C8 C 0.2575(7) 0.5165(6) 0.4927(5) 0.0259(16) Uani 1 1 d . . . . .
H8 H 0.281714 0.505500 0.557763 0.031 Uiso 1 1 calc R . . . .
C10 C 0.3201(7) 0.3122(6) 0.3781(5) 0.0274(16) Uani 1 1 d . . . . .
H10 H 0.344969 0.273465 0.427064 0.033 Uiso 1 1 calc R . . . .
C13 C 0.2641(7) 0.3541(6) 0.1300(5) 0.0240(15) Uani 1 1 d . . . . .
C11 C 0.3207(7) 0.2694(6) 0.2746(6) 0.0279(17) Uani 1 1 d . . . . .
H11 H 0.347949 0.194875 0.237727 0.033 Uiso 1 1 calc R . . . .
C14 C 0.3184(8) 0.2508(6) 0.0559(5) 0.0298(17) Uani 1 1 d . . . . .
C23 C 0.1596(7) 0.6185(6) 0.1025(5) 0.0255(16) Uani 1 1 d . . . . .
C21 C 0.2106(8) 0.4528(7) -0.0076(5) 0.0315(17) Uani 1 1 d . . . . .
H21 H 0.227883 0.393322 -0.067648 0.038 Uiso 1 1 calc R . . . .
C22 C 0.1722(8) 0.5607(7) -0.0026(5) 0.0351(19) Uani 1 1 d . . . . .
H22 H 0.156814 0.591483 -0.057818 0.042 Uiso 1 1 calc R . . . .
C20 C 0.2204(7) 0.4445(6) 0.0944(5) 0.0274(16) Uani 1 1 d . . . . .
C5 C 0.1935(7) 0.7091(6) 0.5825(5) 0.0232(16) Uani 1 1 d . . . . .
C28 C 0.1773(8) 0.9073(6) 0.4208(6) 0.0302(17) Uani 1 1 d . . . . .
C6 C 0.0379(8) 0.7009(6) 0.5971(6) 0.0333(18) Uani 1 1 d . . . . .
H6A H -0.024150 0.696554 0.532758 0.050 Uiso 1 1 calc GR . . . .
H6B H 0.019216 0.769760 0.652717 0.050 Uiso 1 1 calc GR . . . .
H6C H 0.020095 0.631315 0.614962 0.050 Uiso 1 1 calc GR . . . .
C7 C 0.2885(8) 0.7031(7) 0.6777(5) 0.038(2) Uani 1 1 d . . . . .
H7A H 0.260306 0.634044 0.693060 0.058 Uiso 1 1 calc GR . . . .
H7B H 0.280625 0.772578 0.736244 0.058 Uiso 1 1 calc GR . . . .
H7C H 0.386352 0.698774 0.665478 0.058 Uiso 1 1 calc GR . . . .
C30 C 0.5304(9) 0.6321(8) 0.2682(7) 0.050(2) Uani 1 1 d . . . . .
H30A H 0.627380 0.614206 0.291580 0.060 Uiso 1 1 calc R . . . .
H30B H 0.475883 0.557943 0.228199 0.060 Uiso 1 1 calc R . . . .
C25 C 0.1001(8) 0.8898(6) 0.3101(6) 0.0336(18) Uani 1 1 d . . . . .
C2 C 0.3580(9) 0.9886(7) 0.5676(6) 0.043(2) Uani 1 1 d . . . . .
H2 H 0.427951 1.048679 0.605916 0.051 Uiso 1 1 calc R . . . .
C29 C 0.2852(8) 0.9916(6) 0.4756(6) 0.038(2) Uani 1 1 d . . . . .
H29 H 0.308144 1.050971 0.449197 0.046 Uiso 1 1 calc R . . . .
C3 C 0.3326(8) 0.9007(6) 0.6062(6) 0.0365(19) Uani 1 1 d . . . . .
H3 H 0.388965 0.897472 0.667692 0.044 Uiso 1 1 calc R . . . .
C19 C 0.4588(9) 0.2533(7) 0.0463(6) 0.037(2) Uani 1 1 d . . . . .
C15 C 0.2341(9) 0.1540(7) -0.0034(6) 0.044(2) Uani 1 1 d . . . . .
C18 C 0.5126(11) 0.1555(8) -0.0211(7) 0.050(2) Uani 1 1 d . . . . .
C26 C -0.0572(9) 0.8966(7) 0.3072(6) 0.044(2) Uani 1 1 d . . . . .
H26A H -0.103662 0.883766 0.236072 0.066 Uiso 1 1 calc GR . . . .
H26B H -0.077188 0.973376 0.351430 0.066 Uiso 1 1 calc GR . . . .
H26C H -0.092838 0.837008 0.332070 0.066 Uiso 1 1 calc GR . . . .
C17 C 0.4242(13) 0.0619(8) -0.0789(6) 0.053(3) Uani 1 1 d . . . . .
C27 C 0.1565(10) 0.9774(6) 0.2656(7) 0.050(2) Uani 1 1 d . . . . .
H27A H 0.255254 0.964306 0.258232 0.075 Uiso 1 1 calc GR . . . .
H27B H 0.149758 1.056268 0.312191 0.075 Uiso 1 1 calc GR . . . .
H27C H 0.100537 0.967875 0.197773 0.075 Uiso 1 1 calc GR . . . .
C16 C 0.2866(12) 0.0577(7) -0.0706(6) 0.055(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Fe1 2.4957(12) . ?
Fe1 N2 2.092(5) . ?
Fe1 N3 2.094(5) . ?
Fe1 N4 2.363(6) . ?
Fe1 N1 2.353(5) . ?
Cl2 C30 1.752(8) . ?
Cl1 C30 1.724(9) . ?
F5 C19 1.316(9) . ?
N2 C9 1.337(8) . ?
N2 C12 1.377(8) . ?
N3 C23 1.335(8) . ?
N3 C20 1.381(8) . ?
F1 C15 1.341(9) . ?
N4 C24 1.269(8) . ?
N4 C25 1.503(8) . ?
N1 C8 1.276(8) . ?
N1 C5 1.509(8) . ?
F3 C17 1.349(9) . ?
F4 C18 1.345(10) . ?
F2 C16 1.313(10) . ?
C9 C8 1.453(9) . ?
C9 C10 1.415(9) . ?
C1 C4 1.392(10) . ?
C1 C28 1.383(10) . ?
C24 C23 1.443(9) . ?
C12 C13 1.402(9) . ?
C12 C11 1.408(9) . ?
C4 C5 1.521(10) . ?
C4 C3 1.400(10) . ?
C10 C11 1.360(9) . ?
C13 C14 1.503(9) . ?
C13 C20 1.391(9) . ?
C14 C19 1.378(11) . ?
C14 C15 1.371(11) . ?
C23 C22 1.424(9) . ?
C21 C22 1.354(10) . ?
C21 C20 1.441(10) . ?
C5 C6 1.547(9) . ?
C5 C7 1.509(10) . ?
C28 C25 1.547(11) . ?
C28 C29 1.395(10) . ?
C25 C26 1.511(11) . ?
C25 C27 1.530(10) . ?
C2 C29 1.370(11) . ?
C2 C3 1.381(11) . ?
C19 C18 1.416(11) . ?
C15 C16 1.398(11) . ?
C18 C17 1.361(13) . ?
C17 C16 1.347(13) . ?

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
N2 Fe1 Br1 105.73(15) . . ?
N2 Fe1 N3 81.0(2) . . ?
N2 Fe1 N4 150.7(2) . . ?
N2 Fe1 N1 73.2(2) . . ?
N3 Fe1 Br1 102.06(16) . . ?
N3 Fe1 N4 73.0(2) . . ?
N3 Fe1 N1 151.9(2) . . ?
N4 Fe1 Br1 92.97(14) . . ?
N1 Fe1 Br1 95.52(13) . . ?
N1 Fe1 N4 128.1(2) . . ?
C9 N2 Fe1 119.3(4) . . ?
C9 N2 C12 106.6(6) . . ?
C12 N2 Fe1 133.9(4) . . ?
C23 N3 Fe1 119.1(4) . . ?
C23 N3 C20 106.8(5) . . ?
C20 N3 Fe1 133.8(5) . . ?
C24 N4 Fe1 111.3(5) . . ?
C24 N4 C25 119.9(6) . . ?
C25 N4 Fe1 128.7(4) . . ?
C8 N1 Fe1 112.2(4) . . ?
C8 N1 C5 120.0(6) . . ?
C5 N1 Fe1 127.8(4) . . ?
N2 C9 C8 117.0(6) . . ?
N2 C9 C10 110.9(6) . . ?
C10 C9 C8 132.1(6) . . ?
C28 C1 C4 122.7(7) . . ?
N4 C24 C23 119.0(6) . . ?
N2 C12 C13 122.2(6) . . ?
N2 C12 C11 108.9(6) . . ?
C13 C12 C11 128.7(6) . . ?
C1 C4 C5 117.6(6) . . ?
C1 C4 C3 117.8(7) . . ?
C3 C4 C5 124.4(7) . . ?
N1 C8 C9 118.0(6) . . ?
C11 C10 C9 105.9(6) . . ?
C12 C13 C14 116.6(6) . . ?
C20 C13 C12 125.3(6) . . ?
C20 C13 C14 117.8(6) . . ?
C10 C11 C12 107.6(6) . . ?
C19 C14 C13 118.8(6) . . ?
C15 C14 C13 122.9(7) . . ?
C15 C14 C19 118.3(7) . . ?
N3 C23 C24 116.7(6) . . ?
N3 C23 C22 111.5(6) . . ?
C22 C23 C24 131.7(6) . . ?
C22 C21 C20 107.7(6) . . ?
C21 C22 C23 105.9(6) . . ?
N3 C20 C13 122.3(6) . . ?
N3 C20 C21 108.1(6) . . ?
C13 C20 C21 129.5(6) . . ?
N1 C5 C4 102.8(5) . . ?
N1 C5 C6 106.5(5) . . ?
C4 C5 C6 110.3(6) . . ?
C7 C5 N1 113.3(6) . . ?
C7 C5 C4 114.2(6) . . ?
C7 C5 C6 109.3(6) . . ?
C1 C28 C25 116.2(6) . . ?
C1 C28 C29 118.0(7) . . ?
C29 C28 C25 125.5(7) . . ?
Cl1 C30 Cl2 111.3(5) . . ?
N4 C25 C28 102.8(5) . . ?
N4 C25 C26 107.9(6) . . ?
N4 C25 C27 112.8(6) . . ?
C26 C25 C28 111.1(6) . . ?
C26 C25 C27 110.3(7) . . ?
C27 C25 C28 111.6(7) . . ?
C29 C2 C3 121.9(7) . . ?
C2 C29 C28 119.9(7) . . ?
C2 C3 C4 119.4(8) . . ?
F5 C19 C14 121.5(6) . . ?
F5 C19 C18 118.9(8) . . ?
C14 C19 C18 119.6(8) . . ?
F1 C15 C14 120.0(7) . . ?
F1 C15 C16 117.7(8) . . ?
C14 C15 C16 122.3(8) . . ?
F4 C18 C19 118.6(9) . . ?
F4 C18 C17 121.6(8) . . ?
C17 C18 C19 119.8(9) . . ?
F3 C17 C18 117.4(10) . . ?
C16 C17 F3 121.1(9) . . ?
C16 C17 C18 121.5(8) . . ?
F2 C16 C15 120.6(10) . . ?
F2 C16 C17 120.9(8) . . ?
C17 C16 C15 118.5(8) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.089
_oxdiff_exptl_absorpt_empirical_full_min 0.923
# start Validation Reply Form
_vrf_PLAT910_j2008_239_1         
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         13 Note  
RESPONSE: This has been noted, but is not serious. The independent reflections/parameters 
is equal to 14.2. Indicating there is no issue with the data collection. 
;
# end Validation Reply Form
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_j2008_347
_database_code_depnum_ccdc_archive 'CCDC 2051273'
loop_
_audit_author_name
_audit_author_address
'Karlotta van Rees'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2020-12-18 deposited with the CCDC.	2021-01-22 downloaded from the CCDC.
;
_audit_creation_date             2020-08-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H22 Br F5 N4 Zn'
_chemical_formula_sum            'C29 H22 Br F5 N4 Zn'
_chemical_formula_weight         666.78
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C29 H22 F5 N4 Zn1 Br1'
_chemical_oxdiff_usercomment     '@ 190 K'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8072(2)
_cell_length_b                   11.5434(3)
_cell_length_c                   12.0315(2)
_cell_angle_alpha                86.721(2)
_cell_angle_beta                 86.179(2)
_cell_angle_gamma                84.625(2)
_cell_volume                     1351.28(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15378
_cell_measurement_temperature    170
_cell_measurement_theta_max      24.9100
_cell_measurement_theta_min      3.5500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.449
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.992
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull brownish red'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             668
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -16 1 0.0509
3 16 -1 0.0509
2 1 17 0.2482
-14 2 0 0.0476
14 -2 0 0.0476
-1 -1 -17 0.1822
-4 -14 -8 0.1134
4 14 -6 0.0688
13 6 -1 0.0444
11 -8 0 0.0393
-6 13 4 0.0964
-11 -6 7 0.0887

_exptl_crystal_preparation       'Transmetallation ofn lithium salt'
_exptl_crystal_recrystallization_method 
'slow evaporation from a diluted n-hexane solution'
_exptl_crystal_size_max          0.437
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.095
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.7828 -16.0055 1.3655 0.0257 0.9981 0.0554
2.7828 16.0055 -1.3655 -0.0257 -0.9981 -0.0554
1.6321 0.9240 16.9397 0.0042 0.1297 -0.9915
-13.5135 1.8556 -0.1438 -0.9979 0.0257 0.0596
13.5135 -1.8556 0.1438 0.9979 -0.0257 -0.0596
-1.4288 -0.8772 -16.9507 0.0098 -0.1347 0.9908
-4.4493 -14.2567 -8.1641 -0.0636 0.7977 0.5997
3.5163 14.4998 -6.0623 0.0767 -0.9718 0.2232
13.0610 6.3478 -0.8026 0.8511 -0.5210 -0.0647
11.1518 -8.3412 -0.0033 0.9237 0.3830 0.0092
-6.0802 13.4544 3.9113 -0.6567 -0.6929 -0.2976
-11.3418 -6.4977 6.7602 -0.7603 0.5832 -0.2859

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            51141
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         3.238
_diffrn_ambient_temperature      170
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00  51.00   1.00    6.00    --  -17.55  57.00  90.00   90
  2  ω    -48.00  39.00   1.00    6.00    --  -17.55  77.00-120.00   87
  3  ω     -2.00  88.00   1.00    6.00    --   19.26  57.00-150.00   90
  4  ω     -2.00  88.00   1.00    6.00    --   19.26  57.00 -60.00   90
  5  ω     -2.00  88.00   1.00    6.00    --   19.26  57.00  30.00   90
  6  ω     -2.00  88.00   1.00    6.00    --   19.26  57.00 120.00   90
  7  ω    -20.00  61.00   1.00    6.00    --   19.26 -99.00  30.00   81
  8  ω    -39.00  49.00   1.00    6.00    --   19.26 -77.00 150.00   88
  9  ω    -50.00  41.00   1.00    6.00    --   19.26 -57.00 -30.00   91
 10  ω    -93.00 -39.00   1.00    6.00    --  -17.55-178.00 -90.00   54
 11  ω    -20.00  61.00   1.00    6.00    --   19.26 -99.00 150.00   81
 12  ω    -20.00  61.00   1.00    6.00    --   19.26 -99.00 -90.00   81
 13  ω    -54.00  92.00   1.00    6.00    --   19.26   0.00-180.00  146
 14  ω    -54.00  92.00   1.00    6.00    --   19.26   0.00-150.00  146
 15  ω    -54.00  92.00   1.00    6.00    --   19.26   0.00-120.00  146
 16  ω    -11.00  39.00   1.00    6.00    --   19.26  77.00  60.00   50
 17  ω    -54.00  92.00   1.00    6.00    --   19.26   0.00 -60.00  146
 18  ω    -54.00  92.00   1.00    6.00    --   19.26   0.00 -30.00  146
 19  ω    -54.00  82.00   1.00    6.00    --   19.26   0.00   0.00  136
 20  ω    -54.00  92.00   1.00    6.00    --   19.26   0.00 -90.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0719006000
_diffrn_orient_matrix_UB_12      -0.0146080000
_diffrn_orient_matrix_UB_13      -0.0058816000
_diffrn_orient_matrix_UB_21      -0.0102079000
_diffrn_orient_matrix_UB_22      -0.0595726000
_diffrn_orient_matrix_UB_23      0.0118884000
_diffrn_orient_matrix_UB_31      -0.0048353000
_diffrn_orient_matrix_UB_32      -0.0075405000
_diffrn_orient_matrix_UB_33      -0.0576566000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4347
_reflns_number_total             4931
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         4931
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0349P)²+1.0998P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0783
_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.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C1(H1), C24(H24), C22(H22), C11(H11), C21(H21), C10(H10), C3(H3),
 C29(H29), C2(H2)
2.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C7(H7A,H7B,H7C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Br1 Br 0.52377(3) 0.70695(3) 0.69253(3) 0.03677(10) Uani 1 1 d . . . . .
Zn1 Zn 0.73112(3) 0.58485(3) 0.69017(3) 0.02607(10) Uani 1 1 d . . . . .
F5 F 0.90556(17) 0.16494(16) 0.95303(17) 0.0490(5) Uani 1 1 d . . . . .
F1 F 0.44009(18) 0.30561(17) 0.95618(17) 0.0520(5) Uani 1 1 d . . . . .
F2 F 0.3752(2) 0.12604(18) 1.09494(16) 0.0552(5) Uani 1 1 d . . . . .
N3 N 0.7066(2) 0.41330(18) 0.67700(17) 0.0241(5) Uani 1 1 d . . . . .
F3 F 0.5745(2) -0.03339(18) 1.16601(17) 0.0642(6) Uani 1 1 d . . . . .
N2 N 0.7904(2) 0.53258(18) 0.84622(17) 0.0239(5) Uani 1 1 d . . . . .
N4 N 0.7586(2) 0.54031(18) 0.48952(17) 0.0237(5) Uani 1 1 d . . . . .
F4 F 0.8393(2) -0.01577(18) 1.0911(2) 0.0719(7) Uani 1 1 d . . . . .
N1 N 0.8817(2) 0.72935(18) 0.75344(18) 0.0246(5) Uani 1 1 d . . . . .
C8 C 0.8900(3) 0.7118(2) 0.8579(2) 0.0269(6) Uani 1 1 d . . . . .
H8 H 0.926090 0.767138 0.900676 0.032 Uiso 1 1 calc R . . . .
C20 C 0.6875(3) 0.3266(2) 0.7589(2) 0.0237(6) Uani 1 1 d . . . . .
C28 C 0.7901(3) 0.7385(2) 0.4341(2) 0.0262(6) Uani 1 1 d . . . . .
C23 C 0.6870(3) 0.3699(2) 0.5799(2) 0.0245(6) Uani 1 1 d . . . . .
C25 C 0.7886(3) 0.6179(2) 0.3884(2) 0.0254(6) Uani 1 1 d . . . . .
C1 C 0.8683(3) 0.7471(2) 0.5245(2) 0.0251(6) Uani 1 1 d . . . . .
H1 H 0.929019 0.681980 0.546265 0.030 Uiso 1 1 calc R . . . .
C24 C 0.7086(3) 0.4441(2) 0.4797(2) 0.0239(6) Uani 1 1 d . . . . .
H24 H 0.685945 0.421277 0.409015 0.029 Uiso 1 1 calc R . . . .
C9 C 0.8430(3) 0.6048(2) 0.9109(2) 0.0256(6) Uani 1 1 d . . . . .
C14 C 0.6744(3) 0.2414(2) 0.9517(2) 0.0240(6) Uani 1 1 d . . . . .
C13 C 0.7071(3) 0.3405(2) 0.8711(2) 0.0238(6) Uani 1 1 d . . . . .
C4 C 0.8617(3) 0.8466(2) 0.5846(2) 0.0281(6) Uani 1 1 d . . . . .
C12 C 0.7564(3) 0.4372(2) 0.9138(2) 0.0255(6) Uani 1 1 d . . . . .
C22 C 0.6527(3) 0.2531(2) 0.5946(2) 0.0284(6) Uani 1 1 d . . . . .
H22 H 0.633526 0.203890 0.538090 0.034 Uiso 1 1 calc R . . . .
C15 C 0.5403(3) 0.2283(2) 0.9902(2) 0.0294(6) Uani 1 1 d . . . . .
C11 C 0.7885(3) 0.4554(2) 1.0251(2) 0.0299(6) Uani 1 1 d . . . . .
H11 H 0.774112 0.404466 1.088735 0.036 Uiso 1 1 calc R . . . .
C21 C 0.6530(3) 0.2256(2) 0.7066(2) 0.0272(6) Uani 1 1 d . . . . .
H21 H 0.633915 0.153212 0.743020 0.033 Uiso 1 1 calc R . . . .
C10 C 0.8437(3) 0.5594(2) 1.0231(2) 0.0303(6) Uani 1 1 d . . . . .
H10 H 0.876116 0.594649 1.084461 0.036 Uiso 1 1 calc R . . . .
C19 C 0.7739(3) 0.1578(2) 0.9886(2) 0.0308(6) Uani 1 1 d . . . . .
C5 C 0.9325(3) 0.8366(2) 0.6943(2) 0.0290(6) Uani 1 1 d . . . . .
C3 C 0.7819(3) 0.9442(2) 0.5461(3) 0.0367(7) Uani 1 1 d . . . . .
H3 H 0.777550 1.014480 0.584197 0.044 Uiso 1 1 calc R . . . .
C26 C 0.6846(3) 0.6145(3) 0.2999(2) 0.0320(6) Uani 1 1 d . . . . .
H26A H 0.691714 0.536479 0.270714 0.048 Uiso 1 1 calc GR . . . .
H26B H 0.703651 0.671832 0.238934 0.048 Uiso 1 1 calc GR . . . .
H26C H 0.591774 0.632984 0.333266 0.048 Uiso 1 1 calc GR . . . .
C27 C 0.9326(3) 0.5760(3) 0.3401(2) 0.0326(7) Uani 1 1 d . . . . .
H27A H 0.997471 0.570954 0.399044 0.049 Uiso 1 1 calc GR . . . .
H27B H 0.961484 0.631305 0.280218 0.049 Uiso 1 1 calc GR . . . .
H27C H 0.930625 0.499044 0.310101 0.049 Uiso 1 1 calc GR . . . .
C29 C 0.7098(3) 0.8373(2) 0.3977(2) 0.0342(7) Uani 1 1 d . . . . .
H29 H 0.655835 0.834427 0.335385 0.041 Uiso 1 1 calc R . . . .
C16 C 0.5065(3) 0.1375(3) 1.0620(2) 0.0347(7) Uani 1 1 d . . . . .
C17 C 0.6068(4) 0.0565(3) 1.0971(2) 0.0389(8) Uani 1 1 d . . . . .
C7 C 1.0886(3) 0.8121(3) 0.6733(3) 0.0384(7) Uani 1 1 d . . . . .
H7A H 1.131273 0.799553 0.744883 0.058 Uiso 1 1 calc GR . . . .
H7B H 1.125344 0.878780 0.631423 0.058 Uiso 1 1 calc GR . . . .
H7C H 1.108591 0.742286 0.630260 0.058 Uiso 1 1 calc GR . . . .
C6 C 0.9008(3) 0.9449(2) 0.7619(3) 0.0392(7) Uani 1 1 d . . . . .
H6A H 0.801750 0.956917 0.779966 0.059 Uiso 1 1 calc GR . . . .
H6B H 0.931270 1.012994 0.717995 0.059 Uiso 1 1 calc GR . . . .
H6C H 0.949072 0.934449 0.830968 0.059 Uiso 1 1 calc GR . . . .
C2 C 0.7084(3) 0.9396(3) 0.4522(3) 0.0413(8) Uani 1 1 d . . . . .
H2 H 0.656383 1.007703 0.424995 0.050 Uiso 1 1 calc R . . . .
C18 C 0.7420(3) 0.0656(3) 1.0600(3) 0.0402(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Zn1 2.3627(4) . ?
Zn1 N3 2.034(2) . ?
Zn1 N2 2.044(2) . ?
Zn1 N4 2.489(2) . ?
Zn1 N1 2.510(2) . ?
F5 C19 1.341(3) . ?
F1 C15 1.333(3) . ?
F2 C16 1.339(3) . ?
N3 C20 1.380(3) . ?
N3 C23 1.329(3) . ?
F3 C17 1.339(3) . ?
N2 C9 1.332(3) . ?
N2 C12 1.384(3) . ?
N4 C25 1.498(3) . ?
N4 C24 1.271(3) . ?
F4 C18 1.332(3) . ?
N1 C8 1.269(3) . ?
N1 C5 1.501(3) . ?
C8 C9 1.456(4) . ?
C20 C13 1.396(4) . ?
C20 C21 1.434(4) . ?
C28 C25 1.528(4) . ?
C28 C1 1.385(4) . ?
C28 C29 1.390(4) . ?
C23 C24 1.454(4) . ?
C23 C22 1.418(4) . ?
C25 C26 1.527(4) . ?
C25 C27 1.537(4) . ?
C1 C4 1.386(4) . ?
C9 C10 1.419(4) . ?
C14 C13 1.501(4) . ?
C14 C15 1.384(4) . ?
C14 C19 1.383(4) . ?
C13 C12 1.393(4) . ?
C4 C5 1.525(4) . ?
C4 C3 1.386(4) . ?
C12 C11 1.428(4) . ?
C22 C21 1.366(4) . ?
C15 C16 1.371(4) . ?
C11 C10 1.360(4) . ?
C19 C18 1.375(4) . ?
C5 C7 1.537(4) . ?
C5 C6 1.527(4) . ?
C3 C2 1.386(4) . ?
C29 C2 1.382(4) . ?
C16 C17 1.363(4) . ?
C17 C18 1.382(5) . ?

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
Br1 Zn1 N4 100.54(5) . . ?
Br1 Zn1 N1 97.65(5) . . ?
N3 Zn1 Br1 114.01(6) . . ?
N3 Zn1 N2 84.21(8) . . ?
N3 Zn1 N4 71.44(8) . . ?
N3 Zn1 N1 145.78(8) . . ?
N2 Zn1 Br1 113.06(6) . . ?
N2 Zn1 N4 144.48(8) . . ?
N2 Zn1 N1 71.16(8) . . ?
N4 Zn1 N1 116.66(7) . . ?
C20 N3 Zn1 130.17(18) . . ?
C23 N3 Zn1 121.90(17) . . ?
C23 N3 C20 107.3(2) . . ?
C9 N2 Zn1 121.75(18) . . ?
C9 N2 C12 106.9(2) . . ?
C12 N2 Zn1 129.48(18) . . ?
C25 N4 Zn1 130.19(16) . . ?
C24 N4 Zn1 107.56(17) . . ?
C24 N4 C25 120.2(2) . . ?
C8 N1 Zn1 107.59(17) . . ?
C8 N1 C5 120.6(2) . . ?
C5 N1 Zn1 130.52(16) . . ?
N1 C8 C9 118.5(2) . . ?
N3 C20 C13 122.7(2) . . ?
N3 C20 C21 108.2(2) . . ?
C13 C20 C21 129.1(2) . . ?
C1 C28 C25 117.2(2) . . ?
C1 C28 C29 118.0(3) . . ?
C29 C28 C25 124.6(3) . . ?
N3 C23 C24 117.4(2) . . ?
N3 C23 C22 111.2(2) . . ?
C22 C23 C24 131.3(2) . . ?
N4 C25 C28 104.2(2) . . ?
N4 C25 C26 112.7(2) . . ?
N4 C25 C27 107.0(2) . . ?
C28 C25 C27 109.9(2) . . ?
C26 C25 C28 113.0(2) . . ?
C26 C25 C27 109.7(2) . . ?
C28 C1 C4 122.8(3) . . ?
N4 C24 C23 117.9(2) . . ?
N2 C9 C8 117.4(2) . . ?
N2 C9 C10 111.1(2) . . ?
C10 C9 C8 131.5(2) . . ?
C15 C14 C13 120.6(2) . . ?
C19 C14 C13 122.6(2) . . ?
C19 C14 C15 116.9(2) . . ?
C20 C13 C14 116.7(2) . . ?
C12 C13 C20 125.6(2) . . ?
C12 C13 C14 117.7(2) . . ?
C1 C4 C5 117.1(2) . . ?
C1 C4 C3 117.9(3) . . ?
C3 C4 C5 124.8(3) . . ?
N2 C12 C13 122.1(2) . . ?
N2 C12 C11 108.4(2) . . ?
C13 C12 C11 129.4(2) . . ?
C21 C22 C23 106.1(2) . . ?
F1 C15 C14 119.4(2) . . ?
F1 C15 C16 118.6(3) . . ?
C16 C15 C14 122.1(3) . . ?
C10 C11 C12 107.3(2) . . ?
C22 C21 C20 107.2(2) . . ?
C11 C10 C9 106.3(2) . . ?
F5 C19 C14 119.6(2) . . ?
F5 C19 C18 118.4(3) . . ?
C18 C19 C14 121.9(3) . . ?
N1 C5 C4 104.0(2) . . ?
N1 C5 C7 106.9(2) . . ?
N1 C5 C6 112.7(2) . . ?
C4 C5 C7 110.8(2) . . ?
C4 C5 C6 112.6(2) . . ?
C6 C5 C7 109.7(2) . . ?
C4 C3 C2 120.2(3) . . ?
C2 C29 C28 120.0(3) . . ?
F2 C16 C15 120.3(3) . . ?
F2 C16 C17 119.9(3) . . ?
C17 C16 C15 119.8(3) . . ?
F3 C17 C16 120.2(3) . . ?
F3 C17 C18 119.7(3) . . ?
C16 C17 C18 120.1(3) . . ?
C29 C2 C3 120.8(3) . . ?
F4 C18 C19 120.6(3) . . ?
F4 C18 C17 120.1(3) . . ?
C19 C18 C17 119.2(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.092
_oxdiff_exptl_absorpt_empirical_full_min 0.877
####################################################################### 
# 
# 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_8v00036_0m
_database_code_depnum_ccdc_archive 'CCDC 2051274'
loop_
_audit_author_name
_audit_author_address
'Karlotta van Rees'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2021-01-18 deposited with the CCDC.	2021-01-22 downloaded from the CCDC.
;
_audit_creation_date             2021-01-07
_audit_creation_method           
;
Olex2 1.5-dev
(compiled 2020.12.01 svn.rb'be22f01f' for OlexSys, GUI svn.r6224)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H23 F5 N4, C2 H3 N'
_chemical_formula_sum            'C31 H26 F5 N5'
_chemical_formula_weight         563.57
_chemical_absolute_configuration ?
_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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.0603(2)
_cell_length_b                   9.3452(2)
_cell_length_c                   14.9643(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.9940(10)
_cell_angle_gamma                90
_cell_volume                     1365.12(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9834
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.75
_cell_measurement_theta_min      2.781
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.7194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0550 before and 0.0515 after correction. The Ratio of minimum to maximum transmission is 0.9629. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear greenish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             584
_exptl_crystal_preparation       
'In-situ Schiff-base condensation and oxidation from the dipyrromethane formylate and diamine'
_exptl_crystal_recrystallization_method 'Slow evaporation from MeCN'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            91541
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.999
_diffrn_reflns_theta_min         2.782
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                10665
_reflns_number_total             12936
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 4286 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         12936
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0408
_refine_ls_restrained_S_all      1.034
_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)+(0.0535P)²+0.1205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.1031
_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. Others
 Sof(H2)=1-FVAR(1)
 Sof(H3)=FVAR(1)
 Fixed Uiso: H3(0.015) H2(0.015)
3.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C10(H10), C8(H8), C3(H3A), C2(H2A), C29(H29), C1(H1), C24(H24),
 C22(H22), C21(H21)
3.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C27(H27A,H27B,H27C), C26(H26A,H26B,H26C),
 C30S(H30A,H30B,H30C)
;
_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
F5 F 0.30488(10) 0.63146(12) 0.11233(7) 0.0232(2) Uani 1 1 d . . . . .
F4 F 0.18016(10) 0.66099(12) -0.06678(7) 0.0260(2) Uani 1 1 d . . . . .
F3 F 0.31084(12) 0.58173(13) -0.19833(6) 0.0296(2) Uani 1 1 d . . . . .
F2 F 0.56422(12) 0.46082(13) -0.14773(7) 0.0304(2) Uani 1 1 d . . . . .
F1 F 0.68862(9) 0.42768(11) 0.03047(7) 0.0227(2) Uani 1 1 d . . . . .
N3 N 0.56459(13) 0.39474(14) 0.32216(8) 0.0151(2) Uani 1 1 d . . . . .
H3 H 0.630(3) 0.446(4) 0.355(2) 0.015 Uiso 0.61(3) 1 d . U P A 1
N2 N 0.74574(12) 0.59741(14) 0.30787(8) 0.0147(2) Uani 1 1 d . . . . .
N1 N 0.88881(15) 0.67283(16) 0.48356(9) 0.0218(3) Uani 1 1 d . . . . .
N4 N 0.60179(14) 0.32865(14) 0.50630(9) 0.0190(2) Uani 1 1 d . . . . .
C13 C 0.56970(14) 0.51165(15) 0.17742(9) 0.0134(2) Uani 1 1 d . . . . .
C12 C 0.68151(13) 0.60023(15) 0.21472(9) 0.0137(2) Uani 1 1 d . . . . .
C11 C 0.74471(16) 0.70851(16) 0.17084(10) 0.0173(2) Uani 1 1 d . . . . .
H11 H 0.721640 0.732904 0.107321 0.021 Uiso 1 1 calc R U . . .
C10 C 0.84503(16) 0.76980(17) 0.23874(10) 0.0189(3) Uani 1 1 d . . . . .
H10 H 0.905460 0.844535 0.231312 0.023 Uiso 1 1 calc R U . . .
C9 C 0.84092(15) 0.69912(16) 0.32312(10) 0.0157(2) Uani 1 1 d . . . . .
C8 C 0.92066(15) 0.73180(16) 0.41655(10) 0.0168(3) Uani 1 1 d . . . . .
H8 H 0.995400 0.796775 0.426105 0.020 Uiso 1 1 calc R U . . .
C5 C 0.95995(16) 0.70310(16) 0.57993(10) 0.0175(3) Uani 1 1 d . . . . .
C6 C 1.11561(17) 0.6858(2) 0.59556(12) 0.0284(4) Uani 1 1 d . . . . .
H6A H 1.149936 0.754430 0.556960 0.043 Uiso 1 1 calc R U . . .
H6B H 1.136611 0.588290 0.579214 0.043 Uiso 1 1 calc R U . . .
H6C H 1.159676 0.703748 0.660498 0.043 Uiso 1 1 calc R U . . .
C7 C 0.9242(2) 0.85642(18) 0.60283(13) 0.0305(4) Uani 1 1 d . . . . .
H7A H 0.961797 0.924327 0.565484 0.046 Uiso 1 1 calc R U . . .
H7B H 0.963531 0.875558 0.668275 0.046 Uiso 1 1 calc R U . . .
H7C H 0.824412 0.867197 0.589323 0.046 Uiso 1 1 calc R U . . .
C4 C 0.90325(13) 0.59746(15) 0.63998(9) 0.0137(2) Uani 1 1 d . . . . .
C3 C 0.94903(14) 0.59980(16) 0.73622(10) 0.0161(2) Uani 1 1 d . . . . .
H3A H 1.016835 0.666844 0.765146 0.019 Uiso 1 1 calc R U . . .
C2 C 0.89506(15) 0.50370(17) 0.78953(10) 0.0169(2) Uani 1 1 d . . . . .
H2A H 0.926835 0.505648 0.854694 0.020 Uiso 1 1 calc R U . . .
C29 C 0.79539(15) 0.40514(16) 0.74851(9) 0.0161(2) Uani 1 1 d . . . . .
H29 H 0.760714 0.339320 0.785638 0.019 Uiso 1 1 calc R U . . .
C28 C 0.74599(14) 0.40258(15) 0.65272(9) 0.0137(2) Uani 1 1 d . . . . .
C1 C 0.80186(14) 0.49899(15) 0.60024(9) 0.0134(2) Uani 1 1 d . . . . .
H1 H 0.769564 0.497342 0.535107 0.016 Uiso 1 1 calc R U . . .
C25 C 0.63244(16) 0.29790(15) 0.60588(10) 0.0167(2) Uani 1 1 d . . . . .
C27 C 0.50288(18) 0.3224(2) 0.64108(12) 0.0262(3) Uani 1 1 d . . . . .
H27A H 0.471896 0.421462 0.628691 0.039 Uiso 1 1 calc R U . . .
H27B H 0.523512 0.304457 0.707538 0.039 Uiso 1 1 calc R U . . .
H27C H 0.430602 0.256952 0.609467 0.039 Uiso 1 1 calc R U . . .
C26 C 0.6841(2) 0.14328(17) 0.62466(12) 0.0268(3) Uani 1 1 d . . . . .
H26A H 0.765449 0.129285 0.600521 0.040 Uiso 1 1 calc R U . . .
H26B H 0.612105 0.076603 0.594250 0.040 Uiso 1 1 calc R U . . .
H26C H 0.707634 0.125436 0.691165 0.040 Uiso 1 1 calc R U . . .
C24 C 0.51611(16) 0.25581(16) 0.44864(10) 0.0179(3) Uani 1 1 d . . . . .
H24 H 0.469160 0.178102 0.468166 0.021 Uiso 1 1 calc R U . . .
C23 C 0.49057(15) 0.29341(15) 0.35123(10) 0.0164(2) Uani 1 1 d . . . . .
C22 C 0.38960(16) 0.23921(17) 0.27521(10) 0.0194(3) Uani 1 1 d . . . . .
H22 H 0.324674 0.166106 0.277000 0.023 Uiso 1 1 calc R U . . .
C21 C 0.40419(15) 0.31357(16) 0.19811(10) 0.0178(3) Uani 1 1 d . . . . .
H21 H 0.350951 0.301607 0.136836 0.021 Uiso 1 1 calc R U . . .
C20 C 0.51448(14) 0.41151(15) 0.22841(9) 0.0144(2) Uani 1 1 d . . . . .
C14 C 0.50119(14) 0.52843(15) 0.07782(9) 0.0138(2) Uani 1 1 d . . . . .
C19 C 0.37107(14) 0.58712(16) 0.04935(10) 0.0158(2) Uani 1 1 d . . . . .
C18 C 0.30586(15) 0.60462(17) -0.04268(11) 0.0181(3) Uani 1 1 d . . . . .
C17 C 0.37138(17) 0.56369(17) -0.10959(10) 0.0197(3) Uani 1 1 d . . . . .
C16 C 0.50061(17) 0.50376(18) -0.08400(10) 0.0195(3) Uani 1 1 d . . . . .
C15 C 0.56370(14) 0.48700(16) 0.00856(10) 0.0158(2) Uani 1 1 d . . . . .
N5S N 0.1051(2) 0.3265(2) 0.00878(13) 0.0409(4) Uani 1 1 d . . . . .
C31S C 0.06454(18) 0.3987(2) 0.05745(12) 0.0279(3) Uani 1 1 d . . . . .
C30S C 0.0145(2) 0.4928(3) 0.11952(15) 0.0344(4) Uani 1 1 d . . . . .
H30A H 0.087997 0.510511 0.174715 0.052 Uiso 1 1 calc R U . . .
H30B H -0.063182 0.447586 0.137215 0.052 Uiso 1 1 calc R U . . .
H30C H -0.014899 0.583843 0.088459 0.052 Uiso 1 1 calc R U . . .
H2 H 0.718(5) 0.554(6) 0.349(4) 0.015 Uiso 0.39(3) 1 d . U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F5 C19 1.3442(16) . ?
F4 C18 1.3364(17) . ?
F3 C17 1.3311(17) . ?
F2 C16 1.3323(18) . ?
F1 C15 1.3398(16) . ?
N3 H3 0.86(3) . ?
N3 C23 1.3406(18) . ?
N3 C20 1.3801(18) . ?
N2 C12 1.3876(17) . ?
N2 C9 1.3291(19) . ?
N2 H2 0.84(6) . ?
N1 C8 1.252(2) . ?
N1 C5 1.4741(19) . ?
N4 C25 1.4751(19) . ?
N4 C24 1.2615(19) . ?
C13 C12 1.3995(19) . ?
C13 C20 1.4042(19) . ?
C13 C14 1.4913(19) . ?
C12 C11 1.4357(19) . ?
C11 H11 0.9500 . ?
C11 C10 1.372(2) . ?
C10 H10 0.9500 . ?
C10 C9 1.434(2) . ?
C9 C8 1.466(2) . ?
C8 H8 0.9500 . ?
C5 C6 1.535(2) . ?
C5 C7 1.536(2) . ?
C5 C4 1.535(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C4 C3 1.4021(19) . ?
C4 C1 1.3956(19) . ?
C3 H3A 0.9500 . ?
C3 C2 1.395(2) . ?
C2 H2A 0.9500 . ?
C2 C29 1.390(2) . ?
C29 H29 0.9500 . ?
C29 C28 1.3992(19) . ?
C28 C1 1.3992(19) . ?
C28 C25 1.538(2) . ?
C1 H1 0.9500 . ?
C25 C27 1.537(2) . ?
C25 C26 1.538(2) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C24 H24 0.9500 . ?
C24 C23 1.460(2) . ?
C23 C22 1.423(2) . ?
C22 H22 0.9500 . ?
C22 C21 1.385(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.4252(19) . ?
C14 C19 1.3879(19) . ?
C14 C15 1.391(2) . ?
C19 C18 1.384(2) . ?
C18 C17 1.379(2) . ?
C17 C16 1.382(2) . ?
C16 C15 1.386(2) . ?
N5S C31S 1.139(3) . ?
C31S C30S 1.454(3) . ?
C30S H30A 0.9800 . ?
C30S H30B 0.9800 . ?
C30S H30C 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
C23 N3 H3 128(2) . . ?
C23 N3 C20 108.37(12) . . ?
C20 N3 H3 124(2) . . ?
C12 N2 H2 126(4) . . ?
C9 N2 C12 107.46(12) . . ?
C9 N2 H2 125(4) . . ?
C8 N1 C5 122.78(13) . . ?
C24 N4 C25 121.82(13) . . ?
C12 C13 C20 124.25(12) . . ?
C12 C13 C14 117.98(12) . . ?
C20 C13 C14 117.73(12) . . ?
N2 C12 C13 121.57(12) . . ?
N2 C12 C11 108.83(12) . . ?
C13 C12 C11 129.53(13) . . ?
C12 C11 H11 126.8 . . ?
C10 C11 C12 106.45(13) . . ?
C10 C11 H11 126.8 . . ?
C11 C10 H10 126.7 . . ?
C11 C10 C9 106.68(13) . . ?
C9 C10 H10 126.7 . . ?
N2 C9 C10 110.55(13) . . ?
N2 C9 C8 121.21(13) . . ?
C10 C9 C8 128.17(13) . . ?
N1 C8 C9 119.02(13) . . ?
N1 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
N1 C5 C6 111.40(13) . . ?
N1 C5 C7 108.22(13) . . ?
N1 C5 C4 106.75(11) . . ?
C6 C5 C7 110.45(15) . . ?
C4 C5 C6 110.68(13) . . ?
C4 C5 C7 109.22(13) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C4 C5 121.00(12) . . ?
C1 C4 C5 120.77(12) . . ?
C1 C4 C3 118.21(13) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 C4 120.05(13) . . ?
C2 C3 H3A 120.0 . . ?
C3 C2 H2A 119.6 . . ?
C29 C2 C3 120.84(13) . . ?
C29 C2 H2A 119.6 . . ?
C2 C29 H29 119.9 . . ?
C2 C29 C28 120.22(13) . . ?
C28 C29 H29 119.9 . . ?
C29 C28 C25 121.22(12) . . ?
C1 C28 C29 118.20(13) . . ?
C1 C28 C25 120.57(12) . . ?
C4 C1 C28 122.47(12) . . ?
C4 C1 H1 118.8 . . ?
C28 C1 H1 118.8 . . ?
N4 C25 C28 106.69(11) . . ?
N4 C25 C27 109.26(13) . . ?
N4 C25 C26 110.27(12) . . ?
C28 C25 C26 109.47(13) . . ?
C27 C25 C28 110.30(12) . . ?
C27 C25 C26 110.76(14) . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N4 C24 H24 120.7 . . ?
N4 C24 C23 118.62(13) . . ?
C23 C24 H24 120.7 . . ?
N3 C23 C24 121.10(13) . . ?
N3 C23 C22 109.71(13) . . ?
C22 C23 C24 129.17(13) . . ?
C23 C22 H22 126.6 . . ?
C21 C22 C23 106.77(13) . . ?
C21 C22 H22 126.6 . . ?
C22 C21 H21 126.6 . . ?
C22 C21 C20 106.76(13) . . ?
C20 C21 H21 126.6 . . ?
N3 C20 C13 122.20(12) . . ?
N3 C20 C21 108.39(12) . . ?
C13 C20 C21 129.42(13) . . ?
C19 C14 C13 121.47(12) . . ?
C19 C14 C15 116.36(12) . . ?
C15 C14 C13 122.17(12) . . ?
F5 C19 C14 119.80(12) . . ?
F5 C19 C18 117.72(13) . . ?
C18 C19 C14 122.48(13) . . ?
F4 C18 C19 120.32(14) . . ?
F4 C18 C17 120.04(13) . . ?
C17 C18 C19 119.64(13) . . ?
F3 C17 C18 120.36(14) . . ?
F3 C17 C16 120.04(14) . . ?
C18 C17 C16 119.61(13) . . ?
F2 C16 C17 120.42(14) . . ?
F2 C16 C15 119.88(14) . . ?
C17 C16 C15 119.70(13) . . ?
F1 C15 C14 119.95(12) . . ?
F1 C15 C16 117.85(13) . . ?
C16 C15 C14 122.20(13) . . ?
N5S C31S C30S 179.0(2) . . ?
C31S C30S H30A 109.5 . . ?
C31S C30S H30B 109.5 . . ?
C31S C30S H30C 109.5 . . ?
H30A C30S H30B 109.5 . . ?
H30A C30S H30C 109.5 . . ?
H30B C30S H30C 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
F5 C19 C18 F4 -1.4(2) . . . . ?
F5 C19 C18 C17 178.49(14) . . . . ?
F4 C18 C17 F3 0.9(2) . . . . ?
F4 C18 C17 C16 -179.15(14) . . . . ?
F3 C17 C16 F2 -1.5(2) . . . . ?
F3 C17 C16 C15 179.18(14) . . . . ?
F2 C16 C15 F1 0.3(2) . . . . ?
F2 C16 C15 C14 -179.23(14) . . . . ?
N3 C23 C22 C21 -0.71(18) . . . . ?
N2 C12 C11 C10 -0.59(17) . . . . ?
N2 C9 C8 N1 -7.3(2) . . . . ?
N1 C5 C4 C3 -179.05(13) . . . . ?
N1 C5 C4 C1 -0.83(18) . . . . ?
N4 C24 C23 N3 5.8(2) . . . . ?
N4 C24 C23 C22 -172.24(16) . . . . ?
C13 C12 C11 C10 176.47(15) . . . . ?
C13 C14 C19 F5 0.7(2) . . . . ?
C13 C14 C19 C18 179.55(14) . . . . ?
C13 C14 C15 F1 1.1(2) . . . . ?
C13 C14 C15 C16 -179.40(14) . . . . ?
C12 N2 C9 C10 -1.84(17) . . . . ?
C12 N2 C9 C8 175.23(13) . . . . ?
C12 C13 C20 N3 2.0(2) . . . . ?
C12 C13 C20 C21 -178.21(15) . . . . ?
C12 C13 C14 C19 -109.49(16) . . . . ?
C12 C13 C14 C15 70.26(18) . . . . ?
C12 C11 C10 C9 -0.49(17) . . . . ?
C11 C10 C9 N2 1.48(18) . . . . ?
C11 C10 C9 C8 -175.33(15) . . . . ?
C10 C9 C8 N1 169.24(16) . . . . ?
C9 N2 C12 C13 -175.83(13) . . . . ?
C9 N2 C12 C11 1.51(16) . . . . ?
C8 N1 C5 C6 -52.3(2) . . . . ?
C8 N1 C5 C7 69.3(2) . . . . ?
C8 N1 C5 C4 -173.24(15) . . . . ?
C5 N1 C8 C9 -177.76(14) . . . . ?
C5 C4 C3 C2 179.35(13) . . . . ?
C5 C4 C1 C28 -178.92(13) . . . . ?
C6 C5 C4 C3 59.55(18) . . . . ?
C6 C5 C4 C1 -122.22(15) . . . . ?
C7 C5 C4 C3 -62.26(18) . . . . ?
C7 C5 C4 C1 115.97(16) . . . . ?
C4 C3 C2 C29 -0.2(2) . . . . ?
C3 C4 C1 C28 -0.6(2) . . . . ?
C3 C2 C29 C28 -1.1(2) . . . . ?
C2 C29 C28 C1 1.5(2) . . . . ?
C2 C29 C28 C25 -178.00(13) . . . . ?
C29 C28 C1 C4 -0.6(2) . . . . ?
C29 C28 C25 N4 177.56(13) . . . . ?
C29 C28 C25 C27 59.00(18) . . . . ?
C29 C28 C25 C26 -63.12(17) . . . . ?
C1 C4 C3 C2 1.1(2) . . . . ?
C1 C28 C25 N4 -1.88(18) . . . . ?
C1 C28 C25 C27 -120.44(15) . . . . ?
C1 C28 C25 C26 117.43(14) . . . . ?
C25 N4 C24 C23 179.58(14) . . . . ?
C25 C28 C1 C4 178.84(13) . . . . ?
C24 N4 C25 C28 177.02(14) . . . . ?
C24 N4 C25 C27 -63.74(19) . . . . ?
C24 N4 C25 C26 58.2(2) . . . . ?
C24 C23 C22 C21 177.48(15) . . . . ?
C23 N3 C20 C13 179.21(14) . . . . ?
C23 N3 C20 C21 -0.65(17) . . . . ?
C23 C22 C21 C20 0.29(18) . . . . ?
C22 C21 C20 N3 0.20(17) . . . . ?
C22 C21 C20 C13 -179.65(15) . . . . ?
C20 N3 C23 C24 -177.52(13) . . . . ?
C20 N3 C23 C22 0.85(17) . . . . ?
C20 C13 C12 N2 -1.4(2) . . . . ?
C20 C13 C12 C11 -178.17(15) . . . . ?
C20 C13 C14 C19 68.20(18) . . . . ?
C20 C13 C14 C15 -112.05(16) . . . . ?
C14 C13 C12 N2 176.08(13) . . . . ?
C14 C13 C12 C11 -0.6(2) . . . . ?
C14 C13 C20 N3 -175.58(13) . . . . ?
C14 C13 C20 C21 4.3(2) . . . . ?
C14 C19 C18 F4 179.65(13) . . . . ?
C14 C19 C18 C17 -0.4(2) . . . . ?
C19 C14 C15 F1 -179.11(13) . . . . ?
C19 C14 C15 C16 0.4(2) . . . . ?
C19 C18 C17 F3 -179.03(14) . . . . ?
C19 C18 C17 C16 0.9(2) . . . . ?
C18 C17 C16 F2 178.57(15) . . . . ?
C18 C17 C16 C15 -0.8(2) . . . . ?
C17 C16 C15 F1 179.61(14) . . . . ?
C17 C16 C15 C14 0.1(2) . . . . ?
C15 C14 C19 F5 -179.11(13) . . . . ?
C15 C14 C19 C18 -0.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
