# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_2a

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H11 Fe N O5'
_chemical_formula_sum            'C18 H11 Fe N O5'
_chemical_formula_weight         377.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1357(9)
_cell_length_b                   10.0365(13)
_cell_length_c                   12.6590(16)
_cell_angle_alpha                92.570(2)
_cell_angle_beta                 104.792(2)
_cell_angle_gamma                105.483(2)
_cell_volume                     838.51(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6603
_cell_measurement_theta_min      2.540
_cell_measurement_theta_max      25.37

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.296
_exptl_crystal_size_min          0.282
_exptl_absorpt_coefficient_mu    0.927
_shelx_estimated_absorpt_T_min   0.761
_shelx_estimated_absorpt_T_max   0.780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7252
_exptl_absorpt_correction_T_max  0.8192
_exptl_absorpt_process_details   '(Sheldrick, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Apex CCD diffractometer 01-670'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            9209
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.676
_diffrn_reflns_theta_max         25.368
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3065
_reflns_number_gt                2833
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/1 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0478P)²+0.1540P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3065
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0818
_refine_ls_wR_factor_gt          0.0800
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.09648(4) 0.89185(2) 0.25742(2) 0.04197(11) Uani 1 1 d . . . . .
O1 O 0.5888(3) 1.11376(16) 0.39373(11) 0.0724(5) Uani 1 1 d . . . . .
O2 O -0.0332(3) 0.68750(16) 0.05926(12) 0.0672(4) Uani 1 1 d . . . . .
O3 O 0.1820(3) 1.10271(18) 0.44698(14) 0.0841(5) Uani 1 1 d . . . . .
O4 O -0.0589(3) 1.07979(18) 0.10961(15) 0.0830(5) Uani 1 1 d . . . . .
O5 O -0.1854(3) 0.6998(2) 0.35368(17) 0.0925(6) Uani 1 1 d . . . . .
C1 C 0.5231(3) 1.06764(19) 0.29644(14) 0.0474(4) Uani 1 1 d . . . . .
C2 C 0.4017(3) 0.92099(18) 0.26004(14) 0.0421(4) Uani 1 1 d . . . . .
H2 H 0.4228 0.8778 0.1947 0.050 Uiso 1 1 calc R U . . .
C3 C 0.3543(3) 0.82992(18) 0.33745(14) 0.0425(4) Uani 1 1 d . . . . .
H3 H 0.4161 0.8722 0.4141 0.051 Uiso 1 1 calc R U . . .
N4 N 0.3389(3) 0.62304(17) 0.22594(13) 0.0536(4) Uani 1 1 d . . . . .
C5 C 0.3296(3) 0.67881(18) 0.32178(14) 0.0439(4) Uani 1 1 d . . . . .
C6 C 0.3020(3) 0.5999(2) 0.40695(16) 0.0553(5) Uani 1 1 d . . . . .
H6 H 0.2947 0.6411 0.4725 0.066 Uiso 1 1 calc R U . . .
C7 C 0.2854(4) 0.4597(2) 0.39311(19) 0.0663(6) Uani 1 1 d . . . . .
H7 H 0.2656 0.4049 0.4488 0.080 Uiso 1 1 calc R U . . .
C8 C 0.2987(4) 0.4028(2) 0.2960(2) 0.0668(6) Uani 1 1 d . . . . .
H8 H 0.2908 0.3090 0.2849 0.080 Uiso 1 1 calc R U . . .
C9 C 0.3240(4) 0.4872(2) 0.21535(19) 0.0649(6) Uani 1 1 d . . . . .
H9 H 0.3312 0.4474 0.1493 0.078 Uiso 1 1 calc R U . . .
C10 C 0.5698(3) 1.16058(18) 0.21147(15) 0.0455(4) Uani 1 1 d . . . . .
C11 C 0.4660(3) 1.1281(2) 0.10075(15) 0.0516(4) Uani 1 1 d . . . . .
H11 H 0.3640 1.0445 0.0762 0.062 Uiso 1 1 calc R U . . .
C12 C 0.5139(4) 1.2198(2) 0.02660(17) 0.0614(5) Uani 1 1 d . . . . .
H12 H 0.4427 1.1983 -0.0475 0.074 Uiso 1 1 calc R U . . .
C13 C 0.6668(4) 1.3427(2) 0.0623(2) 0.0674(6) Uani 1 1 d . . . . .
H13 H 0.6992 1.4037 0.0122 0.081 Uiso 1 1 calc R U . . .
C14 C 0.7715(4) 1.3755(2) 0.1719(2) 0.0686(6) Uani 1 1 d . . . . .
H14 H 0.8758 1.4580 0.1958 0.082 Uiso 1 1 calc R U . . .
C15 C 0.7220(3) 1.2863(2) 0.24615(18) 0.0565(5) Uani 1 1 d . . . . .
H15 H 0.7909 1.3102 0.3205 0.068 Uiso 1 1 calc R U . . .
C16 C 0.0237(3) 0.76387(19) 0.13627(15) 0.0464(4) Uani 1 1 d . . . . .
C17 C 0.1566(3) 1.0227(2) 0.37574(17) 0.0556(5) Uani 1 1 d . . . . .
C18 C -0.0013(3) 1.0071(2) 0.16780(17) 0.0563(5) Uani 1 1 d . . . . .
C19 C -0.0815(3) 0.7762(2) 0.31545(18) 0.0595(5) 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
Fe1 C18 1.804(2) . ?
Fe1 C19 1.807(2) . ?
Fe1 C16 1.8254(19) . ?
Fe1 C17 1.829(2) . ?
Fe1 C2 2.1104(17) . ?
Fe1 C3 2.1242(18) . ?
O1 C1 1.220(2) . ?
O2 C16 1.126(2) . ?
O3 C17 1.125(3) . ?
O4 C18 1.139(2) . ?
O5 C19 1.134(3) . ?
C1 C2 1.478(2) . ?
C1 C10 1.498(2) . ?
C2 C3 1.412(2) . ?
C2 H2 0.9800 . ?
C3 C5 1.478(2) . ?
C3 H3 0.9800 . ?
N4 C9 1.337(3) . ?
N4 C5 1.338(2) . ?
C5 C6 1.389(3) . ?
C6 C7 1.379(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.369(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.371(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.385(3) . ?
C10 C15 1.393(3) . ?
C11 C12 1.385(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.377(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?

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
C18 Fe1 C19 116.34(10) . . ?
C18 Fe1 C16 87.77(8) . . ?
C19 Fe1 C16 90.18(9) . . ?
C18 Fe1 C17 89.79(9) . . ?
C19 Fe1 C17 89.15(9) . . ?
C16 Fe1 C17 176.87(8) . . ?
C18 Fe1 C2 108.18(8) . . ?
C19 Fe1 C2 135.36(9) . . ?
C16 Fe1 C2 88.37(7) . . ?
C17 Fe1 C2 94.26(8) . . ?
C18 Fe1 C3 146.79(9) . . ?
C19 Fe1 C3 96.81(9) . . ?
C16 Fe1 C3 94.37(7) . . ?
C17 Fe1 C3 88.75(8) . . ?
C2 Fe1 C3 38.97(6) . . ?
O1 C1 C2 121.61(16) . . ?
O1 C1 C10 119.50(17) . . ?
C2 C1 C10 118.89(15) . . ?
C3 C2 C1 120.70(15) . . ?
C3 C2 Fe1 71.04(10) . . ?
C1 C2 Fe1 111.39(12) . . ?
C3 C2 H2 115.3 . . ?
C1 C2 H2 115.3 . . ?
Fe1 C2 H2 115.3 . . ?
C2 C3 C5 123.66(16) . . ?
C2 C3 Fe1 69.99(10) . . ?
C5 C3 Fe1 115.19(11) . . ?
C2 C3 H3 113.6 . . ?
C5 C3 H3 113.6 . . ?
Fe1 C3 H3 113.6 . . ?
C9 N4 C5 117.25(18) . . ?
N4 C5 C6 122.13(17) . . ?
N4 C5 C3 118.39(16) . . ?
C6 C5 C3 119.46(17) . . ?
C7 C6 C5 119.2(2) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C8 C7 C6 118.8(2) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C7 C8 C9 118.5(2) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
N4 C9 C8 124.0(2) . . ?
N4 C9 H9 118.0 . . ?
C8 C9 H9 118.0 . . ?
C11 C10 C15 118.79(18) . . ?
C11 C10 C1 122.96(16) . . ?
C15 C10 C1 118.23(17) . . ?
C12 C11 C10 120.14(19) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 120.1(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C10 120.8(2) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
O2 C16 Fe1 175.20(17) . . ?
O3 C17 Fe1 176.0(2) . . ?
O4 C18 Fe1 178.0(2) . . ?
O5 C19 Fe1 176.1(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 1.3(3) . . . . ?
C10 C1 C2 C3 -179.95(16) . . . . ?
O1 C1 C2 Fe1 81.3(2) . . . . ?
C10 C1 C2 Fe1 -99.93(17) . . . . ?
C1 C2 C3 C5 -148.29(17) . . . . ?
Fe1 C2 C3 C5 107.55(16) . . . . ?
C1 C2 C3 Fe1 104.15(16) . . . . ?
C9 N4 C5 C6 -1.2(3) . . . . ?
C9 N4 C5 C3 177.47(18) . . . . ?
C2 C3 C5 N4 -4.8(3) . . . . ?
Fe1 C3 C5 N4 77.12(19) . . . . ?
C2 C3 C5 C6 173.90(17) . . . . ?
Fe1 C3 C5 C6 -104.21(17) . . . . ?
N4 C5 C6 C7 0.6(3) . . . . ?
C3 C5 C6 C7 -177.98(18) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C6 C7 C8 C9 -1.3(3) . . . . ?
C5 N4 C9 C8 0.5(3) . . . . ?
C7 C8 C9 N4 0.8(4) . . . . ?
O1 C1 C10 C11 -164.8(2) . . . . ?
C2 C1 C10 C11 16.5(3) . . . . ?
O1 C1 C10 C15 14.0(3) . . . . ?
C2 C1 C10 C15 -164.73(18) . . . . ?
C15 C10 C11 C12 -0.1(3) . . . . ?
C1 C10 C11 C12 178.76(18) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C12 C13 C14 C15 -0.8(4) . . . . ?
C13 C14 C15 C10 1.7(4) . . . . ?
C11 C10 C15 C14 -1.3(3) . . . . ?
C1 C10 C15 C14 179.9(2) . . . . ?

_refine_diff_density_max         0.306
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.052

_shelxl_version_number           2014-1


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_database_code_depnum_ccdc_archive 'CCDC 1026201'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_2h

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H13 Fe N O5'
_chemical_formula_sum            'C22 H13 Fe N O5'
_chemical_formula_weight         427.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.5432(4)
_cell_length_b                   15.2269(5)
_cell_length_c                   12.0419(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.7210(10)
_cell_angle_gamma                90
_cell_volume                     1932.34(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5097
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      25.29


_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.326
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.814
_shelx_estimated_absorpt_T_min   0.721
_shelx_estimated_absorpt_T_max   0.895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6425
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   '(Sheldrick, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker Smart Apex CCD diffractometer 01-670-01'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            11033
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.932
_diffrn_reflns_theta_max         25.345
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3544
_reflns_number_gt                2913
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/1 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0530P)²+0.2684P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3544
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0934
_refine_ls_wR_factor_gt          0.0868
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.66329(3) 0.83184(2) -0.07248(2) 0.04152(13) Uani 1 1 d . . . . .
O1 O 0.8490(2) 1.02433(11) -0.09997(15) 0.0786(6) Uani 1 1 d . . . . .
O2 O 0.46614(17) 0.90865(12) 0.06606(14) 0.0688(5) Uani 1 1 d . . . . .
O3 O 0.69176(19) 0.68782(13) 0.09011(16) 0.0759(5) Uani 1 1 d . . . . .
O4 O 0.5571(2) 0.70035(14) -0.22615(16) 0.0899(6) Uani 1 1 d . . . . .
O5 O 0.6157(2) 0.96620(13) -0.24636(15) 0.0822(6) Uani 1 1 d . . . . .
N1 N 0.95212(19) 0.71504(14) -0.01355(18) 0.0626(5) Uani 1 1 d . . . . .
C1 C 0.8295(2) 0.98385(15) -0.01489(19) 0.0510(5) Uani 1 1 d . . . . .
C2 C 0.83605(19) 0.88665(14) -0.01195(17) 0.0442(5) Uani 1 1 d . . . . .
H2 H 0.8710 0.8611 0.0571 0.053 Uiso 1 1 calc R U . . .
C3 C 0.8588(2) 0.83862(15) -0.10994(19) 0.0499(5) Uani 1 1 d . . . . .
H3 H 0.8762 0.8757 -0.1742 0.060 Uiso 1 1 calc R U . . .
C4 C 0.7639(2) 0.99353(15) 0.18472(18) 0.0497(5) Uani 1 1 d . . . . .
H4 H 0.7665 0.9326 0.1894 0.060 Uiso 1 1 calc R U . . .
C5 C 0.79608(19) 1.03327(14) 0.08775(18) 0.0454(5) Uani 1 1 d . . . . .
C6 C 0.7938(2) 1.12610(15) 0.0822(2) 0.0588(6) Uani 1 1 d . . . . .
H6 H 0.8176 1.1541 0.0175 0.071 Uiso 1 1 calc R U . . .
C7 C 0.7574(3) 1.17467(16) 0.1700(3) 0.0702(8) Uani 1 1 d . . . . .
H7 H 0.7556 1.2356 0.1641 0.084 Uiso 1 1 calc R U . . .
C8 C 0.6818(3) 1.1835(2) 0.3632(3) 0.0893(11) Uani 1 1 d . . . . .
H8 H 0.6781 1.2444 0.3591 0.107 Uiso 1 1 calc R U . . .
C9 C 0.6486(3) 1.1431(3) 0.4573(3) 0.1009(13) Uani 1 1 d . . . . .
H9 H 0.6222 1.1762 0.5172 0.121 Uiso 1 1 calc R U . . .
C10 C 0.6536(3) 1.0512(3) 0.4657(3) 0.0944(11) Uani 1 1 d . . . . .
H10 H 0.6301 1.0239 0.5310 0.113 Uiso 1 1 calc R U . . .
C11 C 0.6926(3) 1.0019(2) 0.3791(2) 0.0736(8) Uani 1 1 d . . . . .
H11 H 0.6969 0.9411 0.3861 0.088 Uiso 1 1 calc R U . . .
C12 C 0.7266(2) 1.04239(16) 0.27817(19) 0.0542(6) Uani 1 1 d . . . . .
C13 C 0.7222(2) 1.13495(17) 0.2698(2) 0.0609(7) Uani 1 1 d . . . . .
C14 C 0.92419(19) 0.75329(16) -0.11130(19) 0.0518(6) Uani 1 1 d . . . . .
C15 C 0.9589(2) 0.71724(19) -0.2117(2) 0.0695(7) Uani 1 1 d . . . . .
H15 H 0.9399 0.7462 -0.2781 0.083 Uiso 1 1 calc R U . . .
C16 C 1.0218(3) 0.6380(2) -0.2117(3) 0.0926(11) Uani 1 1 d . . . . .
H16 H 1.0444 0.6121 -0.2782 0.111 Uiso 1 1 calc R U . . .
C17 C 1.0502(3) 0.5983(2) -0.1129(4) 0.0937(11) Uani 1 1 d . . . . .
H17 H 1.0930 0.5449 -0.1107 0.112 Uiso 1 1 calc R U . . .
C18 C 1.0144(3) 0.6385(2) -0.0163(3) 0.0817(9) Uani 1 1 d . . . . .
H18 H 1.0347 0.6109 0.0508 0.098 Uiso 1 1 calc R U . . .
C19 C 0.5419(2) 0.87900(15) 0.01265(18) 0.0482(5) Uani 1 1 d . . . . .
C20 C 0.6867(2) 0.74363(16) 0.02813(18) 0.0498(5) Uani 1 1 d . . . . .
C21 C 0.5973(2) 0.75311(16) -0.16779(19) 0.0560(6) Uani 1 1 d . . . . .
C22 C 0.6361(2) 0.91684(16) -0.17852(19) 0.0558(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
Fe1 C21 1.786(3) . ?
Fe1 C19 1.812(2) . ?
Fe1 C20 1.821(2) . ?
Fe1 C22 1.835(2) . ?
Fe1 C2 2.113(2) . ?
Fe1 C3 2.125(2) . ?
O1 C1 1.218(3) . ?
O2 C19 1.134(2) . ?
O3 C20 1.131(3) . ?
O4 C21 1.141(3) . ?
O5 C22 1.126(3) . ?
N1 C14 1.338(3) . ?
N1 C18 1.339(3) . ?
C1 C2 1.482(3) . ?
C1 C5 1.498(3) . ?
C2 C3 1.415(3) . ?
C2 H2 0.9800 . ?
C3 C14 1.471(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.367(3) . ?
C4 C12 1.415(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.415(3) . ?
C6 C7 1.355(4) . ?
C6 H6 0.9300 . ?
C7 C13 1.405(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.345(6) . ?
C8 C13 1.422(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.403(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.358(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.419(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.414(4) . ?
C14 C15 1.387(3) . ?
C15 C16 1.376(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.360(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

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
C21 Fe1 C19 111.18(11) . . ?
C21 Fe1 C20 88.56(11) . . ?
C19 Fe1 C20 89.98(10) . . ?
C21 Fe1 C22 88.66(11) . . ?
C19 Fe1 C22 90.91(10) . . ?
C20 Fe1 C22 177.21(10) . . ?
C21 Fe1 C2 143.31(10) . . ?
C19 Fe1 C2 105.33(9) . . ?
C20 Fe1 C2 87.92(9) . . ?
C22 Fe1 C2 94.39(10) . . ?
C21 Fe1 C3 104.94(10) . . ?
C19 Fe1 C3 143.77(9) . . ?
C20 Fe1 C3 93.68(9) . . ?
C22 Fe1 C3 87.15(10) . . ?
C2 Fe1 C3 39.00(8) . . ?
C14 N1 C18 116.9(2) . . ?
O1 C1 C2 121.1(2) . . ?
O1 C1 C5 119.3(2) . . ?
C2 C1 C5 119.60(19) . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 Fe1 70.97(12) . . ?
C1 C2 Fe1 110.32(14) . . ?
C3 C2 H2 115.7 . . ?
C1 C2 H2 115.7 . . ?
Fe1 C2 H2 115.7 . . ?
C2 C3 C14 123.8(2) . . ?
C2 C3 Fe1 70.04(12) . . ?
C14 C3 Fe1 114.67(15) . . ?
C2 C3 H3 113.7 . . ?
C14 C3 H3 113.7 . . ?
Fe1 C3 H3 113.7 . . ?
C5 C4 C12 121.9(2) . . ?
C5 C4 H4 119.0 . . ?
C12 C4 H4 119.0 . . ?
C4 C5 C6 118.5(2) . . ?
C4 C5 C1 123.6(2) . . ?
C6 C5 C1 117.9(2) . . ?
C7 C6 C5 120.9(2) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C13 121.4(2) . . ?
C6 C7 H7 119.3 . . ?
C13 C7 H7 119.3 . . ?
C9 C8 C13 121.3(3) . . ?
C9 C8 H8 119.3 . . ?
C13 C8 H8 119.3 . . ?
C8 C9 C10 120.5(3) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 120.5(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C4 118.5(2) . . ?
C13 C12 C11 119.0(2) . . ?
C4 C12 C11 122.5(2) . . ?
C7 C13 C12 118.7(2) . . ?
C7 C13 C8 123.1(3) . . ?
C12 C13 C8 118.2(3) . . ?
N1 C14 C15 122.5(2) . . ?
N1 C14 C3 117.7(2) . . ?
C15 C14 C3 119.7(2) . . ?
C16 C15 C14 119.1(3) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C17 C16 C15 118.9(3) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C18 118.9(3) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
N1 C18 C17 123.7(3) . . ?
N1 C18 H18 118.2 . . ?
C17 C18 H18 118.2 . . ?
O2 C19 Fe1 179.8(2) . . ?
O3 C20 Fe1 174.9(2) . . ?
O4 C21 Fe1 177.4(2) . . ?
O5 C22 Fe1 176.6(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -3.3(3) . . . . ?
C5 C1 C2 C3 175.60(19) . . . . ?
O1 C1 C2 Fe1 -82.5(2) . . . . ?
C5 C1 C2 Fe1 96.3(2) . . . . ?
C1 C2 C3 C14 150.2(2) . . . . ?
Fe1 C2 C3 C14 -106.9(2) . . . . ?
C1 C2 C3 Fe1 -102.92(19) . . . . ?
C12 C4 C5 C6 1.1(3) . . . . ?
C12 C4 C5 C1 -176.7(2) . . . . ?
O1 C1 C5 C4 175.2(2) . . . . ?
C2 C1 C5 C4 -3.7(3) . . . . ?
O1 C1 C5 C6 -2.6(3) . . . . ?
C2 C1 C5 C6 178.5(2) . . . . ?
C4 C5 C6 C7 -1.7(3) . . . . ?
C1 C5 C6 C7 176.2(2) . . . . ?
C5 C6 C7 C13 0.8(4) . . . . ?
C13 C8 C9 C10 0.2(5) . . . . ?
C8 C9 C10 C11 0.3(5) . . . . ?
C9 C10 C11 C12 -1.1(4) . . . . ?
C5 C4 C12 C13 0.4(3) . . . . ?
C5 C4 C12 C11 179.8(2) . . . . ?
C10 C11 C12 C13 1.4(4) . . . . ?
C10 C11 C12 C4 -178.0(2) . . . . ?
C6 C7 C13 C12 0.6(4) . . . . ?
C6 C7 C13 C8 -179.1(2) . . . . ?
C4 C12 C13 C7 -1.2(3) . . . . ?
C11 C12 C13 C7 179.3(2) . . . . ?
C4 C12 C13 C8 178.5(2) . . . . ?
C11 C12 C13 C8 -0.9(3) . . . . ?
C9 C8 C13 C7 179.9(3) . . . . ?
C9 C8 C13 C12 0.1(4) . . . . ?
C18 N1 C14 C15 -1.0(4) . . . . ?
C18 N1 C14 C3 -178.4(2) . . . . ?
C2 C3 C14 N1 7.0(3) . . . . ?
Fe1 C3 C14 N1 -74.7(2) . . . . ?
C2 C3 C14 C15 -170.5(2) . . . . ?
Fe1 C3 C14 C15 107.8(2) . . . . ?
N1 C14 C15 C16 1.6(4) . . . . ?
C3 C14 C15 C16 179.0(2) . . . . ?
C14 C15 C16 C17 -1.2(4) . . . . ?
C15 C16 C17 C18 0.3(5) . . . . ?
C14 N1 C18 C17 0.0(4) . . . . ?
C16 C17 C18 N1 0.3(5) . . . . ?

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.047

_shelxl_version_number           2014-1

_database_code_depnum_ccdc_archive 'CCDC 1026202'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_3g

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H15 Fe N O4'
_chemical_formula_sum            'C24 H15 Fe N O4'
_chemical_formula_weight         437.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1323(6)
_cell_length_b                   10.4497(7)
_cell_length_c                   11.6044(8)
_cell_angle_alpha                87.7000(10)
_cell_angle_beta                 82.5140(10)
_cell_angle_gamma                69.3430(10)
_cell_volume                     1027.36(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4996
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      25.35

_exptl_crystal_description       platty
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.458
_exptl_crystal_size_mid          0.292
_exptl_crystal_size_min          0.108
_exptl_absorpt_coefficient_mu    0.764
_shelx_estimated_absorpt_T_min   0.721
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6539
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   '(Sheldrick, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker Smart Apex CCD diffractometer 01-670-01'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            8848
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.770
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3736
_reflns_number_gt                3053
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/1 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0318P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3736
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0737
_refine_ls_wR_factor_gt          0.0698
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_restrained_S_all      0.945
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.49172(3) 0.28110(3) 0.37574(2) 0.03636(11) Uani 1 1 d . . . . .
O1 O 0.61714(17) 0.50534(14) 0.30728(13) 0.0523(4) Uani 1 1 d . . . . .
O2 O 0.34452(18) 0.06963(15) 0.43949(13) 0.0532(4) Uani 1 1 d . . . . .
O3 O 0.2003(2) 0.50090(17) 0.46770(16) 0.0749(5) Uani 1 1 d . . . . .
O4 O 0.6824(2) 0.23842(18) 0.56796(15) 0.0763(5) Uani 1 1 d . . . . .
N1 N 0.6483(2) -0.06716(17) 0.25437(15) 0.0469(4) Uani 1 1 d . . . . .
C1 C 0.5690(2) 0.4147(2) 0.29577(18) 0.0405(5) Uani 1 1 d . . . . .
C2 C 0.5102(2) 0.36131(19) 0.20286(16) 0.0375(5) Uani 1 1 d . . . . .
C3 C 0.5678(2) 0.21691(19) 0.20170(16) 0.0384(5) Uani 1 1 d . . . . .
H3 H 0.5147 0.1668 0.1633 0.046 Uiso 1 1 calc R U . . .
C4 C 0.6926(2) 0.14595(19) 0.26676(17) 0.0392(5) Uani 1 1 d . . . . .
H4 H 0.7805 0.1800 0.2532 0.047 Uiso 1 1 calc R U . . .
C5 C 0.3872(2) 0.45243(19) 0.13542(16) 0.0374(5) Uani 1 1 d . . . . .
C6 C 0.3333(2) 0.5937(2) 0.15082(18) 0.0471(5) Uani 1 1 d . . . . .
H6 H 0.3743 0.6307 0.2048 0.056 Uiso 1 1 calc R U . . .
C7 C 0.2202(3) 0.6800(2) 0.08763(18) 0.0505(6) Uani 1 1 d . . . . .
H7 H 0.1864 0.7739 0.1003 0.061 Uiso 1 1 calc R U . . .
C8 C 0.1554(2) 0.6301(2) 0.00536(17) 0.0398(5) Uani 1 1 d . . . . .
C9 C 0.2116(2) 0.4888(2) -0.01121(18) 0.0461(5) Uani 1 1 d . . . . .
H9 H 0.1718 0.4520 -0.0662 0.055 Uiso 1 1 calc R U . . .
C10 C 0.3247(2) 0.4020(2) 0.05179(18) 0.0456(5) Uani 1 1 d . . . . .
H10 H 0.3598 0.3082 0.0382 0.055 Uiso 1 1 calc R U . . .
C11 C 0.0299(2) 0.7243(2) -0.05988(18) 0.0419(5) Uani 1 1 d . . . . .
C12 C -0.0779(3) 0.8445(2) -0.0089(2) 0.0563(6) Uani 1 1 d . . . . .
H12 H -0.0710 0.8666 0.0666 0.068 Uiso 1 1 calc R U . . .
C13 C -0.1957(3) 0.9323(2) -0.0689(2) 0.0662(7) Uani 1 1 d . . . . .
H13 H -0.2675 1.0115 -0.0326 0.079 Uiso 1 1 calc R U . . .
C14 C -0.2075(3) 0.9037(3) -0.1806(2) 0.0618(7) Uani 1 1 d . . . . .
H14 H -0.2854 0.9633 -0.2210 0.074 Uiso 1 1 calc R U . . .
C15 C -0.1013(3) 0.7845(3) -0.2322(2) 0.0592(6) Uani 1 1 d . . . . .
H15 H -0.1082 0.7637 -0.3080 0.071 Uiso 1 1 calc R U . . .
C16 C 0.0150(2) 0.6956(2) -0.17285(19) 0.0481(5) Uani 1 1 d . . . . .
H16 H 0.0844 0.6154 -0.2090 0.058 Uiso 1 1 calc R U . . .
C17 C 0.7456(2) -0.00431(19) 0.28131(17) 0.0398(5) Uani 1 1 d . . . . .
C18 C 0.8895(3) -0.0757(2) 0.32019(19) 0.0508(6) Uani 1 1 d . . . . .
H18 H 0.9543 -0.0295 0.3377 0.061 Uiso 1 1 calc R U . . .
C19 C 0.9360(3) -0.2158(2) 0.3327(2) 0.0638(7) Uani 1 1 d . . . . .
H19 H 1.0314 -0.2651 0.3597 0.077 Uiso 1 1 calc R U . . .
C20 C 0.8383(3) -0.2812(2) 0.3044(2) 0.0661(7) Uani 1 1 d . . . . .
H20 H 0.8670 -0.3757 0.3105 0.079 Uiso 1 1 calc R U . . .
C21 C 0.6976(3) -0.2035(2) 0.2668(2) 0.0595(6) Uani 1 1 d . . . . .
H21 H 0.6318 -0.2484 0.2487 0.071 Uiso 1 1 calc R U . . .
C22 C 0.4022(2) 0.1477(2) 0.41134(17) 0.0399(5) Uani 1 1 d . . . . .
C23 C 0.3141(3) 0.4155(2) 0.43405(19) 0.0481(5) Uani 1 1 d . . . . .
C24 C 0.6045(3) 0.2552(2) 0.4955(2) 0.0472(5) 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
Fe1 C24 1.792(2) . ?
Fe1 C23 1.801(2) . ?
Fe1 C22 1.858(2) . ?
Fe1 C1 1.931(2) . ?
Fe1 C3 2.1037(19) . ?
Fe1 C2 2.1522(18) . ?
Fe1 C4 2.1612(19) . ?
O1 C1 1.194(2) . ?
O2 C22 1.135(2) . ?
O3 C23 1.139(2) . ?
O4 C24 1.141(2) . ?
N1 C21 1.342(3) . ?
N1 C17 1.349(2) . ?
C1 C2 1.474(3) . ?
C2 C3 1.412(2) . ?
C2 C5 1.481(3) . ?
C3 C4 1.415(3) . ?
C3 H3 0.9800 . ?
C4 C17 1.481(3) . ?
C4 H4 0.9800 . ?
C5 C6 1.393(3) . ?
C5 C10 1.394(3) . ?
C6 C7 1.380(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.392(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.394(3) . ?
C8 C11 1.492(3) . ?
C9 C10 1.381(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.390(3) . ?
C11 C16 1.391(3) . ?
C12 C13 1.390(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.387(3) . ?
C18 C19 1.380(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.372(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?

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
C24 Fe1 C23 100.30(10) . . ?
C24 Fe1 C22 98.51(9) . . ?
C23 Fe1 C22 92.28(9) . . ?
C24 Fe1 C1 96.80(9) . . ?
C23 Fe1 C1 90.30(9) . . ?
C22 Fe1 C1 163.75(8) . . ?
C24 Fe1 C3 129.16(9) . . ?
C23 Fe1 C3 128.36(8) . . ?
C22 Fe1 C3 93.83(8) . . ?
C1 Fe1 C3 72.15(8) . . ?
C24 Fe1 C2 134.92(9) . . ?
C23 Fe1 C2 97.44(8) . . ?
C22 Fe1 C2 121.86(8) . . ?
C1 Fe1 C2 41.89(8) . . ?
C3 Fe1 C2 38.73(7) . . ?
C24 Fe1 C4 91.14(9) . . ?
C23 Fe1 C4 166.10(8) . . ?
C22 Fe1 C4 93.82(8) . . ?
C1 Fe1 C4 80.45(8) . . ?
C3 Fe1 C4 38.73(7) . . ?
C2 Fe1 C4 68.76(7) . . ?
C21 N1 C17 116.65(19) . . ?
O1 C1 C2 137.09(19) . . ?
O1 C1 Fe1 145.11(17) . . ?
C2 C1 Fe1 77.10(11) . . ?
C3 C2 C1 111.10(16) . . ?
C3 C2 C5 126.60(18) . . ?
C1 C2 C5 121.62(17) . . ?
C3 C2 Fe1 68.78(10) . . ?
C1 C2 Fe1 61.01(10) . . ?
C5 C2 Fe1 130.64(13) . . ?
C2 C3 C4 118.99(18) . . ?
C2 C3 Fe1 72.49(11) . . ?
C4 C3 Fe1 72.83(11) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
Fe1 C3 H3 120.3 . . ?
C3 C4 C17 121.83(17) . . ?
C3 C4 Fe1 68.44(10) . . ?
C17 C4 Fe1 121.35(13) . . ?
C3 C4 H4 112.8 . . ?
C17 C4 H4 112.8 . . ?
Fe1 C4 H4 112.8 . . ?
C6 C5 C10 117.24(18) . . ?
C6 C5 C2 120.70(18) . . ?
C10 C5 C2 122.02(18) . . ?
C7 C6 C5 121.36(19) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 121.7(2) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C7 C8 C9 116.82(19) . . ?
C7 C8 C11 121.10(19) . . ?
C9 C8 C11 122.07(18) . . ?
C10 C9 C8 121.76(19) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C9 C10 C5 121.13(19) . . ?
C9 C10 H10 119.4 . . ?
C5 C10 H10 119.4 . . ?
C12 C11 C16 117.40(19) . . ?
C12 C11 C8 120.75(19) . . ?
C16 C11 C8 121.8(2) . . ?
C13 C12 C11 121.1(2) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 118.6(2) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
C14 C15 C16 121.0(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C11 121.0(2) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
N1 C17 C18 122.23(18) . . ?
N1 C17 C4 116.95(17) . . ?
C18 C17 C4 120.81(19) . . ?
C19 C18 C17 119.6(2) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C20 C19 C18 118.7(2) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
C21 C20 C19 118.3(2) . . ?
C21 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
N1 C21 C20 124.5(2) . . ?
N1 C21 H21 117.7 . . ?
C20 C21 H21 117.7 . . ?
O2 C22 Fe1 175.91(18) . . ?
O3 C23 Fe1 177.9(2) . . ?
O4 C24 Fe1 176.7(2) . . ?

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.046

_shelxl_version_number           2014-1

_database_code_depnum_ccdc_archive 'CCDC 1026203'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_4a

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H11 N O'
_chemical_formula_sum            'C15 H11 N O'
_chemical_formula_weight         221.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   15.2083(8)
_cell_length_b                   6.5450(3)
_cell_length_c                   21.7516(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2165.12(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4113
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      27.12

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.442
_exptl_crystal_size_mid          0.403
_exptl_crystal_size_min          0.156
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6295
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   '(Sheldrick, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker Smart Apex CCD diffractometer 01-670-01'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            13809
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.872
_diffrn_reflns_theta_max         27.442
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             4802
_reflns_number_gt                3459
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.887
_reflns_Friedel_fraction_max     0.935
_reflns_Friedel_fraction_full    0.958

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/1 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0736P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1280 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4802
_refine_ls_number_parameters     307
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1431
_refine_ls_wR_factor_gt          0.1249
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5151(2) 0.5095(4) 0.15499(16) 0.0457(8) Uani 1 1 d . . . . .
C1 C 0.4743(3) 0.9788(6) 0.0347(2) 0.0400(11) Uani 1 1 d . . . . .
H1 H 0.4658 1.0855 0.0071 0.048 Uiso 1 1 calc R U . . .
C2 C 0.4478(3) 0.9981(6) 0.0951(2) 0.0377(11) Uani 1 1 d . . . . .
H2 H 0.4206 1.1191 0.1070 0.045 Uiso 1 1 calc R U . . .
C3 C 0.4595(2) 0.8471(6) 0.13926(17) 0.0351(8) Uani 1 1 d . . . . .
C4 C 0.4998(2) 0.6586(6) 0.12184(16) 0.0348(8) Uani 1 1 d . . . . .
N5 N 0.52599(19) 0.6438(5) 0.05841(14) 0.0339(7) Uani 1 1 d . . . . .
C6 C 0.5638(3) 0.4616(7) 0.0398(2) 0.0430(10) Uani 1 1 d . . . . .
H6 H 0.5714 0.3576 0.0685 0.052 Uiso 1 1 calc R U . . .
C7 C 0.5897(3) 0.4309(7) -0.0182(2) 0.0514(11) Uani 1 1 d . . . . .
H7 H 0.6161 0.3080 -0.0290 0.062 Uiso 1 1 calc R U . . .
C8 C 0.5772(3) 0.5831(8) -0.0629(2) 0.0556(12) Uani 1 1 d . . . . .
H8 H 0.5938 0.5606 -0.1035 0.067 Uiso 1 1 calc R U . . .
C9 C 0.5408(3) 0.7621(7) -0.04594(18) 0.0459(10) Uani 1 1 d . . . . .
H9 H 0.5333 0.8639 -0.0753 0.055 Uiso 1 1 calc R U . . .
C10 C 0.5135(2) 0.7996(6) 0.01570(17) 0.0357(9) Uani 1 1 d . . . . .
C11 C 0.4276(2) 0.8787(6) 0.20273(19) 0.0394(10) Uani 1 1 d . . . . .
C12 C 0.3876(3) 0.7252(7) 0.23646(19) 0.0456(10) Uani 1 1 d . . . . .
H12 H 0.3856 0.5934 0.2205 0.055 Uiso 1 1 calc R U . . .
C13 C 0.3507(3) 0.7638(8) 0.2930(2) 0.0561(12) Uani 1 1 d . . . . .
H13 H 0.3233 0.6591 0.3147 0.067 Uiso 1 1 calc R U . . .
C14 C 0.3545(3) 0.9590(10) 0.3178(2) 0.0657(15) Uani 1 1 d . . . . .
H14 H 0.3288 0.9860 0.3557 0.079 Uiso 1 1 calc R U . . .
C15 C 0.3958(3) 1.1097(8) 0.2866(2) 0.0653(14) Uani 1 1 d . . . . .
H15 H 0.3998 1.2393 0.3038 0.078 Uiso 1 1 calc R U . . .
C16 C 0.4322(3) 1.0732(7) 0.2290(2) 0.0505(11) Uani 1 1 d . . . . .
H16 H 0.4598 1.1788 0.2078 0.061 Uiso 1 1 calc R U . . .
O21 O 0.2449(2) 0.0164(4) -0.02738(18) 0.0515(9) Uani 1 1 d . . . . .
C21 C 0.2863(3) 0.4807(6) 0.0937(2) 0.0422(11) Uani 1 1 d . . . . .
H21 H 0.2947 0.5872 0.1214 0.051 Uiso 1 1 calc R U . . .
C22 C 0.3126(3) 0.5029(6) 0.0335(3) 0.0402(12) Uani 1 1 d . . . . .
H22 H 0.3387 0.6252 0.0216 0.048 Uiso 1 1 calc R U . . .
C23 C 0.3020(2) 0.3512(5) -0.00999(17) 0.0362(9) Uani 1 1 d . . . . .
C24 C 0.2606(2) 0.1634(6) 0.00660(17) 0.0370(9) Uani 1 1 d . . . . .
N25 N 0.2351(2) 0.1470(5) 0.07044(13) 0.0362(8) Uani 1 1 d . . . . .
C26 C 0.1978(3) -0.0334(7) 0.0883(2) 0.0436(10) Uani 1 1 d . . . . .
H26 H 0.1894 -0.1353 0.0591 0.052 Uiso 1 1 calc R U . . .
C27 C 0.1726(3) -0.0695(8) 0.1469(2) 0.0555(12) Uani 1 1 d . . . . .
H27 H 0.1479 -0.1943 0.1579 0.067 Uiso 1 1 calc R U . . .
C28 C 0.1844(3) 0.0852(7) 0.1911(2) 0.0553(12) Uani 1 1 d . . . . .
H28 H 0.1673 0.0640 0.2317 0.066 Uiso 1 1 calc R U . . .
C29 C 0.2204(3) 0.2624(7) 0.17427(19) 0.0495(11) Uani 1 1 d . . . . .
H29 H 0.2279 0.3638 0.2038 0.059 Uiso 1 1 calc R U . . .
C30 C 0.2478(2) 0.3022(6) 0.11299(17) 0.0376(9) Uani 1 1 d . . . . .
C31 C 0.3335(2) 0.3848(6) -0.07388(19) 0.0398(10) Uani 1 1 d . . . . .
C32 C 0.3736(3) 0.2299(6) -0.10768(19) 0.0453(10) Uani 1 1 d . . . . .
H32 H 0.3755 0.0978 -0.0920 0.054 Uiso 1 1 calc R U . . .
C33 C 0.4106(3) 0.2719(8) -0.1646(2) 0.0554(11) Uani 1 1 d . . . . .
H33 H 0.4382 0.1675 -0.1863 0.066 Uiso 1 1 calc R U . . .
C34 C 0.4074(3) 0.4652(9) -0.1896(2) 0.0608(14) Uani 1 1 d . . . . .
H34 H 0.4325 0.4920 -0.2277 0.073 Uiso 1 1 calc R U . . .
C35 C 0.3659(3) 0.6185(8) -0.1567(2) 0.0580(12) Uani 1 1 d . . . . .
H35 H 0.3620 0.7489 -0.1735 0.070 Uiso 1 1 calc R U . . .
C36 C 0.3299(3) 0.5811(7) -0.0992(2) 0.0511(11) Uani 1 1 d . . . . .
H36 H 0.3034 0.6867 -0.0774 0.061 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.236(5) . ?
C1 C10 1.379(6) . ?
C1 C2 1.381(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.389(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.428(5) . ?
C3 C11 1.478(6) . ?
C4 N5 1.439(5) . ?
N5 C6 1.384(5) . ?
N5 C10 1.393(5) . ?
C6 C7 1.336(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.405(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.347(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.425(5) . ?
C9 H9 0.9300 . ?
C11 C12 1.385(6) . ?
C11 C16 1.397(6) . ?
C12 C13 1.375(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.388(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.351(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
O21 C24 1.237(5) . ?
C21 C30 1.373(6) . ?
C21 C22 1.376(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.381(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.427(5) . ?
C23 C31 1.486(6) . ?
C24 N25 1.446(5) . ?
N25 C26 1.367(5) . ?
N25 C30 1.388(4) . ?
C26 C27 1.352(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.408(7) . ?
C27 H27 0.9300 . ?
C28 C29 1.334(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.421(6) . ?
C29 H29 0.9300 . ?
C31 C32 1.393(5) . ?
C31 C36 1.398(6) . ?
C32 C33 1.387(6) . ?
C32 H32 0.9300 . ?
C33 C34 1.378(6) . ?
C33 H33 0.9300 . ?
C34 C35 1.385(7) . ?
C34 H34 0.9300 . ?
C35 C36 1.388(6) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?

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
C10 C1 C2 119.3(4) . . ?
C10 C1 H1 120.4 . . ?
C2 C1 H1 120.4 . . ?
C1 C2 C3 123.7(4) . . ?
C1 C2 H2 118.1 . . ?
C3 C2 H2 118.1 . . ?
C2 C3 C4 119.1(4) . . ?
C2 C3 C11 120.3(4) . . ?
C4 C3 C11 120.6(3) . . ?
O1 C4 C3 127.5(4) . . ?
O1 C4 N5 117.0(3) . . ?
C3 C4 N5 115.6(3) . . ?
C6 N5 C10 119.5(4) . . ?
C6 N5 C4 117.0(3) . . ?
C10 N5 C4 123.5(3) . . ?
C7 C6 N5 121.8(4) . . ?
C7 C6 H6 119.1 . . ?
N5 C6 H6 119.1 . . ?
C6 C7 C8 120.5(4) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 118.9(4) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 121.8(4) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C1 C10 N5 118.8(4) . . ?
C1 C10 C9 123.7(4) . . ?
N5 C10 C9 117.5(3) . . ?
C12 C11 C16 117.8(4) . . ?
C12 C11 C3 122.5(4) . . ?
C16 C11 C3 119.5(4) . . ?
C13 C12 C11 121.3(5) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 119.9(5) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 119.8(5) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.8(5) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C11 120.3(5) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
C30 C21 C22 120.3(4) . . ?
C30 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C23 122.8(4) . . ?
C21 C22 H22 118.6 . . ?
C23 C22 H22 118.6 . . ?
C22 C23 C24 119.8(4) . . ?
C22 C23 C31 119.8(4) . . ?
C24 C23 C31 120.4(3) . . ?
O21 C24 C23 127.1(4) . . ?
O21 C24 N25 117.7(4) . . ?
C23 C24 N25 115.2(3) . . ?
C26 N25 C30 120.0(4) . . ?
C26 N25 C24 116.7(3) . . ?
C30 N25 C24 123.3(3) . . ?
C27 C26 N25 122.5(4) . . ?
C27 C26 H26 118.8 . . ?
N25 C26 H26 118.8 . . ?
C26 C27 C28 118.8(4) . . ?
C26 C27 H27 120.6 . . ?
C28 C27 H27 120.6 . . ?
C29 C28 C27 119.4(5) . . ?
C29 C28 H28 120.3 . . ?
C27 C28 H28 120.3 . . ?
C28 C29 C30 122.5(4) . . ?
C28 C29 H29 118.7 . . ?
C30 C29 H29 118.7 . . ?
C21 C30 N25 118.6(4) . . ?
C21 C30 C29 124.6(4) . . ?
N25 C30 C29 116.8(4) . . ?
C32 C31 C36 118.5(4) . . ?
C32 C31 C23 121.8(4) . . ?
C36 C31 C23 119.4(4) . . ?
C33 C32 C31 120.3(4) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C34 C33 C32 121.3(4) . . ?
C34 C33 H33 119.4 . . ?
C32 C33 H33 119.4 . . ?
C33 C34 C35 118.5(5) . . ?
C33 C34 H34 120.7 . . ?
C35 C34 H34 120.7 . . ?
C34 C35 C36 121.1(5) . . ?
C34 C35 H35 119.4 . . ?
C36 C35 H35 119.4 . . ?
C35 C36 C31 120.1(4) . . ?
C35 C36 H36 119.9 . . ?
C31 C36 H36 119.9 . . ?

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
C10 C1 C2 C3 1.1(6) . . . . ?
C1 C2 C3 C4 -1.1(6) . . . . ?
C1 C2 C3 C11 -178.8(4) . . . . ?
C2 C3 C4 O1 179.9(4) . . . . ?
C11 C3 C4 O1 -2.3(6) . . . . ?
C2 C3 C4 N5 0.6(5) . . . . ?
C11 C3 C4 N5 178.3(3) . . . . ?
O1 C4 N5 C6 1.7(5) . . . . ?
C3 C4 N5 C6 -178.9(3) . . . . ?
O1 C4 N5 C10 -179.7(3) . . . . ?
C3 C4 N5 C10 -0.3(5) . . . . ?
C10 N5 C6 C7 0.7(6) . . . . ?
C4 N5 C6 C7 179.3(4) . . . . ?
N5 C6 C7 C8 -1.5(7) . . . . ?
C6 C7 C8 C9 1.7(7) . . . . ?
C7 C8 C9 C10 -1.0(7) . . . . ?
C2 C1 C10 N5 -0.7(5) . . . . ?
C2 C1 C10 C9 178.1(4) . . . . ?
C6 N5 C10 C1 178.9(3) . . . . ?
C4 N5 C10 C1 0.3(5) . . . . ?
C6 N5 C10 C9 0.0(5) . . . . ?
C4 N5 C10 C9 -178.6(3) . . . . ?
C8 C9 C10 C1 -178.6(4) . . . . ?
C8 C9 C10 N5 0.2(6) . . . . ?
C2 C3 C11 C12 139.6(4) . . . . ?
C4 C3 C11 C12 -38.1(5) . . . . ?
C2 C3 C11 C16 -36.0(5) . . . . ?
C4 C3 C11 C16 146.3(4) . . . . ?
C16 C11 C12 C13 2.2(6) . . . . ?
C3 C11 C12 C13 -173.5(4) . . . . ?
C11 C12 C13 C14 -1.1(7) . . . . ?
C12 C13 C14 C15 -1.1(7) . . . . ?
C13 C14 C15 C16 2.0(8) . . . . ?
C14 C15 C16 C11 -0.8(7) . . . . ?
C12 C11 C16 C15 -1.3(6) . . . . ?
C3 C11 C16 C15 174.5(4) . . . . ?
C30 C21 C22 C23 0.1(7) . . . . ?
C21 C22 C23 C24 1.3(6) . . . . ?
C21 C22 C23 C31 -178.9(4) . . . . ?
C22 C23 C24 O21 178.4(4) . . . . ?
C31 C23 C24 O21 -1.5(6) . . . . ?
C22 C23 C24 N25 -1.8(5) . . . . ?
C31 C23 C24 N25 178.4(3) . . . . ?
O21 C24 N25 C26 1.9(5) . . . . ?
C23 C24 N25 C26 -178.0(3) . . . . ?
O21 C24 N25 C30 -179.0(4) . . . . ?
C23 C24 N25 C30 1.1(5) . . . . ?
C30 N25 C26 C27 -0.4(6) . . . . ?
C24 N25 C26 C27 178.7(4) . . . . ?
N25 C26 C27 C28 0.6(7) . . . . ?
C26 C27 C28 C29 -0.3(7) . . . . ?
C27 C28 C29 C30 -0.1(7) . . . . ?
C22 C21 C30 N25 -0.9(6) . . . . ?
C22 C21 C30 C29 178.4(4) . . . . ?
C26 N25 C30 C21 179.3(4) . . . . ?
C24 N25 C30 C21 0.2(5) . . . . ?
C26 N25 C30 C29 0.0(5) . . . . ?
C24 N25 C30 C29 -179.1(3) . . . . ?
C28 C29 C30 C21 -179.0(4) . . . . ?
C28 C29 C30 N25 0.3(6) . . . . ?
C22 C23 C31 C32 140.9(4) . . . . ?
C24 C23 C31 C32 -39.3(5) . . . . ?
C22 C23 C31 C36 -33.6(5) . . . . ?
C24 C23 C31 C36 146.2(4) . . . . ?
C36 C31 C32 C33 1.4(6) . . . . ?
C23 C31 C32 C33 -173.1(4) . . . . ?
C31 C32 C33 C34 -1.3(6) . . . . ?
C32 C33 C34 C35 -0.2(7) . . . . ?
C33 C34 C35 C36 1.5(7) . . . . ?
C34 C35 C36 C31 -1.4(7) . . . . ?
C32 C31 C36 C35 -0.1(6) . . . . ?
C23 C31 C36 C35 174.6(4) . . . . ?

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.053

_shelxl_version_number           2014-1

_database_code_depnum_ccdc_archive 'CCDC 1026204'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_4d

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 I N O'
_chemical_formula_sum            'C15 H10 I N O'
_chemical_formula_weight         347.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.492(4)
_cell_length_b                   21.091(13)
_cell_length_c                   9.629(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.311(10)
_cell_angle_gamma                90
_cell_volume                     1288.1(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4896
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      25.20

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.478
_exptl_crystal_size_mid          0.232
_exptl_crystal_size_min          0.174
_exptl_absorpt_coefficient_mu    2.472
_shelx_estimated_absorpt_T_min   0.385
_shelx_estimated_absorpt_T_max   0.673
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.3689
_exptl_absorpt_correction_T_max  0.6666
_exptl_absorpt_process_details   '(Sheldrick, 2000)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker Smart Apex CCD diffractometer 01-670-01'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            10484
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.931
_diffrn_reflns_theta_max         25.436
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2368
_reflns_number_gt                1859
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/1 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0522P)²+0.1091P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2368
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1033
_refine_ls_wR_factor_gt          0.0973
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.86398(6) 0.23563(2) 0.76419(4) 0.1022(2) Uani 1 1 d . . . . .
O1 O 0.2933(4) 0.44615(13) 0.2557(3) 0.0639(7) Uani 1 1 d . . . . .
C1 C 0.7907(6) 0.5583(2) 0.2267(4) 0.0626(11) Uani 1 1 d . . . . .
H1 H 0.9029 0.5851 0.2221 0.075 Uiso 1 1 calc R U . . .
C2 C 0.8236(6) 0.5061(2) 0.3136(4) 0.0579(9) Uani 1 1 d . . . . .
H2 H 0.9598 0.4975 0.3636 0.069 Uiso 1 1 calc R U . . .
C3 C 0.6622(5) 0.46573(17) 0.3300(4) 0.0488(8) Uani 1 1 d . . . . .
C4 C 0.4526(5) 0.47724(17) 0.2523(4) 0.0487(8) Uani 1 1 d . . . . .
C5 C 0.2282(6) 0.54373(19) 0.0817(4) 0.0582(9) Uani 1 1 d . . . . .
H5 H 0.1184 0.5172 0.0924 0.070 Uiso 1 1 calc R U . . .
C6 C 0.1866(7) 0.5923(2) -0.0081(4) 0.0675(11) Uani 1 1 d . . . . .
H6 H 0.0501 0.5988 -0.0600 0.081 Uiso 1 1 calc R U . . .
C7 C 0.3499(7) 0.6338(2) -0.0242(5) 0.0697(11) Uani 1 1 d . . . . .
H7 H 0.3222 0.6681 -0.0862 0.084 Uiso 1 1 calc R U . . .
C8 C 0.5445(7) 0.6233(2) 0.0506(5) 0.0654(11) Uani 1 1 d . . . . .
H8 H 0.6518 0.6509 0.0397 0.078 Uiso 1 1 calc R U . . .
C9 C 0.5944(6) 0.57133(17) 0.1465(4) 0.0522(9) Uani 1 1 d . . . . .
N10 N 0.4288(4) 0.53134(13) 0.1594(3) 0.0478(7) Uani 1 1 d . . . . .
C11 C 0.7032(5) 0.41049(17) 0.4257(4) 0.0495(8) Uani 1 1 d . . . . .
C12 C 0.8879(6) 0.37510(19) 0.4371(4) 0.0592(10) Uani 1 1 d . . . . .
H12 H 0.9822 0.3853 0.3802 0.071 Uiso 1 1 calc R U . . .
C13 C 0.9322(6) 0.32535(19) 0.5315(4) 0.0634(10) Uani 1 1 d . . . . .
H13 H 1.0556 0.3021 0.5375 0.076 Uiso 1 1 calc R U . . .
C14 C 0.7941(6) 0.30983(18) 0.6171(4) 0.0606(10) Uani 1 1 d . . . . .
C15 C 0.6093(6) 0.34333(19) 0.6061(4) 0.0606(10) Uani 1 1 d . . . . .
H15 H 0.5148 0.3325 0.6624 0.073 Uiso 1 1 calc R U . . .
C16 C 0.5648(6) 0.39296(17) 0.5113(4) 0.0550(9) Uani 1 1 d . . . . .
H16 H 0.4394 0.4152 0.5043 0.066 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C14 2.095(4) . ?
O1 C4 1.231(4) . ?
C1 C9 1.370(5) . ?
C1 C2 1.371(6) . ?
C2 C3 1.386(5) . ?
C3 C4 1.426(5) . ?
C3 C11 1.474(5) . ?
C4 N10 1.438(5) . ?
C5 C6 1.331(6) . ?
C5 N10 1.382(5) . ?
C6 C7 1.409(6) . ?
C7 C8 1.333(6) . ?
C8 C9 1.426(6) . ?
C9 N10 1.393(4) . ?
C11 C16 1.393(5) . ?
C11 C12 1.396(5) . ?
C12 C13 1.378(6) . ?
C13 C14 1.380(5) . ?
C14 C15 1.377(5) . ?
C15 C16 1.378(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
C9 C1 C2 120.7(3) . . ?
C1 C2 C3 122.7(4) . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 C11 121.1(3) . . ?
C4 C3 C11 119.2(3) . . ?
O1 C4 C3 127.5(3) . . ?
O1 C4 N10 117.4(3) . . ?
C3 C4 N10 115.2(3) . . ?
C6 C5 N10 122.4(4) . . ?
C5 C6 C7 119.8(4) . . ?
C8 C7 C6 119.0(4) . . ?
C7 C8 C9 122.5(4) . . ?
C1 C9 N10 118.1(3) . . ?
C1 C9 C8 125.1(4) . . ?
N10 C9 C8 116.8(3) . . ?
C5 N10 C9 119.6(3) . . ?
C5 N10 C4 116.8(3) . . ?
C9 N10 C4 123.6(3) . . ?
C16 C11 C12 117.6(3) . . ?
C16 C11 C3 121.8(3) . . ?
C12 C11 C3 120.6(3) . . ?
C13 C12 C11 120.9(4) . . ?
C12 C13 C14 120.2(4) . . ?
C15 C14 C13 119.9(4) . . ?
C15 C14 I1 119.7(3) . . ?
C13 C14 I1 120.4(3) . . ?
C14 C15 C16 119.8(4) . . ?
C15 C16 C11 121.5(3) . . ?

_refine_diff_density_max         0.479
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.078

_shelxl_version_number           2014-1

_database_code_depnum_ccdc_archive 'CCDC 1026205'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_4e

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H10 F3 N O'
_chemical_formula_sum            'C16 H10 F3 N O'
_chemical_formula_weight         289.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.9430(15)
_cell_length_b                   12.7966(14)
_cell_length_c                   7.3613(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.394(2)
_cell_angle_gamma                90
_cell_volume                     1299.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3386
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      24.76

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.486
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.236
_exptl_absorpt_coefficient_mu    0.122
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.9405
_exptl_absorpt_correction_T_max  0.9764
_exptl_absorpt_process_details   '(Sheldrick, 2000)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker Smart Apex CCD diffractometer 01-670-01'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            10269
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.171
_diffrn_reflns_theta_max         25.452
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2388
_reflns_number_gt                1557
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/1 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0526P)²+0.0559P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2388
_refine_ls_number_parameters     247
_refine_ls_number_restraints     181
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1223
_refine_ls_wR_factor_gt          0.1076
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.048
_refine_ls_shift/su_mean         0.001

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
O1 O 0.44379(11) 0.79605(11) 0.2070(2) 0.0714(5) Uani 1 1 d . . . . .
C1 C 0.33198(17) 0.50348(17) 0.1836(3) 0.0587(6) Uani 1 1 d . . . . .
H1 H 0.3047 0.4372 0.1848 0.070 Uiso 1 1 calc R U . . .
C2 C 0.42882(16) 0.51729(16) 0.2496(3) 0.0531(6) Uani 1 1 d . . . . .
H2 H 0.4660 0.4593 0.2905 0.064 Uiso 1 1 calc R U . . .
C3 C 0.47276(14) 0.61452(14) 0.2571(3) 0.0454(5) Uani 1 1 d . . . . .
C4 C 0.41648(15) 0.70463(17) 0.1998(3) 0.0503(5) Uani 1 1 d . . . . .
C5 C 0.26331(18) 0.77019(18) 0.0510(3) 0.0617(6) Uani 1 1 d . . . . .
H5 H 0.2923 0.8358 0.0546 0.074 Uiso 1 1 calc R U . . .
C6 C 0.17060(19) 0.7604(2) -0.0214(4) 0.0762(8) Uani 1 1 d . . . . .
H6 H 0.1357 0.8188 -0.0682 0.091 Uiso 1 1 calc R U . . .
C7 C 0.12526(19) 0.6621(2) -0.0273(3) 0.0770(8) Uani 1 1 d . . . . .
H7 H 0.0603 0.6552 -0.0772 0.092 Uiso 1 1 calc R U . . .
C8 C 0.17671(18) 0.5784(2) 0.0397(3) 0.0700(7) Uani 1 1 d . . . . .
H8 H 0.1466 0.5134 0.0356 0.084 Uiso 1 1 calc R U . . .
C9 C 0.27535(16) 0.58638(17) 0.1162(3) 0.0518(6) Uani 1 1 d . . . . .
N10 N 0.31776(12) 0.68471(13) 0.1212(2) 0.0496(5) Uani 1 1 d . . . . .
C11 C 0.57751(14) 0.62553(15) 0.3242(3) 0.0454(5) Uani 1 1 d . . . . .
C12 C 0.64149(16) 0.54724(16) 0.2867(3) 0.0538(6) Uani 1 1 d . . . . .
H12 H 0.6177 0.4894 0.2179 0.065 Uiso 1 1 calc R U . . .
C13 C 0.73870(16) 0.55400(17) 0.3496(3) 0.0609(6) Uani 1 1 d . . . . .
H13 H 0.7801 0.5010 0.3227 0.073 Uiso 1 1 calc R U . . .
C14 C 0.77581(17) 0.63906(18) 0.4529(3) 0.0593(6) Uani 1 1 d . . . . .
C15 C 0.71379(17) 0.71718(18) 0.4913(3) 0.0609(6) Uani 1 1 d . . . . .
H15 H 0.7381 0.7743 0.5614 0.073 Uiso 1 1 calc R U . . .
C16 C 0.61616(16) 0.71129(17) 0.4267(3) 0.0547(6) Uani 1 1 d . . . . .
H16 H 0.5754 0.7653 0.4518 0.066 Uiso 1 1 calc R U . . .
C17 C 0.8806(2) 0.6437(2) 0.5236(4) 0.0854(9) Uani 1 1 d D . . . .
F1_a F 0.9116(6) 0.7430(4) 0.5578(9) 0.093(2) Uani 0.517(3) 1 d D U P A 1
F2_a F 0.9367(7) 0.6063(5) 0.4034(10) 0.096(2) Uani 0.517(3) 1 d D U P A 1
F3_a F 0.9066(8) 0.5908(6) 0.6812(9) 0.129(3) Uani 0.517(3) 1 d D U P A 1
F1B_b F 0.9118(13) 0.7251(7) 0.6299(17) 0.114(4) Uani 0.277(3) 1 d D U P A 2
F2B_b F 0.9336(13) 0.6437(11) 0.3835(18) 0.098(4) Uani 0.277(3) 1 d D U P A 2
F3B_b F 0.9092(13) 0.5566(8) 0.6224(17) 0.112(4) Uani 0.277(3) 1 d D U P A 2
F1C_c F 0.9198(14) 0.7341(8) 0.478(2) 0.112(4) Uani 0.206(3) 1 d D U P A 3
F2C_c F 0.9353(10) 0.5666(9) 0.476(2) 0.123(4) Uani 0.206(3) 1 d D U P A 3
F3C_c F 0.8897(11) 0.6441(11) 0.7097(9) 0.101(4) Uani 0.206(3) 1 d D U P A 3


_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
O1 C4 1.229(2) . ?
C1 C9 1.371(3) . ?
C1 C2 1.378(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.384(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.424(3) . ?
C3 C11 1.479(3) . ?
C4 N10 1.436(3) . ?
C5 C6 1.330(3) . ?
C5 N10 1.388(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.406(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.343(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.412(3) . ?
C8 H8 0.9300 . ?
C9 N10 1.389(3) . ?
C11 C16 1.395(3) . ?
C11 C12 1.395(3) . ?
C12 C13 1.370(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(3) . ?
C14 C17 1.479(4) . ?
C15 C16 1.377(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 F2C_c 1.324(6) . ?
C17 F1B_b 1.336(6) . ?
C17 F1C_c 1.343(7) . ?
C17 F3_a 1.347(5) . ?
C17 F2B_b 1.353(7) . ?
C17 F1_a 1.353(5) . ?
C17 F3C_c 1.358(7) . ?
C17 F2_a 1.352(5) . ?
C17 F3B_b 1.358(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 C1 C2 120.7(2) . . ?
C9 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C1 C2 C3 122.3(2) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C2 C3 C4 119.64(19) . . ?
C2 C3 C11 120.58(18) . . ?
C4 C3 C11 119.78(18) . . ?
O1 C4 C3 127.2(2) . . ?
O1 C4 N10 117.33(19) . . ?
C3 C4 N10 115.48(18) . . ?
C6 C5 N10 121.5(2) . . ?
C6 C5 H5 119.3 . . ?
N10 C5 H5 119.3 . . ?
C5 C6 C7 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 119.3(2) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 121.7(2) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C1 C9 N10 118.10(19) . . ?
C1 C9 C8 124.4(2) . . ?
N10 C9 C8 117.5(2) . . ?
C5 N10 C9 119.79(19) . . ?
C5 N10 C4 116.76(18) . . ?
C9 N10 C4 123.43(18) . . ?
C16 C11 C12 117.7(2) . . ?
C16 C11 C3 122.71(18) . . ?
C12 C11 C3 119.62(18) . . ?
C13 C12 C11 121.2(2) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 119.2(2) . . ?
C15 C14 C17 121.1(2) . . ?
C13 C14 C17 119.7(2) . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 120.9(2) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
F2C_c C17 F1C_c 107.8(6) . . ?
F1B_b C17 F2B_b 106.2(6) . . ?
F3_a C17 F1_a 105.9(4) . . ?
F2C_c C17 F3C_c 107.2(6) . . ?
F1C_c C17 F3C_c 105.5(6) . . ?
F3_a C17 F2_a 106.1(5) . . ?
F1_a C17 F2_a 104.8(4) . . ?
F1B_b C17 F3B_b 106.3(6) . . ?
F2B_b C17 F3B_b 104.9(6) . . ?
F2C_c C17 C14 117.0(7) . . ?
F1B_b C17 C14 117.2(8) . . ?
F1C_c C17 C14 111.4(9) . . ?
F3_a C17 C14 114.3(5) . . ?
F2B_b C17 C14 110.7(9) . . ?
F1_a C17 C14 112.0(4) . . ?
F3C_c C17 C14 107.3(7) . . ?
F2_a C17 C14 113.1(5) . . ?
F3B_b C17 C14 110.7(8) . . ?

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
C9 C1 C2 C3 2.2(3) . . . . ?
C1 C2 C3 C4 1.7(3) . . . . ?
C1 C2 C3 C11 -178.33(19) . . . . ?
C2 C3 C4 O1 176.0(2) . . . . ?
C11 C3 C4 O1 -3.9(3) . . . . ?
C2 C3 C4 N10 -5.6(3) . . . . ?
C11 C3 C4 N10 174.47(16) . . . . ?
N10 C5 C6 C7 0.3(4) . . . . ?
C5 C6 C7 C8 -0.4(4) . . . . ?
C6 C7 C8 C9 0.0(4) . . . . ?
C2 C1 C9 N10 -1.7(3) . . . . ?
C2 C1 C9 C8 177.4(2) . . . . ?
C7 C8 C9 C1 -178.8(2) . . . . ?
C7 C8 C9 N10 0.4(3) . . . . ?
C6 C5 N10 C9 0.1(3) . . . . ?
C6 C5 N10 C4 -178.6(2) . . . . ?
C1 C9 N10 C5 178.74(19) . . . . ?
C8 C9 N10 C5 -0.5(3) . . . . ?
C1 C9 N10 C4 -2.6(3) . . . . ?
C8 C9 N10 C4 178.16(18) . . . . ?
O1 C4 N10 C5 3.4(3) . . . . ?
C3 C4 N10 C5 -175.12(17) . . . . ?
O1 C4 N10 C9 -175.24(19) . . . . ?
C3 C4 N10 C9 6.2(3) . . . . ?
C2 C3 C11 C16 -144.2(2) . . . . ?
C4 C3 C11 C16 35.8(3) . . . . ?
C2 C3 C11 C12 35.0(3) . . . . ?
C4 C3 C11 C12 -145.0(2) . . . . ?
C16 C11 C12 C13 0.5(3) . . . . ?
C3 C11 C12 C13 -178.81(19) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C12 C13 C14 C17 178.4(2) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C17 C14 C15 C16 -179.1(2) . . . . ?
C14 C15 C16 C11 1.2(3) . . . . ?
C12 C11 C16 C15 -1.2(3) . . . . ?
C3 C11 C16 C15 178.07(18) . . . . ?
C15 C14 C17 F2C_c -178.4(8) . . . . ?
C13 C14 C17 F2C_c 3.0(9) . . . . ?
C15 C14 C17 F1B_b 1.8(8) . . . . ?
C13 C14 C17 F1B_b -176.8(7) . . . . ?
C15 C14 C17 F1C_c -53.8(8) . . . . ?
C13 C14 C17 F1C_c 127.6(7) . . . . ?
C15 C14 C17 F3_a 95.5(5) . . . . ?
C13 C14 C17 F3_a -83.2(5) . . . . ?
C15 C14 C17 F2B_b -120.2(7) . . . . ?
C13 C14 C17 F2B_b 61.2(7) . . . . ?
C15 C14 C17 F1_a -24.9(5) . . . . ?
C13 C14 C17 F1_a 156.4(4) . . . . ?
C15 C14 C17 F3C_c 61.2(7) . . . . ?
C13 C14 C17 F3C_c -117.5(7) . . . . ?
C15 C14 C17 F2_a -143.1(4) . . . . ?
C13 C14 C17 F2_a 38.3(5) . . . . ?
C15 C14 C17 F3B_b 123.9(7) . . . . ?
C13 C14 C17 F3B_b -54.7(7) . . . . ?

_refine_diff_density_max         0.132
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.031

_shelxl_version_number           2014-1

_database_code_depnum_ccdc_archive 'CCDC 1026206'
